Winter Break 9

Thank you for reading, please rate and feedback is always welcome. Reminder, all characters and locations are fictional, and everyone is 18 years of age or older at the time any sexual encounters occur. This is also an entry for the

Literotica Winter Holidays Story Contest 2024

.

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Overview of a previous story connected to this one. Kevin, 19, and his younger sister, Karen, 18, recently attended a pool party with a neighborhood couple that was friends of the family. Even with their mother, Pam, hanging out around the pool, both siblings were able to lose their virginity to the couple inside the house.

First John found Karen using his wife's dildo in the bathroom, which she continued to use until John was hard enough to replace it with his own cock. Kevin was asked by Emily to assist her in the guest bedroom and then she returned the favor with a blowjob and a little cowgirl action.

After dinner, Pam received a phone call asking her to return to the office, even though it was a Saturday night. John and Emily convinced Pam to allow Kevin and Karen to stay and swim for a few more hours.

While cleaning off the table, they confirmed that both siblings were wanting the other sexually. Soon after getting in the pool again, everyone was naked, and Kevin was able to fuck his sister for the first time. If you would like more details, please read the Neighbor's Pool Party.

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When Karen started college, she decided to stay local and went to the college only a few miles away. She decided to live on campus so she could get the full college experience. However, she still got home a couple weekends a month to see her mother and to do laundry.

Her brother was in his second year at a college across the state. During the school year, he couldn't get home to see his sister or mother. Last year this wasn't a big problem, however, now that Kevin was having sex with his younger sister, the semester seemed to draw out. He couldn't wait until winter break to spend some time with her.

During a video call about a month after school started, Karen decided to flash the camera and give Kevin a little show. This quickly led to both stripping off their clothes and masturbating over the call with each other.

They planned on mutual masturbation sessions about once a month, but they were certainly wishing for the touch of the others body and couldn't wait until they were both home for winter break.

Karen arrived home for winter break a day earlier than Kevin. The semester had been fun, but she had never found the right guy to get intimate with. The only cock she had seen was that of her brother over the calls they had. She had purchased a vibrator that she used whenever her roommate was in class or on a date, but even that was not keeping her from dreaming about her brother's cock.

Upon arriving home, she announced her arrival with a loud, "I'm Home!" knowing that it was only her mother in the house, but there was still no response. She looked around on the first floor and didn't find her mother. She started up the stairs and finally got a response from her mother.

"Is that you Karen? I'm back here and need your help," her mother said.

Karen walked through the master bedroom and bathroom before finding her in the closet, trying on dresses.

"Which one do you like," her mother asked as she held up three very different dresses.

Karen replied, "What's the occasion? They are all great, but what situation are they to be worn in?"

Pam replied, "Tomorrow night I have a date and thought I would get your opinion on which dress I should wear."

"Oh, you want to get laid," Karen blurted out, not thinking she was talking to her own mother.

"Watch your mouth, young lady!" her mother responded. "But yes, it has been 5 years since your father passed away. Even longer sense he had last made love to me. I figure it is time that I return to the dating pool."

Karen responded "Mom, I completely understand. The black dress you have on right now is all wrong. It looks like you are going to a parent-teacher conference with Mr. Brown. You know, the one that I had in my freshman year of high school. The overweight science teacher who had a combover to cover his bald spot."

"That bad," Pam asked her daughter.

"Yes," Karen continued. "Try on the red one. I think that will show off your body quite well. While your changing, I need to run to my room."

"Well, if you think that is the best dress?" Pam said. "Also, you don't have to leave, but hurry back."

Karen left the closet and headed to her bedroom to get comfortable. Over the weekends she was at home, she had gotten into the habit of not wearing a bra around her mother. Heading down the hall, she pulled her shirt over her head as she walked, reached behind her back and unhooked her bra.

Once in her room, she took a quick look in the mirror on the wall to admire her B cup breasts. Karen caressed them, making her nipples perky before grabbing a different shirt from the closet. She typically didn't want her mother to see her nipples poking through her shirt, but even grabbed a shirt that was tight on her body to emphasize her nipples even more and put her long hair up into a ponytail.

