Cheerleading Drill Team

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Status: Finished  |  Genre: General Erotica  |  House: Booksiesilk Classic Group

Affirmative action at my college let me join the previously off-limits cheer squad. And did the girls make me welcome? Hell, yes.

Back in College, I was the only guy nominated for the 1991 season cheer team at our college. So, you can imagine the ongoing ribbings I got from my mates instead of choosing basketball, or even lacrosse or badminton before ‘cheering’, let alone the snide remarks from the footy jocks and the threats if I even looked sideways at their ‘women’.

 I just liked gymnastics, and given that our college didn’t have a team in that sport, I gravitated naturally to the cheer team. I hadn’t had the guts the previous year, but in my senior college year and technically an adult at eighteen, I decided to do what I wanted and screw the peer pressure. It was better than being the footy water boy, being named an ‘emergency, emergency’ and never getting game time. And besides, I naturally liked girls, not just for sex. They were great social company. Okay, I wanted the cute little cheer squad member, Toni.

Our college was also, at the time, deep into a new affirmative action program; for girls in particular. The ladies were doing automotive; design in wood and metal classes and were outperforming plenty of guys. The pastry and cake classes had also got a couple of guys last year, which pleased the affirmative do-gooders. Still, they suddenly knew they needed a reverse-reverse gender discrimination policy as girls dominated the honours board and the practical traditional male skill areas. However, gender segregation still ruled more than the toilets and change rooms at our college and in the minds of most of my peer-dominated boys and girls, they were stuck in the traditional man/woman future paths. Okay, I suppose here, so was I; I’d end up too driving in my family trucking business.

You can imagine how weird it was to attend my first non-compulsory cheer drill training session. Some girls wanted to get the season off to a flyer and seemed very committed. Especially cheer captain, the stunning blonde Heather and her bestie, Abigail, the athletic brunette.  I wanted to make a good impression on the girls and convince them I was serious and not just here to perv up their short skirts; if I got to lift them. However, it led to an incredible wet dream the other night. There was cheerleader Heather in her Chieftains uniform, sitting on my face. Her thin red cheer lyrca rubbed right into my tongue. I was about to pull her knickers to the side when I gushed under the sheets. Messy but breathtakingly strong. I wondered why the wet dream hadn’t been of Toni. Was I after the wrong arse?

Just as I entered the changing room, I saw a group of several girls approaching the change block from the main school area across from the oval. I hesitated. Should I stay outside and introduce myself or wait till I changed into my cheer gear? I chickened out. I went inside the guy’s changing room.  I felt I could handle myself in my cheer colours. I’d be the same as them. All of us in uniforms. A team member. None of us guys or girls, just team members. I could only hope for acceptance; otherwise, I’d be left with an expensive uniform and another year as the water boy.

Weirdness hit me; being in a changing room alone. I was used to male banter—the smell of socks and jocks and liniment and tosser comments. Complete silence greeted me as I started to undress to change into my new cheer uniform for The Chieftains. Yeah, the colour scheme was a bit corny, white at the neck and short sleeves, a bright red dominating the rest of the top apart from two downward black stripes with the Chiefs emblazoned between them. Then long black pants. I’d cope. The special underwear had me. That was a surprise and got me thinking of the girls, too—microfiber with moisture management for guys. I’d have thought that would be for the girls. Plush tight elastic waist, well, I suppose I needed that. Moisture management? I guess we really worked out.

As for The Chieftains, political correctness redacted the logo to The Hawks by 2005.

I knew the chicks’ uniforms were hotter. They always are with cheering. Well, you can’t hide that the focus is on the lasses. I remembered starring too long the previous year, at petite Toni’s boobs nearly bursting out of her top during a strenuous halftime routine. Though I heard they had a new design for this year; some motion-wear stretch tops, lycra or spandex. Who cared? The girls always looked great in their cheer uniforms.

I had my gear off; I was naked. Then, finally, I was ready to change into my new tight-fitting underwear. Then the rest of my uniform.

It was so quiet that I heard the growing chit-chat as the girls came in next door in a boisterous group. I realised there was only a brick wall between me and watching the girls change. However, as there was no noise on the boy’s side, I was suddenly privy to the girl’s increasingly distinct conversations and to my surprise, they centred on me, not their jock boyfriends.

 “Joel, Joel Palmer? What are we going to do with Joel?” it was Heather’s distinct soft lilting voice.

“Oh, come on, Heather,” and I recognised Abigail’s silvery but firm tone, “I think you want to set up poor little sex-starved Toni with the perving prick.”

