Crossdressing Stories


Crossdressing Story

Although I was actually the 20 year old babysitter in my second semester at the local community college, at this moment I looked quite similar like Sally Douglas, the wife of Jack and the mother of their three children. I was dressed in one of Sally’s outfit in front of Jack, who had arrived home unexpectedly and found me dressed as his wife during one very snowy night.

Three years earlier, I had started babysitting a few nights a month for the Douglas family, and being a somewhat confused high school student at the time with no real relationships with girls of my own age, I soon found myself overtaken with a serious case of puppy love for Sally.

I was also a closet cross dresser, but only had a very limited wardrobe since I was still living at home with my parents and siblings. Sally was about 35 years at the time, in the midst of a second marriage to Jack, who was a few years older than her. Sally favored a stacked bob hairstyle that she could keep consistent by wearing two of her three wigs in that general style, with the third wig being a collar length style that was fuller in shape.

As it was, Sally was simply amazing in style and personality, with a very sweet manner. She always seemed to dress in an alluring, yet understated feminine style, but I had found during my explorations of her closets that she had many trendy and sexier outfits in her closets for special events and evenings out. Jack was easily four inches taller than me and while carrying a few extra pounds, I could see why Sally was attracted to him.

He was a mid-level executive with a local electronics firm that frequently had him making extended overnight business trips around the country. As a result, he was rarely home when I was called to babysit, but unlike him, I was not sports oriented so we rarely had any in depth kind of conversations even when he was the one that drove me back and forth from my home on the nights and days I babysat for them.

However, Jack always Jack paid me a lot more than the rate Sally had established for my babysitting services, so I did like it when he was there as often as he was.

Sally had a son about 6 years old from her first marriage, while Jack’s kids were in college and did not live at home. Just before I started babysitting for her, Sally and Jack had adopted two infants, so there was definitely a need for someone to care for them on the nights that Sally and Jack had other commitments.

While Jack was gone, Sally was also managing a shop owned by her family in Buffalo Hills a few nights a week, as well as most weekends. As a result, there was a recurring need for someone to babysit the children, and my parents had arranged for me to begin babysitting for them when the Douglas’ previous babysitter had graduated from high school and headed off to college. Sally and Jack had both wanted me to continue babysitting even after I graduated high school and had begun college.

I gladly welcomed the opportunity for both the chance to make some extra spending money, but mostly to continue my practice of secretly transforming myself into Sally for the few precious hours available to me between the time the children went to bed and when Sally or Jack were scheduled to return. For three years it had never been a problem, as they were both very punctual whenever I worked for them. I remember the first night that I was to babysit had me anxiously waiting to be picked up by Sally for the drive a few miles across town to her home.

I had previously seen Sally many times at social functions and church, and while I had never had any kind of conversation with her, from what I was able to overhear, she seemed to be well regarded by everyone, and she was the ideal wife, mom and lover in my young mind. So I was naturally excited and expectant waiting to finally be in direct proximity to her.

When her car pulled up and the horn honked, I said my goodbyes to my parents and was soon sitting beside the object of so many fantasy dreams, and the magic began almost immediately. After some brief chatting during the drive where I was relishing every second of being there beside her, drawing in her fresh perfumed scent, admiring the outfit she was wearing, and glancing at her profile without looking obvious, Sally explained, “Our last sitter was with us for almost four years, and we even went to his high school graduation, so I hope this will work out with you, too.” “That’d be really nice, Mrs. Douglas.” She parked at the curb in front of her home, and I noted it was a split level colonial in a pretty nice area of town.

The status of the home was an indicator of a fairly well off middle class family, and I was already looking forward to seeing how she had decorated and furnished the inside. As I walked behind her along the walkway toward the home, I couldn’t help but admire how she looked from even that view. Not exactly gorgeous, but obviously the type of woman that I knew I would completely fall in love with, and I regretted immediately the age difference between us…she would always be unobtainable for me.

As we reached the door, I waited while she used her key to unlock the door, and I noted that I was probably only an inch taller than her. I had a fairly lean build, so I was already wondering if I would be able to fit comfortably in her outfits. For the past few years, I had dabbled with dressing in women’s clothing, with most of my pieces liberated from the occasional charity clothing drives supported by our church. Nothing sexy, but I had so far collected a few skirts, blouses and two dresses.

If Sally was a size 8 or larger, I knew that I would be able to fit into her things, and I was already longing to check her hamper to see what was there. I managed to control my desires for the first several times babysitting for Sally, but one evening I discovered a very alluring black bikini left to dry on a rack in the laundry/utility room.

