Crossdresser

Darling Cassie

I often read your posts and wonder how you are getting on.
I am a male to female transvestite, I started cross dressing very young and in those days loved the feeling of dressing in girls clothes. I knew I fancied males and developed a more feminine approach to life.
I wore my hair long and fortunately I had, and still have an athletic figure. I had my first gay experience with a middle age man when I was working at his house after school gardening to earn some extra money.
Remembering that day, I guess he must have been in his fifties and I was fourteen, he was very friendly from the day I started work there and I know I was naughty and flirted with him when I found out he lived on his own.
On that particular day, it was hot, I was wearing short shorts and no underwear, he invited me into the house for some refreshment. I saw, when he called me in that he had changed into a nylon robe and that robe looked very feminine and frilly as I followed him into the house.
Once inside, he turned around, the robe parted and I could see that he was wearing some white nylon knickers underneath and he had an erection!! He came closer, held my face gently and kissed me, I was aroused, I couldn't help myself as I put my hand on his erection. I was hooked, I tore my shorts off and we were kissing and caressing in seconds.
He took me to a bedroom which was decorated in a very feminine way, all pink, with lots of silky bedclothes. He went to a set of drawers and retrieved some silky knickers and got me to put them on, then from a wardrobe he got a baby-doll nighty very short and lacy, I was seduced and in no time we were in bed.
That day I had my first fuck, he was very gentle but persistent, we were two crossdressers making love.
He had me for nearly two years, bought me lovely feminine things and helped me to become a she-male. Also, because of my experience with him, I much prefer older men.

I hope the date goes well and leads to many more.

Because a dude wears a dress and a wig doesn't make him a girlfriend. Because you play girl dress up doesn't make you a girl. However it does show the two of are simply mental projects.

Me and my bestfriend wear our sister's stuff and go to the mall, it's so cool!

Well I hope all goes well and all the best hun

Thank you

That's great!! I hope you enjoyed the date, please share how it went.

Sorry it took so long to get back to about my date well he came over to pick me up had a dozen red roses and handed to and kissed me and told I looked beautiful so we went to dinner. And then we just walking around and talking about different things. He ask me why I dressed up in women's clothing and told it was that I was 100% women on the inside So I show it on the outside by dressing like a woman and to my surprise he that's so great. We wear holding hands and he pulled my up to his lips and kiss it so gently it made tear up a little so he ask me if I like to go to his place well I said yes so we get there and he opens the car door for me takes my hand helps out the car put his arms around me and give me a big kiss I love it so we in and we had couple glasses of wine and dance for little and one thing lead to another and we were in his back yard under some stars making love and he was so gentle with it was the first time that I felt like I was women and he was the man the sex was so good I had 3 or 4 orgasms my and he is NOT SMALL it was the best night ever and we are going out a lot not always about sex but when it happens it just gets better and better

You will end up with a very sore bum