Chicago Cheer 2025

This entry marks my 20th submission to Literotica. I am grateful for the support of all the readers who have chosen my stories to enjoy. Please keep the feedback coming! I look forward to my next piece, which will be a bit longer, but hopefully just as intriguing as my body of work thus far!

--Dani

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.

We kissed before I left, and I promised her that I would get her back to her room when I returned.

I was about halfway through my work ceremony when I got a text from Avery:

"Jenna is bringing Dylan back to our room tonight. Can I stay in your suite?"

I replied, "Of course you can sleep in my room, Aves!"

She replied, "Sleep? Fuck that! I have plans for you...."

This might just be the best work trip ever....

=====================================

I didn't know how to respond to Avery's last text, so I didn't. I just relived each delicious moment we shared in my hotel suite just before I left for what ended up being the longest awards ceremony ever. As district managers from seemingly everywhere in the country presented their plaques, made speeches filled with clichés and corporate lexicons, and floated lame and sometimes cringy jokes, I shifted in my chair, the events of the day playing in my mind.

Sluggish minutes became nearly stagnant hours. My mind returned to Avery again and again as the evening crawled. I returned to the moment where I saw her differently for the first time, massaging her spasming calf, my hands adoring the unworldly smoothness of her skin and the supple muscle underneath.

Then later, in my room, the moment when our eyes locked...followed by our lips....the primal need in her expressive blue eyes...her taste...her skin against mine..her moans as I found her center...the way she came around me...her deepest recesses drawing me in and draining me...the look on her face as her orgasm ebbed...the way she laid in my arms.

I shifted again in my seat, my cock twitching while each memory spun like a carousel in my mind. I realized I couldn't stay in this dreadful banquet room a moment longer. I felt my phone vibrate in my pocket. It was a text from Avery.

"Heads up. Jenna is hanging out with me in your suite. Apparently things did not go well with Dylan. He turned out to be a douche canoe."

I wasn't familiar with the particular term "douche canoe," but I was picking up what she was putting down, so to speak.

Avery continued, "So we are just here hanging out in your room on our phones."

The anticipation of my return to my room--to Avery--instantly vanished at the thought of the two 18 year-olds scrolling through their phones in my room.

Another text came through from Avery.

"By the way, I told her. I told her what happened before you left for your work thing."

I couldn't believe that words I read. My stomach sank to the basement as I quickly answered, "Told her WHAT??" I closed my eyes and waited for her reply like I was waiting for biopsy results.

"I'm fucking around! Of course I didn't tell her, Mr. B!"

Relief washed over me like a warm, soft wave.

Thank goodness.

"I didn't have to tell her. She knew. She came right out and told me, 'You're glowing--like you just got fucked.' So much for my poker face."

All at once, my warm wave of relief was pummeled by a tsunami of shock.

My fingers felt numb as I tried to type a reply. If Jenna knew that I fucked Avery, the entire cheer team--and possibly even the coaches--might know as well. My heart rocketed to my throat, the gravity of the situation erupting in me as my co-workers stood next to me to receive their sales award.

"You alright, Mr. B?" Avery texted.

I didn't know whether to call or text her. I figured I would yell if I called, which would draw attention, so I texted back.

"So Jenna knows?????"

"Yeah. There was no hiding it from her. I'm sorry, Mr. B."

"Avery, PLEASE SAY YOU ARE FUCKING WITH ME!"

Her response was immediate. "I'm not. But we're all good, Mr. B."

"Good, Avery?? How are we good? Your friend--who is Lexi's friend too--knows that we....you know...that we did IT. Can you imagine the consequences?"

"I'm nearly 19, Mr. B. It happens. Sex happens. It happened....and it was fucking awesome. Plus, there's a silver lining."

I was certain that there could be no silver lining in this situation. I fucked my daughter's best friend and now another 18 year-old knows I did.

I

was utterly fucked."

"Silver lining, Avery? WTF?" I hit send and nearly shattered the glass on my phone screen.

The ellipsis indicating that she was typing appeared and disappeared, then appeared again, then disappeared one last time before the next text came through.

"Jenna wants to fuck you," she texted.

I couldn't believe what I was reading. Things were completely out of control. I had to end this insanity.

"Avery, are you nuts??? I won't...I can't! This is lunacy!!!"

