Andy Becomes Mandy

Polly and Andy had met some weeks before (A chance reunion. She arranged for Andy to call by and this is her story of the next encounter.

I waited a week after that first meeting with Andy. We had known each other for quite some time and flirted often but I would never get involved with colleagues. I had left the firm regretting this inflexible rule, so the meeting at the conference was just perfect. The fact that Cheryl, my half-sister and sexual playmate could join us was a bonus. We all parted with the unspoken agreement to meet again soon, possibly at our place as Andy travelled with his work.

As I only had his work e-mail I was relatively discreet, but I hoped the underlying message would be clear - when would the games continue? The reply was prompt and promising - Andy was arranging something for a couple of weeks time, would I be available for further discussion of priorities? Too right I would and I know Cheryl would be too. Before replying I agreed with her how we would play it and then I called him.

After a few pleasantries whilst others were listening, the banter and innuendo started just as good as it always was. But this time there was something more, and I could tell Andy knew it as much as I did. I reeled him in eventually with the plan Cheryl and I had agreed.

"Our last meeting was pretty adventurous, but are you ready for more?. If you decide to come over you will play our game. We each have a 1 in 3 chance of losing and becoming the sex toy of the other two, which will include going out for a walk in an outfit matching one of the two winners. If you are up for this, we each wear 6 items only and play cards for them. First to lose them all will be used as the winners wish. You do have a 2 in 3 chance of being in control of one of us! Let me know by Friday," and I rang off.

Andy rang first thing Friday morning. Clearly in a hurry he came straight to the point, saying, "Sounds fantastic, I hope to be choosing the outfit but regardless of the outcome we should all stay smooth, if you understand."

As he cut the call I smiled, his request for smooth was a link back to our first meeting and one which we would all enjoy. Cheryl and I spent the next week or so refining the outfits and plans for Andy as our sex toy, as we were sure he would lose the game.

The knock was spot on time and I made my way to let Andy in. Cheryl was just squeezing in to one of her items of clothing as I opened the door and flung my arms open. I was pleased to note his wide eyed look before he gave me a huge hug and stepped inside. Breathless from his crushing embrace I stepped back to let him look me over, as he clearly wanted to. I had chosen carefully and he would be intrigued by my choice. I normally don't like tights, but the sheerness of the nylon and the shimmering grey was so sexy on my slim legs that this pair was perfect for the short skirt.

The skirt is one of my favourites but is far too short for my normal stockings. Its slightly flared and finishes barely below the tops of my thighs, and the denim blue silk adds to the vision. I have chosen my best heeled mid calf length boots, soft leather caressing my feet and ankles inside their slinky nylon sheath. So that's four, though Andy may be thinking five. My wide necked white blouse shows no straps though I know my small round breasts will be barely visible. Item 6 is important for my modesty - a thin, tight thong to cover my still smooth mound.

Andy was still drinking all this in when Cheryl finally appeared. She is taller and fuller in figure than me, and showed this off well. High heeled sandals with sexy ankle straps, an asymmetric skirt that showed a lot more of one thigh than the other and a clinging tee shirt that showed a few lines of something underneath. I knew what was kept hidden but Andy had to wait. Cheryl's lightly tanned long legs were perfectly displayed as she and Andy exchanged welcome kisses.

I quickly moved through to the lounge and sorted a drink before getting ready for the start of the game. I went through the rules again and got the cards out. Andy, as I thought he might, shuffled them, smiling as he did so. As we were about to start I offered more drinks, asking Andy to help get nibbles. The game began, with the prepared pack of cards Cheryl had replaced whilst we were out. This would be good!

The first few rounds were even, and as the drink flowed we all enjoyed teasing each other as the first items were removed. Typically we all took off our two shoes before it started to get serious. Cheryl was the first to get a third item to lose, and she stood up before tempting us both. Lifting her top she slowly revealed her fine breasts, captured in the tight black corset! I watched Andy's delighted reaction as her full breasts were straining and stretching the slinky fabric, and her nipples were pushing it out.

Andy was not paying too much attention to the next couple of rounds because he lost them both. Only as he removed his t-shirt, leaving only chinos and whatever he had underneath, did he realise his predicament - he was only two hands away from becoming our plaything!

