A Bear Cub Taes My Virginity

I had never really been fussed about sex. I was 21 and hadn't even kissed another guy. I wasn't in any rush to, either. It'll happen when it happens, I thought. Besides, I was a student living at home and I wasn't out of the closet, so I couldn't bring the sort of guys I liked home.

My first sexual encounter happened when my dad went overseas for a month and a half. After a week or two of sitting on the fence, I jumped on Craigslist. I wasn't new to Craigslist; I had been on the site before, browsing the personals section and reading the casual encounter ads. Another man's horniness always made me horny.

I quickly found an ad posted by a 25 year old cub that lived close by, looking to get his dick sucked and more. I had seen this guy's ad before, and his cock photos looked amazing. More girth than length in a bed of brown pubes, a mouthful of head tucked under foreskin, and with an ample hairy belly hanging overhead. I responded late at night, and the next morning received his reply. We exchanged information, and he came over.

I was waiting in the garage, pacing back and forth endlessly.

'I'm here', he texted me, and my heart was in my mouth. I opened the garage door and watched the letterboxes where I had told him to go. A tall, broad shouldered bear of a young man waved at me as he climbed the short flight of stairs and lumbered over. He wore a blue singlet; I could see his muscled arms and heavy-set body, tanned from hours spent shirtless in the sun; a real football player's build. He had a broad, chubby face, slightly unshaven, and stood half a head taller than me.

"Hey," he nodded brusquely, with a strong Australian accent. His eyes raked my body, and mine his.

"Come in. I hope this is okay," I said, waving to the makeshift mattress I had set up.

"Yeah, it's fine," he assured me, stepping in and peering around. I closed and locked the door behind him. Off went his singlet, quickly followed by his board shorts and then his boxer-briefs. I quickly undressed, but my eyes were glued to his bearish body. His cock was still thick when it was soft; it rested on his hairy nut sack. I ran my hands down his fuzzy arms, nervous. I had never gotten this far with another guy. Here we were, naked side by side, with nothing in interrupt us. He was probably going to be the first guy inside me.

The next thing I knew, he had reclined back on the mattress, and I was on my hands and knees with my head between his thighs and his flaccid cock waiting under my lips. It smelt faintly of the soap he had used when he showered earlier. Gently with my fingers, I stood his member up, pulled the foreskin back and put it in my mouth without hesitation.

"Ohhh, yeah," he moaned, hips bucking a little. His cock swelled in my mouth, thickening at an alarming rate. It surprised me that he could get so much pleasure before I felt I had even started. I swirled my tongue around the head as it grew firm, and tasted the salty-slimy precum.

I began to bob my head up and down while my hand rubbed his hairy stomach and legs. He was fully erect by now, and I was having trouble fitting him in my mouth. "You're clean, right?" I said between gulping down his meat and licking his soft, hairy balls.

"Yeah, I'm clean," he said, and placed a hand behind my head, forcing me down his shaft. When I buried my nose in his pubes, his throbbing cock made me gag. I retched and pulled up."Fuck yeah," he murmured, grabbed my head and slowly fucked my mouth for a bit. I closed my eyes, focused on breathing around his girth, and let it wash over me. This was what I had been secretly looking forward to all my life, and I loved it.

He pulled me off his cock. Spit ran down my chin and down his shaft which stood straight up. I wrapped my hand around his cock to stroke it, and could barely get my hand around it. How was that in my mouth just now?

"Let me suck yours for a bit?" He rolled off the mattress and I took his place; he spread my legs and got right up between them. I was rock hard already. He took my cock full in his mouth; warmth and wetness enveloped it, and he made moaned in approval as he devoured my cock. His hands groped at my chest, squeezing and rubbing me while his excitement escalated until his head was bouncing up and down between my legs. "Mmmrphm, so good," he gasped when he surfaced for air, before stuffing me back into his mouth again.

