Tristan and his Tired Fingers

New York City, Spring 2018

I like to joke that my brand is a Big, Dump Top. Generally speaking, I don’t get as much satisfaction from bottoming as real Bottoms do. On the other hand, I always enjoy topping, so I fill that role more often than not. Every now and then, however, I feel an itch to bottom. I need the satisfaction of being filled up, and when that happens I tend to seek out a challenge.

I actually first met Tristan when I was 18. He must’ve been in his early 30's, dark skinned, with long braids tied back. Slightly taller than my 6’1 but much broader thanks to hours in the gym. He was always easy to talk to and embodied polite Southern sensibilities. Tristan might have been the first man I bottomed for in New York, come to think of it, but from what I remember I wasn’t quite graceful.

Three years later, Tristan and I inevitably reconnected because New York is, in fact, the smallest city in the world. I was a little older, a little wiser by then, and the itch was back. Tristan was just the challenge I needed, and we fucked up a handful of times that spring until I could take his hung dick gracefully.

One night Tristan let me know an old friend of his was crashing at his place and the two were out dancing. He invited me to join them. I wasn’t in the mood to be out right then, but I tempted Tristan to invite me over after and we flirted back and forth about the possibility. Their night ran late, but I had been fixating on Tristan’s cock for so long by that point that I didn’t give a damn about the time. Finally, some time around 2 am or so I got the call to come over.

Tristan’s place was a short walk away and took me no time at all. He greeted me at the door, I could see from his heavy eyelids that Tristan was losing energy quickly, but I hoped to get him properly inspired.

Tristan told me his friend was staying in the spare room. The friend had gotten lucky that night, bringing home not one but two hot guys from the bar. I thought I could hear their muffled laughter from the room and felt a jolt to my cock imagining the scene playing out just past that door.

I strode right into Tristan’s dark room, tossed off my t-shirt and jogging shorts. I threw myself back on his bed and looked up at him expectantly. His lips curled up into a gentle grin that warmed his sleepy eyes as he noticed the blue jockstrap I wore for the occasion.

I ogled him as he carefully took off his own shirt, revealing taut muscles underneath. Biceps to envy in comparison to my slender frame. Noticeable abs coated in gentle swirls of hair. Slowly he peeled his pants off, revealing silky tiger striped briefs encasing thick, solid thighs. I smirked at him, daring him to get a move on.

He got the message and landed on top of me, just enough so I could enjoy his weight. His lips enveloped mine as our tongues fought one another, releasing our pent up anticipation. I rolled Tristan over and positioned myself on top of him, just the right angle to grind my bare ass on his silky briefs and rapidly expanding 10” cock.

I remembered that just on the other side of his wall, there were three men going at it just out of reach. Large, warm hands slid down my body and palmed my ass, squeezing them a little recklessly as Tristan fought the alcohol and fatigue. I wondered about the arrangement of the lucky threesome. Were they going to flip fuck each other? Was there only one bottom? Might they need another?

That thought inspired me to slide down Tristan’s body, tracing my tongue from his ear, detouring across his Adam’s apple, and resting at his left nipple. I let my finger tips fall gently from his right nipple, down his side to the waist of his briefs. My hand skipped to his inner thigh, smoothly gliding across his sensitive skin to the pouch of his briefs. My mouth followed a similar path until I found myself face to face with his thickness.

I grabbed the band of his briefs with my teeth and pulled it up and away to free his straining dick. I fisted it with my right hand, marveling at how it’s weight filled my hand so differently than my own 7”. There was something about it’s solid mass that I could never get enough of. I lowered my mouth to his balls, licking them gently before sucking one and then the other into my mouth, catching the sound of Tristan’s appreciative groans above me.

I let my tongue flatten against the underside of his shaft and began the long ascent up his length and to the head. I glanced at his fat mushroom head before I started to swallow, not wanting to hesitate any longer. I’ve never claimed to be an expert cock sucker--eating ass has always been my forte--but for a piece like Tristan’s I pulled out all the tricks I could.

I swallowed as much of the length as possible before coming back up to gasp for air. I pooled spit in my mouth and let it coat Tristan’s cock skin as I descended on his pole again, getting his length slick. I wrapped my fingers around the base of his cock, firmly jerking his cock to meet my lips as I bobbed up and down. I hoped my hands could make up for not being able to deep throat his 10 inches like I wanted.

All the while Tristan was murmuring appreciatively until he leaned up and flipped me back onto the bed, pulling his briefs off completely in the process. He laid me down on my back and settled himself in between my legs.

I realized now that the door to his bedroom was left open and light filtered in to accentuate my pale skin against his. Tristan grinned up at me as he found his way to that spot where the jock straps meet. His strong tongue made contact with my skin and I gasped sharply. Tristan moved quickly to the ring of my hole, flattening his tongue against my opening and leaving a wet trail in its wake as I arched my back against his bed. He didn’t spend as much time eating me out as I would have liked, but with a body like that I could forgive him.

