Fitting in with the Upper Crust Ch. 04

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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CALEB THE SEDUCER

The tennis team won the sectional match on Friday and advanced to the second round which would be played on Tuesday. Saturday was a relax day for Buddy as he was not that busy at the club. The pool was open now and many people were swimming and hanging out there. He cleaned up and locked up that evening and then he and Cindy went to a movie and had some car sex later.

Sunday was a very different day. Buddy was busy right up until it was time for Caleb's two hour lesson. The lesson went well and Caleb progressed nicely Buddy was even able to introduce the backhand stroke. Afterward Caleb followed Buddy into the pro shop. Buddy had a woody again from watching Caleb's lovely ass. He was surprised when Caleb asked for a massage.

"Would rub my shoulders they are very tight from all those ground strokes," Caleb requested.

"Sure, I can do that."

Buddy stepped in behind the pretty blonde who sat in one of the chairs. He began to rub the shoulders and Caleb cooed and leaned back into Buddy. He felt Buddy's erection and teased him. "Do you keep another racquet in your pants?"

"Oh sorry about that I don't know why that happened."

"Can I take of my shirt? It would feel great if you rubbed some lotion into my shoulders."

"I guess if you want to."

Buddy began to put lotion on Caleb's shoulders and as his hands massaged the shoulders, Caleb let his hands drift to Buddy's tennis shorts. He felt the hands fumbling with his fly and jock and then he realized that Caleb had freed his cock.

Buddy tried to step back but Caleb held on to the big thick shaft. "Relax and let me enjoy your beautiful cock," he said as he stroked the long thick penis.

"Haven't you ever had sex with a man?"

"Just once," Buddy lied but he still wanted Caleb to know that he had been there.

"Good, I know you like my ass. I see you checking it out all the time."

"We shouldn't," Buddy said nervously.

"Sure we should, let's just enjoy this," he whispered again just before he lowered his mouth onto Buddy's cock.

"Oh my God it's going to happen," he thought to himself but this is what he wanted.

He knew that it was a big step to let Caleb suck his cock but it felt so good. He proved to be an excellent cock sucker and Buddy knew that he would cum soon. He pulled Buddy closer to him and he began to fondle his balls and stroke his perineum. Buddy was so turned on that he busted his nut quickly and flooded the succulent blonde's mouth. Caleb handled the discharge expertly and sucked every drop out of the big pulsating cock. He lowered Buddy's tennis shorts and jock down to his knees and pulled him closer. He held onto the muscular buttocks as he continued to suck Buddy's cock keeping him hard.

"Now I would love for you to fuck me. I want to feel that marvelous cock in my ass. Why don't you massage my ass and lubricate my anus this time," Caleb directed.

"I need to lock the door," Buddy stated and he hurried to lock the entrance to the pro shop.

Caleb dropped his shorts and briefs and knelt on the chair facing the back of it. He had a way of arching his back that made his ass irresistible. Buddy was mesmerized by the beautiful ass and followed Caleb's instructions. He began to massage the absolutely gorgeous ass. He worked Caleb's ass just as he had with Cindy, Diane, Sandy and Jay. He lovingly massaged the shapely buttocks and lubricated the receptive asshole. Buddy put one then two fingers in Caleb's ass and finger fucked him for several minutes. It was obvious that he would not be the first to penetrate this killer ass.

"I'm ready for you Buddy. I'm ready for you to put your big dick in me. Go slow and make this last a long time," Caleb whispered sexily.

Staring the entire time at the beautiful curvy ass, Buddy got up behind and lowered his body onto Caleb. He held his erect cock in his hand and guided it to the twitching anus. Caleb held his breath as the thick but soft mushroom head opened up his anus and stretched the sphincter. Buddy was thoughtful and gentle as he slowly penetrated the receptive ass. Caleb's ass opened up and welcomed the big cock into the warm snug passage. Buddy held still and let the hot blonde move beneath him. Once he was satisfied that Caleb had loosened up he began to fuck him with long steady deliberate strokes.

The two of them moved together as if they had done this many times before. Caleb rose up slightly on his knees while keeping his chest pressed against the back of the chair. The move further accentuated the round shape of his curvy ass. Buddy like the feel of the firm buttocks as he drove his cock all the way home. Normally Buddy liked his lovers in bed in a doggy style position but he found he liked the way Caleb felt in that position. Caleb groaned repeatedly each time Buddy buried his cock deep in the blonde's ass.

