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Thread: Have you been with a guy?

  1. #1
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    Have you been with a guy?

    Hi,
    I am thinking about being with a guy when dressed up fully but only in presence of a girl. I am a straight guy who likes dressing up but I have never ever ever thought about a guy before. Now slowly I am opening up to the idea of being with a guy and letting him drill me while a girl is present.

    I really want to do it but I am wondering if I am going to regret it later. My questions are
    1. Has anyone done it before?
    2. Did you feel guilty later about it?
    3. Did you get addicted to being with a guy?
    4. Did you decide to go fulltime after being with a guy?
    Most Importantly
    5. Was it more pleasurable than straight sex? How did you feel?

    Before dressing up, I used to see shapes as masculine and feminine. Like certain shoes are obviously feminine (slim).. you know what I am saying.. Now I dont have those thoughts any more since I started dressing up. I am wondering if being with a guy would make one gender fluid. I am thinking about it but I want to know other's physical, emotional experience before taking this step.

  2. #2
    AKA Lexi sometimes_miss's Avatar
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    It kind of sounds like you feel the need to have a girl present because subconsciously you suffer from the same guilt about anything homosexual that pretty much every guy does. If you want to have sex with a guy, try it. There's nothing wrong with that! Really! Who knows, it might be the best thing you've ever experienced. Just be careful, learn how to prepare for it, USE A CONDOM, etc..
    Some causes of crossdressing you've probably never even considered: My TG biography at:http://www.crossdressers.com/forums/...=1#post1490560
    There's an addendum at post # 82 on that thread, too. It's about a ten minute read.
    Why don't we understand our desire to dress, behave and feel like a girl? Because from childhood, boys are told that the worst possible thing we can be, is a sissy. This feeling is so ingrained into our psyche, that we will suppress any thoughts that connect us to being or wanting to be feminine, even to the point of creating separate personalities to assign those female feelings into.

  3. #3
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    Quote Originally Posted by leonal123 View Post
    Hi,
    I am thinking about being with a guy when dressed up fully but only in presence of a girl. I am a straight guy......
    No you are not. You are in denial. Being dressed does not make homosexual sex "straight." There's no need for pretense.

  4. #4
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    Jennifer, I think he wants to be with a guy because of the self-sexualization induction autogynephilia can have. So no, I highly doubt he is in denial of anything, he's probably straight with a sex fantasy, that might end up not liking the result. Hey not to scare you off here, try whatever you feel you want, I'm just implying that you might be thinking it is one thing, and could end up very different to how you think it is.

    I doubt you are gay leonal, tell us something...

    Are you attracted to guys in the sense they turn you on (you being dressed up or not), or are you just attracted to the idea of being dressed up and let a guy touch you?

    If the affirmative response is the second option, then the guy is just a tool in your sexual fantasy, and you are not attracted to guys per se.

    Because really, these are two very different things... dressing up does not change sexuality nor sexual tastes.

    EDIT: I almost forget...

    1 - Never been with a guy, and will never. Zero interest.
    2 - Not applicable since 1 is negative
    3 - Again N/A
    4 - You don't go full time just because you've been with a man. You go full time if you find that it is the best for you, but not because some external reason.
    5 - No idea, I can't answer you here since again, this is not applicable in my case.
    Last edited by Ezekiel; 08-20-2015 at 06:50 PM.

  5. #5
    Sweet 'n Sassy sugarbabe's Avatar
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    I have never been with a guy dressed, but I have fooled around with guys before. I know that I am at least bisexual and apparently somewhere on the transgender scale since I switch between male/female brain mode a lot and like to dress up more and more as I go along. I have felt guilty in the past with the same sort of hangups a lot of men experience after homosexual activity, but I'm not letting it ruin my life or anything.

    However, I often fantasize about being with another man while I am in girl mode and how it might be different being treated as a woman instead of a man.
    Last edited by Shelly Preston; 08-21-2015 at 07:22 AM. Reason: please read the rules

  6. #6
    Senior Member Ceera's Avatar
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    Personally, it sounds more like you want the fantasy and not the actual situation. Though I suppose it is possible that your feminine aspect is more inclined to the idea and might like it. Dressing doesn't change your sexual orientation. But your frame of mind while dressed might make you more willing to explore things you're already inclined to.

