Schoolgirl Obsessions 2

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by Cristiano Caffieri

Being a pool cleaner was not Chuck’s ultimate goal in life but it paid the bills, and he was taking a correspondence course hoping to be a lawyer. The thing that really pissed him off was that three of his customers were ex-school friends, people that had done extremely well for themselves, and loved to flaunt it. As he cleaned the crud from their pools they’d sit drinking cocktails with a look of superiority on their faces, it made him want to crawl into a hole and just disappear.

To add to his misery, while he was trying to drum up some new business in an upscale area of Miami, he ran into a woman, who was not only at the same school, but who used to treat him like shit. He’d been madly in love with Angela Hayley, she knew it and she made his life an unbearable.

She treated him like a slave. He did her homework, carried her books and at her request, he wrote numerous love poems to her. These she passed around the school and everyone laughed at his mushy efforts, even the teachers.

When he rang the bell at the Swannington Mansion, dressed in his coveralls, the last person in the world he wanted to see to see was Angela. However, after the butler had asked him to step inside the marble vestibule, she came tripping down the Scarlet O’Hara staircase with a big smile on her face and her arms outstretched.

“O my god, Chuck Harris, I never ever thought I’d see you again,” she cried, and she gave him a big hug. The woman who used to gag if he sat across from her in the school cafeteria actually hugged him.

Over tea, she told him she had suffered terrible guilt over the way she used to treat him.

“I was a miserable little cunt,” back then, she sighed, “And yet for some reason you seemed to idolize me.”

“Oh well – that’s all in the past,” he said, trying to put a brave face on the situation.

“As a matter of fact, you could do me a great favor Chuck, we’re having a charity orgy tonight and we’re a man short, do you think, “ she paused and smiled, “after all I did to you at school, you could forgive and forget and agree to join us.”

The idea of fucking some of the rich bitches that made his job so difficult at times appealed to him. And of course – it was for charity.

Scheduled to start at 8 p.m. the festivities began by the indoor pool. Everybody was in the nude when he arrived and as the introductions were made he had difficulty keeping his dick down. There were some incredibly good looking women there, and Angela was one of them.

The only thing she was wearing was a diamond choker but one hardly noticed that as her tits were her crowning glory. Unlike most of the women, she didn’t shave her pussy and it had developed into quite a bush.

Of course, there was some dowager looking brods there too and he wasn’t quite sure how they intended to partner everyone off. There was certainly a few he didn’t fancy but as they say, “you don’t look at the mantle when you’re poking the fire.”

After munchies and champagne, they got down to business. Everyone was herded together and the first competition began with all the losers warned they’d have to put $500 in the charity pot.

All the ladies left the area and the butler lined up all the men behind a curtain made from sheets. There were 10 Glory Holes cut into the drape and the men had to lob their cocks through them. When the women were brought back in they had to browse the dangling appendages and guess which one belonged to their partner. When they’d believed they’d recognized a familiar schlong they had to give him a blowjob.

Angela, although she’d certainly never seen his man- o’- war before, said he had to be her partner as her husband wasn’t up to taking part in the festivities. He was almost three times her age and chose just sit behind a window that overlooked the pool and observe.

Larry had no idea who chose his dick to suck but they sure gave it everything they’d got. They seemed to have a method all of their own and it felt great. When he was about to cum his legs went a little weak and even weaker when the sheets dropped and he found he’d been blown by a woman who must have been seventy if she was a day. She winked at him as if she knew it wasn’t her husband but wanted a bit of fresh.

After more munchies and drinks it was the turn of the men to recognize their women. This was to take place in the ballroom, where 10 massage tables lay in a row. The women left the pool area first, while the men lingered under the guardianship of Simmonds, the dour-faced butler.

Before they were allowed to follow their spouses they had to don rather tight fitting blindfolds. Like prisoners on a chain gang, they placed their hand on the shoulder of the man in front and Simmonds led them to where the action was about to begin.

There was a lot of giggling from the women as they entered, as the men all crashed into one another when the butler came to a sudden halt. He’d seen the ladies lying naked with their legs open before but it still gave the old guy a bit of a jolt. Clearing his throat and taking, what could have been his last breath, he explained the rules to the men folk.

“The ladies are laying in wait for you. You must feel your way along the row until you believe you have found your partner and then you must kneel down and on my signal, you must begin to perform cunnilingus on them. Those who are not able to determine which is their partner, or would like to drop out must pay five hundred dollars.”

