While heading out to buy the morning newspaper, I would often see a guy 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, red or blue, white dress shirt, and polished Italian shoes. He paid attention to dress, which impressed me partly because I don’t. He would say hello and smile as I smiled back and ogled him in my faded jeans and stretched-out T-shirt, Red Sox or Patriots cap on my head.
He looked to be in his early 30s, about 6 feet, slender, blue or green eyes – I still can’t say -- light brown hair, or was it dark blond? — and glistening white skin. His rosy cheeks and innocent look made me think he had grown up on a farm outside Leeds or Belfast. He was obviously of English or Irish stock. He had that white boy UK look about him.
His looks grabbed my attention and fueled my fantasies. Had he naturally gravitated to this neighborhood because it was comfortably gay? Or was he married to a woman who nagged him to take the dogs for their early walk, or nagged him about everything? Was he straight, gay or something in between?
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 my legs into a jockstrap, donning my tightest jeans, and a white T-shirt. I am 5-9, wiry build, 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 Saturday; yet it was close enough to the weekend to entice guys like me who couldn’t wait to spin the wheel of sexual fortune.
The Eagle was a long, narrow club – perhaps 125 feet long by 50 feet wide. A mahogany bar ran along 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 warmed me up. I made my way up a small ramp toward the back 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 the smoke wasn’t bad enough to send me home yet. There were too many handsome guys, and I was hot in every way.
As I panned the crowd, 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 had enough VO to summon the courage to walk up to him. I didn’t have to. He saw me and walked up to me, said hello and shook my hand. “I’m James,” he said, “and you are …” “Peter,” I answered. “I was hoping I’d actually get to meet you one of these days,” he said.
I asked how his dogs were, and his face lit up. Their names were Flora (the black one) and Fauna. “Is that too cute for words?” he smiled. I answered 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 (I had that right), that he loved this city and that he was a lawyer. What really thrilled me was that he believed that when I told him that I was an editor at a Boston daily newspaper he believed it. When I tell some guys I work for The Boston Globe, they automatically assume that I drive a truck delivering newspapers. My friends, ever ready to zing me, howl with laughter when they overhear that.
Why do I take the heat? Working class guys are hot. So what if I look one of them, Mr. Blue Collar with my olive skin, uncoifed hair and clone Levis and T-shirt. I’m an ethnic with a certain look, and that’s that..
It was getting past 1 o’clock, so I asked James if he wanted to go back to my apartment. He nodded yes, but would I mind if he brought the dogs. “I’d love it,” I replied.
We walked the five blocks, and while the dogs sniffed around my living room, James relaxed on the leather sofa with a Heineken in hand. I sat next to him, put my arm around him and touched his upper back. I admitted to my fantasies of his being married and 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 leaned back, making it easier. His body was lithe, with a sprinkling of hair on his chest and nipples the size of quarters. He was toned, not muscular with freckles on his upper back and shoulders, the sure sign of British Isles roots that I appreciate. I used my fingers and thumbs, running them gently down his back before I turned my attention to his perky nips –pink and ready for me to lick. I could smell that he wore deodorant, but did not overdo it, even on this hot and humid summer night. I wanted to smell him, not some product that a GQ ad insisted he use on his body.
As I kissed his nipples, he let out a sigh. Yes, he was sensitive there – some men are and some aren’t. I bit gently on his nubs to see what response I would get. He moaned and slouched backwards in a sign of submissiveness. I bit a little harder. He moaned louder. I took a swig of his cold beer and pushed my full mouth onto his nipple, eliciting another gasp of ecstasy as cold liquid met hot skin. I brought my still full mouth up to his lips and let a trickle of his beer into his mouth.
I could see that he had an erection as I studied his light brown treasure trail. His beauty took my breath away. It was time for more action. I unbuckled his belt and unbuttoned his pants.
At my urging, he lifted his pelvis high enough for me to slide his khakis off his hips and down his legs. His penny loafers – he was such a preppy – slid off and onto the floor. I couldn’t believe my luck as I looked up. He was wearing white classic Jockey Y-front briefs, not the preppy light blue boxers I would have guessed he favored. White briefs are my favorite underwear.
