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Thread: Have you been with a guy?

  1. #176
    Member Anneliese's Avatar
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    I have never been with a guy, and at this point, the closest I've ever come to a gay experience was attending a gay wedding shower in college, and having a gay professor tell me he was attracted to me, on which I passed.

    I am not interested in men as men. They do nothing for me. However, I am finding myself more and more interested in a penis on a woman, whether it be trans or cross-dressing, as long as they had some actual female features. (I am not attracted to a CDer who looks like a man dressed up as a woman)

    In fact, I am more interested in acting that fantasy out than I am in getting into another hetero relationship. Been there, done that. Was married once. Have had several serious relationships, but I don't think I have the strength to get into another. It's simply too much work.

    I would hire a TS prostitute...believe me, I've looked...but I am horrified by the dangers of STDs and I don't enjoy sex with a condom, so I'm at an impasse. I've even told my last two girlfriends, who both told me first that they were bisexual, that if I was in the situation of "The Crying Game", I would absolutely Go.For.It. Dil was HOT!

    I am 61. I would like to try it before I die.

    Not sure if I will, but my cross-dressing got more serious when I shaved off my beard a couple of months ago.

    I am quite sure if I tried the fantasy, I would like it and feel no guilt. I'm also quite sure I'd want to do it again. I might even become addicted. There's just something really exciting about a pretty woman with a different sex organ.

    And yes, due to my fear of STDs, if I could somehow do myself, it would be the ultimate, because I'm safe and I think for my age I'm pretty hot. Too bad I can't. LOL.
    Last edited by Anneliese; 11-15-2015 at 11:54 AM.

  2. #177
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    Quote Originally Posted by Anneliese View Post
    I am 61. I would like to try it before I die.

    Not sure if I will, but my cross-dressing got more serious when I shaved off my beard a couple of months ago.

    I am quite sure if I tried the fantasy, I would like it and feel no guilt. I'm also quite sure I'd want to do it again. I might even become addicted. There's just something really exciting about a pretty woman with a different sex organ.

    And yes, due to my fear of STDs, if I could somehow do myself, it would be the ultimate, because I'm safe and I think for my age I'm pretty hot. Too bad I can't. LOL.
    Losing the beard is probably a good place to start.

    Your last sentence reminds me of the old Woody Allen line from (I think) Annie Hall, updated for the age of AIDS and personalized for you: "What's wrong with masturbation? It's safe sex with someone I love, and she's pretty hot."

  3. #178
    Member Anneliese's Avatar
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    "The Man Who Folded Himself" by David Gerrold, who wrote the Star Trek episode, "The Trouble with Tribbles", is a book about time-travel, and one of the results is he is able to make love with himself. I read it many years ago, but can't remember details.

    http://www.amazon.com/Man-Who-Folded...7621335&sr=1-1

  4. #179
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    I've never been with a man, but I want to see what's it's like. Life's too short not to experience it, and I want to experience sex with a male....

  5. #180
    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.

  6. #181
    Member Anneliese's Avatar
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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.

  7. #182
    Member Allison_CD's Avatar
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    8+ guys this year. First guy 40 years ago in Bermuda !!

    I am on a Fab UK site and having been a pro photog my pics make me look exceedingly glamourous if a trifle pregnant.

    One guy I threw out the house within 2 mins. 4 guys have returned and one mmm is 40.
    26 y/o was the youngest and I had the most fantastic orgasm with him.

  8. #183
    Member Allison_CD's Avatar
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    I had been chatting to a guy online and when he came to my door I was surprised to see he had a beard!

    A hairy beardy man atop me kissing and being hairy made me feel really girly. xx

  9. #184
    Crossdresser-At-Large BillieAnneJean's Avatar
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    While I sympathize with anyone who is going this route, and this post is in no way judgmental.....

    Never going to happen for me ever never ever.

    So my answer is NO
    NO
    NO
    NO
    NO

  10. #185
    Junior Member Jaylah414's Avatar
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    I've been with other bisexual men and women during our swinger days. It was fun, I reckon, but not exactly satisfying. We only played safe, but with swinging, there was always the worry of whether someone is devoting enough attention to their spouse and hoping you don't do something that would break the other couple's secret rules. My wife and I always wondered why so many people got involved in swinging if they were going to get jealous over any little thing. To be honest, it was pretty weird, sometimes.

    On the other hand, we did know a few couples that were very open and we enjoyed more than just sex with them. They had become friends with benefits.

    As for me, I've always imagined having sex with a particular type of man while I was dressed as a woman. It's a little strange, but dressed in men's clothing, I feel more masculine and would prefer to be with a beautiful, feminine woman - My wife for instance. While dressed as a woman my fantasies tend toward a man that is very strong, larger than me and absolutely in charge. Funny how our brains work.

  11. #186
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    I'm bisexual so I've been with guys in male form but I haven't dressed with one yet.

  12. #187
    Super Moderator char GG's Avatar
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    @Allison:
    So do you think that is why GG's like their SO's to look like men?

