Gay, Bi? Scared

[missynicole]

As my crossdressing urge has become stronger and more frequent I am feeling the need to experience sex as a woman. But I am scared. I have had a couple of very minor gay encounters with two other girls but nothing major. I now feel the need but am also scared about what might happen. Will I get cold feet? If I get cold feet what should I do? How do I stay safe? How do I find the right man? What if he isn't nice? What will I feel like afterward if I go through with this? What emotions can I expect? What if I love it? I am not looking for a hookup here, just advice. Has anyone else been through this? Please feel free to post here or send a message. I really do want to try but am scared too.
Thanks to all in advance.
Missy Nicole

[MonicaPVD]

It's OK to feel apprehensive about what you're experiencing. Take it slow. Talk things through ahead of time with your play friends. You may decide that something is or is not for you. That's OK.

[Lana Mae]

To add to what Monica said, don't do anything that you are not comfortable with and know that you can say no! Other wise relax and enjoy! Hugs Lana Mae

[Helen_Highwater]

Nicole,

Do you go out to LGBTQ friendly places? If yes then I'd suggest getting to know a few regulars, over a period of time and see how that develops. If you're not going out then I feel you're going to struggle to do this safely. Your safety over-rides all other considerations.

[ShelbyDawn]

Missy,

A lot of what you describe can be applied to your first time with a girl, the apprehension, the doubt, the questions, it all fits. The difference is the social stigma attached to what you are considering. Your body and your partners body are erogenous zones from head to toe regardless of gender. Being intimate is, or should be, so much ore than who puts 'it' where, it's about giving your partner pleasure and receiving the same from them.

You say you're not looking for a hookup, then don't settle for one. Find a man you can trust and build a relationship with him. Build a relationship and when the time is right, focus on the moment and make it count for both of you. Be honest and straightforward, don't play games, unless they're the fun kind, and let it happen.

Most of all, don't freak out and don't do anything you don't feel comfortable doing, with anyone.

Good luck.

[shortskirt87]

go in head first lol

[kimdl93]

I would suggest you speak with a counselor about clarifying your gender and sexuality. One caution I would offer is that its very possible to conflate fantasy with reality.

As for how to be safe, you certainly know about safe sex. But in the larger context, the world can be very dangerous for transwomen.

[missynicole]

That dear is what scares me. What if when I am with him I discover that I only wanted the fantasy and not the reality? What then????

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Thank you Micki for your words. They gave me a lot to think about. I guess the date idea maybe the way to go. Thank you again.

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Thank you all who responded. You all gave me some ideas I can think about and hopefully arrive at the best decision. Thank you all!!!!

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That may be the way to go dear. I guess I would find out very quickly. Kisses and thanks.

[LilSissyStevie]

Just keep telling yourself, "It's not gay if your wearing a skirt."

[Lori Ann Westlake]

Nicole, I'm afraid I have no practical advice to offer from personal experience. I've never had (nor sought out) an encounter of this kind, though I concur with the advice of others regarding personal safety especially.

I do appreciate the obstacles in your way, because they would apply to me as well. I'd be concerned about health issues as well as the risk of violence. Then I wouldn't be sure how to go about finding a suitable partner, plus, being married, I wouldn't want to cheat on my wife anyway. Apart from all that, I've never wanted "gay" sex in the first place.

However, I can identify with what you said about wanting to experience sex in the role of a woman. That's different from being "gay," because it's about the role in which we imagine ourselves during sex, as distinct from the partner we imagine ourselves with. So from the time I started crossdressing, some of my own fantasies ran toward "lesbian" encounters.

That's one place where it's necessary to distinguish between fantasy and reality, as others have pointed out. There's a mental exercise here. If I imagine sex from the viewpoint of an onlooker, a third party, it's only attractive to me if the scenario has a woman in it. Normally of course that means sex between a man and a woman, and for this reason alone I could see the appeal of actually being the woman in such an encounter with a man. However, the idea of sex between two men does absolutely nothing for me, So if you're looking for a sexual experience with a man, then as Stevie said:

Just keep telling yourself, "It's not gay if your wearing a skirt."

And maybe it isn't "gay" sex, not in your mind. It's "TRANSex"! But what happens when the skirt comes off, and a lot of other clothes too? If female clothing is an indispensable prop to imagining oneself as a woman, then if you end up naked in bed with a man, it seems to me the illusion of femininity and "transex" would pop like a bubble, and "gay sex" is what you'd be having.