“Yeah, sure and watch you join in;” Heather got back fast.

“Well, hey, he is cute,” from someone I couldn’t recognise. But the sound was easy on my ears.

Then in the sweetest, most appealing voice; Toni and well, I liked what I heard; “Girls, you don’t have to push his cock into my butt; I’m perfectly capable of directing myself there. Now he’s on the cheer squad. I like him.”

“Oh, you like him,” it was a chorus of voices; “Oh, she likes him;” it was like a cheering chant.

Then that voice I couldn’t place: “I bet your butt will like him even more.”

Lots of twitters and sniggers and voices over the top of each other.

Then a voice quieted them all; ‘Well honey, let’s go get him.”

Fuck I knew the tone but couldn’t place a name; I had her goddess-gorgeous pixie face, with her short dark hair and almond eyes. The smoky, sexy voice of a girl so seriously out of my league that I usually dropped my eyes in the corridor when she passed.

Then all I heard was a strong female togetherness: a raucous but sexy cacophony:

Cheer for the Chieftains. We are the best,

A better team you’ll never find

Put us to the test

Yeah, we know how to grind

What the fuck, I thought; I was privy, getting their dirty secret cheer.

We’ve got the pussy power

We love to suck on cock for hours

What the fuck? I was muddled. Where were the girls? What were they doing? Their dirty ditty was getting closer!


We love having our arseholes deflowered.

Yeah, our sweet butts greasing your manpower

God, they sounded like they were just outside my changing room. I was frozen in exposed guilt.



Here we come. Here we come.

And you will...CUM... CUM... CUM... YUM.

I was fuckin caught fully naked. Several cheer girls in their underwear, not their cheer uniforms, were in the male changing room with me.

“Oh, you dirty, dirty eavesdropping boy,” from the sexy smoky voice of Talia. I remembered her name, “but you’re forgiven, as you’re nicely hung.”

The first time the bitch had even spoken directly to me in over five years of high school and college.

I knew I’d never forget her high-cut black G-string and stunning black sports bra barely containing her delicious tit wobble. Her short hair was so sexy, too—my college’s undisputed goddess.

“And getting up fast without any help,” from the luscious Toni, whose tits looked so inviting in her white lacey big boob-defining bra.

Heather Devine, who was currently looking divine in red matching underwear, well, that was a misnomer because they were strategic pieces of clothes hiding nothing. I had the passing thought, what is it about college girls and matching underwear? But I knew the answer; it’s just frickin sexy. God, she was flaming hot; the red fabric matched her lipstick. Her blonde hair flounced. Her tits looked like they wanted to be free. I could only hope.

Only later on reflection did I place the rest of the cheer squad girls. First, there was Abigail Thomas, a crisp white high-cut thong accentuating her hips and her pubic puffiness. Her bra, well, not quite matching, but very eye-catching. White with a thin apple green trim and a cute central petite pink bow, where her ample boobs were nicely separated.

Serena Jones, dark-haired, mauve, or light mulberry underwear. Too much eye candy to take in as the cheer squad well pressed in on me, and Toni was pashing my mouth to my tonsils. And someone grabbed my erect cock, and someone else cupped my nuts, and God knows who squeezed their soft big tits into my back. And Abigail, yes it was Abigail, guided my hand to her nipple under her bra.

Andrea, yeah, Andrea from my Chem class lost her knickers and bra first.  Pert cute boobs. And her sweet pink nipple was given to my seeking tongue as Toni went down on my stiffy, sucking my cock; with Abigail then joining in; teasing my balls with her long raking fingers, an exquisite surprise and a stunning one as her tongue sauntered around my nuts.

“Enjoying yourself, you dirty perv;” it was the sultry smoky Talia in my ear, and I assumed it was her finger in my bum as my cock shot forward deeper into Toni’s accommodating mouth.

“Steady girl,” Talia urged Toni not to over-excite me. It was nearly too late for that. But I was in good hands. Plenty of hands as they got me lying on the bench, and hands explored everywhere on my body except my cock. It was Janice Grey, now naked. No idea what underwear she had come into the changing rooms with, but her nipples were now circling my nipples. God, it felt both kinky and arousing.