The next to lose was me, and I quickly stood to slip my very short skirt off. Andy gasped as my sheer tights and thong were revealed. I twirled slowly around, teasing both my admirers with my tight, nylon covered cheeks. Andy then lost again and removed his chinos, showing off a fine pair of silk boxers being pushed outward by a developing erection. I reached forward as if to grasp it, but Cheryl reminded me this was against the rules. The next to lose was Cheryl again and both Andy and I were watching with interest as she slipped her hands under her skirt and tugged her knickers into view. As she stepped out of them completely we could see they were made of shiny black latex, glistening and slinky in her hands. Cheryl handed them to Andy saying, "I hope these fit you, I can't wait for you to try them out."

Andy was swift to reply, "Don't count on winning yet, you could still be my sex toy."

However, the next round of cards was to be the last, and Cheryl and I waited expectantly for Andy to remove his last item. He stood up, smiled ruefully and slid the boxers down, saying, "I'm all yours then!"

His erect cock sprang free, and I smiled in anticipation. Andy's cock is not overly large but perfectly proportioned (well it seemed to fit me pretty well last time!). The swollen pre-cum covered tip was shiny and round, and the slight inward and upward curve certainly had reached into my love hole to great effect. Still, more of that was to come as we had to prepare Andy for his night of control. I slipped my skirt back and boots back on before approaching Andy, sliding my hand around his firm cock and tugging him towards me with it. I kissed him soundly on the lips but broke away before we could get too engrossed, as Cheryl had now returned to some semblance of decency as well, shoes and top replaced but interestingly her latex underwear was left in view.

"So, you are ours to do with as we will! I see you have kept yourself 'smooth' as you suggested we all did?"

This was a reference to Andy keeping his legs shaved following our time together a few weeks ago. Cheryl and I always maintain perfect smooth flesh in areas that matter, which Andy had discovered to his joy last time. However, Andy was going to get smooth in places he originally would not have expected.

"I think we need to make you feel comfortable and ready to go out in an outfit of our choosing, as the loser agreed to do. We think a similarity to Cheryl's outfit would be just perfect, but you do need to be a little more prepared. So, we need you to really be smooth...... everywhere a girl would be."

Andy looked shocked and was starting to protest when I stopped him with a press of a finger to his lips. I reminded him he entered this game freely and agreed to the rules, and that he would be very upset if at this point one of us was trying to dispute the proceedings. He nodded ruefully, and followed me out of the room to the bathroom. Cheryl came along too, smiling all the while as we proceeded to cover Andy with hair removing cream. In particular we made sure his cock and balls were well and truly coated, along with his arms, legs and chest. Finally we targeted his face to make sure there would be no five o'clock shadow for our outing later, an outing Andy seemed to have forgotten about. Andy's cock stayed erect for the whole time, hardly surprising as he had two sexy women covering him with cream and playing with him.

We left him coated in it for a few minutes and then using the shower head I slowly washed off the cream, and with it all of Andy's body hair leaving him as smooth as he had been for quite some time. Andy was swaying slightly as he tried to push himself towards our hands, and I could see precum forming on the head of his glistening cock. Whilst I was drying him gently Cheryl opened the tub of body lotion. Taking it in turns we started to moisturise Andy's slim calves and toned thighs. Ignoring his pleas for relief and his now straining cock we worked on the rest of his body before kneeling down, one either side of his firmly erect flesh. I scooped a little of the cream into both hands and started to massage gently into the tight, hairless balls. As they slipped nicely around in my hands Cheryl started to moisturise the erect member, easing the flesh back and forth and eliciting a groan from Andy as he enjoyed the silky sensations. If anything his cock grew more and its lightly glistening head became more swollen as we teased and tortured him. Looking across at Cheryl I nodded slightly and with a gently stroke we both stood up and left his rock hard flesh quivering on its own.

"Nooo, you can't be serious? Leaving me like this? I will never get inside any of that clothing like this.... pleeeease," Andy almost begged us as we stood up. I smiled, and I knew we had his attention for the rest of the day. I indicated for him to follow me along to the spare room where Cheryl had laid out what we hoped would be Andy's 'winning' outfit. Just before we walked in I decided not to show him his all of what to expect quite just yet, so diverted Andy and Cheryl into the main bedroom whilst I collected a couple of the items to tease him with.

