Question: First sexual experience with a man, how did yours happen?

[Alex]

I've been a crossdresser for 17 years or so, but have only recently been allowing myself to truly explore who I am. I know it's more than casual crossdressing, but I don't think I am quite transgender. For sure more on the femme side of the gender binary, though. I've never been intimate with a man, but i've recently become curious about it. I wanted to ask some advice from any of you whom have been primarily with women, but have "tried out" men.

How did it happen?/What did you do to make it happen?

I don't really want to try hook-up sites/apps because I am wary about safety (both physical and remaining STI free). I don't really know a lot of gay/bi men, either. All the guys I know are pretty straight (or at least appear to be)...it's not like I can casually ask if they were up for it.

Any ideas/advice?

[sometimes_miss]

Well, let's see, I was six years old.....you can figure out the rest.

[Ceera]

I went to an LGBT bar and nightclub en-femme, and was enjoying socializing with anyone who wanted to talk to me - chatting or dancing - regardless of the other person's gender. Male, female or trans, it was all good. After a few months as a 'regular' in that club, going every week or so, it wasn't that uncommon for an admiring guy to occasionally offer to buy me a drink, and to want to talk or dance with me. Occasionally a girl would buy me a drink as well, and lots of the girls there liked to dance with me and chat with me, even if they didn't buy me drinks. I liked going to that club, a lot.

Well, one night, while I was walking around inside the club while cooling off between dances, a guy caught my attention and complemented me on how beautiful I was, and then he offered to buy me a drink. I accepted, and sat and chatted with him. He was fairly average in appearance. A bit on the heavy side, but not obese. But his personality was quite charming. He said he was a salesman, in town on business, and I knew he was not a regular in the club. He was quite happy to treat me like a lady, though he apologized for not being up to getting out on the dance floor with me. Bad knees, he said, and not up to dancing to the lively music the DJ was playing. Still, though I got up and danced with others severs times, he always cheerfully invited me to join him again, and he bought me more drinks. I appreciated that he actually talked with me. He made jokes, and though he asked the sort of questions one needs to ask if seeking a suitable partner, he also wanted to talk about things other than just 'so, how long have you been trans', or 'so, do you go both ways?' In short, he seemed like a nice guy, and he seemed interested in me as a person, and not just as a sex object. Eventually, he did ask if I wanted to 'go someplace else and fool around'... He also said he'd enjoyed a trans lover several times before, so he knew what he was in for if he got intimate with me. I decided to accept his offer. After a nice kiss in the parking lot, and several frustrating tries at finding an affordable hotel room nearby, (an event in town had all but the most insanely expensive rooms booked solid), we ended up with me taking him to my place for a few hours. It was quite nice, and he treated me quite well. We both enjoyed the evening. But when all was said and done, I didn't bother to see him again. He wasn't that good in bed, and I was going to be leaving that town soon, and didn't want a relationship when I would soon have to break it off.

That was the first time I ever went beyond kissing and cuddling in a corner of a nightclub with a guy while en-femme. (There had been a few other intimate encounters in my life with males long before I accepted I was trans, but I'm not counting those, since they all just sort of 'happened', and weren't a planned thing at all.) I don't regret it at all, but I haven't repeated the experience since moving to a new town. I've gone out in the new town the same way, and had a few nibbles, but nothing worth following up on yet.

I'd treat it like any other sort of dating or socializing. Go out solo, or better yet with a platonic friend, to a nightclub, dance, bar, or other social event - preferably one that is LGBT friendly. See if you can make friends with someone you find attractive, and be up front about your own circumstances. And if it feels right go for it! Of course, be careful when getting together with a stranger. Try to get to know them first, and have a backup plan if it goes sour. Probably not a bad idea to call a friend, so they know where you are and who you are with, and make sure they call back to check up on you occasionally. Good luck!

