A Bear Shows A Twink How It’s Done

Right after I graduated college I took a job at a small insurance home office. I was aware that I was twinklike (then it was just physically immature, I was slender and smooth)and set off gaydar with a lot of men.

I went through college allowing myself to fantasize about sex with men but wouldn't let myself relax and yield to their flirtations. It was the 80s and in conservative Kansas, so I was afraid of the ramifications and had never heard of being bisexual. I dated a few girls and had sex with a few but never as many conquests as my friends seemed to get.

A sales executive in the insurance company began to show some interest in me. I didn't see it as flirting but I was confused by why an older (30s) man would have any interest in me He was tall and good looking. He was in sales so had a lot of charisma and was comfortable and made those around him comfortable in any situatio. One day he asked if I would help him launch his new sailboat this weekend. He was going to put it in a large lake a few hours away. His boat was pretty big complete with a berth for sleeping. It sounded like fun because I knew nothing about sailing and thought it would be an adventure.

I met him at his house dressed for summer in tshirt and cut offs. He came out dressed similarly showing his extremely hairy legs.

I kept stealing glances at his muscular, legs not really understanding why. I got in his pickup and we drove pulling his boat to the lake.

We launched his boat and he was eager to raise the sail and take it for a virgin voyage.

We were out for awhile talking and enjoying the experience. Eventually he dropped the sail in a cove, grabbed a bottle of wine from an ice chest he had prepared and poured us each a glass. He took off his shirt to catch some sun showing his hairy upper chest and happy trail disappearing below his wasteband. I began to fidget as blood rushed to my crotch. I followed his lead and removed my shirt too, my chest showing no signs of hair.

We talked about his new noat and about how perfect the day had been when he began questioning me about my life. "I don't see you with any girls, are you interested in girls?" I told him I had dated a few girls but I didn't attract much attention from the opposite sex. "Well, do you ever cross the fence?" long pause "Have you ever fooled around with a man?"

I knew where this was leading. I told him I had experimented with a few guys on overnights and in scout camp outs when I was a kid but didn't think of it as anything more than curiosity.

"You know a lot of men have sex with women and men." And he put his hand on my leg. "I saw how you looked at me earlier."

"How would you like to fool around with me." Once again I was speechless. "What happens on the boat stays on the boat " His hand slipped up my leg to my inner thigh. Our eyes met and feeling no resistance he took my hand and led me down to the berth. He brought me face to face with him and reached for my shorts, unsnapped, unzipped and slipped his hand down my underwear taking my cock in his hand. "Something has aroused you." He said holding my rock hard erection. My shorts and underwear fell to the floor and my smooth body except the bush around my cock completely exposed.

He then unsnapped his shorts and let his clothes slip to the floor. His body was hairy and beautiful. His cock was huge, blood vessels bulging and a huge tuft of dark hair around it's base. I was like a deer in the headlights. "Touch it" he said snapping me out of my trance. "Touch me" he repeated. I slowly took his cock in my hand and felt his girth and hot skin. I knew I wasn't getting out of this, and I really didn't want to. I slowly sank to my knees and was face to cock with him. I got in close and felt the heat radiating from his hard dick. "Taste me." I put out my tongue and took it up the length feeling the roughness of his veins and hot skin. Eventually taking his head into my mouth. I could taste his precum oozing out the tip, I nursed and sucked it in. "Do you like it?" I let his cock slip out of my mouth and whispered "yes." I took my hands and felt his cock and hairy balls and took him back into my mouth. I made slow love to his cock with my lips and tongue. My fingers rolling his large balls in his sack.

"Let's get in the bed." I stood and slid onto the bed on my back. He came in on top of me. He kissed my lips lightly and not feeling any resistance began making out with me like a couple on a hot date night. His hands were all over my body squeezing and groping every part and crevice. He got back on his haunches and took me in with his eyes. "You are beautiful." He began kissing down my chest and continued down my abs and took my engorged shaft into his mouth. He was an expert cock sucker his hands feeling my balls as he slid his finger down to my taint. He satback, pushed my spread legs back so I was on the round of my back my ass up off the sheets, spit on my pink puckered ass and began tracing around it with his finger. I felt completely vulnerable. I had never felt anything like that. I gave myself completely over to him. My eyes were rolling back in my head, my mouth was going dry and soon was moaning and squirming to his touch.

He stood up and opened a small cabinet retrieving a bottle I soon found out was lubricant. He got back on the bed between my legs and lubed up my ass and his finger. I relaxed and let him have his way. He pushed his finger slowly into my ass. I arched my back pressing into his digit and emitting a response from "Oh Gawd" as my body began to involuntarily tremble.

"You like this don't you?"

"Oh fuck yes" I somewhat guiltily whispered. He just chuckled. Soon he introduced another finger spreading me even further "You're so tight, relax" and then a third digit. He worked them slowly in and out of my ass making me tremble in pleasure.

Afte a rew minutes of him pleasuring me he took out his fingers making me feel a cool vacancy in my opening. I opened my eyes to see why he stopped. I saw him lubing his beautiful cock.

He saw me watching "Don't worry, I'll take it slow ." He hunched over me his spear pointing at my target, his cock made contact with my gaping hole and pressed his cock slowly into his virgin boy.

I felt a closeness I had never felt before. Having him invading my body gave me a fullness that took over my whole body not just my ass. He began easing in and out of me sending me to pleasure places i had never been. Eventually, whe he thought me ready he began to pound away on me our skin slapping together loudly but not as loudly as my grunting the urged him on. I felt like I was being wound up like a clock spring, tighter and tighter knowing something was going to have to give.

"Oh FUCK YES!" I shouted with abandon. "Fuck me... " my voice trembled as I talked into his ear. His hairy chest was pressed against my smooth chest and he rocked my whole body with each thrust.

I could feel my cock pressed between our bodies. It felt hot and the tip ached in a good way. Suddenly like a firecracker it exploded shooting one, two, three seemingly not stopping and I felt my cum shoot in waves and soak both our bodies and running down my side onto the bed. My head felt lije i was having an out of body experience, my cock pumping more and more. He didn't seem to notice my trembling orgasm or my juices all the way up to our chests. Thrusting harder and harder. "You're just a fucking whore, you can't get enough cock can you."Then-he went ridged and I could feel his cock pumping pumping his seed into my body. Ky ass feeling the convulsions as his cock expanded and released its gift. Once, twice.. he must have erupted five times into my now well used ass. He froze and then collapsed on top on me. I felt his manly hairy body covering my boyish body. We enjoyed the afterglow.

Finally he pulled his giant cock from my no longer so little opening and I felt the tidal wave of his cum drain out of me onto the bed between my legs. Both of our cocks still ridged and pointing up but this time not quite so hard.

We lay there silently, l a little unnerved and embarrassed. He reached over and ran his hand over my cum soaked chest and down to my cock. I flinched "Oh, a little sensitive is it?" He broke the silence and we laughed and I cuddled up to his warm protective body. He said "let's wash off in the lake" and we got out of the bed went up on deck and jumped in nude rinsing the sperm off our bodies.

The rest of the afternoon was consumed with cuddling caressing and repeating our main event.

That was my first real experience with another man, but not my last.