Andy stood and stared down at the short skirt and high heels in front of him and gulped. He looked across at us as if for confirmation, and I nodded as Cheryl said, "There are a couple of extra items that I am not wearing, but as you lost and are ours to do with as we wish, I don't think that's a problem, do you?"

Andy took a deep breath and shook his head, smiling almost to himself. His stiff cock stood proudly out in front of his smooth body, just waiting for our attention. I could see him contemplating the clothing in front of him and what it meant. The extra items I had left in the spare room included a blonde wig, corset and stockings and a neat shoulder bag, which would leave him in no doubt we were going to dress him up properly and take him out. It was time to start, so we had to do something about that erection which would not fit neatly into the latex knickers recently vacated by Cheryl!

"Andy, lie down, arms back and let the sensations flow, Cheryl is going to experience something she didn't get chance to last time - you!"

Andy did as he was told and lay on the bed, his cock standing proudly up from his taut stomach. Cheryl knelt astride his thighs facing him and lifted her skirt slightly. Staring straight at Andy she reached under the folds of her skirt to spread her sex lips wide and without looking away slipped down onto Andy's erect cock. As she started to impale herself slowly onto his flesh Andy groaned and I could see him fighting hard not to start to screw her himself and release his load straight away. Cheryl continued her downward progress, taking all of Andy's hot flesh inside her, settling herself at last onto his thighs, her smooth pubic bone no doubt resting on Andy's similarly hairless one. At last Cheryl smiled and started to slide off Andy before plunging back down again. Gradually I watch her pick up a rhythm and speed as she ground away for her own pleasure. Andy was trying hard to do as he had been told, but every now and then he thrust slightly upwards to meet Cheryl's downwards plunge, taking his cock as far into her as he could.

I remember only too well what that feeling was like, and I knew both of them would be getting close to their climax. I wanted Andy to empty himself completely inside Cheryl's steaming sex and I needed it to happen quickly. Stepping towards Cheryl I leant in and planted a kiss firmly on her lips, sliding my tongue in her familiar mouth right in front of Andy's eyes. I knew how hot he would find this as she continued to ride him slowly towards his orgasm, and as we kissed passionately I slipped my hands under the front of her skirt and inched my fingers lightly towards the action. Missing the thrusting cock and slurping lips I reached around for the sensitive bit right at the base of Andy's impaled flesh. Scratching gently with my finger end I knew he would not be able to resist too long, and his panting and groaning confirmed this. Just as a I stretched out to touch the outer ring of his puckered ass Andy cried out, "No, Polly, nooo I can't stopppppp ungh" and I felt him thrust up hard into Cheryl and hold himself as the first powerful spurt came out of his balls and into the waiting folds of Cheryl's cunt.

I kept my fingers as close to Andy and Cheryl as I could as he thrust several more times upwards into her, before finally collapsing. Cheryl looked almost disappointed as we parted. She was disappointed she had not reached her own climax as I had deliberately speeded up Andy's. We still had our sex slave at our mercy and I whispered in to Cheryl what I suggested next. She grinned delightedly and let Andy slide out of her, turning quickly around and moving her well used sex lips towards Andy's waiting face.

"Please finish Cheryl off before we get you dressed to kill, but only your tongue can be used whilst I just help with a little teasing," I said with a smile and Cheryl lowered her cum-filled cunt towards Andy, who had no choice but to start licking. Cheryl groaned delightedly as Andy got to work on her aroused and dripping love tube, and I reached under her skirt and sought out the pleasure button that is her clit. As I felt the tiny bud harden and slide under my fingers Cheryl really started to yell loudly, "Yeesss, yessss, suck harder, aaarghh...." as Andy and I combined to quickly bring her off in a noisy, shaky climax. As Cheryl slumped forward and freed Andy I could see his face was wet and sticky, covered in a mix of Cheryl's prolific juices and his own creamy white cum. I was getting really horny now myself, and could feel my outer lips getting moist and engorged. I tried to put this aside, smiled at Andy and asked how he found this new experience.