Of course, other than imagining how it looked on Sally, I was next wondering how it might look and feel on me, and it seemed like hours had passed before I was certain her kids were sleeping soundly. Satisfied that now was as long as I could wait, as I wanted to be sure that I would have enough time to experience wearing the bikini before carefully restoring everything as it was.

I was extremely nervous as I made sure the den drapes were fully closed, which was next to the laundry/utility room. I knew what I wanted to do was wrong, but I could not resist the desire, so minutes later, I had been standing naked in the laundry area holding Sally’s bikini in my hands. I distinctly remember how I had admired the texture of what I realized was a faux leather-like fabric. It certainly gave me a new appreciation for Sally’s sexiness, since the bikini would not cover much any woman’s body. After slipping into the bikini, I was happy that it fit my waist and hips.

The top was equally form fitting, although I clearly was missing the essential flesh to fill out the cups. While sexually stimulating, it was an incomplete feeling, as I knew I needed to truly be as feminine as possible, to include hair, makeup and even a hint of Sally’s perfume. Of course, I satisfied my urges, and was careful to not get my wetness on the bikini fabric.

From that point forward, I was intent to make my transition to Sally as complete as possible, even if I had to bring my own wig in the form of a Halloween fright wig that was not too bad looking once it was brushed out. However, that turned out to not be necessary, as my next guilt ridden babysitting job led me to a thorough inspection of Sally’s bedroom, which revealed two of her wigs and an empty wig form, which meant Sally was wearing that one this particular evening.

As a result, from that point forward, I would always have the benefit of Sally’s hair style when I dressed as her. Sally also had so many wonderful makeup and beauty products in both the upstairs full bath and the downstairs half bath. In actuality, the half bath had a nicer and more complete assortment, and it was the room where I did most of my transformations.

I began to practice my makeup skills virtually every time I was babysitting. Since my intent was to emulate Sally, I took care to notice the way she wore make up for regular functions, as well as when she dressed up for what was obviously a special event or function, such as New Year’s Eve. I also had the family’s photo albums from the den to use as guides, and these sometimes inspired me to capture the exact look, such as a photo from when she was out with a girlfriend, with both of them wearing the classic little black dress at an upscale bar. Sally was consistent with never once arriving home earlier than she stated before leaving, and often she would call to give me any update as the evening went on, so on those evenings, I knew almost to the minute how long I could stay in character.

It was always so amazing to answer the phone while I was dressed as her and talk for a few minutes, giving her every assurance that the kids were great and were now sleeping soundly. How could anything bad happen to the kids when “mom” was so close to come immediately to address every need? The evening when everything changed for me was a chilly Friday in January. The now six year old son was away at a band camp for the entire weekend, so after putting the two young children to bed at 7:00 PM, I had absolute freedom to transform myself into Sally.

Although the forecast had been for otherwise, snow started falling at a rate where it quickly began to accumulate. However, I did not notice that as I selected that night’s outfit and settled in at the makeup table in the downstairs bath. As the snow fell, I was totally unaware of the change in the weather, as every moment brought me to look more like the woman I adored. My feminine transformation began with undressing completely from my boy clothes and then slipping on a pair of Sally’s black satin panties and a lacy black underwire bra. I then stuffed the bra cups with faux breasts made from an old pair of stockings.

Sally’s size 34B breast size was perfect for me, and I happily emulated her by matching the breast forms to fit comfortably in her bras. I also wore a pair of nude pantyhose augmented with the set of foam hip pads that I had created months ago to give me a more curvaceous and feminine body, and it really gave the impression of wider womanly hips once I put on a dress or skirt.

I gingerly began my makeup ritual of foundation preparation. Having literally no facial hair and little signs of acne gave me a good platform to work with. I used a somewhat lighter liquid foundation than my actual skin tone, but it was only a subtle difference, and I then used a light dusting of powder to set it. Since I had enough time to do a thorough makeup removal, I applied black eyeliner to frame my eyes, and then delicately applied mascara to my lashes, not too much, just right. Then I finished the eyes with a blended mix of shimmery taupe and light blue eye shadow.

With a somewhat practiced manner, I then feathered the eye shadow to a nice effect before leaning back to assess my efforts. I was very pleased and smiled as I reached for a cranberry red lipstick. Pulling off the top, I turned the tube and smiled even more as I saw the well used shape of the lipstick emerge.

