tagTranssexuals & CrossdressersWoman Cross Dresses for Power & Sex

Woman Cross Dresses for Power & Sex


Tucked in the far corner of a dark, dancehall parking lot, Sarah, also known as Robert, was having sex in a car with Joseph, also known as Josephine. Having sex in a car was no big deal. A lot of couples have sex in cars. Yet, if a passerby could see through the steamy windows, a sight to behold, even at a Halloween Masquerade party, which this wasn't, they'd see a woman dressed as a man and a man dressed as a woman having sex in the backseat of a car.

With her shirt unbuttoned and her bra lifted to her shoulders, Josephine's hands were all over Robert's big tits. Unable to control themselves, unable to wait to make love at his house or her apartment, he filled her pussy with his cock in the backseat of his black Chrysler 300. In an out, they humped, while fucking. Deeper and deeper, Josephine pushed his cock in Robert's pussy.

"I love your tits, Robert. So big, so firm, and so round, I love sucking your nipples, while fucking you."

"Fuck me, Josephine. Stick your big, hard cock in my warm, wet pussy."

Unusual for Sarah to be so openly sexual, with all the dirty talking she was doing, she was always able to maintain her decorum, even during her college days, when she was a sexy cheerleader for a horny football team that were free with their comments and quicker with their hands, when on the official team bus. Even though she was invited, more than once, to give some college jock a hand job and/or a blowjob, as their reward for winning a football game, whether on a plane, a train, or a ship, she never had sex in a vehicle. Sure, when dressed as Sarah, she kissed, fondled, groped, and felt plenty of men in cars before, while allowing men to kiss, fondle, grope and feel her, but she never did the actually sexual act in a car, that is, until now.

Beyond reasonability, as weird as it was wildly erotic, with her tongue down his throat, Sarah was making out with a man she had just met, a man who was dressed as a woman, while Joseph was making out with her, a woman he had just met, a woman who was dressed as a man. All a bit convolutedly topsy-turvy, their cross dressing not only added to their physical attraction to one another but also to their sexual excitement. Sometimes difficult to tell one from the other, with Joseph dressed as Josephine and Sarah dressed as Robert, reporting the sexual activity of their actions may be a bit difficult without a scorecard.

She wondered if Joseph was married or attached to someone? Unlike her to fool around with a man that was already in a committed relationship, Sarah no longer cared. All she knew was, after dancing with him all night, after feeling his firm, tight ass through his short skirt, and after going up the front of his miniskirt to feel his cock through his silk panties, she had to have him.

While on the dance floor, already wet with sexual desire for him, she imagined sucking him, before fucking him. With his cock nearly sticking out the side of his panty, the contrast of his hard cock against the softness of his silk panties was so very exciting. Between the floral scent of his perfume and the musky aroma of her cologne, their combined fragrances were intoxicating. With his body pressed and rubbing against her, nearly dry humping her with the beat of the music, no longer able to control her sexual lust for him, she needed to feel his big, hard cock in her hand, in her mouth, and in her pussy.

Now that the dance was over and with everyone gone home, they were alone, while sitting in the backseat of his car, a car that had a seat wide and long enough to accommodate whatever they wanted to do sexually. After feeling his big prick through his panty all night, she couldn't wait to see it. She couldn't wait to reach beneath his short skirt, push his panty aside, pull out his cock, and hold his prick in her hand, while stroking him, before sucking him. Never has she wanted to blow a man as much as she wanted to suck Josephine's cock. Wanting to feel the heat of his hardness in her hand, in the way that he was feeling the warm wetness of her tongue in his mouth, never had she given a blowjob in a car, until now. A first time for everything, never has she had sex with a man dressed as a woman, while she was dressed as a man, until now. Never has she wanted anyone to remove her suit pants, pull down her boxer shorts, finger, lick, and fuck her pussy, as she wanted him to do to her, until now.

"Oh, Josephine, I love the feel of your hard cock through your silk panties," said Sarah kissing and kissing Joseph. "Never would I have imagined the feel of silk would be so exciting against my fingertips. I can't wait to suck you," she said whispering in his ear, while licking the inside of his ear.

"Oh, Robert, I love the feel of your big, bra clad breasts through your men's shirt and necktie," said Joseph kissing and kissing Sarah.

