Previously
“Wow! My entire face looks better. I love what you did with my eyes.” His hand involuntarily fingered his earrings. He leaned over and gave Jackie a gentle kiss. “Thank you” he said. Jackie returned his kiss with more ardor and said “I’m glad you came over today Mike; it makes me feel pleasantly slutty too.” Jackie tweaked Mike’s panties and kissed him again.
Jackie handed Mike his drink. “To us!” Jackie said. Mike smiled, echoed the toast and they both took a swallow. Jackie put her hand on Mike’s knee and said, “I can’t call you Mike anymore. You’re much too pretty to be called Mike and after what you just did to my penis you deserve a new name. You earned it.”
The story continues
As Mike continued to sit at the vanity Jackie looked around and located Mike’s strawberry blond wig. Bringing the wig and a wig cap over to where Mike sat, Jackie fitted the wig cap to Mike’s head, carefully brushed the wig, and positioned it into place. Facing Mike Jackie stepped back to make sure all was right. A few more brush strokes gave Mike some nice looking bangs. “Strawberry blond really looks good on you. You look pretty and more importantly it makes you look very girly. What do you think?” asked Jackie.
Mike stared, in awe, at his image in the vanity mirror. He shook his head to make his new hair toss about. His gold hoop earrings gently tapped his cheeks as he shook. Stopping to stare longer at the pretty image in the mirror he smiled and said “”That’s a pretty cute girl looking at me.” Picking up his tube of lipstick he leaned forward and applied more lipstick in an effort to create the ultimate image of a woman playing with her makeup. Looking up he giggled and lamented “I’d love to see what I’d look like if I was doing this but was only wearing a chemise!”
Jackie chuckled and quipped “That image (as she pointed to the reflection in the vanity mirror) would make a very interesting photo on your Christmas cards!”
Jackie stepped behind Mike with a brush and two scrunchie hair bands and she quickly created a sexy, double sided, ponytail. Each ponytail stuck out and gave Mike a young school girl look. “There’s so much that you can do with long hair. Look how this shows off your earrings.” Leaning over Mike’s shoulder Jackie gave Mike a quick kiss on his neck. “You’re looking very gender fluid at the moment” Jackie noted.
Looking at Mike’s reflection in the mirror Jackie gave his bra strap a playful snap. “Like I said you’re much too pretty to be called Mike.”
Goodbye Mike
Sitting down on the vanity seat Jackie placed her hand on Mike’s knee and asked “What do you think about ‘Michelle’ with ‘Mickey’ as a nick name?” Mike gave it a thought and said “Michelle sounds nice.” They toasted to Michelle. Michelle leaned over and gave Jackie a deeper, tongue involved, lover’s kiss. Michelle gave Jackie’s panties a reciprocal tweak. It was a beautiful thing.
Jackie pulled on a fresh pair of panties, redid her lipstick, and suggested that they return back to the living room couch for awhile. “Bring your drink, Michelle”. Before exiting the bedroom Jackie grabbed a bottle of nail polish and a pair of the custom pantyhose she had made. “Let me paint your toe nails while we talk and relax, ok? Remove your thigh highs.” Michelle did.
Jackie reached over and gave Michelle’s bare leg a gentle stroking. “Wow, you’ve got some smooth legs! Smoother than mine and I shaved my legs this morning just for you. I guess you are serious about exploring your female side” Jackie said. In reply Mickey said. “I’ve been shaving for years and have recently tried a crème. I’m not sure if it’s worth the hassle but I really like smooth legs and armpits.” He smiled and leaned back on the couch.
Shaking the bottle of blue polish Jackie asked what sort of experiences that Michelle would like to experience, what sort of help she wanted in looking feminine, how feminine did she want to go, how slutty, how permanent should these things be, and a variety of other questions. In short time all ten toes were painted bright blue. Jackie told Michelle that her blue toes would remind her of today. She applied a coat of polish ‘quick dry’ to speed up the drying process. It sure beat having to blow on her toes for five minutes.
Eventually the subject returned to ‘what next’. Michelle sat quite, in deep thought, for a period of time and had painted her own finger nails on her left hand before she spoke. “You know how I said that I want to have sex with you? I meant it. More precisely, because of your porn video, I more precisely mean that I want to have sex with you in me! I want you to fuck me and never tell anyone. That, and other reasons, is why I’m paying you $75k a year. I just want you to be gentle with me.” There was that sound of desperation that Jackie was glad to hear.
