1 comments/ 49227 views/ 10 favorites Janet's Gotta Regatta By: tmanners25 Janet had been sad to see her niece and nephew 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! ***** I hope you enjoyed reading this short story! Please consider leaving feedback and rating this story. I read them all and appreciate your honest feedback. Janet's Gotta Regatta Ch. 02 Janet is on a sex cruise for a weekend. This is a continuation of "Janet's Gotta Regatta". ***** Janet decided that she wanted to be a cum bucket that afternoon. She collected a dozen condoms from the bowl on the table and announced "Who wants a gang bang?" Several guys crowded around as she announced it again. "I want at least eight guys to fuck me in every hole. I want my pussy full, my asshole stretched out and my mouth to have a cock in it the whole time. Rules are that condoms are on while in my ass and pussy. After that take them off. I want everyone to wait and to jerk off on my face at the end. Double penetrations are encouraged. I like having my boobs and nipples pulled and bit ever so lovingly. Any questions?" Janet's pussy was already dripping from anticipation. She was hungry to suck dick and she was excited to get her ass reamed. One guy lay down and she sat on his cock. Straight up her cunt. No foreplay, she impaled herself on that dick quickly. As another man stood behind them she said, "Put some lube in my ass and finger fuck me a bit before putting that man meat in me!" As instructed he took a gob of lube on his middle finger and started to rub it around her starfish opening. Quickly he got another gob and pushed his middle finger up her ass. Janet was in heaven. Anal sex was probably on the top of her list of pleasure. Janet told the guy, "Stick it in my ass now!" She could feel both cocks in her as she took another in her mouth. The cocks in her pussy and ass completely filled her up. She could feel them sliding in and out, only separated by a thin sheet of muscle. She tried to concentrate on her blow job. She didn't want that cock to feel neglected. She grabbed his shaft and ran her mouth up and down it. Then she pulled it out, spit on it and started to deep throat. As the cock passed by the gag reflex she knew that she would have the entire cock in her mouth and throat. It was so far down that she stuck out her tongue and licked his balls. He pulled out and Janet said, "Give another guy a chance here. Roll that condom on and fuck my pussy!" She pulled away from the two cocks in her ass and pussy and had another guy lay down and she got in the reverse cowgirl position and slowly took his dick in her ass. Another guy stood between the other guy's legs and was soon in her pussy She grabbed two cocks and started to alternate stuffing them in her mouth. Soon she put them in her mouth at the same time. Then out again and stroking them both as another guy stuck his cock in her mouth. She took this guy in her mouth and started to pump his cock in against her cheek as he penetrated her mouth. Soon he started to tense up and Janet pulled away, "No coming yet. Save that jiz for the grand finale! Who's next? I need a couple of new cocks in me!" Another round of this and she was ready to be soaked in cum. "OK boys, everyone around and start stroking those cocks. I want to have cum all over my face and tits. Let 'er rip!" Soon she had cum in her hair, on her chin, eyes, forehead and mouth. More cum was falling down her breasts. There was a pool of cum in between her tits. "Grab me a towel boys, I need to clean up a bit. She used the towel to clean most of the cum off her and she disappeared down below for a quick shower to clean up the rest. Janet went back above board and lay down in a lounger and watched the others on board fucking and sucking. She actually took a quick nap when Celeste lay down in the lounger next to her. After a bit of small talk Celeste suggested that they might be able to pleasure each other for a bit. Janet quickly agreed and took some toys out of her bag she had brought with her. Celeste was on top of her in a flash and sucking on her large boobs. Her nipples were completely erect, jutting out a half inch. Celeste was nipping at them with her teeth and using her hand to massage her other boob. She would grab her nipple and pull on her boob until it came away from her body and looked like it was suspended in mid air. Lovely! Janet wasn't neglecting Celeste's tits either. She played with them rough, grabbing, pulling and slapping her generous boobs. Then she stuck a finger in Celeste's mouth and told her to get it wet as she was going to be sliding it in her pussy. Janet slid her finger right between Celeste's cunt lips and ran into a large and swollen clit with her thumb. She squeezed the clit between her thumb and index finger as Celeste moaned and started to rock her pelvis. "Come for me," Janet commanded. Celeste let herself go and came quickly. Now Celeste eyed the toys and picked up a vibrator and turned it on and slid it up Janet's cunt. Stroking it up and down, twisting it as she did so, Janet was soon ready to come as well. "Pinch my nipples, and don't be too gentle about it," Janet said. That took her over the edge as wave after wave of orgasms hit her. "Wow" she exclaimed. Celeste was now lubing up a double ended dildo. "I want to feel this in my brown hole," Celeste exclaimed. Janet called Tony over and asked him to insert the dildo in their asses as they backed up to each other on all fours. As their butts approached each other Tony inserted the dildo in Celeste's ass and then did the same to Janet. Then he started to pull and push the dildo in and out of their assholes. The ladies were in ecstasy feeling the dildo pulse in and out of their asses. Tony meanwhile used his other hand to stroke his cock. "You ladies look fantastic with your tits hanging down and that dildo in your