Sheila had been going on Jared's golf vacations for years. An accomplished softball shortstop, she should have found golf easy, but it soon became clear that this was not her game. Truth is she didn't try very hard - no driving range work, no practice putting green work - so she was embarrassed at the number of times another group called "Play through." Just riding along with Jared turned into an exercise in his analysis of each stroke, and she'd lost interest in those rides as well.
So it was that on this vacation, Jared had an early afternoon tee time. Sheila put on her dark red bikini and a well matched beige wrap and headed down to the resort's private beach. She paid a boy for a cabana and gave him her towel and book, but then she realized that the tiki bar was already open. She figured that a drink at the bar would be a good way to deal with her increasing resentment of how these golf vacations were going.
She was well into her third gin and tonic when a pair of middle aged duffers and their caddy came back from their round and sat down at the bar. As it turned out, she was sitting in the middle seat, so the men ended up on either side of her. She couldn't remember their names when she told me about this, so let's call them Abel, Baker and Charlie - make that Carlos since the caddy was clearly Latino and a fine specimen in Sheila's eye.
A round of the usual small talk was further loosened up by a fourth drink. Jokes ensued and Sheila realized she was intensely attracted to the caddy. "So I guess you guys were looking for your nineteenth hole," she offered in jest, and parted her legs a bit. It's well known that drunks find their own jokes much funnier than they really are, but the men were kind enough and interested enough to laugh.
Abel took a moment to get the joke and but finally reacted with an equally un-funny comeback, "I suppose there should be a pin in it, ha ha." Sheila giggled, and the men drifted off into silence.
Baker had a thought. "I don't suppose we could see how the nineteenth hole lies, could we?" he suggested when the lady bar tender was distracted on the other side of the bar. Sheila blushed at that but then checked to see if anyone was noticing them. Looking straight ahead to give the impression that nothing was happening, she reached between her legs and tugged the crotch of her bottom aside. Abel and Baker got a nice look at her shaved pussy. Then she quickly pulled the cloth back in place with another giggle and took the last sip of her gin and tonic.
Abel, not one to miss an opportunity, asked, "I don't suppose there is somewhere we could, uh, uh, you know, get a more complete picture, heh heh?"
Sheila held up her ring finger, "You know I'm married?"
Abel and Baker showed their rings, too. She thought about it for a few more minutes.
"Well we sure can't go to my room," Sheila said, "I can't be having my husband asking questions."
"Yeah, my wife would have questions too, when she gets back from her air-boat tour," Abel offered, "but you know Baker says he didn't bring his wife."
Everybody agreed that a visit was in order to Baker's room. Abel and Baker wandered off separately so as not to be too obvious. But Sheila knew what she wanted most and turned to the buff and attractive Carlos, "You're coming too, right?"
"I didn't know I was invited."
"I won't go if you don't," she lied. And so it was that the three men were gathered in Baker's room a bit later. The door was ajar when Sheila arrived and she pushed it open. The men were sitting around in various places in the room sipping beers from the mini-bar. But they all stood up at once.
"We weren't sure you would really come," one of them remarked, as they surrounded her between the door and the bed and started taking turns kissing her and running their hands over her body.
Abel and Baker pushed up her bra and began stroking and squeezing her tits. Sheila slipped the wrap off and dropped it to the floor. Carlos tried to push his hand into the bottom of her bathing suit, but the waist was too tight and his hand only made it part way in. He gave up in frustration and just pulled her bottom down to her ankles. Meanwhile Abel and Baker had managed to pull her bra off over her head as she stepped out of her sandles and the bottom piece.
Carlos was now kneeling in front of her naked body as she stepped out of her bikini and started to kiss her belly, and then her thigh and then her mound. She sighed as he probed her pussy with his tongue while Abel and Baker each suckled one tit. She widened her legs a bit and moaned when Carlos's fingers pushed up inside her.
"You know guys, I'm not going to undress all three of you," she managed to remark. Then she pulled Carlos to his feet and muttered, "You first."
While the men were throwing off their clothes, Sheila laid on her back across the bed with her head at one corner. All the men reacted in unison at her beautiful body splayed out on the sheet, "Oh wow!" Sheila's boobs were 34D globes that hadn't yet begun to flop down. Her dark nipples complemented her black hair and brown eyes. "Oh wow, you've shaved off your pussy." It seemed like Baker and Abel had never seen that in an adult woman, something that Jared had asked for. Sheila motioned the two duffers to the corner of the bed and took their fully erect cocks in her hands.
