Gay, Bi? Scared

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

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.

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

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.

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.

go in head first lol ;)

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.

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

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.

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.:hugs:

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.:battingeyelashes:
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!:thumbsdn:

It has been my experience that all the guys I was with are dirty, hairy, controlling egotistical boys who can't take no for an answer and feel slighted because you walked by them in a skirt and looked like a tease. I never found a true gentleman who has sisters and understood how to actually converse with a woman.
It jaded me so much I am now a lesbian in my own mind and cannot even think about dating a male in any form of dress.
Good luck with your experience, may I suggest if you do not like your situation, turn into a guy and carry a pair of brass knuckles in your purse.

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.

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.

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.

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.

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

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)

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

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

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.

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.

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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.

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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....

It's a bit like asking if getting married is a good thing. That depends...
I really enjoy sex with a man and have been doing it for many years. I met a fellow who was kind, considerate and always went out of his way to make me feel comfortable. We were fwb for many years until I moved to a different city and he entered into a ltr. Rats...
I would love to have a relationship with another guy but I really don't care for the auditioning part. My first fwb really spoiled me and I realize that it will be tough to replicate with someone else. I am certainly open to it though. It was absolutely the most fulfilling sex that I've ever experienced but as I say, it really depends on the person...

Remember, if in doubt... don't!

What if you discover the reality isn't what you wanted but only the fantasy??

Be upfront about your newness and uncertainty. If someone hesitates then that's not the man you want to be with your first time.
If things aren't to your liking as things progress then say NO.

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:

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Originally Posted by LilSissyStevie

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

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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.

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.

We all come here with different goals in mind. They are all ok. As long as every idea is safe sane and consentual, it's fine. Once you get over the taboo feelings you can open up to the experience and decide if it is right for you. Ask others in the community about safety and specific people. Explore you're interests but do it safely.

This topic always fascinates me when it comes up, so thanks for posting. I really enjoy reading others thoughts and experiences in this area.

I would love to have sexy time with another crossdresser, but have no interest in sex with men who don't dress. My only experience has been watching crossdresser/tranny porn. I like watching two crossdressers together and tranny on female, but when it's crossdresser/men I don't care for it. I'm pretty sure it would be the same in reality, maybe someday I'll find out. I've already experienced sex crossdressed with women, and know I really enjoy that!

Nycole,

I can say I have enough experience to give you a good advice.

I was writing and thinking exactly about this last night.

This is what I wrote:

"It's a known fact that's not a good idea to go shopping to the grocery store when hungry. You'll leave with a lot of food, most of it just sugar and many things you won't actually eat."

I was a crossdresser. Now I know that I wasn't a crossdresser but a transexual or transgender woman

As many here,, my main release valve was to dress but it wasn't enough, sex was a huge ingredient that could pacify me, at least that's I thought, but it didn't too. In the way of exploration as you (I post something here) I arrive to the conclusion I was gay, because sex was more satisfying for me as a woman than sex with a woman, not that I didn't enjoy sex with a woman but with a men fitted better in my non-ending search for satisfaction and identity.

In that moment, when I still feeling not satisfied, I confess all my feelings to my wife. I was looking and asking for freedom to experience my identity, that in that moment was deeply rooted in my sexual identity.

Luckily, my wife accepted but with the condition on no meet guys, at least for sex,.other crossdressers would be ok but not for sex.

So now, I had all the freedom, at least to dress every single day.

I start going out on a weekly basis but still not being enough so I decide to look help on a therapist.
I was around a year on therapy with a family therapist with experience on crossdressers.

Affortunately, she advice me to talk with my PCP and she referred me to an endocrinologist.

When I started in hormones everything start changes included my sexuality. All those cravings for sex began to fade, of course testosterone was blocked.

Then, and just then, I could see my life and find that it wasn't even to dress but to be a woman.

