Losing My Virginity

[DragoCronzo]

I'm 26 and I've never had a relationship before, romantic or sexual. I have kissed some guys, do sext with a guy from another country every now and then, but that's as far as it goes. Since I'm turning 27 next month, I figured I should get it over and done with.

Here are my setbacks: I'm not terribly social. I find it hard to meet and interact with people. I'm also not super confident with my body. I was obese in school until I lost 30kgs in senior year. I do work out regularly and try to eat right, but I have bits of loose skin that erk me. Being the "fat kid" I never really felt sexy until I turned 22 and realized that people actually found me attractive. I did flirt with the idea of hooking up during that time but never went through with it.

Really I'm just looking for pointers on where to start, the dos and don'ts and whatnot.

 

[LoveMyPeppermill]

@KaraBulut always has excellent advice about this kind of thing.

 

[curiousbob]

I lost my same sex virginity at 13 and with a female at 16, both times were a bit shit and could have been a lot better.
You don't have to get anything over and done with just because your a certain age. The first time can be the most fun if you don't see it as something you have to achieve. Take the pressure off yourself. All I got was an arse full of cum a rock hard boner and the wet patch. The "lady" gave me an nsu and as I was drunk I couldn't get my load off so not the best start.
For pointers don't rush into anything and relax, it took me a failed marriage and over 40 years to find the right person, you have plenty of time.

 

[TX-Beau]

First times are rarely good sex. Start where you are comfortable. You could use a hookup site if you're not looking for a boyfriend, if you are looking for a relationship before you have sex, focus on that and leave the sex until later.

Be more specific, what exactly are you looking for?

 

[KaraBulut]

Really I'm just looking for pointers on where to start, the dos and don'ts and whatnot.

To get the superficial out of the way... I remember your pictures when you posted them probably 5 years ago. You won't have any issue finding someone to get naked with you.

Probably the most important thing for you to decide is exactly what you're wanting. Your choices are:

1. The "get it over" approach
2. The dating, progressive step-by-step approach
3. The "someone special" approach

None of these has any particular advantage over the other, in terms of the quality of the experience. First time sex, particularly first time anal receptive sex, is a roll of the dice. If you're wanting something/something that you'll remember, probably options #2 or #3 is what you're after.

Which brings us to the definition of what "virginity" means in the gay world. For some reason, some gay men, like their straight counterparts, still equate virginity with getting fucked. That's also something you need to decide: what is the threshold that you're wanting to cross so that you can say that you have "lost your virginity"?

My advice to you? Don't try to do it all in one night. Given what you're described in your opening post, I don't think the issues is that you haven't fucked or been fucked. I would suggest that maybe dating and putting yourself out there is the path to your objective of getting laid?

 

[DragoCronzo]

Update: So I went looking on dating apps. Ended up talking to a guy on snap. Attractive, fit, willing to host... but wants me to sign up with a "safety site". Checked it out; requires card details to register, under a year old, no social media, no links anywhere else, googling it takes you to links about scams... so obviously too good to be true lol.

 

[KaraBulut]

Update: So I went looking on dating apps. Ended up talking to a guy on snap. Attractive, fit, willing to host... but wants me to sign up with a "safety site". Checked it out; requires card details to register, under a year old, no social media, no links anywhere else, googling it takes you to links about scams... so obviously too good to be true lol.

"Thank you, next."

 

[LoveMyPeppermill]

Update: So I went looking on dating apps.

This advice is usually given to women, but it's generally good for us to follow, too: the first time you meet up with someone, do it in a public place. If you don't want to have a meal in a restaurant or café, go for a walk together. Keep all your spidey senses aware and trust them ("trust your gut") about whether or not to go home with him.

I think it's better to go to his place for the first time rather than having him come to yours, because if something goes bad, or even if you just decide you don't feel like pursuing it, it's easier to leave yourself than to throw someone else out.

And continuing from what KaraBulut said about "virginity," for your first time getting naked and doing something sexual with a guy, I'd suggest that you just plan to keep it to mutual handjobs and oral. If he pushes for anal, just bat your eyes and smile real pretty and say something like "On the first date? I'm not that kind of girl."

 

[DarkHelios]

What do you hope to accomplish by "getting it over with?"

If you want to have sex, great, go for it. But having done it once isn't going to suddenly make you an expert.

 

[LoveMyPeppermill]

What do you hope to accomplish by "getting it over with?"
If you want to have sex, great, go for it. But having done it once isn't going to suddenly make you an expert.

No, but it will get first-timer's nervousness over with.

 

[DragoCronzo]

lol just got ghosted
He liked my pics, engaged in conversation, said he was willing to meet up, even told me the days he was available so I said "ok this time tomorrow good for you?" and like a magician he was gone.

 

[KaraBulut]

lol just got ghosted
He liked my pics, engaged in conversation, said he was willing to meet up, even told me the days he was available so I said "ok this time tomorrow good for you?" and like a magician he was gone.

That seems to be part of it.

Continue being patient and understand that a lot of these guys are online because they're socially awkward and flaky.

 

[LoveMyPeppermill]

That seems to be part of it.

Yeah, @DragoCronzo, welcome to online dating ... [sigh]

Continue being patient and understand that a lot of these guys are online because they're socially awkward and flaky.

And/or they are more ambivalent about actually meeting someone than they might admit, even to themselves. (There are a surprising number of those people on the non-hookup apps.) You may actually be ahead of some of them that way, despite your lack of physical experience.

 

[DragoCronzo]

That seems to be part of it.

Continue being patient and understand that a lot of these guys are online because they're socially awkward and flaky.

And/or they are more ambivalent about actually meeting someone than they might admit, even to themselves. (There are a surprising number of those people on the non-hookup apps.) You may actually be ahead of some of them that way, despite your lack of physical experience.

I did sort of get that vibe throughout the conversation. A lot of calling me cutie and finishing his sentences with "hehe".

 

[LoveMyPeppermill]

I did sort of get that vibe throughout the conversation. A lot of calling me cutie and finishing his sentences with "hehe".

See? You are actually ahead of some of them!
Go forth and be confident and proud!

 

[Mackster]

HI My guy. Basically, put yourself out there.

I'm 26 and I've never had a relationship before, romantic or sexual. I have kissed some guys, do sext with a guy from another country every now and then, but that's as far as it goes. Since I'm turning 27 next month, I figured I should get it over and done with.

Here are my setbacks: I'm not terribly social. I find it hard to meet and interact with people. I'm also not super confident with my body. I was obese in school until I lost 30kgs in senior year. I do work out regularly and try to eat right, but I have bits of loose skin that erk me. Being the "fat kid" I never really felt sexy until I turned 22 and realized that people actually found me attractive. I did flirt with the idea of hooking up during that time but never went through with it.

Really I'm just looking for pointers on where to start, the dos and don'ts and whatnot.

Look around and see what attracts you. If you don't let it be known you're available nobody will know. And when you do become interested in a person, be honest with them. Be yourself but let them know hey, I'm new to this and I just want enjoy being with somebody...