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Garys Unexpected Vacation Joy

Garys Unexpected Vacation Joy

by averagegary
19 min read
4.46 (7700 views)
adultfiction
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Gary Silvers was not looking forward to his upcoming family vacation. It had been a few years since he, his wife Amy, and his 17-year-old son Jack had been able to get away for a week-long summer vacation trip due to work schedules and Jack's camp schedule.

They lived near Philadelphia, so weekend trips to the Pocono Mountains or the Jersey Shore sufficed. Most of the trips and prior vacations were also with Amy's 80-year-old mother Deborah who was like part of the family as she frequently picked Jack up at school when he was younger and cooked dinner for the family. Gary couldn't remember the last trip where it was just him, Amy and Jack.

Amy's older sister Ashley, lives in California and constantly complains she never gets to see anyone. Ashley recently bought into a timeshare program with properties nationwide. She said if Amy and Gary pay the resort fee, she could book a week-long stay in Virginia Beach so they could all see each other for a vacation. Even though Ashley and Amy get along about as well and oil and water, Amy reluctantly agreed. It should be noted that Ashley also doesn't get along with her mother.

Gary's 56 and thought that with a teenage son who would want to go off and do his own thing and three women who would be constantly arguing it would be a long, miserable week. His wife and her sister are both younger than him as Amy's 50 and Ashley's 52.

Gary's feelings about the trip appeared to be correct even before they even arrived in Virginia Beach. What should've been an easy 5-hour drive turned into a traffic-filled, rainy 8-hour drive when Ashley insisted needed to get picked up at a friend's house in Richmond instead of simply meeting them at the resort. With lots of bickering in the car, they finally arrived at the resort at close to 8 pm. Another brief argument ensued over what to do for dinner before deciding to order in Italian and then call it a night.

The bickering and name-calling among the women started up again the next morning and made for an uncomfortable first day. The fact that the worst heatwave in years was hitting and Gary doesn't handle extreme heat well made things even worse.

They spent some time on the beach and boardwalk but by early afternoon Gary was miserable and ready to go back to the room. While he stayed alone in the air conditioning, the rest of the family checked out the resort's swimming pool.

Gary is just an average guy - 5-foot-7, medium build, with short brown hair. His wife Amy is only 5-foot-4, curvy, bordering on full-figured, with straight dirty blonde hair to her shoulders, green eyes, and 38D breasts. Ashley on the other hand, while only an inch taller, has a thin physique, with curly hair she's dyed red that extends past her shoulders, brown eyes and 34C breasts. When he and Amy got married 20 years ago and he met Ashley, she had a runner's physique and he lusted after her. The years haven't been good to her as she's showing her age in her face and her figure has faded. Her bitchy attitude toward his wife has also cooled the lust, but he still thinks she's hot and wants to fuck her.

Their rental had two bedrooms and a sleeper sofa. Amy let her sister and mother share the master bedroom, which had a king bed, while she and Gary took the smaller bedroom (with a queen bed) and Jack slept on the sofa bed in the living room. The sofa bed was right outside of Gary and Amy's room so Amy was reluctant to do anything Jack might hear. Plus arguing with her sister and hearing her sister arguing with her mom, caused her not to be in any type of romantic mood, let alone a mood for sex.

The next two days were more of the same with the arguments. Attempts to go sightseeing in Williamsburg and Busch Gardens didn't work as Gary was miserable and in need of air conditioning by lunchtime.

On day four the family decided to go to take it easy and just use the pool after lunch. Gary said he'd stay behind. His wife was in a white sexy one-piece suit that emphasized her breasts and hugged all her curves just right. Ashley was in a bikini that showed plenty of cleavage and hugged her ass so a hint of the bottoms of the cheeks were showing. The opportunity to watch them get wet in those suits made his decision more difficult. Just looking at them was causing him to start getting hard. Less than five minutes after they left, Gary decided to use the alone time to check out the whirlpool tub in the room.

He climbed in nude, grabbed his earbuds and picked an audio story off Literotica to listen to while he thought about Ashley and Amy. He got the jets going, leaned against the wall and closed his eyes. He was feeling good and relaxed.

After about 10 minutes he began to absent-mindedly stroke himself. By coincidence, once he was fully hard the jets stopped wrecking the mood. The story was also over so he climbed out, took out the earbuds and placed them on the counter next to his phone, restarted the jets and climbed back in.

