Head Cheerleaders Anal Cherry

The year was 1994. I was 18 years old and about to graduate high school. The prom was only a week away and I did not have a date. I was an average looking guy. I was 5’10, 190 lbs, short dark hair, and dark eyes with a decent build. I guess my best quality was tucked away in my pants. My dick was nearly ten inches long and very thick. Having had a girlfriend in private school for three years, whom I had just broken up with, word had not really spread throughout school about my goods.

Through out my senior year I was in love with the Jeanine. She was the captain of the cheerleaders, the Student Government President and had been elected homecoming queen easily back in the fall. However, she had been dating this guy named Dan and I figured since they had been together for two years, they were never breaking up.

Much to my surprise the week of the prom, Jeanine & Dan broke up and Jeanine was now dateless to the prom. I seized my opportunity and asked her to go. Since we were friends and she knew, I too was coming out of a relationship, she figured we would have fun.

The night of the dance, Jeanine looked gorgeous. Decked out in a black strapless dress, that ended two inches above the knee, her 34 C tits were well accented and of course her blonde hair and blue eyes started giving me dirty thoughts as soon as she opened her front door. To make matters worse, Jeanine was wearing this sexy red lipstick and all I could think about was what it would be like to have her luscious lips wrapped around my dick.

I got a limo for Jeanine and me since she did not want to go with her friends because Dan would be there with his date. I took her to dinner and then off we went to the prom. In the limo we shared a bottle of wine and we were both feeling very good as we entered the prom. I was loving life considering I had the hottest girl in school on my arm.

Jeanine was also a member of the school dance team so needless to say she was a fun date. It was during the song Rump Shaker by Wrecks N Effects that I knew our night might get interesting. Freak dancing was huge at the time and during this song I was behind Jeanine who of course at the start of the song was grinding her ass on my cock. I could not stand it and got full erect almost immediately. Jeanine reached one hand behind my neck and pulled me in and whispered into my ear, “Easy tiger.” As that song ended a slow dance came on and of course Dan came over and asked if he could cut in. Jeanine said no, and of course Dan made a scene. I suggested he go back to his date but instead he pushed me. So I clenched my fist and clocked him in the nose. Jeanine smiled and thanked me, a few others patted me on the back, but the principal suggest I leave.

Jeanine and I got in our limo and she immediately grabbed face and stuck her sensational lips on my mouth and kissed me deep. Her tongue darted into my mouth and did amazing swirls. It was with out a doubt the best kiss of my life. She tasted so sweet and I wrapped my arms around her, held her tight and enjoyed her tongue in my mouth. As we were kissing, I could not help myself and had to grab her ass. It was so firm and of course the perfect size. I mean after all, she was a cheerleader and dancer. She stood 5’4″ weighed 115 lbs.

After a few minutes of kissing, the phone rang and the limo driver asked us where we wanted to go. It was 11 o’clock and we had the limo until 2 AM. Jeanine told him to just drive us anywhere he wanted and keep the car moving. She told him we just wanted to ride around until 2 AM. Since we were in Baltimore, I think we drove to DC, followed by Annapolis, but I can’t remember.

Jeanine hung the phone up and turned back to me and noticed the bulge in my pants and smiled. She said, “I thought I felt a monster pocking at my ass while we danced.” I replied that the monster loved the feeling of her ass.” It was a lame line, but I did not care.

She kneeled in front of me (gotta love limos) and said that she was not looking for a relationship and I was probably a rebound. She said she was going to college out of state and was not looking to start a relationship. She also said that she was fucking a guy with a little dick for two years and wanted nothing more on prom night then to fuck a man who could really make her cum.

With that in mind she undid my tux pants and slid them down to my ankles. Since I don’t wear underwear my cock was fully erect and the near ten inches just popped into her face. She started to lick the head of my dick. The tip of her tongue teased the opening of the head of my dick and drove me wild. She used her right hand to hold my cock and her left hand was massaging my balls. After a couple of minutes of licking the head of my dick, Jeanine pulled away and popped her boobs out of her dress.

She then leaned forward, opened her mouth and wrapped her red lipstick clad lips around my cock and started to suck. Her combination of lip pressure and tongue licking was amazing as her head bobbed up and down on my cock. The entire time as her mouth moved up and down my dick, Jeanine kept massaging my balls. She even stopped sucking my dick after about six minutes and took the time to put each ball in her mouth and suck them one at a time while stroking my shaft. At this point I was squeezing her tits and her nipples were rock hard.

After sucking my balls for a while Jeanine brought her sexy mouth back to my shaft and continued with the best blow job of my life. Her bobbing head was now doing its best to deep throat me. She got about 75% of my cock in her mouth, but my thickness and length was too much for her. So I decided to help. I placed my hands on her blonde hair and head and skull fucked her. I pushed my cock all the way to the back of her throat and at this point her nose buried in my pubes, but my whole cock was in her mouth. I held her in place. She gagged for a second or two but then she adjusted and I helped her resume her blow job, though now she was deep throating me.

Between her tongue, her lips, the fact she was deep throating me and of course her hand that was constantly massaging my balls, I could not take it any more and exploded a massive cum shot into her mouth. AS soon as a drop of cum hit her tongue I could feel her mouth become more like a vacuum as she literally tried to suck all of the cum out of me. I am lucky in that I shoot massive loads of cum and it turned me on so much seeing her try and swallow every drop, but still see a little bit creep out the corner of her mouth.

