Who has had sex with a CD?

[chris313163]

Would like to hear from other men who have had sex with a CD. What was it like for you? Was it what you expected? Was it a one time thing or did it change your desires for having sex?

 

[mark217mark]

May I PM you chris?

 

[Escierto]

Would like to hear from other men who have had sex with a CD. What was it like for you? Was it what you expected? Was it a one time thing or did it change your desires for having sex?

What do you consider a CD? Someone who lives as a man and sometimes dresses? Or a transgender woman who is actually transitioning or has transitioned?

 

[chris313163]

What do you consider a CD? Someone who lives as a man and sometimes dresses? Or a transgender woman who is actually transitioning or has transitioned?

Good question. For me, I consider a person a CD when I'm with them and they are dressed. I have known some CD's when they haven't been dressed; going to work, playing sports, etc. But for any sexual activity to take place between myself and a CD, they have to be dressed. I think these days, there are more CD's that dress full time. Years ago, most CD's were "closet" CD's; only dressing in comfortable situations. That has been my take.

 

[chris313163]

May I PM you chris?

You're going to think I'm a total idiot; I have never used PM. I usually like to use my personal email, but I know Lit doesn't encourage that. I'm guessing for a PM you need my cell phone number? I rarely have my cell phone ringer or alerts turned on.

 

[BiDrew42]

My first experience with a crossdresser was in 1982 in Miami. I had been having sex with a shemale prostitute for several months and I was constantly looking at shemale/crossdresser porn at my favorite adult bookstore. I was at a hotel bar one evening when a couple came in and they immediately caused a buzz. One was obviously a male dressed as a female, and the other was much more passable. They sat at the table next to mine and I began a conversation with them shortly thereafter. Up close the second girl was also obviously a male, but she was much prettier and much more feminine. Her friend just looked like a guy wearing female clothing. After a few drinks, I asked the pretty girl to come up to my room while her friend was in the bathroom. She said she would love to but only if her friend was invited as well. I readily agreed and then she said "you know we're both guys, right?" I said that I was aware and when the friend came back we headed up to my room. They both remained mostly dressed during the amazing sex that followed. The prettier of the two was very feminine and preferred to bottom only. The less passable lady had a massive cock and didn't mind sticking it in my mouth and ass at all. It was a great night.

My current girlfriend was crossdressing when I first met her although she was passable before she had her first hormone injections. The fact that she was young and Asian had a lot to do with her ability to pass as a woman. She was working in an office during the day and as an escort at night when we first met. I knew she was a crossdresser when we met, but until I saw her panty bulge I could have been convinced she was an actual female.

 

[Escierto]

My first experience with a crossdresser was in 1982 in Miami. I had been having sex with a shemale prostitute for several months and I was constantly looking at shemale/crossdresser porn at my favorite adult bookstore. I was at a hotel bar one evening when a couple came in and they immediately caused a buzz. One was obviously a male dressed as a female, and the other was much more passable. They sat at the table next to mine and I began a conversation with them shortly thereafter. Up close the second girl was also obviously a male, but she was much prettier and much more feminine. Her friend just looked like a guy wearing female clothing. After a few drinks, I asked the pretty girl to come up to my room while her friend was in the bathroom. She said she would love to but only if her friend was invited as well. I readily agreed and then she said "you know we're both guys, right?" I said that I was aware and when the friend came back we headed up to my room. They both remained mostly dressed during the amazing sex that followed. The prettier of the two was very feminine and preferred to bottom only. The less passable lady had a massive cock and didn't mind sticking it in my mouth and ass at all. It was a great night.

My current girlfriend was crossdressing when I first met her although she was passable before she had her first hormone injections. The fact that she was young and Asian had a lot to do with her ability to pass as a woman. She was working in an office during the day and as an escort at night when we first met. I knew she was a crossdresser when we met, but until I saw her panty bulge I could have been convinced she was an actual female.

You are not the only one. The first cock I ever saw on a woman was a Filipina that I used to chat on cam. I talked to her for months until she confessed that she was transgender and even then I didn’t believe her. She had to show me her cock to convince me - my head just about exploded.