I had to sit down and catch my breath. This text exchange was exhausting. I turned my phone away so I couldn't see the screen. I felt a buzz and turned the phone over.

"You can, Troy. Fuck her."

Then a moment later: "Come up to your room. We'll be waiting."

"Troy! That's your crew!" A colleague sitting to my right jabbed my arm. I immediately stood and clapped as my team approached the stage, my phone falling from my lap to the floor. I immediately dropped to get it, banging my head into the chair in front of me as I reached for the carpet to collect my phone.

"You OK, buddy?'' he asked.

"Yeah, yeah. I'm good. Just proud of the team." I resumed my applause until the awards were distributed to each member of the team. After they returned to their seats, I gave them a collective thumbs up, pointed to my phone, and mouthed "family issue."

They all nodded and returned the thumbs up. I bolted from the ceremony and headed to the elevators.

On the elevator ride up to my floor, the absurdity of the situation inundated my brain. I had the audacity--and stupidity--of allowing myself to be seduced by someone less than half my age. Or did I seduce her? If I did, that's even worse! The events surrounding my encounter with Avery were now a blur.

I walked down the hall to my room with a plan: I would just let Avery and Jenna spend the night in my suite. It would be more comfortable for Avery and her injured ankle anyway. I would sleep in their room--alone. No more antics. Period. That was my plan.

As Mike Tyson once said, "Everybody has a plan until they get punched in the mouth." I was about to get punched in the mouth--twice.

I entered my hotel suite and before me were Avery and Jenna, sitting up in my bed and smiling. Jenna must have grabbed Avery's clothes from their room because she was no longer wearing the baggy sweats. Instead, she was wearing white athletic shorts and a white tank top. The outfit perfectly contrasted her tanned skin and the shorts revealed almost the entirety of her toned thighs as well as the very bottom of her ass. Her wavy dirty blond hair cascaded down over the gentle curves of her bare shoulders. My cock swelled at the mere site of her. That was the first punch in the mouth.

The second punch came from Jenna. She was lying in my bed wearing a short, sheer black dress. I could faintly make out her skin through the fabric, except over her breasts and pelvis. It was sleeveless with a boat neckline and a hem that fell just above the knee.

Jenna was one of the most dedicated cheerleaders on the squad. A former gymnast, she was about 5'2" with a muscular build. Though she wasn't as curvy as Avery, she was still singularly feminine in her compact frame. The swell of her small breasts filled out the front of the dress and created a shallow valley that disappeared under the bust of the dress. The length of the dress showed off her toned thighs and calves. She had straight black hair in a bob that went just above her shoulders, olive skin, and hazel eyes.

She crossed her legs on my bed and looked me square in the eyes.

"Dylan is an asshole," she announced.

"I heard, Jenna. Avery texted. Guys suck--not all guys--but most," I felt the need to explain the shortcomings of the male sex.

"It happens," I continued. "But at least you found that out before things went too far, right?" I tried to reassure her as much as a guy in his forties could.

She looked down at the bed and then back at me intently, as if she was peering into my soul. I felt completely exposed and vulnerable. I sat down on the chair next to the bed without getting too close.

Jenna turned her body towards me on the bed, her legs now dangling over the side. Her right knee grazed my pant leg as she changed her position. I not so subtly pulled away.

"What else did Avery text you, Mr. B?" Her voice was low. Her words were dripping from her lips and her eyebrows raised in unison as she asked me the question.

Every molecule of hemoglobin drained from my face. I prayed that I misunderstood what Avery texted me minutes before. But there was little chance of misinterpreting the message that Jenna wanted to fuck me.

"It's not right, Mr. B," Jenna stated, crossing her legs, the mini dress riding up her sculpted thighs.

"I know, Jenna," suddenly feeling the need to apologize to Avery's friend, as if that might make this awkward moment disappear.

"I'm sorry. It just happened between us---between me and Avery." I was growing paler by the moment.

"No, Mr. B," Jenna continued. "It's not fair that Avery gets you all to herself." She leaned over to me so that her lips were inches from mine without breaking her gaze into my eyes.

"Jenna, I think you're just upset about Dylan," I suggested, nervously.

"Fuck Dylan," she retorted.

I could see Avery watching this exchange, sporting the same mischievous grin from when I went down on her a few hours before. She loved the seduction that she was witnessing--a seduction that she happened to be facilitating.