As she walked back to the master bedroom, she found her mother basically standing where she had left her. Karen had to take a double take as her mother looked stunning. The red dress was formfitting and emphasized all her mother's curves. It was knee length and showcased her legs quite well. Not so much that anyone would think she was begging to be laid, but enough to let her date know that was the outcome she wanted.

The top of the dress may have exposed a little more cleavage than her mother wanted to reveal. Her beautiful blonde hair draped over her exposed shoulders, with only the thin strap of the dress and her red bra strap draped over the shoulders.

"Wow mom," Karen finally commented after swallowing a mouth full of saliva. "You are going to cause people to do a double take when they see you walking in. Anyone would be out of their mind if they didn't find you attractive right now. I'm your daughter and even I am finding you extremely attractive."

"You think so?" Pam asked. "You don't think I am showing too much cleavage?"

Karen responded, "Actually mom, remove the bra. The dress is formfitting enough that I can see the outline of the bra and the extra bra straps does nothing."

"I had such a hard time getting this dress zipped up," Pam commented, "Would you help me unzip it, please?"

Pam slowly turned around as she lifted her hair from her shoulders. Karen stepped forward and found the small zipper. She slowly started to pull it down her mother's back, revealing the clasps of her bra. She reached up and started to unhook her mother's red bra. Karen could feel the juices from her pussy soaking her panties.

Once unhooked, Pam turned around to face her daughter again. She reached for the strap of her dress over her left shoulder and dropped it to mid arm. She again reached for the other strap and dropped it down her right arm, allowing the dress to drop and reveal her bra covered breasts.

"Baby, would you do the honors of removing my bra?" asked Pam.

"Are you sure, mom?" Karen awkwardly responded.

Pam directed, "Oh, yes, I am sure. I have been trying to figure out a way to try and take our relationship to a more personal level ever sense you turned 18. Every weekend you are home, you walk around without a bra, and I haven't found a way to express this desire."

"I also heard you and your brother one late night before he left for college," her mother continued. "This house is quiet at night, and you were making enough noise that I had to investigate. I walked down the hall and listened outside your bedroom. At first, I was surprised, but instead of barging in, I simply walked back to my room and grabbed my vibrator. I usually am quiet if I use it while either of you are home, but that night I thought for sure you would hear me pleasuring myself."

Karen smiled and leaned forward to hug her mother. Deep down she knew she was right and was looking for a full family experience. Her hands slipped up her body and found the straps of her mother's bra on her shoulders. She started to pull the straps down each arm but encountered the straps of the dress as she got around the elbow. Pam stepped back, pulling her arms up through each strap, allowing both the bra and dress to drop from her body and onto the floor.

"Mommy, you're not wearing any panties!" Karen proclaimed as she stood there looking at her now naked mother. Her eyes jumped back and forth, taking in how stunning she looked. At nearly the same time, Karen noticed that her mother was completely trimmed and could clearly see the lips of her pussy between her legs. She also noticed her voluptuous breasts which were larger than her own, and guessed they were at least C cups.

As Pam stood there naked in front of her daughter, she asked, "By the expression on your face, you like what you see. Are you comfortable with us taking this to another level?"

Karen simply nodded and tried to voice a response of acceptance, but her mother pressed her finger against her lips to stop her from talking further. Pam stepped forward and hugged her, pressing her naked body against her daughter. She reached down and grabbed the bottom of her daughter's tight top.

Pam quickly pulled the shirt up and over her head, revealing her perky nipples begging for attention atop her breasts. Karen quickly reached for her leggings and panties to drop them to the floor.

Clothing was flung everywhere, and it was now Pam's turn to examine the naked body of her daughter. One that she had not seen since she was last running around the house in diapers. Karen had blossomed into an attractive young woman. Pam was unsure how to proceed, fighting with her inner voice about what was appropriate.

Karen reached out and took her mother's hand. "Let's take this into the bedroom, mommy."

