KSB79

KSB79

M44

Role playing as Sarah

December 20 2020

“Next time I want to see you dressed as Sarah” M had said.. the words repeating themselves as I walked back from his apartment to my own, the cool autumn night air refreshing me, but doing nothing to ease the muscle fatigue in my legs. I had just spent another evening with M, my fist male-on-male partner who had not only introduced me to submission but had also expressed genuine interest when I mentioned I like to role play as ‘Sarah’ now and then.

Three weeks later he got his wish. ‘Was it his wish, or was it mine?’ I thought to myself, as I quietly sauntered over the footbridge towards his apartment. Whilst I had dressed up in private before, I had never been out in public dressed as ‘Sarah’. I hoped the cover of darkness would conceal me.. but secretly also hoped that just one or two people would see me and know what was happening.

I was wearing tight fighting women’s jeans with simple black boots that had a four inch heel on them and a fitting black t-shirt covering a padded bra. Underneath I had stay-up nylons and a g-string, and wafted intoxicating perfume as I click-clacked over the stones past the bridge. The night was very quiet, with the restaurant noises from across the lake drifting on the cool breeze.

I dialled in his apartment number and heard the familiar click of electronic locks releasing. I went through the foyer, the smell of the building triggering desire almost like Pavlov conditioning. I waited. The lift came up from basement and opened at ground for me. I hesitated to enter, as I stared into the sparkling green eyes of a gorgeous woman in her late 20s. She wore a short pleated skirt with opaque nylons, devilish heels and a tight blouse that barely kept her perky breasts from bursting out. It was not the outfit nor deadly curves that stirred me; it was the combination of sparkle in her eyes and mischievous grin that gave away her private persona. ‘Fuck’ I thought.. ‘she’s gorgeous’.

We rode the lift in silence to the fourth floor where she was getting out, both of us looking the other up and down in not-so-secret measurement. I am not the sort of person to ‘pass’ as a woman. I am 40 years old, in very good shape and have nothing feminine about me from the waist up. I can however, pull off skirts and pants that make other women jealous with slim legs and a n ass toned from years of bushwalking. It was obvious I was dressing as a girl for a night and not trans in any way.

Her perfume stirred my tightly confined crotch as she walked past, brushing past me slightly for emphasis, turning with a hand on the lift door… “I hope you have a fucking good night girlfriend” she taunted sweetly, every word deliberately chosen for impact. “Me too” I smiled back just as sweetly, and just as deliberately, the sexual tension immediately palatable. She winked as she turned and walked off, her skirt drifting up slightly and her perfect hips swayed from side to side effortlessly exuding sexual prowess that I felt I could never replicate.

I exited the lift at level nine and headed to M’s apartment which was already left ajar for me. I entered the dark room, greeted by M with a large glass of wine. “Thank you” I smiled up at him. He was much taller than me which is not easy given I am already six feet. His dark skin glistened in the lights thrown by lamps and candles. His rich accent making me melt yet again.

“You look gorgeous Sarah” he proclaimed, welcoming me and my alter-ego into his home. He reached out with one hand around my waist, drawing me close, “and you smell divine” he continued, his hand drifting down my sides to my ass, pausing and tightening at that delicate spot.

We then sat on the couch for ages, chatting over wine, talking about work and family and life, just enjoying each other’s company and relaxing music. I sat at the end of the couch with my legs draped over his lap, his hands quietly running up and down my legs, over and sometimes under the jean fabric feeling my nylon feet and ankle. “Excuse me for a moment” he said after a while, heading to the bathroom. I used the absence as a chance to stand up and go check my phone, then placed it away but remained standing as he returned.

M came up behind me, and I deliberately did not turn around. He grabbed my ass with both hands, moaning into my ear. “Mmmm, I do love this” he murmured into my ear, one hand coming around to cup my padded bra. I smiled.. and sank back into him further. For a man who used to be straight, the feeling of turning on another man made me weak at the knees.

His hands began to search in earnest, running themselves all over my body. I started to sway with the music, my own hands reaching around to caress his legs. I felt him undo the buckle of my jeans, and bit my lip at it’s implication. After he pulled my belt free, I placed my thumbs inside my jeans and slowly wriggled them down, bending at the waist as I lowered them to my ankles before stepping out of them.

I felt him against my lace covered ass, his moans and groans indicating his approval. I then stood back up keeping my ass pressed against him, sliding my hand back between us and feeling the bulge of his pants.

I licked my lips again, then took one more breath of courage before turning around and sinking to my knees. I looked up at him as my fingers fumbled with his pants. He didn’t hesitate to help me undo them, and I pulled them down releasing his cock from its confines. ‘Jesus’ I thought.. his size and shape never failing to startle me. I helped him step out of his clothes, as he tore off his T-shirt and now stood stark naked in front of me.

I didn’t waste any time in taking him in my mouth, his scent melting my inhibitions. His cock was like soft warm velvet covering a hardness and power that I could only ever dream of. We had never spoken of roles, but in the several encounters we had had, he had never once touched my cock… almost like our roles were pre-determined by destiny.. it would be his cock being sucked and my ass that was to be taken.. that was our place in life I guess. I didn’t mind. I felt at home in my role and wondered again if I would ever be brave enough to wear my chastity cage over to his place.