Jenna leaned in further, her soft lips grazing mine. She spoke one last time, tilting her head. "Avery's gonna watch me fuck you, Mr B."

And with that second punch, my resistance, my self control, and my restraint evaporated. I came to my knees on the floor in front of her. She uncrossed her legs at the edge of the bed and spread them, allowing me to nestle in between them.

My erection surged under my dress pants as she devoured my lips while undoing the button on my pants and unzipping my fly. I've heard the sound of a zipper coming down thousands and thousands of time, but this time it sounded so provocative as this teen's curious hands were started to invade my underwear.

She briefly traced the outline of my erection as it strained the fabric of my briefs. She then placed her palms side by side on my lower abdomen and deftly slid her hands downward, her fingers slipping effortlessly underneath the waistband. To my surprise, her hands coursed around either side of my cock and continued down below the base to my inner thighs.

She looked into my eyes as her finger tips barely touched my scrotum. She moved her fingers over the folds of my sack and sent unimaginable pulses of erotic bliss to my core. She hadn't even touch my cock yet and I was nearly paralyzed by the meandering tour her finders were taking. My balls tensed as her fingers grazed me. She resumed nibbling at my lips.

"Fuck, Jenna, that feels amazing," I moaned, feeling a stream of precum saturate the front of my briefs.

I ran my hands up along the outsides of her thighs. They felt like heaven against my palms and pushed my erection further up against the straining fabric.

I kissed Jenna, my tongue parting her lips and exploring her mouth as her tongue swirled around mine. My hands slipped under the hem of the dress to her hips, the dress traveling up as my hands went further north and explored the curves of her torso.

Her left hand continued its mastery over my scrotum while her right hand found my base. She gently gripped me and started to stroke me slowly, stopping at the tip to allow her palm to collect precum to coat my shaft as her hand returned slowly to my base. She did this a few times as my moans grew louder. She paused for a moment to tug my waistband down, allowing my cock to spring free.

She raised her arms while I promptly relieved her of the little black dress and cast it on the bed. Avery smiled in approval, her friend now almost completely naked, save for her black lace bra and panties.

"Let me help you with that," Avery said, coming to her knees behind Jenna and undoing her bra clip. Avery's hands came up over Jenna 's shoulders and the bra fell free, revealing the petite mounds that were her breasts. Her small brown nipples became erect before my eyes.

I took the entirety of each breast in my mouth, first the right, then the left before finishing at her peaks, flicking each firm nipple with my tongue while both Jenna and Avery moaned in approval.

Avery stayed behind Jenna, gently cupping Jenna's upper arms in her hands while her thighs flanked Jenna's hips. She put her lips up to Jenna's right ear.

"Want me to tell you what to do, Jenna? What to do with Mr. B?" she asked, whispering in Jenna's ear and nibbling around its outer rim.

"Hmm hmm," Jenna replied, deep in a kiss.

Avery continued, her voice barely a whisper, "I want you to suck his cock. I didn't get to before, because he ate my pussy until I came and then he fucked me." My cock ached hearing this 18 year-old goddess who I fucked a few hours before her tell Jenna what to do to me.

"I want you to be the first one to suck his cock," she continued. Avery rose to her knees behind Jenna, still holding her shoulders gently in her hands. Her thighs slid smoothly along Jenna's hips as she rose to look me in the eye.

"Stand up, Troy," Avery commanded, softly but emphatically.

I complied. My erection was now squarely in front of Jenna's face.

Jenna looked up at me, her lips millimeters from my purple hood.

"Say 'please,' Jenna," Avery insisted.

"Please, Mr. B," Jenna said softly. My cock twitched, feeling her breath on my tip.

"Please what? Jenna," Avery asked.

"Please may I suck your cock, Mr. B?"

All I could do is nod "yes." I had no words for the fantasy that was unfolding before me.

Jenna gently gripped my base while she place a soft kiss on my tip. She then continued to kiss along the entire surface of my glans while gently stroking my shaft. It was pure ecstasy. I couldn't take my eyes off this bombshell cheerleader as she began to work her oral magic. She was just getting started and it was already the best oral sex I have ever had.

A steady stream of precum greeted Jenna's lips as she took me to new heights of pleasure. When her lips parted over my tip and her tongue grazed my frenulum, I let out of series of moans and expletives. She continued to take me in until her lips met her hand at my base and then she slowly withdrew my shaft from her mouth, her hand following along, continuing to stroke my now slick cock. It was a simple and effective maneuver--slow deep transits of my cock along her lips and into the depths of her pharynx while Avery stroked Jenna's upper arms from behind.

