Whenever people compliment my stories I tell them they're hot because they are all true. This one should have tipped me off on my future I guess. In my early 20's I lived in an apartment and my neighbor was a drag queen. He was the funnest and we'd hang out even though I "barely" had a bi or gay bone in my body at that time (so I thought). I had been drinking way too much, as most of my bad decisions start out in life, and I went to see what he was up to. He was out but his boyfriend (who I also knew) was there. We decided to hang out in their apartment. After some more drinking he joked and convinced me that I should dress in some of the drag clothes to surprise our friend. We did our "hetero best" to get me dressed up sexy, I remember it was a slutty schoolgirl outfit, long red hair wig, thigh-high stockings and heels. My makeup and everything else was surely rough but we were crazy drunk and just thought it would be funny.
I remember us standing in the bathroom me in front and him behind as we looked at my outfit in the mirror. He jokingly put his hands on my hips and said I looked super sexy, as we stood there like that for a minute his hand slowly started sliding around my hip and down my thigh a bit; I was drunk and turned-on at the same time. his hand slid down my schoolgirl skirt and you could hear a pin drop in there. I remember him saying "is this ok?" and I nodded, he slid his hand up under my skirt and started rubbing my balls and cock under the skirt. I was rock hard instantly, so turned on by all this.
I know he was excited too, I could feel him pressing against my ass from behind. He told me to bend over the counter, he reached into a drawer and pulled out some lube. He started rubbing it in my hole while he kept one hand stroking and holding my rock hard cock underneath my schoolgirl skirt. He asked me if I wanted him to fuck me and I nodded yes again. I asked him to wear protection and he did, he knew I was so nervous.
With me bent over the bathroom counter in my sexy schoolgirl outfit I felt him press his hard cock against my tight hole, he was so good and took it so slow - seemed like it took forever for him to slowly slide it in, wait and stroke me, slide it further, then after and eternity he was all the way inside of me.
I was so turned on (and a bit wasted), he kept stroking me while he slid in and out of my tight hole. He asked if I wanted to feel what it felt like without the condom and I nodded yes. He slowly pulled out and took his condom off, added more lube and slid back inside of me unprotected. It was the most amazing and sexual thing I've ever felt. The feeling of a man's bare cock sliding in and out of my hot hole while I'm dressed as a sexy gurl. He started going faster, telling me how tight and good I felt. Then, he told me he wanted to cum inside of me, I was in ecstacy and just said yes while the whole time he's stroking my rock hard cock; he was an expert at edging my 20 something cock. He started pumping faster and I could feel his balls slapping against my ass. He pushed all the way in me and I felt his hard cock pulsing and shooting warm jizz inside of me, I came and shot strings of cum as soon as I felt him cumming inside me. I never came so hard in my life and I feel that was the start of the rest of my life.......