Chicago Cheer 2025

After a few months off, I found myself inspired. Enjoy! As always, I welcome constructive comments and suggestions!

All characters are fictional and over the age of 18. These events are intended to portray a sexual fantasy while intentionally not addressing the potential real life consequences and morality of such interactions.

Prologue

"Mr. Barton? Are you going to Chicago too?"

I looked up from my laptop to see the smiling facing of Avery Probst.

"Avery! How are you? What are you doing here?" I answered, not realizing that there were any army of girls standing behind her looking at me like I was from Mars.

"I'm heading to Chicago for a Cheerleading competition with my squad from school," she answered, gesturing to the pod of teenaged girls flanking her, all of whom had on "East High Cheerleading" warm ups on.

"It's called 'Chicago Cheer 2025,'" she continued. "It's a national competition--the best of the best. It's the first time our school has made the cut!"

"Congratulations! That's great!" I answered, smiling at Avery and her crew.

Avery was the almost 19-year-old daughter of my friends Lisa and David Probst. Her daughter and my only daughter, Lexi, had been friends since they were little. Now in their senior year, they were inseparable, with the exception of cheerleading. Lexi was a swimmer and field hockey player. Their differing sports interests were the only thing that kept them from being joined at the hip. In fact, I did recall Lexi mentioning something about Avery and her cheer squad when we were out to dinner recently. Chicago Cheer 2025 must have been what she was referencing.

"So, Mr. Barton, are you coming to Chicago to cheer us on?" Avery asked, her lips curling in a curious grin.

"Yes, of course I am. Lexi didn't tell you? I'll be in the front row all weekend! You didn't bring any East High stuff for me to wear?"

Avery broke out laughing and the girls next to her snickered in delight.

"I'm sure we can find

something

for you to wear to show your support, Mr. B. But really, what brings you to Chicago?" Avery asked.

"Work. A team I oversee is getting a sales award. I am heading out to support them."

"Awe, that's so nice of you, Mr. B," Avery replied. "Well, if you have some free time, we'll be in the convention hall at the Lexington Hotel tomorrow as of 8:00 a.m.!"

"That's actually where I'm staying! I'll try to stop by. The awards dinner isn't until the evening, so I've got nothing going on," I admitted.

"Well, now you do, Mr. B!" Avery said with a sly wink.

"Your parents aren't coming out, Avery?" I asked, scanning the seats at the gate for Lisa and Dave.

"Nope. Dad's working all weekend. He couldn't switch his shifts at the hospital. Mom is with my little brother at a soccer tournament. So it's just me...and the girls of course," she answered, once again motioning to the girls around her, who were now all checking their phones, having reached a point of sheer boredom with the conversation between Avery's and me.

"That's too bad. Well, I will text them to let them know I'm in Chicago too, in case you need anything. In fact, take my card with my cell number on it. Reach out if you need anything at all."

"Thanks, Mr. B!" Lexi replied, taking my business card. "See you in Chicago!"

I watched as the cheer team, seemingly led by Avery, roamed the gate in a large herd, ignoring the admonitions of their two coaches to sit down and be still. I didn't envy the coaches, having to wrangle over 20 high school girls from small town USA all weekend in one of the country's biggest cities.

I texted Avery's parents before the plane boarded to let them know I ran into her at the airport and that I am available if she needed anything. They each responded almost immediately, thanking me. They sounded relieved that someone they knew would be close by for the weekend.

The flight to Chicago was uneventful. I arrived at my room just before 6:00 p.m. with about a half hour to get ready form the welcome reception my company was hosting in the hotel restaurant. I heard giggling and music through the thin walls from the rooms on either side of me, no doubt cheerleaders from other schools at the competition. The halls were also filled with girls--and a few boys--talking loudly as they found their rooms. I imagined that they would all be turning in early to be at their best for the start of the competition tomorrow--or hopefully they would be--which meant quiet for my slumber. I chastised myself for thinking like an old man.

I showered and got dressed for the reception. I was putting on my blazer just inside the door of my room when I heard a group of girls chatting in the hallway.

"...He's really hot," a voice said.

"Total DILF!" Said another.

"Who?" Someone else asked.

"Lexi's dad! At the airport! Mr. B!" They cackled all at once at my Avery-given nickname.