Jenna continued to work my cock with her mouth for what was the best few minutes of my existence. My lust boiled over as I took Jenna's head in my hands and pistoned slowly but deliberately in and out of her mouth. I fucked her mouth as she moaned around me, a soft sucking sound accompanying each invasion of her oral cavity. I could feel my climax welling up as Avery watched intently.

"Mr. B, do you want Jenna to make you come with her mouth?" Avery asked. She was now kneeling up behind Jenna, nearly face to face with me.

"Yes, please," were the only words I could muster.

Avery's lips returned to Jenna's right ear. "Make him come, Jenna," Avery whispered while looking up at me lustfully.

I let my hands fall to the side but then immediately felt a bit light headed while Jenna quickened her pace. I steadied myself by grasping Avery's upper arms and closed my eyes, allowing my impending climax to build. Her tongue began to swirl around my bulging veins, discovering every contour of my slab as I reached the point of no return. She deep throated me as my climax shot through me.

"Jenna, I'm coming!" I moaned. Jenna released me from her mouth. The first wave erupted from my tip and painted a white rope of cum from her forehead diagonally over her nose and down to her lips. A second rope landed on her right cheek and chest and also doused Avery's right hand. Jenna deep throated me again before the third wave coated the back of her throat. She swallowed multiple times as I emptied my balls into my second cheerleader in a day.

I fell to my knees breathless, cum oozing from my glistening cock. I just ejaculated on two of my daughter's friends in a hotel room in Chicago. Avery licked the little bit of my semen from her hand and left Jenna to get a warm washcloth from the bathroom.

She returned promptly and helped Jenna clean my seed from her face. She giggled, "Mr. B, you just fucking came on us!"

I was again without words. "I'm sorry, ladies..."

"Stop Mr. B!" Jenna interjected. i wanted you to come on me. I felt it happening. That's why I pulled you out. I didn't mean for Avery to take some of your load, but hey, she was in the line of sight, right?" Both girls laughed. I was again in disbelief over the whole interaction. They were cleaning my ejaculate off themselves while joking freely about it.

I stood up slowly while the girls cleaned off, wondering what would happen next. After they finished, Avery returned to the chair where she was siting earlier this afternoon. Jenna moved to the center of the bed. I kicked off my pants and shoes and unbuttoned my shirt. Moments later I stood completely naked with a fresh erection in front the two beautiful young women.

Jenna gave me the same lustful look that Avery had given me earlier. With that, I knew what my role was. I would totally dominate her.

"Turn around, Jenna," I commanded softly.

She immediately complied, coming about on her knees and facing away from me and Avery. I climbed onto the bed and placed a series of kisses along her shoulders while my hands roamed along her taught abdominals. I pulled her underwear down over her smooth thighs. They fell around her knees on the mattress. I would leave them there.

I lined up behind her and looked back at Avery, who was smiling her approval. Jenna obediently came down on all fours. I held the base of my cock and guided my tip from the small of her back down between the domes of her ass and settled my tip at her sex.

I paused for a moment and saw her head drop as my tip explored her outer lips and continued along her inner lips before pausing at her opening. My tip parted her inner lips and slowly disappeared into her tight little hole. A tight ring greeted my tip and then gave away to firm yet velvety smooth walls that hugged my shaft as I gradually buried myself inside her, tidal waves of pleasure assailing us both.

"Jenna, you feel incredible around me," I gasped.

"Mr. B....fuck...fuck...fuck!" was all she could say, her breaths ragged.

I looked back at Avery. She was exploring her own body as she watched her teammate start to get fucked. Her hands were under her tank top caressing her breasts. Her erect nipples made indentations on the white athletic material.

I pistoned in and out of Jenna slowly as she adjusted to accommodated me. After a few minutes of gentle thrusts, we were both ready.

I placed my hands upon her hips and buried my entire length into her. I held her steadfast as I continued to fuck her. We each exchanged expletives as my thrusts grew in intensity and fervor, our skin slapping together rhythmically as lust devoured us. Our moans turned into soft screams of pleasure. I quietly hoped that none of the coaches happened to have the rooms on either side of me.