She was even more impressed than before as she eyed Carlos's toned and well muscled nude body. Her craving for him only grew stronger. He came around to the other side of the bed and crawled between her legs. Then he began sucking on her toes and kissing her feet and her ankles. She was already rubbing Abel's and Baker's cocks when Carlos moved up to her shins.
Abel's cock went in her mouth first and she sucked on it vigorously. Then it was Baker's turn. Back and forth between them as Carlos pushed her legs further open and lightly licked her thighs and then her tummy and then, "Oh yes, Oh yes," the space between her pussy lips and her thighs. Her hips were already rocking up, up, up when she felt him sucking on her plump lips. His tongue pushed in between. "Oh god, Oh god," she gurgled with Baker's cock fucking her mouth as Carlos's fingers pushed up inside her once again.
Carlos eventually climbed further up over her and sucked and squeezed and twiddled her dark nipples with his shaft pressed against her leg. Sheila was sucking and slurping Abel's cock when she felt Carlos's penis positioned at her opening. She stopped and looked straight at Carlos. "Yes Yes Yes."
Carlos thrust his organ deep into her vagina as her tummy convulsed to push up against him. She wrapped her legs around him as he pressed his cock against her cervix for almost a minute and her orgasm began. Then he started his long deep lunges that left her groaning in pleasure.
Baker's fuse was the shortest. While Carlos was fucking her, she had been rubbing Baker's cock between her fingers and taking it deeper and deeper in her mouth. His reaction and quickening strokes told her he was about to cum. Soon the first jet hit the back of her throat. For some reason she didn't really want to take everything in her mouth. She pushed him out and squeezed his shaft in her hand as she dragged every drop of semen out of him.
Carlos, who had reared up on his haunches to get out of the way, watched as Baker's eruptions landed on Sheila's face and hair. She finally turned and looked at Carlos, her smiling face a mess as she tried to see his cock shoving in and out below. Suddenly, she emitted a loud orgasmic scream. Carlos couldn't hold on much longer and soon, jet after jet of his semen filled her vagina. Sheila turned her head and took Abel's cock in her mouth trying not to bite in her ecstasy.
When Carlos's cock was finally limp and popped out of her pussy, she turned in the bed and laid her head on the pillow. Abel climbed over her next, and without even a pause, slid his shaft up inside her. He played with her tits and was going to kiss her before he thought better of the white stuff on her face. But all the oral sex had gotten him close and he quickly felt his climax let go. Stroke after stroke discharged every drop he had, til he collapsed on the bed beside her.
Baker had finally recovered. Sheila wanted a different position, so she got on her knees. Baker couldn't help but notice all of his conrads' output oozing out of her opening, but he climbed over her, shoved his cock in and grabbed her tits from behind.
Carlos was standing next to the bed, his cock slowly coming back to life as Sheila wrapped her lips around it. Meanwhile, she was loving the doggy style position, her favorite, and Baker's round two staying power gave her another rocking orgasm.
By the time Baker was done, Carlos's cock was rock hard. Sheila motioned him to lie back on the bed and climbed over him. She laid his cock flat on his tummy and pressed her sloppy pussy lips around it. She slid back and forth over it until both of them were moaning. Then she reached between her legs, held it upright, and eased herself down. Abel and Baker watched in amazement as she rocked down and up down and up. Carlos's cock repeatedly disappeared inside her each time and her boobs bounced up and down rhythmically.
Carlos was lasting a lot longer and Sheila was getting tired and feeling the excess drinking. Without separating, the two of them rolled over til she was on her back. Even as Carlos was finishing, she was starting to drift off to sleep.
Abel looked at her and turned to the other guys, "Is she asleep? ..Are you asleep?" Sheila seemed to mutter, "No ...," so Abel climbed over her, pushed her legs apart and entered her. When he was done, Baker followed, holding her legs up over his shoulders as he took advantage of the sleeping woman. Her eyes opened briefly, she murmured and fell back to sleep. In and out of wakefulness, she felt and saw Abel on top of her and inside her and then the same for Baker.
When the others left his room, Baker covered her with a sheet and blanket and wiped off her face with a damp washcloth. He woke her an hour later. "Don't you have to get back to your husband?"
"Oh God, did I fall asleep? Oh God, I need to take a shower! Where is everybody?"
"The other two left. Abel had to get to his room before his wife came back and Carlos had another gig."
