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  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
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    Quote Originally Posted by Ezekiel View Post
    dressing up does not change sexuality nor sexual tastes.
    I'm not sure that's true. It is a frequent report by "straight" CDs that they do experience sexual attraction to men when fully in the female role by dressing and interacting. I know it's tempting to analyze the phenomenon as acting out a fantasy or tweaking one's autogynephilia (a problematic and controversial hypothesis at best), but the phenomenon is very real for some. I view it as the social training that tries to pound any femininity out of us as boys producing such an inhibited and suppressed sense of self that, without the "permission" we give ourselves by being fully in the role, something inside us just won't allow us, presenting as "men", to find males sexually attractive. Thus, we're quite different from gay men who love being men and love being with men. And quite different from CDs who love their straight sex lives with wives or SOs but just like to dress up.

    Case in point: Samantha's candid and clarifying comment this morning, which I hadn't gotten to before posting the foregoing comment. 'Nuff said.
    Last edited by Acastina; 11-09-2015 at 06:05 PM.

  6. #6
    That guy in a dress Sky's Avatar
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    Quote Originally Posted by Acastina View Post
    I'm not sure that's true...Thus, we're quite different from gay men who love being men and love being with men. And quite different from CDs who love their straight sex lives with wives or SOs but just like to dress up.
    Right on the money.

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    Acastina, I was reading your post and thinking "See! Its not just me !!

  8. #8
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    Ok, the five questions:

    1. Yes. More than thrice. Some anonymous, more than one repeat partner. Never without presenting and acting in the female role.

    2. Not really. For most of my adult life, I felt a strange kind of guilt after sex with a woman. It passed quickly, but a kind of remorse nevertheless.

    3. No, if addiction means obsession and promiscuity. Prominent in my mind when I feel horny, ponder sexual things, or need a surefire fantasy to finish with my spouse, yes, but all-consuming, no.

    4. No. I was in a full-time experiment (that lasted nearly eight years) before the first time. For me, it was more about social adjustment and learning how to blend into the human mix on the other side of the gender binary, rather than seeking sexual fulfillment. Sometimes I regret ending the experiment and enduring some of the compromises since, but I am happily married to a wonderful woman who has known about my differentness from the very beginning and could not be more understanding and indulgent. I am virtually full-time in private, and she is fine with that.

    5. It absolutely is different, and much more pleasurable and natural-feeling to me than being the man with a woman. The need to be potent and stay potent and penetrate at length always felt burdensome to me, and I've always had to work really, really hard at it to finish. Pretty sure that's not how most "normal" men would describe the act. With guys, the orgasms have just come out of nowhere in a delightful surprise because I was so engrossed in the feelings of surrender and being desired. In contrast to the sorta-guilt described under Question 2, I have this incredibly warm and fuzzy feeling of affection and contentment after satisfying a nice man, whatever my orgasmic outcome might have been, and I think that's a pretty womanly emotion to experience; I feel wonderful that he finished, whether I did or not.

    All of that said, I love my wife as I've never loved anyone in my life, and we are happy and secure in our partnership of more than a decade. Our sex life is definitely a compromise and probably quite atypical, but those words also describe my entire heterosexual experience. But, as to the pure animalistic response of one side or the other of how we all got here in the first place, I do wish I had a magic wand at times...
    Last edited by Acastina; 11-12-2015 at 03:20 PM.

  9. #9
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    Quote Originally Posted by Acastina View Post
    I'm not sure that's true. It is a frequent report by "straight" CDs that they do experience sexual attraction to men when fully in the female role by dressing and interacting. I know it's tempting to analyze the phenomenon as acting out a fantasy or tweaking one's autogynephilia (a problematic and controversial hypothesis at best), but the phenomenon is very real for some. I view it as the social training that tries to pound any femininity out of us as boys producing such an inhibited and suppressed sense of self that, without the "permission" we give ourselves by being fully in the role, something inside us just won't allow us, presenting as "men", to find males sexually attractive. Thus, we're quite different from gay men who love being men and love being with men. And quite different from CDs who love their straight sex lives with wives or SOs but just like to dress up.

    Case in point: Samantha's candid and clarifying comment this morning, which I hadn't gotten to before posting the foregoing comment. 'Nuff said.

