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By Patricia Marie Allen
or how I became a cross-dresser
We’d been married for about five years and I was very much in love with my wife. I saw her as a sexy desirable woman who was smart, capable, practical and confident in her own-self. I was sure that she would do any reasonable thing I’d ask of her. All I wanted desperately was to make her happy and I was sure that she wanted the same for me.
Valentine’s Day was coming up. Each year, I tried to get something I thought she’d really like. I ran the gamut of flowers and candy until that was just too mundane. ‘This year,’ I thought, ‘I’ll get something that tells her just how attractive and sexy I think she really is.’ To that end I found an erotic lingerie shop online and after stealthy checking out the size of her lingerie, I ordered a diaphanous little number. It was pale red, with spaghetti straps, a built-in pushup bra, a loose gown that would strike her mid-thigh and it came with a matching bikini panty.
The company promised discrete packaging, so I had it sent to me in care of my work address. It arrived about a week before Valentine’s Day. I sneaked it into the house and when Jenny was out on Saturday morning, I took it out and luxuriated in the feel of the fabric. A lot of times lacey clothing ends up scratchy. Not so with this little nighty. The fabric was soft and sensual to the touch. ‘I wonder what it would feel like to wear something like this,’ I thought.
I quickly boxed it up and wrapped it in red wrapping paper with white hearts on it. Back out to the garage and into the trunk of my car, hidden in with the emergency supplies I kept there. I waited until the fourteenth to bring it back in and put on the shelf in my closet.
That evening, we went to dinner with, it seemed, every couple in the city. I’ve got to give the waitstaff props. Even with the overflow dinner crowd, the service was good and the meal was excellent. The bottle of wine we split put us in good mood. As we prepared to go to bed I retrieved the nightie.
“One last gift for the love of my life,” I told her as I handed to her.
She was all smiles as she sat on the edge of the bed and opened the box. Her face fell when she lifted the nightie out of the box.
“You’ve got to be kidding,” she exclaimed. “When have you ever seen me wear something like this?”
She had me there. In the summer, she slept in a long tee-shirt and what could easily be men’s boxers except there was no fly and in the winter, it was flannel nightgowns knee length or longer.
“I thought since it was Valentine’s Day, something sexy would be in order.”
“Michael, it’s the middle of winter. Didn’t you notice the snow coming down as we drove home? If I wear that to bed, I’ll freeze my rearend off.”
“You wear that to bed and I’ll warm you up in short order. Feel the fabric. It’s positively sensuous. I thought it would really enhance our performance on this romantic night.”
“Well I’m not wearing it. If you think it will ‘enhance our performance’ all that much, then you wear it. You can freeze you hinny if you want.”
“But I thought…”
“I’m serious, just try it. After one night in that thing, you’ll see why I go for flannel in the winter.”
“Me wear it?”
“Sure, it’s a win-win. You get your enhanced performance, and I get to prove to you just how impractical something like that is.”
“You’d freak if I did.”
“No I won’t. Go ahead, it’ll be a little kinky and I won’t tell if you don’t.”
I paused, looking at her and dealing with warring thought patterns. I was a little angry at the rejection of the perfect Valintine’s gift. There was some thought to do it just to prove her wrong. Thinking a little clearer, I’d just about laid to rest any reason to do as she suggested when she spoke again.
“What’s the matter? Afraid I’m right and if you wear it you’ll get frostbite on your tush?”
With that, I snatched it up from where she’d tossed it on the top of my dresser and storm into the master bath.
‘I’ll show her. Frostbite on my tush? Ha! The furnace never lets the temp get below fifty-five and we have two blankets and a comforter on the bed. I could sleep nude and still be too warm.’
I plunked the nightie on the counter and attacked my teeth. I brushed the so hard and vigorously that my gums were sore when I was done; all the while looking at the nightie. I really went all out for that gift. It wasn’t some cheapo Fredrick’s of Hollywood knockoff. This was a top-quality garment by a leading fashion house. ‘Freeze my tush indeed!’
I angerly stripped down and separated the panty from the nightie and pulled them up my legs. It was a little tight, but not uncomfortable once I tucked everything inside. You’d think that putting on a nightie would be pretty straight forward, but the built-in bra made it a bit of a mystery. I was familiar with bras; I’d taken enough of them off women in my time. They either had a hook-and-eye clasp in the back or between the cups in the front. But this was part and parcel with the garment. The material in line with the bra cups was more substantial and quite stretchy. I decided to just bunch up the nightie and stick my arms up into the bra portion; then pull it down.
Easier said than done. I struggled with it. At one point I thought I was stuck trying to get it past my shoulders. I finally managed one shoulder at a time. It seems my chest must be a bit larger than Jenny’s; the bra was quite tight, pushing my flabby pecs flat in a most uncomfortable way. The top of the cups seemed to have a little room, so I reached down and pulled the flab up into the cups. That was a lot more comfortable. The bottom of the cups were padded and pushed up the flab to pretty much all the way to the top so that there was a swelling that kinda looked like boobs.
