Jason’s brother, Dennis, was about to turn seventeen in another week. Dennis was the ‘Dennis the Menace’ in the family. Things would happen to him, not because he did wrong, but because of his curiosity.
Here are a few examples: Their father had a burn barrel. During the week, he would gather anything that could burn from around the house and throw it in the barrel. On Saturday mornings, their father would burn whatever was in the barrel and warn all his boys to stay away from it, as it could be dangerous. Being the curious one, Dennis would throw things in the barrel to see what would happen. On one Saturday, Dennis threw in a bag of popcorn. Dennis looked into the barrel just as the popcorn bag exploded. The small explosion sent popcorn and paper flying, catching Dennis’s eyebrows on fire. It was a freak accident that left him with no eyebrows until they grew back.
On another occasion, Dennis searched for something he dropped on the living room carpet. He was on his hands and knees when suddenly he let out a yell. He found the sewing needle his mother had dropped; the only problem was the needle went under his skin, and he had to be taken to the doctor to dig it out.
Elaine had agreed to come over to the house early to give Dennis his birthday present from Jason. She wore a short summer dress below her nicely shaped ass, no underwear, and no bra.
Jason met her at the door and gave her a kiss and a tight hug. Pressing her body against him, she felt the lump in his pants.
“This is turning you on, huh, Jason?”
“You look so good, Elaine; I could take you right here; you are so sexy.”
“So, what do you want me to do?” asked Elaine.
“I know his room is messy, clothes lying around that need washing and his computer games scattered around. So go in, make some noise, and start picking things up. Make sure he sees you bending over and watch if he gets a hard-on. Don’t let him touch you; you have him jerk off while you watch. Is that ok?”
“I will do as you ask, you know that, so yes, it is ok. But you are still my man, and I do not want that to change.”
“I am falling in love with you, Elaine, so that will not change.”
“I am already in love with you and will do what we agreed on.”
With that, she walked into Dennis’s room. She closed the door to wake him up. His eyes began to open to the early morning sun sliding into the room. He yawned and stretched out his arms, wondering what Elaine was doing in his room.
“Jason asked me to pick up your room a little, so I hope you don’t mind.” Elaine bent over, her bare ass facing Dennis. She spread her legs apart so he could see her sweet honey hole.
She turned to see if Dennis was hard; he was. Her nipples hardened as Dennis’s eyes seemed to grow twice their size.
“Are you hard, Dennis?”
“I am sorry, I can’t control how my cock reacts to how you look.”
“That’s ok; I understand, it is a normal reaction. Can I see your erection?”
“What will Jason say? I don’t want him upset at me; you are his girl.”
“It’s all right. It was your brother’s idea. He wants to wish you a happy birthday. He said to look but not touch.”
Dennis threw back the covers so Elaine could see the bulge in his underwear.
“My, how nice. Did I cause that erection?”
“You sure did.”
“Can you take off your underwear?” Elaine said passionately.
Dennis pulled them off, revealing his bare cock to Elaine. He made his cock vibrate for her eyes.
“Grab your cock, Dennis, and massage your balls. Maybe this will help.” Elaine pulled her top down, showing Dennis her smooth, round breasts and perky nipples.
“Oh hell yes, that helps. Do you want to watch me jerk off?” Dennis let his eyes roam her body, her pert nipples and her young womanly juice dripping between her hairless folds.
“You are so hard, Dennis; run your hand over that swollen head for me.”
Dennis grabbed his cock and gently let his fingers stroke his cock head. He placed the other hand cupping his ball sack.
Elaine started to rub her clit with one hand and massage her breasts. Elaine shoved two fingers inside her now wet fuck hole, moving them around to make a sloshing noise, then bringing her fingers to her lips, tasting herself.
“I will come closer to see the slit on top of your cock. The slit will soon release the contents from your balls. Remember, no touching me.”
Dennis was not only hard viewing Elaine’s beautiful assets but also in the heat for his brother’s girl. He wanted to touch her, to replace the fingers in her cunt with his. Not being able to feel Elaine made him that much hornier. He would soon need release, but he enjoyed glaring at this woman standing before him. He was making a memory but desired more.
Dennis moved down the bed, allowing him to place his legs above his head with his stiffened member over his face. He opened his mouth and brought his tongue out to lick the tip of his cock.
“Dennis, are you going to taste your cum? That is so hot. Keep jerking your cock for me. You are doing so well. Mmm, stroke it for me, stroke it faster.”
Dennis did not want to hurry, yet was too excited to stop. He loved looking at Elaine’s tits as she pinched her nipple between her fingers, letting Dennis see their dark pink color.
Dennis’s breathing became more sporadic.
“That’s it, Dennis. I want to see you cum in your mouth. Rub your balls for me.”
Dennis grabbed his balls, gently squeezing them, then jerking his cock.
Elaine could see his balls tighten. She knew he was close. She encouraged him more by letting him see her finger flicking her clit.
