Chris - Street Walking (Patreon)

In 2014, I lived on the Upper East Side in Manhattan and worked nearly 80 hours weekly, if not more, as a freelancer. I didn’t have much time for my friends and definitely didn’t have time for a relationship.

As a bisexual man, it was pretty easy for me to get my needs met, but I had to put in a little effort. At this point, I had gone almost two months without any sex and more than a week without jerking off. When I had a Saturday gig canceled, I realized I could go out on a Friday night, and I sent out a blast of texts to my closest friends so we could have some drinks and catch up.

Everyone I reached out to came out, and I went wild. I drank way too much, but I didn’t want the night to end. Unfortunately, it did end around 2 AM.

We were at a bar on 2nd Ave, just around 49th St. My apartment is on 74th St. between 1st Ave and York. So, instead of paying for a cab or, worse, taking the subway, I decided in my infinite drunken wisdom that I should “walk it off.”

As I walked, I increasingly found myself needing to take a piss. Instead of popping into one of the many open bars along the way, I had the genius idea to pee under the bridge at 59th St., which I did. While pissing and spreading my legs wide so the stream didn’t roll back onto my shoes, I felt something, I guess a flashback to the last time I spread my legs wide like that, and the images of a guy fucking me from behind flashed through my mind.

When I was done, I took my time shaking it and tucking it back into my briefs. Looking around, there was no one around, and the perv in me was feeling horny and getting a rush from being slightly exposed with my pants undone. Looking down the tunnel under the bridge, I noticed it was a long city block in length, and I wondered if I could make it to the other side, pants undone, without having to pull up my pants or get caught.

With each step, my pants slid a little further down, exposing my grey briefs a little more. Midway down the block, I was really challenging myself to not pull my pants up out of instinct.

About two-thirds of the way through the walking tunnel, I saw a man turn off the street walking toward me. A part of me was thinking I should pull up my pants which were now almost halfway down my thighs, but the drunk horny part of me wanted to see his reaction. As he got closer, he made no effort to look away, staring directly at my package, and I got a huge rush out of it. As he passed me, I checked him out, too, and he was hot. Shaggy dark hair, probably late twenties, thin but not too thin, slightly baggy clothes, a little taller than me, cute face with a five o’clock shadow, big round eyes that were partially closed, looking like he had been out drinking as much as I had. I turned to watch him as we passed by each other in an almost slow motion. We both assessed what was happening in our own way, walking backward as I continued. He turned, watching me watch him, and then started back toward me. I stopped walking to let him close the gap.

I grinned, “What’s up, man?”

“What’s up?” He didn’t hesitate, reaching out and cupping my package with his right hand, my cock instantly reacting to his touch, my balls tingling from the rubbing.

“I’m just horny,” I slurred, shrugging my shoulders and grinning like a fool.

He smiled back. “I can see that,” he said, looking back and forth down the tunnel. So what’s up?”

My heart was pounding, my dick now straining in my underwear as he continued to grope me through the thin fabric. “I…I don’t know,” I shrugged and grinned, trying hard not to seem like a desperate loser.

His other hand reached around to my ass, palming my left cheek, “You trying to get fucked?” I could smell the beer on his breath. His glassy eyes searching mine let me know he was just as far gone as I was at that moment, and he leaned in and kissed me. Not just a peck, but straight to deep tongue action, holding the back of my head with one hand and cupping my ass with the other, pulling my crotch into his as my pants slipped straight down to my ankles. The cool night air on my upper thighs came with such a rush of excitement. Just as quickly as the kiss began, he broke it off, pulling back from me gently. His left hand dragged from my ass around my hip, his fingers tracing the outline of my hard cock through my briefs and then cupping my balls before. His eyes burned a hole in mine, waiting for an answer to his question. I was putty in his hands.

I shrugged, “If you want.”

“Yeah, I want,” his hand left my crotch and grabbed his, adjusting his hard dick in his jeans. “You live near here?”

“I’m on 79th,” I said, “No, 74th,” I laughed at myself for being drunk and dumb.

He looked at me like he didn’t believe me, then pulled a spliff from his shirt pocket and lit it up. "That’s too far. I know a spot.” Then he started walking back in the direction he came from, giving me another look, up and down like a piece of meat, expecting me to follow him as he smoked.

I quickly pulled my pants up, not zipping them or buttoning them, just holding them up with my hands in my pockets, trailing behind him like a drunk five-and-a-half-foot-tall puppy.

