So, after I had been with a few men, maybe six or so, I really got it in my head that I was gonna crossdress into something sexy. The problem was that I lived at home and couldnt risk getting caught, so I needed someone who would buy one. A daddy of sorts. I put some ads up on Craigslist that an 18 year old boy with long hair, petite with a bubble butt, wanted to hook up with an older guy, and wanted to dress in some women's clothes. Eventually I got a response from a fifty-something who had lingerie for me to wear. Despite my thumping heart, I drove over - but only after making sure to straighten my hair and shave every inch of my body. I was the closest to a woman I've ever been, when I walked up and knocked on his door. It was already ajar, and he came to quickly open it. He was much taller than me, a little chubby, but overall a nice guy. We talked for a minute or two, before he handed me a newly-opened lingerie outfit - a black corset with garter straps attached, a pair of silky black stockings, and a teeny black thong. I slinked off to the bathroom to put it on. I honestly had doubts as I was dressing, I'd never done this for someone else and I felt extremely embarrassed, until I peeked myself in the mirror. The corset and thong made my ass and overall body look like a little teen girl, hiding my masculine features and accentuating my feminine ones. I stepped out shyly, and he was sitting on the couch; at spying me in the outfit, his jaw dropped, and I knew it was gonna be a good day.

I first walked up to him slowly, turning around and arching my body, teasing him, letting him touch and grab my back, shoulders, and my ass and silken legs. I sat in his lap, grinding my ass against him, and could feel and see his already engorged cock under me. I remember specifically, I was so petite, and he was so big, that I could lick my fingers and rub under his cock in a circular motion, almost like what you'd do with a pussy. His moan at my first touch told me he hadn't been with anyone in some time, and so I thought it was only fair that I wouldn't hold back. Standing back up, I turned around to face him, then slowly lowered myself onto my knees as I took him in my hand, pulling lightly as I stared at it. I remember he was over 7 inches, probably close to 8 to be honest. He was at least a thick 7. I licked my lips, and bending my head over his cock, opened wide and stuffed it in my mouth, eliciting deep moans from him. I slid my lips and tongue up and down, slowly at first, enjoying the feel of a hard cock in my mouth, letting him play with my hair, or place his large hand over the back of my head as I sucked him. Looking down at me, through moans, he goes "You look just like my daughter" which made me go wild, I sped up my blowjob, taking him deeper and faster, trying to get him to bust in my mouth. I think he was close but didnt want it to end, cause he stopped me and asked if I wanted to go to the bedroom.

Now, originally I'd told him I didnt want to do anal - my last experience was rough enough, I didnt think I could do it again, but I was so turned on, when we got to the bedroom, I hopped up on the bed, got on my hands and knees, arching my back and bending my ass uphard, I asked him coyly "Do you wanna try and see if it fits?". He eagerly attended to it, eating and fingering my ass to loosen me up, pulling the teeny black gstring to the side before trying to slowly shove himself inside of me. Just like last time, it hurt way too much though - I let him fuck me as long as I could stand, until turning over my shoulder and asking him the same thing I asked the last guy to fuck me from behind: "do you wanna cum on my face?" He slid out of me and, standing over me and furiously rubbing his cock in my face, with a great cry of pleasure he covered my open mouth and tongue with his warm, salty cum. I swallowed every drop, and then kept his cock in my mouth as I jerked off onto my own tummy for him. Overall it was the best time I've had with a man, and I wish I could find him nowadays. I'd lied to him, told him I had turned 18 "two weeks previously", even though I was 20, and he seemed really into it. In fact I kept it in my mind, almost like roleplaying, that I was this barely 18 little thing looking to have dick in my mouth. Overall it was a fun summer lol