San Francisco Treats: Ordering Room Service in the City by the Bay

Shaking off the veil of grief that enveloped my last days of summer, I began looking forward to the change promised with the beginning of autumn. I dread winter, but also know that the comfort of coffee houses with free wi-fi will see me through the worst of it. In the meantime, I am making the most of the warmer, sun-drenched days of early fall, hiking along familiar trails and seeking out adventure where and when I can.

I began to travel a good deal; three separate weekends with three different destinations, each trip coming fully equipped with both obligations and potential pleasures. I was in the midst of planning these trips when sorrow came uninvited and having committed myself, viewed them in a new light; as a possible means for casting out the visions and shadows that haunt me.

First up: San Francisco

San Francisco is a dirty, filthy place, steeped in grime and debris, be it The Warf, Union Square, Chinatown or wherever else you might visit. Spit, jizz, and heaven knows what else covered the sidewalks everywhere. I was amazed that this was such a tourist trap, for other than cruising for a hot fuck in the Castro District – it held little in the way of visual enticement. There were a few good restaurants that I was lucky enough to stumble upon, but my distaste for culinary mediocrity was continually called into play. One in particular, an Italian eatery cozily adjacent to a rather famous night club of the classic variety failed to impress. Its food was as bland as it was over-priced. The calamari dish was particularly disappointing, encrusted in a tasteless, impenetrable shell; it was like eating starched parchment. The best food? A dicey little sushi/sashimi place a half block from my hotel. What it lacked in atmosphere it made up for with in-your-face flavor. I also quite enjoyed the East Indian fusion cuisine offered at the restaurant on the main floor of my hotel.

I liked my hotel, a little boutique place which caters to Europeans. My room was everything it needed to be and the windows (which actually opened) looked out onto a corner populated by tranny-hookers in the wee hours of the morning. It was like having a free, late-night floor show right outside your bedroom window. Not that the street walkers were the only entertaining thing to be found in my room, but more on that in a bit.

When I wasn’t busy playing tourist, dismayed by the detritus of human and real debris, or being mildly disappointed by the local food scene, I was burning up the free wi-fi offered by my hotel. Cruising all my usual internet hot spots, albeit with a change of venue, I managed to snag the attention of quite a number of men interested in getting naked with yours truly. In three short nights I managed to play with five very decent dudes (and one not so decent).

The first to visit my room was a tall, thin black man in his early thirties. He wore black-rimmed glasses and looked a bit bookish. He was a no-nonsense sort, not big on small talk. He was there to only to nut. When he first arrived, he was totally ill-at-ease, adjusting the lighting, the shades on the windows, and the pillows on the bed. As he moved silently through these machinations, I sat on the edge of the bed wondering at what point he was going to bolt from the room. Finally, after inspecting the bathroom, he sat in the easy-chair next to the windows. I sidled up, and sitting in front of him, on the floor between his legs, reached up and began caressing the crotch of his trousers. In no time, I unearthed and brought to life a healthy, throbbing, nine-inch wonder. I had no poppers with me, due to my fear that they would be confiscated by security at the airport, and he had neglected to bring any, so I was quite surprised and pleased when I managed to expertly deep throat his monster cock with an ease that impressed us both.

After 20 minutes of playing digital tonsil hockey, during which my dark prince uttered only the occasional, deeply-felt guttural sound of appreciation, he ordered me onto the bed. Stripping off his remaining clothing, he propped both pillows against the head board and proceeded to lay back with his legs spread eagle. I pretty much knew that kissing was off the table with this one, so I didn’t even attempt anything bordering on romantic. Instead I wound my way between his legs and quickly resumed deep-throating his rock hard dick. Wanting to tempt him with what his future might hold, I got on all fours with my ass in the air. With my throat still wrapped around his dick, I reached back and began to play with my hole, testing it for readiness and hoping that he’d take the hint. He did. Pulling me up, I straddled his crotch, and without so much as a whiff of poppers, and just a little bit of lube, slid down the length of his cock like a high-paid hooker working a stripper’s pole. I think we both gasped. The friction of his massive prick filling and rubbing up against my insides had me moaning and steel hard.

We fucked for only about ten minutes, but it was certainly quality time. Once we’d both shot our loads he was quick to make a break for the bathroom to clean up. He surprised me by asking a few questions about myself, but, by that point, it all felt perfunctory. It was late (too late) and I was tired, so I didn’t encourage conversation. All told, it was exactly what I wanted before turning in and I slept very well that night.

The next day, after seeing a few sights – including a really beautiful cathedral – I decided to try my luck and see if I could snag a little afternoon delight. It came in the form of Nathan, a short, furry, bald, goateed, strawberry blonde with a 7 inch dick. There was something incredibly appealing about him. His body was tight and covered in fur. He’d advertised himself as a dominate top, which turned out to be something of a misnomer. In reality, he confessed, he was an energetic cuddler who loved to kiss, rim and suck dick. We got on really well, with both of us commenting on how nicely we were hitting it off. We talked as much as we made out. I kept waiting for him to make a move for my hole, but, other than eating my ass big time, he seemed hesitant to dive in. He told me about his job and then asked me if I smoked 420. He told me had some and would love to share it. I was game. He didn’t have it with him, but only lived a few blocks away. That’s when I noticed the clock.