If that still floats your boat, then that's fine, but it is a point to consider when weighing fantasy against reality before seeking such an experience. You've used the term "gay" yourself, so if you think you'd be content with an encounter you accept is "gay," that's fine. You mentioned previous encounters with "girls," which I took to be T-girls, though I don't know what exactly a "minor gay encounter" entails! I can only hazard a guess, but this may seem different from sex with a male who's presenting as a man.

Apart from that, sex, like any experience, involves all of the senses--sight, hearing, touch, taste, smell, and all kinds of behaviors. That's where fantasy can collide with reality. In fantasy we can make things happen any way we want to. In reality we have to deal with everything we perceive with all of our senses, and with whatever a partner chooses to do with us. So while I can imagine in limited ways how sex as a woman might be exciting with a man, I've always thought that if I ever tried it, too many extraneous elements would simply repel me.

It's just something to think about realistically, including what "kind" of sex you're looking for, or might end up with. Of course, "your mileage may vary," so if after thinking it through thoroughly you're still irresistibly tempted, I admit the only way to find out is to try it out for yourself. Good luck anyway, whatever you do.

[Sometimes Steffi]

I just have one thing to add. Make sure that the man your interested in really knows that your not all woman.
,There's a case getting a lot of press around here where it didn't turn out very well for the "woman" involved.

A college football player had sex with a woman, but didn't realize that the woman was actually a man en femme. He came back for a repeat a few days later, but this second time, he found out. The medical examiner concluded the death was due to "blunt force trauma". In fact, every bone in her face was broken.

The man was arrested and is being tried for murder. His excuse, "He shouldn't have fooled me."

Never underestimate the power of a man's insulted ego.

[Mackem Sue]

For me it's about dressing and feeling like a woman. I have no desire for a same sex encounter and dressing is if you like my natural boundary.

To me is seems you are not sure who or what you are. You may well be a bi-crossdresser or it may be alot deeper in that you are a woman in the wrong body.

As said elsewhere, you need to seek counselling not just for yourself but in the interests of those close to you too to determine who you really are as regards gender and identity. If you determine you are somewhere else on the gender scale, then find that place rather than be miserable being someone you're not.

I've given up trying to deny my cross-dressing need and I feel happier for it.

You also need to do the same in your own way for your own good and wellbeing.


Sue

[GretchenM]

Kim's advice regarding conflating fantasy and reality is very good and wise. It is really easy to mix gender and sex in your mind and then find out the connection is not at all what you thought was the case. Unfortunately, there is no way to easily figure out when it is a false association or when it is a real desire for same-sex sexual intimacy. Keep in mind that many of the taboos on same sex contact may exist, at least in part, because of beliefs rather than realities. Many intelligent animals, particularly the apes and the whales and porpoises, engage in same sex play with a very sexual aspect to it. Intelligence generates curiosity and imagination is a big part of that. So it would be strange if humans did not have the same curiosity even without genetics entering the picture and creating the predispositions with respect to sexual orientation and gender variance. Taboos may be more to maintain a social norm that really doesn't need to exist biologically. The fact is sexual play in humans is, in part, a way to develop strong connections between good friends which seems to be so very important in a social animal like humans. Our thinking and traditions sometimes appear to be contrary to the natural reality. But how does anyone know if it is or isn't?

That said, sexual diseases are one of the downsides to reproducing sexually and having sex play a reproductive as well as a recreational aspect in our lives. Be safe.

[docrobbysherry]

Missy, there r safe ways to meet men. I was at a R event last nite. Maybe 80+ T's and men? This is part of a larger group of 500+/- who met regularly in my area, LA, SoCal.
By the end of the evening the place is always packed with male "admirers" hoping to meet or hook up with a T. In my experience, they r polite, considerate, and safe. Altho, men r not my thing! If I was, I would ask one of the regular T's who is, about the man in question.

I suggest u find a local T friendly bar or club. You'll meet other T's and men, in a safe venue. Then, be able to move at your own speed. To decide if it's a fantasy or not!

I have met some wonderful, flattering, and persistent young men.
They were fun to be around. But, I try not to encourage them. I know what it's like to be after a woman that seems friendly but in the end is into u just for the attention and the drinks u buy her!

[mbmeen12]

men can't deal with a phenomenon known as post nut clarity, whence they become overwhelmed by guilt as soon as the deed is done

Well written when dealing with newbies/1st timers too. "IF" you do decide to date, take the actual date slow i.e. drinks, talking, dinner. Quality vs quantity!

[MonicaPVD]

I have met my share of that type. Yet, I have also been with some considerate, wonderful men. We tend to be fetishized by a lot of men, who see us not as humans but as sex toys. However, you can't lump them all together.

Sex with men can be exciting or gross or it can simply be a very effective mechanism for self affirmation. You make of it whatever you want to.

