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My best friend and I.

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Ok, before I start, I want to say I am in no way trolling, this story is 100% true, I just need advice...

First of all, my best friend is 32, recently married (Decemeber of this past year), and as far as our relationship goes, he treats me like the older brother I have always wanted. We both play WoW which is how we became friends, and we are both major video game addicts.

I'm 21, bisexual, and very horny as you can imagine at my age. I'm also completely a virgin.. I've jerked off with guys before, but never any touching, just guys watching porn and doing their own thing...

I guess it all started back about a year and a half ago when Mike (not real name, but good filler for secrecy purposes) was over at my house on a night my parents were away at a casino/ resort overnight. We were playing some games on the xbox when he started tellin me about some of his past girlfriends and their sexual exploits. This ended up giving me a boner which I tried to hide as this was only the second time I had hung out with him, and we weren't close enough friends to the point that a boner wouldn't be awkward... My hiding it didn't work, and he called me out on it. I apologized and told him it's his fault for talking about hot sex to a horny college student, and said I'd take care of it later when he left... To my surprise he told me to just pull up some porn and take care of it right there, he wasn't afraid of seeing penises at all.

So, after a second of consideration about it, I did. pulled up some straight porn and beat it while he played the xbox some more. he did look over a couple times at the porn and me, but never joined in or anything. Acted like it wasn't even happening, I think to make me feel a little more comfortable.

I finished fast and he said "feel better? haha!" and we went back to playing the xbox for an hour, than he headed out. This happened once or twice more over the next few months as he came over and gamed with me, it was always started by him and his damned super hot stories.

Last July is when things took the next step. For my 21st birthday, my parents wanted to take me to the same casino they go to a few times a year, and let me gamble a bit. I was hesitant, but they said I would have my own room with 2 beds if Mike or another friend wanted to join me. I asked him and he was instantly up for the trip. We drove separately, and talked about guy stuff on the way (lil over two hour drive), anything from chicks he had been in, to goofy "what if" situations like "what if your buddy broke both arms and needed some "help" haha!" that kinda stuff. Our friendship was constantly going places like this, kinda a "who can freak the otehr out" type thing.

Anywho, once we got to the casino, we went up to the room and got acclimated, sat down for a second, than headed to the game room. We played for about 4 hours, slots, blackjack, all that, and then went to our room to take a breather away from the smoke for 10 mins, and back down to dinner/ more gaming. When we finally went back to the room at around midnight, we were just talking a bit, and than we turned out the lights and tried to sleep, he, jokingly said "you're about to whip it out and beat it, aren't you", I said "not if you don't want me to", he gave me the go ahead, and I started spanking it to knock myself out. He than asked if he could join me (as in, if I minded if he did the same, not actually jerked me or anything), I said something along the lines of "By all means" and so he did.. turned on the light, showing me his gorgeous cock for the first time. We talked during it, looked at each others from one bed to the other, and compared a bit (he's cut, I'm not), before having a "who can nut first" contest. He won, and we laid there, letting it all hang out for a couple hours, just talking, making comments on each others dicks, but not really in a gay way, more in a way that two friends who are comfortable with each other would. over the couple hours, we played with ourselves a bit, but nothing else happened.

The next morning we drove home, nothing really happening except our normal conversations. That night however, on Wow (world of warcraft for those that don't know, computer game), we were talking, and we got ont he subject of the night before. I can't really remember how the full conversation went, but it ended up in him telling me that he wanted me to "suck his dick, use the cum as lube, and fuck him for the first time", as he said, along with a few other things about how we could have done so much the night before. (Mind you, he was a little drunk)... We than made plans for him to come over to my place to test some of it out the next night, which ended up being canceled and never really talked about again. Anytime I would bring it up, he would just brush it off as his "super horny, perv friend", and it became kind of a joke. I hadn't whipped it out in front of him since that night, made jokes about how he owes me some things,a nd on ngiths when I was super horny, I even took it too far, which i felt horrible about the next day thinking "he's not interested at all, I'm gonna lose a great freind if I keep this up", but when i get super horny, I would do the same thing. whether it's asking for pics of him, or saying things like "Hey, you should come over and blow me, I'll return the favor!" and again, it was just brushed off.

To this day, we go out every week to grab pizza at the best pizza place in town, and we always have our normal pervy convos. Tonight it took a new step tho... Earlier today, I had told him about how horny I was, and made a joke along the lines of "You should drive on the way back to your place (as I normally picked him up and dropped him back off so he could have a beer while we were there) and we'll both have happy endings!" he just laughed. Later that night, we went out for pizza after i got off of work, I picked him up per our usual, we ate dinner, and on the way back (me driving), we got on the subject of highschool, and he was telling me a story of how his highschool gf would jerk him under the table during science. I told him "Hey, knock it off, I'm gettin a stiffy over here" he said something along the lines of "Why's that bad, boners are always good!"I said "because I can't do anything about it now"... We laughed and brushed it off. as we got about 5 minutes from his house, he started the stories up again, and I told him if he keeps talking, I'm whippin the boner he's causing out and he's taking care of it" he cracked up and stopped before finishing the story...

