Why I Liked School Ch. 6

Story Info
Party, girls, cheerleaders - a great combination!
4.2k words
4.48
101.6k
9
0

Part 6 of the 6 part series

Updated 10/17/2022
Created 12/02/2001
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

For a week or two, I either avoided or was not approached by anyone for sex. I was not sure why id did this, or maybe I may had lost my charm, I didn't know.

Nearly two weeks after my Holly and Jenny encounter, I got an invite to an end of term disco, at Anna's local town hall. After some confidence building I asked Helen to go with me, and on the night we turned up in the appropriate fancy dress, it was an "American night". Most girls (including Helen, Anna, Alison, Debbie, Holly and Jenny) were dressed as cheerleaders. I'd turned up as an American baseball player, though most boys were dressed as American football players. The idea of the party was that everyone would sleep in the hall at night, and we would all go into town the next morning and go home.

However it had already been decided that some girls would go back to Anna's house (where her parents had conveniently left her alone) in order to save space. What everyone else didn't know was that I would be joining the girls that slept at Anna's.

Helen and I danced most of the night, sometimes splitting off and dancing with other people, but always coming back and dancing together again. At around 11.00pm the DJ left, but the pizzas arrived. We all dug into a slice of pizza and Anna decided what was gonna happen.

She decided that She, Helen, Holly and Debbie would sleep at the house, while the rest stayed here. This surprised me. I didn't think that Anna knew about me and the Holly/Jenny experience, but obviously she had found out. I wasn't bothered. The rest of the girls would sleep in a separate room inside the hall, while the boys would sleep in the main area. After the pizzas everyone sat down and we played a game of spin the bottle/truth or dare. It was interesting to see how nervous some of the girls and boys were when they had to kiss each other, but even more interesting were the reactions whenever I got a dare (I dare not do a truth in case I was asked if I had slept with anyone, or who I'd slept with, or what I was gonna do later, etc). Everytime I was picked it would get more and more sexual. First it was a kiss, then feel the breasts, then hand up the skirt, and so on, however it didn't get any further than me kissing the breasts of Alison. The people were amazed at how far I was willing to go, how far most of the girls were willing to let me go, and how little they seemed to mind. I noticed that John was trying to convince Anna to let him stay at her house this evening, but he made up a cock and bull story about her parents arriving early the next morning.

Eventually there was a unanimous decision (at about 1:30am) to go to bed. I decided to walk Helen to Anna's house, for two reason: number one, so I could find my way to Anna's house in the dark, and number two I am a gentleman by nature and it is only good manners to walk your date to her door (even when you are gonna see her in less than an hour and fuck the brains out of her and her friends). On the walk, Anna told me to appear in the next hour. I agreed and she said that all the girls would remain in their cheerleaders outfits.

I returned to the hall to find that the girls and boys had mixed and were no longer in separate rooms. Most of the girls were in the main hall, but only a handful of the boys were present. Apparently, they had gone to get some more booze. I said that I would go and try and find them.

Some of the girls were suspicious, but I said that I would be back as soon as possible. I didn't care about their suspicions, I was more interested in the immediate future, which involved me, four girls, cheerleaders costumes and a whole lot of pleasure. I knocked on Anna's door and Debbie opened it.

Helen gave me a deep kiss as I entered Anna's house, she and Debbie led me to what I assumed was Anna's parents bedroom (as it had a double bed). Anna began by explaining that Holly was going to be held down a year, so the girls had invited her to calm her nerves, knowing that I had already fucked her. As the new girl, apparently it was Holly's turn to go first. I was still standing by the door, so Holly led me by the hand to the bed, and sat me down. She slowly slid my trousers down to my ankles and off, and then slid my boxer shorts off, exposing to the four admiring girls, my upright, rock hard prick. Holly kissed the head. I been waiting for this night since Anna had suggested it, and now it was just beginning. Holly engulfed my cock in her mouth, and sucked like a goddess, her tongue playing havoc with my head. I got into it, and without asking, used my hand to force her head onto my cock. I got no complaints, except the odd gagging noise, as I deep throated this beauty. I felt the pressure mounting, and said so:

"I'm cumming!"

