HELP/ADVICE needed! I want to suck my best friend, what do I do?

[Caseylove99]

So it's a long story but I really want to suck my best friend's dick really bad. He is already aware I have a major fetish for both his ginger pubes as well as his foreskin and we always joke flirty about him showing it to me some day. We compared back in the day but never done anything sexual at all or since. There was a period of time where he just wanted to get his rocks off and I was worried he'd do something sketchy with a girl that would give him something but he assured me that if it was a random hoe it was condom even during oral and he has never lied to me so I believe him. I told him if he wanted to get off that bad I'd give him a brojob whenever he wanted and we know each other are fully clean so no protection required. He said he didn't know how to reply so he didn't say anything for a few days until he asked me if I was serious about that a few days later to which I said yes and he said ok. We didn't mention it again for a while and everything continued like normal with our friendship. He entered into a longer term relationship with a girl for a year or two after that so the need never came about but that ended up going south and he has been single for over a year and hasn't done anything with anyone. We've always stayed flirty over texts and in person about his junk and he has teased showing me it since he still knows I have the earlier mentioned fetishes that apply to him but always refrained from actually showing it to me.

We hung out last weekend, as we do quite often, and ended up passing out on the same couch watching a movie. I woke up a few hours later with him as the big spoon and a boner poking me and his balls slightly hanging out of the bottom of his shorts. I carefully got up and noticed that his balls were out and I pulled his shorts leg down to cover him up and he moaned a little and his dick flexed a little, luckily he is a sound sleeper and I didn't wake him. I went and got a blanket and covered him and then went and fell asleep on the other couch. In the morning I woke up and I was the little spoon again and he had a boner again. He woke up at some point and came over to the other couch and slept and spooned with me intentionally. I felt him stirring shortly after I woke up and he said "thanks for blanket last night, you looked cold so I thought we could share ." We both got up and he was obviously boned up and was trying to hide it which was difficult in the basketball shorts he was wearing. I jokingly asked if he needed "help" with making it go away. He was so embarrassed and didn't know what to say or do. I reminded him of the offer I made a few years ago and he just looked at me and thought I about it. He eventually said something like "you're always joking around, good one." He stretched and went to the bathroom while I started cleaning up. After about 2 mins I was walking the blanket back to his bedroom and as I walked by the bathroom door I could here the foreskin slapping and I knew he was jerking off in there. I kept listening and eventually heard him grunting very faintly and then I heard the sound of his cum hitting the floor when he squirted. I hurried back to the living room after tossing the blanket on his bed and he came back out and sat down and turned on the tv and we started watching a show. I looked over and saw he had a little cum left on the edge of his shorts and I threw him a tissue and said he missed a spot. His face was pure white and he just stared at me then wiped it up without saying anything. I told I was serious about my earlier offer and he'd never need to worry about a mess with me because I'd swallow if that's what would make him happy. We didn't talk for a while again and just kept watching the show and he wouldn't look at me. I finally got up and went over and sat next to him and put my arm over his shoulder and he started boning up a little and he told me thanks and that I'm his best friend but that he just isn't gay. I told him that he didn't need to be gay to enjoy a blowjob. We laughed and we watched a few more episodes and and then did the super bowl thing with some other friends coming over too. I went home after the game as did everyone else. He messaged me on Monday night and said "I know how much you've wanted to see it" and sent me some softie pics showing me his ginger pubes and his foreskin in various stages of being retracted and then 3 boner pics, one with his skin pulled back partially and the other with his skin pulled so far back it actually looked painful. The last pic was a closeup of the tip showing where the foreskin connected at the frenulum right below his slit. It had a stream of precum dripping down his frenulum. These were not just some "old" pics and he had definitely taken them specifically for me. Not gonna lie, I busted before I could even get fully hard and have jerked off so much to them that I actually have a small sore on the side. I responded "thanks" and he liked my reply. It's now been 2 full days and he hasn't replied to a single text or call or anything since. I know he's ok because he has read receipts enabled, which he knows he does. I told him if he ever wanted it, there would be no reciprocation on his part and I would do it just to make him happy and give him the pleasure.