    My answers:
    1. Has anyone done it before?
    Yes. Only once while Dressed, and a few times prior to that as a guy with another guy. Never had a girl watching while that happened.

    2. Did you feel guilty later about it?
    My first few gay encounters were not initiated by me, and they left me feeling very confused and conflicted. I suppose somewhat guilty that I had enjoyed it, but I got over the guilt pretty fast. However, I knew my father would be very unlikely to accept the idea of me being bi or gay. So for most of my life I repressed that urge and tried to live a straight life. I married a nice girl, had a kid... No regrets for that relationship. We had a good marriage, over all. But all that time, although I remained faithful to my wife, I still knew that I found some males attractive. I just didn't act on that attraction. That is VERY different from how you describe yourself.

    As fate had it, I outlived my wife, as well as both of my parents. When she was gone and I was single again, I decided to explore cross dressing and to experiment with the bi side of my nature. I found that, when en-femme, I was more receptive to attention from males than when not. But in both cases, I would just as soon have a female partner. Still, I have had one time where I accepted an offer of intimacy from a male while I was out en-femme, and I brought him home with me. I quite enjoyed him treating me like a classy lady that he wanted to be intimate with. I knew what I was doing, and no, I didn't feel guilty at all. There was nothing to be guilty about. I wasn't cheating on anyone, and it was a mutually consensual evening.

    3. Did you get addicted to being with a guy?
    Nope. It was fun, and we both enjoyed it. But it wasn't any better than being with a girl, and honestly, not good enough for me to seek his company again after that. Since then, I am still open to either gender, with a general preference for girls. I guess you could say Ceera is closer to being a lesbian than being bisexual.

    4. Did you decide to go fulltime after being with a guy?
    No. I still only cross dress about once a week. The experience didn't change my desire to cross dress at all.

    Most Importantly
    5. Was it more pleasurable than straight sex? How did you feel?
    Honestly, it was about the same. Neither better nor worse than an average-quality encounter with someone I didn't have a deep emotional attachment to. Fun, yes. But not incredible.

    My advice to you is that you should try pleasing yourself with suitable sex toys first, to make sure you find the experience of 'being drilled' a pleasant one.

    If you do, then you might carefully approach a gay or bi male that you trust, and as the others mentioned, by all means use a condom! Or at the very least, make sure he's been tested recently to be free of STDs and HIV. There are free testing centers that give out cards that certify when you were last tested and what the results were.
    Last edited by Ceera; 08-20-2015 at 07:28 PM.

  7. #7
    Full Geek Status Adriana Moretti's Avatar
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    Quote Originally Posted by leonal123 View Post
    Hi,

    I really want to do it but I am wondering if I am going to regret it later. My questions are
    1. Has anyone done it before?
    2. Did you feel guilty later about it?
    3. Did you get addicted to being with a guy?
    4. Did you decide to go fulltime after being with a guy?
    Most Importantly
    5. Was it more pleasurable than straight sex? How did you feel?

    .
    1. I do "IT" all the time
    2. No...not at all why should I feel guilty...whats the big deal? it's just sex
    3. No....but I do like sex
    4. Fulltime after being with a guy? no.....
    5. Whats the difference between straight sex and cd sex ??? I just like sex.
    Handsome, rich men get to the front of the line.....

  8. #8
    Member jasminepp's Avatar
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    I have never been with a man but i have very similiar fantasies. I consider myself semi bisexual meaning i have no romantic attraction to men but i have very specific sexual attraction. I personally wouldnt consider you straight as i believe straight for men is only having attraction/desires for women. I would think that you are at least semi bi and your interest in men may be very limited. I also have no desire in being with a man without being fully dressed. You could try a woman with toys to start.

  9. #9
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    Need validation of your sexuality? Dressing like a girl won't change the reality...that is one guy doing it with another. Not that there's anything wrong with that. But sex is sex. CDing need not be a beard. But if that's what you need to express yourself sexually, have at it.

