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Chapter 7 — The Hotel
***Hello Readers
Quick note, my stories tend to progress a bit slower, if you’re looking for quick paced sex scenes try another story.
Also some past people have nitpicked about small consistency details in my stories. I’m not writing a classic novel, I’m not going to take time to explain every little change in a scene. If you’re looking for 100% accuracy in stories, buy a book.
I hope the rest of you enjoy 😀
*****
As we made our way through the hotel lobby I wondered how ridiculous our little gang looked.
There I was, wearing a rainbow-colored kilt so short it barely passed my ass, with a cum stain in the front. Clinging onto a man twice my size, wearing a torn kilt held on by safety pins. Then there was Brian sporting a fat lip, and old man John carrying my passed-out girlfriend.
If the situation was odd the hotel staff didn’t show it, on the contrary a few of them greeted Frank back as a regular.
As we all crammed into the elevator Frank called over one of the teenage bellhops named Daniel. The boy was about 18-19 years old and looked proud that Frank had called for him personally.
As the door closed behind him Frank addressed the teen.
“I’m sorry but we’re going to need few items cleaned and repaired.”
Frank then proceeded to remove his vest.
“The little boy here” he gave me a nod “Accidently came all over my vest, I would like it washed by tomorrow morning if possible.”
The teen was struggling not to laugh as he glanced at me and took the vest.
Frank continued “Next this will need to be repaired” without ceremony he then removed his kilt and handed it to the boy, who’s jaw had now dropped, staring at the naked man’s HUGE cock.
“The little tyke tore my favorite kilt, if you don’t have anyone that can fix it working this weekend; I think Mr.Ben’s in town should be able to fix it.”
Now standing naked he turned to me and gave me a stern look like a father scolding a child.
“The naughty boy also managed to soil his own kilt which will need to be washed”
Everyone turned to me as the elevator stopped on our floor, with a slight ding the doors opened to the 7th floor. Frozen and unable to move I just stood there as Frank chimed in;
“No need to by shy little Tommy, I’m sure Daniel has seen lots of little willies in gym class. Some boys just hit puberty late”
I could feel blood flowing to my cheeks as I blushed, at 30 years old I wasn’t really a little boy anymore…
While I was rooted to the spot in shock John squeezed past me carrying Karen and started walking down the hallway. Brian meanwhile was holding the door with a cheeky grin on face, waiting for my response.
Frank cleared his throat a little more serious now; “Either remove it boy, or I’ll do it for you”
I snapped into action and slowly started to remove the kilt, Brian licking his lips as he watched.
My hands were shaking so much that once unhooked the kilt fell through my hands, unraveled quickly and falling to the floor. A cool breezing washed over me as my smooth dick bounced free, still rock hard from all the pills they had fed me. Caught off guard I froze for a moment before quickly covering up with both hands.
Glancing at the teenager however I could tell the damage was done; a slight grin had now appeared on his face as we locked eyes.
Trying not to panic I slowly bent forward to pick up the kilt, making sure to cover. Frank however seemed unimpressed with my speed and gave my ass a hard SLAP.
The force of the blow caught me off guard and reflexively I stood upright, both my hands going back to protect my sorely beaten ass as I gave Frank and angry glance.
I realized a moment to late however that I was once again exposed as I returned to lock eyes with the bellhop. The boy was chuckling as he looked down at my small dick, and said;
“You’re smoother then my baby brother man!”
The surprise passed as I saw the boy fishing his cell phone out of his pocket. Before I had a chance to cover up however, Frank grabbed both my arm keeping them behind my back.
[SNAP SNAP SNAP]
The bellhop took a couple photos as I watched on helplessly; with encouragement from Frank he even made sure to capture my face in a couple of the shots.
Then after a few seconds that felt like an eternity Frank released my hands. Not bothering to cover up I quickly bent down and grabbed my kilt, pushing it into the bellhop’s arms. Then I darted out the elevator to follow John with my hands cupping my swinging dick. I had almost forgotten that my ass was spanked purple and had been drawn on by Frank, until the bellhop yelled out “Nice buns BAD BOY”.
