Craigslist Pt. 02: The Two Bears

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It’s been years now since they vanished, but I still miss the Craigslist personals. Sure, they were filled with fakes, phonies and pic collectors. Even if you managed to hook up through one there was no guarantee that you’d actually have a good time.

Once in a great while, though, answering an ad could lead to a unique, unforgettable encounter. The one I’m going to tell you about was one I remember for several reasons, most of all because it turned out totally different from what I’d been expecting.

“Pimping out my bear boyfriend” was the title that caught my eye one weekend morning. What was going on here?

“My boyfriend really wants to get fucked bareback while I watch. We’re two big WM bears. If you want to be the guy who makes our fantasy come true, hit us up. Cool with any race, age, body type. Just have a hard dick and be ready to plow some bear ass.”

There was a photo of a beefy body lying ass up on a bed, which I assumed was that of the boyfriend.

As you might have figured out from the first Craigslist adventure, I have a wild streak. Normally I’m not into the bear type—I’m HWP and pretty fit if I do say so myself—but something intrigued me about this ad. This couple apparently had an open enough relationship to be comfortable with watching each other with another guy. I liked that they didn’t fill their ad with requirements: “Under 40, W only, no fems, must be hung,” etc. etc. And the thought of performing for an audience was a turn-on.

I clicked on the Reply button. Even though the ad hadn’t asked for it I gave my stats and attached a photo.

“Wow, hot!” The reply came a few minutes later. “Where are you and when can you get here?”

As luck would have it the address they gave was just a few minutes’ drive from my place. I took a quick shower and dressed in what I thought of as my hookup gear: skimpy underwear, polo shirt, loose shorts and sneakers, no socks—stuff I could easily slip out of.

It was Saturday and the traffic was light. I got to the address my contact had sent five minute ahead of the estimate I had given them. It turned out to be a shiny new mixed use building on a main thoroughfare, with shops facing the street on the ground floor and condos above.

I turned into the parking garage which occupied most of the rest of the ground floor and found a visitor’s spot. I slipped through a locked gate using the passcode I had been given and took the elevator up to the third floor. When I stepped out I found myself standing on a walkway onto which all of the unit doors opened. It was edged with a wrought iron fence that ran around the entire perimeter of the large building. I looked down and saw an elegant courtyard beneath with a swimming pool. Clearly this was a high-end residence.

I headed down the walkway until I found the apartment number they had given me, my excitement rising along with my dick. The door opened just moments after I rapped on the smart looking brass knocker. I stepped in and found myself amid piles of boxes on a hardwood floor.

“Sorry about the mess. My partner and I moved here from out of state just last week. I’m Mike,” the man standing next to me said. I sized him up as I shook his outstretched hand. He was dressed in a gray velour bathrobe that was undone and hanging open, revealing a hairy, substantial belly. His dark hair was luxuriant and he sported a neatly trimmed gaziantep escort beard and mustache. Definitely a bear, and definitely a looker. This was going to be fun.

“Come meet Jerry. He’s waiting in the bedroom.”

We headed down the hallway. The bedroom was the only tidy room in the apartment and was dominated by an appropriately king-sized bed. Another large, naked man was lying face down on it.

“Jerry. Come meet your next top,” Mike’s voice said behind me.

Jerry raised himself up and looked over his shoulder. His eyes checked me out with practiced ease. He smiled. “Very nice.”

I felt Mike’s hands on my shoulders. “He is, isn’t he?” He bent and whispered in my ear. “Why don’t you get a little more comfortable.”

I obeyed and began to strip. Taking my clothes off in front of a couple of guys who wanted to play normally would have had me hard already, but I wasn’t feeling nearly as turned on as I had a minute ago. The problem was that Jerry, though he seemed nice, wasn’t as handsome as Mike, not by a long shot. I hated myself for being so shallow, but my body knew what it liked.

So far the bear couple hadn’t noticed my sudden lack of enthusiasm. “You have a great body,” Jerry said, as soon as I pulled off my shirt.

That made me feel worse. “Thanks,” I mumbled. I dropped my shorts and kicked off my sneaks. There was no turning back now.

