Penny's weekend adventure.
This erotic story is a work of fiction. There are elements of erotic man and woman sex, light bondage, voyeurism, interracial sex, lesbian sex, incest, and wife sharing. All characters are over 18 and of consensual age. If any of these subject matters offend you, please exit now.
"One more thing Penny, did you get the email about our upcoming charity auction?" Paige asked.
Paige is Penny's colleague in the legal department for the corporation they both work at. She is a pretty woman in her late thirties, tall, but never lost the baby fat from her last pregnancy, leaving her overweight. Some would say pleasantly plump.
"I read it this morning while I was having my coffee. New twist, auctioning employees time for a night of companionship, this year. The email makes it sound like fun, but it's certainly could get touchy." Penny replied.
"It did say, a night of consensual fun. Sounds like just a evening of dinner, drinks, companionship and laughs."
"Well, lets be real Paige, they couldn't very well say it's a night of fucking debauchery."
"Well if I wasn't married, I'd consider it. A carefree evening, can't be forced into sex, but if the guys hot well... why not. Besides, it's for a great cause."
"I need to think it over." Penny replied. Her friend was right, but this was still outside of Penny's comfort zone.
*****
"Jade, please bring me the Woodson file" Penny called out to her assistant.
Penny liked the younger woman almost immediately during the interview process. She even loved her full name, Jade Rose, a name as exotic as the woman herself. Jade is in her early forties and she has a bubbly and warm personality. Penny remarked how much she looked like actress, Tia Carrere. Jade loved the comparison. While Penny is her supervisor, Jade helps the whole department. Early on during their friendship, Jade said something to Penny she would never forget. "Penny, the secret to a woman's beauty is confidence and a warm smile. You're a very attractive woman when you smile." From that day forward, Penny tried to wear a smile as often as she could. Jade was right, people smiled back and were nicer to her. Jade would always say, "Keep smiling Penny"
"One moment Jade, this is the Woodford file, I need the Woodson file." Penny said before her assistant left the office.
"Oh, I'm sorry. I'll get that for you." The woman said very apologetically.
"This is the third mistake this week, what's up with you?"
"I'm sorry, I've been distracted lately. I'm trying to think of the perfect birthday gift for my husband, just preoccupied. He's turning fifty, so I want to make it special. Let me get you the file you need." Jade replied. She is a private person and never really talked about home.
"Fifty huh? So he robbed the cradle with you, very sexy. You never really talked about him before. If I can help you with that, let me know, I'm happy to do what I can." Penny said.
"Thanks Penny, I will. Have you decided on the auction? That could be fun."
"Still thinking about it. It's not really my thing."
"Well I think you should. An evening of fun, flirting, who knows where it could go." Jade told her boss.
"Thanks. But what if it's sleazy Trevor. That is my big concern."
"I certainly understand that!"
"Jade, I do mean it, let me know if I can help you figure out your hubby's birthday."
"I will, you already gave me an idea."
*****
"Penny, it's strictly consensual. There is nothing to worry about. Just a little fun for charity." Her manager tried to assure her.
"Steve, how can you be so sure? This is open to our employees, customers, and their guests. You don't know what their intentions are. The last thing I need is Trevor bidding on me, worst he could win." Penny said. She always thought Trevor was sleazy and underhanded. She couldn't stand the thought of spending anytime around him, let alone a night.
Penny added, "Be honest, would you let your wife do this?"
"Actually, she will be. We have a plan, if she's at all uncomfortable with the person bidding on her, she will signal me and I will outbid them. She has fun, and charity wins. You could do that also. Bring someone that can place the winning bid."
"Your wife could be a model, I'm in my fifties and overweight. I'll tell you what Steve, I'll think about it, okay?"
"Charity wins either way. Don't forget that Penny, it's all for charity." Steve Castle said as he left her office.
*****
Five o'clock couldn't come fast enough for Penny. Steve, Paige and even Jade, were pushing her to sign up for the auction. Colleagues complaining about Jade's work and Steve telling her she had to address it with Jade. The weekend finally here, Penny stopped to get a bottle of red wine as she drove home.
At home, she found her son Tom swimming with his latest girlfriend, Sandy. Tom never left home even though he is almost twenty one now. Since Penny hated being alone, they found ways to make the arrangement work. When he entertained his girlfriends, Penny would give them space. At night she wore earplugs to block out the sounds of them having sex. Tom worked at being discrete. There were some awkward encounters, but they both made it work.
"Hi Mrs. Carpenter." Sandy called out. "Tommy asked me to have dinner with him and an evening of pool time. You don't mind, do you?"
"Not at all Sandy. This is Tom's home, he can have guests anytime he wants."
"You are so cool, Mrs. Carpenter, I just love you. I made spaghetti, please join us."
Penny liked the young blond girl. Sandy is a tiny girl, on the short side, very thin with a cute round bubble butt. At nineteen, she is a year younger than her son. The first time Penny saw Sandy, was when she walked in on them while she was on her knees, giving her son a blowjob poolside. Penny left before they saw her, but it was an erotic image burned into her mind.
Dinner was pleasant, Sandy is a good cook. The dinner conversation was enjoyable and flowed easy. When the kids went to change for the pool, Penny excused herself and headed to her bedroom. Penny laid in bed reading a book with her earplugs in. She didn't know when they would be having sex, but Penny knew sooner or later, her son would be fucking this young woman.
Sandy spent another night at their house. Penny went shopping and spent time in the park to give the young couple more time to themselves. Every now and then, Penny would open the app for the security cameras to see if it was safe to go back. The first time, she saw her son going down on the young woman's pussy poolside. She turned it off when Sandy arched her back and cried out as she orgasmed. Twenty minutes later when she checked, Sandy was bouncing on her son, in the reverse cowgirl position on the sofa.
Penny hated to admit the erotic images were turning her on. Penny didn't date much these days, so she found herself getting turned on easily. She felt her own pussy getting wet. The park was no place to touch herself, but she had an almost uncontrollable urge to finger her pussy to orgasm. She knew it was wrong, she was watching her son after all.
Penny returned home an hour later. Tom and Sandy were sunning by the pool, side by side, holding hands. That evening, when she heard Sandy crying out in orgasm, Penny could not resist sneaking across the small house to listen better.
"Oh fuck Tommy, you have such a big cock. I love the way you fuck my little cunt baby. Gawd, who taught you to fuck. I need to thank her."
"Your pussy is so tight baby."
"My cunt, Tommy! Call it my cunt. It's so much dirtier. AHHHH. I'M CUMMING TOMMY!!! POUND MY CUNT BABY, FUUCK!!! YES! YES! YES! AHHH FUCK!!!
