First Online Hookup

I got to my hotel room and set my bags down, pulling out my laptop to check e-mails. I didn't see any from work, so I switched over to my private e-mail account and saw one from Jim, which immediately got my heart racing and made my mouth go dry.

Jim was a guy I'd been chatting with on an online hookup site for gay & bi men. He was older than me by about 15 years (I was 31 at the time) and, like me, he was married and his wife didn't know about his bisexuality. Also like me, Jim traveled a lot for business and, according to his e-mail, he was in the same town as I was that night.

I quickly fired off an e-mail to him to tell him I'd just got into town and what hotel I was at. I set about undressing and putting away my things, and checked my e-mail again. I saw he'd responded with, "What a coincidence... I'm in room 327, come on up whenever you want." Attached to the e-mail was a picture of his cock, and I have to tell you that it looked delicious.

After I took a few deep breaths, I called my wife to let her know I'd made it to the hotel, but that I was wore out from the trip and was going to shower & go to bed. We made small talk for a few minutes, exchanged "I love you", and hung up.

I sprinted to the bathroom and turned on the shower to let it warm up before jumping in. I quickly shaved my face, then lathered myself from head to toe - paying attention to my cock, balls, and ass - before rinsing & drying off. I put on a pair of gym shorts, a t-shirt, and tennis shoes, then grabbed my room key and headed out.

I couldn't believe that I already had a semi when I got in the elevator, that's how keyed up I was. I'd been to a number of glory holes by this point, both giving and receiving oral, but this would be my first time actually being naked with another man in the same room, and I couldn't wait.

I got to room 327, took another deep breath, and knocked softly. I only had to wait a few seconds before the door opened to reveal Jim standing there. He was wearing only a pair of boxers, and he looked exactly like the pictures he'd sent me: about 5'10", 180 pounds, short hair starting to go grey, brown eyes, built like the high school and college wrestler he said he'd been in his younger days.

Jim let the door close when I stepped in, and he moved until we touched. "Is this for me," he grinned as he reached out to stroke my now fully-hard cock through my shorts.

I moaned back, "Only if I get this first," as my hand dropped to the front of his boxers to wrap around his cock through the fabric and caress it gently. Our moans mixed when his head dipped forward until his lips touched mine, and our grips on each other tightened as we began a passionate kiss that turned into an almost wrestling of our tongues as we walked - him backward and me forward - toward the bed, never breaking contact until we were at the bedside.

I reluctantly broke off the kiss and stepped back, letting go of his cock so I could grasp the waistband of his boxers and push them down over his hips to fall to the floor. I peeled off my t-shirt and tossed it aside before lifting my hands to his shoulders to push him back until he was laying on the bed, his legs spread wide. I slowly crawled up between them, kissing back and forth from one leg to the other until I'd made my way to his cock.

Moaning softly again, my lips parted to wrap around the head and suckle gently, tongue swirling around the head as one hand lifted to slide up his body and find his nipple to tweak, the other sliding under his balls to cup them and roll them softly. I looked up at him over his body and moaned deeper as I slid my mouth down slowly, gradually increasing the suction until I felt the head of his 6" cock pushing at the back of my throat. I hadn't learned to deep throat yet, so I never went any deeper than that as my head bobbed up and down, alternating between sucking tightly and then so softly that my lips just barely touched him.

I could have kept doing this until I got my reward, but I jerked my mouth from him and spun around when I heard the toilet flush in the bathroom. "What the fuck?" I gasped, wondering what the hell was going on.

"Relax Steve, it's just a friend of mine, I think you'll like him," Jim said as the bathroom door opened. A naked man stepped out, and until that point I never knew that I had a thing for bears, but after looking at him I knew I did.

"Hi, I'm Alan," he said softly, his eyes dancing as mine traveled over his body. He was about the same height as Jim, but a good 40 or 50 pounds heavier, with much broader shoulders. He had a little bit of a gut, but wasn't fat. He was hairy on his chest and shoulders and stomach and arms and thighs, as well as between his legs, but there wasn't near enough hair there to hide that cock.

It was thick, much thicker than Jim's, and hardening slowly as he walked towards me. I could tell that, by the time he was done growing, he'd be a good 2 or 3 inches longer than Jim's, and I knew that those full, heavy balls swinging beneath it would shoot a massive load.