Every time Buddy drove his cock into exquisite bottom, Caleb pushed back to receive the cock. They fucked slowly and maintained their rhythm and Buddy wrapped his arms around the smooth slender upper body. Their bodies pressed together as they made love and Buddy felt just like he was in the ass of one of his female lovers. He was so wrapped up fucking Caleb's hot curvy ass that his ejaculation snuck up on him. Almost without warning he shot another massive load, this time into the clenching rectum.

Caleb groaned aloud when he felt the first stream shoot into him followed by several more streams nearly as forceful. Buddy moved his hips in and out as he ejaculated until he was nearly drained. He pressed his body into the hot blonde and remained still as Caleb clenched and unclenched his sphincter muscle around the thick shaft. Buddy was still hard when he removed his cock and moved away. Caleb turned over and took a hold of his own erection and stroked it in search of his release. Buddy watched him jerk off.

Caleb saw that Buddy was still hard and spoke softly, "Put your cock back in me. Just fuck me until I cum."

He moved back to Caleb who lifted his legs to receive the huge cock once again. Buddy eased his cock back into the loosened passage and began to fuck him. Caleb stroked his 5" stiff cock and he was pleased that Buddy was still hard after cumming twice. He watched as the blonde closed his eyes and felt the sphincter tighten around his cock as Caleb ejaculated. The load shot out in four or five streams and landed on his chest, abs and pubes.

Caleb smiled and said, "I think that you liked fucking me."

"I did. You have a beautiful ass. I loved fucking it."

"Everyone likes my ass."

"I know why they do."

He pulled out of Caleb and got towels for both of them. They wiped the semen from their bodies and then they got dressed. "Buddy, I hope we can hook up again and I'm sure you know that it is important to be discreet. However, I would like to hear about your other male experience and if possible meet him as well."

"I'll think about and I would have to talk to him first."

"That would be great. It would be great to have someone to suck and fuck."

GOOD NEWS, BAD NEWS AND BETTER NEWS

After the second round of sectionals the team advanced to the sectional final which would be played on Friday. If they won they would head to the state championships the following weekend. Buddy was at Jay's house after the matches that Friday dining with the Shafer family.

"So Buddy any plans for college?" Albert asked.

"I'm still working on it. I have a couple of tennis scholarship offers but my dad doesn't want me to go away to college."

"Why in heaven's name doesn't he want you to go to school?"

"He's old school and thinks that I should get a job and help support the family."

"Are things that bad at home?"

"Oh no, everything is fine with both my parents working. It's just they never finished high school and education doesn't seem important to them."

"What are you going to do? Would discussing it with a school official help?"

"No my folks are pretty stubborn. I'm thinking about moving out and finding a place to stay until college starts in the fall. I'll wait until after graduation to do that. I'll be 19 in July."

"Dad, why not let Buddy stay with us. We have the guest rooms available."

"That's okay Jay, I don't want to be a burden."

"You wouldn't be a burden. I think it is a fine idea," Diane injected. She felt her pussy twitch with the thought of it.

"I guess that would be alright. It would just be for the summer and I could always use some help around here," Albert agreed.

"Really, that's wonderful. That is so nice of all of you. I will be glad to help out with chores. I'll still be working at the club and I'll pay my share for food and things."

"Well it's settled then. Buddy will move in with us after graduation," Albert concluded.

Jay was ecstatic and Diane was quietly thrilled. They both would have the handsome stud around to satisfy their insatiable needs. The family finished dinner and then Buddy headed home with renewed enthusiasm. He needed a good night's sleep as he had a busy day at the club on Saturday. He was thrilled that now he would realize his dream of attending college on a scholarship. He also knew that he would have the opportunity for plenty of sex at the Shafer house. Things could not have worked out better.

BUSTED WITH SANDY AND SUNDAY WITH CALEB

Buddy had not made any plans with Cindy for Saturday night as he knew that he had a full day. As it turned out he did not close up the courts and pro shop until 9:00 PM. Sandy was still there and the natural thing was for them to have sex again in the shop before they left for home.

