I Dressed My Boyfriend in Women's Clothes

I had always been the one in control in our relationship. It’s not that my boyfriend was totally submissive or anything, but more that I just had a more dominant streak. If I suggested something, we usually did it and we often used to joke about how I wore the pants out of the two of us! But whenever we said this, I used to think that what would really be interesting would be if I actually dressed my boyfriend in women’s clothes - I wear the pants, he wears the dresses. Sometimes, I suspected that he imagined it too, but I knew he would never say anything first. He would wait for my lead.

One night, on a quiet evening at home, I decided I was going to go for it. I knew him well enough to know that the best way to go about this was to come straight out with it. He’d be surprised but he’d do as I asked. “I’ve always wanted to dress you up in women’s clothes,” I said. His head whipped round, his eyes wide. I quickly added, “let’s face it, you’ve definitely got the legs for it,” with a reassuring smile. Looking uncertain but intrigued, he replied, “ok”.

Taking his hand, I led him up to the bedroom. I started to undress him, to unpeel the layers of his male clothes and to look at him naked, to think of how I would feminise him with this new look. The best place to start of course, I thought, is lingerie. I walked over to my lingerie draw and pulled out a silky, black basque with matching silk panties. Looking over at him, I smiled as I then reached for a pair of my smoothest black stockings, “and we’ll need these of course.”

His eyes were fixed on the underwear as I walked back to him, never having worn anything like it before in his life but anticipation building in him. “This will give you the shape you need to look like a woman,” I said, fitting the basque around him. I walked around to the back and pulled on the lace to nip in the waist, tying it up and running my hands over his feminine curves. I then picked up the panties, slowly sliding them up his thighs. He shuddered slightly at the light, soft touch of the silk against his skin. “Sit down on the bed,” I instructed him. I carefully, placed a stocking at the end of his foot and gently slid it onto his leg, smoothing it against his skin as I moved upwards. I took the suspenders at the top and clicked the stocking into place. His face flushed, I knew he had enjoyed the delicate touch of the nylon and so was extra indulgent when putting the second one on him. I caressed his leg as I moved up to the top of his thigh, complementing him on his long, slim and feminine legs.

And what better way to show off a great pair of legs than with some sexy heels. My size wasn’t too much smaller than his and I knew just the pair that would fit. Killer heels, with a metal stiletto but with a dainty strap around the back of the heel. “You’re going to have to learn how to walk in these fuck me heels,” I said, winking at him. He half smiled back at me. There were still some nerves, I could see them in his face. I knelt down and lovingly placed my favourite pair of heels on him, gliding them on easily over his stockinged feet.

“Stand up and let me look at you,” I said to him. As he raised himself up, I saw a totally different figure. The shape was lean with a curve around the hips and as he turned around for me it made his behind more shapely too. To complete the look, he needed the icing on the cake of womanhood - make up. Sitting him down on the bed again, I got my make up and started to get to work on him. Full dark, smoky eyes and red lips with a hint of gloss, his face was beautiful and seductive. How can I not share my long, black haired wig with him to complete the look? I’d worn it many times when dressing up for him. Now I realised that when he’d run his fingers through it he was yearning to wear it himself.

“Now,” I said gently taking his hand in mine, “come see how beautiful you are my sweetheart.” I took him over to the mirror and let him take in the vision that was before him. He had never been so resplendent, so enticing. His hands hovered over his figure, wanting to touch the soft fabrics on his skin. He hesitated, so I did it for him. Running my hands all over him, down to his thighs and between his legs. I had dressed my boyfriend in women’s clothes and now I was going to enjoy deflowering him!

Steamy Stories

Caught Pleasuring Myself at Work

Being the only woman in an office can have its downsides. No one to talk about shoes to, a lack of interest in my favourite TV programmes! But one of the plus sides is that I get to see a stream of good looking, horny guys come past my desk every day. Some of them make me so hot it’s hard to tear my eyes away from them. What I wasn’t expecting was that one day my staring would lead to me getting caught pleasuring myself at work!

It was late and I had a few emails to finish off. There was no one else still around as I had checked when I nipped to the bathroom and so I thought I may as well make use of a bit of privacy for a change. I decided, “Hey, what’s the hurry, emails can wait 5 minutes!”