Holly, however, made no signs of withdrawing and continued sucking me. I was surprised, as when with Ms Jones, Holly had seemed to dislike oral sex, but none of that mattered as my dick exploded and filled her mouth with cum. It was obvious that she couldn't swallow it all, as I was extremely horny, so I withdrew my dick and let lashing of my cum land on her face and upper torso, soaking her cheerleaders outfit. I lay back on the bed, not exhausted, but just in ecstasy. Helen lay next to me, and kissed me. She slowly pulled my shirt over my head leaving me completely naked. She then rolled over ontop of me and straddled me. As I looked around, I could see none of the other girls, but I could here the shower on in the ensuite. Helen was now kneeling up, and was sliding her panties off. Still dressed as a cheerleader, she lowered herself onto my cock. She was still tight, but not half as much as when we first "encountered" each other. She began raising and lowering herself on my prick, and got up a steady rhythm. I meanwhile, used my hands to fondle her ass and breasts thought her top. She began screaming in delight, as she came, and I too began to feel the need to cum. I held her waist and began forcing her up and down harder and harder. I came and filled my date with an almighty wad of cum. this in turn made her cum. She collapsed onto me, as I lay in wait of what the other girls were doing in the bathroom showers!

To my surprise the other three girls came out of the shower, soaking wet, but still in their clothes. Such was the tightness of their cheerleaders uniform, was that I could easily see their tits. As I watched them, kiss and pinch each other, Helen disappeared into the shower and emerged soaking too.

I was horny again and needed to cum:

"Anna, Debbie, get over here, your turn!" I said

"Not quite," said Anna, to my disappointment, "Holly here says you never fucked her in the ass. Before we get involved, you've gotta take her ass!" This made me happy.

Holly propped herself up against the wall, and I came in behind her. I took a tub of Vaseline from Debbie, and lubbed up my dick. I began by kissing Holly's wet legs, them slowly working my way up her body, I lifted her skirt. She wasn't wearing knickers. I kissed her ass cheeks, and them put lubricant in her hole. She grunted a little as my fingers went in, and I could feel her tightness. I removed my fingers, then positioned my member infront of her ass entrance. I pushed in slowly. She groaned in pain, and I could feel her ass muscles, tense around my prick. I began kissing her on the neck, and playing with her tits, through her sopping wet top, but she remained tense. I whispered in her ear:

"its much less painful if you relax!"

She did relax a bit, but she was still very tight. She continued to moan as pushed further and further into her. Anna saw this and positioned herself sitting under holly. She used her tongue to stimulate Holly, and her hands to stimulate my scrotum. I got the familiar feeling of when my dick could go no further, so I withdrew a bit and slowly began pumping. She moaned every time I went in, but soon got used to it, and I became a little more aggressive. Anna then left Holly, without orgasm, so I began pumping quite hard, and she began pushing herself onto me, till she came with ecstasy. Only a few seconds later my dick swelled and I dropped my load in Holly's ass. Cum was dripping out of her crack as I withdrew myself. Anna took her into the shower, still fully clothed, and I could hear the familiar sound of kissing. (god I love lesbianism).

I walked over to Debbie, and began to kiss her. I was ready to get someone naked. I slipped off her sopping top, to reveal that she wore no bra. I used my tongue on her nipples and slowly slid off her skirt, leaving her completely naked. I pushed her onto her back on the bed. I walked up and slid my prick inside her, plenty wet. However after a couple of strokes, I withdrew my cock, much to Debbie's annoyance. I lifted Debbie up and turned her around, so she was on all fours, I thrust my cock into her pussy, in and out, over and over again. She began moaning, but Helen hiked up her skirt and planted it infront of Debbie's face. Debbie began eating her out, while I pumped her pussy from behind. Debbie came quite soon, and I soon after that, filling her pussy with my cum, and groaning in pleasure. But I noticed that Debbie had yet to please Helen, so I took over, using my tongue to stimulate her clitoris. I flicked and sucked and licked, and eventually she came. Normally I couldn't stand giving oral sex to women, but there was something about Helen and Debbie and their beautiful crotches, asses and generally her bodies, which made me enjoy eating them out. But now Helen and Debbie were satisfied for the time being, but I was still hard. So I decided to venture into the shower.

