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

[ILoveGames48]

I am just wondering 1 you both drink?

What kind music listen to?

Trust me .. these questions are important

 

[Exdoria]

TRUE STORY: I don't recommend it, when I was 19/20 I had sex with my straight friend from school. We moved to the same city for university. We went out one night and since my apartment was closer to the club we decided to sleep at my place if we got too drunk. So we were. We came to my place talked about him not having a girlfriend for more then a year, he got very insicure and asked me if I thought his dick was ok. (mind you he showed me it through his underwear). I don't know what came over me but I just said "I wouldn't know I normally have to have it in my mouth to see if its a good dick", and I just did. He didn't say anything and I could see that he was enjoying it even if I saw that he had a confused expression.
But after a while he had a crazier behavior then mine.
He turned me around and fucked me till he came inside me.

I loved it and in a way clearly he did too but we never spoke about it.
After that every time he came to me for a "sleepover" he straight up put his dick out and wanted me to suck it or have sex with me, still whiteout commenting on what he was doing.
It felt good first, I always had a bit of a crush on him but at the end I noticed that from one of his best friends I became basically his personal flashlight.
Sometimes he came to my apartment just to fuck me because "he had a stressful day and needed to cool off" but instead of talking to me like we used to do he just left me after he came inside.
As you can see it's not a happy ending, after a few months he finally find himself a new girlfriend and we never did it again, never talked about it and now I basically see him once a year.

I just know he was embarrassed for what he did, probably couldn't comprehend why and how he could have had sex with a man if he is straight.

So I treaded a close friend for sex for a few months, so I really wouldn't do anything with him if I were you.

 

[Tommys4goodtimes]

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.

Hi! I hope you've had luck so far; if not, you should have a " guys night" together, you know, watch a movie together & during your time together, casually drift into a discussion about adult relationships & " things in common" & see what he thinks about things going to another level. Having different things in common & openly discussing them helped bring my BF & myself together, So you never know. Good luck!

 

[Lucius2s1]

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?

Would be my approach too.

 

[thefatcow200]

Update: so since my last post he has been very nice to me, talking about how good I look since I've started going to the gym (he even said I was caked up a few days ago lol)

 

[thefatcow200]

I try to pretend to be straight as well and we talk about girls and sex and stuff like that, he even asked me how big my thing was and I put both of our phones together to exaggerate lol and he said he needed to see for himself, he actually said that twice that day lol

 

[ILoveGames48]

If he is your best friend.. for how long?

Is talking him into sex worth ruining a friendship?

 

[Lucius2s1]

I try to pretend to be straight as well and we talk about girls and sex and stuff like that, he even asked me how big my thing was and I put both of our phones together to exaggerate lol and he said he needed to see for himself, he actually said that twice that day lol

Good stuff. Little by little building it up.

 

[kasturi]

How old are you?

Just a hunch.. i feel he isn't 19 and you are making this all up

 

[Jakeyboi_04]

He got big balls?

 

[thefatcow200]

How old are you?

Just a hunch.. i feel he isn't 19 and you are making this all up

no we are both 19 to be exact, I know it's hard to believe but its the truth

 

[thefatcow200]

another Convo we had today. we played some tennis and afterward the conversation in person led to him asking to see my dick again, and later tonight I asked him if he was joking on discord...

 

[thefatcow200]

 

[Dontask321]

View attachment 139269841

U should share some of the pics he’s sent you

 

[thefatcow200]

U should share some of the pics he’s sent you

I haven't actually sent it yet, I responded by saying that I will when the time is right and he hearted that comment

 

[thefatcow200]

the weird part about is that I did actually confess to him that I am bi-curious a couple of days before he asked to see my dick, and he said that while it wasn't weird, he is currently trying to become more religious, so he couldn't approve of it.... and then he asks to see my dick, multiple times lmao so he may be in the same boat I am in regards to finding our sexuality

 

[thefatcow200]

and he's given me even more hints, as he's complemented my progress at the gym, saying that my legs look good, and that I'm caked up too! he's said I am beautiful multiple times as well.

 

[Lucius2s1]

maybe go out and talk about it in the car.

 

[Dontask321]

and he's given me even more hints, as he's complemented my progress at the gym, saying that my legs look good, and that I'm caked up too! he's said I am beautiful multiple times as well.

It sounds like he’s acknowledging to himself that he does have attractions or at the very least sexual curiosity with other males and he is a little insecure about this/is afraid it’s wrong so he’s leaning a little more into religion to “fix” it. Just a guess. But he will very likely come to the conclusion that it’s ok and it’s not wrong and want to act on/experiment with these feelings. How about some pics of u?

 

[FrankieGuile]

Although I have my doubts based on the original post, I'm going to assume the question is a genuine one and not an excuse to show photos of, or discuss the physical attributes of, a stranger.

First, you characterize "broaching the subject" of "convincing" him to experiment sexually with you as a delicate one. If you are gay and attracted to him -- which is evident -- and he is gay and attracted to you -- which is yet unknown -- then you have nothing to lose by simply saying words to the effect, "I am attracted to you and want a sexual relationship. How do you feel about that?" If he is attracted to you and homosexual, then the answer will be "yes" and you can get on with it. If he is not attracted to you and homosexual, then the answer will be "no" and you can get on with it. If he is not homosexual, then the answer will be "no" and you can get on with it.

Second, there is something desperate and disrespectful about "convincing him" to have sex with you. A better approach, which respects his sexual orientation, whatever it is, would be to ask him his sexual preference, as I suggest above. Surely, you must know that attempting to convince someone to have sex with you is bound to be unsatisfying at best and an utter failure at worst.

In the meantime, spare us the photos. You want to have sex with him, not us.