I loved the idea that the last person to have used this lipstick was Sally, herself, and each time I used her lipsticks, it was a loving touch of her own kisses that adorned my lips. After carefully applying a coating of the lipstick, I used a tissue to imprint the lipstick, and placed the kissed tissue to the side as I deftly used a brush to add blush to my cheeks.

Looking at myself in the makeup mirror, I could not help but smile as I turned side to side to inspect my results. All in all, a bit understated, as Sally would do, herself, and I slid the chair back and turned to glance at tonight’s outfit. A 3/4 length sleeved satin and rayon top with an emerald green and black leopard spot pattern, and a black pencil skirt were the main elements, with a pair of 3 inch strappy back black heels to complete the look. By this time, I was totally at ease wearing high heels, and loved the way they set off my legs. I also relished how the heels forced me to assume a much more feminine gate with a subtle hip sway when I walked.

I slipped the skirt up and zipped the back, and then fastened the button tab to keep the zipper in place. It fit perfectly, as I already knew it would, as I had worn it a few times with other tops, but tonight was to be my first time wearing the green and black top. I then slipped on the heels and fastened the buckles and stood. Next, I took Sally’s medium length wig and adjusted it into place, perfectly framing my face and falling to just above the shoulder line.

I felt almost complete as Sally at that moment and only needed earrings and jewelry to finish the look. I put on a pair of dangly screw back earrings, three gold bangles on one wrist and single, heavier bracelet on the other, finished off by two rings on my wedding finger, wishfully thinking of them as an actual engagement ring and a wedding band… oops, one more thing, since I would even have time to shower to clean up after my time as Sally, two light spritzes of a flowery perfume.

Oh my god, I thought as I turned and looked at my reflection in the full sized mirror. I saw in the reflection a younger version of Sally, me! As any good wife and mother, I knew that I should take a quick check on the children, and I effortlessly moved up the stairs and turned the corner which is when I noticed the accumulation of snow.

Easily four inches had fallen, and it was still coming down heavily, and the snow plows had not yet even touched the street. I sensed that Sally would not be able to travel home that night with the snowy weather, and at that very moment the phone rang. I stepped quickly to the phone, “Hello, Douglas residence,” I answered in my boy voice, but in all other respects I was the woman of the house. “Hi, honey,” Sally replied, “I just wanted to check on things… and, I know this is unexpected, but it looks like the roads aren’t going to be clear until tomorrow morning…” “I know, I was just looking outside.” “Well, I already called your parents and they’re okay if you could spend the night.” My heart leapt with joy, “Uhm, I guess that’s okay then. I don’t mind.” “Are you sure? I could ask Thelma to come over, instead.” Thelma was Sally’s single older sister who lived nearby in the next town.

While generally a very pleasant woman, and sometimes quite funny, she had somehow not been blessed with the beauty that Sally had inherited, but she definitely had a much more shapely and full figure. “Oh no, the roads look pretty bad, I’m worried she might have real trouble…” “Okay, you’re sure, then?” “Totally, the kids and I’ll do fine,” as I admired my reflection in the picture window with the snow continuing to fall outside. “Just in case the babies need anything, would you mind sleeping upstairs… you can stay in my bed.”

“Are you sure? I just figured I’d use your son’s bed.” “No, no, that’s too small for you. It’s fine. The sheets are fresh, and it’ll make me feel better knowing you are there, okay?” “Well, okay, I guess.” “Alright, I’ll call you in the morning. You won’t mind feeding the kids and getting them cleaned and changed before I get there, will you?” “Of course not, and they’ll be great as always. You don’t have to worry.” With an obvious tone of relief, Sally quietly said, “I feel so much better knowing you’re there, and please, just make yourself at home.” “Okay, Mrs. Douglas, see you tomorrow.” “Night, night,” and she was gone.

Breathlessly, I considered how perfect it would be to actually sleep wearing one of her negligees or night gowns in her own bed! Oh, this was heaven! I peeped into the children’s bedroom and saw them both sleeping soundly. I quietly stepped into the room and checked on them both, such sweet babies. Satisfied that the children were fine, I slowly backed out and gently closed the door.

I was actually weak kneed at that moment, and felt in awe about Sally’s ability to be the perfect mom. With the whole evening now totally uninhibited by any need to transform back to my boy mode, I decided to emulate being Sally as the hostess of an imagined get together with her neighbors. I thought my choice of outfit was nicely suited to that type of social engagement, and as I passed by the kitchen, I took a can of ginger ale from the refrigerator.

