I Need Something Tight

First some backstory: I'm a gay man in my early thirties. I've known my best friend since 4th grade, he's one year younger than me and he's straight. Let's call him Andy.

Freshman year of high school, I started playing with his dick after he fell asleep. I don't know how long this went on with him unaware, but at some point it became clear that he was faking being asleep and letting me suck his dick.

Young gay me was voracious. Anytime we stayed over at each others, I couldn't wait for bedtime. At one point he asked me to tutor him after school, but without fail every day it was 10-15 minutes of tutoring, then he would "get tired" and take off his belt and take a nap on his couch. I'd swallow his load and then he would "wake up" and we would hang out and watch TV or play video games or whatever.

Since high school we haven't really lived very close to each other. Always off in different places for school, living our own lives. But we would occasionally visit each other and sure enough, when bed time rolled around Andy would do something to signal to me that he wanted head: cough/sniffle a ton, vibrate his legs, I don't really know how to explain it but you could feel the tension.

For the last year, we've been living in the same city, so we've been getting to see a lot more of each other. He now has two kids, but shares custody so every other weekend he's alone to hang out.

So fun for me, I get to hang out with my best friend, and every couple of weeks swallow a fat load out of a hot straight dick. But still, I hold these lingering feelings of resentment that this is all done while Andy is "asleep". Even with all of his signs, I can't shake this underlying feeling of "what if" I'm just some guy molesting his friend. Over all the years, we've never spoken at all about the things we've done.

That all changed recently. About a month ago my boyfriend, myself, and a female friend (let's call her Jessica) of ours went skinny dipping at the river after sunset. This night could be a whole post itself, but long story short there was a couple older fellas there, all of us were drinking and smoking pot, and one of the guys serviced my bf and I right there on the shore while Jessica watched with glee. Once one of us was sober enough to drive, we went back to Jessica's house to crash, and all the hormones and shit got us so pumped up that we both ended up fucking her.

So I tell Andy about our fun river shenanigans, and I don't really leave out any details. He expresses his desire to go swimming, how he's never gone at night, and it sounds so fun, etc etc. We make plans to go back to the river, same location, the next weekend.

But I can feel something. I can tell things are about to change. I can anticipate, just like you dear reader, that something is gonna go down at the river with my straight best friend.

To the river we go, just myself, my boyfriend, and Andy. There is no hesitation getting nude. We wear glowsticks for cock rings and spend a good while swimming around and smoking a little weed. This is my first time being nude in front of him, and I was enjoying showing off a ton. I know he's straight and doesn't care, so I'm just pushing boundaries and playing with myself casually here and there.

We are standing rib-deep in water, leaning against a rock, Andy right next to me and my boyfriend just a few feet away. We are looking up into the night sky, not talking a lot. Even though it's dark, the glowsticks give enough light that I can see Andy is erect. I immediately bone up, take a breath, and say "the water is so nice I'm getting hard". Andy says "ha ha, yeah, me too"

The next few seconds felt like hours in my head. I gathered all my strength to reach across and grab his dick. It's searing hot through the cool river water. I've sucked it hundreds of times before and it just felt so much thicker than ever before. My mind is racing, and I just jerk it. I'm jerking myself good too. Still, nobody says anything. He even tries to make some sort of casual comment, as though nothing is happening under the water at all. With my bf standing right there and me not wanting to push my friend too far, I back off after a good solid minute or two of stroking.

We go back to swimming around and chatting and I can't focus. Yes, I've had that dick before, but this is different. Now he's for real, no doubt, awake. Still not quite acknowledging it, but a barrier is broken. The conversation is about sexual history and stuff, and I take my opportunity to push further: "Hey Andy, remember when I was 15 and I 'jokingly' said I would suck your dick anytime, you just have to ask? Offer is still on the table haha" we laugh about it and move on, but sure enough a couple minutes later he asks "so if I want a bj, is there like a codeword?" and I say "if you want there to be, sure, but I'm fine with just 'hey, you wanna suck my dick?'" My memory is fuzzy now but pretty sure we just dropped it there and went back to swimming and chatting about other things. My bf was starting to get cold so headed for the shore.

Andy is leaning against the same rock as before, and I'm standing sort of in front of him. He's not hard anymore, but I've decided to make my move so I reach out and grab him. It doesn't take long for him to get hard, and while I'm fondling his dick he even says "I don't know why, but I'm getting hard again" like really? About 5 strokes after getting him fully hard, I reach towards his hips and he knows exactly what I'm going for. He swings his legs up to float on the water as I engulf his shaft. He starts mumbling about how this is first time getting head in the river, first time getting head outside, and says he isn't going to last long. I pull off just long enough to say "that's fine, cum whenever you want" and I go back down on him, his hand following my head and he holds my neck and repeats "i'm not gonna last very long, i'm gonna cum soon, i'm gonna cum, ooooooh i'm gonna cum" and then his grip gets firm and I just lose my mind. I'm gagging myself on his dick swallowing it as he throbs, we lose balance in the water and both sort of fall over and correct, laughing and panting and groaning. He says "huh, who knew getting a bj while floating could be so hard". We head over to shore and my bf smiles at me and told me he just jerked off. I assumed he could see/hear us in the river, but when we talked about it later he had no idea. He was so upset he couldn't see. Smoke a little more, chat a little more, enjoy being naked in the cool night air, and eventually we wrap everything up and head home.