The voices trailed off and became indiscernible as the girls continued down the hallway. I giggled to myself. At nearly 44, having a bunch of 18 year-olds admiring me wasn't too bad I guess. I kept fit, despite a crazy work schedule, not to mention vying for time with Lexi.

Lexi lives with her mother. We divorced 5 years ago. It was difficult for all of us, especially our only daughter. But Camille (my Ex) and I were committed to navigating Lexi through our breakup and maintain strong relationships with her, despite the breakup of our family unit. And we seemed to have done that relatively successfully. Lexi was at the top of her class and had a group of friends who would lay in traffic for her if she asked.

I did my best to spend as much time as possible with Lexi. Whether it was our weekly dinners out or the weekend or two a month that she stayed at my place, we connected and had quality time amidst our crazy lives. It wasn't perfect, but nothing is really perfect, is it?

Since the divorce, I didn't date much. A couple of attempts at relationships led to dead ends, unfortunately. I am not sure why I couldn't maintain an adult romantic relationship in the past five years. Maybe I was irrevocably damaged by the end of my marriage.

I shook off the fleeting admiration of Avery's teammates and headed to the welcome reception, which was nice but after a nearly full day of work and the flight to Chicago, I was beat. I headed back to my room and hit the sack, grateful for the silence in the rooms around me. Thankfully, the legions of cheerleaders who had raided the hotel for the weekend were fast asleep ahead of tomorrow's start of the competition.

Chapter 1: The Turn of the Ankle

I arose at 5:00 a.m. and went for a run along coastline of Lake Michigan. It was the perfect way to spend a Saturday morning, and the vistas of Chicago and Lake Michigan along my 5 mile journey on foot would make up for the lackluster corporate affairs that I must attend later in the day.

I ended my run early to get back to the hotel in time to shower and stop by the cheer competition for a bit to see Avery. I wanted to text her folks to let her know she was doing well in the Windy City with her team.

I arrived at the competition just after 8 o'clock. The conference hall was filled with dozens of cheer squads from around the country. I wondered if I would even be able to find Avery and her team amongst the hundreds of cheerleaders around me. I toured through the massive hall and eventually came upon the East High team warming up, but I did not spot Avery. As I approached the team on the floor, I was surprised to see Avery sitting in a folding chair off to the side while her team warmed up. Her right leg was out straight in front of her, her right ankle wrapped in an ace bandage. An ice pack sagged over the front of the bandage.

Ugh. She's hurt.

I thought to myself.

I approached the chair where she was sitting from behind and gently tapped her on the shoulder.

"Hey, Aves (The nickname given to her by my daughter), do I even want to ask what happened?"

Avery looked up at me and, staving back tears, told me the story. She had a mis-step during her warm up routine with the squad and rolled her right ankle. It swelled up immediately.

"I think I'm out," she admitted. The disappointment in her voice was palpable.

"I'm so sorry, honey. What can I do? Do your folks know?" I asked.

"Not yet," she answered. "This just happened like 5 minutes ago. I think the swelling is getting worse by the minute."

At this point one of the coaches walked over to us. We introduced ourselves. The coach just got off the phone with Avery's dad. He wanted her to go back to her room and elevate her ankle to keep the swelling down--sound advice. I was shocked that there weren't an army of trainers and tables around for injured participants. But it was so early in the day that the medical services weren't completely set up yet.

"Mr. Barton can you get me up to my room? That way coach can stay down here with the team," Avery asked. "The competition is about to start, and she has to figure out what to do without me. I'll be OK."

The coach, wary of sending one of her squad members away with a "stranger," looked at me in desperation, knowing that she had to scramble the squad to do their routine without Avery.

"I'm happy to help, Coach. Avery and my daughter Lexi are best friends. I am in Chicago on business, coincidentally."

The coach seemed relived at my serendipitous presence and was happy to accept my offer. We exchanged phone numbers to keep in touch on Avery's status, and the next thing I know I was helping Avery hobble up to her room to nurse her sprained ankle. She wrapped her right arm around my shoulders to keep weight off her right leg as I supported her torso with my left arm. She hopped along at my side to the elevators and up to her room.

The hotel room was a mess of clothes, makeup bags, phone chargers, and all manner of footwear. I cleared the almost covered floor as we moved from the door to one of the 2 queen sized beds in the room and gently assisted Avery onto one of the beds. She sighed in relief as I carefully lifted her right leg onto the soft comforter.

