A Painfully Exhilarating First

I had a feeling from my first time being penetrated that, if the limits of my body were tested, truly tested with almost unmitigated resolve, I wouldn’t tap out. But, I had no clue that, at the still somewhat inexperienced age of 26, those limits wouldn’t just be tested, they would be stretched and worked over by a few guys who had synergy in bed like the '98 Yankees had on the diamond (I had to look that stat up. I’m clueless about baseball).

I accepted an offer to take part in a four-way. That’s three tops and me. Now, that’s nothing too over the top until I mention that we all met at a club in NYC called Splash, which ramps up the expectation that, by night’s end, there’s gonna be a little fornicating, that the three tops, Clyde, Del, and Berto (nicknamed Bags) all had ethnic backgrounds of the darker-skinned persuasion, and that at some point that night, the three of them all got turns cramming me full of two cocks at a time. And in the size department, the three of them all concealed massive members, all with special characteristics. The experience began on the dance floor. It was summer, the kind of night where, if you stepped out of the club, you went from the air-conditioned inside to a face full of humid, dank air outside.

I loved to dance in my 20s. Aside from how much I enjoyed it, it always caused a stir amongst onlookers interested to see what was hiding beneath my tight jeans as I switched my hips to make my ass pop up and down to simulate how it looks when I’m riding a guy’s lap hog. As I bobbed and slid, raising my arms above my head and closed my eyes, I felt a set of hands touch my forearms and slowly travel down my sides, ending at my hips. My eyes opened immediately and I looked to my friend for guidance. The look he gave me said I should acknowledge this brash interloper. Arms still raised, I turned to find Clyde, a tall, black man in his early 30s.

After we spoke for a bit, he invited me to the bar to hang and chat with him and his buddies. He introduced me to them, “Alan, these are my friends Del and Berto, but we call him Bags.”

Del and Berto were black and of some Hispanic descent, respectively. I was immediately intimidated. Handshakes all around. Clyde’s wrapped entirely around mine. I had and still have no idea what that indicated, but it still turned me on.

Things seemed to be going fine as we all sat and, after some preliminary questions came my way and were easily fielded, the three friends chatted for the next hour and I listened as I attempted to understand how these three came to become men of importance via separate paths. I don’t normally watch the guy that hit on me chat with friends while I sit, but their lives were really interesting. The conversation between them was anything but dull, so I learned a lot in that hour, enough to feel confident that Clyde was a stand-up guy and that I wasn’t going to be accosted and left on a tiled, subway floor.

Eventually, I began to get antsy. I decided to send a signal. My gaze fell on Clyde. 100% of my attention, my body language, my eyes, my desires were completely and utterly locked on his face until he broke free from his friendly chat and looked back at me. As soon as his eyes met mine, as soon as I knew he would see the signal, I sent it. My eyes, which were laser focused on Clyde’s face, shifted their attention to the part of his body where his cock resides, just for an instant, then immediately back up to his face.

He saw it. I knew he saw it because he gave his two friends, Del and Bags, a look of some sort of confirmation, like he was saying, “This is the guy,” without uttering a word. All three of their moods went from ‘comfortable conversation between old friends’ to ‘we play as a team’.

The answer to that question came very quickly. Clyde came close, leaned down and whispered in my ear, “Yo, my friends and I are looking for a fourth.” A fourth, I thought to myself. Never heard of that. That sentence usually goes ‘my friend and I are looking for a third’. “We like finding guys like you to see if you’d be into hanging out at our place.”

“Where is your place? And what would I be doing during our time together?”

“It’s three buildings down on the same street and you wouldn't be doing anything or anyone. That’s because you’d be the bottom. By how you were dancing, it wasn’t hard to tell that you are really subservient,” Clyde responded instantly. I got a raging hard on and started feeling slightly dizzy. I want this!! I’ve wanted this since the first time I stuck a finger up my ass, but I wasn’t sure I’d be able to handle this. I wasn’t sure if I was scared or excited. Those two tend to get mixed up often. These uncertainties mixed with that feeling of being on my own (by this time, my ride had already left with a trophy of his own), fending for myself, made me shiver uncontrollably.

I looked at the three of them. Del proclaimed, “We think you’re hot. Are you considering it or just stupefied that we just asked to gang up on you?”

