I suppose it all started after my friend told me his girlfriend liked to dress him in her clothes before sex. I couldn’t quite believe it – he was masculine and muscular, a real man’s man. He’d confided in me and I teased him about it unmercifully.
I mean, really? Being dressed in women’s clothes? That was supposed to be a turn-on? He seemed to think so, but I couldn’t see it myself. And the more I teased him the less he wanted to talk about it. Eventually, after a couple of weeks or so, we stopped getting together for drinks after work – and I suppose looking back it’s not hard to see why. After weeks of laughing at him about it, I guess he’d just about had enough.
So when I bumped into his girlfriend in a nightclub months later, it came as little surprise that they’d split up. She didn’t seem bitter when she told me, although there was a look in her eye that suggested she blamed me for the whole thing.
I kept my mouth shut until she asked me if I wanted to join her friends’ table across the club. I did so and went and sat with the trio. I knew Gen, of course, but I had no idea who her friends were.
I was quite amazed. Gen was beautiful enough herself, her short dark bob framing her flawless face and perfect makeup well enough. She had a slender, almost boyish body with small breasts and long thin legs that tapered down to her ankles. But her friends… well, they were even more desirable. Nikki was the shortest, at about my height. Her tiny black mesh minidress showed her black underwear clearly – a satin bra, matching boyshorts and a wide black satin suspender belt which supported black stockings with a deep lace band at the top. The outfit was almost indecent, although this club tended to encourage outrageous costumes.
Becky, the long-haired blonde, was dressed severely in a black leather miniskirt, a black leather corset top which laced at the back, and black high-heeled knee-boots. She was slightly taller than me, and I noted a look of slight disdain pass across her face as Gen introduced me.
Only Sara looked pleased to see me, and gave me a crushing hug. As she did so, her breasts pressed against my chest and I could feel a corset of some sort underneath her white velvet dress. She wore white plastic go-go boots that set the outfit off, and a string of large white beads around her neck.
Only Sara chatted to me while the others drank and danced, and we became fairly close quite quickly. She told me Gen was pissed off with me about my friend, David. As I’d suspected – I’d been firmly blamed over the failure of their relationship. I laughed it off and Sara didn’t press me about it.
After a few drinks, I realised I was feeling slightly woozy – strange, really, because I can usually hold my drink. But for whatever reason I found my vision slightly blurred and I was a little unsteady.
Sara noticed, and suggested we head out from the club. She told me she – and the others – were supposed to be staying at Gen’s house, but perhaps I could take her back to her flat instead?
Of course, I agreed. What red-blooded male wouldn’t? We went outside and caught a cab, and as we sat in the backseat heading home, Sara’s hands began to wander over my legs and thighs. But when I tried to return the favour, she simply brushed by hand off her and continued exploring my body.
I was starting to get hard, and my jeans tightened appreciably. I’m sure Sara noticed, because she started rubbing around the top of my thigh gently. She almost – but not quite – touched my stiffening dick, and I started trying to squirm my hips to place it under Sara’s hand.
She was driving me mad with lust, and I could barely throw money at the taxi driver fast enough as she walked up the path to her door and opened it. I came almost running behind her, although I was still so woozy I had to watch my step or risk ending up in a heap in her garden.
Inside, I followed her to her room, where she already had a bottle of red wine open.
“I like my wine to breathe,” she told me, and handed me a glass. I sipped it carefully, conscious of my drunken state.
“You know, you were awfully hard on David,” she said, “Gen wasn’t at all pleased with you over it. And I can’t say I was impressed either.”
I tried to reply, but my tongue felt numb and I found I was unable to form words. I must have looked as confused as I felt, because Sara looked carefully into my face for a moment, before laughing.
“I have a feeling it’ll all be alright now though,” she mused, “Everybody else will be back shortly, and I need to make some preparations.”
I wanted to ask her what she was talking about, but again my deadened mouth let me down. The unsteadiness which had plagued me in the club and on the way home returned with a vengeance, and I nodded my head drowsily.
“It’s OK,” said Sara, “You just have a lie down on the bed here.”
