Advice: I'm Trying to BLOW my "straight" best friend!
 

We have been best friends for 21 years. He just left his wife (bad marriage/no cheating or anything just anger). Anyway, he has not had any sex in 3-4 years. He is Mr. Saved Himself sexually for his wife and really hasn't had lots of sex (never been done on a woman and only a few bjs in his life).

We stroked each other's cocks once back in high school. It was intense. He swears that he is totally loves women, but we have swapped cock pics with each other in the past year.

I offered over a year ago to give him a blow job one day when we are chatting on-line. He said he isn't ready for something like that and it became very tense and uncomfortable. I don't want to ruin our great friendship, but I think he really wants me to, but just too afraid to ask.

Last May, went on a Guy's Only Weekend, just him and I. Tons of beer, hiking, fishing, great laughs...anyhow 2nd night we are in the hotel. He starts FURIOUSLY jerking his cock thru his boxers, I mean I have never seen him this horny or intense before.

It's funny because I love sucking cock, but not a huge fan of swallowing...I know that is the best bjs; concerning my best friend, I have told myself that I would deepthroat him, (lick/suck/fondle his balls, which he has NEVER had) and give him the hottest, nastiest cock sucking ever! I will drain his balls dry, swallowing his whole fucking load. :D

My Questions:

-did he want me to blow him and was too scared to ask?

-Should I just go for it?

any advice or share any similar experiences so I can learn???


We are going on other Guys Weekend this Summer (we agree it is Annual must-have for our calendar). So I will report back with what happens.

I don't think there is an easy answer - depends on the guy.

Had one buddy back in high school were it ALMOST happened but didn't that night and after that we never again had a sleepover or anything - and clearly he did not want to be in that situation again.

But if he goes for it and you both like it it could be the perfect set up for both of you -

So afraid no advice - all I can see is good luck.

Put him at ease first
 

The worst thing you can do is hurry him to a decision. Even if you get your lips around his dick and give him the ball draining bow job of all time, if he is not ready for it; you will lose any future chance and possibly his friendship.

My recommendations since you'll be spending some time at the next event is get him use to nudity around you first. Leave the bathroom door open when you shower "so you can talk". Walk out of the bathroom after the shower naked while you dry your hair. Don't blow it by leering at him if he gets naked. It's alright to compliment him on his body and even his package.

Secondly, be yourself around him. Don't be a flaming queen, but don't be a closet homosexual. Comment on other guys and how they look. Great line "Glad I'm rooming with you instead of that guy. I'd be blowing him so much, I'd never get any sleep. Hey, but I'd rather have your company over any casual piece of meat in here, buddy. You know how they say Bros before Hoes, I say Bros before Blows."

Hope you have success.

Seems pretty clear that if you end up servicing this friend, you'll end up without a friendship. Is sucking this particular dick worth that?

UPDATE!!!

My friend has been mentioning lately that he hasn't fooled around in ages and is sick of jerking off! He jerks off everyday, sometimes TWICE a day. He has also basically demanded that we NEED to go on our yearly Guy's Only Weekend.

Do you think he is thinking about me blowing him and
is just afraid to ask now????

Thanks.

Duh - Do you need a written invitation
 

Ask yourself, has your friend typically told you his sexual frustrations in the past? If this is a new thing, invite him over for a boy's night in. Fetch him a cold beer, look him square in the eye as you offer it to him and say "Do you want a blow, er I mean beer?" He might say "I'll take both!"

No seriously, it would indicate that he is thinking about the situation. Taking the annual trip might be good. However, keep in mind, some best buddies hit the rocks after that initial "gay" experience. He might avoid you in the future, afraid of the memories and a repeat slip. He may use your services until the right woman comes along, and then completely disassociate himself from you. Or it might be the best thing that ever happened to your relationship.

Before it gets too far, have a man to man talk. Let him know how you feel. You are physically and sexually attracted to him, but don't want to do anything to harm the long friendship between the two of you.

In my opinion, you should avoid the "you won't have to do anything back, just enjoy what I do to you." This makes you nothing back an available mouth (or ass). It makes you a sex toy to be discarded when the novelty wears off. If you do start something, let it progress as it will. Don't force it.

