This is the story of how I transformed from your rule straight married guy `` Michael '' to sissy hussy `` Michelle ''

I 've always been singular about cocks since I was a teenager but I 've never had the sand to try it. I 've watched muckle of porn and wank chatted to C of guys online but that 's it, until now.

I 've had a few jerking off Old World chat and roleplays with Gary before and it was fun, he 'd go into detail how I 'd be dressed up as a schoolgirl and he 'd be my teacher and he 'd use and ill-use me and it was hot as infernal region. Then one day he suggested we meet.

I 've been here before and either I chickened out or they never showed up but after a few twenty-four hours thinking about it I agreed. My wife was at piece of work all day so we arranged to meet in a local umber shop, just a quiet meet and see how it went.

It was just gone three pm when I walked it, the coffee shop class was n't too busybodied but a quick spirit around and I could n't see him anywhere so I got my usual deep brown and took a seat in the corner.

I was nervously fiddling with my telephone set, panicking about meeting another man when suddenly he was standing right in front of me. I looked up in jounce that he turned up at all. I nervously said hi and he smiled and sat down. Gary was pretty dainty looking for a guy, I never really found men attractive, but to me it was all about the cock and cock turned me on all the time. He was nicely built, lean with some nice brawn, six pick neat shaven and a shaven head, he was in his mid forties while I was in my thirties. I already knew he was packing a courteous seven column inch cock under his jeans though. I did n't get the fascination he had with me though, I was n't that attractive, I was a lilliputian minuscule than him but I was n't that fit, curvy image, small man boobs and a big bum with my niggling four inch shaft as well. Anyway we started chatting about goose egg while we drank coffee berry and he happily calmed my nerves down eventually.

He was individual but I was unhappily married and our sex lifespan was abysmal, maybe that 's why I was here, in a coffee berry shop with some guy I 'd met online suddenly thinking about his cock.

Gary noticed I was looking down at his privates and smiled at me, he took my manus and placed it on his fork. I felt my look go red straight away, I was looking around the coffee workshop expecting people to be staring but nonentity took notice of us.

I looked back at him as I started to grope his cock.

'' Do you like the feel of that '' ? He asked.

I let a little nervous laugh out and nodded.

I felt it getting bigger, I also felt my own piddling cock getting rock candy hard, stretching my wifes pantie that I had on which I cheekily took out of her draw.

I could n't block rubbing his tool which was rock music hard now and I could see he was getting hot under the apprehension as I groped him through his pants.

Gary suggested we leave and go to the local anesthetic sex shop. I was surprised he suggest a sex workshop but he said it would be fun as we could browse the costumes and toys and blab more than about my fantasies.

So we left and walked the ten proceedings to this sex shop Gary was on about. A sleazy looking shop which looked worn down and a mess from the outside but when we walked in, it was gracious and tidy brightly lit, you would never of guessed it from the out-of-door. We walked in and noticed no one was here, just the fair sex behind the retort who smiled and welcomed us in.

Her gens was Claire and she was a hot tall blond, probably around my age, slim with a Nice pair of pap on her which was easy to see as she did n't let a bra on through her bloodless blouse. She definitely liked to put a show on for the punters and even though I was curious for cock I still loved a hot lass.

Anyway we had a tone around, we flicked through the DVDs and asked if we could put a sure effeminate porn DVD on the TVs and she was happy to do so.

As we looked at the habiliment they had the DVD blasting on the 6 TV 's as a young fit pantywaist was servicing a few pecker, watching and hearing it had my panties wet. I could see Gary had a heavy on too which made me even more horny.

We found a schoolgirl outfit that was straight out of our fantasy.

White blouse, grey skirt, red thigh high stockings with some matching red frilly pants and red bra along with a dark ginger wig.

We asked about this outfit and to my surprise she said I could try it on, I went bright red and started getting my nerve back again.

Claire smiled at me and took my helping hand and reassured me that it was fine, they had some large changing rooms and the shop was glad for the great unwashed to try wearable on as they always had sets that they cleaned and it was all part of their sex shop experience.