I looked in the mirror over the sink. I wore my hair a little long in a retro style that I usually brushed behind my ears, but with the struggles getting into the nightie, it was hanging over them. That gave the reflection an interesting look. What with the swelling over the bra and my hair covering my ears; if it hadn’t been for the fact that it was my face, it could have been a twenty-something young woman looking back at me.
I smiled at myself.
‘Well, Mike, my old friend, you wondered just what it would be like to wear something like this; now you know.’
Strangely, it gave me a little thrill. I was inexplicably happy with the reflection and the feel of the garment; panties, bra and all. There was something going on in my psyche that seemed to satisfy a need I hadn’t known I had.
I shook myself from my reverie. It was time to show Jenny that a person could wear this and still be comfortably warm. I marched into the bedroom with a smug look. I struck a pose and looked at her as if to say, “Well?”
She was already in bed with that detestable flannel nightgown. She got wide-eyed when she saw me.
“Ohm’god, you did it. I didn’t think you’d go through with it.” She paused and studied me a moment. “Are you sure that you didn’t buy that for yourself? It looks really good on you.”
“No, I didn’t buy it for me. I’m wearing it just to show you that it’s not too cold for the middle of February.”
She got a naughty look in her eye and smiled a wicked smile.
“So what do you think? Do you like it? It’s definitely you.”
I didn’t know how to answer. If I said that it was just clothes and I didn’t think anything of it, which I would have liked too, it would be a lie. She’d probably see right through it. She was right. I’d seen it in the mirror, this nightie was great on me. I decided to tell the truth, though I did try to mitigate the strength of my answer.
“Actually, I don’t know why anyone would object to wearing this. The fabric is soft and sensual. It even makes me look sexy.”
“You got that right.” She grinned as she said that. “Come hither, my sweet,” she continued, turning back my side of the bed.
Over a late breakfast, she asked a question I’d hoped she wouldn’t.
“So, do you think you’ll be wearing that nightie again?”
“Why would you ask that?” I asked, sidestepping the question.
“Because, it looked really good on you and it did ‘enhance’ your performance last night.”
I blushed three shades of red. She was right. I was in rare form and not only me. She matched my ardor in every respect the result being a very satisfying coupling.
“I … I don’t think so. But I’d like it if you would. I’ll have you know that there’s no frostbite on my tush.”
She smiled.
“Somehow, I don’t think the result would be the same if I wore it. You might get off on it, but on me, I don’t think I would so much.” She grinned that wicked smile she gets and continued, “Feel free to wear it anytime you get the urge.”
She came over and kissed me a sensuous kiss.
“Maybe I’ll see if I can find a matching robe. You could wear it on Fridays and if you just put on the robe in the morning, it would keep me, and I think, you in the mood and we just might get lost for the weekend.”
We hadn’t had a prolonged weekend of love-making since our honeymoon. I couldn’t tell her but the prospect excited me. I don’t know if it was the thought of such a weekend or if it was wearing that nightie for the weekend that was responsible for the excitement.
I had a walk and driveway to shovel so I bundled up and went out to take care of it. As I worked, I pondered my wife’s sanity. What kind of woman invites her husband to wear something so feminine? Then I was taken with what kind of man wears the blasted thing and likes it? ‘Maybe we’re both nuts.’ That thought put my reasoning process in neutral. Then out of nowhere I thought, ‘Are you going to wear it on Friday like she said?’
I’d have thought that I’d get involved with my job and forget all about my aberrant Valentine’s Day, but no. In every job, there’s a certain amount of slack time. Sometimes you have to wait on someone else for something, or on a job to print and every job has break times and lunch built into the day. Then there’s those times when your mind just wanders for no reason. All of the above happened through that week. I’ll give you three guess what was on my mind during those times and the first two don’t count.
I was going crazy. I was obsessed with the idea of wearing that nightie. I called to mind the feel of the fabric and how I looked in the mirror; how I felt seeing my feminine persona.
When I came home on Friday I was fit to be tied. When Jenny came in, she picked up on it. As usual I had been home about twenty minutes when she came in. I was in the family room with the TV on and a beer in my hand. She stood in the door watching me.
“What’s up with you Mike?” she said, finally. “You keep staring off into space and when you’re not doing that you’re all fidgety and seem to be nervous about something.”
I didn’t know how to answer. I couldn’t tell her that I’ve been obsessing over the prospect of wearing the nightgown again this weekend. But I couldn’t claim it was nothing or some other lie. She knew me too well. The problem was I wanted to, not just this weekend either, from Sunday night all the way through last night, I’d resisted the temptation to just put it on and get in bed.
“I’m concerned about what’s expected of me this weekend.”
“I don’t understand, expected of you by who?”
“It’s that nightie. Last time you said that I should wear it on Fridays and not take it off the whole weekend. I’m concerned that you might have been serious. Wearing it the first time was a mistake. Men shouldn’t wear things like that.”
“You mean because it’s a woman’s garment?”
“Well yeah.”
