Seeking Advice: Convincing My 19-Year-Old Best Friend to Experiment Sexually

[thefatcow200]

Hi all,

I hope you're all doing well. I find myself in a bit of a unique situation and could really use some advice. I have a close male friend, 19 years old. We have a great bond and enjoy playing tennis, going to the gym, swimming during the summertime, talking on discord every single day, and just hanging out.


Lately, I've been feeling curious about taking our friendship to a more intimate level. I believe there might be some mutual interest, but I'm not entirely sure how to approach the topic with him. I value our friendship immensely and want to be respectful and considerate in any approach. The reason why I think he wouldn't mind is because of the fact we talk almost everyday, he hasn't had a girlfriend since 2021, we have the life360 app so we know where we are at all times, he has complemented my leg progress in the gym and causally touched my legs, chest, back, and face a few times, and says that I am beautiful along with thinking my hair is better looking than his, and has been my friend even through bad things I have done in the past that he doesn't seem to care about.
I would appreciate any advice or suggestions on how to broach this subject delicately. Also, I will share pictures of him to provide context, but I want to make sure it's appropriate and respectful. What do you think would be the best way to navigate this situation?
Looking forward to hearing your thoughts.

 

[chrisrobin]

Firstly does he know you like sleeping with men - if not you should drop that fact and go from there. Mind you theres a risk you might lose a friend, which is more important, sex or friendship?

 

[thefatcow200]

Firstly does he know you like sleeping with men - if not you should drop that fact and go from there. Mind you theres a risk you might lose a friend, which is more important, sex or friendship?

good question, I do value our friendship and I don't think me asking will ruin it, but if it does it won't be that big of a loss for me

 

[thefatcow200]

do you want to see pics of him?

 

[chrisrobin]

do you want to see pics of him?

always

 

[art]

I wouldn't post pictures of somebody else without his permission. That seems like a violation to me.

 

[thefatcow200]

even if they don't show his face? he has really hot legs and ass

 

[zaynmlk1626]

you could hide his face and show gym pics for example, how old is he? why don't you start a discusion about gay men and see what he thinks about them?

 

[bravesoldier]

This is what I would suggest even though if it were me, I'd probably have a hard time doing it.

Being you have experienced the things you have with him, (touching, compliments, level of friendship, etc.) I'd suggest to simply plan what you're going to say without overthinking it too much. Gather your thoughts, find the right uninterrupted time and place and say something like this- We've been close friends a long time. I respect you more than you know but because of what I hope could be true, I'd like to respectfully ask if you're interested in taking our friendship to a sexual level.

It might be a shocker to him, but I think only you know the chances you have with him reciprocating positively. Remind him before he answers that you have total respect for him and if he's not interested, you hope he won't be offended, and your friendship will continue.

Of course, be prepared for a negative response because it is as possible as a positive response. Based on what you shared about your relationship, I think you have an excellent chance of hearing what you want to hear.

 

[theplayerking]

The easiest way to play with straight-curious guys is to out yourself and then it’s up to him. The scenario where to straight-ish guys are playing sports and then start fooling around is hot in a movie, but rarely happens in real life.

 

[ILoveGames48]

Over the years I’ve had a bad thing about seeing someone I liked and getting to know them..

And I wouldn’t flat out say I had the hots for him ( at least not always )but I’d ask him if he ever had any guys tell him they think he is hot .. see his react ..

Sometimes nothing would happen.. others the guy would say sometimes but then turn the table on me and ask me if I thought he was hot. And I never ever hid that answer on that .. I’d tell him is is freakin hot .. ..

When he’d ask.. if I let you what would you do to me. And I’d tell him suck his cock n balls and rim his ass .. he smiled and asked if I swallowed and if I liked being fucked .. and if I said yes and yes then he’d be like prove it.. so we’d go to my place where I prove it.. sometimes more than once

 

[RJ5on1]

Hey @thefatcow200, keeping it simple is usually a good way to broach something like this. Remember, you're just wanting to open a line of conversation with him, and see where it goes, right?

(Without being timid, shy; nor boastful, but with true confidence in knowing that all guys do it, so it's no big deal...)

Simply say (in one short sentence) something like, "... I've been horney all day, I think I'm gonna bust one out... what about you?"

Say nothing else, even if he hesitates a little. Give him the time he needs to respond - He will, and then you'll know where the conversation will go next.

Have fun with this, and keep us posted, OK?

 

[Brodie888]

You've listed yourself as a shade of bisexual on this site, so I would go with that in discussions with your friend.

I'd suggest watching a tv show or movie with sexually fluid themes and discuss.

Something along the lines of "I like girls but if the right opportunity came along I probably would be curious enough to see what it was like with a guy".

 

[Topher the Gopher]

Given your name and number of posts, I think you're a troll.

 

[Meisme]

As it's been said, keeping it simple is the best advice, IMO. If it turns to appear romantic, 'serious', creepy or even truly 'gay', you might just lose your chances. The best way to succeed is to make it appear like a sort of game, something just between you and him, nothing involving the possibility to conclude that one of the both of you may be interested in other men, and by so being really gay. The label 'gay' is something that scares straight guys in a way, even the curious ones and even the closeted bi ones. They don't want to lose their straight privilege of being part of the 'normality'.
You have to dodge every aspect which might scare the guy, mostly by having to question himself about who he is.
Good Luck !

 

[thefatcow200]

Given your name and number of posts, I think you're a troll.

Trust me I'm not I just wanted actual advice

 

[thefatcow200]

you could hide his face and show gym pics for example, how old is he? why don't you start a discusion about gay men and see what he thinks about them?

He is 19 just like I am

 

[thefatcow200]

Here he is

 

[viscountwxyz]

even if they don't show his face? he has really hot legs and ass

Unless he explicitly told you he's cool with it, don't even think about it.

 

[thefatcow200]

More of him