That was enough of an encouraging comment to let that little voice inside of Pam know that this was something her daughter also wanted. Pam followed her daughter to the bed and watched her recline. Karen spread her legs a little, revealing a little tuff of hair neatly trimmed above her pussy.

"Do you like what you see, mommy?" she asked. "Kevin likes it trimmed so there is not as much hair to deal with when he munches on my pussy."

"Oh yes, and you are so wet my horny daughter," Pam said. "Is my little girl ready to have her pussy licked?"

"TAKE ME MOMMY!" Karen screamed.

Pam leaned down and spread her daughter's legs further, causing her pussy lips to separate. She looked at her daughter and wiggled her tongue, causing Karen to giggle. As she giggled, juices started dripping from her pussy.

Pam playfully commented, "Your pussy seems to have sprung a leak. Let me assist in cleaning it up."

Karen's giggles turned quickly to moans as her mother's tongue slipped across her wet pussy. Just once at first, to prolong the anticipation of what was about to happen. When Pam licked twice, Karen closed her legs a little, pinning her mother's head between her legs. Pam used her hands to press Karen's legs apart so she could continue.

And continue she did. No more breaks, just lick after lick quickly drove Karen wild. Her body stiffened as her first orgasm caused her to scream again with pleasure. Her mother didn't stop and continued to press her tongue deeper inside. Karen was trying to control her body with deep breaths, but as her mother changed from licking to sucking, her next orgasm broke free and flowed through her body.

Karen screamed, "OH, OH, MOMMY! That's, that's the spot. OOOOOO!"

Pam had to catch her breath. As Karen looked down over her naked body, between her breasts, she watched her mother's face appear from between her legs. Her own juices were now glistening over her mother's mouth and face. Karen tried to sit up, but her mother decided instead to crawl onto the bed and rest next to her daughter.

They kissed and Karen commented, "Yum, I taste good on your lips."

Pam smiled and returned to kissing her daughter. Their hands roamed over their naked bodies as they rolled around on the bed. Their breasts pressed between their bodies allowed their nipples to be an extra point of stimulating contact. Their legs intertwined to maximize as much skin that was able to be touched at one time.

Pam suddenly broke off their kiss and said, "Oh, I haven't been touched there by another person since before your father passed."

Karen had reached between her mother's pussy lips and started to rub her clit with her fingers. She started slowly, knowing her mother was wet but also may need to be warmed up a little more. As her mother took deeper and deeper breaths, Karen's fingers worked their magic as they moved faster and faster over her mother's joy button.

"Oh God, Oh God," Pam screamed as her body squirmed on the bed. Her legs squeezed together, but Karen kept her fingers on the prize and didn't relent but continued the pleasure she was giving her mother. Pleasure that only her vibrator had until recently applied to that spot.

Pam started to open her legs to release their vice grip on her daughter's hand. She reached over and placed a hand on her shoulder, directing her to get between her legs. "Please baby, finish me off with your tongue."

Karen was only too happy to comply with the request of her mother. Although her fingers could continue, her hand was sore from being pressed between the legs and needed a rest. She quickly got her tongue into position and inserted it into her mother's pussy. Pam's body jumped just a little as the tongue found its mark and picked up where Karen's fingers had left off.

Pam placed both of her hands on the back of her daughter's head, encouraging her tongue deeper inside her pussy. She closed her eyes and enjoyed the moment, as moan after moan escaped from her mouth.

Suddenly Pam felt a feeling she hadn't felt since college and the last time a woman was between her legs, eating her pussy. She released her hands from her daughter's head, as she screamed, "Oh, OH, OH GOD, I'M CUMMMMING!"

This was unlike any orgasm that Karen had ever witnessed as she was soon being sprayed in the face by her mother's juices that were being squirted from her pussy. With her tongue still sticking out of her mouth, fresh from licking her mother's pussy, she was now getting a mouth and face full of something she didn't know her mother could do.

As Pam finally relaxed on the bed, Karen sat up with her juices dripping down her face and the rest of her naked body.

"Mom!" she said, "I didn't know you could do that?"

