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

I was 11. And I knew what they were looking for from the get-go. They were a gay couple, (this would have been what? 1975?) who were scoutmasters of my boy-scout troop. In all seriousness, they got arrested.. one of them fled to Canada.

They had like seven or eight of us on the hook. Almost every one of those boys ended up violently screwed up. Except me, as I was already so inclined.

It was fun for me, actually. I knew what I wanted, and they were all too willing to give it to me.

I knew I liked XY's from pretty damn early.

Then in my 20's, there was Lugh. This pretty goat of a man who really wanted me romantically. He was a real sweetie, with him the difference between predation and interest became clear. It changed almost everything about how I saw gender interests and relationships. I guess I owe the abusers a small thank you for opening my eyes.

You have the right to like and want you like and want. Men are nice... big and strong and furry and.. UNF.

- MM

Truth be told, I am Bi but at the time I didnt really know what that meant. I was in middle school and had just started exploring my feminine side - read, i'd just started to dress. The guy was my best friend although a few years older than me. We were both on a swim team. One day I was at his house watching TV and without so much as a How do you do, he planted a kiss on me. I didnt resist and it didnt take long before we were exploring. After a few weeks, i told him i liked to dress up. I essentially became his girlfirend - in secret of course. Both our our dads were in the military so, needless to say, we kept it a secret. He moved away about a year after. We kept in touch for awhile but eventually lost track.

Lots of different responses to this thread. Some stories seem happy and some so sad. So I just want to add one experience into the "Happy" category. I had fantasized about hooking-up with a guy for a long time. I started corresponding with a guy on a dating website. We kept in touch for about a year. He knew all about me. And I felt like he was a decent guy after "numerous" e-mails back and forth. So, after a year we set up a date. We were to meet at a hotel bar for drinks. Yes I was very nervous but I trusted that the guy was OK since we had a long relationship. We met. Had a few drinks. Then went up to my hotel room and had an "Incredible" evening together. Everything I had dreamed about and more. Defintitely have no regrets. I am still in touch with him and we are trying to get together again. Can't wait. Anyway, that is my first experience with a man. For me it went very well.

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Originally Posted by Ceera

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!

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Good advice, thanks! I supposed "being on the prowl" is the same, but just perhaps different venues. My issue is that i've bee married for a long time and don't really remember how the whole game works...and even how to flirt and stuff as a woman. I think some research is needed :)

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Originally Posted by 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.

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I am looking to try men with no commitment first, because I don't honestly know if I even like them. Love is all great and everything, but...
What if I fall in love with a guy, or he falls for me and I find out I really don't like the sex?
What if I can't fall in love with a guy because I don't know if I will enjoy the intimacy?

I've wasted a lot of time on my journey of self-discovery, I don't really want to waste any more of my time, or the time of others.

Not saying I want a parade of dicks at my door, just a casual date with some mild fooling around and see what happens then.

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Originally Posted by 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.

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That sounds amazing!

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Originally Posted by 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

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Not looking for super casual, like a Tinder hook-up or anything. I'd want to hang out and at least get to know him a bit, first.

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Originally Posted by Sabrina133

Truth be told, I am Bi but at the time I didnt really know what that meant. I was in middle school and had just started exploring my feminine side - read, i'd just started to dress. The guy was my best friend although a few years older than me. We were both on a swim team. One day I was at his house watching TV and without so much as a How do you do, he planted a kiss on me. I didnt resist and it didnt take long before we were exploring. After a few weeks, i told him i liked to dress up. I essentially became his girlfirend - in secret of course. Both our our dads were in the military so, needless to say, we kept it a secret. He moved away about a year after. We kept in touch for awhile but eventually lost track.

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That sounds like a dream. Pretty much my ideal situation, without the secrecy.

We met on a dating website and went out for drinks in a bar in the lgbt friendly part of town (with me dressed). I didnt see him again but it was an enjoyable experience

Hey Alex,

This is a really interested thread as there is so much difference from girl to girl. I will share you my experience and hope you understand the message I'm sending you. Please feel free to disregard anything as you are a free woman to make your own decisions.