“You are aware that women wear men’s clothing all the time. One of my roommates in college wore men’s boxers for underwear. She just sewed up the fly so it wouldn’t hang open. My sister wore men’s high top tennis shoes going to high school, there’s no end to the examples of women in men’s clothes.”
“What are you trying to tell me?”
“If you want to wear it to sleep in, then go ahead and do it. If you do, I’ll think you’re crazy. Not because you’re wearing a woman’s nightie, but because it’s the middle of winter and you’re wearing lightweight sleepwear when something heavier, like flannel would make sense.”
“You think it’s alright for a man to wear women’s nightwear?”
“Nightwear, daywear, outerwear, underwear; it makes no difference. Clothes are just clothes.”
“You make it sound like if I think I wanted to, I could or even should buy myself a whole wardrobe of skirts and dresses and wear them whenever I wanted to.”
“Pretty much. But I don’t think you’re ready for that just yet. But given your reaction to the nightie, I’d say you might enjoy laying in a supply of panties and maybe camisoles to wear as underwear. That and a small selection of nighties. You shouldn’t limit yourself to an overly sexy nightie. There are plenty of nice satin finish nightgowns available to the woman with that inclination,”
She was serious. That comment blew my mind. Two things; one, I couldn’t believe she would say that without it being a tease. Two, the very idea of wearing something like the panty that came with the nightie daily made me want to drop everything a run, don’t walk, to the nearest lingerie store for the purpose of “laying in a supply of panties.”
I left the conversation there. It was my night to cook, so went to the kitchen to get started on the sides to go with the roast I put in the oven when I came home. Jenny, headed upstairs to change out of her work clothes.
Nothing more was said about the nightie or exploring the delights of lingerie on a daily basis Nothing was said, but the thoughts ricocheted around my brain like a pinball hitting all the bumpers for a grand slam score. The evening was strangely normal. We watched TV; critiqued the inconsistencies in the story lines. We had a little desert. About eleven, we went to bed; taking our turns in the bathroom. In short, it was just an ordinary Friday night; everywhere except in my head.
The only other thing that was odd was on the usually empty hook next to my robe in the bathroom, was that nighty. I didn’t hang it there; it had to have been Jenny. It was the first time I’d seen it since the day after Valentine’s Day. It gave me pause. My hand reached for it trembling, but stopped short and withdrew when I forced my mind to think clearly.
I couldn’t let her know I had been tempted. I schooled my face as I entered the bedroom and slipped into bed. After a quick kiss and a mumbled, “Goodnight,” I turned my back and feigned sleep. But in truth, my eyes remained open looking at the bathroom door. I couldn’t ignore the fact that through that door, hanging on a hook was that nightie waiting for me. Jenny put it there, I knew it; it was an obvious invitation to wear it again. I forced myself to modulate my breathing to simulate a sleep state. My breathing rhythm was at odds with my heartrate; somewhere in the mid-90s. I don’t know how long I kept that up before exhaustion claimed me and I actually did sleep.
I was heading out to the hardware store for supplies I need to complete a project I had going in the basement. I was about to leave when Jenny told me that she needed to go into work for a couple hours and asked me to swing by the dry cleaners on the way home. As I pulled into the parking lot of the cleaners, my eyes fell on the business next door. I’d been to the cleaners a hundred times or more and never once paid attention to what was next door. But that day the words painted in golden script on the window glass jumped out at me and demanded my attention.
They read: “Lingerie and More.”
I sat in the car for many minutes trembling. After a time I pulled myself together with a little self-talk.
‘Come on dummy. Just pick up the dry cleaning and go. They’ve got nothing in there for men to wear, and you’ve already demonstrated that you buy for you wife at your own peril.’
I was a bit shaky when I went into the cleaners, but I managed to get the job done. With the dry cleaning in the back seat, I backed out of the parking slot. Slowly I drove in front of the lingerie store. There was a parking spot open just past the store. Without making a conscious decision to do so, I turned into it. Again, I sat staring at the displays in the window.
‘It won’t hurt to just look.’
I entered the store in a kind of trance. My mind was filled with the memory of wearing the nightie and the feel of the panty that went with it. The store was wall to wall delicates. A sea of lace and satin in a rainbow of colors. I wandered into the midst of it. A voice broke the spell.
“Welcome to Lingerie and More. Can I help you find something?”
I turned and there was a middle-aged woman smiling at me. I swallowed hard. I wanted to say, “I’m just looking.” But even the thought of saying that sounded perverted. What kind of a man comes into a lingerie store just to look? A pervert, that’s what kind of man.
“I… I’m looking for some special panties and matching camisoles.”
She smiled a knowing smile.
“Do you know your… what size you need?”
I recalled the size I’d found when ordering the nightie.
“Ah, the panties should be a size 7.”
She smiled again.
“And the camis?”
“I’m not sure.”
“Knowing the panty size, I should be able to estimate the size. You used the plural… how many sets did you need?”
“Well, ah, I’m not sure.”
“Let’s leave that for now. If you’ll come this way, what you’re looking for is right over here.”