asses." Celeste was bucking back on the dildo hot and heavy now and Janet was getting hot as Celeste came and Janet followed shortly after. Celeste then had Tony get on all fours and inserted the dildo in his asshole. "What do you think Tony? Do you like having this dildo in your ass?" "Oh yes, yes," he panted as Janet had started to masturbate his cock. Tony didn't last long as he spurted all over Janet's hand. Janet then placed her hand to Tony's mouth and told him, "Lick it up!" Tony was joined by Celeste as they licked it off Janet's hand and then kissed, swapping spit and cum between them. That evening's activities included playing an adult version of Simon Says. Everyone was supposed to bring a partner, but everyone was invited, partner or not! Since the Rear Admiral owned the ship, he got to be Simon. "Simon says men stroke your cock. All women rub your clits." After watching everyone play with themselves the Rear Admiral commanded, "Simon says find a partner and stick your middle finger in their asshole." Next, "Simon says stop what you're doing and take turns sucking on your partners nipples. Simon says bite those nipples!" The Rear Admiral had his wife, Lauren, as his partner and they were demonstrating up front! "Simon says to get into a 69 and perform oral sex on your partner. Use that tongue to please your partner." On the deck of the boat their were numerous variations of "couples" with heads buried in their partners "sex," licking clits and sucking dicks. "Simon says to lick your partners asshole." Each of the partners were now running their tongues over their partners starfish. Most had their hands on their partners ass cheeks, spreading them apart to get access to their partner's butt hole. "Simon says to switch partners. Find a dick and take it in your butt." The Rear Admiral and Lauren had switched partners so that the Rear Admiral was now on the receiving end of having his ass plugged. After several minutes the Rear Admiral declared "Simon says if any cocks have not come yet, start stroking your own until you come. Ladies you are to satisfy yourself as well, if you haven't already come." After another 5 minutes the Rear Admiral declared, "Simon says you're on your own. Have fun!" Later that night Lauren asked Janet is she would like to "serve" at brunch next morning, starting around 11am. Janet told Lauren that she would be at the kitchen around 10:30 to prepare. Janet was exhausted and her pussy was a bit sore, so she decided to relax the rest of the night and go to sleep early. The next morning Janet was served at 11am. She was prepared on a plastic sheet atop a serving table. She was laying on her back and decorated with fruit and veggies. She had pineapple rings surrounding her nipples. Whip cream was in her pubic area. Chocolate sauce had been placed all over her body. Grapes and strawberries were placed all over and around her body. She had a long seedless cucumber inserted in her pussy and had a carrot shoved in her ass. The green carrot tops were sticking out of her butt. There were cans of whipped cream and bottles of chocolate sauce arranged around the table. A serving table also had vanilla and chocolate pudding as well as several flavors of ice cream. Jello shots were arranged on the serving table as well. The only rules were that all food had to be eaten off Janet's body. It seemed that couples loved to have their partner eat food off Janet. Husbands had their wives eat the whipped cream from Janet's snatch. Then the wives placed pudding and chocolate sauce on Janet's nipples to have their husbands lick and suck that off. Jello shots were placed on Janet's flat stomach and were quickly snatched off by waiting mouths. Ice cream was placed on Janet's nipples just to see them come to attention! Janet had a difficult time staying still on the table as both sexes used the food as an excuse to have sex with her. Lauren came by and grabbed the cucumber and started to slide it in and out of Janet's pussy. She followed that with a shot of whipped cream on her clit and spent an inordinate amount of time licking it up. Janet tried to stay still as she came from Lauren's tongue thrashing. At noon she was carted off and she went into her shower to clean up and get ready for the show that afternoon. She was looking forward to seeing Rufus and Marcus, the father and son servers. Their big, black cocks were supposed to be a sight to be seen. They were putting on a sex show at 1pm, just before the boat was going back to port. Lauren and Nicole were going to put on a sex show with Rufus and Marcus. The Rear Admiral's wife, Lauren was pushing 40, and was now a full figured woman. Her face was still youthful looking. Her boobs had gotten bigger with age and were now a full D cup and sagging a bit with age and the extra weight. Her areola were large and dark. Her nipples could still stand up rock hard when excited. Her snatch was shaved except for a closely cropped landing strip directly above her clit. Her hips and thighs were no longer as slim as when she was younger, but they still attracted young men. Nicole was long and tall. There was not a bit of hair on her body, except for her head. Her hair was shoulder length and curly. She was a natural red head, with freckles on her cheeks and all around her body. Her pussy lips were large and covered a very large clit. Even when it was at rest it jutted out, but when excited it looked like a mini cock sticking out. Her boobs were nicely proportioned, a C cup on her frame looked just right. Her areola were small and her nipples when erect were still small. She loved to suck cock and take a good stiff cock up her ass, especially if she had another cock in her pussy! Lauren and Nicole arrived at the main deck together. They were to be the sex partners for Rufus and Marcus. Each of the women had on bikini briefs and short camisoles. Barely