Early cross dressing and wanking xx

Carrying on from my story regarding sex in the park I can relate another revelation from my youth. One of the times, with my friend Trevor, we'd been watching the sexual goings on in the toilets and bushes ,near to our homes it all went a bit further than we'd intended. We were watching a couple of older men having sex in the bushes and, as it usually did, it had got both Trevor and myself quite aroused. What had got us hard was that the two guys were having quite a heavy sex session and had moved on from a bit of cock rubbing to one of the men dropping his trousers and Y fronts, kneeling down in front of the other guy and was then giving him a good fucking. While all this was going on Trevor and I had both got our cocks out and were wanking each other whilst led under the bushes which we were watching from. We were quite enjoying each other and, as always, quite looking forward to bringing Trevor off as he was very big and always spunked absolutely loads which always amazed me and I loved watching all his spunk spurt out. Before it went any further we were disturbed by a rustling in the bushes beside us and another friend of ours, called Barry, joining us. Obviously we quickly pulled up our jeans and tried to pretend that nothing was happening, although it was pretty clear to Barry what we had been up too.

Barry was at least two or three years older than us, much bigger and probably in his early twenties. Barry joined us in watching the two guys fucking and when they had finished and left he asked us to come back to his house, telling us he had some 'dirty' magazines we could look at. Well both Trevor and I were up for that so we agreed and started back to Barry's house which was not far away. We'd only gone about half way when we bumped into Trevor's mother who collared Trevor for some errands and just left Barry and myself to go back to his house. Barry lived there with his mother and father but both were out at work and not due home till much later.

We went up to his bedroom and Barry got out the magazines, which he'd hidden under the bed. We both sat on the bed and started to scan through them and before long Barry got out his cock and started wanking, well I thought why not and started doing the same. Soon we were wanking each other, Barry's cock being much bigger than mine with a large bulb end, very hairy and I was quite enjoying it and him. I'd neve been with Barry before, certainly not in a sexual way but I did know of his reputation of liking young boys rather than girls which I think, at the time, was quite normalish. Anyway, before long we were both lying flat out on the bed, half naked and just playing with each other supposedly till we both cum.

Barry, who had a younger sister called Carol about my age, then suggested that as I looked quite feminine, which I definitely did, instead of just wanking off would I like to put on one of Carols dresses as he thought I would look nice in it. Well, as history and my desire still to cross dress, even today, suggests I was well up for a bit of dressing and Barry was soon leading me to Carols bedroom where he took a little blue gingham dress from her wardrobe, a pair of her pink knickers and a pair of white knee length socks. I soon had the knickers and socks on and Barry helped me into the dress and I felt really really good. I'd already dressed previously in my mothers undies and dresses so It didn't feel at all strange. Barry was now wanking frantically whilst sat on her bed and looking at me and asked me to come over and sit on his lap but before I could sit on his lap he made me take off carols knickers and then I sat on him. I could feel his hard and lovely warm cock rubbing up my bum and I pulled it up between my legs and started wanking both cocks off together. Like I said earlier Barry's cock was much bigger than mine and soon I could hear and feel that Barry was about to cum and when he did it was lots. It was lovely and warm and covered my hand with white creamy spunk and the sight, feel and smell of all that spunk soon made me cum too although nowhere near as much as Barry who by now had completely collapsed under me. We just led there for ages all warm and cuddly but then reality clicked in and we started to clean ourselves up and to worry how we were going to get all the spunk off carols dress and socks, which were in a bit of a mess. Barry sponged most of the spunk off the dress and we put both in the washing basket and I suppose, hoped for the best. I saw Barry a couple of times after that first adventure together, sometimes at his house when we again had fun in his bedroom but mostly in the bushes in the park when we would both wank each other off.

As a little aside to this story I later had a few dates with Carol, his sister. Obviously I never let on about me and her brother but, and this is a time when you were scared to death to get a girl pregnant, we did do a lot of heavy petting and she would never let me go home without always making me finger her pussy and her wanking me off.