Fitting in with the Upper Crust Ch. 08

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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AN EVENING WITH DIANE

After an afternoon encounter that scratched Diane's itch she was already looking forward to the evening with Buddy. He reminded her that he was going to make love to her bottom and that she needed to be squeaky clean. It was Tuesday and that was always anal day for them and she knew that Buddy was not going to pass up that opportunity.

Jeannette had arrived home from shopping and noticed that Diane had the glow that said, "I just had my brains fucked out." She suspected that her sister-in-law and Buddy may have been intimate that afternoon. She could not prove it but she suspected as much. When she was alone with Buddy she posed the question.

"Buddy, have you and Diane been having an affair?"

"Of course not, I have a good thing going here and I wouldn't do anything to screw that up. There are only two more weeks before I head off to college and living here this summer has been a dream come true."

"I see but I will tell you as only another woman knows, it looks suspicious."

"Well we are not having an affair and even if we were I would not tell anyone. No more than I would tell anyone that I have been fucking you."

Jeanette smiled and countered, "I appreciate your discreteness, speaking of which are you available right now?"

"Don't be ridiculous, Diane is in the house. I'm going to clean the pool now."

"Okay but I want to be with you again before I leave for home tomorrow."

"We'll see, now please excuse me."

Buddy went out to the pool and began his chores. Normally Monday was pool cleaning day but Jeanette had occupied most of his time yesterday. While Buddy was cleaning the pool, Diane was taking a bubble bath. She loved the way her skin felt in the oily water and it made it easy to cleanse her anus. Her oily finger easily entered her rectum as she went about cleaning her bottom. She was already anxious about that evening and would impatiently wait for the others to leave for dinner.

After Albert and Jay got home from the office they picked up Jeanette and headed out for dinner. Albert made one more plea to his wife to join them but Diane refused. When the three of them left the house Diane made a bee line for Buddy's room where he was waiting for her. She knew it was an hour drive to the restaurant and they would probably dine for two hours. That gave her at least three but close to four hours with Buddy.

Buddy knew that the best way to Diane's ass was through a thorough pussy fucking that left her completely sated and receptive to anal sex. Diane had only worn a robe over her naked body when she went to his room and he was sitting on the bed equally naked waiting for her.

"Let's start with a massage Diane. I want to feel your body."

Diane just nodded her head accepting the offer as she dropped the robe and lay face down in his bed. He began to work on her shoulders and neck. She cooed appreciatively as he massaged her body. He worked his way down from her neck and shoulders to her lower back. As he always did, he purposely bypassed her buttocks and moved to her calves. He massaged her calves and then moved to her thighs where he spent more time. She could feel her body heating up again and driving toward another orgasm. He finally moved his hands to her shapely fleshy ass and molded the soft globes in his hands.

He loved the look and feel of her ass and he thought about fucking her in her ass first but then decided against it. He would wait until she was ready. Buddy lifted Diane to her knees and slipped his cock in her pussy and fucked her doggy style. She turned her head to the side and groaned when the big cock filled her again. He fucked her in the doggy style position and caressed her curvy bottom. He sensed that she was hot again so he pulled out of her pussy and turned her over on her back. Then he positioned himself between her legs and fed his cock into her pussy again.

"Oh yes, oh it feels so good, oh, oh, fuck me, yes fuck", she cried as she was close to another orgasm.

Buddy slid in and out of her pussy slowly allowing her to adjust once more to his size and he continued to go deeper with each thrust until he was buried balls deep in her pussy. He pounded her pussy making sure that his cock was in constant contact with her clit. She had a seemingly continuous orgasm as he fucked her. Diane was one hot lady. He could feel his balls start to tighten and he knew it wouldn't be long before he filled her pussy with his cum for a second time that day. She stiffened and then had another violent orgasm.

She called out to him, "Hold me, please hold me, I'm cummmming!"

He reached around behind her back and pulled her toward him as she shook and trembled throughout her intense orgasm. As she was cumming, he did too and he fired another barrage of cum into her pussy. As she started to recover he gently laid her back down on the bed and slowly fucked her until his cock softened. He slowly eased his semi-erect cock from her womb.