    I would say this is right on the nose for me... I never have romantic thoughts about men... Never any desire to date a man, hold hands with a man, go out to dinner with a man, cuddle with a man, etc... Any attraction I have is exclusively to women.

    It's only when I'm dressed that thoughts about men come into my head... As I've stated on here before, it's never about a specific man like an actor, model, celebrity, etc... And I've never in my life encountered any man where I even remotely felt any attraction at all. And I still feel that way to this day.

    However, as time went on and I experienced more and more women that rejected me after I told them about my dressing, I began to try to find other ways to experience and share my CDing with others and not just keep it to myself. That turned into me going out late at night dressed in public places to practice a femme walk and feel the rush of the risk of getting caught. With digital cameras, where I didn't have to worry about having someone else develop the film, that translated into taking pics of myself dressed that I could pose in my various outfits and see myself- which quickly translated into joining MBs and websites where I post those pics. Which translated into comments from other members- etc.

    I think it's a natural progression of being a straight man who is attracted to women only but also loving to dress and wanting to experience it with others. naturally, the thoughts of being with a CD, TG, TS, etc. come into play as we share the love of dressing. Even though I love women and want to be in relationships with women, marry a woman, and live my entire life with that woman, I've never been able to have the two together... It's always one or the other.

    Obviously, i can have both if I find a CD, TG, or TS to be with. My desire to dress with someone had gone on for so long and became so strong that I eventually found that I would enjoy being with someone else who dresses like myself. That, however, doesn't really ever work because I keep my "hobby" a secret and I don't frequent places dressed or not dressed where I would meet someone who dresses.
    I try to do it online, but most of us know how online dating goes. Even on the most popular dating sites I've used in dating women, it's a bit of a headache. Now try to use a site where you are trying to find someone to dress with and it becomes much more complicated. Almost all contact I get from trying to find a dressing partner and playmate online is men. Obviously, we all know that, but after awhile, I did become aroused at the comments and emails I would get and I did eventually start fantasizing about letting a man use me. Once again, Never a specific man that I was ever attracted to... Just the act of putting myself in that vulnerable position, and letting a man have his way with me. I'm still not sure how I will feel if it ever happens- maybe it's just the idea that I love, but I do know that my desire to dress in front of someone - ANYONE - is so strong that I'm absolutely open to doing it with someone regardless of gender or sexual identity.... and it doesn't even have to be anything where there is actual sex involved. Just dressing and playing would be great at this point. I'm so eager to do it, that I'd be happy if I could just dress in front of someone and be seen by someone- ANYONE- while dressed! Still, given my dressing style and look, I'm only gonna find someone who is looking for sex! Lol "dress like a tramp and they'll treat you like a tramp."

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    Quote Originally Posted by LydiaL View Post
    I have had sexual experiences with another cross dresser, while cross dressed myself. Very enjoyable. However, guilty thoughts did cloud my mind and killed any success at intercourse.

    Frankly, I find myself mostly attracted to other cross dressers. However, I admit to fantasizing about being taken by a man while en femme.

    Straight sex is mighty fine, but I find it stimulating to think about future sexual experiences with other cross dressers. So guess that I am more lesbian leaning than gay.

    I think this is pretty much where I'm at... I think being with another CD, TG, TS, ETC. would be amazing because it's everything I love about women, but everything I understand about men.
    Last edited by SHINY-J; 11-30-2015 at 02:31 AM.

  10. #10
    Member Tashee's Avatar
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    Won't answer every question asked. My 1st exp same sex was with a gay friend who I was not attracted to in terms of looks. His personality & constant chasing I was fond off even though I (thought) it was secret. He me wore me down and one night as I sometimes would sleep there instead of risking a DUI I let myself be seduced. I was not in Xdress mode. I love him to pieces & gave in willingly. I was surprised to find all my hidden femininity just poured out. I was shocked to find I rather enjoyed it a bit more than I ever would have expected. Even w/out the female attraction I have I found my time with him very intense. I tried this with someone else & did not enjoy it at all. I enjoy dressing enjoy the fantasy but understand that sex for me has to be with someone I have a real connection with. I just can't find that male connection often-Nearly ever is more like it. My times with him were few but fun & not easily replicated. So I let it be a thing of the past & enjoy the memory and keep the future fantasies, fantasies. I had guilt when I thought I could replicate the time with him with another. So I guess I'm Bi to an extent but could careless and realize for (me) its a personal connection that wins me over not just the act. In a fantasy hell the act works, in real life it doesn't. Hope this confession helps, it probably doesn't its probably me just recalling a very interesting time in my life that I'm not ashamed of. Everyone is different and it sounds like your a wee bit confused & that is ok.