Jackie mulled over what she was just told. “No problem, Michelle, I’ll be gentle. I brought you some special pantyhose that will help us both. Your nails are dry so remove your panties and put these on. I’m going to need full access. ” Michelle found the front of the pantyhose, rolled them up as needed and easily pulled them up her legs nonchalantly smoothing them up her legs. The silky style looked great on Michelle. Jackie noted her familiarity and ease in her donning hose.
Noticing that there were two holes in the pantyhose Michelle asked. “What’s with the holes?” Jackie stuck her hand into the front hole, grabbed Michelle’s penis, and pulled it out. It looked funny hanging out like that. “The pantyhose will add to the experience. They are very silky and will enhance your feeling of being slutty and feminine. The feeling of two people fucking while both are wearing pantyhose and making love is not to be missed. It’s a beautiful thing.”
To the bedroom
“Let’s go to the bedroom, Michelle.” Michelle was leading the way. “Ok Jackie, why the opening in the rear?” Rather than say anything Jackie slipped her middle finger into Mickey ass crevice and poked her sphincter, maybe gaining a half inch of penetration. “Oooo! I think I understand.”
“Michelle, let me give you a quick explanation of what you’ve asked for and what we’re about to do. But first, I think I need a work-at-home provision added to Jack’s contract, don’t you?” Michelle stopped walking, turned to face Jackie, let out a laugh and said “Done! I might have to set up an office at my mountain home too.” Michelle hugged Jackie and gave her a sensuous kiss while rubbing her butt.
“Before the night is over you will have experienced your darkest secret (more than once), you’ll have been on your back and have had your legs over my shoulders. We will have gone through a half tube of lube and half a half box of those lambskin condoms. If you really want to feel slutty we could do it bareback… use no condom. You’ll imagine sperm wiggling around in your deepest orifice. It might enhance the slut feeling you’re searching for.”
Reaching her bed Jackie picked up the other pair of special pantyhose, cleaned off the bed, placing all items on a nearby chair, making sure to have a tube of lube within arm’s reach. Jackie placed a few hand towels and a box of baby wipes near the head of the bed.
Taking Michelle by her hand Jackie guided her to the foot of the bed. Jackie had Michelle stand with the back of her legs touching the bed. Jackie stood in front of Michelle and gave her a warm hug and a soft kiss. “Are you ready for this Michelle?” Michelle nodded and in a barely audible whisper said “Yes…I’m ready. I want you in me; I want you in me bareback. I want to see if I can feel the little swimmers.” They both giggled at Michelle’s joke. Jackie removed her panties, sat on the bed and slipped into the same style of silky pantyhose that Michelle was wearing. She stood up and walked over to Michelle to try to ease her mind about what was in store for her.
“Baby doll, here is what needs to happen. You need to make my cock as hard as possible. A repeat of the earlier blowjob would work quite well. We’ll use the wetness from what you leave on my penis as lubricant. You’ll lay on your back, on the bed, with your legs bent. I’ll crawl up between your legs and we’ll wing it from there. I will be using that other hole in your pantyhose. If we have problems we have KY on standby. I’ll be very slow and gentle. Eventually, out of pure horny lust, you’ll probably hook your legs over my shoulders so I can get in you as deep as possible. I want to feel your vertebrae with the head of my dick. You may be able to feel me squirt. As a favor for me, when you feel that, clench my dick with your sphincter muscle once or twice. It adds to my experience and may add to yours too. Especially as I withdraw. Clench and see if you can feel the veins in my shaft as I slowly pull out. I hate to be so clinical. When we’re done and rested I have a favor to ask of you. Ready?” Michelle grabbed my face and gave me a very passionate kiss. “Yes, I’m ready. Now shut up and let’s do it.”
Shut up and do it
Michelle reached into Jackie’s pantyhose hole and extracted Jackie’s penis which was already beginning to firm up. Jackie told Jackie to hold on a minute and she quickly went to the vanity and applied another coat of lipstick. Returning to Jackie she said “Sorry, I don’t want chapped lips”. She took hold of Jackie’s penis and slid to her knees and flipping her long blond hair out of the way. She began jerking Jackie off to get her hard enough to fellate. As soon as Jackie’s penis was pleasantly rigid, Michelle began sucking Jackie into her mouth. After few minutes of head bobbing, Michelle had accomplished in making Jackie hard enough for her penetration. Michelle was tempted to continue the blowjob to ejaculation but decided she had more urgent needs.