When I drop Andy off after the river, I tell my bf to wait in the car. With everything going on, now was the time to confront the past head on. So I tell him thoughts and feelings, about my self discovery over the last few years, about what we just did and have been doing since childhood, and I end it with "so, while I don't want to feel like a molester, I also don't want to stop sucking your dick."

His response? "Water under the bridge my friend". No real feelings. No rejection or acceptance or dismissal of my offer to keep sucking his dick. No anything really. I would have been so frustrated if I wasn't so completely turned on by the fact that he had just held my head down on his dick about an hour prior.

The bf and I were trepidatious the next few days. Did I take things too far? Are things gonna get awkward? Nope! Things carried on like normal. We still chat and hang out exactly the same, but no sleepovers.

Until we made plans last week to hang out on Saturday. He's got a bottle of vodka, work has been shitty, he wants to get drunk. I haven't gotten drunk in years, sounds fun, let's do it.

As the night goes on, the bottle runs out. We try to walk to safeway to pick up more, it's not even 11 yet, they should still be open. Andy is making a point of being obnoxious about his lack of sobriety. Making loud conversation with homeless people and various inanimate objects as we go. Alas, safeway is closed so we turn around to head back. Andy goes to piss off the side of the road and once he's done my drunk ass tries to get down and suck him. I was half expecting him to freak out about it, being the straight guy he is, and with this being very... public. But he just says "wait till we get back to your apartment".

Back to the apartment we go. When we get there, my bf says he is sober enough to drive to an actual liquor store and pick some up. Really, he just wants to leave me and Andy alone so that Andy is comfortable to fuck around. Bf leaves, Andy goes to piss again. Again, once he's done I drop down and undo his pants. He lets me suck him for a bit. Thank god for alcohol, I never would have made these moves sober. I barely start sucking him when he says "let's take it to the bedroom".

Immediately he's naked on my bed, I'm in between his legs, and I'm going to town on his dick. Like, I'm gay, I like dick, I give good head, but if I'm really honest with myself I'm generally more enthused to get sucked than do the sucking. Aside from occasionally bottoming for my bf, I'm all top.

But y'all know what straight dick does to us. And since he's now "officially" willing, I've lost my mind. There's slobber pouring down his dick. He's not afraid to push me down and I'm waaaaay more willing to be gagged than I ever have been before. He says "what happens here stays between us, right? Well, and your bf" and I say "of course". He makes me scoot around to bring my waist closer to him. For a brief second I think he's going to maybe suck me too, but he's straight, that would never happen. But he grabs my dick and starts stroking me. Okay, this is definitely unexpected I think to myself. I knew I'd be sucking that dick tonight but never thought he'd ever touch mine. I'm moaning through his meat, can't get enough precum and he's delicious. He's groaning, whispering how good it feels. How much he's needed it. I'm working, I want to earn this load. He stops moaning and says/asks/tells me "you've wanted this" and I respond "forever". slurp slurp slurp moan "What do you want?" he asks me. I don't know exactly what he means. Like, recip? I just want to keep sucking his dick. I say "whatever you want man, I just love your dick".

Now, I already thought our entire relationship, my best friend in the world, had crossed wild new levels that night in the river. But like the rest of 2020, things were not done escalating. What happened next will be burned into my mind until I die.

Andy pushes my lower half back away from him, and pulls my head off his dick as he starts to move out from under me. As he starts to position himself at the lower end of my bed, he says "I need something tight". My soul left my body right then. I can't reach for the lube without pausing the activities: looks like I'm not using lube tonight. I'm tight. He's huge. He prods at my hole and it burns and I tell him to wait a sec. I know I'm not going to get relaxed anytime soon so I help him line it up and then I just bite my pillow and bare through the initial pain. He slides in and immediately gets to pounding. I catch myself grunting and think "shit, is that too masculine for him? Should I be more femme" but I can't decide so I just sort of go silent, only letting through muffled groans and I can't even remember how many times his dick forced the phrase "oh my god fuck me" out of my mouth. The pain subsides (or is masked by the booze and endorphins, whatever) very quickly leaving me there, on my knees, face down, with my straight bud behind me, and his fat raw dick thrusting in and out of my practically unused hole. Just like the river he says "I'm gonna cum soon" but this time much louder. I yell back "please, go for it" and he lets out a crescendo "uh, uh Uh, UhhhHHHHH" and pulls out and falls on his side.

He thanks me and says he really needed that. I said something about being glad to help. And with that, we put on a minimal amount of clothing, went back to the living room to join my bf and continued on with our night. The next morning I sneak over to where he's laying to suck him off like usual. But now that the pretense of sleep is gone, he gets into it. Once his dick is hard, he "wakes up". He's vocal. He's writhing. His dick feels thicker and longer than usual. He puts his hand on my head and talks to me "thank you" he says "just keep sucking" he says "it's cumming" he says. I swallow another of his loads, and even though he just bred my hole not 6 hours prior, it was one of the biggest I've got from him. I say "nah, thank you...and good morning"

18 years it was a shameful secret. And then suddenly, it wasn't.