Exploring the Tranny

At first I didn’t like that my wife, Jan, was hanging out with a “guy” several times per month. She insisted, however, that her friend “Crystal” was actually a girl trapped in a man’s body — and as such was attracted to men. Since she posed no sexual threat, she enjoyed their time together because they shop and talk and hangout without expectations. To be fair, my wife had a soft spot for gay men - she’s had numerous gay friends over the 8 years we’ve been together.

Crystal (formerly Chris) was even more special to her for a few reasons. First, she was actively transitioning from male to female. Jan liked the idea of having a “new” female friend and was excited to watch and help her along the transition. Second, Crystal was much younger than Jan at only 20 years old while Jan was 35. This let Jan feel like the big sister to the little sister she never had. Finally, she really enjoyed listening to Jan’s stories and exploits. As a young single femboi, Crystal actually had a pretty active sex life. She would tell my wife about times she would meet up with men for sex in cars and theaters and public parks. My wife loved the stories and would also share with me.

There were several times this made me uncomfortable for several reason. First of all, Crystal still had a dick! I’m a horny 40 year old man and I know what happens when the dick takes over. In other words, I knew that enough drinks and that dick might try to find it’s way into my wife. Secondly, she was single and always flirting - even with my wife around. The last thing I wanted was my wife hanging out with somebody that attracts a bunch of guys.

I should take a second to describe each of us. I’m a good looking, confident man. I stand about 5’7” and have a pretty fit body with tan skin, dark hair, and a seven inch cock that I love to use regularly. I am pretty sexually experienced having done threesomes, gangbangs, and a few swinging orgy stuff. One thing I haven’t done is suck dick or take anal. I’ve always enjoyed the female more than the male.

Jan is a sexy MILF. She is about 5’5”, 125 pounds with c-cup tits and tight body. She also has tan skin but short blonde hair. She is not nearly as experienced as I am sexually but we’ve explored several kinks over the past 8 years and even had one swinging event that we enjoyed but it didn’t get too crazy - very soft swap only. Other than that, Jan enjoys some anal and likes being tied up and rough fucked. She has never done a threesome but admitted she wanted to try a MMF at some point.

Crystal is about 5’7” with a runner’s body, dark hair, and a very passable feminine face and body. She apparently also isn’t as experienced as me but has lots of one-on-one sex. Supposedly she “hates” pussy and love dick.

The two of them would hang out every other week or so and I eventually just got used to it. She would come to our house for game nights and drinking sometimes and other times they would go out dancing or shopping or just for lunch. This story starts on Crystal’s 21st birthday. She asked for us both to go out with her to celebrate. Since we live about an hour from the club area she wanted to go to, we decided to get a room near the club.

After we checked in, we got dressed and headed out to meet Crystal for dinner. After a nice dinner, we went dancing. By 10, we were already pretty buzzed and dancing and Crystal was flirting with guys. We joked that she was probably going to get fucked tonight but we were also planning on going at it pretty good in our room. I told my wife she could bring a guy back to the room with us if she found a guy she liked and would be willing to do a threesome. I doubted she would actually do it, but the idea is always a turn on. We danced and drank more until about midnight.

Finally I said we should head back. We were all getting a little too buzzed and flirty and the club was packed. Although they called me an “old guy” they both said I was right and we got our stuff. On the way out, my wife whispered some regret that she never really talked to to many guys due to the loud music. We decided to go get some more food at a local pizza place that stays open late. While we ate, the conversation quickly turned sexual with Crystal talking about how she was sad she didn’t have a guy with her. She said she was going to spend her 21st birthday alone.

Jan felt bad for her and invited her to our room for a while. I immediately questioned the decision silently. I was hoping to go back to our room and fuck! I didn’t want to hang out and talk longer. Oh well, shit happens so I went with it. We got some on the way back to the room and Jan lulled out a joint she rolled earlier. We walked back to the room and smoked the whole way. By the time we got to the room, less than 10 minutes later, we were pretty high. It was about 1am at that time so I was hoping Crystal would only stay maybe 30 minutes and then it would be sexy time for me!