I realised after I'd started to write this that you may need some background to make sense of it, so I've added it here at the beginning. Jason is my best mate and has been for about 4 years since his dad died in a car accident. My Dad had walked out on my Mum at about the same time and we seemed to have something in common. I'm only 5' 5" and skinny whereas Jason is 5' 9" and does a lot of sport. Physically we look like an odd couple and Jason has always been more popular with girls than me. I make friends with girls easily but they usually just see me as a friend. Although we're both 18, I still look about 15 years old and haven't got much in the way of big muscles or even body hair. I only have to shave my top lip once a week.
Anyway, it all started when Jason told me about this site he'd found, URNA. We've been around so many free girly sites and were always looking for something new and a bit less hard core - those hard core sites just aren't real. I went round to his place one evening and he showed me some pics he'd downloaded of a fantastically sexy woman. I was blown away by her and, ok, we've both wanked off over pictures of great women before and we did it again. It wasn't until I asked him where he'd found all the pics of this hot woman that he told me she was a tv. I was more than a bit surprised but when he showed me the site I was completely blown away by the whole thing.
It wasn't long before one night, after a few beers and a cruise around loads of personal websites of real TVs, that we thought we'd both try on some of his sisters clothes. Jason is taller than me and much better built as a guy, so he struggled to find anything that didn't look stupidly too small. He settled for a wrap-around dress which looked quite cool and I fitted into a skirt and blouse quite easily. We were too scared to try out any underwear in case she noticed or in case we stretched it. We paraded about and checked ourselves out in the wall mirror. To be honest we didn't look that hot, but then Jason stood behind me and wrapped his arms round my waist
"Look, two lesbians making out" he whispered in my ear. I was in instant heaven. I could feel his cock on the small of my back and it was rock hard, so when he leant down and kissed my shoulder I was about ready to blow.
Then he broke away, sat on the bed with his dress opened up to the waist and started to wank himself off. I just leant against the mirror, lifted my skirt and did the same. He never took his eyes off me until he came all over his hand. I spurted out over the carpet a moment later. We panicked to clear everything up and make sure nothing got on Claire's clothes. By the time we cooled down and both changed back into our own clothes we were both a bit unsure of what to say, then Jason said I looked quite hot in a skirt and with some make-up he'd definitely fancy me as much as any of the girls we'd seen on URNA. I just blushed, was a bit confused as to what I actually felt and didn't know what to reply, but I was definitely quite flattered.
A couple of nights later, when we were round his place again, Jason suggested we dress up again and said he'd got a dress of Claire's he wanted to see me in. I was happy to go along with him as I'd been hoping we'd do it again. Jason had also sorted out some panties of Claire's which he said I could put on if I wanted as I wouldn't stretch them, and some clip-on ear rings from a old box of his mother's jewelry, and even some lipstick which he said would look good. I went off to his sisters room to change and assumed he was dressing too. I stripped off, put on the dress and panties and sat down at Claire's dressing table to put on the lipstick and ear rings. I brushed my hair across my forehead in a sort of fringe and blew myself a kiss. I was in heaven and floated back into Jason's bedroom. He was sat on the bed in a pair of boxers and a T-shirt.
I was a bit surprised but he held out a bottle of beer for me and said he was worried that he'd stretch Claire's clothes if he tried to get into anything. I took the beer and leant against the wall, not really feeling that comfortable being dressed when Jason wasn't. I took a sip from the bottle and Jason smiled at me.
"You look really hot in that dress".
I smiled back at him and I began to relax and sort of enjoyed the feeling of being looked at like that. I'd never had a girl look at me as if she really desired me and Jason was obviously feeling quite randy, especially if the way he was pushing against the front of his boxers was anything to go by.
I tried to look even sexier by biting my lower lip and sort of moving against the wall a bit. It must have been working quite well because Jason slid his hand inside his boxers, started stroking himself.
"I hope you don't mind, but you look really hot and I'm hard as a rock here?" he said as his hand moved slowly under his boxers.
In reply I put my beer down and just pulled up my dress a little showing more of my legs. Jason was jacking off as fast as he could by now and I was fascinated by the whole scene. I'd never ever the been the object of someone's fantasy and it felt fantastic to be looked at that way. By the time Jason came, which wasn't very long, I was leaking precum in a way I'd never done before and I think I'd probably come without even touching myself because when I put my hand under my dress I was already going limp and my panties were soaked.
Jason simply said "That was amazing, you are so hot"
He was still milking the cum from his cock. I said I had to go to the bathroom and as I left his bedroom he called after me.
"Why don't you keep the dress on for a while?".
I had to get my panties off and put them in the sink to rinse them out, then tidied myself up a little, took a deep breath, and returned to Jason's bedroom. He was sat on the bed in his jeans and T-shirt and sipping his beer. I took mine and sat next to him. We didn't really talk for a while, then Jason turned to me.
"That was cool, you make a really hot girl" and as I turned to him to thank him, he gave me a small kiss on the lips and I sort of froze.
He asked if that was ok and I just managed to squeak out yes before he kissed me again. We stayed for some time just kissing and his hand stroking my leg before I got the nerve up to put my hand in his lap. As soon as I did he kissed me harder and slid his hand up the outside of my thigh and under my skirt. I could feel him getting hard again and slowly rubbed him through his jeans. Jason pulled away from our kissing and looked me in the eyes.
"Is this ok with you?" he asked quietly. I didn't say anything just leant in and kissed him harder with my tongue deep in his mouth and my hand sliding his zipper down.
That first touch I had of his cock was electric and I'll remember it forever. It was so different to playing with my own because it felt alive and I felt it harden more as my hand went round it. Jason's cock is bigger than mine and slightly thicker too. I'm about 5" or 6", depending on the day, and jason is a good inch longer. I can't tell you how wonderful it felt to be playing with Jason's cock, but it wasn't something I'd ever thought about before that evening. If he'd asked me I think I would have gone down and sucked him off right then, but we were both still beginners at this and I think we were both rather nervous about where we were going.
We kept kissing as I wanked him and he had one hand behind my head and the other caressing my ass. He didn't try to finger me but kept brushing a finger up my crack which had me whimpering into his mouth each time he did it. Even though he'd only come about half an hour before it wasn't long before I felt his whole body stiffen and he just stared into my eyes as his cock jerked in my hand. I squeezed hard at the base and milked his cock upwards, just the way I liked doing it to myself. He spurted 4 or 5 times before his body relaxed a little, I leant in to kiss him again. We stayed like that for some time, me massaging his cum over his cock until it went limp and shrunk back.
"I'd better go clean up again." I said and he just gave me a little kiss and smiled at me. I felt on top of the world.
When I got in the bathroom I realised that I'd leaked on Claire's dress and quickly took it off and gave it a rub with some tissues which seemed to clean it up pretty well. I slipped back into Claire's room and reluctantly put my jeans and t-shirt back on. I took the dress back into Jason's room and showed him the mark, which was only just visible. He said it would be ok as she wouldn't guess what it was, even if she noticed it. We both sat back on the bed and Jason said
"We're just going to have to get you some of your clothes". I honestly didn't know what to say and I hadn't even thought about what was going to happen next.