"Do you want to fuck me?" I offered all of a sudden. I had planned on letting him fuck me after a bit more sucking, but I couldn't wait any more. I wanted to feel his cock up my ass right now. This young, hairy bear with the beer-can cock... I wanted him to break me in for the first time.

He paused to look at me, perhaps to see if I was serious. His hands continued to slide up and down my cock, lubricated by his spit and my precum. "Yeah, I do," he admitted, and then continuing to suck my cock. "What, now?"

I nodded, and got up to grab the lube and condoms. "You can fuck me bareback if you're clean."

"I'm clean," he assured me again, and took the lube I offered. I shouldn't have done that, especially being my first time. But thankfully, he really was clean.

He pointed to the mattress and set the tube of lubricant on the ground. "Get on all fours, doggy style. I want to see your ass."

I did as I was told and stuck my ass in the air. This is it, I thought. I'm about to finally get fucked. I can't believe this is happening. A chubby guy with a big dick -- a man straight from my fantasies, and he was getting ready to fuck me. He spat on his finger and fingered my ass for a few seconds, and the mattress shook as he dropped to his knees behind me.

"Fuck, that's a nice, tight hole," he growled, spreading my ass cheeks apart to run his tongue up and down my crack. His tongue was warm and wet, and for a while, pleasant, before he started worming it into my ass. It felt like a finger and thicker than I thought it would have been.

I shifted my ass to make his tongue go up and down over my hole again. The mattress shook again as he straightened and slapped his rock-hard cock over my ass-crack. He squeezed lube onto his cock, then leaned back to apply a few cold drops over my hole.

"It's my first time, go slow," I pleaded, but I don't think he heard me; his cock was rubbing hard against my crack, and making brief jabs at my entrance as his hips started to rock back and forth out of habit. I wonder how many other guys and girls this man had slept with, and knew I was simply another conquest in a long line of his bed partners, and I was okay with that. In fact, it excited me.

His thrusting slowed. He began to push his cock up into my virgin hole in earnest. It was warm... so warm, and so thick. It felt like he was trying to push a beer can through me, and my hole wasn't budging. He relented for half a heartbeat, took one hand off my hip to grasp his shaft, before trying to push his cock in me again, and this time he managed to force the head in. I cried out, or swore, or moaned -- I can't remember exactly what crude sound I made as he proceeded to bear down on me, relentlessly shoving his manhood deeper and deeper inside me.

When I felt his body pressed up against my ass-cheeks, his heavy balls resting against my cheeks, I couldn't believe how thick and solid his cock was. It was soft and fleshy in my hand and mouth, but in my ass it felt like a slab of wood. It stretched my ass out to the limits; it must have been a nice, tight fuck for him.

"Give me a second," I said, reaching back with a hand to touch his leg. He heard me, and chuckled in his deep voice as he brushed my hand off, and continued to fuck me anyway. He pulled out a tiny bit before plunging himself deep within me again. With each stroke, he withdrew a little more than the previous thrust, and his dick was so snug inside me he was tugging my insides with every minute movement.

He moaned in satisfaction as he fucked me, his hands tightly grasping my hips as he pulled me in to each thrust for deeper penetration. "Fuck, you're tight. You're really fucking tight, oh man." He fucked me slowly, almost tenderly, but with enough force to make my body shake as his cock drove home each time. "You like it?" he asked, and as I replied, he unexpectedly pulled his cock all the way out -- I gasped in shock- and he rammed it back in. He chuckled again at the distressed sound I made, and the effect on my body his dick had.

I lost track of time when he was pumping away behind me. At some point, he pulled my legs back so I laid flat on my stomach, mounted me again, and entered with a rumbling 'Mmm' of content. He slid in easily this time, and my hips rose to meet his thrust eagerly of their own accord. He fucked me this way for awhile, before lowering himself to slobber and suck on my neck.

