My Early Crossdressing
I started cross dressing around 12. At first it was knickers or tights. As I got older I started to get more serious with it. Just after I turned 16, I'd often go out round the streets round town dressed in full girls clothes. I'd always prefer going out late in the evening in winter, as I'd not pass many people and id normally only pass a few cars, some would slow down as I walked along the side of the road.
One day I was home alone, my parents were away for the week and my s****r was staying with her boyfriend. I turned up the music and got dressed from head to toe. I was pretty much smooth already so I faked tanned my body, added fake nails, painted them pink, did my makeup, put in my extensions and dressed in a corset, stocking, suspenders and high heels. I looked at myself in the mirror as I strutted about the house with a glass of wine in. As it got later I decided to go for my usual walk. So I pulled on a skirt and a hoody and headed out.
With my high heels on and feeling a bit tipsy I was struggling to walk on the icy paths. As I walked along a car pulled up next to me and asked the way to the petrol station. I'd never spoken to anybody while dressed and I was like a rabbit in head lights, I froze. I quickly composed myself and managed to point the direction. The car drove off after the driver gave me a look up and down.
I carried on walking, as I came up to a layby the car that had stopped me earlier was parked. The driver leans out the window and offers me a lift. All of a sudden I felt brave and noded, I jumped in the passenger seat and looked the driver up and down. He was a lad from my old school, years 3 ahead of me. He didn't seem to notice so I kept looking forward as we drove down the road, as we got closer to mine he asked if he could come in! I was shocked. Feeling confident that I'd got this far, I could manage a bit longer I said yes.
As soon as we walked through the house door he grabbed me and pushed me up against the wall, started tightly grabbing my ass. He moved his hand round to my concealed cock, I panicked! I pushed him back then lent forward and kissed him. It was the first time I'd kissed another guy, it felt so good! He put his hand on my shoulder to persuade me to drop to my knees, within seconds I was staring at his jeans, he undid them and pulled out his already hard cock. Without hesitating I grabbed it and started licking. I learnt quick to suck deep, I'd always practised on ice lollies and sweets.
He held the back of my head and pushed me gently onto his cock. I loved it so much. I felt him cumming as he pulled my head closer towards him and he fired his load down the back of my throat.
I made my excuses and pushed him out the door telling him my parents would be back soon.
It'd all happened so fast I couldn't believe it, within minutes I'd gone from never having spoken to a guy while fem, to sucking one off!
I decided after that to try and meet more guys. I started going out to near the local night club in town, but I'd never go in! I'd wait down the road till I see a lad on his own and then walk a little in front. I'd tried loads in hope that a guy would approach me, but it wasn't till around the 10th time that anything happened. I got to my usual spot around 3am, kicking out time. I sat on the bench and waited smoking a cigarette.
I spotted a guy walking up the subway and started walking the same direction as him. As we walked up the hill he caught up just as we got to the dark bit, he catches up with me (I made it easy enough) and speaks to me! A bit d***k his first words were hardly romantic when he said "nice ass". I quite enjoyed it! I responded with a remark to test him, "good enough to fuck?" it was simple and to the point. He turned to face me as he'd continued his pace and now past me, looking me up and down and says "damn right!". I thought sod it and grabbed his hand. I pulled him into the side ally. This time I know I want to be fucked and get straight to it. I tell him that he can fuck me aslong as its only in the ass. He agrees, I think he must of thought I meant I was on my period. I bent over and placed my hand one hand on the wall and with the other I guided his cock under my skirt and into my tight virgin ass.
I'd never had anything inside me before. I could really feel it, as it throbbed harder with every pump deeper into my little round ass. I moaned, he told me to be quiet so I moved his hand from my waist over my mouth.
He whispers that he's about to cum and I pull his dripping wet cock from my ass and toss him till he cums. He walks me back to my estate and kisses me good night.