She led me to her bed, a king-sized affair with black satin sheets on. As I lay back, my vision dimmed, and the last thing I saw was her lifting the hem of her dress as though she were going to take it off. Despite my arousal and curiosity, I drifted off and sleep overtook me.
My wrists were aching and my thighs were going numb. That’s what brought me back to the situation.
How long had I slept? I had no idea of what time it might be, and that made me groggy and a bit slow on the uptake. My thighs were pressing uncomfortably on my calves and my wrists and shoulders felt cold. Not as cold as my fingers though.
I realised I was kneeling up with my wrists attached to something. Bed posts. I was cuffed to someone’s bed. And what the hell was I wearing?
I looked down my body and saw lingerie. Black and red. I looked up and around desperately, looking for an escape from the bonds. But all I saw in the room was a mirrored wall, with me perfectly framed.
I was indeed kneeling. I doubt I could have stood, not in the black leather knee boots with wicked three-inch heels. They glistened against black stockings which whispered up to my thighs where they ended in deep bands of black lace.
Suspenders, taut and black, led up past a scandalous pair of whore-red mesh and lace knickers which were tight across my buttocks and rubbing my cock softly. I began to get hard but suddenly stiffened as I saw the baby-doll my stockings were attached to.
It was black, and backless, with a short frilled lace skirt. Up the front ran a satin panel which slithered across my tummy and chest. The lacy bra was far from full, but the gathered satin and lace worked magic on my nipples. Long suspenders stretched down each side of my legs, tugging my stocking tops.
I tried to fight my arousal – what if someone should come into the room and find me like this? Chained up, dressed in stockings, knickers, boots and baby-doll… and sporting a throbbing erection. The shame might kill me, but it was more likely I’d have to live as a laughing stock.
I thought frantically, trying to dredge my memory for any clues as to where I was and how I’d gotten here. The last thing I remembered was… was… Sara undressing.
Was I still in Sara’s room? I couldn’t remember much about it. I’d been too busy gazing at her, hoping to lay her, to have noticed the decor. The sheets were satin, and Sara had had satin sheets on her bed, but I couldn’t remember if it was even the same bed.
And amid all the confusion, I had another problem. What to do about my cock, which was now tenting my red knickers. I tried not to think about it, but every movement seemed to slide my knickers across the sensitive underside and tip. I closed my eyes and moaned in frustration. I shuffled my knees forward, shifting my weight until I could press my cock against the satin-covered headboard.
As I began moving my hips, delicious feelings coursed through my pole as the mesh and satin conspired to tease me towards orgasm. Just as I thought I might be able to get off that way, I heard a door open behind me. I tried, ridiculously, to draw myself into a ball. Unable to see who it was, and utterly terrified it might be someone I know, I tried to make myself as small as possible. That wasn’t really possible with the manacled wrists, and all I managed to do was rattle the short chains and draw attention to myself.
“Oh god! You startled me,” a voice said. My heart sank. Sara.
“Look it’s not what you think,” I said, “I’ve no idea what happened last night or how I ended up like this. I’m not even sure where I am although I do remember coming back to yours – is this your place?”
I looked up at her, and saw she was grinning. And looking me over, in a critical sort of way. She seemed to be sizing me up, and her grin slid into a thin predatory smile of satisfaction.
I looked in the mirror and saw I was wearing dramatic, over-the-top makeup. My black false lashes had diamante tips that glistened as I turned into the light. Heavy black kohl and silver and red eyelids seemed to heighten the girlish contours of my face. My foundation and powder gave me a china doll look, although any pretence at innocence stopped ay my lips. They were masterworks of makeup, lined and coloured into a cocksucking bow. The gloss I was wearing made them impossibly red, and tiny glittery sparkles danced around my mouth.
My long hair had been let down and moulded into a feminine style which hung around my face but became a mass of curls just under my ears. They, too sparkled, and I looked closer to see I was wearing a pair of large diamante studs.
My cock was dancing in my knickers as I felt myself blush from head to toe. Here I was, dressed like a true slut, and I was ragingly hard. In front of Sara.
She moved behind me. I watched in the mirror as she kicked off her high black court shoes, and pulled her clinging black wool dress over her head before dropping it on top of her shoes in an untidy pile.
