After Closing (M/M) - A one-off story about a bondage bet

[CaptiveDan]

The whack of the pool stick hitting the cue ball echoed through the nearly empty bar. Followed immediately by a softer echo as the cue hit the 8 ball, knocking it into the wrong pocket.

“Shit” I said, “almost had that one.”

I unbuckled my belt and took off my jeans, throwing them onto the pile of clothes I’d taken off after each lost game. I was now only in my underwear - possibly one round away from losing.

“You’re not very good at this,” Henry said. He smiled and handed me the glass of beer we were sharing. He was shirtless, but otherwise fully clothed; of all of our games, Henry had only lost one, and I was starting to suspect he might have thrown that one.

I took a drink and helped him reset the table.

It was half an hour past closing. We’d turned the front lights out and locked the front door. We were in a part of the bar that couldn’t be seen from the road. Our manager had scheduled him to close, but I had decided to stay with him past my shift so we could try something we’d wanted to do for a long time. We had the bar all to ourselves, no one to interrupt our game of strip pool.

Henry took the break shot, and sank a solid. A few turns later he had two balls left and I’d only sunk one. Unless I managed to pull a miracle, it was pretty clear I was about to lose our bet. My dick was already getting hard at the thought, bulging in my high cut, colorful briefs. It didn’t help that Henry’s bare chest and toned arms were distracting me. I missed the ball I was aiming for and sank the cue into the back pocket.

“Are you sure you’re not trying to lose, Derek?” Henry asked, as I put my hand over my face and shook my head. He took the cue stick from me and gave me a gentle whack on the ass with it.

A few turns later, I’d managed to sink one more by the time Henry was shooting the 8 ball. He pointed towards the pocket in the middle right side. Not the one I would have picked. It looked like a tricky shot to land. Either Henry was planning to lose this one to keep the game going a little longer, or he was much better at pool than I thought.

‘WHACK’ The stick hit the cue ball. The cue ball bounced against the back rail, then hit the 8 ball. The 8 ball rolled slowly and then fell directly in the pocket Henry had called.

“Fucking show off” I said, pulling my briefs down. As I bent down to pick them up and toss them on the pile of clothes, Henry hit my now bare ass with the pool stick.

I let out a welp and stumbled forward.

“Fucking pussy,” Henry said, stepping over to me and grabbing my wrists, “You better toughen up quick, I’m going to do a lot worse than that.”

With his strong wrists holding mine, he pushed me up against the wall. He kissed me and pulled my wrists up so they were above my head. We made out for a few minutes, with me pinned against the wall. When he pulled back, he bit my bottom lip and pulled it just enough to hurt a little before he let go of me and stepped away.

I was already breathing heavy, hard as a rock, standing there naked, exposed, and ready for whatever Henry had planned.

Before we started our strip pool game, we’d gone ahead and set out all the rope and leather odds and ends the winner could use on the loser. Henry switched the music playing over the bar speakers from the mellow, slow classic rock to a playlist that better fit the mood. He grabbed a coil of rope.

Henry grabbed my wrists again, this time pulling them in front of me and holding them together. I held them there as he let go and began wrapping coils around my wrists. A few loops around my wrists, then one loop between them was all it took. I was helpless. With the excess rope he yanked my tied hands up above my head. He walked around behind me, pulling the rope lead down so my tied hands were behind my head.

Henry stood behind me, holding the rope tight so I couldn’t pull away from him. He pressed up against me, his bare chest against my back. I could feel his hard dick through his jeans, a single layer of denim being the only thing between his hard cock and my ass.

With his free hand he reached around and felt up my chest. He kissed my neck as he played with my nipples. Then, without warning, he bit the side of my neck and pinched my nipple. I instinctively winced and tried to pull away, but between the ropes and his strong hold on me I was trapped. He could do whatever the fuck he wanted to me.

For a few wonderful minutes he alternated between gently caressing and kissing me and hurting me. The moments of erotic teasing broken up every time he’d slap my ass, squeeze my balls, or gently choke me. Eventually his hand slid down my chest towards my dick. He wrapped his hand around my cock.

“Oh fuck.” I arched my back, only for him to let go of my cock and release the excess rope he held in his other hand.

I brought my tied hands back in front of me. Henry walked away and came back with more rope and a leather collar. He fastened the collar around my neck - not too tight to hurt, but tight enough there was no way I could ignore it. He grabbed the ring on the front of the collar and led me to the floor. I sat on the floor, my back against the wall he’d pinned me too earlier.

