My Best Butt Buddy

Last night I was at one of my favorite local bars after a softball game with the guys and I saw a guy sipping brown liquor at the bar who reminded me a lot of a guy I once knew in Savannah. He had a found place in my memories because he and I had the best guy on guy sex I ever enjoyed. His name was Henry, and he worked in the library at the school where I was a 23 year old M.A. student in the English Department. Henry was in the Interlibrary Loan Department (ILL) and I saw him around quite a bit, pushing trucks loaded with books from his office to the outgoing departments and such. At that library, you had to actually go to the ILL office to pick up your books when they arrived from another university so I got to know him in a small talk fashion through picking up and dropping off books.

I didn't know he was gay, though I had a sense he was. Henry always comported himself professionally when we talked. I suspected he was into me because I caught him watching me walking around the library but I didn't know what to do about it. I certainly found him alluring. He was hardly a queen—he looked a bit older (I later learned he was 41) he was almost as tall as my six feet; with wide shoulders and a light beard. He had a sense of composure about him that I felt drawn to.

At that time in my life, I had just started exploring my bisexuality and it was still pretty rough going. I had hooked up with a few guys but never felt like it was all it was cracked-up to be. The only time I left an encounter—out of the half dozen or so I had at that point—feeling like I wanted to try it again was with a man in his late 50s and his thirtyish lover. When I reflected on all of this I realized that people I lusted after were usually older than I was—in their thirties to early sixties. I've never known why, but I prefer that—I don't think I fit into the whole mommy/daddy/son thing—I don't want to be cared for and used, but I like knowing my lover is comfortable and turned on. And I've felt that from people who've lived life an earned a certain comfort in themselves and a patience with the world.

At any rate, I did not know how to test Henry until the opportunity fell into my lap one summer afternoon. I was pulling a few journals to copy and I saw him chatting with a colleague. I realized I needed to walk by him to get to the copy room. I waited a minute while pretending to thumb through a publication while fantasizing about what it might feel like to have a hot pair of lips settle on the shaft of my cock then suck and pretty soon, my cock had swelled into a raging hard on. I had boxers on under my shorts and my cock had dangled down my left leg. As it hardened it strained against the material and my cock head was visable pressed up against my shorts against my thigh. My hard on was evident but not obvious.

I walked toward him nonchalantly with my arms piled high with books and my cock throbbing. His friend walked off and I could see out the corner of my eye that Henry was watching, as I passed him I turned my head slightly and saw he was staring at my cock. So I knew but didn't know what to do about it.

About the same time I started looking on line for a guy in town to meet as a regular play buddy. I made it quite clear to the people I chatted with that I wanted to meet an older guy who wanted a no-strings type commitment, who was safe and was reciprocal.

I eventually met a fellow named GAtopman, who sounded great. Tall, early forties lived alone in his own home and claimed to have an 8 inch cock. I arranged to go to his place one evening for drinks and conversation.

His house was just off a main road, but it was set back in the trees a bit. It was a small wood structure, very neat and inviting. It was late—eleven or so—and the place was dark except for a porch light and a warm glow inside.

I took a deep breath, got out of my car and strode to the front door. Dressed casually, I had on a polo shirt, relaxed knee length cargo shorts and my trusty sports sandals (when it gets warm I try not to wear socks—let's just call it the relaxed southern boy in me). I climbed the front steps in the blanketed softness of a southern summer, filled with humidity and the chirping of cicadas and knocked. My mystery date appeared from the kitchen and opened the door.

You can imagine how pleased I was when it turned out to be Henry.

He smiled and invited me in and we both laughed over the situation.

"I thought you were checking me out," I told him.

"Oh Jesus." he laughed, "I'm sorry, I try to be very low key about that kind of stuff—in that library people gossip so much, I'd hate to start an unfounded rumor about some guy. Would you like a drink? I've got beer, but I usually drink bourbon and Coke."

I'm now a confirmed bourbon lover, though I've moved beyond mixing it, I prefer the sharp taste of straight, chilled bourbon against my tongue and the warming affect it has sliding down my throat. I'm sure I have Henry to thank for that along with the acquisition of other tastes.

He went to get drinks and I sat on the couch in his small living room. I was excited but nervous—my palms were moist and my stomach twisted, my hear thumped in my chest and I tried to breath slowly and deeply to calm down.

"Enjoy," Henry smiled, as he handed me the clinking glass and sat next to me on the couch.

I relaxed a little as I sipped the drink. The room was cooled and a few candles provided the only light other than one from above the sink in the kitchen. Henry certainly knew how to set a mood.

We talked a bit and got to know each other--I told him I was bi and shared a little background, where I was from and that sort of thing. He listened and nodded and told me about himself: he was gay, worked at the library and owned a small house cleaning operation that made his money.

"So tell me about what you like in bed," he asked.

"I'm pretty open-minded, I guess. I really like oral sex, but I've never cum from it—I enjoy giving and receiving. I like having my ass played with and have liked fucking guys and girls in the ass or otherwise. I've fucked a couple of guys but have yet to find a guy that could fuck me without it being horrible--the guy who I let get into my ass shoved in and thrust away, it sucked."

"That's too bad," he commented and talked about his sex life, which was pretty consistent. "I don't cum from oral either," he told me and sighed, "I'm a top, that is, I like fucking but don't really take it."

He also didn't like effeminate men and liked privacy and discreetness in a lover.

I hadn't really been paying attention but my sports sandals had slipped off and he was caressing my leg--running his hand up and down my thigh languidly.

He stopped mid sentence—"Is this ok?"--and I assured him it was.

He picked my legs up and placed them over his lap and he began to rub my feet. I relaxed enjoying my drink. He rubbed up my calves and over my quads as I reclined moaning softly. This felt great, so comfortable and fun. I moaned again as the candlelight flickered relaxing me even more. He read me well, because his next move was sliding a hand up my shorts, under my boxers playfully squeezing my hard cock.

