Bi men who cross dress

dimru

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I did it, it was fun. My fantasy is to completely transform into a woman and suck cock in a public place.
 
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latinluva

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So in my twenties, I met a married man. Great looking guy, huge cock and very masculine. When we met (at the adult arcade) he said, "I only like guys that wear womens clothing". I told him,"I don't do that kinda stuff". He entered his own booth that had a gloryhole, as I watched him pull his cock out and jerk off, I was amazed at the size of this mans cock. Eventually we talked again, and I told him that maybe I could dress up for him, but that only if he came to my place. So we agreed to meet the following night. I had went down and bought a wig, some make up and womens clothing. We often met over the course of 12-18 months, and serviced his cock several times. One of the best sexual relationships I ever had. As for the rest of my sexual life, I never went back to crossdressing, but I do love a lot of gay mens clothing or attire. Things like, gay mens thongs (yellow, red and hot pink), leather chest braces, leather jock straps, black thigh high leggings and leather chokers. Very feminine mens clothing, such as thongs under very short jean shorts. No hair on my body....lotioned up legs and arms.
 

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I don't cross dress, per se. However, since "becoming bi" 10 years ago, I very much prefer thongs, bikini everything, silk. I shave as much as my wife will allow (not lower legs and arms) and love it....I also like tight stuff on guys, and wish we had it even with women on bikinis... I have even just recently, begun enjoying some nipple jewelry... and some time may piece a nipple. Biggest thing, though, is I find this change in me, quite pleasant, and so does my wife...!
 

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I’m not really into cross dressing for myself. But if a man i was with asked me to… absolutely yes.
My first male partner got me introduced to cross dressing. I thought it was a lot of fun. He would ask if I would wear really short skirts when I would hang around his place. It was harmless role playing which I enjoyed. Being made to feel girly and feminine actually made the sex hotter for me and obviously for him.
 

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My first male partner got me introduced to cross dressing. I thought it was a lot of fun. He would ask if I would wear really short skirts when I would hang around his place. It was harmless role playing which I enjoyed. Being made to feel girly and feminine actually made the sex hotter for me and obviously for him.
That IS hot!
 
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goldscorpguy

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I’m not really into cross dressing for myself. But if a man i was with asked me to… absolutely yes.
Exactly the same here. Few years back one of my previous FBs used to send me links to a sexy clothing site and what he wanted to see me in. I didn't try it out then but if asked now I would definitely do it.
I do have some gear like a mesh body suit, chest straps and a hand made leather collar which I've worn to a few parties. So clothing would just be a natural extension to this.
 

bi2

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That IS hot!
There was a big age difference between us back then, so me complying with his request wasnt an issue, nor did I challenge it and I could easily fit into slim tight short skirt, lol. I was fairly petite then.

As I mentioned before, wearing it turned me on and in a kind of way preconditioned me to feel and act feminine with him. I enjoyed it and he enjoyed me being that way.

If I had to look back at it, I guess because his wife had left him, he viewed me as some form of replacement.

When we had sex, plenty of times, he wanted me to keep the dress on while we did it.
 
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bi2

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Exactly the same here. Few years back one of my previous FBs used to send me links to a sexy clothing site and what he wanted to see me in. I didn't try it out then but if asked now I would definitely do it.
I do have some gear like a mesh body suit, chest straps and a hand made leather collar which I've worn to a few parties. So clothing would just be a natural extension to this.
Most definitely as you mentioned a natural extension is how it took place for me. I probably would have been freaked out if he had suggested earlier. He was my first, so naturally following his lead was something that came natural and over the course of several months.

By first I mean, for everything with MM sex. So really it felt a natural progression of our relationship together.
 

18wheeler

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There was a big age difference between us back then, so me complying with his request wasnt an issue, nor did I challenge it and I could easily fit into slim tight short skirt, lol. I was fairly petite then.

As I mentioned before, wearing it turned me on and in a kind of way preconditioned me to feel and act feminine with him. I enjoyed it and he enjoyed me being that way.

If I had to look back at it, I guess because his wife had left him, he viewed me as some form of replacement.

When we had sex, plenty of times, he wanted me to keep the dress on while we did it.
Oh yeah. I get it. Personally. I wouldn’t/don’t feel sexy cross dressing for myself.
BUT if the man I’m with thinks I’m more sexy or is more turned on by it. That turns me on doing it for him.
 
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18wheeler

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Exactly the same here. Few years back one of my previous FBs used to send me links to a sexy clothing site and what he wanted to see me in. I didn't try it out then but if asked now I would definitely do it.
I do have some gear like a mesh body suit, chest straps and a hand made leather collar which I've worn to a few parties. So clothing would just be a natural extension to this.
I could NOT pull off a body suit. Hahaha

now…. Give me some garters and thigh highs and a nightie. I could totally rock that for a man if he wanted me too.
 

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18wheeler

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bi2

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Oh yeah. I get it. Personally. I wouldn’t/don’t feel sexy cross dressing for myself.
BUT if the man I’m with thinks I’m more sexy or is more turned on by it. That turns me on doing it for him.
For me now, its now an important step when I "prepare" to meet my fuckbuddy to have MM sex.

My fuckbuddy expects/wants/demands sex the moment we are alone. So naturally I need to be prepared for that. So cross dressing provides the foreplay to get more sexually aroused and ready to go. I get turned on while wearing it, but its because I know it pleases my partner and turns him on.

There is very little I wouldnt do to turn him on for our encounters.
 

18wheeler

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Highly recommend for any bottom or submissive bi guy.

Its part of the foreplay for me and makes MM sex so much hotter.
I have no interest in it solo

But as a bottom. It’s one of my biggest fantasies. I’d love to wear lingerie, some sort of dress(babydoll/sun dress) and get laid in someone’s backseat.