Cheer Moms

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."

I thought she might sit at the table near the wine, but she sat on the bed, peeking at my laptop screen as she did and only seeing the spreadsheet I'd been working on. I sat facing her and, as she started talking not only about the teens who'd been getting on her nerves, but some of the other moms, too, her foot was soon in my lap and I was massaging it. I also learned that her name was Deidre (like "daydream" without the "m" she said). It wasn't long after I'd finished the first foot, which remained in my lap, and was working on the second when she both finished her glass of wine and started massaging my cock with the foot not currently in my hands. My cock immediately began to grow and obviously tented out my loose lounge pants. She pulled her other foot from my hands and massaged my tool between her feet as I slipped a foot between her thighs and ran my toes over her pussy. Soon after that she pulled her feet back and got up on her knees, pushing me onto my back as she reached for the waistband of my lounge pants.

Lying on my back, I raised my ass so that she could get my lounge pants down and she soon had them off and cast aside. Kneeling between my spread legs, she took my cock in her hand and pumped it briefly before wrapping her lips around it. I moaned as her hot, wet mouth engulfed my tool and began to slide slowly up and down it while she pumped the base and caressed my balls. I relished her oral talents while I had the opportunity because it was only a few minutes before she abandoned my cock and stood on the bed. I was fully attentive as she dropped both her track pants and panties, exposing her light brown bush, then stepped out of them and kicked them aside.

She was quickly on her knees again, straddling me as she guided my throbbing tool into her dripping pussy. I easily slid all the way in as we both moaned and she closed her eyes. I reached around to squeeze and caress her sweet ass as she started to slowly ride me. It felt as spectacular as it had looked so I was focused temporarily on the soft, smooth flesh while she bounced up and down on my tool. Watching her tits bouncing slightly along with her, though, while still covered by both her shirt and bra, I wanted to get a better look at them and see them bouncing a bit more freely. I slid my hands up from her ass and pulled her shirt up until she was slipping her head and arms out of it. Letting it drop beside us, my hands went to her tits, feeling her hard nipples pressing out through her bra. I caressed them through the material before reaching back and unfastening it. She tossed it aside once it had slid down her arms but my hands were immediately on her bare tits.

Her tits were not large but they were nice handfuls and her nipples were nice and hard. I caressed the soft, smooth flesh and brushed my palms over her hard nipples while still appreciating the feel of her pussy sliding up and down my tool. Her eyes were closed but her mouth was open with the occasional gasp or moan escaping from it. As my hands traveled over her tits, down over the smooth skin of her waist and back around to her ass, she was gradually increasing her pace while her moaning grew louder. I was pushing up into her each time she came down so that she could get the full length of my shaft, which was a little easier when she leaned forward, supporting herself on her arms. I was able to lick and suck her nipples in this position while continuing to push up as she rocked back on my cock.

My hands had gravitated back to her ass, and I relished feeling it in my hands, feeling her hot pussy sliding up and down my tool and feeling her hard nipples against my lips and tongue while she rode me harder. She suddenly went into slow motion when she started to cum and I could feel her body trembling as a whimper escaped her lips. I let my head drop back and just lay there, letting her do whatever she needed to in order to prolong the pleasure she was experiencing. Her pussy felt hotter and wetter as it was flooded with lubricants during her orgasm so I was thinking that I'd take control once she was done and give her a good, hard fucking.

"Can I fuck you from behind?" I asked once she'd opened her eyes again and had smiled down at me. She nodded and, staying on her knees, moved off beside me. I was quickly up on my knees, moving around behind her. Her ass was truly a work of art so I caressed it and ran my tongue between her cheeks, causing her to shiver, before guiding my cock back into her. She pushed back against me as I went back to caressing her cheeks then I started thrusting my cock in and out of her good and hard. Each time my hips tapped her ass, it jiggled just a bit. I found it just a bit more difficult to fuck her hard with my hands on her ass, so I moved them up to her waist and pulled her back with each thrust. Her head was resting on the comforter and I noted that one arm had reached down below her, presumably to stroke her clit.

