Consequences of Cross Dressing by Cindy Johnson ([email protected])
My dilemma was that I masturbated all over my mother's gown and nylons and I frantically tried to clean everything up as fast as possible. I was frightened that it would leave a stain and I didn't know what to do but after twenty minutes of cleaning everything with soap and water, I felt like I was in the clear. I put everything back where it I found them and ran to my room reflecting on what had just happened. I slept restlessly that night as I worried if my mother would notice anything. Nothing happened, and for the next few weeks I avoided going into her room so that I wouldn't even see her lingerie and have that overwhelming temptation to put on her clothes again.
Over the next few weeks, I constantly thought about wearing her lingerie and how amazing it felt. I also had some bad feelings about wearing her things. The good feelings came with a feeling of guilt but the good feelings I experienced made me want to go back into her room and do it again. The temptation to dress in her things was overwhelming.
For the next year I did occasionally go in there and re-live that event and each time the feelings grew stronger and stronger. By this time my brothers were out of the house and off to college it was just mother and I living together. I was 14 years old when they went off to college and mother and I were even closer than ever as I was all she had left to fuss over.
I found myself in her room more often as I had more free time with everyone out of the house and mother away at work all day, to experiment and dress up. I was now comfortable putting on her pantyhose, panties, bras, and lingerie and started trying on some of her dresses and heels. At one point I would rush home from school every day and spend hours dressing and walking around the house in her things and having intense orgasms before I undressed, and she came home from work. I thought I was careful in wearing her things and putting them back in the same place so that she would never discover I was wearing dressing in her clothes.
One weekend I came home to find mother finishing up the laundry and putting things away when I found a pair of her panties in my underwear drawer. I didn't say anything and started wearing them to bed at night. The next week there was a pair of pantyhose in my sock drawer and I started to wonder if mother just made a mistake or was putting them there on purpose. It continued for several weeks until one night when we were eating dinner, I mentioned casually that I had found some of her things in my drawers.
"Mom, you must have accidentally put some of your panties in my dresser drawers. Do you want me to put them back on your dresser or in the laundry?"
"No need, baby. Let's just keep them where they are for now and next time, I put the laundry away I'll take them out, unless you want me to leave them there?" she said with a sweet smile.
"Why would I want you to leave them there, Mom?"
"Sweetheart, you know I love you and whatever you do would never change that. So, if you like wearing some of my panties or lingerie, it's OK. I don't mind and I think it's kind of sweet."
I misjudged my mother and I got indignant and made a fuss and yelled at her. "How could you accuse me of such a thing? I can't believe it, that's stupid'" I yelled.
"Listen to me, you little brat, I've known that you've been wearing my things for the last year. Do you honestly think that a woman doesn't know when her things have been moved or worn? Moreover, I didn't even mention anything about all the stains you've left on my good things. I've left you alone and even tried to make things easy for you by leaving you little things to play with so you wouldn't have to sneak around. Don't you ever raise your voice to me, or you'll regret it. Understand?"
I didn't know what to say and just sat there quietly. We did not discuss it again that night and I stopped dressing in her things that afternoon.
College Years
Mother and I stayed extremely close and never discussed my dressing up again. When I went away to college, I had grown a little but still only 5 foot 8 inches which is small for a guy and I never gained much weight, so I remained a small thin boy throughout college. Meeting girls the same height is hard when they are looking for big strong guys.
Most girls aren't interested in small gentle beta-guys but are more attracted to strong Alpha males. What I did learn is that girls like to laugh, and I was always told how funny I was. I developed a way to get attention with girls with my jokes and the knack I had to make them laugh. It worked for me and I was soon dating some of the best looking girls on campus. Other guys would look at me and the sexy girls I dated and could not understand how a hot girl would rather be with me. I had more girls after me then I can remember and became very popular on campus. I found a way to be happy and had some of the best years of my life.
That is the time I met Grace, one of the sexiest girls I've ever met. Her beauty made me weak and just putty in her hands. I was in love with her and did anything she wanted just to be around her. She, of course, had lots of guys after her all the time and she had just broken up with Joey, an enormous bodybuilder guy when she started calling me to hang out.
She loved how I made her feel and laugh. Grace loved being with me and we became a couple. Joey never got over her and openly asked her out in front of me several times, "Why are you with a little wimp like this when you can have somebody like me?"
Grace just smiled and said, "You could never make me feel the way he does, and you'll never understand." It made me feel so good and at that moment my size never bothered me again. I realized there were more important things to relationships then looks or muscle. Dating a girl on the rebound has its advantages but over a long period, the relationship can become complex.
We were married just after graduation and I had an offer to run an IT department at a major media company. Grace got a job as marketing director at Sports Marketing and Consulting Company with international reach. The first couple of years of our relationship were amazing but over time we got busy with work our schedules, which made things difficult for us to have quality time together. My job demanded me being on call 24/7 and her job took her on trips for several days at a time, visiting customers. Recently Grace had to travel to Italy and Paris for over a week at a time.
Because of our jobs, our sex life became infrequent. To be honest, over the last six months Grace had become distant and not engaged in sexual activity. She blamed it on being exhausted from the travel and long hours at work. I started to feel insecure as not being able to meet her needs and satisfy her as she was used to with other guys. You see, as well as being small in stature my penis was also on the small side. Grace never complained but I always felt she wanted more because she seldom came from intercourse and lately, only came after I performed oral sex after we made love. Her disinterest made me concerned since she was around powerful men all day long, either working directly for them or with the clients, which were also usually strong outgoing men. She was either out to dinner or some type of entertainment which kept her out late and tired when she came home after midnight or 3 in the morning. I never complained as I was just feeling lucky and blessed to have someone as beautiful and sexy as Grace for my wife.
Once she started her week-long trips overseas, I saw one of her nightgowns on a hanger behind the bathroom door and I soon found myself exploring her enormous walk-in closet admiring her wardrobe, lingerie, and shoe collection. For some reason, the feelings I had before my college years came flooding back and I had all the old urges to touch and feel the silky material of her dresses and lingerie.
That evening before going to sleep I took her long nylon nightgown off the hanger and put it on before getting into bed. Wearing the gown brought back all the old feelings I've kept suppressed and hidden. The urge to touch myself and rub the nylon over my legs and body were beyond my control. After not being with Grace for so long and frustrated, due to a lack of any relief, the orgasm I had that night was amazing, which lead to me thinking about spending a day in my femme mode once again. I told myself it would only be a one-time thing, and that would be enough.
After getting a text from Grace as I was having my coffee, I called into work and told them I'd be working from home for the rest of the week which gave me lots of time to prepare for my day of a reunion with my alter ego, Amy. Grace said she was busy and working late with her team every night and was completely exhausted and couldn't wait to get back home.
I felt bad for her having to work so hard and be out late with clients, but I also was happy about having the week alone and exploring some old feelings and hobbies. As I had my coffee, I browsed several sites for women's clothing and imagined ordering outfits that I would love to wear. After about an hour of this, I realized I was hard and excited again and had a great idea. With almost a full week to explore the past, I came up with a wild notion. If I ordered some outfits on Amazon Prime, I could have them tomorrow and dress up all week. Could I do that? Would that be considered, cheating on Grace? I pondered this for the next few hours after cleaning up the house and placing her nightgown back on the hanger.
The feeling of the nylon and sexy lace helped me decide. I would do it. Order some things and dress up and get it out of my system. Before Grace gets home, I can return or dispose of everything and nobody would have a clue. So, for the next several hours I shopped on Amazon and loaded up the cart. It was so fun to shop for feminine clothing and I got carried away as my shopping cart grew.
Knowing my size and what looks good on me I ordered several dresses in different styles, leather skirts, skater skirts, tight skirts, silky skirts, sweaters, blouses, lace tops, 3 matching pantie and bra sets, Spanx for the tight skirt and dresses, 4 pairs of heels all 4" including a cute pair of flowered wedge sandals. Several pair of Wolford Pantyhose and some thigh high stockings in different shades and colors to match the cute outfits I purchased.
I ordered all kinds of make-up for my skin tone. I found some adorable wigs and ordered 3 in different styles, along 3 purses, earrings, bracelets, belts, and all the accessories I could imagine. It was fun to create an outfit with everything to wear with it right down to the hairstyle and earrings. As I shopped, I also came across some sex toys that were available for the next day delivery and ordered several toys that I could play with. Shopping for anything I could imagine was addicting and so much fun.
When I was done the shopping, basket came to almost $1600, which I placed on my credit card knowing Grace would never see the charge, as I did all the bills and managed all the money. The amount wasn't an issue as I saved a great deal of money as we both earned a great living in our positions. Nobody would ever know, and I felt completely safe as I selected Next Day delivery and checked out. I also knew I could return some items that I might not like.
Amazon is astonishing. I was able to shop for every style and item I needed and wanted at a great price, order it online and have it all the next day in complete privacy. I smiled as I planned how I would spend the week. I already called work and took a few days off and I would spend Wednesday through Saturdays Amy. I would have four full days as Amy Rose, I would pack everything up Sunday morning, clean up the house, and make sure that I left no evidence. I will pick her up at the airport on Sunday at 4 pm and bring her home to a nice dinner I'll have ready.
With all my plans in place, I spent Tuesday shaving my body hair, taking a scented bath and excitedly waited for my deliveries to arrive. At 2 pm on Tuesday, the Amazon Prime Truck pulled in the driveway and delivered 7 large boxes into the garage. I was so excited and brought all the boxes down to the guest room in the lower part of our house. I opened each box and smiled as I carefully placed everything in the closet and the dresser drawers. The makeup, perfume, lotions, nail polish and remover, and I placed on the bathroom makeup table. I carefully placed the wigs on the marble counter top.
The panties and bras I placed in the top drawers and the stockings and pantyhose in the other top drawer. The Spanx shape wear along with the slips I placed in another drawer next to the draw that now held the toys I ordered. I checked and everything I ordered was delivered in the correct sizes. I was so pleased when I tried on the heels and found that I selected the right size because it's so hard to order high heels without trying them on first but the ones I ordered would work perfectly.
I prepared a salad for dinner, cleaned up the house, checked emails, sent Grace a text, and took care of all the errands I needed to complete for the week leaving Amy free to live and enjoy herself for the next four days.
Tuesday night I took another scented bath, shaved again and put on some new lavender-scented lotion all over my body. With my blonde hair and a shaved body, my skin was smooth and subtle. After I was done and satisfied with my primping, I sprayed a little perfume on my pulse points and put on some light makeup before selecting a pair of panties and a nightgown to wear for the evening.
I didn't get much sleep as the feelings and sensations of nylon and the scent of perfume kept me excited. Thinking of all the outfits I would be wearing and being dressed 24/7 was stimulating and exciting. Finally, I got some sleep and woke up around 9 am, took a shower, shaved any possible signs of hair again, applied some lotion, slipped my nightgown over my soft scented skin, and went to the kitchen for some coffee.
Sitting there in the red nightgown, panties, and a pair of heels drinking my coffee was amazing. I forgot how much I loved wearing these clothes and feeling so feminine and knew it was going to be hard to contain these feelings. It was as if I let the genie out of the bottle, the cat out of the bag, or opened Pandora's Box. I wasn't sure I could ever put these feelings and desires back in the box again and it made me nervous and excited at the same time.
After my coffee, I went to the guest room downstairs and picked out a fresh bra and pantie set and sat at the makeup mirror in the bathroom to contemplate how to dress for the day. I saw the red nail polish and decided to start with that as I opened the bottle and painted my toenails the Revlon Red polish. I opened the nail extension package and carefully glued the nail extensions in place and filed them to a medium length and a soft square before polishing them with the same color as my freshly painted toenails. They looked so beautiful and feminine as I held up my hands and admired the pretty color and long nails. I loved how it made my hands look dainty and feminine and when I looked at my feet the red toes just screamed, girly and feminine. Because I wanted to enjoy the process and have an expert result it took over an hour to finish my nails.
I made some more coffee and enjoyed the new feelings of my long nails as I touched things and got used to having longer nails. Long nails have a way of making your hand movements more controlled and purposeful as I found myself moving slower, using the pads of my fingers more often and by doing so I realized the movements appeared much more feminine. Exactly what I was hoping for!
When my nails were dry, I started on my face and make-up after I watched several YouTube videos on my laptop computer. I tried several different techniques from watching Grace do her make-up over the years and some ideas from the videos. I even succeeded in applying false eyelashes after a few attempts. All in all, the results were better than I expected, and I knew over the next few days I would perfect my skills.
After I was happy with my new-look I picked out the short blond wig with the cute bangs and pinned it in place. After I had it just right, I took a step back and felt butterflies in my stomach as the image in the mirror was a young cute girl, no way a man. In less than 4 hours I had transformed my look and became the girl I've kept buried inside for over the last 10 years. The feeling was sensational, exhilarating, and gave me a happiness I hadn't felt in a long time.
Smiling and excited I went into the bedroom, sat on the bed and opened the new package of Wolford sheer black pantyhose and slid them over my smooth, silky, fresh shaved legs. The way the pantyhose and nylon felt as I rubbed my legs together and touched them with my new long red nails, was intoxicating. I was experiencing feelings that I never had before and didn't want to stop. I took the dress that I had hung on the back of the door and carefully stepped into it before zipping it up in place.
A perfect fit and with my padded bra cups and the shape wear, I squeezed into gave me a perfect figure. The final highlight was stepping into my new patent black leather 4" heels. Between the make-up and sexy hairstyle, combined with my long legs and high heels I became the girl of my dreams. I found myself just admiring the girl in the mirror and lost track of time. I posed and moved as I tried to imagine myself being this gorgeous girl.
It was not 1 pm and I had been getting dressed and made-up for the last 4 hours and realized I needed to have a snack and finally pulled myself away from the mirror and headed down to the kitchen and made a light lunch and a protein drink. As I sat at the table I tried to sit and move as I know girls do naturally. I've admired Grace and always noticed how she sat and used her hands and tried to emulate what I had remembered.
Suddenly I noticed things I had never experienced before and realized what it is like living as a woman. In addition to the feelings of all the nylon and silky material from the dress and pantyhose along with the tightness from the bra and shape wear, I noticed how I had to use my hands with my new long red nails. I was now more focused and careful on what I picked up and how I touched things. I noticed the faint color of my red lipstick on my coffee cup and how my new long lashes seemed to constantly be in view. I was in sensory overload as I was experiencing so many new things all at once, but I was also happier than I had been in a very long time and relished every second of these new experiences.
For the rest of the day, I pranced around the house, changed outfits several times, and touched up my make-up uncountable times. It was so much fun.
Grace sent a text message and complained about the long days and late dinners with her clients and co-workers every night and wished she was back home. Her group liked to go out and have fun every night and she always complained about having to attend the parties and dinners. I felt guilty as she was working hard, and I was home playing dress up, but the good feelings overwhelmed me, and I accepted things for what they were. Since she isn't here and would not find out I told myself it was OK, and she would understand if she was in my place.
After a small salad for dinner, I cleaned up the house and slipped into one of my cute new nightgowns and lay in bed with my laptop. I spent two hours watching videos on how to act and move more gracefully and womanly. There were training videos that would help me look more natural as a woman and be as passable as real females that have a lifetime of practice. I watched some more videos on additional make-up techniques that I would use tomorrow and finally shut it down and laid in bed trying to soak in all the feelings and things that I did today.
The silky material and the scent of the perfume made me very aroused and I played with myself and had the best release and orgasm I have had in years. I let out a scream and squirted a tremendous stream of semen all over myself and the nightgown. I knew it would need to be washed tomorrow. I cleaned up, put on a fresh nightgown and had the best night sleep I had in years. Life was amazing now and I was thrilled it would continue like this for a few more days.
For the next several days I remained in my female mode and continued working on my makeup skills, my feminine movements including hand motions, walking in heels, sitting and standing in short skirts, and making sure I continued to use the feminine movements in everything I did. Removing over 25 years of male habits in 4 days was not easy but I did get much better and found myself making some motions more naturally.
Saturday night I knew I would have to return to being male and dreaded having to put everything in boxes get rid of the evidence as I knew I would not be able to dress and act like this in front of Grace. She always admired macho, strong, and controlling guys, which always made me wonder why she stayed with me. I know my humor and good nature attracted her at the beginning but over the years I always felt she wanted and needed more than I could give her.
After my pity session, I realized I had to get busy and piled everything on the bed and chairs and contemplated what to do with my treasure. Originally, I wanted to just throw it all out and get rid of the evidence, but another thought came into my head. Why not box everything up carefully and put them in a safe place where nobody would find them because the next time Grace had to leave for the week, you could dress up again.
Of course, this thought took over and I did pack things up and hide them downstairs in the back of the guest closet under some other boxes we stored there. Nobody would find them and if I had the desire to dress again, I wouldn't have to spend all the money because everything would be safe and sound.
I spent over two hours making sure all the evidence was gone, my makeup was removed, and the house looked normal again. I had a restless night sleep as I re-lived the last few days in my mind and how much I loved living as a female. I loved every second and really wanted it to continue but I knew that would never happen and I had to snap back into reality.
After I brought Grace home from the airport, I had a dinner ready for her when she got home. I told her to relax as I brought her to the kitchen after I put her bags up in the bedroom. I served her dinner and her favorite drink, a mimosa, showing her how much I missed her.
"Very impressive, baby! This is so nice, and you went all out with my favorite drink. The house looks spotless and all the dishes are put away. I'm stunned. You would make the perfect housewife," she said giggling.
That comment really rocked me at her even thinking that. I did like the idea but as her husband, I couldn't tell her that I loved the idea, so I acted like a typical guy. "Very funny, I just wanted you to come home to a clean house since you've been working so hard."
"Well, I appreciate it and it was a long week. The guys took me out every night and being the only female in the group made it even worse. Guys act so weird and don't know how to treat a lady. I didn't get much sleep and I'm exhausted. I hope you don't mind if you take a hot bath and just relax in bed for a while, do you?"
I never liked the idea of her being out with these sports guys late at night, but Grace always made me feel safe and secure and that it was part of the job and something she didn't really enjoy. The thoughts of her with all those large, well-built men, started to get into my head but I put it aside and offered to draw her bath while she got unpacked.
While she started unpacking, I finished the dishes and started a nice warm bath for Grace. I added some bath beads and made sure the temperature was just right for her and even put out a few candles and put on some gentle meditation sounds, before lowering the lights and telling her that the bath was ready.
She just smiled when she came in; she hugged me and thanked me for the wonderful welcome home surprise. About an hour later she came back to bed and even though it was still early, I laid there with her as she just relaxed from her long trip.
Soon I was cuddling into her and playing with her wonderful breast, rubbing them and gently kissing them through her sheer pink nightgown. I wasn't sure if it was her breast of the silky nylon that was getting me hard, but we made wonderful love that afternoon, something we hadn't done for a very long time. After we finished and just lay next to each other in bed.
Grace was smiling and said, "If that's how you're going to treat me whenever I leave town then I'm going to go out of town every week, my love."
I smiled to myself thinking about that statement and thought about the last four days and how wonderful things were just about perfect.
Over the next three months, Grace continued to make this trip once a month and my dress up games continued except instead of just 4 days per week, I dressed up an hour after her plane took off and spent the next 6 full days living as a natural-born woman.
Of course, I added to my wardrobe and makeup collection, added lots of accessories, including some adorable earrings, bracelets, rings, and a few necklaces. Practicing my feminine movements and make-up skills had paid off, because now when I was in my female mode, I was completely comfortable as a female. If anyone observed me, they would know I was born female and would never guess there was something hidden below my pantyhose.
One night I found a video on how to control your voice and develop a female voice and after weeks of practice, I got quite good. I would practice by singing and using the techniques I learned. My feminine voice became natural after several weeks of practice.
On her third trip to Germany, I had a desire to go out as my female self and got up the nerve to do it one night. I spent hours getting dressed and making sure I looked perfect, I picked out a cute outfit, touched up my makeup, fixed my hair, grabbed a purse and went into the garage. I carefully got into the car as I practiced and swung my legs inside. Started the car and opened the garage door and slowly pulled out of the driveway and left the neighborhood. I passed several neighbors walking down the street from behind, so they didn't have a chance to see me and drove out to the highway.
