Loading...“Here’s a picture of me at Mt. Rushmore.” The girl in the picture was a High School aged version of my Jan. The similarities were obvious, though over 10 years had passed since this photo was taken.
It was a rainy Saturday afternoon; our planned picnic had been aborted. Looking for something to do after a morning of sex, Jan brewed a pot of coffee and we started going through old photo albums.
Though a wantonly sexual creature, I had always enjoyed Jan’s sentimental side. We had been at it for hours, looking at the photos of her childhood and High School and college years.
She turned a page in the album. She grimaced. “Oh, this is me on the cheerleading team.” Once again the girl in the photo was my Jan, looking very girlish. The blue sweater she wore in the photo fit relatively loosely, her skirt shorter than anything I’d seen her wear in the six months we’d been dating, her dirty blonde hair pulled back into a ponytail.
“I like it!” I smiled wickedly. Jan wasn’t the kind of girl I would have pictured as a cheerleader. A staunch feminist, she was very vocal about girls being pigeonholed into gender roles.
“Oh, I was so dumb!” She was on the verge of getting mad. “I can’t believe I did something so stupid!”
“It’s just something girls that age do,” I stroked her hair lightly, “besides, you were definitely cute enough to pull it off!”
“Oh stop!”
“No, really,” I grinned, “you could still pull that look off if you wanted to.”
I was trying to flatter her, but I wasn’t exaggerating. In her late twenties, Jan still had a cute quality about her with her slightly upturned nose and infectious smile. Her body was still trim, though her hips had widened a bit over the years.
“I don’t ever want to look so stupid again!” She was a little angry.
“I’m sorry,” I said, “I’m just teasing you a little.”
“It’s not you.” She turned the page in the album. That page contained a number of cheerleader photos as well.
“What is it then?” I asked. I was a little concerned about her mood. “Bad memories?”
“Sort of. Do you see this picture?” She pointed to a photo of her and the rest of the squad in a posed photo. “This was before my first game. Just before the game my boyfriend saw me in the hallway. We stepped into a doorway and made out for a couple of minutes. His dick was so hard! He was feeling me up under my sweater and I was getting really hot for him. I told him how bad I wanted him and we decided to meet after the game.
“During the game, boys I knew from school came up and talked to me. Boys who normally didn’t talk to me now acted like we were old friends. I noticed a few of them had hard ons.” She grinned at me. “Yeah, girls notice that sort of thing. I started realizing the effect I had on boys, and it was getting me a little worked up. I was a little more enthusiastic, my leg kicks were higher, and I wiggled my ass more seductively. Cheering was making me really hot!
“By the end of the game, my panties were soaked! I needed my boyfriend so bad! We met just outside the locker room right after the game. I pushed him into an unlocked Janitor’s closet and started kissing him. I had planned to take him home and fuck him, but I was so horny. I could feel his hard cock as he ground it against my belly.
“I got down on my knees in front of him and pulled his hard cock out. I just started sucking him like crazy. I was so into it. When I looked up at him, he was in the throws of ecstasy. He grabbed me by my ponytail and started jamming his entire cock into my mouth. I was gagging on him, but I was so hot I didn’t care.
“After a couple of minutes, I needed his thick tool in me. I tried to pull my mouth off of him, but he resisted. A second later he came in my mouth! The dirty bastard came in my mouth. My pussy was on fire and he wasted his load in my mouth.
“He kissed me on the forehead, zipped up and started to leave! I told him how my pussy was aching for him, but he didn’t seem to care. He said he had to meet his friends but he’d call me. He’d call me?!? I didn’t want to talk to him; I wanted to fuck him!
“He kissed me on the forehead again and left. I was livid! I called him a fucking dick and told him to never talk to me again. I sat there and cried for a few minutes after he left.
“But that wasn’t the worst part. The next day at school all the boys started calling me ‘the Head Cheerleader.’ At first I thought they were mistaken, I wasn’t the captain of the team, then I realized what they meant. That bastard! He told everybody.
“I was pissed that he told everyone, but the worst part was how he got off, left me frustrated and now was bragging about it. That dick was bragging about how he popped in the ‘Head Cheerleader’s’ mouth. I decided I didn’t have a choice, I quit the boyfriend and quit the team.”
“Boys are so cruel at that age.” I replied as I hugged her. “He was just some high school asshole, he’s not worth getting upset over.”
“It’s not just that.” Jan returned the hug. “For the first time I felt sexy. Boys were interested in me and I liked it. It made me horny. I thought doors were opening for me, but I was just an object. That bastard just wanted to get off, he didn’t want me. I was his fantasy, he didn’t care about my needs.”
I kissed her, assuring her that I cared about her and her needs. We spent the next few hours making love tenderly. I was careful to make sure she was completely satisfied by the time I had to leave.
A few days later, Jan called and asked me to come over. I gladly jumped in the car and drove over to her place. I knocked on her door and heard her call for me to come in. I entered and said hello.
“Hi there,” she said through the closed bathroom door, “I’ll only be a minute, I have to finish getting ready.”
Getting ready? Getting ready for what? Her phone call had come out of the blue.
“Thanks again for giving me a ride,” she called through the door, “I didn’t know how I was going to get to the game.”
I was confused and at a loss for words. I had no idea what she was talking about or what was going on. My confusion continued as the bathroom door opened and my Jan stepped out in her high school cheerleader uniform.