He had closed his eyes and began to stroke, thinking about Amy and Ashley double-teaming him, when he heard Ashley shout.

"Holy shit! What are you doing in here? I thought you were in your room because the bathroom door was unlocked!"

Gary's eyes shot open to see Ashley standing there holding a towel over her presumably nude body.

"I'm relaxing in the tub and I didn't lock the door because I thought I was home alone. What are you doing back here so early?" he said.

"I had a big argument with them and came back here to relax, now get out of the tub."

"How do you know I'm not nude in here?"

"You would've locked the door if you were and I'm willing to bet you're not."

"Seeing your mood, how about we make a simple bet?" Gary said. "If I am nude, you drop the towel, let me see your nude body and I'll leave. If I'm not nude, I'll simply get out and leave."

"I'm so sure you're not nude, that I'll join you in the tub and straddle your lap if you are and if you're not you simply get the hell out."

"It's a bet," Gary said, extending his hand out and Ashley shook it.

"Stand up!" she shouted.

Gary stood up with his thick 7-inch erection sticking straight out in front of him.

"Drop the towel and let me see you," Gary taunted.

She dropped the towel exposing her breasts and pussy. Her breasts had perfectly sized areola with eraser-nub nipples and her pussy had a nice landing blonde strip above it. Gary simply started for a minute.

"Your breasts are more perfect than I imagined," he said.

"Glad you like them, now make room for me," she replied.

She smiled as she climbed in and stood in front of Gary. She gave him a hug and licked his neck pressing her breasts against him while reaching down, taking his cock in her hand.

"Had I known you were packing this I would've seduced you years ago," she said and licked his ear. "Now sit down, we probably don't have much time."

Gary sat down and Ashley placed a leg on either side of him, reached between them to grasp his cock in one hand and placed the other on his shoulder as she lowered herself onto him.

Gary could only moan in pleasure as he felt Ashley's tight cunt envelop his cock.

"Fuck you feel so good," Ashley moaned as she lowered herself.

"So do you," he moaned back.

Once he was fully inside her, he leaned forward and began to lick and kiss her tits on the surface of the water as she rocked herself back and forth on his cock.

The water was beginning to splash out of the tub and the jets made moving a little difficult as they their movements were limited.

"Get off me," Gary whispered.

She stood up as he quickly got up and sat on the edge of the tub.

She moved to straddle his legs and taking his cock in hand, held him in place as she lowered herself onto him.

She started to rock herself back and forth on his cock wrapping her arms around his neck.

His hands went right for her ass and squeezed as his face went immediately to her breasts.

She started to ride him and licked his neck and ear.

"Amy was right," she whispered. "Your cock is wonderful. Now get ready to be ridden hard."

Her riding intensified to the point where Gary had to take his mouth off her breasts and simply sit there and watch them bounce.

"Are you always this wild and horny?' Gary laughed.

"Only when I'm with a cock like yours," Ashley panted as she rode.

"Oh fuck, I'm close," Gary groaned. "Get off me. I want to fuck your face and cum on your tits."

"Not this time," Ashley groaned. "I need to cum while I'm riding and feel you shoot in me."

Gary grabbed her ass as he started thrusting his hips up into her.

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"Yes, yes, yes." Ashley panted.

"I'm sorry, but I'm gonna cum," Gary groaned and with one final hard thrust he held himself inside her as he shot spurt after spurt into her.

Ashley simply moaned loudly as her body shook.

After she came down from her orgasm, Gary licked her neck and squeezed her tits.

"We have so many lost years of fucking to catch up on in the next few days, think we can do it?" she asked.

"Are you the same woman who threatened to cut my cock off if I cheated on your sister?" Gary laughed. "We can keep fucking, but under one condition -- you treat your mom and sister with respect and stop arguing with them, even if you don't like what they say or how they act."

"I'm giving you a hall pass for me," she laughed. "I'll try to get along with them, but there's a lot of hurt and history there."

"Good to hear that you'll try to be nice. I don't know how many times we'll be able to do it, but it will be fun trying. Now let me get out of here before we're caught."

Gary quickly left the bathroom, got into his room and put on shorts and a t-shirt a few minutes before everyone else came home.

