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Making of a Crossdresser Ch. 01

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This is the first 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 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, Dave was in complete character when dressed as Kelly. Perhaps, evidence that he should have been born a woman instead of a man, making a very pretty and sexy woman, he looked more like a woman than he looked like a man.

When in character, 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. 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.

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. Having sex with men, women, and couples increased his chances of getting lucky with someone. By being bisexual, he doubled his sexual field of sex partners. By being a crossdresser, he sexually appealed to women and men who had a secret, sexual fetish to have sex with a man dressed as a woman.

# # #

Author’s Warning:

If you are someone who hates everyone who is not like you, you should read another story. If you have a problem with gay sex, bisexual men, crossdressing, crossdressers, and individuals who are transgender then you should read another story. If you are prejudicial, closed minded, opinionated, a white supremist, and/or a Nazi disguised as a Republican wanting to make America great by giving to the rich and taking from the poor, then you should read another story. There’s nothing here for you to read.

“Go on. Get out! I’ll wait until you all leave before continuing. And take off those stupid, red hats. Give me those hats. Instead of making America great, you have ruined our country. Shame on you! How dare you? Shame on all of you!”

I turned to my personal bodyguard and protector, my big brother, literally, my really big brother, 6’9″ and taller with boots, 400-pound, Big Louie, to clear the room. Blessed with four brothers, my eldest brother Freddie, is 6’3″ and 230-pounds. He’s the meanest and the toughest of my brothers. Then, there are the twins, Vito and Guido, standing 6’6″ and weighing 260-pounds. They’re the most fun loving and always playing practical jokes.

“Big Louie, show these men the door. Go on. Go. Beat it. Scram. Get lost. Leave. Get the Hell out of here. I’ll wait until they all leave before continuing. Wow! Do you believe that? One man was a police officer and another man was a priest. I recognized my old high school gym teacher in the crowd and my mailman, too. It takes all types. I’m glad they’re gone. Good riddance to them. Bye! Adios! I’ll see you later.”

My ex-prostitute and stripper of a mother, Natty, had five children by four different men. With my whore of a mother having drunken and drugged out sex with all four of her sons, and with me an accident of birth who was born 20-years later, I suspect one of my brothers is my father. With me trying to sleep in my room with my bureau pushed up against my bedroom door, I’d hear my drunken mother having sex with a variety of men she brought home for the night to suck and fuck for money.

‘How’s that for fucked up? My mother is a stripper, a prostitute, and an incestuous whore, and one of my brothers could be my father,’ I thought. ‘I’m just glad that my mother wasn’t invited to this speaking event for those reading this story? Sorry Mom, but you’d never behave yourself in group of men. Once a whore always a whore.’

Had I invited her; she would have whored around to make some extra money. Had I invited her; she already would have been on her knees stroking and sucking cock. Had I invited her; she already would have been bending over the sink in the men’s room while being fucked in her pussy and/or in her ass.

Yet, enough about me, about my giant brothers, and my whore of a mother. This story isn’t about me. This story is about David and his alter ego, Kelly. This story is about a bisexual, crossdressing man. This story is about illicit mother and son sex. This story shines the light of blame on his mother as to not so much why he’s a bisexual but why he’s a crossdresser.

# # #

Maybe his mother had nothing to do with him being bisexual. Yet, perhaps, she had a lot to do with him needing to dress like a woman. Who knows? Based on the Kinsey Study and other similar studies, biological in origin and nothing to do with a controlling mother, gay men are predisposed to that sexual orientation at an ataşehir escort early age.

Yet, crossdressing is a different matter entirely. A need and a sexual desire that some men have, crossdressing men just want to emulate women. What’s wrong with that? There shouldn’t be anything wrong with a man dressing as a woman and a woman dressing as a man. What’s the big deal?

People need to mind their own business. They need to keep their opinions to themselves. Indeed, because of his mother’s longtime sexual fantasy to have sex with a crossdressing man, his mother, Vanessa, not only influenced him by encouraging him to dress as a woman but also to have sex with her. In the way that he had the sexual need to dress as a woman, she had the sexual need to have sex with a crossdressing man, even if that man was her son, especially if that man was her son.

