So after reading story after story of situations similar to mine, I figured I'd fess up and ask about everyone's advice and prior experiences.
I could easily go on and on and note that this is a long read. I will say this tho, there are some juicy parts so it might be worth it
Let's call my friend Bobby. I've sorta fallen for the straight guy that I've kept under my wing. He's got growing pains, college and what not and so I've helped him a lot by being there for him. I talk to him on the phone, text, help him with his daily problems. He get's upset very easily and he's currently in counseling for signs of ADD and OCD (it's his old divorce children's councilor).
Well since we met we got really close. He's a loner and doesn't have very many friends. He has a huge wall and I literally had to break it down by finally getting upset with him (yeah, sounds like I have gay traits) and said, you know, when you want to be real friends you just let me know. Well eventually he did let me know, said he doesn't let many people if any in, yada, yada, yada.
Well, he lives a few hours away and the first time we met (through the straight internet) he came over and I took him around town, showed him a good time, etc. We have a really weird relationship because prior to meeting we talk about sex and weird guy stuff that most straight guy friends don't ever talk about (personal grooming habits, masturbation, style, fashion, underwear preferences, dick size etc)
I even gave him some of my clothes that I didn't want any more. It was weird because I asked him to try stuff on and rightly so, he went into the next room to try stuff on. I was like, what's wrong. He said, it's just weird. Needless to say, I've broken him down, I mean made him more comfortable, because he went from that to sitting around in his boxer briefs (two pairs of which I game him to which at first he said wearing other guy's underwear is weird ) you can definitely see the outline and flopping of himself, gorgeous.
I did make it a point to hang out in the mornings in my underwear and it worked cause he was obviously more comfortable. He walked around in his towel before waiting for the shower to heat up. The next time he spent the weekend here, I was cutting his hair in my kitchen with clippers even.
Back story, he's a fitness buff and he's into working out big time. Back when we first started talking he used to send me a lot pictures of himself shirtless (let me tell you it's great). We in fact send pictures of everything from clothes we're wearing to food we're eating, anything. I haven't gotten a shirtless pic in awhile, but I think I have like a dozen by now.
So A LOT has gone on since we met. Each time I push the envelope further and further. The second time he came over I texted him that spied on him in the shower (I know can you believe it). I had planned to cause I just couldn't stand not knowing what his dick looked like after we talked about each others. He said his 7 incher was average and he was small flacid. I called shinanigans and told him I wanted to see it. He said, that was weird. Anyway back to telling hime, he at first didn't text back anything bad, and said, shit happens. But later that week we got into some sort of argument (probably because it was awkward and I think it was time I told him we were good friends and he said we weren't, that whole break down his wall stuff) and he said, come on, you need to quit comparing yourself to guys, you're how old? (it was the reason I gave him for spying on him
I do compare tho 
) We had a conversation before about how guys peek at urinals. He does not at all and he knows I do.
As an aside to you guys , lemme say that he has the most perfect junk ever, not to long, not to short, hangs well in a shower without threatening you. It's symmetric and tailored perfectly and far far from being small in a flacid state 
I digress.
Well as part of my pushing the envelope further, I told him that I've never seen HD porn and I was thinking about getting some. He told me I was weird. Then I asked him if we could watch it together. He agreed, at first and I asked him what kind, he said MILF porn. As it got closer to the date I was going to order porn and I told him, he backed out completly and said it was extremely awkward and under no circumstances is he watching porn with a guy ever, end of story. I told him is sex drive is zero and he could just borrow it. He said, no thanks to that, :sigh".
Back story, he has incredible sexual hangups with women. He's a V and is terrified of women. He has zero success with them, he doesn't go out or want to. He doesn't even masturbate all but 1-2 times a month (I know!). Right now, he has the self-esteem of a zero. I always talk him up, encourage him and tell him that one day when he gets confidence, he'll be my wing man and we'll score that devils threesome we always talk about.