Henry brought my legs together and tied my ankles with another double column tie. He pushed my legs so they were bent in front of me, brought my bound wrists past my bent knees and tied them to my ankles, so my arms were on either side of my legs.

I struggled in the bonds for a minute as he stood up and walked away. The ropes were tight, and the position was hot, but I was pretty sure I could maneuver my arms and legs in a way to break free if the scene got too intense and I wanted out.

I should have known Henry wasn’t done. I should have known he was going to make sure breaking free wasn’t an option.

He returned with a pool stick,a blindfold, and a gag. He slid the pool stick under my knees and above my elbows, tying it off with more rope to make sure it was secure.

Shit. I couldn’t get my arms up over my knees, I couldn’t stretch my legs, I couldn’t roll onto my side. I was trapped, sitting against the wall, tightly restrained, unable to do more than rock side to side.

He put the blindfold over my eyes. Then nothing. I couldn’t see anything. I could hear the music playing over the speakers, but nothing that gave me a sense of where he was or what he was doing. I expected him to force the gag he’d brought over into my mouth, only to be surprised when he slapped my face with his cock.

Henry grabbed my hair and pulled it. I opened my mouth to shout in pain, but he muffled my yell by shoving his cock into my mouth.

He started fucking my mouth. Slowly at first, giving me a chance to get used to his dick. I danced my tongue around the head and sides of his cock as he slowly slid it in and out. Every few minutes, whether to keep from finishing too soon, or to give me a much needed break, Henry would pull back. I’d stretch my jaw and take a few deep breaths, only for my break to be ended with a playful but firm slap across my face.

After my fourth or fifth one of these little breaks, Henry forced his dick back into my mouth, this time a lot faster and deeper. He was done being sucked off - he was ready to fuck my throat. He held my hair tight in his hand, making sure I couldn’t pull my head away from him. He fucked my throat faster and deeper until I came close to gagging. I struggled and pulled at the ropes, desperate to get loose, desperate to gasp for air and give my jaw a reprieve, but I was tied to tight. I could do nothing but sit there and take it as he finally thrust as deep as he could and came down my throat.

He pulled out, tussled my hair, and gave me another complimentary slap across the face. I coughed and caught my breath, breathing heavily as my whole body shook. My brief reprieve was cut short as Henry gagged me with the leather panel gag. The panel gag had a soft ball on one side, that filled my mouth, pushed my tongue down, and reduced anything I tried to say or scream into quite muffled ‘mpppfs’. The strap of the gag went around my head and fastened in the back, far out of reach.

“I’m going to close up,” Henry said, “shouldn’t take more than an hour. Then I’ll be ready for a round two.”

He left me on the floor, tied tight and inescapably, blindfolded, collared, and gagged. I tried to stretch the ropes, wiggle my hands, or maneuver myself into a position where I could break free, catch him by surprise, tie him up, and make Henry my bitch. No luck.

My cock stayed hard for a while, thinking about everything that he’d already done to me and anticipating what would come next. Eventually though, when I did start to get soft, I felt Henry’s fingers pinch my nose closed - fully cutting off my air. I remained calm for a few seconds, but then started to thrash violently when he didn’t release. Then, right as I thought I was going to pass out, he released my nose, and gave me a chance to inhale.

Every ten minutes or so, he came back and did it again. I started to associate any moments when I didn’t hear him cleaning with impending suffocation. Any time he got a little too quiet, I would start shaking, whimpering into my gag, taking deep breaths - all preparing to have my air cut off.

I had no idea how long my prolonged bondage and sporadic torture had lasted. My whole body was sore from being forced into an uncomfortable position. I’d given up on trying to get free, and instead spent all of my energy trying to get as comfortable as possible, with little success.

Finally - long after I would have given up and begged for release if I’d been able to - Henry came and untied me. My arms went limp and I laid down on the floor of the bar, stretching out my incredibly sore limbs. I slowly stood up, and then reached behind my head to unbuckle the gag.

“Not yet,” Henry said, “I’m not done with you.”

I obeyed, too sore to fight and too horny to let this end now. Henry removed my blindfold, grabbed the metal ring on the front of my collar, and led me over to the one barstool he hadn’t yet put upside down on a table. The rest of the bar was fully clean and ready to close. All that remained was whatever he had planned for me at this stool.

He bent me over the barstool so my chest was on the cushion and my arms were dangling down. With rope he tied each wrist to one of the legs of the stool. When I was secure he put the blindfold back over my eyes.