I had been thinking all afternoon of a particular guy that had been in that morning. I had been moist all afternoon just thinking of what he would do to me. I sighed and put my head on the back of my seat, closing my eyes as I slid my hand up my skirt and towards my wet pussy. Pulling my thong to one side, I dipped a finger deep into my cunt to get myself going. Just the thought of imagining this guy’s finger in my pussy was enough to send shivers up and down my spine. Just a quick flick was not going to be enough today!

I slid off my underwear and raised my feet onto the desk so that I had total access to my hungry clit. With one hand circling my shaven pussy, the other started to reach inside my blouse and into my bra. My nipples were rock hard. I threw off my top and bra now as I wanted to be able to stroke all around my big, sensuous breasts, teasing my nipples while imagining his tongue sucking away on them. Back to fingering my pussy, I just couldn’t get deep enough to imagine his cock thrusting into me so off came the skirt and I was now totally naked but for my heels. Laying down over my desk, I now spread myself wide open and caressed my tits and cunt as freely as I liked.

I was moaning as I lightly flicked my sweet, little clit, thinking of him licking me to heaven. I didn’t give a second thought to getting caught pleasuring myself at work, I was lost in the fantasy of getting expertly fucked at work! I licked my juices off my fingers and plunged them straight in again, starting to ache for a real cock in me. My hips were raising up and down trying to let my fingers work faster and harder, to make me come in the one environment I knew I would get in trouble for it.

I didn’t care. All I wanted was the sweet release and kept thinking of him fucking and pounding me over my desk. The ecstasy was building and I knew I was going to come. It was then I heard a noise outside my office. Looking over, I saw another colleague of mine, Harry. He was standing just behind a door and had been watching the whole thing! He was flushed, his eyes wide and he was clearly wanking himself as I rubbed my clit. I knew the shame of getting caught pleasuring myself at work, of being spread eagled and naked across my desk and of furiously stroking my dripping wet pussy was going to get to me afterwards. But right now, I just wanted to climax.

Looking straight at him, I parted the lips of my cunt with one hand, letting him see every bit of me, every bit of the furious stroking and flicking I was doing with my other hand. I threw my head back and revelled in my new audience, letting the pleasure out and shrieking as I finger fucked myself.

I felt the blissful rise of my climax coming to me. Crying out, I called, “I’m coming” as the pulsing pleasure tore through me.

With my erratic breathing starting to calm again, I was now ready to look up and into the face of my voyeur. He had shot his load too and now looked at the floor, too nervous of looking back at me. I drew my legs back together and jumped down off the desk to dress myself again. I figured the best thing was to act normal and get on with my emails!

But in my mind I wondered whether I was secretly pleased, whether I would enjoy more men watching me and if Harry would tell. I was already starting to look forward to the next time I got caught pleasuring myself at work!

Bar Tales

Dave was always at his local bar. There was precious little else going on in his life and at least he wasn’t in every night staring at the four walls. He was at least staring at the girls that came into the bar instead. There were some pretty hot ones too, particularly at the weekends as they dropped by the bar, dressed up to the nines ready for a night on the town.

There was one in particular he had his eye on. She was a petite brunette but with curves in all the right places and she certainly was not afraid to show them off. She wasn’t slutty, more confident in her own skin - something Dave certainly wasn’t. Stare was all he could do, safe in the knowledge that he would never find the courage to approach her or in fact any of them.

Occasionally he wondered if she looked over at him but figured that if she did it was only because he was starting at her. Or maybe it was that time of the night when the beer starting to work its magic and he was imagining things. Either way, he never got a second look out of her and frankly, him not being exactly a catch, he wasn’t surprised.

One Saturday she came into the bar quite late. There were fewer friends with her than usual and she had a pretty, white dress on that didn’t look like it had been chosen for a night out on the pull. In fact, she looked quite sweet in it. Dave was even more transfixed than ever.

He went up to the bar to get himself another drink and to his amazement he suddenly found himself stood right next to her. He was desperate to look at her but kept his gaze ahead. In looking forward he had forgotten the mirror behind the bar and turned headlong into full eye contact. He was so stunned he didn’t look away. Amazingly she stared right back, breaking into a coy smile. Without knowing were the nerve came from, he turned right round to her , “Can I get you a drink?”

