Andy as Mandy Lose His 'Virginity'

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Andy finally loses his anal cherry to a strap-on.
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Andy continues the tale where Polly left off... just heading home after a trip to the sex shop.

I couldn't really believe what was happening to me, nor what had happened so far. I had just walked out in town as a slim and sexy woman, with my new friends in tow and my cock tightly constrained in the shiny latex knickers given to me by Cheryl. I had even bought a strap-on fake cock, having never been in a sex shop before. And Polly had made it very clear that as well as using it themselves, they intended me to sample its delights. I had stoked its long, ridged and apparently very lifelike form and shivered before paying a very slim, sexy female assistant for it. No drinks for us, we decided to go home, and although I was looking forward to it there was a certain trepidation in not knowing just what they had planned.

In the car Cheryl started the moves, and we were soon entwined in a very passionate kiss. I let myself go, and melted into her arms, fully playing up my role as submissive playmate. I felt Cheryl's hands roam around my back and onto my tight buttocks, her tongue insistently probing between my lips and exploring my mouth and tongue. I wrapped my hands around Cheryl and slowly slid them down her back. I rolled her firm cheeks in my hands through the silk of her skirt. All the time I could see that Polly was watching us in the re-positioned rear view mirror and twitching in the driver's seat. Cheryl was now fondling my fake breasts, but as far as I was concerned they were mine, sending shivers and electric jolts straight to my cock as they were held, rolled, tweaked and caressed through the clothing I was wearing. I tried to edge my hands down to the hem of Cheryl's skirt, but my hands were moved carefully back up to her breasts and the signal was definitely to stay clear until later.

Soon we were back at the house, and Polly took immediate control. "In, Mandy remove your knickers and kneel in readiness to serve both Cheryl and I with your very under used tongue." I immediately responded and slipped my hands under my skirt, reaching for the latex knickers Cheryl had given me earlier. I knew my cock was aching beneath them and it sprang free as I pulled the shiny fabric down my stocking clad legs and off over the heeled shoes I was wearing, almost with pride now. Putting them to one side I knelt as Polly approached.

"Cheryl, I believe she is yours first. Mandy - no hands, I want her writhing before she goes off to get ready for your next treat." With that Polly turned and went out of my view.

Cheryl lifted the hem of her skirt slightly and took off her knickers, and I could see they were already damp in the crotch. She came up to me, put her pubis in my face and told me to lick until my tongue was worn out. I got to work, taking care not to use my hands. My tongue slithered over smooth flesh above her hard clit, peeping from the shiny wet hood. Easing down I wasted no time for fear of punishment, and stabbed my curled tongue between soft, silky and aroused lips. Reward was a gasp and a slight give in Cheryl's knees as she grabbed my head and held me tight. I got into a rhythm, stabbing in and out between warm, gushing lips that I could feel getting more engorged and wider as Cheryl's gorgeous honey flowed out. I slurped and sucked, my tongue working hard, my lips fastened on hers as I drank her nectar. She was writhing above me now, my head held tight against her mons, my tongue unable to move from her cunt lips. I licked from side to side, and then drew her clit into my mouth, closed my lips around and gently nibbled the hard flesh. I was rewarded with a tensing of thighs around my head, a stifled cry and a warm gushing of ever more of her heavenly juices as Cheryl's came into my mouth and over my face.

As she moved away I realised I was rock hard under my skirt, and my lipstick was smudged, tell-tale signs of it over the bare flesh of Cheryl's mound. Before I could say anything, Polly whispered in her ear and then approached me, skirt held high. Almost before I had time to collect myself I felt her skirt settle around my head and Polly's warm cunt lips were settling on my mouth. Her hands went behind my head and pulled me tight against her smooth flesh. My tongue went to work again, and I rolled it to make it hard as I stabbed it between her puffy cunt lips. I noticed a difference in taste as Polly's juices filled my mouth and her scent my nostrils. Licking hard I could sense Polly struggling above me, clamping me tight against her as I frantically licked between her lips. I was enveloped by the glorious tastes and odours of Polly as I stabbed again and again with my tongue into her dripping love tube. Finally, almost breathless myself, I began drawing a hard clit into my mouth. I grazed it lightly with my teeth, then tried to blow on it, though getting far enough back from Polly was difficult. Her knees were shaking slightly as she pulled me back in and I sucked as much of her lips and clit as I could into my mouth, bathing them in a mix of my saliva and her own juices. Suddenly she came hard, and this time my mouth was flooded, Polly almost gushing juices as she bucked and writhed above me.

