First Time Concerns

[MattyMoonTonight]

I’ve recently been in contact with my primary care doctor, and I’ll be starting on Prep soon. So, I was wondering if there were some words of advice you more experienced and well-traveled members here could give to someone who is unfamiliar with these experiences but would really like to know.

The common sense ones I’m well aware of; safety and consent. I’ve researched this topic many times before on other online forums or knowledge market sites, but I’m wondering if you folks have others. If nothing else, it’ll ease some of my trepidation.

I’ve convinced myself that I’m ready for sex, but I know I’m not; a desperate want for human contact and physical connection in lieu of an emotional one aren’t really good credentials, not when coupled with the thought that I still haven’t found some sense of self-worth. But maybe some chance encounter in the future will lead to a feeling of self-worth, or maybe a genuine relationship that I’d be willing to enter, though I know that’s becoming rarer and rarer. I’m not going to be obnoxious and say I’m too old to be trying this, but I’m not young enough to be seduced by the idea that I’m very attractive, or that others in a similar situation are looking for the same things that I am. Things aren’t going to go to plan.

This year, I’ve been working on-and-off on a novella that explores how the reality of sexuality, identity, and expression often conflict with one’s fantasies, and it’s been making me try to further understand my own wants and needs from a sexual standpoint. There are plenty – plenty – of activities I’ve fantasized doing with potential partners, but I’m pragmatic enough to know they might not be into those things or aren’t ready, or maybe even I wouldn’t be ready when eventually faced with the situation.

This is starting to sound like cathartic venting and I apologize. Point being: What are some advisory notes you would give, as someone with sexual experience, to someone who’s grown tired of using toys and is starting to get out into the world?

 

[KaraBulut]

The first question for you is, "What are you wanting out of the experience?".

We tend to focus on "first times" as a single event. When it comes to sex, it's usually a series of events. Don't try to get all of the first times in a single night; that's not a reasonable expectation.

When it comes to "First times", they have a lot of different purposes. Some first times are the equivalent of jumping off of a diving board for the first time. It's something that you have to get done in order to remove the barrier to jumping off again. After all, there has to be a first time for everything.

Where we tend to be less aware of first times is when it comes to dating. Going out to on a date can be equally as nerve-racking as a sexual first time. First time PDA is another milestone. Introducing a boyfriend to friends and family is yet another.

 

[MattyMoonTonight]

The first question for you is, "What are you wanting out of the experience?".

We tend to focus on "first times" as a single event. When it comes to sex, it's usually a series of events. Don't try to get all of the first times in a single night; that's not a reasonable expectation.

When it comes to "First times", they have a lot of different purposes. Some first times are the equivalent of jumping off of a diving board for the first time. It's something that you have to get done in order to remove the barrier to jumping off again. After all, there has to be a first time for everything.

Where we tend to be less aware of first times is when it comes to dating. Going out to on a date can be equally as nerve-racking as a sexual first time. First time PDA is another milestone. Introducing a boyfriend to friends and family is yet another.

It took me a while to see this, and a bit longer to think about it. I suppose I was being intentionally vague for answers, but I can see it was a bit all over the place.

Combating impatience over things I feel I “should have” done by now is something I’m still trying to do. It’s immature, but I feel like these wants aren’t entirely individual, right?

The answer is somewhat multifaceted. A sexual encounter, positive or negative, would at least let me know that somebody might see me as attractive or interesting enough as a partner, and I’m sure it would help with my self-confidence communicating with guys and indulging in the act in the future. Fiction tells me that sex ought to be as much an emotional as a physical act, and I do agree with that, but particularly in the LGBT community, finding partners isn’t all that easy, and even though I’m interested in a genuine relationship, I know that many are not. If a sexual encounter leads to something more serious, I’d be open to it.

It would also make me feel better if I knew I was good enough to please a man.

Dating, public affection, just going out and being confident that I'm with someone who could compliment me and I could compliment back (from an emotional aspect), is something I’d love to happen. But until that happens, I’ll settle for being a sex object.

 

[KaraBulut]

...The answer is somewhat multifaceted. A sexual encounter, positive or negative, would at least let me know that somebody might see me as attractive or interesting enough as a partner, and I’m sure it would help with my self-confidence communicating with guys and indulging in the act in the future. Fiction tells me that sex ought to be as much an emotional as a physical act, and I do agree with that, but particularly in the LGBT community, finding partners isn’t all that easy, and even though I’m interested in a genuine relationship, I know that many are not. If a sexual encounter leads to something more serious, I’d be open to it.

