Fitting in with the Upper Crust Ch. 03

AUTHOR'S NOTE: This story includes a bisexual encounter to two consenting 18 year old boys in addition to straight sex.

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MONDAY

Diane was lying in bed on a Monday morning after her husband left for work and her son was off to school. She was fondling her breasts and toying with her vagina as she thought of Buddy. They had not had sex in over a week and she was getting a bit desperate. She had to figure out a way to spend time with him but it was difficult given his busy schedule. She missed his big cock and she knew that she had become addicted to it.

If she invited him to stay for dinner she knew that Jay would try and have sex with him. It would have to be an evening when her husband had a late board meeting. That happened once a month and the next scheduled meeting was this Thursday. Maybe she could meet him somewhere but she would have to be careful. The last thing she needed was a scandal.

She got out of bed and tossed on her robe. After making a pot of coffee she took it the Jacuzzi. She slipped into the hot tub naked and enjoyed the bubbly water with her first cup of coffee. When she finished the coffee she moved around in the hot tub and found a jet to her liking. She positioned her body so that jet was right on her clit. The constant pressure soon got to her and she orgasmed in the Jacuzzi. It took some of the pressure off of her but she still missed Buddy's impressive cock.

While Diane was masturbating in her hot tub, Buddy and Cindy cut their study hall class and hooked up in an empty school room. They locked the door from the inside and left the lights off. Buddy sat in one of the chairs and Cindy stood next to him. He ran his hands up and down her thighs sending chills through Cindy's body. He lifted her skirt with one hand and stroked her pussy with the other. Then he fingered her pussy causing her to groan. He ran his hands over her shapely buttocks and let his fingers dip into the crack of her ass. He tested her nether hole and found it to be moist. She must have lubed it in the girl's room earlier. Buddy stood up alongside of Cindy and instructed her to take out his cock.

She dropped to her knees and unbuckled his belt. Next she unfastened his trousers and pushed them down over his legs and let them puddle around his ankles. Buddy's erection was poking through his boxer shorts and Cindy slowly peeled his shorts down his legs. His cock caught in the elastic of his shorts and sprung out when it cleared the waistband. She always loved that when it happened. She stroked Buddy's cock and then looked up at him.

"You have such a nice cock. Would you like me to suck it?" she teased.

"You better, you better suck it."

She took her boyfriend's cock in her mouth and used all of her oral skills to bring him to the brink of ejaculation. She removed his cock from her mouth and looked up at Buddy as she stroked his cock.

"Do you want to cum in my mouth? Or would you rather fuck me?"

"Get on the desk babe and I'll fuck you."

Cindy stood up and Buddy bent her over his desk, flipped her skirt up over her back and exposed her lower body. He always loved the look of her bent over a desk with her skirt flipped up and her panties pulled down to her knees. He moved in behind her and buried his cock to the hilt in her pussy. Cindy was already wet and his cock slid in easily. He held onto to her hips and he fucked his shapely girlfriend from behind. He began to fondle her lovely ass and then he pushed a finger in her bottom. He was pleased how easy his finger went into her ass as he knew she expected to be butt fucked.

"Do you want to fuck my ass too?" she teased him again.

Buddy didn't answer; he just pulled his cock from her pussy and slipped it into her ass. His cock met little resistance as it entered and settled in her rectum. He was so close to cumming before that he didn't last long at all. His body stiffened and he fired a barrage of cum deep into her ass. He remained pressed against her ass cheeks as she used her sphincter to squeeze every drop of cum from his cock. He remained in her ass until his cock softened and slipped from her nether hole.

He handed the paper towels she took from the girl's room to her. She wiped the semen from her bottom and then sat on the desk. He knew that she needed to cum too so he dropped down and ate her pussy until she doused his face with her sweet juices. They got dressed and waited until just before the bell sounded signaling the end of that period. Stepping out of the empty room they made their way to their next class.

THURSDAY - FIRST JAY AND THEN DIANE

Tennis practice was intense the first three days that week and the team welcomed the rain on Thursday to catch a break. There would be more practice on Friday, Saturday and Sunday. The team would be announced on Monday and all the players were anxious.