“Don’t get me wrong! You guys just made me quake when Clyde said ‘the bottom’. So don’t think for a second I don’t want this. It’s just that far from home base feeling…”

Clyde cut me off in order to set my mind at ease. In a plain speak, matter-of-fact tone he said, “Alan, we live three buildings away. Well, they live three buildings away. I’m just visiting their little city here. How about we walk you to the apartment, you can come in and relax and NOT let us fuck you, OR……” A long pause ensued, but he was not done speaking, so I waited a few seconds, “You allow us to fuck your brains out like that Russian twink back in Queens, HAHAH!!” This was clearly a throwback comment about a prior conquest because they all smiled wide. Then they all high-fived each other (UGH! I hate high-fives) while passing familiar phrases back and forth, and finally, in unison, returning attention to me. “What I’m saying is, it’s up to you, but times wasting and we wanna fuck.” He tapped his watch several times to punctuate his last remark about the time. Then they all waited for a very brief moment.

“Alright, let’s get the fuck outta here!” As their eyes lit up at my affirmation, I downed the last of my drink and we made our way to the street, Clyde in front, Del and Bags behind. Foreshadowing.

So within three minutes of exiting Splash, we arrive at Del and Bags’ building. Three fucking minutes!! And that was walking slowly. I thought, how lucky these guys are to live near such a place as Splash. I suppose that makes this Option #3: Clyde throws a curveball and introduces me to his friends who intend and execute the wildest evening of my young life only a few steps down the road from Splash.

Their apartment resided on the fourth and top floor of the building. It was a massive studio with a vaulted ceiling, making this an older building, decorated with mood lighting via sconces that jutted from the light brown walls every 6 feet or so, a large, single chandelier that hung in the center of this room providing the rest of the light, while also casting an array of shadows outward from my feet. There were framed images of long dead despots. This was an odd thing to see. Attila the Hun painted onto canvas in expressionist style, Vlad the Impaler also in expressionist, and two or three others were in clear view from the bed’s perspective. These images only served to make the situation even more intimidating. I was very curious about the idea to place these paintings on these walls. There was so much detail about this place that would have made for exquisitely deep and topical conversation, but I’m shallow as fuck!

We sat in the living area on an L-shaped couch. There was reassurance concerning my safety when Bags asked me, “So is there any act you would rather not partake in? We are open to and have tried a lot of stuff before, but maybe you might be turned off by something. You tell us and we will avoid with all restraint.”

What a great last word for me to segue, “Restraint! Well I’m not against that.” They chuckled. “I do have a thing about intimacy, though. Kissing, caressing, spooning me to sleep and shit like that is nice if you’re into that sort of thing, but I’m shallow about how I want to be treated. The primal acts involved in being a submissive like me are the acts I enjoy. Rough treatment, verbal tops, tying me down and teasing me with your cocks, making me wait until I’m practically enraged, before finally and swiftly going deep inside.” Del and Bags began rubbing their hands against their thighs, both traveling well past the halfway point of the thigh, then back up toward the waist. Very intimidating to be so young in experience surrounded by three men who seem to be very well in tuned with each other’s bedroom manner.

“Nice. What else?” Bags urged.

“Well what about you guys? What do you want from your conquests? How would you like me to treat you?” This question got the three of them very stimulated. Del actually slid his wide shouldered frame from his back on the couch to the edge of the couch leaning forward, hands clasped, when I turned the tables like this.”

They interrupted each other, not knowing who should retort, laughed uncomfortably (I just smiled knowing it would be the only time tonight where I would have the upper hand), then Clyde took the reins, “Intimacy isn’t something we do in these gatherings. It’s us three……and you.” He paused a lot when speaking and the pause was always followed by something I wanted to hear. This was no different. “Like I said at the club, we want to fuck. We want the experience to be controlled by us. The guy we invite over is going to be treated with respect before the encounter and after…” Oh goody, another pause, “but during, you should know we are going to make you work. You gotta be able to take dick.” Oh God, they’re big. I got confirmation!! “We ain’t small, none of the three of us are. You need to be ready for that. We go for a while, too, and you gotta be ready for that, as well. After that, what we do will ultimately be decided by your reaction to our behaviors. We are good at this, but if you see something you don’t like and your face doesn’t register a negative reaction to it, we are going to continue. So react with honesty. If you want, at any point, we got food and drink in the fridge you can help yourself to. Actually, you might want to have a water or something on tap so you can stay hydrated throughout. Oh, and you should decide on a safe word. One syllable, short. A word you can say with a cock in your mouth if need be.” I chuckled this time.