"I was caught by surprise and didn't really have time to think about what was happening, and I didn't expect to enjoy it at all. But the sound and movement from Cheryl, the taste of her sexy juices mixed in with my own was surprisingly erotic and I really got into it. I see Cheryl did too.... but I think I will need a clean before we go out!"

He was absolutely right, and although I found it a highly erotic sight we would indeed have to clean off the trickling white juice before we applied his evening make-up. Cheryl had now recovered and was making herself presentable as we led Andy to the bedroom where we had laid out the clothes we needed him to wear to match as closely as we could to Cheryl's outfit. Andy's face blanched when we walked in.

"You are really serious about this? You honestly think I am going to go out dressed like this? I,.. well, we.. just .. how... are you...," he burbled, finally running out of objections as we reached the clothing. I led him past and into the bathroom, giving him time to clean up before we got to work. Whilst he did I snuck a quick hug with Cheryl, as I hadn't had any opportunity to deal with my own frustrations. I knew I was moist and ready for anything, but I wanted to let the feeling build. I knew that when my first climax came it would be well worth the wait but I did want to keep my juices flowing so I slipped my tongue between Cheryl's ruby red lips. As we kissed I kneaded her tight cheeks through the silky fabric of her skirt, and she got the message straight away. Her hands finally began to roam around my own small butt, slipping under the short skirt and sliding lightly over the nylon covered flesh. Just as I felt her begin to reach for the top of my pantyhose we heard Andy finish up in the bathroom. As we separated we grinned at how easily the plan was working out.

Andy walked back in looking clean and fresh, and completely naked ready for our ministrations. For the next 15 minutes Cheryl and I fussed around Andy, turning his looks from male to female. Foundation, blusher, lipstick were all applied carefully and subtly and slowly Andy's looks changed into softer more feminine ones. Cheryl trimmed and files his nails and then applied the varnish, whilst I did the same to his toes. All the time he sat still, but his previously softening member began to show signs of arousal again - hardly surprising as the two of us touched, stroked and manicured him to perfection. As Cheryl applied the last of the varnish I stood back and looked at Andy, and was pleased with what we had done. A couple of finishing touches and he would be able to get away with a walk out into the big wide world. I went to fetch the next items.

Andy seemed to be enjoying the attention from Cheryl as I returned, his glistening lips and tinted nails in quite sharp contrast to his ever hardening member between his shaven legs. As he spotted the blond wig in my hands he smiled ruefully, saying, "In for a penny... I guess if I have got this far I can't really stop now." I smiled too, it seemed we had got over his initial reservations and he was now going to proceed happily enough with this. I spent the next few minutes attaching and perfecting the wig over Andy's short hair and the transformation of his face was astonishing. He was now a very sexy woman from the shoulders up, and I was feeling very wet between my thighs at the thought of a three-way romp with Cheryl and Andy. Andy is slim and can easily get into size 12, and even some size 10 clothing Apart from more strongly developed thighs and broader shoulders than most women we would have no trouble getting people to treat him as a woman.

What we needed now was a waist, and I brought out one of Cheryl's corsets. Slipping its white, boned fabric around Andy and starting to do it up I felt him shiver slightly. Before starting to tighten the straps up properly Cheryl revealed another surprise for Andy - false breasts! His eyes were glued to the small orbs in Cheryl's hands as she approached him with them.

"These will help the corset stay in its rightful position and create the perfect figure for attracting admiring glances," she said, smiling at his astonished look. Before he had time to object she had placed one onto his left nipple and pressed it firmly into place. The second one soon followed, the two pale coloured mounds of pliant silicon filling the cups on Andy's corset perfectly. With the shoulder straps on we completed the tightening of the straps, Andy breathing in slightly as we gave him a slimmer than usual waist. I was going to open a new pair of stockings for Andy but fancied seeing and knowing that he was wearing some more of Cheryl's clothing. I really took my time sliding the nylon sheath up Andy's right leg, smooth flesh disappearing into the barely black stocking which I attached to the three clips on this side of the corset. Repeating the trick with the other stocking I could see Andy getting more and more aroused, his member visibly growing in front of me as I fitted the last clip over the stocking top, breathing gently on the hot, swollen head next to my cheeks. Andy groaned his arousal but Cheryl tapped me on my shoulder, reminding me that we had to hide his maleness, not flaunt it!