I have been married to my wife for 8 years now. I did a very small amount of dressing when I was young and many years had passed w/o any interest or even thought of doing so. After the intimacy between my wife began to dissipate, I needed to find an outlet. My wife works as a bartender on Friday and Sunday evenings so after my kids fall asleep, i find myself home, alone and very bored. I have always had a fetish with beautiful women's clothing and lingerie and had purchased so many items for her that was never ever worn. I weigh in at 170lbs and my wife is about 160. I began trying on small things here and there, this pair of panties or that pair. I really enjoyed the feel of the fabric and this also lead to self enjoyment. weeks and months passed and I wanted to try the next step. I had began this dress or that form of lingerie and began to wonder how I would look to someone else. I hadn't gone as far as make-up and a wig as that is such an in depth conversation for another day and I frankly have yet to learn what to do. I made an account on adam4adam.com. I'm not really sure how I learned about the site but I secretly searched around for a long time at other people in the area. I really was looking to find another lady in my area but I learned after so much time I won't be finding another lady that lives near me on that web page. I met this really nice guy on there who was open about the idea that he was a married man looking for a no strings attached situation. we messaged each other back and forth for months while I always found a reason not to meet with him. I wasn't attracted to a man and I didn't want the idea of putting a man's xyz in my mouth. He finally convinced me to meet him at a coffee shop. far from both his house and mind so that we could leave if we wanted to and wouldn't give up any indication of where we lived. He was very sweet but a bit older than me (30 years to be exact as I am only 32) he told me he was 45 but I eventually learned that he was pressing 65. none the less. I felt very scared but I wanted to try this experiment for a few reasons. 1. I wasn't getting any at home, I wanted to be touched by someone else but myself. 2. I wanted to know how it felt to turn someone else on. I asked him if I could dress and he said only if I don't wear make-up or a wig. that he was not really into that scene. Being that I have yet to acquire a good wig or learn how to use make-up that was a very easy decision. I met him at his office. He had a single office in a small business building so I knew that if I wasn't happy with anything, just by being a little vocal I could attract unwanted attention. He let me in and allowed me to change in the sub office within his space. My heart pounded through my chest but I felt beautiful. he was so gentle, I thoroughly enjoy kissing and it was a new experience kissing someone with a beard. I wanted to make this man happy, I wanted to make him feel the way my wife used to make me feel. we went on to having an incredible experience.

It was very safe and he was very respectful. We only communicated through the site so he did not have my phone number. He called me Cassie at my request and I called him mark at his. I love women but when I dress or I get the very small opportunity to meet with this man, I want to feel like a woman who pleases her man with her body. I love knowing that this is a man who is aroused just by the look of me standing there in a cute piece of lingerie.

My wife does not know of this side of me, she doesn't know about Cassie or my lust to be desired.

Hi Alex,
If you are married, I'd say forget it- and indulge in fantasy only- adultery is going to rip the guts out of your relationship and it will not be pretty. Being with a man can be fun and every bit as interesting as you imagine, or it can be cold and degrading. But, having the real experience is just like having a good meal, and then wanting more or another different meal. Doesn't satisfy.

As Traci said, love and trust and warmth fill the hole in us, and sex doesn't. If you have a mate, build that relationship! If you don't then dating is what it is- you just have to go out and decide how you want to spend your time and with whom. Always looking for anew person to fantasize with will leave you empty and looking, looking...

Fooling around with a friend, he put his hand down my trousers and I knew he could feel my soft panties I had on. For a moment I thought he would stop in shock but he didn't. Pretty soon we had our hands and mouths all over each other and we spent the whole night at it. I loved being treated as a girl! It felt so good!:)

I was raped in a seedy Times Square NYC hotel.

I still haven't ever been with a man... ever... dressed or undressed...

Truth be told, I'm really not attracted to guys at all - now, I'm not saying that I can't see a guy and say to myself , " hey,... that's a good-lookin' guy"... but, that's really the extent of it... It doesn't ever lead to me thinking about kissing them,... dating them... having sex with them.. holding hands... etc... it's just me being able to acknowledge in a heterosexual way that another guy is good looking. Honestly, I live my life as a 100% straight guy dating women only... and that's really what I hope for and want... I'm not in denial because I've accepted this whole dressing thing that I have and come to terms with that... I think being openly gay would be SO much easier than being an open crossdresser... I truly love my life and have no qualms with my sexuality... the only hiccup in my life is my dressing fetish which is unbelievably overwhelming for me... but it's just that... a fetish...