  11. #11
    Junior Member Kimberley May's Avatar
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    I've been bi-curious for many years but never did until a couple of months back. I see the crossdressing bit as totally unconnected to it. A totally different issue altogether. Although the crossdressing I found made it surprisingly easy to pick up guys. The offers I received were unreal, bloody flattering really. Why can't I have this kinda luck with the ladies?

    Anyway as I was saying, I tried it with a guy a couple of months back for the first time, and I regret it.

    I immediately ran a hot bath after he went to wash it all away. I felt violated, although it was my fault but now I kinda understand how women must feel. His smell seemed to linger in the room for days. I didn't feel turned on like I do with a woman and just went through the motions just waiting for it to be over. I do feel shame and regret, but then if I never tried it then I would still be thinking about doing it for the rest of my life which would drive me bonkers.

    So, being bi-curious and even experiencing it to find out I believe doesn't automatically mean you're gay, confused sure until after you find out if you like it or not. I didn't care for it. I'm not in denial, I now consider myself straight and not bi. At least I know now, at a heavy cost.
    Last edited by Kimberley May; 01-20-2016 at 10:49 AM.
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  12. #12
    Pink and Quirky FeliciaCDSNJ's Avatar
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    I've been with a guy before. It was interesting to say the least and without turning this post into a xxx story. Would I do it again? Yes, I've come to terms with myself that not only am I trans but also bisexual. I don't act on my urges because I'm with a wonderful woman, who I would not trade anything in the world for. It was different as I'm use to holding someone and to get held was different in a good way.

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    The Number One reason I haven't experienced a man or a CD/TS is the need for that dreaded raincoat. If there was no such thing as STDs, I would be a much wilder, crazier, free-er person. Many people don't worry about it, and nothing ever happens, but I'd be unlucky enough to get something the first try. WHEN I try, I want to feel reality, not latex, just as I've always wanted to in all situations with women. Have I used them? Of course. Have I ever had a good experience with them? Never, but some have been ok, I guess. OK is no longer worth it, however. I want "good" at a bare (lol) minimum, and it just isn't possible.

  14. #14
    Member Tashee's Avatar
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    Quote Originally Posted by FeliciaCDSNJ View Post
    I've been with a guy before. It was interesting to say the least and without turning this post into a xxx story. Would I do it again? Yes, I've come to terms with myself that not only am I trans but also bisexual. I don't act on my urges because I'm with a wonderful woman, who I would not trade anything in the world for. It was different as I'm use to holding someone and to get held was different in a good way.
    Your last line You nailed it in my case--Being held (in that way) by someone who just happened to be the same sex was intense. It brought out ALL the same sensations I get when dressed. Can I replicate that as I searched? Nope Just as I can't replicate the call me Bi? I don't care. I dig & found the key to me is a deep connection Now if I was 18 and with all the BS Propaganda on the web I'd probably do things because of the heinous BS these young kids see repeptively: your a worthless man be a pretty girl you an do it while your young & objectify yourself & you will be happy-Awful advice- As time goes on that leads to alphabet diseases & as you age that once young shine goes away I swear some of these sites that promote that are borderline pedophiles and predators...JMHO

  15. #15
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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

  16. #16
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    ummm, i've a fantasy to do it with a guy and go all the way but it also creeps me out. I want to have that experience but its really hard. If i ever do it which i don't think will happen it would be with a stranger.

  17. #17
    Junior Member Kimberley May's Avatar
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    Quote Originally Posted by Jenniferathome View Post
    No you are not. You are in denial. Being dressed does not make homosexual sex "straight." There's no need for pretense.
    That's not always the case. Bicuriousity does not mean you are definitely homosexual and/or in denial of such. To suggest they're all in denial will only create more confusion with bicurious people. Otherwise we could just as easily say that like straight guys, bicurious gay guys are just as much in denial of being straight.

