Fitting in with the Upper Crust Ch. 06

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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JAM PACKED WEEK OF SEX

Buddy reported to the tennis center Friday morning and it was the first day that week that he had not had sex in the morning. First it was all day with Jay on Monday and then all day with Jay's mom Diane on Tuesday. He also banged Diane Wednesday and Thursday mornings before reporting in at the tennis center. He arrived early Friday and had the courts ready to go by 8:00 AM.

Sandy arrived at 9:00 AM and she had a group lesson with young beginners. There were other players arriving and soon the courts were occupied. It was popular to play in the morning and hang out at the swimming pool after lunch. There were some cute girls and some fit older women on the courts that day and Buddy enjoyed watching them play. He loved watching them serve as their little skirts flipped up and showed off their panty covered shapely bottoms. He was surprised to see Caleb there that afternoon.

"Hi Caleb, did you book a lesson?"

"Oh no I just came by to invite you and Jay to my house on Monday. My parents are leaving Sunday night and won't be home until Tuesday."

"Okay, I'll check with Jay. He has been anxious to meet you ever since I told him about you."

"Good, I hope you can both make it. I've been looking forward to meeting him too."

Caleb walked away and Buddy ogled his round curvy ass in the tight fitting shorts. "Damn, what a great ass!" he thought to himself.

Just then Sandy walked over as she was done with her lesson. "Buddy would you help me pick up all these tennis balls?"

"Sure Sandy, I'd be happy to."

"Listen Monique really likes you and she was wondering if we could get together tonight after work."

"I guess we could but remember we have to be here by 8:00 in the morning."

"I know. We can do it. We may be a bit tired but I'll be here for sure."

"Okay it's a date then."

"Thanks for your help with the balls."

Buddy ate lunch first and then Sandy so that one of them was at the pro shop. It got really hot and the courts were empty until the evening. The pro shop closed at 6:00 PM but Buddy left a couple hoppers of balls out just in case any members needed them. He and Sandy left the club and drove over to Monique's house. Monique had wine and cheese ready for them which Buddy appreciated.

After enjoying the wine and cheese the three of them went to Monique's bedroom and got naked. They arranged themselves in position as Monique got into bed and Sandy dove right into her pussy. Buddy rubbed his cock up and down between Sandy's buttocks and she cooed and moaned before she said, "If you want my ass remember you are going to have to put some grease on that monster."

Monique said excitedly, "Do it Buddy, you know how she loves it in the ass. I want to see you fuck her there again"

He got the cream from where Monique told him it was in her bathroom. He took out some and began to finger Sandy's asshole. He again marveled at her lovely ass. Her cheeks were firm and her ass was incredibly round. He fingered her anus applying an ample of lotion to it as he relished in its beauty. Satisfied that she was well lubed he lined up his cock and pressed forward into her snug chute. She gasped as he pushed his cock into her ass. She gradually relaxed and he slid in further and then she returned her attention to her girlfriend's pussy.

Sandy's moans were muffled and lost in Monique's pussy. Buddy held her hips firmly and continued to push his cock in deeper and deeper. She moaned with joy into Monique's cunt. She reached for her pussy with her fingers and rubbed her clit frantically as she sucked on her lover's clit.

He had finally buried his entire cock in her ass and he held still as her rectum relaxed a little adjusting to the intrusive invasion. Sandy realized that she had been holding her breath and then she started to breathe easier and relieve some of her tension. Buddy began a slow fucking motion and caressed the shapely buttocks. Sandy never really felt any pain but once again she felt that pleasurable pressure in her rectum and bowels. The pressure was starting to subside and she began to enjoy the ass fucking. Buddy sensed that she was relaxing and loosening up so he began to fuck her with long deep strokes.

Sandy rotated her ass in response to the fucking and Buddy thought to himself, "Oh man I love this fabulous ass."

Sandy started sucking on Monique's pussy at a furious rate which signaled Buddy that she was approaching her own orgasm. He picked up the pace and really began to pound her ass. His cock would come almost all the way out and then he would shove it back in to the hilt. Monique grunted and groaned in orgasm as Sandy sucked up all of her juices. Sandy then lifted her mouth off of Monique's twat and groaned aloud as Buddy pounded her ass.

"Oh, oh, oh, yes give it to me. Fuck my ass, fuck it!" she screamed for the both of them to hear.

