A gay story: Craigslist Pt. 03: Fucking the Innkeeper It’s been years now since they vanished, but I still miss the Craigslist personals. Sure, they were filled with fakes, phonies and pic collectors. Even if you managed to hook up through one there was no guarantee that you’d actually have a good time.
Once in a great while, though, answering an ad could lead to a unique, unforgettable encounter. Or more than one.
In recent years I’ve gotten into anonymous hookups. Not only no names, no faces. Weird and perverted? Maybe to some. But if the other guy wants the same thing, why not? There’s something primal and honest about not even looking the person you’re balling in the eye. It’s all about your cock, his mouth, his ass, and your using them to get yourself off. Sound cold and heartless? Nothing could be further from the truth if you run into someone who lives to light that fire.
Glory holes are the first thing that comes to mind when you think of going anonymous, and I’ve had some smoking hot hole-in-the-wall sex, both giving and receiving. There are other ways to stay hidden from each other without having a wall between you, though. I’d topped guys anonymously a few times before I answered this particular ad. Somehow it all came together that January day in a way that’s haunted me ever since. Even better, we got to do it again.
The New Year had come in chilly, wet, and dreary, no surprise since I was in New England spending the holiday season with the fam. Not that I was having a bad time at all, but still I was glad I had elected to stay in a hotel room by myself. It was a place to retreat to when all that togetherness got overwhelming. I could have predicted that on the second of January, exhausted from all the holiday celebrating, horny as hell, I would be alone in my room sitting at my laptop, looking at the local Craigslist personals.
“Masculine guy face down, ass up.”
Well, this was interesting. I took the clickbait.
“Come find me in a room of my spacious private residence. WM will be on the bed blindfolded and ready to take your hooded cock. No names, no faces, no questions. I’m HWP and reasonable looking, UB2. Give me a rainy day to remember.”
He didn’t give his exact location, but I had a rental car and a free afternoon, and it wasn’t snowing at least. What the hell. I sent a reply, keeping my expectations low.
“When can you get here?”
He was at least a half hour’s drive away when I looked up the address he gave. I debated whether or not to go through with it, but boredom and my sex drive won out. Ten minutes later I was speeding northward on the interstate to meet the unknown and, I hoped, equally horny stranger.
By the time I got off the freeway the scenery had thinned out and definitely become rural. The town I found myself in was one of the pleasant small shoreline communities that dotted this region and attracted a lot of visitors in the warmer months. I passed the common with its carefully manicured lawn and a snow-white, spired church dominating. Traffic was sparse and the main street, picturesquely restored and lined with shops and businesses, was empty of people. I threaded my way into a narrower side street that led to the shore and the town beaches and finally stopped, looking open-mouthed at the building I had located.
I double-checked. Yes, this was the address that I had entered into my GPS. A rambling Victorian structure met my eye, gabled and ringed with a covered veranda on all sides. A trimmed hedge and flowerbeds surrounding it must have presented a pretty sight in spring and summer, though now they were denuded of foliage. A tastefully small, hand-painted sign planted near the imposing front door, which was painted a contrasting color from the walls, announced the establishment’s name: “Seaside Manors.”
I was in front of what the travel books would call a “quaint, charming Bed and Breakfast.” Not at all the usual place for a casual hookup—and why was someone on holiday here on a cold day in early January? I quickly typed on my phone.
“I’m at Seaside Manors. Right place?”
“Yes,” the reply came. “Front door is locked. Go up the side steps onto the porch and walk around the house until you get to Room 3. Knock and come in. Wait a few so I can get ready.”
So this was the place, and it was showtime. In spite of the few qualms I had on the way my pulse was now racing and my dick was pressing painfully against my pants. I opened the car door and stepped out into the misty cold. The weather was chilly enough that I could see my breath in the fading light of a late New England afternoon.
