Penny’s Weekend Adventure

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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 iskenderun escort 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!!!

Penny quietly returned to her bedroom, grabbed her dildo. She pumped the toy into her pussy until she had a couple orgasms. The sounds of sex from across the house were muffled, but Penny still enjoyed them.

When she was putting her toy away, she decided to take part in the auction. Who knows maybe it will be an attractive man. She just had a couple orgasms listening to her son fuck his girlfriend. She realized, perhaps she needs more than a toy to satisfy her needs, at least now and then. She could always use Steve’s plan and have someone trusted buy her.

***** Tuesday Evening

Tom was watching TV alone when Penny came home.

“No Sandy tonight?”

“No, she has to work late this week. Besides I think we may need to take a break for a while. She’s fun, but she wants to get more serious than I’m ready for at this time. So I’m trying to cut us back to only a couple nights a week for now.

Anything good happen at work today?” Her son asked.

“Not really, I decided to go ahead and sign up for the charity auction I told you about. I may need your help. Oh and your Aunt Nikki called me today. She asked if she could live with us for a little while, I know you like her, so I said sure.”

“Mom, we only have a two bedroom house. I’m not sleeping on the sofa.”

“She can share my bed, it’s a king size, don’t worry. Besides, it’s almost time for the two of you to bar hop again. She takes you every year to celebrate your birthday.”

***** Tom thought back on how he became close to his aunt.

It began a few years ago, Tom recalled. For his birthday, his Aunt Nikki would always take him to the amusement park a few hours away. When he turned eighteen, they added a little bar hopping to celebrate. They drank to the point they had to get a hotel. Nikki rented two adjoining rooms. She guided Tom into one, helped him remove his shoes and pants, then went to her room to sleep.

Tom recalled his aunt helping him take his pants off, he thought he felt her hand lingering on his cock as she removed his pants. He was too drunk to do anything but fall back on the bed and pass out. Tom didn’t know that after Nikki got comfortable, she opened the adjoining escort iskenderun door to check on him, and found the tip of his cock peeking out of his shorts. With the young man snoring, she took advantage of the opportunity to touch and stroke him.

It was very early morning after Tom used the bathroom, he went into his aunt Nikki’s room. He found her sleeping under the blankets. The horny and still intoxicated young man, pulled off the rest of his clothes and slipped into bed with her. Nikki stirred awoke when she felt the bed move, before she could say anything, her nephew was spooning her. The strong male body holding her was nice and comforting, as she drifted back to sleep.

A few hours later, Nikki stirred again. She found herself now spooning him, she also discovered he was completely naked. Since he was lightly snoring, Nikki again took the opportunity to feel his body. She discovered his dick was very thick and also very hard. She was surprised at the size of his balls when she fondled them. Nikki rationalized her brazen actions as, she was still intoxicated, as she groped her nephew like a wanton slut. Being intoxicated was exactly the excuse she used to convince herself to reposition so she could taste his cock.

When the fog of sleep lifted for Tom, he felt the wonderful lips and hot mouth of his aunt sucking on his cock. It was when he groaned, that Nikki swallowed his cock, giving Tom his first deep throat experience. It only took a few minutes until Tom was holding his aunts head, as he came hard down her throat.

“FUCK AUNT NIKKI, I’M CUMMING!!! AHHH FUCK!!!”

Nikki stripped the rest of her clothes off and laying next to her nephew, fell back to sleep.

Toms hand was holding her left tit and she felt his hard cock poking between her legs when she woke again. His hot breath and lips on the back of her neck.

“Tom no. We can’t do this.” Nikki said.

“Sure we can, nobody knows, it’s our secret aunt Nikki.” Tom said tweaking her nipple

“Tom, I’m your aunt, stop.” She weakly protested, while moving her leg to give better access.

“You were my aunt when you sucked me off too. I’m so hard for you right now. Feel how hard I am.”

“No we can’t… Fuck…” Nikki said when she reached felt her nephews hard cock. She was protesting, even as she guided him to her now open pussy.

Tom pushed himself into Nikki’s very wet pussy. He slowly started to pump into his aunt from behind. When Nikki got on her hands and knees for him, Tom pounded her hard holding her hips firmly. The young man didn’t last long before he slammed into her and came hard. His climax, triggered hers.

“AHHH!!! FUCK!!! CUUMMMING IN YOU!!!”

“OOOHH, TOM!!! I FEEL IT!!! HOT AND DEEP!!! FUCK ME TOM!!! FUCK ME!!!”

“AHHH YOUR PUSSY… I FEEL YOU CUMMING!!! SQUEEZING MY COCK!!!! FUCK!!!!”

After they recovered Nikki got up to take a shower, of course Tom joined her. They washed each other. Nikki was surprised to see how quickly he recovered, as his cock began to harden in her hands again. Bending over, she let Tom fuck her again in the shower.

“Do you sneak around and screw your girlfriends like this Tom?” Nikki asked as they dressed for breakfast.

“Actually, I don’t really have that much experience. I just don’t have confidence around girls.”

“You seemed to have plenty of confidence this morning. So only one or two girls huh?” Nikki said winking at her nephew.

“To be honest with you, no. Aunt Nikki, you’re my first.”

Nikki froze at that revelation. She wasn’t sure if she should be proud or ashamed that she took her nephews virginity.

“Ohh My. I don’t know what to say Tom. A persons first time should be special. Not something like this. Not a quick bang with a horny aunt. I’m so sorry, if I knew, I would never have done that. I feel terrible.”

“It’s okay, I loved it. Besides, who better to teach me.” Tom said trying to comfort her.

They discussed it as much as they could during breakfast, Nikki trying to be discrete so anyone listening wouldn’t know she just fucked her nephew. Tom would have been proud to announce it over the loud speakers, he was so happy to finally have sex with a woman.

