The third was the first time I had my ass fucked. I was staying at my parents' again, and got talking to a guy on the Cottaging site really late one night. I drove over to his at probably 3 or 4am. He was older (probably late 40s), and shorter than me. He was top, and I'd been wanting to take cock for a while now. He started to strip me, fondling as he went.

Because crossdressing had always been an exciting part of things for me, I'd swiped a g-string from my sister's draws before I left, and he soon had me down to just this, which I was pleased he enjoyed  ;) he put me on my knees and began to fuck my mouth, which I loved. He wasn't especially large, so his thrusts were fine to cope with, although I was gagging whenever he hit the back of my throat. This was the beginning of me wanting to become really good at deep-throating; something I've still not managed. 

He moved me to his bed, and got me on my back before lifting my legs for a deep rimming - another first for me. Once he was satisfied that I was wet enough (and I was soon to find out that this was all he had in mind for lube!), he slipped inside (surprisingly easily), and pounded away for a good few minutes. At some point here, he drew my foreskin back, which is very painful for me: this is the moment that I found that out! I gingerly put it back in place as he apologised... He carried on, wanking me the whole time, and eventually pulled out to cum on me: my own soon joined his ;) I cleaned up and left soon after. We parted on friendly terms, but never met again.

Fourth one was a few months later, and was the second, and currently last time that I had my ass fucked. This one was arranged on Adult Friend Finder. While this ended up being a fairly vanilla session, we had both wanted to try out some pee play, and had both been drinking water to prepare.

I visited him in his home one day while his wife was at work, and his kids at school. We began by chatting a bit: I shared a bit about my limited experiences to that point, and he told me about he and his wife's experiences with swinging. She didn't know he was secretly meeting other guys on the side though.

We were both nervous to begin, but got going by helping each other to undress, and soon began to suck one another. After a little while, he grabbed some baby oil, and began to lube himself, inviting me in. I hadn't done this before, and was unfortunately just about ready to cum at that point, and trying to push in, I could feel myself about to erupt already! I tried to save embarassment by pulling away and waiting, letting things subside. It felt strange at that point though, which I wouldn't figure out until much later... We switched roles, and he oiled me up and began to take me from behind. I loved it ;)

We went for a few minutes before he wanted to delay his own orgasm. We went back to sucking and wanking each other, with him eventually pulling out of my mouth to cum on my chest - I had been planning on having him cum in my mouth, but in that moment felt glad that he hadn't in case it was a bit much for me. I did scoop some cum into my mouth to taste though.

I was finding myself unable to stay hard now, and we eventually gave up on me cumming. It was a few years later, when I developed an interest in chastity that I first read about ruined orgasms: I finally realised what I must have done to myself! We never id get round to the pee play though - still something I fantasise about trying though.

Fifth time out was the only one I've ever really regretted. Met another guy from Cottaging, and went to visit him. This one happened without seeing pictures beforehand, which was part of the later regret.

The host was friendly, but I didn't find him at all attractive. He was overweight (not necessarily a problem in itself), but the main thing was some questionable hygiene, particularly with how he kept his home (and being part way through a large McDonalds order didn't add to it much). I was feeling slutty though, and something about a guy who I'm not attracted to using me is appealing when I'm in certain moods, so I stuck it out.

We didn't get up to much: I came over his face after he sucked me, and then wanked him off (couldn't stomach sucking), and then got out politely, but as quickly as I could. I left with a lesson learned as he resumed his burger...

 

In the aftermath of that one, I was feeling quite disgusted with the whole thing, and tuned my back on all this pervyness for quite a while. I never met anyone else in the Kent area, and wouldn't resume my illicit activities until a while after I'd moved to Essex.