I got up the courage to go to a Wendy's drive-thru and ordered a diet coke. The teenage boy didn't have a clue when I gave him the money and the sensation of passing and being out at for the first time as a female was beyond description. I drove up to the next window to get my drink when the store manager handed me my diet coke and gave me a warm smile as I nervously took it and watched my long red nails touch his hand as I took the drink. "Have a lovely night, miss," he said smiling. "Thank you, sir," I said in my new voice. I realized that he liked what he saw and that made me feel warm and tingly as I drove away. I had the biggest smile on my face and realized I had passed in public without any problem. That night I thought about that guy at the drive-thru as I played with myself and exploded with tremendous orgasms. Being a female was becoming more and more exciting.
It was right after that when I started using some of the toys I had purchased. At first, I wasn't sure I would enjoy putting something inside me, but I found myself so excited and turned on after a day of dressing up that one night, I lubed up one of the lives like penis phallic and played with it at my opening. I rubbed my nightgown over my chest and started tweaking my nipples until I was so hot and excited that I pushed the tip of the penis dildo just inside my opening and gasped when it entered me.
My eyes opened wide when I felt the bulbous head enter me and rested inside as I continued to play with my now excited nipples. Soon I realized that I had pushed the entire penis inside me and started rubbing my cock. I could not control my feelings as I moved the penis in and out slowly and thought about that guy at Wendy's smiling as I drove away. I stroked myself and within a very short time exploded with an even greater orgasm than I had ever had before. From that moment forward I became very familiar with all my toys and enjoyed them to the fullest.
My imagination grew as I thought of myself being with a man that made love to me as a woman, over and over again. I felt fulfilled and satisfied as my desire continued to grow. I often fantasized about being out in all my feminine self and some handsome man asking me to join him for a drink, having a conversation as I flirted with him until he kisses me gently and took me up to his bed as his woman, and became his girlfriend.
What started as a few days of dressing had become a much bigger part of my life and a realization that I needed more of this in my life to be completely happy. I recognized that this could never happen and had to appreciate the time I had to experience these feelings.
Grace continued to text me every night while she was away and continued to complain about all the dinners and parties she had to attend. A few nights she had to spend the evening with one of the players alone because the client had to cancel their trip. She said she didn't mind it as much as he was a nice guy and fun to be with, unlike the client so it wasn't horrible. Of course, being on another continent while your hot wife is having drinks and dinner with a Pro Athlete could wear on you unless you were dressed in a sexy cute dress-wearing thigh high stockings and super cute high heels. No, I didn't care that she was alone with some guy and even pleased that she was having fun because it made me feel less guilty, as I dressed and self-indulged more often. My guilt was gone and all that was left was happiness and pleasure.
I still treated Grace special when she came home and re-established our relationship in bed each time. It was if I reclaimed her as my wife each time, she returned from one of these trips and it seemed as if we even grew even closer. She appreciated the fact that I never questioned her anymore about her trips and evenings out at parties with other guys. Things were much better between us and I rationalized that it was my dressing that was helping our relationship. This made my guilt feelings go away and got even more excited about living as Amy.
Italy was going to be a 10-day trip and I was all prepared for my longest period living as a female. I planned to go out to a movie, food shop, and out shopping to buy a new outfit at one of Grace's favorite dress shops to prove I was as passable as I believed I was. This was a big trip for her marketing team as their new client was the Italian men's soccer team. It would mean a big pay-raise for her and most likely a nice promotion. I was excited for her, but not as excited as I was for myself for what I had planned while she was gone.
Work for me was not a problem as I now had my employer used to me working out my home for a week at a time. Having over 5 weeks’ vacation also helped as I used several of them during this time to ensure my plans work out perfectly.
As always, an hour after her plane took off, I started my transition. Things were going perfectly as I tried on some of the new outfits I had ordered, and they fit me perfectly. Losing 8 pounds also helped me get into a smaller size and allowed me to wear tighter fitting outfits.
After spending the day all dressed up, practicing as always, and having a cocktail to steady my nerves, I decided to go to the 8 pm movie alone. Once I checked my make-up and hair, I finished my cocktail and then pressed forward and drove to the local movie theater, after buying my ticket online. I sat in the parking lot for twenty minutes getting the nerve to get out of the car and walk into the theater as Amy. I wore a silky floral print dress that hugged my waist that flared out to about six inches above my knees. The push-up bra I wore hinted at some cleavage under the lace fabric. I wore 3-inch heels so as not to stand out too much and with my makeup done just right along with the shoulder-length wig, I felt confident as I adjusted my drop earrings in the mirror and touched up my lipstick.
I grabbed my purse and opened the movie application on the phone and headed into the theater. Nobody looked or said anything as I entered and walked up to the attendee where I swiped my phone. He smiled and said, "theater 2 on your left and enjoy the movie, miss."
I just smiled, pushed my shoulders back, and walked confidently in my heels into theater 2. I don't even remember what I saw as I sat there just smiling and feeling what it was like to be out in public, living as a girl. With my hand on my lap and legs crossed I sat there and enjoyed the moment knowing it was a rare or even a once in a lifetime experience.
Some young man with his date held the door for me as we left, and I smiled and said thank you. As I expected I was completely passable, and all my practice must have helped because even the women and girls I came across didn't blink or give me a second look. This gave me a warm feeling inside and helped my confidence as I walked confidently back to my car. I even passed one of our neighbors in the parking lot and noticed him look over and just smile as he walked by, nothing else. Nobody could recognize who I had become. I smiled when I realized that I had 9 more days to live like this full time, and I planned on enjoying every moment.
That week I had dinner out at a restaurant, smiled at countless men, turned down their attempts to join me, a pretty girl all alone. I shopped and purchased more outfits at the dress shop, purchased some shoes at a shoe store in the mall, purchased groceries which was so much fun. I loved pushing the shopping cart all dress up in my heels, I felt like a Stepford wife buying food for her husband and family. Every adventure became more and more exciting.
Needless to say, my new outfits were out on hangers ready for me to try them on along with my new heels, my lingerie was in the hamper or on the bed; my makeup was out next to my wigs. It was a female paradise, and I was enjoying every second. My clothing collection had grown substantially, and I now had a wardrobe to give Grace some competition.
It was Sunday morning and with 4 days left I was in full girl mode. Being all dressed and made-up for the day, I was extra careful with my makeup this morning as I was going to go out shopping at the mall and didn't want anyone to recognize me. I picked out one of my new outfits, a sheer summer dress that showed off my curves and long legs. I enjoyed the looks I got from men whenever I wore an outfit like this. It took me all morning to get ready and I planned on leaving around noon and even considered stopping for lunch on the way. Living this way was now natural and my confidence made it easy to function.
I was downstairs in the guest bathroom putting on my jewelry and perfume when I saw that it was almost one o'clock and I grabbed my purse and headed upstairs to get my keys and leave for the day.
Confidently I walked in my 4-inch heels up to the main level of the house and turned towards the hallway when I froze in complete horror. I stood there in total fear, petrified, and couldn't even catch my breath as I came face to face with Grace and some guy behind her.
We stood there for what seemed like an hour just staring at each other. I really could not move or speak. I have never felt so scared in my life. After a long time, I saw Grace blink and step back and almost tripped on her bag until the man caught her. She had a look I've never seen before and started talking.
"Is that you?" Grace said in a voice and tone I didn't recognize. I didn't answer. She stood up and walked around me looking me up and down. Wow, I sure didn't expect anything like this. This is some surprise, isn't it?"
The guy behind her didn't know what was going and asked, "What's going on, who is she, Grace?"
Grace chuckled and looked at him, "She, is my husband. Yes, believe it or not, this sexy looking girl standing before us is my terrible excuse for a husband. I'm as shocked as you are, Tony. When I left a week ago, I was married to a man, not a tough guy man like you but a sweet, caring, man. It appears that he has been living a lie because you can't be a man and look like this. I have to admit, you make an amazing looking woman."
Tony blinked, "She's your husband? She's a he? Really? Holy Shit, that's amazing!"
"I know, right? She is amazing. What's your name?" I didn't answer as Grace waited for an answer.
Grace slapped me in front of Tony and asked again, "What is your name? What do we call you from now on? You've embarrassed me in front of my co-workers, everyone will know about you, so we need to know what to call you from now on. What is your name?"
Tears started running down my face as I was still afraid to move. She glared at me again and I just lowered my head and said, "Amy Rose."
"Amy Rose, very nice to meet you! Tony, this is my husband Amy Rose."
Tony laughed and said, "Nice to meet you, Amy Rose, you do make a pretty girl." I kept my head lowered and didn't answer.
"Amy, did you hear Tony? A girl always says thank you, to a compliment. Now answer Tony."
"Thank you, Tony, it's nice to meet you as well," I answered in my female voice.
Grace "Oh my god, that voice. You really are a girl, you sound and look just like one. Who are you? Well I guess we will find out, won't we? You have lots of explaining to do, Amy. Tony, do me a big favor and let's keep this between us for the time being. After I get a handle on this, I'll invite you over for dinner and let Amy explain everything. It's the least she can do for making you part of this."
"No worries, I'll keep it quiet for now and I look forward to that dinner. Where do you want me to put your bags?"
Grace pointed to the bedroom and said, "Upstairs to the left is my bedroom, please put them in there." Tony brought the bags upstairs as she continued to look me over. When he was out of sight, she talked to me in a calmer tone.
"Well Amy, we closed the deal with the soccer team faster than expected and I was able to leave early. I was hoping to surprise you and I guess I'm the one that got the surprise. Tony had his car at the airport and offered to drop me off since the car service wasn't scheduled. I can't believe he had to walk into something like this?
You do know that I work with a bunch of horny jocks and professional athletes with high levels of testosterone. If they get word of this, it will be open season on your wife. I'll become fair game to every guy at the office and their flirtations will be out of control. You've put us in a bad situation by embarrassing me in front of my friends' and co-workers. We have a lot to work out and when Tony leaves you will start explaining things to me, understand?" I nodded.
She continued, "I need a drink. Go open a bottle of wine and bring out a glass for me into the living room. I'm going to go upstairs and change into something more comfortable and then we will talk."
Tony came out while I was in the kitchen opening a bottle of wine. I heard them speaking and then I heard Tony call out, "Nice meeting you, Amy Rose. Hope to see you again." I knew I had to answer if I didn't want Grace to be angry again.
"Bye Tony, thanks," I said.
I saw Tony hug Grace in the reflection of the dining room hutch, and I heard him ask her if she would be OK. I heard her answer, "I'm not sure Tony, but promise me you won't mention this to anyone, it would devastate things for me at work." He nodded and said OK as she walked him to the door.
These last thirty minutes were surreal, and the feelings of panic and terror were overwhelming. When I heard the door close, I came out with the bottle of wine and a glass which I placed on the small table in front of her as she sat with her legs under her on the couch.
"Pour me a glass Amy, and then I want you to unpack my bags, put my soiled things in the hamper, and them come back down here. That will give me some time for the wine to kick in and calm me down a little." I went to the bedroom where Tony brought her bags when I heard her call out.
"Do not change a thing, I want you to wear everything you have on when you come back here. Understand?"
"Yes," I answered in a low voice and went to the bedroom where her two bags were on the bed. I took out her things and started putting the clothes in the laundry basket. The wonderful feelings I had wearing the silky nylons and dress were now gone and the horror of watching my long red nails handle her lingerie brought me back to reality. I felt like I wanted to throw up or run out of the house but there was nowhere to go. I had no choice but to try and explain things to my wife. I've never seen Grace so angry or embarrassed and I'm afraid I triggered something. I never planned on telling her about my feminine desires and I certainly never expected to get caught, let alone be outed by one of her co-workers. Yep, things went for amazing to horrific in less than a minute.
I took my time and gave Grace half an hour to cool down and straighten the bedroom before I went back to the living room to face my wife and come clean about things. She motioned for me to refill her wine glass and for me to sit on the opposite couch which I did without saying a word. I've been dressing as Amy for so long that I didn't realize I was still acting and moving in my female role. I gently sat on the couch and crossed my legs as she sat quietly and took everything in as she sipped her third glass of wine.
"Well, this is quite surprising, Amy Rose. Do tell me everything and do not leave any detail out or I will put you out on your ear. Do you understand? I expect complete transparency and if I think you're lying or holding back on anything, I swear you will pay for the rest of your life. Now, how did we get here?"
For the next two hours, I told her everything from when I dressed at home with my mom to this moment. I explained how the feelings came back when she was gone, and I came across some of her things which triggered some desires I believed to be gone forever.
It was hard and I cried and cried as I spoke, but Grace just sat there listening and instructing me to continue whenever I stopped. "Don't stop there, Amy. I want to know everything and keep speaking in that cute feminine voice. Sitting here with you looking like this, watching you move so gracefully, and speaking like that makes me think of you more of a girlfriend and no way a man. I think it's making everything easier for me to understand. Please continue."
She got angry when I explained how much I spent. She made me tell her about each item I purchased and why I purchased them, she wasn't going to make this easy. She asked me where I kept them and told her that right now, everything was in the guest room and that the clothes were in the closet and the makeup on the makeup table along with my wigs. She listened intently and had me get another bottle of wine. I could feel her eyes watching me walk in short dress and heels and wondered what she was thinking.
As I filled her glass she smiled and said, "What you are telling me is amazing and I wouldn't have believed any of it if I didn't see you like this. The way you walk in a dress and heels seem so natural for you, the way you move and use your hands with those adorable long nails makes me realize you have spent a great deal of time perfecting Amy. I think Tony is still in shock that you were my husband. I can't wait to talk to him tomorrow about all this and hopefully, he keeps his mouth shut and keeps our secret. You better pray he keeps this between us, Amy."
I left nothing out as I continued to tell her everything including my ventures outdoors, going to the movie, food shopping, dinners, and even the men who tried to join me when I ate alone. She was fascinated by everything and she encouraged me to continue. I knew I had to tell her everything before she found out I left something out and told her about the toys I had purchased and started using to give myself pleasure.
To my surprise, Grace didn't look upset or for that matter she didn't change her facial expressions with anything I told her, and I finally started to relax when I felt like I told her everything.
"Well, all that is a lot to take in Amy. Taking all that time off, working out of the house so you can live full time as a female was a big commitment and I now realize how important it is to you. But let me make sure I have it all straight.
When I was gone you saw some of my lingerie which made you think of dressing up as you did with your mom when you were young. You then ordered a complete wardrobe and accessories from Amazon to dress-up while I was away."
"Yes," I answered. She continued,
"Whenever I went away for a week overseas you became Amy twenty-four hours a day until I returned. You practiced becoming as feminine as possible, learned your makeup skills, feminine movements, how to walk in heels and a dress, how to wear pantyhose and stockings, shape wear, dresses, and everything else girls wear?"
"Yes."
"I see, and then every time I left you would arrange to work from home or take time off to live as Amy."
"Yes."
"You continued to buy more clothes and accessories and kept them hidden from me in the guest room and you never planned on telling me about this or getting caught."
I hung my head and said, "Yes, I'm so sorry."
"On my last few trips, you started going outside as Amy and went to movies, restaurants, dress shops, and even grocery shopping without anyone guessing you weren't a woman."
I smiled and said, "Everyone thought I was a girl."
She didn't appreciate my getting comfortable and lashed out at me.
"You think that's cute? That everyone in our area thought my husband was a girl, a woman? Do you not realize how that reflects on me, Amy? I have a husband that is prettier than most of my girlfriends, that likes to go out by herself and attract the attention of men, you said so yourself! While you dressed as Amy, you even lay in bed and dream of being with a man sexually as you take a life-like penis inside you.
As a woman and your wife, how do you think that makes me feel? I'll tell you! You see, while I'm on the other side of the world, working eighteen hours a day, my husband is here with another woman. Yes, in my eyes you've cheated on me, and by not allowing me to be part of this you have intentionally kept it hidden. That is called an affair, Amy.
You, my husband, have been having an affair with Amy, while I'm thousands of miles away fighting of men that want nothing more than to get me into bed and fuck my brains out. Big, Manly Men. Pro athletes, who could probably rock my world, have wanted me every night but I turn them down and remind them I'm happily married.
How does that make me feel? Betrayed! I feel like you have betrayed my trust, cheated on me with this woman, flirting with men and dreaming of them taking you, and making you their girl. Frankly, I'm devastated! Honestly, I'm not sure where this goes from here. This will take me some time to understand and to forgive you, and to see if I can cope with the situation. One thing is certain; things will never be the same between us again. Once someone betrays my trust, I can longer continue to trust them in the future. Once someone breaks my heart, I usually leave them, but this is different, we're married, for now, and I did take a vow for better or worse and I won't betray our vows as you have.
I do love you but right now I am angry, hurt, and embarrassed. You've made me feel inadequate as a wife and let strangers outside our marriage know this as well. Your betrayal has broken my heart and I can hardly stand to be with you right now. I'll need some time to figure this out and try to salvage this marriage, but I am not making any promises except that I will try hard to understand and forgive you, but it might not be easy for you and I hope you're prepared for whatever I decide.
Since Amy has taken over the guest room, that will be where she spends her time and sleeps until I work things out. Do not hide any of Amy's items, do not pack anything up or put anything away. I want to examine everything you've purchased and see what type of taste Amy has. If you disobey any of my requests or if there is anything else you need to confess or tell me, this is the time because if you disobey me, or if there are any other surprises, I swear, I'll kick you out of this house and ruin your life! In the meantime, I don't want to see you anymore tonight. I'm going up for a hot bath and to get some sleep as I'm exhausted from all this travel.
You know, it's oddly funny, but even though it hurts, in a way I'm happy the truth came out and that I was able to meet the girl you've been having an affair with. Amy seems sweet and someone I might have enjoyed as a girlfriend. Not sure where she will fit into or relationship, if we can still have one.
When I get home tomorrow, I will expect to see my husband and discuss our future together. I have a meeting in the office tomorrow late morning, and I don't want to see you, so stay in your room until I'm gone. Now, I don't want to hear one word from you, no apologies because they would not be sincere. So, please go to your room and leave me alone."
I went into the guest room and rolled up in a ball on the bed and cried like a baby because of all guilt I was feeling and the pain I had caused Grace. It was never my intention to hurt anyone, and I never gave it a thought on how all of this would impact others or make Grace feel.
Her explanation of me having an affair was valid and I was devastated when she described the feelings of betrayal I had caused. I never would have intentionally betrayed or tried to hurt Grace in any way. This was worse than getting caught dressed up as Amy. I love Grace and would never try to hurt her, but it appears I've done just that by hiding and having the so-called affair with Amy, my feminine persona. I just wanted to go to Grace, beg for forgiveness and tell her how sorry I was but knew she wouldn't accept that from me tonight. After all, if I hadn't gotten caught, I would not have apologized and how real is an apology, after you got caught having an affair. No, I was in deep trouble and there was a real risk I would lose Grace forever. I had to somehow make it up to her and beg for another chance. I just wanted to die as this weight on my heart was too heavy to bear.
I cried myself to sleep and woke up early, I took a shower and removed every trace of Amy. I placed the wig back on the stand, hung up the dress I was wearing, and straightened the room. As Grace instructed, I did not pack or hide anything I had purchased. The full closet, along with all the dresser drawers full of panties, bras, and lingerie, the 7 pairs of heels, all the makeup, jewelry, and wigs, were going to reveal to Grace, just how obsessed I was with Amy. I wanted to get everything together, put them in a bag, and bring them to the charity drop box, but I knew that would send Grace over the edge.
Since the guest room only had Amy's clothes, I had to wait for Grace to leave for work in order to get some of my male clothes from our bedroom. I decided to quietly lie in bed and wait for Grace to leave, as she instructed last night. For the next several hours I just laid in the bed trying to come up with a way to explain or make things right. I realized that there was nothing I could do but wait for Grace to make the next move.
It was about ten o'clock when I heard the garage door open and Grace left for her meeting. I went up to the bedroom and got dressed in jeans and a tee-shirt and then went to the kitchen to get some breakfast. There was a note on the table that simply read, 'Good Morning, I have a brief meeting at the office and should be home before 5 o'clock. Let's go out to dinner at a quiet restaurant so we can talk. Love Grace."
Love Grace! That made me smile and feel a little better. Maybe this was going to be OK.
I got a text from Grace around 3 pm and told me to make reservations for the two of us for 5 o'clock at Morton's Steak house by the mall and she would meet me there. That was something we occasionally did and usually when we were celebrating something, but I didn't give it much thought and made the reservations and drove there to meet Grace at 5 pm.
