Summer Shenanigans

This my entry in the

Literotica Summer Lovin' Story Contest 2024

. I had been working on this story for a while, and SUMMER LOVIN 2024 gave me the inspiration to finish it. I hope you enjoy it. Some of it is based on memories of people and places from days gone by.

All characters are 18 or older.

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Part 1: Moonlight Shenanigans

We were enjoying a couple months of part-time jobs, parties and clubbing between semesters at university. We were lucky to all be together for one last summer. Co-op work terms were coming up, and university transfers would send some of us away. We wanted to make the most of the remaining free time, and warm months.

As a group, we had started to form in junior high through the district school band. We had gathered a couple more folks in high school, and finally coalesced the summer we all graduated. Jake, Willy, Andy, Marsha, and me, Barry, livin' large!

In hindsight, I should have understood the undercurrents; the sub-text, but no one said I was the brightest boy when it came to reading the tea leaves of love. I almost missed out on a prom date, until I was saved when the girl i wanted to ask asked me! Anyway, this would turn out to be a fateful weekend, late in the summer.

This summer, Marsha and I were the two singles in the group. People might have mis-took us for a couple because we always seemed to be together. Marsha had dated one of my other peripheral friends through senior year of high school, and our freshman year at college. This left me feeling like Marsha was off-limits to me. As it was, each of us had been dating other people on and off throughout the year.

We often took the same classes at college, and regularly commuted there together. Since I had a car and Marsha didn't, we usually travelled together as our friends group moved around the area. I'd pick her up early, then drop her off as the night closed. Totally platonic. But we were spending a lot of time together, and we'd gotten into some soul-searching discussions.

I couldn't deny that Marsha was attractive. I would sneak a glance to check out her ample chest. She must have had DD cups. She could stretch a sweater thin. She had a descent ass, too, but she was never athletic, so she didn't have that round, muscular athletic look. She did know how to show it off though, and her choices of mini-skirts or tight jeans made her popular at the clubs. She usually kept her dark brown hair about mid-shoulder length, and wore it in a ponytail, braided, or loose depending on how she was feeling.

Today we had all met at our favorite summer destination. Andy's parent's had a cabin on the Bras D'Or Lakes about 45 mins outside of town. It was in a really nice spot, set back from the shore a ways, overlooking a small bay where they kept their sailboat moored. It was probably our favorite place to hang out because we could swim, or party, or just laze around.

The cabin had a spacious layout. There was a full kitchen, two and half bathrooms, and three bedrooms. The main living room had a couple of sofas that pulled out into beds, and a fully furnished basement had two more pull-out sofas. It was a made for entertaining, followed by crashing, and we loved to take advantage.

We were a responsible group, though. We always made sure someone (we referred to as "the custodian") was staying fairly sober to keep an eye on the people and the property, and we always cleaned up. Andy's Mom would often comment that our parties resulted in a cleaner house than she could manage herself.

Tonight, the fellas had decided to throw a party for some of our closest friends. We were expecting about 30-40 people. I had volunteered to be the custodian to keep track of things as the night progressed. This didn't mean I wasn't going to have any adult beverages, though. I was planning on having a couple of beer.

Because the cabin was about 25 miles outside the city, we knew there would be a pile of cars to deal with. We had had a standing rule for a long time that if you came with a car, someone sober had to drive it home. It would be my job to see people back to their cars and make sure everyone was driving off safe.

However, by 10:00 it became clear that the crowd wasn't going to grow much beyond fifteen or so guests, and the folks who came were drinking light. We were all a little disappointed. There were other things going on in town we were competing with, including a decent band playing at a hockey rink.

I had been wandering from conversation to conversation, but I was a little bored. Everyone was well behaved. To relieve the boredom, I was considering going for a night swim, but I needed a swim buddy (safety first!). None of the guests would have swim trunks. Skinny dipping wasn't out of the question, but I wasn't interested in a dick parade. So, I didn't start publicizing my idea.

I was standing on the deck overlooking the bay and considering my options when Marsha came over and leaned against me, drinking a vodka cooler. I put my arm around her.

"What's up Barry, you bored?" she asked. "You've been standing here by yourself for a while."