Michelle was scooting back on the bed, pulling Jackie by her wrists, up and between her legs. ‘Dang, this girl is anxious’ thought Jackie. Michelle had her legs bent and Jackie was kneeling in place. Jackie leaned forward and went in for one more kiss. Jackie too was excited since she had never fucked a man before. It was going to be a first for both of them. Being with a man was high on Jackie’s fantasy list.
Sensing a need, and to make Michelle’s first time easier, Jackie used a generous amount of KY jelly to grease her shaft thoroughly.
Widening the hole in Michelle’s pantyhose Jackie inched forward and had her penis at Michelle’s anus. Jackie was just about to begin penetration when Michelle reached down and pulled Jackie into her about an inch.
Unknown to Michelle was that this was Jackie’s first experience with this kind of sex. Jackie talked a good show but was totally improvising everything. Porn and locker room gossip was the basis for what appeared to be her prowess. Also unknown to Michelle was that Jackie was a virgin and yearned to be on the receiving of a man’s penis. For these reasons Jackie wanted to watch Michelle’s face as she was being fucked. She wanted to know what she could expect.
Michelle’s virginal tightness was an obstacle they both had to overcome. Being highly motivated, and with Jackie being compassionately gentle, full penetration was achieved. Jackie began slow fucking Michelle, partially withdrawing with each thrust, so that she could feel Michelle’s tightness with each stroke. “Are you doing ok, baby doll?” Jackie asked. “Relax yourself and it will get easier.” Michelle nodded and Jackie felt Michelle loosen up. Jackie picked up the tempo and she watched Michelle begin to smile. Michelle began to arch her back and was soon meetings Jackie forward thrusts.
As predicted by Jackie, Michelle soon had her legs over Jackie’s shoulders to attain maximum penetration, and was eagerly humping towards her first anal orgasm. The sexy feeling of their nylons rubbing and sliding together was indeed sensuous. The slick friction and sound of the materials rubbing together enhanced the moment for them both.
Pulling back a little Jackie made an effort to rub his cock head into and along Michelle’s prostate. She must have found her target as Michelle began rapidly thrusting her pelvis up to meet Jackie’s down stroke. Michelle’s eyes rolled back, she let out a load groan, and maintained her upward arching of her back. She quivered, she shook and she clenched Jackie’s shaft with her rectal muscles repeatedly and shot a stream of her warm sperm up her belly and onto her chin as she orgasmed. Michelle collapsed back onto the bed and lay still with Jackie still deep within her. Jackie shot a penile throb out to Michelle and Michelle reciprocated with a clenching of her own. They both giggled and clenched again.
“Did that feel good, baby doll?” Jackie asked. Michelle whispered “That was great… it was orgasmic.” Leaning down to kiss Michelle she used two fingers to collect some of Michelle’s goo that was on her chin. Making sure that Michelle was watching Jackie made a show of licking the sperm from her fingers. Michelle was wide eyed. Scooping up another glob onto her fingers Jackie extended her fingers and offered some to Michelle. Maintaining eye contact with Jackie Michelle sucked her seed from Jackie’s fingers performing a mini blowjob on Jackie’s fingers. A last swirl of her tongue and Michelle laid flat to relax.
Jackie was about to pull out of Michelle when Michelle grabbed her by the waist and said, “Be slow.” Jackie felt Michelle clench down on her penis as she began his withdrawal. ‘Damn, she is trying to feel my vein!’ Just as her dick popped free Jackie said “Baby doll that was a slutty move.” Michelle smiled widely at the compliment.
Reaching for baby wipes and towels the couple cleaned up a bit and then lay on their backs, side by side, staring at the ceiling. Jackie imagined that she could hear Michelle purring. Michelle grabbed Jackie’s hand and pulled it to her lips and kissed it. “Thank you, Jackie. That felt better than I imagined. I’m sure glad I came over today. I was very nervous about how things would go. You’ve made me feel so relaxed and special. I don’t feel like a pervert being with you. It all seems so natural.” She kissed Jackie’s hand once more and then dropped their hands to the bed. Holding hands, with their fingers interlaced, they allowed themselves to recover.
Jackie rolled over facing away from Michelle, and encouraged Michelle to spoon her. Michelle pulled Jackie back until they were snug and tight. Michelle was enjoying feeling Jackie’s heart beat. She leaned forward and kissed Jackie’s neck. “You smell nice” Michelle whispered, “And even without your wig your hair looks nice. Your face and nails add to your beauty.” Michelle shot Jackie a penile throb as her penis was laying against Jackie’s butt. Jackie smiled. Reaching behind her Jackie touched Michelle’s penis and gave it a brief squeeze.