We did make plans prior to this last weekend and the pics happening to hang out this upcoming weekend because we both have Friday off this week and I also have Thursday off too. I have a key so I usually go over before he gets out of work, play with his pup, and make something for dinner, get video games and stuff all warmed up, etc. I already asked him if he wanted me to pretend last weekend and the pics never happened and if he didn't want me to come over this weekend. He read it but didn't reply. I told him to let me know tonight before 8pm otherwise I'm going to keep our plans as scheduled and head over tomorrow morning and keep his dog company until he gets home and make chicken parm for dinner. He saw it but didn't reply. That time has passed so I'll be keeping our plans as scheduled. I said I'd be over around 11amHe saw it and didn't reply.

Questions for everyone: what do I do? Why did he send me the pics? Does he want me to suck him? He has never actually said "NO" when i offered. He either just took it in, just laughed it off or said "but I'm not gay." Like personally I am bi, and I definitely love him, but not in a "I want him to be gay and marry me" way. In a he is my best friend in the world, and it just so happens that I want to suck his dick whenever he wants me to, Friends with one way benefits style lol. If he got a gf again or a wife that stuff would cease and there'd be no jealousy or anything on my part and friendship would continue minus the brojobs. I'm sure this is a bizarre situation but if anyone has advice or thoughts I'd appreciate it. Thanks in advance.

I will follow up with details of whatever happens.

 

[tnman]

Sounds like regret on his end? or he' does not know how to reply to your advances that he really may be wanting? It's hard the first time letting aa man suck your cock especially when it's your best bud

 

[Caseylove99]

Sounds like regret on his end? or he' does not know how to reply to your advances that he really may be wanting? It's hard the first time letting aa man suck your cock especially when it's your best bud

Well I texted him again this morning before I went over that I was on my way over. He saw it and reply. I'm at his house now playing with his doggo and he gets home around 5pm. I just feel sick in the pit of my stomach. Do you think he is just afraid that it will change our friendship if I've had his dick in my mouth? I mean I'm a virgin so I've never been with anyone. He has been with a lot of girls so he knows what it's like to be intimate with another person. To me I'd be like bro just watch some porn or VR and enjoy the sucking. He has told me that he LOVES blowjobs but barely ever got them. His last gf wouldn't do it because she didn't like his foreskin so only did sex and handjobs and some of the previous girls didn't like the foreskin either and we're the same way. I guess we will find out when he gets home where we stand. Any other thoughts? Like the cuddling with me and the boner against my ass and then sending me the pics, was that just to make me happy by going to the absolute maximum he was willing to go boundary-wise?

 

[Caseylove99]

If anyone can give some advice in the next hour I would appreciate it

 

[Trhwa194]

I wouldn't recommend you push him too much. You've made it pretty clear that your serious. If it happens it happens, otherwise just keep on living.

Be free from the shackles of obsessing over straight men.

 

[RJ5on1]

Not so much as advise, but a suggestion. First, I'd suggest you not push him at all on not replying those times. I would suggest you mention to him something like, "I know I already said this, but I want to say it to you, in person; Thank you, again, for sending those pics, I think they're awesome!" and then ask him, "Is it OK with you if I keep them?" ... give him the chance to feel comfortable with making that choice. This way he won't feel pressured in any way, if he had second thoughts about sending them, after he sent them to you.

He's been quiet ever since he sent them, so... let him have some breathing space, and let him direct where the conversation goes for now.

 

[RJ5on1]

Oh, and FWIW, he knows you felt his boner, and he's obviously OK with that, so...

 

[Caseylove99]

Not so much as advise, but a suggestion. First, I'd suggest you not push him at all on not replying those times. I would suggest you mention to him something like, "I know I already said this, but I want to say it to you, in person; Thank you, again, for sending those pics, I think they're awesome!" and then ask him, "Is it OK with you if I keep them?" ... give him the chance to feel comfortable with making that choice. This way he won't feel pressured in any way, if he had second thoughts about sending them, after he sent them to you.

