Everyone is over 18 in this.
So here I am, a man who is 16 years older than I am has his hands in my hair, pushing my head down on his cock and pulling it back up again while two teenagers go at it like rabbits in the hotel room next to ours. I'm so horny I can barely control my hands, my arms, or anything. With my one shaky hand I'm holding the base of his cock while my mouth sucks hard as he's pulling me up again, breathing heavily, demanding I look up at him while I suck his cock. I need to be fucked so badly. How did I get here? I am on one hand hoping it never ends, while on the other hand can't wait until it does so we can do it again.
I have a friend, Jessica, who is about 2 years older than I am. I'm almost 28, she just turned 30. She has been a student teacher at a nearby high school for a few years now, and this is the first year she was asked to help out with the school's cheer leading team. I remember laughing pretty hard when she told me that. If you knew her, you would understand why it's just a ridiculous thought. Why? Well... it isn't that she is a tomboy, per se. It is that she's not exactly a girly girl. She's geeky, a little overweight, does nothing with her hair, I don't think she even owns lip gloss, and when she has to dress up she seems that she doesn't even know what to do with herself. Throughout our school years, she always had things to say about "cheerleader bimbos". She's a hilarious girl, and she has the most adorably bubbly personality. She would probably do best in an elementary school setting rather than high school, as she's always seemed like a big kid to me.
But nevertheless, there she was telling me all about agreeing to help with the cheerleading team. I didn't have to tease her; she did all of it for me. We had a few drinks while watching Game of Thrones reruns and laughing about her upcoming adventures. I told her I'd come watch her sometime. Hell, it would probably be more amusing for ME than anything else.
I remember the first time I went to see it, expecting a big old mess, but not much was going on. They were out on the field doing a lot of nothing. The girls were in little groups, some stretching, most talking and doing a few moves. There were 2 guys on the team and I admit to wondering if they were gay. They were good looking, about the same height. One was built with a bit of a tan, and wavy hair with natural looking highlights. The other wasn't built or muscular but in good shape, with short black hair. The girls, all your typical high school cheerleader stereotypes: Blonde, brunettes, a few redheads, all skinny and perky and pretty. The coach seemed preoccupied on his phone, my friend on hers as well. This high school had a reputation for having a pretty good cheer leading team. Not the best, but pretty damn good, so I was wondering why everyone was slacking.
My friend noticed me and came over to me excitedly.
She explained that they were warming up, or at least supposed to be, and that the coach was on the phone with one of the girl's moms because of something stupid and irrelevant to this story.
We talked for a little while, when the coach who had previously been facing away had turned towards us before heading in our direction. As he got closer, I got a good look at him. I remember thinking "wow, those eyes!!" They were light grey, with a hint of blue. He wasn't exactly tanned, but his skin showed he had obviously been in the sun, which made the color of his eyes pop, even with his sun visor on.
"Hello... visitor..." he said extending his hand.
"Hello... coach dude..." I replied in my usual smartass fashion, giving a quick hand shake.
Coach-dude smiled and said "Coach Dude. I like it. Although I'm known around here as Mr. Hammond. But to faculty and friends, just Shawn."
I introduced myself and there was a moment of idle chit chat, but I do not recall exactly what was said, just before Jessica cut in saying "Anyways... Shouldn't we start now? And what did Mrs. Paton say?"
Shawn turned to me, told me it was nice meeting me, and walked off with my friend to fill her in on his phone call, and then they got to work. I watched for a little as they did their thing. It was pretty boring.
My boyfriend Jackson (who had been mentioned in previous stories) and I broke up not long before all of this, so I did not feel bad about checking out Shawn or the boys on the team. But after a little the boredom took over, and I waved goodbye to Jessica and took off.
Later that night, I asked Jessica if she wanted to get together. She came over and we did some random crafty things and some shopping on eBay. At some point, Shawn was brought up. She told me she noticed he was flirting a little, and she figured she would "save me" by distracting him. I told her I didn't need saving, I thought he was attractive. She gave me an "eww" face, and went "Dude, he's old. And married. That's just weird." I reminded her that I liked older men, and that flirting was harmless. She just shook her head, telling me "you're weird," and went on about our business.
I decided not to go to any more practices because they were boring. I've never been a cheerleader, or even interested in cheerleading, so it just didn't interest me. So when I was asked to go on a 3 day trip to keep my friend company and to help chaperone, my first instinct was to say no. It was a competition in Maryland, though, and I've always wanted to visit Maryland anyway. It wasn't far from the beach, even though the weather was too cold for that. Plus, there'd be more time to look at the coach and maybe get the chance to flirt back a little. So I finally agreed.
The day of the trip came, and the school had paid for rooms that had two beds, but I wasn't sure if mine would be covered or not so I just got my own room, with one queen size bed in it.