How would you feel if, after having sex with your best friend, he decides to fall in love with you? This is always a risk. They fall for the first person who seems to validate their feelings.

In the end, the answer to all this is so simple: just ask him very directly if he wants you to service him. What could be lost from asking? Nothing more than what might be lost from simply making a move on him! Right?

Hopeful and Careful at the same time
 

I've been through this. Had a best friend. We traveled together on and off on business. I was very hot for him but had to be careful since I'm married and he was straight with serial girlfriends.

We became close, so much so that one night he was having trouble sleeping in a sorry bed and I invited him over to mine. He said that he couldn't do that and I said "Oh, don't worry about it. You sleep over there, I'll sleep over here." He said that he couldn't do that and after a little discussion he said that when he got close to me sometimes he got an erection. I laughed, blew it off and said, "Yeah that happens to me too." So he came to bed. Starting a few nights later, we started sleeping together all the time and even holding each other. No sex, though.

One day, I was lying in bed with him, almost asleep and he said, "Don't open your eyes. This may never happen again." And he lightly kissed me on the lips. An unforgettable moment.

Finally, one day, I made the move while we were and he freaked out. Even though he was hard, he really couldn't deal with it. He got up and left. And though we continued to be friends for a while, that was the beginning of the end of our friendship.

He's married now and with children and lives several states away so we never talk or see each other. I'm sure he's more comfortable with that.

On the other hand, you're getting invitational signals. But go slow, be careful, and be prepared for it to turn out differently than you hope.

How will it end
 

Your question inspired me to compose a story for the DIRTY STORIES: INSTANT JACK OFF MATERIAL section of the forum. Check out "The Story Isn't Over Yet!"

I have no idea how your story will go. Be sure to let everybody know. Of course, pictures area always suitable :D, but even just a short "it was a good idea" or "I never should of done it" would make us happy.

I think he really really wants it, but just afraid to ask. I also think he is terrified that he will fucking love having his cock really worshipped for once in his life. He is extremely limited when it comes to sex.

There comes a time when you have to go "all in" or throw in your hand. The ONLY person who knows that is you. You will either score or spend the rest of your days wondering, "what-iffing" and "I-should- have" . Bottom line is, if the juice is worth the squeeze then f@cking squeeze it.

Any developments in your quest? Let us who have no sex life know so we can live through you. As always, in lieu of pictures, we want graphic details.

No way of knowing...
 

Actually, there is absolutely no way of knowing what may come out of this.

Powerful as collective wisdom may be at times, every guy is a story for himself, and his behavior may be ranging anywhere between very rational to totally irrational.

We all know of a number of cases, where sexual intimacy between a gay dude and his best 'str8' friend ended their friendship. I also strongly suspect that there are many cases, where the arrangements worked out just fine, only very few guys are reporting this since the matter at hand is obviously best kept private.

Last but not least, many friendships do run their course, one way or the other. At times, the sexual intimacy element may or may not speed up the inevitable end of it.

KD

Obviously, the final word remains with LSC. The question is now (after seeing some sage advice) which stings more/longer rejection or regret?

Speaking on a purely personal level, the hardest and most enduring is the regret that I should have been more direct but was not. I lost touch with a man that I have been looking for since high school. Coulda, woulda, shoulda... I will not make that mistake again.

David, if you read this; you SHOULD have gone for it. I was waiting on you.

It Takes Two to Tango...
 

Hey Chris:

Sorry to read about your regret.

On an equally personal note, I too, have gone my part of the way in offering whatever was on the table at the moment.

Yet, you CAN bring the horse to the water, but you can't make him drink it... .

So, I have learnt not to have regrets of this kind. It always takes two to tango. The other guy must be able, wise and willing to receive your signals, too. If you are sending them against the concrete wall, not much of a smart response will ever echo back...

KD

Well think about this.
 