Diane ran her hands over Buddy's muscular arms; pecs and washboard abs. Then she looked down at his soft cock and took it in her hand. Even soft it was bigger than her husband's cock. She felt his cock harden in her hand and at first she couldn't believe that he was ready to go again. Even in her near exhaustion, she held her arms open to him welcoming him between her legs again. He moved between her legs and slipped his hard cock back in her pussy. He fucked her as long as he could before she pleaded with him to let her rest.

"Please stop, I have to rest. I am not sure I can cum anymore."

Those were the words he was waiting to hear and he began to pick up the pace. Soon he was pounding her pussy and fucking her into submission. She moaned and groaned as he relentlessly fucked her. He just kept at her with his big dick until she screamed and pleaded with him to stop. Buddy pushed his body up and he eased his cock out of Diane's well fucked pussy. A sated and exhausted Diane rolled over on her stomach to protect her pussy. He knew her ass was now for the taking and he pulled her up by the hips.

Buddy looked at Diane's ass and he could not resist running his hands over her shapely cheeks. Her ass was so amazing that he had to fuck it. He got to his knees behind her and kneaded her gorgeous ass cheeks. He then began to kiss her cheeks and run his tongue lightly in the crack of her ass. The scent of her told him that she had done what he told her earlier. She wiggled her ass feeling very wicked as he tongued and kissed her. Diane's head was still on the bed and she turned it to one side and let out a gasp as his tongue licked close to her anus. Buddy ran his tongue from her pussy to her nether hole causing her to tingle in anticipation of what she knew was next.

Buddy spread her ass cheeks with his hands and dipped his tongue into the crack locating her nether hole. His tongue slowly circled her amber ring and she flinched at the contact. He then pushed his tongue as far as he could into her anus. She had been ass fucked enough in the past but each time she was still worried about his size. He continued to ass fuck her with his tongue and she was at his mercy. Her desire grew as he worked her to the point that she really wanted more in her bottom.

She reminded him to use some cream and he reached for the tube on the nightstand. She arched her back and pointed her beautiful ass back at him. He coated her anus with a generous amount of cream and slid his thick finger in her hole. He took his time preparing her relishing every moment. He then coated his entire cock with the cream and placed the head at the entrance to her dilated anus. He pushed forward and the thick soft mushroom cock head squeezed into her tight opening.

Diane winched and she gasped, "Go slow let me get used to it."

Buddy withdrew his cock head and then pushed it back in this time causing more pleasure than discomfort. He pushed until a couple of inches were in her. She found herself holding her breath and her body covered in goose bumps. As many times as he had been there, he was so thick that she stretched to new dimensions. He slowly slid his dick in and out of her each time going a little deeper. The pressure had subsided and was replaced with a feeling of fullness.

She relaxed a little and then felt more of his cock slide into her asshole. She grunted out loud as she felt fuller and then a wave of pleasure through her body. The sensation felt like he had his whole cock in her now but really he only had about half of his big dick in her. She felt so full so had no idea that he had another four inches before he was done. He kept adding more and more of his cock to her ass. There was pressure then fullness and then pleasure each time he went deeper. Diane would tense, relax and then enjoy it. This pattern continued until had all eight inches buried in her ass.

Buddy methodically fucked her in her tight ass with his sizeable cock. He loved watching his big dick slide out of her shapely ass and then plunge back in as his hips slapped against her curvy ass cheeks causing them to jiggle with each thrust. He loved the view as he watched her ass impaled on his cock. Her moans were very audible as he fucked her ass harder and faster.

Diane's rectum pulsated as he drove his big cock in and out of it. Her ass involuntarily squeezed and released his huge member causing him to finally lose it. He slid his pecker deep into her rectum as his cock spasmed and sent a thick stream of hot cum into her channel. Buddy kept fucking her as load after load was fired into her ass as his cock kept twitching and spurting inside the impaled housewife. Her passage was full of cum and there was no place for it to go blocked by his swollen cock buried in her ass. He slowed his pace and eventually stopped allowing his dick to remain buried in her ass. He did not go soft right away and he gently moved his hips pushing cum around in her bottom. Some of it gradually trickled out and ran down over her pussy lips.

She could not take any more fucking and she pleaded, "Please no more, I can't take any more, please stop."