I intended for the ginger ale to be my white wine, and headed down the stairs to the entertainment room that was opposite to the den. The entertainment room had a modern theme, with sleek black leather furniture, a large flat screen TV and a very nice stereo system. The room also had a bar set with five bar stools and all of the fixings for proper entertaining, and the lighting mood could be set to a softer tone for what I imagined to be a more intimate setting.

As I poured the ginger ale into a champagne flute I noticed the only flaw with my transformation to Sally, my finger nails. They were drab and hardly feminine looking. I knew that Sally had several packages of press on nails, and while I had never used them before, I decided tonight required perfection. I seated myself again at the downstairs makeup table and carefully read the instructions on one of the packages. Pretty simple, and the nail polish remover would make it easy to remove them in the morning.

I picked the French manicure style, since it was the most numerous of the packages, and after a few false steps, finally had each of my hands transformed into much more feminine looking style. The false nails extended beyond my normal length, and I was surprised at how different it felt to pick things up while wearing them.

I thought briefly about how hard it would be to unzip the skirt or do almost anything else in the morning, but figured that I would remove the press on nails the first thing before having to do anything. Of course, the first task at hand was to re-position my full hardness, which had become uncomfortable as I had worked on applying the press on nails. I usually tucked when I dressed, but somehow, I had slipped out of place. I loved the look of my now totally feminine left hand holding the hem of the skirt as my right hand slipped into the pantyhose.

As I touched myself, the feeling of the nails had an amazing effect on me. They really changed the sensation of touch, and it was a bit awkward forcing my hardness back into position, but as I finished, I once again had a nice smooth feminine front. Pleased with the now total transformation, I decided that I would hold off masturbating until I changed into whichever negligee or nightgown that caught my eye later in the evening.

I was actually quite proud of my ability to resist the usual temptation, but my sexual satisfaction was secondary to me fully assuming the role of Sally as the hostess, and I hurried back to attend to my imaginary “guests.” Holding my champagne glass of ginger ale, I turned the stereo on and dialed in one of the local pop stations and ‘Womanizer’ by Britney Spears was playing. I couldn’t resist starting to twist and dance to the music the way real women and girls would do.

Hips swaying, mouthing the words, and playfully brushing at my hair as I moved, I was so taken in the moment that I never heard the front door open, the stomping off of the snow, or the steps on the stairs. But I definitely heard the questioning word that came from Jack, “Carole?” I almost dropped the champagne glass as I otherwise froze in place. “Honey, what’s going on, I thought…” and then the realization hit him, I wasn’t Carole. I turned to face Jack with tears welling up in my eyes, as I murmured, “No, Mr. Douglas, it’s me, Kevin.”

The sound of my voice was the only thing that gave identity to the person who in all other respects looked like Carole from across the room. “What’s going on, why are you… I mean, why?” Tearfully, the crying started immediately as I clutched the champagne glass with both hands to my faux bosom, my body racked with sobs.

I couldn’t bear to look at his face as I realized the sense of betrayal of trust I knew my actions had caused. I stood there, sobbing, for about the longest minute of my life, my mind racing with thoughts of the anger my parents would have, as well as the public humiliation that was surely to come.

Jack then told me to clean myself up and said he would wait for me downstairs. I went to the bathroom and started undressing as fast as I could. I felt so ashamed with so many questions in my head. I kept wondering how I would be able to explain myself to Jack. It was one of the longest night I ever had. I cleaned myself up and went downstairs. Jack was sitting on the couch looking much tensed. I apologized to him, crying all the time. He then told me that he would forgive me and forget everything but I would never be allowed to babysit for them again. I agreed and thanked him for being so generous and left the house, not once looking back.

The End

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  1. Its to bad the story ended the way it did. I think a better ending would have been that Jack took you into his arms and started kissing you. At this point you could have dropped to your knees and unzipped his pants and reached in and took his hardening manhood out and kissed it. A man can’t resist a blowjob and from a pretty “woman” it can’t get any better. After he shot his load into your mouth and down your throat he probably would have taken you up to the bedroom and made love to you. There is no sensation quite like having a hard cock in your ass.

