Jamaican Getaway Sex Stories for free 2024 – Y2Stories.Com

Tina and Danny’s vacation is not what they expected…

“Mooom! Mom? Where are you?” Danny called out walking in his mother’s front door.

“I’m in here, honey!” Tina replied from her bedroom.

“Look what I have. I got these tickets on Groupon super cheap. It’s two-for-one airfare and a 5 day, 4 night stay at a resort in Jamaica,” he said showing her the details on his phone. “I know it’s been ages since either of us have been on a vacation, and with dad no longer around, I figured it would do us both some good.”

“Oh, hunnn. That’s amazing! Oh, my gosh. You are such a sweetheart,” Tina replied as she kissed the side of his head and wrapped her arm around his shoulder. She smiled and shook him a little and continued, “So, when does our little getaway begin?” Danny answered enthusiastically, “Next week. That way we have plenty of time to get things in order, buy some new clothes, and I already asked off for work. So, we’re golden.”

Tina’s ex-husband and Daniel’s father, Tom, was a serious drag. She loved him for being the father of her one and only son, but he was the furthest thing from affectionate, and was so focused on work, that his relationship with his son dwindled as well. The divorce two years ago left Tina lonely and looking for love, and Danny couldn’t care much less that his dad was out of their lives.

As the plane touched down, and Tina and Danny stepped out on the tarmac from the small twin engine jet, they caught a cool breeze off the ocean and smiled at each other; this was going to be the trip of a lifetime. They took a shuttle from the airport to the hotel, looking at the all the tourist attractions and things to do in a little booklet along the way. After about 30 minutes, they arrived at the resort, but the second they stepped in the reception area, they knew something was off.

“Hi, guys! I’m Jackie, welcome to Blue Bay resort, where all your dreams will come true… and then some,” a beautiful, peppy girl said walking up with a clipboard. Jackie was a tan brunette, about 5’7”, slim but top heavy, and wearing nothing but a red, mesh bikini top, with a white sarong covering her bottom half. You could clearly see her dark, silver-dollar nipples through the bikini, and Danny was having a hard time keeping his chin off the floor.

Several other guests loitered or passed through the lobby, giving away more that things were not as they seemed. One older, yet fairly attractive couple sat fully nude in a couple of easy chairs, conversing and sipping down some cocktails. Another group of two younger, fit guys, along with a middle-aged woman walked by. She was wearing a gold bikini with heels, while they weren’t wearing anything. She walked between them, leading the way with each of their phalluses in her hands. Danny had unknowingly bought reservations to a swinger’s resort.

“Daniel. What… the hell… is going on?” Tina said before her jaw dropped open and looked at her son with the same expression on his face. Jackie interjected, “Ok, guys, I’m going to show you around a little, and then to your room.” She walked them along at a leisurely pace, pointing out all of the amenities as they passed. She showed them where the sauna was, the massage room, the banquet hall, and finally, what seemed to be the main attraction, the pool.

In each of the areas, they saw people of all age groups in different levels of disrobe, and about half of them in the middle of some sort of sexual act. You’d see one girl sucking off a guy in a chair in one corner, then on the pool deck, you’d see an older gentleman with one woman riding his dick, and another sitting on his face. Tina and Rob were both beet red with embarrassment, they couldn’t even look at each other.

Finally, Jackie showed them to their room, and after she unlocked the door and handed the key card to Danny, she gave a smile and pecked him on the cheek before walking away. He blushed even harder as he dragged both their bags into the room. Since Rob had gotten such a good deal on these tickets, part of the catch was that the room came with only one queen-sized bed.

“Mom, I had no idea. Seriously. If you want to leave, we can find somewhere else to go,” Danny said in a remorseful tone. As she took a walk around the room, Tina shrugged and said, “Why not just stay here? I mean, you did spend a pretty penny on the trip, and it’s not like we have to stay here all the time. We can go out and just come back here to sleep. Right? Plus, maybe you’ll get to see Jackie again.” She followed up with a wink and a smile.

Dan blushed again for about the 18th time since they stepped onto the property, and replied, “Really, mom? Really?” She chuckled, laid down on the soft bed, and suggested a nap, then maybe the beach and some drinks to relieve the shock of what they’d just walked into. After making a clear demarcation line with pillows on the bed, he laid down and drifted off.