Polly stepped back, breathing hard herself and I looked up from my subservient position. She smiled and said, "Thank you Mandy, that was fantastic and as a start to your serving of our needs it was good. Now, Cheryl, are you ready to enjoy our toy a little more?"

I looked around, my face wet with a combination of cum from two horny females. Polly was now slipping her skirt off to leave her with those glorious legs exposed fully. But it was Cheryl to whom my eyes were drawn. She had returned in sheer white stockings held up by a white, quarter cup basque. What drew my eye was the straps around her tight cheeks holding a long, rubber cock in front of her. This was not the one we, well, I had chosen but slightly shorter and wider, but with the same realistic moulded head and ridges. I gulped slightly, but Polly soon indicated it was not yet my time but in fact hers.

I watched in awe as the two half-sisters wrapped themselves around each other and kissed hard. Polly reached between them and stroked the fake cock as their tongues fought a loving battle between their lips. I was just left to watch as Cheryl slid her hands round Polly and rolled her smooth, tight ass cheeks around. I was still knelt down and quite uncomfortable but knew I shouldn't move. My erect member was pushing the front of my skirt out as I watched the raw sexual activity taking place in front of me. Almost as if planned (which they later told me it was), Polly turned around and looked at me as she bent over, presenting her tight ass for Cheryl's closer inspection. Cheryl bent down and leaned in towards the tight globes of her half-sister's perfect rear. Her tongue lid its way between them and into the crack, and by the way Polly writhed and moaned I knew Cheryl was teasing the puckered ring of Polly's tight rear hole. She worked at this for what seemed ages, and I watched mesmerised as Polly's breathing became ragged and her face flushed.

Eventually standing up Cheryl moved away from Polly's ass, making her groan in frustration. Cheryl then told me to lie down on the sofa, and positioned me with my heels on the floor and stocking covered legs exposed. Lifting my skirt further up, Cheryl leant over and gave my rock hard member a brief lick, removing the drops of pre-cum gathered on its purple head. I jumped at the touch, the end was so sensitive and ready for action! Reaching down Cheryl found a tube of lubricant and gently, almost coyly slicked some all over my cock. Turning Polly to face away from me, she eased her playmate's perfect cheeks towards the head of my waiting cock and I realised Cheryl was intent on sliding my cock into Polly's wet and waiting ass. I tried to prepare myself for what was to come, to think of anything else to keep myself from cumming too soon. However, nothing I had experienced before had me ready for my first anal fuck, as Cheryl and Polly between them worked Polly's the tip of my sensitive cock into the crack between Polly's tight cheeks. Polly relaxed and I felt the head pop inside but, god, it was tight.

Polly eased down and back, getting my rock hard cock further into her tight rear hole with each one. I couldn't believe how tight it was, and I knew I would struggle to hang on for too long. With Cheryl's help Polly slid slowly onto me, and eventually took the whole of my solid flesh into her ass, groaning as it filled her completely. I could only see her back and wasn't really aware of what Cheryl was doing as she made Polly lie back a little towards me. Polly slid up and down a few times on me, the gripping sensations almost too tight for me despite the lubricant.

"Fondle my tits, and don't be gentle about it... I want to cum," growled Polly as she lay back further, "Grind your cock into me now," she went on.

Doing as I was told I started to hump upwards into Polly, the difficult position giving me little room for movement but clearly making Polly more aroused. I reached around and started to fondle Polly's small, pert breasts through the thin fabric of her shirt. Her nipples were already like little bullets, hard points of aroused flesh that I rolled around between my fingers before pulling each one out slightly and tugging. I was rewarded with a positive groan from Polly and encouragement to be 'rougher, now'! I slipped my hands under her shirt and took hold of the nipples again. Pulling hard I teased and stretched as far as I dare, and pinched them tight between my finger tips, all the time keeping up a steady thrusting into her rear. Grabbing each breast completely in my hands, I rolled and pummelled them as best I could, as Polly ground her tight ass up and down on my cock and slid her legs against my stocking-covered thighs. I had almost forgotten quite how tight this felt, as the lubricant and the effort were clearly relaxing Polly, but without warning Cheryl's hands stilled Polly.