The confusing part is how my sexuality changes when I dress...


What I really want is to finally find another CD to be with.... I dream of that nonstop,....but the opportunity never presents itself.. Granted, I don't really run in those circles... I literally know ZERO crossdressers, transgender, etc... it's not that I don't want to... I just don't run in those circles... I also don't go out in public places dressed and keep it very secret... so it's not like I really put myself out there to meet other gurls....

But, even after being online for YEARS... I haven't been able to find another cd to be with.., Even if it's not sex, I just want to get fully dressed and be standing in the same room in full view of another gurl who isn't going to judge me and just "be in that moment!" Completely out and in the open ... fully dressed and talking to them about how it feels and what it's been like to live with this secret and tell them what it feels like to finally have crossed that line that has escaped me for so long! And if that leads to some fooling around and monkey business, then great! :o lol but in all seriousness, I do want to be with another CD sexually... asap. I think that experience would be SO positive and uplifting for me both physically and emotionally..

But, unfortunately, I just don't have that type of attraction for "just plain guys"... which stinks because that's pretty much the only ones interested in me... I will admit that my trampy, outrageous dressing style is inevitably going draw that type,of interest and it's going to be from almost exclusively men, but it's the way I love to dress and express myself and I figured it's better to be honest and up front...

Now, when I dress, and am "alone on the internet"... lol I do often fantasize about being with a "guy"... but it's never a specific guy... it's no particular actor or celebrity... there's no "secret crush" regular guy that I know... it's always me just being fully dressed, exposed, and vulnerable and letting the "guy" have his way with me... it's more of me yielding to him and being submissive... but there's never a specific image... it's a faceless "guy" ,... no particular hairstyle, skin color, age, race, etc.. of course, he's hot, ripped, and hung, lol... but in all honesty, it's just the idea and the fantasy of me being used and giving in to a "man" that turns me on.. but again, once I "achieve results"... the feeling is gone and I undress and go back to being a "guy's guy"...

When I do get interest from guys online, it's never a hot, ripped hunk posing in a shiny thong... it's usually an old, overweight, pale, hairy, guy posing nude in his kitchen in dirty white tube socks.. nobody is going g to find that attractive...

I think the only way i would ever be with a guy is if he came onto me as I was a guy and then I said "wait a minute"... and ran back home to change and get fully dressed lol... then, I would definitely do it... just for the experience of finally being dressed in front of someone.

Sorry.. I tried to not get too explicit on here and keep it PG... I know many,on here get their panties in a bunch when someone even burps sex... but I'm just offering my experience and thoughts...

Adult theatre outside of town right where the farm fields start in one of the booths. Nothing ... verbal ... just a ... handshake ... if you will.

18...childhood friend. We were talking one night, led to talking sex. Led to us making out, oral sex, body grinding. We tried anal sex but we were young and had no idea lube would have helped. I wasn't dressed but certainly slipped effortlessly into the female role. Loved it, we did it on several occasions. I'd be open to it again if I met a guy I trusted enough, and I'd be willing to be dressed as well. Like Shiny, I'd also love to be with another CD as well.

Nope. Only dated women my entire life.

A tricky question as when this topic has come up in the past many members have expressed their aversion to any relations with males.
Based on my experience I have found that interest in males has tended to become more overt as one gets older. I have read many accounts of men who have been married and had children who, when they reach their 50's suddenly find that they are gay, or perhaps more precisely, they find they cannot suppress their homosexual urges any longer. I'm sure the cross dressing community is not immune to the same effect.

Personal ads. i have only met four admirers, and only one in the last four years. No penetration sex, is my boundry! The last guy i met, two months ago, was rather harsh, and mean. He even called me B___H!. I think he had a bad marriage, in the past, and was down on women, anyway, not necessarily at me. But, i had some fun, during the visit. I would not meet him, again, though. Usually, i let the man give me a foot and leg massage, and touching, but no penetration. I won't allow it. Be very careful to communicate a lot before ever meeting anyone, at all. I am single, and will not meet marrieds, also. I do not want to end up, in some triangle mess!