After about an hour’s slumber, the two each took their turn in the bathroom changing into their bathing suits. The beach was literally across the street from the hotel, so they were there in about two minutes. They commandeered a couple of beach chairs that were there for guests and set down their towels.

Danny took off his shirt, and having grown up surfing, he was lean and muscular with washboard abs showing above his shorts. Tina had always been mindful of her health, and was toned and athletic, with long, auburn hair. As a “trophy wife,” and being concerned with her looks, she’d chosen to have plastic surgery, with a perfect set of huge 34F’s. You’d be hard pressed to figure out they weren’t real; the doctor had done such a good job.

As Tina sat down her bag and kicked off her sandals, Danny set off to grab some drinks for the two. Walking back to the chairs, he saw his mother taking off the shawl she had covering her swimsuit. He was expecting some old granny-style one piece, but instead she was wearing a fluorescent yellow, string bikini. The little triangles over her breasts were having a hard time hiding her brown areola, and the bottoms were down so close to her pussy, that you could see just a small tuft of thin pubic hair above it.

Bending over to grab something out of her bag, Danny could see the thin yellow string wrapping around high on his mom’s tan hips. They continued between her perfect, oval ass cheeks, and then splitting right down the middle of her smooth vulva; he almost dropped their drinks.

Danny sat on his beach chair, mind racing at the thought of his mom’s pretty twat and handed her a mojito. “Oh! My God, baby. Just what I needed, thank you. Mmm,” Tina exclaimed, taking the drink from him. She continued with a smile, “You like my new bikini, hun? I wanted to try something new.” Adjusting the thin material on her large breasts, her nipples were easily seen as she lifted and moved the small pieces around.

“I need to go swimming,” Danny announced abruptly as he stood up, trying to hide a semi growing in his shorts. His excursion to the water helped settle the activity downstairs, but he was going to have to be very careful about where he laid his eyes when he returned. Thankfully, when he walked back up to his mother, she had her feet propped up below her butt, and a large magazine was blocking his view of her big tits. Crisis averted, for now.

After a few more beverages, the two got up and walked back to their room. Danny trailed behind his mom and could not take his eyes off her tight rump. Although she worked out almost daily, she still had a little bit of jiggle and bounce in the cheeks with each step. He’d never noticed his mom had an ass and legs like that, it almost made him cry. Still being tired from traveling, and not caring to see anymore strangers fucking in the wild, the two decided room service and a movie was enough for them that night.

The next morning, Danny woke up to find his mom wasn’t in bed, or even the room. He threw his shirt and shoes on and started roaming the grounds in search of her. Finally, after encountering a number of clothed, and non-clothed patrons, and in a number of “activities,” he found his mother in the main restaurant area.

Across from her table were five men of different shapes, sizes, and colors engaged with a sandy blonde, suburban soccer mom type; she was being totally man-handled by the group. She sat reverse cowgirl with a dick up her asshole, two of them inserted in her in cunt for some double vaginal action and was sucking off one more. The fifth guy I’m presuming might be her husband, sat back a few feet just jerking his dick, getting off to his wife being worked out.

Tina was once again in her string bikini, and some little booty shorts. She was focused on the group of men taking turns on this lady, with her hand between her legs frigging her pussy. Being three fingers deep, Danny’s mother didn’t even notice him walk up.

“Mom. Mom. Mom?” Danny snapped his fingers in front of her face.

“Oh, my God,” Tina was in shock; she’d just been caught by her son masturbating to a live gangbang. Removing her hand from between her legs, and covering her face with the other, she laughed a little and said, “Yes, honey. What’s up? What can I do for you?”

“What the hell were you just doing!?” he asked in total surprise.

Before she could answer, a cute waitress interrupted, “So, what can I get the happy couple today? Drinks? Food? Or are you just here for the scenery?” She winked and turned to look at the soccer mom, still getting plowed and chugging dick.

Danny started to blurt out, “Oh, we’re not a couple. She’s my mo…” Tina quickly covered his mouth and said, “Actually, we’ll have some daiquiris, please. Thanks.”