[ClaudineD]

After hour cocktails of many, many, many Jamesons and nature took hold !!! ....LOL

[Aly Cat]

For me, I had been talking to this guy for almost a year but it was long distance. We had met once for a camping trip, but behaved ourselves. The next time we got together, it was no holds barred. It was AMAZING! Now, of course, he and I live together and have been together forever two years now and living together for over a year. We have an amazing life now

[Tracii G]

I find it sad that some here just want sex with out love.
The love part never enters their mind they just seem to think you just pick out a guy to have sex with for a fantasy.
Falling in love with a guy is the same as falling in love with a woman for you straight people.
I would love to find a decent guy I could fall in love with.
Maybe I am old fashioned but sex and love go hand in hand for me.
I have dated guys and the connection was just not there after a few dates. Could I have had sex with them yeah maybe but sex isn't all I am after in a relationship.
There need to be a connection.
My first foray into this life style I met a guy I worked with who was "out" but I was not.
We went to a movie and I made a move on him and he reciprocated.
It was at a drive in movie so we made out for what seemed like hours and it was fabulous.
We became really tight friends and even shared an apartment together.

[atlflygirl]

I'm a gay man (really a woman in the shell of a gay man), so I've dated men as a guy all my life. I've only had sex with a couple of guys en femme. One was a football player from Oklahoma, and he wanted me to do him as a woman. As I pummeled him, he kept saying, "Ah! Yes! You're SUCH a pretty GURRRL!" Without a wig and heels, just makeup and earrings. Yeah. It was fantastic, as I was allowed to be my usual aggressive self in bed, but I didn't really feel that womanly then. Another I met was a very straight, married man with a mustache. Very handsome and a real gentleman. He was a great kisser and really made sure I was comfortable. Those are the kind you keep! Get a married father, and he'll treat you like a lady, just as he's been trained to do. Avoid bi guys at all costs. 99% of them have no amorous interest in us and just want to get off. They usually have cis women waiting for them at home. Try tsmeet and get a gold subscription. They seem to have the most active users.

[TrishaTX]

12 years old best friend was older, asked me to wear my sisters clothes...well I was already doing that anyway...the rest is history

[JenniferMBlack]

I was 12 he was 12 i wore gorls clothes he loked guy's in girls clothes. So 2 horny 12 yr olds into samething what more needs to be said.

[Ceera]

Traci, I would be overjoyed to find a real love connection with someone. I truly hope that lightning will strike a second time for me, and that I will find someone I can be with for many, many happy years, and who accepts and enjoys both sides of me this time. But until I find that special someone, I'm not going to turn down affection when I can get it - even if it is just a one night stand. Being alone sucks, horribly, after over 30 years of having a lifemate.

[Nikkilovesdresses]

It's hard to make a gay hook-up without going to an overtly gay scene, at which point your first thought is going to be risk of STI.

My own encounters have been some of the most exciting sex I've ever had. They've all involved gentle, thoughtful people, rather than cold pick-ups, and I do miss the possibilities of being single.

All I can say is think of it like losing your virginity- try to select a partner who is gentle and kind, and make sure you're very safe in terms of infection and personal risk. Beyond that, you're probably going to find it pretty darn exciting. Once you've broken the ice, you may feel more confident to seek more specific fantasy fulfilment, eg role playing, cosplay, or whatever.

I tend to prefer the passive role in any kind of sex, so for me it's about being 'taken' by a man, which ties in closely to that side of me which wants to feel like a traditional female, and how women reconcile that urge with feminism I will never understand. I see myself at home in the cave, improving the nest, while Ug goes out hunter-gathering, occasionally coming home so that I can polish his spear for him.

Does that help at all?

[Stacy Darling]

Two people; The first was my ex-wife and after I let her have her little Dom fantasy she kept at it for the next few years and I wouldn't want another man taking me like she hurt me!
After the divorce I was safe from her and often went out with a gay mate of mine (just for beer drinking and fun times, not a relationship!) whom I've known for years and I felt comfortable with him. So, as we all know drinking an inhibitions mix well! It started in the bar and soon in a nearby park as we weren't going to make it any further. I stopped when he wanted to go all the way, probably a subconscious thought of what my ex-wife had done.
So in a strange way, I've sort of done it.

I just hope that you can find some loving, caring and gentle!
You don't want to have your face pushed into a pillow to stop you from saying STOP!