I don’t know why I chose this, but it came out almost immediately, “Bank!” A ‘b’ sound is easily made with a cock in my mouth and the ‘k’ at the end can be executed by simply rolling the tongue along the base of the shaft and separating them as I exhale.

Clyde gave me a calculated look and joked, “You’ve done something similar to this before, haven’t you?” He, Del, and Bags laughed a little.

But I responded, “Several times, yeah,” without so much as a blink. I probably could have done without this lie. It was only my third time and it was with guys who, I predicted, wouldn’t be able to perform to the level these guys would.

Their smiles receded from their faces and, at once, the trio rose and walked toward me until my face was flanked by their pants zippers. Clyde demanded, “Unzip my pants and take out my cock.” I dared not refuse.

I could see through his loose fitting slacks made of some very light material, probably linen, that he was semi hard already. My hands did as I was told to and once unzipped, I decided not to unbutton, but rather, to pull his tool through the opening where the zipper was. The instructions were followed to a T. Unzip pants, take out cock. So that’s what I did. His rigid member sprang out of his zipper opening like a jack-in-the-box. I felt my eyelids widen as I took a look at this beautiful specimen as my hands hitchhiked from the base to the head and then aback to the base. The smell rising from it was intoxicatingly pungent. I wanted to inhale through my nose the rest of the night. I began sucking his cock getting it half way into my mouth before my gag reflex kicked in.

The natural way of the top is to push the mouth’s limits, so Clyde did just that, using both of his hands to push on the back of my head, not assaulting my mouth so much as training it. His cock was very, very thick and a great length, about ten inches, but like I said, very thick, as well. I was able to relax my throat enough to bury it inside my mouth until my nose was pressed right against his smooth shaven stomach. It was the first cock I ever took in my mouth that stopped me from breathing. It was the first I ever took down my throat, too. I'm not good orally and taking cock far to the back of my mouth has proven to initiate the gag reflex very easily. The only explanation I could come up with for throating Clyde (and eventually Bags and Del) was that I was drunk. Very drunk. As this was happening, my hands released Clyde’s fuck stick and changed their duties, each one charged with stroking Del and Bags’ cocks. Several minutes of my tongue saturating the entirety of Clyde’s fire pole passed and things shifted and I was now facing Berto.

Berto was uncut, not record-breaking girth, but very long and smooth. My favorite thing to do to a cock with a foreskin wrapped tightly around the head is to grab it halfway down the shaft and slowly peel back the skin, revealing the bulbous crown, which I love tasting! Berto’s cock head tasted so wonderful and gave off a flavor of a man who had recently showered (thank God, since an uncut cock can get pretty ripe if unchecked). But the aroma got me so hot, one of my hands left Del’s cock and began rubbing my own over my jeans, which was ill received.

Del cut in with a rebuke aimed at me, “Get your hand back on my dick, bitch!” He reset my priorities pretty fast. “Our pleasure is all you need to concern yourself with. Yours will come soon, but when WE say. Now, squeeze my cock and stand up. But keep your hands and mouth around our cocks, you greedy little ho!” I liked his tone and the choice of words. They combined to make him sound confident and concerned about his friends receiving pleasure from this experience while also reminding me that, though there were 4 in attendance, I was the only one with the holes, so I had to do my best to mind all three at once as often as I could.