Tina did not want it known that a mother and son were staying together at a swingers’ resort. Also, considering she had given birth to Danny at 19, he was currently only 25, and she was still a smoking hot bombshell at 44, so it was totally feasible they could be partners on vacation. Maybe she was a good-looking MILF in her prime, looking to have some fun with a young stud; nobody else knew their true relationship.

The waitress came back with their drinks, “Don’t forget there’s a masquerade ball tonight at 9 o’clock. Obviously, everyone is welcome, and participation is not required, you can just come and have a good time.” Tina signed the check, and after the girl walked away, she looked at Rob and smiled, “Let’s do it, c’mon. Like she said, we can come, have some drinks, and see how wild this place can get. It’ll be a good story for your grandkids.”

Danny was convinced his mother had gone crazy, but after a little more convincing, he reluctantly agreed. Returning to their room, they found the hotel staff had left two masks on their bed, both were black, One was very non-descript and somewhat plain, the other must have been the lady’s, with lace fringe and some feathers; it was beautifully done.

After dinner and a bit of relaxing, Danny put on a pair of black slacks and a black suit jacket, that he’d brought in case they went out for a nice dinner. Underneath the jacket, he had no shirt, with his smooth, muscular chest and stomach showing; he thought he’d at least get into the part for the evening.

“Oooh! Look at my baby, so handsome,” Tina pinched her son’s cheek and stepped back to look at him. “Go get ‘em, honey. Momma’s gotta finish getting ready,” she said while still wearing a bathrobe, and pushed him out the door.

Not knowing what to expect, Danny went ahead to the banquet hall which was thumping with music and people gyrating to the beats. It was still a little early, so people were talking and laughing, loosening up with a few drinks; the good stuff had yet to begin. One thing Danny noticed though was that all the masks were completely the same as the ones he and his mother had. So, unless you knew the person or came with them, you had no idea who anyone was.

About an hour later, the party-goers were really getting into it. You had people sucking, licking, eating, and fucking in every square inch of the building. Even going into the bathroom, there was some girl bent over the sink getting hammered by a total stranger. It was sensory overload.

Not knowing the etiquette at such parties, and being somewhat shy, Danny had limited himself to just dancing with several women and had gone as far as groping a few of them, but that was it. He was still having a blast, though.

The excitement raged on as Danny noticed a tall, buxom woman that really caught his attention, flirting with a few men. She was tall with reddish brown hair, wearing a set of shiny, black stripper heels, along with some black silk stockings that ran up almost to the crease of her perfectly round ass cheeks, then a black thong below a shiny green bustier, and of course, the mask.

Occasionally, she would look in his direction and make eye contact, so Danny said fuck it, all this other craziness was going on around him, he was finally going to make a move. As he closed in behind her, he started lightly kissing her neck and shoulders. Surprisingly, she reached back with her hand and started groping the crotch of his pants, and his swelling member beneath.

He began caressing her magnificent breasts and cupping her firm ass. She gasped as Danny stripped down her bustier in one swift motion, exposing her massive chest, and large, light brown nipples. Turning her around, he was amazed at how glorious her big tits were, and she dove in for a deep, passionate French kiss. He couldn’t believe this vixen, practically the hottest woman in the room was so into him.

Taking the tip of her right breast in his mouth, he reached down slid his hand inside the front of her underwear and found the cleft of her soft vagina. She moaned as he slowly circled her swollen clit with his fingers. Moving his hand further down, he found her snatch was soaked already. “God, I need to taste her,” Danny thought to himself.

Laying her on of the couches, Danny reached down and pulled her thong down around her ass and up over her long legs, he then balled up the drenched panties and shoved them in her mouth. He gave her a smile and moved down her voluptuous body to find her soft, smooth labia, smelling its sweet aroma.

She started whimpering and moaning as Danny tongued and licked her dripping wet box. After flicking his tongue on her clit, he turned his attention to her clean, pink asshole, and was giving it as much love as he’d given her beautiful snatch. At his young age, he’d never known a woman’s asshole could just as tasty as her cunt.

Apparently, she’d had enough of him munching her box, when she sat up, spit out the undies, and grabbed him by the throat, once again shoving her tongue forcefully into his mouth, tasting her juices on his lips. She switched positions with him, and now on her knees in front of the couch, she pulled down his pants. It was her turn now.

