I’m a 57 year old single man, a tech nerd and video game collector, so I don’t have much interaction with people my own age. I live in a medium-sized unit complex that has a lot of single-mom families with teenage kids, which leads me to my love: teen girls. I have had sex with many of the teen girls in the complex, a lot of which don’t ever see their fathers, so I’m also kind of a daddy to them. Most of their moms think I’m a sweet guy that helps their daughters with homework and lets them come over to use my PlayStation, which they do, but they don’t know is that most of the girls love to get fucked by me and call me daddy. I don’t really initiate things with them, they are the ones that usually come on to me and well, I can’t say no to a pretty teen girl.
Anyway, that’s not really the subject of this story. What the girls and moms don’t know is that I also love fucking teen crossdressers – guys from about 15 to 20 that love to be feminine and wear makeup and girls clothes. I am not attracted to just plain ol guys, just the pretty crossdressers.
Recently I had gotten my hands on a PS5 by sheer luck, and was walking thru the units on the way home with it. A lot of kids were watching me and were jealous, coming up to me and asking to look at it. I mostly ignored them except for one of them – the brother of a girl that I fucked a few times. His eyes lit up at it and he asked if after set I up if he could come over and use it. I told him half-jokingly “You can come over and play it when you come to my door dressed as a French maid”. I chuckled and walked away. He gave me a funny look and went home.
I thought no more about it until a week later. It was a Saturday early evening when there was a knock at my door. I got up to answer it. And he was standing there with a long trench coat on. He was wearing a black pixie cut wig, and I could see he was wearing white stockings and low heeled Maryjane’s on his feet.
“Your maid is here sir”, he said sweetly, and took off the coat to reveal a French maid uniform, complete with garters, corset, the whole works. He was also wearing makeup that him look totally feminine. “Hi there Chris”, I said smiling, “don’t you look good”. He blushed and said “Thanks, my sister helped me with the makeup and clothes”
I invited him in and said “I was joking, I didn’t actually believe you’d do it.”
“Well, I really really want to try the ps5 so I thought I’d do anything to see and play one, so here I am”
“Well, since you look so pretty and took the time and effort, you’ve earned it”, I said smiling at him. He blushed furiously and said thanks as he sat down on the floor in front of my entertainment center as I fired up the ps5 and let him have at it.
I sat watching him play. He was 17 and his sister was 15, and he looked so cute as his face lit up each time he tried a new game. I though he looked really good and I was getting a bit horny, so I asked him to pause the game and come over to me.
“You know you really look like a pretty girl”, I said, eyeing him up and down, “is there any other reason you wanted to come over?”
“Well, my sister told me about how you have sex with her and some of her friends, and I was umm kind of jealous of them,” blushing furiously. “I think you’re cute and I really like you but I didn’t think you like guys so I wanted to dress up as a girl to see what you thought”.
I stared at him, “I had no idea you liked guys, but I don’t like just regular guys, I’ll tell you something your sister and her friends don’t know—I love guys like you that dress like girls”
He smiled, “R-really? You like the way I look?” I said “you look absolutely beautiful”
He blushed again and I could see a small bulge in his crotch that matched mine. He noticed mine and said “I guess I can tell that you do like me”, a bit nervously.
I grinned and said, “I cure do, come over here and sit in my lap” HE did as he was told, wobbling a bit in the shoes. I took his face in my hand and kissed him on the lips gently. He responded back pressing his lips against mine and moaning a bit softly. We made out like this for a few minutes and then he reached for my crotch, I sat up a bit and slid my pants down exposing my stiff cock. He gasped and said “Did I do that? I said yep it’s your job to take care of it”
Slowly he got down on his knees and licked the tip of it gently, then put the head in his mouth and started sucking on it, bobbing up and down as he did so. I could see the bulge in his panties getting bigger and bigger as he sucked.
“Well let’s see what got you big girl” I said as I slid his panties down and his nearly 8 inch cock popped out. I took a breath and looked at it. IT was thick and veiny and throbbing as a clear liquid oozed out of the tip.
I took my shirt off and told him to straddle me spreading his legs. “Sit on my cock and take it up your ass” He smiled and slowly started lowering himself on my own dick as his stood up straight and eventually rested on my chest ad he went balls dep on me. He started bouncing up and down on it and I looked at his pretty face as it twisted in pleasure, hos own cock bouncing up and down on my chest as we fucked.
After a bit I felt myself building up to a powerful orgasm and he ais “so am I Daddy” I felt myself exploding into his ass shooting cum as I saw his own dick splurt a thick stream of cum onto my chest, then another and another, My whole chest was drenched as I even got some on my chin as my own cum filled him up. He feel down onto me and kissed me again breathing heavily. “Mmm that was good daddy” I said “yes it was and now you can come over to use my ps5 anytime you want.
Since then he comes over twice three times a week to play and fuck. I still fuck his sister and the other girls but I think I have a special relationship with Chris.
Thanks for reading, I hope you enjoyed it, let me know what you think and if there are any cute teen crossdressers out there who need a daddy or even you little girls, please get in touch with me on wickrme, I’m oznus.
👄This will be the best oral sex you have ever experienced.👅