Spring Break Chaperones

Thanks again to Todger65 for editing my hodge-podge of a story.

* * * * *

Bill and Carol Starkey pulled into Denise Bolton's driveway. It was their regular Saturday night dinner date. Carol had lost her husband to a massive heart attack three years ago. His loss devastated both families. They had raised their children together and were one big family in spirit, if not in fact.

Their houses were next to each other and Denise could have easily walked over and entered the car, but Bill insisted on picking her up. He was a romantic soul and he wanted Denise to feel special. Bill and Carol had gotten good at making Denise feel special.

Denise has a son, Keith, who was out and about with Bill and Carol's son Joel this evening. Denise also has a daughter, Robin, who was at a high school dance with Bill and Carol's daughter Chelsea. The boys were freshmen in college. The daughters were seniors in high school and had just celebrated their eighteenth birthdays. The girls had been born just days apart.

Bill drove to one of their favorite restaurants where the three enjoyed a wonderful meal. During the meal conversation flowed over subject after subject as happens when close friends talk. There was one subject that all three had put off. Bill decided it was time to deal with it, "So, our sons want to go on a spring break vacation?"

Denise was thoughtful, "I don't mind them having a vacation and some fun, but I don't want them running around without some oversight. I am concerned that they will get into trouble with the bad elements that stalk spring breakers."

Carol nodded in agreement, "I wouldn't mind them going if we could chaperone the trip."

Bill shook his head, "I just can't do it. I can't be gone for a week right now. My workload won't allow it."

Carol perked up, "Why don't Denise and I go? Two of us would make it easier to keep track of things. I feel like some beach time would be awesome."

Denise nodded in agreement, "I don't want Robin home alone. If we do this, can she stay with Chelsea at your place?"

"Duh, of course."

Bill stroked his chin in thought, "You will never find hotel rooms this late in the game. I suggest you rent a house on the beach. It will be a bit expensive, but the odds of spring breakers being able to afford a house rental are slim. Even if they can, the owners won't rent to them. There is too much risk of damage from the constant partying."

The two women were getting excited at the idea and began searching for houses on their cell phones. Bill let them search for a while before interrupting, "OK, phones down please. You know our rule. No cell phones at dinner. You two will find something."

Carol frowned, "What if we don't?"

Denise was as usual cheerfully optimistic, "We will find something. Let's get together tomorrow and figure it out."

"All right then. You two have a plan and I will leave you to it. In the meantime, I have a plan as well, and it is much more urgent."

Carol smiled at her husband, "And what plan would that be?"

"I plan on getting you both into a bed as soon as possible."

Denise cupped her face with her hands as if in shock, "Sir, are you saying you want to put your big cock into my pussy? What about your dear wife?"

Bill smiled mischievously, "Yes I plan on fucking your brains out. As for my wife, I think she will be fine. She will be sitting and watching."

Carol frowned, "I don't want to sit and watch."

Bill reached across the table and took her hand in his, "Trust me dear you won't mind. You will be sitting on Denise's face."

"Oh! In that case I'm in!"

Bill put his credit card on the table, "Then let's get out of here.

* * * * *

On the drive home Bill thought about how the three of them had ended up as lovers. It had started innocently enough. When Denise's husband had died, she needed the comfort of her friends. Her family would stay at the Starkey house when their own house overwhelmed them with memories. Accommodations were tight and Denise was forced to sleep with Bill and Carol.

After a few months of sharing their home Bill came home late from work one night. He was as quiet as possible walking through the house. He slowly opened the bedroom door and the dim light from the hallway revealed Carol and Denise in the throes of passion. Bill was not in the least upset, just as Carol knew he wouldn't be. Carol loved her friend and Denise needed the closeness that love making provided.

He stood in the doorway and watched the two women lovingly touching and pleasing each other. It was a magical moment for Bill. Yes, the view was erotic as all hell but what touched him was the love between the two women.

Bill began to undress as Carol began kissing her way down Denise's body. Her mouth lovingly suckled Denise's tits before licking her way downward. Soon she found her center and began to caress her pussy with her tongue. He moved to the bed and waited until Denise was in the throes of orgasm before joining the couple. He slowly stroked his cock as he watched his wife kiss her way back up Denise's body. The two women kissed passionately. It wasn't until they separated from the kiss that they noticed Bill had joined them.

