Janet's Gotta Regatta

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Janet is on a sex cruise where everyone takes it in the ass!
2.3k words
4.04
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Part 1 of the 2 part series

Updated 06/07/2023
Created 02/14/2015
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Janet had been sad to see her niece and nephew in-law leave. Roxy was always fun to have sex with and Billy had been a wonderful surprise. But now she had to get ready for the Regatta in two days down at the marina. It would be one long and sex filled Saturday and Sunday on the Rear Admiral's yacht. It would be completely clothing optional after they were a mile off shore. This would keep casual voyeurs from seeing them. Janet was excited to meet some new men and women and to have sex with them.

Saturday morning arrived and Janet set out around ten in the morning so that she would be there by eleven with time to spare. The party was supposed to start by noon, but Janet knew that getting there early would give her a chance to get settled. The Rear Admiral and his wife welcomed her on board, the wife slipping her some tongue as they kissed hello. The Rear Admiral was past 70 and his wife, Lauren was forty years his junior. She was a full figured hellion. The Rear Admiral loved to show her off, and often times they had threesomes with another man. Lauren took full advantage of the young cock and often times the Rear Admiral finished by taking the young man in his ass, hence the moniker, Rear Admiral. He had no military service at all.

The yacht set sail at noon with about twenty five people on board, fifteen men and ten women. Janet loved those odds, she would have a fun filled weekend. The yacht was staffed with four men. Two to navigate and two that served the guests on board. The servers were a black father and son, Rufus and Marcus. Occasionally they would enter the fun as they had huge cocks. Some of the party goers would insist and if the Rear Admiral gave the okay they would bring their cocks out for their pleasure.

The yacht was filled with light fare on tables on both decks above board. Cut up fruit and cheese on the first deck and above more substantial fare. Both tables had bowls of that famous blue pill, Viagra, directly in the middle. At the ends were condoms and lube. Champagne flowed and liquor was consumed from an open bar. When the Rear Admiral announced that they were a mile off shore, far enough away from casual observers, the clothes started to come off. The women were all topless and the men were largely dressed in speedos and swim trunks only.

Janet sat back and watched as two men approached another women, Francine. As they spoke to Francine, she dropped to her knees and pulled down one of the men's speedos and started to give him head. The other man dropped his swim trunks and stroked his cock to a full erection and then pushed it toward her mouth. Soon the woman had both cocks in her mouth. After a bit they came out and she started stroking them. She told them that she wanted to have one in her ass and one in her pussy at the same time. Wow! No warming up on this trip. Janet was starting to play with her clit a bit, through her bikini bottoms, as she watched.

Now Francine was impaled on one man laying in a lounge chair, bouncing up and down on his cock. Soon the other man positioned himself behind the woman and placed his middle finger on the woman's beautiful puckered brown hole. He spit on his finger and pushed in slowly as she continued to bounce on the cock. He got into a rhythm and was soon finger fucking her ass, first with one finger and then with two. He withdrew and got directly behind her and she stopped bucking on the other's cock while she was getting a cock shoved in her ass. With both cocks in her, she started to rock back and force so that the cocks were moving in and out of her holes. She picked up pace a bit, careful not to have either cock slip out, and she was soon about ready to explode. She was a quiet one, but her body arched and then started to shake as she came. After a brief period she ordered both men to get out of her pussy and ass. She told them to stand in front of her and stroke themselves and come on her tits. Each man did their duty and the woman got a towel and cleaned up. She would be on the prowl for some more sex, after a brief respite. Janet knew that there was plenty of time so she relaxed a bit, waiting for the perfect moment. She too was looking for some group sex, but all in good time.

Another woman that Janet had met on another of these regattas was Charlene. She looked like a gymnast. About five feet tall, very slim and with boobs that weren't much more than a bit of areola and protruding nipples. My how she loved to show off that body! She was lying on a lounge chair, fully reclined as two men and a woman were placing fruit and whipped cream all over her and then licking it off. Charlene was asking that they shoot some whipped cream in her pussy and then have the other woman lick it out. The men loved it! Next she wanted whipped cream in her asshole and the guys to lick it up. While laying on her back she lifting her legs high in the air and held them with hands as the nozzle penetrated her pert starfish and whipped cream soon oozed out. The men took turned eating the whip cream and licking her anus. Charlene was in heaven.

Next Charlene told the men to wait while Karen, the other woman, and she had some fun with each other. "Keep those cocks erect though. The hardest boner gets a full blowjob when I'm finished with Karen!" Karen was full figured with full hips, a slender waist and large boobs. She had what would be described as a voluptuous figure. She made Charlene look like her younger daughter. Charlene soon had her head in Karen's tits. She started to lick all around her left nipple. The areola was large and dark brown. Her nipples came right to attention as Charlene was licking and then sucking those tits. She bobbed from left to right and back again, sucking and pulling. Karen meanwhile had been playing with Charlene's pussy. Charlene's clit had emerged and was quite pronounced. Karen had her thumb on the clit and started with her middle finger penetrating Charlene's pussy. After stroking in and out she added a second finger in her pussy and started to pick up the pace. Both women were in ecstasy, but they both realized they needed to get their tongues in the other's pussy, so they started to 69.