Pointing towards the cove with a mostly empty bottle of Molson I said, "I want to go for a swim. It's humid, and the water would be a nice relief," I said.

"It's a full moon, too, so it would be easy to see. You should go," said Marsha.

"Well, Marsha," I said in a sarcastic voice. "I'd need a swim buddy. You said earlier you brought a swimsuit. Do you want to go?" I asked, hopeful.

Marsha was non-committal.

"Umm, maybe. I was talking to that guy over there," she gestured vaguely, "Chad. He came with Andy's brother. Never met him before, and he's kind of interesting," she said, then looked back at me and winked.

"Oh, I see." I replied sarcastically. "Girl's gotta get some fresh meat!" I winked back at her.

"Don't hate the playa'" said Marsha, and she hiccuped.

"Oh, so classy," I mocked. Michelle gave a forced belch and walked away laughing.

Well that was that: no swim tonight. I walked back inside and made my way to the kitchen. There were some empty beer bottles, and take-out food containers spread around the counters. I grabbed the garbage can and dropped the food containers in them. Then I went out to the porch and found an empty beer case to put the bottles in.

I started to head outside to put everything by the trash bins when I heard noises beyond the screen door. I stopped and listened.

"Oh fuck, yeah. Oh yeah. Oh that's so good... mmmmm" some guy was moaning.

I didn't recognize the voice, but decided it wasn't the best time to put out the garbage. I didn't want to beak up someone's good time. So, I left everything inside the door and went back to get another beer.

As I got to the fridge, Marsha came into the kitchen. She had on jeans shorts over her one-piece bathing suit.

"There you are, Barry. Let's go swim!" she exclaimed.

I smiled. "Now you're talking," I said slapping my hands together. "Hang on, I'll go change."

"Ok, I'll have another cooler while you're gone," she responded.

I ran upstairs to the bedroom with my bag and quickly switched to my swim trunks. I was gone less than five minutes, but when I got back, Marsha was finishing her cooler.

"Whoa, you really sucked that one down," I said with a laugh.

A couple of other people in the kitchen laughed along with me. Marsha gave me the finger and said "wouldn't you like to know." And then she belched, again. Classy girl.

We headed down to the cove to swim. Getting into the water and swimming out was going to feel great. The air was still warm and there was no breeze. The music coming from the cabin was the only other sound to be heard.

"What happened to your fresh meat?" I asked.

Marsha snickered. "Poor Chad, he had to run to the bathroom to puke, I think. I'm pretty sure he was younger than he was letting on," she sighed. "Another dead-end; story of my life."

"You get your share of attention. This dry spell won't last much longer," I said side-hugging her shoulder.

"Thanks," she replied.

"Let's swim," said Marsha. She kicked off her thongs, and dropped her shorts. It was a full moon so I could see her pretty well. As usual, she wore a stripped, one-piece bathing suit. All the other girls wore bikinis, but she never did. I wondered why, but never asked.

She did look good in the suit though. It was tight-fitting, almost like a competitive swimmer suit, and with boobs like those she probably appreciated the support. It looked good on her butt, too.

We both waded into the water. Because the cove is fairly shallow at low-tide, the water was getting warmer than usual this summer. The common descriptor was "like bath water." So, it was easy to get in.

After floating a few minutes, splashing each other, and generally horsing around, Marsha had an idea.

"Want to do something naughty?" she asked while treading water.

"Me? Naughty? Never!" I goofed.

"Let's go swim to the boat, and get on it," she said.

"Hmm," I said, "that could be fun."

I turned to look at the boat. It was only about twenty-five yards away. It had a ladder that wasn't fully extended, but it didn't look that far from the waterline. I figured we could swim out there and I could either surge out of the water that short distance to grab it, or maybe lift Marsha out of the water to get to the ladder.

I said, "OK, let's go" and I started swimming to the boat, with Marsha right behind me.

My Mom had put me through years of YMCA swim classes, and in high school I played some water polo. Though swimming was never my main focus, I was competent. I knew Marsha could swim, but she wasn't an athlete. I glanced back over my shoulder a couple of times to make sure she was going to make it. I needn't have been worried, she was right behind me, looking strong in the water.

