Chaperone Becomes a Bitch by Jack Sone
I was chaperoning again since I didn't have anything else to do over break and the band director was one of my friends on staff. I knew most of the kids in the band and they were good kids, so I agreed to help out. Most of the chaperones were responsible for 16 kids or 4 rooms of 4 at the hotel.
There were two extra seniors who had a room all to themselves and those got assigned to me too, since I had experience chaperoning band trips.
Every night, the chaperones would go room to room and check on the student rooms, just to make sure they were all there. The boys would be getting ready for bed in various states of dress and joking about sharing a bed with another. It was a turn on for a 48 year old guy like myself who appreciates the young male body. The kids ranged from 14 - 18 and each room was a cesspool of hormones and sexual tension. These kids were used to jerking off at least once a day and as the trip went on, their need to release would grow to the point you could smell it.
On the third night, I made my rounds as usual. Joking with the students and reminding them what time they needed to get up for the next day's performance. I got to the room of 2 seniors last as it was at the end of the hall right next to the stairwell. It was about 15 minutes past curfew and no one answered the door. I knew better than to think they had already fallen asleep. These two were best friends and were rumored to have fucked half the girls in the band. Evan was 18, 5'8" and about 140 pounds of lean muscle. He wasn't a large guy, but he was muscular. His dirty blond curly hair was always a mess which added to his charm. His best friend, David was a little taller and a bit skinnier than Evan. His light brown skin was probably from his dad, who he didn't know, but was obviously Latino or Black because his mom (who was a well known pain in the ass at parent/teacher conferences) was blond, blue eyed and as white as you could get.
I used my key to the room to unlock it and checked to see if they were inside. It was a typical hotel room. Two double beds, dresser with a mirror, and a tv. Strewn about were bags of snacks, drinks, and clothes.
It was messy, but nothing out of the ordinary. I don't know who they belonged to, but there were a pair of boxers on the floor next to the far bed. I looked around at the door to make sure it was closed and picked them up. Putting them up tight on my face I inhaled deeply at the smell of boy musk. These had obviously been worn a while and the odor was strong enough to give me a semi. I wanted to stay and have my way with those shorts, but figured I better go let the band director know that two of the students were missing. I dropped the shorts and turned around to find Evan and David standing in the doorway watching me.
It was no use to deny anything. I had been caught red-faced and with a semi hard on sniffing their underwear. What do you say in that situation?
I was impressed with my quick thinking. I cleared my throat and said in my most authoritative voice, "Boys! You're late! You know you have to be in the room at 11. That doesn't mean 11:15. I'm going to have to report this."
They didn't respond. They just stood there looking at me. Still trying to come across as a tough guy, I added, "Where were you anyway?"
Evan broke first and smiled in a knowing, kind of controlling way. "Where were we Mr. Jones? Don't worry about it. We had some things to do down in the lobby." At that, David slapped his buddy on the shoulder and said, "We would have been a lot longer if those girls had given us what we need."
They both laughed. "Looks like we were looking for the same thing, huh Mr. Jones?"
"What? No, we're not Evan. The fact is you guys are late. I don't care what you were doing. I still have to report it."
"No you're not." Said Evan. He seemed angry. The smile had left his face.
"Don't pretend we just didn't catch you sniffing David's dirty underwear you sick fuck. One word by us and you're fired or maybe worse."
"What?!?" I replied as incredulously as I could. I was just picking up some things. You can't keep your room so messy. It's a fire hazard. I should report you for that too."
"Mr. Jones. Nice try. But we know what we saw. Show him the picture David."
Damn, I thought to myself. They had taken a picture. I couldn't get out of this. Well, technically, I hadn't done anything illegal. I would probably lose my job, but no jail time for sniffing underwear. David showed me the picture on his phone. My head dropped. I was nailed.
Caught. Nothing I could do.
Evan walked toward me and lifted my chin and looked directly in my eyes.
