JAMES
By Dudley Jarvis-North
Occasionally, while headed to buy the morning newspaper, I would see a young man walking his two pugs on the streets of Boston's South End. One of the dogs was fawn-colored, the other black. They were a mismatched pair, but there was nothing in their master's fashionable clothing that didn't go together. He always wore an expensive looking suit, a tie, often red, white dress shirt, and smart Italian shoes. He paid attention to detail, which impressed me partly because I don't. He would always nod a hello and smile, as I slinked informally in faded jeans and stretched-out T-shirt, with Red Sox or Patriots cap on my head.
He was in his early 30s, tall and slender, blue or green eyes -- I still can't say -- dark hair, and glistening white skin. He had the rosy cheeks of a boy who had grown up on a farm outside Dublin or Belfast. Yes, he was definitely Irish. He had that glint in his eye. I had seen it many times. This was Boston after all.
He piqued my interest. Was he one of the young men who naturally gravitated toward this neighborhood because it was comfortably gay? Was he married to a woman who nagged him to take the dogs for their early walk, or nagged him about everything? Was he sexually ambiguous as Boston Irishmen can be?
One night I learned more about him.
It was a hot Thursday night and I was restless. I usually don't go to clubs on a work night. But there I was, threading legs into my jockstrap, sliding on my tightest jeans, donning a white T-shirt. I am 5-9, wiry, with olive skin and blue eyes that were eager to see what was "out there." Thursday was a "tweener" night." It wouldn't be as crowded as a Friday or a Saturday; yet it was close enough to the weekend for guys like me who couldn't wait to spin the wheel of sexual fortune.
The Eagle was a small club -- perhaps 90 feet long by 30 feet wide. A mahogany bar clung to the right side. Jack -- the manager -- was there to say hello, if he liked you -- or growl an insult, if he didn't. He didn't like many people, but he was always friendly to me. I got my usual VO and water. That and the crowd gave me a warm feeling. I made my way up a small ramp in order to get a closer look at the real reason I was there. It was smoky, crowded. My eyes already stung and I was cursing the smokers, but I wasn't going home yet. There were too many handsome guys, and I was hot in every way.
As I panned the place, I got a start. In the corner was my dog-walking, dedicated follower of fashion quaffing a drink. Gone was the suit, replaced by a crisp, yellow summer shirt and neatly pressed khaki slacks. I hadn't really had enough VO to summon the courage to walk up to him. I didn't have to. He saw me and sidled up and said hello. I asked how his dogs were doing, and his face lit up. He confided that their names were Flora (the black one) and Fauna, and wondered if that was too cute for words. I told him -- honestly -- that it was the right touch -- why not have fun with their names since he obviously loved them so? He asked if I would like another drink. Yes, I did.
About 20 minutes of chitchat ensued, and I learned that he was from Ohio -- grew up in farm country, that he loved Boston, that he was a lawyer. What I really liked was that he was impressed that I was an editor at a Boston newspaper. When I tell some guys that I work for a newspaper, they automatically assume that I drive a delivery truck, Mr. Blue Collar. It's not an image that pleases me -- but what can I do? I am a dark ethnic with a certain look.
It was getting past 1 o'clock, so I asked if he might like to go back to my apartment. He nodded yes, but would I mind if he got the dogs. "I'd love it," said I.
We sauntered the six blocks, and while the dogs sniffed around my living room, James -- that was his name -- sat on the leather sofa, with a Heineken in hand. I sat next to him and put my arm around his neck, gently massaging his shoulders. I told him my fantasies of his being married and being ordered around by a demanding wife. He laughed, then dropped his eyes to the floor and mumbled that he once had a wife but was divorced.
I began to unbutton his yellow shirt, as he slumped back, making it easier on my fingers. He had a lithe, slender body, with just a little hair on his chest and the right size nipples for his slender frame, perhaps as large as quarters. He was toned but not muscular. He had freckles on his upper back -- the sure sign of the white-boyness I appreciated. I used my fingers and thumbs, running them gently down his back before I turned my attention to the front and his supreme nips -- pink enough for me to have a lick. I could smell that he wore deodorant -- but not too much, even on this humid summer night. I wanted to smell him, not some product that a GQ ad insisted he overuse on his body.
As I kissed his skin, he let out a sigh. Yes, he had sensitive nips -- some men do and some don't, so I used my teeth gently to see what response I would get. He seemed enthralled, ooohing as I bit down a little harder. I took a swig of his still cold beer and pushed my full mouth onto his hot nipple eliciting another gasp of ecstasy. I brought my still full mouth up to his lips and kissed him, letting a slight flow of his beer turned mine into his grateful mouth.