We took an immediate right outside the tunnel, following the bridge and then crossing the street, past an old bar and a side street. A few people walked past us, two of them glancing at my obviously undone pants and chubbed-up bulge, but they kept walking without saying anything. My new friend occasionally glanced back to make sure I was still right behind him. I was too turned on and too drunk to be smart enough to disappear on him, and I just smiled bashfully every time he glanced back.

He kept smoking his spliff as we walked, his smoke blowing in my face as we kept heading along the bridge until we came to a chain-linked fence where a building had long been torn down and then the lot left undeveloped. He pulled at a section of the fence and slipped into it, holding it for me to slip in. As I did, my pants fell down when I held my arms out to squeeze through the narrow gap. I went to pull them up, and he just said, “Nah, keep them down,” biting his lower lip and cupping my ass with both his hands before kissing me again. Again, with a large wet tongue that tasted of weed and beer but felt so good, I just let him grope and grind on me.

He broke the kiss, grabbed my hand, pulling me deeper into the abandoned lot, my pants acting as ankle shackles that forced me to take twice as many small steps for every one of his strides.

Near the back corner of the lot, a poorly built, dilapidated wooden fence had a few boards missing, and he pulled me through the fence which put us in a dark alleyway behind the building on the next block. He kissed me, pushing me against the wooden fence. I felt the rough texture of the wood through the thin fabric of my briefs on my ass and the hardness of his cock through his jeans, grinding against my crotch. My hands started exploring his body, up the back of his shirt, his tight back muscles, his narrow waist, and his ass as he gently grinds his crotch into mine. I couldn’t help but let out a soft moan. He was hitting all of my erogenous zones. I didn't give a second thought to where this was happening because I needed it to happen. I moaned a little louder, wrapping my arms around his shoulders as he sucked a hickey into my neck.

“You have to be quiet,” he whispered, then nodded to an open window with the light on two floors just above us. I nodded in understanding. Then he dragged me a little further down the alley, away from the window where a few wooden pallets were haphazardly stacked at waist height, and he whispered, “Bend over,” nodding with his head to turn around and face the pallets, and like the horny guy I am…I listened. Putting my entire torso flat on the dirty and rough raw-milled wood as he leaned right into me, his pants already undone, so his bulging dick in his boxer briefs was grinding into my ass.

With my head swimming, I was so horny, and it had been a long time since I hooked up with a guy that wasn’t my fuck buddy. I couldn't help but squeeze my ass cheeks around his bulge, letting him know I needed it. The excitement of this guy I just met wanting to dick me down was pushing all the right buttons for me. I reached behind me and slipped my waistband over my ass, lowering my underwear enough to expose my hole to him. He wasted no time pulling down his underwear and spit on his cock, then my ass. “You have a condom?” I asked, feeling the head of his raw cock smearing saliva onto my hole.

He let out a chuckle, “Nuh-uh, do you?”

I started to stand up straight, “No.”

He pushed me gently back down, rubbing the head against my hole with a bit more pressure, “I’m clean, man, let me fuck you raw.”

I shook my head, “uh-uh, I don’t do that,” I told him, letting him continue to rub the head on my ass.

“You’ve never been fucked raw?” He asked, letting his shaft slide up my crack to tease my hole.

“Mmmm…I didn’t say that,” I looked back to see his lips curl up into a sexy smile as my ass arched to meet his teasing cock.

“Then let me fuck you raw. I won’t bust in you,” he pressed harder, his precum adding lube to my outer ring.

“Mmmm…You swear you don’t have anything?” I stretched my arms out and gripped the bare wood of the pallet.

“Of course,” he said, adding saliva to my hole and popping the head into my tight sphincter, knowing he had won this hole over without waiting for confirmation.

The sting shot into me, and I tried to reach back and slow his penetration, but his torso was leaning too far back from me, and his dick continued to push into me slowly. I remembered the warning to be quiet and just clenched my teeth as I held onto the wood with a death grip, feeling him slowly push all of his inches into my tight hole. “Fuck yeah,” he groaned almost inaudibly as his hips pressed against my ass, and his hands slid up my back and under my shirt.

“Mmmngh…just wait,” I whispered, flailing one of my hands behind me like a stop sign, needing to adjust to his girth before he continued.

He didn’t pull out but didn’t wait either, just holding himself in my hole and wiggling his hips to get himself some pleasure while waiting for me to adjust to his massive tool. Even that seemed only to last a moment before he started pulling out slowly, adding some spit to his shaft before pushing himself back in with a low groan, “shit that’s it, fuck yeah, dude,” he grumbled, the sound of his belt buckle clanking on the ground as he rocked his hips.