A small paved path branched off from the front walk and led me behind the hedge to a set of steps leading up to a screen door. I opened it and stepped up into a spacious common area, dotted with wicker chaises and small round glass tables surrounded by chairs with wrought iron backs—a pleasant place to have breakfast or tea when the weather was a bit warmer. Beyond this the veranda narrowed into a passageway with successive doors leading into individual guest rooms. No. 3 was, no surprise, the third one. I pulled open the screen door and knocked once, sharply. There was a slot for a magnetic hotel key, the first modern touch I’d seen, but the door was not shut firmly and opened easily when I pushed it.
I stood in one of the guest rooms, as elegant as the outside, with carved oak furniture, hardwood floor dotted with throw rugs, antique lamps and light fixtures, and an imposing, tall four-poster bed covered with a quilted duvet. The lamp on the table next to it was lit, drawing my eye to the items placed there, the only ones not matching the carefully planned effect-a squeeze tube of lubricant and a couple of foil-wrapped condoms.
Then my eye went to the bed, where there was something else out of place—a bath towel had been laid on the comforter, and on it was my partner in crime, fair-skinned and auburn haired, naked, face down and ass up as promised. He was on his knees with his head turned to one side on the bed, palms down, a strip of cloth tied around his head serving as a crude blindfold. His position gave me a perfect view of his smooth, hairless cheeks and a shadowy one of the prize that lay between them.
I held my breath. Dead silence, except for the soft patter of rain that had begun to fall outside. Clearly, we were the only ones in the place. My man was no guest of this establishment, but the innkeeper, taking advantage of the offseason to have a little kinky fun.
I had a lot of clothes to take off but did in record time. The guest room was chilly and I moved quickly toward the bed once I got naked, picking up one of the foil packets and hooding myself as he’d requested. I picked up the tube of lubricant with one hand and reached out and cupped one pale butt cheek with the other, drawing a soft intake of breath, the first sound he’d made since I’d entered the room.
“Sorry,” I said. “It’s cold outside.”
“Warm me up. Hurry.”
I squeezed lube into my cold hand and ran slick fingers down his crack and into his tight, hot hole, making him gasp again. I smeared the rest onto my erection and clambered onto the bed behind him, pushing him forward to make room. Somehow the oddness of the setting was a tremendous turn-on and I found myself literally shaking with excitement as I got the head of my cock against his hole and grabbed on to his hips. My eagerness made me push a bit too hard-all of a sudden I slipped inside him and he cried out.
“Sorry,” I said again, as his breath came in short gasps. We held still for long moments. Then I heard him sigh and relax.
“Oh yes,” he said. “It’s been so long.”
He reached out and took hold of a phone that was lying on the bed cover, stretching back and offering it to me. “Take a pic of your dick inside me. I want to see that view.”
He was really into this. I obliged, taking a few different angles, pulling out to get more of my rod into the shot. I wanted to take some with my own phone, but it was in the pocket of my pants that were lying in a heap on the armchair in the corner. Oh well. I threw the phone back on the bed and got down to the business at hand.
An anonymous encounter is always a bit of a gamble, especially one like this, where we hadn’t even exchanged pics. My man hadn’t lied—he was reasonable looking. Chemistry is a chancy thing, though, even when your partner is attractive. Just a few moments into this fuck I knew it was going to be a hot one. It wasn’t just the eagerness of his hole clenching around my thrusting cock. It was his mouth, hanging slackly open in concentration beneath the blindfold, the muscles in his back and shoulders, tense and rippling, and his hands, clutching the duvet and pushing it into wrinkled peaks. I knew that all he was thinking about was the rod of hard flesh splitting him open, giving him the pleasure he had craved for who knows how long.
I fucked him methodically, not too fast, not wanting to go over the edge too soon, wanting this to last. I pulled back until the bottom of my dickhead started to emerge, then plunged it back in to the hilt, drawing a moan from him every time.