Still naked, Sheila began to have vague memories from her nap. "Did you ... you know ... keep going ... I remember ... I think I was asleep ... Oh God, you guys fucked me when I was asleep!"
Baker nodded tentatively hoping she wouldn't be angry. But she actually thought it was hilarious.
"It was fun wasn't it," she said, causing him to sigh in relief, "but I better shower now." He admired her backside as she ran naked into the bathroom, and he watched her through the glass as she washed herself and seemed to be cleaning between her legs with extra vigor. His eyes were fixed on her as she stepped out of the shower, shivering, and toweled herself off. Then she came through the bathroom door and stood in front of him totally naked.
He was awstruck yet again. "You are so beautiful," and they embraced and kissed deeply. She realized she really liked him best of the three.
"Make love to me one more time, but then I have to go."
He had put his shorts on and she helped him out of them and took his cock in her mouth. She didn't have time to take him to his climax and wait for him to recover, so she stopped and stood up.
"You know, nobody ever did that for me before," Baker offered.
"Really? Your first blow job?"
"Second," he laughed. "The first was earlier," he laughed. After a brief pause while they kissed and caressed, he asked her, "Would it be OK if I tried to lick you down there?"
"You want to eat my pussy? ... I'd like that very much."
They collapsed together on the bed. Baker did a reasonably good job of giving her an orgasm.
"Put your fingers in, too," she begged between ragged breaths.
And when her own climax started to peak, she asked, "You can fuck me now." Baker slipped his cock inside her, kissed her deeply as their tongues played and caressed her boobs. His strokes were slow and gentle. Her orgasm continued quietly at first and then became louder and louder. "Oh Sheila, Sheila, Sheila," he moaned as he erupted inside her again. And then it was over.
Sheila ducked back into the bathroom, cleaned herself off with the already damp washcloth and came out to put on her two-piece. She kissed him quickly, slipped on her wrap and sandels and hurried out the door.
That evening as she sat with Jared at dinner, she watched Abel and a plump women be ushered to a table. Must be his wife, she realized. He nervously started to smile and then quashed that. Baker sat alone at a table way across the dining room. He smiled broadly at her in the knowledge that Jared was facing away. Sheila felt her pussy get wet, but she was glad later that evening when Jared had a stomach ache and didn't initiate sex. She was pretty sore.
Abel and Baker had checked out the next morning and Sheila was lounging by the pool in a different two-piece. She got up to order another gin and tonic and saw Carlos sitting on a bench smiling at her. "I looked up your husband's tee time. My car is in the employee lot not too far from here," he offered. Sheila followed him at a discrete distance.
His car was actually a full sized SUV. He clicked to unlock it and opened one of the back doors. She was expecting to have to make love on the back seat, but Carlos had lowered both seats, creating a flat deck big enough for them to lie on. There was a beach blanket that would protect them from the scratchy deck covering. They got in, laid next to each other and began kissing and tearing at each other's clothes.
Sheila managed to go down on Carlos, sucking on his balls, licking his shaft and finally taking it in her mouth. In the cramped space her sex ended up near his face as they both laid on their sides. Carlos started kissing her tummy and then her pussy as she raised one knee. Soon his tongue lapped at her pussy lips and forced its way to find her clit.
Sheila's orgasm erupted as she felt two fingers push inside to work in tandem with his tongue. She was sucking and stroking Carlos's cock and soon he joined her with his own climax. Sheila swallowed shot after shot.
When that was over, they lay face to face caressing and kissing and saying how wonderful it all had been. When Carlos was at last ready again, he entered her. Stroke after stroke and soon she felt his cock filling her for the last time.
Sheila got back into her bathing suit and kissed Carlos. As she was dressing she thought about the blanket in the bed of the truck. "I'm not the first girl to be back here with you am I?"
"No. It happens three or four times a season."
Sheila thought for a while, "How many years have you been working here?"
"Seven"
"Seven times three or four? More than 20 ladies?"
"Well, some of them are regulars," he chuckled. "It's not your first time either is it? I mean cheating."
"No. But this has to be the worst if it ever came out, hehe."
She and Jared were leaving tomorrow. "Thank you. Thank you so much," she said and gave him a parting kiss.
Sheila went back to the pool and jumped in. When no one was looking she pulled the crotch of her bikini bottom aside and tried to get the water in to clean out the evidence of her sins. She was already thinking about next year.