I could see the hardness in his pants as I peered down at his brown treasure trail. I liberated the rungs of his belt from its khaki prison. I wanted him badly.
At my unspoken urging, he lifted his pelvis high enough for me to slide his khakis off his hips and down his legs. I removed his penny loafers-- he was such a preppy -- and tugged them past his feet onto the floor. I couldn't believe my luck as I looked up from beneath. He was wearing the whitest pair of classic Jockey briefs -- not the preppy plain blue boxers I would have guessed he favored.
I clutched his hands -- he was a little tipsy -- and led him down the hall to my bed.
I pushed him downward and climbed aboard for a kissing session. He was receptive to my lips and tongue. Then I turned him on his stomach and kissed the back of his ears and neck. I could feel the heat emanating from his skin as he gasped. As I moved down his spine, I began to pull at the elastic band of his Jockeys, using my fingers to open a small fissure in the fabric. This seemed to turn me into a ravenous beast atop his prey as I love the sound of ripping cotton separating from elastic. Finally, the band around his waist was free. As I pulled the cotton away, I could see brown hair peeking out from the top of his crack. Who would have guessed that this boyish guy had butt hair? I ripped the rest of his shorts free and felt a nervous shudder from his body.
"I haven't been fucked in a long time," he said. "I don't know if I can." But I whispered in his ear that we would go slow, that it was going to be all right. I also told him firmly that he was going to get fucked.
I used what was left of his shredded Jockeys to tie his hands behind him. I had handcuffs in the drawer, but thought they would to be too intimidating for my preppy prey. I wanted to excite him, not frighten him into a puddle.
As I moved my tongue toward his hairy cleft, he seemed to relax. Getting rimmed is so much less invasive than opening up for a dick. He seemed grateful that I was using a softer part of myself on his hot hole. He was clean -- just a slight tangy taste of sweat as I plunged my nose into his All-American butt and breathed in for what seemed a lifetime.
After perhaps 10 minutes of this, I reached down beside my bed for the lube of choice I kept handy for such occasions. I plucked just enough of the Crisco-like substance out of the container to coat his hole and my uncut dick, rubbing the skin back and forth to let the grease take hold. I let one finger stay in his socket and moved it slowly in and out. He wasn't kidding--he was tight. He was also burning hot inside. I tried a second finger and he opened up a little more.
I whispered how gentle I would be -- a white lie -- and how good it would feel if we took our time -- the complete truth. As I held the back of his head with my two hands, I touched my foreskin to his pucker and rubbed it up and down his hairy crack. I waited for him to relax and coached him to breathe in and push out. I soothingly whispered how good it was going to feel -- repetition of these words always helped -- how much he really wanted to have an Italian dick inside him. He whispered that he really wanted it -- that he had thought about it, even when we had chatted while he was walking his dogs. He told me he thought I was hot and that he had never been fucked by an uncut guy.
The talk reduced his anxiety and increased my desire ten-fold. He was beginning to trust that I wouldn't hurt him. I could feel him loosen up as I pushed my dick slowly beyond the ring inside him, and just like that, I was all the way inside -- my dick as hard as it has ever been, feeling the furnace of his innards enveloping my dick.
Gently, I pushed in and out, kissing the back of his ears again and caressing the nape of his neck. He tasted so sweet I thought I'd die the little death then and there.
I could tell from the way he was pushing his butt against my legs and crotch that he was having just as good a time. Then I heard him utter the words that always get me super hot: "Please fuck me. It feels so good."
And that's what I did. I pumped in earnest, pulling it nearly all the way out and slamming it home. His butt was so hot, I thought it would burn my pecker into toast. As I got closer, I grabbed his mushroom-capped dick -- not too long, just plump enough to fill my hand -- and made him cum, just before I shot my load into his creamy, delectable ass. I collapsed on top of him and kissed him.
The next day -- all day -- as I tried to concentrate at work, all I could think of was his face, his ears, his neck, his nipples, his dick, his scent, and his sweet, hairy butt.
Maybe I'll get up early tomorrow when he's walking Flora and Fauna and see what he thinks about morning sex.
Guys, appreciate any feedback on my stories at doctordestiny@comcast.net.
I'm a retired Boston journalist who enjoys writing these and hoping they're good. I've already posted The Bass Player and The Pact (Encounters, Sept. 2017) and Aaron's Basement (Adult Youth, December, 2017) and Drink It (Urination, Dec, 2017).
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