Jay was glad that it had rained and practice was cancelled. He invited Buddy over to the house in hopes of having sex with him. The only way they could though is if his mother was occupied. He recalled the time in the Jacuzzi when it was raining and decided that was the best location.

When they got to Jay's house and he suggested the Jacuzzi in the rain, Buddy knew what was on his mind. He had enjoyed fucking Buddy before in the hot tub so he was cool with it. Besides he wasn't seeing Cindy until Saturday and he was up for some action. The changed into swimwear as Buddy had a swimsuit at the house now. They took towels and Jay grabbed some lotion before they headed to the Jacuzzi.

Diane suspected that the boys might have sex while she was in the house. She was tempted to spy on them but then thought better of it. The boys still did not know that she knew they were having sex. There was nothing to be gained by letting them know or getting caught spying on them. Diane concocted her own plan to hook up with Buddy after dinner.

At the hot tub the two teens took off their swimsuits and entered it naked. They were confident that Jay's mother would not come out in the rain and it was private in the small gazebo. Jay wasted no time fixing his mouth to Buddy's cock and getting nice and hard. He was anxious to feel it in his ass again so he handed the lotion to Buddy.

As Jay sucked on the impressive cock, Buddy reached around and fingered his friend's anus. He coated the anus thoroughly and then they were both ready to fuck. Jay knelt on one of the seats and leaned over the side. Buddy moved in behind him and eased his cock into the sweet round ass. Jay let out an audible gasp as the big dick wormed its way in.

As usual they started slow and then Buddy picked up the pace. The noise of the two firm bodies slapping together was drowned out by the sound of the Jacuzzi jets and the rain. Buddy caressed the super fine cheeks as he drove in and out of his best friend's ass. Jay surprised himself when he ejaculated without his cock being touched, that's how turned on he was. When he came his sphincter gripped the massive cock and Buddy felt the tightness.

Placing his hands on Jay's shoulder, Buddy picked up the pace and drilled the curvy ass until he too came. Streams of semen shot into the clenching rectum and filled it to capacity. Buddy leaned over and wrapped his arms around his close friend and held him for several minutes before he backed away and let his cock slide out of the anal chamber. They sat back in the hot tub and Jay located a jet to douche and soothe his anus.

Jay was the first to speak, "That was great. I have missed your cock."

"Yeah, I needed that. I came in buckets."

"I know I could feel it. Do you know that I came without touching my cock?"

"I sensed that happened when you got tighter."

"We better get back the rain has let up and mom may come looking for us."

The two teenagers got out of the hot tub, dried off and put their swimsuits on before heading back to the house. They went up to Jay's room to get dressed and as they did they played grab ass. Jay played with Buddy's cock and Buddy with Jay's ass. They were tempted to fuck again but knew it was too risky. They finished dressing and went down stairs. Diane invited Buddy to stay for dinner and he accepted.

After dinner the boys helped her cleanup in the kitchen. At one point Diane whispered to Buddy, "When you leave tonight, move your car part way down the driveway and wait for me."

He looked over his shoulder to be sure that jay wasn't watching and then he grabbed Diane's ass and whispered back, "I'll be waiting."

Once the kitchen was cleaned up Buddy left the house and Jay went to his room to do homework. Buddy pulled his car far enough down the driveway where one could not see in the windows from the house. It was still secluded from the street as well. He waited patiently for Diane who appeared minutes later.

"Let's get in the back seat," she whispered urgently

When they were both in back, she reached under her skirt and took her panties off. Diane that evening had just worn a full skirt without hose. His hands roamed over her sweater covered breasts and she groaned aloud. He then put his hands under her sweater and fondled her bra covered breasts. Next he unhooked her bra with one hand and pushed it up along with her sweater baring her firm tits. He lowered his mouth to her breasts and sucked on her nipples. The nipples responded and soon they were like hard pencil erasers sticking out.

She was crooning and groaning as he fondled and sucked her tits. Her pussy was soaking wet and the smell of her sex was present in the car. He slipped his hand under her full skirt and caressed her legs. Diane responded by moaning and opening her legs. Buddy slipped his fingers into her twat and she humped his hand rapidly. She had a quick orgasm and her body thrashed around on the seat of the car.