Another back story, somewhere along the way we established that we are going to conquer a threesome together. I told him jokingly that I was going to give him a bear hug and he said he'd punch me in the face. When I ask him that I still can't believe he'd join me in a threesome, he says, hey you only live once.
Well back to the porn. I told him that I was going to order it and I told him and pretty much argued that he previously agreed to watching it and that he said to get MILF porn. He said, well you can ask me again but I still find it incredibly awkward. I know, makes me feel bad.
Zoom to the present. I told him I ordered it. To which he texted, oh lord. I asked him I hope you liked big breasted women. As soon as I sent the text and was scared he might just shoot it down. He texted back, "You know it" I texted him the title of the DVD and he said that was a good name. Then I texted him a picture of the front cover of the porn! He didn't look at it yet because he was sitting bitch driving cross country from a wedding with his family. Now confirm this with me, this was full disclosure that I was getting this for us for when he is coming down, right? And I already told him that I was intrigued about it.
Side story, when we come back to the house after going out, I put on the skinamax and we watch it. (he doesn't get aroused or anything, remember he's close to being asexual with the lowest sex drive for a 22 year old ever)
Another side story (right?) for some reason we have this ongoing fantasy where i'm going to do a photo shoot of him. He really wants to do this, I keep asking him what he wants, he said he doesn't know. All he knows is he wants to make it so that he looks tough. I told him that he needs to get a pair of fitted shorts. He says he already has a pair. Then I was like, my house wouldn't be a good place for the shoot so I suggested the gym. He liked the idea. Before I suggested he do two thing, a rated G photo and a Rated PG-13 photo. He thought it was funny. But recently when I joked that he could "wear" nothing but a medicine ball and I smile and I could take the pic in the locker room, he texted it was creepy. To which I texted, back, the whole thing can either be creepy or funny. He texted back, "I vote funny". so I guess we're back on to that too.
So one more thing about the porn. I told him that I won't deny that I'm intrigued by watching porn together. I told him it'll help him get rid of his hangups about sex (which he's been opening up to both me and girls). That's when he said, to ask him again about watching it, he might change his mind. but recall, I told him I ordered, ask him if he liked boobs and told him the title and sent him a picture of it and he didn't bat an eye this time.
So there's the thing
Normally, a guy would post some same form of this same story and everyone would give the advice and it would be, leave him along, confess and chances are be turned down, or just come out to him see if he responds.
I feel that I've let my curiosity part loud and clear (with the porn stuff) and I'm going to find out this weekend just were we stand we me being "curious".
But I wanna try what no one on here has ever done yet, the road not taken. I want to back out and almost tell him completely why. I want to say, my curiosity is not doing well for us and I want us to have distance. I will still be friends and whatnot, but I don't want to make you do things you don't want to do. (we talk about that a lot, not sexual stuff, just stuff in general). And I don't want to continue to think that this is going to have a happy ending.
I want to do this to at least has a feel for where his curiousity level is. He obviously entertains everything I throw at him within his boundaries, so it's not like I'm intested in a homophobe.
I've been down this road before with and they don't end happy, so I want to tell him I'm getting to curious and it's not healthy (it may not be the truth). I don't want to spill the full beans cause there's no point. Even if he was curious and I spilled the beans, i'm so far ahead of him, I'd scare him away anyway.
I'm not out but I'm no spring chicken and I realize that if someone comes along that will actually respond back comes into my life that it will help tremendously with just letting Bobby be a friend.
The thing is, I feel that I'm a difficult person, I'm demanding and I'm challenging. I will probably lay my life on the line for you but I expect a lot. Bobby has been there for me in that he's great at dealing with my personality. We're a lot alike and he knows and sees it and thats why we're some of the best of friends. But I need this in guy that is available.
Any thoughts on what to do?
Really, I hope he's struggling with this inside and found JUB on the net and recognizes that it's him in this story (how could you not?). So yeah, Bobby if you're reading this just text me and we'll live happily ever after I love you bro. 