There was more giggling as the naked men felt their way blindly along the row, sometimes bumping into each other and occasionally trying to feel the same twat. Now Chuck knew that Angela had one of the few bushes and he’d also noticed she’d had her vajajay pieced. He felt he’d have no problem identifying her but he did finger a few juicy cunts just for the fun of it. However, a big smile broke out on his face when he located a bunch of hair with a ring in it. She gave a gasp as his finger moved playfully around her pink petals and then plunged inside.

When all the anxious recipients had been recognized or at least believed to have been recognized, the eating began. There was a great deal of moaning and groaning from the outset and it got louder and louder.

Larry pulled Angela’s delicate lips open with his fingers and then began to move his pussy flicker up and down her wet crack. She was really on heat and began slapping her arms on the upholstery as if she was desperate to cum. When she did, she started to cry out,”Holy fuck, holy fucking fuck!” in that sophisticated accent of hers.

It was total chaos as all the women were yelling obscenities as they went into orgasm. One woman, with a particularly shrill voice, was screaming, “That’s so good – you’ve never done it like this before.” Which led one to believe it was not her husband’s tongue that was sliding up and down her happy flapper.

As the screams and vibrations died down, the blindfolds were removed and mistaken identities revealed to the sound of a great deal of laughter. It seemed that less than half of the women had been on the end of the right tongue. Now Angela suggested all the couples retire to their rooms with a bottle of champagne and she’d see them at breakfast, noting that the last one at the table would be fined a thousand dollars.

Although Chuck had fully planned to return home that night, he couldn’t resist the temptation to follow the delightfully round ass of his hostess as it led the way up the stairs.

“We’ll use the Ashford Room,” she said, as they walked down the corridor.

It turned out to be a massive, ornate room with a four poster bed.

“My husband is not able to service my needs anymore and so I want you to fuck me and fuck me hard,” she said, kissing him on the lips before diving onto the bed. “Give it to me for all those nasty things I did to you at school.”

The mattresses were built high off the floor and so he stood at the foot of the bed, grabbed her opened legs and dragged her towards him so that her cunt was in direct line with his throbbing cock. She looked up at him and smiled, waiting anxiously for penetration, she didn’t have to wait more than a split second. Holding on to her legs he moved forward and rammed it in, as far as it would go. Withdrawing it fully he rammed it in again, and again and again. Angela was groaning as if she was in pain but when he developed a rhythm and slid it in and out of her quivering quim at an ever increasing pace her groans changed into a whimper.

With her eyes closed tight and her tits swinging in time with his stroke she looked so fucking beautiful. He would have liked to have just kept that up for an hour – but it rarely works out that way. His balls were beginning to tingle as they crashed against her ass and it was long before he felt his cum surging upward and he shot his load deep inside of her.

Angela’s screams seemed to indicate that she came at the same time and her body started to vibrate violently.

“Holy fuck Chuck,” she cried, somewhat poetically, “that was fucking amazing.”

The way that she’d treated him since he arrived at her door had, to a great extent, erased those unpleasant schoolgirl memories. However, there was a little spot in one corner of his brain that still yearned for revenge. He quickly turned her over so that her ass was in the air, spit on his still erect dick, and drove it into her ass. She was not expecting that and started to breathe heavy as he grabbed onto her tits and plowed it into her.

Angela was certainly taken by surprise and was just huffing and blowing as each stroke seemed to be more forceful than the next. When he’d blew his goo she just sagged forward on the bed and lay there motionless for a while.

“When you were driving your dick into my ass you were punishing me weren’t you?” she said later.

“I suppose I was thinking of the times you made a fool of me,” he replied, apologetically, “Sorry if I hurt you.”

“Oh it didn’t hurt – but I’m not much into anal – I prefer it in the bush,” she smiled, fingering her twat as if she was ready for another round.

After consuming countless glasses of champagne and fucking half the night, Chuck fell into a dead sleep. When awoke the next morning he found himself floating on a rubber raft in the middle of the pool with a red ribbon tied around his dick. The other guests, along with his host, sat at the poolside attempting to sip their drinks while laughing hysterically.

Angela had made a fool of him once again. THE END

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Rusty was just standing, waiting for a bus, when a beautiful woman in an expensive car pulled over and asked him if he wanted a ride. And did she ever give him a ride!

Copyright 2015 Cristiano Caffieri

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