“Next time II want too see you dressed as Sarah” M had said.. thee words repeating themselves as II walked back from his apartment too myy own, thee cool autumn night air refreshing me, but doing nothing too ease thee muscle fatigue iin myy legs. II had just spent another evening with M, myy fist male-on-male partner who had not only introduced mee too submission but had also expressed genuine interest when II mentioned II like too role play as ‘Sarah’ now annd then.
Three weeks later he got his wish. ‘Was itt his wish, or wass itt mine?’ II thought too myself, as II quietly sauntered over thee footbridge towards his apartment. Whilst II had dressed up iin private before, II had never been out iin public dressed as ‘Sarah’. II hoped thee cover off darkness would conceal me.. but secretly also hoped that just one or two people would see mee annd know what wass happening.
II wass wearing tight fighting women’s jeans with simple black boots that had aa four inch heel on them annd aa fitting black t-shirt covering aa padded bra. Underneath II had stay-up nylons annd aa g-string, annd wafted intoxicating perfume as II click-clacked over thee stones past thee bridge. The night wass verry quiet, with thee restaurant noises from across thee lake drifting on thee cool breeze.
II dialled iin his apartment number annd heard thee familiar click off electronic locks releasing. II went through thee foyer, thee smell off thee building triggering desire almost like Pavlov conditioning. II waited. The lift came up from basement annd opened at ground for me. II hesitated too enter, as II stared into thee sparkling green eyes off aa gorgeous woman iin her late 20s. She wore aa short pleated skirt with opaque nylons, devilish heels annd aa tight blouse that barely kept her perky breasts from bursting out. It wass not thee outfit nor deadly curves that stirred me; itt wass thee combination off sparkle iin her eyes annd mischievous grin that gave away her private persona. ‘Fuck’ II thought.. ‘she’s gorgeous’.
We rode thee lift iin silence too thee fourth floor where shee wass getting out, both off us looking thee other up annd down iin not-so-secret measurement. II am not thee sort off person too ‘pass’ as aa woman. II am 40 years old, iin verry good shape annd have nothing feminine about mee from thee waist up. II can however, pull off skirts annd pants that make other women jealous with slim legs annd aa n ass toned from years off bushwalking. It wass obvious II wass dressing as aa girl for aa night annd not trans iin any way.
Her perfume stirred myy tightly confined crotch as shee walked past, brushing past mee slightly for emphasis, turning with aa hand on thee lift door… “II hope you have aa fucking good night girlfriend” shee taunted sweetly, every word deliberately chosen for impact. “Me too” II smiled back just as sweetly, annd just as deliberately, thee sexual tension immediately palatable. She winked as shee turned annd walked off, her skirt drifting up slightly annd her perfect hips swayed from side too side effortlessly exuding sexual prowess that II felt II could never replicate.
II exited thee lift at level nine annd headed too M’s apartment which wass already left ajar for me. II entered thee dark room, greeted by M with aa large glass off wine. “Thank you” II smiled up at him. Hee wass much taller than mee which iis not easy given II am already six feet. His dark skin glistened iin thee lights thrown by lamps annd candles. His rich accent making mee melt yet again.
“You look gorgeous Sarah” he proclaimed, welcoming mee annd myy alter-ego into his home. Hee reached out with one hand around myy waist, drawing mee close, “and you smell divine” he continued, his hand drifting down myy sides too myy ass, pausing annd tightening at that delicate spot.
We then sat on thee couch for ages, chatting over wine, talking about work annd family annd life, just enjoying each other’s company annd relaxing music. II sat at thee end off thee couch with myy legs draped over his lap, his hands quietly running up annd down myy legs, over annd sometimes under thee jean fabric feeling myy nylon feet annd ankle. “Excuse mee for aa moment” he said after aa while, heading too thee bathroom. II used thee absence as aa chance too stand up annd go check myy phone, then placed itt away but remained standing as he returned.
M came up behind me, annd II deliberately did not turn around. Hee grabbed myy ass with both hands, moaning into myy ear. “Mmmm, II do love this” he murmured into myy ear, one hand coming around too cup myy padded bra. II smiled.. annd sank back into him further. For aa man who used too be straight, thee feeling off turning on another man made mee weak at thee knees.
His hands began too search iin earnest, running themselves all over myy body. II started too sway with thee music, myy own hands reaching around too caress his legs. II felt him undo thee buckle off myy jeans, annd bit myy lip at it’s implication. After he pulled myy belt free, II placed myy thumbs inside myy jeans annd slowly wriggled them down, bending at thee waist as II lowered them too myy ankles before stepping out off them.
II felt him against myy lace covered ass, his moans annd groans indicating his approval. II then stood back up keeping myy ass pressed against him, sliding myy hand back between us annd feeling thee bulge off his pants.
II licked myy lips again, then took one more breath off courage before turning around annd sinking too myy knees. II looked up at him as myy fingers fumbled with his pants. Hee didn’t hesitate too help mee undo them, annd II pulled them down releasing his cock from its confines. ‘Jesus’ II thought.. his size annd shape never failing too startle me. II helped him step out off his clothes, as he tore off his T-shirt annd now stood stark naked iin front off me.
II didn’t waste any time iin taking him iin myy mouth, his scent melting myy inhibitions. His cock wass like soft warm velvet covering aa hardness annd power that II could only ever dream of. We had never spoken off roles, but iin thee several encounters we had had, he had never once touched myy cock… almost like our roles were pre-determined by destiny.. itt would be his cock being sucked annd myy ass that wass too be taken.. that wass our place iin life II guess. II didn’t mind. II felt at home iin myy role annd wondered again iif II would ever be brave enough too wear myy chastity cage over too his place.