I moved toward the bed. As soon as I got close enough Jerry’s outstretched arms pulled me close until his face was in front of my crotch. I felt his warm breath on my still soft cock. “Nice,” Jerry said again, and took me into his mouth.

He turned out to be a skilled cocksucker, noisy and wet, just the way I liked it. After a few minutes I felt myself starting to get hard. Jerry must have decided I was ready, because he flipped around onto his knees and spread his generous cheeks. “Have at it, buddy.”

I poked at his asshole, which was slick with lube and probably cum from whoever had already been here today. Normally that would have got me going me too, but it just wasn’t happening. By the time I got my dick against his hole and tried to push in, it was back to semi-hard, not nearly enough to get the job done.

My face was flaming. In another minute I’d have to admit defeat and slink out, having disappointed these two nice guys. “Sorry,” I mumbled through gritted teeth. “I guess I’m kind of nervous.”

Jerry looked around. To my surprise his expression was sympathetic. “I am kind of tight. Maybe Mike can fluff you up a bit more.”

I looked around. Mike was dropping his robe. “Sure. Sit on the bed.”

A bit stunned by this turn of events, I obeyed. Jerry’s boyfriend knelt between my legs and began to blow me. I should have been more turned on now that I was messing around with the hotter guy, but I was still too embarrassed for even this to have much effect. In desperation I appealed to Jerry.

“Would it be okay if we kissed?”

Jerry shrugged. “Why not.” He seemed totally cool with everything that was happening, even though he was the one who was supposed to be getting the attention, and the dick up his ass.

I bent down toward Mike’s upturned face. His lips and tongue were eager and slippery and I finally felt some serious juices begin to flow. Mike must have felt the same, because he stood, pushed me onto my back on the bed and stretched out full length on top before beginning to kiss me again. As we continued to tongue wrestle I shot a sideways glance at Jerry. He was watching with rapt attention, a slight smile on his face.

“You are hot,” Mike murmured above me. Then he said, “Maybe you could fuck me.”

My jaw dropped. “Really? But I thought…”

Mike said to Jerry, “Darling, would that be all right?”

“Sure,” Jerry said. “He can top both of us. Like the one this morning.”

I doubted that was going to happen, though my dick finally seemed up to at least one fuck.

Mike said, “The guy this morning came in my ass so I’m already lubed up. Let’s do it.” He hoisted himself up, still straddling my body. His own dick stood out stiffly, dwarfed by his belly but impressive enough. I felt a hand grasp mine and guide it between his cheeks. He rubbed it up and down his ass crack, wetting it with whatever was there.

Getting in took a minute, long enough so that I started to get nervous again. Then I felt squeezing warmth surround my shaft and the full weight of Mike’s body pressing down on me. His jaw grew slack and his eyes lost their focus. “Oh yeah,” he breathed.

We stayed absolutely still, enjoying the moment. Then Mike began to ride me, his ample hips and thighs working, his hands cupping and working my pecs. I thrust my hips upward to meet each downstroke of his ass.

I saw Jerry pick up a phone from the nightstand by the bed. He moved behind his partner, aiming it at us. I must have looked suspicious, because he said, “No faces. Only his ass and your cock. Fucking hot.”

I decided to let it go. Truth to tell I was really getting into reaming Mike’s tight, cum-lubed hole. The big bearded guy and I had some serious chemistry. He felt it too, judging by the enthusiastic way he was using my rod to fuck himself, pulling on his own cock and smiling down at me.

“Fucking nice,” was all he said. I nodded.

“He likes it with him underneath too.” I heard Jerry’s voice behind us. “Want to flip?”

Mike nodded and lifted himself off of me so we could change places. Once he was on his back he raised his legs. I took hold of his ankles, spread him wide open, pushed my cock in and went back to work, enjoying the sight of my shaft sliding in and out of his hairy, greasy hole. I wasn’t worried any more about staying hard.

Mike grabbed the back of my head and drew my face down to his. Kissing him again kicked me up another notch and I stepped up the pace of my thrusts. All too soon I felt myself edging up to the point of no return.