WHACK

He hit my bare ass with a short pool stick. I screamed into the gag.

WHACK

He hit me again, then again, then again. Over and over he smacked my ass, first with the stick, then with his hand. I yelled as loud as I could, but my cries were muffled. No one outside would be able to hear me. No one would come and free me.

After every few hits, Henry would take a pause from beating me to lean over my bent body and massage my shoulders, back, and ass. And then, always too soon and with too little warning, he’d switch back to hitting me.

I was a mess, whimpering and shaking. Feeling the full range of pleasure and pain. His hands could be so firm and relaxing, and then seconds later so painful. Half of me desperately wanted out; the other half never wanted the moment to end.

Eventually Henry either got tired of beating me or got too horny to wait any long. I felt his lubed up finger slowly slide into my ass, opening me up.

I moaned as he took his time entering me, feeling his hard cock fill me up.

He grabbed my hips and began to thrust. He started slow. I clenched my bound hands around the barstool legs, gripping tight as he pounded my ass.

He sped up, taking a hand off my hip and reaching around to grab my dick. He pushed his cock deeper inside me. The whole stool rocked as he picked up speed and intensity. My wrists strained against the ropes, his weight pressed my body against the stool, I planted my legs as sturdy as I could, desperate to keep balance as he fucked me.

I couldn’t break free, couldn’t get away, as he found his perfect rhythm and pushed as deep inside of me as he could. He started to jerk me off with the lubed up hand he’d wrapped around my cock. After everything that had happened, after this incredibly hot end to the night, it wouldn’t take much to push me over the edge. I could tell he was close too.

Henry slapped my ass with his other hand, and then reached over and pulled my hair back. He pushed as far inside me as he could, nearly knocking us both forward to the ground. Henry gripped me as tight as he could and cum deep inside my ass. I screamed into the gag - this time not in pain - as I shot my load well past the stool, my whole body filled with ecstasy from the best orgasm I’d had in months.

We caught our breath. Henry pressed against me, hugging me as best he could with me tied to the stool. After a few seconds of much needed rest, he unbuckled my gag, took off my blindfold, and kissed me.

*****

Henry untied me and we sat on the floor for a few minutes, holding each other tight in comfortable silence. Eventually I stood up and headed to the bathroom to do what I needed to do, while Henry cleaned up the mess we’d made.

Once we clothed and the bar was clean, we headed out. I drove Henry to his apartment - an apartment I’d spent many nights and hoped to spend many more. On the drive we talked about everything we’d done. He checked that I’d enjoyed everything he’d done to me, and I assured him everything had been incredible, better than I could have imagined. He asked what I had planned on doing to him if I had won.

“I could tell you,” I said, pulling up in front of his apartment, “or you could wait a few days and find out. I’m closing next Wednesday.”

Henry smiled, “Sounds fun. We should probably do something besides pool though if you want even a chance at beating me.”

“How about darts.”

“Perfect,” Henry kissed me and then opened the car door, “just know I won't go easy on you. During the game or after.”

“I’d want it no other way.” I said, as he closed the door and headed inside. As he walked away I thought about all the things I’d do to him once I had him tied up.

Wednesday couldn’t come fast enough.

[gag1195]

Really cute story! Love Derek and Henry! They've got a great chemistry! Also love the premise of the bet, and the idea of Henry playing with Derek occasionally in between his closing tasks, teasing him and then leaving him to struggle!

[CaptiveDan]

Really cute story! Love Derek and Henry! They've got a great chemistry! Also love the premise of the bet, and the idea of Henry playing with Derek occasionally in between his closing tasks, teasing him and then leaving him to struggle!

Thanks! I'm glad you liked it

[blackbound]

Fun and to the point, with many of my favorite elements. Good work!

[CaptiveDan]

Fun and to the point, with many of my favorite elements. Good work!

Thank you!

[DeeperThanRed]

Lovely story!

While I enjoyed Henry tying up Derek thoroughly, I think my favorite part is them playing pool alone in the bar, both of them half-naked. Makes for such a fun image.

I hope Derek got his revenge at the end, haha.

[CaptiveDan]

Lovely story!

While I enjoyed Henry tying up Derek thoroughly, I think my favorite part is them playing pool alone in the bar, both of them half-naked. Makes for such a fun image.

I hope Derek got his revenge at the end, haha.

Thank you!

I don't plan on writing a followup, but I like to think Derek did get his revenge