"Whoa," Henry laughed, "What are you packin' there? Can I see?"

I smiled nodding and he unbuttoned my shorts, tugging them down before pulling my boxers off and freeing my cock to the cool air.

I smiled with encouragement and he gently ran his palms over my crank and caressed my sac.

"My, my," he laughed, "This thing is nice—what is it, about eight inches?"

I nodded feeling anticipation like never before. Other guys had touched me before and I had gotten with men a number of times—but never like this. Never had I felt so relaxed and comfortable, never had I felt like I was being seduced like this. I was ready and willing for anything Henry suggested that night, he knew how to turn me on.

"It's great. Nice thickness and a huge head—let me see if I can figure out how to handle this puppy."

He pulled me up onto his lap and as I lay back with my head propped up by the arm of the couch, he stood my throbbing member up with his hand while he began to suck it greedily down to the base. I could feel his tongue slide down my shaft as it slid into his throat as he moaned.

Pretty soon Henry had it tamed by sucking me off like the expert he was. I slowly thrusted up to meet his mouth fucking his lips. After awhile, I sat up, stood, and then planted my feet on either side of him on the couch and presented my proud cock to him once more before leaning forward to hold onto the top of the couch while beginning to fuck his mouth more seriously. Henry, for his part, had one hand squeezing my balls—the hand squeezed in just right, then tugged down gently and repeated. The other had held me in place grabbing my ass. He moaned and stopped to tell me he wanted my jizz. I grunted and pumped more. An orgasm welled up into my balls suddenly and I stopped pumping, which made John suck harder. As I began to shoot he pulled my cock into him deep by clenching my ass. My cum poured down his throat.

Suddenly my knees went weak from the explosion and I settled onto the couch, with my shorts lying nearby and only my shirt on. It was the first time I came that way and I loved it but there was more to come.

That night I first learned how enjoyable being fucked could be.

After our escapade on the couch, we adjourned to his bedroom. He led me into the dimly lit room. From the soft light of the living room I could see a large queen sized bed (no puns please!) with a brass head and footboard and a patchwork quilt comforter. We stood and kissed before I stripped off my shirt and began undressing him. I slowly pulled his shirt and shorts off and discarded them to the corner of the room towards a hamper. He looked hot in his white boxer briefs--a nice broad chest, light chest hair, with a tight ass. As we stood and kissed our hands just roamed all over each other's bodies.

I knelt in front of him and tugged his underwear off. I felt his cock flop against my cheek in the dark--it was huge. Eight inches, as big as mine. Henry had nicely trimmed pubes (something I soon imitated) and cupping his shaved balls while ticking the underside of his cockhead with my tongue was a pleasure.

He sat on the edge of the bed encouraging me, "That feels great man, keep going."

I worked as much of his cock into my mouth as possible while stroking his balls and running my fingers through his short pubes—I really wanted to repay him for the pleasure he had given me.

Henry rubbed my shoulders and head while moaning my name as I worked--I wanted him to enjoy every second. This turned me on and I got hard again.

After a few minutes he whispered "Greg, I can't come orally."

I asked him how he did and he reminded me.

"I'm a top, I love to fuck a guy--can I fuck you?"

I wanted him to but I was worried because it had not gone well with me and dicks in my ass--but I wanted him to enjoy himself so after exacting a promise to go slow--agreed.

He rummaged through a drawer and brought out a condom and a tube of lube as I got comfortable on my back in his bed. He rolled the hat on and lubed up and then, after I pulled my knees back, he began painting my asshole with lube--he slid in a finger and then two, which felt good.

"I want you," I told him and he smiled and positioned himself--then he slowly slid his engorged cock in my ass as he sighed happily--and I felt like I was being split open.

I didn't like it but wanted to try, so I asked him to pull out and we tried another position.

"Get onto your knees for me," he instructed, "Don't worry, I'll be careful."

I got on my knees and grabbed onto the footboard of the bed. I felt Henry behind me, with one hand on the small of my back as I tried to relax. I bowed my back down and stuck my ass in the air.

"Go for it big one," I moaned.

For whatever reason this way worked. He slid in an inch or two and slowly and gently fucked me with the tip of his cock while rubbing my back and ass cheeks (which, he claimed, with a biased opinion, were my best feature).

After a minute I breathed, "Give me more" and within five deepening strokes he had all eight inches in my tight hole—it felt awesome.

He was still going slowly but I felt my ass accommodate him while his hands squeezed my hips.

With one hand on the footboard, I reached back and grabbed his balls and squeezed—

"Shit, Greg," he announced, "yes, do that, man."

As I squeezed a little hard and faster I spread my knees and breathed into the quilt, it felt so good—his cock bottomed out and tickled me in all the right spots. My ass was slick with lube and it was pure pleasure feeling his pelvic region bumping against my round ass!

He reached around grabbing my cock and stroked me in an increasingly faster pace which matched his fucking.

"Henry, I'm going to cum again," I told him as he picked up the pace, breathing hard in my ear, kissing my neck, shoulder and back—he was so fucking masculine, it got me unbelievably hot.

To be spread on his bed there in the dark, getting fucked the right way, I knew I'd found the guy to return to.

His moans got louder and he was saying my name over and over, "Greg, oh shit, God I love that ass."

Soon he was yelling it as he came. He pulled out and I sat up, turned around and continued to jerk off while kneeling.

Henry still knelt opposite me, sweating and smiling as he laughed, "Come on stud, cum for me."

Soon I sent arcing spurts of cum across his chest and bed. We collapsed on the now rumpled comforter and kissed deeply. There were plenty more nights to come where we enjoyed each other that way and other ways.