  13. #188
    Member EllieMayxxx's Avatar
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    I am so sorry if i offend anyone it is 100% unintentional. I am straight and sometimes when im dressed up I have thoughts of being with a guy but they are so rare. I find that guys don't do anything for me im sorry.
    Ellie May 😘

  14. #189
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    I have always been a fem gay man but dressing is entirely new to me. I am hoping to engage in sex with one of the handsome gentlemen I've been getting to know recently. Grrrrrr!
    Lol
    Josie.

  15. #190
    When in doubt? Smile! Chrissi's Avatar
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    Like a couple of others here: I have a boyfriend.
    Smile! You'll always brighten someone's day, including your own from their return smile!

  16. #191
    Member SandraInHose's Avatar
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    Quote Originally Posted by Anneliese View Post
    ...I am not interested in men as men. They do nothing for me. However, I am finding myself more and more interested in a penis on a woman, whether it be trans or cross-dressing, as long as they had some actual female features. (I am not attracted to a CDer who looks like a man dressed up as a woman)

    I am quite sure if I tried the fantasy, I would like it and feel no guilt. I'm also quite sure I'd want to do it again. I might even become addicted. There's just something really exciting about a pretty woman with a different sex organ.
    Those snips from your post above hit the nail on the head for me. Well stated.
    "Masquerading as a man with a reason, my charade is the event of the season" ('Carry On Wayward Son' by Kansas)

  17. #192
    Non-binary/Questioning
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    Quote Originally Posted by DJono View Post
    I am so sorry if i offend anyone it is 100% unintentional. I am straight and sometimes when im dressed up I have thoughts of being with a guy but they are so rare. I find that guys don't do anything for me im sorry.
    No need to apologize. There is no right answer except what works for you.

  18. #193
    New Member denisepascali's Avatar
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    Guys do not do a thing for me; however when I am dressed I do imagine things. Usually this involves pretty harmless stuff. I think of going shopping together or holding hands. I imagine cooking for a man or going for a walk together. Perhaps watching tv together on the couch, I could see that

  19. #194
    Hi, I'm Kate gokatiegirl's Avatar
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    Many guys and several cds

  20. #195
    Member aussie cd's Avatar
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    not yet...but the urge to try is getting strong...only had these feelings in the last year ...and I'm 52 been cd since about 5....I want to be taken out and treated nicely by an preferably older and taller guy....so I can wear some 4 or 5 inch heels and still be smaller than him...and want to be taken home after a nice night and be taken for the first time....after all this time of feeling the pressure to perform (I hate that pressure) I want to be the receiver at least just once....and guessing it wouldn't be my last...just one problem and that is I will never do this to my wife ....well not without her permission ...

  21. #196
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    I had a boyfriend for a few weeks when I first started being aware of my gender issues. I really feel as though it was more important as a trans experience than a bi for me. I'm still predominately straight, but being with him I didn't have to be the guy in the relationship, I got to let go and be me. And I have to say, post cuddles with a muscular military man... That does make you feel soo girly.

  22. #197
    Junior Member Just4me's Avatar
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    No haven't been with a guy men don't do anything for me I love the look of a women dressed sexy
    Miranda

  23. #198
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    I have been with men as a gay man but, I have never been with a man whilst dressed.
    That's coming though.
    I have been talking to some guys and I'm trying to see how this plays out.
    I have to say, I never received so much attention, even as a fem gay man!
    It's mind-bending!
    Who knew???
    It's also a bit un-nerving.
    I think I understand a bit of the vulnerability women must experience.
    All those wolves at the door! 😳

  24. #199
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    I have been out with guys. I was reluctant when a gf of mine introduced me to a male friend of hers I agreed to go out with him and that would be the end of her telling me I needed to meet guys. This man was so incredibly nice to me. He treated me like I had always imagined a man would treat me as a woman. I dated him several times until he moved. I must admit that after my first date with him I was hooked - just like my gf told me I would be - I have dated several guys since but I still remember how fantastic my first date with this wonderful man.
    Attached Images Attached Images

  25. #200
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    I'd like to add my thoughts here. Generally speaking, I am not attracted to men. I am 98-99% hetero. But there is one man I am attracted to. I have had sexual encounters with him on several different occasions. He is the only man I have ever been with sexually, and I am the only "man" he has ever been with sexually. I am always dressed for the experience. It helps to get me in the mood. But it does absolutely nothing for him. He doesn't care if I am dressed or not. I have no desire to be with a man while not dressed.

    No, I did not feel guilty afterward. If you feel guilty after doing something, then you shouldn't have done it in the first place.

    It is always a pleasurable experience for me. I really enjoy it a lot, and I always look forward to it. The last time we met, I couldn't wait to meet him. I fixed myself up nice and pretty. I wore purple satin and lace bra and panties, black pantyhose with a backseam, black lingerie, and a black minidress. He loved my outfit. I flirted with him the entire night. We had so much fun. He treated me like a girl the whole night. I loved it. He made me feel so feminine.

    I must disagree with some posters here who feel that clothing doesn't change your sexual desires or thoughts. When I am dressed as a man, I think about being with women sexually. But, when I am dressed as a woman, I think about being with men sexually. So, at least in my case, the type of clothing I am wearing does influence my sexual thoughts and desires. Maybe I am in the minority here?

    I have always fantasized about being with another CD/TV/TS/TG, but I have never done it.

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