"How are you honey?" Amy asked.

"Good," Gary said. "Have I ever told you how hot you look in that suit? How was the pool?"

"It was nice and refreshing and I did notice a few guys trying to act like they weren't checking me out," she laughed.

"How about we put a couple of pillows behind the headboard, lock the door and have some fun?" he said as he moved behind her and pressed his semihard cock against her ass while groping her tits and kissing her neck.

"What's gotten into you?" she laughed.

"You always call me your horny old man with a one-track mind," he said. "Seeing you like this makes me extra horny. Plus, the fact we haven't done it in over a week makes me want you more."

"I want you too," she whispered reaching back to grab his cock.

"Then what's stopping us?" he said as he eased her bathing suit straps down over her shoulders.

"I don't want to be heard," she protested.

"That's why we put the pillows behind the headboard, so we can avoid any noises coming from the bed," he said.

"That's so tempting," she sighed.

"Then what's stopping you?" he whispered as he moved a hand down and sild a finger underneath her suit to rub her pussy.

"Nothing," she said as she turned to face him and peeled off the suit, stepping out of it.

Gary quickly moved some pillows behind the headboard and returned to embrace her. He hugged her tightly kissing her lips before moving his head down to lick her breasts.

"You're over-dressed," she chuckled as she pushed down his shorts, forcing him to step out of them while he peeled his t-shirt off.

She was stroking his cock with more urgency as he began to finger her pussy.

She moaned softly into his neck how good it felt.

"God, I've missed being with you in this way," he moaned before kissing her passionately.

They continued to stroke and finger each other for several more minutes before Gary pushed her back onto the bed.

"Snack time," he chuckled as he knelt between her legs.

He immediately moved his face to her pussy where he licked slowly up the length of her labia. He used the flat of his tongue against her lips feeling them moisten. He moved his left hand up and began to gently rub her clit as he continued to tease her labia with his tongue.

She grabbed a pillow to stifle her moans as he slid his mouth and tongue to her clitoris. He quickly flicked his tongue against her clitoral hood, kissing it gently as he reached up to caress her breasts. He gently took her clitoris between his lips as he squeezed her breasts. He began to run his tongue over her clit as she began to moan louder into the pillow and run her free hand through his hair.

He continued like this for several more minutes before raising his head and licking his way up her body. He paused lick her breasts, one at a time, gently taking each nipple between his lips. As he made his way up her body she had reached down and was urgently stroking his cock.

After leaving her breasts he looked into her eyes and smiled.

"I love you," he said before pushing the pillow aside and plunging his tongue into her mouth for a passionate kiss.

They kissed several more times as he held her face in her hands.

"I love you too, now get in me," she panted after the last kiss broke.

"Whatever the lady desires," Gary laughed as he stood up, put her legs on his shoulders and swiped his cock over her pussy a couple of times before pushing himself into her.

"Yes" she moaned as he entered her.

He started with slow thrusts, gradually building up speed, loving the feel of her pussy around his cock and the sight of her breasts heaving with each thrust. He continued this for several minutes before easing her legs off his shoulders so he could lean in and kiss his wife passionately.

She wrapped her arms around his shoulders and her legs around his lower back as they kissed. She started bucking her hips up to meet his thrusts. They were both groaning softly as they locked eyes.

"You... feel....so.... fucking.... good," Amy panted.

"So do you," Gary moaned as he continued to thrust into his wife.

After several minutes Gary said he needed a change and rolled them over while holding himself inside her.

Now Amy was on top, rocking herself back and forth on Gary's cock. He moved his head up so he could bury his face between her breasts. He started to lick her breasts as he grabbed her hips and started to thrust up into her.

"I'm close, do you want me finishing in you or on you," Gary panted.

"Ooooooooooh," Amy moaned as her orgasm began to hit. "Yes! Yes! Yes! Don't you dare pull out! Mmmmmmmm! You feel so good!"

His wife's body started to shake and her pussy clamped down on his cock as she rode out her orgasm.

"Yes!" Gary groaned as he held her hips and fired what felt like a gallon of cum into her pussy.

They kissed and looked lovingly into each other's eyes.

"That was amazing," Amy whispered as she rolled off him. "So, did you finish this way with Ashley or did you pull out and cum on those tits you're always looking at?"