Buddy rapidly unfastened his own pants and pushed them along with his underwear down his legs. Diane quickly grabbed his cock with her hand and then covered it with her mouth. After sucking him for several minutes, she straddled him and lowered her cunt onto his throbbing hard cock. She groaned softly as the shaft penetrated her and filled her pussy. She began to rock back and forth as he thrust up into her.

He pushed her sweater and bra back up so he could suck her tits as he fucked her. He then grasped her buttocks with both hands and played with her ass. He loved holding her beautiful firm ass as he banged away at her pussy. The two of them fucked each other with passion as they raced toward their orgasm. They seemed to cum at the same time. Buddy grunted as his body stiffened and he fired a barrage of cum deep into Diane's womb. She lowered her head onto his shoulder to muffle her scream as she experienced a massive orgasm. Her body shook and rocked as she drenched Buddy's pubes with her love juices. Buddy's cock was swimming in their juices comingled and they held to each other.

Buddy did not give Diane a minute of rest as he began to remove her clothes. He wanted her completely naked in the car when he fucked her again. He removed her sweater and bra baring her fantastic tits. Next he removed her shoes and skirt. She was completely naked in a boy's car for the first time in her life. She truly felt like a naughty teenager.

Buddy turned Diane so that she faced away from him and she felt him as he embraced her from behind. He put his hands around her and cupped her firm tits. His cock slid up into the crack in her ass and nestled in between the cheeks. She leaned back into him and he kissed her on the neck. He then let his hands slide down the front of her body over her flat tummy and down to her luscious thighs. She cooed as his hands made their descent. He next moved his hands up to her pussy and cupped it gently. Diane was soaking wet and she couldn't stand the teasing any longer.

"Buddy, please I need you inside me again now," she whispered.

His cock slid easily into her sopping wet pussy and she gasped as it penetrated her deeply. They began a slow and steady fucking motion but before too long they were pounding each other racing toward their orgasms. Diane came first, her eyes rolled and her body went into spasms as she reached her climax. She covered her mouth with one arm to muffle her cries of ecstasy as he humped her for all she was worth.

He kept right on fucking her and fingering her clit. Diane had a continuous string of orgasms before Buddy finally shot another load deep into her womb. His body went rigid as he drove his cock in as far as it would go and fired warm streams of cum into her womb. Diane totally forgot they were in her driveway as she was overcome with the sex in her car. She stretched out face down on the back seat.

Diane located her clothes in the back of the car and got dressed. Buddy also redressed and then he was ready to head home. "That was wild," he said.

"I felt like a school girl again," Diane giggled as she got out of the car.

She walked back up the driveway and into the house as he drove away. She made herself a cocktail and relaxed in the family room. Checking the time she saw that she had been with Buddy for just over an hour. It hadn't seemed that long as it was non-stop sex. She really could have lost track of time and Albert could have come home while she was still in Buddy's car. Wouldn't that have been a scene? She knew she would have to be more careful in the future.

TENNIS SEASON BEGINS AND THE CLUB OPENS

Both Jay and Buddy made the tennis team. Buddy was still number one singles and Jay number one doubles but he had a new partner. A junior named Brian was paired with Jay. He was an excellent doubles player and Buddy was pleased as he could concentrate on singles. They had a strong team and won the first four matches handily. They faced another good team on a Tuesday afternoon at the other team's court. They came away with a hard fought 3-2 victory. They won two singles and one doubles with Buddy and Jay and Brian both winning their matches. They would face that team again later in the season at sectionals.

Buddy was employed by the country club again and the head pro was glad to have him back. While school was still in session he would work on weekends. He could not assume the title assistant pro since he was still playing high school tennis. He would stay very busy the remainder of the school year, playing tennis, working at the club, keeping his grades up and balancing his sex life with Cindy, Diane and Jay. He didn't realize it at the time but his sex life would get even more complicated.

The club hired another assistant a 19 year old bleach-blonde girl, Sandy. She was average looking with a fit body but not a head turner. She was a decent tennis player but she was hired because of her wealthy parent's influence at the club. She stood at 5'6" and weighed a trim 130 pounds. Her legs were shapely and athletic. She had a 32-26-34 figure with a cute round ass, her best asset.