About a minute later he tests me and finishes it... Unlucky him the light ahead of us jsut turned red... I pulled my pants down and told him to get to work (I was joking, expecting to stroke my dick a bit in the car while I was on the way to drop him off)... He just laughed and kept lookin back at me. I told him that he caused it, he's gotta fix it. he didn't do anything, so I pushed (while laughing, and so was he) that he's gotta atleast grab it as he's teasing a very horny virgin. He grabbed it for a second and said "there, happy?". First of all, it was like a fucking jolt of lightning through my body when his warm hand grabbed it... I told him to keep going, that he's got me goin too much now. after me telling him to keep goin a few more times, he grabbed it and started stroking it, completely shocking me as I thought all these years he was just messing with me,and nothing would ever happen. We approached his neighborhood and I said "Damn, I wish we weren't already here", he told me to just keep driving, I did as commanded.

About a minute down the road I asked if he wanted a hand too, he said maybe, and continued stroking me. A couple more minutes later I told him to whip it out... much to my surprise, he took off his belt and pulled his pants down.. we're now driving down an old country road at midnight stroking eachother... I asked him if he knew anywhere we could park as I was willing to go a step further on him, and we continued stroking as we drove aimlessly looking fora parking spot. We stroked for about 20 more minutes, couldn't find anywher to stop when we came back to his neighborhood, we looked around for any houses having construction work going that we could park by, but no luck.. He told me we would have to resume this some other time because he had to get to work in a few hours and needs to get some sleep first, so we stroked eachotehr until we got back into his driveway. he said there were too many lights on outside his house to really do anything in his driveway,a nd his wife is asleep inside... so once we pulled in, he looked at me and asked if I wanted a taste before he puts it away... I took it and took his dick into my mouth a couple times, and that was it.. I asked if he was doing anything monday afternoon as my rents would be gone at around 1pm after I got home from class at around 11am. he said he had a better idea. his house is close to campus, and he told me to just swing by his place after class, his wife would be at work, and we had so many thigns we could try if I wanted, and that he would have to get back to me to make sure his wife worked that day... but as of now, that's the date for something to happen...

Here's what I need as far as advice... One, should I go? if I do go, do you think I'm risking a friendship if it gets awkward, as he a married "straight" man. Also, if I do go, what should I do to make sure he's satisfied, just go with the flow? I've never had any form of sex and while I'm not nervous at all, because I'm so comfortable around him, I don't want anything to go wrong. Also, if he blows it off, should I bring it up a different time? and should I try for a repeat of the road jerk/ head next time we go out?

Sorry for the wall of text.. it's a long time int he making for this...
 
This is a touchy situation and you have to ask yourself a couple of questions none of us can answer.
#1. Are you REALLY willing to gamble with a friendship?

More often than not sex changes things between friends. I would imagine this is especially true for someone who identifies as 'straight'. Even if he is bisexual, closeted, or curious, he made a commitment to another person...roughly two months ago! I could speculate about his motives for doing that, but it would only distract from the main point...he's a married man.

#2. Are you REALLY content with being on the side?
Think about it, you're ALREADY having to plan things around his wife's schedule.This is setting the tone for the remainder of your encounters while he's married. Of course it may not be a problem for you now because the attraction is strong and your curiosity is in overdrive, but given enough time this will become a problem.

My honest advice would be to pump the brakes my friend. This is a guy you refer to as your best friend so if you gamble and lose (he becomes awkward, she becomes more demanding, he's less available etc.), its a big loss. Just my two cents.

KEEP US POSTED.
 
This story took an unfortunate turn with the word "wife".

There were lots of red flags- the fact that you're friends, that he's 32, that he's hanging out with a 21 year old telling him sex stories, encouraging his younger friend to jackoff in front of him, the fact that this happens only when he's in control of the situation...

But when you throw in the word "wife" and that he's willing to have a guy blow him in the house he lives in with his wife, it becomes a deal-killer.
 
Yikes,

And to start this whole thing on Valentines' day! I could see it going horribly if his wife planned some sort of surprise for him that day.

And sex does change everything. It sounds like this has already happened to you - when you had an opportunity for something more - and he kept pushing it off. He's likely grappling with guilt - and while that's not your problem. That guilt will likely be a bad thing for your friendship - and perhaps his marriage.

Everything sounds so hot between you - but you aren't quite at the point of no return.
 
He's a cheater.

With the emotional depth of a 14 year old.

Sorry guys.

Can't have it all ways.
 
^ I agree with KaraBulut. The wife is a deal-breaker.

And I agree with both KaraBulut and Just_Believe18.

Your first time should be special, because it is your first time and you will remember it good or bad - - make it good, make it with someone you care about as something more than a horny friend.

If you are in a college town, you should be able to find several more gays closer to your age and interested in things you are. You should concentrate on finding a BF.

The above is just my opinion. It will be a difficult decision for you, but I do think you are being played. Keep the relationship as friends.

Rand
 
I agree with everyone here. The red flag came up with the word, "wife," not to mention you're encouraging each other.

