Back To Stories

Trapped and Humiliated Sissy by Suzi
Story Contest Winner 2014

Lisa’s head lay on Jonathan’s stomach as they watched TV together. She yawned, bored with the program and a head that had been spinning with the same question that had been bugging her for the last few days.

After a few seconds of shuffling, her face looked up towards his and she playfully blew a mouthful of breath up towards is nose; he wrinkled it and look down at her face.

“What’s wrong?” He asked.

“Nothing”, she lied back.

He tried to ignore her stares for a few minutes before giving in and asking again.

“What’s up?”

She smiled before answering. “You know how we promised to tell each other everything?”

This sounded bad he thought. “Yeah?”

“Well,” She paused. “Well, how long was it going to be before you told me that you liked wearing my satin panties?”

His face went bright red, and she thought CAUGHT YOU to herself.

“What do you mean?” He tried hard to sound cool and collected but had spurted it out.

“Well, it’s just that you’re terrible at putting things back, or in the wash after you’ve used them.” Carefully she watched as he started to sweat. “And you’ve ruined three pairs. I can’t wear them as you’ve bulged out the front and loosened the elastic waist band.”

She sat up and grabbed his hand, pulling him up and dragging him off to the bedroom. Jonathan just followed along, numb and struggling to think how she’d discovered his secret and what was going to happen next. When they entered the bedroom she dropped his hand and went over to the draws that held her panties. Opening it, she removed three sets of satin and lace panties from her special collection part of the drawer. She gently pressed one of the pairs around her waist, and showed how the waist was loose and slightly too big for her now.

“See, you’ve pulled the waist band out on these three.”

His face was bright red and sweat began dripping down his face. He knew that she’d caught him and he couldn’t think what to say. He looked down, like a naughty boy who had been shown the evidence of his misdeeds.

“Sorry.”

Something inside her found his current demeanor such a turn on and wanted to keep him all pathetic and submissive. How far could she push this, she wondered?

“So you’re admitting to wearing them are you?”

He couldn’t look at her. “Sorry, I didn’t...”

“What, didn’t mean to?” She interrupted him. “Which bit didn’t you mean to do? Was it the stealing my satin undies? Was it getting naked and putting them on, or was it wanking off in them?”

He couldn’t reply and his mind just spun with what she was going to do. Obviously she was going to drop him as a boyfriend, but what else? He’d never seen her like this and didn’t know what she would stoop to. Maybe it would be telling her girlfriends that she’d dropped him because he’d been caught in her panty drawer or worse, all of his friends. He could just imagine the humiliation of what was ahead of him when her voice cut through.

“So you like these three? Well, you’ve ruined them for me so pick your favorite and put them on. I want to see what you look like in girlie undies.”

She watched him uncomplainingly obey her. He pulled off his t-shirt, jeans, socks and boxers before pulling on the pinkest and frilliest of the three satin bikini bottoms. As he pulled the soft material over his cock, she noticed how it had started to grow.

“Oh, and don’t think I hadn’t noticed that you’d also been at my baby-dolls as well.” She walked over to the wardrobe, opened it and pulled out a matching pink satin and lace nightie.

Throwing at him she said; “Put it on too, since you like it so much.”

He picked it up and slipped it over his head. The material fell over his body and stopped just above his crotch, framing his thick, oozing cock. She couldn’t have missed his full erection, and it was only time before she would start screaming at him he thought.

“Look at you.” She felt so powerful looking at her cross dressed boyfriend. “I don't know if the cock is hard because you’re dressed up like a sissy, or if it’s because you’ve been found out as a fag-boi.”

He mumbled something back but Lisa just ignored it. “So what do you do next then sissy?”

Her voice dripped with contempt. “I bet you get on the bed and wank off. Go on, get on there and show me.” She pointed at the bed.

He climbed into the centre of the bed and pulled the panties to one side and exposed his cock before beginning to pump. What else could he do? Trapped and now humiliated, his mind had stopped working and now his hands had taken over an just obeyed her commands.

“You can stop that sissy.” She walked over to the drawers and took a roll of satin ribbon that she’d placed there earlier in the day.

“Hands above your head.” He obeyed and she began binding them together before tying them to the headboard. Now she had him, dressed up and in bondage; and it had been so easy!

Lying down next to him she could see the fear in his eyes.

“You know that you’re totally fucked now don’t you?” He nodded. “You’re a little sissy and, if I want to, I can tell every one that you’re into dressing up like a girl.” He gulped and knew that there was nothing he could do about it. “And do you know what pisses me off about this?”

He shook his head. “You didn’t tell me, and I had to loose three nice pairs of panties.” She plucked up one the remaining pairs and pushed them into his mouth. “Now look at you. You’re tied up, dressed up, and totally fucked.” She giggled.

Her hand reached down to his cock, took hold of it and began stroking it. “And this is what you do next then?” He flinched as the shock hit him. The first of her strokes nearly made him instantly cum.

“Oh, not yet sissy boi, I want to tell you what’s going to happen from now on.”

She sat up and reached to the night stand, and plucked off a couple of items and rested herself across his stomach. He could feel something being wrapped around the base of his cock and balls, and then tightened almost painfully. “There you go, they’ll not escape now.” She patted his balls making him flinch.

She moved herself so she could look into his face and started playing with his cock again.

