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Thread: Dating a man

  1. #1
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    Dating a man

    I have Been talking to this guy online for the past couple of months and he wants to take me out on a date, dinner/ movies, he seems like a nice guy always friendly remembers stuff about me, he is 25 years old, should I go ahead and do it I will be out dressed of course, has anyone else done this

  2. #2
    Senior Member Diversity's Avatar
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    Personally, I believe what you are about to do is wrong. It is an emotional bomb waiting to explode. People can get hurt. Honesty is the best policy. My advice is that you should be honest with the man and let him know you are not who you are pretending to be. Emotions and feelings are not things to treat a a game. Level with him. Be honest with him. Then let the chips fall where they may.
    Di.

  3. #3
    Member LisaMallon's Avatar
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    Well, obviously he should know you are TG, otherwise it is a no go.

    If he knows and still want to take you out then great, just some basic tips, including the all important safety ones:

    Go somewhere public. Let a Friend know that you are going (and where) and tell them you will contact them, at a certain time (or times) that you are ok, otherwise they call out the riot squad. Plus give them all the details of the person. Your final safety call should be at your home when you get back and there should be a time set on that. "If you haven't heard from me by 1am then call the police I am with ...." and all that

    Don't overdress. Wear something nice and attractive but not over the top.
    Makeup, same, nice but not '****ty'.
    Sex: not on the first date (like a major no-no). If you get on like a house on fire .. jump his bones on the 3rd date ok (and don't forget the condoms)?
    Kiss is nice, hugs are good, holding hands is wonderful. Lip kiss is only at the end of the night, and only if you liked him and had a good time and want to see him again.

    Edited to add: And tell us all everything afterwards .. we all love good gossip.

    Enjoy and relax, just be yourself. Laugh and enjoy. Ideally he has a good sense of humour. Talk about things you like. Listen to what he is passionate about (tells you a lot about his heart). Talk to him about what you are passionate about (lets him know where your heart is at as well .. it is a 2 way street).

    Don't get drunk, but a bit tipsy is ok .. but don't forget your safety calls (or texts) otherwise you will both get arrested, when your friend call the cops out.
    Watch what he drinks and match him but a bit less. If he gets drunk then you can get a bit tipsy. If he stays sober .. then you do, especially if he plies you with drink (big warning sign that and dump him fast).

    Personally I'd prefer (but that is a matter of taste) that he gets a bit drunk. Basically because the true person comes out a bit more. If he is a sweetie when half drunk then you can reasonably be sure he really is a sweetie.
    The risk is that he gets more frisky .. and remember no sex on the first date.
    Never forget: IT IS OK TO SAY TO HIM "I'd prefer it if you don't drink so much".

    Give you a tip. When it comes to the bill thing for dinner if you have decided you want to see him again, then let him pay (after a little bit of an argument, and you must have a little bit of an argument), but on the proviso that he agrees that you do it (or share) next time. If you really like him, then hint about cooking for him sometime (but that is best on the second date that one).
    If you don't want to see him again, make a really big noise about sharing the bill. Now you might, in the end, let him pay, but you have given yourself the perfect excuse not to go out with him again.

    Another big tip: keep enough cash money that you can just walk out and get a cab home by yourself.

    Another, really serious tip: don't get isolated from other people. Make sure you are around others all the time. Stick to a restaurant, bar, etc.

    Good luck .. and good hunting.
    Last edited by LisaMallon; 08-15-2012 at 05:49 AM.

  4. #4
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    Hi Jess, Be careful what you wish for!!
    Having my ears triple pierced is AWESOME, ~~......

    I can explain it to you, But I can't comprehend it for you !

    If at first you don't succeed, Then Skydiving isn't for you.

    Be careful what you wish for, Once you ring a bell , you just can't Un-Ring it !! !!

  5. #5
    Aspiring Member Amy R Lynn's Avatar
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    I agree with what Lisa said. If he knows you are a Trans and still wants to take you out then go for it. Just be careful.

    If he doesn't know that you have boy parts, you could be setting yourself up to be in a very dangerous situation. People have been killed over things like this. Just be careful. And def no sex on the first date, maybe on the third or fourth. Do let us know how it went!
    "Oh my God, I realized, it's not that we're screwed up; it's just that we've been trained to thnk so."
    ~Rick Novic, Alice in Genderland

  6. #6
    Platinum Member Beverley Sims's Avatar
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    Quote Originally Posted by BLUE ORCHID View Post
    Hi Jess, Be careful what you wish for!!
    This is my view exactly.
    Work on your elegance,
    and beauty will follow.