It would also make me feel better if I knew I was good enough to please a man.

Just to set expectations...

It's unlikely that a sexual encounter with someone is going to fulfill the expectations that you have. As the saying goes, "You can't find your self-esteem in someone else's pants". Self-esteem, at least the lasting kind, is going to come from within you.

Something you might consider is a friends-with-benefits (FWB) situation. The nice thing about a FWB is that you get to be friends without undue expectations, it's a comfortable way to explore and you can get honest feedback about how you interact with people, etc.

 

[MattyMoonTonight]

Just to set expectations...

It's unlikely that a sexual encounter with someone is going to fulfill the expectations that you have. As the saying goes, "You can't find your self-esteem in someone else's pants". Self-esteem, at least the lasting kind, is going to come from within you.

Something you might consider is a friends-with-benefits (FWB) situation. The nice thing about a FWB is that you get to be friends without undue expectations, it's a comfortable way to explore and you can get honest feedback about how you interact with people, etc.

You're right. The damning thing is I know you're right, but my mind will still get stuck in my presumptions of what should be. I keep looking for silver bullets to my worries and issues without bothering to take the time to fashion them on my own. I'm not so sure how to go about finding friends-with-benefits; truthfully, I've never really thought it was a real thing. At the very least, it doesn't seem like a sustainable kind of relationship to me. Just by hearing stories, it feels like over time, either the friend aspect of it will fall apart, or the sexual aspect will.

Since my expectations are too high, what would be something more reasonable? I'd like to approach this thing sensibly, just so I don't come across as a nervous fool like I am now.

 

[KaraBulut]

You're right. The damning thing is I know you're right, but my mind will still get stuck in my presumptions of what should be. I keep looking for silver bullets to my worries and issues without bothering to take the time to fashion them on my own. I'm not so sure how to go about finding friends-with-benefits; truthfully, I've never really thought it was a real thing. At the very least, it doesn't seem like a sustainable kind of relationship to me. Just by hearing stories, it feels like over time, either the friend aspect of it will fall apart, or the sexual aspect will.

FWB, both gay and straight, is common. It describes a relationship where you're sexually comfortable with each other but there's no romantic interest. This can be friends that you hang out with or just someone who comes over when you're both wanting to have sex.

What usually ends the FWB arrangement is that one of the friends finds a romantic interest or moves on to something else. Occasionally it ends because someone develops romantic feelings.

Since my expectations are too high, what would be something more reasonable? I'd like to approach this thing sensibly, just so I don't come across as a nervous fool like I am now.

There's an "analysis paralysis" theme to your predicament. When faced with opportunity, you have a tendency to over-analyze it until the opportunity passes.

This might be the point where you consider working with a therapist to determine what is at the root of the self-doubt and why there are these obstacles preventing you from finding the things that you want?

 

[MattyMoonTonight]

FWB, both gay and straight, is common. It describes a relationship where you're sexually comfortable with each other but there's no romantic interest. This can be friends that you hang out with or just someone who comes over when you're both wanting to have sex.

What usually ends the FWB arrangement is that one of the friends finds a romantic interest or moves on to something else. Occasionally it ends because someone develops romantic feelings.


There's an "analysis paralysis" theme to your predicament. When faced with opportunity, you have a tendency to over-analyze it until the opportunity passes.

This might be the point where you consider working with a therapist to determine what is at the root of the self-doubt and why there are these obstacles preventing you from finding the things that you want?

I know I'm repeating a previous post I made, but I just don't have a social circle. Nobody comes to my place, and nobody invites me anywhere. Where I live, there are no queer people, and even the straight people appear averse to socializing. For some people, these things are just hard to come by.

That's a good and pretty accurate assessment. I've never heard of analysis paralysis, but it's certainly something I may have, coupled with a fear of humiliation, or at least being in a position of negative consequence. have been seeing a therapist for just over a month already, but sex and intimacy haven't been topics that's been brought up. It's more about getting a handle on chronic depression and past experiences, not really fixing things in the present.

I know I have to take things slowly and actively seek out being in these situations rather than bemoaning everything, but these things are too far away.

 

[BiBtm64]

As always, KaraBulut gives the best advice. I'll add my two bob's worth for what it's worth.