“Remember when we got on the bed that I said I would ask you for a favor when we were done?” Michelle had her eyes closed as they lay there almost entwined and managed an “Um-huh. Why do you ask?”
Jackie slowly sat up and turned to face Michelle. Looking into each other’s eyes Jackie picked up and held Michelle’s hands. “You said that you wanted to feel me inside of you, right?” Michelle nodded an affirmative ‘yes’. “I want you to be inside me. I’m a virgin and can’t think of a nicer person to give my cherry too.” Jackie pulled Michelle forward and they shared a passionate kiss.
Michelle paused a moment and said “When I first got the idea of us being together I was only interested in giving blowjobs and being taken from behind. I never really thought about being fellated or in giving anal sex. I guess I’m more of a ‘receiver’ than a ‘giver’ but I could do it, on occasion.” Jackie smiled, leaned closer, kissed her and whispered “How about helping a girl out? I need to feel what you felt. Now. You won’t know that you like or don’t like it unless you try it.” Jackie reached over and grabbed Michelle’s penis as it drooped from her pantyhose. Giving it a few gently strokes Jackie could feel it begin to swell.
Jackie leaned back and got her tube of lipstick from the vanity and returned to facing Michelle. Establishing eye contact, Jackie expertly painted her lips and tossed the tube up by the pillows. As a token of sincerity and proof of her urgent need, Jackie leaned forward, grabbed Michelle’s shaft, leaned over and kissed the top of her cock. Michelle throbbed against Jackie’s lips. Embolden by her first dark red lip print Jackie hefted and felt Michelle’s penis, gently squeezing and exploring. It felt soft and smooth. Unknown to Michelle, Jackie had never been with a man and had never touched another penis.
Looking into Michelle’s eyes Jackie pulled Michelle’s penis over to her mouth and gently gripped it, with her red lips, just behind the glans, pressing her lips snugly together, in an effort to leave a red ring, Jackie tickled Michelle’s penis with her tongue. She sucked in another inch of meat and re-gripped the shaft lower with her lips. Jackie ran her tongue up, down and around. ‘My god, I’m actually sucking a man’s dick”. Jackie could feel the penis stiffen as she sucked and licked it. Michelle clenched out a throb to tell Jackie ‘thanks’. Jackie went back down Michelle’s shaft as far as she could go and began a slow, sucking withdrawal using her tongue in a way that she liked done to her. Her mouth popped free with an audible sound.
Holding Michelle’s penis, like it was a garden hose, Jackie used her thumb to smear the pre-cum around and around the tip. Michelle sent Jackie an involuntary throb. Jackie leaned closer and gave Michelle a kiss, never stopping her thumb action. ”Well” she whispered, “could you help a girl out?” She bent over and gave Michelle’s erect penis another kiss. “Please” Jackie asked. ‘I can’t believe I‘m begging to be boned! Latent fantasy or not I hope it satisfies my curiosity’ thought Jackie to herself.
“If you want me to help you out you better stop with your thumb action.” Michelle said. Taking that as a ‘yes’ Jackie quickly moved to the end of the bed and sat with her feet on the floor. Motioning Michelle to come over Jackie grabbed Michelle’s hand and pinned her between her legs. She reached to the side of the bed and picked up a tube of lube. She removed the top.
Michelle, and her raging erection, were both ready. Jackie grabbed Michelle’s smooth penis and kissed and bobbed her head up and down it a few times. She used her tongue to shove it from her mouth. Holding Michelle’s erection with one hand Jackie used her other hand to squeeze out a thick line of lube along Michelle’s entire penis; from tip to shaft and back again. Putting the cap back on she tossed the tube back onto the bed. Jackie had an odd grin on her face. “I want it bareback too, baby doll.”
Jackie took hold of Michelle’s dick and began lubricating the entire length with long, slow pulls up and down her shaft. The gel was very effective and soon Michelle’s shaft glistened in readiness. Jackie wiped the leftover lube onto her own dick enjoying the slipperiness that would aid her first penetration. ‘God, I’m so damn horny’ thought Jackie. She leaned back onto the bed and used her legs to pull Michelle closer. “Let’s try it with you standing and we’ll move onto the bed if we have to.”
Jackie pointed her legs at the ceiling, reached back and spread her butt cheeks through her pantyhose. Michelle poked her penis through the rear hole in Jackie’s pantyhose and into Jackie’s sphincter with her cock head and stopped. Using her cock Michelle made a few circles around Jackie’s opening which helped spread the lube. Michelle noticed that Jackie’s hole was making little puckering moves of anticipation. ‘Her butt is trying to kiss my dick!’ thought Michelle. “Lean forward so I can rest my legs on your shoulders.” Jackie requested.