Grace had gotten out of her meetings early and arrived at 4:30 and was at the bar having a cocktail. She was chatting with some guy in a business suit when I approached her and said hello. Grace looked amazing sitting on the bar stool in a short black skirt, black pantyhose, and Louie four-inch red heels. Her makeup was exquisite, and her hair was as beautiful as ever. Every time I look at her dressed like this, I ask myself why she stays with someone like me, she was clearly out of my league but for some reason, she seemed to be happy with our relationship. Until yesterday, that is. I walked up to the couple as my wife saw me approach.
"Hello honey," she said as we kissed. That was a good sign, I said to myself.
"I got here early, and this nice man bought me a cocktail. How rude of me, allow me to introduce you guys. This is my husband, Cary. Cary, this is William Right, the nice man that bought your wife a drink." I could tell it was probably her second drink as she was already acting tipsy."
Thanks William, may I buy you a drink?" I asked acting like her husband.
William realized he wasn't going to get lucky with Grace, now that her husband was there and just said, "No Thanks, I'm about to leave here in a few minutes but it was nice meeting you, and your wife is quite charming."
"Yes, she is an amazing woman and I love her dearly." She winked at me and smiled.
Grace finished her drink and we sat in a quiet booth away from any other quest, as Grace had requested when they seated us. Before the hostess left, she quickly ordered a bottle of champagne.
"What are we celebrating, Grace?" I asked
"Today was an amazing day, Cary. We didn't get a chance to discuss my trip and why I came home early but it was a big success. This was just our first meeting to pitch our company and marketing programs, but we hit it off with the owner of the team. We spent the entire week working together, going to dinner and spending all the time with the owners and some of the team players.
By Friday night Antonio, the owner of the team, informed us he loved our presentation and was ready to sign up with our agency. We met Saturday morning and he signed a five-year Fifty Million dollar contract with the stipulation that I would remain as the lead on the account. Of course, we agreed and came back with a signed contract and the largest account we have signed since the Jacksonville Jaguars."
The waiter came back with the champagne and filled our glasses as Grace continued to speak.
"Well, after we had the contract, we called the President of our company to give him the news and he wanted to see me this morning in the office. Since we were able to close the account so quickly, we all left a few days early and since you've been so nice to me lately, I wanted to surprise you and take you out to dinner but that didn't work out exactly as I had planned," she said with a little smile.
Anyway, our president, Clay Maxwell, met me in his office at 11 am and congratulated me on the success. He also told me how much he has appreciated all my hard work over the last year and how I have risen above everyone else at the company in his eyes. So, here's the news, pick up your glass baby.
You are now looking at the new EVP of Sports International! I'll be reporting to the president with new responsibilities and opportunities. It will mean a great deal of money, bonuses, and stock options." We raised our glasses and drank to our success.
It was an amazing night as we laughed and talked about her new job and how wonderful things at work were going. She explained that her salary would immediately triple and to expect large amounts of stocks and bonuses as the year progressed. Everything seemed back to normal and we enjoyed each other’s company and a wonderful meal. We finished a few hours later and left to go back home. I followed her as we drove the five miles back to our gated community and into the garage.
I followed her inside and tried to give her a kiss when she pushed me away and gave me a surprised look. "What are you doing?" she said.
"Just kissing my beautiful wife."
"No, that's not right. We haven't even started to discuss what happened yesterday. Tonight, was about me and my success and I needed someone to share it with. You deserve to know about things in my life and I love to share them with you even though you don't share everything with me. No, we aren't even close to normal.
Clay gave me a few days off to recharge from my trip and I know you're off until Thursday so tomorrow you and I will discuss Amy and our future. You will spend another night in your room, and we can start to figure things out tomorrow."
I went to my room and tried to figure things out. Tonight, seemed good as we got along great and she didn't bring up what happened until I tried to kiss her. Maybe we can get through this, I thought to myself.
The next morning, we had breakfast when Grace told me to clean up as she wanted to take a shower and for me to do the same and meet back in the living room in an hour. I found myself eager to please her and follow her instructions without any objections or questions.
I sat in the living room apprehensive about how this was going to go and didn't know what to expect. Grace came down looking refreshed and as beautiful as ever, smiled and grabbed a bottle of water before she came into the living room. She continued to look at me and gave me a little smile as I heard a car pull up into our driveway. I looked at her and asked, "I didn't hear the call from the guard gate, and I wonder who that is?"
"Just open the door, you'll understand," she said sternly.
When I opened the door, I was surprised to see my Mother coming up the walk. I turned to Grace with a shocked look and said softly, "Did you ask her to come over?"
Mom came in and gave me a hug and a kiss and then did the same with Grace.
"Thanks for inviting me over for coffee. It's been so long but I'm so happy you called. What's going on with you two? I could tell from my conversation with Grace that it important that I came over this morning. Mothers can always tell when something is wrong."
Grace spoke up and said, "We'll get to that Catherine, but let's have a cup of coffee and catch up first. Cary, will you please serve us some coffee as I get your mom settled in the living room?"
"Of course, I'll be back in a few minutes." I was upset that she would bring my mother into this but realized that Grace was intelligent and that if she wanted to understand all about me then mother would be an important part of the process.
About ten minutes later I brought the coffee in and they were both staring at me with a look that chilled the blood in my veins.
"She told you, didn't she?" I blurted out due to my nerves being so on edge.
"Well, she mentioned something about it. I guess it makes sense for us to discuss it together if this has come back." I sat silently and listened as Grace questioned my mother. It was awkward, to say the least, to hear your mom tell your wife about all the times you dressed as a girl when you were small. How you used to dress in her things and walk around the house pretending to be her daughter. Things came out that I didn't remember, and I struggled to sit there as they talked about it in a matter of fact way.
They discussed all my teenage years and how I used to keep girls’ clothes in my closet and hidden in my drawers and how mom knew but never said a word. She took the blame for some of this which made me feel even worse.
I had to speak up and just not sit there being tortured, "Mom, No! It wasn't your fault and it wasn't even a problem. I just liked wearing some of those things but when I went away to college, I forgot all about it and I guess I suppressed things deep inside."
It was very emotional, and I cried as they both sat next to me on the couch and put their arms around me. "It's ok, we'll get through this," mom said. Grace remained quiet and tried to take everything in.
"Catherine, I'm not sure how to process everything we discussed. You should have seen Amy Rose, that's the name he selected for her. She was so pretty and completely female. It's as if Cary never existed and as you can imagine how it made me feel very uncomfortable and I'm not sure I can handle this."
"Really? He went all out, and dressed up to that extent?"
"To answer that question, I have an idea. I told Cary not to put anything away so that I can see Amy's collection and the things he purchased. Let's go to the guest room where Amy is living now and see exactly what your son has been up to."
Grace and mom stood and started downstairs to the guest room. Grace turned and looked at me, "Come along, dear."
What followed was another devastating moment when they opened the closet door and heard them gasp when they saw the entire closet full of dresses, skirts, blouses, high heels, purses, and my new cocktail dress. They were equally stunned when the opened the dresser drawers and saw all the lingerie, panties, pantyhose, stockings and that bottom drawer with all my toys. I saw them look at each other and giggle.
Then they discovered my now large makeup collection, my wigs, jewelry, and perfume all out on the counter as Grace had instructed. Mom turned to Grace and sympathetically said, "Well, I think that answers my question about how committed he was to become a female. It's clear, from this wardrobe, that it's not just a one-time thing or a hobby."
"Catherine, I have an idea. Can you stay for dinner tonight?"
"Well, yes but not too late because I hate to drive at night."
"Wonderful, that's perfect," Grace said turning to me and continued speaking.
"Cary, I want your mother to meet Amy Rose. Mom and I will go out for a little shopping and should be back around three o'clock. I want her to meet Amy and please wear the same outfit you had on yesterday, it looked cute on her. I expect you to look as good as you did yesterday. Oh, and while Amy will be visiting, I think it would be nice if she made dinner and served us tonight, before Cary's mom goes back home."
I tried to protest but Grace put up to her hand and stopped me, "Honey, the worst is over. The truth is out there, we've seen your things, and how committed you are to this. Your mom and I have already seen you dressed as a girl so it's is no big deal. Stop your whining and please do as I ask. We are trying to fix this, and I expect you to help us, understand?"
All I could do was nod my head and look down at the floor as my wife and mom stood there staring at the man I used to be.
"Oh, and if Amy needs to pick anything up for dinner please don't hesitate to do some food shopping. I know how much she enjoys that." She said as my mom and Grace just gave me a knowing smile.
And then they were gone, and I was all alone to contemplate what had just happened and what was about to happen. Now after being completely exposed and mortified in front of my wife and mother, there was no longer any secrets. They have just seen my collection of clothes, lingerie, makeup, and all the accessories any girl would love to have, including my toy collection. She was right, there was nothing else to hide and they have both seen me in girl’s clothes. I saw no alternative than to do what they asked and allow them to see Amy Rose again.
I looked at the clock and I had a little over three hours to get ready and knew I had to get started and took a hot bath with scented oils, shaved my legs and body, dried myself and then applied the expensive body lotion I had purchased. Without wasting any time, I opened a new package of nail extensions and started the process. After gluing them in place, filing them, and painting them Revlon Red I then used the same color on my toenails.
After they were dry, I started on my face and easily applied my fake eyelashes this time, as I've become adept at putting them on correctly. I applied some eyeliner, eye color, before adding a little extra mascara for a dramatic effect. I told myself to just go for it, enjoy what might be your last time dressing up and have as some fun, and I did!
The clock said I had about ninety minutes to dress and plan a dinner for the three of us, so I took the dress that Grace told me to wear out of the closet along with my heels and placed them on the bed. I took out my bra, pantyhose, and shape wear and started dressing. Putting the black lace padded bra seemed natural as I smiled to myself as I inserted the silicone pads that helped give a very full set of breasts. I put on the sheer black silky pantyhose over my smooth silky legs that sent waves of happiness throughout my body as I put them in place.
The only thing left was to put on the Spanx which was always difficult to put on with my long nails, but I took my time and carefully slid it up my legs and over my midsection allowing me to completely hide may sign of my maleness which also gave me a cute shaped butt, and a thin waist. The shape wear was high cut and came up to my crotch, allowing my legs to be completely free and exposed. The tight Spanx also gave me the girlish figure most girls would just die for.
I stepped into the silky dress that I had only worn for a short time yesterday and then sat down to work on getting my wig set properly. This took some time as I knew it was a key element in the process. After putting on the wig cap I was able to use lots of pins to set it correctly and stable on my head. I brushed it and worked on the style for twenty minutes before it was perfect, and I smiled as the girl that was now staring back at me in the mirror. The transformation was complete, Amy Rose had returned.
I attached the earrings, necklace, rings, bracelets, and liberally sprayed myself with perfume and then walked to the full-length mirror to examine my work and today I might have outdone myself as the image was one of perfection. The tight silky dress, large breast, long legs in the four-inch heels, the sexy blond wig and perfect night time makeup helped me present as a sexy and sophisticated woman in the mirror.
At this point, I had thirty minutes before they got home, and I went to the kitchen to figure out what to do for dinner. I had 3 hours to prepare something for us and I decided on what to make. The good news is I had just gone shopping and was planning on making vegetable pasta while Grace was gone to practice my cooking skills and took out all the ingredients and set up the kitchen.
I cut up all the vegetables and made the sauce I would use to cook everything and when I just got done with the preparation, I heard a key in the front door and realized the girls were back from shopping.
With my apron still in place, I fluffed my hair, put my shoulders back, and walked to the front door to greet them. I could feel my heart pounding as the moment of truth was about to arrive. I had no idea how mom or Grace would react when they saw me. Would they laugh, make a face in disgust, or something worse? I would find out in a few seconds.
Grace opened the door for my mom, and I saw her shocked expression when she entered and saw me in full dress. I could tell she was shocked and surprised by how I looked. Grace walked in behind her and looked me over expressionless.
Grace held out her hand and motioned to me and said, "Catherine, I'd like you to meet Amy Rose. Isn't she lovely? Amy, that dress is perfect for your figure and long legs, you certainly are a looker. She said the men are always complimenting and flirting with her when she goes out, and you can see why, can't you?"
"Oh my, yes. Amy, you are lovely, and I never would have expected you to look so much like a girl, I mean from what I can see, you are a girl and that tight dress can't hide a thing. What did you do with your little pee-pee?" Mom said giggling.
Grace was also smiling now and said, "Yes Amy, how did you hide it and keep your front so smooth. Please lift your dress and show us, please."
Now I was completely humiliated as she instructed me to lift my dress and expose myself to my wife and mother, but I did as she asked and held up above my waist as they examined my figure.
"OK, I see. That tight shaper has kept your secret hidden and it's very convincing," Grace said as they looked closely.
"You do have wonderfully shaped legs darling, most girls would kill for legs like yours, and your shape is just marvelous. You must have worked hard to get where you are today, haven't you?" Mom asked.
I nodded. "I lost a few pounds to get into this dress and the shape wear does help, even though it can get to be very uncomfortable," I answered honestly.
Grace spoke up, "Well, I'm sure by now you understand how we girls have to wear things that aren't comfortable to fit into a certain dress or the pain in wearing high heels all day. To look feminine and nice for the opposite sex is one reason we do that, Amy. It's part of being a girl, but you already know that, don't you sweetie?"
Grace was looking for an answer and I didn't see any reason to hold back now.
"Yes, I know, but it's worth it when you can fit into that certain dress or shoe you've wanted to wear," I said as a reacting to Grace.
Mom had an odd look as she continued to assess me and how I looked and said, "Amy, your voice is so different now, and the way you look makes me feel like you are a girl and somehow, have become Amy. Grace, I now understand what you were saying before. It's obvious to me that Amy has a strong desire to be a girl and I can only imagine how you must feel, when another woman suddenly comes into your life in place of your husband," she said trying to console Grace.
Looking at me mom said, "I do hope we can work things out for the two of you but it's clear the normal husband and wife routine is not going to work, honey. You will need to explore your feminine side and hopefully, Grace will allow you to stay and do just that. How do you feel about this Grace?"
"To be honest, I’m still not sure but I do agree that Amy needs to stay around and explore her feminine side. I think we should plan on Amy being around for at least the next two weeks and see where this goes. Just seeing you like this, hearing how you talk, and how feminine you act, makes me consider taking your mom's advice and help you live as Amy until we decide differently.
You said you were off from work until Thursday so you will remain here with me as Amy but tomorrow morning, I will call your boss Jonathan and explain that you've hurt your back and can't get out of bed and will need the remainder of the week off. I'll then ask him if it would be possible for you to continue to work from home for the next two weeks and if not, you will need to take the next two weeks off for your back to heal. Whatever he says won't really matter because either you continue to work and get paid or you will take a two week leave for health reasons.
I want you to live as Amy for the rest of this week and the following two weeks. You will live with me as my girlfriend and we will both see how things go. It will give you a real opportunity to live as a woman for a much longer period, which will help you find out if it's something that you want to continue or go back to your previous life as a man.
What this will also do is allow me time to adjust to Amy Rose living here, and it also gives me time to understand your needs and hopefully find a way for us to continue to live together. This isn't up for a debate, I've made up my mind and unless you want to be kicked out of our home which would end our relationship, you will do as I say. If not, maybe you can move back in with your mom," she said in a harsh tone.
Mom spoke up and said, "Grace, that is a wonderful idea. This will give her time to see if this is just something to get out of her system and to really understand what it's like being a girl and how hard it can be. I assume you will have Amy Rose perform the domestic role as you will be working, right? I mean what better way for her to learn what being female is all about. Amy Rose, that means you will have to take care of all the household chores, cooking, and cleaning and staying in character always. This will give you a better understanding of what it's like for women everywhere. It's not just about wearing a cute dress or doing your makeup to perfection and I think after a couple of weeks you will be happy to return to your old male self."
"Catherine, that's a marvelous idea. Yes, that's exactly what you will do Amy. I always want you to be all dolled up wearing your cutest outfits while you take care of the house, do the grocery shopping and run any errands I need to be done. It will be like having a wife, oh Catherine you are so smart. I'm so happy I had you come over to help us through this."
I stood there in disbelief. Would she actually call my boss and have me stay home for that long and live as Amy? They both appeared serious as they plotted my role in the house and what I would need to do over the next 2 and a half weeks.
"Yes, this will be fun, and I want to be involved, if you don't mind Grace. I always wanted a daughter and for the next two weeks, I will have one. She is so darling, isn't she?"
"I love that, Catherine. Maybe you can help Amy learn the correct way to do laundry and iron and even teach her how to maintain a house. You've always kept such a perfectly clean and neat house Catherine; can you teach her how you do that? You two can even do lunches and a little shopping while I work and getting used to my new role at work."
"New role, Grace?" mom asked as I served dinner and sat down to join them.
"Yes, I didn't get a chance to tell you, but I got a massive promotion and I will be making more than double my previous salary. I'll be making enough to keep Amy at home as my housewife, if this works out," she said, giggling with Catherine.
"Amy, this dinner is marvelous and so delicious. I didn't know you could cook and even the presentation is lovely. You would make a wonderful housewife," Mom said as I felt my face turn red with embarrassment."
"Where did you get this recipe, Amy? I love it and please be sure to add it to the list of favorite dishes. I surely want you to make it again for me and any guest that visit," Grace added.
"I found it on Pinterest and knew you both would enjoy the receipt. I'm so glad you liked it," I answered trying to fit in as one of the girls.
Mom was looking at me with a surprised look on her face and said, "I can't get over how natural you are as a girl, Amy. The way you talk matches your looks, and your hand movements and gestures are just perfectly feminine."
"I was thinking the same thing, Catherine. Amy, you are a fast learner, because most girls spend years to learn grace and beauty and it seems you've achieved this in just a few months of practice. Femininity obviously comes naturally to you, honey."
I sat quietly and endured the embarrassment and humiliation as my mother and wife spoke about me in the feminine. They were now speaking to me as if I was actually Amy and asking me about fashion, gossip at the office and if there were any available men at work, and just things they knew would humiliate me and embarrass me. They seemed to really enjoy this new-found part of my life and I was forced to just sit there and play along.
Finally, after a few hours, mom was getting ready to leave and gave me a hug when she was leaving and whispered in my ear before she kissed me goodbye. "I suggest you listen to Grace and explore your feelings while you have this opportunity, because you may never have a chance like this again. I will love you and support you regardless of what you decide to do Amy," she said as she gave me a motherly kiss goodbye. I waved to her as she got in her car and drove off and stood there thinking about what I just went through and still survived
Grace walked up behind me and said, "Your mom's a smart woman, Amy. I overheard what she said, and you should take advantage of this and embrace the opportunity to find out exactly who you are, and what you really want. I'll help you along the way, but I'll expect you to listen to me and obey my wishes. If not, things could get real ugly and you might blow the only chance to find out things about yourself you may otherwise never know.
Dinner was fabulous and you were the perfect hostess. Now please clean up as I need to prepare for work tomorrow as they will announce my promotion and I want to be fresh and look perfect. You'll be sleeping in the guest room or what will now be known as Amy's room until further notice. Goodnight, Amy Rose," she said as she gave me an air kiss before leaving me in the kitchen to clean up the dishes and table.
An hour later when everything was clean and put away, I removed my apron and headed off to Amy's new room. I got undressed, washed off my makeup, slipped into a silky gown and almost immediately fell asleep. Since I hadn't had a good night sleep in a couple of nights my body needed the rest. I didn't wake up until nine the next morning and Grace was already gone. There was a note on the table which I picked up and read.
I hope you had a good night sleep, Amy Rose. I looked in on you, but you were resting so peaceful I didn't wake you. I'll let you know what time I'll be home for dinner so please prepare something nice for us. There is a pile of clothes on my bed from my trip that needs to go to the cleaners. Please bring them in today and pick up whatever we need from the grocery store. That's going to be your role from now on, sweetie. Love you."
This was going to take some getting used to as I was being treated as her housekeeper but to be honest, I didn't mind and in fact, being able to stay dressed in her approval made things more comfortable.
The following days I did stay home and remain as Amy, slept in her room, took care of the housework, dinner, and shopping and Grace was extremely pleasant and understanding. She even started treating me as a woman or even her girlfriend as we chatted like girls do every day of their lives.