I have never told anyone this before. I was sixteen and I regularly visited the New York World's fair with my student pass. One day I spotted an artist doing a quick charcoal and pencil sketch of the female dancers at the Mexican Pavilion. I used to love to watch these beautiful girls in their traditional very full dresses loaded with colorful petticoats. I used to draw a lot back then and the artist finally caught me closely watching him as he drew. He was very good. We struck up a conversation and he said he would look at my work the next time I was in Manhattan. He had an apartment off of Washington Square and the rest is history as they say. He started showing me pictures of an orgy that had taken place right in the room we were sitting in. It was not long before he did oral on me. I was a babe in the woods and had no idea what was happening until it was too late. That was my first sexual experience ever, man or woman. Like another post early on this thread, I too went into the seminary the following year to fight my crossdressing urges and only stayed for my first year of college. It would be years before I started to realize that my being transgendered was not a bad thing. A later boyfriend treated me with gentleness and respect that finally washed away the guilt that the artist had heaped on me.

All alone. No one else around.

mine was terrible. It was with a close friend who was the only one who really knew my secret long before i came out to anyone. I was a very bad alchoholic at the time (im sober now but he still drinks) we were drinking buddys. I felt desperate to feel feminine and thought i would feel more like a girl if i did sexual things with another man. Anyways we got drunk one night and i was getting really desperate. we were both drunk and ended up doing sexual things with eachother. I have no physical attraction to this person at all or emotional attraction. I just thought it was the thing to do. I felt very ashamed of myself and disgusted with myself. This continued on for a while until i finally came out and became more open about cross dressing and finally realized that i dont need that to feel like a girl. We are still friends but agreed we would not talk about any of that stuff we did anymore but he is still awkward about my cross dressing. Anytime i do it around him i can tell he wants to have sex even tho we agreed that we would not do that anymore. It bugs me because he does not understand what ive been through and he seems to think i had some sort of attraction to him and still thinks i do even tho i have tried explaining that i was not attracted to him and that i was just really really confused.

i would also most likely like to get intimate with another cd that dresses like i do

The idea of meeting with another CD locally is something I have wanted for quite some time. But I would probably be picky and want to find someone closer to my age and hopefully somewhat passable as that is my goal. maybe someone who can teach me a few pointers and just engage in a conversation. I would love to try on different outfits and get someones opinion. Only 1 person in the world knows that I enjoy the feel of women's fabric and she lives 2500 miles away. Having sexual relations with another CD would just be the icing on the cake.

I have a lady friend on line, and she loves corsets (for her DD natural breasts) and likes that I'm a guy in lingerie who is really excited when she talks about feminine things, and her body, and her nipples and...you get the idea. She told me about a man she knows in my city who was curious about being with another man, and she put us together. He's a man's man and his idea was we'd look at porn and jack off together. We watched video clips of Fantasy Fest, and he had a running commentary on how hot a girl's tits were or her ass, and how he wanted to **** her, but I had a really different commentary going on in my mind--the more I watched the more girly I felt, and the more girly I felt the more I wanted to make love to his ****, and so I asked if I could and I did. It was my first time giving oral to a man and it felt sooo natural, just a girlfriend wanting to please.

The next time we met I asked if he was ok with me wearing panties and he said yes. I felt so happy that way (with a little lipstick, too), free to feel just like a women, while he thought about ****ing them. This time, when I slipped between his thighs to suckle his ****, I felt femme like I never had before--I don't have words for it!

Well, since then, I' met more gentlemen. Most of them that I like are not interested in me dressing, but I do tell them to think of me as their girlfriend, wanting to please and enjoying their masculine power. I'll usually dress in lingerie before and after they visit, so it's really like Aileen just gets naked for them, and I'm untroubled by being self conscious about my appearance. Meeting men this way has added a new and deep dimension to my femininity. I've always been comfortable with my femme self around gg's, and have shared my dressing and feelings with certain women, but my relationship to men was hidden and often ambiguous. Now I feel much more natural with my girly feelings when I'm around men....

https://www.youtube.com/watch?v=XAokP26E-_s

Not gay, not attracted to men. That is a pretty voyeuristic question. Appropriate for this forum?