Disclaimer: This is a work of fiction concocted entirely within my imagination. Any resemblance to real people shouldn't be surprising since most of my stories are based on people I know. While I hope you enjoy this story and are compelled to provide feedback, I don't expect the subject matter will appeal to everyone who reads it. As such, I discourage venomous, nasty feedback full of violent wishes against essentially fictional characters in fictional situations. If this story does not appeal to you, there is undoubtedly one somewhere on Literotica that will, so your energy will be better spent on finding it rather than on vilifying me.
If I told you that I'm 42 years old and I closely follow cheerleading competition schedules for high school age girls, you'd probably assume that I'm some sort of pervert. You may be right, but not in the way you would likely be expecting. It isn't the high school age girls I'm interested in hooking up with when I just happen to book my business trips in the same city as the competitions; it is their moms. It was pretty much by accident that I discovered how the mothers chaperoning these events typically leave their husbands behind and quite often are open to an adventure, especially when it allows them to escape from all of the teen drama. I was initially intrigued by all of the young, nubile, athletic bodies running around the first time I encountered one of these events until I recalled how loud and annoying teenage girls could be. I was seriously considering changing hotels when I got a few smiles and some flirting from not just one but a handful of the moms. After a wild night with one of them, I not only decided not to check out, but decided to initiate some further investigations.
After a few business trips scheduled to coincide with competitions, and a memorable hook-up at each one, I became a follower of the schedules, if not of the actual competitions themselves. I had to be careful to spread them around, though, so I didn't run into the same cheer moms and start to arouse suspicion. I probably put what might be considered an unusual amount of thought into trying to get laid by married women with teenage daughters, but when these women cut loose, it could quite often be mindblowing. And it wasn't as if they were cougars, because in most cases, we were very close in age.
I still had to be careful because, as I was prowling for a MILF, I could very easily be mistaken for somebody prowling for a teenager. I would typically try to avoid anywhere that the younger girls were congregating if possible and focus on figuring out where their moms were. If I had to work on them in a group, that typically wasn't a problem, because the daring one would make an excuse to isolate herself to flirt with me alone. More often, though, I'd chat up a number of moms individually until I found one who was interested in playing. There was never a type, either; I'd never have been willing to make a bet on who the horny or adventurous one would be. Sometimes it was the one who'd put the most effort into her appearance, sometimes it was the pudgy, boisterous one with the big titties, sometimes it was the quiet, mousy, unassuming one; not knowing was always part of the adventure.
There was one particularly memorable occasion when I caught a look at one of the moms in the lobby amongst a gaggle of giggling girls, but it was clear that she had total control of the room. She was cute but on the plain side with short, curly light brown hair and glasses. She was wearing track pants and her ass looked just as nice as most of the teenage girls' asses, if not better. Otherwise, she looked like she was in pretty good shape. It just so happened that, by the time I made it over to the elevator, she ended up joining me waiting there before the elevator arrived.
"I have to tell you," I said, "the level of control you commanded back there was quite impressive."
"Thanks," she replied with a smile, "but if you don't have control, it can be like herding cats."
"Do you get a break now?" I asked, not really flirting yet, just testing the waters.
"No," she replied, "I just forgot something up in my room. I might get a break after their curfew, but not before then. It's too bad there's not a spa in this hotel, but it'd probably be closed by then anyway."
"I wish I could help," I said as we boarded the elevator, "but I can't offer you much more than a glass of wine and a foot rub. On the plus side, it'd be much cheaper than a spa treatment."
"You never know," she replied, surprising me with her sultry smile, "I may be desperate by tonight."
I casually threw out my room number without much expectation but I thought there was a little bit more swing in her walk as I watched her ass when she exited the elevator. Just in case, I made sure to slip out and pick up a bottle of red wine and a corkscrew. It wasn't hard to tell what time curfew was because the hotel suddenly grew very quiet. I was in lounge pants and a t-shirt by that point, fiddling around on my laptop while drinking my first glass of wine. I was pleasantly surprised when there was a knock on my door and beyond pleased to see the woman from the elevator standing outside. I opened the door and let her in.
"I hope you weren't kidding about that wine," she said, sounding a bit stressed out, "because I may just need the entire bottle and a straw."
She was still dressed the same and I watched her ass as she entered the room, heading toward the wine bottle. There was another glass sitting there for her, so she filled it and topped off mine, as well.
"To restraint against the urge to murder a teenage girl," she toasted.
"And a lack of restraint when the situation calls for it," I replied as we clinked glasses.
"Sit down," I said, once we'd taken a sip and she'd smiled at the taste, "vent a little if you need to."