“I am cumming, my God; it never felt so good.” He lined his cock up to his tongue as the first squirt hit the back of his throat. The second squirt landed on his upper lip, the third and fourth on his tongue. He licked the cum from around his mouth and swallowed.
Elaine was panting heavily as her body tensed and cum ran down her leg. “That was awesome, Dennis; happy birthday.” Pulling up her shoulder straps and tightening her dress, she left the room. “Please do not tell anyone; you will be rewarded later.” With that, she closed the door behind her.
“How did that go?” asked Jason.
“Just like you planned. All Dennis needed was a little encouragement. It was pretty intense.”
“We have been invited to Swap Night this Friday. Are you open to that, Elaine?”
“If you are, I am game. Let’s go to your room. I want to jerk you off.”
Elaine and Jason were spending time together. Elaine had transformed into a beautiful young lady. They agreed that when either wanted to have sex with someone else, they would let the other know first and then share the experience.
Friday Eve
It was time for Swap Night. Dot (story 4) and her husband, Jack, had a swimming pool surrounded by a privacy fence. On one end of the pool was a sauna, and at the other end, a diving board. On the side of the pool, away from the house, were four changing rooms with eight lounge chairs. On the opposite side were four tables with four chairs and an umbrella.
Jason used to babysit for Dot’s two girls many times. Dot was a BBW MILF; Jason has always had eyes for her. He thought, outside his mother, that Dot was one of the sexiest older women he knew. Dot was wearing a green bra, struggling to keep her thirty-eight-inch d breasts in control. Each step she took, her breast moved from side to side. She also wore a green G-string, her prominent ass cheeks bouncing up and down as she walked. Jason had a deep desire to make out with her. Jack was a stonemason and had the build to prove it.
Barbara (story 4) and her husband, Carl, were also there. Jason babysat for their four children. Barbara wore a multi-colored bikini that held her forty-inch breasts. Barbara had a few scars on her stomach but still looked sexy. Her husband worked in the same mill as Jason’s father. According to Jason’s father, Carl had bet everyone he had the biggest dick.
Jason’s mom wore a light blue bikini top and a pink bottom. She was the sexiest of the three in Jason’s eyes. Even at forty-five, she kept that hourglass figure.
They were all there waiting when Jason and Elaine arrived. Underneath her light silk summer dress, she wore a red bikini.
Everyone sat around the tables talking, drinking beer, and sharing chips, salsa, crackers, and various snacks.
The night was warm, the stars were shining, and the swap group was about to have the best swap night they would experience.
“Ok, tonight we are going to do something different,” announced Jack. “I want to welcome Jason and Elaine to our get-together. I think you ladies know Plow Boy.” The women looked at each other and laughed. “Elaine will join the men, and Jason will join the women if that is OK with Jason and Elaine. Betty, do you want to stay with the women since your son will be with them, or do you want to come over to the men’s side?”
“I will stay with the women and my son. I know it is incest, but if nobody minds, we don’t either.” Betty replied.
“Oh, my god Betty, you and Jason! I am wet already just thinking about it. I can’t wait to see you and Jason having sex together. So you knew all the time who Plow Boy was. What a great swap night this will be,” declared Barbara.
Jason and Elaine said that would be fine.
“The only rules are for everyone to enjoy each other, that nothing that goes on here leaves here, and everyone must get naked.”
All removed their clothing. Elaine gasped at the size of Carl’s cock; he won the bet at work. His cock looked to be about ten inches. Jack’s dick was about seven inches.
Two large mats lay at each end of the pool. Bob grabbed Elaine’s hand and led her to the middle of the mat, away from the diving board. Jack was the first one to kiss her. Bob grabbed her nicely shaped breasts and kissed them. Carl stood behind her, pushing his hardened member in between her ass crack, his mushroomed head rising above her ass.
Dot led Jason to the center of the other matt, placed her hands on Jason’s face, pressed her breasts against Jason’s chest, and drew him into her lips. Barbara kissed his shoulders while running her hands over Jason’s ass. Betty reached down, grabbed Jason by the balls, and gently rolled them around.
“Betty, I want to see you kiss Jason,” Dot requested.
Jason’s mom moved in front of her son, smoothed his hair with her hand, then pulled him into her soft, warm lips, and they kissed, opening their mouth wide and licking each other’s tongues. Reaching up and massaging his mother’s breasts and pulling on her nipples left the other women speechless and horny.
Grabbing both their asses, Dot pushed them together, causing Jason’s hardened member to part his mother’s fold and slide across his mother’s clit. Betty let out a pleasant sigh. Betty’s body felt warm as they hugged each other.
“Mother and son, damn, that is so erotic, Betty. You are a lucky woman,” Barbara exclaimed.
Reaching down and grabbing Jason’s cock, Barbara pushed it up against Betty’s pussy. Jason moved his cock back and forth, fucking her pussy but not entering her.