"I'm Steve," I said when he got to the bedside, and I wrapped a hand around Jim's cock to stroke it slowly as I leaned my head over to wrap my mouth around Alan. He tasted different than Jim, a little saltier, but still delicious. I knew there was no way I'd be able to suck him deep, he was too thick for me, so I took him in as far as I could while my free hand wrapped around the base.

I alternated between the two of them, sucking first one then the other, but always keeping a hand wrapped around each of them. Again, I would have done this until they both fed me their loads, but Alan put his hands on my head and pulled my mouth from him, whispering softly, "You have a sexy little ass, Steve."

He moved slowly behind me, and I rested my head on Jim's thigh and kept stroking his cock, waiting to see what Alan had in mind. I let out this low, guttural groan when I felt his thumbs pull my asscheeks apart and his tongue find my hole. Up until that point, there'd only been my fingers in there, and I didn't even know what rimming was, but the feel of his tongue dancing around my pucker was just about the most incredible feeling I'd ever had with another man.

Jim's hand covered mine on his cock and started me stroking again, as I'd almost forgotten about him from the pleasure Alan was giving me. I pushed my ass back against Alan's mouth as I nuzzled into Jim's balls, moaning softly into him. The moan turned into an almost growl when I felt Alan's tongue stiffen and push inside of me, wiggling as much as he could in the tight confines.

I was almost gasping for breath when Alan finally pulled his tongue from me, planting a soft kiss on my asscheek as I felt him stand. I jerked a little when I felt the coolness of the lube he'd coated his finger with touch me, and made myself hold still as he pressed gently, feeling that sharp little instant of pain when his slicked finger popped inside. "That's it man, nice and easy," he said, pulling his finger back until just the very tip was inside me before pushing back in a little further than the first time. The little instant of pain quickly subsided and turned to pleasure, an almost need to have my ass filled, as with each stroke of his hand he pushed his finger a little further and deeper into me, 8 or 10 strokes before I felt the knuckles of his other fingers pushing against my flesh.

"Damn you are tight," he said, keeping his finger pushed fully into me but twisting it round and round. I moaned more, pushing back against his hand, wanting to feel the thrusting again. "And a hungry little ass it looks like, too," he chuckled as he pulled his finger from me and I heard the tube of lube squeezing again, the moans coming from deep in my stomach this time when I felt his first and middle fingers both stretching me, this time pushing in fully in one steady stroke, rotating back and forth as he went.

"Oh god oh god oh god," I moaned, not stroking Jim's cock any longer but gripping it tight, the feel of Alan's fingers preparing me so incredibly amazing.

I nodded my head quickly when I heard Alan ask, "You sure you're an anal virgin, Steve, you're taking to this much better than most first timers." Even though it was the first time I'd had something in my ass other than my own finger, I knew that it wouldn't be the last.

Alan slowly pulled his fingers from me, almost causing me to whimper, but it quickly changed to a gasp when I felt the coolness of the lube being squirted on my hole. I sensed Alan moving behind me, and I felt his hands grasping my hips just as the head of his cock pressed against my pucker.

"Take a deep breath, and push out like you're trying to take a dump," he rumbled, and I followed his directions, not knowing what to expect when I felt his fingers dig into me to hold me steady as he began to slowly push forward. I gasped and moaned into Jim's balls as Alan kept pushing, pausing only for a moment when the head of his cock slipped past my sphincter, then resumed his stroke into me as the thicker part of his shaft stretched me further than I thought possible.

I was shaking and moaning and my throat was dry when I finally felt the fronts of Alan's hips against my asscheeks and his balls against mine. The pain, like the quick sharp pain from when he'd fingered me but much deeper, coursing through me. Alan's hands began to move while the rest of him held still, massaging my hips and cheeks and lower back gently. "That's it man, just relax."

I have no idea how long it took, but I gradually noticed that the pain was subsiding and pleasure was taking its place. My grip relaxed on Jim's cock to the point where I could slowly begin stroking it. "Whenever you're ready, just start sucking Jim again," I heard Alan say, and I slowly let go of Jim's cock so I could plant my hands on either side of Jim's hips and, dipping my head, sucked Jim as deep as I could go.