His eyes were calm. He stared deep into me and said, "Don't worry Jack."
Him using my first name caused me to shudder. "We can work this out.
See, David and I were just about to score some pussy when this damn curfew fucked it up. Those girls are long gone, but we still got needs. You know what I'm saying?"
"Look boys..." I started to say but was interrupted by a slap across the face.
Evan brought my gaze back to meet his. "Men. We're not `boys' Jack.
We're men. Say it."
I wasn't sure what to do. What the fuck was happening? I just wanted to get the hell out of there. I'm not a big guy, about the same height as Evan, maybe an inch taller and about the same weight, just not much muscle.
I started to move around Evan, but he was stronger. Small, but wily. He grabbed my arms and moved me back. "Say it," he repeated with more force.
David came up to his side.
It was two against one and they had the proof. "Men," I muttered. "You're both men."
"That's right princess," said David. "Now you know your place." Suddenly a side of David was showing that I had never seen before. Both of these boys (MEN, I mean) were not who I thought they were. "Men have needs," continued David while Evan still had a tight hold on my arms.
Evan released one arm and grabbed his package and laughed, "My need is right here Jackie boy."
"Look guys. I understand you have needs, but I can't do this." This was getting weird. And hot. My semi had deflated but I felt my dick getting hard as I pleaded. Their eyes told me they didn't really care though.
They were cold. Evan put his hands on my shoulders and forced me to my knees.
David got the his underwear from the floor and threw them at me. "Finish the job faggot."
They both laughed. I felt like crying, but all the time my dick was getting harder which was pretty obvious in my sweats. I pushed the dirty boxers into my face and inhaled deeply. They smelled like teen sweat and spunk mixed with some piss. I think I even closed my eyes, but was brought back to reality with the sound of David's zipper and him saying, "Here's some fresh underwear teach." He unzipped and stepped to my face. Putting his hand on the back of my head, he pulled me in deep to his underwear. My nose was just under his balls. It was damp. It smelled amazing. I groaned.
Evan laughed and said, "Look boy, we have pictures. You're going to get us off. But face it. You want it, don't you. Your little faggot cock is hard and you're getting off smelling my man's spunk. This might be the best school trip ever teach."
David was hard as rock. "Get them off teach. You deserve some man dick."
I went to pull his boxers down, but he slapped my hands away. "Teeth." I looked up to see his dark eyes and saw commitment. These boys were going to use me like a bitch. I used my teeth and clumsily pulled his boxers away. His hard cock sprang up and slapped me in the face eliciting laughter from them both.
"He looks good with a cock in his face don't he Dave? Looks natural, like that's what he is meant to do." Evan looked down at me and spit in my face. "Some men are meant to fuck," he growled. "And some are meant to get fucked."
David grabbed my ears and started face fucking me with a dick that had more in common with his black father than his white mother. It had to be 8" and looked even bigger on his skinny body. His pubic hair was jet black and course and curly. My nose was shoved in tight while he held his cock in buried in my throat. My chocking didn't seem to concern them. He would let me off just to push back in again. Meanwhile, Evan had striped naked and pulled my shirt over my head. He lifted me up and threw me on the bed which gave David a chance to get naked.
I was on my back with two naked and hard as rock teenage boys in front of me ready to use me like a bitch... as THEIR bitch. Truth is, it's a dream come true, but when you're being forced, you have an innate desire to get out and escape. It wasn't smart but I tried to make a break for it. I still had my sweats on and they were naked. If I could just get out maybe this would all go away.
Wrong move. This guys had muscle and two against one is bad odds anyway.
They grabbed me and threw me back down on the bed. I had no chance. Evan was pissed now. He straddled my chest and started slapping my face calling me a fucking loser and faggot. His knees held down my arms and I was defenseless. "You are ours bitch. Now I'm not holding back. I was going to break you in easy like I did to that little freshman clarinet player.
But you are getting it full force now you faggot." While he was slapping me, his hard dick bouncing on my chest, David pulled off my sweats.