As always, I struggled to accommodate his size in my soft wet mouth, trying to make up for it by licking and kissing and stroking him all over. A few times I tried to take him as deep as I could, willing my throat to open as I took him deeper. “Oh you brave girl” he praised, breathing heavier and heavier as my mouth turned him on even more. His fingers played with my hair, portraying his pleasure through their caress, occasionally griping my hair or back of my head and driving himself a little deeper, conscious not to make me gag too badly. I was trying so hard.

“Come with me” he called softly, voice a lightly raspy with lust. He took my hand and led me to the bedroom. I never get over that feeling; being led by the hand to a bedroom where you know without question that you are about to be fucked hard. It is both scary and exciting, and in no small way addictive.

The room was dark and already set up with a large towel on the bed and bottles and tissues nearby. I knew my place. He let go of my hand as I climbed onto the bed on my hands and knees, ass facing him. He took hold of my panties, and gently slid them over my ass, down my legs and over my heels. Now naked except for my stay-up stockings and bra, I arched my back a little and looked back at him smiling.

“Move back here,” he instructed, and I complied shuffling backwards towards his powerful frame, my body nearly quivering at the thought of what was about to happen. His hands went straight for my exposed ass, playing with my anus a little and running over my hips and legs. I heard the plastic sounds of condom wrappers and a squirt of lubricant before the coldness of lubricated fingers on my ass. They slowly penetrated me, first one finger and then two, sliding in and out gently. Before long I was almost panting, pushing back into his fingers, my body screaming at him to take me.

His fingers were replaced with the head of his cock pressing gently but firmly at my entrance. ‘oh jesus’ I thought, his size exaggerated by my tightness. His soft but relentless pressure was rewarded by my body giving way and allowing the head to enter a couple of inches. I sucked in another breath, and willed my body to relax further. He paused for a little, then with two hands on my hips he pressed forward even more, inch by slow inch he slid into me until I felt like it was all I could take. “Wait” I breathed heavily.. accommodating his girth and length. He did wait.. going no further but thrusting ever so slowly back and forth helping my body adjust.

‘Aarrgh, that’s it.. good girl’ he moaned quietly, as he felt my muscles relax slightly, and in one final push I felt his pubic hair press against my silky soft ass cheeks. He was all the way in now, and very proud of that fact. “Of fuck Sarah, your pussy is tight tonight” he said loudly, beginning to fuck me more deliberately than before.

My eyes watered slightly as I continued to will my body to accept the invasion, his thrusts into my soft and tight anus forcing my internal muscles to part. It hurt. I wont lie.. it hurt, but I stayed put. One thing he always admired about me is the way I never complained, and I wasn’t about to start now. Besides, I could feel the pain lessening as my body relaxed into it.

Before too long the pain had subsided, replaced by the amazing sensation of internal stimulation. He noticed this too, pausing briefly to apply a little more lubricant before fucking me harder and deeper than ever. “Oh god Sarah.. Oh god!!” he called out, my hips pushing back now to meet his every thrust, my body losing itself in the moment of being fucked.

I felt what was nearly a climax several times, the last couple with me flat on the bed and his body bearing down on me. He didn’t though, and eventually he collapsed into a heap onto of me, the sweat from his body mixing with mine. ”oh you’ve worn me out Sarah” he admitted, slowly pulling himself out, rolling over onto his back and throwing away the condom. I snuggled into him, running my hands along his thighs.. just a little disappointed.

‘Bugger this’ I thought to myself, and let myself sink into Sarah’s character even more’ I straddled him, grinding myself into him a little as my hands ran over his broad chest, fingers tracing their way through his chest hairs tweaking his nipples slightly. I felt him grow again beneath me, his interest returning as I used my ass cheeks to run up and down his shaft. It did not take long before he was rock hard again, head rolling back in obvious pleasure.

He began panting. I leaned back, my hands bracing me better as I let the moment build. I pressed into him more and more, re adjusting myself when needed to make sure his cock was sliding right along my ass between my cheeks. I could see it’s head when I slid my hips back, then it would disappear has I raised my hips up again masturbating his cock with my ass. It was incredible. I had never felt so feminine as I was right now, trying so hard to bring this man to orgasm and utterly enjoying every second of it. I smiled down at him, licking my lips and getting even more into it.

His grunts and groans and moans were primal by now, his hands holding onto on my silky thighs.. “Urrgh!! he finally cried out, his cock spurting cum all over itself and all over my ass… “Arrgh.. ohh… fuck..” he moaned out, blissfully on another planet. I wriggled my ass around a little, milking his cock and balls for every last drop. We rested in that position for a few minutes, collecting ourselves before I raised myself up out the awkward position and looked down at his softening cock covered in cum.

I ignored my better judgement and sunk to my knees, quickly licking up my reward. “I earned this tonight” I thought to myself, and lapped up the sweet but salty fluids, cleaning up his cock and inner thighs. His hands rested on my head lightly, surprised at my sudden slutty behaviour, but doing nothing to stop it.

I was in heaven. Whilst it had not happened how I expected, my night role playing as Sarah had ten to me new levels of dressing up and playing as a girl. It felt liberating, empowering and more than anything enticing - It would not be the last time I dressed up for sex. The walk home did not feel like a walk of shame, it felt like a walk of accomplishment, and I strutted my self home with pride and a permanent smile on my face.