Cross Dressing
9 May 2025


I had known Simon for as long as I remembered, he was same age as my brother 3 years older than me, that's how I met him he was my brothers friend first but as they got older they went different ways but I still used see Simon at school and around the estate when out playing.

One day he caught up with me as I walked home after school, we started talking but soon the chat took a turn for the odd when he started to mention sex.

At first it was just how he was craving it and that the girls round our way were so uptight and hard to get, then he talked about how he knew others would say it was wrong but he would try other things just to satisfy his need.

Not knowing that much about girls I just agreed with him thinking him being older meant he knew more, little did I know.

Few minutes later we parted as I turned down a different street to head home, with that the chat was over and I soon forgot all about it.

The next day he was waiting for me at the school gate and we started to walk with each other, very soon he was talking about sex again only this time he was going on about how I agreed with him last time, not sure what he meant I just kept nodding my head.

As we passed by the garages he said this one will do pointing at a garage with the doors broken open I followed him in side, no sooner were we in then turned to face me his cock already out on display, see he said its already hard just thinking about, he told me to give me his hand.

Not even thinking about it my mind just fixed on this hard cock before me I put my hand out, Simon took it pulled it closer then put his cock in it and holding my hand tight around his shat with is right hand he started to move my hand back and forth using it to wank him self.

I was so caught out I could not think straight and I just let him move my hand back and forth on his now fully hard 6 inch cock.

I could not take my eyes off it and yet no thoughts in my mind except for how big it looked, suddenly I became aware Simon was talking, I knew you would like it he said, I looked him in the eye and said I'm not sure about this people will say its wrong and call us gays or something.

After I spoke Simon replied then why are you still wanking it? I looked at his cock again but this time he had moved his hand but I was still wanking him off and even as I realised it I still didn't stop.

He spoke again about it being ok no one will know and that he didn't want me to stop as it felt really good then he told me to go faster and just as if I was some kind of robot I complied.

I couldn't get over how warm and soft his cock felt in my had despite him being so hard, I was still looking at his cock thinking about how strange t felt but how I liked when all of a sudden he shot his load all over my had and lower arm, don't stop he growled keep going till I stop cuming.

We had had PE at school that day so I still had a towel in my bag from the showers, I pulled it out to clean my hand, Simon said I should have licked it off as I may have liked it.

Once we were both cleaned up we left the garage and we both headed home neither of us saying another word.

Wednesday finished and I started home only to have Simon shout out for me to wait as he caught up with me, he started talking about normal things till we got near the garages at witch point he said come on and again I obediently followed him in and just like the day before he got me to wank him off.

After he cum I asked if he had something to clean my hand with, he told me just eat it you will like it I promise, to this day I cant explain why I did all these things so easily but I raised my hand to my mouth and stuck my tongue out to take just a little and was really surprised that it tasted good.

This was the start of the next step as Thursday we went back in the garage after school only this time he only let me wank him for a minute before he told me he wanted to cum in my mouth seeing as I liked the taste yesterday.

I said I wasn't sure about doping that but he just looked at me and said wow I thought you wanted to be mates, I do I said and that was all he needed as he told me a mate would do it for him and so I said ok.

He told me to get on my knees and open my mouth this I did after a few seconds hesitation, he said yea that's it and then moved forward till his cock touched my lips, suddenly I closed my mouth fear taking over, what you doing he said, I told him I was to worried about this but he said its ok I am almost ready to cum and you know you like the taste and as I said before no one will ever know.

I thought for a moment then opened my mouth, Simon moved quick and had his cock in my mouth before I could change my mind again, his hands were on the back of my head pulling me down on his cock.

He started to moan yea that's it just keep you lips locked tight on my cock, I did as he said and he started to move his hips back and forth fucking my mouth.

He started slowly but as he got more excited I felt him go faster and harder I almost chocked a few times he went so deep but as much as I tried to pull away he kept me on his cock with his strong hands, he was now talking, saying things like yea that's it suck my cock bitch make me cum in your mouth.

This went on for like 3 or 4 minutes then again with out warning he pulled my head hard on to his cock and I felt his warm thick sweet sperm fill my mouth and all I could do was swallow it all.