Back at the hotel room after breakfast, Tom stripped his aunt Nikki. She gave him a lesson on how to go down on a woman. Nikki was happy to discovered that Tom was such a quick learner.

“Ohhh TOMMM! THERE, YES LICK ME RIGHT THERE!!! FUCK, I’M GONNA CUMMM!!! OHHHH FUCK TOM!!!”

As soon as she let his head go, Tom mounted his aunt again and fucked her till he flooded her pussy for the third time in a matter of a few hours.

Before they would check out, Nikki showed Tom how to fuck her big tits. Nikki was laying on her back, squeezing her big tits around his cock. Tom stroked the tunnel Nikki created for his cock. When he pushed forward hard enough, Nikki would lick the head of his cock. He spewed that load into Nikki’s mouth.

Nikki would treat Tom to a night of bar iskenderun escort bayan hopping and sex for his birthday every year after that.

***** Back to reality *****

“But what if Sandy wants to spend the night again? What then?”

“So what, your aunt knows you’re a young man. She will understand. You and Sandy don’t need to hold back just because your aunt Nikki is here.”

“It’s gonna be weird.”

“Really? Any stranger than having you mother across the house? She’s just your aunt.”

“Right. Just my aunt Nikki.” Tom replied sarcastically.

*****Nikki Moves in *****

After moving a few things in on Friday night, Penny invited her younger sister to dinner out. Over dinner she explained how Tom has a girlfriend that typically spends the nights over the weekend. Penny told her how they try to be somewhat discrete, but they are young and enthusiastic. She confided, she can hear them sometimes, but she has ear plugs which drown out most of the sound. Well, at least enough sound so a mother can sleep.

Nikki assured Penny she would be fine, she jokingly asked, “So can I have an overnight guest too?”

“You and I are sharing my bed.” Penny replied.

“I’m sure I know a couple guys that would love sharing a bed with sisters! The man could sleep between us and be the meat in our sandwich.”

“Not funny Nikki.”

“Maybe I will just share Tom’s bed. He could be the meat between me and Sandy.”

“Really not funny.”

“Maybe when I entertain, you share a bed with Tom and I use the other bed.”

“Stop it Nikki. You need to entertain, have your guy rent a room.” Penny said.

After dinner, Penny check the app on her phone, then said, “Okay it’s safe to go home.”

“Safe?” Nikki asked.

“I check the security cameras to make sure I won’t be walking in on anything.”

“So you spy on them?”

“No, just take a quick peek to make sure they are not, let’s say… engaged in activity anywhere outside of his room.”

“Do you spy often?”

“It’s not spying Nikki. I just don’t want to embarrass anyone. Just a quick peek then I shut it down. I don’t watch like it’s some live action porn.”

“Will you let me spy on them?” Nikki asked

“No, he’s your nephew.”

When they got home, Sandy and Tom were swimming in the pool. They asked Nikki and Penny if they would like to join. Penny said no, but Nikki was eager to change and spend time with the young couple. When Sandy got out to refresh their drinks, Tom joined his aunt along the pool wall.

“Sandy said ‘Thank You’… in a way.” Tom said.

“How’s that?”

“She said she wanted to thank the person who taught me how to please a woman.”

“She knows!” Nikki said in a panic.

“No. I’ve never told anyone. But Sandy likes what you’ve taught me, and I really enjoyed learning.”

“Stop it Tom, we can’t talk about this around here.” Nikki said worried.

Sandy came back out with drinks, handed Tom one and Nikki the other.

“You’re welcome Sandy.” Nikki slipped.

“Huh?” Sandy replied.

“I mean, Thank You Sandy. Maybe I should stop drinking and head to bed… well after this one.” Nikki said, as her and Tom laughed.

Nikki finished her drink and headed to the bedroom where Penny was reading a romance novel.

“Have fun with the kiddies?” Penny asked her sister.

“It was nice, Sandy is a pleasant girl. Tom seems to really like her.”

“Wear your ear plugs or you will hear just how much they ‘like’ each other.” Penny snickered.

“So, what is that app you use to spy on them? Just in case I hear something strange.”

“I know you’re my little sister, but at your age, I hope it doesn’t sound strange. And you’re not spying on your nephew! Good night sis, I’m turning in.” Penny said as she put the ear plugs in and rolled over.

Nikki laid there playing a silly game on her phone for a while. It must have been around midnight when she started to hear the undeniable sounds of the young couple, coming from the other side of the house. The sounds of her nephew moaning started softly, but continued to build in volume, until he cried out in orgasm. Then it was Sandy’s moans that filled the house. Nikki figured Sandy probably sucked him off and now he is going down on her. She was trying to envision the young couple, when she got out of bed and snuck across the house. They were in his bedroom with the door closed. Nikki was just horny and brazen enough to quietly turn the door handle.

Nikki only opened the door a tiny bit, hoping they wouldn’t notice. Sandy was in doggy position, with Tom fucking her from behind. Nikki was in luck because they were facing away from her.

“Fuck Tommy.” Sandy moaned. “I love the way your cock fills my hungry cunt.”

“Your pussy is so wet and tight.”

“My cunt Tommy. I told you, to call it my cunt, I love it!”

“You are so tight Sandy. I can’t get enough of the way your little cunt squeezes my cock baby.”

Nikki slipped a hand into her panties and started to rub her clit as she watched her nephews ass, pumping his hard cock in and out of Sandy. Nikki knew just how good it feels to be fucked by Tom’s hard cock. She has celebrated three of his birthdays getting fucked by him. Nikki watched until they moved to a different position where they might catch her. She quietly closed the door and returned to her sisters room.

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