"Don't cum in me, okay?" she requested, "I want to finish you with my mouth."

Since I hadn't had the opportunity to eat her pussy, I was thinking sixty-nine as I continued to fuck her and was feeling the stirrings of my orgasm. I ran my hands over her ass and back and around to cup her swinging tits as my cock slid in and out of her and the level of pleasure I was feeling increased. Wanting to thoroughly enjoy her oral skills as much as her pussy, I didn't wait until I was on the verge of cumming to pull out of her. She was able to remain on her knees as I moved to lie beside her on my back. She positioned herself over me and immediately took my throbbing, slippery cock in her hand, pumping it before wrapping her lips around it again. I gazed up at her trim, light brown bush above me as her mouth engulfed my tool and I couldn't help but moan.

As she started sucking my cock, I was running my hands over her ass before raising my head to lick her pussy. She was overflowing with pungent juices, so I attempted to lap up as much of them as I could before licking and sucking her clit. One finger slid into her so easily that I added a second and pumped them while my lips and tongue stimulated her clit. Her moaning indicated that she was enjoying what I was doing, but she still remained focused on sucking my cock and caressing my balls. I was definitely savoring the feeling of her mouth sliding up and down my tool while one hand pumped the base. She was a talented cocksucker and I appreciated being on the receiving end of those skills.

As the level of pleasure I was feeling continued to increase and I knew I was getting closer to cumming, my cock was starting to grow even thicker. Deidre wasn't put off at all and just continued making me feel incredible. Even when I exploded into her mouth, she swallowed my load and kept milking it out of me until I had absolutely nothing left. I'd paused in eating her pussy as I came, but went back to it with a vengeance once I was spent. She let my cock fall from her mouth and rested her head on my thigh while moaning loudly as I devoured her pussy. I could feel it becoming more engorged around my thrusting fingers as I licked and sucked her clit and it wasn't much longer before she let out a cry and her body started shaking. I continued what I'd been doing while she rode out a long, intense orgasm, stopping only once she'd let out a long sigh and had gone completely still.

I dropped my head back and slipped my fingers from her pussy into my mouth, still gazing up at her trim bush above me. After a bit, she rolled off beside me and I moved up next to her.

"That was fun," she finally said, "and I hate to run out immediately after, but I probably should go check in."

"Don't sweat it," I assured her, "You know where to find me if you end up with some more free time."

I watched as she got up and gathered her clothes, slowly pulling them back on. She came over and gave me a kiss goodbye and a big smile, so I knew she wasn't regretting what had happened, which was something I had witnessed on occasion. This encounter was fairly typical of what I'd experience when I was on the prowl for cheerleaders' moms, but there were a few atypical and incredibly memorable occasions as well. A really good example is the time that I was riding the hotel elevator down to the lobby and two moms who I'd seen separately earlier got on together. One had short blonde hair, a narrow waist and a decent rack while the other was brunette with more curves. They were in the middle of a discussion that I tried not to obviously listen in on.

"Do you know if there is a bar nearby?" the brunette finally asked me.

"Sure," I replied, "there's one right down on the lobby level."

"Really?" asked the brunette, "I never noticed it."

"It isn't right out there in plain sight," I told her, "You kind of have to be looking for it."

"I don't know, Jane," the blonde said, "We don't want any of the kids seeing us having a drink. It might send the wrong message."

"Actually," I interrupted, "unless somebody is specifically looking for you in there, it is unlikely that anyone will accidentally find you."

They seemed skeptical, so I offered to show them since I didn't really have a destination in mind other than wherever I could find a horny MILF. They were surprised by the isolated location of the hotel bar and pleased that there was a table available that wasn't visible from outside.

"Thank you so much," Jane said, with a bit of smolder in her eyes, "Can you join us for a drink?"

"Only if you let me buy the first round," I insisted.