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"What are you talking about?" Gary asked shocked.

"I got tired of hearing her complaining how long it's been since she's gotten laid," Amy said. "She was complaining how hard it's been for her to pick up guys lately. So, I told her that you've had the hots for her and she should go back to the room and fuck you."

"Really?" Gary said. "What was her reaction?"

"She said you weren't her type, but she might make an exception and asked how good you were."

"I told her you're amazing and never fail to get me off."

Gary broke into a huge grin with that.

"So, you wanted her to fuck me?"

"I didn't want her to, but I wanted to shut her up and give you a treat, I'm sure this vacation has been hell for you."

"Thank you, it has been a rough week. Would you mind if I had some encore performances with her?"

"Not at all. It will hopefully keep her quiet. I know you love me and with her it will be just sex, hopefully fucking some sense into her."

"I do love you and thank you. Any chance you could grant me a fantasy and join in one of those encores?"

"We'll see," Amy laughed before she and Gary hugged and kissed again.

The next evening, Ashley was standing behind the kitchen island in just shorts and a t-shirt complaining that she was aching. The island was in the middle of the kitchen, which was open to the living room.

"Let me give you back massage," Gary said and got up and stood behind her. He was also in shorts and a t-shirt. The island blocked the below the waist view of anyone looking in that direction.

He rubbed his hands up the length of her back from the waist, parting them at the shoulders to rub her shoulders and then down the side of the back to her hips before beginning the process over again.

"Should I behave or misbehave?" he whispered in her ear.

"How do you misbehave during a backrub?" she asked.

"Well one way is my hands could slip," he said as he reached her shoulders and then reached around to squeeze her breasts before moving them down.

"Mmmmm," she sighed softly.

He moved his hands down and squeezed her ass before beginning the next rub.

After cupping her breasts again, he began moving his hands down and whispered to her again.

"My hands could also slide down too far," he said as he gripped the waist band of her shorts and pulled them down, with her panties.

He took a minute to pull his shorts and boxers down and press his semi-hard cock against the crack of her ass.

"I like the way you think," she whispered as she looked over her shoulder and smiled.

Her right arm reached behind her and took Gary's cock in her hand and began to stroke it.

He let out a soft moan as he continued to rub her back, grabbing her tits each time he was going to slide down her body. Each time he got to her hips, he'd reach around and rub her pussy.

After a minute or two Gary was rock hard and Ashley was wet, whispering for Gary to finger-fuck her.

He started pumping his index finger into her at the same rate she was stroking him.

"Be honest, you want my cock, not my fingers," Gary whispered.

"We can't fuck here, we'll get caught," Ashley whispered.

"No we won't, they're all too into the movie," Gary whispered back before he bent her over more to expose her pussy as he pushed himself inside her.

He grabbed her hips and started slamming into her. Ashley was biting her lips to suppress her moans.

She started bucking her hips back to meet his thrusts.

Gary raised her right leg and placed it on a barstool next to the island to give him better access.

At this point Gary was leaning over slightly with his hands on her hips. They were trying to keep quiet but the sound of the skin slapping together was undeniable.

Amy glanced over and smiled before shaking her head.

"What's that slapping sound I hear?" Deborah asked.

"I'm just massaging her thighs," Gary responded.

"Oh okay," Deborah said without looking away from the screen.

"Massaging my thighs?" Ashley laughed.

"I had to think of something," Gary laughed.

"We need to finish quickly," Ashley hissed as she bucked back and clamped her pussy around Gary's cock.

Gary wasn't able to thrust hard anymore as she had a vice-like grip on him.

She grabbed the counter tightly for support and rocked herself back and forth against him.

"Oh fuck!" Gary groaned softly. "You're squeezing the cum right out of me."

He grabbed her hips and fired half a dozen shots into her before he started to slide out.

They quickly pulled up her panties and shorts before any cum could start leaking out and he pulled up his boxers and shorts.

"Thank you," she whispered. "I needed that."

"No, thank you, that was amazing," Gary whispered back.

They made their way to the living room and sat down, Ashley on an empty chair, Gary squeezed in on the couch next to his wife. Ashely could feel the cum dripping out of her into the panties and excused herself before it started to show through the shorts. After the movie ended Gary and Amy returned to their room, where Amy confronted him.

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