Buddy stopped and slowly withdrew his cock from her loosened passage. He marveled in the sight of his enormous cock sliding out of her shapely ass. The man seed flowed from her nether hole and ran like a river down over her pussy and between her sweet thighs. They stayed in the same position for several minutes and he massaged her beautiful ass as she remained on her knees with her tush perched in the air. He pushed down lightly on her back accentuating the shape of her lovely ass even more. He loved looking at it and playing with it as she cooed into the bed sheets. His cock remained hard and looked menacing around the nether hole. It was hard to believe that a cock that size had just fucked such a beautiful tight ass again. She looked magnificent with her just fucked curvy ass in the air.

"I am absolutely worn out," she sighed.

"Me too, that was great but we should get cleaned up. I think that I heard a car door close."

That comment sent Diane into a panic state. She leaped out of bed, gathered up her robe and dashed for her bedroom. She turned the shower on and as soon as the water was warm she was in it. Buddy had been right and the others had returned home from dinner. He looked at the time and realized that he and Diane had been at for over three hours. He decided to wait to take a shower, turned on the radio and looked at a magazine. He was naked under his bed sheets when he heard a knock on his bedroom door.

"Come in, I'm awake."

Jay entered the room, closed the door and sat on the foot of the bed.

"How was dinner?"

"Dinner was very good, it's a great restaurant. You should have joined us."

"Nah, it was a family dinner. It was better that I stayed here."

"I guess. I'm glad that my aunt is leaving tomorrow; too much tension between my mom and her, besides she kind of interrupted our time together."

"We'll make up for it Monday and I have a suggestion. Remember my old girl friend Cindy, well this girl Sandy and I have been talking about a threesome. I thought we could invite her over on Monday."

"I'll think about it. I did like it with Cindy since she let me fuck her ass but I have missed your cock too."

"Well think about it and I'll talk to Sandy this weekend."

"I wish I could suck your cock right now."

"Christ Jay, not with everybody home, go to bed, I'll see you tomorrow."

Jay let the room and Buddy was just about to turn the light out when he heard another knock on the door. This time it was Jeanette and she didn't wait for his invite. She entered the room and smiled at him, closing the door. She moved alongside of him and sat on the side of the bed.

"How was dinner?" he asked trying to remain cool about her presence.

"Very nice, it is an excellent restaurant. How was your time alone with Diane? Did you make her happy?"

"Diane and I don't do anything, I told you that."

"Really," Jeanette said sexily as she slid her hand under the covers and located Buddy's cock, "I bet she loves this."

"You're crazy, everybody is home now."

"I doubt anyone is going to come in your room. I'm sure that Diane is content and I wouldn't expect the guys to come in."

He cock started to stiffen in her hand but he knew he didn't have much left in the tank. Besides it would be insane for them to have sex with everyone else in the house.

"I bet that you would not pass the floating ball test."

"What's that?"

"If you were in the bathtub and your balls are full they would sink. If they are empty they would float. I bet yours are empty."

"Maybe, I did jerk off before."

Jeanette laughed and said, "Nice try, don't worry your secret is safe with me. Get a good night's sleep because I'm going to fuck your brains out before I leave tomorrow."

She gave his cock a firm squeeze and left the room. Buddy knew that she had things figured out. At least she didn't know that he had been fucking Jay too. He leaned over and turned out his lamp. He looked at the ceiling in the dark and wondered what the morning would bring.

AN EROTIC WAKE UP CALL

On Wednesday morning Buddy sensed that someone had entered his bedroom. He rubbed his eyes to try and clear them and then he saw Jeanette drop her robe and crawl in bed with him. Her naked body rubbed against his and her hand locked around his stiffening cock.

"I have to pee," he whispered.

"Not until I ride you, I'm going to make good use of this morning erection."

She straddled his body and rode his cock until she climaxed and then she collapsed on his chest. His hands caress her back and her ass as she slowly recovered from the intense orgasm. She eased off his big dick and sat on the side of the bed.

"I'll see you later. You can take your piss now."

Jeanette got up put on her robe and left his room. Buddy indeed had to pee as he felt his bladder was about to burst. He got out of bed and tossed on a pair of boxers. He went down the hall to the bathroom across from Jay's room and entered it. He was surprised that Jay was in there and had left the door unlocked.