I saw Anna and Holly fingering each other under their skirts while kissing. I walked over behind Anna and kissed her on the neck. She stopped kissing Holly, and grabbed my pecker with her hands. She then got down on her knees and began jacking me off. Holly followed suit and got onto her knees and positioned her hands on my cock. There were 20 nubile fingers masturbating me, in a shower. The girls looked gorgeous in their soaking outfits, and I couldn't help myself from cumming quickly. It was a large load, and it shot all over Holly and Anna. Their faces, and hair, covered in my love juices. Anna engulfed my penis and sucked the last bit of cum out. She then stood up and kissed me, while using her hands to again stimulate my penis till it was hard again. She then guided my dick, till it was infront of her entrance. I then thrust up, and she thrust down, so I entered her rapidly. I pushed her against the wall, and ripped her top off, exposing her wet tits. I sucked on them as I pumped into her hard. I ripped of her skirt as well, so we were both naked. I held her against the wall as she hooked her beautiful legs around my back, and pulled me in deeper and deeper. I forced myself further and further in, harder and harder. She was now screaming with pleasure as I fucked her hard and fast. I could feel that I was gonna cum, so I stopped. I could feel that she too was on the brink of cumming too. She had made me wait, so I wanted to make her wait. She began sucking on my neck, obviously trying to entice me into re-entering her. I placed her on the floor and began rubbing my cock around her entrance. She was going mental, squirming around on the floor of the shower. Now I would have liked to make her suffer more, but at this point my dick was going crazy, and it took over my brain. I rammed my exploding cock into her quickly, she came immediately, and screamed in pleasure. She was so loud, I would swear that the guys at the hall could hear. I came within seconds, shooting my load hard into Anna. We lay back, both immensely happy. I would have been ready to relax after an intense fuck like that, but I was a man in demand. Helen came in and kissed me. She led me into the bedroom, where Holly and Debbie were fucking with didlo's, like nymphos. Helen led me onto the bed, and lay me on my back. She climbed ontop of me:

"time for some quality time with my date!" she said

She slowly pulled her top off, exposing her sopping wet tits. I leant up and sucked on her tits for a while. She pushed me back, and removed her skirt, revealing everything. She lay and slid her tits all over my body, making me hard again. She used her hands to jerk me off for a couple of seconds, then guided my cock into her mouth. Her tongue worked like magic, and she sucked me good, but she didn't make me cum, instead she released my member and slid her pussy onto my prick. She humped up and down for a while, then slid ontop of me. We kissed deeply as I fingered her ass. I then rolled ontop of her and we assumed the missionary position. I pumped for a while, and she came to orgasm. I stopped for a while, moved up the bed and fucked her tits for a while, still not cumming. Instead I went back and continued pumping in her pussy. I picked up one of the dildos Holly and Debbie weren't using, and began using it on Helens ass and clit. I shot my load into her, rather quickly, but bring both of us to an immense orgasm. I lay next to her, and we kissed.

She spoke softly to me, "I want you to take me in the ass. I know you enjoy it, and I want you to be able to do it with me!"

This surprised me no end. Helen hadn't liked when I first ass fucked her, and had specifically asked me not to, on our second encounter. I asked her whether she was sure, and she told me she was. The anticipation had me hard again. I reached over and got the Vaseline I had used on Holly, and lubbed up my dick and Helen's ass well. I lay next to her, so as not to seem too domineering. I kissed her on the back of the neck, and down her back, then began using the dildo on her muff with my left hand. I held hands with Helen with my right. I slowly slid the head of my prick into her ass. She was relaxed, so the dildo was doing its job. I pushed further and further into her beautiful ass, till I could go no further. She had groaned a bit as it had gone in, temporarily clenching her buttocks and preventing me from going any further, but she always relaxed as the dildo worked on her clit. I began slowly pumping in Helens ass, slowly so as not to hurt her, but also as it was hard to get a steady rhythm going when I had no hand to brace myself. I was now seriously horny at the thought of cuming in my gorgeous date's ass. Without warning she squeezed my hand tightly, and tightly clenched her buttocks, as she came to orgasm from my dildo work. The sudden clenching of her buttocks, squeezed my prick, which in response, shot its load up Helens ass. My dick went limp, and Helen calmed down. I whispered to her as I removed my member:

"How was it?"

"better this time," she said, "we have to do it again, you know practise makes perfect."

I looked over to the clock on the wall, 3:00am. I saw that Debbie and Holly were asleep on the floor, and Helen was drifting off herself. I thought of finding Anna and giving her another good fuck before I went to sleep, but I hadn't got the energy. The night had gone well, so I lay my head down and fell asleep.