He increased his speed and his cock was flying in and out of her ass. His thighs were slapping into her buttocks causing her ass cheeks to jiggle with each thrust of his cock. He then shoved his cock in all the way, stiffened and grunted as his cum shot out of his pecker into the receptive ass. He emptied his balls and flooded her passage with his spunk. She felt bloated as cum filled her to overflowing. He kept fucking her ass and he could feel his semen squishing around in her rectum. Monique was humping Sandy's face as she too approached her orgasm.

"Oh God Sandy, don't stop please, make me cum. I'm going to cum. I'm cumming Sandy, oh Sandy!" Monique screamed as her body thrashed around with the intensity of her orgasm.

She continued tongue fucking her and playing with her clit until Monique could not stand it anymore as her body went rigid. She moaned and lifted her hips toward Sandy's face as if she were trying to get the tongue deeper into her pussy. Sandy grabbed Monique's ass as she continued with her tongue lapping and squeezed the shapely ass at the same time. This final act took Monique over the edge with a mind numbing orgasm.

Sandy and Buddy collapsed and fell forward with his cock still in her ass. He lay on top until his cock softened and began to slip from her ass. He rolled to the side and his cock slipped from her well fucked bottom. As she lay on her stomach his sperm seemed to bubble up and ooze from her anus. Sandy clenched her sphincter and more cum squirted out of her ass and ran down between her ass cheeks and inner thighs. Monique watched and was mesmerized as his cum seemed to trickle out for quite a while.

Sandy rolled to her back and Buddy and Monique stared at Sandy's rock hard extended nipples. Her nipples stood out like erasers on pencils and they were just as hard. Her nipples looked even bigger given the smallness of her breasts.

"I love your hard erect nipples," Monique replied and then kissed the tits and took her nipples in her mouth one by one.

She moved from one to the other taking the entire breast in her mouth and sucking the nipples. Monique let each nipple pop out of her mouth with an audible sound and Sandy's nipples seemed to get harder and longer each time. Sandy moaned aloud and grasped Monique's head holding it to her breasts. Buddy got hard again just from watching the two girls.

The three of them lay back on the bed and the girls moved into a 69 position and began to lick each other's pussy. He lay down behind Sandy and played with her fabulous ass for a while before sliding his cock back into her ass. Sandy grunted softly in Monique's pussy as the cock slid all the way in. He fucked her slowly as he wanted to make it last as long as possible. Sandy grabbed onto Monique's firm ass cheeks and held her tight as she worked on her pussy. She then began to finger Monique's pussy with one then two fingers. Her juices were overflowing with desire and she was panting as she approached another orgasm. Sandy started to play with Monique's anus and she moved pussy juice to her and lubricated it with her natural moistness.

The finger teasing her nether hole felt good as Sandy ate her pussy but Sandy caught her off guard when she inserted a finger into Monique's asshole. Monique gasped into Sandy's pussy as the digit sank into her asshole. The single digit felt good as she moved it around in the rectum as she continued to suck on her pussy and nibble her clit. Monique was the first to cum this time and her body spasmed in orgasm as Sandy held her mouth firmly to the gushing pussy and plunged her finger as deep as she could into the lovely ass.

Buddy despite all his efforts to control himself finally gave in to Sandy's ass milking technique. He shot another impressive load into her ass and let his cock stay in her as she milked it dry with her anal muscle. His deflated cock finally slipped from her hot ass. He noticed a trail of cum oozing out of her asshole and he pushed it back in with his finger. Sandy rotated her ass in encouragement as Monique continued to eat her pussy. She finally orgasmed dousing her lover's face with her female nectar and Monique gobbled it all up.

They rested for several minutes as they lay together in the bed and stroked each other's body. Monique still had not been fucked and she wanted Buddy to fuck her next. He slipped between her legs and eased his cock into her pussy. She was glad that he had already cum twice because she knew he would last longer this time in her pussy. He knelt between her legs as he fucked her and Sandy played with Monique's tits and nipples. Sandy decided to straddle Monique's face and lower her pussy to Monique's mouth. She wasted no time in locating Sandy's clit and she began to lick it and gently nibble it driving her wild.

Monique and Sandy had multiple orgasms before Buddy came again. He dumped his seed in the sweet pussy just as Sandy came on Monique's face again. That sent Monique over the edge and she had one more mind blowing orgasm that rocked her body. The three of them collapsed alongside one another in the bed and cuddled together. They rested for nearly 30 minutes with their three naked bodies touching one another. Buddy then got up and announced that he had to get going.