The rest is history, I'm legally a woman, still happily married to the same woman of the last 42 years. I'm a very different person now and have certainty what's my sexual preference and no more promiscuity.

Btw, it's a very dangerous road, in many ways, to explore sexuality especially with men, most of them are Iike dogs, you know what I'm talking about.

I can't tell here the dangers I was in, the bad experiences I had. If someone would had told me what I'm saying now thi gs would be different.

My humble opinion based in my own experience.

Devi

Take off my makeup, wig, clothing and shapewear and I'm a man.

There's no hiding that fact, and if I were to have sex with a man, it wouldn't be "I'm femme so it's not gay". It would be gay, and there's nothing wrong with that, but there's no lying to myself.

There's just no appeal really. The sex itself would be fine, I enjoy pure mechanical sex of different shades, but I don't find men attractive. Do I want to feel beard or stubble? No. Arm or leg hair? No. Rough hands? No.

I love everything female, both as what I aspire to be, and as what I want to be with.

Sexuality is a 64 count crayon box. There are many different shades. Most of those shades you will never, ever use. Others will be a mainstay in every picture. As you sit coloring with one of those mainstay colors, your eyes constantly drift to those rare colors as you search for some place to use them.
As someone else has already said, have you ever looked at a man and found yourself attracted to him? Or is it a fantasy, where there is always a faceless man and the only clear parts are you and his penis? Personally, there are very few men I have found attractive, and none that I have ever kissed on the lips. I have, however, found a great number of women I have loved, and kissed (one that I love and married) and a fair few penises I found attractive. There are sexual acts that attract me. There are sexual acts I find pleasurable that women cannot complete. So that created my initial quandary. "What does that make me?" For years now, I don't care. Why do I have to label myself? For the ease of others I describe myself as "sort of bi", which of course initiates the conversation wherein I can go more into detail. The important part is the conversation, and ensuring the other participant is completely clear on boundaries. If they are not okay with your boundaries, you should not be okay with them. Exploring your sexuality and establishing your likes and dislikes is fine. Just remember, you are an adult and you need to think and act responsibly in your exploration.

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Originally Posted by Sometimes Steffi

I just have one thing to add. Make sure that the man your interested in really knows that your not all woman.

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I would add, make sure that the man you're interested in is not mentally unstable or ill. Here's why. Every single man that has ever become violent or deadly because they "didn't realize that she was a he" was lying. Well, maybe a few were tricked by a gorgeous, slender 19 year old "trap" crossdresser, but even that is difficult to believe.

Of course they all knew. Of course they were turned on by the kink of it all. However, some dangerously insecure - or mentally ill - 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 and may be motivated to act violently. This is a real thing. I've experienced this to a lesser degree in the past, particularly with younger guys. Some men will react by pushing you out the door as quickly as possible and others may react by becoming violent to the point where your life is in danger. You can avoid this by being careful about who you play with. A general rule of thumb is to avoid men who are both really pushy about getting busy with you and really paranoid about being spotted with a CD.

MonicaPVD that is great advice!

I try to set expectations and ground rules before going out. If someone won’t communicate by text or phone what they are looking for and hearing what you are interested in, the likelihood of having a good time seems pretty small.

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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

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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!

I would say, take it slow and be open about your lack of experience. Be aware most men do not want a real relationships with us. These people will also mostly self indentify as straight. Id avoid those as they are nore likely to be really bad. I had some good times amd some very bad times delving into the world of men. You will get a feel on how they talk to you if they are right for you.

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

Stephanie, sorry to read about your loss. We all have or will experience that one way or another eventually. Stay strong, and get dolled up.

I have found a couple of guys on Doublelist. Simple rule I follow is meet them at a nice hotel in a room they paid for. It pretty much ensures civilized behavior for the most part.

Since the OP has not been back on for two weeks and not seeing everyones advice I am closing this thread.

To everyone that took the time to answer and stay within the rules to help the OP figure things out thank you.