Fiction: Chained and Forced to Choose

"So," said the captor to her prisoner. "Have you ever worn women's clothing?"

"Of course not!"

"You've never worn a dress as a practical joke?"

"No."

"Your big sister never forced you to play dressup?"

"I don't have a sister."

"You never snuck into your mom's dresser to try on her panties?"

"What the Hell are you talking about?"

"Aren't we defensive? And you're blushing, too!"

He didn't answer.

"We know all about your little secret, Mister. We know that you wear lingerie for fun. We know that you secretly want to be a girl, just so you can wear pretty little frilly lace undies that boys aren't allowed to wear."

"What?"

"Oh, I understand. Your fragile little masculine ego won't let you admit it to anyone. But I know that you want to be just like me."

"Am I supposed to be scared?"

"Not really. You're supposed to be excited, though. And I know that you are. Just thinking about wearing a sexy little garter belt turns you on."

"This is a joke."

She moved her face to his, and the scent of her perfume invaded his nostrils. She looked him in the eye, and he couldn't hold her penetrating gaze. Her breast brushed against him as she leaned over his shoulder to smell the back of his head. She stayed there a few moments, breathing heavily. Suddenly, she backed away, breaking the spell.

"Do you think I'm sexy?" she asked. 

 
She was, indeed, gloriously beautiful. She looked like a supermodel. Plus, she was in her skivvies, revealing her perfectly shaped body in its curvaceous majesty.

"Yes," replied the prisoner.

"Do you want to fuck me?"

"Yes."

"Oh, that's so sweet!" she exclaimed coyly, as she threw her arms around her prisoner's neck, and moulded her body against his. His naked body almost convulsed in ecstasy as she touched him. Unfortunately, he could do nothing, suspended by the chains on his arms and restrained by those on his legs. She backed away seductively as he gasped at this unexpected pleasure.

"You know," she said, "I'm not supposed to fuck my prisoners. So we'll have to make a little deal."

He was speechless. 

 
"I can't do anything for you unless you do me a little favour first."

"What? Tell me, what must I do!"

"You have to admit that you want to wear women's underwear."

He paused, shocked. "Is that all I have to do to fuck you?"

"Yes. That's all."

"But that's ridiculous! How can I fuck you if I don't feel masculine? How can you want me to be feminine?"

"Fine!" she snapped, and turned sharply away towards the door.

"Wait! Wait!"

She turned, fury distorting her gorgeous face.

He hesitated. He knew that this was a trick. She had him backed into a corner. He desperately wanted to have sex with her, and he knew that she probably wouldn't anyway. Moreover, he knew that she would likely torture him and force him to her will anyway. It was a tough call. "OK, I'll do it."

"You'll do what?" she asked, unable to conceal the glee in her voice. "Say it!"

"I'll wear women's clothes."

"You'll what?"

"I'll wear women's clothes!"

She clapped her hands joyfully and skipped over to him to kiss his nipple. "I knew you'd cave in, you little sissy! I can't wait to see you in a bra! You'll be so cute! You'll be so effiminate that you won't even want to fuck me anymore! Hee hee!"

He couldn't believe what he had gotten himself into. He began to think about his near future, and dreaded its approach. What would she do to him? He couldn't stop thinking about her in her wonderful underwear, and fantasized about all the different things in her dresser that she would force him to wear. He could hardly contain his shame when he realized that the thought of it aroused him in a strange, unwholesome way that aroused him all the more for its perversity.

When the time came, she did not force him to wear something of her choice. Instead, she presented him with many options. He had before him all kinds of underwear, lingerie, swimwear, leotards, garter belts, stockings, chemises, and nightgowns. All were unmistakably feminine. His very proximity to these dainty items brought hormones rushing through his body. He was very nervous. She left the clothes in his cell, and released him to pick out something girlish to wear. 

 
He picked through the clothes with apprehension, still unable to believe that he would have to wear it. He couldn't picture himself in any of it, but had no trouble imagining his captress.

"Pick something! You're worse than a woman!" she boomed from the microphone. She watched him from the room above, which overlooked his cell. Trembling, he snatched a one-piece swimsuit- the least sexy item he could find. He didn't want to give in too much.

"Put it on!" she screeched from above.

He slipped into the swimsuit, which clung to him like a second skin. The soft fabric and high cut gave him an instant erection, of which he was desperately ashamed. He was quickly chained up again, unable to remove his new garment. All he could do was writhe.

"Do you like it?" she asked when she came down from her perch to see him. She wore a bikini for the occasion, picking it from the selection he chose from and changing into it in front of him.

"What if I don't?" he retorted.

"Oh, I can tell you love it! Look at this bulge!" He reddened in guilty shameful pleasure as she stroked his covered penis. "Do you feel feminine?"

"You promised you'd have sex with me if I wore women's clothes! I wearing it now, so let's do it!"

"Tsk, tsk. Not so fast! You're all chained up there, and you can't exactly do anything about it, can you? Don't worry, I'll fuck you. But not now. For now, I just want to do girlie things with you.

She began to rub up against him. "I want you to feel like a woman. Just imagine what I'd look like wearing that."

She showed him pictures of her wearing exactly what he was wearing. "And just think: you're wearing it now!  You're dressed like a girl. And you seem to like it! Isn't it great to have something caress your body like that?  Don't you just love the delicate material?"

He convulsed with erotic shame. He writhed and struggled, disgusted with himself for becoming feminine. Listening to every word she said, and feeling jolts of exquisitely forbidden pleasure rising from his cock. He struggled to escape from her swimsuit. He felt trapped in it, but relished guiltily every moment of it. "Do you feel feminine?" she asked again.

"YES! YES!"

"Do you like it?"