"AArrgh, ummmm... ooooh god." I couldn't stop myself from crying out as I exploded uncontrollably into Polly's unbelievably tight ass. Cheryl had just driven her strap-on fully into Polly's waiting cunt, and the unexpected sensation of something sliding along the length of my embedded cock was just too much. The thin membrane was no guard against the thick veined, moulded head as it ploughed its way in and made a tight situation even tighter. I spasmed again and again, feeling Polly start to contract her muscles as she too reached her own orgasm. I could feel Cheryl driving the fake cock mercilessly into Polly, as I strove to keep her fastened securely to me. She was screaming and yelling obscenities at us both as her body buckled and writhed above me, held in place by two cocks in her. Her contractions felt so tight I thought my cock was being broken in two as she finally started to come down, slowly easing and now panting as she lay back on me and took my hands from her tortured nipples. I realised I had held on tighter and tighter to the pointed flesh as first my own, and then Polly's orgasm swept through.

I felt Cheryl slip the strap-on out of Polly and then help her half-sister to stand up, slipping my softening cock out of her rear hole. I just about remembered where I was and didn't stand up. I was likely to be in trouble for coming early and ahead of Polly, so I didn't need anymore. I was, after all, still very much a woman with a real cock, the tight sexy clothing seemed barely ruffled, the heels still keeping my calves tight inside the nylon stockings. A dishevelled Polly stood shakily and passed me a cloth, saying, "Clean up, don't move far, lie back and expect to be used again."

Realising the game had yet to reach its conclusion, and really not wanting it to, I did as I was told. Cleaning my slightly softening cock I smoothed my skirt down in a modest attempt to hide it before laying back on the bed and awaiting my next orders. I could hear Polly and Cheryl moving around out of sight, but what they were doing was not for me to find out until they wanted me to. I was not to be kept waiting long, as they soon returned with what I knew was a butt plug. It looked like a softly, pliant rubber with a wide base that would nestle between someone's cheeks once the full 5 or 6 inches of it was eased in. I was intrigued, until I had the instruction to turn over and get onto my knees. I felt some hands lightly touching my stockings and inching up my legs, taking my skirt hem with it as they exposed my ass cheeks. The light touch on the nylon stockings was electric and went straight to the root of my penis, starting its upwards progress once more. The hands continued and bared my taught flesh completely, teasing me by rolling my cheeks around a little before easing their way to meet at my rear hole. The plug was clearly coming my way, and I was both excited and a little worried. I had never had anything in there, well anything other than the odd finger from a more innovative girlfriend.

I felt the cool lubricant being rubbed into the tight ring, and a finger teasing and easing inside,... oohh god, that actually felt good. It explored a little, roaming around and moving in and out to expand the ring and make way for the plug. A second finger joined the first after a while, and I lay nose down, ass up as someone played around and aroused me again. The fingers were slowly withdrawn, and I felt a sort of emptiness, but not for long. The slim point of the plug was nudging against the slickness of my lubricated ass and being slowly but surely twisted and slid into my ass. I gasped as it got further and further in, whoever it was doing it was slipping it back and forth but further in each thrust. The wider part of the plug was stretching me, and I was gasping and groaning, somehow liking the sensation yet feeling invaded. Finally, the widest part slid past my ring of muscle and with a gently slurp settled the flange against my cheeks.

The hands smoothed my skirt down over my cheeks, leaving the plug in place, and I was acutely aware of it, and the effect it had no my cock, which was now straining the front of my skirt. I was instructed to turn over and saw yet another toy for someone to experience. Cheryl, still in her white basque and stockings, was holding another solid looking cock, but this time with a ball shaped end and straps on it.

