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” strappy 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 and play bondage with us some today”. I was embarrassed but didn’t want to seem prudish, so I said “Hi. Nice to meet you”. He seemed pleasant and a little shy so I didn’t feel threatened. Kasey and Julianne seemed to be at ease with him there. I saw him look me over but not in a way that made me uncomfortable. It was exciting seeing another man look at me as a woman.
Julianne said that it was my turn to get tied now and that I was going to be tied to a large pillar in the entry way of her house. I had seen pictures of her tied to it but I had never been tied to it before. It is marble and maybe two feet in diameter. Julianne explained how she wanted to do it. She wanted my hands over my head and then tie my wrists so that one was around one side of the pillar and the other wrists around the other side. The pillar was so big that my hands wouldn’t touch together behind the pillar. They were maybe a foot apart with the rope running between them. Julianne did the tying while Kasey and Chris just watched. With my hands tied over my head and around the pillar, I did notice that my already short skirt was pulled up higher and my breasts were protruding. I did feel sexy and having someone new look at me was exciting.
“Okay, Chris, now it is your turn”, Julianne said laughing. “I think she needs more rope”. I just sort of smiled, not knowing what else to do or say. Chris didn’t seem to hesitate. Christ took a long piece of rope and said he wanted to tied me tight against the pillar by running ropes around me and the pillar above and below my breasts. In order to reach the rope around me and the pillar, he had to get very close to me so that he could reach around and get the other end of the rope. That is when I felt his chest against my breasts. A thrill ran through me and I may have even gasped. His head was along side mine and I could hear him breathing near my ear. He seemed to take a long time to reach the other end of the rope and I wondered if he was just taking his time or if he really just wanted to stay pressed against me.
He got the one end of the rope and pulled it around and over the top of my breasts and then pressed against me again to wrap the rope around so the could run it below my breasts. This time I though he pressed harder against me and I felt our hips against each other. And, he whispered in my ear, “ You look very cute, Honey”. I may have had my eyes closed, as I didn’t really even notice Kasey and Julianne watching but I heard her say something like “I think Larkin is enjoying herself. Let’s leave them alone for a little while” They then walked down the hallway that leads to the bedrooms and the bathroom where I had changed.
Chris stood back a few steps and just looked at me. He said that I looked cute again and I remember thanking him. Maybe sort of a dumb thing to say in my position. He then walked toward me again and I felt that thrill again even before he put his arms around me. He gave me a quick kiss and quietly asked if I minded. I said, “no”. It really felt so natural. A man kissing a woman. He put his around my waist and between the pillars and began kissing my neck. I am sure that I must have moaned as it felt so good to feel him against me. He began to kiss me again on the lips, this time with our tongues touching. His hand ran down across my breasts, down my belly and then down left thigh. I felt him touch my bare, hosed leg and then move up my thigh again, lifting my skirt more. I looked around to see if Kasy and Julianne were watching but they weren’t. He pressed against me harder and I could feel his hardness against me.
I felt more like a woman than I had ever dreamed of. I wanted this man. Then, Julianne shouted that she was coming out. He backed away as Julianne entered the room. “You having fun in here? She asked. “I have to leave for a while and Kasey needs to go home. You are free to stay for a while, if you want. But, we had better untie Larkin before we go”. I hated to be untied but thought that it was better that I wasn’t left alone with Chris while still tied. I didn’t know him or what he would do. Plus, at that point, he really didn’t need to have me tied up to have me stay with him.
Julianne untied me and left Chris and I alone. He and I sat down on the sofa and he put his arms around me and we kissed some more. He moved one hand down to my hip and rested it there. I put one hand on his thigh and slowly rubbed it back and forth as we continued to kiss. He then stood up and took my hand and led me down the hallway toward the bedrooms. I wondered as I went why I was going so easily. But, I really knew.
A couple of weeks later, I talked with Julianne and we didn’t go into any details. She just asked if I had enjoyed meeting Chris. I said that I did. She told me that she had noticed during some of our previous bondage sessions, that I seemed to be aroused my the touch and closeness of either her or Kasey. That is why she had shown Chris my pics and asked him to come over that day. Thinking back, I knew that was true and maybe the first time that I had thought about being with a man. But, I would have never pursued that thought in real life had it not been for the ropes and Chris.
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