“Now, where was I? Oh yes, you’ve been caught little sissy, you’ve been caught with your hand and cock in my panty drawer.” The word sissy had made his cock jump and harden even further. He tried to plead but the panty gag just dried his mouth and killed any sound.

“So what am I going to do? Should I drop you and then humiliate you in front of all of your friends? Should I photo you like this and send it to everyone you know?” She laughed. “Or should I keep you as a sissy pet? Maybe I can use you like the little sissy you obviously are.” She dug her nails into his shaft before carrying on with the slow, deliberate strokes. “What ever happens from now on, you will never go into my panty drawer!” Another dig and pain shot through his body.

She leaned into him and began whispering

“So, now you’re fucked and I’m going to have my fun. I totally own you and I can give you pain and pleasure; how much and when will be totally under my control. Firstly, you’d better get used to the idea that I own you and I can do anything. If you don’t like it then...” She giggled. “You’ll find that EVERYONE will know your little secret.

Secondly, I’ve decided to indulge your passion for dressing as a girl. This weekend we’re going out and buying you some new soft, sexy clothes. I like the idea of having a 50’s housewife look after me from now on.

Thirdly, you’re never going to be allowed to forget what’s happened. From today onwards you will not be allowed to wear boy undies unless I allow it.

And finally, given that you’ve been wanking off behind my back, in my undies, I can't trust you having control over your cock so...”

She reached over, picked up something and dropped it onto his nose. He couldn’t make out what the plastic device was. “Oh, this is a cock-cage. A chastity device and after we’ve finished here you’ll be living in it.” It rolled off his nose and onto the bed next to him.

“So you’re going to get your balls cleaned out tonight, and then it will be at my whim when it occurs again. Be good and you’ll be allowed to play with me. Be bad and we’ll see how blue we can make these.” She patted his balls.

“Now, since you’re still stiff and not far off cumming, it’s time that I told you what you’re getting. Well, on Saturday we’ll be going out and buying you some nice satin panties that fit you. I think you’d like bikinis like these, some French knickers to replace your boxers and some thongs - well you do have a nice butt. They willl all be soft and shiny and so smooth on the skin and you’ll wear them every day, even at work.

Can you imagine how you’ll feel? The soft material holding your trapped cock in and rubbing against your butt. You’ll be so turned on and ashamed about wearing them. Maybe, yes, maybe we’ll get some really lacy panties and get you to wear those to work and see if anyone spots them. I'm going to have so much fun shopping for your undies and you’ll wear what I buy. Don’t worry, they’ll be silky or satin and very lacy.

You’ll need matching sets as well. You know, matching panties and bras. Every girl needs several matching sets and yours will be so nice. I’ve seen a couple of sets with polka dots on them. Gel bras, not under wired, but nicely fitting for my little sissy. Maybe even get you some lovely corsets to give you the proper look that all girls need.

And you’ll need slips and camisoles and garters. Well, you’ll definitely need garter belts because you’ll be wearing the softest, silkiest stockings I can find. You can have some hold-ups for going out, but you’ll be wearing silk stockings in the house.”

He was nearly there and she slowed the stroking

“And then you’ll need petticoats, skirts, blouses and dresses. All of them will be satin soft and tease your skin. Just think about the uniforms you could have. I’ve always wanted a maid to wash and iron, maybe even make my meals and serve me dinner. I bet you’d love that wouldn’t you?”

He nodded. He was so near the edge that he would agree to anything just to be allowed to cum.

“Good, then you’re going to be my dress-up, sissy maid-wife. You’ll do what I want and be allowed to dress it the prettiest of clothes. And what I want is you pretty, made up, in high heels and obedient.

So, if this is what you want too all you have to do is nod...”

He nodded. Now the strokes had become so slow that she kept him hovering on the edge, neither building up or relaxing, just hanging on the edge of orgasm.

“Good, so tomorrow you’re going into work in the remaining satin panties. On Saturday we’re going off to buy you your new clothes, shoes and make-up and I’m going to take charge off your current account and credit cards. Now you’re my slave, my sissy and my money pig aren’t you?”

He nodded, lost in near ecstasy

“I’m loving this sweetie, but I think we should have a new name for you. I want something that I can call you all of the time, where ever you are. I know, Victoria. So Victoria, I want you to change my name on your phone to My Owner and I’ll change yours to Victoria.

Okay Victoria, are you ready to cum for your Owner? Well before I let you, there’s one more thing to remember, you will always address me as Ma’am or Princess.

And now I’m going to give you permission to cum, but only when I say. So, today you’ll have to cum within 10 strokes of me saying or else you have to wait until at least Saturday. Ready?”

Wild nodding.

“So, you can cum now...10...9...8...7...6...5...4.” Her strokes were slowly bringing him to the edge but not fast enough. He knew that it would take longer and began whimpering. “...3...2..” And then she did something magical that threw him over the edge.

It was like a volcano exploding. She kept stroking, pumping out more and more cum which flew over him and splashed on his baby-doll, face and soaked his panties. Soaking wet and still being pumped, he passed out.

Lisa kept going until nothing was left in him and he was pumped dry. She pulled out the gag panties and smeared his cum across his lips and let it drip into his mouth.

She got up and washed her hands before digging out her phone. Several incriminating shots later, of the cum soaked sissy with his own cum in his mouth and on his lips, she decided that it was time to get ready for bed. She left Victoria tied and wet all night so that, when he woke up in the morning, he’d know that she’d been serious about his new life.

Back To Stories