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.