    As for th questions, frankly they are a bit silly... Kinda like once you go gay you'll never go back in their tone. Our sexuality isn't what leads us to CDing. And no, one doesn't decide to live as a woman because they had a night of great sex while CDing. I was going to use the word juvenile, but I decided against that rather unflattering characterization.
    Last edited by kimdl93; 08-20-2015 at 09:31 PM.

    Easy come, easy go;
    Easy left me long ago...

  10. #10
    wiggle it, just a lil bit Julia Welch's Avatar
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    No, not ever ... Women are far more attractive.
    Fun loving skirt wearer

  11. #11
    Junior Member Kelsey21's Avatar
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    Well, isn't this interesting???? I guess I'll answer the questions first.
    1. Way more than I'd like to admit
    2. No guilt, seemed pretty natural to me
    3. It's more like a habit than an addiction
    4. Nope, haven't swayed in the least
    5. Straight sex is far superior "hands" down.......

    Seriously though, I'm attracted to beauty and men are not beautiful to me. Now, that being said, the fantasy of being with a sexy cross dresser??? For the time being, this could be exactly what it is, a fantasy, as I really don't know if I could go through with it.

  12. #12
    Silver Member Barbara Dugan's Avatar
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    Is very simple for myself " I have a boyfriend"

  13. #13
    Crossdresser-At-Large BillieAnneJean's Avatar
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    I have not fantasized about sex with other men.
    I have not had sex of any kind with anyone other than my wife.
    Compared to her, everything else, everyone else, is like "downsizing".
    It is never going to happen.
    When I fantasize, I fantasize about her.

  14. #14
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    Sounds like the idea of sex with a man is just a fantasy for you.
    Is the lady that will be present going to be part of a threesome thing or just a spectator?
    Being dressed won't change your sexuality if you are "straight".
    Usually people that make the comment "but I am straight" usually aren't and haven't come to grips with admitting they might be gay.
    Sex with guys? sure I have.
    Casual sex isn't my thing because for me being in love before I engage in sex.
    Not many gay guys want to date a CD so I'm batting 0 right now.

  15. #15
    Member Elli87's Avatar
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    Ive never been with a guy, but Ive been with others like me, and ive been with a guyish girl, she used to push me onto the bed and snatch off my underwear she could be rough but it was fun
    well even if i'm wrong, you know i'm right

  16. #16
    Non-binary/Questioning Mayo's Avatar
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    1. Has anyone done it before? Yes, I've had sex with several guys.
    2. Did you feel guilty later about it? The first time or two, when I was in my teens and unfamiliar with sex as anything other than 'something naughty' that one shouldn't do. Not as an adult.
    3. Did you get addicted to being with a guy? No more (or less) than sex with women has made me 'addicted' to women. I do have a preference for women but I enjoy sex with both.
    4. Did you decide to go fulltime after being with a guy? See #3. Being with guys hasn't made me any less attracted to women. For what it's worth, I've had 2-3 times as many female sexual partners as male and that roughly reflects my level of interest in each.
    5. Was it more pleasurable than straight sex? How did you feel? I wouldn't say so. It's similar but different at the same time. I enjoy it but, as I said, I have a preference for women.

    I've only been dressing for a few months and all my experiences with other men happened before I started wearing women's clothing (I do currently have a girlfriend with whom I'm quite happy). I wouldn't mind having sex with a guy while I'm dressed, but it would be for the experience and wouldn't (I suspect) change my relative interest in men or women.

    If you want to be with a guy, by all means, do so. Take appropriate precautions (as you should when you have sex with anyone!). Try it both when dressed and not, if you wish, and see if it makes any difference for you. As others have said, being dressed won't change your sexual orientation - or your gender identity. You might possibly realize that you are bisexual instead of straight, but so what? If so, it just gives you more choices in life. If not, then things are no different for you than they were before.

  17. #17
    Member melanie206's Avatar
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    yes, yes, no, no, sometimes - you are what you are - nothing external can change that. counseling can help you sort out your feelings.

  18. #18
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    I have not been with a guy but a man dressed in sexy lingerie really turns me on yet looking at at a guy not in female doesn't do anything for me
    Maybe one day I will go with anther CD

  19. #19
    Adventuress Kate Simmons's Avatar
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    It's okay but it may not be for everyone who likes to dress up.
    Second star to the right and straight on till morning

  20. #20
    Silver Member Mollyanne's Avatar
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    Well I guess the only way you are going to find out is to try it, you may REALLY like it, ALL OF IT!!!!!!