Carol smiled lustily at her husband. Denise was shyer and Bill tried to reassure her, "I am so glad that you two could make each other happy. Is there is anything I can do to help now I am here, but you don't have to do anything you don't want to."

"Uhm... If it is alright with Carol, I could use a good fucking."

Bill chuckled and looked at his wife. Her response was to move off Denise. She then pulled Denise's legs open, "There it is babe. Fill her up with high test!"

Denise enjoyed what followed immensely. Bill was a considerate and skilled lover. It didn't hurt that he was also very well endowed.

After that night, the threesome made sure to set aside a few Saturdays a month for a romantic evening. Their children were of an age that ensured a busy social life. It wasn't too difficult to find a way to get together for some conversation, fun, and fucking.

The threesome had no idea that their children had been aware of their sexual shenanigans for some time. Joel even managed to sneak in a video camera in on one momentous occasion.

One Saturday evening when they knew that the parents were going to end up at the Starkey house for the night, Joel invited his sister to join him at the Bolton house.

When they arrived Robin and Keith were waiting. Joel held the camera aloft like some sort of first place trophy. The four went to Keith's bedroom which was on the side of the house opposite the Starkey's. He hooked the camera up to his television and Joel pressed 'Play'.

The guys tried to focus on each other's mother but couldn't help noticing their own mother while doing so. It didn't take long for them to get over the weirdness of seeing their moms naked. They are incredibly attractive women. The girls on the other hand were fascinated by Chelsea's dad, his obvious skill, and his big cock. It is true that Joel and Keith had an ulterior motive for inviting the girls. Joel thought Keith's sister was hot as a firecracker and Keith felt the same about Robin. The guys were hoping to do more than watch a video.

The evening they watched the video turned into an evening of discovery. Things got a bit heated as the video progressed. The fact that the four horny teenagers were crowded together on Keith's bed certainly contributed. The pressure on the boys from the tightness of their jeans became too much. Keith was the first to unzip and release his rock-hard cock. Joel followed within seconds.

Chelsea saw her brother's cock standing erect and let out a little gasp, "Oh my god! You're as big as dad. Uhm, can I touch it bro?"

"I guess. I mean, yeh. Please touch it."

His sister wrapped her hand around him and squeezed. Joel let out a groan as her hand slid up and down, "Sis you need to be careful or I'm gonna cum."

"Does it feel that good?"

"Yes. I don't know if it is your soft hands or that you are my hot sister, but you are really getting to me."

"You think I'm hot?"

"Hell yes. I think about you all the time."

"Do you think about me naked?"

"Oh god yes!"

While the brother and sister Starkey were getting to know each other in a whole new way the brother and sister Bolton were doing much the same. Robin didn't even ask if she could touch her brother's cock. She fell in love with it as soon as she saw it. One thing Robin loved to do was suck cock and she wasted no time wrapping her lips around her brother's.

The slurping noises coming from the other side of the bed didn't faze Chelsea or Joel. Chelsea began to strip slowly in front of her brother. She pulled her top over her head and dropped it before sliding out of her shorts. She unhooked her bra and let it drop, "Do you like my titties Joel?"

"I love your tits sis."

She pulled off her thong and laid back. Her legs slowly parted displaying her pussy, "Do you like my pussy?"

Joel started sliding up between his sister's legs, "I need a closer look."

He stopped with his mouth inches from her pussy and looked at it. His tongue came out and he licked her from her entrance up and across her clit. His mouth formed over her pussy and his tongue began to lick.

"Oh god Joel. I didn't know you could see with your tongue. Please keep looking. Stare even. Stare as hard as you can!"

Robin and Keith had managed to get into a sixty-nine and were have a wonderful time revving each other up. The oral ministrations continued until Robin and Chelsea came within seconds of each other. Neither girl was much surprised to find a large, angry red, erection pointed toward each wet pussy. They were both ecstatic when their brothers began to slide in deep. Neither brother lasted long the first time.