When we got to the boat, I came to two realizations: first, the ladder was further from the water line than I had thought. Second, I wasn't Aquaman so I wasn't going to surge out of the water high enough to grab the lowest rung. But I was sooooo close when I tried.

Ok, it was going to be plan B: trying to help Marsha up to the ladder. We tried several versions of this, including the chicken-fight posture on my shoulders, and trying to lift her up, which in reality meant pushing myself under, because physics.

The last version was her idea, and appealed to my inner pervert. She suggested with both sink a little under the water, with me below her, then we would both swim up as fast as possible. When she would hit her maximum height, I would continue up with my hands on her ass, pushing. It had potential for success, and calamity.

I briefly considered having to hold her ass in my hands while trying to push up. All kinds of consequences starting running through my head, including what if my hands ended up under her suit? Or, I could end up giving her an epic wedgy, and if I got my placement wrong, I could end up with hands full of her pussy. All of these would result in failure, of course. Bah, failure is for the meek.

So, I said, "let's go for it." I was willing to give it the old college try, mainly because she had suggested it. She must have understood the risks. This was also an indication that she had consumed just enough alcohol to throw all caution to the wind.

It took a few attempts to get the setup right, and each attempt involved me holding Marsha's ass in my hands. I tried to keep it "professional," but it was her ass, and my dick was starting to call from the bench for some game-time. On the third attempt we got the timing right and hit maximum lift. But it wasn't enough. I had a strong suspicion that my tenting swim trunks were creating enough drag to spoil the effort.

The realization that holding Marsha's ass gave me a hard-on should not have been a surprise. I had actually seen her in her underwear previously, and she did look pretty sexy, though she was mid fast-change from school garb to something more suitable to go out on the town. She was in the front seat of my car, but she changed so quickly all I got was glimpse while driving.

We sank underwater after our last attempt, then we came up sputtering and laughing at the sheer ridiculousness of the whole failed endeavor. We were treading water in front of each of, when Marsha's hand accidentally brushed my hard-on. I immediately moved backward a little. She didn't react, so I assumed she thought she brushed my leg.

"Well that sucks," said Marsha while we floated, catching our breath.

Yeah," I said, "but it wasn't a total loss."

Marsha looked at me quizzically.

"How's that," she asked.

I smiled for a while before I answered.

"Well, I did have your ass in my hands quite a few times," I said, looking a little too contented.

Marsha looked back at me, unimpressed. "Boys...," she said shaking her head.

By the time we got back to shore, we were both tired. My hard-on had subsided enough that it wasn't so obvious I felt I needed to hide it. We found our towels and clothes, but we only put on our thongs to walk back to the cabin. The air was warm so we wouldn't get cold. We weren't saying much but Marsha leaned into me for support. I put my arm around her shoulders, and she put her arm around my waist.

We hadn't gone far before I heard someone moaning in pleasure, for the second time tonight. Marsha heard it, too, and stopped. We waited to hear it again while looking around for any sign of other people. There wasn't much around more than trees and bushes along the property boundary, and the water behind us.

We heard it again.

"That feels so good. Mmmm..." It was definitely a guy, but I couldn't quite make out the voice. The source was off to our right.

Marsha giggled. "Let's go see who it is," she whispered.

Taking my hand, she led us in the direction of the action. We tried to quietly creep past the bushes on the boundary to get a look. The full moon was casting shadows through the trees, and we had to squint to see into the darker areas.

"Over there," Marsha whispered, pointing towards a large birch tree. I could see the couple, partially illuminated by the full moon, partially in shadow.

"Who is it?" I asked.

"I think it is Willy and his new girlfriend, what's-her-face," she said.

I saw where she was pointing. It was Willy. Willy getting a blowjob.

"You mean it's Willy with his-dick-in-her-face," I replied in a whisper.

Marsha covered her mouth with both hands to stifle a laugh, and then elbowed me in the ribs.

They were about 20 feet away in perfect profile, and Willy's girl was really going to town on his dick. Willy was leaning back against the tree, mostly looking down at the top of her head, but occasionally his head roll back when he would moan.

His girlfriend was on her knees. Her shirt was wide open and her bra was pulled up. Her perky tits were swaying a little as she sucked him. I could clearly see Willy's dick disappearing most of the way into her mouth. She had one hand at the base of his shaft and the other was cupping his balls. I could hear the slop of her sucking, too. I guessed it was getting pretty messy over there.

