sexstories.com

Introduction:

This is the first of a series of stories that I hope to write about Michael and this is the first story that finally turns him to the Sissy life.

This is the story of how I transformed from your normal straight married guy "Michael" to sissy slut "Michelle"

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

I've had a few wank chats 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 abuse me and it was hot as hell. 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 days thinking about it I agreed. My wife was at work all day so we arranged to meet in a local coffee shop, just a quiet meet and see how it went.

It was just gone three pm when I walked it, the coffee shop wasn't too busy but a quick look around and I couldn't see him anywhere so I got my usual coffee and took a seat in the corner.

I was nervously fiddling with my phone, panicking about meeting another man when suddenly he was standing right in front of me. I looked up in shock that he turned up at all. I nervously said hi and he smiled and sat down. Gary was pretty nice 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 muscles, six foot clean shaven and a shaved head, he was in his mid forties while I was in my thirties. I already knew he was packing a nice seven inch cock under his jeans though. I didn't get the fascination he had with me though, I wasn't that attractive, I was a little smaller than him but I wasn't that fit, curvy figure, small man boobs and a big bum with my little four inch cock as well. Anyway we started chatting about nothing while we drank coffee and he happily calmed my nerves down eventually.

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

Gary noticed I was looking down at his crotch and smiled at me, he took my hand and placed it on his crotch. I felt my face go red straight away, I was looking around the coffee shop expecting people to be staring but nobody 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 little cock getting rock hard, stretching my wifes panties that I had on which I cheekily took out of her draw.

I couldn't stop rubbing his cock which was rock hard now and I could see he was getting hot under the collar as I groped him through his pants.

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

So we left and walked the ten minutes 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 nice and tidy brightly lit, you would never of guessed it from the outside. We walked in and noticed no one was here, just the woman behind the counter who smiled and welcomed us in.

Her name was Claire and she was a hot tall blonde, probably around my age, slim with a nice pair of tits on her which was easy to see as she didn't have a bra on through her white 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 look around, we flicked through the DVDs and asked if we could put a certain sissy porn DVD on the TVs and she was happy to do so.

As we looked at the clothing they had the DVD blasting on the 6 TV's as a young fit sissy was servicing a few cocks, watching and hearing it had my panties wet. I could see Gary had a hard 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 knickers 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 nerves back again.

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

So I got the clothes 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 little hard wet cock, she smiled and said it was a cute sissy cock. She helped me get my clothes on and sort me out. Claire told me to wait there as she said she had some makeup for me to finish my look. I stood there looking in the mirror just staring at myself, feeling these stocking on my shaved legs, grabbing my bra and squeezing them, I felt so horny. My new panties were getting wet already. Claire came back and proceeded to apply some red lipstick on me, eye shadow and some blusher then put my wig on.

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

Once I was done Claire opened the curtain to reveal my outfit to Gary but I didn't hear the young couple that waked in. I was stood there suddenly embarrassed and red faced in my school uniform but they all said I looked great in it, the young lass commented she'd fuck me if she was a man and her boyfriend agreed I was a hot little sissy.

Still blushing I closed the curtain 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 seconds and looked into her eyes and said

"No, I can do this can't I?"

"Yes you can" Claire replied.

Gary poked his head through the curtain.

"Everything alright ladies" he asked.

Claire smiled

"We're fine thanks"

"Do you want a closer look?" 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.

"Don't worry, I know Claire, we go way back, so she lets certain things slide, anyways you look so hot Michelle"

I couldn't stop thinking Gary had laid this trap for me but I felt so hot and horny that I couldn't stop my little cock from getting hard again and poking my skirt up which Gary noticed.

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

"This outfit 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 mind 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 cocks 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 feel so hot, then I noticed the changing room curtain was actually half open and the young couple where sitting watching me being ravaged by Gary but it was too late now. I'd gone down the rabbit hole and I didn't 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 knees and fumbled his pants open, without hesitation I grabbed his hard cock and started stroking it.

"Yes Michelle, stroke my cock" Gary moaned.

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

I wasn't sure if I was wanking him right but he seemed to enjoy it.

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

"Mmmmm yes yes, that's so good"

I continued sucking and edging more and more of his cock into my wet mouth, before I knew it I'd got about half in, going back and forth sucking the best I could.