Then he took me by surprise, suddenly rising to his knees, making me rock back until he was sitting on my lap, still impaled on me. He worked his hips and thighs, fucking himself with my organ, a low keening wail rising from his throat. I wrapped my arms around his body, ran my fingers through his lightly hairy chest, and felt for his cock. It was soft.
“You like this, don’t you?” I whispered into his ear.
“God yes. Love it.” His hips moved faster and I grabbed his torso to make him stop.
“Not yet.” I pushed him forward into our previous position and held perfectly still, willing my excitement to go down. It finally did, and I resumed my slow fucking.
Time slipped by in that overstuffed, chilly, airless room in the inn as we cycled between those two positions, my cock never out of his ass for a moment. Anonymous sex can be the most intimate sex of all when the two of you are on exactly the same wavelength. We were two naked male strangers with nothing on either of our minds except indulging our appetites, celebrating the perfection of our chance coupling.
It had to come to an end, though. I’d pushed him back down on the bed again and realized this time I couldn’t hold back any longer. “I’m going to cum,” I told him, and began to pound into him harder and harder, until there was an audible slap every time my pelvis made contact with his butt.
“Do it,” I heard him gasp, and then I heard and saw nothing more as the orgasm exploded inside my head. Choked grunts emerged from my throat as I felt my cock fill the rubber buried in his rectum with spurt after spurt. My back arched convulsively until I was staring at the ceiling. Then all of a sudden the storm was past. My forehead dropped onto his back, my eyes squeezed shut as I gasped with release.
Finally I began to come down to earth. I rested my weight on his back, still panting as my hands stroked his chest and stomach. “Nice,” was the single, inadequate word I managed to get out.
“Mm hmm,” was the equally lame reply.
I sat up and pulled out of his ass, slowly and reluctantly, then backed up and got off the bed, my now stiff muscles protesting. As soon as we separated the innkeeper collapsed flat onto his stomach. He hadn’t cum, hadn’t even gotten hard, but I figured that wasn’t the point.
“Toss your rubber in the basket. I’ll take care of it.”
“Thanks.” This was the awkward part. I got dressed quickly, without really knowing why I was in such a hurry to leave. At the same time I felt the need to make small talk.
“Not very busy right now, are you?”
The innkeeper turned over, the blindfold still around his head. “January is always a slow month, especially with weather like this. Gets boring, so I want to scratch the itch.”
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“Well, glad I could help you scratch.” Yikes. Time to go.
When I got back to my hotel room there was an e-mail from him.
“You forgot your hat.”
I typed back a reply right away. “I’ll pick it up next year.”
***
I didn’t retrieve the hat a year later, when I was back in town. Or the year after that. Today it’s just after New Year’s Day three years later, and the blindfolded innkeeper and I have finally managed to reconnect. It wasn’t for lack of trying. He was skittish on my previous attempts to arrange another encounter. The first year when I contacted him he had the flu and was flat on his back in bed. The year after that he said that offseason guests had booked a room the day after New Year’s and he couldn’t risk a meeting. It seemed to me that it was a big enough place that if we chose a room somewhere far away from them, met late at night and kept quiet that it would be okay. When I said so, though, he stopped answering my messages.
I was a bit frustrated at the fruitless exchange that second year and had given up on him in my mind. Then out of the blue this year came a message after Christmas.
“Regretting the missed connection. Hope we can meet this year.”
The images from our one secretive, passionate fuck came rushing back into my mind. I didn’t have to think long about replying. This time he seemed eager to make it work.
So I’m stopped in front of Seaside Manors once again on a cold, gray early January day, a bit down the street from the entrance to be discreet. This time, when I step out of the car, I head straight up the walk and up the steps to the front door. I pull it open and enter the reception area. It’s laid with a hardwood floor, of course, furnished with tasteful understatement, and lit with ornate antique lighting fixtures.
I head up the flight of stairs on the right side up to the second floor and turn right at the landing, toward the rear of the inn. He’s asked me to come to Room 9 this year. Looking down the hallway I see doors on both sides. One on the left is cracked open. I push it open slowly and head into the room.