She forced me to admit that I was enjoying my time dressed as Amy and even liked doing all the housework. I admitted to her that I was enjoying the new role and even looked forward to being Amy for the next two weeks. Grace seemed pleased and complimented me on how clean the house was, and marvelous dinners prepared for her when she got home from work
I found myself smiling and pinching myself to see if this was a dream and to my delight, it wasn't a dream. I was living as a girl, doing everything I dreamed I would, and sharing it with the woman I loved. It was pure bliss, until Friday night.
Friday night Grace apologized for getting home a little late but explained that she had wonderful news. She explained that she had called Jonathan on Wednesday and asked him to meet her for a drink after work tonight and that's when she explained to Jonathan the situation.
She told him that now that she has the promotion and is the real breadwinner in the family and that it was her idea for me to stay home and take care of the house this week as a trial. She explained to Jonathan that I didn't hurt my back but that she wanted to see if I could handle being a housewife, so to speak.
When Jonathan heard how much I enjoyed being home and the housekeeper she could tell he was stunned and shocked to hear about the situation but mature enough to accept our life choices.
He said, "Grace, we rely on Jonathan for our IT needs and this will be a huge loss for our company and workload. Is there any way he can at least come in a few days a week and help us?"
"Jonathan, does he really need to come in because we might be able to make this work if he can work remotely. Why not a trial run to see how it goes, maybe lower his pay and be more flexible with his hours and that might work for the both of us."
"That's not a terrible idea, Grace. He has been able to keep up with most of the work for the last two weeks without coming into the office and if he can handle things from home, then I'll allow it and of course, we will have to renegotiate his contract if the test works out."
"Isn't that wonderful, Amy? This means that you can now work from home, do the housework, food shopping, prepare dinner, and be just Amy all the time. Isn't that wonderful?"
Suddenly I felt as if things were spiraling out of control, I felt anxious and scared and completely shocked at this new twist.
"Grace, what have you done? I loved that job and it was my career."
Somewhat surprised Grace glared at me and said, "What's wrong? I thought you would be happy and appreciate what I've done for you, sweetie. We all know how much you like living as Amy and to be honest, I love the idea of having a housewife taking care of things for me at home. Besides, you don't even need to work with my new role in the company. If this works out and Amy wants to quit work, she can be a stay at home wife, work on her appearance, go to the gym every day, have your nails done every week, and just be the perfect homemaker. I'd rather you just quit but at least now you have a choice."
There wasn't much more to discuss, and I continued to live as Amy, taking care of the house and spending about 5 hours a day working on IT issues for work on the PC. I had to admit, I enjoyed the prospect of living as Amy. The only complaint I had was I had to sleep in the guest room which Grace now called Amy's room. She explained that she was not comfortable sleeping with another woman and that's what she considered Amy now, another woman, a pretty single girl, and the new homemaker. Overall things were working out and Grace and I became closer in ways we had never been before. She talked to me as I would expect she spoke with all her girlfriends and treated me different, in a good way. Grace made me feel accepted and comfortable with our new living arrangements.
She invited my mom over several times to visit and of course, I served them dinner or tea as the occasion dictated. Mom was very loving and accepting of me and was now referring to me as her daughter. Mom gave me some housekeeping and cooking ideas. They both gave me makeup and hair tips, took me shopping for new outfits several times and I loved every minute. Mom still couldn't get over how I was able to adapt and become so convincing in such a short time, but Grace explained that my desire to be feminine created the amazing results.
Of course, things never go perfectly and one night when Grace got home from work, I could tell something was troubling her. After the dinner I prepared I cleaned up and she asked me to pour us a glass of wine and chat in the living room. When I put the last dish away, I took out a chilled bottle of wine and poured two glasses and went into the living room to talk with Grace.
"Let me get right to it, Amy. That night when Tony and I first met Amy, it was in shock and not sure about anything including our future but as things turned out so far, I can accept your need to live as Amy and honestly, things have been so much better between us since then. I don't have to tell you that for the last year things between us were not that great, but for whatever reason, I feel much closer to you now living with you this way.
For the last year, as husband and wife, we rarely had sex, so this transition hasn't been much different. You know how much I love sex and over the last year I've found other ways to satisfy my needs but that's not why what I wanted to talk to you about.
That night when we caught you dressed as Amy, you not only shocked me, but you also humiliated in front of one of my co-workers. Knowing that my husband was a sissy in front of a co-worker and pro-athlete was terrible and I thought I would never forgive you, but Tony was very cool about things. He said it would be our secret and he know that every relationship is different and wished us the best.
Remember, I work with a bunch of male jocks, alpha men, who would make me the joke of the office if they found out about you and the fact that I was living with a sissy. It would be 'open season' on Grace and every guy would be trying even harder to get me in bed. Now with my promotion, if they learned about you it could jeopardize my position because I'm not sure our lifestyle would be accepted and I would probably be pushed out of the company, so this must stay our secret. Do you understand how important this is to me, Amy?"
"Of course, Grace. I know you love your job and the new position is going to make our lives even better. I would never do anything to jeopardize that for you or hurt you in any way."
"That's what I was hoping to hear you say, Amy. What I'm going to say next might be difficult so go get us another glass of wine and we can continue."
I sat there nervously drinking the second glass of wine as I started to feel the effect the wine when Grace started back on the conversation.
"Well, today Tony came into my office and said he was ready for that dinner we had promised him."
"What dinner is that? I asked him."
"He reminded me of a promise I made to him. That night when we saw Amy for the first time, I begged Tony to keep this our secret and told him I would have him over for dinner with both of us, and at that time I would have you explain things to him. Well, he said he has been waiting to hear the explanation and wanted to know when we were having him over for dinner. Tony is a friend and will keep our secret, but just to be sure, I knew we had to have him over, so I invited him for dinner this Saturday night. That gives you two days to prepare and come up with a nice plan for the three of us. He will be here at 6 pm, on Saturday."
"What? Really? What does he expect me to say or explain? I don't think this is a good idea, Grace."
"Well, we really don't have much of a choice as I want to keep him happy and we did promise him a dinner for his silence. Besides, you've been around other men and all you need to do is just be Amy. Over some drinks, you can explain how things led to where we are today and who knows it might be therapeutic for you to discuss it with other people."
"Grace, this sounds crazy. You want me to make dinner and serve another man in our house and explain how I went from being your husband to now living as Amy full time."
"Yes, that's exactly what I'm asking you to do and I if you think about it you will see that you owe it to all of us. That night you humiliated me and sometimes I wonder what other women would have done, if they came home to find their husband dressed up as a beautiful woman. To be honest, it took me time and several conversations with your mom to understand things better. I can only imagine Tony's confusion and his need to understand. It will be fine and after it's over I'm sure we will all laugh and feel much better about everything. Amy, this isn't open for debate, it's happening and I'm just attempting to get you ready for this.
To make it easier on you this time, we can have one of our favorite restaurants prepare the meals and deliver them before Tony arrives, and all you'll have to do is serve the dinner. That will give you more time to relax and get ready for the evening. I'm sure you will want to look perfect for the evening and god knows you better not embarrass me again in front of my co-worker.
I think I'll make a reservation for you at my salon for Saturday afternoon. I think it's time that Amy got a makeover to find out just how pretty she can be. Won't that be fun, baby?
You will also wear that cute black dress your mom and I bought for you last weekend, along with those sexy four-inch black pumps, you'll look so cute. I think this might turn out to be a fun weekend after all."
Salon appointments and Dinner
I struggled through the rest of the week constantly thinking about Saturday night and having to explain myself to some guy. A big strong guy that will make me feel quite inferior in front of my wife. I thought about begging Grace to cancel dinner, but I knew there was no way she would allow that to happen.
Friday afternoon she called me from work and told me that she had made an appointment for me at her Salon with her stylist Nikki. She said that she explained everything to Nikki and that they would be discreet and take care of you as instructed. She told me that I was to arrive at 1 pm and to plan on being there all afternoon. All I had to do was show up in skirt and blouse with just light makeup and they had instructions on exactly what Grace wanted.
"I'm having dinner with some of my co-workers at Jackie's house and I might spend the night so if I'm not home I'll expect you to make it over to the salon by yourself, on time. I've explained to Nikki and she was cool with everything. They have other clients like you and understand how important it is to keep things discreet and not divulge any of their client's secrets or discussions. They are professionals, so you don't have to worry about anything.
I've given her instructions on what I want to be done and I expect you to allow them to complete things without objections. I'll make sure that dinner arrives before you get home and I'll help you serve dinner so that you have enough time to get ready for our guest. Everything is set and all you will have to do be at the salon at 1 pm sharp. Nikki will be waiting for you and will take you to her private area to work on you, don't be late.
Wear some comfortable clothes, a skirt and blouse will make it easy on you. No nylons or stockings tomorrow, just comfortable shoes and light makeup. Just wear that cute denim skirt with the yellow top you wore last week, and you can borrow my yellow ballet flats. You'll look cute and comfortable and that's all you'll need. Nikki will take care of the rest. When you get home, I'll have the outfit I want you to wear on your bed and you will have enough time to dress and ready yourself for the evening. Do you understand everything? If I'm not home, I'll expect you to be at the salon by yourself at 1 pm sharp. Do not keep her waiting. Understand?"
"Yes, but what are they going to do? Why aren't you coming home tonight?"
"Oh Amy, don't worry about anything. Nikki will enhance what you've already created and helped turn you into an even more convincing woman. The reason I may not make it home is that we are celebrating our recent success in Italy along with my promotion and I plan on enjoying myself. I don't want to worry about getting home late after drinking and partying all night so when Jackie told me to spend the night, I agreed. I would have invited you to the party but I'm afraid I'm not ready to introduce Amy to all my co-workers just yet."
I didn't like the thought of Grace celebrating with all those alpha males. I knew there was nothing I could do except to hope nothing would happen. I had to trust her but also knew how a desirable she was around those guys. I knew I had no right to say anything and managed to put it out of my head and not think about it as I contemplated my ow n upcoming appointments at the salon and dinner with Tony. It was all I could do to maintain my composure.
Saturday morning, I kept busy doing laundry and cleaning up the house. Grace never came home, and I tried not to think about her night out with her friends. I felt butterflies at noon when I realized I had to get ready for my appointment and leave in less than 30 minutes to make sure I got there by 1 pm.
I showered and put on the skirt, blouse and shoes that Grace suggested, I then put on some lipstick and fixed my hair. Trying not to think I just focused on getting ready and leaving on time and drove over to the salon in the nearby shopping center. I got there ten minutes early and sat in the car until a few minutes before 1 o'clock. I got out of the car and quickly walked into the salon with my head down trying not to be noticed. As soon as I walked in there was a young girl dressed in a cute red dress and matching heels, large breast, and sweet smile. I felt intimidated by her beauty and how sexy she was dressed.
"You must be Amy. Grace told me what you would be wearing and to tell you everything is taken care of and for you to just enjoy yourself. Follow me and I'll take care of you, sweetie. Grace was correct, you make a lovely woman and you have lots of potential. She gave me all the details and we have a busy afternoon, so I suggest you just relax and enjoy it, Amy."
I was happy to see that we were in a private booth that was off to the side away from the other woman and decided to just relax and enjoy the experience. Nikki removed my wig and placed it on the side and then played with my hair.
"Yes, Nikki was right about your hair Amy. It's long enough to work with and when we're done with the extensions, you'll not need a wig, isn't that exciting?"
"Yes, it would be wonderful to not have to wear them anymore but how?"
"That's why you're here to watch and learn," she said handing me a glass of wine. "Just relax and I'll explain things as we go along."
I was taken to the shampoo area where the washed my hair and added a new color that Grace had selected. After I was back in Nikki's chair, I saw my new blonder colored hair which really changed my look. Nikki then carefully somehow placed dozens of extensions to my hair which created an amazing new look. I now had blond shoulder-length hair that felt thick and natural. I sat there stunned as the new girl I saw in the mirror.
"Now don't you look pretty?" Nikki said.
"I can't believe it's my hair."
"Yes, it's yours now and it won't be coming out anytime soon. Before you leave, I'll explain how to care for it and how we will keep it healthy and looking natural. Now I just need to cut, and style Grace wanted for you so let's get you finished."
When she finished, I had a cute stylish cut that framed my face and screamed "Girl!" With this cut, there was no way I could ever convince anyone I was anything but a female.
"Well Amy, it looks like Grace was right about this style. The color and cut are just perfect for you features and it will be simple for you to take care of and manage. Now I'm going to bring into Jessie's room where you are scheduled for a body wax. I suggest you finish your wine as this part won't be as fun as your hair styling. I'll see you back here in an hour. Jessie has instructions so just try to relax and you will be done before you know it."
The room seemed clinical with just a table for me to lie down on with a counter full of tools and wax. Jessie was another cute girl dressed in a white clinical coat and had me remove my clothes and placed a clean sheet over me and turned on some relaxing music as she started working on my legs.
Over the next hour, my entire body was waxed, and all hair removed. There was no embarrassment or comments as it was apparent that this was something she had done quite often. At the very end of the treatment, she announced we were almost done and said the only thing left was my eyebrows. She meticulously waxed and trimmed them as Grace had instructed and with, she was finally done she instructed me to get dressed and she would be back in to take me to my next area.
Thankfully the lotion she applied after removing all my hair seemed to ease the pain caused by all the hair removal and the jasmine scent also kept me relaxed. My skin felt so smooth and silky, I loved the results.
I was brought over to the manicurist where this young Asian girl placed me in the massage chair and placed my feet in hot scented water. It was extremely relaxing as the massage chair did its magic while the young girl worked on my pedicure. I now understood why girls liked getting a weekly mani-pedi, it was such a lovely feminine experience. When she was done, she dried my feed and opened a preselected red colored nail polish and painted my toenails as I took in the scent of the nail polish and admired the pretty toes I now had.
She took me over to her table where she put my nails in warm soapy water and started the process of adding long acrylic nails on my slender fingers and finished them off with the same red color on my toes. Long sexy nails now bright red color that made them stand out and draw attention.
Next thing I knew I was in a chair and introduced to the cosmetologist. She explained that she was going to do my face for the evening and to teach me exactly how to replicate the look so I can do it by myself.
"The notes say you have a special dinner this evening and we will do you up for nighttime which means darker and a little more than you would use for daytime activities. First, we are going to give you eyelash extensions. Now this will give you a dramatic look from the moment you wake up which will save you lots of time and trouble. Of course, you'll have to come in for fillers ever 3 weeks but believe me you will just love the results."
When she was done with the extensions she started on my foundation and went step by step on completing my look. She explained things thoroughly making sure I understood how and why she did each step.
"Since you'll be coming in every few weeks for your eyelashes, I'll help you get proficient with all different looks. Soon you'll be better with your makeup than most girls which will increase your confidence and turn you into the pretty girl you are. Now, one more thing we need to do before you leave. Grace said she wants your ears pierced and this will only take a few minutes."
She took out the piercing gun and sterilized my earlobes and the gun with solution, placed small dots on each earlobe, lined up the gun and a few minutes later I had pierced ears with gold studs in place. She told me how to care for them and led be back to Nikki at the receptionist counter.
"Wow! Amy, you look amazing. Let's take some photos and I'll send you on your way. After several selfies and some poses, she smiled, "Well Amy, we are so happy to have you as a new customer and Nikki already booked your next appointment in three weeks. Everything is already paid for and Grace added some generous tips for the girls.
Tell Grace that if she is unhappy with anything that we will be happy to fix and just to bring you by, OK honey? Now, have a fun dinner and be sure to tell us all about it when you come back."
I drove home overwhelmed by the afternoon I just had. As I looked in the car mirror, I saw a pretty, blonde-haired girl with long eyelashes, sexy makeup, and kissable red glossy lips and a bag full of makeup and nail polish for any touch-ups I might need. Everything I had dreamed of was now a reality and I smiled to myself as went over the day. Pedicure, manicure, hair color, hair extensions, body wax, pierced ears, eyelash extensions, and a complete facial makeover. I was now more of a woman than I ever was able to achieve or dreamed of and it was all thanks to Grace. She seemed to have accepted my desire to dress and act like a woman. She spent time planning and paying for all these treatments and I'm sure she wouldn't have done all this unless she accepted me for who I am.
Grace was waiting by the door when I came in the house and was smiling from ear to ear. "You look amazing! I knew that hair color and style would look great on you and best of all you won't have to wear those wigs any longer. They did a fabulous job on your makeup and I just love your new earrings. Let me see those nails, Oh how pretty!"
Well, as much as I would love to hear about your day, we don't have much time before Tony gets here. You have less than an hour to get dressed and get ready for our guest. The dinner delivery is on the way and will be here in a few minutes. While you're getting ready, I'll set up the food so that it's ready to serve. Hurry up, the clothes you are wearing on the bed and your dress is on the back of the door.
You'll need your best performance tonight and show us how convincing you can be as Amy. Don't forget your Amy voice and your girly movements. You're going to do just fine, now run along."
I quickly went to the bedroom and saw what she had laid out for me to wear. I undressed and cleaned up and then sat slipped on the black lace padded bra with the built-in forms and black shapewear that I struggled getting in place with my new longer nails. I sat on the bed and opened the new package of Wolford pantyhose and slid them over my silky smooth legs and Spank. Next came the silky black dress that mom and I purchased last week and carefully stepped into and zipped it into place. It fit perfectly and felt amazingly sexy over my smooth hairless body and my nylon pantyhose. The tight fit and sexy feelings were heavenly. On the floor next to the bed was the new four-inch heels we also purchased to go with the dress, and I stepped into the as I've seen Nikki and other women with ease.
I took some steps to get my balance and walked over to the mirror and stood there stunned for several minutes. The woman looking back was completely real. There was no trace on any masculinity, only that of a young woman in a cute black dress with sexy long legs looking back. I never thought I could ever look this convincing and realized at that moment that I've become what I've always considered just a dream. I was now a female in all visual aspects and if I could just remember to move properly and speak in my feminine Amy voice, I'd completely pass as a female. I was excited about the results and just proud of what I was able to achieve until I heard the bell ring. It was at that point that I remembered why I was dressing up and that when I felt the butterflies in my stomach as I started to panic and not wanting to come out of the bedroom.
I heard voices as Grace let Tony in and as I stood there in fear not knowing what to do the bedroom door opened and Nikki came in and said, "Oh my, look at you. Aren't you the prettiest little thing? Your mom has great taste, that outfit is perfect for you, but we don't have time for chit chat baby. Our guest is here, and you need to come down and get the evening started. Spray on a little perfume and let's go."
She handed me my perfume and she watched as I sprayed myself and checked my makeup and hair in the mirror. I took a deep breath as she took my hand and led me into the living room.
Tony
I took small steps and remembered to watch my movements and followed Nikki as we entered the living room. Tony stood up and from his expression, I could tell he was a little shocked. He smiled and then whistled,
"Oh my god, you two ladies are a picture of beauty and so sexy. You really went all out for me tonight and I appreciate that very much."
It was then I realized that Grace was also dressed up super sexy. I was so focused on myself that I didn't even notice her dress. She had a silky short red dress with a very deep neckline that showed off her very large breast. The red high heels also made her legs super sexy in that short dress. We were both dressed up for night club or fancy affair and it was clear that Tony liked what he saw.
"Thank you, Tony. Amy and I had fun getting dressed up together for you tonight. What would you like to drink?"
"I'll take a glass of Crown if you have it, over ice please."
"Great, have a seat and we will be right back with your drink."
He sat on the couch as we went into the dining room where we had a little bar set up. Grace had me open a bottle of wine as she got ice and poured Tony's drink. I filled our wine glasses and Nikki handed me Tony's drink. Grab your wine and Tony's drink and let's go back to Tony.
Tony was on the couch and looking very relaxed in his blue blazer and tight jeans. He wore a crisp white shirt and expensive designer sneakers, which you would expect a pro-athlete to wear. You could see his large chest and muscles though the tight clothing he wore. He is a handsome man that would be considered a catch for just about any normal woman. Rich, handsome, muscular, tall, and gentle, he had it everything a girl could want in a man. I handed him the drink and he motioned for me to sit next to him as Nikki sat across from us on the other couch.
