I’ve always cross dressed, when I was 18 years old I became a Teen Cross dresser. I started by wearing my mum’s knickers and bra, tights, knee high boots and a dress or skirt and top. It felt fantastic walking around in high heels, in the back garden of our house in Bloomington, Illinois, knowing that all the neighbours had to do was look over the fence and see me all dressed up! My cock got so hard and I’d wank myself senseless. I carried on all through my teenage years, using girlfriends underwear. At the swimming pool, where I used to work, I’d often have a shower wearing the girls high cut swimming costumes. The feel of the wet lycra around my ass and cock was so horny. I ended up as a delivery driver in Bloomington, for a catalogue company. I bought myself a pair of knee high boots, some lace knickers and a short black denim skirt. I used to dress up in the van and find somewhere quiet. I also used to dress up in the returned clothes. Beautiful dresses, stilettos, leather skirts, I’d try them all on, drive round in them and then park up somewhere quiet and jerk off.
One day, I decided I wanted to know what is was like to be fucked by a man. I called a chat line and got talking to a black guy. We decided to meet up at his flat near Peoria, one day. I wore my black thong, black knee high boots, my arse tight jeans and a tight top. He invited me in and we sat down for a coffee. He was looking me up and down and I could see that his cock was getting bigger. We went into his bedroom and got undressed. I kept my high heel boots on, as I wanted him to fuck me while I was wearing them. We got into bed and started kissing. it was the first time I’d ever kissed a guy and it was sooooo intense! My hand traveled down his smooth body and found his thick black dick. It was massive, At least 10 inches! I was getting a bit nervous, but he soon calmed me down, by kissing my balls and then taking me in his mouth. His tongue licked my cock and his lips slid up and down my shaft. My cock was the hardest it had ever been.
He told me to go down on him. I could only just fit his giant black cock in my mouth, but I sucked him and teased him with my tongue. He told me to turn round and kneel on the bed. My mouth went dry and I felt lightheaded. I heard him squeeze the lube onto his hand and then I felt his fingers around my balls and sliding into my arse. My breathing got heavy and ragged as he placed one hand on my hips. With the other hand, he guided his huge cock towards my tight hole. It hurt to start with, as he gently pushed into me. He slowly started to slide in and out of my hole and suddenly, I relaxed. The sensation was amazing and I pushed back towards him, taking the whole of his massive cock inside me. I lost count of time as he fucked me. He fucked me so hard, my balls were slapping on his. I asked if I could turn round and face him. He pulled out of me, but not all the way, so I turned over onto my back and angled my ass up at him. My boots curled round his back as he leant into me. I held him towards me and my tongue explored his mouth as his cock pounded my ass, harder and harder. I had one arm round his upper back, pulling him into me and my other hand was stroking my big erection as he fucked me. I kissed him and the sensation became too much for him as he built up to a huge orgasm. I could feel his cum pulsing inside me as he let out a moan. He stayed inside me as he collapsed backward on the bed, but he hadn’t finished with me. He was still hard and started pumping me again, while I lay there. His smooth hand was stroking my cock and balls. I could feel his cock get harder again as he was wanking and fucking me. I couldn’t hold out much longer and came with a scream. As I came, my arse pulsed and tightened round his cock making him cum in me again.