This was hot stuff, even if it was very pervy. Very quickly I was hard again. My suit was tenting, so I turned slightly sideways, to not accidentally poke Marsha.

Marsha was as transfixed as I. She was standing next to me, and I could hear her breathing. I think she was getting a little worked up. I was definitely getting worked up. I was also feeling like trying to see if I could get a favorable reaction from Marsha.

Marsha was on my right. I quietly moved slightly behind her so I was watching over her shoulder. I had to move slow to avoid making sounds, and also not to startle Marsha. I moved a little closer and put my right hand on her right hip. I heard her take a breath, and she stiffened up, a little.

Willy's girlfriend pulled his dick out of her mouth and played along the tip with her tongue for a few seconds. Then she stood up. She embraced Willy and they had a deep passionate kiss. Willy's hand went to one of her tits, squeezing and kneading it. Soon she started to murmur something I couldn't quite make out.

Willy leaned down and took her nipple into his mouth. Whatever he did with it received an encouraging response from his girlfriend. Her murmurs were soon audible moans as Willy moved back and forth between nipples, taking the time to spread the love.

I leaned in closer to Marsha so my face was was close to her neck. Her hair was still damp, and loose about her shoulders. I took some deeper inhales, blowing my breaths against the bare nap of her neck. She shivered a little.

Marsha let her head fall ever so slowly to the right, exposing her neck to me. I reached up with my left hand and pulled back the strands of her wet hair. I placed my lips on on her shoulder near her swim suit strap. She made a quiet, pleasurable noise. I started delicately kissing her shoulder, working towards her neck.

Willy returned to kissing his girlfriend on the lips. As they kissed, she reached down and started stroking his dick. Taking his cue, Willy's hands dropped down to her jeans shorts and started working the clasp and zipper. Releasing them, he pushed his hands across her hips and then dipped them into the back of the shorts. She moaned a little has Willy massaged her ass and angled his hands to force the shorts past her hips. Once freed, they fell down her legs.

Willy's right hand made its way under her panties, and continued to massage what looked like a great button ass.

Marsha's breath continued slow and deep. She reached back with both her hands searching for me. I was close enough that she found my trunks, and grabbed hold. She pulled me closer, centering me behind her until I was pressed right against her ass. There was no hiding my erection. She could feel it against her ass, and she started slowly grinding into me.

"Ohhh," I whispered, "this is incredible. This feels so good."

"Mmm, hmmm" I heard Marsha quietly replying.

I continued to kiss Marsha's neck and worked my way to her earlobe. I reached out with my tongue and touched it. Marsha quietly moaned as I took it into her mouth. She had made enough noise that we could have been heard, but Willy and his girlfriend were completely oblivious to the world around them.

I whispered into Marsha's ear, "you are so fucking hot right now."

She responded by increasing the pressure of her grinding. I think she was breathing only through her open mouth at this point. It sounded like slow panting.

Willy hooked his thumbs under his girlfriend's underwear and started to pull them down over her ass. She continued to stroke his dick as he worked them free of her hips to let them fall and join her shorts. When they landed at her ankles, she stepped back and shook each foot free. She took off her shirt, then she reached behind her back and undid her bra, dropping it on the rest of her clothes.

Taking in her full nakedness in the light of the moon, I could see tan lines, and the all the glory of a twenty year-old beauty (I was thinking Playboy model). Whats-her-face had a small patch of pubic hair on her mound and her nipples were sticking out farther than any I had ever seen previously. Willy also took a moment to admire her, then quickly stripped out of his shorts and t-shirt. Apparently Willy had gone commando in anticipation of the night's fun. With his dick on full display, I had to say I was impressed with my friend's rod.

I didn't realize how captivated I was by their stripping because everything I had been doing to Marsha had stopped. I was literally mid-suck on her earlobe, but completely stalled out. Marsha's grinding also paused as she was captivated by what was happening, but she recovered quicker than I did. When she realized I was frozen like a deer in the headlights, instead of grinding against me, she gave me a couple of subtle butt bumps to jar me back to present.