The following is (sadly) fictional. Hoping it won't be for too long.
I finished work early in Thursday. It had been an early start but I wasn't tired, I was far too excited to be tired. I got back to my flat and started running a bath, stripping off my work clothes and leaving them strewn on the floor wherever they fell. I had to get ready, I was going on a date. For the first time in my life I was going to let someone else see me dressed as a girl, as Karen.
I'd always dressed up, I don't even remember when I started. I began borrowing my mum's clothes, later aquiring some of my own and from time to time I would have a fair stash of underwear, skirts and tops, until I went through another 'purge' and decided I wouldn't do it again. With me it was always sexual. I dressed because I found it a turn on, and I loved to fantasise about sex with a man (or several). Actually all my fantasies are about that. Now I was finally going to meet a guy and show my hidden self.
The bath filled, I washed and shaved myself and set out my clothes for the date. I'm not subtle when it comes to dressing, I'd already chosen the 'slutty whore' look and anyway, it was pretty much all I had. The basque went on first, tight to help shape my waist. I don't have a natural 'girly' look, I'm not really passable but I like to try my best. The stockings slid up my legs and the straining hard on I'd had for the last hour quivered as I began to anticipate the night ahead. I fixed my makeup (bright red lips, too much blusher) and threw some jeans and a jumper over my underwear. I needed to drive to Mike's house and finish getting ready there.
Sitting outside the house I tried to summon the courage to get out of the car. My heart pounding, legs like jelly I made it over to the door and rang the bell. I was nervous as hell. Mike opened the door. "Hi, come on in" He looked just like the picture he'd sent (fortunately). Late forties, nice if plain looking, reasonable shape if a tad 'spread out' round the middle. Perfect. I hated this bit, I was here to be Karen. "Can I run up andget changed?" I asked, wanting to get out of the jeans so badly. Mike directed me up to a spare room and said he'd be waiting downstairs when I was ready.
Upstairs the rest of the clothes came out - leather mini skirt, red silky top. 3" heels. Brown shoulder length wig tied back in pony tail. I sat as Karen on the end of the bed. "well, this is it then" I told myself. Slowly on heels I wasn't used to wearing I walked down to start my date.
Mike was sat on the sofa as I walked in, flicking through a magazine. I took in the scene and noticed it was a Transvestite porn mag, hardcore by the look of it. He saw me looking and put it down, embarrassed. We'd agreed to meet and talk, get to know each other. He knew I was inexperienced and wanted to go slow. He started to apologise but I laughed and said it was OK. Actually, I found it quite exciting.
We talked alot, got on really well, I was starting to feel pretty comfortable. He didn't try to force me, never suggested we do anything, it just happened that way. We'd been talking and there was one of those silences you get sometimes. I reached over and picked up the magazine. He looked at me as I opened a page at random. There was a couple on the bed, he was naked, lying on his back. She (well, the tranny) was draped over him. Cock in her mouth, hand round the shaft, looking right at the camera. "You like this magazine?" I asked cheekily. Pretty obviuosly he did. He stared right at me and made me feel weak in the knees. Finally he said "Yes, very much. Do you?". I looked again at the picture, understood what he was saying and found I could hardly speak. My voice was quiet and hoarse as I looked away from him. "Yes" was all I could manage.
He stood and took my hand, leading me out of the room and up the stairs. We went into his bedroom together and I stood by the bed, not knowing what to do. I felt clumsy, awkward. He adjusted the lights, fished some things out of a drwawer and came up behind me. I felt him kiss my neck, felt the hard presence of his cock push into my bum, felt myself push back and grind into it, loving how it felt and how it made me feel. He moved to the bed and lay down in the middle, motioning for me to join him. Lying by his side we rolled toward each other and he kissed my mouth, it was odd, being led, feeling him probe me, feeling his stubble. His hand traced my back and began to grope my bum, then lower and I felt him slide it up under my skirt, causing me to catch my breath. Damn I felt so bloody horny. I knew what I wanted to do now and reached one hand down to his flies, rubbing my hand over his bulging crotch. He stiffened his body, pushed into me as I rubbed him through his trousers. In no time I had the zip down, fumbled for the button and we both laughed as he had to roll onto his back to let me use both hands. Having got the trousers undone, I sat up to my knees and pulled them down and off. I was kneeling on the bed, my hand slipped into his boxer shorts and grasped his cock. The first cock I'd ever held apart from my own. His eyes were closed, one hand over his face as he moaned "Mmmm, that feels good". I withdrew my hand and drew down his underwear, returning my hand to his hard dick. I thought of the magazine, the girl leaning over her man and positioned myself so I was resting on his stomach, leaning on one elbow, the other hand stroking his cock. I looked at it, felt its hardness and warmth in my hand. As I continued to stoke I felt his hand run behind my head. He didn't push, but the intent was clear - suck it.
I'd never given a blowjob although I've received many. I know what to do, maybe not for the best ever bj but enough. I bent my head and began to lick the tip. It tasted a little like my own pre-cum (yes, I had tried it) but also different. A faint smell of muskiness and sweat greeted me as I pursed my lips and gave a big sloppy kiss to the end of his cock. He twitched, his dick jerked in my hand. I pulled back, held up his cock and licked along the shaft. I know that feels good but I could tell he just wanted it in my mouth, so I came back up and slid the whole end right in, taking about half his cock in my mouth. Next I drew back up, swirling my tongue over the tip as it reached my lips. His hands began searching again, I felt them move down to my bum and again got the thrill as they slipped under my skirt. I felt his fingers trace up my legs, running up to the top and my black silky knickers. He pulled back the elastic and a finger slipped in. I moaned as I felt it, moved myself to allow my legs to part slightly and felt him probe for my hole. Suddenly he stopped, pulled me off him and rolled over the bed. Confused I was about to ask what was going on until I saw him squirt Lube onto his hand. "Trust me", he said. I did.
we resumed our positions, me with his cock in my mouth, him with his hand in my knickers. I felt his finger return, this time it was wet. It moved purposefully to my hole and straight inside. I nearly choked on his cock but after the initial shock the feeling of being fingered whiile I sucked him off was very, very horny. My bum wiggled on his finger, he responded by thrusting into my mouth. Again he stopped and drew me off him. "If you carry on like that I'm going to cum" he told me. Quietly, nervously and longingly i replied "sounds ok to me. Just one request" "Whatever you want" he said, keen to get back in me now he knew where it was going. "As it's my first one, would you tell me when you're going to cum?" He laughed, told me I'd know, but yes, he would.
I took him back in my mouth, sucked faster now bobbing my head on his cock, wanting to taste my first cum. I didn't have to wait long. He began to writhe on the bed, force his finger deeper and harder into me. I felt him tense, his free hand holding my head in place and heard him cry "uuuuuhhh I'm cuming!". About a second later I felt the twitch as he started to shoot into my mouth, felt the sticky hot cum pump into me and tried not to gag. A second, a third shot, my mouth full I began to dribble his cum feeling it drip down my chin. The twitching subsided. I took his shrinking cock out and swallowed down his hot spunk. It tasted strong, spicy. Odd.
I looked at Mike and he smiled at me. "How was your first blowjob then Karen?" Just hearing those words made my buzz with excitement. I felt hot, wanton, sexy. I wanted more. "Nice. But now we have a problem" I told him.
"What's the problem Karen?". I smiled at him. "Well you see, I'm now so incredibly horny having scucked your cock like a whore, that I'd really like you to fuck me. Problem is, you look a bit....soft?"
What happened next? Want me to continue?
kareninshortskirts@hotmail.co.uk