After picking up a basket, she led the way to a small alcove that had three racks of panty and camisole sets. There were some in white and some in black plus a miriad of pastels in every hue imaginable. White for at least one was an obvious choice. Black seemed to be as well. But the rainbow of pastels seemed call to me.
“Pick out the panties you want and I’ll get the matching cami for you,” she told me.
I quickly put a white one and a black one in the basket. I noticed that the camisoles she got to match them were adorned with a lace panel over the bust line. It took a bit longer for me to decide on the colors. There were eight colors in all; lilac, peach, yellow, lime, purple, blue, red and pink. Each of them had a band of lace a half an inch wide at the waist and the leg holes. In the end, I couldn’t decide and just got one of each. Counting the black and white ones, I had ten sets in all.
“Do you need any bras?”
‘Bras?’
The question must have been written on my face. I hadn’t even considered bras.
“With these nice camis, a plain bra wouldn’t do.”
‘Ten bras? My wife doesn’t have ten bras.’
“I wouldn’t suggest ten bras. I was thinking that two white, a black and two nude would be in order,” she said putting to rest the idea of ten.
Unable to think, I just nodded.
As she led te way to the bras, she asked, “Do you know the band size?”
“Thirty-six B, I think.”
She paused and looked at me for a moment and nodded. A few steps more and we reached the rack with bras. Again there were many colors, though not as many as panties. She searched a moment and showed me a white one that had nearly the same lace as the camisoles.
“Isn’t this one nice?”
Again, I just nodded.
“We have it in all these colors, but as I suggested,” she started putting bras in the basket, “two white, one black and two nude should do for a start. If you find you want more, you can always come back.” When she had the five bras in the basket, she asked. “Is there anything else?”
She already had more in the basket then I thought I’d ever need. Heck, one pair of panties was more than I’d ever thought I’d need.
“No, not right now.” ‘Now why did I put it that way?’
She headed toward the front of the shop. At the register, she began ringing up the items. The total floored me. It came to just over four-hundred dollars.
“I’ll give you the new customer discount; twenty-five percent.”
That knocked the total down to about three-hundred dollars. Too embarrassed to do otherwise, I got out my credit card and paid for them.
“You’ve been such a good customer; I’d like to give you a little present.” She reached under the counter and brought out a small box. “These are to enhance cleavage.” ‘These’ were silicone quarter moon shaped blobs. She took one of the bras and inserted them into a little pocket inside the cups. The bra, which was already thicker at the bottom of the cup, now had a lump down there. “You just pull the loose flesh up into the cups and these enhancers will keep it there and give you… the wearer a nice-looking cleavage.”
She put the bra back in the bag and handed it to me.
“Come again,” she said smiling.
I headed for the door, but she stopped me, just before I got there.
“Look,” she said, “the next time you feel the need to purge, you might want to take advantage of our purge insurance. In the back of the store, I have five-by-five lockers you can rent at five dollars a month for a maximum of six months. Just box everything and bring it in. For thirty dollars, you have one-hundred-eighty days to change your mind. That’s just ten percent of what you’ve spent here today. Add in the cost of replacing your outerwear and shoes, not to mention jewelry, it comes down to less than one percent. Well worth it don’t you think?”
I had no idea what she was talking about; purge.
“Well yeah, I suppose,” I stammered.
She pressed a business card in my hand.
“If you ever want to buy some nightgowns, we have a great selection.”
I nodded and opened the door.
Back in the car, I sat dazed. I honestly hadn’t intended to buy anything, let alone three-hundred dollars’ worth. I’m not sure how I made it home; conditioned reflex, I guess. My brain was a whirl of confused thoughts. I was glad that Jenny’s car wasn’t there. I had a chance to stash the lingerie in the trunk. Who’d have thought that three-hundred dollars’ worth of clothing would fit into the extra room in the spare tire well? Well four hundred, but with the discount three hundred.
Inside, I really was a bundle of nerves. I grabbed a beer and went out on the patio. I put my sunglasses on and sat in a lounge chair. I sipped my beer as I willed my heartrate back to normal and my nerves to flat-line into some semblance of normal.
‘I must be out of my mind. Three-hundred dollars’ worth of lingerie and just when will I wear it? Oh sure, Jenny suggested that I go buy them. But I doubt she counted the cost. I really doubted that she thought I’d actually do it. I know for sure I didn’t think I’d do it. But I did.’
Before I knew it I’d drained the beer. I ditched the empty into the container in the mudroom and grabbed another from the fridge. I took it slower with that one. At the rate that I slugged the first one, I’d be drunk when Jenny came home and that wouldn’t do.
While I cooked most weeknights, Jenny was the weekend cook. That left me with too much time on my hands. Suddenly I remembered the dry cleaning. Out to the garage to retrieve the cleaning. After I put it away I got the things I needed for my project. Maybe I could get lost in the project. At a minimum it was be something for me to be doing, besides sucking up beer, when Jenny got home.
I was mostly successful and actually made good progress on my project. It was an hour or so later that Jenny called down from the top of the stairs.