I was horizontally prone, excluding my ceiling vertical pointing boner. Toni, it seemed to be about the girls supporting Toni, who was suddenly sitting over my face. Her smooth girly region was so soft against my face and open mouth. My tongue was allowed to catch her pink dangling open flapettes as she teased me. Giving me her pussy to lick and then withdrawing it. Then giving it back. Then she was face-sitting me. I loved it. I pushed my tongue into her pussy and clit as she ground into my face. What a grind. What a grind. She knew how to grind into a face and tongue.

Some unknown bitch was teasing my cock with their tongue. Some unknown filthy slut was fingering my areshole. Some lovely skank somehow had a tongue in there, too, sweeping over my hardening tightening ball sack. Talk about a cheer team drilling to the essentials together.

I heard Talia say, “Oh, share his frickin pecker, girls; let’s do this as a team.”

I became aware of a series of mouths taking turns on my cock. Each was warm and sensuous in their sucking action, but each individual in their tongue play and intensity. My cock loved every unseen cheerleader taking their turn.

 Talia said, “Toni, Toni, honey, you’re over ready; sit on his cock; now, honey.”

And my face was free, and my eyes took in tits and shaved and trimmed pussy everywhere. God, Heather looked great down there. Just a light blonde landing strip above her pink crinkled opening. Talia Heath, well, I only caught a glimpse of her nether region, and boy, was she shapely down there. Eye-catching unique lips and a clit pressing out under her cowl. Then Toni, sweet dream, masturbatory fantasy Toni, was poised over my cock and then riding it in one occupying motion.

“Oh, shit yeah...oh yeah,” I managed.

 My pecker nicely slotted in her slit.

“He likes it,” said Serna Jones.

“He better,” panted Toni, really riding me, “I’m putting frickin effort into this...oh Mmmh...Mmmh,” she went.

She was drilling down and then tugging up repeatedly with my cock and building friction. She was panting.

“Oh, help the bitch;” said Talia.

And suddenly, Toni’s body had two assistants, Janice and Andrea, helping to tug her body up with my cock and press it right down to a grind against my pubic bone. So sensational. It meant the speed of the sex was insanely fast. My cock was like a greased piston being turned up to maximum pumping. My dick was working like a pump-action shotgun in her lovely pussy. Back and forth, back and forth. My pecker slid in the generous seductive juices of her flesh tube.

My work rate in Toni’s hot pussy got even more manic as I saw Heather play with Abigail’s lush, bountiful, bumper breasts.

“Oh girl, girl, he won’t last,” it was that bitch Talia again, “Give him your arse before it’s too late.”

Suddenly Toni was off my cock. She was bending over, presenting her cute little arsehole to my dick.

“Oh god, girl, you novice;” said Talia, the choreographer of my sexual induction to the team, taking stock of the proceedings; “He has to prep your crack first, sweetie; otherwise, you won’t want his pecker in your butt ever again.

“Finger her butt, lick her butt, gape her butt, dude”, Talia instructed me.

Talk about easy instructions to follow even if issued by the seeming cheer dominatrix.

Toni quickly understood the pleasure and benefits of arse prep as much as I enjoyed giving them. I licked her cute, tight little pink hole. So tiny. Surely it couldn’t take my cock. I’d never seen a butt hole so small and tight. I spat in it. I worked my tongue round and round while the cheer team cheered me on. The skank whores were all watching their friend get her butt licked out. Though I noticed fem-hands and fingers were straying to each other’s tits, butts and pussies: the bi-sluts.

I was too busy with Toni’s slowly giving arse to worry about which girl was touching which girl. Though I gave Toni a rapid series of tongue injections straight up her arsehole as I saw Abigail finger Heather’s indented tight pink starfish out of the corner of my occupied eyes. I did, however, focus back on delightful Toni’s tiny butt hole.

I thought Toni’s butt wouldn’t manage to take even my delving crooking finger, but it did. It slipped into a giving space.  Then I had a second finger gaping at the lass. Her soft moans turned to more resounding groans.

It was, of course, bitch princess Talia who told me to hold the sweet innocent Toni’s butt hole open with my spread fingers while she generously spat in it and made the rest of the team, in turn, spit in their friend’s arsehole too. Janice, in particular, really enjoyed shooting off a big dribbly gob full into Toni’s poised posed pucker.

I saw a slurry of filmy spit splattered in and lining and churning in Toni’s now-ready butt hole. Then, finally, it only remained for my cock to enter her back pleasure wonderland. She was eased down over my dick by the supporting cast of Heather and Andrea.

“Just rest over it, honey,” instructed Talia, “rub your arse rim around and over his knob. Let your arse find its natural gape.”