With her hand fingering the head of his cock through his pink panty, while his cock pushed and pulsated against her fingers, Sarah felt Joseph's big bulge grow harder. Unable to wait any longer, she pushed Joseph's panty aside with her manicured finger and pulled out his prick. Fondling him, while stroking him and French kissing him, eager to take a peek, she lifted up his short skirt to see his big prick.

"Your cock is so big, Josephine," she said stroking him faster, while fondling the head of his cock with her fingertips.

"Your breasts are so big, Robert," he said feeling her through her clothes. "I love your big, hard nipples," he said taking them in his mouth to suck them.

While Sarah was kissing him, feeling his cock through his panties, before freeing and stroking his cock, Joseph was unbuttoning Sarah's shirt. Feeling her abundant breasts through her bra, before lifting her bra and exposing her beautiful breasts, he fingered her nipples, before sucking them. With no turning back now, unable to stop to find a more private place, the attention that he paid to her nipples was all that Sarah needed to put her over the edge. While Joseph reclined back in the comfort of the leather seat, Sarah lowered herself down to take his cock in her mouth.

"Suck my cock, Robert. Suck me. Blow me, Robert. Blow me."

"My pleasure, Josephine. I can't wait to take your big cock in my mouth."

Robert sucked Josephine's cock, until he was hard and ready. Then, Josephine removed Robert's dress pants and pulled down her boxer shorts. With his finger fingering her clit and fucking her pussy, Josephine leaned Robert back in the softness of the black leather seat. Then, draping her legs over his shoulders, before lowering himself and burying his makeup clad face and lipstick decorated mouth in Robert's warm, wet pussy, he licked and fingered her pussy. Once she was wet enough, once she was on the verge of having an orgasm, so wet that Josephine could slip his erect prick in Robert's pussy with the first forward thrust and deep hump, Joseph fucked Sarah.

* * * * *

With a tailored, pinstriped, blue suit, a fitted shirt, a complementing tie with gold tie tack, bejeweled cufflinks, a pair of crisply ironed, flattering slacks, coordinating socks, an alligator leather belt, a colorful pocket square precisely place in a suit coat, highly polished dress shoes, and a Fedora hat perched atop her head, appropriately tilted to one side, Sarah was now Robert, her Dad's first name. The whole nine yards, resplendent in men's clothes from head to toe, looking so very elegantly dapper, even better than how her father used to dress, pleased at what she had created, Sarah gazed at herself in the full-length mirror. A wish come true and a long time coming desire that manifested itself in her dressing as a man, when her Dad died, with her missing him etched forever in her brain, her need to continue her life dressed as her father permanently altered and transformed her feminine side to more of a masculine one.

In the perfected way that she looked, looking better than Julie Andrews in the movie, Victor Victoria, better than Madonna, when she dressed as a man in her music videos, and even better than Terri Griffith in the movie, Just One of the Guys, men's clothes were Sarah's intended, albeit not so subtle statement to make. By wearing men's clothes, the power uniform accepted in a male based society and one that opened so many doors for her, when dressed as a mister that were closed to her dressed as a miss, even though everyone knew she was a woman dressed as a man, her transformation would be complete, if only she had a penis. Then, again, if she had a penis, she'd no longer be a woman dressed as a man and the only thing she enjoyed more than dressing as a man was being a sexy, sexual woman.

Of course, her firm, C cup breasts, nearly impossible to hide, unless tightly bound and flattened against her chest, her blue eye makeup, long eye lashes, and blush rouge, her full lips colored with ruby, red lipstick, and her long, straight, blonde, hair declared that she's a sheep in wolf's clothes. Only, she was no sheep. In the way that the wolf never looked like a sheep, looking very much like a woman, even when dressed as a man, looking so much like one of Prince's entourage, back in the day, she was, indeed, the female version of Boy George. Oddly enough, as if she wore a uniform that equally attracted and appealed to both sexes, as well as all sexual orientations, whether heterosexual, bi-sexual, gay, lesbian, transsexual, transgender, and/or cross dresser, the uniqueness of how she so provocatively dressed was arousing not only to men but also to women.

