Me and My First Time
I've been cross dressing for a number of years now, on and off. In those periods of indulgment I've used butt plugs and dildos to heighten my pleasure and I've also dreamed of having sex with a man I've always considered myself to be straight, I don't go through life looking at men and fancying them, but when I go into my feminine state I dream of having a cock to play with (rather than just my own). It's generally one of two things me dressed up in stockings and lingerie having a guy tell me how pretty I am and me rewarding him with a loving blowjob followed by gently making love, or, me being pounded by a black guy with a massive 12 inch cock. My first experience was nothing like either of these fantasies. It was the summer of 2004 and it was a good summer that year, in terms of the weather. My girlfriends parents had a very large detached house with lots of gardens and an outdoor swimming pool. They went away to their house in Spain for the duration of the summer and we agreed to call round to the house a couple of times a week just to check all was ok. As it turned out we would go round more often than that and would spend our weekends there and use the pool and BBQ etc. One weekend my girlfriends step brother, Steve came down to stay. On the Saturday night we had arranged to stay over and we had a BBQ with loads of wine. It was a gorgeous warm evening and we stayed outside chatting well into the night. My girlfriend went to bed at about 11.00pm but Steve and I chatted on. He suggested to me that we should have a midnight swim but I declined on the basis I didn't have any swimming shirts. He suggested that that didn't matter as it was just the two of us, I could just swim naked. I don't know why I agreed, but I did and at that stage it didn't even enter my thinking what could happen despite knowing that Steve was an openly gay guy.I walked down to the pool and stripped off while Steve went to his room to get swimming shorts. I walked down the steps and into the water. I gently swam a couple of lengths in the dark and I heard Steve say, do you want the pool lights on or off. Again, there was no thoughts of anything at this point but I don't know if my sub conscience had taken over, I just replied and said yes, as it was a bit dark. I don't know why I said that, if I'd have said leave them off I could have kept my privacy. The underwater lights went on and there I am, suddenly exposed, but not even thinking about that. I just continued to swim up and down while Steve sat on the steps in his shorts and we chatted. I don't recall what we chatted about. At some point I stopped swimming at the opposite end of the pool from Steve, I was just holding on to the side, resting. Out of the blue Steve states that he has an erection. I don't remember how I replied exactly but I ended up swimming back towards him and his hard cock.I would love to say that at this point I teased him for a while, but I didn't, I just put my hand down his shorts and grabbed his shaft and I started to wank him off. I would also love to say that Steve had a massive cock, but he doesn't - it's about 6 inches with just a bit of girth. After a minute of so of this he stands up and pushes his shorts down which leaves his cock just inches from my face. I grab it again and take him in my mouth. I was actually giving my first blow job to an actual proper cock, rather than a plastic one. Oddly, I wasn't at all turned on by it, I didn't get an erection my self, at this stage. After a while Steve pulled his cock out and said he needed to go back to the house for something and he just walked off. I was a bit confused and still trying to work out what was going on through my alcoholic state. He was gone for long and when he retured he just fold me to stand up, turn around and bend over, which I duly did. I parted my legs when he asked and he told me to to reach around and pull my ass cheeks apart as he wanted to see my asshole. I just did it but it was this point when I was feeling so vulnerable with everything on display and nothing left to his imagination that I actually realised what was about to happen and that's when my cock started to get hard. It felt like I was there, bent over for hours but time had become almost irrelevant and I had no concept of it. Steve was then right behind me and he told me to reach underneath and grab his cock. I massaged his cock while he poured lube over his cock and my fingers, then he poured lube down my ass crack and started working at my asshole with his fingers. I was literally shaking! I knew what was coming was going to hurt but I couldn't stop shaking with sexual excitement.Then, he is working his cock inside me. Yes, it did hurt and yes, it was an odd feeling being penetrated by another man, maybe a guilty feeling. It was a totally different feeling than using a doldo on my self. For a start his cock felt red hot! Also, with a dildo, I'm in control of how deep is goes, how fast it goes etc. With Steves cock it was attached to Steve and he was making those decisions. I remember thinking this is what it's like to be fucked. Then I panicked a bit when I realised he wasn't using a condom but I was lost in the moment really and didn't give it a second thought. He was a gentleman though and asked my where I wanted his cum. I don't know what I said or if I even said anything but he just creampied me. When he pulled out of me we both sat down in silence on the steps of the pool. We joy started talking but it was totally bizarre and neither of mentioned what had just happen I think we talked about a new car Steve was thinking of buying or something similarly mundane. He went to bed and left me there, just sitting, trying to work out what had just happened and wondering if my asshole would ever stop hurting.So that's it, I've indulged myself with my little story of my first time. I anyone does read this, I hope it was an enjoyable read. That wasn't my only and last time with Steve we had quite a summer with his cock either in my mouth or up my bum at every opportunity really and yes, I did get my sex when cross dressed. I may do a part two to this and tell you all about some of the other things we did that summer.