"Well, we can only really have one," the blonde, Cheryl, replied, "We have to be prepared even if we aren't on-duty."

"Okay, one drink," I replied, "your choice, my treat."

They ordered three margaritas which I was pleased turned out to be pretty strong. I was getting a good vibe from Jane but Cheryl definitely needed to loosen up just a little.

"Do you know if there are any other adults-only activities here in the hotel that wouldn't impair our judgment but also would give us a break from the kids?" Cheryl asked after we'd been drinking and making small talk for a bit. I smirked and Jane raised her eyebrows then gave me a sultry smile before turning to Cheryl.

"I have a pretty good idea of how to spend a few hours together," Jane said to Cheryl, clearly also making a point of some sort with her eyes. Cheryl's look went from inquisitive to realization to a big smile as she turned to me, giving me a good feeling about where this was heading.

"Cheryl and I have been looking forward to sharing a room on this trip so that we could play together, but I think we both agree that an additional playmate will make playtime even more fun," Jane explained.

We made short work of the rest of our drinks and, while I settled the tab, they headed up to their room where I would meet them. I made sure the hallway was clear before I knocked lightly and the door was immediately opened by Cheryl. They were still dressed, which pleased me because I wanted to either watch them undress or help them. Cheryl closed and locked the door behind me then followed me into the room where Jane stood waiting.

"Why don't you take a seat and let us entertain you first," Jane said, so I sat on the end of the bed as Cheryl approached her. They started to make out and my cock was immediately hard. Cheryl's arms went around Jane's neck while Jane reached down to squeeze Cheryl's ass. Jane started to pull Cheryl's shirt out of her jeans so they parted as Cheryl raised her arms. Her white bra was revealed and, as soon as her top was cast aside, Jane was caressing her tits. Cheryl relished this momentarily before working Jane's blouse up to reveal her black bra. Their tits were about the same size, but Cheryl's looked bigger against her slighter frame. They caressed each other's tits as I noted both had very hard nipples standing out, then each reached for the other's jeans. Cheryl worked Jane's jeans down first, revealing her black thong panties then Jane worked Cheryl's down to reveal her white bikini panties.

"Let me see," I requested and they both turned to face me then turned around and showed me their asses. They bent over briefly and, once they'd straightened up, turned sideways so that Jane was facing Cheryl's back. She unfastened Cheryl's bra then they both turned and Cheryl unfastened Jane's. Holding the cups against their tits, they turned to face me again and let the bras slide down their arms simultaneously. They both had large areolas and thick, hard nipples, but Cheryl's were lighter pink due to her fair skin while Jane's were darker. My cock was ready to burst from my jeans and they still had their panties on.

They held their breasts up to me then Cheryl moved behind Jane and cupped her tits while kissing her neck. She slowly dropped to her knees and started to take Jane's thong panties down, revealing a narrow, dark brown bush just above Jane's shaved slit. My mouth was watering as I thought about eating her. Cheryl was massaging Jane's ass but soon stood and allowed Jane to stand behind her and caress her tits before dropping to her knees. Jane slowly slid Cheryl's panties down, revealing a very blonde, trim bush.

"You like?" Jane asked as she stood, running her hands over Cheryl's skin on the way up.

"Why don't you come over and see just how much I like?" I suggested and they came over and knelt before me. I leaned back on my elbows as they opened my jeans while taking turns rubbing the bulge that was threatening to burst through my fly. I lifted my ass as they worked my jeans and briefs down, my throbbing cock springing outward. They both gasped and took turns caressing it before getting my jeans, underwear, shoes and socks the rest of the way off. I yanked my shirt off myself and was quickly as naked as they were while they moved in close and Jane wrapped her lips around my tool while Cheryl fondled my balls. I moaned not only at the incredible feeling of her hot mouth but at the visual, as well. Watching Cheryl take her turn sucking my cock was equally hot, but I knew they must both be dripping wet, so I suggested I do something for them, too.