"What," Pam answered. "This is the first time you have licked my pussy. Did you expect me to warn you that I could squirt? Besides, I kind of forgot as your father never did that well enough to get that reaction out of me."

Karen relaxed next to her mother on the bed and simply cuddled with her as they recovered. The juices continued to drip and pool on the bed.

"I think you may want to sleep in my bed tonight, mommy," Karen commented. "I think your bed needs a little time to dry."

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Kevin arrived home from college the next day shortly before dinner. He dropped his bag on the floor and hugged his mother who was the first to greet him at the door. It was a little longer than their typical hugs but he didn't think much of it since he had been away for a few months.

Karen was next to give him a big hug. He knew exactly what she had in mind, as it was the same thing that he had been thinking about for most of the week. Kevin hadn't gotten any pussy this past semester. The calls with his sister were great, but he was ready to feel the inside of her wet pussy.

As they separated, Kevin quietly commented, "You're not wearing a bra, and neither is mom. What happened while I was gone?"

Their mother smiled and commented while she walked upstairs. "Why don't you two catch up. Dinner is ready in the kitchen, but I need to get ready for tonight."

As Karen pulled the lasagna out of the oven and sat down at the table with her brother. She commented, "Mom knows everything. She knows we are fucking and has listened in on us from the hallway."

Kevin wanted to comment, but Karen continued, "She invited me into her bedroom, yesterday, to help her pick out a dress, as she has a date tonight. In addition to coming clean about knowing about us, she also expressed her desire for me. One thing led to another, and we gave each other multiple orgasms last night in her bed. I also found out she is a squirter and we got her bed so wet that she ended up sleeping in my bed last night."

Kevin barely had taken a bite of his food, as he was shocked at the information that he was getting from his sister.

After taking a couple bites herself, Karen continued, "We slept naked together last night, and I woke up this morning with her fingering my pussy. She had switched directions so that I had her pussy directly in front of my face, so I started fingering her as well."

"We brought each other to an orgasm and then proceeded to fall back asleep, only to wake up again in each other's arms. We finally got up and took a shower together. It felt amazing having her breasts glide over my body with the water flowing between us. We didn't get dressed until shortly before you got home."

Kevin took a couple more bites of food before finally commenting, "I know mom has been lonely since dad passed, but I didn't think she would have considered dating again. Let alone seduce her own daughter."

They finished dinner and started cleaning up. As Karen was putting the leftovers into a container, Kevin came up behind her and wrapped his arms around her. He cupped her breasts through her shirt and kissed her neck. Karen stopped and moaned at the attention.

"Ah hem," came from the opening into the living room. Karen and Kevin broke their embrace to find their mother standing there, watching them. "I'm heading off to my date, and I think I know what you two are going to do while I am gone."

"Mom!" Kevin finally said, "You look hot. I don't think you have worn anything before that has shown off that much cleavage. Be safe on your date tonight."

Pam quickly gave each of her children a quick hug before heading for the car and leaving for her date. Karen and Kevin finished cleaning the table. Once they were sure their mother had left, they turned to each other and locked lips in a wild kiss. Their arms flung around each other to hold the other close. It had been several months of them being apart at different colleges that they were trying to catch up on.

Already breathing heavily, as soon as they broke off their kiss, Karen stepped back and quickly lifted her shirt. Kevin followed his sister's lead and removed his shirt, followed by his shorts and underwear. His hard cock sprung to attention as it was freed from the constraints of his clothes. Karen also dropped her shorts, revealing that she was also not wearing any panties.

They stepped from their discarded clothes on the kitchen floor to embrace each other again. Pressing their naked bodies against the other, the contact of skin sent a shiver down Karen's body. They locked their lips again, holding the other close with just one arm. Kevin worked his free hand between them to cup one of his sister's breasts. Karen's free hand worked its way down to start stroking her brother's cock.

Kevin broke off the kiss this time, pushing his sister against the counter. He started down the side of her neck with little kisses, sending shivers again through Karen's body. When he had kissed his way to her shoulder, he continued down the front and onto her breast. He circled her nipple with kisses before sucking it into his mouth and Karen left out a soft moan.