“Hey Mike, I’m home. Did you get the cleaning?”
“Yeah, it’s on the bed. I didn’t know where you wanted it.”
“OK, I’ll take care of it. Dinner in about half an hour.”
Over dinner, Jenny recapped her day.
“I got all the paper work cleared up and I think the boss will be happy with the deal we cut.”
I really wasn’t interested but if you’re a married man you know that when your wife wants to talk, you listen and act interested. So I nodded and said, “Well good.”
“Oh,” she said. “Mom called. She needs my help tomorrow. She’s got that big social after church to cater and one of her girls is sick. So I’ll be gone from about eleven ’til probably around four or five. As a bonus, she’ll send home dinner with me.”
Jenny had worked her mother’s catering business all though high school and college. I think that her mom had hoped she come back and take over the business one day. But in the meantime Jenny couldn’t live on the wages her mom could pay and took her current job instead. But she often helped out whenever her mom was caught short on the weekends.
I had a hard time sleeping that night. I just couldn’t turn my mind off. First of all there was that damnedible nightie on the hook in the bathroom. I could hardly keep my hands off of it as I got ready for bed. Then there was expensive stash of lingerie in the spare tire well of my car.
Where was my good sense when I bought that stuff. I knew I couldn’t take it back. There’s a state law that says once underwear leaves the store it can’t be resold. When did I think I could wear that?”
I know, I know. Jenny suggested that I buy the stuff and wear it. But there was no way she could have been serious. She was just putting me on; teasing. ‘Three-hundred dollars!’
In the morning I didn’t wake up well. I groggily pried myself out of bed sometime after nine. I didn’t bother to get dressed but just put on a robe and went to the kitchen hoping that Jenny had left me some coffee. She was a morning person and no doubt gotten up at the crack of dawn for a morning run; OK, so seven o’clock isn’t exactly the crack of dawn
Good fortune found me and there was coffee and it was still hot. I poured a cup and slumped at the kitchen table. I closed my eyes and sucked up the brew, allowing the steam to bathe my eyelids. I was on my second cup when Jenny came in.
“You look like something the dog dragged in.”
“Unnn; I didn’t sleep well last night. I think I’m a quart low on caffeine.” I hadn’t slept the night before either. Sleep deprivation was catching up to me.
“Get a hot shower. That should make you feel better.”
That sounded like a good idea. I poured a third mug of coffee and grabbed a two-bite muffin and headed for the shower, munching the muffin as I went. I had about half the coffee gone when I got there. I plunked the cup on the counter and got some clean clothes for after and went to hang them on that hook. That nightie was there taunting me. I hung the clothes on the hook my bathrobe usually hung on. I took the offending garment into the bedroom and found a spot on the shelf in Jenny’s closet; hopefully somewhere she wouldn’t notice too soon.
Back in the bathroom, I slugged down the remaining coffee, stripped and got into the shower. Jenny was right. I cranked up the heat as hot as I could stand it and just stood there as my blood streams dilatated and spread the warmth though out my body. I don’t know how long I just stood there before I reached for the shampoo and got on with my shower. It must have been some time because I could feel the water starting to cool before I got out.
I was feeling almost human as went back down to the kitchen. My stomach was growling something fierce. Jenny was there in her catering uniform; black skirt, white blouse and black patent leather flats.
“Feel better?” she wanted to know.
“Pretty much. My stomach thinks my throat’s been cut.”
“I’m not surprised. It’s ten-thirty. It’s been more than sixteen hours since you had a real meal. That’s a long time to go on three cups of coffee and a mini-muffin.”
By the time I rustled up something to eat and sat at the table Jenny was gone.
‘Well, Michael, my boy, you’ve got the house to yourself. So what are you going to get up to?’
That was a dangerous question to ask myself. I knew where I’d hidden the nightie and then there was that stash in the spare tire well in my car. It was like they were singing in harmony. I didn’t know the lyrics or the tune, but I could hear them just the same. Their tune rattled around in my head.
‘Come on Mike, she’s gone for hours. You know you let that woman railroad you. You never really looked at what you bought. What harm can come from looking.’
On autopilot, I got up and went to the garage. I popped the trunk lid and lifted the spare tire hatch. There it was; right where I left it. Three hundred dollars of lingerie in a bag that proclaimed, “Lingerie and More” in golden lettered script. I picked up the bag. It felt damp; maybe it was just the cold plastic. But I wasn’t taking any chances. Three hundred dollars’ worth demanded a little respect. I secured the car and hurried back into the house.
‘I’ve got to find some place safe and dry to store this.’
I wracked my brain for a few as I went to our bedroom. I thought about my closet, but rejected it until I remembered the attic access was in there. We had a plethora Tupperware knock off containers with snap on lids. Leaving the bag on the bed, I went back to the kitchen and found one big enough to hold the loot. I got ready snap the lid in place when I remembered that I was going to look at the stuff.
I turned the bag upside down and dumped the contents on the bed. More lingerie than any man had reason to own. ‘The bra with the extra.’ I searched it out and examine it. The cups had a bit of bone to them kinda like the one built into the nightie. ‘She said this would give me a nice-looking cleavage.’