    Molly

    PS: I have had some "encounters" and I prefer to be dressed or partially dressed.
    "To thine own self be true"

  21. #21
    Silver Member I Am Paula's Avatar
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    Yet another 'I'm not gay, just having sex with men' post. Having a woman in the room does not make it any straighter. Wearing a skirt does not make it any straighter.
    Sex with guys will NOT make you TS (want to go full time).
    You can call it anything you want.

  22. #22
    Reality Check Krisi's Avatar
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    Many of us may have fantasized about what it would be like to have sex as a woman, but dressing up as one is not the same thing. Strapping on a pair of boobs and a wig does not make you a woman, just a guy with fake boobs and hair. You don't have a vagina so you can't have sex as a woman. What you are describing is gay sex. Wearing fake boobs doesn't change that. Having a female watch doesn't change that.

    If you do it once, you might be able to call it "experimenting", but if you like it and continue to do it, you are gay. Not that there's anything wrong with being gay but you have to admit it to yourself.

  23. #23
    @--}----- Sissy_Michelle's Avatar
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    Leonal123,

    I know I may regret this. But I feel that I should open up more of my feelings. "Have I been with a guy?" Yes. Did we have sex? Yes. Did we have intercourse? No. Two people that found each other attractive, spent an evening together enjoying not only each other's company, but a romantic time in each other's desires.

    Did I feel guilty after? No.
    Did I get addicted to being with him once? No
    Did I decide to go "fulltime" after being with him once? No
    Was being with him, more pleasurable that straight sex, how did I feel... There was no doubt that I enjoyed my time with him. I felt drunk (we were hitting the jagermiester a little too much) though I felt comfortable with him.

    However real life existed outside my barrack's door. We shared a moment that I still haven't forgotten. Would I do it again? With the right person, and attitude... Very possibly. Do I consider myself "homosexual"? Not really. I consider myself lucky to have experienced a caring and emotional event with someone I could trust. Does that make me Bisexual? For sleeping with a guy once? Call it however you like. I tell everyone I'm lesbian when people wish to label me...

    @--}----
    Michelle

  24. #24
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    Dressing up can enhance gay sex, just as it can straight sex. As much as we talk about "duality", persona #1 doesn't get a pass on anything just because it was done by persona #2. That excuse just doesn't work. We as a group are quite homophobic, which I find fascinating.

    It's interesting, too, that some of the responders said that straight sex and gay sex were virtually the same (obvious differences aside). I find it to be TOTALLY DIFFERENT! Physically, emotionally... I find very little similarity.

    In general, if you're married don't do it. Again, persona #1 doesn't get a pass just because persona #2 did it. If you're not married, there's nothing to feel guilty about.

    Especially with the qualifier that there be a girl watching, sounds like the likelihood of you actually doing this are very slim. I'd say zero. That makes it a safe and harmless fantasy. Nothing wrong with that, either.

  25. #25
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    Leonal, I think what you are feeling is what a lot of CD's feel as they advance along their CD journey which is adding more and more as we go along. Each additional step makes impersonating a woman feel better and better and we get more and more comfortable in the clothes. So it's only natural for you to be curious and have the desire to want to be in the same place as a woman having sex with a man, it would make you feel more womanly and validate yourself in female clothing. When we think along these lines we think of a sexy curvy beautiful woman dressed in lingerie or sexy clothing having sex with what else, A MAN. This illusion makes us curious to the point where we want to try it. Like Sometimes said, try it and you might like it, it could be a game changer like "hitting it right out of the ballpark", getting dressed in sexy clothing, meeting a guy for a date, being treated like a lady and finally performing as that sexy female, you won't know unless you try. You could be doubling your sex life plus the variety. Just use condoms, starting out try oral to get use to it and then to the next level if it's for you. As some of the previous threads have stated they had to try it "first", they liked it and it added something they never would have had if they hadn't tried it at least once. Remember smoking that first cigarette or drinking a beer, it took several times to like it and then you looked forward to it. Forget the woman, you definitely don't need her.

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