One leg at a time, I stood, still bent over, but now with Del’s smooth, fat, cut cock readjusting my jaw. Del was thick. His cock went into my mouth semi hard, so my mouth was able to handle the girth at the start, but as I took him in deeper, he grew longer. It wasn’t his length that gave me trouble, though. His cock length was ample, but the width had me trying to fit his shaft in my mouth without my teeth interrupting. While still pumping furiously at Clyde and Bags’ mounds of cock flesh, I was slowly inching Del between my teeth little by little, tonguing the base as it crept in. I eventually got him buried in my mouth with the head of his beautiful cock pressed against the back of the roof of my mouth. At that point, my jaw hurt so much, I carefully, but expeditiously, recoiled. Seeing this, Del said, “No, no, no. Stop.” He was still half inside my mouth when I froze, waiting for a command. No command came. Instead, both of his hands calmly traveled to the back of my head and he pressed my face into his crotch like he didn’t care about my teeth scathing his veined shaft. Once my face was being smothered against the area just below his belly button, he started pumping my face rapidly and with every thrust of my face into his tummy, I was unable to breathe. My gag reflex surfaced a few times during his forceful entry, but it didn’t cause any…regurgitative response.

“Oh, this is good, boys! So fucking good!” Del received affirmations from his two buds as he used his positioning and power to repeat this unmitigated act on my mouth. Once he finally allowed me to catch my breath, his cock came out of my mouth, stiff and fat as a redwood tree, followed closely by my saliva, which collected during Del’s savage skull fucking. Can’t waste saliva. I caught it and rubbed my hands together, returning them to their rightful places. Once I caught my breath, Clyde grabbed my hair, which, at the time, was long enough to grab, and did the same as Del, but only half his cock entered, so my breathing wasn’t affected, but when he finally relented, my salivary glands worked overtime to produce a glob of spit. This time, my eyes, which flooded tears down my cheeks and dripped off my chin, looked up at Clyde’s and I spat the entire wad onto his cock, making it slick and preparing it for my ass.

“You’re a good little bitch. Your little butthole is gonna open wide for us tonight! Now bend the fuck over, you fucking hand puppet!” He called me a hand puppet. This is ironic since I’ve tried and failed a dozen times at fisting, but it remains on my bucket list to this day. He pushed me and my hands instinctively left the grasp they had on Del and Berto so they could stop me from falling head first onto the carpeted floor. I lay on my back, the three of them stroking and looking down at me as a pack of tigers would look at a herd of gazelles. “Take off his shit,” Clyde said.

Within 30 seconds, my clothes were off, all but a jock I was wearing (no undies), covering my cock and balls, which I exposed myself by pulling on the fabric of my jock strap until my cock and testicles, dwarfed by Clyde, who was clearly the overwhelming winner in the cock length AND width categories, ventured into the open, though I had no desire to use it. “Man that looks so good,” Bags commented, after my clothes had been yanked away from my body. He commanded, “Get on all fours. Stick that fuck hole way up high so we can all see it.” I did as he said. The position I was in gave all three a clear view of my sweet pucker. They saw my ass framed by the black, cloth straps of my jock along with my semi-hard shaft and sack hanging just beneath, only about two weeks of hair grown in, and all commented on it.

From the looks they gave my body, I assumed they were enjoying the view, my ass in particular. Bags fell to his knees and buried his face between my ass cheeks like it was a race to see who could get there first. He spat on it, then his tongue pistoned out from his mouth and entered my sleeve. Clyde and Del both got to their knees on each side of Bags to inspect my hole with their fingers, that is, when Bags was able to back his face away. I rested my head on the carpet and reached both hands back to grip onto Clyde and Del’s beautiful cocks. Then, all three took turns tongue fucking my ass while the other two would pull my cheeks apart and finger me. The cocks in my hand were hard as cobalt. Unforgivingly erect and solid. I was going wild, begging for more as they began hooking their fingers into my hole and pulling it apart to stretch me wider and wider. Then the fingers would release so one of them could tongue it.

Suddenly, and with no warning, I came. With Bags scruffy face pushing against my tender ass flesh, his short stubby whiskers scratching at my soaking wet hole, and all those fingers probing me deep, I felt my body shiver and all in attendance witnessed the first of several orgasms I would have that night, all of them occurring involuntarily. Amazing!

“Damn! He nutted,” Bags reported with vigor. “This little ho is ready for the dick! Clyde, you hunted him down, you get to loosen him up. You hear that, ho? That big dick that plugged your throat up is gonna stretch you out!” Bags backed away, so Clyde could position himself behind me. His body seemed so far from my flesh, yet as his hand maneuvered his cock about, I felt the head travel up and down my wet crack. It made me nervous. It was a long way for his body to go before he would be balls deep inside me. I reasoned to myself that if my mouth could handle the length, my ass can, too.