She raised an eyebrow at him, as surprised as he was at his sudden confidence. “Great”, she said, “make mine a white wine.”

With drinks in front of them now, still stood at the bare, Dave found himself having to stand close to her as they talked. It was a great excuse, there not being much room! Pressed up against her and leaning in to hear what she was saying, he got a magnificent view down the front of her dress and her tits were as good as he could ever hope for. A good size for someone so petite elsewhere!

She wasn’t backing away from him at all. In fact she was pressing her body against his groin now and the look in her eyes was unmistakeable. She wanted to get fucked and was coming onto him without question. He had no idea why she had picked him and didn’t care. She leant in even closer and took him by the hand. He looked back at her confused for a second but then realised she was leading him outside to the back of the bar. It was a private area for staff only, darkly lit and empty during this busy time - perfect.

Immediately she kissed him, her tongue going deep. Hungry and with a promise of so much more, her kiss was experienced and passionate. Her hand reached straight for his cock, reaching inside his fly to unleash him, wasting no time in getting closer to the banging she longed for.

His hands were straight onto her tits, pulling her dress off her shoulders and letting it fall down over her breasts and he felt a rush of excitement at exposing them to the night air. She moved backwards, walking towards a ledge by the wall. He lifted her up onto it and instantly put his arms tight around her, kissing her deeply as he pushed his whole body against her as she wrapped her legs around him.

With one hand he reached down and slid his hand into her underwear and straight to her dripping wet pussy. She was ready to be fucked right here and now and he had wanted her for so long he was going to go ahead and take her. With one move he pulled off her thong and drove his cock into her cunt, all the way in. She threw back her head and sighed a deep sigh, arching her back and looking like just the feel of him inside her was enough to make her come instantly.

He pulled out and thrust roughly into her again. Again, she sighed, rolling her head to one side, her eyes closed. She was his and he knew he could do what he wanted. He reached his hands round to her curvy, smooth behind and in the process pulled himself deeper into her. She groaned, tightening the grip of her legs around his waist, her whole body begging him to take her to the climax she was desperate for. Again, he thrust hard. This time he didn’t stop to see the effect, he started to pump into her with only one aim. Quickening, he had never fucked so hard before. He was aware of her breathing, the light whimpers, but all he could do was look down, watching her pussy take the length of his member time and again, right up to his balls.

He could feel the pulsing in his cock, the rise of ecstasy as he fired a jet of creamy come into her with more force than he’d ever known. Clasping her, he made sure every drop went into her cunt.

He looked up at her face and saw she was flushed, her breathing slower and her eye lids slightly heavy so he knew she was sated. He pulled out of her and straightened his clothing, ready to go back into the bar. The relief at not being caught started to catch up with him, for the first time noticing the shadows of people from inside. But would he do it again next she was in? Of that he was certain.

Steamy Stories

She Had the Power

Every day he saw her from afar, every day he yearned to fuck her. She was tall, blonde, cool and aloof and she turned heads wherever she went. She was a top student at the university they attended; he was a nobody getting by through the skin of his teeth. He doubted she even knew who he was. But everyday he would try to be near her, to get a glimpse of her in the pub, lecture or with her friends.

There was always their mutual friend, he was always trying to strengthen that connection. But when it came to an introduction, would he grab at the chance? No, he would walk away frustrated, go home and wank over her, imagining all the things he would do to her if he had the chance.

But he’d started to notice something different about her recently, he was certain. Whereas before she had hardly acknowledged him, now she seemed to look at him for slightly longer. There was a curiosity there.

This look met him when he bumped into her one evening on his way home from a night out. She was walking alone. Was this the perfect chance to get close to her, to walk her back to her place? She seemed keen to let this happen and gave him that curious smile. Somehow, he was not feeling in control of this situation! She did most of the talking, he tried to avoid her gaze.

“Do you want to come in for a coffee?” she asked when they arrived. Nervously he accepted. She led him to the kitchen and he sat down.

