Maing of a Crossdresser

Pandora's Box and new nightclub for drag queens.

Introduction:

This is the second part of a two-part, true story as told to me by David, a bisexual man who sometimes enjoys dressing as a woman. When dressed as a woman, he goes by the name of Kelly. Unlike other drag queens who don't even disguise their voices and/or who don't even shave their faces, their arms, their chests, and their legs, David was in complete character when dressed as Kelly. He wanted to look as much like a woman as he could.

Perhaps, evidence that he should have been born a woman instead of a man, when dressed as Kelly, making for a very pretty and sexually desirable woman, he looked more like a woman than he looked like a man. When in the character of Kelly, he not only looked like Kelly but also, he walked like her, laughed like her, and talked like her. Anyone seeing David dressed as Kelly would be completely fooled to know that he was a man in drag.

Moreover, any straight man seeing him dressed as Kelly would want to have sex with her. Any gay man seeing him dressed as Kelly would want to have sex with him. Any swinging couple seeing him dressed as Kelly would want to have a threesome with them both. A win/win/win for David, whether with a man, a woman, or a couple, he was always having sex. Sucking, licking, and fucking, Kelly was his key to his admission of promiscuous sex.

Shocking to some, I know, but not to him. Having sex with beautiful women, with handsome men, and with swinging couples while sometimes dressed as a woman was normal for David. Totally comfortable when dressed as a woman, he fooled more people than not. He looked more like a woman that some born female did. Helping him to get what he sexually wanted, having sex with men, women, and couples increased his chances of getting lucky with someone. Already, by being bisexual, he doubled his sexual field of sex partners.

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Continued from Chapter 01:

"Do you need to cum," asked Vanessa, David's mother while shocking him? She paused while staring down at his naked erection before staring up at him with her big blue eyes. She moved back her red hair with a flip of her pretty head. "I can help you with that," she said with a sexy smile while reaching out her hand to touch his erect prick when he didn't answer her.

'His mother touched his erect prick again. He couldn't believe she fondled the head of his cock with her manicured fingertips,' he thought.

She continued staring at his prick while fondling his big dick. With her hand wrapped around his exposed cock, she slowly stroked him while staring at his prick before staring up at him. Like mother like son, in the way that he was enamored with his mother's naked breasts, she was obviously enamored with his naked prick.

'I can't believe my mother asked me if I needed to cum? I can't believe she's stroking my prick while staring at my prick,' he thought while staring at his mother's hand fondling his cock and stroking his cock. 'Sexually tempting me with her offer to make me cum, she makes my cock hard and my will to refuse her sex when she stares up at me with her big, blue eyes.'

"Tell me. You decide," she said pausing again to ask her question again while slowly stroking him. "Do you need to cum?" She stared down at his erect prick again. "With your cock so big and so hard, you look like you need to cum," she said giving him a sexy smile.

Then, sexually teasing him, she laughed while continuing with what she obviously knew would get to him. She stared up at him while feeling and fondling her nightgown clad breasts and fingering her nipples with one hand. She stroked him a little harder and a little faster with her other hand.

"Tell me Davy, would you like Mommy to get you off," she asked staring down at his naked prick? "Would you like me to masturbate you," she asked giving him the eye? "Tell me, Davy, where would you like to cum? Would you like to cum all over my hand," she asked?

She wiped her hand with her other hand as if he had just cum on her hand.

"Or would you like to cum across my naked breasts," she asked?"

Sexually teasing him, while puffing out her chest as she slid a slow hand across her nightgown clad tits. Stopping at her nipples to erect them, she fingered one nipple before fingering her other nipple through her nightgown. Pulling them, turning them, and twisting them, with her nipples pressed hard against the thin material of her sheer and sexy nightgown, she made her nipples bigger.

"Or would you like to cum in Mommy's mouth," asked Vanessa?

She slid a slow tongue across her red, full lips while staring at him and making eye contact with him. Instead of scolding him to cum in her moth, daring him to do so, she encouraged him to cum in her mouth. Then, as if doing a striptease, she slowly and sexily removed her nightgown.