Michelle took a deep breath, thrust forward a little and slowly began the insertion, sliding in almost two inches. The pair of them both gasped in unison. “Wow” said Michelle, “Arrrgh!” said Jackie. Michelle pulled back and repeated the process gaining more than three inches entrance. Applying almost no pressure Michelle could feel Jackie relax and stretch. It sounded like Jackie was doing yoga or Lamaze breathing exercises. Still applying very little pressure Michelle watched in awe as her penis was slowly sucked in to Jackie’s warm ass. Her penis began to disappear deeper and deeper. “Hold on a minute”, Jackie gasped. “Let me catch my breath.” Michelle held still. Wiggling her butt and adjusting her legs so as to get more comfortable Jackie gasped out “Ok… I’m ready.”
Michelle quickly pulled back and just as quickly thrust forward. Jackie gasped. Michelle repeated her in and out technique three more times, savoring the warmth and uniform tightness around her shaft. It felt really good! Trying to be cute Jackie clenched down on Michelle’s dick and maintained a firm rectal grip. Michelle slowly pulled back enjoying the way Jackie’s sphincter milked her cock. “Jackie, I gotta tell you, I think you made a convert out of me. This feels fucking great! Our pantyhose’s rubbing together makes it even better.” Jackie had a double handful of bedspread in an effort to steady herself.
Michelle fell into a pleasant, steady rhythm that was working well for them both. Her strawberry blond hair swayed to the rhythm. Jackie had become passionate with experiencing her first fuck. She clenched, she grunted at each thrust, she wiggled and was making upwards thrusts of passion. ‘God, it is good!’ Jackie thought.
In an inspiration of lust Michelle partial withdrew from the sanctity of Jackie’s bowels. Michelle transferred some of the KY from her dick into the palm of her hand. As she thrust forward into Jackie Michelle wrapped her greased hand around Jackie’s easily available penis and began jacking her off. Jackie screamed loudly, “Don’t stop! Go faster! Faster, I’m so close…!” There was no mistaking the urgency in her voice.
Michelle was also close to orgasm and the tension was extreme. When the moment happened she yelled “Fuck!” thrust forward, and ground her shaft as deep as possible into Jackie. She shoved Jackie a foot further up the bed with just her dick and then spewed her warm seed deep in Jackie’s bowels. The feel of Michelle squirting was all it took to push Jackie over the edge into a sensory over load orgasm.
Jackie bucked upwards several times and wrapped her legs around Michelle, not wanting to let her pull free. Jackie blew her load and it leapt up to her neck and chin. It felt warm as it hit. Jackie relaxed and began softly crying, her legs hanging limp off the edge of the bed. Michelle pulled out. “That was a beautiful thing” Jackie sobbed. Michelle got on the bed and started trying to comfort Jackie, stroking her hair, kissing her face and whispering “It’s all good, all will be fine, take a few deep breaths, there, there…” Michelle grabbed a few baby wipes and began cleaning cum off of Jackie as well as the wet results of their act from her penis.
Jackie scooted herself further up the bed and laid back to compose herself. Michelle lay next to her and began kissing her forehead and eye lids. “Are you ok? Can I do anything for you?” Michelle asked. Jackie looked over, wiped her tears away, smiled beautifully and said “No, I’m ok… it’s just that… I mean… wow! I’m not sure what I expected but this moment was fantastic! How was it for you baby doll?”
Michelle flopped onto her back, stared at the ceiling and began talking. “I had no idea. I told you that I wasn’t keen on fucking people in the ass. What we did here, today, has changed my mind forever. I’m a new man… I mean, I’m a new woman. And I owe it all to you. Maybe it was the way you clenched and milked me, maybe it was because I felt so damn horny.” “And did you feel slutty?” Jackie probed. Michelle turned on to her side and faced Jackie. She smiled and gently stroked Jackie’s cheek. “Jackie, you have made me feel very slutty… and naughty and…and horny… and pretty. I can’t thank you enough. My wondering about how I could experience the things we’ve done just today are over. It could not have been any better. I’m glad I came over. There’s so much to look forward to.” Pulling Jackie closer Michelle gave her a lingering kiss of passion. “Anything else, baby doll?’
Rolling back Michelle sighed and said, “Not only did you make me feel slutty you gave me the chance to be slutty. Never in my wildest dreams did I think that I would ever give someone a blow job, be up their ass, have someone pleasure me anally, wear lingerie and makeup… or hire a full time sex partner/gender trainer” Jackie was thinking the exact same thing about her day! “You did fine on all accounts baby doll.”