  7. #7
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    Remember tell him you are TG and yes have a friend call you while you are on the date or you call them at a specified time to let them know you are OK.
    If he doesn't know about you and he finds out Katie bar the door you are in trouble.
    This is not a game you are dealing with a mans emotions here.

  8. #8
    Silver Member Mollyanne's Avatar
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    Talking to someone on line is totally different then "meeting face to face"!!!!! Me personally, I would tell him who I am, and would meet him in a public place with a friend. After that if things go well "do your thing" Remember this though---" Woman can run faster with skirt up then man can with pants down"

    Molly
    "To thine own self be true"

  9. #9
    Platinum Member kimdl93's Avatar
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    The question is whether you are gay or not. Maybe you don't know. I'm assuming he knows you are a CDr, right? And he's gay, right? If the two of you are on the same page in that regard, then the question is how to do so safely. People can be differnt in RL than on line. So why not meet in a public place the first time and the decide if you want to get together again in the future.

  10. #10
    Member katie_barns's Avatar
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    Jess

    First of all it is good you posted this before hand. Please adhere to the advice giving here. Mostly that he be aware what you are up front. Please be careful. It can be a great experience but can go terribly wrong also.

  11. #11
    Miss Conception Karren Hutton's Avatar
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    As long as you didn't meet through craigslist....
    Current Obsession - Breasts and Lingerie!

    .......My Photos

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    Quote Originally Posted by Jess6887 View Post
    I have Been talking to this guy online for the past couple of months and he wants to take me out on a date, dinner/ movies, he seems like a nice guy always friendly remembers stuff about me, he is 25 years old, should I go ahead and do it I will be out dressed of course, has anyone else done this
    Are you gay? If not, why would you consider dating a man?

  13. #13
    Member Marcie R.'s Avatar
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    I know of a situation in Florida, several years ago. A married man was out of town and decided to have some fun while he was away from home. He met a girl in a bar and they became very friendly with him inviting her back to his hotel for a drink, plus whatever else came up. After a few drinks, things heated up and they jumped on the bed. She started to take her clothes off when with total shock, the man saw the surprise of his life, some large genitals on his partner. She had not told him she was a crossdresser which caused him to go into an uncontrolable rage. He hit her with everything he could get his hands on, ending up with her death. Consquently the man was charged with murder and sentenced to life in prison. He gets his three meals a day and a place to sleep, however it was his family that suffered the most, just because of his careless actions one evening away from home.

    Please be careful Jess

  14. #14
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    In your post about being caught, you stated that you were straight. Now you want to date a man?

  15. #15
    Silver Member BRANDYJ's Avatar
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    Quote Originally Posted by Heather Daniels View Post
    In your post about being caught, you stated that you were straight. Now you want to date a man?
    You noticed too? Straight guys don't date men any more then straight men dating a CD. Sounds like his dream might turn into a nightmare.

  16. #16
    Ice queen Lorileah's Avatar
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    Quote Originally Posted by Jess6887 View Post
    I have Been talking to this guy online for the past couple of months and he wants to take me out on a date, dinner/ movies, he seems like a nice guy always friendly remembers stuff about me, he is 25 years old, should I go ahead and do it I will be out dressed of course, has anyone else done this
    Did I miss the part where Jess said they had been pretending to be female online? Everyone seems to have jumped to that conclusion. I read it as he knows her gender.

    If that is the case just like any date you should take the correct precautions. You may want to tell someone else where you are going and what you will be doing. Maybe have them call you sometime just to check. I meet people all the time in public, that is the key,keep it public to start with.
    The earth is the mother of all people and all people should have equal rights upon it.
    Chief Joseph
    Nez Perce



    “Love isn't a state of perfect caring. It is an active noun like struggle. To love someone is to strive to accept that person exactly the way he or she is, right here and now.” - Fred Rogers,

  17. #17
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    As a CD I never considered myself gay when dating men. It's just natural for a "girl". Guys like CDs and TVs, especially guys feeling insecure
    about their sexual preferences. After all a lot of men seem to consider a TV close enough to a girl. At least that was my experience. I "dated" or at least met with married men. Of course they knew very well beforehand that I was a TV. Just go for it!