I admired the way she looked. Though it had been over 10 years since she’d worn the uniform, it still fit relatively well. The blue sweater was a little tighter, but this only served to accentuate her beautifully firm B cups. Her skirt rode very high on her hips, it’s hem reaching to mid thigh. Her look was completed with a cute ponytail and a minimum makeup application. For a moment, I believed that this girl was a high school cheerleader.
“Thanks again,” she kissed me on the cheek, “we have a few minutes before we have to go. Do you want something to drink or anything?”
I nodded stupidly. Jan went to the fridge and poured me a glass of lemonade. She grabbed my hand and led me to the living room where we sat together on the sofa.
“We’re doing some new cheers tonight, wanna see?”
I nodded again, completely confused by what was going on. Jan went into a couple of cheers. I began to become aroused, especially since she kept looking at my crotch. Her cheering became more enthusiastic; she began showing me her panties more, kicking her leg higher and higher. My cock became harder and harder.
“That’s very nice, baby!” My breathing became shorter, I was definitely aroused. “Do you have anything else for me.”
“Maybe…” she giggled. “I made this one up especially for you!”
She began bouncing in that classic perky cheerleader style. Rhythmic clapping followed. Finally standing just in front, of me hands on hips, she began her cheer: “No Place To Run! No Place To Hide! I Want Your Cock! Deep Inside!” She leapt high into the air, landed and went into the splits right in front of me. Her head dropped to my crotch and she began kissing my now pulsating cock through my jeans.
I began stroking her hair as she unzipped my fly. Her tongue was all over my head as soon as it popped out. I pulled my pants down to my ankles, struggling to keep my cock in Jan’s mouth as I did so.
“I’m so horny,” she said as she momentarily removed me from her mouth, “promise you’ll take care of me. Don’t come in my mouth.”
I nodded in agreement and pushed her head back to my throbbing tool. She sucked me for a good ten minutes, constantly monitoring my level of arousal, making sure not to take me to the point of release.
“Get those panties off!” I demanded as I pulled her sucking mouth from my quivering manhood. “I need to fuck your cheerleader cunt!”
Jan stood in front of me, slowly remove her panties. She then winked at me before shooting he soaked panties at me like a rubber band. I caught them in mid air, wrapped them around my stiff tool and began jerking myself slowly. Jan lifted her cheerleader skirt with her left hand and inserted first one, then two and finally three fingers into her dripping snatch.
I could have gotten off just watching this spectacle, but I knew Jan wanted my cock to get her off, not three of her own fingers. “Sit on my cock!” I demanded and Jan quickly obliged.
She rode me, squealing like a cat in heat. She dropped herself onto my hard cock, nearly throwing herself onto me with every thrust. My hand went under her sweater and squeezed her nipples. Jan flailed her head around wildly as her squeals became full throated screams. She was getting off as never before.
Jan calmed down after her orgasm, still riding me slowly. She dropped her head to my shoulder and began whispering in my ear, “I’m a dirty cheerleader.”
“Yes,” I replied, “You’re the dirtiest cheerleader.”
“I want to be dirtier.” She closed her eyes and smiled. “I want to do the dirtiest thing.”
“What’s that?” I asked knowing what she meant, but wanting to hear it from her.
“I want you in my ass!” She reached between the cushions of the couch and pulled out a bottle of lube. She had obviously planned this. “Will you fuck my ass?”
“Get on the floor and lift that skirt for me!” I demanded. Jan climbed off my cock and lay, face down, on the carpet. I spread lube over my cock anticipating the pleasure to come. Jan and I had been doing anal for a few months now, though always at my request. What a turn on to have her ask for it.
I dipped my middle finger into the bottle of lube to coat it, then jammed it into Jan’s ass. She was tight around my finger and I enjoyed watching her squirm as I made sure her rectum was good and lubricated for me. Next I knelt between her legs and place the head of my cock against her anus.
“Do it!” she moaned. “Fuck my ass!”
She had never even asked me to do this before, now she was practically demanding it. I wanted to really enjoy this. I slapped my thick cock on one of her ass cheeks.
She squealed in delight. “Oooh, yes! Do it! Fuck my dirty little cheerleader ass!”
I couldn’t hold out any longer. One deep thrust and I was all the way in her. She asked for it, so she was going to get whole dirty treatment. I hammered her tight asshole. I banged her little ass harder than I had fucked her cunt. My hips slammed into her ass so hard that it sounded like I was spanking her, spanking her extremely hard and fast. Jan pushed her hand between her legs and started rubbing her clit. I could tell that she was getting close to coming again. Her moans became louder and more unrestrained.
“OH, JESUS!” She screamed. “FILL MY ASS WITH YOUR COME!”
She didn’t need to ask me twice. I let loose a torrent in her dirty asshole as I hollered out a loud moan. I collapsed onto her, lying there for a few moments before removing myself from he anus. My load came running out and Jan reached back and collected a big gob on her finger. She then rolled over and stuck the finger in her mouth, smiling. I ran my cock through her bush, leaving a trail of my seed over her mound.
I leaned forward and kissed her, having never appreciated her so much. “That was great,” I said, “thank you.”
“Thank you,” she replied, “I finally got laid as a cheerleader.”
That asshole has no idea what he missed.