Through no fault of his own, due to his life altering events, there are somethings in David’s life that have clearly defined him. Different from other men, he’s a bisexual crossdresser. Yet, unlike some men who hide in the closet with their wardrobe of women’s clothes, he’s proud of being a bisexual crossdresser. He’s pleased with the way he looks when dressed as a woman. He even had a hat and t-shirt made in gay pride, rainbow colors that read.

‘I’m proud of being a bisexual crossdresser.’

When in the sexy, exhibitionistic mood, David sometimes enjoys dressing as Kelly, his alter ego, a beautiful and sexy woman. There, it’s written and he/she are proud that they had me write it. It’s out there. They’re both finally out of the closet. Able to finally enjoy their newfound sexual freedom in public, they’re finally free. Spreading their wings, no longer clipped by the uptight morality and closed minded, sexual opinions of others, they can fly and soar now.

Yet, curious to know the answer to the longstanding question, was he born this way, made this way, or a little of both? David doesn’t know. Kelly doesn’t care. Psychology professionals go back and forth about it. It’s sort of like the age-old question, which was first the chicken or the egg? No matter. A bisexual man who enjoys dressing as a woman and having sex with men as much as he enjoys having sex with women and swinging couples, so what?

“Who cares? Why does it bother you so much? Mind your own business. Get a life.”

Seriously, what’s your problem? Except for President Trump and Senate Majority Leader, Mitch McConnell, no one is perfect. We all have our own crosses to bear. What’s yours?

# # #

Perhaps, unjustly judging you by that incestuous look in your eyes every time you look at your mother, if you haven’t already, I bet you want to have sex with her. Am I right? Is that it? Is incest your thing? I bet you want to fuck her. I bet you want to have sex with your mother. I bet you want her to suck your cock. I bet you want to put a gentle hand behind your mother’s pretty head and hump her mouth, fuck her face, and cum in your mother’s mouth.

‘How hot would that be for your mother to give you a hand job and/or a blowjob anytime you wanted one? Wow!’


David imagined looking at his mother, Vanessa.

“Yes, dear. What is it?”

He imagined his mother looking at him with love.

“I’m horny. Would you mind blowing me while I fondle your naked breasts and finger your erect nipples?”

He imagined watching her put down her newspaper, stand from the couch, before lowering herself to her knees in front of him.

“Sure, no problem son. Only, you don’t mind if I swallow your cum, do you? I don’t want to stain the carpet.”

# # #

Even with you being so judgmental, I bet you continually masturbate yourself while imagining having sex with not only with your mother, but also with your sexy sister. I bet you masturbate while imagining having sex with your MILF of an aunt, your hot cousins, your MILF of a mother-in-law, and/or your sexy sister-in-law. I bet you masturbate while imagining them all naked. I bet you masturbate while imagining have sex with all of them.

“Pervert! Incestuous pervert! How dare you point a finger at me for being a bisexual crossdresser when you’re a motherfucker and an incestuous deviate who’d willingly have incestuous sex with all of his female, blood relatives?”

Whether it’s your mother, your sister, your aunts, your cousins, your mother-in-law or your sister-in-law, I bet you’d love nothing more than for them all to suck your cock. I bet you’ll love to cum in all of their mouths and watch them swallow your cum while fondling their naked breasts and fingering their erect nipples. I bet you’d love to give them all a cum bath. Perhaps, kinky to the extreme, especially now with you out of the closet, I bet you’d love to have sex with them while dressed as a woman.

Maybe, you’re not a motherfucker. Maybe, your thing is exhibitionism. Maybe, you enjoy exposing yourself to unsuspecting women.

I bet you love flashing your hard, avrupa yakası escort erect cock in public to women. I bet you hide in doorways and spring out at women walking by while showing them your erect, naked prick while masturbating yourself and cumming on them. As long as you’re not seen by the police and arrested, what do you have to lose? Either they’ll turn away, look, stare, or stop to touch you, stroke, and/or suck you.

“Surprise! Look at me. Look at my cock,” you shout out while masturbating and ejaculating cum in their hair, all over their face, and on their clothes.