The second time took longer, and sibling bonds were strengthened to a whole new level. The third time they swapped. By morning they were as thoroughly fucked out as their parents and just as happy.

They almost got caught that morning. The girls managed to sneak back to Robin's room before Denise got in the door and down the hall. Denise listened in the hall and determined that everyone must be still asleep. In just a few minutes she was in her own bed and back asleep.

* * * * *

Sunday afternoon the two mothers sat down with their sons. Carol had a legal pad ready to take notes. Joel and Keith were curious about why their mothers wanted to talk with them. Both were thinking about the sister sex fest and were nervous that their parents had found out. Denise eased their tensions, "We want to talk about spring break. There is no way we are sending you guys off alone. So, we decided that Carol and I will go with you as chaperones."

Keith was beside himself, "Oh No! We'll never have any fun with our moms watching us all the time!"

Joel was equally upset, "My face will be so red from embarrassment people will think I have a terminal sunburn!"

Carol raised her hands in a placating gesture, "Relax guys. We aren't planning on hanging over you every minute. You'll be free to run around during the day and evening. We just want to make sure you have a safe place to sleep and that you have someone looking out for you.

"Denise and I plan on enjoying the beach. Who knows we might find some young studs to play with!"

"MOM!"

"Just kidding. Anyway, we are thinking about renting a house on the beach."

Keith perked up, "A house on the beach would be way cool! The girls will be impressed."

Joel wasn't as happy, "Yeh, and when we want to bring them home for some fun our mothers will be waiting. Talk about a buzz kill."

Denise held up her hand, "That is just the kind of thing we are talking about. If you bring girls home, we won't interfere, but we will make sure you have condoms. You can just shoot us a text and we will get out of sight while you guys close the deal."

"There is one more problem mom. Mike and Charley were going with us too. I don't want to go and not take them. It would be a dick move."

"No problem. We can rent a larger house. I am sure there are homes big enough for the six of us."

"I don't know mom."

"Know this. If you want to go on spring break this is how we do it. Capice?"

"OK. I'll talk to Mike and Charley."

Unknown to their mothers, Joel and Keith were happy about the fact that their moms were coming. They had serious crushes on each other's mother and were looking forward to watching them strut around in bikinis. They knew that their moms were fun and open minded. If the truth were known they would much rather be with each other's mom than some vapid college girl drunk on her ass.

The idea of seducing each other's moms began to percolate in both their heads. They didn't notice their mothers watching their rising erections. Carol and Denise sat with flushed faces as they watched substantial bulges pressing against their son's shorts.

Joel called Mike while Keith called Charley. Both were a bit surprised at how quickly their friends agreed. Joel and Charley were not the only ones with a crush on their mothers.

* * * * *

Bill and Carol laid in bed together the night before spring break vacation. Bill held his wife close, "I expect you to have a good time. If you meet some young stud and want to have some fun, you have my permission. Just make sure he wears a condom. I don't want you bringing anything home with you."

"You would let me screw another man?"

"You let me screw another woman. It only seems fair."

"Yes, but Denise is our friend, and we love her. That isn't the same as some random stud."

"Not really regarding the sex part of it. In fact, I would prefer you not have feelings for whoever you have fun with."

"Well, I guess I understand what you mean. Not that I intended, or intend, to do anything about it. You must know that I love you only and I always will. Anyway, I'm not planning on hooking up with some random college student. A drunk partier trying to score points with a MILF isn't my thing. I won't be a mark on some guy's scorecard.

"You are going to be stuck here with Chelsea and Robin. I think Robin has a bit of a crush on you. Truth be told, I think our daughter does too. I bet they will strut around the house in as little clothing as they can get away with just to get a rise out of you."

"I don't doubt what you are saying. I will do my best to hide any rise I may have. It will be a sacrifice having to watch their nubile young bodies, but I will do my best to struggle through it. The sacrifices I make for this family. It is a thankless job."

The couple kissed deeply. Their love for each other would have been obvious to any onlooker. They wouldn't have cared one way or the other what an onlooker thought. In that moment all they could think of was each other and how lucky they had been that the random chance of life had led them to find each other.

