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Hey guys, kind of a long one. Still very fresh, my head's still swimming. Tl;dr, the title.
A little background; I'm bi (always have been) and my friend (we'll call him Caleb), who's been on-off dating his gf of 3 years, has occasionally brought up thinking about/having a handful of bi experiences too. We partied together a lot in our 20s; we've always been very open with one another, and this kind of thing usually only came up when we were both intoxicated and alone; he'd admit he'd been watching some bi-threesome video or fantasized about giving a blowjob or some such. Nothing ever really came of it (other than trading porn links a handful of times he stayed over when he was too gone to drive home), mostly because he was in a committed relationship, which we both fully respected.
Fast forward to this past week, and I was in town surprise-visiting family. Caleb called me almost as soon as I got in on Tuesday, so when I answered I asked him if he wanted to make time to hang out. Turns out, his gf had just given him the "let's take a break" talk; which as it turns out was a mutual feeling, but stung nonetheless. I told him as luck would have it, I was staying in my old garage apartment at my parents' house for the week, and I'd be free on Saturday night if he wanted to have a few beers and unwind.
After spending a few days with my family, I was ready to unwind too; so I messaged Caleb on Saturday afternoon a photo of a full case of beer next to the my couch with the text "U down or what?"; he responded with a few snowflake emojis, meaning that he intended this to be a big night for us, just like the old days.
And it was. We settled right back into the old routine; gaming, catching up, and talking top-shelf trash. About half the case in, Caleb started to open up about how things went down with the gf (let's call her Katy, for simplicity)-- outside pressures with work and family obligations, trying to find time for each other, compatibility concerns and so on. The thing, it seemed, that was keeping them together in the end was that the sex was good. Buzzed as I was, this revelation piqued my interest, I buttered Caleb up as a stud and I pushed for some details.
We traded a few stories back and forth, and in the end he said that the breakup was especially straining for him, because I guess Katy had turned him onto this NNN idea where he wasn't allowed to relieve himself in any way for the whole month-- no porn, no masturbation, no sex, nothing--complicated by the fact that she was doing everything in her power to tempt him. But since the breakup, he was still holding out. We both laughed it off, but the wheels were turning.
As the night progressed, things got more heated. Caleb pulled out the baggie he picked up for us, and we got into it. We moved to the couch and I let my friend vent about anything that came to mind, but it kept coming back around to how good the sex was. By the time midnight rolled around, we were both feeling very charged. I noticed at the steamiest height of the conversation that Caleb was straining against his jeans, and he caught me drooling over it. We sheepishly grinned at each other, threw a background movie on, and continued the conversation as normal.
He shared some very detailed accounts of Katy's love for sex toys, including the fleshlight she'd bought him for his birthday, which she used on him regularly. In my excited state, I blurted out that I had one too-- but a smaller, "pocket-sized" one. I nodded to the side table next to him, it was still in the drawer.
We caught each other's gaze, and some combination of the drinking, drugs and dirty talk suddenly took control. I paused the movie and rifled around in my phone for a minute or two, until I found a porn clip Caleb had sent me over the summer: two guys and a girl, in an apartment not unlike this one, followed by a "this could be us but u playin" meme. I stood up, leaned over Caleb and pulled the fleshlight out of the drawer, with a small bottle of lube. I thrust my phone into Caleb's hands, "Hit play."
Caleb did as he was told, and when the tv flickered on it was a scene of the girl on her knees between both guys. I could see Caleb piecing together what was happening in real time as I positioned myself on the floor in front of him-- I flashed him a "green light?" look. He caught his breath and loosened his belt.
I'd seen Caleb's cock a dozen before, but never hard. It was gorgeous-- clean, curved and uncut. I pulled the foreskin back and grabbed him gingerly by the base, giving it a playful little wag to test the stiffness. I squeezed a little and stroked about a quarter of the way up until a clear bead of precum appeared. He was ready, and so was I.
I nodded toward the fleshlight on the couch next to him, and quickly glanced over my shoulder to see the girl in the video giving up her throat to the boys sitting next to each other, alternating back and forth. I took the fleshlight from Caleb while he fiddled with the bottle of lube, uncapping it and drizzling it over himself.
"Lay back and imagine it's December 1st," I joked. Caleb chuckled and laid his head back on the couch, glancing between the tv and me through half-closed eyes. I pressed the toy down around him, twisting as I went, and he couldn't help but roll his hips against it. I asked him how it felt.
"Cold, but good." he responded, letting out a soft breath as I started to build up a rhythm.