 

[chris313163]

My first experience with a crossdresser was in 1982 in Miami. I had been having sex with a shemale prostitute for several months and I was constantly looking at shemale/crossdresser porn at my favorite adult bookstore. I was at a hotel bar one evening when a couple came in and they immediately caused a buzz. One was obviously a male dressed as a female, and the other was much more passable. They sat at the table next to mine and I began a conversation with them shortly thereafter. Up close the second girl was also obviously a male, but she was much prettier and much more feminine. Her friend just looked like a guy wearing female clothing. After a few drinks, I asked the pretty girl to come up to my room while her friend was in the bathroom. She said she would love to but only if her friend was invited as well. I readily agreed and then she said "you know we're both guys, right?" I said that I was aware and when the friend came back we headed up to my room. They both remained mostly dressed during the amazing sex that followed. The prettier of the two was very feminine and preferred to bottom only. The less passable lady had a massive cock and didn't mind sticking it in my mouth and ass at all. It was a great night.

My current girlfriend was crossdressing when I first met her although she was passable before she had her first hormone injections. The fact that she was young and Asian had a lot to do with her ability to pass as a woman. She was working in an office during the day and as an escort at night when we first met. I knew she was a crossdresser when we met, but until I saw her panty bulge I could have been convinced she was an actual female.

Over the years I've been with quite a few CD's. One of the reasons I prefer CD's is; a lot of times when one is a shemale, they have been taking hormones which makes it difficult for them to become erect. I've been with CD's that are incredibly "passable"; even in public you would never know. Being fairly small in that area, it is always exciting when I'm with a "woman" who is larger than me. I also have found CD's tend to be either tops or bottoms; it's pretty rare when one finds a CD that is comfortable with giving as well as receiving. Up until recently, I have been seeing a CD for six years. During that time, I was getting the best sex of my life.

 

[OlderBtm4U]

I’ve been with lots. In my fantasies.
BTW, I find the CDs who aren’t very visually convincing more exciting.

 

[chris313163]

I’ve been with lots. In my fantasies.
BTW, I find the CDs who aren’t very visually convincing more exciting.

That's interesting. For me (and my feelings only), I really enjoy the experience of a good looking woman with something extra; especially is sex is involved.

 

[Escierto]

I’ve been with lots. In my fantasies.
BTW, I find the CDs who aren’t very visually convincing more exciting.

It’s funny. My girlfriend is very feminine and passable but sometimes she lets her facial hair grow out a bit. I find that it makes me really horny for her when I see that trace of masculinity in her. At this point I don’t care if she’s a gay guy - I love her.

 

[KinkyLaughs]

You are not the only one. The first cock I ever saw on a woman was a Filipina that I used to chat on cam. I talked to her for months until she confessed that she was transgender and even then I didn’t believe her. She had to show me her cock to convince me - my head just about exploded.

Which head?

 

[chris313163]

It’s funny. My girlfriend is very feminine and passable but sometimes she lets her facial hair grow out a bit. I find that it makes me really horny for her when I see that trace of masculinity in her. At this point I don’t care if she’s a gay guy - I love her.

View attachment 2143894

She looks very attractive. Curious, why does she sometimes let her facial hair grow out?

 

[KinkStevens]

TS yes. CD no. Not because I wouldn’t but because I haven’t met one in real life

 

[Escierto]

Which head?

Now that you mention it, both heads!

 

[Escierto]

She looks very attractive. Curious, why does she sometimes let her facial hair grow out?

She doesn’t let it grow out very much, just a little on her chin and along her jaw line. She used to be a fanatic about plucking but I told her it doesn’t bother me so she isn’t as hard core about it. Most of the time she still does it - in fact I am going to bring her a laser hair removal machine when I see her in July.

 

[darenCA20m]

Where do or how do you go about meeting a crossdresser, or trans girl, or a femboy? I love feminine anything even love wearing more feminine clothes such as panties lingerie heels dresses and would love to try dating one of any of the 3...

 

[Carnevil9]

CD, no. But I've had sex with a number of DVDs.

 

[chris313163]

Where do or how do you go about meeting a crossdresser, or trans girl, or a femboy? I love feminine anything even love wearing more feminine clothes such as panties lingerie heels dresses and would love to try dating one of any of the 3...

Over the last 8 or 9 years, my contacts have been friends of CD's I know. Craigslist used to be a great resource; sadly their personal section no longer exists for making contacts.

 

[Escierto]

Where do or how do you go about meeting a crossdresser, or trans girl, or a femboy? I love feminine anything even love wearing more feminine clothes such as panties lingerie heels dresses and would love to try dating one of any of the 3...