Now, the three of them worked over my hole pretty good with their tongues and fingers, so I was confident I would be able to take some of Clyde at first, then all of him eventually. But I recalled he was also quite thick, and it was his girth that was so challenging. He looked at me as I shifted my head around to meet his look, a look of sternness, but concern, too. “Are you ready?” I just nodded and started breathing long, rhythmic breaths as he pressed his manhood hard into my slick opening.

He let his weight do the work, oscillating his hips back and forth slowly, allowing the head to inch further in past my untested o-ring. “Tight,” he commented, smacking my ass hard like he was scolding it for not allowing him easier access. My body jolted when his hand connected with my right cheek. He seemed to enjoy my reaction because as he continued to use the tip of his member to pry me apart, he began repeatedly smacking my ass hard enough to make audible ‘clap’ noises while talking dirty to me. As he did this, his pals brought their cocks to my face and made me suck them both as I waited to feel Clyde’s massive head breach my tight fuck hole.

It took several minutes. He was pressing very hard because I could feel that his cock was bent in half from the pressure of not yet pushing past my initial defense. Then, I felt the head suddenly pop inside me, Clyde’s cock wobbling back to its unbent state. I sighed the kind of satisfied sigh when you are getting exactly what you wanted, as a cock continued assaulting my mouth with another clubbing me in the face. It was demeaning. I liked that. Within a few minutes of my pucker parting ways for Clyde’s entry, he was about halfway in and began backing out with more speed. Once my hole looked as if it might release the head, Clyde reinserted his fat cock back in half way. This pattern repeated itself, with only the speed changing, becoming faster and faster until he was able to maneuver in and out of my ass more easily.

Then, a point came when I felt his cock push to the halfway point, but not pull back. He intended to push the rest of his 10-inch monster in my ass. I already felt so stretched. If he got his way, I’m not sure how I would possibly be able to walk afterward. And that’s not even considering Del and Bags, both of whom sported some real nice sized lap hogs of their own. And eventually, as he inched toward his goal of the skin of his waist meeting the skin of my ass, I turned to find him holding a bottle of lube. A big bottle. He proceeded to squirt a long stream of the slippery stuff right at the point that my ass was swallowing his cock. As soon as the stream splashed the area, he thrust hard.

A wave of pain hit me with enough power to make me whimper. “Bitch, shut the fuck up! Why do you think you’re here?! You wanted to serve. So serve! Suck my friends’ dicks! You need something in your mouth!” He did the same thing again. I felt him recreating the shape of my anal cavity. Literally. Each time the lube hit its mark and he thrust, I could feel each and every imperfection on his cock either from how tight I was or how swollen his cock became as he continued to slowly engorge as he fucked me, my anal cavity squeezing against his rigid missile. He finally reached his goal and that’s when he really began to fuck me. Long strokes! He would trap the blood in his shaft, squeezing at the base, to swell his cock up, making it solid as a roll of quarters and as thick as a billy club, then all at once, skewer me with the entire length.

With his cock completely submerged in my lube-coated ass, I felt him start to remove himself, then stab it back in me to the balls, which slapped against the back of my jock and I would occasionally catch with my hand. He had a beautiful set of testicles. Like an ankle sock with two golf balls weighing it down. They repeatedly swung upward in sync with Clyde’s unmerciful pounding. He roughed me up for a while, making me shoot a load onto the floor twice, as I tongued, sucked, and jerked Del and Bags.

When he finally removed his cock from my ass with a popping sound, he told his buds to come check out what he did to me. I was gaping very wide and Del and Bags were impressed. I could tell they were considering their next move, the move that would be the highlight of the evening, a highlight repeated several times, but for brevity’s sake, I’ll only describe once. My first ever experience where two guys put their dicks in me at the same time was done by Del and Bags.

“Alright ho, get up!” Clyde’s command was a welcome one since I wasn’t sure how much more I would be able to withstand. I slowly stood, legs shaking like jello in an earthquake. The orgasms I had while Clyde all but forced his cock all the way inside me were glorious, but once completed, left me feeling spent. Even after these orgasms, I was so hot for more than just tapping my cock a few times would have, once again, elicited ropes of man juice to be fired from my bulbous crown.