Following that experience I had some rather erotic dreams that night. I awoke with a jolt as someone grabbed my rock hard cock.

"Dreaming of me?" said Debbie

I was surprised to find Helen gone, leaving just Debbie and Holly.

"Among others" I replied, it was 7:00am. 3 hours till we had to meet everyone else. Debbie must have noticed that I was paying her little attention, as she decided at this point to lick the side of my prick. This of course got my attention. I sat up, so I was sitting over the edge of the bed. I noticed Holly was still asleep, but didn't care. I used my hands to guide Debbie towards my member. I used my hands to make sure that she could not escape. She licked the underside of my prick, then took my balls in her mouth. The feeling was incredible. She released my scrotum and continued by taking my entire cock into her mouth, and I could have sworn she would swallow it. She took it in as far as possible. I was using my hands to play with her hair, and hold her in position. She was using one hand to milk my prick and the other to stimulate herself. I pushed myself further and further into her mouth, and then I came, like an exploding volcano. She began coughing as the cum filled her throat. I removed the cock, as she let the cum dribble out of her mouth, and my still squirting cock squirted the rest of my cum onto her body.

I could see that she hadn't satisfied herself, so I decided that she deserved an early morning fuck. I pulled her up off of her knees onto the bed, so she was positioned over my cock, I then thrust her down, as if stabbing her with my cock. She understood what I was doing and used her legs to push herself up and down on my cock. Everytime I felt as if I was going to cum, I stopped for a minute then carried on. This drove Debbie crazy, she came at least twice, and then I took my prick out of her wet kunt. I felt horny, and I wanted to have a really good fuck with Debbie before moving on, so I flipped over, so she was laying face first on the bed. I hoisted her up in the doggy position. However instead of entering her kunt, I pushed my dick between her beautiful ass cheeks. She screamed in pain as I had applied no lubrication, but I continued to pound her ass. I used one hand to stimulate Debbie, but the other, I grabbed Debbie's hair and used it to get into a rhythm. She began to moan as she reached her climax, and finally she came. I too could no longer contain myself, and shot my second load into Debbie. It was another large load, as I withdrew my cock, cum leaked from her ass crack. She collapsed in a heap of ecstasy.

However, despite this, I was still horny, and my cock was still hard. With Debbie collapsed, Helen and Anna absent, I walked over to Holly, still asleep face up on the floor, and the only member of the four girls (or 2 who were present at least) with any clothes still on. I decided to wake her up in a cruel way. I knelt above her face, my throbbing cock inches above her. I slowly began massaging my rod back and forth with my hand. I wanked myself over Holly's face till I came. As the cum splashed on Holly's face, she awoke, but before she could say anything, I pushed my dick between her lips. She automatically sucked the remaining juice from my prick. I withdrew and kissed her deeply, tasting some of my own cum still on her face. I stood her up and told her:

"Those clothes have a lot of cum stains on, you better take them off."

She was a little more shy with neither Anna, or Ms Jones around, so she went into the shower to change. I wasn't having any of this, so I followed her in.

"cum on Holly, its nothing I haven't already seen."

I kissed her on the back of the neck, and slid my left hand up her skirt and massaged her pussy. She turned around and I kissed her deeply. She returned the favour and grabbed me, pulling me in closer. I moved back and helped her take her top off. There were her tits, rounded and succulent. She dropped the skirt leaving her completely naked. I couldn't help myself, so I leant over and sucked her breasts. I pushed her backwards, so she was supporting herself against the wall, but inadvertently turned the shower on. The droplets of water splashed onto our bodies, as we licked, sucked and nibbled each other. But my cock was throbbing, it was telling me to fuck her. I positioned my prick infront of her muff, while continuing to kiss her on the lips. I slowly pushed into her, further and further, which resulted in small groans form Holly. I began pulling out, then pushing in further, like a 1 out, 2 in, motion. Holly began groaning shorter, faster and louder. I picked up either of her legs with my hands, and she immediately wrapped them around me. We continued to kiss deeply, as I pummelled her muff with my cock. She came, while I continued to pump her, so I sat down and lay back, so she was in control. She moved up and down on my aching cock, using her pussy muscles to milk my cock. She came again, and I could no longer hold it in. I squirted my wad into her pussy, much to her delight.

12