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

The Gary grabbed my head and pushed me against the wall, now sucking his cock was out of my control. He started to force 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 wriggle away but he kept going, I started to drool and my eyes were watering as he wouldn't stop. Gary was loving ruining my face, he was moaning more loudly now, telling me how much of a dirty slut I was but I couldn't reply, everytime he let go all I could do is try and catch my breath. He stopped the odd time to slap his wet cock around my face, making it a sticky 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 couldn't replay as I had a mouth full of cock but Gary replied

"Oh yes Claire, Michelle is a natural"

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

"Come on Gary give her a break, she's new to this, give her a rest" Claire said.

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

The other young lass walked in and her face was as much of a mess as mine! Eye shadow running with our tears, lipstick smudged from cocks being in our mouths. I stood there confused

"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 skinny tall woman with petite breasts, brown hair and blue eyes and a nice tight looking ass.

I finally caught my breath and smiled

"It's definitely a new experience for me"

I looked out the changing room to see Gary and James both had there cocks 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 hand 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 rock her back and forth on my little wet cock 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 suck it when James came around the other side and I was greeted with another new cock, it was probably slightly bigger than Gary's and I didn't hesitate to start sucking it.

We both sat there sucking cock for a while, gorging on them like we've never had cock before until they pulled Vicky off me and lay her down doggy style over the side of the sofa. Saliva drooling down my face and down my top I watched as James spread her legs, lift her skirt up and guides his cock into her wet pussy. Meanwhile Gary gets in front of her and slides his cock in her mouth and they both get to work on her.

Claire comes to me and tells me it's time to take the next step and proceeds to bend me over the other side of the sofa and pull my soaking wet panties 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 finger down, prodding my boi hole, she finally slides a finger in as I let a little moan out and she begins to twirl her finger around my anus.

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

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

As I'm getting fingered, Gary in front of me still face fucking Vicky grabs my head and guides me to his big dangling balls and without needing to be told I start to lick his balls as they bounce back and forth fucking Vicky's face.

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

Vicky is now getting a good pounding off James, muffled moans and screams coming from her mouth as Gary ruins her face but then it was my turn. Gary slides his soaking wet cock out of Vicky's mouth and walks around to the back of me.

Claire suddenly slides her fingers out of my ass and Gary's cock was quickly inserted. He slid the head of his bulging cock into my virgin hole. I gasped as my ass was stretched for the first time by a real cock. He slowly inched his way more and more into my ass, he got about half I'd say then he slide 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 couldn't help but moan now, every thrust into me made me moan "yes!" "Fuck" "fuck me harder"

I wasn't the only one, Vicky in front 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 cock. 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 kiss 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 cock was now leaking cum down the side of the sofa but I resisted to move my hands to wank myself.

Gary and James had picked up the pace now though, thrusting there cocks in our asses harder and harder, I let out a yelp every 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 rampant rabbit. His cock fucking me so hard I started to lose control of my body. Vicky on the other hand 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 didn't bother holding herself up now, just laying there screaming into the cushion as her ass was being fucked but I could tell deep down she was in ecstasy getting fucked so hard.

Both of us screaming as our asses were being pounded.

I screamed out what I think was my first sissygasm.

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

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

Then James 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 hesitation he slid his cock into my gaping hole

"Oh fuck fuck fuck" I screamed

I'd never been stretched so wide before.

I tried to hold him back with my hand but I was too weak to stop him sliding his cock balls deep in me.

James was wider than Gary and I'd say a good inch longer than him, the burning sensation and pain making me scream out loud 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 wasn't a pleasant taste but my mouth was wide and being fucked nether the less.

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

James was going rampant on my ass now though, slapping my ass every so often and calling me a good little sissy slut.

It wasn't long until I'd orgasmed again. James's thick cock pounding me made me lose control all over again.

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

He shoved his cock down my throat as much as I could handle and shot after shot of sweet salty cum spurted down my throat.

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

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

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

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

Cum dribbling out of my mouth as I panted.

Cum dribbling out of my now virgin less gaping ass and cum dribbling out of my little limp cock.

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

"Mmmm this tastes good"!

Vicky crawled up in front of me and passionately kissed me as we shared the last 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 other clean ourselves up.

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

I still couldn't stand or walk properly after my pounding, my legs where still weak like jelly and my ass sore but for my first time experience.

It was AMAZING!

---