See about going out for a few beers, and bring him to an abs with viewing booths. Then, if he likes it, take him to a booth where there is a glory hole, and have him try that, but you would be on the other side of the hole to blow him. You can reveal it later to him, especially if he says he liked it. That was how I started. A gay friend of mine lured me in that way. He told me about the holes, and what happens, so I tried it, and found out later that it was him. Ever since then, I have not given it a second thought. I love a BJ from a guy, and I love giving them. What ever you do, don't be pushy, just provide the right atmosphere, and let him try comming to you. Plus, if you stay low key after words, he more than likely will come back for more knowing it is discreet. What ever you do, do not push the issue.

Thanks, bbsckbottom!

Update!!!
 

My best friend and chatted about sex, porn, etc for hours a few weeks ago.

He has thought about a 3 some with my wife, i was stunned. Also he was stroking and hard most of the time we were chatting, asked if he could send another pic, he said sure and sent me one of him hard right then.

i saw it...WOW! He is thicker than I remember. He wanted to get my opinion about his cock pic, i didn't know what to say...wanted to be honest, but afraid. I was blunt, said, "looks amazing and would like to suck it." I crapped my pants that i actually blurted that out.

He wasn't grossed out or upset, he said, "i guess i should say thank you." I apologized and said don't want to upset you...he said, "don't worry, it's cool."

he keeps telling me how he is so fucking horny over and over again recently, especially since he is hanging out with woman he has befriended and zero action from it.

I still think deep in the back of his mind, he doesn't want to admit it, but he has thought about me blowing him and he is just repressing it.

If he is telling you he is "so fucking horny over and over again" then he is telling you he wants you to do something about it. Try the "if you tell me that one more time I am going to have to take care of you" and see what he says. If he bites go for it! If he doesn't play it off like you are tired of hearing about his blue balls. Nothing ventured?

I kinda think he is no longer "repressing it." What more do you want? For the guy to push you onto your knees and force you to blow him? Hello! Time to just go for it.

Keith

Keith, That sounds good!
 

Not for the newbie, but I know a few "I'm strictly straight"s who only took a slight push to kneel and blow. Some just like to be dominated.

If he has no interest in you sucking him he would not be sending you pictures of his cock hard...

It is now just the matter of having the courage for one of you to actually make the first move...

I am a TOTAL chicken at making the first move - but if I had a buddy being that open I think even I would dare make the move!

:)

You've already seen him hard in the past...or more? He's bi as well.

Clear signal he wants some action. Go for it at the next opportunity.

***update***
 

Just chatted again with him today, exchanged more cock pics.

i mentioned a fantasy of mine is share a cock with my wife, her and I blowing a cock/kissing with it in between us. He said sounds hot! Then I said I had thought about the cock being his, he said hot!

I EVEN sent him a gay video of a dude blowing his married buddy, amateur, one guy was standing on sofa, humping the other's face. He wasn't grossed out, said looks difficult to pull off!

fuck i wanna blow him sooooo bad!

Jesus, if you are still waiting, forget it. Send me the picture of his cock and his phone number. The guy is going to end up going elsewhere anyhow to get his needs handled as you continue to drag your feet.

Agreed Grumps! He can come to me. I'd be happy to oblige.

I'm not rejecting or stalling!
 

*****UPDATE******

LOL, he lives 3 hours away from me. We see each other MAYBE 3-4 times a year and we both have kids.

He is driving up and asked me when we would be alone! If he even gives a remote hint, I'm going for it.
He reminded me again how he is sick of jerking off and needs to fool around REALLY badly.

I'm still shocked that he liked and was impressed with my cock pic due to it's rigidness and how it stand rather straight up.

TOTAL DISAPPOINTMENT!

He acted strangely, caught him rubbin' his jeans on my sofa looking at straight porn and when i came down into the room; he freaked and stopped immediately.
:mad:

***Another UPDATE***
 

We chatted days after he came up and stayed the night and nothing happened. He agreed that he wanted to at least have us both jerk off in front of each other. He also wants to stroke my cock and have me stroke his. I mentioned me giving him a blowjob, he said we can work up to that!!!!

I think he wants me to suck him sooooo bad, but he is nervous to either ask or have me do it AND it being so hot it blows his mind!