  18. #18
    Platinum Blonde member Ressie's Avatar
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    I'm noticing a lot of straight guys in their 20s that have a strong curiosity of what it would be like to be with a transexual or CD. When I was in that age group there was an occasional photo of a TG in Penthouse and similar mags. Now days on the internet if you visit one porn site, every category will pop up whether you want it or not.

    There just seems to be many bi-curious out there, maybe including Jess6887. So being gay isn't a prerequisite to date someone out of the norm.

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    Quote Originally Posted by velvetmb View Post
    As a CD I never considered myself gay when dating men. It's just natural for a "girl".
    But you're not a girl, you're a crossdressing male. Male + Male = homosexual aka gay.

  20. #20
    Happy to be alive. Wonderwho's Avatar
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    Really, unless your TG you're looking for a whole lot of problems. Maybe what you should do is get together just as two guys having a drink and explain the fact that you are a CD.
    Just remember it's very hard look good after you had the s**it kicked out of you by someone who thought they were dating a woman and found out that they
    were not.
    Black eyes and broken noses are hard to cover with makeup. Be careful and good luck.
    Wonderwho
    .... and someday I too will become a butterfly screamed the catapiller!!!

  21. #21
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    First off I have to go with Lorileah in a way here. The initial question is does he think you are a GG or does he know the whole story to paraphrase Paul Harvey.

    Now if he thinks you are a GG you had better fess up pretty quickly and realize that although there is a definite fascination amongst the "straight" male concerning us it generally ends there for the most part. Few act on it and those that do are not what you want as a dating partner. If he knows the truth and is still interested in meeting for you drinks then go for it gurl!

    I have been dating men for over 25 years now and have had some tremendous relationships and developed some friendships that still go on tioday even though the romance part of the relationship is long past. I know many of the gurls here proclaim themselves as heterosexual however I would be shocked if most of those if not all haven't at one time or another wondered what it would be like to be on a date with a man.
    Some ask why? Some ask why not? I ask "Does this pump come in a 9 1/2?"

  22. #22
    Member JohannaSophia's Avatar
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    I would suggest meeting on neutral ground for coffee but if you have boy parts he needs to know all about you now before you go any further. If he is OK with it great, have fun. Be up front and honest and be careful.

    If you are Trans-Gender and all the parts work great you probably perceive yourself as a girl. You should assume he will eventually find out and could react negatively and even violently, better you tell him up front in the coffee shop or sooner.

  23. #23
    Member karinels's Avatar
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    I have just recently explored the thoughts of being with another man, twice within this week, with two different guys. I have to say, do be careful what you wish for. I was upfront, both knew who and what i am, they both said what they were, but neither were completely honest with what they were offering, if you know what i mean.

    I was expecting same age, better shape, better, well, equipment, better hygene, neither were 100% honest about what i should have expected. I have learned from that, but also have regrets that will have probably changed my life in a way I never expected, nor wanted.

  24. #24
    New Member jenny76's Avatar
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    well I'm assuming the guy knows he'd be dating a TG, and that Jess wants to try it. If thats the case, I really like what Lisa listed. Seems like something to save if you ever thought of dating a guy one day. Also, talking to him on the phone before meeting him might be good too
    Last edited by jenny76; 08-17-2012 at 08:14 AM.

  25. #25
    Silver Member linda allen's Avatar
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    Quote Originally Posted by kimdl93 View Post
    The question is whether you are gay or not. Maybe you don't know. I'm assuming he knows you are a CDr, right? And he's gay, right? If the two of you are on the same page in that regard, then the question is how to do so safely. People can be differnt in RL than on line. So why not meet in a public place the first time and the decide if you want to get together again in the future.
    I agree with Kim. Find out beforehand what each of you expect from the other. And meet in a public place the first time. Maybe the first few times.

    Dating someone you met on the Internet is a risky process even between hetrosexual males and females. Thow crossdressing, transgender or gay into the mix makes it really risky.
    [SIGPIC]http://www.crossdressers.com/forums/image.php?type=sigpic&userid=82706&dateline=137762 0356[/SIGPIC]Linda

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