I crossed my legs and sat with my shoulders back, mirroring Grace as she did the same. We drank our wind as I kept my other hand on my lap and tried to be as graceful as possible
Tony raised his glass and said, "Well, a toast to the most beautiful women I ever seen."
We giggled and drank our drinks and chatted. It was a casual conversation about the weather, sports, and food. He said he was looking forward to this dinner ever since that night and was sure to bring his appetite.
"We're happy you're hungry because we have lots of tasty food for tonight. We're also happy you came over for the dinner we promised. Amy, why don't you refill Tony's drink and then you and I can start getting dinner ready to serve?"
I stood and walked over to the bar and as I looked back, I noticed Tony staring at my ass as I was wiggled over the bar. It made me uneasy but excited for some reason at the same time.
In the kitchen, we both worked on getting the food out and ready to serve. When things were almost ready Grace told me to start placing the food out and she would keep Tony company in the meantime.
I heard them talking on the couch as I started placing the food out on the table and filling the water glasses. I couldn't hear what they were saying and decided to just focus on the dinner.
They came into the dining room and Tony took the seat at the head of the table and Grace and I sat next to him, across from each other. For the next hour, we sat and enjoyed a very nice dinner and drinks. Several times I had to get up and refill our water glasses and get Tony another drink. It was clear that I oversaw the food and serving our guest and Nikki was sure to reinforce this as well.
"Tony, when Amy found out you were coming over for dinner, she was excited about cooking you this meal. She spent the day getting ready and cooking all this for you, didn't you Amy?" she said looking over and smiling at me.
"Yes, I wanted this to be a nice evening. I hope you liked everything." I said trying to maintain my control.
"Girls the food and company were just perfect, and I really appreciate your hospitality, but I have a confession, I had an alternative reason for coming over tonight."
Looking at Grace and in with a serious tone said, "When I brought you home from the airport that night and found your husband dressed as an attractive woman intrigued me and it's been on my mind for some time. I have several questions and wanted to have this dinner to better understand things. Since we will be working so closely it's important to me that we don't have any secrets and come to an understanding."
I could tell that Grace was uncomfortable and just nodded. Tony turned to me and in a friendly voice, looked deep into my eyes and started asking me questions.
"Please don't be intimidated by my questions because I'm fascinated, and I find you very attractive and please understand that I am a very open person. So, tell me, when did you start dressing up in women's clothing?"
"I started when I was very young."
"Please tell me about it, all of it so that I can understand better."
Not knowing what else to do I looked over at Grace as she nodded and permitted me to tell him everything. And I did. I told him how I've been dressing all my life, how my mom knew and helped me when I was young, and it was something I never outgrew. I explained how I tried several times, but it was always something I needed deep down inside. I stopped for several years and when Grace was away on long work trips, I found myself dressing again. I loved Grace but this was something I just needed and could not resist."
For the next hour, he asked many more questions including if I enjoyed being Amy with his wife tonight. "Did you enjoy the evening, and being Amy tonight? Do you enjoy living and being a woman like this?"
Between all the wine, and all the frank conversation, I found myself being completely honest and said yes, I loved being Amy and enjoyed the entire evening. I saw the shocked look on Grace's face as I said those words and realized that I had just confessed to something she already knew but until that moment, never heard me say. I wondered what she was thinking and how things might change after my confession.
Tony said, "Thank you for being so open and honest, Amy. I would also like to be honest and open and maybe that will explain my deep interest in your dressing up as a woman. I'm about to tell you something nobody knows, and I'll expect both of you to keep it between us and at the same time, I'll keep your secret safe as well.
As you probably know the media always likes to call me a Playboy because I am always seen with different beautiful women and famous models. It's kind of funny because it's not something I ever wanted but just happened and in order to keep my fans and friends happy just continued dating one after another.
In our office, all the Pro's and management are constantly hitting on Grace because she is so beautiful, confident, and always wears such sexy clothes all the time. As a man, I'm not sure I would be able to put up with all of that but that's beside the point. Grace, have you ever wondered why I've never hit on you like all the other guys?"
Grace looked puzzled and said, "Now that you mention it, yes!"
"OK, well since we are all letting out our deep secrets, I'm bi-sexual and prefer to be with men over women. There are several us in the Pro Athlete world that are like me, but we choose to keep it quiet and put on a show for everyone else for many reasons. It's difficult for me, especially when there are company affairs and events that call for me to have a companion. I usually have to bring someone I would rather not be with.
I've always had desired to be with a girl just like Amy and when I saw her that night it was like lightning bolt went off inside my head. Amy was what I've been looking for a girl that can offer me the best of both worlds. I've always wanted to date a girl like Amy but never knew how to find one that would be able to keep my secret until now."
This changes everything because Amy Rose, you have everything I find attractive in a woman. Since I'm six foot six and a big guy I need a companion that has a relative height and you're perfect. Most of the other girls I date too small and make me feel awkward but you're the perfect complement to my size. Just like Grace, you dress elegant and sexy and I love that in both of you. You would make a perfect complement to me with that something extra I need and enjoy. To be honest, I came here tonight with low expectations but after getting to know you and seeing how comfortable you are as a woman, I want to spend more time with you.
Grace, you asked me to keep this secret and I want to do just that. I can't imagine how living with Amy would impact your new position. If all the macho men at the company and our customers learned that your husband is living as a woman, it would ruin your career. I promise never to say a word and it will remain our secret, however, I will do this with this one simple demand, and I hope it’s something you both will be comfortable with."
Tony looked at Grace and then me and said, "Ever since that night last week when Grace and I saw you dressed as Amy, and we learned about your secret, I couldn't stop thinking about how sexy you were and how I wish I could find a woman like you. I always wanted to be with a beautiful woman that met all my needs and when I saw you, I realized that a girl like you is what I need in my life.
To be honest, when I started thinking about this situation, I realized there could be a way for everyone to get what they want and I'm willing to start slow and let you get comfortable with the situation.
As I said earlier, whenever I go to all the events and need a companion to accompany me and I find myself always asking women to go as my date, but I never have feelings for them, and nothing ever happens. I know when I leave them, they aren't happy and I know they must talk with the other girls and I'm always afraid my Playboy reputation could be hurt which would affect my income and public image, as you can imagine.
Grace, if you agree to this what I'm suggesting is that you will allow Amy to be my companion on these dinners and events. Amy would be someone that knows me and will keep my secrets safe. You see, we will be helping each other get what we want, and nobody is harmed, and I promise to take good care of Amy at all times."
With my mouth wide open in shock I saw Grace thinking about what he said and looked over at me, "Well, see what you've gotten yourself into Amy? It appears you now have a boyfriend. Isn't that special? I don't know what to say except you are getting exactly what you deserve, Amy. You will have to do this and accept this in order to save my career and our marriage."
I protested and tried to back out but Tony and flat out declined the offer. I said it was out of the question and he will just have to get another date for the event.
Tony made it very clear that this wasn't a request in a loud forceful voice that shook me deep inside and let us both know that he was in charge.
"Girls, this is not open to discussion. Next Friday there is a Charity dinner event in the city, and I will have my limo pick Amy up at 7 pm for a formal dinner so dress accordingly. I will also expect you to act warmly towards me in front over everyone. Is that clear? This is not a game and I'm trying to be nice about it and I was hoping that you would be open to this offer and accept my request and friendship. Either way, you will be my date. I'm hoping you'll reconsider your feelings and try to be happy about the opportunity to be out with me in public, as Amy.
Grace, this is the annual charity event that you will be hosting next Friday, so the good news is that you will be there for support if Amy needs some. Let's just take some time to think this through and you'll see how this can be a benefit to all of us, I'm sure."
That was how we ended the dinner. Tony thanked us for the great food and wonderful hospitality and once again said the limo would be picking me up at 7 pm next Friday and how he was looking forward to our time together next week.
He gave both Grace and I a hug and kiss before leaving us to clean up the mess.
After she closed the door she turned and looked at me with an odd look and said, "Well, that was unexpected. I mean, you make a pretty girl, but I never anticipated this or the fact that my husband is now dating a hot pro athlete. It makes me kind of jealous," she said with an odd laugh.
I was so nervous and said, "Are you really going to make me do this and go out with a man? Are you kidding, I said almost in tears?"
A little angry she said, "Don't cry to me Amy, this is all you’re doing. You're the one that was sneaking around dressing up and acting like a girl and careless enough to get caught. It's not my fault he prefers special girls like you, but that's exactly what's happening. Yes, you're going to do this and you're going to do it right, nothing halfway. I've worked too hard to get where I am today, and you will not screw up my career! Do you understand? It's bad enough I have to learn about your feminine side the way I did, but I am not going to let you screw up everything I've worked for, so get used to it quickly, Princess.
I suggest you try to accept your fate and accept your new role as Tony's companion because we don't have any other choice. Once you accept it you will have fun going to all these fancy events. I remember how you used to complain that you never got to go to all of these affairs and meet the Pro-Athletes, so now you have your opportunity.
Listen, this wasn't my idea and I can understand how you feel but you need to consider the situation here. My new position is going to make us very comfortable and you won't even have to work if you don't want to, which means you'll have more time to spend as Amy and my housewife. Just give it some thought and I'm sure you'll see the advantages. I can tell you there are lots of women that would love to be in your place right now being Tony's female companion. Amy, it's just like everything else you've recently experienced like having your ears pierced, your new hairstyle, long nails, and eyelash extensions. You'll quickly get used to the idea and enjoy another part of being a woman, which is what you told your mom you always wanted. I can't wait to tell her the news, she'll be so excited for you, sweetie.
We will have to shop for a new outfit for the Charity Ball this week. I'll call your mom to join us because she knows exactly what looks good on you and I enjoy seeing how different you act around her, it's really amusing. We'll have fun and we can do dinner when we're done shopping. I'll arrange another salon treatment for Friday afternoon to get you ready for the evening. Tell the truth, you do enjoy the shopping and salon visits, don’t you?"
"Yes, I do love that part of it, but I only want to be with you."
"I know you love it and I love taking you shopping and seeing how girly you act when we're out together. As far as only being with me, well that seems to have changed tonight. No, you will get used to it and I have a feeling you'll enjoy the attention you get on a date and how women get treated by a real man. You may never want to come back from this, Amy."
Tony's Companion
All week I tried to come up with ways of getting out of this date with Tony. I cried, begged, and pleaded with Grace to come up with another date for Tony, and to convince him to let me out of being his date to the Charity Ball.
She would have no part of it and engaged my mother to take me shopping for an evening gown suitable for the event, and something to compliment Tony who will be in a tuxedo.
"Amy, you have to stop begging. Tony is excited about Friday and has mentioned it several times so there is no way out. He has been a gentleman about all of this, and even asked for my permission to take you out, while knowing you really are my husband. Tony wanted to ensure that this was going to be OK with everyone. I explained that now that I have seen your true inner girl, that you are more of a girlfriend to me and that I want nothing more than the two of you happy."
"What? Why did you say I'm more of a girlfriend, not your husband?" I asked.
"Well, to be honest Amy ever since I've seen you in dresses and make-up, I have not been able to think of you as my husband. I do love you, and want you in my life, but right now I think of you more as a woman or my girlfriend, and I'm not sure I can ever think of you as my husband again. I'm sure you understand, because you know how feminine you have become, you can't think of yourself as a man, or in that case my husband, can you?" She asked gently. I could tell she wasn't being mean or trying to hurt my feelings, but she made it clear that our relationship has definitely changed.
"I guess I can understand what you're saying, and I don't blame you, but I can't lose you, I love you too much." I said.
"Oh sweetheart, I love you even more now, and I have no intention of letting you go. Let's just see where this goes, but in the meantime, I suggest you enjoy the ride, and live out your dreams of living as a woman. Not many people in your position would ever have this opportunity, or an understanding wife to help, so please just try to enjoy the things you cannot control.
I promise that you are going to have fun and you will be safe because your Tony, your Mother, and I will be making sure everything goes well. Now, tomorrow afternoon your mom is picking you up at 2pm and taking you to Nordstrom’s, where I'll meet up with you after my meetings. She is going to help you shop for an outfit for Friday. Since I'll also be at the event, I'll need a new outfit as well, so we can just have fun shopping together, as girlfriends." Grace added.
I was horrified, "You really told my mother that I'm going to be going on a date? How could you?"
"Amy relax, your mom was so happy for you and wants to be part of your new life as a woman. She was so excited and said she always wanted a daughter to go shopping with, and now she finally has the chance. You're really making her happy and I'll expect you to go along with this, be her daughter, and let her enjoy the experience. She knows all about the affair, and exactly what you will need for Friday."
After cleaning up the house the next morning, I took a warm scented bath and tried to relax before getting ready for an afternoon of shopping with Grace and mom. I picked out a flowery sun dress, that would be easy to change in and out of as I would be trying on outfits all afternoon. I wore my black heels that I knew would be helpful for the outfits they would be selecting for me to try on. After putting on my makeup and fixing my hair, I put on my jewelry and perfume, and grabbed my purse just in time, as mom pulled into the driveway. I was walking up to the front door and let mom into the house when she looked me over and smiled, "You look lovely today Amy, and I love what you've done with your hair, it really fits your facial features well. Are you ready to go?"
We sopped in several stores but finally found some nice outfits at Nordstrom’s, her favorite store. Mother picked out several outfits and had me carry them into the fitting room as she followed. I was a little taken back when she explained she was going to help me dress.
Mom giggled, "Don't be silly Amy, us girls do this all the time and besides, I'm your mother, now step out of that dress and let's try this on," as she held up the first of many silky black cocktail dresses.
I took off my dress and stood in front of my mom in my push up bra, sheer pantyhose, and heels. She looked me up and down and smiled, "You have such a nice figure, I'm sure we'll find the perfect dress for you, honey."
There are no words to explain how I felt standing there in my lingerie and heels in front of my mother as I watched her examine the figure of her new daughter, me. For years I wished for this when I was young but now, I didn't know how to respond and covered my breast with my hands. I saw that amused mother, as she just smiled.
She took the dress off the hanger and held it open as I stepped into it and slid it up into place. Mom zipped me up, and I put my heels back on and turned to the mirror.
"Mom, this is beautiful I love it" I said as I saw the pretty girl in the mirror. The lace top covered my breast and the short dress came to mid-thigh. Sexy and elegant, was how mom described it as I enjoyed the image in the mirror."
"Ok, that's enough we have several more to try on, let's try this one," she said as she unzipped the dress and hung it up as I slipped into the next dress just as Grace showed up. They had me try on several different styles until they decided on the first one that mom picked out, a short silky black cocktail dress that worked will with my body and not too revealing up top. It really fit perfectly, and the silky material felt heavenly as it moved across my body and nylons.
Grace brought back several dresses to try on for herself, and the one the both liked was also a black cocktail dress but hers was very low cut, which put her large breast clearly on display. I didn't like her wearing something that sexy and suggested other dresses that had weren't as revealing, but my own mother gave her opinion and encouraged Grace to go with the low cut dress.
"Oh Grace, that looks spectacular on you and shows off your wonderful figure, you just have to buy that dress. You will have every head turning, I'm sure." Mom said.
"It's a little over the top, but I will be the hostess with all the Professional Athletes, it can only help my position and popularity, so yes I agree. Besides, I have to look as good as Amy will look in her dress."
It made me uneasy to imagine my wife dressed in a sexy dress, with her breast on display with all those jocks for the evening. I wasn't sure if I could handle watching her with other men, but realized I had lost control of the situation and just sighed to myself. The rest of the day was fun as we shopped for some accessories and picked up some makeup. Shopping for all these feminine items with my wife and mother was fun.
As Friday approached, I continued to try to get out of my date with Tony and kept asking Grace to help. She listened to my pleas, but said we really had no choice and finally on Thursday night she told me that Tony had come into her office that morning.
"Honey, I spoke with Tony today when he came into my office. I was going to see if he would reconsider, but before I could discuss it, he explained how excited he was about tomorrow night, and promised that he will keep everything a secret.
He said, "I've given this a lot of thought this week and I promise nobody will find out about your husband, but that depends on his performance. I'll expect Amy to be attentive, as any girl would be with her date. My image is important, and I need you to make sure she understands that she needs to pass as Amy, not only for herself but for you and me, as it will ruin both of us if she lets us down. What I'm saying here is she needs to remember that she's my date, and girlfriend, which means that she will need to react correctly, if I give her a hug or a kiss and not pull back or make a scene. It would be helpful if she would reach out and touch my arm or hold my hand. You know exactly what girlfriends do on dates, and I want to ensure she is not going to embarrass us tomorrow night. I think it will be fine if she has a good attitude about this, so please prepare her for tomorrow.
What about your marriage? Clearly, you can't consider Amy as your husband any longer. Are you going to divorce him?"
Amy looked shocked as I repeated what Tony had said and asked me, "What did you tell him?"
"Well, once he made it clear that you were still going on the date and how important it was for you to behave, I told him not to worry and I'll prepare you for tomorrow. I also told him that I had no intention of divorcing you, however, I didn't believe that I could think of you my husband anymore. I told him that I loved you, and that you would stay with me as my girlfriend until we figured things out.
Now more important, let's talk about tomorrow night. As you know I'll be the main host at the charity event, which means I won't have much time to be with you or keep an eye on you. For the most part, you will be on your own and Tony's date. You understand that as his date you will have to act a certain way. I know you don't have the experience so let me help you understand what's expected.
You will be his eye candy, his girl, and you will need to act as any girlfriend would with their guy. He will kiss you and hug you in front of people, and it's important you respond like his girlfriend and welcome his attention and act happy to be with him. When you stand next to him, be sure to hold his arm or his hand, and show everyone that he is yours because, everyone will notice.
You will always have to mentally be in your girl mode, which you should be comfortable with by now. I'm sure you'll be dancing with him, so just always follow his lead and look thankful and happy. You need to pull this off for both of us tomorrow night. The good news is that the event will only last about three hours, so I'm sure you can pull it off without any problems. Make us proud, Amy."
"Oh my god, I'll have to kiss him and hold his hand?"
"Well, of course. You are his date and his girlfriend, and that's what girls do. Don't act surprised we both know what will happen. What's important is that you stay in character, and don't show your male side at any time. He expects you to be a woman, all night, and if you don't accept his advances it will be trouble for both of us," Grace said.
"Grace, what if he wants something else?"
"Well, then you'll understand what being a girl is all about. Come on, you have played with all those toys and you know exactly what to expect. I suggest if things get a little hot that you either jerk him off, or give him a blow job, no big deal. Remember, It's only sex and we're both adults so it's really no big deal."
I looked at her in shock and said, "No big deal? A blow job is no big deal, are you serious?"
She looked at me with a smile, "Come on honey, we aren't teenagers anymore. Sex is just sex, nothing more. It's not like you love the other person, it's just sex nothing more. It doesn't mean you don't love me anymore it's just a physical release between two people so don't make it such a big deal."
I felt a wave of panic come over me as I wondered if that's how she felt about other guys, and if she was having sex. A wave of jealousy came over me and I had to ask, "Does that mean you are having sex with other guys?"
She laughed, "So that's what concerns you? Me having sex with other guys not the thought of putting Tony's cock in your mouth, and giving him a blow job? You're more concerned about me being with a man, then you are about sucking another guy's cock? That's priceless, Amy."
That brought the main problem back in focus and I started thinking about having to do that and all types of new feelings were coming over me all at once. I sat there silent as she continued.
"For your for your information, I have not had sex with other guys, but if I did it would not mean that I didn't love you because I do, more then you know. On the other hand, I do have sexual needs, and you must know I haven't been sexually satisfied for quite some time. To be honest, I do think about it often, however, I've never acted on all the offers I'm constantly bombarded with, but ever since I saw how happy you living as Amy, I realize that sex between us will probably never satisfy me again. I am not into sex with another woman, so being with Amy is not appealing.
For the last year I have considered having sex, just to relieve my own needs and to be honest. after I met Amy, I've been thinking about it much more often. But if I did have sex with some guy, I would just consider it just sex, not a relationship or anything like that, which is why I consider a blow job just sex, nothing else. No emotional involvement but just a natural human event. Society places all these thoughts and meanings to sex, but if you think about it carefully, it is only twenty minutes of getting off with another person.
