My name is Jon & I started Crossdressing was I was young, it started with me trying my sisters’ clothes on as we were the same size, and when alone would go up to her room trying dresses and panties on, this carried on for a few years till one day my sister returned home early.
She came into the room, and I was standing there wearing her new summer dress “I always knew you way too fem and like girlie things, more than me sometimes” afterwards Karen, my sister helped me with my dressing.
A few years later and I have moved into a small bedsit in Colchester and whilst dressing more I was still a virgin or had any type of sex with a man. It was a Saturday night and Karen came round bringing some clothes that she couldn’t fit into so wondered if I liked them.
They were a very tiny denim shorts, and crop top, the shorts were very tiny and didn’t think I could get into them, but they fitted like a glove although my arse cheeks were hanging out “fuck Jon those shorts look better on you than me”….”let’s go out” “WHAT” I had only been out a few times but never dressed so slutty.
It was then Karen told me about a party with some uni friends and did I want to go “like THIS”, “yeah sure lets get some makeup on and wearing those shorts you will pull”. So after another 30 minutes and my sisters makup skills, we headed out getting a taxi to this house in Colchester not far from where I lived.
We walked in and it was busy with loads of people drinking and dancing and Karen soon got pulled away from me and was dancing with some guy.
I went to bar section and sorted a glass of wine when this guy Paul walkes over “hi, not seen you here before” “um, nope” not really knowing what to say, “I’m Paul” “hi” and you are “my name is Jon” we chatted for a while and drink more and he slowly got round to putting his hand around my waste that gradually slipped onto my arse. “Would you like to go somewhere more private, I live here”
Following him upstairs once in the room he moved forward to kiss me and I knew i needed to stop him, “wait, you know” and before I could carry on he smiled putting his hand into the crouch of my shorts “sure I guessed I see a slight bulge when you walked into the house” with that pushed me against the wall and kissed me. His hands were all over me.
I reached down and undid his belt, pants, unbutton and reached into his pants and found his semi hard cock, I needed more space as I couldn’t get my hands around his cock so I pushed his pants down and his cock fell out, fuck he was big! and I knew I was drooling looking at it. I pulled his foreskin over his cock and head his large head in my hand.
I started to wank him slowly and he quickly responded to get hard, by now I was on m my knees and i licked the end of his cock and using my tong to tease the end he groaned in appreciation, it was then I saw a little pre cum so licking it off it made me want more and I did my best to give my first blowjob. Fuck I loved it feeling his hard cock in my mouth as I worshiped his cock sucking him and letting him fuck my mouth.
I was licking him and sucking, whilst walking him off directly into my mouth and I so wanted his cum, I could feel his body tense up and quickly put his cock back into my mouth before I got my first wave of cum hit my throat. I tried swallowing but it was so much that I had to pull out shallow then return onto his cock just before another load this time taking it all.
Standing up he told me he had never had sex with a crossdresser before, and I told him it was my first too. Since then, I’ve lost count the number of times I’ve sucked and been fucked. It all started at that party and never looked back