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My Char-bear

by Colehann


I've always been attracted to Charlie, and assumed that he was straight. I mean, what's not to love about him; 6'0 180lbs, short blond hair with blue eyes. Just out of college Char was smart and young. His smile melted my heart every time. I loved him but never had to courage to push our friendship until.… I don't remember the occasion, but it was summer in Boston and the two of us had gone out drinking with friends. Charlie looking for a girl to hook up with, myself "looking for the same." I'm pretty much in the closet. By the 8th beer Charlie was staggering around complaining how boring bars could be. I recommended we go back to his place and chill. As I followed him up the steps to his place I couldn't help drooling over his soccer player ass, which teased me all the way up his 4 flights. I had to help Char with the key to his place as his coordination began to escape him. Placing his hands on my shoulders and resting his head on my back he followed me into his single apartment. Bragging about all the beers he consumed (about 10 at this point) he went to into the bathroom. I fixed two glasses of water and was pleasantly surprised when I turned to hand Char his glass. There he stood. The man of all my fantasies is in a pair of white Banana Republic boxer briefs and V-neck t-shirt. All the exposed blond hair, on that athletic body made me hard instantly. "Thanks for the water. It's too late for a cab. Why don't you stay over in my room tonight?" Char slurred. I understood that sleeping on the couch could not be an option since the A/C was in his bedroom. I took him up on his generosity and we headed to bed. Before I had striped down to my boxers my drunken bear was fast asleep. His heavy breathing was apparent and reflected a deep sleep. I did a test nudge to see if I could wake him. Nope, he was definitely out cold. As he slept on his side with his back toward me, I debated whether I should cuddle up next to him. I decided that I would never have a better opportunity, so I started to explore the back of his neck with my nose while my hands began to creep up the back of his shirt. I took in deep whiffs of his short blond hair as I lifted his shirt to massage his back. Sliding in closer I started to lightly kiss his neck and ear as I wrapped my arm around to stroke his hairy chest. As I squeezed one of his nipples Charlie rolled onto his back as a moan escaped his lips. I proceeded to pull off his shirt with little resistance. Lying on his back with both arms above his head I leaned into a hard kiss on his neck. I didn't care about leaving a mark. I wanted this hot jock here and now. Grinding my nose into the armpit of my best friend I took in his manly scent and began to kiss my way down to his navel. His strawberry blond chest hair was so soft and framed his muscular top well. I stopped to analyze my situation before I proceeded any further. Then to my surprise I heard Char whisper, "Mmm, don't stop." Not sure whether he was conscious enough to realize what he was inviting I licked my lips and began to massage his soft package. Charlie's head twisted from side to side, and his cock began to swell. I pulled off his boxer briefs to free the part of Charlie I had dreamed about for 2 years. His pink cock was 7" with a small head and thick shaft. I kneeled in between his strong hairy thighs that I spread with my hands. On his back eyes closed massaging his own chest, I knew Charlie was enjoying the attention. He moaned as I continued to suck his cock. The salty taste of his pre-cum as his fat cock throbbed in my mouth was surreal. I had Charlie in the palm of my hand. All my obsessing over this bearish jock had finally brought us together. One last thing remained. As I circled my tongue around Charlie's shaft and balls I could feel him approaching climax. So I eased off and started kissing his thighs. "Oh, please...don't stop," Charlie moaned. "Don't worry Char-bear I've got a plan that'll drive you wild." I assured him. Lifting his knees to his chest I instructed my drunken bear to hold them there. The sight of his pink virgin cherry surrounded by curly strawberry blond hair almost made me cum. I propped his ass up with a pillow and started to lick his juicy manhole. The funky musk smell was something straight out of a locker room. "Oh...yes," Charlie moaned as his pucker relaxed and my tongue slipped in slightly. He was spread nice and wide now with his feet up by his head and his ass lifted in the air by the pillow. I massaged 2 fingers on the surface of his rosebud taking care not to penetrate any further than my tongue earlier. Reaching under the bed I found his personal KY stash. I slicked up the surface of Char's hole and my own 8" rod and positioned its head. "I'm nervous," Char confessed. He's so cute when he's scared. "What about?" I replied as I began to apply pressure to his tightly clenched pucker. He began to moan in pain. I could tell he couldn't hold on much longer. Looking into his blue eyes as I helped hold his ankles and asked him to relax. The combination of KY and Char's fleeting strength helped open his ass ever so slightly. Once past the initial opening I was suddenly 3" deep. "There goes your anal virginity Charlie,” I thought with a grin as Charlie's head thrusted back as a soft yell of sudden pain escaped. I paused for a moment lightly fucking him 3" deep. I love how he thought that remaining completely still would help ease the pain. For such a cocky jock he was vulnerable as a teddy bear in bed. Slowly I rocked his body pressing deeper into his ass. Charlie attempted to squirm away as I pushed 6 inches deep. With that sign I pulled all the way out. Char let out a sigh of relief. Then all of a sudden I started in harder than before, this time all the way in. His loud moaning and pleas for mercy only made me fuck him harder. With all 8" of myself in Charlie I leaned forward and began to kiss him. Our tongues swirled together muffling his moan as I split him wide open. His ass clenched my dick as Char started shooting cum. Charlie's moaning as he came drove me to climax. I pulled out of his ass, which remained wide open and straddled Char's face. With an open mouth Charlie welcomed my cock. As I held his head and fucked his mouth, I reached back to play with all the cum on Char's hairy stomach. I came in his mouth and made sure he swallowed every drop of my load. Exhausted the two of us cuddled together and kissed until I passed out in his arms. In the morning I awoke to a finger sliping up my ass, but that's another story.

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1 Gay Erotic Stories from Colehann

My Char-bear

I've always been attracted to Charlie, and assumed that he was straight. I mean, what's not to love about him; 6'0 180lbs, short blond hair with blue eyes. Just out of college Char was smart and young. His smile melted my heart every time. I loved him but never had to courage to push our friendship until.… I don't remember the occasion, but it was summer in Boston and the two of

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