# # #

Tell me. Be honest. There’s no one here but me and you. I’m curious to know. How many times have you walked around your house wearing a bathrobe and nothing underneath? A freeing experience, it feels good to have your prick dangling and swinging while nakedly exposed, doesn’t it? It’s sexually entertaining to wonder when someone will see your naked cock. It’s sexually entertaining to wonder how soon you’ll have an erection that will expose itself by parting open your bathrobe.

“Oh, please don’t look at my naked prick, Sister Mary Elizabeth. I’m so embarrassed. I didn’t know that I was exposing myself to you when kneeling to pray,” said David to a nun going door-to-door collecting for charity.

“It’s okay, my son. I’m used to seeing a man’s erect penis. Father O’Malley exposes his naked cock to me all the time,” said Sister Mary anointing herself while rolling her eyes. “When he’s not exposes his naked prick to me, he’s feeling my breasts and ass through my habit. One time, he even lifted my habit over my head and lifted my bra and pulled down my panties.”

As if asking God’s forgiveness for staring, leering, and reaching out to finger David’s prick while holding and stroking his cock, she looked up to Heaven to pray.

“Please forgive me Lord, but instead of falling to my knees to pray, I need to fall to my knees to suck this man’s prick while stroking his big dick. He needs to cum. He needs to cum in my mouth. Amen.”

That happened to David a lot. As soon as women see his huge flaccid or erect cock, as if mesmerized by it, they want to stroke it. As if hypnotized by his big dick, they want to suck it. As if they’re on sexual fire, and as if he’s a sexy fireman and his cock is his firehose, they need his cum to put out their sexual fire. They need him to cum whether in their mouths, all over their faces, or in their pussies to cool them down.

# # #

Be honest, there’s no one here but me and you. Tell me. While making it appear unintentional, how many times have you exposed your naked prick to your mother, your sister, your aunts, your cousins, and your neighbors while imagining having sex with them? How many times have you deliberately allowed women to see your naked prick and/or to catch you masturbating and cumming? Just take a wild guess, how many women have seen your naked prick?

“Wow! That many? That’s a lot. If your wife or girlfriend had seen as many cocks as you have shown women your naked prick, you’d think they were whores. So, what does that make you?”

Maybe flashing your cock isn’t your thing but who knows? Who cares? Just because they both love showing their nude bodies, neither David nor Kelly care what you do behind closed, bedroom doors or in public places. That’s your business. So, why should you care what they do behind closed, bedroom doors? Isn’t that their business?

They don’t judge you for you wanting to have sex with your blood relatives, so why should you judge him for being bisexual and crossdressing. They don’t judge you for deliberately flashing your erect, naked prick to unsuspecting women, so why should you judge them for occasionally sucking a cock when dressed as a woman? The best of both worlds, whether having sex with a woman, a man, or having sex with a swinging couple, or a threesome with two men and one woman, some women are into that, having a threesome with a crossdresser.

Being a crossdresser is his/her thing and he/she is proud of who he/she is and will not allow you or anyone else to belittle them, make them feel guilty, or make them feel less than who they are. How dare you judge them? Before you cast the first stone while living in your glass house, look at yourself in the mirror.

Now, tell me, what do you see? Besides you standing there without pants and underwear while holding your erect dick in your hand, what do you see? You’re no better than him. You’re no better than anyone.

“Shame on you! How dare you? Shame. Shame on you!”

Certainly, David nor Kelly blames themselves for being a crossdresser and for sometimes wanting to dress as a woman. This is their life. This is who they are. This is who he is and this is who she is. Take him or leave him and take her or leave her. He/she doesn’t care, really, they don’t. They’ll not waste their time with what you think about them.

Yet, whether good or bad, if he was to point a finger of blame at anyone, perhaps he bağdat vaddesi escort wouldn’t blame his mother for his bisexuality but he’d definitely blame her for his crossdressing. By flattering him and complimenting him, by making him feel beautiful and sexy, and by making him feel special when she’s dressed as Kelly instead of dressed as David, indeed, his foray into crossdressing started with her. His desire to dress as a woman started with his mother. Who knows, maybe his mother wanted another daughter instead of a son?