Neither of you can/will "have your cake and eat it too." There is a consequence with this.
 
No, no and no. He's already proven he's untrustworthy by cheating on his wife. He's proven that's he willing to expose her to STDS without her knowledge. This is someone he vowed to cherish and love.
If he disregards her safety and wellbeing that much,what makes you think he'll care about yours any differently?
You want your first time to be special, do it with someone who cares about you, not a person like this guy.
 
No, no and no. He's already proven he's untrustworthy by cheating on his wife. He's proven that's he willing to expose her to STDS without her knowledge. This is someone he vowed to cherish and love.
If he disregards her safety and wellbeing that much,what makes you think he'll care about yours any differently?
You want your first time to be special, do it with someone who cares about you, not a person like this guy.

He's not opening his wife to STD's. He's been my best friend and basically older brother for 2.5 years total now. He's told me everything about him, including the fact that he has cheated in the past, but not on the girl that is currently his wife (They had been together for over 8 years before they got married). He know's I'm completely a virgin and completely clean. He's not the type of person that would normally cheat. I almost think he is doing this because he knows it would be a very special "First time" for me.

Some thigns I left out about our relationship:

-We met at work (he no longer works there, I still do)

-We hung out for quite a while before any of this started.

-He stopped me from committing suicide after my parents called me a failure repeatedly by convincing me that I have a good enough life to not let them end it.

-He has taught me more about being an adult than my parents ever could:

-How to go about getting my first place when I'm ready.
-How to break up with my first real girlfriend after 2 years (I didn't know what to do, just knew I didn't want to be in the relationship anymore, he gave me advice on it and even offered to go with me for emotional support)
-How to fix both my car, and my computer.
-Quite a few other things.

-He knows I don't drink for personal reasons, and when he invited me out with his friends on new years eve this year, he made sure his friends didn't pressure me to drink (Larger party, people from my age to older than him).

-He knows how shy I am and tries to make me feel welcome anytime I go out with him and his buddies.

-He's the only person that said happy birthday to me on my 21st, and offered to take me out for my first beer. I declined the beer (again, don't drink), so instead he brought me a case of mtn.dew code red (favorite pop), and we played video games for 5 hours.

So for those of you that are saying he doesn't care about me, forgive me if I didn't explain our friendship enough. To me, he is the only real friend I've ever had. No, I don't want to risk that friendship, but it's also been a fantasy of mine to do anything with him at all. I talked to him the first time he brought it up, and asked if there was any way it would make things awkward between us, or if there was any chance it would effect our friendship, back then, he told me absolutely not. I'm still hoping that is true I guess.
 
So for those of you that are saying he doesn't care about me, forgive me if I didn't explain our friendship enough. To me, he is the only real friend I've ever had. No, I don't want to risk that friendship, but it's also been a fantasy of mine to do anything with him at all. I talked to him the first time he brought it up, and asked if there was any way it would make things awkward between us, or if there was any chance it would effect our friendship, back then, he told me absolutely not. I'm still hoping that is true I guess.

If he's the only real friend you've had that would be even more of a reason not to do this. Why contribute to something that could end his marriage if his wife found out?

Sex does change things. You may not think it does, but it does.

What are you expecting out of this if you do have sex with him? Are you expecting sex every once in a while?

Wouldn't you like to have a boyfriend or girlfriend that you could have sex with and not have to sneak around with?

Trust us, this is not a good idea. If you value your friendship with him, don't go through with it.
 
As to what I'm expecting out of this... a first time with someone I trust, and who doesn't find me repulsive? I'm not posting pictures of myself because it's not pretty... I said I'm 21, you all assume I'm some catch and he's after some skinny 21 year old college kid. I'm 6'1", 240 lbs, have wicked stretch marks all over my body, and suffer from a condition called "Phimosis"... I've rarely found a person who I trust enough to see me shirtless, and I've never really had someone find me attractive, especially not enough to do anything with me. But you may be right, no, I don't want to lose our friendship.

I have some thinking to do, maybe I'll talk to him about it.
 
As to what I'm expecting out of this... a first time with someone I trust, and who doesn't find me repulsive? I'm not posting pictures of myself because it's not pretty... I said I'm 21, you all assume I'm some catch and he's after some skinny 21 year old college kid. I'm 6'1", 240 lbs, have wicked stretch marks all over my body, and suffer from a condition called "Phimosis"... I've rarely found a person who I trust enough to see me shirtless, and I've never really had someone find me attractive, especially not enough to do anything with me. But you may be right, no, I don't want to lose our friendship.

I have some thinking to do, maybe I'll talk to him about it.

There are guys out there who won't find you repulsive. I like older guys and a lot of people don't find them all that attractive, but beauty is in the eye of the beholder. It may be cliche, but it's true.

I have scars on my body and stretch marks and I've still had sex with guys and have had and have a boyfriend. I'm not heavy, but my point is the majority of people have physical flaws, you just don't always see them.

Phimosis does suck though. I had it and I'm still working on clearing it up.

I hope you do talk to him and I'm glad you're doing some thinking.
 
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