"Monique is it okay if I take a quick shower?"

"Of course it is."

He showered and dressed as the two women remained in bed. He smiled at them as he took in their beauty.

"Buddy, I may be a few minutes late in the morning."

"Don't worry Sandy, I got you covered. I'll be there early."

"You're a doll."

Buddy kissed them both on the cheek when he said goodbye. As he left the house the two women turned to each other and kissed. They cuddled together and caressed each other lovingly. Sandy would stay the night and they would make love again in the morning.

MONDAY AT CALEB'S PLACE

The rest of the weekend was busy for Buddy and by Monday he was ready for a relaxing day but he was also up for more sex. Albert left for the office and Diane went to her Monday social gathering. Jay told his mom that they would be at a friend's pool that day but would be home for dinner. Diane wondered if Buddy, Jay and this new friend Caleb would be having sex that day and then dismissed it knowing that she would have Buddy to herself on Tuesday.

The boys arrived at Caleb's house at 9:00 AM that morning and they were all horny. Buddy decided to let Jay and Caleb go first before he joined in. He sat in one of the soft family room chairs and watched with interest. Jay and Caleb were hugging and kissing as they began to remove their clothes. First the tee shirts came off, then the shoes and socks and lastly the shorts. Both left their briefs on as they caressed each other's body and rubbed against one another.

Jay pulled Caleb's briefs down to just below his buttocks and Buddy stared at and admired the super fine ass on the young man. Caleb's ass was perfectly shaped and stood out from his lower back and the back of his thighs. His skin was flawless and his body virtually hairless. The contrast between Caleb's tanned body and his snow white buttocks emphasized his lovely ass even more. Buddy stared at the pretty gay and admired his effeminate figure. Caleb had great looking legs, a narrow waist and a killer ass.

Caleb then dropped to his knees and pulled Jay's briefs down and off his legs. Jay stepped out of his underwear and Caleb fastened his mouth to Jay's small erect cock. Caleb was all over it. He sucked Jay's cock taking all of it in his mouth without gagging. Buddy's eyes were focused on Caleb's ass and not Jay getting a blow job. He felt his own cock stiffen in his pants as he visualized himself fucking Caleb once again. As Caleb sucked cock he managed to remove his own briefs and knelt naked on the floor. He then stood up and turned his back to Jay who wrapped his arms around him. Buddy watched as Caleb's cock bobbed up and down in front of him as he rubbed his ass over Jay's cock. It was quite an erotic display and Buddy's cock was now throbbing in his pants.

Caleb leaned over at the waist and pushed his ass back into Jay's groin. The stiff cock rested in the crack as Caleb moved his ass up and down letting the rigid prick glide between his buttocks. The two of them kept this up until they were so turned on that they needed to cum. They separated and got on the floor on their sides in a 69 position. There they sucked each other's cock until they came.

Jay came first as Caleb stroked his cock and nibbled on the head. Jay warned Caleb of his impending release, "Get ready Caleb, I'm going to cum. Oh shit here it is, I'm cumming."

Caleb took the cock from his mouth and stroked it as Jay shot streams of semen into the air. The sperm landed on Jay's thigh and Caleb's forearm and Caleb's hand was cum covered. Jay moaned loudly and he momentarily stopped sucking Caleb's cock. Buddy watched with interest as Caleb licked up all the semen from his forearm and Jay's thigh. Then he licked his hand and fingers clean. By then Jay had resumed sucking Caleb's cock and it wasn't long before it was spewing cum into the air and landing on their bodies. Jay duplicated the scene and licked the sperm from their bodies.

They rested momentarily and then they stood up and played some more. They were still hard when they stood and Caleb again pushed his ass back at Jay. After a few minutes of foreplay, Jay sat on an ottoman and pulled Caleb into his lap. Caleb straddled Jay and slowly lowered his ass onto Jay's stiff dick. Buddy watched as Caleb was able to take the smaller cock in his ass in one steady motion. Caleb moved up and down on Jay's cock as Jay reached around and stroked Caleb's equally hard cock.

After a few minutes of riding Jay's cock, Caleb stood up and they moved back to the floor. "I need to fuck that sweet ass of yours Jay," Caleb said excitedly.