“Mom. I love you and I forgive you. Only, you must forgive me, too. I haven’t done anything wrong. I’m just living my life as who I am. I’m a bisexual man who, occasionally, enjoys dressing as a woman. If you want to help me, buy me bras and panties. Women’s underwear is so much more expensive than men’s underwear,” said David to his mother.

# # #

Something that’s difficult to understand for someone who’s not a crossdresser, whenever he’s dressed as a woman, he feels so pretty. He feels so sexy. Whenever he’s dressed as a woman, he feels so horny. Whenever he’s dressed as a woman, he gets such a huge erection. The good thing about being a bisexual, whenever he’s dressed as a woman, he wants his cock sucked whether it’s being sucked by a woman or a man blowing him. It doesn’t matter as long as he’s allowed to cum in someone’s mouth.

With most people unaware that he’s a man dressed as a woman, he receives lots of compliments for his hair, his makeup, and his clothes. Whenever he’s dressed as a woman, with him accepted and complimented as a woman instead of ignored as a man, he wanted to dress as a woman again. Enough to turn his head, he always received enough attention and compliments to make him want to continue dressing as a woman again and again.

Seemingly people notice him because he’s so very pretty. When dressed as a man, when dressed as David, he’s just another, average guy. When dressed as a woman, when dressed as Kelly, he’s someone who is wanted, desired, and sexually lusted over. As do we all, we all want that kind of sexual attention. In the way that David wasn’t wanted, desired, and/or sexually lusted over, Kelly was. Kelly sexually enjoyed being wanted, desired, and sexually lusted over. Who wouldn’t?

Sometimes, not all times but sometimes, especially when he’s dressed as Kelly, he wished he was born female instead of male. If he was born female, he wouldn’t have to shave his face, his arms, his legs, or his chest. If he was born female, he’d have breasts and a pussy instead of a cock and testicles. If he was born as a woman instead of a man, he wouldn’t feel guilty for fooling and deceiving people into thinking that he’s someone that he’s not.

As if playing a role, he enveloped the essence of Kelly’s character as if he’s a character actor on stage. He takes on her role as if he was born a woman instead of a man. The more he dressed as a woman the more he wished he was born a woman. Blurring the lines of male and female, sometimes he wondered if, one day, he wouldn’t want to continue being a woman. Always he wondered if he’d be happier having the elective surgery and becoming a sexually desired woman instead of living the rest of his life being ignored as a man.

Sometimes, he wondered how different his life would have been had been born a woman. Instead of being chastised, criticism, and called names, no doubt, he’d be welcomed as a woman. Instead of being rejected in the way that people view him as a crossdressing, bisexual man, he’d not only have men who wanted to have sex with him but also, he’d be surrounded by women and swinging couples who want to have sex with him, too.

# # #

A road with lots of twists, turns, and potholes, he didn’t pick an easy road to follow but this is the road he chose nonetheless and he’s going it alone. This is his life. Everyone needs to back off and worry about their own, little lives instead of having opinions about what he does, doesn’t do, who he does it with, why he does something, doesn’t do something, and what he’ll do next.

No apologies necessary, he’d never apologize for being true to himself. He’d never apologize for being a bisexual or for being a crossdresser. If anyone needed to apologize, they’re the ones who need to apologize to him for being small minded, judgmental, and mean. They’re the ones who make him feel bad about himself when he should feel good about himself.

“Shame on you! Shame on all of you! Fuck all of you!”

As if they were all there in front of him and being critical of him, David surveyed the crowd of readers, those men who didn’t understand gay sex, bisexual sex, crossdressers, and crossdressing. Kelly surveyed the crowd of readers while picking out which men she’d have sex with, as if they were really there. With David somewhat shy and not very trusting, Kelly was outgoing and friendly, albeit a little slutty. She enjoyed meeting people as much as she enjoyed having sex with strangers.

There was a lot to like about Kelly. David liked the fact that she was a bit of an exhibitionistic whore. She enjoyed showing her panties in up-skirt peeks, and her bra and cleavage in down-blouse views. She enjoyed sexually teasing men and shocking men by stealing a kiss while groping their hardening cocks through their pants. Moreover, she enjoyed sucking cock as much as he enjoyed sucking cock.

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