How To Ask An Awkward Question ????

[DeQwanNayshon]

Hey guys I have a question , I really wanna masturbate with my gay bestfriend and jerk each other off but I don't know how to bring it up in a text conversation without it being awkward and if I was at his house how would I just randomly say let's jerk off together , I just don't wanna make him uncomfortable

 

[gumshoe]

How old are you guys? I'd guess teenagers perhaps?

What is it about your best friend that makes you want to jerk off with him rather than another guy? I've had a few guys that I considered good friends that I would have jerked off with but I never made any sort of move because I figured they wouldn't be into it and I think it's important for yourself, the other person and the relationship to keep things on a strict friend level. Depends on how you view sex and sexual activities, whether as just a fun thing you do as a passtime, or something more, but sometimes things like that aren't really something a lot of people want to do casually with close friends. So there's a certain expected limitation there.

If you're sure that you're okay with crossing that line, should such a line exist for you, then I think it depends on how open you guys are to talking about sex in general. I know myself and my friends are pretty open with talking about it, mostly just our own experiences or joking around or anything. I've never jerked off or done anything sexual with a majority of my friends though but if I were to want to, I'd probably bring up the topic of sex. Talk about masturbating perhaps. Lead the conversation to talking about things like where you like to do it. Techniques. Maybe ask if he's ever jerked off in a circle jerk or with friends or whatever. Judge his answers and comfort level and if you're okay with it, maybe ask if he wants to jerk off then and there, or say that you're suddenly horny and see how he responds.

Be careful not to make it seem like it's something you've planned, even though it clearly is since you made this topic. But you don't want him to think you're coming on to him or that you're a pervert. It's just a casual thing and give him the freedom to say no without being disappointed if he does. Laugh it off or whatever.

 

[DeQwanNayshon]

Wow thanks a lot , you give great advice , bur the reason I wanna do it with him is bc I'm actually in love with him , and it doesn't help that I'm a virgin I'm 19 btw & he's 18 , virgins think about sex way more than people that do have sex so its even harder for me and the fact that my sign [ sagittarius ] loves sex doesn't help matters either

Its crazy tho bc we planned to have sex together months ago and that I would loose my virginity to him , but than he changed his mind bc he thinks things would change between us friend wise and I really don't believe that I think sex only changes things if you let it

Iguess bc I have deep feelings for him ijust can't stop thinkin about him like I wanna do things with him , but I'm assuming if he doesn't wanna have sex with me than he probrably wouldn't wanna masturbate with me either ?? :-/

Its just so hard falling in love with your bestfriend [ sigh ]

 

[Rolyo85]

Um, if he is straight, you need to back off, instantly, and forever. If he's not, and you love him, you don't want to start with jerking off, but with actual romantic stuff. And before even that - with some bonding, letting him know how you feel...

 

[KaraBulut]

Your friend is wise to consider how sex could complicate your friendship.

He probably is on to the fact that you have a crush on him.

You would probably be better just following his lead and not taking a friendship into a place that he doesn't want it to be.

 

[sixthson]

Um, if he is straight, you need to back off, instantly, and forever. If he's not, and you love him, you don't want to start with jerking off, but with actual romantic stuff. And before even that - with some bonding, letting him know how you feel...

He said he was his "gay best friend" in his opening sentence.

To the OP: If you love him, why are you settling for mutual masturbation? Is he because he doesn't feel the same?

 

[Rolyo85]

Yeah, I saw that. Sorry. Well, the rest of the post stands.

 

[thisisinteresting]

but than he changed his mind bc he thinks things would change between us friend wise and I really don't believe that I think sex only changes things if you let it

While this rings true, you would obviously let it. You have deluded yourself into thinking you're in love with him, for one - with feelings this strong, as someone who's never been with anyone, I'd gamble that you're not capable of having sex with this person and seperating your romantic feelings for him.

You are in lust with him, not in love with him. Being in love with someone is not this romanticized movie-ideal where you watch someone from afar and are captivated by them and that makes you in love with them. It may be very very powerful lust, but you're not in love with this friend. And if you really think you are, you need to do something about it. You need to at least tell him you have feelings for him so that you can hear how he feels about it. If he's not interested then you can start trying to get over it now, rather than letting these feelings brood and muster for years until it truly becomes something as powerful as love.

As for how do you ask an awkward question? Via text? Just do it. There's no easier way to ask an awkward question than behind a screen (i.e. text message, e-mail, etc) because you don't have to deal with awkward body language or wanting a reply right away. Texts can have very random subject matter and you should just go for it and ask him something.

Something needs to change here. Make it happen, instead of just dwelling on it.

 

[DeQwanNayshon]

I Just Feel As Though He's Not Ready For Me To Express Those Feelings For Him , He Knows I Like Him , But He Doesn't Know How Deep It Is , What's The Point Of Expressing Yourself To Someone If They Aren't Ready Or Even Willing To Have An Open Mind About Enterting Into A Relationship , I Wanna Confess Everything I Feel About Him So Bad , But It's So Much &nd My Pride Gets In The Way Of Everything I Absolutely Hate Rejection .