…
I dashed into the hotel just as John was carrying my girlfriend into adjoining suit. Frank’s room was quite large, reminding me that not only was Frank my superior in basically balıkesir escort every physical aspect; he was also a very successful businessman.
Looking past the living room area into the bedroom I panicked as I saw what looked like a mini sex shop, the room was filled with a variety of dildos and other toys. With kilts, leather garments, and bright pastel colored clothing scattered about. A sex swing was also set up in a corner with a video camera pointed at it. There also looked to be a leather sleeping bag next to the bed.
Tearing my eyes away from the scene I followed John into the next suit. The layout was exactly the same except without all the toys; I saw John tucking Karen into bed. Quickly I went to go join her when Frank grabbed my wrist turning me around.
I pleaded with Frank “Please… you said we could sleep alone tonight”
Frank just returned a stern look and said “That was only if you BEHAVED, since you hurt Brian’s jaw we’re going to need you to give us a HAND first”
I gulped, looking back at Karen in shame as I was dragged into the next suit; John followed closely behind closing the door shut softly. I was once again trapped alone with these 3 men.
…
Frank spoke:
“You will receive 3 more punishments for your disgraceful behavior on the way home”
All I could do was look down at Frank’s shoes as he scolded me, like a little boy before his father.
“Since you hurt Brian, your first punishment will be filling in for Brian for the night”
I looked up in panic at Frank and started to object before he cut me off.
“Don’t worry, we won’t go too crazy. We know you’re not a capable bottom like Brian” he gave Brian a pat on the shoulder making him smile.
“You’re just going to have you take over some of his other responsibilities”
“Your second punishment will immediately follow, since you can’t seem to control your own orgasms, we will do it for you.”
“Then, your final punishment will come tomorrow morning…” he gave me a wink “Don’t want to ruin all the surprises!”
“First go to the washroom and clean yourself up, you will be awake for a while still and this may be your only bathroom trip of the night, make sure you’re well and empty.”
As I turned to rush towards the bathroom I felt a hand placed on my shoulder, Frank growled in my ear
“First though I think Brian wants his toy back”
With one quick yank he pulled the vibrating egg out of my ass. The shock and pain kept me rooted to the spot until Frank gave me a quick push. “5 minutes alone to get ready boy, or we can continue with your bathroom spankings instead.”
I quickly raced off to the bathroom and slammed the door behind me, locking it.
…
I had just finished washing my hands when I heard Frank pounding on the door. Taking a dump had proven quite painful after all the assaults my anus had taken today.
“Times up! Little boys aren’t supposed to lock the door when they go potty. Come out now! or I’ll break the door down.”
I stopped with my hand on the doorknob, stealing myself for what I was about to endure, for Karen, then I turned the handle.
…
While I was in the bathroom the others had gotten things ready. All three men now stood naked before me.
Frank and John who I had already seen naked were wearing metal cock rings and were rock hard. Sporting 11inch and 8inch cocks respectively. Both men kept everything fairly well groomed down below, even trimmed they made me feel like a little boy with my hairless crotch and small dick.
Behind them stood Brian, who was still nursing his fat lip I had given him. He was completely hairless from the neck down and was wearing a chastity case. A little curiosity crossed my mind as I wondered why anyone would voluntarily wear such a thing.
Frank seemed to read my thoughts;
“A proper boy only cums when Daddy wants him to and takes pride in showing others that he belongs to someone else.” Brian shook his hips proudly at this remark, making the cage rattle.
…I would never understand these men.
Frank then held out an orange pill, I hesitated but then reached out to grab it; Frank closed his hand. “Open Wide” he said. Reluctantly I opened my mouth; Frank then slowly slid the pill into my mouth, grazing my tongue with his fingers. He made sure to push all the way back making me gag a little, before dropping the pill. I swallowed and showed him my empty mouth.
“Good Boy”
Frank then steered me into the bedroom. I was slightly relieved to see they had cleared away most of their bondage gear as Frank plopped me down onto the bed.
Frank continued talking; “Now for your 1st punishment we are going to play a little game, the better you perform the quicker it will be over. I warn you though; we’re all pretty good at this game”
Another smile crossed the group’s balıkesir escort bayan faces, making my uneasy stomach lurch.