"Sorry bud but I have to pee. Lock the door please."

"No problem," Jay replied as he reached to lock the bathroom door.

Jay watched the urine shoot out of Buddy's semi-hard cock and he reached for his own. Buddy looked at his friend and smiled. He watched Jay jerk off and he ogled the curvy buttocks. It had been a while since he fucked his friend's sweet ass and he felt his cock harden at the thought of it. Jeanette had gotten his juices flowing and Jay's ass was there for the taking. Buddy moved behind his friend and slipped his hand down the undershorts and cupped the curvy buttocks in both hands.

"Here use this," Jay advised as he handed the tube of cream over his shoulder.

Buddy pulled the shorts down and Jay let them slide down his legs and then stepped out of them. He leaned forward over the sink as Buddy lubed the scrumptious ass. He cooed softly as one then two fingers entered him and prepared him for a morning butt fuck. Buddy pushed his shorts down and liberally greased his throbbing cock. Stepping in closer he guided his stiff dick to the snug anus and pressed forward. The rubbery ring gave way and the soft head and several inches entered the receptive bottom. Jay grunted as the big cock slowly wormed its way in and stretched the anal passage.

"Agh, easy, it's really tight," Jay whispered as he reached back and placed a hand on Buddy's abdomen.

Buddy held still momentarily and Jay dropped his hand to the thick shaft. He wrapped his hand around the base of the thick cock to control the penetration. Buddy began fucking his friend with just half of his cock buried in his ass. Jay held on to the base until he loosened up and then he released it but placed his hand on Buddy's abs again. Little by little using Jay's hand pressure as a guide, Buddy eased his thick cock into the clenching gripping rectum.

He was worked up from his brief session with Jeanette and given Jay's tightness, he did not last long. Placing both hands on his friend's shoulders he drove his cock in deep and let loose a massive discharge. Jay groaned as the seed rapidly filled his rectum and his hand went to his own cock to masturbate. Buddy held onto him and let the clenching sphincter milk his cock. He stayed hard in the snug ass and watched in the mirror as Jay jerked off.

Jay rolled his eyes and his sphincter tightened around the thick cock just as he shot an enormous load into the bathroom sink. He stroked his small cock and squeezed every drop from it. Buddy's hands had wrapped around Jay's upper body and he held him tight throughout the ejaculations. Jay then leaned forward and Buddy's eased his cock out of the lovely ass. Both teens cleaned up and Buddy left Jay in the bathroom to finish getting ready. Buddy was on his way back to his room when he ran into Albert.

"Good morning Buddy! Have you seen Jay?"

"Yes Mr. Shafer, he's in the bathroom getting ready."

"Oh good, Mrs. Shafer is still asleep. I'm letting her sleep in."

"Would you like me to get the coffee going?"

"That would be great Buddy, thank you!"

Buddy went back to his room and put on athletic shorts and a t-shirt. He went to the kitchen and got the coffee started. While he waited he had juice and cereal before Albert and Jay came into the kitchen. They both had breakfast and then were on their way to the office.

"Oh Buddy, please remind my sister that a car will take her to the airport and it should be here by 1:00 pm."

"I'll do that, Mr. Shafer."

After Albert and Jay left the house, Buddy kicked back with another cup of coffee and contemplated the remaining two weeks of summer. It had been quite a ride given all the sex he had in the previous weeks and he knew that he was still in for more. This week would be busy at the tennis center as the club championships get underway on Thursday and run through the following weekend. Buddy and Sandy would be putting in extra hours to help out with the tournament. His thoughts were interrupted when Jeanette appeared in the kitchen.

A FINALE WITH JEANETTE

"I smelt that coffee upstairs. Please pour me a cup," she requested as she slid her lovely body into a kitchen chair.

"Would you like some juice too?"

"Not yet, I'll just have the coffee for starters."

"Albert said to remind you that the airport car will be here at one."

"Okay, what time do you leave for work?"

"I have to be at the club by noon and I usually leave by 11:00."

"Okay that gives us a couple of hours."

"Us, it gives us time for what?"

"I told you silly that I am going to get some more of your cock before I leave. As soon as I finish my coffee we'll go down to the Jacuzzi."