First man.
It was all Clare's fault, that is what I Like to tell myself, when I realise I am a submissive sissy whore.
After months of making me a pretty doll girlfriend, dressing me up, taking me to have my hair done, and teaching me to do my make-up. All of which I was kind of a willing participant in, Clare decided it was time I had sex with a man.
I was not sure, it would change everything, our relationship, my image of myself and who knew what else.
When I had told Claire I liked having sex in a nightdress, and had crossdressed in the past, one drunken night on holiday, my world had changed. That I loved her deeply did not help as I was willing to do anything to please her.
What I had expected my confession to lead to, I do not know, certainly not to have sex with a guy. Yet here I was coming back from a club, in a pink mini-skirt, black t-shirt, with princess in gold writing on the front and a pair of flat sandals.
Clare as usual drove, and my first guy sat in the back, looking kind of cute and vulnerable, I assumed he had been talked into it, though he had been eying me up while I danced. Yes I had been clubbing dressed like this, so I was kind of out,
We lived in Scarborough, where I did not go out dressed. Our usual destination was Leeds, it was the early 90’s and Back to Basics was the club we often went to, everyone or at least most just took it in their stride, that there was an exceptionally tall possibly male? Girl in their midst. Occasionally a guy would come on to me, and more rarely thankfully, someone would call me out, a sissy or worse.
Clare took pride in her work, and chose clothes for me that I must admit suited me. Though it had been a long process,from telling her to getting me to go out completely en-femme, not a term I knew at the time FYI.
My hair was sometimes blonde, sometimes bright red, long past the shoulder. I wore it in a ponytail when in guy mode, the cut was very feminine when down. My makeup when out was immaculate, sometimes Claire would spend over an hour doing it. The reality was I was her exhibition item, slowly she had taken me from being androgynous to full on girl over the past couple of years. Well as I say, when we were playing that game, as she called it.
We had friends who clubbed with us, mainly Claires’, she was originally from York, so knew more people in this part of the world. Though she had worked in London, and made a good deal of money working for a finance company there. Enough that she was now practically retired, despite only being 36, seven years older than my 29.
Most saw me as her project, a plaything that she liked to dress up and show off, I went along with it, I had no reason not to. I acted the part well, following Claire's instructions on who i should sit with, who I should dance with, what drinks and drugs I took. As if I was an empty air head, to coin a popular phrase at the time.
However I held down a good job in Scarborough, managing a holiday park, which was exceptionally busy during the season, but eased up a lot during the winter months. It was the reason I had come to Scarborough, though I had started out in maintenance,the high turnover of staff meant I had risen quickly to manage the whole park.
Was I her toy, I do not actually know, I thought I was just acting to please her, or myself, or was actually slowly being converted, becoming a prisoner in walls I was building for myself. I certainly now felt a little trapped and coerced as we went from the car to the flat, with my first date following.
Inside clare got him a drink and took me to through to the bed room, on the bed was a black babydoll style nightie, with a built in bra. Slip into this was her instruction, I did as i was told. The panties i wore all ready suited, a pair of lace top hold-ups was provide next. Nervous I let clair slide them up my waxed earlier in the evening legs.
She fussed with my make up a little, then showed me to myself in the mirror, as the male part of me lusted at what it saw, she came up behind me.
Stand still I was told, then she placed soft silicon breasts each of the cups of the babydolls bra. She had chosen the nightie well. There was enough material to cover were the false breast and my own skin joined.
The next bit was new, she slipped a pink velvet collar round my neck, and attached a thin chained leash to it. I could feel my cock stir in its cage. Coming between me and the mirror, she looked me in the eye, “now just be a good girl for me!”
A tug on the leash and I went down on my knees. “Yes on all fours my little pet” she told me now wait here i will tell him you are ready.
I will never forget how sick I felt as I waited on my hands and knees, I could hear muffled voices, after all in the flat the lounge was just across the hall from the bedroom.
Clare came back picked up the leash and pulled me out of the bedroom, “actuallly stand up” she said.
I got on my feet, my baby doll finished at the gap between my panties and stocking tops, my false brreasts weighed more than I remembered.
I walked forward into the lounge.
Our guest looked me up and down, “wow “ was all he said, but now stripped down to a T-shirt, I could see his cock approved also.
“Isn’t she just” said Clare “ taking the complement as an approval of her work as much as the way I looked. To be fair, all I had to do was follow instructions regarding dieting and exercise. I did mainly look this way because of Clairs efforts.
She stroked my arm gently and tugged my leash to get me to take a few more steps into the room.
Do a twirl for our guest Lisa, come on be good. I turned slowly, clair walking round me so the lead did not get tangled, by time I was facing him again, I would swear his cock had grown bigger still.
Clare whispered in my ear now. “If you want to kiss him tell me , otherwise on all fours and go suck that magnificent cock” adding “you lucky girl”
I was not sure about kissing, I do now regularly and love it when fully dressed, but back then it felt strangely personal rather than a sex act for what Clair called me and i thought of myself as being, namely ‘her sex doll’
So i dropped back to all fours, and covered the last six feet to between his legs at a crawl.
I looked up at him before I reached out to take his prick in my hand.
He smiled and said “please don’t rush”
I had no idea what to do regarding being quick or slow. So i just worked my hand over his cock as I would my own if it had been that big.
He leaned back in the sofa, i felt Clair drop the leash and heard her step back.
The tip of his cock glistened with pre cum, it looked strangely inviting, i poked my tongue out between my pink painted lips and licked it. The cock twitched in my hand as i did so and its owner moaned a little.
I tried another lick, the rush of getting a reaction, was immense, I simply felt wonderful.
“Good girl” said Clair from behind me, I realised I did not need her praise, but it was welcome.
The cocks owner joined in “yes good girl’
With both of them calling me girl, I felt a shiver down my spine, and knew I wanted to be this creature that made people pleased with me, dressed as I was.
The ecstasy I had taken earlier still heightened all my senses, the press of the straps on my shoulders, the brushing of the fabric on my bottom, my own caged cock stirred despite the drug. I knew the rushes from feeling girly were also in part caused by it, but it was more than that.
It was a calling almost, I had got used to being in dresses and sexy feminine underwear, but to see and understand the effect this was having on a guy, as well as knowing it was going to please Clair so much. Well it just changed the way I felt about my sexuality.
Another rush, as i realised I wanted to feel that cock in my mouth, I had been having lessons from clair with a very phallic dildo, that she sometimes used to peg me.
As my lips spread around the real thing though, it was very different, as you may or may not know or imagine! Another sigh encouraged me and I felt his hand stroke my shoulder, setting off a tingle that filled my body. I built up a rhythm too quickly it seems after as he was too soon bucking and filling my mouth with hot cum.
“Sorry sorry” I heard him say, as i tried to keep going, despite knowing my pleasure was also now over.
“Its okay” i heard Clair say, speaking for me.
She was now stroking my arm and neck, the way she did, when she was aroused and wanting me.
“ go and rinse” she told me.
Going through to the bathroom, I knew I was in for a far rougher sexual experience with Claire later.
Before I rinsed I swallowed, I wanted to see if I could. I heard clair thanking him, I know from the way she had looked at me as I left the room that there would be many more men in my life from now on.
