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Gather round, boys and girls, and let me tell you the story of my craziest, most memorable sexual experience. I hope you enjoy it. I know I did.
First a little background. This is real. It took place 14 years ago. I was in my mid-40s, just divorced and constantly horny.
I traveled a lot on business back then and the internet made it shockingly easy to re-engage with my long dormant bi side. Years before marriage and real life intervened, I’d had a college fraternity brother who secretly sucked my cock. I still remember his whiskers scratching against my thigh and his smiling blue eyes looking in mine as he happily licked my cum off his lips. I wondered if I could find something like that again.
I quickly discovered that Craigslist, in that day, was essentially Dial-a-Cocksucker for bi business travelers. I loved women but they were…complicated. For those few crazy years I appreciated the fact that I could find a guy — usually a married dude on the down-low — and have him slurping away at my tool in my hotel room within an hour or so. It was all too easy to find blow-and-go satisfaction as a “masculine top seeking oral bottom.”
I hate to make it sound totally transactional or suggest that it was always a one-way deal. I was very much in touch with my bi side then. I loved kissing and making out with the right guy. I had a couple of “regulars” who were fun and sexy. I keenly remember a flight attendant in Myrtle Beach who sucked me off then kissed me full-on with a mouth full of cum. I still recall his soft tongue swirling my own semen around in my mouth. It was very kinky and I loved it.
But I digress…
Our tale begins in earnest one fine summer day when I got a message from a guy I’d previously chatted with on a hookup site. He had an invitation: Would I like to come spend the evening with him and his partner at their place by the lake? They were in a committed relationship but they liked to occasionally add a third and they preferred married or divorced guys.
They seemed like cool people. Jim was a semi-retired history professor and his partner Doug was a good-looking 30-something former student of his. I assumed they were a bookish gay couple who wanted to share a nice new cock but Jim quickly disabused me of that notion: “We’re both tops and we love breaking in guys like you.”
It took me a moment to process the meaning of “breaking in.”
Wait…what? Holy shit! Seriously? I’ve never really bottomed. Two guys?? Could I actually do this? How would it feel to catch instead of pitch? I swear the hair on the back of my neck stood up.
As I stared at his message on the screen, I realized I wanted it. I wanted to be submissive for a bit. I wanted to not be in charge for once. I wanted to be used just for someone else’s pleasure.
My stomach was full of butterflies and my cock rock hard as I replied, “I’m in.”
* * *
The drive to their place was about an hour. Trepidation doesn’t begin to describe how I felt. I thought about bailing several times but, suddenly, there I was in their driveway. Their home was beautiful and I could see a nice deck overlooking the lake in back.
Jim was there to greet me. He was tall, a little bald but deeply tanned from life on the lake. Not bad for a guy in his 60s. Doug, was dark with salt-and-pepper hair, tall and athletic looking. He came out, shook my hand and wowed me with compliments, “God you’re good looking. I’m so glad you came. Let’s get you a drink.”
Jim showed me around their home’s main floor and I couldn’t take my eyes off of the amazing view of the lake. We talked fishing for a bit and sipped some whiskey and smoked a little weed. I relaxed because it seemed like they really were good guys and probably not serial killers after all.
The mersin escort conversation ebbed and Jim said, “Let’s have a look at you.” I knew the moment of truth was at hand.
I walked over to where they sat together on a couch and stood in front of them, like a nervous teenager at the dance, wondering what would happen next. What did happen was Jim stood up, came close and kissed me. Not a little peck but a really nice mouth kiss that I felt all the way down to my balls. It left me a little breathless. He pulled off my shirt and slid my shorts and underwear down and threw them in the corner. “That’s the last you’ll need of those for tonight.” I stood naked in front of them.
Doug rose and came up behind me and reached around to rub my stomach and play with my nipples. He kissed the back of my neck and pulled me to him. He reached around to give my hard dick a gentle pull and then he ground his crotch against my ass. I was naked between two big guys who were kissing and rubbing me. I liked it a lot.
I’d been thinking about sucking their cocks for days. Jim had told me they both had above-average dicks, but every guy says they have an above-average dick. I assumed the reality would be closer to my six-inch stiffy.
