1. My First Encounter


    Date: 2/5/2016, Categories: Crossdressing, Author: larkin3445, Rating: 5, Source: LushStories

    I had been cross dressing for years but only in private. I had also had a thing for bondage for a long time. A couple of years ago, I met two other cross dressers who were into bondage. We had been getting together every couple of months and playing bondage games with each other. We would take turns tying each other up and taking photos and videos. But, it was always clear that the other two were completely straight and nothing sexual would be involved. I was fine with that as I thought that I was completely straight too. I had read a lot about cross dressing and found out that most are straight and just enjoy the feeling of looking, acting, pretending to be a woman for a while. I never thought in my whole life about having sex with a man. I was interested in only women. That is until about a month ago. It was a Saturday morning and my two friends and I had met at one of their homes, as usual, to play with some bondage. When I arrived, the other two girls had already gotten dressed. I used the bathroom to change and put on my make-up. I tend to dress rather conservatively and had put on a short grey skirt, black panty hose, white blouse and black 5” strapped heels. I looked in the mirror before I exited the bathroom and fancied myself as a sexy secretary ready for work. For some reason, I am always the last one to take my turn at being tied up and it was the same this day. Julianne had injured her shoulder a couple of days before and said that she didn’t want to be tied ...
    today but would participate in helping tie the other two of us up and take the photos. So, I began tying up Kasey. She wanted to be tied to a chair by her arms and legs and I tied her very tightly and gagged her with a ball gag. Once I had her secure, I started tickling her. She hates (loves) to be tickled. We kept her tied for about 30 minutes and were undoing her ropes when the door bell rang. I was startled, not having any idea who it might be (mailman, neighbor, etc) and so I quickly retreated down a hallway before Julianne opened the door. I thought it was strange that she seemed so casual about greeting somebody en femme without knowing who it was at the door. I heard her say, “Hi, Chris." Nobody had mentioned to me that somebody else was going to join us and the name “Chris” didn’t ring any bells to me as somebody that Julianne had talked about before as being another cross dressing friend. But, I assumed that she may have invited someone else to join in our fun. Kasey seemed to know Chris too. Julianne said, “Larkin, come on out. There is someone that I want you to meet." I must admit that I was hesitant as I really had only met a few people while I was Larkin but I went out into the living room. There was this guy, maybe 45 or 50. Not bad looking. Sort of slender. Dressed in jeans and a shirt. Neat looking with short hair, slightly balding. “Larkin, this is Chris, a friend of mine. He knows about what we do for fun and he has seen some pics of you and wanted to meet you ...
«1234»