Buddy stripped off all his tennis attire and stood naked as he watched Sandy remove her outfit. They stood by the sofa and kissed and caressed one another. He then turned her toward the sofa and had her lean over with her hands on the seat cushion. She felt him lean into her and his erect cock caressed her ass cheeks. She turned toward him and dropped to her knees.

She took his cock in her mouth and swirled her tongue around the shaft. She then took it from her mouth and played with it. She stuck out her tongue and tickled his pee hole. Buddy's body tingled as Sandy worked over his cock. She took her time playing with it and kissing it but when she sensed Buddy was close she took him back in her mouth. He loved the way her sensuous mouth worked his cock and he knew that he would cum soon. He stiffened and she knew he was going to cum. She pulled him by his buttocks close to her and held to him as he ejaculated in her mouth. The cock pulsated as stream after stream shot into her welcoming mouth. Glued to his cock, she swallowed every drop of cum.

They finally made their way onto the sofa and Sandy stretched out on her back with her long blonde hair spread over the arm rest. He crawled between her legs and made her pussy the next target. She told him that earlier she had douched both her pussy and ass for him. He smiled and lowered his mouth to her sweet pussy. He knew his way around pussy and she loved the way he ate hers. It didn't take long for him to get her all worked up and his talented tongue soon had her moaning. She felt her orgasm building within her and she thrust her pussy into his face. He reached around and grabbed Sandy by her shapely ass and drove his tongue deep into her pussy. He swirled his tongue around her clit and then nibbled it gently. Her body rose and fell as he ate her to another climax. She warned that she was cumming and she grabbed his head and held it tightly to her cunt as she juiced his face.

He drank down every drop of the love juice and continued to lick her pussy until her body stopped moving. She was drained from her second orgasm but she enjoyed his mouth and tongue on her body. He kissed her inner thighs and tickled her labia with his tongue. He then moved away and rolled Sandy over so that she was face down. He gave her a brief massage starting with her shoulders and working down to her lower back. He bypassed her shapely ass and massaged legs down to her ankles. Then he worked his hands back up her legs and this time stopped at her buttocks. Buddy rubbed the firm flesh of her ass and then he lifted her up by her hips until she was on all fours. Remembering that she had douched her ass, he ran his tongue along the crack in her ass and tickled her anus. Sandy's buttocks instinctively tightened when his tongue touched her anus.

Sandy loved being rimmed and Buddy loved doing it to her. He was rock hard again and he knew that he soon would be balls deep in her hot ass. He continued to rim her rosebud until she called out to him.

"Oh Buddy, I'm ready, give me your cock. Fuck me in the ass," she gasped.

He took the nearby lotion and squirted some on his cock. He pushed some in her ass and fingered her as she cooed in delight. He took his time as he loved to watch his finger disappear into her anus.

"Buddy, please don't tease me. I'm so ready for your cock. Please fuck me," she begged.

He knelt behind her and eased his cock into her ass. She loved his cock and the way it slid in so easy. He filled her ass with his cock and he marveled how she could take it all the way into her ass. He fucked her slowly trying to savor every moment of the ass fucking. He caressed the shapely ass as he fucked her. As much as he wanted to fuck her ass for hours, he felt his ejaculation building in his balls. His body tensed and he flooded her ass with his seed. Cum flew out of his cock deep into her ass and she used her talented sphincter muscle to extract every drop of cum from his pulsating cock.

"I love it when you cum in my ass."

"I love it too."

"I'm going to miss this when you leave for college."

"I'm going to miss it too Sandy."

"I'm sure that you will find plenty of girls in college."

"I certainly hope so," he replied with a laugh.

Buddy kept his cock in Sandy's rectum and she continued to squeeze it with her muscle. He knew that he would remain hard and be able to fuck her ass again. He fondled her body and curvy ass as his cock began to harden once again. They never heard Cindy enter the pro shop through an unlocked window.

She had arrived at the club and decided to surprise Buddy. When she got to the pro shop she found the door locked. She walked around the building peeping into one window at a time. She was sure that she saw movement through one of the windows and it definitely looked like a couple having sex. Her heart was racing to think that Buddy was fucking someone else and she had to find out. She went around and tested each window until she found one unlocked.

Cindy crawled in through the window and found herself in the storage room. She moved into the shop and heard a girl's voice. She figured out that it came from the pro's office. Cindy rushed up the door and listened.