So I got the apparel and I went to the changing room with Claire while Gary stayed outside watching the porn.

Claire helped me get changed, she cheekily pulled my wet panties down herself revealing my petty hard wet tool, she smiled and said it was a cute sissy tool. She helped me get my clothes on and sieve me out. Claire told me to look there as she said she had some makeup for me to terminate my look. I stood there looking in the mirror just staring at myself, feeling these stocking on my shaved stage, grabbing my bra and squeezing them, I felt so horny. My new panties were getting wet already. Claire came back and proceeded to implement some red lipstick on me, eye fantasm and some blusher then put my wig on.

'' With a little work I think you could pull this girly face off ! '' She said.

Once I was done Claire opened the curtain to uncover my outfit to Gary but I did n't get word the young couple that waked in. I was stood there suddenly embarrassed and red faced in my schoolhouse uniform but they all said I looked capital in it, the young jeune fille commented she 'd screw me if she was a man and her fellow agreed I was a hot minuscule sissy.

Still blushing I closed the drape back, Claire held my arms and reassured me I looked great and not to feel embarrassed.

'' We can stop this if you want ? '' Claire asked me.

I stood for a few s and looked into her eyes and said

'' No, I can do this ca n't I ? ``

'' Yes you can '' Claire replied.

Gary poked his head through the curtain.

'' Everything OK noblewoman '' he asked.

Claire smiled

'' We 're hunky-dory thanks ''

'' Do you want a closer aspect ? '' She asked Gary.

He walked in and Claire asked if we 'd be alright now.

I nodded and she walked out leaving Gary in amazement at my transformation.

'' What sort of sex shop is this '' ? I asked.

'' Do n't vex, I know Claire, we go way back, so she lets certain thing glide, anyways you look so hot Michelle ''

I could n't bar thinking Gary had laid this trap for me but I felt so hot and horny that I could n't blockade my niggling cock from getting hard again and poking my skirt up which Gary noticed.

'' It looks like someone 's happy to see me '' ?

'' This turnout makes me feel so sexy '' I replied.

Then Gary grabbed my ass and pulled me towards him and suddenly kissed me.

I 've never kissed another man before, never creative thinker in a dressing room dressed as a schoolgirl in a sex shop ! But lust and horniness kicked in and I kissed him back, I grabbed his ass as we grinded our dick together, his hands now groping my body.

He started kissing my neck and I let out a moan as his hands moved around my body making me palpate so hot, then I noticed the changing room curtain was actually half open up and the young couple where sitting watching me being ravaged by Gary but it was too late now. I 'd gone down the rabbit cakehole and I did n't give care. I was loving the attention, I knew the couple were turned on as I seen she was groping his cock and had her hand down her pants.

Gary then pushed me onto my knee joint and fumbled his pants open, without hesitation I grabbed his arduous cock and started stroking it.

'' Yes Michelle, stroke my cock '' Gary moaned.

His cock felt so full in my hired hand, slowing stroking it, feeling the strong pulsating member I 'd only seen on a phone screen weeks earlier.

I was n't surely if I was wanking him right but he seemed to revel it.

It looked so juicy though, rubbing his pre cum over his bulging head, making his cock nice and wet. I could n't help it anymore and thought to myself, I need to taste this peter. So I opened wide as full I could and started to work the head of his turncock, I swirled his pasty pre cum around my tongue. I grabbed his cock with one hand and guided his stopcock on my tounge and I started sucking the wet bulbus nous as Gary let out a moan.

'' Mmmmm yes yes, that 's so skilful ''

I continued sucking and edging more and more of his turncock into my wet mouthpiece, before I knew it I 'd got about half in, going back and Forth River sucking the best I could.

I knew I was n't brilliant, I 'd only draw my wife 's dildos in the past but I was trying my best.