“What are you doing?” I asked her, “Can you see the key for these cuffs anywhere?”
She crawled onto the bed behind me, wearing just her lingerie. I tried not to notice it, but my turgid cock made me drink in every detail of her matching black bra, waist-cincher, girdle and knickers. She looked like a 50s starlet dressed entirely in the smoothest black satin. Even her gossamer stockings were black, with a seam at the back and reinforced heels and toes.
I was transfixed as she moved up the bed behind me and pressed her breasts against my back.
“Sara, can you get me out of these cuffs?” I asked, acutely aware of her breath on my shoulder as she rubbed her face with my hair.
“What if I said I preferred you like this? Would you really object?” asked Sara, as she ground her crotch against my buttocks and making me shiver as the satin of her knickers and the mesh of mine rustled across each other.
“I – er, well I,” I began. But I couldn’t finish. My concentration was non-existent as Sara moved closer, forcing me to spread my legs. Our stockings felt as though they cracked sparks of sheer bliss as they moved together.
“Tell you the truth, sissy, I’m the person who left you like this last night. Gen told me so much about her sissy slave David that I thought I’d go out and find me one, too. The thought of having a feminised man, smooth and sexy with a rock-hard cock to ride, makes me so fucking hot. To dress a man in frilly whores’ outfits and see how his cock stiffens as he submits his manhood to me, that’s what I want.”
“But I’m no sissy,” I said, “Far from it!”
“I know,” said Sara, “You don’t think you’re a sissy and you hate sissy men. You cracked jokes about David’s crossdressing, hurtful jokes. Secretly I think you’re jealous.”
“Jealous?!” I was shouting now, “How the hell could I be jealous? He dressed like a pansy for Gen!”
Sara didn’t respond immediately, but I heard her rummaging in a bedside drawer. before I knew what was happening, Sara had pushed a pair of knickers in my mouth, and slipped a stretchy fabric band over my head to form a very effective gag.
I tried to tell her how unhappy I was, but could only managed muffled grunting.
“That’s better,” she said, “Because from now on I’ll talk and you’ll listen. I’m going to turn you into my little frilly sissy fuckslave and you’re going to love it. You’re going to bend over for me in flouncy lingerie and stockings and high-heels and beg me to fuck you. I’m going to dress you as a naughty French maid and fuck you on your back over the kitchen table – looking straight into your pleading eyes as I pound your arse. I’m going to do things to you Gen never did to David. And all the time you’ll be begging me for more. Craving the lingerie. The humiliation. But most of all… the great fucking sex.”
Her hands had started wandering and I felt her fingers insinuate themselves up my stockings, pausing at the lace band to gently caress it, before moving onto my knickers. She teased me front and back, rubbing tiny strokes of her fingers across my engorged cock and squeezing my mesh-clad buttocks. I couldn’t help myself and I started to respond, no matter how much I was trying to resist.
I moaned and pushed my arse back against her hand and crotch.
“Naughty little girl, I think she’s actually enjoying this, being tied up, dressed up and now about to be fucked like a nasty little tramp.”
Sara’s hand on my cock began a massage both forceful and gentle. Behind me her hand slowly moved inside my knickers to my arse. She eased a finger between my cheeks and explored around my sphincter.
That elicited a long, agonised moan of pleasure from me, and I clenched and unclenched my arse as her slim digit teased and probed. Her other hand worked my cock insistently through the lacy fabric. As I writhed beneath her touch, my suspenders tugged at my stockings which in turn rubbed Sara’s. My whole body was lit up with new sensations, and I felt myself open up to her sexually.
Sara must have sensed my total fall into submission, because she removed her finger from my behind and moved in still closer until she had me pressed against the satin headboard. She left enough room to slip her hand back around my cock, which she resumed stroking.
“I’m going to dress you in a pink satin corset and knickers, roll pink and white stockings up your legs and then put you on your knees to suck my dildo and make it wet enough to fuck your pretty arse with. I’ll put you in a schoolgirl outfit with a tiny skirt that won’t even cover your stocking-tops and suck your cock through your tight knickers until you beg me to stuff my prick in your eager little hole.”