"YES!"

"I think you've had enough. Let's get that off of you."

"NO!" he screamed. "Don't stop!"

The bathing suit seemed to shape his body into a girlish hourglass. He imagined that his crotch looked just like a girl's, that his chest looked busty. These thoughts sent jolts of intense ecstasy through his body. He had always found it sexy to see empty suimsuits and panties and bras, because it meant that there was probably a naked woman nearby. He felt that knowing the inside of a woman's underwear was incredibly intimate - and arousing. Only this time, he felt the inside of his mistress's bathing suit clinging lewdly to his body. Only women know what that feels like. And now, he does, too. And he felt proud and lucky for it. And feminine.

Diary: The Seed Grows

The thought, I am sure, has at least occurred to everybody.

I mean, everybody's heard of transvestites, so they can certainly admit to having imagined a man wearing women's underwear. The first thing I think of is how disgusting and un-feminine they look, no matter how hard they try. It's a short step from there, though, isn't it? Girlfriends will cajole and kid when seeing a transvestite that, "yes, darling, why can't you be more like him?" Or ask straight out if they've ever worn panties. For most men, it's shockingly perverted. They wouldn't dream of forsaking their manhood, or even joke about it, around their girlfriends or wives or mistresses.

But then, that little seed has already been planted. 

Add to that living with a woman: even if she's the mother or sister or some other relative, there's always women's dainties around. What man doesn't get turned on thinking about women's underwear? I've read that men need to see their women in underwear, that it's more appealing to them; they need a signal of femininity. What's more feminine than women's underwear? Not only does it cover the sexiest parts, it accentuates them.
It's difficult for any man to shop for lingerie. That's because there's an uncomfortable stigma about being seen in such a den of girlishness. Who but a girl - or a sissy - would be seen in a place like that? And men know what's pretty, too.

So there's definitely an association.

Secretly, they think about it. They're embarrassed to admit that they're interested in women's underwear - so much so that they can't shop for lingerie without breaking into a cold sweat.

Imagine picking up an article of gorgeous, absolutely female underwear, and being aroused by it. It's so feminine. I have no right to touch it. Merely touching it jeopardizes my manhood. How can I handle being exposed to something so powerfully girlish? I can't: I get so horny that I have to do something about it. Even when I see it on a girl, it drives me crazy. It used to be when I was five or so that girls were icky. A boy could never survive the stigma of hanging around with a girl, or else suffer the humiliation of being called a sissy. The other boys would think that I'm one of them. They would think that I'm secretly a girl. All boys had to resist girls, because we all knew that they were out to assimilate us and make us do all sorts of stupid girl things, and make us wear frilly pansy pink girlie clothes. I'm not surprised if I carry a remnant of that with me even today.
As a matter of fact, there's the idea of the old ball and chain: she'll domesticate you if you commit; she'll turn you into a sissy! You won't be a man anymore, because you can't go bowling or boozing with the guys anymore. Girls are dangerous that way. They want you to be a girl, too.

But men commit all the time. There comes a time when they have to betray the boys, and give in to the girls. The danger exists from day one, when little boys clump together in frightened cliques, berating anyone who dares to show that they feel that same, strange attraction to girls that they each secretly feel individually. They make each other sense that it's powerfully wrong, yet they each feel that they desperately want to. And so the seed is sown.

I know it's wrong, thinks the little boy, but it feels so good when I think of girls. Maybe I am one of them, after all. Imagine: what if my parents are wrong, or what if they've decided to pull some cruel joke on everyone, and I really am a girl, but everybody thinks I'm a boy? That must be it! The girls want me to join their ranks, I can feel it. I am drawn to them. Oh, I would be so free if I could only join them! They would take care of me. They would rub me right here where we're different, and make me like them. Right here they would rub me. Rub me right off. And I would be a girl. Rub me here. Rub me! Oh, rub me! Girl! I'm a girl now! Oh, God, I'm going to turn myself into a girl if I just rub myself! Oh, it feels so good! I want to be a girl! I love feeling like a girl. 

Then it's over and I'm ashamed, and I know that I'm a boy, and that I let everybody down.

Then it starts again. The longings come back. Then I begin to think that girls wear some pretty specific clothes. Boys don't have flowers and frilly lace on their underwear. Girls look so good in their underwear. If I want to be a girl, then I have to wear some of that, don't I? But do I dare? That's the trick, isn't it? I don't want anybody to know, but I want to try it. I start to imagine all sorts of bikinis and bathing suits and stockings and garter belts and panties and bras and teddies. . . I want to wear them all! Just thinking about it makes me feel so good! Imagine how good it must feel to be that sexy! I figure that I've only thought about being a girl so far. I've never actually tried to be one by wearing girls' clothes. Surely doing that will instantly transform me into one, and I'll never be able to regain my manhood. I know it's dangerous. I'm afraid to try.
I try. I don't care that I'll never be a man again. I just want to be a girl now. To Hell with being a boy! It feels so good when I touch women's clothes! I imagine myself wearing only silky women's panties and garter belts and bras from now on. I'm Hell-bent on becoming feminine. I'm only wearing pantyhose on top of my own underwear, but I'm picturing myself in lingerie, bikinis, etc. etc. etc.. Physically, I've barely done anything; mentally, I'm willingly going way too fast. I can't go too fast physically, because I'll never be able to turn back. If I take it slow, I'll be able to work my way up to it, and hang onto my manhood. If I go too fast, I'll be totally transformed overnight, and I'll have a lot of explaining to do. But it's so much more fun to go fast! I want to be girlish NOW!

Before I know it, I'm wearing all the stuff I fantasized about, loving the way it makes me feel so delicate and girlish. And I can't stop.