Author: Sissyjennycuckold

Crossdresser dream cum true [cuck][anal][soft nc][huml][MFMMM]

Feel free to let me know what you think, comment or pm. Thanks.

We were packing for a well needed vacation. Anne and I had been married for 12 years and this is probably our fourth vacation. We got married at a young age, while sometimes it seems to early, most of the time it seemed perfect for us. A couple of years ago, I came out to Anne as a crossdresser. She didn’t take it well. Months of stress built up but, things seemed to level out as we found out what worked for the both of us. You see, I love her dearly but, my desire to dress was in need of an outlet. I had pushed those thoughts from my mind for about 5 years each time. Each time, the desire came back with a vengeance. I decided a couple years ago, to come clean and share my deepest darkest secret. Anne had other thoughts. She didn’t want anything to do with it. We came to an agreement that I wouldn’t do it near her or around her. And as long as I stayed faithful to her, she would deal with occasionally finding my girl clothes around once in a while. Read more »

[MC][MFMMM][BDSM][SM] Anne & Jenny in Chicago

Feel free to let me know what you think, comment or pm. Thanks.

We were packing for a well needed vacation. Anne and I had been married for 12 years and this is probably our fourth vacation. We got married at a young age, while sometimes it seems to early, most of the time it seemed perfect for us. A couple of years ago, I came out to Anne as a crossdresser. She didn’t take it well. Months of stress built up but, things seemed to level out as we found out what worked for the both of us. You see, I love her dearly but, my desire to dress was in need of an outlet. I had pushed those thoughts from my mind for about 5 years each time. Each time, the desire came back with a vengeance. I decided a couple years ago, to come clean and share my deepest darkest secret. Anne had other thoughts. She didn’t want anything to do with it. We came to an agreement that I wouldn’t do it near her or around her. And as long as I stayed faithful to her, she would deal with occasionally finding my girl clothes around once in a while. Read more »

Becoming His Daughter, [crossdressing, Mm, Older/young]

Note: I wrote this a couple weeks ago, looking for input before I write another.

How I became a Crossdressing Sissy Slut –
When I was 16, the summer before my Senior year in High School; I use to chat and cyber with men and women from around the US. I use roleplay/catfish as a teenage girl, most of the time if they asked, I would tell them the truth. I found a guy that lived near me and he convinced me to meet him. He knew I was a boy and enjoyed being a girl.

We talked about what we could do together. We concluded that I could probably fit in his daughter’s clothes, who’s a year older and just graduated. She was out of the house a lot and he found himself alone on his days off while his wife worked.

The day came and I showed up at his house. He was super nice and offered me a alcoholic drink that I took him up on, to calm the nerves. We both were nervous, neither of us had done this before. He showed me his daughter’s room and he had laid out an outfit he would like me to wear. Short while skirt with a lacy tank top. Matching bra and panties of course. Read more »