Best of Luck with it,
Stacy

[Lori Kurtz]

I had only only one sexual experience with a man: a chance encounter with someone whom I clocked as a crossdresser while I was in drab. For me, crossdressing had for many years been an intense sexual (though completely solitary) act, nearly always ending up with an orgasm. When I saw this "woman" and recognized her for what she really was, I was immediately excited and aroused sexually. In a secluded outdoor spot, I showed her something that indicated my interest (trying not to be too explicit here!), and I told her that I was a CD too. We started making out--kissing and hugging, with my hands wandering all over her body. Neither of us took off any clothing, although she did lift up her dress so that our bodies could rub together down there. She was leaning back against her car as we did that, and the scene would have looked to any observer as if we were a man and a woman having stand-up fully-clothed sex. She must have had her male goodies tucked back, because I felt nothing of the kind, and I believe that she, in her female mode, enjoyed my male interest in her as much as I was imagining how wonderful it would have been for me to be in her shoes (and wig and bra, etc.!) and have a man be as turned on by me as I was by her.

Although I consider myself mostly heterosexual, part of the thrill of dressing up when I did it was to become a very sexually exciting women who would appeal to men. I was a sex object to myself, and enjoyed the thought that I could be sexually exciting to other men--but only when I was in my female identity.

I loved this one-and-only real-life sexual experience with a man, and would have loved to meet up again--maybe en femme--with this man who had something important in common with me. But I was afraid of all the possible complications. I was still married to my first wife, who had no idea that I was a crossdresser. I felt guilty about cheating on my wife, and guilty as well about letting my new friend believe that I would see her again.

The experience was incredibly exciting, and scary at the same time. From this perspective in my life many years later, I am comfortable with this having been a homosexual experience, and also with it having never been repeated.

[Periwinkle]

Well, my first sexual experience with a man was my first one in general. With the only partner I've ever had. XD

I don't necessarily know if this post refers to just getting a little touchy-feely or going all the way, but those happened at drastically different times. They were both really nice times though.

[Ressie]

I was living with a friend back in 1972, I was only 19. He hit on me one day so subtly that I didn't know he was doing it! Flash forward to 1980 - we were still very close friends, and he was getting a little more suggestive. We were in the car with a 3rd friend and he asked him "so, are you gay or what?".

Then one day he had some hetero porn that he let me check out, of course I was getting aroused from that. That summer, he got a job painting his brother's house (in another town) with the other friend. I started thinking, "I wonder if they're doing something sexual" and I was getting curious about it. I was added on as another worker so I was spending nights there. I don't know what came over me, but I kind of flirted with him. I kind of swiveled my hips as I was changing my shorts lol. Nothing happened though.

So another night back at his house he kept on rolling and smoking one joint after another. I was very high and he just came out and asked if he could do something sexual to me. I said no at first, but then I wanted to try it. We had 3 encounters all together, then we both felt kind of weird about it. Anyway, as Tracii G pointed out, I could have fallen in love with this guy. We were already really good friends, the sex was amazing, and he was very good looking.

It would be 17 years later before I did anything sexual with a man again, and another 17 years passed before I did anything a 3rd time. So my answer is to either advertise, answer others' ads or do some flirting like I did If you keep thinking about having sex with a man, it will happen eventually.

BTW, I wasn't crossdressing with my first, but I asked him if he liked that sort of thing and he said no. I could only fantasize that I was cross dressed when I was with him.

[Heather Anne]

Never have and never will ever.

[SometimesKairi]

Since I am not attracted to men I can't see it happening to me but I have noticed that since I have become slightly more open about the dressing I HAVE received a few 'offers' from men to 'meet' them.

Haha I now see why women moan about pervy men a lot

[Lilly 40C]

A woman I was dating at the time liked it when I dressed before we started having sex. One night she said she wanted to have a threesome with a guy we both knew but wanted me to be dressed so he would think he was with two women. When the night came my girl friend and I were dressed provocatively when the guy came over. We all sat around drinking a few cocktails when they started making out. It was not long thereafter when he and I were making out. I could not believe how natural it was for me to be kissing this guy even French kissing. Before the night was over after some fondling with him, we had sex. Again, I could not believe how natural it was for me to be so intimate with a guy. The rest is history. Now, a good looking guy turns me on as much as a good looking woman. Since then, I've been with three other men. All of them treated me well and I enjoyed every moment of being with these men.