“Gonna cum,” I mumbled. By now I was thudding against Mike’s ass like a machine.

“Do it buddy. Give me that load,” Mike urged, smiling into my eyes, pulling faster on his own cock. I felt Jerry’s hand between my legs, cupping my swinging balls.

“So hot, having two loads in him. Fill him up.”

My eyes squeezed shut as my breath began to come in short, harsh gasps. A few more frantic thrusts, then a long “Ahhh!” rose from my throat as I felt the first hard spurts shoot from the head of my cock buried deep inside my bear bottom’s butt. I arched my back upward until my unseeing eyes were turned almost up to the ceiling, gasping and cursing as the orgasm ripped through my body.

Finally the storm began to pass and I could open my eyes. I looked down and saw a few splashes of white fluid across Mike’s heaving, hairy belly. I smiled at him. “You came too.”

“Uh-huh.” We shared one more languid kiss. Then I remembered, and looked up at Jerry. He looked perfectly content like he’d also cum, though as far as I could tell he hadn’t—he wasn’t even hard.

“That was hot,” he said.

Guilt rushed into me. They had put in the Craigslist ad looking for guys to fuck Jerry, and here I’d gone and fucked his boyfriend instead. “Sorry,” I said, feeling lame and inadequate. “I got a bit carried away.”

“No!” He leaned over and kissed me. “Don’t apologize. You were terrific. I really got off on watching you, and I’m sure Mike enjoyed it too, right, Mikey?”

Mike nodded vigorously. “Uh-huh. You are hot. And a great fuck.”

They were both smiling at me. I slipped my rapidly softening cock out of Mike’s ass and turned over, wishing that a hole would open up in the floor and swallow me.

“Well—I really hate to say it, but I think I’m done. Really sorry.”

Jerry made a dismissive gesture. “The day is young… the next one will be for me. Or maybe you could come back sometime. Not to worry.”

“You sure?”


“You want to get cleaned up?” Mike asked. He pointed. “Bathroom’s over there. Use any towel, they’re all clean.”

I headed for the bathroom, shaking my head in wonderment at this most unusual and, I was beginning to think, super cool couple. I took a quick shower, leaving the bathroom door open. As I toweled off afterward I heard their voices coming from the bed.

“You really enjoyed that, didn’t you, darling?” Jerry said.

“Mm hmm. Not often I get to play with a nice muscle boy.”

“You know, I’m not sure we got his name.”

“True. His e-mail address only shows his initials. K.N., or something.”

At that I wrapped the towel around my waist and headed back in. Mike and Jerry were still lying in bed with their arms around each other.

“My name’s Ken,” I said.

“Nice to meet you, Ken. Thanks for coming by.”

I shrugged. “Pleasure’s all mine.” I was telling the truth. The encounter had been fun, though not in the way I’d expected at all. I found myself wanting to know more about these two guys, how long they’d been together, how they’d worked out a relationship that was so supportive and free of jealousy. I knew now wasn’t the time to ask, and that I probably would never know.

I found my clothes and shoes on the floor and quickly got dressed. Mike got up from the bed and put his robe back on. “I’ll see you out.”

At the door he shook my hand. “Thanks Ken. You were great.”

I had to say one last thing. “Next time it’ll be Jerry’s turn.”

He smiled. “He’d like that, I’m sure. Have a good weekend.”

There wasn’t a next time, of course. I don’t have Mike’s e-mail address any more, I’ve long since forgotten exactly where he and Jerry lived, and I have no idea whether they are are still there. A couple of years after that meeting, just before Craigslist stopped carrying personals, I put an ad in their Missed Connections section. I didn’t use their names but described our encounter in enough detail (I hoped) that they would remember it, and invited them to reply if they wanted to get together again. No response. I have no idea whether they saw the ad or not.

Every now and then, like when I’ve been writing this story, I remember with fondness the two bears I met on Craigslist. I went over to top one and ended up topping the other, and it was all good. I hope you’re still together and still sharing the love, guys.


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