Sexually confused – should I hire a female escort?

[Rawalicious]

I'm 28M and a strict 'side' (no anal). I've only ever had sex with men and never actually enjoyed it. Yes, I enjoy seeing naked guys and I've had intense crushes. I've had a brief relationship at uni, hookups, been to a gay sauna, etc – and yet I never orgasmed or felt much pleasure. Frankly, it was super boring.

There's this whole rich psychological landscape around maleness that I can tap into: the shared understanding between men, the idea of "knowing EXACTLY what it feels like" for them, the visual of male bodies and physiological responses. Here are some erotic stories I've written that channel it: 1, 2, 3, 4, 5. But I never fantasize about anything but being a passive observer. I worry that I might be stuck in this voyeuristic phase forever, feeling empty and unfulfilled. I've also never been in love.

In the past few years, I sometimes felt attraction to women. Surprisingly, a few times I even found myself drawn to a woman's "scent" (skin, hair, perfume). But this happens rarely, and I have zero psychological context for it: no scenarios, nothing I can put into words. Just this very occasional wordless pull.

This got me interested what sex with a woman would feel like. But I'm also completely unprepared to dating women or even if I'd enjoy that. This got me thinking: should I try meeting with an escort for a hour as an experiment? Or would that be a bad idea / unethical to the woman? I've never done it before, but it's legal where I live (Central Europe).

Regarding trying anal sex, I don't think I'd be open to it, as it's always made me icky

 

[GayBootyLover69]

I'm 28M and a strict 'side' (no anal). I've only ever had sex with men and never actually enjoyed it. Yes, I enjoy seeing naked guys and I've had intense crushes. I've had a brief relationship at uni, hookups, been to a gay sauna, etc – and yet I never orgasmed or felt much pleasure. Frankly, it was super boring.

There's this whole rich psychological landscape around maleness that I can tap into: the shared understanding between men, the idea of "knowing EXACTLY what it feels like" for them, the visual of male bodies and physiological responses. Here are some erotic stories I've written that channel it: 1, 2, 3, 4, 5. But I never fantasize about anything but being a passive observer. I worry that I might be stuck in this voyeuristic phase forever, feeling empty and unfulfilled. I've also never been in love.

In the past few years, I sometimes felt attraction to women. Surprisingly, a few times I even found myself drawn to a woman's "scent" (skin, hair, perfume). But this happens rarely, and I have zero psychological context for it: no scenarios, nothing I can put into words. Just this very occasional wordless pull.

This got me interested what sex with a woman would feel like. But I'm also completely unprepared to dating women or even if I'd enjoy that. This got me thinking: should I try meeting with an escort for a hour as an experiment? Or would that be a bad idea / unethical to the woman? I've never done it before, but it's legal where I live (Central Europe).

Regarding trying anal sex, I don't think I'd be open to it, as it's always made me icky

i think as long as there's 100% consent and you openly communicate the escort exactly what you're looking for and what your intentions are, it's noth unethical at all

 

[Brodie888]

I really doubt having sex with a woman is the answer. If you had any heterosexuality in you, it's so small that it's insignificant.

Firstly, I would suggest getting a blood test to check if everything is normal. It's possible that you could have a deficiency in a particular nutrient or hormone that is blunting your libido.

If that is all normal, it's possible that you are more on the asexual part of the spectrum with a touch of homosexuality. Possibly reading the asexual posts on this site will lead you to a realization.

Being a side doesn’t make you any more or less gay and has nothing to do with anything really.

 

[jdphnx]

I've only been with a couple of women way back in my 20's. I liked it and it was very satisfying but I couldn't shake my attraction to guys. I've only been with guys since then until a couple months ago. I was traveling and went to an Asian massage place. The google reviews made it clear they would do happy endings. The massage lady was VERY pretty, in her early 30's, and she did give me an amazing hand job. She let me feel her up as she was doing it, eventually removing her top and letting me feel her bare tits and put my hand down her panties and play with her pussy. I admit it was VERY erotic. You might try going to one of those places to see how you feel.

 

[ericktho]

You're attracted to men, but it doesn't seem strong enough to actually feel anything for them. It seems obvious that you'll end up having relationships with one woman and staying with one.

 

[RomanG82]

There comes a time in every man’s life where he chases with his primal side. Don’t ever feel the need to apologize for it because it’s no one else’s business, but yours. Remember, not all chapters have to be read out loud. Everyone does it, and it’s a really healthy thing.

Sexual experimentation should 100% be explored in one’s personal life.

When it comes to sex work… just be pro sex work! …Ensure she’s comfortable, and feels as secure as possible in your room.
*Consent and payment are priority.*

Think of the payment as a clean boundary. It’ll never be an issue again, unless you decide you’d like a second round down the line, or you come up short lol.

 

[dana2]

I'm 28M and a strict 'side' (no anal). I've only ever had sex with men and never actually enjoyed it. Yes, I enjoy seeing naked guys and I've had intense crushes. I've had a brief relationship at uni, hookups, been to a gay sauna, etc – and yet I never orgasmed or felt much pleasure. Frankly, it was super boring.

There's this whole rich psychological landscape around maleness that I can tap into: the shared understanding between men, the idea of "knowing EXACTLY what it feels like" for them, the visual of male bodies and physiological responses. Here are some erotic stories I've written that channel it: 1, 2, 3, 4, 5. But I never fantasize about anything but being a passive observer. I worry that I might be stuck in this voyeuristic phase forever, feeling empty and unfulfilled. I've also never been in love.

In the past few years, I sometimes felt attraction to women. Surprisingly, a few times I even found myself drawn to a woman's "scent" (skin, hair, perfume). But this happens rarely, and I have zero psychological context for it: no scenarios, nothing I can put into words. Just this very occasional wordless pull.