Finally, in the way of Lady Gaga on steroids, no longer tortured and confused by her need to dress as a man, not wanting to be classed as one sex or the other, she understood how dressing as a man relieved her of her defined stamp that she was a heterosexual female, albeit a beautiful, heterosexual female, dressed as a man. Now, firmly planted somewhere in between, if only by her manly attire, with her physical transformation nearly complete, she left people scratching their heads, while wondering, is she straight, bi-sexual, lesbian, transsexual, transgender, or just a male impersonator?

As if demonstrating her personal dawning of a new age of Aquarius, no longer defined by just one word, woman, she was someone that begged a redefinition. Maybe ahead of her time, whether men or women, everyone would dress the same, as they do in North Korea and in George Orwell's 1984 world. The female world, as she knew it, ended, once she tied a full Windsor knot in her necktie and pulled up boxer shorts, instead of panties.

To Sarah, her alter ego Robert wasn't a cross dresser. Cross dressing as a man wasn't just for play or part of a sexual fetish, cross dressing as a man was serious business that stemmed from the love lost, when her father died. Much in the way that a service person in the military dons their uniform or a police officer transforms their person, when wearing the badge, the gun, and taking the oath to serve and protect society, as if putting on a uniform that not only disguised but also that redefined who she is, Sarah soon realized that donning the clothes of a man affected her not only physically but also mentally and emotionally. No longer feeling like an ordinary woman and unable, of course, to feel like a real man, in limbo between female and male, unable to go back and unable to go forward, feeling how a male cross dresser must feel, when needing to wear a dress, she was stuck somewhere in the middle.

With insights inspired by dressing like a man, already there emotionally, Sarah knew, not that she wanted to be a man, that she couldn't pull her sexuality change off in the way that Chaz Bono had done. If she didn't know any better, if Chaz hadn't been the daughter of Cher, a celebrity, but an ordinary person, she'd think that Chaz was born a man. Yet, truth be told, Sarah wasn't trying to fool anyone. Truth be told, she wasn't even a lesbian or a bi-sexual. No doubt, in honor and in memory of her father, perhaps a woman who needed therapy, she was just a woman who wanted to dress as a man. Surely, if she was trying to make people believe she was a man, she'd bind her breasts, remove her makeup, cut her hair, and take massive doses of testosterone to change her voice and to give her facial hair, in the way that Chaz had done.

If she was trying to deceive people in thinking that she was a man, instead of looking like some abnormality from the cover of Esquire and GQ magazines gone wrong, she wouldn't dress as perfectly, as she does. No man, but Carson Kressley, Tim Gunn, and Mr. Blackwell, dresses that way. If she really wanted to deceive people into thinking that she was a man, she'd buy a pickup truck, don a sweatshirt, and wear jeans, sneakers, and a baseball cap, which, by the way, is not only how most men dress but also how most women dress, too, but for the baseball cap.

* * * * *

It began two years ago when Sarah attended a dance at the Switchers Club. It was a club that catered to the cross-dressing crowd, typically men with women there, too, supporting and helping their man to make the cross dressing switch from male to female. They had contests every month not only for the best outfit but also for the best ability to fool the public in thinking that they were female. Yet, just in the way that Sarah dressed as Robert, a woman who looked nothing like a man, there were plenty of men who, when even in heels, makeup, and wigs, looking nothing like a woman, especially those men who refused to shave their mustaches and beards. To them, as it was for her, not really wanting to fool anyone, wearing the clothes was what was important. There were some gays and drag queens, who frequented the club, but it was mostly cross-dressing, heterosexual men who filled the dance floor every week with their wives, girlfriends, and/or significant others.

Sarah heard about the club and wanted to see what happened there for herself. Dressing as a man and not as a woman, this was her perfect opportunity to experiment, while not being deemed a freak and accepted for who she was. She had a great time dancing, talking, laughing, and drinking. While dressed as a man, with dating men and looking for a man out of the equation, not having to worry about the male/female rules of looking for someone in a crowded club, she could be alter ego, manly self. Everyone was so open and friendly at the Switchers Club that, for the first time, she felt comfortably accepted, while dressed as a man.