You can find transgender on Tinder and Grindr. Definitely CDs on Grindr. If you are adventurous like me you can find them on sites like ThaiFriendly and Pinalove for someone in Asia. My girlfriend lives in the Philippines.

 

[cubbyfire04]

Would like to hear from other men who have had sex with a CD. What was it like for you? Was it what you expected? Was it a one time thing or did it change your desires for having sex?

My ex-wife and I swapped partners with another bi couple we met at a party. They met us at a cabin rental and after some drinks, his wife directed me to their room to wait on her husband. After several minutes, she opened the door and presented him to me fully dressed with makeup and his hair done. She closed the door and left us to it. The ladies went to their separate quarters for the night (oh to be a fly...).

I wasn't expecting him to be a CD, and never really explored the idea. It took me a minute to get into the right mindset, because although he was almost passable, he was quite masculine in our encounters leading up to it. I'm very masc myself, but I am submissive. He knew this and proceeded to take on the role of a dominant mistress.

It was wild. He only let me cum that night because I fired off a hands-free load when he was fucking me. He came multiple times, and finally we fell asleep. I woke up very early to him showering. I snuck into the bathroom to pee, and he invited me in. I was rewarded for being a good sub with a mind-bending blowjob after we both scrubbed and stroked each other until the water ran cold.

Wasn't what I would expect from a CD experience, but a pleasant surprise to say the least. So for the sake of new experiences, 10/10 would recommend and do it again.

 

[chris313163]

My ex-wife and I swapped partners with another bi couple we met at a party. They met us at a cabin rental and after some drinks, his wife directed me to their room to wait on her husband. After several minutes, she opened the door and presented him to me fully dressed with makeup and his hair done. She closed the door and left us to it. The ladies went to their separate quarters for the night (oh to be a fly...).

I wasn't expecting him to be a CD, and never really explored the idea. It took me a minute to get into the right mindset, because although he was almost passable, he was quite masculine in our encounters leading up to it. I'm very masc myself, but I am submissive. He knew this and proceeded to take on the role of a dominant mistress.

It was wild. He only let me cum that night because I fired off a hands-free load when he was fucking me. He came multiple times, and finally we fell asleep. I woke up very early to him showering. I snuck into the bathroom to pee, and he invited me in. I was rewarded for being a good sub with a mind-bending blowjob after we both scrubbed and stroked each other until the water ran cold.

Wasn't what I would expect from a CD experience, but a pleasant surprise to say the least. So for the sake of new experiences, 10/10 would recommend and do it again.

Sounds as if your first encounter was a great one. My first encounter was also great. She was very, very passable (could go out in public and no one would know), very, very well endowed. The fact that she was wearing boots and leather only added to the attraction. I never thought I would do that, but I found myself wanting to satisfy her orally; and I did several times. After that, we were together for the better part of a year. She changed my sexual desires.

 

[cubbyfire04]

Sounds as if your first encounter was a great one. My first encounter was also great. She was very, very passable (could go out in public and no one would know), very, very well endowed. The fact that she was wearing boots and leather only added to the attraction. I never thought I would do that, but I found myself wanting to satisfy her orally; and I did several times. After that, we were together for the better part of a year. She changed my sexual desires.

Also sounds like a wonderful experience!

 

[SexyInTyvek]

Would like to hear from other men who have had sex with a CD. What was it like for you? Was it what you expected? Was it a one time thing or did it change your desires for having sex?

What about women who have?

 

[FeelingLikeMyself]

Would like to hear from other men who have had sex with a CD. What was it like for you? Was it what you expected? Was it a one time thing or did it change your desires for having sex?

I have a thing for guys in women's clothing that's gotten my consent attention since I was 16. I don't know what it is. I even dress a little bit myself.

The first time I did it, I was so nervous. I've had sex with other guys. Once we were both wearing hose, sometimes I was wearing panties, but never fully dressed up. The first time I was with a guy who was fully dressed I was so excited and distracted and nervous that I had some difficulty getting hard at first. He was patient and eager and so, so, good. Easily one of my top three experiences along with being pegged into subspace and finding out wearing heels and thigh highs flips a switch in me that turns me unashamedly dominate.

It was everything I expected and more. 10/10 highly recommended.