This got me interested what sex with a woman would feel like. But I'm also completely unprepared to dating women or even if I'd enjoy that. This got me thinking: should I try meeting with an escort for a hour as an experiment? Or would that be a bad idea / unethical to the woman? I've never done it before, but it's legal where I live (Central Europe).

Regarding trying anal sex, I don't think I'd be open to it, as it's always made me icky

What do you think about when you JO?

 

[Rawalicious]

What do you think about when you JO?

I mostly think about guys, either alone, with women, or being pleasured by any gender. I picture a man getting turned on.

Sometimes I also watch women masturbating, especially squirting scenes. But I’m not sure if that’s what excites me *per se* or if it’s imagining another man getting turned on by what I’m watching. There's just so much depersonalisation, or a sense of watching through someone else's eyes, in my fantasies.

 

[dana2]

I mostly think about guys, either alone, with women, or being pleasured by any gender. I picture a man getting turned on.

Sometimes I also watch women masturbating, especially squirting scenes. But I’m not sure if that’s what excites me *per se* or if it’s imagining another man getting turned on by what I’m watching. There's just so much depersonalisation, or a sense of watching through someone else's eyes, in my fantasies.

It sounds like you are primarily male attracted (gay) but also have a voyeuristic or cuckold kink/fetish. You say "I've only ever had sex with men and never actually enjoyed it". Everyone has had mediocre sex experiences. You have just not found the right person. Your kink and fetish will not go away. Accept that a monogamous/traditional relationship will not be satisfying for you. I suggest rather than fighting it you embrace your kink/fetish side. You will have to find a partner who with an exhibitionist kink/fetish to complement yours. Someone who will get off on having sex with other men/women in front of you. Such men exist though it will take more work to find them.

 

[justahornyguy174]

I'd go for it. I've done similar. I'm straight but I've had a fascination with trans women for years but the opportunities to meet one are limited. I hired an escort and it was wonderful! honestly I was nervous, I thought this could go wrong, I might get grossed out having a real cock in front of me, not just a fantasy on my computer screen. I started giving her a massage and it felt totally normal, like I was massaging any other girl. When It got down to trying her cock it felt great, felt totally natural sucking it, like licking pussy feel natural to me. I was so glad i did it, a great experience.
The key is it answered what I wanted to know, so when i did finally meet a beautiful trans woman on a dating app I wasn't nervous at all and had a great time.

The worst that could happen is that you get grossed out, you find out it was just a fantasy and that is fine. You may find you like it, if you do you have answered that question before meeting a woman in the normal way.
Just make sure you meet an escort with lots of reviews from a legitimate website, they will be very understanding if you explain your situation.

 

[BIGBULL29]

There comes a time in every man’s life where he chases with his primal side. Don’t ever feel the need to apologize for it because it’s no one else’s business, but yours. Remember, not all chapters have to be read out loud. Everyone does it, and it’s a really healthy thing.

I absolutely love this!

There should be no shame in having sex, unless it involves violence.

We don't need to disclose our primal desires to anyone. It's nobody's business.

I have a few primal desire yet unexplored.

I love being male and having a dick. Nothing is better than sex.

 

[BIGBULL29]

I'd go for it. I've done similar. I'm straight but I've had a fascination with trans women for years but the opportunities to meet one are limited. I hired an escort and it was wonderful! honestly I was nervous, I thought this could go wrong, I might get grossed out having a real cock in front of me, not just a fantasy on my computer screen. I started giving her a massage and it felt totally normal, like I was massaging any other girl. When It got down to trying her cock it felt great, felt totally natural sucking it, like licking pussy feel natural to me. I was so glad i did it, a great experience.
The key is it answered what I wanted to know, so when i did finally meet a beautiful trans woman on a dating app I wasn't nervous at all and had a great time.

The worst that could happen is that you get grossed out, you find out it was just a fantasy and that is fine. You may find you like it, if you do you have answered that question before meeting a woman in the normal way.
Just make sure you meet an escort with lots of reviews from a legitimate website, they will be very understanding if you explain your situation.

I agree with you. He might need to explore his sexuality with a woman. Couldn't hurt. Just make sure it is safe and that she is highly rated.

I was thinking of getting both a man and a woman escort. I need release! Thinking more a muscular man, but not into penetration so much with men or oral. I just like the feeling up of each other. With woman escort, I'd want penetrative sex.

It is normal and natural to have sex. It's how we were all created.

 

[justahornyguy174]

I agree with you. He might need to explore his sexuality with a woman. Couldn't hurt. Just make sure it is safe and that she is highly rated.

I was thinking of getting both a man and a woman escort. I need release! Thinking more a muscular man, but not into penetration so much with men or oral. I just like the feeling up of each other. With woman escort, I'd want penetrative sex.

It is normal and natural to have sex. It's how we were all created.

Do it, you only live once!

 

[BIGBULL29]

Do it, you only live once!

You're exactly right.

I'm tired of repressing sexual urges. It's normal and natural to have sex. I am over the repression and shame. We're wired to have sex. Just look how our penises work, as men.

I plan to at some point. I want a muscular dude for an evening. Then, if I feel good about that, I might go for a fuller woman with big titties.

 

[Micheal Derry]

Thanks for sharing your experience — sounds like it gave you some clarity and a new perspective. If you're open to exploring more in a comfortable, low-pressure setting, you might want to consider checking out platforms that offer a bit more choice and control over the experience. One option worth looking into is Girls London official site, where you can browse discreetly and see what appeals to you. It can be a great way to reconnect with your preferences without any expectations or judgment.