While he was nearly naked, his mother was now standing in his bedroom naked. Having seen her totally naked lots of times before, he couldn't believe his MILF of a mother was naked again. A sucker to her sexual charms, she was such an incestuous whore. Now that he was seeing his mother naked again, he couldn't remove his eyes from her big, C cup breasts and her red, trimmed pussy.

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Not scolding him for being sexually excited, but encouraging him again instead, she wrapped her hand around his erect prick again, squeezed it, and briefly stroked him while fondling the head of his cock with her fingertips. Obviously, his mother loved his big dick as much as he loved her naked body. She was as enamored with his naked, erect prick as much as he was enamored with her naked and shapely, C cup breasts and erect nipples.

As if she was his lover instead of his mother, she stared up at him while waiting for him to answer her. As if he was her lover instead of her son, he stared at her with sexual lust and forbidden love. Continuing to sexually tease him, she stroked him a little faster and a little harder. Then, while making solid eye contact, as if hinting where she wanted him to cum, she slid a slow tongue across her red, full lips again while staring at him.

"In your mouth," he said while staring at her lips and watching her tongue. "I'd love to cum in your mouth, Mother," he said sliding a slow finger across her red, full lips.

Continuing to sexually tease him, she took his finger in her mouth. Then, she licked and sucked his finger as if she was licking and sucking his cock. She continued to sexily stare at him while sucking his finger. This was his mother and not some whore that he picked up and brought home for the night. Yet, with them together, yet again, he'd rather have incestuous sex with his mother than with anyone else.

"I love you, Mom," he said. "I want you to blow me. I want you to suck my prick. I need to cum in your mouth, Mother. I want to watch you swallow my cum before licking my cock clean," said David.

Assuming the position, with this obviously not her first blowjob, Vanessa moved to her knees in front of her son while staring up at him. She continued staring up at him while fondling the head of his erect prick with her fingertips. She slowly stroked him before lowering her mouth to lick his prick.

"Feel free to touch my breasts and finger my nipples while I suck your cock, David," said Vanessa removing his cock from her mouth to speak before taking his stiff prick in her mouth again. As if she was a clinician performing a medical procedure, she sucked her son's prick before removing his cock from her mouth to speak again. "I love having my breasts fondled and my nipples pulled, turned, and twisted. And just so you know, I love sucking cock and I can't wait to suck your big dick, my son's erect prick."

If it wasn't enough that his mother was on her knees in front of him and sucking him while naked, he couldn't believe that she invited him to feel her naked breasts and finger her erect nipples. Breaking all of the mother and son boundaries of forbidden and illicit sex, he couldn't believe that she willingly volunteered to blow him. A sexy vision he always imagined seeing while masturbating himself, he stared down at his naked mother staring up at him with his hard, erect cock in her mouth.

Something he always imagined doing while masturbating himself, he couldn't believe he was seeing her naked breasts, feeling her naked breasts, and fondling her big tits while fingering her erect nipples. Something he always imagined her doing while masturbating himself, he couldn't believe his mother was blowing him while stroking him again. Something he always imagined her doing while masturbating himself, he couldn't believe that she was allowing him to cum in her mouth.

"Oh, Mom," he said feeling her big, naked breasts and fondling her erect nipples. "Suck my cock. Blow me," he said putting a gentle hand to the back of his mother's red, pretty head while humping her mouth and fucking her face. He humped her mouth harder and fucked her face faster.

With her stroking him faster, stroking him harder, and sucking him deeper, it didn't take David long to cum in his mother's mouth. Something he never knew until he was older, much like the sexual fantasies of many women, he didn't know that his mother's sexual fantasy was to have sex with a crossdresser. If it wasn't sexually exciting enough for his mother that he enjoyed dressing as a woman, he was her son. His mother was having sex with her crossdressing son.

"With your cock in my mouth, call me Vanessa instead of Mom or mother," she said with a sexy laugh. "I feel weird when you call me Mom while I'm sucking you," she said with a sexy laugh.

Sexually aroused when she was dressing him, she had been patiently waiting for him to turn 18-years-old before sexually seducing her son. Now that he was of legal age, she took sexual pleasure in dressing him as a beautiful woman before having incestuous sex with him. No denying her, she was determined to stroke her son, suck her son, and fuck her son. Wanting him to give her sexual pleasure in return, she expected him to finger her pussy, lick her pussy, and fuck her cunt and give her multiple, sexual orgasms.

