The Cheerleader - Cover

The Cheerleader

by Jimmy Lee

Copyright© 2025 by Jimmy Lee

True Story Sex Story: The bitch head cheerleader in high school has turned hooker. I pay her pimp and get revenge for her previous behavior toward me.

Caution: This True Story Sex Story contains strong sexual content, including mt/ft   Reluctant   Heterosexual   True Story   Humiliation   Rough   Anal Sex   Oral Sex   Revenge   .

I’d heard she’d turned to being a call girl, and I’d seen her around town wearing expensive furs and jewelry she could have never afforded on her own, but apparently she couldn’t even stay at that level.

She had been the head cheerleader in high school, only dated the quarterback, and routinely fucked the entire team (so I’d heard), but she would never look at me other than with disdain, and never made a sound in my direction except for one time. “If you ever speak to me again, I’ll have David (the quarterback) beat the shit out of you.” That from a simple, “Hi” one morning passing in the hall. Not much fun being the only nerd in a football school.

And holy shit, here she was naked in bed in front of me. “Hi, Francis,” I said with a smile.

“No way, Jake. No way is this puke fucking me,” she snarled at the pimp. My smile turned to a sneer as I slipped Jake a $50 so she could see. This was 1969, so $50 was good money. I’d already explained the situation to Jake and he was on my side. The implication was that I’d already paid him, which was the norm, and this was a bonus.

“Child, he’s paid plenty extra, so you will fuck him however he wants to be fucked, and you will make him love every second of it. You know what will happen if he doesn’t,” Jake warned. A flicker of fear crossed her face. So, Jake beat his girls. Not surprising.

I began undressing the instant the door clicked shut. Francis lay there looking like she was ready to hurl. This was going to be some sweet revenge. When only my Jockeys were left, I told her, “On your knees in front of me, take these off, and love me with your mouth.”

She slid off the bed and walked over to stand directly in front of me, eyes defiantly locked on mine. “You think your special shit now, but you’re still having to pay to have me.”

Grabbing her hair in both hands, I yanked her down to her knees. “How it happens is irrelevant. I AM having you how ever and how long as I want.” Pulling her face to my crotch, I continued, “Now start with your mouth.”

Eyes still defiant, she yanked my Jockeys down to my ankles, then turned her gaze to my dick. “Is it dead?” she asked in a sarcastic tone. I really hadn’t expected her to be this feisty, especially after Jake’s warning.

“No, it just needs some mouth-to-head resuscitation. Now get busy,” I ordered. Lifting it with her tongue she slid it into her mouth, closed her lips around it, and began a milking action that was amazing. Francis had some skills. I wondered briefly if she’d ever sucked David’s dick like this, or if it was something she picked up while turning tricks.

Flaccid, I’m nothing special to look at; pretty puny actually. But I swell up nice, and pretty soon her mouth was stuffed. There were about two inches that weren’t getting any attention. “Take it all in,” I ordered. She pushed toward me but stopped when my dick hit the back of her throat, then pulled back. As I repeated, “All!” I grabbed the back of her head and pulled her toward me as I drove forward, burying her nose in my pubic hair. I held her there for several seconds and she never gagged once. Fucking deep-throating bitch was holding out on me.

When I pulled my dick out of her throat she tried to gasp for air, but soon as she exhaled, I drove back into her and clamped her head to my groin. She waited a few seconds, then began trying to push me back. I felt her teeth on my shaft. “Bite me and you will wish Jake had a chance to beat you, bitch.” The teeth relaxed and her wet blue eyes turned up pleading for release. A few more seconds and I let go of her head. She yanked back off my dick and gasped for air. Long, thick strands of mucus strung out between her lips and my crotch.

“More,” I commanded after she seemed to begin to catch her breath, “I want to fuck your face.” She opened her mouth and leaned forward. Grabbing her head, I sank my dick to the hilt again and began driving in and out in earnest. She was making gagging noises and mucus was running out onto my balls and legs while her fingers dug into my butt cheeks. Eventually, I pulled her tight against me for several seconds, then pushed her off hard enough she landed on her back on the floor. Mucus covered her breasts and belly, her eyes were red and tearing heavily, and her lips were now swollen.

“Are you wet?” I asked. She nodded. “Prove it,” I ordered. She slipped two fingers into her pussy and they came out glistening with her juices. Guess she’s enjoying this after all, I thought. “Taste yourself. Is it good?” She slipped her fingers into her mouth and sucked them clean, then nodded. “Grab a towel and clean us up. I’m ready to fuck your cunt.” She did as told and jerked my cock a bit as she dried it off. I really had no interest in having it all wiped up, I just wanted to order her around a bit more.

 
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