Once I got her situated, I called her dad and let him know that she was resting in her room. He was relieved that I was there and that she was doing ok, though he sounded like he was on the verge of getting on a plane and flying out here. I assured him that Avery was in good spirits and that the swelling seemed to not be getting any worse.

I confirmed that Avery had my number, got her some water, and was about to excuse myself.

"Mr. B, can I ask a favor?" she asked looking up at me, her eyes still saddened by the injury that began her day.

"Sure, Aves. Anything," I answered.

"I need to get out of these warm ups."

Fuck.

I thought.

How the hell am I going to manage this?

At that moment, there was a knock at the door. It was one of Avery's teammates and her roommate for the weekend, Jenna. Avery had left her bag down at the competition.

Thank goodness.

I thought.

"Jenna, can you help Avery get into some comfortable clothes? I am going to get some more ice packs and some Motrin at the drug store around the corner from the hotel," I said.

"Sure!" Jenna started to root through Avery's bag, looking for some comfortable sweats.

"How 'bout these, Aves?" Jenna asked, holding up a grey hoodie and oversized joggers. Avery nodded in approval, a look of disappointment welling up in her eyes.

I excused myself after grabbing her key card to the room so that Avery wouldn't have to get up when I returned, and made my way down to the corner drug store. I stocked up on ice packs, Motrin, gatorade, and snacks. By the time I arrived back at her room, Jenna had left and Avery had changed into the baggy waist length grey hoodie and sweatpants. She looked despondent after traveling all this way for the final competition of her high school career, only to be sidelined by a turn of her ankle.

I sat down on the corner of the bed next to her wrapped ankle.

"You hanging in there?" I asked.

Stupid question.

"I'm alright. Jenna cheered me up. She has her eye on a boy cheerleader from California named Dylan." Avery rolled her eyes and sighed. "That's our Jenna," she said. "Always has her eye on someone!"

"Do you think the swelling is worse?" She asked, changing the subject while looking down at her injured extremity.

"Can I take a look? I'm no doctor, but I've seen my share of sprained ankles over the last 43 years." I deemed myself at least a little qualified for this assessment.

"Be my guest, Mr. B," Avery answered. She pulled the cuff of the grey sweatpants up her lower leg, reveling her light brown sculpted calf, the product of years of cheerleading and other athletic endeavors.

I gently pressed on the ace bandage that surrounded her ankle, careful not to cause her any further discomfort. She winced a just a bit as I probed through the bandage.

"I'm sorry, Avery. That hurts?"

"A little...not too bad though."

She was being stoic, I could tell. Her wavy dirty blonde hair, which was in a bun when I left the room, now cascaded over her shoulders and down the back of the hoodie. Her big blue eyes conveyed a blend of sadness and physical discomfort with a touch of intrigue as my fingers cautiously examined her ankle.

"I'm OK, Mr. B. Keep going."

"I think the swelling is about the same, Avery. No worse. The new ice packs I got will help for sure."

I took an ice pack out of the back and hit it with my fist, activating the chilling agent. In an instant, the bean bag sized pack was freezing cold. I placed it on Avery's ankle, which prompted an immediate squeal from her.

"Fuck! Take it off! Take it off, Mr. B!" she exclaimed.

I flicked the ice pack to the floor. Her calf contorted itself into a ball, spasming in reaction to the sudden frigid ice pack.

"Ouch, ouch, ouch!" Avery shouted, rolling to her belly and almost kicking me in the jaw with her left foot.

"Get it out! Rub it out! PLEASE, MR. B!" she begged me, her breaths quickening.

I looked down at the spasming calf, which looked like a bag of quivering worms under her skin and immediately began to knead it with the fingers of both hands. The muscle initially felt like a rock but responded to my intervention, the knots gradually softening as my fingers worked.

After a minute or two, her breathing steadied and the muscle relaxed completely.

"Want me to stop, Avery?" I asked, worried that Jenna would come through the door and see Avery face down with my hands all over her right calf.

"No, no. It will come back--the spasm. Keep going for a few minutes, please. It feels so good."