[Just Nikki]

Well Alex, I wish I did know how to make it happen.
~Nikki

[Ozark]

It was 1969. I was in the seminary. I had worn panties in high school and thought I was a horrible, horrible person. I entered the seminary to drive those thoughts away. I was wrong. Was I ever wrong

[Lacey CD]

It was a warm night in my 15th summer. I decided to go for a walk by myself to clear my head a bit. It was late and traffic was light which made for a peaceful stroll. A car with a man about 35 drove by and slowed down as he passed me. I could tell the driver was checking me out. I was a skinny long haired rocker and had started to realize certain men paid me more attention than others. A few minutes later he passed by again only this time he stopped and asked me if I needed a ride. I knew very well that offering me transportation was not his primary objective. I had been asked this question before during my late night walks and always refused the offer, but this time I said yes. He asked me where I was going to which I replied coyly, "no place in particular". He asked if I would like to go to his place and with a lump in my throat and barely able to speak I nodded my head in the affirmative. When we got to his place just around the corner, he led me upstairs to his bedroom. It was all so surreal but etched in my memory forever. Afterward, he told me I could come by any time. I had a bit of a lingerie collection at this point as my mother had passed away a few years prior and I "inherited' a lot of her things before my father gave most of it to the Salvation Army thrift store. I had also been able to sneak some other items from a buddy of mine's mother who had an enormous collection of very sexy things.
A week or so later, I gathered some of my favorite items in a backpack and headed out for my evening walk. His house was close and I made a bee line for it. He answered the door and greeted me with an ear to ear grin. We sat down for a few minutes and he asked me what was in the backpack. I was shaking I was so nervous and was unable to speak so I opened up the pack and showed him. I could sense his approval by the look on his face. He showed me to the bedroom and told me to take my time and get changed and to join him in the living room when I was presentable. I could barely get dressed I was shaking so badly. When I was dressed, I looked at myself in the mirror and something profoundly changed in me that moment. I didn't know the person looking back at me. I had no idea what was happening to me, only that I felt a deep sense that I had changed not only my clothes, but something far more significant and I would never be the same. Afterward I was filled with all of the shame, guilt and disgust that would plague me for years to come when I indulged in such activities. I saw him a few more times before he moved away, he was a sweet man and I am forever in his debt for showing me another side of life and another side of myself. It would be years before I was able to shed the negative emotions and accept myself for who I was.

[Maria Blackwood]

College. When I was first exploring the BDSM scene.

I find it sad that some here just want sex with out love

Oh, please... :-P

[Kendra Sue]

I had one experience with a man. He was on a street corner and I knew he was a man. We had anal sex which I enjoyed but have not had it since

[Jeri Ann]

Hey Alex,

I debated responding to your OP for several days before deciding to contribute because you seem to imply casual sex which I could never consider. In fact, the notion of it grosses me out. Although my experience is totally different, here goes.

Not even considering, much less looking for, a relationship, fate intervened. It started with a casual meeting followed by thousands of emails. Then that special night came. I knocked on his hotel room door and there he was, tall and handsome as all get out. Stepping into that room was like stepping into a dream. He had candlelight, soft music, dinner, champagne, chocolates and a dozen roses for me. We danced. We kissed. We...

It was an amazing night. He is an amazing guy. I am so fortunate.

Jeri

[Pattie]

I was sort of hesitant on replying to this but after some thought I will.
I was about 16 and was out to the corner store for some ice cream one evening not late but after dark and was approached by 2 older teens they grabbed me and reaped me in an alley way, when I told my mother about what happened she enrolled me in a martial arts class the next day. She said it will never happen to me again, by the way they caught the A&&^^%les who did it and are sexual crime registery participants. And it will not ever happen to this Girl again. This brought back some erie memories for me thanks for listening.
Pattie