Jackie gently tugged on Michelle’s hoop earring and said “It’s getting late baby doll and we have so much to do, you have so much to learn and we haven’t even tried on our beautiful wigs yet, you only have nail polish on one hand, and I’d like to see you in 3 inch pump heels.”
“We need to plan how you can wear some of your sexy lingerie under your male clothes at work and in off work activities. With a little planning we can have you wearing a bra, panties, garter belt and stockings, jewelry, light makeup, lip color, nail polish; so many ways to express your inner girly self. You need to let your hair grow so we have something to work with. Pixie shag would be a good start for you and it could easily be brushed into a guy look. You might like being adventuresome.”
Jackie crawled out of bed and immediately sat at her vanity. Applying a fresh coat of lipstick she began brushing her hair while explaining to Michelle what needed to be done today. “Let’s get out of bed and get on with our day. Come here doll face.“ She motioned for Michelle to come stand by her. Gently holding Michelle’s face Jackie expertly applied lipstick to her lips. Jackie then put a short smear of lipstick on Michelle’s and her cheekbones. “Blend it in with your finger tips and it makes a quick and easy blush. Add more if you want.” Leaning towards the vanity mirror Jackie showed Michelle what she meant, rubbing the colored streak into a healthy looking blush. Michelle followed the lead and smoothed in her own blush. “Wow, that sure makes a difference.” proclaimed Michelle. Michelle took the opportunity to add some mascara to her lashes.
“Pull off your pantyhose and get a fresh pair of panties” Jackie directed. “You may want to use the restroom and clean up a bit. I see you are dribbling a little down the back of your leg. Clean that up and I’ll help you deal with it later. I’ll use the restroom first and then we’ll meet in the kitchen. I have some deli sandwiches and chips that we can eat.” She gave her hair a brief spray of lacquer and then removed her bustier. She had kept that on for Michelle’s benefit.
Adjusting her bra Jackie got busy getting dressed in the same casual, but feminine ‘beach’, gear that she had worn the day before. The only difference was she used a fresh blouse. Michelle was observing her every move. Jackie was pulling on some pretty lace trimmed French style panties but stopped when they were just above her knees. Opening the box of Kotex Lite Days pads, that was on her vanity; Jackie removed and opened a thin pad. Peeling the adhesive from the back of the pad she pressed it into her panties. Looking over to Michelle Jackie said, “Look and learn. This thin pad will soak up any leakage that you may have from having bareback anal sex. It’s an easy way to avoid a messy or embarrassing situation. You’ll hardly know it’s there. It has little plastic wings that spread out and provides better protection from ugly wet spots soaking through your clothes. Sperm will leak out no matter what you do.” Pulling her panties completely up Jackie grabbed a pad and tossed it to Michelle. Michelle stared at it in amazement. ‘My little Jackie is damn resourceful’ she thought.
Following Jackie’s suggestion Michelle lowered her panties and affixed the pad and re-positioned her panties.
Jackie continued dressing and opted for new set of cocoa colored Silky pantyhose quickly pulling them on. Next came her mid rise jeans and a blouse. She slipped into a feminine pair of sandals and started for the kitchen. “I’m going to fix us some nice deli sandwiches and chips. Call me when you’re dressed. I have an extra pair of pantyhose if you’re interested. Oh, and for God’s sake, please toss out our dirty ones.” And then she was gone.
Michelle took the time to use the rest room and cleanup a bit. Looking in the mirror Michelle took a quick inventory of her situation: Matching Navy blue bra and panties, breast enhancers, camisole, cocoa colored pantyhose, beautiful shoulder length strawberry blond hair (with dual pony tails), makeup, eye shadow, eyeliner, mascara, dark red lipstick, blue toe nails and one hand with blue polish. Michelle giggled at her own image. She smiled widely at how feminine she had become in such a short time. She was pleased.
She was about to join Jackie at the kitchen table when Jackie came back in. “Whoa, there Missy, let me see what you have going there.” No doubt about it Michelle was looking nice. “We can’t have you running around in only your camisole and panties. I have a white tennis skirt with an elastic waist that will show off your great legs and add another layer of femininity.” Jackie opened a drawer, found what she needed and brought it over to Michelle. Holding the skirt open Jackie said “Step in to this baby doll.” Michelle did and Jackie pulled it into place.