Bags lay on his back, his cock stoically pointed directly at the ceiling. He told me to lower my ass onto his cock while I was facing him, so I did as he told me to. He wanted me to ride him, I thought, but what started out as a simple cowboy position changed dramatically when Bags looked at Del and said, “It’s time to finish what Clyde started. Climb on, bro.” Del positioned himself behind me with the intent of fitting both his AND Bags' cocks in at once. Combined, if I were to guesstimate, I’d say their thicknesses added together would be about the same width as the base of a bowling pin. Not the pin at its thickest, but the flat bottom of a bowling pin, and that’s how much Del and Bags intended to test my pucker’s ability to take a beating without waving the white flag (AKA: saying the word “bank”).

I finally spoke up. “Guys, I’ve never done thi…” A hand covered my next words so fast, I wasn’t sure whose it was. It was Del’s. With the head of his engorged member pressed against my already impaled opening, he chided, “What the fuck did I tell you? Our pleasure is all you need to mind. We got you open. You’re going to like this. You gotta trust us. No choice at this point.” God damn, he was right. These two were definitely my betters in the strength department and I was sandwiched between them, locked in for the ride? And so, my body language changed. My back arched. I rested my elbows both on the floor to the right side of Bags’ head so I could look over my right shoulder at what Del was doing. I felt the head of his missile pushing very hard against my sleeve. I waited, knowing that at any point, my hole would eventually relent, allowing his cock to join Bags’ cock prying me wider than I’ve ever been stretched. Something had to give in order for it to happen. Either that or I would need an assist.

Suddenly, the assist came, Clyde provided it. “Y’all looking for this?” In his hand was the bottle of slick lube he used earlier. He shot a long stream at the point of impact and Del’s cock shot up my ass so fast, my eyes widened, I inhaled for what seemed like 2 minutes, and yelled, “HOLY SHIT!!! Fuck me!!” In earnest, it did hurt. The reason I was into it was because it didn’t hurt enough to drown out the fact that one of the guys was hitting my g-spot and I didn’t give two fucks who it was. At that point, I just wanted them to both fuck me like my well-being was not a priority, though all three were giving off vibes all night that my well-being was paramount. They both proceeded to pump my hole at a furious pace as I emitted several ropes of jizz onto Bags' stomach, who reacted with a celebratory, “Hell yeah, motherfucker! Yo Del, this ho just nutted all over me!!” I started laughing hysterically from his reaction. This is fun, I thought to myself. They pumped away at my fuckhole for 10 minutes when I suddenly became energized to the point that I started backing myself into both cocks as they pushed into me. That orgasm I just had did something to make me want more. It was like a second wind.

And so for the next 4-5 hours, we continued our romp. All three doubled up on my ass in every combination possible; Del and Bags, Bags and Clyde, Clyde and Del (the two thickest, it felt like you could look up my ass and see my tonsils). By the end, I may have endured their relentless pursuit, but I was also unable to walk. After all three shot their final loads inside my ass, pushing it as far inside me as they could, I attempted to rise and walk to the bathroom. My knees buckled. I felt like my hips were set further apart than usual. I recall thinking that this must be what a woman’s hips feel like after pushing out a newborn. Everything about me was unbalanced. I fell in a heap amongst Del, Bags, and Clyde and we all just lay there.

Clyde saw my condition. “Hey man, however much time you need, rest here. We can see you can’t really get around.”

“No, I guess I can’t. My friend you saw briefly at the club stayed in the city, too. I might be able to get a ride back with him, but I'm definitely taking you up on your offer. Thanks!”

I spent the next two days just hanging out with these three eloquent and interesting men. No sex. Just healing.

I remembered Clyde’s words, “The guy we invite over is going to be treated with respect before the encounter and after…” I suppose this was what he was talking about. I did suck their cocks several times as they requested during my stay. But they knew they had thoroughly worn my ass out, so they ceased fulfilling their carnal desires. My ride eventually arrived and even he ended up fucking Berto before we drove off. What a slut!!

Two days had past and we said our goodbyes. Nothing sentimental or mushy. The word “bank” was never spoken. I guess I felt safe.