The Gary grabbed my head teacher and pushed me against the wall, now sucking his cock was out of my control. He started to pull his cock more and more in my mouth, he 'd got about three quarters in when I started to gag, he slide it out then back in again, then the face fucking began. I could hardly breath and I tried to writhe away but he kept going, I started to drool and my middle were watering as he would n't stop. Gary was loving ruining my face, he was moaning more loudly now, telling me how a good deal of a contaminating hussy I was but I could n't reply, everytime he let go all I could do is try and hitch my breath. He stopped the odd time to slap his wet cock around my face, making it a viscous mess.

Then the curtain got opened fully and Claire came in with a grin on her face.

'' Looks like you two are having fun ''

I could n't play back as I had a backtalk full of cock but Gary replied

'' Oh yes Claire, Michelle is a cancel ''

Gary had released his pecker out of my mouth and I crumpled to the base trying to catch my breath.

'' cum on Gary give her a break, she 's new to this, chip in her a eternal rest '' Claire said.

Gary agreed and walked out as Claire got me up on to my feet.

The early young lass walked in and her aspect was as often of a mess as mine ! Eye shadow running with our rip, lipstick smudged from dick being in our back talk. I stood there flurry

'' It looks like you 've had as much fun as me Michelle '' she said.

Vicky as she was known and her boyfriend James was a boney tall womanhood with flyspeck breasts, dark-brown haircloth and blue eyes and a nice tight looking ass.

I finally caught my breathing place and smiled

'' It 's definitely a new experience for me ''

I looked out the changing room to see Gary and James both had there shaft out busy watching the porn on the TV 's again.

Vicky suddenly grabbed me and stuck her tongue down my throat and passionately kissed.

'' Mmmmm Michelle you 're so hot '' Vicky said as she took my script and took me over to one of the sofa 's and sat me down. Vicky sat on my lap we started kissing again. I grabbed her little ass and I started to shake her back and Forth River on my trivial wet stopcock through my panties. I started to kiss her neck and she arched her head back to be greeted with Gary 's cock. She happily started to go down on it when Saint James came around the former side of meat and I was greeted with another new shaft, it was probably slightly bigger than Gary 's and I did n't hesitate to start sucking it.

We both sat there sucking prick for a spell, gorging on them like we 've never had peter before until they pulled Vicky off me and lay her down barker way over the incline of the sofa. spittle drooling down my face and down my top I watched as James IV spread her legs, lift her skirt up and guides his dick into her wet pussy. Meanwhile Gary gets in straw man of her and slither his rooster in her back talk and they both get to run on her.

Claire comes to me and tells me it 's time to take the next step and proceeds to crouch me over the other side of the sofa and rive my soaking wet pantie down.

She caresses my shaved ass and balls with her soft hands.

She drizzles some lube down the crack of my ass and slowly slides a digit down, prodding my boi gob, she finally slides a finger in as I let a little groan out and she begins to twirl her finger around my anus.

It 's not the first clock time I 've had a finger's breadth up my ass, I 've done it deal of times and I 've tried dildos up there but never have I been at the mersy of soul else.

After a bit more prodding and swirling she adds another fingerbreadth and starts to get a rytham fingering my ass.

As I 'm getting fingered, Gary in front of me still face fucking Vicky snap my head and templet me to his big dangling balls and without needing to be told I start to cream his testis as they bounce back and Forth fucking Vicky 's face.

With my ass relaxed enough aswell Claire adds a third finger's breadth which really turns me on, I start to moan Sir Thomas More and more and tell her how great it feels.

Vicky is now getting a soundly pounding off James, muffled groan and screams coming from her mouth as Gary ruins her nerve but then it was my turn. Gary slides his soaking wet cock out of Vicky 's sassing and manner of walking around to the rachis of me.

Claire suddenly slides her fingers out of my ass and Gary 's rooster was quickly inserted. He slid the mind of his bulging cock into my virgin hole. I gasped as my ass was stretched for the first off meter by a real cock. He slowly inched his way more and more into my ass, he got about half I 'd say then he skid it out, then back in and back out. Getting a good rytham going now. I lay there with my ass up in the air as Gary started to go deeper and deeper in me. I could n't avail but moan now, every thrust into me made me groan `` yes ! '' `` ass '' `` fuck me hard ''

I was n't the only one, Vicky in figurehead of me was now getting her ass pounded off James. Gary had now grabbed my hips, he got faster and faster until he was all in me. It felt so good to be so full of shaft. I could feel his balls slapping off my ass as he pounded me more and more now.

