Dating a man

[Jess6887]

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

[Diversity]

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.

[LisaMallon]

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.

[BLUE ORCHID]

Hi Jess, Be careful what you wish for!!

[Amy R Lynn]

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! :)

[Beverley Sims]

Hi Jess, Be careful what you wish for!!

This is my view exactly.

[Tracii G]

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.

[Mollyanne]

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

[kimdl93]

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.

[katie_barns]

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.

[Karren H]

As long as you didn't meet through craigslist....

[Voulez-Vous]

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?

[Marcie R.]

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

[Heather Daniels]

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

[BRANDYJ]

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.

[Lorileah]

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.

[velvetmb]

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!

[Ressie]

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.

[Voulez-Vous]

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.

[Wonderwho]

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

[Karen_Ski]

:2c: 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.

[JohannaSophia]

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.

[karinels]

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.

[jenny76]

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

[linda allen]

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.

[Badtranny]

Thow crossdressing, transgender or gay into the mix makes it really risky.

I know you don't mean it to be but I think that's a an offensive remark. So because I'm transgender than it's risky for me to meet men online? I was gay before I transitioned and I met lots of guys online. It's really convenient and it's honestly where people meet each other these days.

Maybe it's the average age around here, but there is this pervasive negativity about meeting people online that I just don't get. There was a time when meeting people from the "internet" was unusual but not anymore. I'm a grown person who's seen a thing or two and I am certain that meeting someone online is no different than meeting someone at a park. They're both strangers until you get to know them. There are millions of hookups and friendships and relationships that were facilitated by the internet and every now and then we hear about something awful. The odds are in your favor that everything is gonna be fine.

Life is for living folks. Make a friend, have some fun.

[Lorileah]

Maybe it's the average age around here, HEY! Get off my lawn kid! {
but there is this pervasive negativity about meeting people online that I just don't get. There was a time when meeting people from the "internet" was unusual but not anymore. I'm a grown person who's seen a thing or two and I am certain that meeting someone online is no different than meeting someone at a park. They're both strangers until you get to know them. There are millions of hookups and friendships and relationships that were facilitated by the internet and every now and then we hear about something awful. The odds are in your favor that everything is gonna be fine. I have met so many nice people on line also but I still worry about those who frequent certain sites (cough CL). I am sure it isn't much different than meeting in a bar. No matter where you meet someone, common sense must prevail. Always have an exit plan. (add always have the cell phone set to redial a friend too)

[Shelly Preston]

Well if you choose to date this man you need to take obvous precautions.

1. Make sure he knows you are TG and there is no misunderstanding

2. Consider what you expect from meeting each other.

3. Always meet in a neutral place and make sure its public too.

4. I would also suggest you see each other on webcam first if possible

There are guidelines in the meeting place for anyone considering meeting anyone from the forum

I suggest you read them at least twice. I know I do when meeting anyone I dont know.

[Bree-asaurus]

Wow... soooo little information and so many assumptions.

The one thing I can say is that I agree with BadTranny. Online dating is actually quite cool if you aren't stupid about it. Like her, I was a 'gay man' for a while and met guys online. I didn't have any bad experiences... every guy that passed my 'willing to meet in person' test was pretty cool. Didn't meet any creepers in person and every guy I met was worth a second date. Heck, the first guy I met and dated is now one of my best friends.

[MsJanessa]

As long as you are upfront about exactly who and what you are prior to the meeting and you are both clear on your expectations, go ahead and date him---my advice to you is the same as it would be to any other TG or GG for that matter---meet in a public venue---gay bar would be my choice-for A drink(just one--dont' want to get smashed on the first date)--that way if you don't like what you see or hear you can back out of anything further---have fun


I know you don't mean it to be but I think that's a an offensive remark. So because I'm transgender than it's risky for me to meet men online? I was gay before I transitioned and I met lots of guys online. It's really convenient and it's honestly where people meet each other these days.

Maybe it's the average age around here, but there is this pervasive negativity about meeting people online that I just don't get. There was a time when meeting people from the "internet" was unusual but not anymore. I'm a grown person who's seen a thing or two and I am certain that meeting someone online is no different than meeting someone at a park. They're both strangers until you get to know them. There are millions of hookups and friendships and relationships that were facilitated by the internet and every now and then we hear about something awful. The odds are in your favor that everything is gonna be fine.

Life is for living folks. Make a friend, have some fun.

Totally agree--there is absolutly nothing wrong with meeting folks on line and dating them--I've had some very good lasting relationships with TGs I've met on line for dates---The concern that some of the people here are expressing is for your safety--after the Craigs list murders in Massachusetts, a little caution is a good thing---but that shouldn't stop you from meeting someone who has contacted you via the internet---just be careful until you get to know them personally

[eric45211]

:jumping::jumping:Recently dated a cross dresser I met on line. It was great. Treated her as a lady and it all worked out fine.

[Nicole Erin]

The biggest risk of meeting someone online and having them want some fancy date is they will flake out ("stand you up" in old terms).
Yeah there is a chance they are some weirdo and a slimmer chance they are psycho but that can happen anywhere.

Things should be fine as long as the guy actually bothers showing up.

[Badtranny]

Things should be fine as long as the guy actually bothers showing up.

I KNOW! The worst thing is getting dolled up to meet some guy that you thought was so sweet and finding a parking space, and buying a drink and waiting and waiting... Texts aren't being answered and calls are going to voicemail.

A week later you get an email apologizing and trying to set up another meeting.

No thanks. Sometimes I think every guy wants to walk on the wild side, but then I realize all they want to do is talk about it.

[kellycan27]

But you're not a girl, you're a crossdressing male. Male + Male = homosexual aka gay.

Actually it doesn't have to mean that someone is gay.. it might just mean that someone is curious. A lot of people experiment without having to be labeled as this or that. "gay" addresses sexual preference. One might describe a man having sex with another other man as having had "gay sex"..... but does that necessarily make them "gay"? I always thought of gay as being sexual preference and a lifestyle.... An act does not a lifestyle make.