    I have been bicurious for about 20 years at least, until just a couple of weeks ago. Do I regret it?

    Well, yes and no.

    No because it is something I have at last got out of my system thus I'm now much more calmer about it than I have been for years, now realising that I'm ultimately straight. And yes because I now feel I violated myself because of my true straight hetero orientation. As although the first guy I went with we didn't do as much, the second guy I went with I didn't enjoy it like I thought I would and it really done nothing for me, I didn't find it arousing like I do with a woman. In fact it hurt and couldn't wait until it was all over. I immediately ran a hot bath afterwards because I felt kinda dirty and violated afterwards. Now I realise why many women do the same although I realise this one was my own fault. The odour lingered for a while. I now feel a sense of guilt and shame over it, but at least I fully understand why I did it, and that all the fantasies will now go away, and it's been a hard learned lesson. Plus I could never envisage having a loving relationship with a guy, I only ever dream of that with a woman.

    So at the very most, when I was resolving my bicuriousity, I became heteroflexible, not bisexual. The difference being is that bisexuality means you can fall in love with both genders, but heteroflexible means you can only fall in love with the opposite gender whilst only lusting after your own, making that more of a choice, unlike bisexuality which isn't a choice. Heteroflexible can be either permanent or temporary, for me it's extremely temporary. So although I have now been with a couple of guys which I kind of regret (yet has resolved my inner conflicts), I now realise that I'm ultimately straight.

    I'm also unsure how long I'll continue crossdressing for. I actually do enjoy this more as it's been relatively harmless escapism for me, but I now realise this femme roleplaying and my bicuriousity has all been compensation for the shortage of female intimacy in my life, personally for me. But I would give up all my femme clothes in an instant if the right woman came along, and it became a choice of either her or this.
    Last edited by Kimberley May; 11-07-2015 at 07:18 PM. Reason: elaboration.
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  18. #18
    A Wannabe Catgirl Kaze_'s Avatar
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    Even if I'm a CDer, I'm certainly not a sub.

    No, I've never been with a guy, however I wouldn't entirely cross guys off my list. I just don't have a desire to actively seek them out.

    I got my first taste of male attention as a CDer not long ago... It made me both envy and sympathize with women at the same time. ;p
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  19. #19
    Member LydiaL's Avatar
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    I have had sexual experiences with another cross dresser, while cross dressed myself. Very enjoyable. However, guilty thoughts did cloud my mind and killed any success at intercourse.

    Frankly, I find myself mostly attracted to other cross dressers. However, I admit to fantasizing about being taken by a man while en femme.

    Straight sex is mighty fine, but I find it stimulating to think about future sexual experiences with other cross dressers. So guess that I am more lesbian leaning than gay.

  20. #20
    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.

  21. #21
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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.
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  22. #22
    Member Jazzy Jaz'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.

  23. #23
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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.
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  24. #24
    wiggle it, just a lil bit Julia Welch's Avatar
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    No, not ever ... Women are far more attractive.
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  25. #25
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    Quote Originally Posted by kimdl93 View Post
    Our sexuality isn't what leads us to CDing.
    I know this is not what leads you or other TSs to express yourselves, but sexuality is a prime motive for many CDers. In fact, don't most CDers start off by masturbating while dressed or while fantasizing about being dressed? And once they experience that high, it sticks, even if it becomes less sexual with age. It has not been sexual for my SO for years, but it most definitely started out that way.

    To the OP, you should just bite the bullet and try it. You've been wanting to meet-up with folks on CL for years now. It's the only way to know whether it is for you, other people's experiences don't have a bearing on how you are sexually wired. Unless you just enjoy talking about it?

    You ask if being with a man will make you want to dress more. This all depends on how sexual the CDing is for you. Some CDers can get lost in the fantasy and they can maintain the illusion they are women even when having male-on-male sex. Just be smart about it and meet the person first in public, also let someone know where you will be when you do meet-up for sex. Bring your cell phone and let the person you are meeting know that people know you are there. Also, don't forget to use condoms.

    My SO did experiment with men and this is how he determined that it wasn't for him, even if he does occasionally have homoerotic fantasies. Fantasies are not related to what arouses us in real life. I have a fantasy that would literally be impossible to reconstruct in real life and if it was, it would be a real turnoff. lol.
    Reine

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