Unfortunately, Nathan had shown up about 30 minutes after his scheduled time, prompting me to continue to play on-line and book another trick. I had to interrupt our play, claiming that I had made plans to meet friends for a drink. He was really cool about it, gave me his phone number and told me to call him once I got back from dinner, so he could come over, smoke some weed and play more. I told him I would do my best to be back by 8:00 pm.

The trick scheduled stood me up (karma?), so I did end up meeting my friends for drinks and dinner. Good to my word, I was back at 8:00 and called Nathan. He told me a friend had stopped over, they’d just smoked some, and were fooling around, so he was all set for the night (karma? again?). Feeling a tad let down, I immediately got on-line to see what I could find.

An hour or so later I got hit on by this guy named Mike. Mike’s probably at least five years older than me, very tan, and handsome. When I finally met him face to face he reminded me of a fifty-year old Ken doll. He had a beautiful smile… and a partner! They both wanted to use my ass and invited me over to their place for a little 420.

On-line, Mike was charming and personable and while I was reticent to leave my hotel, I decided to venture out into the night. Before I agreed to come, I mapquested their address and realized that they were only about a dozen blocks away from me. I am not much of a night owl, but it was before 10 pm, so I decided to go for it.

I had the hotel ring me a cab – a cab that never arrived. Instead, I poached someone else’s cab as it dropped guests off at the curb. As the cabbie navigated his way to the address I’d provided I tried to orientate the mapquest route that was imprinted in my brain with the street signs we passed. It’s not a very long cab drive and once I arrived, I was pretty sure I’d managed to keep my bearings. As I approached the panel where I was to buzz their condo I got a sinking feeling. What if I was being set up? What if they planned to rob me? What if someone was just playing a practical joke?

Fortunately, Mike answered after the first ring. I walked up and met him on his floor. All he was wearing was a pair of tight fitting, sky blue, square-legged swim trunks: just like a Ken doll! His hair was as perfect as his tan. It was only the crinkle of the skin in the corners of his eyes that gave away his age. A great conversationalist, he was super personable and a real salesman. Entering their condo, I removed my boots and then met Mike’s partner. His partner was probably a few years younger than me. He was bald, tall, furry, and muscular. It was his barrel chest that caught most of my attention. On-line, Mike had sent me a link to his partner’s profile. It described him as a dominate, take-charge top. Now that I’d met him in person? My ass was just tingling.

We sat down in their large, over-sized living room on their large over-sized furniture. The conversation flowed pretty well. I told them what I’d seen in town, they told me what I yet needed to see. I asked why everybody seemed to have 420 and it turned out that in San Francisco all you needed to do was tell your doctor that you’re having trouble sleeping and they’d write you a prescription! With that, Mike and I crept out onto their balcony for a few hits. I am such an amateur smoker that I was hacking and coughing after one small toke, and told Mike that was enough for me. We headed back into the living room for more conversation. Mike’s partner was having a drink, and I asked for a glass of water. We talked for what seemed like forever, my head muddled just enough from the 420 that I began to lose track of what we’re discussing. In the back of my mind, I kept wondering when the action would start. I also tried to gage just how excited Mike’s partner was about my presence. Was he into me? He was very nice, but his affect seemed very laidback and I was beginning to wonder if he was going to ask me to leave. Instead, he surprised me by saying, “Seems to me we’re all supposed to be fucking, so what do you say we get naked?” Mike, who had been sitting to my left on the couch, leaned over and planted a deep, wet kiss on my mouth as his hands roamed over the front of my jeans. Standing, I shucked off my t-shirt and dropped my jeans. Mike moved to his knees, taking my dick in his mouth. His partner, who had been sitting in an over-sized chair on the other side of their over-sized coffee table, materialized behind me, his crotch nesting in the crack of my ass. I turned my head and my lips found his, warm and receptive. The partner turned me around and guided my mouth down onto his dick. This left my ass exposed and Mike didn’t hesitate a moment. He was up inside me in an instant. Fortunately I came pre-lubed, and with the 420 working its way into my system, I was relaxed enough to take it without recoiling in pain.

This went on for awhile, until one of them suggested we move to the bedroom. My pants were still around my ankles, so I stopped to remove them and my socks before following Mike into the bedroom. Once inside, it was full tilt boogie time. They both fucked me, repeatedly and I fucked Mike twice before losing my load deep inside him. The partner fucked Mike a few times, too, but decided it was my ass he wanted to breed. Mike came twice before the night was over; once in me and once on my face. They took breaks throughout all this, running off to the bathroom. They also paused occasionally to adjust the airflow from an open window. At least that’s what I was hoping they were doing. The paranoid part of me was terrified that they were filming this, or that they had a live webcam going, or that someone in an adjacent building was watching us through the window. Ah, that would be the 420 talking.