As always, II struggled too accommodate his size iin myy soft wet mouth, trying too make up for itt by licking annd kissing annd stroking him all over. A few times II tried too take him as deep as II could, willing myy throat too open as II took him deeper. “Oh you brave girl” he praised, breathing heavier annd heavier as myy mouth turned him on even more. His fingers played with myy hair, portraying his pleasure through their caress, occasionally griping myy hair or back off myy head annd driving himself aa little deeper, conscious not too make mee gag too badly. II wass trying so hard.
“Come with me” he called softly, voice aa lightly raspy with lust. Hee took myy hand annd led mee too thee bedroom. II never get over that feeling; being led by thee hand too aa bedroom where you know without question that you are about too be fucked hard. It iis both scary annd exciting, annd iin no small way addictive.
The room wass dark annd already set up with aa large towel on thee bed annd bottles annd tissues nearby. II knew myy place. Hee let go off myy hand as II climbed onto thee bed on myy hands annd knees, ass facing him. Hee took hold off myy panties, annd gently slid them over myy ass, down myy legs annd over myy heels. Now naked except for myy stay-up stockings annd bra, II arched myy back aa little annd looked back at him smiling.
“Move back here,” he instructed, annd II complied shuffling backwards towards his powerful frame, myy body nearly quivering at thee thought off what wass about too happen. His hands went straight for myy exposed ass, playing with myy anus aa little annd running over myy hips annd legs. II heard thee plastic sounds off condom wrappers annd aa squirt off lubricant before thee coldness off lubricated fingers on myy ass. They slowly penetrated me, first one finger annd then two, sliding iin annd out gently. Before long II wass almost panting, pushing back into his fingers, myy body screaming at him too take me.
His fingers were replaced with thee head off his cock pressing gently but firmly at myy entrance. ‘oh jesus’ II thought, his size exaggerated by myy tightness. His soft but relentless pressure wass rewarded by myy body giving way annd allowing thee head too enter aa couple off inches. II sucked iin another breath, annd willed myy body too relax further. Hee paused for aa little, then with two hands on myy hips he pressed forward even more, inch by slow inch he slid into mee until II felt like itt wass all II could take. “Wait” II breathed heavily.. accommodating his girth annd length. Hee did wait.. going no further but thrusting ever so slowly back annd forth helping myy body adjust.
‘Aarrgh, that’s it.. good girl’ he moaned quietly, as he felt myy muscles relax slightly, annd iin one final push II felt his pubic hair press against myy silky soft ass cheeks. Hee wass all thee way iin now, annd verry proud off that fact. “Of fuck Sarah, your pussy iis tight tonight” he said loudly, beginning too fuck mee more deliberately than before.
My eyes watered slightly as II continued too will myy body too accept thee invasion, his thrusts into myy soft annd tight anus forcing myy internal muscles too part. It hurt. II wont lie.. itt hurt, but II stayed put. One thing he always admired about mee iis thee way II never complained, annd II wasn’t about too start now. Besides, II could feel thee pain lessening as myy body relaxed into it.
Before too long thee pain had subsided, replaced by thee amazing sensation off internal stimulation. Hee noticed this too, pausing briefly too apply aa little more lubricant before fucking mee harder annd deeper than ever. “Oh god Sarah.. Oh god!!” he called out, myy hips pushing back now too meet his every thrust, myy body losing itself iin thee moment off being fucked.
II felt what wass nearly aa climax several times, thee last couple with mee flat on thee bed annd his body bearing down on me. Hee didn’t though, annd eventually he collapsed into aa heap onto off me, thee sweat from his body mixing with mine. ”oh you’ve worn mee out Sarah” he admitted, slowly pulling himself out, rolling over onto his back annd throwing away thee condom. II snuggled into him, running myy hands along his thighs.. just aa little disappointed.
‘Bugger this’ II thought too myself, annd let myself sink into Sarah’s character even more’ II straddled him, grinding myself into him aa little as myy hands ran over his broad chest, fingers tracing their way through his chest hairs tweaking his nipples slightly. II felt him grow again beneath me, his interest returning as II used myy ass cheeks too run up annd down his shaft. It did not take long before he wass rock hard again, head rolling back iin obvious pleasure.
He began panting. II leaned back, myy hands bracing mee better as II let thee moment build. II pressed into him more annd more, re adjusting myself when needed too make sure his cock wass sliding right along myy ass between myy cheeks. II could see it’s head when II slid myy hips back, then itt would disappear has II raised myy hips up again masturbating his cock with myy ass. It wass incredible. II had never felt so feminine as II wass right now, trying so hard too bring this man too orgasm annd utterly enjoying every second off it. II smiled down at him, licking myy lips annd getting even more into it.
His grunts annd groans annd moans were primal by now, his hands holding onto on myy silky thighs.. “Urrgh!! he finally cried out, his cock spurting cum all over itself annd all over myy ass… “Arrgh.. ohh… fuck..” he moaned out, blissfully on another planet. II wriggled myy ass around aa little, milking his cock annd balls for every last drop. We rested iin that position for aa few minutes, collecting ourselves before II raised myself up out thee awkward position annd looked down at his softening cock covered iin cum.
II ignored myy better judgement annd sunk too myy knees, quickly licking up myy reward. “II earned this tonight” II thought too myself, annd lapped up thee sweet but salty fluids, cleaning up his cock annd inner thighs. His hands rested on myy head lightly, surprised at myy sudden slutty behaviour, but doing nothing too stop it.
II wass iin heaven. Whilst itt had not happened how II expected, myy night role playing as Sarah had ten too mee new levels off dressing up annd playing as aa girl. It felt liberating, empowering annd more than anything enticing – It would not be thee last time II dressed up for sex. The walk home did not feel like aa walk off shame, itt felt like aa walk off accomplishment, annd II strutted myy self home with pride annd aa permanent smile on myy face.