"I guess that means you're ready then," Alan chuckled, and I felt his hands gripping my hips again as Jim's gripped my head. Both of them began working in unison, Jim guiding my head up until only the head of his cock was in my lips every time Alan stroked into me, then Alan pulling back until only his head was in my ass as Jim pushed my head down until I just barely started to gag.

For a moment, I almost had an out of body experience. It's like I was watching this 31 year old married man getting fucked at both ends and loving every second of being used like a common slut.

I snapped out of it quickly, though, when I felt Alan's hands tighten on my hips to hold them steady as his pace began to quicken. With each thrust, he was driving into me a little harder and a little faster, making me grunt onto Jim's cock from where he held my mouth on him just at the gagging point. Alan was grunting with me from exertion as he took me fast and hard, his cock swelling in me and his balls not bouncing as much as they drew up tight.

Jim came first, though - I'd been so focused on the pleasure of Alan taking my virginity that I hadn't even noticed that his cock had swelled too, and his precum started to be a constant flow. The eruption of his cock almost gagged me, and I just barely had enough time to jerk my head back to suck on the tip of his cock as spurt after spurt of his salty sweet cum flooded my mouth, all the while Alan fucked me harder and faster.

His spasms had just subsided when I felt Alan slam into me a final time and hold, his body jerking and his fingers digging tightly into my hips. He grunted and shuddered every time I felt a blast of his thick, sticky cum shooting into me, so much that it actually ran out around his cock and down over my balls.

Alan finally shuddered to a stop, his grip relaxing gradually as he gasped for breath. I let Jim's softening cock slip from my mouth and laid my head on his thigh, moaning when I felt Alan easing his spent member from my abused hole.

My eyes were closed, but I could feel them moving - Jim off the bed and Alan from behind me. I felt someone's hands on my hips to turn me over to me back, and felt my legs being lifted over someone's shoulders. I opened my eyes, and saw Alan climbing onto the bed on his hands and knees beside me, and looked down to see Jim between my legs. "Your turn," Alan chuckled, and his mouth closed over my painfully hard cock just as Jim's mouth pressed at my asshole, his tongue delving deep to clean Alan's seed from me.

I screamed, the pleasure was that intense, simultaneously trying to fuck my ass against Jim's tongue and my cock into Alan's hot, wet mouth. Up until that point, I had never cum that hard in my life - it was like a whole body orgasm, the way they made me feel, neither of them stopping until I seemingly didn't have a drop of cum left in either my ass or my balls, and I was barely able to breathe.

They collapsed onto the bed on either side of me, the three of us gasping for breath and covered in sweat. We laid there for a while, not saying anything, just coming down gradually from the sexual delight. When we'd caught our breath, we started talking - not about much of anything, just getting to know each other some.

Jim, I already knew for the most part, from our online chats; Jim and Alan were acquainted through previous hookups. I learned that Alan was the same age as me, single but had been married previously, bisexual but he had a strong leaning towards sex with men and emotional attachment with women. As Alan & I chatted, Jim moved between us and laid on his stomach, using his mouth and hands on our cocks to try to coax us back to life.

It didn't take long for either of us until we were both standing rock hard and straight up. When Jim's mouth found my cock, my hand dropped to his head to guide him up and down on me. I leaned into Alan and we made out passionately, my hand sliding down his body to find his meat and stroke it in time with Jim's mouth on me. I waited until Alan started moaning to begin moving slowly - kissing my way down over his chin, to his neck, over to his ear, down over his collarbone - loving the feel of his hairy skin beneath my lips.

When my mouth found Alan's nipple, just barely touching it with my teeth, I could tell I'd hit the right spot by his sharp intake of breath and the way he arched his back to push his chest up against my mouth. I looked up at him and, gripping his cock tight with my thumb teasing back and forth over the head, grinned as I sucked his nipple in hard, biting down and flicking over the nub protruding through my teeth so I could flick my tongue over just the tip.

It was like he'd been hit with a lightning bolt, the way he reacted. He cried out - one of those strangled cries of pure pleasure. His entire body tensed and his hands moved to grip my head, grinding my mouth against him even harder, which made me bite down more. My hand released its grip on his cock to gently glide down over his balls, and I smiled against him when I felt him spread his legs and lift his hips up off the bed a little to grant me access.

