Screwed like a true sissy.

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 but never did.

A nightie for the weekend.

A nightie for the weekend.

My mom always said I should have been borne a girl. She said as I was growing up, you have the shape of a little girl. Small and skinny with girly features and a small peter to match, Ha Ha Ha! Then she started dressing me in my sisters close at age five. I fussed at first but was told to go naked or dress in them, your close are all dirty and I have not had time to wash them. Each weekend I wore my sisters clothes until the next Monday.

One weekend we went to a family friends place her name was Kelley, she asked if we could stay for the weekend. They had three girls, one my sisters age, one my age and one two years older than me. Mom had not planed on an over night let alone a weekend. The first night we stayed there mom was finishing drying me off with the bathroom door open as Kelley walked by. I remember mom flipping my dick back and forth with her finger saying to Kelly, "look at this little thing". Kelley came over to the doorway and said, "Oh my that is really a little one" then they both laughed. Mom asked Kelly if she had some panties for me to wear for the night? Kelley said I am sure one of the girls have some that will fit him. Do you have a nightie for him? Mom said no I do not. Kelley walked off saying I will be back in a minute with one.

When she returned she had pink panties with a dress which she gave mother saying this should fit him. I let mom put the panties on me with no reaction, I had been wearing my sisters for some time now. When she wanted to put the dress on me I pouted saying "no I do not want to wear that it is a girls". Mom said then go in your panties as she stood up and started to walk away. Then she turned to me and asked do you want to put it on or play in your panties with the girls, reluctantly I let her put it on me. When I walked into the living room the one my age said, I have a nightie just like that. The rest smiled at me and asked if I wanted to play dolls with them, I sat down and played. I slept with the one my age and when we got up the next day we stayed in our nighties until noon time. Mom had returned with some clean clothing for my sister and I and we changed in to them. That night I put on the pink nightie and panties again with no second thoughts. That was the beginning of boyinpink.