Chapter 02:

Shocking him and sexually exciting him even more, the first time his mother saw and touched his naked prick, even today, years later, whenever horny, he still masturbated over that life changing day. Even now, he couldn't believe she removed her nightgown and invited him to touch, feel, and fondle her C cup breasts while fingering her erect nipples. What kind of mother does that with her son? Yet, he was glad she did because if left up to him, he never would have made the first incestuous move. He never would have had forbidden sex with his mother.

The first time seeing his naked cock, he remembered how she stared at his exposed prick. The first time touching him, he remembered her fondling the head of his prick with her manicured fingers. Even now, years later, when he was 18-years-old, now that he's 22-years-old, he couldn't believe she stroked his cock and masturbated him while staring up at him.

Then, something her never thought she'd do and that he'd ever see her do, he couldn't believe it when she took him in her mouth and sucked his prick. While she sexily stared up at him, seeing his cock buried in his mother's mouth was so hot. Then, when he exploded a huge load of cum in his mother's mouth, he couldn't believe she swallowed it before licking his cock clean.

Instead of being embarrassed or ashamed, instead of rebuking her for staring at, touching, stroking, and sucking his erect dick, as if he was her lover instead of her son, he loved the sexual attention she paid his engorged cock. Then, later, after they had sex and rested while enjoying the afterglow of sex, she fixed his hair. As if he was her daughter instead of her son, she allowed him to wear one of her wigs and applied his makeup. When he saw himself in the mirror, happy with the result and liking what he saw, he looked very pretty.

Making him feel special, he loved the personal attention she paid him. When she was fussing over him, even though he had already seen and fondled her naked breasts, so sexy, she gave him uninterrupted down nightgown views of her naked breasts, her areolas, and her erect nipples. Unable to get enough of seeing them, touching them, and fondling them, he loved her tits, his mother's tits.

Never had his mother fussed over him as she did that Halloween. Never had his mother given him her undivided attention as she did that day. She not only made him feel special but also, she made him feel beautiful and sexy. He loved his mother and his mother loved him. Yet, it wasn't until that fateful day years ago when they had incestuous sex, that he discovered how much mother and son loved one another.

Especially after she removed her nightgown and flashed him her naked tits, she made him so hard. She made him so horny. Then, when she stroked his cock, sucked his cock, and allowed him to cum in her mouth, he couldn't believe he had sex with his MILF of a mother. Turned on and sexually excited, he couldn't believe she had sex with him. Hard to wrap his head around all of that happened so fast, as if she had wanted to have sex with him, too, he still couldn't believe his mother sucked his prick.

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"Oh, David, I knew you'd make such a good-looking woman. You're so pretty. You're even prettier than your sister. You're much prettier as a woman than you are handsome as a man," she said with a laugh. "Look at yourself in the mirror. You look like me when I was your age. With you walking like me, talking like me, laughing like me, and looking like me, you could be a much younger version of me," she said with a sexy laugh. "You're so very beautiful. If you weren't my son, I'd never guess that you were a man."

Reinforcing his earliest need to cross dress, he wanted to look pretty again. Fawning over him and giving him their undivided attention, his sister and his aunt made a big deal over how he looked, too. Allowing them to strip him naked and dress him, in the way that he allowed his mother to see him naked, he allowed his sister and aunt to see him naked, too. In the way that his mother touched, felt, and stroked his naked prick, his sister and aunt touched, felt, and stroked his naked prick.

'All in the family,' he thought. 'Incest is best when having sex with not only my MILF of a mother but also with my sexy sister and my MILF of an aunt.'

Taking two to play the incest game, in the way that his mother stared at his cock, his sister and aunt stared at his naked prick, too. In the way that his mother stripped herself naked, his sister and aunt stripped themselves naked too. In the way that he had an erection for his mother, he had an erection for his sister and his aunt, too. In the way that he had forbidden sex with his mother, he had illicit sex with his sister and aunt, too.