The reason I'm telling you this is because guys have expectations after they treat you to a fun night or give you a nice gift, which is the position you will be in, so you need to be prepared. When you're with Tony and things get to that point, you just need to let yourself go and do what all girls do for their boyfriend. Just remember, it's just sex and all part of being a girl. I know you've fantasized about it, so just like everything you've done recently, it's just another step of becoming a complete woman. It is what you've wanted all along, isn't it Amy?"
"Not for real, only in my fantasies," I explained.
"Well, just like everything else in your fantasies, this might become a reality as well. You are now living as a woman, and if it happens just accept it and try to be happy that you are getting to live out your inner desires and appreciate the chance to live as Amy. Most girls like you would kill to be in your position and be able to live out their inner desires and live as a woman full time, have an accepting wife, and a date with an alpha male that finds you beautiful and desirable. You do realize that you are a lucky girl, Amy Rose, don't you?
You know, as I sit here, I realize how selfish you sound. From now on I want you to be more appreciative of your position, and what your Mother and I have given you. I want to see more enthusiasm and hear you say Thank You more often to me and your mother. It's time you started to show us how thankful you are for all we've done for you! Do you understand?"
I sat there stunned. My wife just told me that Amy won't be having sex with her anymore and that she is thinking about having sex with other men. That I must accept having sex with Tony if he wants it. That I must be thankful to her and my mother about being allowed to live as Amy full time. My world has turned upside down, and I felt as if I was falling into a dark hole with no way out. I sat there quietly, feeling worried about what I just heard and didn't realize that she was waiting for an answer.
"Well?"
"Grace, I understand, and I am thankful for what you and mother have done for me. I know I'm very lucky that you haven't kicked me out after you found me dressed up in a dress and heels, and I'm thankful you've accepted me for who I am, and I really do appreciate everything you have done for me. I'm sorry I haven't been able to satisfy you in bed, but the thought of you with other men is something I never thought about. When I think about you with other men, it makes me jealous and I know I have no right to feel that way anymore."
"That's more like it, Amy. I expect you to remember that and show us your appreciation for not kicking you out on the street, and thankful for letting Amy live here and free to become a complete woman. We are still married, and I do love you, and I want you to be happy. If you love me, I would think you want me to be happy as well, whatever it is that makes me happy. Whether it's just sex or something else, I would expect you to encourage me to live my desires, just as I've stood by your side and helped you live your desires. I want to stay married to you baby, but if we can't support each other, then I will reconsider our current arrangements.
You should spend some time and think things over and see if you can live this way, and if not, I will understand but there is not going to be any negotiations. You will live here as Amy from now on and appreciate your place in our relationship. If you can't, then I expect you to be honest and tell me, and then you can move out and live your life without me, but that is not what I want."
“You expect me to continue to live as a woman? For how long?” I asked.
“Well, for now I expect you to live as Amy, full time. You became Amy in my eyes the minute I saw you all dressed up as a passable woman. I’ll help you become all the woman you can be, but for the foreseeable future, you will live here as Amy, my girlfriend and legal husband.
You can continue to work from home or quit your job. Either way, I’ll expect you to be the lady of the house, because we both know that I’m the real breadwinner in this family. I guess keeping your job will give you some feeling of your old life, but if you consider quitting your job you will have lots of time to focus on yourself. You can spend time at the gym and get a better female shape, getting a weekly manicure and salon treatment, shopping and being all the woman, you can become. But, as the lady of the house, I’ll expect you to clean the house and keep it spotless, do the laundry, food shopping, cooking, and any requested errands.
In fact, I wish you would just quit and live as Amy, because it would make things much easier and help you focus on your transformation. I mean, you are passable as a woman right now, but just think how much better you could become with more time to practice and focus on yourself, as I take care of everything else, you can become the perfect little housewife.”
Since she explained my situation like she did, I realized that just living as Amy wasn’t a bad thing, and if I was forced to admit the truth, it was what I wanted. She was also right about the job, but if I did quit, I was in effect giving up my past life and any means to make a living, and fully dependent on Grace. The more I thought about living as Amy and being a housewife, having free time to develop Amy and not having to work, sounded pretty good.
“You might be right, maybe I should give up my job and just stay home and become your housewife, at least for the near future,” I said thinking about the possibilities.
“That’s perfect, I call and take care of everything this week. This will be fantastic, and just last week your mother even offered to help teach you how to keep up the house and do laundry, she’ll be happy to hear about your decision. For this to work we will need to get you a complete wardrobe and everything else you will need.
But we can worry about that next week, we need to focus on your debut with Tony tomorrow. I’ll be home early tomorrow, because I must get ready as well. My limo is picking me up early because I’m the co-host, and I have to make sure things are in order. That means you'll be getting dressed all by yourself tomorrow, and with your hair and makeup already done you should be fine. I've given the girls at the salon detailed instructions again, so all you have to do is show up on time.
I’m sure you’ll be nervous, but I have some good news. Tony said he got out of his afternoon engagement and will be in the Limo to pick you up, which means you won’t have to ride over to the event all alone. You just need to be ready by 7pm.”
That night I didn’t sleep well, as I went over our conversation in my head many times. The realization hit me that I had basically given up my position as husband in the relationship to live as Amy, gave up my job and became a housewife to Grace. I would become dependent on her and truly understand what it means to live as a woman. Eventually I fell asleep and woke up late morning, cleaned the house, and tried not to think about the evening ahead.
Wearing a loose summer dress and wedge heels I put on a little lipstick and blush, brushed my hair and went to the Salon for my afternoon appointment. The girls greeted me enthusiastically and told me they were so excited for me and my first date. They wanted me to tell them all about him as they brought me to the back.
“Grace said he’s tall, dark, and handsome, you must be excited. Don’t worry; we’re going turn you into a very sexy princess tonight.”
I told them he’s a friend of Grace that came over for dinner, and I was extremely nervous. They tried to make me relax, told me jokes, and not to give him too much on the first date. They were having fun as they worked on me and I had to admit, I enjoyed being treated like any other girl, getting ready for her date.
My extensions were adjusted, and my hair was washed and brushed out into a wonderful style, pinned and sprayed into place. They worked on my nails and gave me a new coat of deep shiny red color on my toenails, and my extended fingernails. I had my long eye lash extensions filled in, and given a coat of waterproof, long lasting mascara, after my evening wear makeup was completed.
They were very busy completing Grace's list and they finished with a leg waxing before they said they were done. They finally allowed me to look at their work in the mirror, and I stood there with my mouth open. Looking back was a beautiful girl dressed up for a special occasion. The girl was clearly going to be eye candy for her date, and any other guy that saw her tonight. There was no way I was going unnoticed, especially being Tony’s date. I felt butterflies in my stomach, as the girls were so excited on how I turned out.
“Your date is not going to be able to keep his hands off you tonight, Amy. We’re so excited for you, please come back and tell us all about your date!” The girls said as we all smiled and giggled.
I got home around 5 o’clock and Grace was gone but left a note for me on the table.
The note read, ‘Amy, I had to get to the event, so I'll see you later tonight. I left a few things I want you to wear with your outfit tonight in your room. Please be sure to wear them, because I’ll be checking later tonight. Tony called and told me how excited he was for his date, I hope you’re ready for your first date, it will be fun watching you all night. See you later, Love Grace.’
When I got to the bedroom, I saw what Grace left out of me to wear with my outfit. Some new hoop earrings, some rings, a necklace, several bracelets, and a garter belt with a new pair of seamed stockings. There was another note pinned to the garter belt.
This note said, ‘I know you always wear pantyhose but tonight I want you wearing stockings. I want you to feel the tugging of the garters all night long, the fear of your nylon’s tops being exposed to everyone, and how it feels to be vulnerable. It will make you feel much more feminine and remember, if Tony gets a peak it will certainly excite him, so be careful honey. If you feel nervous and overwhelmed, I left a pill on the nightstand that you should take to calm you down. It's a low dose sedative that will take the edge off and help you relax and survive the evening. Put it in your purse and take it if you feel like things are getting out of control, this will help you. See you soon.’
When the Tony rang the bell, I felt my heart race and knew it was my moment of truth, and things would never be the same. I wanted to run out the back door and hide, but I knew there was no choice but to go through with this and get it over with.
My legs were shaking as he greeted with a quick kiss hello when I opened the door, and then let me to the limo after I locked up the house. The limo driver held the door for Tony and I as we entered the stretch limo, which is when I had my first experience wearing stockings. As I entered the limo, my dress slid up giving both Tony and limo driver a clear view of the tops of my stockings, and the garters holding them up. I quickly slid in and pulled the dress down, over the stockings which unfortunately gave the impression that I was flirting. I now realized what Grace meant when she told me to be careful wearing stockings because unlike pantyhose, they will be visible whenever you aren’t careful. I realized I would need to pay more attention to that, as the night continued.
I saw both men smile and watched Tony slide next to me in the back seat. Fortunately, he didn’t say anything about the incident. I had never been in a stretch limo before and was impressed with the experience. Tony sat next to me and offered a glass of champagne, as we started on our thirty minute journey to the hotel.
“You look amazing Amy, and I love what you’ve done to your hair, you look very elegant."
“Thank you, I’m glad you like it,” I said trying to hold the champagne flute, but my nerves made my hands shake and almost spill the drink. I took a few sips and tried to relax.
“You look a little nervous Amy, are you OK? I know this is your first time out and I will help make you comfortable tonight. Grace told me about the sedative in your purse and maybe you should take it now before we get there. It might relax you a little when we get there because there will be a lot of people and activity, I want you to be relaxed. Hand me your purse,” he said forcefully. I handed him my purse and he found the pill and held it out in front of me. I saw my long red nails carefully take it from his massive hand and put it to my lips.
“Good girl, go ahead and swallow and soon you will feel much better.”
_______________________________________________
I felt small as I sat beside Tony, which made me even more insecure and submissive. I was quiet as I sat there still frightened about what was to come and tried to drink out of glass without spilling anything.
After a few minutes I felt a warmth wash over my entire body and it felt like a huge weight was taken off my shoulders, I relaxed and allowed myself to sit back and lean against Tony. Whatever was in that pill worked it's magic, and I was now completely relaxed. Tony saw my compliance and put his arm around my shoulder and pulled me close, as I just enjoyed all these new feelings. Between the drinks and the pill, I was not only relaxed, but I became ultra-aware as Tony held me.
Everything was now moving slower and more peaceful, as the sensations of the garters pulling on my nylons created a wonderful sensation. I noticed my long eyelashes as I blinked, the creamy feel of my lip gloss, and the smell of my floral perfume. I was awash in a wonderful world of feminine feelings and felt safe with Tony's strong arm as he held me close. I found myself enjoying the attention and that safe feeling as we sat there and smiled at each other.
"I can tell that the little pill you took has started working, and it should help you get through the evening. Grace explained it should last about 6 hours, which is how long this night should last. I'll keep an eye on you and make sure that you're OK, but you need to remember what Grace told you about tonight. It's important that everyone believes you're a woman and my girlfriend," Tony said softly into my ear as I just sat there listening and smiling.
"Yes, I understand and I'm sure you will be proud of me tonight," I said as I wondered why I said that out loud.
When we arrived, the driver opened the door, Tony helped me exit the limo, which was not easy due to the two glasses of champagne and the sedative. I giggled as I pulled the bottom of my dress down and took Tony’s hand, as he led me into the venue.
I asked Tony to slow down, as I tried to keep up with him in my high heels. He was gentle and understanding and led me into the ballroom where we were seated at the front table near the podium, where Grace was standing with someone having a discussion, most likely about the event. She saw me, smiled and waved, and a few minutes later came over to say hello.
“Amy, you look amazing in that dress and you two make a cute couple.” She said smiling. That would have bothered me except for the drinks and the pill, but now all I could do was just smile back at her.
Grace continued, “You look very relaxed for a girl on her first date. You took the pill already, didn’t you?” I nodded and smiled back at her.
“I suggest you don’t have too much to drink tonight or you will lose all your inhibitions, and possibly become an embarrassment. Be careful and remember what I told you about how to act tonight, people will be watching.”
Grace gave the welcome speech and joined us at the table with Jared, the CEO and President of the company. I had never seen Grace in a work environment and was impressed on how professional she acted, and how attentive she was to her boss.
Tony kept me busy with conversation and I enjoyed how he treated me as an authentic female, and his girlfriend. Remembering what Grace had told me how to act, I paid close attention to him, touched his arm and held his hand or arm all evening. I was hanging on to him and from anyone looking at us they would only see a couple enjoying each other's company.
He even commented later in the evening as we sat there together, “Amy I wasn’t sure how things would go tonight but you’ve really gone out of the way to make me feel special, and I am impressed how attentive you’ve been. Every other girl I’ve taken out has always been self-absorbed, but you make me feel special. That first night I saw you I felt an attraction right away, and I’m thankful that things have worked out as they have,” he said right before he leaned in and gave me a gentle long kiss, which I found myself allowing and returning. When we broke the kiss, we smiled at each other and sat back in my chair only to see Grace looking at me with a shocked expression and mouthing the word. WOW!
That sobered me up as I had the feeling of being caught again but this time I it was kissing another man. I can only imagine what she was thinking and feeling. I didn't have time to think about it because Tony took my hand, and led me out to the dance floor, where we spent the next twenty minutes dancing together. He held me tightly as I had my hands around his neck and my head on his shoulder, as he led me around the dance floor.
I felt his strong arms and massive chest hold me safe and tightly, as we danced. I felt his big strong hand wander down my back and rub my bra strap and then my garter belt. It was at that moment that I felt his large cock start to press against my stomach, as we continued to dance. I was not sure what to do and just kept dancing and allowed him to rub my back, and eventuality my ass in the dark recesses of the dance floor.
Without the sedative I’m sure I would have reacted much differently, but I was so relaxed that I just went along and tried to enjoy the evening. We kissed a few more times during the dance and when we broke the last kiss, I saw Grace dancing closely with Reggie, a former NFL running back. She saw us kiss again and gave me a wink, as we both danced with these large muscular men. I should have been jealous, but Tony’s hand was now rubbing my bun so hard it was hurting. I looked up to tell him to go easier, but when I started to speak, he gave me a deep long kiss as we stood in the middle of the dance floor. We were still kissing when the music stopped and when Grace passed by, she said, “The music stopped, you two should just get a room.”
We went back to the table and I could see Tony’s hard-on pushing out of his pants and smiled to myself, thinking that I had done that to him and for some reason, it felt kind of good. Grace was now talking with a few of the players and having a good time, laughing and teasing the men. It was getting near the end of the night and I was getting sleepy from the sedative and drinks and ready to leave. We ended up sitting and talking for another thirty minutes before then Tony said it was time to meet our limo outside.
Grace saw us getting ready to leave and just waved, as she was now alone with Reggie in a deep conversation. I wanted to know what they were talking about and if she was going to come home alone or break our vows and be with Reggie. I didn’t have too much time to think about it as Tony grabbed my hand and led me out to the car.
The drive home was much different than the ride to the event. Tony closed the partition to the driver and wanted privacy. Tony now felt he could just kiss me at will, and freely made out with me on the drive home. He took my hand and placed it on his enlarged cock as we kissed.
“Amy, you are a sexy and exciting girl, and I want to be with you again.” He took my hand and moved it over his cock and said, “Look what you’ve done to me, Amy. Other girls never get me this hard, but you have really proved yourself to me tonight. Unzip my pants and hold it, please.”
How did I get here? A few weeks ago, I was only dressing in woman's clothes but now, I’m not only dressing but living the life of the girl I’ve kept hidden. Not only that, but I’m with a very handsome man who thinks I’m sexy and wants me to rub his cock. My desire to just dress and act like a woman has suddenly changed, and now I have this desire to make this man happy and if that meant holding his cock, why not? After all, tonight I was Amy Rose his girlfriend.
I watched my long red nails fumbling with his zipper as he moved to allow me access. I unbuttoned his pants and put my hand under his underwear. At that moment I wrapped my hand around his pulsating, warm, nine inch cock. It felt strong and alive as I held it in my hand. Tony moaned, as I moved my hand on his shaft and that gave me the encouragement to continue.
The power I felt from holding his large cock was exciting, and I watched him sit back in the seat with his head leaning back. As I stroked his shaft, he closed his eyes and smiled. He was extremely excited and getting even bigger as I continued to stroke him. At this point he moved his hand up my dress. and was now playing with the top of my stockings and rubbing my exposed thigh.
We were both turned on at this point as he said, “Amy, I love when girls wear stockings like this because it is so sexy, and you have such sexy legs, don’t stop stroking me baby. Just like that, yes keep it up just like that. You really know how to get me going baby, we have to do this again.”
I felt the car stop and realized that we were now in front of our house, but Tony wasn’t done and said, “Don’t worry about the car, he will wait for us so just keep that up and kiss me, Amy.”
I moved forward and continued to stroke him, as we kissed. He was now rubbing my ass under my dress and freely exploring my body as I felt him get very hard and then he broke our kiss. He rolled his eyes back and stiffened up as he shot his load all over the car. His hot stream of cum hit the top of the car, my face, the seat and splattered everywhere. I kept stroking him until he was completely relaxed and sat there smiling and satisfied. I grabbed some paper towels and tried to clean everything up including Tony and my face. I couldn’t believe I just gave a guy a hand job and removed his cum from my own face. What have I become?
After a few minutes Tony pulled his pants back up and I straightened my dress before he opened the door. The limo drive was there waiting and smiling. I was embarrassed as I realized that he knew exactly what we were doing back there, and just walked to the front door as Tony followed.
He thanked me for a wonderful evening, kissed me good night, and told me he would call me this week. I went in the house and collapsed on the couch and thought about the entire evening. I woke up on the couch at around 3 o’clock as I heard Grace coming in the door.
“You’re still up? “
“Yes, I was waiting for you to come home. I've been home for hours, what took you so long?” I asked.
“Well, Reggie and I stayed for a few drinks and closed the bar down. He wanted me to go up to his room like he always does, but I told him no and that I was married and came home. You, on the other hand, were all over Tony tonight. You really played the part of his girlfriend well, but I didn't expect you to be kissing him all evening, I heard several girls asking who you were and how lucky you were. You passed Amy, everyone believes you are Tony’s girl. You really are amazing and I’m so happy for you, but I need some sleep. We can talk in the morning. Oh, I invited your mom over for lunch so be sure you're up and dressed by eleven. She wants to hear all about your date tonight, so I told her to come over and we can chat, like all girls do after their dates.
I went to Amy’s bedroom, washed off my makeup, put on a nightgown and fell asleep in record time. Between the sedative and the late night, I slept soundly and woke up to the sunlight shining through the window. The clock said nine o’clock as I laid there slowly waking up.
Remembering that mother was coming over for lunch I got up, showered and put on my make-up. I knew that Grace would expect me to have lunch ready, so I hurried up and got dressed and put on a pot of coffee, as I tried to figure out what to serve for our luncheon and decided on a Mushroom Asparagus Quiche, some fruit, juice, and coffee.
As Grace slept, I set the table on the patio for three place settings, prepared the food, and had a cup of coffee ready for Grace when she finally came down around eleven o’clock.
“Thank you, sweetie,” she said as I handed her the coffee cup. “Looks like you have everything read for our brunch, very nice. You really do make a good housewife, Amy,” she said with a giggle. I didn’t pay attention and continued to start to make the Quiche, knowing that our mother would arrive shortly.
“Did you sleep well, Grace?”
“Oh yes, I was exhausted from having to work that event all night. I didn't get to play and relax like you did all night. It sure looked like you had a good time with Tony.”
“It was all right, from what I remember. That pill you gave me really helped my nerves and allowed me to get through the night. Without it, I’m not sure I could have pulled it off,” I said.
“Well you did because I heard many people make comments about the pretty girl that was with Tony, and how close they were. They were all wondering where he had been hiding you because with all your loving touches and kisses, everyone believed you two have been a couple for quite some time. I bet Tony was happy with the outcome and your performance.”
Mother arrived and we all sat on the patio as the food was cooking, and we enjoyed several mimosas, that I had prepared. It was a pleasant day, with a nice breeze and blue sky as we just sat there, enjoying each other's company.
I served the food and refilled the drinks as Mom and Grace just relaxed outside. We talked about going shopping next week and picking up a few things together as girlfriends do. At this point, I accepted things and started liking our outings together.