The only other odd thing at play was the sexual banter going on between the two of them. Mike’s voice got a little higher immediately after doing poppers and he kept calling his partner by a certain term of endearment that under normal circumstances would have probably escaped my notice. However, there’s something in the pitch of Mike’s voice and his rate of delivery that caused my paranoia to kick into overdrive. It reminded me of something you would hear in the movie “People Under the Stairs”. Thankfully, there were only two brief episodes of this type of banter between them and in the end I just wrote it off as something they get off on. They do… I did not.

In any event, we ended up as one sweaty, cum-stained, seething heap of man flesh. Everyone was totally satiated and coming down from their popper/420/orgasm highs. We made our way to the bathroom where we all showered and made small talk. I got dressed and left, thanking my hosts profusely. I had a wonderful time.

Once on the street, I got my bearings and attempted to retrace the route the cab took. I succeed up to a point. Then? I was lost. Maybe. I kept calming my inner-self down, aware of the late hour and the fact that there were tons of dark corners yet to pass. I changed routes several times, certain that I had lost my bearings. In the end, I ended up going out of my way four blocks south and two east of my hotel.

Let me tell you about the streets of San Francisco! At two in the morning? It’s like a zombie video game. Hookers appeared out of alleyways and floated toward me. On every street corner there was some hooded, cloaked figure whispering, “’sup, dude?” Everyone looked like they were on heroin or crack. It was a world of shadows. I was never so grateful to be back in my hotel. That’s the night I first noticed the tranny hookers outside my hotel window. I watched them in action until I drifted off to sleep.

Based on my experience the previous night, I vowed to be a good boy the next day. That lasted until after dinner. About 10:30 pm, I was back on-line and in short order started a conversation with a very to-the-point black man 12 years my junior. His picture seemed nice, I liked his stats, and I wasn’t getting a weird vibe from him, but then his conversation was so terse I had no idea what to expect once he showed up on my doorstep. They locked the hotel doors at midnight, so I had to go down to the lobby to let him in. Standing out on the front steps was a very pleasant looking black man. There was a softness to his face that I had not expected and his smile totally won me over.

We ended up having a very easy evening together. He’s an excellent kisser and extremely passionate. I was unable to place his accent; vaguely British, colonial. Our conversation flowed as easily as our bodies did into one another’s. No poppers needed this evening. His cock felt like liquid as I slid up and down it; my hole receptive and relaxed. There was no anger in this fuck, but rather something sweet and kind. When, at last, we both came, we melted into one another like deserving schoolboys. This one lingered and as he dressed to go there was a part of me that wished he would stay longer.

I spent the next day on Alcatraz; then drinks, then dinner. It was my last night in town, but I was too tired to haul my ass over to the Castro, and, quite frankly, given my experience walking home the other night, was a little leery of leaving my hotel room. I got on-line and was hit on almost immediately by a short Puerto Rican, who was eager and at least ten years younger than me. His profile featured a pic of his dick, and at 8.5” it held a lot of promise.

He arrived after midnight, so I had to go down and let him in. Right away I realized I’d probably made a mistake. His body reeked of cigarette smoke and his breath, of beer. As we rode up in elevator I noticed, in the harsh light, the bags under his eyes and while I felt a bit sorry for him, I also began thinking of ways of getting out of this situation. Once on my floor, should I just get out of the elevator, push him back, and say, “No.”? No, I couldn’t do that. Wordlessly he followed me to my room.

Once there, we undressed and he sat on the end of my bed. His dick was already hard and while it looked inviting, it was the only part of him that held any appeal for me. So I concentrated on it. Ten minutes later, he slid his back up against the headboard and beckoned me on board. Grabbing the poppers that he had, thankfully, brought, and some lube, I worked my hole down the length of his pole until I was seated firmly on his pelvis. I decided to get this dude off as fast as possible before the stench of his nicotine soaked body penetrated my pillows. Shifting my legs, I moved my feet so that they were flat on either side of his body. Then I began to pile-drive my ass up and down his cock squeezing my sphincter for all it was worth. It paid off. In a matter of minutes the dude shot his load and came gallons. After that, I was civil, but made no effort to engage him further or give him reason to believe that his presence was required any longer. He cleaned up and dressed. He seemed sweet enough, in a sad way, and while there was a part of me that wanted to rescue him, there was also that part of me that wanted to go to bed as soon as possible.

It was not a great ending to my otherwise excellent adventure, but hey, five out of six? Not bad. My memories of San Francisco are a bit tainted, but then, considering the condition of the city, what else could I have expected? I’m glad I went, but not sure if I will ever return. The entire time I was there everyone kept commenting on how they could not believe I’d come there that weekend when the next weekend was Castro Days (or something like that), when gay people run naked and leather clad through the streets.

Now that? That might well be worth returning for.

Next Up: My Weekend in Duluth, MN