I could easily go on and on and note that this is a long read. I will say this tho, there are some juicy parts so it might be worth it
Let's call my friend Bobby. I've sorta fallen for the straight guy that I've kept under my wing. He's got growing pains, college and what not and so I've helped him a lot by being there for him. I talk to him on the phone, text, help him with his daily problems. He get's upset very easily and he's currently in counseling for signs of ADD and OCD (it's his old divorce children's councilor).
Well since we met we got really close. He's a loner and doesn't have very many friends. He has a huge wall and I literally had to break it down by finally getting upset with him (yeah, sounds like I have gay traits) and said, you know, when you want to be real friends you just let me know. Well eventually he did let me know, said he doesn't let many people if any in, yada, yada, yada.
Well, he lives a few hours away and the first time we met (through the straight internet) he came over and I took him around town, showed him a good time, etc. We have a really weird relationship because prior to meeting we talk about sex and weird guy stuff that most straight guy friends don't ever talk about (personal grooming habits, masturbation, style, fashion, underwear preferences, dick size etc)
I even gave him some of my clothes that I didn't want any more. It was weird because I asked him to try stuff on and rightly so, he went into the next room to try stuff on. I was like, what's wrong. He said, it's just weird. Needless to say, I've broken him down, I mean made him more comfortable, because he went from that to sitting around in his boxer briefs (two pairs of which I game him
to which at first he said wearing other guy's underwear is weird ) you can definitely see the outline and flopping of himself, gorgeous.I did make it a point to hang out in the mornings in my underwear and it worked cause he was obviously more comfortable. He walked around in his towel before waiting for the shower to heat up. The next time he spent the weekend here, I was cutting his hair in my kitchen with clippers even.
Back story, he's a fitness buff and he's into working out big time. Back when we first started talking he used to send me a lot pictures of himself shirtless (let me tell you it's great). We in fact send pictures of everything from clothes we're wearing to food we're eating, anything. I haven't gotten a shirtless pic in awhile, but I think I have like a dozen by now.
So A LOT has gone on since we met. Each time I push the envelope further and further. The second time he came over I texted him that spied on him in the shower (I know can you believe it). I had planned to cause I just couldn't stand not knowing what his dick looked like after we talked about each others. He said his 7 incher was average and he was small flacid. I called shinanigans and told him I wanted to see it. He said, that was weird. Anyway back to telling hime, he at first didn't text back anything bad, and said, shit happens. But later that week we got into some sort of argument (probably because it was awkward and I think it was time I told him we were good friends and he said we weren't, that whole break down his wall stuff) and he said, come on, you need to quit comparing yourself to guys, you're how old? (it was the reason I gave him for spying on him
I do compare tho ) We had a conversation before about how guys peek at urinals. He does not at all and he knows I do.As an aside to you guys
, lemme say that he has the most perfect junk ever, not to long, not to short, hangs well in a shower without threatening you. It's symmetric and tailored perfectly and far far from being small in a flacid state I digress.Well as part of my pushing the envelope further, I told him that I've never seen HD porn and I was thinking about getting some. He told me I was weird. Then I asked him if we could watch it together. He agreed, at first and I asked him what kind, he said MILF porn. As it got closer to the date I was going to order porn and I told him, he backed out completly and said it was extremely awkward and under no circumstances is he watching porn with a guy ever, end of story. I told him is sex drive is zero and he could just borrow it. He said, no thanks to that, :sigh".
Back story, he has incredible sexual hangups with women. He's a V and is terrified of women. He has zero success with them, he doesn't go out or want to. He doesn't even masturbate all but 1-2 times a month (I know!). Right now, he has the self-esteem of a zero. I always talk him up, encourage him and tell him that one day when he gets confidence, he'll be my wing man and we'll score that devils threesome we always talk about.