I dipped my finger between his cheeks, just barely teasing the tip against his pucker, circling it slowly, my mouth moving to suck his nipple in and out like a tiny cock. He gripped my head tight and pulled it away from his body, gasping when his nipple stretched until it popped free, lifting my head up so I could see and hear him whisper, "Please."

I figured I knew what he wanted, but I was really enjoying the feel of Jim's mouth on me, and I was incredibly turned on by Alan's sudden submissiveness, so I just kept teasing his hole and grinned. "Please what," I asked, feigning innocence.

"Oh god please fuck me, I need it," he moaned, pushing his hips to try to impale his tight little ass on my finger.

I moved slowly, gripping Jim's hair to pull his mouth off of my cock first, then moving my body until it covered Alan's, his hard cock dancing with mine, my mouth lowering to his ear. "Mmmmmmmmm don't worry, I'm going to, eventually," I whispered before I started to slowly slide my body down his, my lips leaving a moistened trail over his hairy flesh until I felt his so-hard cock against my chin.

I growled softly as I opened wide to suck him in, taking him as deep as I could as a hand slid under his balls to press my middle finger against his asshole. He started to moan when my finger opened him, and I looked up to see why his moans suddenly became muffled, only to see Jim straddling Alan's chest, feeding him his hard cock.

Rolling my head slowly, I worked Alan's cock with an almost evil glee - first fast and hard until I tasted his precum start to flow, then slow and easy, then just barely brushing my lips over the thick vein on the underside. My hand was rocking now, finger-fucking Alan fast and hard, feeling his ass gripping me and his moans around Jim's cock getting deeper and more guttural.

I quickly jerked my finger from him just as Jim leaned forward to grip the headboard for leverage as he started fucking Alan's mouth in earnest. Grabbing the lube, I squirted it along the length of my cock and then more into Alan's cleft, dropping it to the floor as I moved to lift Alan's legs over my shoulders and align my head at his opening.

Gripping his legs tight against my chest, I pushed forward, not even pausing when I felt the head pop inside - just driving on so that I entered him in one long, slow, even stroke, stopping only when I felt my balls pressing against his asscheeks. I didn't stop for long - I could tell by Alan's moans and the way he pushed back against me, by the way I could tell his head was trying to bob between Jim's legs, that he wanted used.

So use him we did. It was just wanton, almost wild, fucking. The three of us covered in sweat, Jim and I using Alan's holes for our pleasure, only the sound of our moans and grunts and sweaty flesh slapping together filling the room. Alan barely lasted two strokes after I gripped his cock and started flogging it in time with my cock pound his ass, cumming hard almost instantly, shooting jets up over his stomach and onto Jim's asscheeks.

"Oh fuck oh fuck oh fuck," I moaned when Alan's ass clenched around my cock as he came, making my thrusts grow shorter and faster, feeling it build too quickly but not even trying to fight it. Jim came first again, and watching his asscheeks clench and hearing Alan gurgle as the cum flooded his throat sent me over the edge. I slammed in a final time and held, shuddering and spasming, my cum erupting from me and flooding Alan's ass, breeding him the same as he'd bred me.

I stayed there, deep inside of him, even after my orgasm subsided, waiting for and watching Jim slowly disengage his cock from Alan's mouth and roll over to the bed beside him. Not able to help myself from teasing him, I drug my fingertips through Alan's cum and lifted them to his nipples, rolling them gently as I rocked my still semi-hard cock in and out of him, stopping only when he grabbed my wrists and pulled my hands away from him, his eyes on mine as he pleaded, "Please, no more."

I chuckled softly and looked down to watch as I so slowly, so tenderly slid my cock out of him. Seeing his ass gaped open and my cum oozing out of him and all over the bedspread. I moved up on the bed on the other side of Alan, laying on my back, still breathing hard and covered in sweat, not moving until Jim lifted up on an elbow to look at us and say, "I hate to be a party pooper, and I would love to stay here and fuck all night, but I have to get up and on the road in a couple of hours."

Alan and I didn't like it either, but we understood, and after trading 3-way kisses he & I moved off the bed to get dressed. We headed out the door together, and walked slowly down the hall together towards the elevator. When we got in the elevator and I pushed the button for my floor, I didn't say a word even though I noticed that he didn't push the button for the lobby. When it stopped, we got off of it together and he followed me as I headed to my room.