He's been quiet ever since he sent them, so... let him have some breathing space, and let him direct where the conversation goes for now.

He messaged me a minute ago, "sorry I haven't replied, I'll be done with work a little late today better have my dinner ready at 5:30 bitch." We jab each other like that all the time so calling me bitch is normal. Hope everything will be ok later.

 

[Caseylove99]

He

Oh, and FWIW, he knows you felt his boner, and he's obviously OK with that, so...

He definitely knew lol, felt it and saw the shorts tent

 

[Caseylove99]

So after we ate dinner last night we were playing video games and he asked me "so, what did you think of my dick?" I told him it was nice but why did you decide to send me pics now after all this time and after the awkward stuff that happened that weekend. He said, "I don't know" and I was like oh, ok, well thanks and I think your foreskin is really cool. Then he asked if I wanted to see it in person to which I of course said yes, so he whipped it out and starting showing it to me and how to retract it and stretching it. I commented how I liked his red pubes too and he said he usually kept them completely shaved because no girl ever liked pubes. He adjusted himself to put his junk away and when he did he had to pull down his boxers all the way and HOLY SHIT his balls are massive. Like full jumbo egg sized. I was like holy shit you balls are fucking huge and he was like yeah I know lol. Put his junk away and went back to playing games and no happenings for the rest of the night UNTIL he said I don't want you to sleep on the couch tonight, my bed is big enough for 2. So that happened but no spooning or anything like that to my disappointment. Anyone think he is flirting with the idea of letting me suck him off now?

 

[hzs3fg]

He was probably disappointed that you didn't make your move. At some point, you've got to step up and just go for it,

 

[Caseylove99]

He was probably disappointed that you didn't make your move. At some point, you've got to step up and just go for it,

If he tells me not to sleep on the couch again tonight I may ask if he wants it when we are in his bed. His room is 100% pitch black so he may feel more comfortable not seeing anything. Worth a try

 

[Caseylove99]

If he tells me not to sleep on the couch again tonight I may ask if he wants it when we are in his bed. His room is 100% pitch black so he may feel more comfortable not seeing anything. Worth a try

So.... I just asked him about 2 hours ago and he said "I'm trying to sleep." I rolled back away from him and we layed there for a little while awkwardly and I said "I'm sorry for asking you that, I just really want to make you feel good. Do you want me to go sleep on the couch?" He said "no, not at all" and rolled over towards me and spooned me and said "and thanks, this makes me feel good" and we just stayed like that until we fell asleep. I just got up to go to the bathroom a few minutes ago and he was asleep, or at least I thought he was, I just walked back past his room because I wanted go grab a cup of water from the kitchen and through his partially open door I could see that he was standing up and had taken off his tshirt, shorts and underwear and was getting back in bed COMPLETELY naked, with a BONER. I'm going to be sleeping with him shortly and he is naked y'all. I hope I can "accidentally" brush/rest my hand on it, lol.

 

[hzs3fg]

So.... I just asked him about 2 hours ago and he said "I'm trying to sleep." I rolled back away from him and we layed there for a little while awkwardly and I said "I'm sorry for asking you that, I just really want to make you feel good. Do you want me to go sleep on the couch?" He said "no, not at all" and rolled over towards me and spooned me and said "and thanks, this makes me feel good" and we just stayed like that until we fell asleep. I just got up to go to the bathroom a few minutes ago and he was asleep, or at least I thought he was, I just walked back past his room because I wanted go grab a cup of water from the kitchen and through his partially open door I could see that he was standing up and had taken off his tshirt, shorts and underwear and was getting back in bed COMPLETELY naked, with a BONER. I'm going to be sleeping with him shortly and he is naked y'all. I hope I can "accidentally" brush/rest my hand on it, lol.