Another back story, somewhere along the way we established that we are going to conquer a threesome together. I told him jokingly that I was going to give him a bear hug and he said he'd punch me in the face. When I ask him that I still can't believe he'd join me in a threesome, he says, hey you only live once.
Well back to the porn. I told him that I was going to order it and I told him and pretty much argued that he previously agreed to watching it and that he said to get MILF porn. He said, well you can ask me again but I still find it incredibly awkward. I know, makes me feel bad.
Zoom to the present. I told him I ordered it. To which he texted, oh lord. I asked him I hope you liked big breasted women. As soon as I sent the text and was scared he might just shoot it down. He texted back, "You know it" I texted him the title of the DVD and he said that was a good name. Then I texted him a picture of the front cover of the porn! He didn't look at it yet because he was sitting bitch driving cross country from a wedding with his family. Now confirm this with me, this was full disclosure that I was getting this for us for when he is coming down, right? And I already told him that I was intrigued about it.
Side story, when we come back to the house after going out, I put on the skinamax and we watch it. (he doesn't get aroused or anything, remember he's close to being asexual with the lowest sex drive for a 22 year old ever)
Another side story (right?) for some reason we have this ongoing fantasy where i'm going to do a photo shoot of him. He really wants to do this, I keep asking him what he wants, he said he doesn't know. All he knows is he wants to make it so that he looks tough. I told him that he needs to get a pair of fitted shorts. He says he already has a pair. Then I was like, my house wouldn't be a good place for the shoot so I suggested the gym. He liked the idea. Before I suggested he do two thing, a rated G photo and a Rated PG-13 photo. He thought it was funny. But recently when I joked that he could "wear" nothing but a medicine ball and I smile and I could take the pic in the locker room, he texted it was creepy. To which I texted, back, the whole thing can either be creepy or funny. He texted back, "I vote funny". so I guess we're back on to that too.
So one more thing about the porn. I told him that I won't deny that I'm intrigued by watching porn together. I told him it'll help him get rid of his hangups about sex (which he's been opening up to both me and girls). That's when he said, to ask him again about watching it, he might change his mind. but recall, I told him I ordered, ask him if he liked boobs and told him the title and sent him a picture of it and he didn't bat an eye this time.
So there's the thing
Normally, a guy would post some same form of this same story and everyone would give the advice and it would be, leave him along, confess and chances are be turned down, or just come out to him see if he responds.
I feel that I've let my curiosity part loud and clear (with the porn stuff) and I'm going to find out this weekend just were we stand we me being "curious".
But I wanna try what no one on here has ever done yet, the road not taken. I want to back out and almost tell him completely why. I want to say, my curiosity is not doing well for us and I want us to have distance. I will still be friends and whatnot, but I don't want to make you do things you don't want to do. (we talk about that a lot, not sexual stuff, just stuff in general). And I don't want to continue to think that this is going to have a happy ending.
I want to do this to at least has a feel for where his curiousity level is. He obviously entertains everything I throw at him within his boundaries, so it's not like I'm intested in a homophobe.
I've been down this road before with and they don't end happy, so I want to tell him I'm getting to curious and it's not healthy (it may not be the truth). I don't want to spill the full beans cause there's no point. Even if he was curious and I spilled the beans, i'm so far ahead of him, I'd scare him away anyway.
I'm not out but I'm no spring chicken and I realize that if someone comes along that will actually respond back comes into my life that it will help tremendously with just letting Bobby be a friend.
The thing is, I feel that I'm a difficult person, I'm demanding and I'm challenging. I will probably lay my life on the line for you but I expect a lot. Bobby has been there for me in that he's great at dealing with my personality. We're a lot alike and he knows and sees it and thats why we're some of the best of friends. But I need this in guy that is available.
Any thoughts on what to do?
Really, I hope he's struggling with this inside and found JUB on the net and recognizes that it's him in this story (how could you not?). So yeah, Bobby if you're reading this just text me and we'll live happily ever after
I love you bro. 