Sarah asked men to dance, at least she thought that they were men, and laughed when she realized she had been fooled by tall and beautiful women that were dressed as men. She didn't know, until nearly the end of the evening that her dance partners were women. With them hitting on her all night, she was shocked when her dance partners went into the ladies restroom to change and emerged wearing woman's clothes. Before leaving, hoping to get her number, they came over to chat with her at her table. Not interested in women, just men, Sarah politely turned them down. Typically the one who had others scratching their heads, it was fun being fooled and she laughed that she had been so deceived. Not knowing anyone else who enjoyed dressing as a man, until now, after having experienced cross dressing herself, now that she knew there were others like her, she more enjoyed dressing like a man.

As a young girl, Sarah had stomped around in her Daddy's shoes and put on his dress shirts. While he was away at work, wearing his clothes and smelling all his manly smells made her feel comfortable and happy. She didn't understand why she felt that way, but pretending she was her father was a wonderful feeling of security. She loved the way the shirts smelled of laundry detergent and starch, and if she got one of his shirts from out of the dirty clothes hamper, it smelled just like her Dad. She felt powerful and safe in his shirts and shoes. Her Mom's clothes didn't give her the same feeling. Her Mom's clothes made her feel weakly subservient. While other girls tried on their Mom's shoes, dresses, make-up, and jewelry, Sarah always gravitated to her Dad's clothes.

Sarah could have been described as a tomboy. She always preferred playing with the boys than with the girls. Whether to sporting events, fishing trips, or a trip to the hardware store, Sarah's Dad took her everywhere with him; they were best buddies. They went to the barbershop, Sears, the lumber yard, firehouse and many other male bastions that were hangouts for mostly men. Maybe it was because of his strong influence on her life, but Sarah found girls to be silly, foolish, self-centered, petty, childish, manipulative, and boring. She hated it when they giggled, teased, and batted their eye lashes at men. She thought them so stupidly subservient to behave in that way.

She used to play football, basketball, and baseball with all the guys in the neighborhood, until her Mom forbade her to do that anymore. Once she grew breasts, her Mom decided that her tomboy days were over. For the chance of a quick feel, a sneaky grope, a dry hump, and maybe even a kiss, when playing touch football, even though it was against the rules, the boys loved tackling her, getting her on the ground, and climbing on top of her.

Sarah wasn't a lesbian, she just preferred hanging around with the guys, instead of with the girls. Probably because of the relationship she had with her Dad and the insights that he gave her about men, she understood boys better than she did girls. Growing up in her neighborhood, she had more best men friends than she did have best girlfriends. With her hormones raging, Sarah discovered that she really loved men and wanted as many boyfriends as she could handle. She had a strong libido and was too hot to handle for many of the guys she dated in her teens. She was all woman, albeit a very strong woman, sometimes a man in a woman's body, nonetheless, she was definitely all woman. There wasn't any doubt in any minds of the guys she dated that she was one of the hottest women they had ever met.

Zsa Zsa Gabor reincarnated, born a natural blonde beauty with big, blue eyes, she was considered busty, curvy, and stunningly pretty. She had a bubble butt that stuck out just the right amount to give her a curvy figure, when looking at her from any side. Always so comfortable to be around, what the guys loved best about her was her great sense of humor and her quick wit. Was it not for her beauty and sexuality being the elephant in the room and always getting in the way of their friendship, she'd just be one of the guys. They were all so relaxed and comfortable with her that they'd talk about the most intimate details of their lives because they knew she'd never tell anyone, that is, until they matured and wanted to have sex with her, rather than just talk with her. Still, helping her process men, she understood the guy code and she'd never break their rules for any reason.

Sarah had plenty of boyfriends, but she hadn't found that special person to settle down with and raise a family. She wanted the kind of love that only comes around once in a lifetime. She wanted it all and wouldn't settle for less. Still a virgin, she didn't want to have intercourse with anyone until she found the right man. She had sucked some cocks, French kissed, touched, licked, and generally done everything short of intercourse, but she wanted to save that for the one special someone.

The men she dated seemed satisfied with a hand job and/or a blowjob and respected her wishes of her maintaining her virginity. There were a few who had a tough time taking no for an answer, so she didn't go out with them again. As she always told her friends, if a date pushed her about sex, they were toast. Yet, now that she enjoyed wearing men's clothes, in the way that Katherine Hepburn wore men's clothes in the 30's and 40's, she needed a man who accepted her in the way that she was.

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bySusanJillParker© 5 comments/ 38681 views/ 9 favorites

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