“I get the feeling you’re not comfortable around me.” He was struck with terror. It was obvious she knew the affect she was having on him - but was this his chance to succeed with her? Or was he walking right into abject humiliation. “I’m a little unsure, perhaps?” he replied.

“And why is that I wonder,” she said with an air of amusement. “Is it because you’re worried that I might see through you?” Frozen to the spot he just looked up at her, standing over him with one hand on her hip.

She flicked back her hair and leant in closer to him. “Do you wank over me?” she said sternly. The smell of her perfume, the closeness of her soft skin, he could no longer tell if he was scared or aroused. He nodded meekly.

He was now cornered and he knew it. “And what exactly do you imagine, sucking on my tits?” With this, she lifted up her top slowly, revealing her big, lightly tanned breasts spilling over the top of her bra. She reached for the straps and slowly pulled them down to reveal the full splendour of her tits, placed just in front of his face. He was transfixed, his cock was rock hard. “What if someone walks in?” he whispered. “Then they’ll see what a pathetic little perv you are, won’t they?” She half laughed as she said this, clearly enjoying the power she had over him.

“Do you imagine sucking on my gorgeous tits?” she continued. “Taking my nipples in your mouth and running your tongue around them?” She ran her fingers slowly around her nipples making them hard. He nodded again, looking up at her with lust and fear. His eyes pleaded with her, half begging for her to take pity on him and let him go and half desperately hoping she would relieve him, to touch his rigid cock if only for a moment.

“What do you do when you think of my tits, do you take your puny dick in your hand? Do you wank yourself off thinking of fucking me?” He nodded. She looked down at his cock straining in his trousers, twitching with the anticipation. “Do it now”, she demanded. “Take your maggot sized cock in your hand, and wank yourself off over me.”

His eyes darted over to the door. He knew he was in danger of getting caught in the act but the desire to pleasure himself was too much.

She pressed her tits close to his face, her nipples only inches away from his mouth. He could barely hold back the desire to reach out his tongue, to lick those gorgeous brown teats in front of him. But the humiliation also coursed through him. He was reaching for his rock hard dick, sliding his hand up and down on the shaft and looking at the cold sense of gratification that crossed her face as he did it.

She moved her hands down her body and slowly slid her skirt up to the top of her thighs, then placing one leg on the chair next to him. He could see the soft flesh of the inside of her thigh and there was a glimpse of the white lace of her underwear. All he could think of was how close the piece of material was to her warm, wet pussy. But as soon as his eyes looked down to take it all in, she demanded he look up. “Look into my eyes, you worthless fuck. And keep wanking that prick of yours ‘til you cum all over yourself. Drain your excuse for a ball sack right over your pants.” She moved her body closer to him. He tried to stay in the same position, fearing what she would do if he accidentally touched her. “Let’s face it, it’s not like you’ll ever get the chance to shoot your load into a real women is it?”

He wanted to grab her, pull her thong aside and push her over the table. He wanted to pound his cock into her pussy and climax as he thrust it into her. But he knew she was right, he was trapped by his inadequacies, his mixture of fear and adoration rendered him useless. The closer he was to cumming, the more he knew she had won. He was wanking hard now, his eyes glazed, his breathing heavy. She leaned in and cupped her tits in her hands, caressing and stroking every inch of the silken, smooth flesh.

He could hold back no more. If one of her housemates walked in now she’d see him, cock in hand, face flushed and cum shooting from him so hard it was like he’d never climaxed before. He cried out as he spasmed and jerked to an end.

She viewed at him with detachment. “Look at you, drenched in your own jizz”, she said with a sneer. “I think it’s time you put your dick away and got the fuck out of here. This little game is so over for me.” She walked away and adjusted her clothing.

He put his limp prick back into his pants and stood up to leave. She didn’t turn around to say anything and he instinctively knew he wouldn’t be permitted to speak to her. He walked out of the door and the thoughts started racing through his mind. What the hell was he going to do when he saw her next? Could he do anything but hang his head in shame? Would she look at him? And most importantly, he thought, could he find the strength to resist her if she commanded him to do it again?