“The game goes like this; in college you may have done a few little circle jerks with your buddies”
He paused and gave me a questioning glance; quickly I shook my head no.
Frank continued looking unphased;
“The point of the game is to make your opponent cum first; you’ll be playing John first.” Glancing at John I could see his hungry eye taking in my body. “If you win you’ll be done for the night and can go to bed with Karen”
My hopes raised a little; I already had John’s balls forced down my throat; a hand job wouldn’t be too bad. Plus having already cum 3 times today, I was confident I could win.
“If you cum first however, then you will no longer be able to use your hands and will need to finish John off with a blowjob. Then, you will be forced to play the next contender… Me”.
I cringed, this was more what I was had expected.
“We will be having strictly a blowjob contest, no hands!”
Frank licked his lips and gave me a wink
“If you win the contest, then once again you will be done for the night”
“If you lose however, then for every extra minute you take, you will need to spend 10 minutes in Brian’s sleep sack tonight.”
He pointed to the leather sleeping bag
“While in the bag Brian will get to choose which toys he wants to use on you.”
I looked at Brian and his fat lip trying not to panic, they would have to make me cum for my 4th and 5th time today, I could hold out…
…
I sat at the top of the bed, naked, waiting for John to join me. My cock had finally gone semi-soft so they had removed the metal cock ring, I was now completely nude, not a stitch on me. Glancing over at the clock I saw that it was just after midnight. As Jon sat down next to me in the bed I looked over at the sex swing in the corner and saw Brian climbing in, Frank was lining up behind him as he glanced over at me.
“I’m just going to have fun with my boy here before it’s our turn together.”
[gulp]
As Frank started fucking Brian I slowly reached over and started stroking John cock, John grabbed my shaft as well, and we started our contest.
…
I looked over at the clock; we had been jerking each other off for 10 minutes now. Reluctantly John had managed to stroke me to full mast. He was obviously very experienced with other men and could react to my every movement heightening my experience.
On the other hand, despite my best efforts I was struggling to do as well. My sloppy hand job seemed to if anything; wilt John’s original hadron away.
As I tried to concentrate on jerking John off, I was finding it difficult to tune out Brian and Frank’s fuckfest 4 feet away. All I could hear was the rhythmic slap slap slap as Frank impaled Brian.
Then, after a couple more minutes of beating John off I heard Frank start to speed up his thrusts. Despite myself I looked over at Brian who was takings Frank’s mammoth cock with ease, while his own cock was bursting through his chastity cage; bouncing against his smooth belly.
Finally, Frank took one last lunge and plunged balls deep into Brian’s ass. I was transfixed as I watched all the muscles on Frank’s body start to tremble and contract. Frank howled as his 300 pound frame spasmed unloading inside of Brian, filling his belly. Brian meanwhile was moaning and was in a euphoric state, wrapping his legs around Frank and forcing his cock as deep as possible inside of him.
Finally, after the trembling had stopped Frank leaned forward and collapsed on top of Brian, almost burying him under his giant body. Then they embarrassed, locking in a deep passionate and wild kiss.
Distracted by the passion the 2 had displayed it finally dawned on me that they may have an ulterior motive. Frank most likely hadn’t cum yet today, meaning he would’ve been on edge for our blowjob contest later. While I originally thought it would play to my advantage that Brian was getting him ready, I now realized that with the first load released, I would have to work so much harder for the next one.
…
I was brought back to my own contest as John started using his thumb to rub the glans just below the head of my penis, a sensitive spot I always made sure Karen spent lots of attention on. I tried to hide my intense pleasure from this, but John caught on and soon redoubled efforts, making my groan and curl my toes in ecstasy. I tried to redouble me own efforts on John’s cock, but I could barely think straight as waves of pleasure shook my body.
I soon realized that my contest with John was probably a lost cause. He was just teasing me; bring me closer and closer towards the edge, than slowing down. Meanwhile I doubt I had made any progress on him at all.