I took a breath and decided to go for it. I knelt down between them. Jim moved closer and I reached over and slid his gray sweat pants down. His pubic hair was white against his all-over tan and his penis was half hard and big. It was longer and thicker than mine. I leaned forward, still looking up at him, and extended my tongue to lick just the tip of his cock. I tasted pre-cum and it made me hot for more.
Jim moaned and smiled. “Good boy,” he said. Doug stepped over and unzipped his shorts. Out popped virtually the same big dick except darker and maybe a little thicker. Damn. They weren’t bullshitting after all.
Doug took my head in his hands and pulled me closer to his gorgeous dick. My mouth opened instinctively and my lips wrapped around the tip. It was hot and tasted like coconut oil. I swooned a little at the moment. Whatever inhibitions I had were melting away.
As I started to take more of him into my mouth, Doug clenched my hair and pulled my head back a bit. I looked up at him, not quite sure what to do. I quietly said, “Please?”
He slapped his hardening cock on my face a few times and said, “Please what?”
“Please let me kiss it?”
Doug smiled and rubbed his thick cock over my lips. Jim leaned over and quietly but firmly said, “Here’s the deal…we’re going to whatever we want with you. With your mouth. Your ass. You’re going to be our little fuck-toy tonight. Do you want that?”
I shivered at the thought of submitting.
“Yes,” I said, “I want that. Please.” Saying it was scary and liberating all at once.
They sat side by side on the big couch while I did my level best to worship those two thick cocks. I licked and sucked and switched from one to the other while they drank and smoked and watched porn. Doug was hard but Jim, even with a Viagra and a cock-ring thingy, was only semi-hard. I took Jim’s hairless balls into my mouth and worked my way down his taint. He said, “Lower. Lick lower.” and I did. I tickled his hole and pushed my tongue in as far as I could. He was loving it.
While I was on my knees intensely focused on getting Jim’s big old cock hard, I felt Doug reach behind me and rub lube on my hole. My eyes flew open and I thought that thick rod of his was coming in next. But instead he eased his big thumb into my hole, stretching my ring and driving me crazy.
I was moaning around Jim’s cock in my mouth when I felt something hard replace Doug’s fingers in my ass. It was a plug that vibrated and I swear it felt mersin escort bayan like it was six inches around. Doug pushed steadily, stretching me wider. I started to whimper a little and he suddenly slapped my ass hard. “Quiet, bitch,” he said. It shocked me into silence but I admit I liked it. The heat from his hand radiated through my body. He was in charge.
I bit my lip as the pushing continued. It was a little scary until the moment it just suddenly popped in. OMG! I was almost paralyzed by the feeling of this huge toy in my ass rubbing against my prostate. My cock was leaking like crazy from the vibration and pressure. My insides felt full and balls tingled.
(The other thing that made me tingle were the poppers they would occasionally push under my nose. I didn’t have much experience with them, but man did they hit me.)
Jim suggested we take the party to their bedroom. I followed gingerly behind them trying to keep that wonderful buzzing plug in my ass. The bed was big and the view of the darkening lake was spectacular. I followed them through another door and was gobsmacked to find a giant tiled bathroom with a big walk-in shower, sauna and jacuzzi tub.
We got in the shower and the heat and steam filled the room. I made it my business to touch and soap and wash and kiss every inch of both of them. I sucked and bit Jim’s nipples (which he loved) and I noticed his cock was finally hard. Doug bent me over under the hot water and eased the butt plug out. It felt so empty until two of his big fingers took its place. He stretched me more and then surprised me by grabbing a hand-held shower wand and shooting it full blast into my stretched, gaping hole. “Gotta have you nice and clean,” he said.
Jim shut off the shower and led me, still dripping wet, over to a spot where the edge of the tub extended several feet creating a raised platform. The spot was set up with a foam mattress pad, a big pillow and a collection of fun stuff: lube, toys and more poppers.
Sensing what was coming, I crawled up on the platform and got on all fours and pulled the big cushion under me. Doug appeared next to me with yet another popper and a terrycloth robe belt. He jammed the popper under my nose, making my head spin again, and then tied my wrists with the soft belt. He pulled my arms forward, stretching me out over the big pillow, and tied the end of the belt to the tub faucet. My naked, wet ass was exactly cock-high for these big men.
It occurred to me in that instant that this was a regular thing for them. The invitation, the pot and the poppers, the set-up in their bathroom…they’d done this before. They’d seduce mostly strait guys and turn them into willing bottoms. And now it was my turn.
