"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?"
"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."
"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?"
"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.
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."
"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.
"Do you like it?"
"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.