I pushed the front of my briefs below my balls and started stroking my half-hard dick, closing my eyes so I could focus on the feeling of this dude's thick dick stretching me out a little more with every thrust. “Fuck,” I groaned. I needed to spread my legs wider to be able to flex those muscles I use to blow my load when I jerk off standing up like this, “Ungh, hold on,” I grunted. Breaking his rhythm, he pushed balls deep and held my hips tight as I slipped my foot out of my shoe and my pants. Before I could put my leg back down, he grabbed my thigh and pushed it up onto the pallet, spreading my ass wide for his pleasure but putting me at an awkward angle to get myself off.

He started thrusting away, grunting and panting behind me. Adding the occasional “fuck that feels good” as he dug deep into me, trying to push himself to orgasm, while I struggled to jerk off without hitting my arm on the splintered wood of the pallet. I was enjoying the shit out of the cock thrusting hard into my hole with my leg up, stretching my hips apart so he pegged my prostate as I leaned over the stack and drunkenly balanced on one foot. I was determined to enjoy every bit of this experience and get my rocks off.

“Fuck, fuck, fuck,” he mumbled, thrusting into me and then holding himself tight, “oh - ungh…fuck,” he twitched inside me, finishing with a whole body shudder and a low groan before pulling out altogether. “Shit, my bad,” he said as he tucked his softening dick back into his boxer briefs and quickly pulled up his pants.

I turned around and leaned on the pallet, stroking my dick furiously, watching him watch me and then come up to gently squeeze my balls the way he did in the tunnel as he held his pants up with the other hand. It didn’t take much stroking before I felt myself getting close. I leaned forward off the pallets and breathed heavily, stifling a moan as his grip on my balls tightened, squeezing the cum from my balls straight out of my cock. I arched my hips forward in an unsuccessful attempt to keep the first wad of my load grin rocketing out and landing on my pants on the ground. Barely missing him with the first shot, he jumped to the side to avoid being hit by the next rope of cum. Three more shots trickled out of my cock, coating my pants and my fist as my balls twitched and my ass clenched down on the phantom cock that my mind was still enjoying in my ass, “shit,” I huffed, out of breath and resting back on the pallets with a loud squeak of the wood.

He just grinned at me with a stupid look on his face.

I smiled back, struggling to focus on him, “what?”

“That was hot,” he said, reaching out to cup my balls again.

I was too sensitive, and a shiver rippled through my body as I instinctively flinched and gently pushed his hand away, “ahh-ah,” I groaned, then flung the excess cum off my hand onto the ground. I just sat there bare assed on the stack of discarded wood, catching my breath and trying not to pass out from the euphoria.

“Do you need me to walk you to the train?” He asked, looking around.

I just shook my head no.

He cocked his head to the side as if to ask, “Are you sure,” but didn’t say it aloud.

I gave him a drunk smile, “I’m good, man, just gonna chill here for a minute and recover from that dick,” I chuckled a little too loud, making him look up at the open window, which now had the light off.

He adjusted his now soft cock in his pants, fastening the button, “alright, if you’re sure,” he smiled.

“I’m sure, thanks for that,” I said, playing with my now soft cock.

A cocky grin came across his face, “Anytime,” and then quickly ducked back through the opening in the fence.

I was too drunk to get his number, so there wouldn’t be a second round.

After a solid ten minutes of post-nut recovery, I slowly untangled my underwear, which had somehow twisted up into a rope around my legs. Tucking my spent cock away and pulling my briefs up over my ass…I shook my head, my clothes were covered in cum. I wasn’t mad, just grossed out by the idea of having to get all the way home with jism all over me…and in me.

I wanted to get home and get to bed, so I ran the entire way back to my apartment. It was probably the dumbest thing I did tonight because my asthma kicked in around five blocks in, and by the time I was in my apartment, I was coughing like a first-time pot smoker as the phlegm filled my burning lungs. I took a hit off my inhaler, then drank a cold glass of water. As my breath caught up, I stripped down and face-planted in my bed.

When I woke up, hungover as hell, I took a shower feeling the dried cum in my ass crack regain its slimy consistency before soaping it off and telling myself, “It doesn’t count. I was drunk.” The rest of the day, I stayed in bed watching reruns of Star Trek: TNG in my clean underwear, nursing my hangover.