After we finished eating, I cleared the table, put things in the dishwasher as Mom and Grace chatted alone. I tried to hurry up so I could hear what Grace was telling her in private. With a pitcher full of lemonade and clean glasses, I came back outside and served more drinks to the girls and sat down.
Mom smiled and said, “Grace is right, you really are becoming a perfect housewife. Are you enjoying your new role as the lady of the house, Amy dear?”
“Yes mother, I do like taking care of Grace and she has been so kind to me that I want to make her happy.”
“Well enough small talk, I want to hear all about last night, after all that’s the reason I came over. Your first date and the first time Grace got to see you out with a man. Did you think he was as handsome as Grace said he was?”
Embarrassed and humiliated I just sat there as Grace and Mother waited for an answer.
“Amy, answer your mother. If you’re going to be my girlfriend you will need to get used to girl talk, it’s what we do, and we expect you to be one of the girls.”
“Yes mother, he is very handsome, tall and well-built.”
“Well, you’re a lucky girl. Grace showed me some photos of you from last night and I must say the dress we picked out looked lovely on you,” mom said.
“What pictures? I don't remember taking any photos.”
Grace turned her phone and displayed several pictures of me dancing with Tony and one of us kissing.
“Was that your first kiss as a woman, dear?” mother asked.
I knew I had to answer and said, “Yes, I never kissed a guy before.”
“Did you enjoy kissing him,” she asked as she casually drank her lemonade.
“I was sedated, and I don’t remember much but from what I recall it wasn’t horrible.”
Grace turned to mom and said, “I had Amy wear nylon stockings with her outfit, no pantyhose last night. I wanted her to feel vulnerable and know what we girls go through.” She turned to me and asked, “Did Tony like your stockings, dear?”
“He saw them by accident when I got out of the limo, and he said he thought they were sexy.”
“Did you like wearing them?” mom asked.
“I did, yes. The tugging on the nylons reminded me why I love dressing as much as I do, and it felt utterly feminine. I love wearing pantyhose, but I can see where stockings have an advantage.”
“Did Tony get to feel your stocking tops, Amy?” Grace asked.
I blushed and tried not to answer but they waited for an answer. I told them all about the ride home and how he felt me under the dress and played with the stocking tops. I also had to give them details about our kisses, how many, how long, if we French kissed, and if I did anything else. Finally, I told them how he asked me to touch him down there and asked me to take it out of his pants.
“So, you touched his cock! Did you give him a blow job as well?” mom asked as I sat there stunned by her words.
“No way. I just kind of stroked him there the limo,” I said.
Grace smiled and said, “So no blow job on the first date, but you did give him a hand job. Did he come for you?”
“Yes, and it was gusher. He came all over the place and I had to clean everything up off the seats and the car ceiling.” I said realizing I just confessed to touching a man’s cock and bring him to climax while we kissed in the back seat of a limo.
“Oh, you little slut, and you did all that on the first date. I’ll bet Tony will be coming around for more of that Amy,” mom said giggling.
“It was the sedative, I’m sure. I never would have done that if I was sober.”
Mother looked at Grace and said, “How does that make you feel, Grace. I mean, your husband or should I say girlfriend having sex and you all alone. That doesn’t seem fair at all. Do you have someone to date? Because it doesn’t seem fair that Amy gets to have fun while you just sit home alone. It’s not healthy for pretty girl like you, to be alone, honey.”
Grace looked at me and then lowered her head. I could tell her mood had instantly changed and I saw a tear in her eye and then she just stood up and said, ‘Excuse me, I’ll be back in a few minutes.”
“Mother why did you say that, it clearly upset her.” I asked feeling helpless. “How could you encourage her to find another man to be with? What were you thinking?”
“Amy, even though you make a very passable and pretty female, you don’t have a clue about our emotions. That would change if you decided to start taking some estrogen but, in the meantime, you need to consider the feelings of others and stop being so narcissistic.
Yes, Grace and I have accepted your desire to dress and live as a woman but where does that leave Grace? Have you considered her feelings? Her husband is now living with her as a beautiful woman and has already been out and sexual with a man. If you can put yourself in her place for a minute, how do you think it makes her feel?
You have so much to learn, and both Grace and I will help you, but you really must start thinking about others more than yourself. Don’t misunderstand me, I’ve accepted your desire to become Amy, and it seems as if Grace is giving you the opportunity to live out your dreams, however, you must realize that by doing so you give up your role as a husband and accept your new role as her girlfriend. And just so you understand, real girlfriends encourage and help each other, and want the best for their friends. You do want to the best for Grace, don’t you sweetie?”
“Of course, I do, but…”
She cut me off, “Stop. You said want the best for her and that’s a good start. Now, do you enjoy sitting here in that cute dress, your hair looking so feminine, nice make-up, as you move and act like a perfect woman? Do you want that to continue or are you prepared to give it all up forever, and return to being a man? Think about that, because your answer will certainly create changes in all of our relationships.
Do you want to continue to live as Amy? Simple question,” she asked.
“Yes,” I answered.
“Then you need to tell Grace and let her know that you will live as her girlfriend and will not stop her from living a full life. When she comes back you will tell her you want what’s best for her, and if that means seeing other men, then you understand, and that it’s completely natural. You’ll tell her you’re giving up your status as a husband and will be there to support her as her best friend, her girlfriend.”
Mother encouraged me to find the strength to let her be free, find happiness, and understand that my decision to live as Amy should not stop Grace from being happy because, all woman need the strength and love of a man.
Mother explained that it’s a choice I’ve already made, and once I give her permission to be happy, my own concerns and worries will be over. She explained that it was time to show some love and understanding, and how thankful you are to have such a loving partner that will support your own desires.
“Whatever happens, I’ll be there for you sweetheart and I feel closer to you, more than I have ever felt before. Having you as my daughter is a dream come true and I want to help you in any way I can, so please don’t shut me out. Allow me to teach you the things every mother teaches their daughter,” she said.
Grace came back and I excused myself and said I was going to refill the glasses. I gave her a few minutes to settle back and chat with mother before I came back with another pitcher of lemonade and poured the drinks.
“Thank you, Amy. This is so refreshing,” Grace said trying to show that she was relaxed and over her emotional outbreak.
I leaned forward and touched her knee and said, “Grace, mother and I have been talking and she made me understand some things. Since I've been living as Amy, I have only been thinking about myself and was inconsiderate to your feelings. I want to fix that and tell you that I love you, and I am grateful to you for staying with me during this time and allowing me to live out my own desires.
I know realize that it would be unfair of me to think you still belong to me as my wife, and fully understand that I gave up being a husband the moment I agreed to live with you as Amy. It's clear that living as Amy means that I am your girlfriend, and that I do not have any restraints on you. In fact, I want to encourage you to be happy. By that I mean, whatever you want and whatever makes you happy is my dream for you, and if that includes being with another man, I understand. Please know that I want to encourage you to follow your own feelings and desires, just like you've done for me.”
I saw mother tear up and watched as Grace smiled and looked deep into my eyes.
“Oh Amy, thank you so much for understanding. It has been so hard for me since I learned about Amy. I wanted to help you because I really do love you but, I have also lost my husband and that’s been hard for me. Thank you for understanding, and not trying to control me or tell me how to live my life, and yes, I will love having you as my girlfriend, but this won’t get you out of your housewife duties. Afterall, you are now a stay at home girl, and I am the money maker,” she said smiling.
We hugged and I told her I would love to be her homemaker, and that I will make her very happy.
Thanks to my mother, that afternoon was a healing experience for both of us as I admitted that I was committed to living as a female and housewife. Grace accepted my desire and I accepted her living her life as she sees fit, including any male relationships. Everyone was happy and we spent the rest of the afternoon making plans for shopping and dinner for the following week.
As mom was getting ready to leave Grace’s phone rang and she turned it towards us showing that the Caller ID displayed that it was none other than Tony.
“Hi Tony,” she said as mother watched on very interested.
Grace listened and said, “That’s great, she told me she had a really good time as well. Of course, I don’t mind, and I think she would love that. Why don’t you give her a call later tonight and tell her yourself? I think that’s a great idea, Tony. OK, see you on Monday."
Grace looked at mother and said, “That was Tony, Amy’s boyfriend.” She then looked at me and said, “He really enjoyed your company and called me to make sure I was going to be OK, if he asked you out for date. You heard me tell him that it was fine and to call you tonight. He wants to take you to his beach condo for the weekend, and I told him that would be a great idea.”
Mom sat there in shock. Grace smiled at mother and said, “Well, it looks like our little girl is a hit with the boys. I hope you told her all about the bird and bees,” she said giggling.
They both had a good laugh as I sat there in shock. This was all moving so fast and I was losing control as Grace and mother were navigating my new life as Amy.
Next Chapter
The following Monday I sent in my resignation letter, effective immediately and at that moment, I became fully dependent on Grace and agreed to remain as Amy and become her housewife. That decision came with expectations that Grace outlined, and I had to agree without objection.
Mother did stop by each day and helped me set up a housekeeping plan, taught me some laundry tricks, and how to iron correctly. I learned how to hand wash our lingerie and special items, and how to fold them and put them away properly.
She gave me her favorite receipts, taught me how to shop for the correct items, and how to cook and prepare meals. The correct way to set the table and how to clean up the kitchen efficiently.
Every morning I got up early and got dressed in an outfit appropriate for the day’s activity, that mother had mapped out for the week. One day I dressed for some heavy house cleaning in a smart dress, one inch heels. Another day I dressed for a day out of shopping, manicure with mom, and lunch.
Mother always treated me as her daughter, and not once did she refer to me as her son or a man. In her eyes I was now Amy, the daughter she always wanted, and I could tell she was enjoying our time together. I could tell how much she enjoyed teaching me things or correcting some of my movements and even what topics we discussed.
She directed our conversations to fashion, decorating, and things for the home, cooking and gossip magazines. I was now fully immersed in the female world, and I had never been happier. Mother was fast correcting me on my posture, how I carried myself and my casual movements. She pointed out how I needed to use and bend my wrist more often, keeping my elbows closer to my side as I walked, even how to be more convincing when I walked in heels.
It was embarrassing at first as she had me walk back and forth in my living room as she perfected my walk and movements. That caused me to move a little differently and after several days, I was used to the new walk which gave me much more confidence. This new movement also made my hips sway from side to side as I walked which I knew would draw more attention to my legs and bum.
At lunch we often talked about my figure, some new hairstyles, and that we need to pick up a couple of bathing suits for my weekend with Tony. As I was eating my small salad, she looked at me, with what I can only describe as a motherly look and finally asked me about Tony. I could tell she had been wanting to bring it up and this was her opportunity.
“Honey, do you like being with Tony? How does he make you feel?”
I almost choked and quickly looked up, “Mother! I don’t want to talk about that.”
“Oh Amy, come now I’m your mother and you can tell me anything. It’s natural for you to be interested in men, and from the photos I saw he is very handsome and besides, we all know what happened in the limo last week. We’re both adults, and I want you to confide in me as my daughter. It’s what girls do, honey.”
Her smile was comforting, and I felt like I owed it to her, for how she’s helped me and accepted me as a woman. I took a deep breath and decided to open up to her.
“He treats me very respectful and special. It’s hard to explain but I really like how he does things for me like open doors, holds my chair for me, takes my hand when we walk, or when he puts his strong arm around my shoulder. Even though I feel like an object sometimes, I like how he makes me feel safe and protected.”
Mom smiled, “That’s how men treat the woman they like and want to be with, and feeling that way is how we girls should feel. You're experiencing feminine feelings, and exactly how they should be felt. Women desire men to take charge, make us feel safe, and treat us special, just like you described.”
“But mom, I feel like I shouldn’t have those feelings. I never thought I would want to feel that way around a man, I never thought of myself as being gay.”
“Amy, you’re not gay or anything like that and you know it. When you’re putting on your make-up, doing your nails or hair, stepping into your dress and heels, or putting on your lipstick, do you feel anything other than being female?”
“Well no Mom, but.”
“No buts, Amy. You’re a woman and having those feelings towards a man is natural. Those feelings are completely normal, and as I’ve been telling you all week, you need to embrace your deep feminine feelings and understand that even though you may not have every part in the right place, you are living as a woman and should act, and feel that way without thinking about it. So, from now on, I want you to watch what you think about and don’t allow any negative thoughts to enter your mind. You are to think of only feminine things from now on, nothing else. Do you understand?”
“Yes, mother. I understand and I’ll do as you say. Thank you again for all your help.”
“Amy, you’re very sweet, and I love you and I'm so happy we can spend time together like this. Now, this weekend you’re going to spend two nights with Tony, are you prepared for that? Have you thought about what might happen this weekend?”
“Well Mom, to tell you the truth, I've tried not to think about it too much. I’m very nervous about going with him, and would rather stay home, but Grace has insisted, and I really have no choice. What did you mean when you said, did I think about what might happen?”
“You need to think about it because men like Tony have expectations and will get what he wants. You need to mentally prepare for anything while you're with him this weekend. Have you considered that he will expect you to be sleeping with him in the same bed? You have already touched him down there and relieved his male urges, so you realize you’ll be doing that again, right? He will be buying you dinner, taking you out, and treating you like a special lady, and for that he will expect you to do things for him, I’m sure of that.”
“I haven’t given that much thought, but I guess I should. What should I do, mom?”
“Well, if you want to see him again you will have to give him what he wants and I’m sure that will mean lots of kisses, letting him hold you close, and probably oral sex. Even your mother knows that men expect that on dates, baby. I know you haven’t had that experience yet, but you should prepare yourself for that with Tony. If things go well, he will probably want to make love to you by the end of the weekend, and that will seal your fate.
Have you given much thought about my conversation about encouraging Grace to live her life without feeling guilty? You know, she needs the touch and love of a man just as much as you, Amy. She has been so understanding with you and for that you owe her a great deal. You must have that conversation with her before you leave for the weekend otherwise risk her continued support and understanding.
I suggest you have a nice conversation over dinner and thank her again for allowing you to flourish into this beautiful woman, and how important it is to you for her to be happy again. Tell her to follow her desires where ever that leads, and that you will be one hundred percent supportive. You need to remove any guilt she might have, about being with another man and that you love her, no matter what.”
“Mom, I know you’re right but it’s so hard to give her up to another man. I mean, I love her dearly and I’m not sure I can see her with someone else.”
“Sweetheart you need to realize that Grace is not bi-sexual and being with Amy is not going to satisfy her needs. If you want to remain in this new role as my daughter and Grace’s housewife, then you have to make concessions. Is it worth living as a woman and giving up your hold on Grace? Can you stop being Amy or more important, do you want to stop living as a woman?”
“That’s not fair, mother. You know the answer already. Amy is here to stay and that just means I will have to understand her needs and be supportive, as you’ve already explained. It will be difficult for me to tell Grace to date other men, and that it’s important to me that she is happy, and that as her housewife I realize that I can’t satisfy her needs. I’ll be officially giving up my role as husband, forever. I know it is the right thing to do mother, but you do understand how hard this is going to be.”
“Amy dear, we all make sacrifices and right now it appears that you’re getting the better part of the bargain. You have your wife and mother helping you transition, a handsome boyfriend that wants to take you away for the weekend, a loving and understanding wife that is encouraging you to be happy. You already know what you have to do, so stop your complaining and tell her before the weekend.”
Tony and Grace spoke a few times that week, about the plans for the weekend. They seemed to enjoy making plans for me without my involvement, but Grace realized that I wasn’t ready to be making these types of plans just yet and was protecting me and helping me along the way.
“You’ll need to be ready by 3pm on Friday so I’ve made a salon appointment for the morning which will give you lots of time to pack and get ready. You’ll be spending the weekend in his beach condo in Palm Beach, you lucky girl. Your mother showed me the outfits you purchased, and I think you’ll look lovely in them but, Tony was a little concerned about the bathing suits and we discussed some options that he believes will solve any potential problems.
Even though his beach area is quiet, there will be other people there that know Tony and he can’t risk anyone finding out that you have a little extra in your panties. We both agree that you look, sound, and act like any other women but he can’t take a chance of an unexpected bump in your bathing suit bottom.
Tony said he had a solution that worked in past with other girls and sent a package over for you to use this weekend. I did some research and I think it will prevent any problems,” Grace explained.
“What is it, what did he send over?” I asked.
Grace picked up a small box off her lap and handed it to me, smiling and said, “Open it and find out.”
I recognized the small metal device right away and just stared at it in shock. “You both expect me to wear this under my clothes? The tight panties and have kept things hidden to everyone, why this.”
“Amy, this is a chastity device or just a little clitty cage, and that’s what Tony likes to call it. It will prevent your little boy bits, from getting excited and keeping things under control and out of sight, in case something happens. That means, the bathing suits you'll be wearing will not give any secrets away. Tony said that he had some close calls with previous girlfriends and can’t take any chances and until you start taking T Blockers, he wants you to wear this for both of your sake. At first, I thought it was odd but the more I thought about how it works, the more it makes complete sense. It’s really no big deal, and you said that you don’t get turned on by men, so you shouldn’t have any objections. Let’s see how it fits.”
She had me pull up my skirt and remove my panties and for the first time in weeks, Grace touched me but, it was all clinical, nothing sexual in how she worked the device into place, and clicked it closed. I felt humiliated as I held up my skirt and allowed her to put my only male vestige into that device.
Surprisingly it wasn't horrible since it was so small. The shape of the device kept my boy bits tight against my body, and presented a noticeably smooth front in my panties, after I pulled them up back into place.
“Looks like Tony was right and the size he picked was perfect. No matter what happens or how excited you get now, there will not be any accidents and you’ll now be able to wear some of those sexy tight dresses. You can even wear your bathing suits without worrying about showing everyone our little secret. Wear it for the rest of the night and try to get used to it because, you'll be wearing it all weekend.”
Knowing I had agreed to obey her wishes, I wore it to bed and the next day after my shower. It wasn’t uncomfortable and it did give me extra protection and a much flatter figure. However, I was a little shocked, and even more humiliated when my mother came over for coffee the next morning, I wanted to run and hide when she asked me how I liked wearing it and if it was very uncomfortable. Grace must have told her about it and now she was asking me how I liked wearing this device. I realized at that moment that nothing was private between Grace and my Mother. It was difficult to get used to, but I knew I had no choice in my new position as a daughter and housewife.
I didn’t want to discuss it, but I knew she expected me to say something, so I said, “It’s OK and I'm already used to wearing it.”
“Well, it will be worth it when you slip on those sexy bathing suits and wear those tight dresses. Now more importantly, did you discuss what we talked about with Grace? Did you encourage her and tell her it was OK for her to be happy and that she needed to live her life however she desired?”
“Yes mother, we talked about its last night. I took some time and told her how much I loved and cared for her and wanted the best for her. I thanked her for helping me and staying with me through all this new stage in our lives. I apologized for not letting her know about my feminine desires sooner, and I also told her I was sorry about the way she found out.
She thanked me and said she only wants the best for me as well, and she can tell that letting Amy live her life was the right thing to do because, she hasn’t seen me this happy in a very long time. She said she loves me and now feels much closer.
“Did you tell her it would be OK for her to have other male friends, if she ever needed their company?” Mom asked.
I lowered my head and said, “Telling the love of my life that it would be OK to date or be with other guys, was one of the hardest things I’ve ever had to do, mother. She was shocked at my honesty but was also grateful and thanked me for my understanding.”
“What did she say, tell me everything Amy.”
“I told her that I have been so wrapped up in my new life that I was not really thinking about her feelings and needs. Living my new life as Amy, going out with Tony, and living as the girl I’ve kept inside me, was overwhelming. After I found out I was going out again with Tony and leaving you alone while I’m out with some guy, has given me a tremendous amount of guilt.
I said, Grace you’re a sexy woman, and I know guys are constantly hitting on you, and that you’ve been nothing but faithful to me, and now that isn’t fair. Since I'm going to be living with you as your girlfriend, I realize that I've given up my position as husband. With that in mind, I want you to be happy and if that means having friends that are men, is understandable and only natural, and something I want if it is what you want.”
Mom was pleased with my comments, “Wow, good for you Amy. That took a lot of courage to do that, but I’m proud of you, and I know you it was the right thing to do. What did she say to that?”