Before we parted he told me to meet him by the flyover on the far side were no one ever goes once I got home and changed, this I did and we spent the next 3 hours till I had to go home for the night sucking his cock swallowing his cum each time he recovered.

This went on for best part of a month, every day after school in the garages i would suck and swallow for him and at least one day at the week end, it went on that way till one the end of the first week of the six week holidays.

It was a Tuesday and we had agreed to meet in a place we had found as the holidays first started, it was an old bungalow that had a few bits of old furniture left in it including a manky old mattress, Simon managed to get a few old blankets from somewhere to cover it and the I would suck his cock and swallow his load.

This time I was wearing some tracksuit bottoms made of nylon, they were black very tight and shiny and felt real smooth to the touch and as I found out later they had another trait I hadn't thought of.

I got to the old bungalow and laid on the blanket covered mattress and waited till Simon arrived, once he was in he laid next to me and soon had his cock out for., I'm so horny for your mouth he said as he pulled my head to his cock.

I had been sucking him for a couple of minutes when I had to stop, I told him I need to pee and so went to the bathroom while he stayed laying down.

When I returned he told me how round my tight trackies made my ass look, he told me to turn around so he could get a better look, I did as I was told and I suddenly felt his hand on my ass very nice he said but he didn't move his hand he just kept rubbing them on my cheeks.

Come here he said and lay down next to me, as I turned I could see he was wanking his own cock, I smiled thinking how luck I was he licked me enough to do that but before I could start to lay he reached up and started pulling my tracksuit bottoms down, as they hit my ankles he told me to take them off and my boxers as well.

Still unable to do anything but obey his every word I took them all off, now lay here next to me he said, call my naive but I had no idea about what was to come as I laid down nest to Simon, before I knew it he had his jeans down and was now kneeling over me legs either side of mine.

I felt his hands pull my cheeks apart then he spit on my rosebud, It dawned on me what he was going to do and I shouted for him to stop but he started with the friends would do this for each other line again and that he knew I would really like it and it would make him so happy to know I wanted to be his friend enough to let him do this.

I just closed my eyes turned my face down and let him carry on, that's it good girl he said, I didn't think about it at first when he called me a good Girl I just let him take me.

I felt his cock pressing against my hole and it was getting a little uncomfortable but he just pressed harder, soon it began to get painful and when I told him it hurt he just said it will stop soon and turn to something I would like.

Just as I thought the pain had got as bad as it was going to get I felt the head of his cock snap the elastances of my entrance and a sudden rush of pain hit me, Knowing he was in he just pushed the rest of the way into me in one go and it made me scream but he didn't stop.

I begged him to pull it as it was hurting so much but he told me he couldn't stop now and that he was sorry but he had to keep going, even as I was crying he just kept fucking me and he was getting harder and rougher, he started to growl at me to tell him how much I liked his cock in my pussy but all I could do was cry.

I'm not sure how long he lasted but it felt like ages that he was pumping his cock into me calling me names like bitch and telling me how tight my pussy was, I hear him moan real load then felt him push his cock so hard into me it took my breath away then a warm wet feeling filling my ass and I knew he had cum.

I wanted to move but Simon just lay on top of me pining me down, every now and then he would pump my ass a few times before laying still again.

Eventually he got up, he said see I told you you would like it, I was still crying and said it hurt to much be he pointed at my cock and said but you got excited see look at how hard you r little cock is, he was right I may have been just 4 inches but that was as hard as I had ever been.

He told me we was going to love to fucking me from now on but I protested saying never again, with that we both left and I went home,

I didn't see Simon all the next week, in the end I went to his house and waited till I seen him, I walked over to him and asked why he had stopped meeting me? he told it was because I had said never again and he took that as meaning I didn't want to be his girlfriend any more.

I suddenly felt very sad, I do want to be your friends I said but what we did last time really hurt me, we ain't friends he said unless you agree to be my girlfriend, worried I would never see him again and that he was my only friend I agreed, with that he told me to meet him at the bungalow 12 midday the next day.

TO BE CONTINUED.

Tags: crossdressing, oral, first time, anal sex, accidental sex


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