I've always loved dressing up in women's clothes and I've had a few gay encounters. For some time I'd been working out a really hot fantasy I wanted to act out involving both these thrills, and this week I decided to go for it.
Early in the evening I prepared myself. I stripped and showered and gave myself a warm enema to clean out my arse. I dressed in my thong, hold-ups, bra and slip - all black -and I topped it off with a fitted yellow jacket. I packed some other stuff in a day sack, then pulled on a sweater and some jogging bottoms over my outfit and drove off to a well known local gay dogging site - a quiet lay-by.
It was getting dusk, the right time of day for this, and I was excited to see there were several cars there. Most guys there were after the same as I was, so there should be an appreciative audience. I pulled up and stopped the car. My plan was to take off my jogging stuff so I was just in my undies and wind down the car window. Anyone passing by would be looking in. I would have my skirt pulled up and be playing with myself. If they were interested, I'd see what happened from there. Anyway, I thought I'd first walk up and down myself - still in my jogging stuff at that stage, just to see who was there. Also I wanted a pee, so I went to the gate at the end of the lay-by and stood against the hedge pissing.
I'd seen a man get out of his car and look at me. I knew he would walk up to see what I was doing. I didn't hurry, so that as he came up to me at the gate, I could go 'ooh' in a mock confused way and make sure he saw my cock before I put it away.
'Quiet tonight', he said, so telling me he was looking for fun. 'Really?' I replied - as I said, it looked OK to me, but we were really just keeping the conversation going. 'Yes', he said, 'not many about'. I saw my chance: 'But it's quality that counts', I quipped, 'and there's you and me here!' He laughed, then asked me directly 'What are you into?
'Well', I said'I'm a cross dresser and a bit of an exhibitionist. I've come to show off my body' 'Oh, I like to meet cross dressers', he said quickly, which was good, as a lot of guys don't go for it. 'Well, I'm going to sit in my car in my gear now, so you can look at me through the window if you like.' He grunted fairly enthusiastically, but I realised there had to be more. 'And what else do you like, then?' 'Fucking. And having my cock sucked' he replied. 'Well' I said, looks like we are quite a match?' He was clearly turned on - just what I wanted, and I was hot too.
'Look', he said, 'How would you like to go somewhere quiet in the lanes, away from here where it's a bit busy?' 'Is there anywhere?' I asked. Anyway, I was soon following his car. He took the first turn left, then, round a bend as he had said, there was a gateway, just right for two cars. We pulled in. The gate had a notice on it that it was kept locked, so we would not be disturbed from there. He got out of his car, clearly ready to get going. I wound my window down. 'Just give me a minute', I asked. I took off my trainers and pulled my track suit bottoms down and took them off. I felt really girly now in that silky slip. I took the top off, revealing the jacket, and felt the necklace, bringing it out on show. I felt in my bag and pulled out my heeled, strappy sandals and put them on. Then I took out my bubbly blonde wig and put it on. I really felt very feminine now, even if I was a disgraceful slut. OK he was going to take me for his pleasure, but on the other hand I'd got him hooked now, and he wasn't going to leave until that ache in his cock and balls had been drained out of him with his spunk. This was it.
'OK' I said, pitching my voice a little higher. I pushed the car door open and swung my legs out together - very ladylike and proper - making sure he saw my heels and stockings. I stood up and straightened my skirt, ensuring I gave a little wiggle as I did. Slowly I walked towards him, putting each foot straight in front of the other, to give my hips a sexy sway. I moved behind his car, land leaned against it, one hand on my hip. 'Well, do I look convincing, at least from a distance?' I asked. 'Oh yeah!' he moaned 'Anyone passing would think I'm shagging my girl friend'. It was unlikely we would be seen: we were sheltered by the hedges and behind the car, and the odd car that went past was going too fast to see us.
He took hold of me and pressed against me. I could feel his cock already stiffening against my thigh. 'What do you call yourself?' he asked. 'Janice', I told him (actually it's after a very attractive former work colleague, not the Corrie character - though I quite fancy her!). 'I haven't asked your name.' 'Jonathon' 'Ooh - Janice and Jonathon', I giggled. 'Oh, Janice, you're gorgeous', he gasped, feeling my bum then pushing his hands up to my bra. 'Get your cock out then' I sighed. He pulled his trousers down and I started stroking his cock, getting it ever harder. It was a good size - big enough to fill me without being tears to your eyes huge! 'Turn around,' he ordered. I turned away from him and leant onto the boot of his car. I then felt the indescribable thrill of my skirt being lifted up over my bum and my little thong being pulled down to expose my arse. 'Oh Janice, you've got a gorgeous arse' he gasped, pushing at my buttocks and my crack with his cock and feeling my cock too. I reached back to play with him. 'Ooh, I've got to fuck you!' he said desperately. 'So soon?' I asked actually wanting it too, but making sure all my fantasy was going to be fulfilled. 'Suck me then?' he said. So I turned and crouched down in front of him, held his cock, and took his knob in my mouth. First I sucked gently, then pulled his foreskin back and licked round his knob. Though I say it myself, I give a good blowjob. I pushed my lips down his shaft, gagging as his knob touched my throat. I concentrated on trying to swallow his tool, and surprised myself how much I got down my throat. 'Make it all wet, Janice' he begged. I took it out and spat on it, licking the spittle around. Then I went back to deep throating him. He was rock hard now, and I wanted a good fucking before he came.
While I was crouched down, I'd flipped the top off a tube of KY jelly and smeared a good dollop on and up my arse. I wanted a good wet slippery fuck, didn't I? I stood up. He slipped a condom over his knob, showing me what he was doing. I went down again and rolled it on with my lips. Then I bent over the car boot again, this time flattening myself on it and spreading my legs wide. This was to give him a good angle and height to enter me. ''Spread your legs really wide, Janice' he commanded - a little unnecessarily I thought! He pushed his cock against my arsehole, and I pushed hard enough to shit - good job I'd washed all that away! His cock opened me and pushed in. He started to fuck me, but I made him stop to let me get used to it. 'Now fuck me!' I told him, and he started pumping away. He said what I was thinking 'Oh Janice, I'm right inside you! My cock's right inside your body' - and it was! And just filling me enough to push on my inner sphincter too.
Do you want me to cum in your arse or in your mouth, when I do?' he asked. I knew - 'In my arse!' I begged. As he pumped away he soon got more desperate. Then 'Oooh, oh, oh, ooh - I'm coming!' he cried. 'I'm giving you every last drop! Oooh' After several more thrusts up my arse to the hilt of his cock, he relaxed. He pulled out with that funny squelchy plop sound. I felt back to find the condom still stuck up my arse. He gallantly pulled it out of me and disposed of it.
As ever, we quickly said our goodbyes and thanked each other. He asked when I would be around again, and obviously wants to have me again. Who knows? Can it ever be as good again, I wonder?