Jackie gave Michelle a hug and walked them in front of the vanity mirror. “What do you see, Michelle? Do you see the two pretty girls looking back at us?” Michelle stood in silence admiring her female self. She made a point of flipping her hair. Jackie produced a cute tennis bracelet and a gold necklace for feminine effect. Clasping the tennis bracelet closed she stepped back to admire her creation. “Damn, you’re cute”. Michelle gave Jackie a good hug and enhanced it with a long kiss. “Thank you, my Jackie. Thank, you.” Still embracing, Jackie gave Michelle’s panties a good rub; there was a stirring. Michelle felt the need to grab Jackie’s crotch and was in the process of pulling on Jackie’s zipper tab. Jackie playfully slapped Michelle’s hand away saying, “Stop that! There’s plenty of time for that later. It’s time we ate. Oh, and by the way if you were to wear a control top pantyhose it would help make that cute little bulge of your less noticeable.” Michelle added this bit of information to memory. ‘Nice to know’ she thought.
They went and sat at the kitchen table where the sandwiches, chips and olives were waiting. They made idle chatter as they ate. Jackie finished first and went and retrieved the bottle of blue nail polish, shaking it as she was sitting down. Without asking she picked up Michelle’s unpainted right hand and began stroking on the first of two coats. “I want to thank you again for helping a girl out earlier. It felt so ‘right’.” Michelle lightly blushed at the reference to their earlier love making.
While Michelle’s nails dried Jackie took the opportunity to make them both a drink. Jackie took a sip of her drink and then sat the drinks on the table. “There are a lot of decisions that need to be made by both of us. You have to decide on how femme you want to go. One thing is clear you need to build a wardrobe, get some jewelry and accessories, find clothes and colors that will accent your potential and grow out your hair and nails. And you need to let me know how often you want to ‘see me’ and how frequently feminine you want me. Am I to always be girly for you? “Jackie stopped talking and enjoyed a sip of her drink.
Pulling her chair close to Michelle Jackie continued. “Look at my face, my eyebrows, my dyed eye lashes and my nails. I had this done for you. I don’t think I can return to our office like this. It would be difficult for both of us.” Michelle gently held Jackie’s face in her hands. She ran her thumbs over Jackie’s girly eyebrows. Taking in Jackie’s face, her eyelashes and red lips Michelle leaned in and gave Jackie a soft kiss. “You’re right again. You definitely would create a distraction if you showed up at work looking like this. You are so… so… so very ‘Jackie’. I think you’re beautiful.”
Placing her hand on Jackie’s leg, Michelle continued with “We could say that you were transitioning to being a woman. We could find you a new office or job site… you could be away on a special project for weeks, maybe we could make it work. I need to be near you.” Softly holding Michelle’s hand that was on her knee, Jackie pulled that hand and pressed it to her crotch. Jackie squeezed Michelle’s hand between her legs. “I just don’t want to be your office whore.” That remark got Michele’s attention.
Leaving her hand where Jackie had placed it Michelle began to speak and also began to seriously stroke Jackie’s crotch. Her thumb was at the bottom of Jackie’s zipper and her middle finger was at the base of where Jackie’s balls should be. She stroked and asked “Have you given these things any thought?” Jackie moved her chair closer so the finger tickling pressure would be more intense. Jackie pulled her zipper down in invitation to Michelle. Michelle took the bait.
“I think,” Jackie began, “that you and the corporation need a Director of Corporate Diversity that reports directly to you.” Jackie rolled the waist bands of her pantyhose and panties as far down as she could, wiggling to loosen her jeans more, exposing about half of her penis. “I also think that you need to find a nice, near bye, condo that could function as an office and a hospitality suite for you, me and special guests.”
Michelle took more of the bait and had fully gripped Jackie’s shaft and was slowly stroking Jackie’s shaft as Jackie spoke. She adopted the ‘thumb-on-the-cum’ method of petting, spreading Jackie’s natural lubricant around and around. Jackie gave out a soft gasp and slid even closer. “Many executives have private retreats and places to relax or conduct business. You can make it happen.” Jackie’s voice was sounding raspy and urgent.
Jackie leaned back and let Michelle tug her pants off. Jackie freed her cock from the remaining confines. As a tease Jackie made her penis twitch in Michelle’s hand. Michelle giggled and playfully called Jackie a ‘slut’. Maintaining a friendly grip on Jackie’s shaft Michelle pulled it towards her, bent forward and sucked in three or four inches of Jackie’s penis. Her tonguing felt so fine to Jackie. Michelle began bobbing her head up and down Jackie’s now slick penis while still milking her with her hand.
