I had always been wearing my sisters clothing up until about age twelve. From then on I would sneak a pair of her panties to wear every so often going through high school. Once I was out of school work and my girlfriend became the main interests in my life. Two years after I had been out of school I married my high school sweetheart. We had two kids and then I started cross-dressing in front of her. She was okay with me in panties and kind of liked it. She bought me a few pairs and I would wear some of hers. This went on for a few years until I wanted more. I wanted mini skirts and halter tops, nylons, garters, but it became too much for a young mother. We had been married for seven years at that point and we ended it with divorced.
Now being single I cross dressed daily and would go to a larger city and walk the parks cross dressed. I loved the feeling and met a few men who taught me how to suck a cock. I had my virginity taken at age twenty eight by a sixty year old man. I went to the city one weekend and met a guy at a night club, he took me back to his place and had sex with me. That was the second time I had ever been screwed in my pussy ass. He sat in a big wingback chair and I sat on his huge cock facing him. I was his sissy slut for the night, once his huge cock was accepted in my pussy ass it felt great! I pumped my pussy ass up and down on that huge cock of his as he masturbated my little clity cock. I climaxed at the same time he did, it was the best sex I have ever had. It was two in the morning so I followed him to his bed and sucked his cock until he unloaded in my mouth. I fell asleep cuddling with him and his big cock in my hand.
The next morning I woke up before he did and I had to check out his big cock again. I grabbed it and with a few stroked it was stiff again. By this time he was awake, he said now that you have him hard again he was going to fuck me again. I turned around and bent over to summit to his man hood, he had his way with me again. Once done I went and cleaned up and returned to his bedroom where he was laying. I kissed him and said thanks for the nice time as I caressed his cock. He told me if I get it hard again he was going to fuck me again. I smiled saying I am too sore to have that monster in me again, I got up and left. I had planed on going back to him for another weekend fling in the future .
SM (Sissy Maker)