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My First Time With a Man While Cross-dressed

my first time with a man while crossdressedMy first time with a man while crossdressed was amazing and unexpected. I had no plans for such a thing to happen but when it did it swept me off my feet. My ex-wife was away on a two week business trip and I had big dressing up plans but only in private. I was also planning to have a few glasses of wine and go online into a crossdressing chatroom and have fun there.

The chatroom wasn’t all that busy so I started looking around and saw a T4M room so I went in there and it was better. I knew I’d have to deal with men but since it was fantasy I figured what harm would that be? I got into a few conversations but one guy got really forward with me and told me I would really enjoy going down on him and having him inside me.

Now to be honest I never wanted to make a woman give me oral s*x because I couldn’t imagine anything more disrespectful than making a woman put my thing in her mouth! My ex-wife had given me a blow-job twice in our marriage and I couldn’t stand it, I pulled out because it felt horrible and asked her to never do it to me again. I ended up chatting a lot more with this man and started getting really turned on and though I was pleasuring myself I wanted more.

I ended up where I couldn’t take anymore of chat so I decided to go out and ended up going to a gay club close by. I was so nervous, I put my ID, my house and car keys, spare panties and pantyhose, some makeup, k-y and some tissues in my purse and decided to get going. I got there about a half hour later and steeled myself to go inside.

I paid a cover charge, the man at the door smiled and let me in, I was a wallflower for a bit and a man come over to me pretty quickly. Apparently the man at the door told him there was someone here he might be ‘interested in’. We sat down at the bar and chatted for a few minutes and got a beer each, he bought.

We moved to a corner so we could hear each other easily. I told him I was a crossdresser, of course he knew, he told me I looked really good, I told him I was married and straight and he said something like “ok, that’s nice” but I think he could tell that I was ‘curious’ at the very least and I definitely was sending vibes that I was aroused. He was very gentlemanly with me and I started getting more settled and comfy with him, also I’d had a second beer with a third in my hand and was getting more relaxed.

He asked if I’d ever gone out dressed, I said I had, he asked if I’d ever been with a man and I told him in my early teens I had experienced being with a man. He asked if I really was straight and I hesitated but admitted I was either bi or more likely gay. He asked me if I’d like to dance so I downed the rest of my beer and went to the dance floor with him.

I’m not much of a dancer but I got into it, mostly just him guiding and me following. It all started on a slow dance and he pulled me close to him, he grabbed my ass cheeks and pulled me tight and I felt ‘something’ and it took me about 10-15 seconds to realize he had an er*ction. I was sooo shocked and actually felt pride that I caused this, I also felt desire like I’d never felt before!

He was smiling away and all of a sudden he leaned over to kiss me, I didn’t so much as let him as he surprised me. I was in shock, so much was going on, I kissed him back and then he put his tongue in my mouth. I was in ecstasy, he kissed my earlobe, took it between his lips and tongued my ear, then he kissed my neck, ran his hand up the back of my thigh and I almost lost control. I wanted him really badly right then, right there!

We went back to our quiet corner, he asked me if I wanted more, I told him I absolutely did but I was scared because I was married but I wanted him so much I was conflicted and ashamed but had never felt before what I was feeling now.

I asked if I could feel his er*ction and he loosened his pants just enough for my hand to go in and when I felt it I told him I needed him to make love to me. We went to his car and he brought me to his house. I couldn’t keep my hands off of him the whole way to his house, I was so aroused the whole time. We got into his house and I practically threw myself on him, I wanted him so much!

We went into the living room and sat together, we kissed, I felt his hardness and I undid his pants and saw that erect p*nis and got ready to go down and I hesitated. I told him I suddenly got nervous because I was a married man and I was about to cross a line I couldn’t cross back over.

He convinced me that I’d crossed that longer a long time ago, when I decided he was right I went down on him in a flash. I never knew this feeling before and I wondered why on earth I ever thought this was a disgusting thing to ask a woman to do because I thought his c*ck was the most beautiful thing I’d ever seen. I kissed the tip, ran my tongue all over it and up and down the shaft as well. I took it in my mouth and though it took a bit I was eventually able to take it in my mouth without any trouble at all.

Through the night we went from oral to an*l. I couldn’t believe the ecstasy and thrills I felt. We met quite a few more times during the remaining week and a half I was free. I didn’t always get to dress for him but the physical and s*xual thrill was just as amazing every time.

I ended up staying married for another 15 years but my ex-wife caught me because I left my email open on the computer. I came out to her on my gender dysphoria and my crossdressing and she filed for divorce..

Submitted by Charlotte

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  1. Thank you Keith and Gerryy and those feelings for men were always there. I do remember my first experiences when I was 12 with an older boy felt so good and since I liked boys I didn’t really know there was any other ‘way’. I had my first experience with a woman when I was 24 and it certainly felt good but after a couple years I really didn’t get into it. I tried to avoid sex with my ex-wife as much as possible but she’d insist on it so it would happen. If I could avoid it I would but she’d force it by waiting until I was in bed and she’d pin me down. My gay experiences I had while I was married started happening after I’d been married for about 18 years and it rekindled the desire for physical pleasure. I think I stopped dating men in my late teens because I was worried about AIDS and since I was married I tried to stay faithful. I’m so glad I’m out now and finally admitting I’m a gay crossdresser has made me so fulfilled! I’m so incredibly happy and so sexually fulfilled!

    Amber, keep trying, there’s someone out there for you too!

  2. I loved it too Elio, it had been a long time since I’d been with a man. My first experience was with boys and men from the time I was 12 until I was 23. I was with a woman for the first time when I was 24 and got married a year after that. I did stay faithful to my ex-wife from 1984 to 2003 when this incident took place. We stayed married until 2021. She knew I dressed and was ok with it for a while bit never liked it. I dated lots of men in the past 20 years. She caught me because I’d left email logged in and to this day I know I probably did it on purpose so she’d catch me. I wish I’d never tried to pretend I was straight, I wasted the best years of my life.

  3. Such an encouraging story for us. I know that one day when I finally get with a man and I feel his hardness for me all my reservations will melt away.

    1. Wanna fuck now?

  4. When you step over that line it all goes so easily. If I’d been more brave I’d have never dated women. In 1973 I was 13 and had my first intimacy with an older boy. He was in High School and he made me excited because he could drive and paid attention to me. We were together until he went to college. I dated a number of boys and men until about 1982 when AIDS really started becoming a problem so I stopped because I didn’t want to get AIDS. A friend fixed me up with a woman and it was weird but I made it work for a while. I kind of figured what breasts were like because they were like mens but bigger but I wasn’t prepared for what’s ‘down there’. The woman took my hand and put it in her naked crotch and I was shocked. She forced my fingers in her and the warm, velvety feeling was interesting. I couldn’t tell if it was wet or what but I pulled my fingers out and smelled them and I got hard pretty quickly. She assumed I was turned on which I guess I was but I didn’t know what was going on. She undressed her bottom and pulled my pants down and and forced me into her. It was ok but nothing great. We dated for a year and she wanted to marry and I figured I could work it out. I went almost 20 years without a man but when I went back I knew it was right right away. It didn’t take long!

  5. Luv this story ready to be that gurl

  6. Wonderful story Charlotte!
    It was very exciting to read how was your date, and it made me dream with have something like that.
    Thanks for writing it with such a great style, and for being so brave…

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