Exposed to them for the first time, my raging hard on left no doubt that they were dealing with a fag.
My dick paled to both of theirs at a little over 5". David especially thought it was funny and toyed with it like a joystick while Evan slid up and put his sweaty balls in my mouth. "Clean them off good, boy. Smell those teen balls." I did my best to get to his ball sack under a jungle of hair.
David was pushing my legs up to expose my hole. "Look what we got here," he said. "Evan," he asked, "men have assholes. They use them to shit. What do you got here?"
"Well," Evan replied, "this ain't no man. We got us a little bitch boy."
"Right." Said David. "This ain't no man, so what's he got?"
They had started talking in a redneck southern accent. These guys were having way too much fun. Evan, still with his balls in my mouth said "I imagine that there is a little pussy then. Is that what you got Jackie boy? You got yourself a pussy back there? He punctuated each word by slapping his cock head on my check.
Evan got up and joined David. Each held one leg in the air and exposed my hole to them. They each slapped my check hard. As it pinked up, they would toy with the hole with their finger. Each rubbing up my crack and pushing in a little. Adding their spit, the fingers started exploring deeper and deeper. Evan put my leg on his shoulder and fingered my asshole with one finger and stuck his other fingers in my mouth. "What a bitch," he muttered to no one. David was jerking off his huge dick literally drooling over my hole. "I gotta get in that Evan. I can't wait."
Centering himself between my legs, David drooled spit onto his 8" cock.
Evan moved back up and sat on my face offering his asshole to my tongue.
David put his cock head at my hole and slowly pushed in. I started squirming and whining so Evan sat down completely covering my mouth and nose with his ass. I felt David inch in slowly. So damn slow. He'd pull out 1/2 inch and move in 1". Slowly. While I felt my hole resist the invasion, Evan continued to squirm around on my face, allowing me to breath and then smother me with his weight. I tried to remember to relax. Push out like you're taking a shit, I thought to myself. I figured if it was going to happen, I should try to make it as pain free as possible. David continued his slow invasion while Evan seemed to dance on my floor of a face. When my tongue wasn't in his hole, he'd slap my stomach. I was in pain everywhere. It seemed like forever, but I finally felt David's pubes hit my ass. He was huge. I don't think I had ever taken anything that big! Yes, I had experimented in college. But that was a long time ago.
And, I was willing. This was a different experience entirely.
Evan, who was the more impatient of the two said to David, "Fuck him dude.
Fuck that pussy." David pulled out slowly. I had just started to think to myself at least he's gentle when he shoved in all the way, long dicking me in one thrust.
He pulled all the way out and then all the way in. I heard him say, "Damn, this is one tight pussy. I'm glad we lost those girls dude. You're going to love this." David increased his onslaught on my ass with long fast strokes of his massive black dick. The only thing that kept me from screaming was the ass on top of my face and Evan's dance to impale my tongue deeper in his hole.
I'm not sure how long this went on. There were smells and sounds that enveloped my world. I was brought back to reality when Evan got up and said, "My turn man. Let me have some." David pulled out and Evan turned me over on my hands and knees and mounted me from behind. He was a bull. No finesse like David. He just rammed his cock up and started fucking. He was smaller though so it didn't really hurt. My dick was still hard and I involuntarily reached for it and started jerking off.
"Dude," said David. "We got ourselves a little whore here. How can you be hard with a dick up your ass?"
David offered me his dick. I sucked it greedily while Evan fucked me from behind. Spitroasted turned into every imaginable position over the next hour or so. Each fucked me multiple times and unloaded two loads of cum each into me.
They wouldn't let me go until I jerked off for them while they took pictures. I was theirs. "You belong to us now bitch" was how Evan put it.
David added that it would be nice to have a set of holes to use whenever they wanted and they didn't even need to leave school to do it.
I limped back to my hotel room wondering how far this would go. I found out the next night...