Charlene was licking Karen's clit and had her finger in Karen, and Karen was doing the same. Charlene tensed up and then let out gasp as she came. After only a second she was determined to have Karen come as well. While licking her clit and finger fucking her pussy, she reached behind and inserted her finger up Karen's asshole! That did it, Karen let out a scream of pleasure as she came. Good to her word, Charlene chose the hardest erection and started a blowjob. Karen felt bad and chose the other guy and gave him a blow job as well. Soon they had both men coming in their mouths and swallowed the entire load.

Janet had come on board for one real reason. She had never had sex with Lauren and the Rear Admiral. She knew that she needed to bring a man with her as well. Lauren and the Rear Admiral liked the butt fucking at the end, so Janet went on the prowl for an old friend that swung both ways. She had seen Randy get on the yacht earlier, and quickly found him drinking a screwdriver at the bar. "Randy, would you be interested in seeing if Lauren and the Rear Admiral were ready to have some sex?" Off they went to the top deck and Lauren and the Rear Admiral were just starting to come down, but stopped.

Janet asked "Lauren would you and the Rear Admiral like to start out the weekend now? I was hoping the Rear Admiral might take care of my rear? And I brought a play thing for you as well." The Rear Admiral didn't wait for an answer and started to suck on Janet's tits. Her tits are a D cup. Nice and soft and hanging down her chest a bit, they are all natural. Her areola are large and dark, with nipples that extend out a half inch when played with. And they were starting to pop as the Rear Admiral was sucking and pulling on them. Next to them Lauren had shed her bikini bottoms and Randy had turned Lauren around, spread her butt cheeks and was licking her cute puckered brown hole.

Janet wriggled out of her bottoms and guided the Rear Admiral's hand to her clit. Meanwhile she had her hand in the Rear Admiral's shorts. His dick was 70 years old, but it still had some life in it. Janet whispered to him and asked if he had taken any Viagra and he said he had taken two earlier. Janet told him that was good as she planned on making good use of it. She dropped to her knees, pulled his shorts down and took his cock in her mouth. It was starting to stiffen up and his cock was nicely sized!

She had both hands fondling his balls. At times she would grab a single ball and give it a tug, followed by the other. The Rear Admiral was groaning in pleasure, "Don't stop!" Janet's head was bobbing on his cock, when she took him down her throat. The Rear Admiral was face fucking her, when she came up for air and then they were at it again. Janet snuck her one hand from his balls and placed her middle finger on his asshole. With a bit of pressure she snuck her finger in to the first knuckle. He moaned, "Stick it all the way in!" Not knowing if he meant his cock in her mouth or her finger in his ass, Janet did both. The Rear Admiral stiffened up and clenched her finger with his butt cheeks. Janet took her mouth off his cock and he told her to finger fuck his ass.

Janet stood up and told him to bend over the table. She spit on his asshole and penetrated his butt hole with two fingers. He moaned with joy. Suddenly he stopped and told her to open the box on the floor next to them. It was a treasure chest of sex toys! Janet took out a dildo, looking just like a well hung black man's cock and a harness and put it on. The Astroglide came out next and she lubed the Rear Admiral's asshole properly. Next she had the Rear Admiral turn around, drop to his knees and suck on her girl cock. "Farther in your mouth," she told him and he finally gagged. "Get it wet," she commanded, "as this is going in your ass!" He performed well and Janet had him stand back up and turn around.

She lubed her girl cock with some additional lube and then she placed her girl cock at his asshole. Then she noticed that Randy had Lauren bent over the same table next to them. He was banging away in her pussy, but told Lauren he was going to ass fuck her at the same time as Janet was fucking her husband. As if on command, they both penetrated the other's assholes at the same time. Fairly slowly they picked up rhythm and were thrusting balls deep. Then the Rear Admiral declared "I want Randy to bugger me and come in my ass! Let's switch partners." Lauren shook her head yes and Randy and Janet switched partners.

Lauren told them " He wants a cock in his ass every chance he can! He loves it and then he is in such a generous mood after. Randy, make sure that you pull out when you are ready to come as the Rear Admiral likes to have your cock in his mouth when you come." Randy was pumping in the Rear Admiral's ass, as Janet had her girl cock in Lauren's ass shoving it as deep as she could.

Lauren had a hand between her legs playing with her clit when she tensed up and then came, shuddering but remaining quiet. She twisted around and said, "Let's watch the Rear Admiral take Randy's cock. I find this such a turn on." When Janet looked at Lauren she was two fingers deep in her pussy as she watched. At last Randy pulled out of the Rear Admiral and said, "Old man suck the cum out of my cock. I am about ready to explode." The Rear Admiral barely had Randy's cock in his mouth when Randy let loose. The Rear Admiral had cum leaking out of his mouth and Lauren bent over and started to lick it away. The Rear Admiral then took Lauren in a deep kiss and they swapped cum, before finally swallowing it all. Janet had the dildo out of the harness now and was plunging it in and out of her pussy when she reached for Randy and grabbed his cock to clean off in her mouth. Soon she orgasmed with a loud scream.

And the weekend was only starting!

*****

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AnonymousAnonymousabout 6 years ago
I enjoyed it.

My pussy was dry as the desert before reading this stoutly. As I was reading each section of the story, I could feel my lists becoming wetter and thriving!!! It was amazing. I’m a virgin.

AnonymousAnonymousabout 9 years ago
Tasteless.

Sex without story.

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