Jackie leaned back into her chair. Michelle got down on her knees. Within minutes Michelle had taken Jackie to heaven and back.
To heaven and back
Grabbing Michelle by one hand Jackie pulled her to the bed room to reciprocate a loving blowjob. Thirty minutes later Jackie was snuggling next to Michelle and was resting on her back with her eyes closed. She was holding Michelle’s hand and could have easily fallen asleep in her contentment. Michelle tugged on Jackie’s hand and said, “I don’t want you to be my paid whore and I wouldn’t expect you to be continually dressed as a female. I think it would be wonderful if you did.”
“I also agree that you returning to your job or office is out of the question. And you’re correct that I could justify the need for ongoing diversity training and a special projects manager. The idea of having an executive retreat, other than my mountain home, is superb. On a personal level I know I’ve found someone that could help me explore my feminine side; someone that could share my new found experiences that were, until today, only far off fantasies. You’ve taught me a lot in a very short time and I feel relaxed being with you.”
Sliding out of bed Michelle sat at the vanity touching up her lipstick, mascara and hair. She removed her dual pony tails and switched to a single pony tail. She was removing the hoop earrings she had been wearing and was inserting a pair of long drop earrings that were lying in view. Snapping on the back of the final earring Michelle casually said: “In short I need you. We could use your first initial on your business cards rather than ‘Jack’ until we arrange a formal name change. How would you like to be my Director of Corporate Diversity and Special Projects? $75k a year, reporting directly to me and working off site. Will you take the job or must I offer it to someone else?”
Jackie leapt out of bed and rushed to hug and kiss Michelle. After a long and sensuous kiss they separated long enough for Jackie to say “Yes! Yes! I’ll do it! We may need to add to my title: ‘Clothing, Makeup and Gender Coordinator’.” They broke into laughter at the thought.
Michelle was heading to the kitchen in order to make them another drink. Over her shoulder she said, “I’m glad your porn tape auto destructed so you have nothing being held over your head. You have the only copy. Maybe someday we’ll have a movie night and watch it together.” She laughed out loud.
“You knew my blackmail videos had disappeared! And you never told me until now!” Jackie almost yelled. “Yes, I knew. That means you did what you did without any coercion. You had sex with me out of your own free will. You really helped a girl out. I truly appreciate that. It proves that we can trust each other. We’ve shared some extremely intimate things today.” Putting her arm around Jackie Michelle pulled her close. “I never thought I would ever say this but I am very attracted to you. You’re intelligent, resourceful, well poised and… delightfully slutty.” Michelle pulled Jackie even closer, kissed her on the cheek and held her hand. “We’re a good match! What’s that expression? ‘You complete me’.
Suddenly Jackie’s future was even brighter. And they hadn’t even made it to trying on skirts, dresses, lingerie or casual girly clothes. There’s so much to do for Michelle. Jackie actually wanted to see how Michele would look in heels.
Unlike yesterday Jackie was looking forward to what lies ahead. Giggling inwardly, Jackie wondered if Jonny from work would actually leave her the tube of lipstick that he had promised, on her desk on Monday. ‘Sure hope his copy of my porn video evaporated to’ she thought. She was very confident that it had.
“I was thinking about taking on a roommate in a month or two” Michelle began. “And my mountain house is in need of a live-in house keeper.”
(The story ends… or does it? the options are many)
A word to the wise: Be careful what you click on!
Epilogue
Here is what prompted this story. Several sites offer gender morphing or adding makeup, hair, a magazine cover of you, etc. That’s okay. However, if you are NOT careful what you click on, the site sends your femme photo to your Facebook page and will be seen by all your friends! Those pretty photos of you could result in many interesting conversations if your femme side is secret.
http://www.clipquiz.net/?all=1
Instructions
1- Click "Login with Facebook and choose profile photo"
2- Accept permission so we can list your Facebook photos
3- click the photo that best shows your face
4- Wait for your result to be ready
I almost did this in error and thought about what sort of turmoil posting such cute photos would have stirred up. On another site I got to the “review image” part of my makeover and was able to ‘save’ my photos BEFORE clicking on the “accept and continue” options. Whew! So I do have several photos of my pretty femme self; they are not seen by anyone (that I know of) but me. Have fun out there but read the fine print.
Maybe you could create a new Facebook page, have no friends, and then morph to your heart’s content. Share if you find a solution. In the mean time “Be careful what you click on”.
Here’s other sites: https://www.esteelauder.com/virtual-try-on & http://www.morphthing.com/
