One weekend the girls took the kids for a weekend trip, leaving Gary and I solo, so we figured we would catch the game and hangout at my place.
We had probably gotten drunk watching sports together hundreds of times, but this time Gary brought some weed; something we don't do often.
I have a large wraparound deck that the one side has a full wall for complete privacy, so we go there with our drinks and smoke the joints.
This is also where I have my hot tub and Gary said we should go in. I agreed, saying I will go get us some suits and he drops his pants super quick, exposing his flaccid dick and strips his shirt over his head saying "Pussy, don't be so gay" and hopped in the tub.
I laughed at him and it's not like it's the first time we had seen each other naked, we have camped together, played sports together, gone to the gym, so what's the big deal? I took off my clothes and joined him.
We continued our drinking and smoked another joint, carrying on the conversation from before, but it now turned to be about past sexual conquests and telling old stories from when we were young and single.
Taking a break from the heat, we sit up on the ledge of the tub, fully exposing ourselves to each other again as I tell him the story about the time I had sex while on vacation with my wife on our balcony and how hot it was knowing that people could see us.
I couldn't help but notice that his dick started to grow as he was listening to the details.
Gary proceeds to tell me that lately he has really been into anal play and can't get enough. He told me how he never would have thought he would be into it, but he was high with his wife, she suggested they try it and the weed in his system meant he had no inhibitions, so why not? He told me he never cums that hard and can't get enough.
I'm not sure if I misunderstood him or if I was so high I overshared, but I got so excited hearing this I couldn't wait to tell him my recent discovery.
'Dude, so funny you say that. I haven't told anyone this, but a few weeks ago Alicia and I were fooling around and she gave me a rimjob for the first time ever. I was the same as you; never thought I would be into that shit, but holy hell it felt so good, I loved it. Honestly? I fucking came so hard without her even touching my dick. It was incredible!" I shared.
"Good for you man" he replies, "But she wasn't playing with my ass, I was eating and fucking hers" he clarifies.
I felt a rush of embarrassment. How could I have been so stupid? I sank back into the tub, not wanting my cock to be exposed anymore and mutter "Yeah, that's cool too" not knowing what else to say.
There is a little bit of an awkward silence, until Gary breaks it by saying "Buddy, don't be embarrassed, the male prostate is the most sensitive region, it makes total sense. Just the fact that she went down on you is fucking hot. I'm getting hard just thinking about it".
It did make me feel a little bit better. My mind started to slow down a little bit and then I start to think about he last sentence. What part of my story was he thinking about that was making him hard?
'Yeah, I can see, put that thing away' I jokingly tell him referring to his hardening cock.
'Oh, what's the matter buddy? Are you intimidated by my big dick?' he mockingly says.
'Yeah right! My dick is just as big, if not bigger' I reply.
'Bullshit!' he yells.
'It is. I'm just a grower not a shower' I say with a chuckle.
'Well get that thing growing and let's measure' he challenges.
I'm sure the weed helped with my thinking, because I stood up in the tub and began to pull on my dick, which did not need much encouraging to get to full attention, matching Gary's already hard cock.
'Alright, let's measure' Gary says walking right in front of me.
He lines up so that his dick is right under mine, sliding it against the bottom of my dick, his head softly pushing against my ball sack with a hand on my right hip.
'See, mine is bigger!' he says in celebration.
As I look down at my now throbbing 6.5" dick, it is pretty clear that he has some length and definitely a good amount of girth on me, but I wasn't willing to concede.
'Bullshit. You're measuring with your fucking foreskin too. Unfair advantage!' I protest.
With that I reach down with my right hand and softly pull the foreskin of his dick back exposing the head of his cock and I give it a couple of soft tugs as he closes his eyes and looks up at the sky.
I interpret that as if he is enjoying himself, so I open my hand and with our cocks stacked on top of each other I begin to stroke them both at the same time to Gary's hips lightly pushing back and forth, moving his hand from my hip to my ass cheek, lightly rubbing it.
I am now so turned on, I am no longer thinking, but simply moving on auto-pilot as I push him back so he is sitting on the edge of the tub again. At this point, I kneel down in the water between his open legs and stare at his cock that I now admire. I specifically like how much thicker it feels in my hand than my own with a few more soft strokes before giving the head a kiss, then down the side of his shaft, licking my way back up the other and then I open my mouth and take it in.
Now, what I have not shared with Gary is that over the past few months I have began to explore with guys while travelling for work. This was not my first time giving a blowjob, not that I was THAT experienced, with probably 4 previous blowjobs to that point, but he definitely did not know that.
I remain focused on my task, bobbing my head up and down, rubbing my right hand over his stomach and chest, while gently playing with his balls in my left to his moaning approval.
Gary's hand rubs my back as I am bent over, then he reaches down further to my ass, and his finger makes contact with my asshole, to which he applies some light pressure, but does not go inside, simply presses in a circular motion, then releases pressure.
He grabs me by my arms and stands us both up, quickly stepping behind me and bends me over the side of the tub.
'I told you I liked eating ass' he said as he kneels in the water diving his tongue straight into me. I was shocked, but pleasantly surprised because he knew what he was doing and it felt amazing.
Gary moved his tongue inside me up and down, then little circles. He would pull his tongue out and gently lick the outside, while cupping my hanging balls and then giving my cock a few tugs, before diving his tongue back in deeper than before.
I was in heaven, no thoughts given other than the incredible feeling going on right now as Gary grabs a cheek in each hand spreading me wide as he makes me quiver with his tongue.
I slap the deck 'Fuck. Oh my God, fuck, fuck...holy shit...fuck me' I say out of breath.
'Yeah?' he says as he stand up behind me, grabbing a handful of my ass cheek.
I don't reply. Why did I say that? I didn't mean for him to fuck me, I just meant 'fuck me, that feels good'. But why wasn't I saying no? Why wasn't I saying anything? Why was I still bent over feeling empty without his tongue inside me and my friend standing behind me?
Gary held his cock in his hand and began to rub it up and down my ass crack. 'Is that what you want?' he asks.
I only let out a loud sigh as I am frustrated with myself for not knowing what I want.
He points his dick right at my hole and presses forward, his head entering me. 'Is that what you want?' he repeats.
Now, the friction from the water did hurt, but the warmth of his cock inside me felt really good. 'Mmmmmm' is all I could muster, not wanting to say no, but not able to pull myself to admit it is exactly what I wanted as I pushed back my hips a little.
Gary took the hint and slowly pressed forward. Stopping so I could adjust before pressing forward again. By the third time, he bottomed out as I felt his balls against my ass. My best friend was deep in my ass.
He held his dick deep inside and I began wiggling my hips, there was no pain anymore, just pleasure. Gary slowly pulled back the length of his dick and then back again, repeating this motion, picking up the pace each time.
He grabs me by hips and starts really going hard causing the water to splash underneath us.
He pinches my nipple, then slaps my ass and I can hear a change in his breathing as he leans his head back pulling me tight and he buries his dick deep exploding inside me.
We hold ourselves there for a few moments and he shudders and empties everything in me. As he pulls out still standing in the middle of the tub, I turn around sitting on the edge and frantically start jerking off with my right hand, rubbing my hand on his chest and rib cage with my left, feeling his cum start to drip out of me and I erupt, sending ropes of cum on Gary's stomach and dick.
'Oops, sorry about that' I say, kneeling down licking my own cum off his stomach and dick; noticing the difference in taste after he had been inside me.
We were both in shock, not knowing what to say, but knowing our relationship just changed forever.