  2. Yes i was looking for to that big ending,,where Jack makes love to you,,after all the effort to look so pretty and sexy as a woman,,,his woman,,,the woman who would put a smile on his face and keep it there,,”No” matter what it takes…oh yes better ending

  3. sweet story, but like the others obviously I was looking for the “other” ending, with Jack keeping you as a 2nd Carole for himself whenever he wanted (and that that also was the reason why he paid you much better than agreed). The given ending is probably more realistic, but as this is a fantasy only anyway…

  4. i know you have already heard this opinion before, but i was hoping for the father Jack to turn the boy into his own crossdressing sex slave using the boys humiliation as leverage to get him to do whatever and whoever Jack says to do. I was hoping for possibly over the summer vacation that the boy would be staying over at their place more and more and Jack would build a secret basement dungeon with hidden entranceway completely soundproof to put the boy on a shelf and torture him in every perverted sexy possible way. Forcing him to act as Carol but a slutty dirty version that Jack always wanted, and the boy would be on call while locked in the dungeon and be constantly in perfect makeup and wig and wear whatever he was told to wear to satisfy his perverted jailer. Jack would slowly stretch his virgin hole to a point that he could take on most big hung men, as Jack would be the biggest most well hung of all. Jack would be absolutely sadistic as well as super perverted and thrives off of the sexual torture, humiliation and just straight up pain that he dishes out to his new toy, Carol two. Id love to read about how he restrains Him very securely so he cannot move at all then brands him on his ass cheek, the boy screaming in agony as Jack laughs and spanks his ass unmercifully! Jack then would apply some burn ointment onto the new brand and as he rubs it in, his insatiable lust kicks in and he rubs some ointment onto and up into the boys rectum, first a finger, then two , as the boy is screaming and crying, unable to move a muscle, weeping loudly from the pain but equally from the pure humiliation of being branded like livestock and being a sex slave to this sick pervert giving in to his most sickest desires and being filmed at every moment. The horror of being forced so suck Jacks enormous cock as well as swallow his disgusting sperm whenever Jack wasnt shooting his giant cumloads up his ass right up into the boys guts and forcing the boy to BEG JACK to be allowed to suck his cock. to tell Jack that he “loves him so much” and is so glad that Jack captured him and is planning on keeping him for the rest of his LIFE ! This thought of endless pain and torture, humiliation and constant unwanted FORCED gay bondage sex with Jack and Jacks friends as well as the random dobermans and german sheppards occasionally is what keeps Carol two ( the boy) awake and openly loudly weeping at night. He yells out to Jack and begs for his release, and promises Jack anything and everything to be free again, and Jack has cameras and microphones all over the dungeon recording everything always. Jack would sometimes elude to the possibility of releasing the boy in the very near future but then yanking the rug out from under him so to speak at the very last second to destroy the boy mentally and drive him to the brink of suicide, which will not be allowed. Way too easy to go out like that! Id like to read about the boy having all his body hair removed permanently using some sort of painful home brewed electrolysis machine, about Jack restricting the boys caloric intake to a tenth of what is considered normal to keep him thin and petite, too weak to resist, and so hungry that Jacks cum is a welcome snack that is gobbled up quickly. Fuck now IM getting a hard on! If you dont write the rest of the story would you allow ME to pick it up and run with it using these ideas? You might enjoy it too! Last thing- just when the boy thought it could not get much worse than it already is, Jack abducts another youth of similar age as Carole two and for a month he never sees the other captive but hears him screaming as he is raped, trained, branded, forced to eat cum, starved, pissed on, fucked by dogs and tormented with the reality of living the rest of his long life in constant pain, torture humiliation, forced gay sex, forced beastiality, and just plain old torture just for the sake of torture. After a reasonable period of training the new slave, and after he has been feminized with hair removal as well as his anus stretched out to accommodate huge cocks and throat fucked until he no longer gags and vomits while he is throat fucked, the two boys finally meet. This can get very interesting now, both boys come from a strong catholic upbringing with tons of guilt, are very hederosexual and hate the thought of homosexual sex as it is repulsive to them both will be tied together into a forced 69 cock sucking session and whoever cums first will be tortured in a SPECIAL EXTRA AWFUL WAY so each boy will be motivated to suck the others cock to get him to cum before he himself cums, and as an added bonus, during this session Jack will be there with random anal stimulating toys inserting them into the boys pussies (assholes) and seeing their reactions. Forcing both boys to make out with each other, tongues darting in and out of each others mouths as they cry, mascara getting smeared, lipstick all over each others mouths and faces, being locked up in chastity cages with no possibility of cumming anytime soon, being fed viagras ground up in their tiny portions of food and force fed estrogen and have their pecs pumped by a milking machine to stretch out the skin to accept breast implants!! oh hell yes!

  5. I love your ending better 💟

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