Steamy Stories

The Geeky Dreamer

Stephen was an ordinary looking guy. Nothing special about him in any way and he knew it. Now in his mid thirties, he’d never been successful with women and had to resign himself to lusting after them from a distance. No girlfriend but a bucket load of sexual frustration was his lot in life. But there was one girl particularly on his mind most at the moment, Olivia, a friend of his flat mate’s and she was perfect. A petite brunette with a tight yet curvy arse and small but pert tits. She looked like she had great nipples too as Stephen could often see them through her top and always felt a twitch of desire as he imagined running his tongue around them.

When Stephen opened the door to her one afternoon he felt mixed reactions at his flatmate being out. Too shy to make a move but desperate to get time on his own with her, he let her in with a mumbled offer of a drink. “Make it a wine and you’ve got yourself a deal”, said Olivia with a undeniably cheeky smile. He’d seen that smile many a time before. It gave him hope but he was never sure whether it went so far as to be an invitation. But this time she kept on looking at him, eyeing him as he opened a bottle.

She followed him into the kitchen and stood right in front of him. She looked right up into his eyes and tugged on his shirt to indicate that he should kiss her. Amazed but instantly aroused he bent down and placed his lips on hers, tasting the wine on her mouth and feeling the warmth of her body as she started to press it against his. He nervously started to put his arms around her and feel some of that great body and she went along with every move he made. Her tongue went deep into his mouth and she started to rub against his crotch.

There was no hiding how he felt this time, his cock was already hard and she in turn showed him how desperate she was for it. Leading him back into the living room she started to undo his shirt and looked lustily at his hairy chest. For a bit of a geek, he was clearly hiding a rugged masculinity and she was ready to unleash it. She lay back on the sofa and hitched up her skirt. She had stockings on and a tiny, white, thong that hardly covered her mostly shaven pussy. He slid his hand into the front of the triangle of cloth that covered her cunt and reached for her wet clit. She pulled his head down to kiss her as her legs instantly parted at his touch.

This was too much for him; he needed to see her breasts now. Undoing her blouse and pulling down her bra he revealed those beautiful, brown nipples - hard and waiting to be sucked on. She reached down to undo his belt and released his pulsing cock, smoothly stroking its length right down to his balls. He was clearly ready to fuck her.

This was clearly the kind of confident and commanding decision that she was waiting for as he looked down to find her she sliding her thong down, spreading her legs wide for him and leaving her pussy open and ready. He was instantly on top of her, taking her arms gently and holding them above her head. She was completely his - he could hardly believe it was happening.

He steadily thrust his cock deep into her pussy in one go and watched her face as she let out a cry of pleasure. She opened her eyes and looked up at him, looking from his face down his body and to his cock that he was now sliding in and out of her. He was all man after all and he was going to show her that. “Spread your legs wider”, he said to her. “I want you to prove how much you want to be fucked by me.”

She obeyed him without question, opening her legs even wider as he started to thrust into her faster and harder. Her pussy was dripping wet and he knew he had her under his control. He leant down and kissed her neck and he could feel her body rise and succumb to him pounding her. This girl wanted to be fucked and was going to do anything to make herself available to him in order to get it.

His dream was really happening. He was banging her pussy and she was begging him to do it, every thrust taking her breath away. He saw her face was flushed, her nipples were hard and her breathing shortened. She cried out his name and quivered, arching her back as she came all over the cock that was fucking her hard.

He could hold back no more and was ready to empty his load into her, to shoot his cream deep into that tight, pretty pussy of hers. With his last thrusts, he fucked her hard as the warm shot of cum filled her up, pumping every last drop into her.

Satisfied and complete, the look in her eye told him she’d never been done like that before. He had a feeling she’d be back for more of the same soon - he was a success with women at last.

Steamy Stories

Steamy stories are designed to bring your fantasies to life, to get you excited by firing up your imagination. Every scenario you’ve ever dreamed of can be found here - your haven from the restrictions of every day life. Our steamy stories can take you through your every dream as well as show you ones you never thought you had!

Whether you like steamy stories that go into the details of what you’ve always wanted to do, or you want short tales to satisfy an urge we’ve got something for all. Ever wondered what is really possible? Our steamy stories even cover true, real life events!

Illicit affairs, domme, lesbianism, cross dressing - our steamy stories will cover the lot.