Buddy watched as Caleb filled Jay's ass and began to fuck him slowly. Jay was breathing hard as Caleb was drilling him. Buddy was more interested in watching Caleb's ass than watching his friend get fucked. The shapely buttocks tightened and relaxed each time he thrust into Jay's bottom. Buddy guessed that they fucked for at least 15 minutes before Caleb pulled out and ejaculated on Jay's abs and pubes. They remained motionless for several minutes before Caleb rubbed the semen into Jay's skin.

They were both still hard and Jay badly need to cum again. They got off the floor and walked over to the ottoman. Buddy stared at Caleb's hot ass the entire time as he waited patiently to fuck it. Caleb knelt on the ottoman and held onto the arms of the chair in front of it. Jay stood behind him and lined up his cock with Caleb's anus and pressed forward. Buddy watched as friend's cock disappeared into the marvelous ass.

"Oh your ass is so beautiful, now I know why Buddy raves about it."

Jay began slowly and steadily picked up the pace. Buddy was mesmerized with the scene before him as his best friend fucked one of the finest asses he had ever seen. Caleb's cock was still hard even though he had already cum twice and Buddy knew that they would be having sex all afternoon. Jay was in no rush to cum as he seemed to savor every second his cock was buried in the curvy ass. Both Buddy and Jay were fixated on Caleb's ass.

Jay caressed the beautiful buttocks as he repeated over and over, "Oh Caleb, I love fucking you. I love watching my cock slide in and out of your hot ass. I want it to last forever."

However the three young men in the room knew that it wouldn't last forever. In spite of how hard Jay tried to prolong his ejaculation he just couldn't help himself and he knew he would shoot a massive load into Caleb's rectum. Buddy watched as he strained to keep from cumming. Jay's head was thrown back and he groaned as the first shot entered Caleb's ass. He then lean forward and hugged his new lover, his chest covering Caleb's back.

"Oh yeah, I feel it. Give it to me. Cum in me," Caleb cried out.

Jay's hands went around the front of Caleb's body and he caressed the chest and abs as he filled the rectum with buckets of sperm. As he emptied his balls, Jay turned his head to the side and placed it on Caleb's shoulder. "Oh God!" he exclaimed as the final stream left his rigid shaft. Both of them uttered continuous sighs of pleasure and they remained coupled for several minutes before Jay backed out of the incredible ass. Caleb dropped one foot to the floor with the other leg still kneeling on the ottoman.

Buddy watched as Jay's cum oozed out of Caleb's asshole and trickled down Caleb's inner thigh. Caleb continued to expel the semen and his anus looked like a cream pie. Buddy hoped that Jay would put his cock back in Caleb's ass and push his cum in with it but Jay just held onto his rock hard cock and moaned softly.

"Let's cool off in the pool," Caleb announced.

This time it was Jay's turn to watch. Within minutes, Buddy and Caleb were in the swallow end of the swimming pool and his impressive cock was driving in and out of Caleb's shapely ass. Caleb was groaning with every thrust of the big cock. He loved having his rectum filled with thick meat and Buddy's cock was the biggest he had ever had. He couldn't wait until he felt Buddy cum in his ass and fill his rectum with the soothing warm liquid. As Buddy drilled the shapely young gay his thighs slapped against Caleb's and the water splashed against the pool wall.

Buddy caressed Caleb's lovely ass as he fucked it. It was one of the nicest if not the nicest of any ass that Buddy had ever fucked, guy or gal. Buddy loved anal sex and he would just as quickly fuck an effeminate shapely gay ass as any girl's ass. Suddenly he felt his balls tingle and his toes curled in the bottom of the pool. He felt his discharge race through his scrotum and he ejaculated into the clenching rectum. Caleb cooed aloud as the milky substance filled his ass, a feeling he never tired of. Buddy held still deep in Caleb's ass as stream after stream shot into him. He used his sphincter to milk Buddy's cock as it stayed buried in his ass. Buddy slowly eased his cock out and he watched as his semen oozed from the dilated anus.

Buddy stared at Caleb's lovely shapely ass as it expelled the sperm from his asshole. Stream after stream ran out between his buttocks, down his leg and into the swimming pool. Caleb wanted to get off again but he decided to save it for Jay.

"So much for cooling off, let's rest for a while," Caleb suggested.

Although he was still hard and ready to fuck some more, Buddy joined the others poolside and stretched out in a lounge. The three of them remained naked on the pool deck and let the morning sun bake their bodies. Minutes later they were ready for more action.

"Let's have a threesome," Caleb suggested.

"I'm all for it," Jay agreed excitedly.