She and Buddy got along fine and he liked her but never looked at her sexually until that one Saturday evening. The lessons were done for the day and the courts were empty when the head pro asked Buddy and sandy to lock up later. It was after the dinner hour when they picked up all the balls, swept the courts and brought the equipment into the pro shop. Once in the pro shop since they were alone Sandy decided to seduce Buddy.

"Buddy, I am going to pick out some tennis outfits and shoes. I'll charge them to my parents account."

"Okay I can help you with the shoes if needed."

"Yes, that'll be great."

Sandy picked out a skirt with a couple of tops and headed for the fitting room. She had become enamored with Buddy and she was already looking forward to seducing him. She knew that he had a girlfriend so she planned to blow his mind sexually. In the fitting room she took off her bra and panties before trying on the tennis attire. Sandy walked out of the fitting room to check out the look in the mirror. She was naked under the outfit. She liked what she saw and then she returned to the fitting room and tried on the other top. Once again she returned to the mirror and approved of her choice.

"That looks great on you. Are you ready for shoes?" Buddy asked.

"Sure, I'm a size 8," Sandy replied wondering what his reaction would be when he looked under her skirt.

"Have a seat here and I'll measure your foot to be sure."

Sandy sat down and when Buddy lifted her foot the skirt rose and he could clearly see her bare pussy. He measured her foot in spite of the distraction but he was turned on by her boldness. He located a pair of tennis shoes in her size that he thought she would like. He gave her a pair of peds to put on with the shoes and he watched as her skirt rose and bared her pussy again. He put on both shoes and tied them for her.

"Walk around in them and let me know how they feel," he told her.

By then Buddy had a boner and he tried to adjust it in his shorts as she walked around the pro shop. "They feel fine. I will need some peds too."

"I think that you have been checking me out," Sandy whispered.

"How could I not, you're not wearing panties."

"I know, I should probably buy some tennis panties too," she giggled.

At this point Buddy had to make his move. He brought Sandy into the pro's office after locking the front door to the pro shop. Sandy dropped to her knees and unfastened his tennis shorts and pushed them down over his legs and let them puddle around his ankles. Buddy's erection was poking through his jock and she slowly peeled the jock down his legs. His cock caught in the elastic of his jock and sprung out when it cleared the waistband. She was unprepared for the size of his cock. She stroked it and then looked up at him.

"You have a big cock Buddy. I bet you would you like me to suck it, wouldn't you?"

"You bet I would. I want you to wrap those sensuous lips around it."

Sandy took Buddy's cock in her mouth and used all of her oral skills to bring him to the brink of ejaculation. She removed his cock from her mouth and looked up at him as she stroked the thick shaft.

"Do you want to cum in my mouth? Or would you like to fuck me?"

"I'll cum in your mouth first and I'll still have plenty left to fuck you,"

She resumed sucking his cock and it did not take long for him to shoot in her mouth. He blasted a huge load into her mouth surprising her with the volume and force of his ejaculation. She quickly swallowed every drop and he remained hard even after she had drained his cock dry.

"Now we'll fuck!"

Sandy stood up and Buddy bent her over the pro's desk, flipped her tennis skirt up over her back and exposed her lower body. He moved in and his cock slid in easily. She was obviously well experienced in sex. He held onto to her hips and he fucked the athletic blonde from behind. He paid attention to her curvy bottom for the first time and began to fondle her shapely ass. Testing the water with her, he shoved a pussy moistened finger in her anus. He was surprised how easy his finger went into her ass and he then knew she was no anal virgin either.

"I think you like my ass. Do you want to fuck my ass too?" Make me cum first and then you can fuck my ass."

He continued to fuck the bleached-blond from behind as he reached around and began to finger her clit. She orgasmed quickly once her clit was rubbed and he learned that she was a squirter. She drenched his cock in her pussy. He pulled his cock from her pussy and told her to stay still. He located the hand lotion and returned to grease up her nether hole. Applying the lotion and saliva to his cock, he slipped it into her ass.

His well-lubed cock met little resistance as it entered her ass and settled in her passage. He was so close to cumming that he didn't last long at all. His body stiffened and he fired a barrage of cum deep into her sweet ass. He remained pressed against her ass cheeks as she used her muscle to squeeze every drop of cum from his cock. Buddy remained in her ass as long as he could and then his cock softened and slipped from her nether hole.