And it was terrific. Toni hovered her butt crack over my cock knob supported by her cheer team. Then I was edging in. My tip was welcome in her little hole. Then my knob had access, and it was paradise. Cock bliss. So tight. So frickin tight. Admission where I hadn’t believed it was possible.  God, my cock felt great. Tucked comfortably in her rear end.

“Spear the bitch; boy,” said Talia.

I was going to anyway, but it was nice being told. I gouged my cock in deep and found Toni’s inner recess of space while her tiny crack expanded to the shape of my hard pecker. I could feel her arse-hole flesh ringing my dick. Then I was cock drilling her arse without thrusting. The girls around her lifted her body up and down off my cock. Unimaginable pleasure, except it, was happening. I got to drill the sweetie with the helping hands of her filthy cheery squad.

The girls pounded Toni’s arse up and down off my cock. Then, Serena and Abigail arched her body back to the cusp of my knob, digging in at an acute angle in her micro, marvellous, minuscule pink hole. Heather and Janice, next, took her forward so I could see, and the skank tarts too, my cock burrowing in and out of her narrow yet stretched, resilient, yet; fixed constriction.

“Do we get his cum;” said Serena, while fingering herself leisurely with her middle finger in her perfect shaved slit indented in her puffy camel toe; looking at Talia.

I personally didn’t care who got it, but it would have taken a good effort to prise my cock out of Toni’s fabulous arse.

“Not today, our sweet anal virgin gets her first back-door cream pie, “added the richly mysterious-eyed maestro of the cheer team.

Oh, I didn’t need to be told what to do. I couldn’t have controlled myself anyway. I filled the cutest tightest arse of my life, to that point, nevertheless, with load after load of jizz. I groaned. Toni above me kept moaning.

I was done. I was sweat lathered. So was Toni. But Talia, the diva of this squad’s kinky complicity, ordered every team member, apart from herself, to lick clean buggered little Toni’s cute cum oozing arse; as it was placed directly over my face.

I never knew other girls could enjoy a girl’s arse so much. Wow, did Andrea have a long-curved tongue seemingly perfect for arse licking and cleaning? Toni’s puckered pink pop hole was made pristine. Just slightly wet and shiny.

Then I hadn’t realised it, but there was only Talia, and Toni’s now sparkling clean arse gape left in the change rooms because I became aware that each girl had taken some male liquid bliss on their tongue; they had quietly scooted off.

“Off you go, girl, we have cheer practice,” Talia said to Toni.

And Toni picked up her underwear and scampered off next door with a cute wave to me.

Talia, the bitch, I noticed, was already back in her underwear.

She looked me over.

Then said: “Get up, get clean; you have serious cheer routines to get through.”

I was up and putting on my cheer under gear. Well, I belonged to this team now.

“Nicely drilled,” she said, in her smoky voice, her glinting almond eyes giving nothing away as she turned to leave.

Of course, I looked at her black G-string cord, sitting deep and disappearing in her crack as her sublime arse moved away from me.

She looked back over her shoulder from the entry door, her almond eyes smoking; “Steady stud, all good things come to those who drill and drill.”

“Oh sure,” I said, “I’ll practice hard; I so want to be a part of The Chieftains.”

My pants were hitched up.

She smirked; “Yeah, boy, you will drill all right, right through this team, as I say so and if you are a really good, good boy, no, make that a bad, filthy, remorseless, twisted, bent, sexual miscreant, just maybe, just maybe, you’ll get even to lick my arse.”

The practice was a blur. They drilled me seriously hard to get me on the path to being ‘up to speed’ in the authentic skilled art of cheering.

But now, many years later, what sticks in my mind, apart from Toni’s ‘just right’ tiny arse making my cock sensationally happy, is Talia’s arse sauntering away from me. Talia’s arse. Yep, what an arse.

But to tell the complete story of Talia, I need to disclose fully what happened next, and for the moment, I’m happy recalling Toni’s petite pink pucker. A perfect sequence from here, though, was set in train by Talia: and each cheer girl deserves their story in my sex life; Andrea’s long curving tongue, Janice’s super nipples, Serena’s beckoning slit framed by her perfect pushy Venus mound, Abigail’s voluptuous boobs made for titty fucking and absolutely everything of Heather’s beckoning tempting body. Still, even then, the inimitable, exceptional Talia will take some telling...please wait; it will be worth it. And the longer you wait, just as I did, the more you will appreciate it. Trust me, I know.

Submitted: January 10, 2023

© Copyright 2023 Janus. All rights reserved.

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