Fingers returned to my arse, this time cold and slippery. Sara began to spread something around my rosebud, before easing her middle finger into me slightly. I tensed as she pushed in, and she began to suck on my bare shoulder. I shut my eyes tight, cooed with the pleasure and relaxed.
She resumed her efforts on my hole, coating it with the greasy substance as her finger worked its way into me. I squealed as she reversed direction and slowly withdrew before ploughing back into me again.
“I know you’re enjoying this, lover,” she whispered in my ear, “All boys do, according to Gen. And why shouldn’t you like it? Dressed as my slut, ready for my cock, feeling my fingers fucking you. Being wanked off into your knickers by a gorgeous girl? I’d enjoy that, and I know you’re loving it.”
The hand on my cock moved and removed the gag.
“All I want to hear from you is that you want me,” she said.
“Oh god, Sara…” I moaned as the relentless rhythm of her finger inside me picked up pace slightly. It was now sliding in and out easily thanks to the coat of lubricant in my passage. Her other hand went back to the tip of my cock, which she rubbed with her palm.
“Tell me,” she said, “Tell me you want my cock, and you want to be my sissy. I’ll make you feel so good. I’ll fuck you into the middle of next week. Just tell me.”
If there was anything masculine left in my lingerie-clad body, I couldn’t find it. Not with one finger twisting inside me, finding breathtaking spots of nerve-endings that went off like fireworks at her touch. Not with a hand rubbing my erection through my lacy knickers. Not with my toes curling inside my high-heel knee boots. With the knowledge I was as sissified as she could make me, the resistance left in me shattered.
“Please, Sara – fuck me!” I panted.
“What’s that, my little tranny lover girl? I didn’t hear you.”
“God – please! Sara! Fuck me!” I yelled.
And with that she pressed an enormous weight against my hole, holding my knickers to one side. I looked in the mirror and saw her strapon cock as she started to feed it into my arse. Even with the lube, it was tough going to fit the monster inside of me. I fought every instinct to tense, and relaxed enough to allow the head to pop through.
That, of course, produced such a shriek from me I thought it would break glass. Sarah kissed the back of my neck wetly, wetting me with her tongue before blowing gently onto the trails of saliva. Each one felt like a river of ice, so sensitised was my skin. It didn’t take much of that treatment before I relaxed again.
Sara, still kissing my neck, began increasing the pressure on my pierced arse. Her cock began to move. I felt it sliding inch by inch past my ring, and I found I was sobbing with the sheer joy of it.
“Here we go my fuck toy,” said Sara, “You’ve taken my whole length. It’s a good start, because you’ll be wearing a remote-controlled butt plug all day every day from now on. And I’ll have you dressed in knickers and stockings every day under your suit at work. You’ll come home with that naughty stiff clitty of yours sticking out of your knickers. And you’ll beg me to suck it.”
Her mound was pressing against the small of my back and I felt utterly impaled by her huge cock. I was trying to catch my breath when she started to pull out. The feeling made me moan again, I was too far gone for words now.
“You’ll love it”, she said, “I’ll dress you as a porno cheerleader, press you up against my full-length mirror and fuck your arse until you cum watching our reflection. But my favourite…”
Sara leaned in close to my ear.
“My favourite…” she whispered, “My favourite will always be fucking you like this. Chained to the bed, dressed like a little fucking whore who can’t wait for my cock. You look so frightened, but so fucking horny. I’ll want to fuck you just this way more often.”
She’d withdrawn almost to the tip, and I groaned at the thought of losing that erotic fullness. I felt Sara’s sides quake and the sharp hot blasts of breath on the back of my neck made me understand.
She was laughing.
At that point, the cock started sliding back inside me and Sara began alternating laughing and planting hot kisses on my neck. I understood then that I was turning her on, that she actually wanted me like this, dressed in knickers, stockings and baby-doll. And that I wanted her to fuck me like this. We’d both handed power to each other – only to find our shared desires were too strong for either of us to abandon.
I grunted as that long stroke slid up and into me. And as she brushed my prostate, I couldn’t help myself. I squealed like a little girl.