I had to find out. I quickly stripped to the waist and tried to get that thing on. It took ages and my arms ached by the time I got it hooked. I did as the lady suggested and pulled the loose flesh up into the cups. I turned to look at Jenny’s mirror and was amazed. Cleavage. Real cleavage, not just sorta, but the kind that if I saw it on a woman, it would have been titillating. I’d heard women complain that bras were uncomfortable, but I didn’t find that to be true of this one. I snatched up the white cami that matched the bra. I needed to see what affect adding that little band of lace would have.
Again at the mirror it was even more attractive. The cleavage disappeared into the lace, but was just discernable through it. After staring at it for awhile I took note of how the cami felt. In a word, luxurious. The satin finish nylon was softer, smoother and just plain nicer than any undershirt I had ever worn. That’s what a camisole is, right? A woman’s undershirt.
I was totally disassociated with reality. With no consideration of what should be, or what a real man would do, I became obsessed with the feel of it all and had to try the panties as well. Off came the rest of my clothes and on went the panties. With a little prodding and pushing I got things out of the way so that in the mirror there was a woman with a bad hairdo standing in her lingerie.
Aside from the hair needing attention and the face was my face that was the case. It wasn’t as if the image wasn’t with out flaws; it was close, but not perfect. ‘I wonder just how close I could come to really looking like a woman?’
As mentioned before, Jenny and I are nearly the same size. A deliciously tempting thought occurred to me. ‘If I were to borrow an outfit and add a little make up, I bet it’d get there.’ Oh, I had no allusions that I’d become a beauty queen but I was sure I could achieve a close approximation of an average woman. Jenny’s closet was standing open and I could see outfits hanging there. That deserved a closer look.
I found an elastic waist skirt that was loose and flowing. I always liked the way it moved when Jenny wore it and would walk somewhere with a purpose. I pulled it up to my waist and found a pullover blouse with a scoop neckline.
Back to the mirror; I was pleased with the look. The neckline of the blouse left about a half inch of lace on the camisole exposed. I’d seen dozens of women with that kind of thing and always admired it. I padded into the bathroom intent on doing something with my hair. I bent forward and brushed my hair toward the top of my head, the way I’d seen Jenny do many times. She said it added volume, but what did I know? That done, I gently smoothed it back down and pulled what came over my forehead to the side a little. It looked really pretty good. I’m sure a hairdresser could make it even better, but I wasn’t about to run out and find a salon that took walk-ins; what I achieved would do for my purposes.
I judged my look in the mirror and it needed just a touch more. Jenny kept some make up in a drawer. Oh, I was smart enough to know that full face make up required a skill that women began developing in their early teens. I was sure if I were to attempt it, I’d end up looking like a clown. Less is more; I’d heard that somewhere. ‘OK, just a little lipstick and some mascara. Can’t go wrong with that.’
When I was done, I went back to the full-length mirror. ‘Pretty good, even if I say so myself.’ The problem was I was the bare-foot Contessa. Jenny had a pair of open-toed mules I thought might be made to fit. Trying them on I found they were a little tight. It looked like I should be able to get my foot all the way in, but the leather dragged against my skin and fought that idea. Then I remembered that Jenny had once bought a pair of heals that she really needed, or that’s what she claimed, that were a width too narrow, but when she wore nylons, she could get them on. With that in mind, I got out a pair of pantyhose to give it a try.
As I looked at the gossamer garment, I began to doubt that I could manage to not ruin them. I went to put them back and noticed a pair of black tights. The fabric was heavier, but just as slick. I’d seen Jenny put on pantyhose about a hundred times. I bunched them up and managed to get them up to my waist. The mules were still tight, but the tights did the trick. Aside from my heel extending nearly half an inch in the back they fit well enough. The heel was only about an inch and a half, so they posed no problem walking in them.
Fully feminine now, I needed to feel how the skirt moved when I walked.
The hall from the entry to the kitchen provided about twenty feet and if I turned into the dining room to get back to the entry through the living room I could double that. There was something intoxicating about the swish of the skirt swaying back and forth as I walked. If I was a woman, I’d dress like that every day. ‘If this is what it’s like to wear a skirt, why do women wear pants so often?’
I don’t know how long I did laps, swishing my hips to help the natural swirl of the skirt. I became aware of the fact I was hungry. I stopped in the kitchen. There was some leftover spaghetti and meat balls in the frig. I drizzle of water and ninety seconds in the microwave provided me with late lunch.
The novelty of wearing women’s clothes, sitting at our kitchen table and eating struck me. I emulated the stereotypical female; small bites, daubing my lips with a napkin and chewing thoroughly. The very picture of a young lady. After lunch I trotted upstairs to touch up my lipstick. Climbing the stairs, I reveled in the feel of the skirt on my thighs as I lifted each one to take the next step. A few trips up and down was called for after I freshened my lipstick.