I don't want to bore you with details, but the first day and night were uneventful. Nothing worth writing about. The second day was the competition and I went and watched. Honestly, the other team was better. Afterwards, some of the kids went to lunch and to the movies with a few of the parent chaperones while we stayed back with the ones who decided not to go. Around 830 or 9, most of the students were in their rooms, the rest were free to roam the hotel I guess. Jessica and I went to the hotel bar, and were sipping on some drinks, and starting to feel pretty good, when Shawn walked in and sat by himself and ordered food and a beer. My stupid tipsy self yelled "Hey!! Shawn-Dude-Coach-Guy!! Come sit over here!!" I looked at my friend who was patting the seat next to her, then looked at me and winked. He sat with us, we all joked around, flirted, with each other, had a good time drinking. Around 10, Jessica announced she was going to bed, and asked if I was going too. I told her I was going to stay for a few more drinks. She left, told me text her if I needed anything, and gave me a "hint hint" look. Wasn't entirely sure what she meant.
So then there was Shawn and I at the bar.
We started talking and even flirting some more. Maybe it was the drinks, but I was finding myself wanting to sleep with him more and more every second. But he was married; I figured at most it was some harmless flirting. But damn was I horny for him. I remember at one point he "accidentally touched my knee, and I felt tremors all throughout me. It was obvious that he noticed because not long after, he did it again, except this time he rubbed my leg a little higher up before letting it rest there, acting rather non-chalant about it while I could see in his face that he knew exactly what he was doing.
As we talked, I mentioned how Jessica and I were basically Game of Thrones addicts, and that I had it on my laptop to watch before I went to sleep up in my room. He said he'd probably end up watching the news because he wasn't about to pay for movies in his room. I then had the drunkenly brilliant idea to invite him to my room to watch a movie. (Yea, a movie. Right.) And he at first gave me a look that I couldn't quite comprehend. So I said "Relax, I know you're married, I mean JUST a movie!"
He said "Well it's not hurting anything, right?"
"Nope." I replied.
We talked for a few minutes, light conversation. He was obviously antsy at this point and said "I'm just about finished here, how about you?"
"Me too. Just one more shot!"
Shawn flagged the bartender down, ordered me another shot of my favorite, Captain Jack, and we were on our way upstairs. Normally I'd have been worried about someone seeing us go into my room together, but I was drunk at that point and wasn't really thinking about it.
We got to my room and I pulled out my laptop to put a movie on. I've got a bunch downloaded, and in that mix is some porn. I completely forgot about that!! He pointed out some of the weird titles with a smirk and I jokingly yelled at him, saying "Hey, don't judge me. I'm single and I have needs too!" He smiled and said "Hey, no judging from me! That's hot that you watch porn! Do you ever—" and then he stopped, saying "Never mind."
"What, play with myself? Duhhh." I said.
"I figured that was a dumb question. Why else would you watch it? I just wanted to hear you say it, " he said, winking.
Damn, was I horny as hell.
So anyways, we ended up not picking a movie, but he sat on my bed, and I sat in a chair next to my bed and we just talked for a while. The conversations went back and forth between being sexual, and casual. I was starting to wonder if anything was even going to happen.
In almost no time, we heard commotion in the next room. Talking, giggling, and then a thud on the bed. Shawn recognized the sound as one of the cheerleaders, Trisha. We couldn't hear exactly what she was saying but we did hear another male voice. One of the male cheerleaders perhaps? Anyways. Two teenagers, alone in a hotel room... what do you think happened next?
It didn't take long before we heard some movement on the bed, with some giggling. Shawn and I had stopped talking and were both listening to see what would happen next, I think hoping we would start hearing this girl get her pussy pounded by this hot young guy. And then it started. It started slow, a few quiet moans. That went on for a while and Shawn and I started talking, both trying to make it seem like we didn't want to be listening. But the frequent silences between us told each other that we did.
Trisha was in the other room, presumably being eaten out, for a good 10 minutes or so. Her moans were soft at first, but over time was getting a little more frequent. I was so horny I considered going into the bathroom to finger some tension away. Her moans got louder and finally I said "Ok, I can't help it. I'm getting so fucking horny listening to those two!" (As though I wasn't horny enough before.) Just then we hear her yell out "Oh fuck... Oh fuck I'm cumming, I'm gonna cum AHHH" followed by some moans and screams.
"Ohmygod, you think you're horny, I'm about to explode. I think I ought to head back to my room, and take care of this before I do something I'm going to regret doing. It's been way too long since I've had sex" But he made no effort to move. He just looked at me, with a look that was begging for me to ask him to stay. I was happy to oblige.
"But wait! Don't you want to hear the rest of the show? I'm anxious to see how long this goes on." I said, sitting on the bed next to him, staring directly at him.
"I guess I can stay for a little while..." he said quietly. I smiled at him, but didn't do anything.