"Open wide, this is also for you", the instruction coming from the smiling, red lips of Polly. I did as I was told and she settled the ball part in my mouth before slipping the straps around the back of my head and locking the ball into place with the velcro. I could breathe through my nose, and the ball didn't go too far into my mouth so I wasn't gagging but I could see the solid, rubber cock sticking out obscenely from my painted lips. Cheryl approached as Polly finished, and she had taken her strap-on cock off, her long, slim legs and smooth, sexy mound and lips clearly wating for excitement. She got onto the bed, a leg either side of me, and I realised what was happening - I was being used again to bring pleasure. Cheryl slid forward until her clit was almost above me, and locking eyes with me she spread her shiny, sleek cunt lips apart and teased herself with the tip of the cock sticking out of my mouth. I was helpless as she teased herself with the hard rubber phallus, sinking slowly onto it an inch at a time. Cheryl groaned and I had the most amazing view of her ruby red sex lips being spread further and further apart by the solid cock above me. Cheryl's juices were running freely now, and with each small slide off I could see the veined member was coated with her juices.

Cheryl finally ground her way down and took all of the cock inside her, groaning with the pleasure and fullness of it all. Her clit was almost rubbing my nose, her scent was everywhere and her juices were beginning to find there tantalising way into my mouth, around the ball gag the two sisters had placed there. I had no idea what Polly was doing, but I didn't care. My ass was full and teasing my tightest passage and Cheryl was grinding away above me, sliding up and down on the cock in my mouth and fast approaching her orgasm. I could do nothing, just laying there with my ruby red lipstick clamped around the base of the cock now giving Cheryl a ride to remember. Her juices were flowing fast again now, slick and tasty as they filled the remainder of my mouth, leaving it hard for me to breathe as I slurped as best I could. My nose was full of her scent as she suddenly arched and clamped her lags around my head, screaming as she came hard onto the fake cock, yelling, "yes, yessss.. yeeerrrrss... aaarghh" as the waves took her. Slowly she came down and slowed up her movement until she rested her smooth bare pubis against me and mouthed, "Thanks".

I couldn't respond, my lips felt stretched wide and I became aware again of the fullness of my ass as I had chance to focus on my own sensations. Cheryl slowly lifted herself off the hard cock sticking out of my mouth, and I was rewarded again with a close up of her engorged, wet sex lips almost obscenely sliding off the hard, ridged flesh coloured member sticking lewdly out of my red lips. With a sigh Cheryl let it go and she stood aside, smoothing down her skirt almost as if nothing had happened. I felt Polly reach from behind me to undo the velcro straps and with relief I felt the ball gag taken gently out of my mouth. I worked my lips and jaw again, savouring the taste of Cheryl's copious juices that were slickly coating my lips and face. Polly quietly told me to kneel up and face her. I did so, and almost fell back with surprise. Polly was now dressed only in a black PVC quarter cup basque and shin black stockings. Her small pert breasts were pushed up and out of the cups, nipples erect and proud, turned on by what she had just witnessed. Her heeled pumps must have been at least 4 inches high, but what took me aback most of all was the new, long strap-on cock in front of my face. Polly just said, "Suck it as you would want yours to be sucked.", and slid it towards me.

This was almost too much, but somehow I just slipped into gear and knelt as told. I couldn't imagine what the sight would look like from the side, as I knelt still dressed sexily in my skirt, stockings and heels with my bulging cock visible against the tight fabric. As I knelt I felt the plug move gently around in my rear, reminding me of its insistent presence. I looked up at Polly's smiling face and was aroused again by the view of the shiny pvc and the small, pert pink nipples proudly erect above it. Deep breath and I opened my mouth, closing my lips around the false cock that Polly pressed forward at me. I knew what I liked, and started to mimic that, without any thought that Polly could not feel what was happening, but could only view my lips, almost obscenely stretched around the hard rubber cock she was insistently pushing further into my waiting mouth. I warmed to my task, sliding my tongue around the ridges this false cock had, engulfing it in my mouth, easing off before plunging back in and trying out how far I could swallow it. With an almost detached interest I pushed my limits, gagging a little as it hit the back of my throat but revelling in the fullness of my mouth and the ride I was giving Polly. She began to buck gently with me, thrusting the cock slowly in and out of my mouth as I slurped noisily at its solid ridges and wide tip. It was long, and I couldn't get it all in, which seemed to be causing me concern as I worked at bringing this fake cock to orgasm! I felt Cheryl re-appear and approach us, and her arms wrapped around my waist lifting my knees gently from the floor so I was more upright but still giving head to Polly's fake cock. I could see above me Polly was tugging at her nipples now, head back and hair thrown aside as she panted and heaved.

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