His hands replaced his lips at my hole, adding pressure as I felt our shared expectation building. He suddenly slipped a fat finger past my ring and I gasped in surprise. “Lube, lube!” I sputtered. He gave a soft laugh as he reached into a side drawer for a pump. His fingers, newly slick, began their entry again as my eyes fluttered closed and I sighed in pleasure. That first insertion is always my favorite part of bottoming. Appreciating that thick fullness entering me, shattering my brand as dumb top and turning me into a thirsty bottom.

Two of his fingers were plunged inside me up to the knuckle as his massive hand palmed my thigh. A small sound jolted me to attention and my eyes opened, landing quickly on a shadowy figure in the open doorway.

In the faint light and the heat of the moment I could only see a man’s outline. Casually leaning against the door jamb, with arms crossed comfortably, it looked as if he had been admiring the view. Face in shadows, his deep voice broke the silence. “Well well…” he exhaled and I imagined a smirk on his hidden lips. “I came to borrow some lube, but you both look like you need it more.”

Tristan laughed, leaning over me and not bothering to stop the thrust of his two fingers in and out of my hole. I was splayed back on the bed, my spread legs giving a perfect view of my asshole to this unexpected voyeur. My ring pulled Tristan’s fingers in as he boldly added a third for the stranger’s enjoyment, causing a groan to escape my lips.

“In the drawer, there’s a second bottle,” Tristan shares as he nods to the side drawer. The stranger stoops to pull out the bottle, pausing for a second in the doorway for a lingering glance. If only it had been light enough to see his eyes, to see if he could read the longing in mine, daring him to join Tristan in between my legs. He turned away, and I could hear the door to the spare room clicking closed. My heart sank, desperately wishing the door had stayed open, so I could hear the sounds of three men’s pleasure. So that they might catch a glimpse of something much thicker than Tristan’s fingers driving into my ass. I shuddered at the thought of what five men could do to one another. My arousal went into overdrive.

Poor Tristan was slowing down, worn down by the long day, but that didn’t bother me. I raised up my body and led Tristan to lie down on his back. I climbed aboard, resting my ass cheeks against his warm cock. I grabbed a pump of lube and coated his dick, refocusing my attention on the sheer beauty of this cock that was about to fuck me.

As a bottom I love to ride to start. I like to focus on my own pleasure, after all. With my jockstrap still framing my ass, I raised myself up over Tristan’s member, and made contact with his mushroom head. The warmth was immediate and I wasted no time letting gravity lower me onto this man’s cock. I took the scenic ride down, appreciating the ridges and bouncing occasionally for good measure. About halfway down I needed to pause, pulling myself off Tristan again to add another pump of lube. Freshly slick, I returned Tristan’s cock to right where it belonged. This time, after the initial stretching, my ass was more accustomed to his width--now to deal with the length.

Bottoming out always comes as a surprise to me. A rock hard appendage in my ass makes each inch feel like a foot of length. Finally lowering myself all 10 inches down onto Tristan’s thighs, I felt proud, but also disappointed, as if wishing for just a few inches more.

This was clearly my party and Tristan was just along for the ride. There was a relaxed smile on his face as his eyes rested half closed, clearly appreciating the sensations of my ass gripping him. His gentle sighs were all the encouragement I needed as I rocked myself back and forth on his raw cock. My pelvis rose up and down, encouraging his length to batter my guts. My own poor cock was half hard but leaking precum every time his head knocked against my prostate.

I knew Tristan was more exhausted than he wanted to let on, but I needed a few more minutes of my own selfish pleasure. I drove my knees into his bed, locked against Tristan’s sides. I straightened up and arched my back, feeling his dick driving straight up into my body. I assumed one of my favorite positions as I stretched back and grabbed his ankles for support. My chest flared up to the ceiling with my head thrown back. Up and down, I rocked, building up the pressure inside my cock. Finally, I was ready and I shoved aside the fabric of my jockstrap to reach my own half hard dick, grabbing it roughly and squeezing my ass muscles tight to force myself to a strong erection. It didn’t take many strokes before the ring of my ass contracted tightly against the obtrusion still lodged deep inside of me. With a mass of Tristan’s size up my ass, my battered pelvic muscles sputtered out dribbles of cum as I moaned in pleasure.

Tristan gently pulled my chest down onto his body as I came back from the high of my orgasm. He traced down my back gently, cupping my ass as I took a deep breath and released his cock from inside of me so I could roll over to rest. He smiled at me in thanks before admitting he was more worn out than he expected, insisting that I didn’t have to worry about getting him off that night. I was torn--on the one hand I wanted his cum. Ideally I would have been walking home with it in my ass, but I wouldn’t have said no to swallowing it all down either. But on the other, my ride had worn me out and I knew my legs would be trembling as I rose to leave.

But leave I did, searching for my jogging shorts in the darkness, already regretting the jockstrap’s lack of coverage over my lube slicked ass. I kissed Tristan gently to say goodbye, not sure if he was still awake enough to even notice. I slipped quickly out of his room but paused in the half light of his hallway,

I eyed the closed door to that spare room again, wondering what acrobatics those three men were up to. My hole clenched, apparently Tristan’s 10 inches hadn’t managed to satisfy me after all. I was so tempted to step closer. To knock gently on that door. To offer up my ass again and again for these three strangers.

But I turned away, relying on unsteady legs as I walked proudly home.