Sara laughed again, and this time I laughed with her. As she withdrew, the head of her strapon caught the same spot, and I shouted my surprise and pleasure. She pounded her cock back into me suddenly, and again I let out an involuntary squeal.
I looked over my shoulder, and saw the pair of us. Me taking a strapon cock. Sarah’s showgirl underwear as a contrast to my trashy slutwear. Sara’s look of pure lust as she took control of her sissy slut.
She picked up the pace inside me, still grinning as she pounded me in the arse with her cock. Every inch of me felt alive – my stockinged legs against hers, the slight rustle as our knickers touched when her length filled me, the satin of the bed head across my nipples under the cups of the baby-doll.
Just as I thought I was going to scream, Sara did something. It quite took my breath away.
The length she was using to beat out a rhythm in my tortured ass started to vibrate. I hissed in shock – but as soon as I registered buzzing inside me, it stopped. I let out a huge sighing moan which was cut short by my off-register squeak as it unexpectedly restarted.
Even as she kept sliding her length into me, Sara laughed.
“I’m playing you with my cock, my little fucktoy,” she gloated, “You sound like a sissy symphony. All those groans – ”
She pulled her cock out of me, and right on cue I groaned with desire as each centimetre rubbed my sphincter and that maddening buzzing ceased.
” – And these squeals – ”
Sara’s stomach slapped by buttocks as she thrust the whole thing back into me in one swift motion. And just when I thought I’d caught my breath enough to scream, it let off another vibrating blast though my innards. I don’t know if there’s a way of measuring plaintive and overwhelmed squeals, but I think I’d have gone right off the top of the scale.
” – Are making me – ”
Another burst of vibration as she pulled out and rammed back into me.
” – So fucking horny – ”
Out, just far enough to allow me to tense my sopping wet and well-fucked arse. But back in before I was ready, forcing her way in. I howled with the thrill of her cock lancing my virginity, and shrieked as she spanked both of my buttocks sharply. Once again a burst of sheer bliss as the vibrator hummed deep in my passage, just as Sara reached around for my steel-hard erection.
” – but not as horny as I bet you are!”
Her hand reached into my knickers and grasped me. The sensation of her cool hands on my red hot cock made me cum almost immediately. She held her cock inside me and rubbed her mount around my sweetly tortured arse.
As her crimson-tipped fingers wanked me, I stopped being in any way intelligible. Sharp flashes went off behind my screwed shut eyes every time the vibrator hummed to life deep inside me. Her strokes were smooth and even now – she’d found her rhythm – and I found myself gasping for air and babbling as she fucked me confidently and expertly.
The mesh of my knickers rubbed across my sensitive glans as Sara’s stroking grew faster and more forceful. I was overwhelmed with sensation: my wrists strained inside the cuffs as I twisted and contorted my body, desperately trying to guide the dildo to the most erogenous spots in my royally-fucked passage.
“Look at the big man now,” grunted Sara as she continued her violation, “All dressed up in red knickers – see-through knickers. With his black stockings and his babydoll on, taking my cock up his arse. You’re loving it, aren’t you?”
She spanked me sharply just as the shrill buzz of her cock burst into maddening life and at exactly the point in my rectum I’d been trying to hit. I froze, tensing in awe of the wave that swept through my body. I was determined to hold that moment for as long as I could but Sara’s hand never stopped its motion on my cock.
I shrieked girlishly as my ring tried to snap shut on Sara’s strapon, and as she felt the resistance she plunged as far into me as she could with a triumphant cry. That was all it took to make me shoot into my knickers, her hand still wrapped around my length. I felt as though each new spurt would turn me inside out with ecstasy – joyous explosions of pleasure ran from my sphincter right the way through to the tip of my cock in its red mesh covering.
Sara slowed the pace and brought me down until I was a gasping, sodden mess. My body slumped forward and I leaned against the headboard, exhausted. She bent forward, her breasts resting on my back.
“Well, now losing your virginity is out of the way, does my pretty sissy bitch was some real fun? Does she want me to dress her in lingerie? Will she do anything I ask?” She whispered.
“Yes,” I said. I couldn’t wait.