how to ask

[turnandburn]

So I have a gay friend that I attemped to fool around with a while back and failed. He has sort of a thing for me but we've never done anything serious. Anyway I think I may want to try anal but how do I ask him without coming off as just some guy who wants to use him as a "test"

 

[medic1]

If he knows that you are bi-curious or whatever you want to call it,sit down with
him and explain that you are wanting to try anal but you feel that it is to precious a gift to offer someone you dont really know.
Explain that after thinking long and hard he is the only guy that you would feel comfortable trying anal with but re-assure him that afterwards you promise not to get into bunny boiler mode,most guys would be so chuffed thay someone is offering them their cherry i think you will get the answer you are looking for

 

[turnandburn]

Thank you! Ill have to sit him down sometime and ask him. We've been growing apart so hopefully his answer is yes. Maybe out to coffee or something...

 

[KaraBulut]

So I have a gay friend that I attemped to fool around with a while back and failed. He has sort of a thing for me but we've never done anything serious. Anyway I think I may want to try anal but how do I ask him without coming off as just some guy who wants to use him as a "test"

You can try- if you've already fooled around and gotten naked together, it's not like it's a shock.

But it's going to be difficult not to come off as just wanting to use him... because honestly, that's kind of what you're doing.

 

[HunterM]

"You have a HOT ass. It would give me great pleasure to fuck you. Are you game?"

 

[turnandburn]

You can try- if you've already fooled around and gotten naked together, it's not like it's a shock.

But it's going to be difficult not to come off as just wanting to use him... because honestly, that's kind of what you're doing.

I know.. i just would just rather i try it with someone i know than to do it with some stranger i hook up with on a website, or worse, craigslist... I definitely dont intend for it to be like im using him at all but unfortunately it is what it is. Maybe its better to just not bother with it now. i wouldn't want to put him in that position (no pun intended... or is there?).

 

[Toddxxx]

If you have attempted to fool around with him before and think he has sort of a thing for you, let it play out in bed. Sounds like the attraction is mutual. Go for it! It usually works out quite well in bed.

 

[KaraBulut]

I know.. i just would just rather i try it with someone i know than to do it with some stranger i hook up with on a website, or worse, craigslist... I definitely dont intend for it to be like im using him at all but unfortunately it is what it is. Maybe its better to just not bother with it now. i wouldn't want to put him in that position (no pun intended... or is there?).

What two consenting adults do in private is perfectly fine. But if you're just interested in a wham-bam-thank-you-ma'am, just be honest about it and let him decide if he wants to take them plunge with you.

It's a pretty good rule to live by- honesty.