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Curious and really wanting to experiment with my sexuality. What do you think?

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Ok, im 30 single guy always considered myself straight. Although for the past 3 years ive been crossdressing, masturbating anally, fantasizing about men, as well as fantasizing about being a woman. I enjoy all this so i can only assume i should test the waters out. My question is. Is this just a fetish or could i possibly be gay or bi? This is something I've wanted to try badly! So i guess maybe im just looking for words of encouragement.
I have what I want,, No need to experiment.
To thine own self be true, do you ever think of females when you masturbate? Can you achieve orgasm if you do? What ever you do, be careful and use protection.
It might not hurt to speak to a professional and get some guidance as well.
Quote by Tiffishot29
Ok, im 30 single guy always considered myself straight. Although for the past 3 years ive been crossdressing, masturbating anally, fantasizing about men, as well as fantasizing about being a woman. I enjoy all this so i can only assume i should test the waters out. My question is. Is this just a fetish or could i possibly be gay or bi? This is something I've wanted to try badly! So i guess maybe im just looking for words of encouragement.


You don't mention is your attached or single. That makes a huge difference in how this ongoing fantasy should progress. I can say from experience that reality almost never matches fantasy. Therapy can't hurt. It sounds like you're seeking.
Quote by Tiffishot29
Ok, im 30 single guy always considered myself straight. Although for the past 3 years ive been crossdressing, masturbating anally, fantasizing about men, as well as fantasizing about being a woman. I enjoy all this so i can only assume i should test the waters out. My question is. Is this just a fetish or could i possibly be gay or bi? This is something I've wanted to try badly! So i guess maybe im just looking for words of encouragement.


Interesting. I got divorced when I was 30 and was able to broaden my experiences so to speak but still avoided my own interest in crossdressing and same sex relationships etc. Now decades later I wish I had been a little bit more open - I probably would still not have been 'adventurous' as even pre-Aids there were lots of ways to get hurt. I think the suggestion of some professional help and guidance is a good idea. I saw a counselor to help deal with the divorce but that never went beyond the realm of traditional heterosexual relationships. I wasn't ready yet to acknowledge bisexuality etc. Good luck and stay safe!
Quote by ChuckEPoo


You don't mention is your attached or single. That makes a huge difference in how this ongoing fantasy should progress. I can say from experience that reality almost never matches fantasy. Therapy can't hurt. It sounds like you're seeking.


actually, yeah, he says he's single.

my advice? explore your fantasies. labels don't matter. try cross dressing, hook up with a guy, that's really the only way to figure it out. you'll never know until you try it out, and yeah, you really should - nothing wrong with being straight, gay, bi, a crossdresser or whatever. *hugs* let us know how it goes.

You can’t truly call yourself peaceful unless you are capable of violence. If you’re not capable of violence, you’re not peaceful. You’re harmless.

Quote by Tiffishot29
Ok, im 30 single guy always considered myself straight. Although for the past 3 years ive been crossdressing, masturbating anally, fantasizing about men, as well as fantasizing about being a woman. I enjoy all this so i can only assume i should test the waters out. My question is. Is this just a fetish or could i possibly be gay or bi? This is something I've wanted to try badly! So i guess maybe im just looking for words of encouragement.


you're probably bi...but hell...life is too short...find someone and suck their cock...you'll love it...no one has ever told me they were sorry they suck that first cock...& no one has ever said they started too early...the only complaint I've ever heard was that they didn't start sucking earlier...
Quote by sprite


actually, yeah, he says he's single.

my advice? explore your fantasies. labels don't matter. try cross dressing, hook up with a guy, that's really the only way to figure it out. you'll never know until you try it out, and yeah, you really should - nothing wrong with being straight, gay, bi, a crossdresser or whatever. *hugs* let us know how it goes.


Opps. Yeah I need to read more carefully. Go for it. I agree with blondie
Could mean that you're gay or bi. Or perhaps you just fall somewhere on the spectrum, you know?

If differentiating means that much to you, just keep exploring and see where you end up. In the meantime, just enjoy it.