It’s smaller and less fancy than the one three years ago, though just as elegantly appointed. The one window lets what outside light there is in. The bed is placed facing the door. There is a lamp on a small table by it as before, lit up so I can see the condoms and lube placed there.
He’s waiting for me, lying flat on his stomach, clasping one of several overstuffed pillows with his arms. He’s wearing a dark red pullover shirt and nothing else except the blindfold. His ass is exactly as I remember it, pale and shapely.
I get my clothes off and head toward the table to hood myself. I’m turned on but also a bit nervous, not quite believing my luck in getting this far a second time. This might be affecting my cock, which is not as hard as I’d like it to be. As I slip the condom on it softens further, and lubing it up doesn’t have the usual effect. Rats.
I stand at the foot of the bed, staring down at his outstretched legs. I stroke his butt, but as nice as it is my dick remains at half-mast. I’m going to have to try something different.
“Can you turn over?” I ask him.
I have no idea how he’ll react, but he obeys, hoisting himself up onto his elbows as he faces me. I can only see half his face, of course, but it seems kind. His mouth is good, with full, sensual lips. His dick is average size, cut, and like the last time, completely soft. No inspiration there.
I climb onto the bed. “Work my nipples,” I say. Mine are really sensitive and this usually does the trick. His hands find my chest and go to work. That gets some electricity going, at least. I reach underneath his shirt and pull it up, baring his chest. I bend down and kiss his stomach, working my way upward until my lips are nuzzling at his throat. I hear his breath quickening and decide to chance it. The next moment my lips are just above his and my tongue darts out and touches his mouth in invitation.
A split second of suspense. Then his lips part and we are in a deep, open-mouth kiss, lips and tongues tangling, clicking as they part and come together again. Soft whimpers rise from both our throats. Quickly I straighten up, grab my finally hard dick and guide it into the shadows between his spread legs. There is a familiar moment of resistance, and then his head falls back and a long “Aaah!” wells from his throat as I slide into him.
It’s even better than I remembered, though I’m basically kneeling on the bed and don’t have a lot of leverage. I grab his calves and spread him wide to get the best view of my latex-covered cock penetrating him, pistoning in and out, sinking balls deep into his yielding canal. Every so often I bend and claim his mouth again, bathing his face with my hot breath. His arms wind around me in a tight embrace as we kiss.
Once again we’re joined in perfect union, two riders galloping toward a place we’ve been waiting years to revisit. It doesn’t last as long this time. All too soon I feel the climax rising in me, and begin to shout rhythmically. My bursting tool fills the condom inside him with gushes of liquid fire as I frantically drill his hole.
“Oh God!” I collapse onto his unresisting body, face in the pillow, drawing air in great gasps as I slowly start to recover. I make a move to raise myself off of him and he surprises me again. A strong hand clamps on the back of my head and I find myself in one last wet, urgent kiss. He lets out a sigh of satisfaction when he finally lets me go.
I pull out, hoist myself off the bend and head for the small bathroom. After peeling off the full rubber and a few swipes with toilet paper I’m ready to put my clothes back on.
He’s up on his elbows again, blindfold still in place, smiling in my direction. “Thanks for the adventure.” It’s the first full sentence he’s spoken since I walked in.
As always my post-fuck awkwardness kicks in. “Sorry I took a while to get going.”
He shakes his head. “You were perfect.”
“Appreciate the jump start.”
His voice drops. “I loved kissing you.”
“We’ll have to do it again. Maybe next time with your hands tied to the bedposts.”
He grins. “Maybe.” He gestures. “By the way don’t forget your hat.”
It’s lying on a chair. He’s kept it for me. “Thanks.”
I take the knitted wool cap with me when I leave, though I have a superstitious fear that means I won’t be coming back. There’s nothing I can do except wait a year, to see whether there’ll be room at the inn on another cold day in January. END