I don’t know how I managed to notice the time, but at three-forty-five I nearly panicked. I dashed upstairs and began divesting myself of the borrowed clothes. When I was down to my, ohm’god, my, lingerie I paused to check out my image. That was nearly my downfall. I heard the garage door opening. I scooped up the lingerie and deposited it in the container and nearly ruined the bra shrugging it off over my head without unfastening it. It went into the container along with the camisole. I quickly put my pants on and pulled my shirt on.
By then, Jenny was on the stairs. No time; the container was tossed haphazardly up on the shelf in my closet. I’d have to get it into the attic later. A quick trip to the bathroom, some tissue to wipe off my lips I tossed the crimson stained tissue in the commode and flushed away the evidence. A quick look in the mirror revealed what a mess my hair was. I finger combed it behind my ears and went to greet Jenny.
“Hi Hun, how’d it go?”
“Pretty good. There were about fifty women there and we were kept hopping during the meal, refilling the drinks. They had a couple of speakers. The crowd seemed to enjoy themselves and they were generous donating to the tip jar.”
“What do we have for dinner?”
“Meatloaf and potatoes au gratin. They probably need to be nuked.”
She seemed to look at my face a little overly long.
“I’ll take care of it,” I told her and headed to the kitchen.
When she came down for dinner it was my turn to look at her. She was wearing some navy capris and the very blouse I’d worn. I worked real hard to not notice. As we ate, she looked at me more often than usual.
“So what did you get up to today?”
“Nothing really hung around the house, did some reading, surfed the net.”
She grinned at me.
“There’s something about your eyes. They look different today. I like them. What did you do to them?”
My mind raced. I didn’t do anything to remove the mascara. I had no answer, so I tried my best innocent look.
“Ah, I don’t know. Nothing really.”
“Do you know why I’m wearing this blouse?”
“No.”
“It was hung in the wrong place in my closet and when I went to move it, it seemed warmer than it should be. Like someone had been wearing it recently. You wouldn’t know anything about that?”
“I, ah, why would I know anything about your clothes?”
She lifted off her chair a little and pulled something out of her pocket.
“Well then, maybe you could tell me how this ended up under the bed.”
She displayed the bag from “Lingerie and More.”
“I've never shopped there. As a matter of fact, I’ve never heard of it. I looked it up online before I came down. It seems they are a specialty lingerie shop that caters to cross-dressers.”
I was finding it hard to breathe. I just couldn’t draw a real breath. She just sat smiling at me.
“Did you take my advice pick up a supply of panties and camis?”
My defenses were gone. Nothing to do but own up to it. I looked down and nodded.
“There was a receipt in the bag. That was quite a hall. Ten each camis and panties and five bras. You wore some of them while I was gone didn’t you?”
I nodded again.
“I notice some tags from the bra. 36 B. You have only a little extra flesh on your chest. What did you put in it to fill a B cup?”
I swallowed hard and found my voice. “The sales lady gave me some silicone things that went into a pocket at the bottom. She said that if I pulled the loose flesh up into the cups, I’d have a nice cleavage.”
“And do you?”
She wasn’t angry, just teasing, so I got brave.
“I think so.”
“You’re not wearing the bra right now are you?”
“No, I changed back.”
“You didn’t have to you know.”
“Well, I borrowed your clothes without permission.”
“Yes, we’ll have to come to an understanding about that. I didn’t see any nightgowns on the receipt. Wouldn’t you like some?”
“I don’t know. I didn’t mean to even buy what I did. I saw the shop and couldn’t resist going in. I only intended to look.”
“But once you were in there, you just had to buy. Where is this shop?”
“Next to the cleaners.”
“If I send you with the dry cleaning will go in again. If you like it all that much, ten sets much, you should get some nightgowns. I’ll bet they have some really cute ones. Since you don’t seem to have any problem with lightweight nightgowns you could get three or four.”
That night while getting ready for bed, I had to show her how my cleavage looked.
The next Friday she had some dry cleaning.
“Mike, can you drop the cleaning off for me after work?”
“OK,”
“It’s in bag by the garage door. Who knows, maybe that shop will lure you in to buy some nightgowns.”
Yes it did and I did and I’m the proud owner of three, four if you count the Valentine’s gift. I’ll likely keep the Valentine’s gift for Valentine’s Day. When I brought the bag in Jenny called me to the bedroom.
“I’ve rearranged my closet. You see all those things to the left, on the other side of the support? Those are clothes you can borrow anytime without asking the others you need to ask individually. What are you doing about shoes?”
“I can get into your mules if I wear hose.”
“As I remember, your feet are a little bigger than mine.
“They are. My heel hangs over just a little.”
“Well, I suppose that will do for this weekend. Let’s go online and see if we can’t find you some of your own that fit properly. Do you want to change now?”
“You’re inviting me to wear a dress tonight?”
“All weekend if you want to. You’ve been wearing panties and camisoles all week and I’m sure you’ll want to wear one of your new nightgowns later, so why not make a weekend of it.”