You say you've convinced yourself that you're ready for sex, but you know you're not. Then I sense that you're low on self esteem and you're hoping to prop that up by being attractive or interesting enough to another man, and good enough to please him. It's a risky thing to try to peg your sense of self worth on how someone else sees you, especially if that's through first-time sex, and especially if it's with a chance encounter.

First time sex - depending how far you go - can be a major thing to do. As KaraBulut says, there are many types of first-times, but I'm guessing if you're starting PrEP you are at least seriously considering receptive anal penetration. There's a lot to deal with, physically and emotionally, to make that a positive experience the first time. You might want to consider taking things a step at a time. If the moment feels right, and you feel ready, by all means go for it, but don't feel that you should do anything to please a guy or to be attractive or interesting.

I also think a FWB would be a good way to test the waters, take things a step at a time, and become accustomed to intimacy with that same guy that you can feel comfortable with. It's not a relationship, and don't expect it to develop into one. It can end any time for a bunch of reasons, and it's good manners to not ask why and to not plead with them to come back. Don't get too attached, just take the opportunity to discover new sexual experiences. Those can be anything from touching, to anything more.

Another thing I'd add is don't peg your self worth against your impatience over things you feel you “should have” done by now. Sexual experiences are not a race. Maybe you're held back by your analysis paralysis, maybe by lack of opportunities. Don't blame yourself for not having had sex by now. You can only change what comes in your future.

I think you should all of this to your therapist.

 

[KaraBulut]

I know I'm repeating a previous post I made, but I just don't have a social circle. Nobody comes to my place, and nobody invites me anywhere. Where I live, there are no queer people, and even the straight people appear averse to socializing. For some people, these things are just hard to come by.

Just for fun... download an app like Grindr. You'll be surprised. If you have a hospital or a university within a couple of hours drive, I can guarantee you that there are gay people living in your area. You just haven't figured out that they are gay.

...have been seeing a therapist for just over a month already, but sex and intimacy haven't been topics that's been brought up. It's more about getting a handle on chronic depression and past experiences, not really fixing things in the present.

That's very good news.

 

[MattyMoonTonight]

As always, KaraBulut gives the best advice. I'll add my two bob's worth for what it's worth.

You say you've convinced yourself that you're ready for sex, but you know you're not. Then I sense that you're low on self esteem and you're hoping to prop that up by being attractive or interesting enough to another man, and good enough to please him. It's a risky thing to try to peg your sense of self worth on how someone else sees you, especially if that's through first-time sex, and especially if it's with a chance encounter.

First time sex - depending how far you go - can be a major thing to do. As KaraBulut says, there are many types of first-times, but I'm guessing if you're starting PrEP you are at least seriously considering receptive anal penetration. There's a lot to deal with, physically and emotionally, to make that a positive experience the first time. You might want to consider taking things a step at a time. If the moment feels right, and you feel ready, by all means go for it, but don't feel that you should do anything to please a guy or to be attractive or interesting.

I also think a FWB would be a good way to test the waters, take things a step at a time, and become accustomed to intimacy with that same guy that you can feel comfortable with. It's not a relationship, and don't expect it to develop into one. It can end any time for a bunch of reasons, and it's good manners to not ask why and to not plead with them to come back. Don't get too attached, just take the opportunity to discover new sexual experiences. Those can be anything from touching, to anything more.

Another thing I'd add is don't peg your self worth against your impatience over things you feel you “should have” done by now. Sexual experiences are not a race. Maybe you're held back by your analysis paralysis, maybe by lack of opportunities. Don't blame yourself for not having had sex by now. You can only change what comes in your future.

I think you should all of this to your therapist.

Yeah, that’s all true. From an outside perspective, I can see that this thread is from someone so desperate for human contact that he considers giving up self-respect for it. At the risk of sounding like someone half my age, I wish I was doing all of this under different circumstances, something where the intimacy part isn’t removed from the equation and I have an established, real connection with a partner. But that just didn’t happen for me, and I have to figure things out in a different way.

It's agonizing that there’s no real roadmap for this sort of thing, something that’s readily available when you want it and you don’t feel like your stepping into the deep end of a pool in the middle of the night.

Not sure where to find an FWB. I know I can’t afford one.

I hope I’m not sounding like those incel psychotics I hear about every now and then. I’m fully aware that I’m as much at fault for lacking love and relationship experience as my environment. I know I can change things, it’s just difficult to know where and how to go about doing things without a friend group to talk to (a real tangible group, I mean. As helpful as sites like this are, there are limitations to online communication).