His thrusting slowed. "I don't wait to cum yet. Your ass feels good, man. Fuck!" He ran his lips across my neck, panting heavily next to my ear. I could feel the coarse hairs on his chest and belly rub against my back. He dripped sweat on me as he straightened, slapped my ass hard, twice on each side with his large hands, and then pulled me back into the doggy-style position and pumped my ass furiously.

He fucked me hard.

The mattress sheets bunched in my hands from the fists I made, and the sound of skin slapping on skin and his laboured breathing was all I could hear. I must have join in, crying out with pleasure or pain at each thrust, but I don't recall -- all I know is that I suddenly stopped doing it when he pulled out and spread my ass cheeks.

"Fuck yeah," he growled, and his seed dripped out of my hole and on to the sheets. I didn't even know he had cum. He buried a finger deep in my ass with a wet squelch, and gave a low chuckle, proud of his work.

*

"If you ever want to fuck me again..." I hinted as he dressed minutes later.

"Yeah, definitely man. I'm moving down to Melbourne next week, but I'll see if I can come over before then." And he left.

It was a true dump-and-go -- I checked the time and it had only been about 20 minutes. He came, we sucked some cock, he used my virgin hole and dropped a load of hot cum inside me, and was gone.

Two hours after he left, I got a text from him.

'Fuck, u were so sexy today! Can I come over 2moro?'

*

The next day, a little bit past midday, he came over again. This time, the mere sight of his hairy shoulders and barrel chest straining under his shirt made me hard. We jumped onto the mattress in a 69 position on our sides, and sucked and licked each other. I fingered his ass while I sucked his meaty cock and squeezed precum out of it.

"Want to fuck me?" he rasped after a short while. I said 'yes', pushed myself to my feet to get the lube, and he got on to his hands and knees. I fingered his ass with the lube, sliding a finger in first. It was tight, silky smooth and warm. I spread lube on my dick and pressed it up against his puckered hole. It took a while, but after several tries and readjustments, my cock slid through up inside him like pushing a pin through rubber. The first thing I felt was how warm it was, warm and snug, and my cock was buried deep in its goodness.

"Fuck me," he begged, face down on the mattress. His fingers gripped the edge of the sheets in anticipation.

I didn't go slow. I pulled out and slammed my cock up his arse, once, twice, three times, and then hooked my hands around his hips and fucked his tight, chunky ass as fast and hard as I could.

"Fu-uu-ck, yeah, yeah, ye-eea-hh, fuck me, fuck me, fuck yeah, fuu-uu-ck," he moaned into the mattress. His arms were stretched out in front of him and his fingers splayed in ecstasy.

That was when I realised I was more of a bottom than a top. For so long, I had fantasized about fucking bears and chubs, but it felt no better than my own hand. In fact, my hand usually felt better than this. But he loved it; his body was quivering and his ass bucked to match each thrust. He couldn't stop moaning, and I didn't want him to stop. I loved making him feel whatever it was that transformed this gruff, husky man in to this moaning, submissive bitch.

But I did stop. I wasn't going to cum like this, so after pounding him for a few more minutes I pulled myself out of him and he looked around, exhausted and confused. I hadn't cum yet, but I could see he was getting close. "I want you to fuck me," I said. "Cum in me again."

I squeezed lube on my hand and massaged his hard cock to spread the gel, before wiping the remaining lube on my waiting asshole. He spun me around, and with one hand on his cock and the other grasping my side, slammed his beer-can cock in me. He was balls deep from the get-go. I must have shouted -- it hurt like hell - when his weight crushed me and I knew he had already given in to his lust and wasn't going to stop. He clambered eagerly on top of me, pinned me down his brawny arms and pounded my rear so hard my legs jostled and bounced on the mattress.

It hurt twice as much the second time around. I think my insides were still sore from his last assault, and on top of that, he was fucking me roughly. I swore each time be bounced and slammed his thick cock inside me, and several times tried to twist and buck him off, but that made him want to dominate me more. He didn't stop pumping my ass until it was full of his cum again. This time, as he pulled his fat, chub cock out, I felt his seed spill out and trickle down to the sheets.