Obviously, this comes too late, but I would have said at this point do not ask, just do. Depending on initial position, caress his ass or his chest and just as soon as you feel comfortable, dive down and take his cock in your mouth.

 

[Caseylove99]

Obviously, this comes too late, but I would have said at this point do not ask, just do. Depending on initial position, caress his ass or his chest and just as soon as you feel comfortable, dive down and take his cock in your mouth.

I cannot just do that, he may never say yes, but unless I get a head nod or something from him telling me to, I just cannot do it. BUTTTTTT last night when I went back in his bedroom I decided to "catch him in the act" of being naked in bed now. After I walked in I saw that his clothes we on the floor near the foot of the bed that I had to walk past to get to my side so as I was walking I "tripped" on them and mumbled quietly to myself "wtf where did this stuff come from" and bent over to see what tripped me up and picked up the shorts and underwear and just stood there for 30-45 seconds with them in my hand knowing he was awake and faking being asleep. He knew I knew they were his an he was naked now and pretended to kinds shift around and groggily "wake up" and he said "oh you're back I didn't know where you went and got up to look for you but heard the fan in the bathroom" I was like, yeah, too much soda haha. But then I just decided to say it and was like these clothes weren't on the floor when I left because I would've tripped on them if they were and he was like "yeah... the boys just needed to breathe a little, I usually sleep naked when I'm alone or with girls." I was like "well you aren't alone and I am not a girl" and he was like "are you complaining" and I was like "I didn't say that I was" and he was like "I didn't think you we're going to" and did a little double pointing gesture towards me with a little clicking sound out of the side of his mouth that he does when he is trying to be corny but flirty (with the girls) or sarcastic (with the boys). And then he was like "well get back in bed and pulled the covers back to let me back under, exposing himself in the process. He was still boned up and I was just like "uhhh idk if this is a good idea, if I get under there I may be stabbed by that thing" he was like "yeah it's been like that for a while now mr happy just needs to breathe a little and he will go away but I'll be careful with it, hurry up it's getting cold and fake laughed" so I got back under the blankets and we laid there for a few minutes and then I was like "did mr happy go away" and he said "no not yet." I tried to make my move and said "does mr happy need help going away?" and he was like "yeah I think he does, do you mind if I take care of him?"'and I said "oh... no, not at all" in a dejected voice and he was like ok thanks, brought his hand up to his mouth licked his finger tips and started sliding the skin back and forth. I don't think I have ever been this sad and horny at the same time but just laid there watching his hand go to town under the blankets while his face gently contorted and his eyes were closed. After a few mins I decided to try a move again and I was like "I think I know someone that can help me happy go away faster than you can" and he was like "I'm almost there" and I said "oh ok, but you're going to make a mess under there" he stopped and was like "yeah that wouldn't be good, do you mind if pull the blankets back to finish" and I said "yeah I mind, and you can only do that if I get to watch" he said "ok, but you're weird" and pushed the blankets down exposing himself to me and proceeded to continue while I watched. I was so happy, even in the dim light I could see every hair, every vein, every inch as he jerked that foreskin up and down. The wet sound of his foreskin and his precum was so hot and when he reached over his head and put his arm behind his head, I knew he was close. I kept watching and he started grunting and his balls that were saggy when he started we pulled up to right I knew he was about to erupt but he just couldn't quite cross the line. He kept going really hard like I thought he may hurt himself or tear the skin and he was grunting still but almost like he was grunting in frustration I couldn't take it anymore and I reached down and grasped his balls and that was it, the shock of me touching his balls make him explode his eyes shot open and he looked right into my eyes as he exploded everywhere and I looked down just in time to see the last squirt come out. We said nothing and he just stared at me and finally looked away with an almost defeated look on his face knowing that my touch I was sent him over the edge. We didn't say anything for a while until I finally said "we really should clean you up" he mumbled "mhm yeah I guess" and I grabbed a box of tissues from the side table and handed them to him and he just rested the box on his chest but didn't do anything. I was like "we'll hurry up before its starts running off onto the sheets haha" and he looked at me and said "well you did this, you clean it up" OMGGGGGGGGGG I obliged and I took the tissues and started cleaning up his chest/abs and was like "do you want to do the rest (his dick/balls)?" And he said "well you've already touched it now, might as well clean that too" so I obliged and took me softy gently in my hands and gently cleaned him off with the tissue pulling his skin down and dabbing the tip being careful to make sure I got a little on the back of my hand in the process and was like "ewwww it's on my hand" and he chuckled and was like "sorry, just wipe it off" and I did wipe it off the back of my hand, with my tongue. His eyes opened so wide and his dick, in my other hand, spasmed. Then I did the same double point back at him with the mouth click that he did to me and we got back under the covers and tried going back to sleep. I thought I crossed to much of a line by licking his cum off my hand because he was facing away from me in bed when I looked to his side of the bed, I few mins passed and he finally said "thanks for cleaning me up and helping me finish" and I said "thanks for letting me watch and for letting me help, haha"'and he said "did you like how my cum tasted?" And I said "yes" and he said "interesting... that's good to know" and we went back to sleep. We woke up about 30 mins ago and he has been in the shower while I'm writing this. I hope he will let me suck him or at least let me give him a handjob.