They were moist with sweat and were tight on him. After getting the front wet with my spittle, I wanted to see his dick. Pulling down his undies, I was not disappointed. Hard and lodged against his stomach was the perfect pink circumcised penis, about 6 1/2 inches long with impressive thickness. The head flared out about a half inch wider than the shaft. I licked his piss slit and tasted a nice sample of his precum. It was sweet and delicious. I wanted to suck him off straight away, but I didn’t want him to cum yet.
I grabbed his hands – he was a little tipsy – helped him up and led him down the hall to my bedroom. My clothes made a pile beside my bed, but I left on my jockstrap. He was on his back, so I climbed up, pinned my knees to his shoulders and moved the front of my gamey jock onto his face.
James wasn’t grossed out in the slightest, nor was he shy about sniffing and licking the fabric. “Damn, that smells hot,” he enthused. “I love your manscent. Who wouldn’t love the smell of a hot guy’s crotch.”
He was showing himself to be many miles from the clean preppy I thought he was.
Rotating him onto his stomach I kissed his ears and neck and enjoyed the heat from his body. As I moved down his spine, I ripped a big hole in the seat of his Jockeys with my fingers. This aggressive act turned me into a ravenous beast as I tore the elastic band completely off what was left of his briefs.
His bare ass was a perfect bubble with a nice surprise. James had a mass of light brown hair running from the top of his crack to the small of his back. Who would have thought that my preppy prey had butt hair?
“Peter, just so you know, I haven’t been fucked in a long time. I don’t know if I can.” But I whispered in his ear that we would go slow, that I would be gentle, that it was going to be fine, that I wouldn’t hurt him. “But you are going to get fucked,” I said forcefully.
I used the elastic band of his shredded Jockeys to tie his hands behind his back. I had handcuffs in the drawer, but thought they would to be too intimidating. I wanted to excite him, not frighten him into a puddle.
As I moved my tongue into his hairy cleft, he seemed to relax. Getting rimmed is so much less invasive than opening up for a dick. He was excited that I was using my tongue on his hot hole. He was clean there– just a tangy taste of butt sweat as I took in his sacred, moist and tender place.
After 10 minutes of licking his hole, I reached beside my bed for my lube of choice that I kept handy for such occasions. I fingered some Elbow Grease out of the container and swabbed his hole and my dick, rubbing the skin back and forth to let the grease take hold. My finger pushed in and he wasn’t fibbing—he obviously hadn’t been fucked in a while. I tried a second finger and his tight butt opened up a little.
I told him how gentle I would be – a white lie – and how good it would feel – the complete truth. I moved his tied hands onto my dick — I had removed my jock — to give him an idea of what he’d be working with.
“You are big,” he said excitedly, “and uncut.” My foreskin painted his hairy crack as he moaned and waited for more. I ordered him to breathe in and push out. “This is going to feel so good,” I self-servingly said. Repetition of that sentiment always seemed to help with reticent bottoms. “You need an Italian dick inside you, James. We both know that,” another shameless self-serving observation.
“I really do, ya know,” he agreed, “It's been so long. I thought you were hot on the street. I wondered what you had in your Levi’s. Plus I’ve never been fucked by an uncut dick.”
He was letting lust overcome fear and felt ready. I slowly pushed the head of my dick inside, then gave him time to get used to my girth.
Slowly -- I wanted to keep my word — I pushed past his ring and stopped. “This is going to feel amazing." And Just like that, my 8-inches were all the way inside.
Still taking a gentle approach, I pushed in slowly and out again and licked the nape of his neck with my tongue. His sweat tasted like warm milk. I thought I’d die the little death then and there.
I could tell from the way he was pushing his butt against my crotch that he was ready for a more vigorous fuck. Then he spoke the words that always thrill guys like me: “Fuck me, please. It feels so good.”
With my dick all the way inside, I got into a rhythm with his body as his hole gripped me.I reached under him and grabbed his dick. He was hard and I wanted to make him cum. Just as my load shot shot into his ass, he let out a moan and filled my hand with an impressive amount of warm cum. I collapsed on top of him, my head on his neck. I drank it right from my hand and licked my fingers.
This was as close to a perfect fuck as it gets.
The next day, as I tried to concentrate on work, all I could think about was his face, the freckles on his back, his cute ears, his pale neck, his nipples, his delicate scent, his mushroom cap that flared out from the shaft, and his surprisingly hairy butt.
The next time I see him walking Flora and Fauna, I’m going to ask if he’s ready for some early morning sex.