I opened my lingerie drawer and got out the bra with the inserts. That evening I wore a turquoise sweater dress that kind of hugged me and showed off my faux bust line. Jenny can do my hair and make up much better than I can. She has promised to teach me.
And there you have it. That’s how a Valentine’s Day gift got me to become a cross-dresser.
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Comments
Ahh, the call of pretty things
Nice story. Good imagination. Loved the visuals.
>>> Kay
Thank you
It's a story idea that's been roaming around my head for a couple of years. I was in the doldrums with my other projects and saw Clara's "Then You Wear It". It's based on the same premise, but she made a much longer story out of it and handled it in a totally different way.
Seeing her title jogged my idea to the forefront and I had just a month to get it fleshed out.
Hugs
Patricia
Happiness is being all dressed up and HAVING some place to go.
Semper in femineo gerunt
Ich bin eine Mann
Happy Valentine’s Day, Patricia!
Lovey, frilly sweet tale for the perfect Valentine. Loved the idea of “purge insurance,” and goodness, the wife was a T-girl’s dream!
— Emma
High praise
Thanks for the comment. I only had just over a month to whip this out. You say you work well facing a deadline. Not so for me. There were time in that month when I thought I'd never be able to bring it to a conclusion in the time I had. But then my muse spotted the road to completion and galloped toward it and I just had to hang on for the ride.
Hugs
Patricia
Happiness is being all dressed up and HAVING some place to go.
Semper in femineo gerunt
Ich bin eine Mann
lucky man!
not only to look okay in women's clothes, but to have a wife who encourages his crossdressing!
Indeed
Isn't that the dream we all have?
Hugs
Patricia
Happiness is being all dressed up and HAVING some place to go.
Semper in femineo gerunt
Ich bin eine Mann
Cover Art
My thanks to Eric who called my attention to a discrepancy in my cover art. I was in a bit of a hurry when I did the cover. There's a difference between Present and Gift. A small one, but I intended "Gift". I've got the corrected art up now.
Hugs
Patricia
Happiness is being all dressed up and HAVING some place to go.
Semper in femineo gerunt
Ich bin eine Mann
Funny Yet Enticing
I used to buy my wife's bras...genuinely. I was better at it than she was. Unfortunately she was a lot smaller than me so I couldn't wear them.
Still, I'm on Mike's wavelength!
I'm glad you enjoyed it
I'm a bit better at buying my wife's clothes now than I was in the beginning. Like Mike, I was operating under the false premise that all women would like frilly feminine clothes. Why not? I did, both on her and on me. I've since learned that her taste in clothes, underwear, outerwear and nightwear, is well into the practical side of the ledger.
Hugs
Patricia
Happiness is being all dressed up and HAVING some place to go.
Semper in femineo gerunt
Ich bin eine Mann
Good one Patricia
Mike could have gone either way, at any stage, but most of us on here would have an idea why he did not!
Yesterday I succumbed to the evil lure of the bright red SALE! sign in Roman.
The slightly blurred current avatar photo doesn't show very well the short butterfly pattern sequin top that my lovely missus gifted to me at her last (rare) wardrobe clearout. It can happen. My heart goes out to those not as fortunate.
Teri Ann
"Reach for the sun."
Thanks
My goal in this work was to avoid all the typical forced femme aspects of "Then you wear it" that seem to crop up.
I wanted it to be purely voluntary on Mike's part. Jenny's role in it was just to provide no hindrance for the choices that Mike made. Mike of course had to struggle with what he thought he should do versus what he wanted to do. It's that kind of conflict that makes the story.
Hugs
Patricia
Happiness is being all dressed up and HAVING some place to go.
Semper in femineo gerunt
Ich bin eine Mann
Just how close could I come to really looking like a woman?
That was one of my thoughts many years ago when I first started exploring.
It actually took me quite awhile before I seriously tried makeup though.
The feel of wearing the clothes was enough for quite a while.
Gillian Cairns
I know what you mean
Getting from that first experience of the cross-gender dressing session to trying to make the total package look right is a journey of years, nay decades. My first experience came at nine years of age... first attempt at make-up at twenty-four. I didn't actually do full make-up well until I got the courage to go to Meryl Normans for a makeover. There I learned the fine art of full face make-up. I spent a few years thinking I needed that when ever I went out.
Only to have my daughter tell me that it just called attention to my face. Not my best feature. These days, less is more rules. Mascara, darkening my natural eyebrows and lipstick. Funny thing is at nearly 80 (on the first) I pass with both men and women as a woman. When I go grocery shopping women strike up conversations with me and men offer to help if I'm struggling to do something.
Once, while in WalMart, I needed the restroom and went to the ladies' room. I use the handicap stall because the commode is taller and easier on the knee I broke twenty-two years ago. On exiting the stall, I was confronted by a woman with a cane. Not for being in the women's room, but for using the handicap stall with no apparent handicap. I pull the leg of my capris up and showed her the scar from the surgery and explained that I have limited range of motion. She wasn't impressed.
Hugs
Patricia
Happiness is being all dressed up and HAVING some place to go.
Semper in femineo gerunt
Ich bin eine Mann