visible under Lauren's camisole was a chain that was attached from nipple to nipple. Rufus was the father of Marcus. Rufus was about 35 years old and his son had just turned 18. Rufus had a full 10 inch cock that was also thick. He called it "Black Beauty." Marcus had a cock that rivaled his father's but at his age it sprung to lfe quicker and was hard as a rock as soon as it was out of his pants. Rufus and Marcus had been waiting for the ladies and walked out to meet them on the main deck. Both had on cut off jeans and nothing else. Their skin glistened with baby oil and their six pack abs were on full display. Rufus grabbed Lauren and gave her a big kiss. Nicole went over to Rufus as well and grabbed his cock through his shorts as she gave him a kiss when Lauren was done. Lauren went over to Marcus, slipped off her top and let her hands dive into his shorts. Marcus had hold of the nipple chain and was pulling her boobs from her chest. The he let go and repeated it. Lauren was moaning in ecstasy as her tits were being stretched out. Lauren took Marcus' shorts and pulled them around his knees. Marcus finished the job by kicking them off. The crowd around the show gasped at the hard on Marcus was displaying. Lauren was stroking it and showing it off to the crowd as they moved in a small circle. Then she fell to her knees and took his cock in her mouth. Nicole was naked as Rufus had her bent over a deck chair. From behind he had his hands wrapped around her tits. The sight of her white skin and his deep black skin was accentuated by the bright sun. Slowly he put his one hand on Nicole's pussy and soon had his middle finger up her pussy. He was stroking in and out as Nicole groaned. Nicole finally turned around and told Rufus to strip out of his shorts. His erection brought another round of gasps from the crowd. Now Rufus bent Nicole over that same deck chair and started to lick her pussy and asshole from behind. He reached around her waist and pulled on Nicole's pussy lips as he was licking her from behind. Nicole's clit was starting to get erect. Rufus grabbed her off the chain and had her sit in it facing the one side of the crowd. He urged them to get closer as he knelt next to her and pulled her pussy lips aside and played with Nicole's huge clit. Rufus urged the crowd, "Look at this beautiful huge clit. It is bigger than some of the husband's cocks on the yacht." One of the women from the crowd walked up and started to suck on it like a small cock. Rufus then asked her to go back and watch. Participants from the crowd were discouraged until after the show. Marcus meanwhile was pounding his 9 inch cock in and out of Lauren's pussy from behind. Lauren invited Nicole over to lean over the same table she was using and have Rufus start to fuck her from behind as well. Soon both couples were getting hammered. Rufus and Marcus then switched partners. Rufus told Lauren to suck his cock. While he was in her mouth, Lauren grabbed Marcus and started to stroke him. Then she let Rufus out of her mouth and stroked him while sucking on Marcus' cock. Next she brought both their cocks together and tried to suck them both at the same time. All she could manage was the tips of their cocks in her mouth. Nicole had taken a moment while this was going on and had slipped into a large flesh colored strap on. Soon she had Rufus leaning on the table as she was lubing up his asshole. First sliding in one and then two and three, she was stretching his asshole out. Then she place the tip of her strap on at the base of his butthole. Slowly she increased the pressure and the strap on slide up Rufus' ass. Rufus had his hand around his cock, stroking it while Nicole was gaining rhythm sliding in and out of his rectum. Next to them Lauren was spread eagled across the table as Marcus was fucking Lauren's pussy. Each stroke made Lauren gasp, as Marcus slammed the entire length into her, pulled out and did it again. Lauren had hold of her nipple chain and was pulling on her nipples while she was being fucked. It didn't take long for her to cum. Soon Marcus followed and pulled out and shot his load on her back and ass cheeks. Nicole pulled out of Rufus and had him turn around while he was stroking his dick. "Marcus, come here! On your knees and suck your old man's cock until he cums." Marcus obeyed quickly and soon had his mouth around his father's cock. Marcus then reached behind his father and slid his middle finger in his ass. Rufus groaned and with a spasm started to shoot cum into Marcus' mouth. Now Nicole and Lauren got on their knees and started to lick Marcus' mouth trying to get their taste of Rufus' cum. Lauren wasn't done yet. She started to suck and stroke Rufus. She wanted him hard again. Meanwhile Nicole had Marcus leaning over the table and was sticking her strap on up his ass. She was reaching good rhythm when Lauren grabbed her and Rufus took her place. Now the old man had his dick pounding his son's ass. Next Nicole got behind Rufus and spread his cheeks and placed the strap on up his butt. After a few strokes they got into rhythm and both Rufus and Marcus were having their assholes being abused! Lauren sat down in front of Marcus grabbed his hard on and stroked it as he was being butt fucked. As Rufus built up another load, he pulled out of Marcus and turned to spurt on Nicole's strap on. Lauren started sucking on Rufus and soon he came in her mouth. Lauren stood and went to Nicole to swap cum into her mouth. Rufus and Marcus took each other in their mouth's to clean off the other's cock. The crowd was wild! It was now a full our orgy on deck. Everyone was naked and sucking, fucking, fingering and blowing. What an end to the weekend on the yacht! ***** I hope you enjoyed reading this short story! Please consider leaving feedback and rating this story. I read them all and appreciate your honest feedback.