Glancing back at the sex swing escort balıkesir I saw Frank fiddling with Brian’s chastity cage before prying it off him. Brian’s cock sprang free, rock hard and throbbing as it pointed straight up. In shame I realized that this prissy man’s cock was larger than my own, sitting at around 6 inches. Frank glanced over at me and saw I was watching; blowing me a kiss he then starts to fuck Brian again; this time Brian’s free penis was flapping back and forth smacking his belly.
Being caught watching their ‘love making’ made me feel embarrassed, so I turned back to my own contest trying not to panic. This was bad; if Frank came twice before our contest even started I would be screwed. Even if I lost to John, I needed to finish as soon as possible so that I could get to Frank before he was pumped dry. Desperate to make some headway with John I braced myself for the one thing I knew the man liked. Reluctantly I release John cock then spun around on the bed, John catching on to my plan scooted down the bed a little so that we were facing each other in 69 positions.
In this position it was much easier for me to reach over with both my hands and play with his ball, which I knew he liked. This brought the immediate reaction I sought as John shuddered. Staring at his cock also made it much easier for me to concentrate on my technique, as I was finally getting accustomed to holding another man’s dick.
While the new position gave me a decided advantage for ending the match sooner, it did have the downfall of giving John full access to my own dick as well. As I stared at the old man’s balls I tried to will my own dick down, without any luck. I was still no match for John, and was almost certain to lose the first round, but at the very least I could hold out and hope for a miracle.
As John once again teased me towards the edge, I noticed that this time he wasn’t slowing down. Panicking I did the only thing I could think of to stop him; I leaned forward and started to suck on his balls. Tasting for the second time in my life another man’s balls, the same balls that 12 hours earlier were being forced down my throat, I was now voluntarily sucking.
The all too familiar salty taste overpowered my taste buds as I sucked on his nuts. Fighting back my gag reflex I sucked, licked and flicked his balls. It seems I finally caught a break and had managed to catch John off guard. He had released my cock, allowing me to regain a bit of control.
I was now desperately sucking on the man’s nuts and stroking his dick, playing towards my advantage. John had snapped out of his daze however and started to jerk me off as well, twisting and pulling my balls while he jerked off my shaft at a rapid pace.
I knew I could only last moments longer as I sucked with all my might on Johns balls and jerked him off, putting more passion then I ever had with Karen, into this man’s dick.
Finally, though John brought me over the edge, my dick exploding for the 4th time that day as my sensitive balls emptied in John’s hands. My orgasm seemed to be all John was waiting for as 5 seconds later he exploded into my hand. I had managed to escape giving John the blowjob, but it was unmistakable that I had lost the first game. As I lay back in bed exhausted, I found myself troubled by the emotion I was feeling at making another man cum… Pride
Panting with my eyes closed I was broken from my daze as I heard the familiar grunting sound from Frank, and then quickly followed by Brian swooning as well. They had finished their second bout; my rush to finish off John had been for nothing…
Still spent I didn’t even react as Brian waddled over from the swing and started to lick my belly and hand clean of cum. I just kept my eyes closed and let him take the prize he wanted, unable to muster any fight, I still had another competition to cum….
Still trying to catch my breath I didn’t struggle as Brian started slipping a harness around my shoulders, chest and neck. Then a second one was slipped up my legs and secured around my waist, both then connected in the middle. Looking down at myself, it looked like I was ready to go rock climbing or jump out of a plane; the harness had clips and straps all over.
…
Then I saw Frank come back into the room wearing a similar harness, it hit me what these were for, we would be locked together. Before I could even muster an objection, Frank cut me off.
“Ready for round 2 with Daddy…” I large grin crossed his face as I gulped
“We will be connected by these harnesses until one of us cums.”
I tried to object and say it wasn’t part of the rules; however I was cut off;
“I’m sure I was clear that once you came, you would have to finish John with ONLY your mouth.”
Biting my tongue and thinking back I realized that however brief I had in fact broken Frank’s rules.
“While I’m sure if I told you the harnesses were punishment for your misbehavior you would understand, but to be honest it’s just because I really like them”
Another childish grin crossed Frank’s face as he looked down at me. I muttered a sarcastic reply
“And what Daddy wants, Daddy gets” [gulp]
I had expected Frank to get mad at me for talking back, but all it did was make him smile more.
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