* * * * *

Carol parked the rental car in the drive of the rental house, 'Now all I need is rental this and rental that and I will be all set.' Her exit of the vehicle was followed by the passenger door slamming. Denise grinned at her friend, "I wonder how long the boys have been waiting on the porch?"

Joel, Keith, Mike, and Charley were standing on the entry porch. They had left the airport in the other rental car and had taken off like a rocket. Carol and Denise followed at a more reasonable speed, laughing their asses off because they knew something their sons did not. The keys to the house were in Carol's possession, along with most of the luggage.

As it turned out the men in the group had only beaten them to the house by just shy of a minute. Of course, they made Carol and Denise think they had been waiting for hours. The two moms stood in the driveway and smiled at the young men standing on the porch. The sun backlit them revealing the amazing figures that were no longer hidden under the light dresses they wore.

Joel was stunned and, by the silence of his friends, they were as well. Arousing thoughts ran through his head, 'I wonder if our moms know how hot they are? Denise looks amazing. I love her blonde hair, but with that body I don't care what her hair color is. Those perfect tits just begged to be touched. I've seen her naked on video, but I sure want to see her naked in real life.'

'And mom! Wow, she looks even better than Denise. She has those long, toned, legs and her tits are even better than what Denise is sporting. I want her. Wait! What!? I want my mom? Holy shit! Be honest with yourself dude. You have wanted to fuck your mom for a long time. Long before you saw that video and it is long past time you admitted that fact to yourself.'

The smile on Joel's face drooped for a second as he realized what he wanted and how impossible it would be to get it. There was no way he would even get a chance to kiss his mother, much less have sex with her. But damn! He was sure if he got the chance to just kiss her, he could seduce her. It was never going to happen. The best he could hope for would be the distraction of a cute college chick. In further honesty to himself he knew that whoever he ended up in bed would just be a vessel for cum. The entire time he would be thinking about his mom or Denise, or probably both.

If Joel could have read Keith's mind in that moment, he would have been surprised at how closely their thoughts meshed. The primary difference was that the names were reversed. As far as Mike and Charley were concerned, they would be overjoyed if either hot mom paid them the slightest attention. One thing was universal among the young men. They all wanted to bed either, or both, of the fine MILF flesh in front of them.

Not being mind readers, which may or may not have been a good thing, all the women knew was that something had definitely excited the four young men on the porch. They were all fighting to hide an erection. They tried to pretend that they didn't see the obvious bulges. It was hard not to stare at the studly young men. Their youthful virility was arousing to both women.

When none of the four young men moved to help with the luggage Carol put two fingers to her lips and a piercing whistle rent the air, "Hey guys! Wake up and help us with the luggage."

A few minutes later the two women and four red-face young men had all the luggage moved inside. The master suite was on the first floor along with a connected bath, a great room, and kitchen. The kitchen and great room made up the open floor plan of the first floor. Two bedrooms and a bath made up the second floor. The back of the house faced the ocean. The view was only obstructed by the blinds on the floor to ceiling windows and between the layers of glass on the sliding doors. The sliding doors fed onto the pool deck anchored on one end by a hot tub. A gas grill sat on the opposite end. The swimming pool looked nearly as inviting as the ocean.

Denise pointed at the luggage, "Guys, your rooms are upstairs. Please get your stuff put away and we will see you shortly. Don't fool around. We still need to hit the grocery store and the liquor store. And before you ask the answer is no. You are not drinking alcohol. The liquor store is for us. If I catch one of you drinking your spring break will come to an end immediately."

Rather than take two cars it was decided that Mike and Charley would accompany Denise and Carol to the grocery store. The decision was made during an intense Rock Paper Scissors competition held by the young men upstairs. The losers had to stay at the house while the winners got to accompany the hot moms to the store. It was probably the first time since the young men were toddlers that they were enthusiastic about going to the grocery store.

An hour later the groceries were put away. The guys milled around the house while Carol and Denise changed into something more ocean oriented. None of the guys wanted to miss the first viewing of the two MILFs. Their attempts to look nonchalant failed miserably when the two women walked into the great room wearing bikinis. All four froze in place and stared, faces turning red and shorts bulging, at the hot women. Joel was the first to find his voice, "Wow! You both look amazing!"