I was screaming with pleasure, we both were, me and Vicky started to osculate each other, I could taste Gary 's cock on her wet sticky lips, our arses being fucked we screamed with pleasure through our kissing, my putz was now leaking cum down the side of the sofa but I resisted to move my hands to jerk off myself.

Gary and James had picked up the gait now though, thrusting there cocks in our shtup harder and harder, I let out a yip every clock time his cock plowed into me. He grabbed my shoulders and got a better position behind me and started to go at me like a rearing rabbit. His prick fucking me so hard I started to recede control of my body. Vicky on the other deal was way beyond that, James fucked her so hard her body was shaking and her head was buried into the sofa as James forced her face down plowing her ass, she did n't annoy holding herself up now, just laying there screaming into the shock absorber as her ass was being fucked but I could tell deep down she was in transport getting fucked so hard.

Both of us screaming as our piece of tail were being pounded.

I screamed out what I think was my first sissygasm.

My body started shaking uncontrollably as my little tool slam out a few flow of cum onto the sofa but Gary continued to plow me as I moaned and screamed in pleasure.

After a few moment Gary stopped and slipped out his wet cock out of my reinvigorated virgin ass. I lay there exhausted but I was n't finished yet. King James was done with Vicky, she was just like me, a trembling mess after getting a salutary fucking.

Then James River walked around to the rear of me and slapped my ass, I let out a scream.

'' Who 's a good girl ? '' James asked

'' I am '' I replied

Then without indisposition he slid his cock into my agape hole

'' Oh fuck fuck roll in the hay '' I screamed

I 'd never been stretched so all-inclusive before.

I tried to hold him back with my bridge player but I was too infirm to stop him sliding his shaft globe deep in me.

Henry James was wider than Gary and I 'd say a good column inch longer than him, the burning sensation and painfulness making me scream out tacky but that was soon muffled when Gary at the side of me grabbed my hair and shoved his wet sticky cock that stunk of my ass in my mouth. It was n't a pleasant taste but my oral cavity was wide and being fucked nether the less.

It did n't sample that bad once he had got going, it was just a wet hot salty gummy cock fucking my throat and the thought that this peter took my virginity had turned me on to the max.

James was going rearing on my ass now though, slapping my ass every so often and calling me a good picayune pantywaist slut.

It was n't long until I 'd orgasmed again. James River 's thick prick pounding me made me turn a loss control all over again.

Gary had then grabbed my head teacher and let out a moan to signalize he was cumming.

He shoved his tool down my throat as often as I could care and fritter after nip of afters salty cum spurted down my throat.

He held it in what felt like an eternity until cum started dribbling out of my back talk and he let go, letting his cock slickness out of my dribbling cum filled mouth.

Now my mouth was free I was screaming and moaning with joy from the continuing piece of tail of my ass but it was n't long until James announced he was going to cum.

He grabbed my bra strap through my blouse and dragged me unsloped, pounding my ass faster and faster, until he gave one lastly long shove of his cock deep down into me and I felt his cock pulsate as he filled my ass broad of his seed.

He let go of me and slip his tool out of my ass and I slumped back down in exhaustion.

Cum dribbling out of my oral cavity as I panted.

Cum dribbling out of my now virgin less agape ass and cum dribbling out of my piddling limp cock.

The lad went away to get cleaned up while Claire had already started licking my ass. Proclaiming

'' Mmmm this tastes sound '' !

Vicky crawled up in front of me and passionately kissed me as we shared the terminal of Gary 's cum together.

'' You where amazing '' Vicky had said

'' It felt amazing '' I said exhausted.

We all went to the changing room and helped each former clean ourselves up.

Claire said she 'd moisten my outfit and it would be ready to collect in a span of days.

I still could n't abide or take the air properly after my hammering, my legs where still weak like jelly and my ass sore but for my beginning time experience.

It was flummox !