Carl placed his hand on Elaine’s head and pushed her down to her knees, his erection waiting for her lips to encompass it. Opening her mouth, Elaine took in his hardness. Jack pushed her head further down Carl’s shaft until Elaine gagged. Carl let out a loud, moaning sigh.
Bob got on his knees behind Elaine and started kissing her ass cheeks. Jack grabbed his cock and placed it on the side of her mouth. Elaine grabbed Jack’s cock and stroked it while placing her mouth on the head of Jack’s erection. Carl grabbed one of Elaine’s breasts and gave it a hard squeeze. Bob reached around to her other breast and played with the nipple.
Elaine’s breathing became heavier, and her moans of encouragement more consistent. She desired to have all her holes filled with cock but did not want to try Carl’s cock in her ass. She knew it would hurt.
Jason’s mother and Dot were kissing and feeling each other’s breasts while Barbara was preparing to ride Jason’s hardened shaft. Jason lay on the matt and used his finger to wave Barbara to fuck him. Barbara faced Jason, placed her cunt over Jason’s post, reached down, put his hungry cock between her folds, and slowly slid it into her. She reached back and grabbed his nut sack and began her sliding motion up and down, causing her breasts to heave. Jason reached up and pressed her and grabbed her breasts in his hands.
“Let me suck on your tits,” Jason told her.
“Damn, Jason, I have wanted to fuck you for a long time. I wanted you to fuck me when I flashed you. But you ran away.”
Elaine lay down on the mat while Jack used his tongue to massage her clit. Carl was sliding his cock on her chest while pressing her tits against his fucking motion. His cock poked Elaine’s lips. Her breath was warm against his mushroomed head.
Bob grabbed Elaine’s legs, holding them up so Jack could wrap his mouth over her wet pussy.
“I want someone to fuck me; I want all of you to fuck me, fill my holes, please,” cried Elaine.
“Elaine, let Carl put his cock in your cunt, I will put my cock in your ass, and Bob, let Elaine suck on you.”
The men rearranged themselves while Elaine got on all fours. Carl’s ten inches were waiting to slide inside her. Could she take the whole thing? It was on the minds of everyone.
Elaine stayed on all fours while lowering her wet pussy against the tip of Carl’s cock head. She felt his cock against her bonnet; she pushed back, picking up his shaft with her swollen pussy until it was well seated in her, then gently slid it in deeper and deeper.
Barbaras rode Jason’s cock, enjoying the slapping noise as she fucked him. His mother sat on his face while Jason sucked out the juice in her cunt. Betty kissed Barbara while Dot rubbed both their nipples.
“Don’t make him cum yet, Barbara; I want a turn on that nice young cock,” said Dot.
Barbara stopped riding Jason and stood up while Dot took her place. Barbara stood over Jason before his mother, allowing Betty to lick her clit. Dot grabbed Betty by the hair and pulled her face deeper into her cunt. Betty could taste her wetness and smell the heat emanating from her fuck hole.
Dot was bouncing on Jason’s manhood. Jason liked the feeling of Dot’s ass slapping against his legs. He could feel her juice running down his cock.
Jason was very familiar with his mother’s smell and how sweet her juice tasted. Jason used his hands to run up and down Barbara’s legs.
“Jason, look over at Elaine; she is taking all of Carl’s cock. She is so pretty, young, and sexy,” said Barbara.
All the women looked over to see their husbands enjoying Elaine. Jason was proud of her and her willingness to explore their sexual side. They had been playing for almost an hour, and the time to cum was getting closer.
“Betty, we want to watch you bring your son to climax,” Dot told her.
Jason’s mom mounted her son while Dot and Barbara gave their pussies a workout using their fingers. They were all breathing heavily.
“Watching Betty fuck Jason is so amazing. I wish I had a son to fuck me. Damn, this is the best swap ever,” Dot panted.
Carl had his lips on Elaine’s nipple. Elaine’s fuck hole was tight around his cock. Bob had his cock in Elaine’s ass, and Jack had his boner in Elaine’s mouth. Hearing the sounds and words of Elaine being fucked by three men made them ready to release their pent-up lust.
Bob was the first to release his sperm into Elaine’s ass. Next was Carl as he held onto Elaine’s legs and rammed her one last time, filling her cunt with his sperm. Bob could feel his cock and balls rub against Carl’s cock and balls.
Barbara was next to release. Dot’s body tightened as she furiously rubbed her clit until she squirted all over Jason and Betty.
Jack sent his cum into the back of Elaine’s throat. Elaine swallowed as fast as she could.
Betty screamed as her body shook and released her cum onto Jason’s cock. Jason kept pounding her pussy until he felt his balls tighten and his cock jerking, releasing his cum into his mother.
Elaine came all over Carl’s cock before it rested, and he fell out of her pussy.
“Oh, my god. What a fucking night. Let’s all go into the sauna and then into the pool,” hollered Jack as the heat of the warm night calmed down.