"Sure, no problem," I answered, assuming my new hybrid role as an athletic trainer and massage therapist for my daughter'e best friend. I placed my gaze on anything I could--other than Avery. I looked at the bland artwork on the wall, the mess of clothes scattered about the room, the alarm clock on the night stand--anything but the 18-year-old cheerleader who was alone with me on her belly in a hotel room bed far away from home.

As the spasm ebbed from her exhausted calf muscle fibers, thanks to my ad hoc skills, I couldn't help but notice the bottom hem of her hoodie. It was a short cut to begin with--the style that all the girls wore these days. But the lower hem was riding up ever so slightly on her midriff, revealing her tanned, hour glass figure. The small of her back formed a symmetric valley that rose up to meet the rounded domes of her ass, the perfection of which could not be hidden by her bulky, thick joggers.

I looked away again, scolding myself for even taking a hint of pleasure from scanning the body of the injured girl--woman--in front of me. She moaned softly into the pillow in which her face was buried.

"Mr. B, that feels soooooo fucking good," she mumbled through the pillow.

"You had quite the spasm," I assured her. "I'm glad we could take care of it quickly. Sorry that the ice pack was so cold. I'll wrap it in a towel next time."

"OK, but not yet. Please keep going. I don't want my calf to spasm again."

"Of course," I answered, again wondering just how long it would be before one of her fellow cheerleaders would come back to the hotel room to check on her.

The muscle now was completely soft, but I dared not to have Avery admonish me for stopping the massage. Though my fingers were starting to tire, the toned yet supple muscle and the impossibly soft skin at my finger tips started to kindle feelings of desire deep within me. I allowed my fingers to travel up and down from the site of the initial spasm so that the entire muscle might relax. My fingers and palms roamed the entirety of her slender yet muscular lower leg, which became like putty in my hands, warm to the touch and limber.

Avery continued to moan into the pillow in approval, which only stoked the desire that was growing inside me. I closed my eyes as my hands continued their journey over her calf and thoughts of what the rest of her might feel like...the concavity behind her knee, the front and back of her thigh...her inner thigh...her...well, you know.

Stop!!

I scolded myself.

What the ever living FUCK are you thinking?

Shame quickly flooded my psyche as I abruptly stopped massaging Avery's calf and let it fall gently to the bed below.

She turned her head and looked at me, bleary eyed and drowsy from her muscle kneading.

"Why'd you stop?" she asked innocently, her eyes expressing her longing for more.

Because I want to fuck you. I want to fuck my daughter's best friend.

I thought, shame pummeling me like a tsunami.

"I think you're good," I answered. "I don't want to bring on another spasm with too much massage." That was probably bullshit, but I had to get my hands off this gorgeous cheerleader.

"Thank you, Mr. B. Will you check on me later?" she asked.

"Of course, but your teammates will be back later too," I assured her.

"Probably not for hours. The competition goes until 6, and then there's a dinner. I'm alone all day. And if Jenna has her way with Dylan...you never know."

"We can cross that bridge when we come to it, I guess," I responded, not wanting to entertain the thought of Jenna bringing a boy back to her shared room with Avery--and potentially displacing her for the night.

"I have to get some things done for the awards presentation tonight," I said. That was a lie. I had nothing to do all day until the ceremony in the evening, but I had to get out of this hotel room fast.

"But I can check on you later. Text me if you need me, Aves. You'll be fine."

"OK, Mr. B," she answered, her expressive eyes looking like a homesick puppy.

I wrapped the ice pack in a hand towel and helped Avery turn over and sit up in bed. With her drinks and snacks next to her and the ice pack in place, she would be good for a couple hours.

"All set?" I asked, placing my hand on hers.

Why the hell did you touch her?

She squeezed my hand and said, "Yes Mr. B. Come back soon?"

"Absolutely," I answered. I gave her a smile and was off.

I returned to my room, which ended up being just a few doors down on the same floor as Avery's, and collapsed in the bed. I texted her coach to let her know Avery was relaxing and doing well.

The events of the morning swirled in my head, assaulting me. Everything had started off fine. I had a great run and, for some reason, had to stop by that cheer competition.

She's not even my kid, for fuck's sake! Why did I stop by that competition?

But then I realized it was probably good that I was there. There were only 2 coaches, and without her folks, Avery needed someone there to tend to her and her injury.

But the hotel room, the bed, the spasming calf, her face down on the bed...her moans...her skin...