Danny was well endowed and was gifted with a very thick 11 inches, so the second she caught sight of his manhood, the woman mouthed the word “Wow.” She just started devouring his cock, slurping and spitting, forcing it down her throat and choking on it; acting like a totally depraved slut.

She was such a pro that she could deepthroat his entire dick, and still manage to tongue his balls down at the bottom. Removing his dick from her pretty mouth, she started licking on his testicles and running her tongue up and down the shaft. Danny looked her in the eyes as she sucked his cock like a cum hungry whore.

All of a sudden, Danny realized who this beautiful slut with a voracious appetite for cock was… it was his own mother. He couldn’t move, he couldn’t believe it, his mother was giving him what was easily the best blowjob of his life. So overcome by depravity and pleasure, he just stared and let Tina continue to slobber all over his shaft and to lick his balls. “You have the best dick I’ve ever tasted,” she said, and the voice confirmed it was her.

His mind and emotions were in overdrive, and instead of being repulsed or stopping because he had been taught it was wrong and immoral, he couldn’t stop himself from what came next. Danny got up and laid his mother on her back on the couch, and looking down he could see his her drenched pussy quivering with anticipation. He then slid his cock from tip to base, deep inside her slick hole, it drove Tina insane.

“Dear God, you feel perfect! It’s like your cock was made just for me,” Tina screamed as her son rhythmically pounded in and out of her. Moans of pleasure surrounded them, as people from all over, and every walk of life continued this massive orgy, filling the air with the sounds and smells of human perversion. No one knew that in front of them all, a mother and son were fucking harder than any of them; incest before their very eyes.

The two switched positions once again, and with Tina straddling Danny’s long, thick meat, she slowly sat on his lap, his girth disappearing inside of her. Danny was mesmerized as his mom bounced up and down on his manhood, he was amazed at how amazingly smooth and soft it felt surrounding his dick, it really did feel like it was made for it.

Riding his dick intensely, her huge, round orbs bobbing in front of his face, Tina leaned in further and whispered in his ear: “It feels so much better than your father’s,” then looked him in the eyes and smiled. “She knew, she fucking knew,” Danny thought to himself, he was blown away. His mother had purposely drawn his attention and started their incestuous debauchery.

Tina stood up and bent over the couch, her incredibly long legs and perfect ass were something to behold. “C’mon, baby, fuck mama from behind. I need that perfect cock back inside me,” she commanded Danny. Who was he to disappoint his mother? So he readily agreed. Grabbing hold of his mom’s beautiful, tan ass cheeks, he thrust his thick meat inside his mother’s waiting cunt.

Danny stood there while Tina began taking control of the movement, and started to push back, fucking herself with her son’s cock. After watching his mother’s ass moving and grinding on his dick, he couldn’t take it much longer. He pulled out of his mother before it was too late, laid her on her back, facing her again, and pushed back inside her wet vagina.

“Fuck me, Danny, fuck me. I want your cum inside me, please give me your cum,” Tina kept chanting aloud. Hearing his own mom begging for his cum was more than he could take.

Danny’s cock let off inside his mother’s pussy like a fire hydrant, pumping her womb full of her offspring’s semen. Tina was in heaven as she came at the same time; being the highest euphoric state she’s ever experienced, her orgasm seemed like it would never end. As his dick continued spurting his man juice deep inside her, her pussy walls gripped and contracted around it.

After their everlasting climax, Danny pulled his still hard dick out of his mom’s slick pussy. Tina got on her knees in front of him, and took his cock, covered in cum and her sweet pussy juices, and put it in her mouth. “Wow. You really are a hungry little cum slut, aren’t you?” Danny asked his mom, and with a mouthful of dick, Tina moaned, “Mm-hmmm.” With that, Tina removed his clean, fat cock out from between her lips.

The next three days of their vacation, Tina and Danny’s relationship bloomed like never before. They were hoping it would never end, and before they left, they made reservations for another trip. Not only did they become better friends, but she took and swallowed countless loads of her son’s cum, and he buried his dick in his mother’s mouth, pussy, and ass more times than any girl he’d ever dated. That “trip of a lifetime,” was only just the beginning…