"What is the quality of your intent?" - Thurgood Marshall


Thanks you all! Im liking this having other people to talk about my sexuality with.
It all started for me hitting puberty at 10. Being bigger than the average boy my age didn't help any. Until I first laid eyes on joe in Parochial school. The first guy I'd ever consider kissing. Had a three-way with a mutual guy friend then & I came all over his thigh & cock area. He loved it. So I guess I'm saying things can happen to make it a positive experience. The first time I sucked a buddy's cock, it felt completely natural to do so. I don't know why? The first time my wife gave me that thick 8 incher up my ass, the stroking is what made it feel so darn great! So like the other's said, suck a cock, maybe even grab some lube & condoms & try anal after that. done right, it feels great!
Do what makes you feel good! If you want to learn more about gender and sexual identities go for it but it's just a label. It's not about whether you're queer or not. The question is how queer are you? biggrin Have fun with it!
Just go with the flow and let your desires take control. Nobody can answer this question well for you you just need to do or try what feels natural to you. Forget trying to put labels on yourself!
Self-labelling is a very personal, subjective thing. As a casual observer, you sound like a bisexual man. We don't really have control over what arouses us (or what turns us off). A guy may fight like hell to avoid popping a chub over pics of naked men, but that boner wants to be born.

Life is short. Embrace it. Protect yourself and play safe, but I say sometimes you have to get on your knees to stand tall as a man. To thine own self be true. Bon adventure!
Its never a good idea to restrict yourself with labels.
I'm sure the only regret you will have is if you don't take each and ever opportunity (I speak from experience and regret missed chances)
Its the only sure way to answer your question, no-one on here can truly answer it for you.
Agree with latecomer above.
My opinion for what its worth is "Don't live a life of regrets" to me attraction is about the person, being they male, female, young, old, disabled or able-bodied. A long as the other person is willing id say go for it, and if it's not for you well, that's that. I wish you well on your road to discovery.


Catherine x
Quote by Tiffishot29
Ok, im 30 single guy always considered myself straight. Although for the past 3 years ive been crossdressing, masturbating anally, fantasizing about men, as well as fantasizing about being a woman. I enjoy all this so i can only assume i should test the waters out. My question is. Is this just a fetish or could i possibly be gay or bi? This is something I've wanted to try badly! So i guess maybe im just looking for words of encouragement.
I came out when I was 30 and I have never regretted it. When I say I came out, I came out to everyone including family.

Quote by Imabadboi66
"Do you ever think of females when you masturbate? Can you achieve orgasm if you do? What ever you do, be careful and use protection."
I think of women when I masturbate. I look at pictures of naked women in hot poses when I masturbate. I think of boys I've played with when I masturbate.

The advice to not worry about labels is excellent, yes, but misses the more important consideration: you need to figure out whether you prefer having sex with males. Get on one of the apps and find someone. Until you have a throbbing, fleshy cock filling your mouth with cum or jizz dripping out your asshole, you won’t really know if that’s something you can’t live without.

Maybe you find out that it's just a "fetish" (OP's word) or side fantasy. Maybe you find you’re the lucky unicorn who could be ecstatic fucking (and eventually falling in love with) either sex. But you also need to face the third possibility, that you will enjoy gay sex more, a preference that is guaranteed to widen with age and become undeniable. Find out now.

Having sorted your sexual preference first, you can then play with cross-dressing or even gender experimentation, Once you've found males to hook up with, it will NOT be hard to find someone willing to help you with that.

Try what you want to try, live as you want to live. There is no need to put a name to your lifestyle or to try and label it.

Quote by Ls63563

Try what you want to try, live as you want to live. There is no need to put a name to your lifestyle or to try and label it.

100% agree with u,

Quote by Tiffishot29
Ok, im 30 single guy always considered myself straight. Although for the past 3 years ive been crossdressing, masturbating anally, fantasizing about men, as well as fantasizing about being a woman. I enjoy all this so i can only assume i should test the waters out. My question is. Is this just a fetish or could i possibly be gay or bi? This is something I've wanted to try badly! So i guess maybe im just looking for words of encouragement.

You are experimenting with both your gender identity and sexual orientation. If you find yourself getting a lot of gratification from crossdressing, thinking of yourself as femme and being entered I'd definitely say it's worth learning more about yourself. There are lots of queer clubs where you can go dressed up and perhaps even meet someone who admires your femme self. If the thought of that excites you, go do it! just remember to be safe about everything. if a guy buys you a drink do not let it out of your sight! also if you can find a more experienced crossdresser or trans woman to help you with all of this that may help a lot. It's more fun going places with a friend and safer too.

We are the same, it took me ages to accept it but I’m bi, the label scared me but I can’t deny it,x