 

[Seasoned]

You're at the point of wondering if taking a risk would end the friendship. It might. On the other hand obsession is painful and scary and your mental health comes before all else. Having a friendship that leaves you frustrated may have more serious consequences than losing the friendship. I don't know. You'll have to decide that. I don't think there's anything wrong with telling him you're horny and you want to jerk off.

When I was 19 I had a friend who whipped it out and started jacking when I was in the bathroom. I came out and wasn't interested in joining in. He put it away and it never happened again. I guess I've been lucky. I've never had a crush on a friend.

 

[DeQwanNayshon]

You're at the point of wondering if taking a risk would end the friendship. It might. On the other hand obsession is painful and scary and your mental health comes before all else. Having a friendship that leaves you frustrated may have more serious consequences than losing the friendship. I don't know. You'll have to decide that. I don't think there's anything wrong with telling him you're horny and you want to jerk off.

When I was 19 I had a friend who whipped it out and started jacking when I was in the bathroom. I came out and wasn't interested in joining in. He put it away and it never happened again. I guess I've been lucky. I've never had a crush on a friend.

Omg yesssssssssss ! Your dead on ! I'm always Frusturated about what its Like I try to act like everything is cool and we're fine but its like I have feelings too and I don't know how much longer I can ignore these urges , but I respect our friendship and value it so much I don't wanna loose him .

 

[gumshoe]

The urges can be ignored if you have something else to distract you.

Not that I'm suggesting you go out and try to hook up with someone but perhaps trying to focus the sexual energy somewhere else will work. It depends on what you value more, guaranteed friendship or the potential of sabotaging it because of sexual urges.

 

[Georgiadude]

I really think you need to think long and hard about this. Are you absolutely sure your ok with losing him as a friend? Look through this forum. It's full of threads from guys that were in the same situation. They went for it and ended up losing their best friend. Of course there are a few threads from guys where things worked out but they are by far the minority. I'm not saying you shouldn't pursue it. I'm just saying you really need to make sure your not going to regret your decision like so many others have.

I think he sent a pretty clear signal when he said he didn't want to risk the friendship over sex. You could test the waters a little bit but I'm afraid your setting yourself up for some heartache and pain. Good luck with whatever it is you decide to do. Just be at peace with your decision before you do it. Once the door is open, you can't close it again.

Best wishes.

Steven.

 

[glasvegas]

virgins think about sex way more than people that do have sex

I feel you mate.

I kinda pop the question with my gay friend. I mean I was being down dirty flirting. ( I have no means to jerk with me. It'll be weird. Is just something I ask for fun. ) But he politely rejected as he has a boyfriend. But we're cool. You should just ask, see how he responded.

 

[maksim9061]

Wow, this sounds like I would have wrote 6 years ago. The only advice I can give is from my own personal experience. When I was your age, I was madly in love with my best friend. He was 25 at the time, and I was a virgin. I had the same fears that it would ruin a friendship, and that I would lose my best friend. (I'm guessing he is your go to person, who you feel the most free talking to, and stuff)
My advice to you is tell him how deep your feelings go. If he is truly a friend, he won't abandon you. Telling him will make you feel like a weight has been lifted off of your shoulders, because you will know longer have to worry about him finding out.
I told my best friend the depth of my feelings for him. He stated he was flattered, but did not feel the same way. We kept being friends, and my feelings went away eventually. Until one day, 2 years later, him and I were at a bar (no, we were not intoxicated) and he leaned over and started talking about the night I told him I had feelings for him. He told me that he wished he could go back to that night, and tell me how he really felt, how he still felt. My feelings all came rushing back, and we started seeing if we could turn our friendship into a relationship. My best friend is now my husband.
I wish you all the best, and I hope you, (and your friend when you tell him) find peace in your friendship, and figure it all out.

 

[Rolyo85]

virgins think about sex way more than people that do have sex

False

 

[DeQwanNayshon]

Wow, this sounds like I would have wrote 6 years ago. The only advice I can give is from my own personal experience. When I was your age, I was madly in love with my best friend. He was 25 at the time, and I was a virgin. I had the same fears that it would ruin a friendship, and that I would lose my best friend. (I'm guessing he is your go to person, who you feel the most free talking to, and stuff)
My advice to you is tell him how deep your feelings go. If he is truly a friend, he won't abandon you. Telling him will make you feel like a weight has been lifted off of your shoulders, because you will know longer have to worry about him finding out.
I told my best friend the depth of my feelings for him. He stated he was flattered, but did not feel the same way. We kept being friends, and my feelings went away eventually. Until one day, 2 years later, him and I were at a bar (no, we were not intoxicated) and he leaned over and started talking about the night I told him I had feelings for him. He told me that he wished he could go back to that night, and tell me how he really felt, how he still felt. My feelings all came rushing back, and we started seeing if we could turn our friendship into a relationship. My best friend is now my husband.
I wish you all the best, and I hope you, (and your friend when you tell him) find peace in your friendship, and figure it all out.

Wow This Gives Me So Much Hope , I Just Never Wanted Something So Bad In My Life , I Just Feel Like We Should Be Together , I Hope One Day He Realizes Everything He Needs Is Right In Front Of Him . [ Sigh ]