 

[hzs3fg]

Dude! He did everything but say, Dammit, suck my cock already!

That look of defeat after he came was probably because he hoped that you would go for it and finish him off, but you didn't and he was left laying there disappointed.

 

[AHandfull]

Yeah buddy you are in like flynn. He's just going through the stages and he's there, you just have to take the initiative to make him comfortable. Just snuggle up to him next time and masturbate alongside of him and one thing will lead to another. You're making too big of a deal about that first blowjob, just first enjoy the fact that you're in bed naked with each other, and then that you can stroke with each other, and eventually you will get what you want. There's a hell of a lot more to intimacy than just a blowjob. Spoon him next time sounds like he's comfortable doing that with you. Lock legs with him as you're lying side by side on your backs and masturbate together eventually stroking each other maybe. Just let one thing lead to another and don't be so singularly focused on the first blowjob.

 

[Caseylove99]

Yeah buddy you are in like flynn. He's just going through the stages and he's there, you just have to take the initiative to make him comfortable. Just snuggle up to him next time and masturbate alongside of him and one thing will lead to another. You're making too big of a deal about that first blowjob, just first enjoy the fact that you're in bed naked with each other, and then that you can stroke with each other, and eventually you will get what you want. There's a hell of a lot more to intimacy than just a blowjob. Spoon him next time sounds like he's comfortable doing that with you. Lock legs with him as you're lying side by side on your backs and masturbate together eventually stroking each other maybe. Just let one thing lead to another and don't be so singularly focused on the first blowjob.

He would NOT be down to see or touch my junk and I respect that but I may something tonight along the lines of "I'm going to suck your cock tonight and unless you say no, I'm just going to do it. If it's to weird tell me to stop and I will"

 

[hzs3fg]

He would NOT be down to see or touch my junk and I respect that but I may something tonight along the lines of "I'm going to suck your cock tonight and unless you say no, I'm just going to do it. If it's to weird tell me to stop and I will"

A first timer may have a hard time actually asking you to do it or even giving verbal permission. And, the more time you give him to think about it, the more likely he is to back off.

If you find yourself naked in bed with him again, you should assume that he is giving you the all clear. Don't ask. Begin with some gentle caresses and, unless he sternly pulls away, just go for it.

It's obvious that is exactly what he wants from you at this point. He's ready. Don't make him wait.

 

[sunandfun]

He would NOT be down to see or touch my junk and I respect that but I may something tonight along the lines of "I'm going to suck your cock tonight and unless you say no, I'm just going to do it. If it's to weird tell me to stop and I will"

why do you think he does not want to see your cock? next time he gets naked in bed, you should take your clothes off and tell him you like sleeping naked.