"Oh God, I love this Buddy. I love it when you fuck me in the ass. Cum in my ass again I want to feel it one more time," Sandy called out.

She opened the office door and saw that Sandy and Buddy were both naked on the sofa and he was driving his big cock into the bleached blonde's ass. Cindy stood in shock before she could muster up the courage to say anything but then she let it out.

"Buddy, my God what are you doing? I can't believe it. You are shameless and repulsive. You're a pig and I never want to see you again," Cindy screamed at the top of her lungs.

"Oh get over it. Come here and join us and I'll eat your pussy for you," Sandy countered.

Cindy gasped at the blonde's suggestion and then ran out of the pro shop.

"I forgot to lock the office door."

"Are you going to keep fucking me?"

"Yes until I cum again. I'm real close," Buddy groaned.

He picked up his pace and fucked Sandy harder and faster as he approached yet another release. His body stiffened as he ejaculated into her ass for a second time that night and then he moved away.

"I wonder how she got in here. I locked the front door," Sandy questioned.

"Probably through a window, I'll check around. It's my fault for not locking the office door."

"She would have known anyway as I'm sure she heard me telling you to fuck my ass."

"Yeah, you're right. Hey did you really mean that about eating her pussy."

"Sure, I've done that before and had girls eat mine too."

"Wow that's wild, have you done it with more than one person?"

"Sure, I had threesomes with two guys and also with a girl and a guy."

"That's cool, we should get going now."

They calmly picked up their clothes, got dressed and checked out the pro shop before they left. He found the open window and locked it. They left together and headed to their respective homes.

The next day Caleb arrived for his afternoon lesson and afterward he invited Buddy to his house. "My parents are away and I have the place to myself."

Buddy accepted the invitation and Caleb helped him straighten up and close the pro shop. Buddy followed him to the stately home and entered the impressive house. Caleb offered him a beer and they both relaxed with one before it was time to move to Caleb's bedroom. Caleb was ready to get fucked and Buddy was anxious to get his cock in that incredible ass again. There was no foreplay as both teens shed their clothes and got in bed and within minutes Buddy was buried balls deep again in the tight asshole.

Caleb was flattened on the bed face down as Buddy drove his impressive cock deep into the bowels of his new lover. The shapely ass moved under him but Buddy's strength and drive kept the blonde pinned under him. His powerful buttocks clenched and unclenched as he pummeled Caleb's ass. His thick cock drove into the passage and then retreated until only the head remained in the rectum. Caleb felt the powerful shaft drive in and out of his anal passage like a piston causing him to cry out.

"Oh man your cock is so big in my ass, so deep. Cum in me like the last time, I want to feel you shooting in my ass!"

Buddy continued to fuck the shapely firm ass of his lover driving his cock into the warm recess. He sensed his orgasm building in his balls and he knew that within minutes he would cum in the blonde's hot ass. He felt the pressure in his scrotum just before he unleashed a torrent of semen into the curvy firm ass underneath him. He felt Caleb's sphincter muscle tighten around the shaft and squeeze every ounce of juice out of it. He stayed hard and he continued to slowly fuck Caleb's ass as the semen coated his shaft.

Caleb sensed that Buddy was up for another round without pulling out of his ass and whispered, "Buddy, you're crushing me. If you are going to keep fucking my ass let's roll on our sides."

He rolled to his side keeping his cock in the sweet ass as he pulled Caleb to the side. His hands wrapped around and caressed the blonde smooth body. He gently pinched Caleb's nipples and kept fucking him until they both came. Caleb came two times before Buddy came in his ass again. The first time Caleb ejaculated; his cum shot passed his face and hit the headboard of bed. The second time he came his seed hit him in the face and neck. Then it was Buddy who dumped another load in the blonde's ass. The two of them rested on their sides as Buddy's cock slowly deflated and slipped from Caleb's asshole. By the time they were ready to get out of bed the semen had dried on Caleb's body.

"Come on we will hit the Jacuzzi with another beer and get rejuvenated."

"Do you have an extra swimsuit?"

Caleb chuckled, "I never use them silly when my parents are out."

The two of them got another can of beer and walked out back to the hot tub. Buddy helped him remove the cover and then they soaked in it for about 30 minutes before returning to the house.