“Mother, she had such a big smile on her face when I said that. She finally stopped smiling and said, ‘Thank You, Amy! I didn’t know how to bring it up and you made it easier for me because you’re right, I do need male friendship and the more I’m around you as Amy, the more I realize how alone in this relationship. I don’t have anyone in mind but just knowing that you understand what it must be like for me, is amazing. I'm so happy for you and I’ll be there all the way to help you with anything you need, and I expect that same from my girlfriend. Let's make a promise to tell each other everything, just like all girlfriends do because, that will make us so much closer as girlfriends. I know this is all new for you but, I’m here to help you with anything you need or any questions you have.’
Date Night
Ever since my conversation with Grace about our relationship, she was now so much more friendly and giggly as she helped me pack for my weekend. She picked out all my outfits, told me what to wear for dinner, what cover-ups to bring down to the beach, and what sandals to wear, what to wear to bed, and encouraged me to remember that I’m Amy, a girl and on a date with a real man. She even said, “Be Amy, and do things Amy would do with her boyfriend, and remember I love you no matter what you do, I just want you to be happy, and discover how great it is being a female in today’s world.”
Going to the salon now was no longer a big deal because, I knew what to expect and the girls were always nice and supportive. That day they added some highlights to my hair, worked on my extensions, had a body wax, got a new manicure and pedicure with coral pink polish, for a nice beach look. They replaced and added some extended eyelashes, cleaned up my eyebrows, and after my facial they did my makeup, as they explained the process with each step. They enjoyed teaching me all their techniques and encouraged me to practice them often. The results were more amazing than ever as the girl in the mirror was stunning, and with the new highlights in my hair and amazing make-up, that girl in the mirror was, sexy. I smiled in amazement at how my life had changed so fast, and how great it made me feel to be living as Amy.
As I pulled up to the house, I was surprised to see mother’s car in the driveway and even more shocked to see Grace home from work when I entered the house.
When they saw me, they both gushed, “Oh my, look at you, my sexy girl. They really went all out today on you, didn't they?” Grace and Mom gushed.
Mom spoke up and added, “Yes they did, my little girl is all grown up.”
Having my mother and wife fussing over how good I looked as a woman, was a new feeling which made me smile.
“Why are you two here?” I asked.
“Well your mother wanted to meet Tony, and I wanted to be here to make sure my girlfriend is ready for her big weekend. It’s your first time spending the night with a man, and I want to make sure you’re ready.
Mother and Grace sat on the couch in the living room as they had me model my outfit for them. They both liked the pink sundress and wedge sandals and said it would be perfect for the dinner on the beach, which apparently is what Tony had planned.
"With all that exercise combined with that diet you have been on, is certainly paying off. Your figure is getting slimmer and more girlish every week. Those tight outfits and bathing suits, will look much better on you now, " Grace said with a happy expression.
Grace and mother helped me dress for dinner as they handed me on piece of clothing after another. Grace helped put the silicone inserts into the new bra as I was pulling up my panty girdle over my caged boy parts. It worked as I was completely flat in front with no chance of anything popping up, so to speak. I saw mother watch as I expertly slid on a new pair pantyhose and finally stood before both.
"Very nice figure, and lovely lingerie you picked out for her, Grace. I stepped into the silky black dress that fell to mid-thigh. Mother zipped me up as Grace adjusted my breast in the dress. Without being told I walked over to the closet, picked up my heels, and as if I'd been doing it all my life, easily stepped into the four inch heels.
I stepped in front of the mirror and took in the pretty girl that was looking back at me, as Grace and Mother adjusted my outfit to insure it was perfect. I put on all the jewelry along with the new chandelier earrings, we purchased this week. I touched up my makeup, and hair, and applied some fresh lipstick and was ready for my weekend.
While I was dressing, my mother and Grace finished packing my things. When I was ready, I turned and took a deep breath, "I'm as ready as I'll ever be."
Grace handed me a gift wrapped bag, which contained an expensive purse and card. The card said it was from Grace and my mother. Inside the purse was my makeup, several packages of condoms, and 5 tampons, and nothing else. They giggled as I held the condoms in my hand and said, "This isn't funny. I'm not ready for anything like that."
"Well ready or not, you might not have a choice sweetheart, and you need to be careful," mother said as they both giggled.
"That's not funny, mother. Where is my phone and wallet? I will need them," I said.
Grace whispered and said, "No sweetheart, you won't need them. This weekend you will have no money, ID, or phone, which will make you completely dependent on Tony. Your mother and I discussed this and, we think it's best for you to fully understand what it means to feel dependent on a man, and completely vulnerable. Trust us, it is for the best.
There is another item we put into the side zipper pocket. You will find 3 sedatives you can take if you find things are making you too anxious. This time you should only take half a pill, in order to be more alert and remember everything. Only take them if you really need them because, it's best for you to be fully awake so that you can remember everything this weekend."
I stood there in shock with my mouth open as Grace told me that last detail. That's when the doorbell rang and I quickly put the condoms I was still holding back in the bag and answered the door, as Grace instructed. Mother and Grace remained on the couch as I led Tony into the living room.
"Hi Tony" Grace said.
Grace smiled and said hi to Tony and then said, "Amy, aren't you going to introduce Tony to your mother?"
"Tony I'd like you to meet Carol, my mother. Mother, this is Tony."
"Hello Tony, lovely to meet you. My daughter has told me so much about you and it's a pleasure to meet you."
I stood there feeling humiliated, scared, and shocked as I listened to my mother and my date discuss me as her daughter, and how I told my mother things about him. It was like an out-of-body experience as they spoke.
"It's nice to meet you as well, Carol. Your daughter is quite lovely and special, as I'm sure you know." Tony said shaking mothers’ hand as they met.
Grace took the opportunity to speak and said, "Oh yes, Amy is very special and has been talking about this weekend all week-long. She is so excited, aren't you Amy?"
Feeling trapped and not knowing what to do or say I just smiled and shyly nodded my head.
"Well that's good to hear because I have a fun weekend planned, and your little girl will have a great time, I'm sure," Tony said.
"That’s wonderful, she deserves someone nice like you Tony. Please take good care of her," mother said.
"Yes, we want our little girl to have a good time and experience all types of new things," Grace said, giving me a hug around the waist.
Mother held up her phone and said, "You two make such a cute couple, can I please get a few photos of the two of you?"
Tony and I stood for several photos of us and then mother took a few of just Grace and I as well as the three of us together. Embarrassing me even more, mother asked Tony to take a few of her and her daughter and then a few more of mother, Grace and I together.
"We have dinner planned and we should get going. Do you have some bags I can bring out to the car?" Tony asked. Grace pointed to the 3 bags and Tony brought them out to the car as I stayed behind with my Grace and mother.
"Just have fun, baby and do not hold back. Enjoy yourself and remember if anything happens, it's just sex, nothing else. Unless you start having feelings for him in a special way, whatever happens is just physical, nothing more. Let yourself go and enjoy everything. Your mother and I know what it's like, and as woman we can enjoy sex without emotional feelings, so enjoy yourself and remember that our feelings will not change if anything happens, as we are sure it will. Do you understand, honey?"
Half in shock I looked at both of them standing in front of me smiling and I said, "Yes, I understand. But this is all new to me, and I'm not sure how to feel."
"Don't think or feel, just go along with whatever happens and live in the moment. Don't think, just do. You'll understand and I'm sure it will be fun. Now here comes Tony, kiss us goodbye and enjoy this new experience and the weekend."
As I left with Tony, I looked back at Grace and Mother and felt as if I was being led away from the woman I loved, to a new experience that was out of my control. I saw them chatting as the door closed.
"Poor dear, she looks so frightened," mother said to Grace.
"Yes, but after this weekend she will have a much better idea what living as a woman is really all about. I guess we will have to wait until Monday to see if Amy is really here to stay," Grace said.
"With a man like Tony, I would agree. You do not get much more manly, that's for sure. He is quite handsome and so muscular. I have to admit, they do make a cute couple."
"Yes, they did. Please have Tony take some pictures and send me a copy of those photos, I'd love to see them tonight," Mother said as they saw us drive away.
In the car Tony started the conversation. "I have to say that Grace has been very supportive of us, and your mother is very nice. I think it's wonderful how much they love you."
"Yes, they are very special."
"I think you're going to have a fun weekend, baby. I have some fun things for us to do and we start with dinner on the beach at sunset, at a very romantic spot I picked out for us tonight."
As he spoke, I noticed how my legs were crossed and my skirt was half-way up my freshly waxed, smooth feminine legs, and the new purse on my lap, which made me feel weak and submissive next to his big muscular man. I was quiet and didn't say much feeling scared, and nervous about being alone with him all weekend.
"Amy, I can tell you're nervous, but I want you to relax and just enjoy the weekend. Grace told me you enjoyed our last date, and were looking forward to seeing me again, so there is no use in being shy with me, OK?"
What had Grace told him? He was under the impression I was looking forward to being alone with him, but the truth was that I was petrified, and this really was Grace's doing, not mine, but I couldn't say that to Tony because of what Grace had told him, and besides I know he wouldn't believe me anyway.
He was very attentive and a perfect gentleman as he took my hand and led me to the restaurant. I noticed several men turn their heads as I walked by, which gave me a little more confidence, as I tried to keep up with Tony's long strides.
He held my chair as I sat down and then he leaned over and kissed me sweetly on my glossy pink lips. "I wanted to get that out of the way, to break the ice. It will make things easier for both of us as the night progresses."
He ordered us some Cosmopolitan's and they went down easily. After a couple more I was much more relaxed and started to enjoy the surroundings as we sat in the only a few yards dimly lighted restaurant, which was only a few yards from the ocean. The view of the city and ocean was exciting as we both watched several expensive boats sailing in clear view. It was a romantic setting and I found myself enjoying myself.
I finally had the courage to start a conversation and said, "This is a lovely restaurant, do you come her often."
"Not too often, only when I'm with a sexy girl like you that wants to spend time with me," he said as he ran his foot up my leg under the table.
"Well, I love the view and these drinks have helped me relax. To be honest, I was very nervous about all this, but now it feels much better, in fact I'm enjoying myself," I said.
He smiled, "That’s perfect, this is just the beginning, and by the end of the weekend I'm hoping you will feel much more comfortable being around me. And I'm also hoping that after this weekend, you will want to spend even more time with me. To be honest with you, since our last date you're all I've been thinking about, and when Grace told me you felt the same way I was so excited. I could not wait for this weekend to get here. I'm hoping you enjoy the rest of the weekend as much as I am. Whatever you want this weekend is yours. It's my way of thanking you for going to dinner with me last week, it really was fun," he said smiling. I smiled and felt warm and tingly as he said all those sweet words. I never dreamed I'd hear those words from a man let alone a hunk like Tony.
I had a small salad and some grilled fish with another drink, and after sunset he paid the bill and helped me walk back to his car, where I carefully got in feeling quite tipsy, no kind of drunk. He drove us to his condo and took me up to his condo on the 19th floor, which had a wonderful view of the ocean. After he brought my bags into the bedroom, he led me out to the large outdoor deck, onto a double wide lounge chair where I laid down and enjoyed the view. "I'll be right back, just relax and enjoy the view," he said.
I was so relaxed and enjoying myself and forgot about all the things that I was worried about. I heard Tony open the door and saw him carrying a bottle of wine and two glasses. He poured two glasses and handed me one, as he snuggled next to me on the lounge chair. He maneuvered his arm around my shoulder as I leaned into him which gave me another warm feeling. I felt safe and protected at that moment, and I to my surprise I really enjoyed how that felt. I smiled to myself and took a sip of wine.
We lay there quiet as he stroked my arm with his strong hand, and I continued to lean into his muscular body. I realized, that there were a thousand girls that would love to be in my place at that moment. After a while I moved a little and turned my head to look up at Tony, who took that opportunity to pull me into him for another kiss, but time it was much stronger and much more passionate. At first, I resisted, but only for a few seconds until I gave in and kissed him back. Yes, I kissed him back, and I was enjoying how he was making me feel and I didn't want it to end!
Before I knew what was happening, Tony led me to our bedroom while we continued to kiss and feel each other's body. His strong hands on my body was amazing, and feeling wanted and desired like that, was a big turn. When we broke our kiss, I realized we were now sitting on the edge of his bed, when he stood up and took off his shirt revealing his muscular chest. I gasped as he unbuckled his pants and they fell to the floor. Before I had the chance to sober up, he took off his underwear, revealing that massive cock. I just stared in wonder, comparing it to my little appendage now locked away.
With an excerpt ease, Tony laid on the bed and pulled me next to him and started to kiss me again. The room was dark except for the moon light, coming from the wall of windows in front of the bed. We kissed and hugged each other as I laid next to this gorgeous naked man.
Tony moved back, and with his arm bent and his head on his hand, looked at me and smiled. "Amy, you are amazing, and really turn me on more than any other girl I've ever been with. Besides being so pretty and feminine I really enjoy being with you, and our chemistry is obviously strong. I've been with lots of girls, but you are so much different. The feminine way you move and that sexy voice, drives me crazy. I also loved it tonight, when all those guys were checking you out at the restaurant. I was proud to be with you as your date, and the fact that nobody had a clue what's hidden under your panties."
Tony looked deeply into my eyes as he continued to tell me how pretty I was and quickly unzipped my dress, and was now pulling it off me, as I moved to help him. I was now laying there in my matching yellow bra and pantie brief. I moved my hands up to cover my bra, because I felt self-conscious as he stared at my body. His touched the lace of my bra and to my utter dismay, his other hand touched my panty, where my clity cage was hidden.
He smiled and said, "Thank you for wearing my gift. I should explain why I sent it over for you to wear," he said as he pulled down my panties exposing the pink cage.
As he touched the device through the nylon he said, "I guessed at the size and picked the smallest one I could find, and it looks like I got you the right size, as it really conceals your clit. There was a couple of reasons for this and the obvious one is it conceals things and prevents any accidents that I cannot afford. But the main reason I like you wearing it is because, even though I love girls like you, I don't really enjoy seeing your clit. I just enjoy knowing it's there, but what turns me on is your presenting as beautiful woman and knowing you have no control of things. When you are like this, I see you as a complete woman, and will treat you accordingly. When you look as sexy as you do it just drives me wild, and when I hear that sexy voice, I'm in heaven. I really want to keep you like this and spoil you, if you'll let me."
He didn't give me a chance to answer as he leaned over and kissed me hard and played with my bra and panties and nylons. I enjoyed the kisses and his attention, and I didn't even mind his demand of me wearing the clity cage. I didn't realize it until my hand was now touching his large cock, Tony had expertly moved my hand there while we were kissing without my knowledge.
"Play with it Amy, please," he said as I took it in my hand. It was so hard, hot, and big, like nothing I had ever felt before. In comparison, mine was just a clit and nothing like his massive tool. For some reason, I wasn't grossed out and allowed myself to be in the moment as remembered what Mom and Grace told me, that I was Amy this weekend and to act as Amy would behave with her date. I did. I held him as we kissed and slowly found myself stroking him, as he got hotter and harder. I liked it. I liked the control I had over this huge man and let myself just enjoy the moment.
We continued to kiss, and he continued to rub my bra as I stoked him for a long time, until Tony could not take anymore and gently pushed me down onto the bed. He placed a pillow under my head and straddled me as I looked up at this massive man now on top of me.
"Amy you really got me excited and I want you," he said as me positioned himself so that my head was propped up and he towered over me with his hard cock in front of my face. I knew what he wanted and realized that if I didn't stop things at that second, that from that moment forward my life would change. If I let him put that in my mouth, I knew I would forever become a cocksucker, and something I can never take back.
I was apprehensive and trying to avoid the inevitable until Tony's testosterone took over. He could not wait any longer and moved himself up on the bed until the tip of his cock was sitting on my bottom lip. He leaned forward and I felt his very hard cock start to spread my lips. The pressure forced me to give in, and his weight forced my mouth opened just a little, but enough to encourage him to push forward.
Almost instantly the head of his cock was now inside my mouth resting on my tongue and I realized I had just past the point of no return. I felt my mouth open a little more and Tony took over and did the rest. I looked up into his eyes as he started to move his cock in and out of my mouth. He was fucking my mouth and I was giving him a blowjob, I had become a cock sucker and something I could never take back. I tried to relax as he looked into my eyes and continued to move his cock in and out of my mouth.
"Oh, that's it Amy. Just like that, don't stop," he said as he let out a small moan.
I felt my boy bits start to get excited, but the cage instantly sent a pain signal to my brain and my clity instantly stopped getting hard. I put all my concentration to the cock in my mouth and tried to focus on everything that was happening.
My tongue now ran up and down his cock as I explored every nook and cranny and became very familiar with Tony's cock. This went on for well over five minutes when he looked down at me again and said, "I'm close Amy, get ready baby I'm about to come in your beautiful mouth. I want you to swallow me baby, take all of me," he said as I felt him grow and start to pulse inside my mouth.
The first squirt of cum hit the back of my throat, and I had to either swallow or choke. I swallowed the first load, and the next seven, that he shot into my mouth. He came so much that his cum quickly filled my mouth and poured out over my lips and face. He finally stopped shooting his come, but he continued to fuck my mouth for several more minutes, as he let out cry after cry of satisfaction until he finally stopped and let it rest inside my mouth.
I looked up at him and wondered if he would ever take it out of my mouth. He had such a satisfied look on his face and smiled, as he looked down at me and said, "Wow, that was the best blowjob I have ever had. Amy, you're amazing, thank you."
He finally removed his cock and laid down next to me on the bed and continued to look into my eyes. He took his two fingers and scooped up the come on my face that I wasn't able to swallow and fed it to me as he continued to look deeply into my eyes.
"That is so sexy, Amy. I can tell you enjoyed that darling, and I'm so happy you like my cum, and I want to give you so much more." He leaned over and kissed me deeply, and once again he played with my padded bra as I enjoyed all of his admiration and affection.
Yes, he was right, I did enjoy it and wanted more, but part of me questioned what I was doing and what I had become. I realized there was no going back, and I had to accept the way things were, and try to accept and enjoy the moment. I wondered what Grace would think of me, and realized that at this point, after telling her she could see other guys, it probably would not matter anymore.
He held me as we lay there and we both drifted off to sleep in each other arms. We were exhausted and I slept soundly safely wrapped in his strong arms and would stay that way for many years to follow, as husband and wife…
…but that story has yet to be written
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Comments
I'll admit I didn't read all of it, but...
I'll admit that I didn't read this novel length work in its entirety, because it's not my usual kind of story, but I have to say I'm impressed with the 2/3 I did read. The prose is very accomplished; but what surprised me was that this was the first forced femme/sissy cuckold story I've ever looked at that really explored the wife's motives + feelings for turning her husband into her submissive full-time girl. You made it all quite believable, and made Grace into someone I could halfway empathize with instead of her just being the standard Saturday morning cartoon show villains that seem to stride so irredeemably cruelly through this genre; which I know is a thrill for some readers but it weirds me out when female characters are portrayed as evil-for-the-sake-of-evil- as if the author really doesn't like women much in spite of their obvious attraction to the trappings of femininity. And even though she keeps the upper hand in their redefined relationship it does sound like after her initial resentment subsides Grace genuinely wants Amy Rose to be happy. Mom still seemed a little weird with her interest in the lurid details of her new daughter's sex life, but even she was more 3 dimensional than I usually see in stories of this type.
Amy Rose's journey to acceptance of her new role in life was handled very credibly too; for someone who unlike me started out with reservations about being a cocksucker, and I have to say I wouldn't mind having a guy like Tony treat me like he did Amy, although I'd prefer to skip the little weenie cage and go right to castration + hormones; since I doubt a "tranny chaser" like him would be happy with his special girl having GRS.
I'm sorry, was that too much information? I'm afraid I do that sometimes.
~but anyway... WELCOME, NEW AUTHOR! Veronica
We now return to our regular programming:
https://www.youtube.com/watch?v=qTl00248Z48
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Thanks Veronica!
Veronica, After reading your review, I can't wait to read some of your stories. I love the way you explained your feelings on the story and the constructive ideas. Nice to meet you and thanks for making me feel welcome :) - Cindy
Cindy Johnson - [email protected]
Nicely Done
For the last few days I've been thinking about writing a similar story. Now I'll have to up my game.
A very good first effort!
Jill
Angela Rasch (Jill M I)
Impressive, detailed and long...
Wow. I was hoping that Tony had a key to Amy's device and would reciprocate the blowjob. Good effort.
Regards,
Donna