Just for fun... download an app like Grindr. You'll be surprised. If you have a hospital or a university within a couple of hours drive, I can guarantee you that there are gay people living in your area. You just haven't figured out that they are gay.


That's very good news.

To be honest, I did download Scruff at the start of the year. I was very enthusiastic about 2025 being the year I would start trying to be more “myself,” more “authentic,” and part of those plans included my making an attempt in the dating scene, which at the time I didn’t know was so scanty, hypercritical, or downright distrusting. I downloaded it, but have yet to set up an account.

I’ve thought about Grindr, a hot little thought in the back of my mind, but I keep thinking about the catfishing acts ending in assaults or manslaughter over the past decade or so. They were bad enough to end up in the media, and I’m sure there are scores of crimes that happen through Grindr meetups that haven’t been made public. I know it happens on all these apps.

Despite this, I still made an account on a popular cruising site, and that’s the one I’ve been putting effort into. Typing this out makes it sound like a contradiction. I’ve had it for most of the year now, but I’ve just been too nervous to do anything more than play around with profile details.

 

[KaraBulut]

I’ve thought about Grindr, a hot little thought in the back of my mind, but I keep thinking about the catfishing acts ending in assaults or manslaughter over the past decade or so. They were bad enough to end up in the media, and I’m sure there are scores of crimes that happen through Grindr meetups that haven’t been made public. I know it happens on all these apps.

Grindr (and the other apps) are evolving. When they originally came out, they were a replacement for dating websites and chatrooms and were a way to online shop for hookups.

Now, each of the apps has taken on a different flavor and in some cities, Grindr has taken the place of rentboy.com for escorts. Most of the people that I know are now just using the geolocation feature. It is a quick way to figure out who at the gym, at Costco, etc is gay. One guy that I know uses it at Whole Foods to zero in on hookups. The apps are also a good way to advertise in public places that you're gay and open the door for other guys to approach you.

The point of my comment about using an app was to quickly dispel you from the belief that there are no gay people where you live. They're there. They're likely more camouflaged than they would be in NYC or LA, but they're there.

Figuring out who is gay is the first step. Letting know you're gay is the second step. The rest is up to you.

 

[MattyMoonTonight]

Grindr (and the other apps) are evolving. When they originally came out, they were a replacement for dating websites and chatrooms and were a way to online shop for hookups.

Now, each of the apps has taken on a different flavor and in some cities, Grindr has taken the place of rentboy.com for escorts. Most of the people that I know are now just using the geolocation feature. It is a quick way to figure out who at the gym, at Costco, etc is gay. One guy that I know uses it at Whole Foods to zero in on hookups. The apps are also a good way to advertise in public places that you're gay and open the door for other guys to approach you.

The point of my comment about using an app was to quickly dispel you from the belief that there are no gay people where you live. They're there. They're likely more camouflaged than they would be in NYC or LA, but they're there.

Figuring out who is gay is the first step. Letting know you're gay is the second step. The rest is up to you.

I've been using the past couple of days to think over this thread. I'm going to make a concerted effort with the apps. Or at the very least I want to make an attempt. I don't like the idea of resorting to them because I know they're not reliable for the sort of relationship I'm looking for and I don't like the risk of violence. For another point, I don't like leaving things to chance, because the only certainty of leaving things to chance results in failure, based on my experience.

But I've set up accounts on Scruff and Grindr (I'm not too chuffed about recent reviews about the app, but I saw that they're trying to do the same thing that Sniffies does, pushing away from a dedicated app for Web use so maybe that will be different), and I'm hoping that at the very least, it will lead to something more positive than what I keep seeing in my mind.

 

[BiBtm64]

I've been using the past couple of days to think over this thread. I'm going to make a concerted effort with the apps. Or at the very least I want to make an attempt. I don't like the idea of resorting to them because I know they're not reliable for the sort of relationship I'm looking for and I don't like the risk of violence. For another point, I don't like leaving things to chance, because the only certainty of leaving things to chance results in failure, based on my experience.

But I've set up accounts on Scruff and Grindr (I'm not too chuffed about recent reviews about the app, but I saw that they're trying to do the same thing that Sniffies does, pushing away from a dedicated app for Web use so maybe that will be different), and I'm hoping that at the very least, it will lead to something more positive than what I keep seeing in my mind.

Good luck buddy. Remember - you don't need to rush into anything.