[Stephanie 334]

Hello all....

I'm sitting here reading some of the threads...

And I am at a particularly difficult time in my life because my wife, best friend, soulmate have left me to be fitted with angel wings.

Some 27 years ago I started dating my wife. She was bi before we started dating and early on, she inquired if I had ever been with a guy. I said not really but said I would try it if she wanted me to. My thinking was she might want to incorporate bisexuality in our lives going forward.

She set it up and as a result, I had my "date night" at our apartment after we met the guy at a restaurant a couple of weeks prior. As a result of our get-together I "lost my cherry" and discovered my bisexuality going forward and enjoyed it.

From taking on the female role with a guy I discovered my female side and that led to my crossdressing for the past 17 years, eventually going out to gay clubs as a female and just enjoying the interactions with crossdressers, lesbian females, gay guys and just being one of the girls in the ladies room.

There is more to this entire dynamics with the wife, crossdressing, and being bisexual that centered around the wife and it was all OK between the two of us and how we handled it.

So now that she is gone and I'm alone I need to move along with my life. Before she passed we spoke about that.

I

[Micki_Finn]

I would say that this is a relatively common urge for many CDers. The problem is that many are really only into it conceptually. The concept of experiencing sex “as a woman” or “having sex with men” can be very appealing because it is all abstracts. Get down to the nitty gritty. Can you name a specific man that you are sexually attracted to?

Also, are you sure that the physical acts you are curious about will even be enjoyable to you? There are ways to simulate certain things without a partner. But even that doesn’t guarantee you’ll actually be attracted to a male.

For some more practical answers to your specific questions. The answer to most of your questions can be summarized in one word. “Date”. Don’t go for hookups. If you go into it as a hookup, then things like cold feet can be problematic because you’ve created an expectation in your partner. If you just date, not only is there generally not an immediate expectation of sex, but it also solves your other problems too. You stay safe by meeting in a public place and getting to know the person before you jump into bed with them. Also it give you a chance to figure out if he’s “nice” or not before the clothes come off.

As for what emotions and feelings to expect, that’s entirely on you and unique to each individual and circumstance.

[TheHiddenMe]

As to being gay or bi, the only one who knows the answer is you, perhaps working with a therapist.

Do you want to meet up with a man while dressed as a woman, or as a man, or both?

Do you want to meet with an admirer? Or with another bi or gay man?

These days, if you want that type of relationship, it's 95% likely you have to meet online. There are fewer and fewer gay/LGTB bars, especially in our post-Covid world.

It means finding the right app for what you are looking for, signing up, creating a profile, swiping left and right, then doing your due diligence to pick out the right guy.

Because in this case, the guys are going to be the aggressors. They will be looking for YOU, you won't have to look for them. You will have to sort through your suitors, take the proper precautions when and if you do meet in person.

[Rachelakld]

go to a mans club, be safe, try it (no strings attached), see if that's where your at and go forward from there.

BTW, my wife and daughters think I'm crap at giving advice (but I did enjoy jumping out of perfectly good aircraft)

[Stephanie 334]

Hello to everyone...

I was a member of this site oh maybe 10 or so years ago, but left because I went back to work full-time salaried 65 hours + a weekend simply didn't have time.

For me, my dressing came out from a point in time when my wife and I started dating, and early on she told me that she was bisexual. A little bit later she asked me if I had ever been with a man? My response was "kinda" but not really.

Well, she asked me would I be interested and I said: "try anything at least once".

Well after we got an apartment together and she one night asked if I would still be interested in meeting a guy and I said sure why not...and a month later she arranged my "date night"...arranged to have my cherry popped and from there I found the female inside me and I became "Stephanie"...

Looking back some 27 years now I can honestly say no regrets and now that I am alone, I am planning on spending 4-5 days in my female mode going forward.

But overall, its been a blast and I've loved the whole aspect of being bi-gendered and Bisexual. JMHO

[rhonda]

Getting into gay relationships is probably like crossdressing once you start you will find you wont be able to stop

[Star01]

Reality as pointed out often differs from fantasy. For example, threesomes sound like fun but one soon finds that there are twice as many a-holes and elbows. I guess the only way to know for sure would be to try it.

[GaleWarning]

The only way to find out is to give it a try.
I did. It was not to my liking. But at least I now know.
One piece of advice - don't pick up a stranger.

[mbmeen12]

I would suggest you speak with a counselor about clarifying your gender and sexuality. One caution I would offer is that its very possible to conflate fantasy with reality.

Well said kim...but eventually it will happen, dont force it and your biography says it all as far as I can read and it reads like a want ad. Dont deny yourself and you are what you are. It is ok to be....