Unbeknownst to him until years later, in the way that his mother's sexual fantasy was to have sex with a crossdresser, his sister's and aunt's sexual fantasies were to have sex with crossdressers, too. In the way that his mother removed her nightgown, his sister and aunt removed their blouses and bras. In the way that his mother stroked his naked prick while sucking his erect cock, his sister and aunt gave him blowjobs, too. They both allowed him to cum in their mouths, while he fondled their naked breasts and fingered their erect nipples.

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As he grew older, when he was 20-years-old and his mother was 40-years-old, what added to his need to cross dress was that he took the same sizes as his mother. From shoes to pants to bras, and to dresses, they took the exact same sizes. Already, whenever dressed as Kelly, borrowing whatever he needed from his mother, she had a full wardrobe of clothes to wear. With them taking the same shoe size, and his Mom having shoes and accessories galore, Kelly already had a complete compliment of shoes, costume jewelry, and accessories, too.

His mother was a shopper. She loved to shop. Whenever she went to the mall, she was gone for hours. Only, oddly enough, instead of taking his sister shopping with her, she took him shopping with her. Not having to twist his arm, he loved shopping with his mother. As if his treat for spending time with her, she always bought him something, too. With him dressed as his sister, they fussed over clothes as if he was her daughter instead of her son.

"I'm taking you shopping with me, David, because I want a man's opinion," she said. "C'mon. Let's go."

Obediently obeying his mother and, submissively never saying no to her, sometimes, she'd even sneak him in the dressing room with her. Where many men who are sexually attracted to their mothers wished they could see their mothers in their bras and panties, topless, and naked, he saw his mother in all manner of undress many times. He remembered the first time she stripped down to her underwear in front of him, having already had sex with his mother, oddly enough, he was more interested in seeing her underwear than in seeing her semi-naked and naked body.

'I like her bra,' he thought. 'I like her matching panties. Men's underwear is so boring and women's underwear is so sexy, lacy, and fancy. While staring at his mother in her lingerie, she definitely had a sexy and shapely body,' he thought.

Then, with her not stopping there, when she removed her bra to try on a new bra or a bathing suit, as if deliberately exposing herself to him, she turned and faced him while undressing and while dressing. She stared at him staring at her naked breasts. Obviously, her exhibitionism matched his voyeurism.

Yet, oddly enough, been there and done that, instead of being sexually excited seeing his mother topless and/or naked, he looked at her as if he was a fashion designer and she was a model. He looked at her as if he was a gay man or a woman. While wishing he had such a sexy and shapely body as his mother, he looked at her while wishing he was her.

He remembered the first time seeing her naked breasts when she blew him and invited him to fondle her naked tits while fingering her erect nipples. He had just turned 18-years-old and just started crossdressing. As if she couldn't wait to have sex with him, giving him her naked body, her motherly hands, her beautiful mouth, and her warm, wet pussy, she was her birthday gift to him. The best birthday gift she could have given him, he couldn't wait to return the favor and give her sex for her birthday, too.

Only, unbeknownst to him, he didn't know his mother had impatiently been waiting for him to turn 18-years-old to have sex with him. Unbeknownst to him, he didn't know his mother had a fetish for crossdressers. He didn't know his mother always wanted to have sex with a man dressed as a woman. A bonus that made her wild with sexual excitement, not only was he her son but also, he was a crossdresser, too. He couldn't have hand delivered a better sexual fantasy to his mother than that.

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David's Mom, Vanessa, has lush red hair, big, blue eyes, freckles, and beautiful C cup breasts. So full and so shapely, she has big nipples, too. If he was wasn't sexually attracted to his mother before, with him having a sexual fetish for women's breasts, especially big breasts, he'd be sexually attracted to her because of her perfect set of tits. Indeed, she has quite the rack, tits that any woman would be proud to have, show, and display.

With him loving women's round, firm, and shapely asses, his mother didn't disappoint him in that regard either. Yet, other than that first time they had sex, he no longer acted on the lustful, sexual impulses that he had. Instead of only having sex with her that one time, regretting his decision not to continue having sex with his mother, he wished he had sex with his mother again.

Only, even though he was sexually attracted to her at first, once he started having bisexual sex with other men, women, and couples, he wasn't as sexually attracted to her now as he once was before. He was more sexually attracted to women and men his age. Yet, still incestuously enamored with her, he loved his mother, of course. He'd do anything for his mother, even take care of her sexual needs when asked.