I was transfixed. Admittedly I'd thought about this before, but it was actually happening. The image of Caleb's thick cock pumping up through the end of the stroker, this solid and flushed and glistening taboo, is burned into my mind. I knew with how pent-up he was, he wasn't likely to last long; but I wanted to draw things out, to savour it as long as I could.
So I took my time. I alternated my pattern, squeezing on the downstroke, loosening on the way up. Every time they switched positions on the TV, so did I. About ten minutes in when Caleb locked eyes with me and nodded his head breathlessly, I pulled the toy off of him, leaving him straight up in the air, twitching. He grimaced, flexing his thighs and grabbed a handful of cushion in his frustration. I smirked, "Not yet."
By this time I was beyond ready for some reciprocation, so I joined my friend on the couch again. The boys on screen were taking turns with the girl, so I followed. I pulled myself out from my boxers and sunk the toy down on myself, still wet and warm from edging Caleb. When they switched, I switched, alternating the fantasy of sharing someone with one of my best friends. He started dirty talking, imagining out loud that we were sharing Katy, fantasizing that her pussy was ours to use for the night.
The fantasy got to me, imagining having a threesome with my friend and his girlfriend sent me over the edge. I told Caleb I was about to cum, and at the last second he grabbed my hand holding the toy and asked "Do you want to cum inside her?" I nodded sharply and he let my hand go as I had a full-body orgasm while I imagined him watching me flooding his ex; it felt so wrong, but in the moment that only made the feeling more intense. Out of the corner of my eye, I saw Caleb reach for the lube, slowly stroking himself and watching waves of cum pool up and spill over the rim of the toy. He settled back, teasing himself, and let out a breath. "That was fucking hot."
I glanced at him from the corner of my eye. "You like that, huh?" He nodded in response.
"Look at her, I think she wants to fuck you now." I smiled, pulling the toy off, still dripping. I hovered it over him playfully, to gauge his reaction. "You don't mind sloppy seconds?"
Caleb smiled and lifted his hips to pull his boxers off. I slid off the couch and settled between his legs, pausing for a moment to take everything in. I rested to toy on the head of his cock and caressed his balls with my fingertips; he twitched at the sensation and I watched a bead of my cum stream down his shaft. He took in a sharp "Oh fuck, I can feel it" before I leaned in and dragged my tongue all the way from the base of his cock to the underside of the head, showed it to him, and swallowed. "That's gonna be you in a minute." His eyes rolled back.
I worked myself into a steady pace: stroking him with the toy, kissing his thighs, and gently sucking on his balls, slowly feeling them tighten against my tongue. He kept adjusting himself so I asked him how he was feeling, and he said it was was good but felt almost too wet. I pulled the toy off and took a moment, stroking his abs and thighs with a feather touch. I took a sip of my beer and said, "Okay, let's try something else then."
Guys, allow me a moment to break the fourth wall to say that THE MOAN this man let out when I guided the head of his cock past my tonsils was the hottest thing I've ever heard. He couldn't be stopped. I bottomed out a couple of times before pulling him out again, a stream of drool hanging between his head and my lips for a moment before he took my face in his hands and mouthed "Ho-ly fuck". I pushed him back into a slouch as I slurped up and down both sides of him, sucking off all the excess cum, lube and spit. At this point he couldn't keep his hands off me so I told him to lay back, relax and let me do my thing.
I spent the next ten minutes giving this man the sloppiest, toppiest, dirty-talkingest head game of my entire life. I told him how perfect his cock was, how Katy was a fool for giving it up, that I could do this for him every day if he wanted. I drooled all over him, and blew spit bubbles all over him, which he loved. He kept saying how he'd fantasized for so long about using someone else's cum as lube, his group sex fantasies about Katy. It was that last thought that pushed him over; while I edged him he stiffened up in my hand and started to buck against my grip. I pulled him close and buried him deep in my throat, and felt him swell up. I slowly, lovingly swirled my tongue around the head of his cock as he tensed hard and unloaded almost three weeks worth of thick, briny frustration into my mouth. When he subsided, I made sure he was watching as I pulled away and blew three huge cum bubbles for him before downing it all and showing him my tongue-- all gone.
We relaxed for a second and let everything sink in. We looked at each other bashfully between fits of laughter and astonished wows. I handed him his boxers from the floor and broke the ice with a silly little "So maybe I could get your numberrrr?" and Caleb chuckled.
"Yeah, I mean I thought you had it already, but let's make sure... in case, yknow, you wanna do something like that again."
He crashed over that night, we slept late and he stuck around for most of the day to help me pack up (which earned him a hungover "thank-you" blowjob). Things have been surprisingly chill in the aftermath and we've sexted a few times since Sunday. We both want to keep things light and casual; but damn if this isn't something I've thought about a lot.
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