Jeanine removed her lips from my dick and I was thrilled to see that there was a small amount of red lipstick around my shaft. She used her finger to capture the small amount of cum around her lips and guided it into her mouth. She smiled and said, “Now you know why I was elected head cheerleader.”

There was no way I was not returning the favor as I was hornier now then before. I pulled Jeanine onto the seat and angled her off the seat so her pussy would be right in my face. I lifted her dress up so it was around her waist and much to my surprise she too was going commando. Even better was her pussy was shaved clean. So smooth and perfect, a true bald eagle.

I spread Jeanine’s legs and began licking her throbbing clit. She was so wet and tasted so sweet. Her clit was very thick… Her actually pussy hole was even better. It was soaking wet and easy to stick my tongue into. I stuck my tongue as deep into her pussy as I could and still worked her clit with my top lip and thumb. As I was eating her pussy, I could not help but notice how sexy her asshole was. I knew she had a great ass, but there was something about her asshole that was turning me on.

I had a lot of experience with anal sex before, but never, had I licked a girl’s ass. It was then I decided that I was going to taste Jeanine’s ass, only first I needed to make her cum. I wrapped my lips around her clit and sucked it very hard as my tongue worked the rest of her pussy. It did not take long, and Jeanine exploded into an orgasm. Jeanine came so hard she was pushing her entire pelvis into my face and I just sucked her clit harder. She was begging me to stop but I kept at her. Finally she pushed me away. Using my finger I gathered some of her juices and guided them down to her asshole. Before she had a chance to realize what I was doing I leaned in and stuck my tongue straight into her sexy tight bung hole. I was expecting it to taste lousy but it actually tasted really sweet.

I gave her asshole a good licking for a few minutes and in the mean time started to finger Jeanine’s pussy. I could tell by the way Jeanine’s body was tensing up that she was about to cum again. So I decided to go with the world famous, “two in the pink, one in the stink method. I licked her clit fast as I fingered her pussy with my pointer and middle finger and fingered her ass with my pinky. Jeanine exploded again and came really hard, this time squirting some visible juice.

I was rock hard again at this point and with out a condom, shoved my cock right into Jeanine’s pussy. It was so wet and so tight and so hot. My huge cock stretched her wide and in seconds her legs were over my shoulders so I was able to get all 9.5 inches deep into her. I swear I think I hit her cervix because she exploded into another orgasm. Her cumming only made me fuck her harder and I am pretty sure she came again about 30 seconds later. My cock was easily flying into Jeanine’s pussy at this point and my balls were smacking her asshole.

Jeanine and I moved onto the limo floor and she got on all fours, using the seat for leverage, and I entered her pussy from behind doggy style. I started out holding her hips and pounding her pussy really hard. I was fascinated seeing her pussy just suck my entire dick in and spit it out. I leaned forward so I could get deeper into Jeanine but also so I could kiss her neck. I wrapped my lips around her neck as my hips pushed my cock in and out of her pussy and left a pretty big hickey on her neck.

She reached back and scratched my back drawing a little blood. I moved back to holding onto her hips and licked my finger so I could stick it into her ass. That was all it took and Jeanine exploded into another orgasm.

I decided to go for it and try to fuck Jeanine in the ass. I pulled out of her pussy. My dick was so wet with her pussy juice. I pushed the head of my cock right up to her asshole and started to push. She freaked and asked what I was doing. I told her to relax, trust me and to rub her clit hard and fast. She obeyed and I pushed my cock hard into her ass. Her tight sphincter resisted but eventually gave way and started to expand. Jeanine yelled in pain, I asked her if she wanted me to stop, but she told me if I did she’d never fuck me again.

I went slow and eventually the captain of the cheerleader’s asshole was full wrapped around my dick. She took all of me in her butt and after a few minutes, she told me to pump her. It turned me on to no end. I felt like I was going to cum, but did my best not to. Jeanine, told me to lie down because she wanted to try riding my cock with her asshole. I did as she commanded and with her dress still around her waist she lowered herself onto my cock and I slid back deep into her gaping asshole. Jeanine seemed to really like it. She bounced up and down on my dick and was going really fast. It was so sexy to see her asshole gaping wide swallowing my cock. I was rubbing her clit as fast as she was riding me and of course her tits bouncing made the view perfect.

I was about to cum and I told her I wanted to cum inside of her. She switched my dick from her ass and clamped down on me with her pussy. I reminded her I was not wearing a condom but she did not care. She bounced on my dick three times faster now that I was in her pussy and within seconds, I exploded into my second orgasm of the night filling her up with cum, I could feel my cum shooting deep inside of her.

She fell forward and we kissed. My cock was still in her pussy and I was still semi hard and still having small cum shots go into her pussy. She finally got off of me and collapsed next to me. She smiled and told me that I was her first ass fuck.

I nodded off to sleep as the limo driver drove knowing that I fucked the head cheerleaders virgin ass. About 45 minutes after we were done fucking it was 2 AM. I slept over at Jeanine’s and the next morning she woke me up with a great blow job. We pretty much fucked for the entire summer and then stayed in touch through college. Whenever we were home on breaks we’d always meet up and fuck for hours.