I even said, well if we jerk off where are we gonna cum? I said I usually shoot a lot and all over the place. He said he could aim in TP. I said i thought I was gonna see you get off? I suggested, maybe right before you shoot your load, you shove your aching cock into my mouth? He didn't say yes or no, but he did agree that getting a bj and unloading into a hungry mouth was hot!!!

I think it's a matter of time now..I will keep you posted!

****RECENT update!***
 

My buddy is coming up for 3 days at least...so hoping to finally get some action.

He said after insisting so many times that he only wants me to JERK HIM OFF, that he is not a selfish and of course would return the favor! I asked him totally blunt question after he has admitted that he is fascinated with seeing dicks,
watching guys get hard, ;)
and not really hot for seeing a pussy :eek:
(he loves TITS and the entire female body).

i said ever thought about sucking cock, he said not really interested in that, but absolutely loves getting sucked. He also said something intriguing, "appears friends or guys experimenting with each is more common than i thought, seen many things about it on the NET."

I'll take whatever I can get from him. :D

So maybe he just needs to warm up and once started "he just couldn't control himself" and you can blow him. Once he is hard and getting all the attention, the big head will start to see things the little head's way.

On a more negative note maybe he is just a total cock teaser and is getting off on his power over you versus the prospect of a blowjob? You won't know for sure but there are other cocks out there more accessible and MUCH more willing. It seems like you have spent an awful lot of time and energy obsessing over this guy. Just some thoughts.

I never knew he was an option until the pics got sent last year. He resent me and sent a new one. Last time he was up, too many people around, but mentioned to me "let's plan it!" I sent him another short gay amateur face fuckin scene, said "hope i didn't gross you out." he said, "not at all." any straight man would say yuck or don't send me that again!

This has been going on for seven months. Even if he had been interested some point in the past, he is now just a cock teaser. Get your head out of his ass, and start looking for some available dick. If he calls, telling him you "are going out to get some". If he really wants you, he'll offer. If not, HE IS NOT INTERESTED, he is just playing bait the gay guy.

Not sure which is more startling: that this guy still hasn't gotten into his friends pants, or that you know how many months he has been trying!

I'm with you: next!

Yeah, I hate to break it to you but I agree with everyone else here: at this point he's more interested in jerking off to turning you on than he is to actually getting anything out of you.

Power Trip
 

There is little doubt that the 'str8 dude' is on a power trip. There are loads of guys out there who get a huge ego boost by discovering that you want something and that they may be in a position to deny you that... It really does not have to be sex at all.

I am all for trying and NOT giving up easily. But there is a limit to how far anyone should really go. Feeding his ego does no one any good. Even the guy who seems to be enjoying denying it, is actually getting a totally wrong message, too. :D

More likely than not, his next victim will simply shrug with his shoulders and move on to the next perfectly willing guy who'll be more than happy to trade off a solitary jerk for a good, hot mouth...

KD

Interesting twist...
 

I thought since he has found a recent woman to date that he would not want to fool around. He reminded me that we have talked about it so much and why not have even more fun!!!

If we didn't live 3 hours away from each other, I think this would happen sooner.

Had a camp counselor roommate once for a summer working at a camp... he was hung like a horse and liked to hang out naked in our room. Used to take off his clothes as soon as he got to the room. Would talk about how hard it was for him to be away from his girlfriend. Once he took off all his clothes and walked around the bed, making the upper bunk while I was in the lower one. He suddenly asked me if I was enjoying the show. I was, and I wanted to blow him, but I didn't trust him, so I didn't. I've thought about it since, and I wonder if I should just have said, "If you want a blowjob, you're going to have to ask nicely" or something like that. He went back to his girlfriend after the summer, then married someone else. He's a famous symphony and opera conductor, and he's on TV all the time. Still looks young and handsome, though he's aged. I can't watch him conduct without thinking about that other baton that I know is underneath his tux. But he wanted attention and adoration more than he wanted actual sex, and if we had had sex, I'm sure it would have been a one-time thing.

Peter -

It is so frustrating - thinking of the times that might have been if you or the other guy had just been braver...

So many missed opportunities - especially younger.

:-(

Let me guess: Michael Tilson Thomas?