I don’t remember every moment of what happened next because it was total sensory overload. Doug came up and shoved his cock down into my throat for real. He used my mouth like a pussy. I gagged but he didn’t stop. He fucked my face hard. I wish I could say I relaxed and skillfully deep-throated him to climax but that’s not what happened. With my hands tied he just kept pushing that big tanned cock into my mouth. I was slobbering and gagging and tearing up. But it was hot.
I felt warm lube being poured over and into my ass. “I’ve been waiting for this moment since I saw that first hot pic you sent me,” I heard Jim say from behind me. “I’m going to give you what you came out here for.” The head of his cock teased my asshole for a long minute and then he started to slowly push it in.
I know guys say this a lot but it felt impossibly big. My brain was screaming that there was no way even half of it would go in. But he kept pushing, grinding that thick piece of meat into me. I remember clenching escort mersin the terrycloth bindings and biting the mattress and squeezing my eyes shut while he grunted and pushed behind me. I really felt like my entire body was full of Jim’s dick.
Slowly, with more lube, he began to fuck me for real. I finally opened my eyes and turned my head to see Doug grinning wickedly at me. He pushed his cock back in my mouth and resumed casually fucking my face.
What was probably only 15 minutes of me being spit-roasted like that seemed like hours. Jim fucked me deep and banged my prostate around and Doug talked dirty to me while I sucked him. It was my sluttiest dream come true: I had a nice fat cock in each hole. I felt lightheaded, like I was floating outside my body, and the occasional popper made it even trippier.
Jim finally started to lose his erection a little and he slipped out of my ass. I remember feeling panicked about how empty I suddenly was. Jim ordered me to roll over and get on my back. Doug moved around and shoved the big pillow under my butt. He lifted my legs in the air and over his shoulders and I looked down to see the tip of his perfect cock poised to push into me.
I felt utterly female at that moment. I was bound, ankles in the air, my “pussy” was open and wet, and a big, handsome man was looking me right in the eyes and getting ready to fuck me. It’s very weird to think back on it this way, but the helplessness was an enormous turn-on for someone who was always in control.
After all the “breaking in” Jim had done on me, Doug’s hard hog slid right in. Honestly, he fucked me sooooo good. Pushing into me, bottoming out, grinding his cock inside me, kissing me, pinching my nipples, and spanking my ass until it was red and hot.
Jim started rubbing his semi-hard cock — which was straight out of my gooey rectum — all over my lips and face. “Oh yeah. That’s what he really likes,” said Doug. I sucked on the head of Jim’s dick hungrily while he jacked himself and watched his lover pound me. Doug was younger, harder and hotter than his partner and at that moment I was willing to be fucked like this by him forever.
As Doug started pounding me faster Jim said sternly “Open that mouth for me you little cocksucker” and he came with a furious growl and shot wads of cum onto my tongue and face and neck. He sat back, apparently exhausted, as his cum dripped down my chin and his partner continued to piston my ass.
“You love this don’t you?” hissed Doug.
“Fuck yes,” I cried.
“Good,” said Jim. “Next time we’ll take you out on the boat and you can be our cock whore all day.”
“Oh god yes, please” I whispered. “I’ll do anything you want.”
Jim laughed. “That’s good. We might have to invite a few friends who’d also love that tight ass of yours.”
The sheer filthiness of that seemed to send Doug over the edge and he stiffened and rammed me five or six last times before he filled my ass with his orgasm.
I was both enormously relieved and infinitely frustrated when Doug slowly pulled that big wet cock out of me. I was shaking and exhausted and covered in sweat and semen. He just stood and stretched and came over to untie my hands. His cock was shiny with cum and lube and my ass juices, but as soon as I was loose I knelt down on that tile floor and sucked it clean while I looked up into his eyes. It was so fucking dirty.
They left me there — wrecked, with cum trickling out of my ass — and went back to the living room for drinks, giggling and sort of high-fiving each other for breaking in another mostly straight guy. I finally wobbled to my feet, figured out how to turn on the fancy shower and cleaned myself off. I found my clothes, told them thanks, kissed each goodbye and headed home with an aching ass and mind-blowing memories that last to this day.
Despite some tempting invites for another round, I never saw them again. We’d had one amazing time but I never went back. Probably because it occurred to me that maybe, just maybe, I liked being used a little too much for my own good.
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