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Hardcore Houseboat Holiday

Hardcore Houseboat Holiday

by beddridden
14 min read
4.26 (24300 views)
adultfiction
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Part 1

My name is Tommy. Our family tree is a complicated one.

The two moms met at a fertility clinic. At first, they chatted while in the waiting room before going for coffee and chatting some more. They learned that they were in the same boat, getting the lowdown on hopes of becoming pregnant. On one teary day, they both learned that having a baby the traditional way was just not possible for them. They became each other's support group, talking on the phone, sometimes crying and other times laughing in despair. The husbands later met at one's barbeque and instantly clicked, as well. Soon they were going on vacation together and spending Christmas holidays at one of their houses. Being only an hour apart made everything that much easier.

My 'Aunt' Jill and 'Uncle' Bob already had a son named Joey from Bob's first marriage but Jill wanted more kids, so the diagnosis from the fertility clinic was devastating for her. Within a few years, they suffered the long wait list at the adoption agency before they were able to bring baby Jeanine home. Now, they had a son from Bob and a daughter from the agency.

For my own mother, April, it was a deeply sad period. Bob and Jill now had two beautiful kids but my mom and dad remained childless. Many phone calls between the two families usually were effusive on one end and sad on the other. At the barbeques together, Bob and Jill brought their older son along with baby Jeanine and, while happy for them, my mom was green with envy. Eventually, my parents finally got a call from an adoption agency themselves bringing me, Tommy, into the family. I was a couple of years old when they got me but Mom still pined for a baby. The agency advised them that babies were popular with prospective parents and there was a long wait list. It was suggested that if my parents were willing, refugee babies from war zones were easier to adopt. Mom and Dad jumped at the chance and within months they brought home my sister, who they renamed her Alice.

Barbeques and Christmases were now happier, with both couples raising two-kid families. Bob and Jill now had Bob's son, Joey, along with young Jeanine. My folks had me and Alice and all was right with the world. The two families became closer than ever. It wasn't until I was 12 years old that I learned that Bob and Jill were not my real 'uncle' and 'aunt'.

My 'cousin' Joey was a few years older and was like a god to me. Since we both spent so much time together, Joey led me through through many rites of teenagers and was much more adventuresome than I. He was not beyond bending rules, which offset my shy side. If I got into any trouble, it was usually due to his antics.

Bliss never lasts forever and one day, both of our dads died in a traffic accident while on a hunting trip. What a shock it was to Auntie Jill and my mom, April. Each were the mother of a son and a daughter. Us kids were all teenagers at the time, and though my mom received a generous life insurance settlement, Auntie Jill was not so lucky. She was forced to move a couple of hours further away for a job. Get-togethers between the families became less frequent. The first Christmas that we all got together was just plain depressing and we skipped the next Christmas altogether.

With his father being dead, Joey had been acting out and got into a bit of trouble with a bad crowd. At Auntie Jill's suggestion, he left home for an extended stay in Japan. For me, it was a hard blow losing both of my male mentors. After I graduated high school, I escaped to a university out of state and didn't get home at all for awhile. Our once close 'family' was shattering.

After my sister Alice graduated, mom was worried that she'd soon leave too, so decided to take drastic action. She used some of the inheritance money to book a week long houseboat trip, informing us boys who lived away that we were expected to attend, no excuses. It sounded like a great adventure to me. Joey and I had kept in touch online, and when I found out that he was coming home from Japan for our houseboating, I informed my mother, as well. The two families were going to be wholly together for the first time since the depressing Christmas a year and a half earlier.

I texted Joey that I'd pick him up from the airport and we'd drive up together to meet everyone else on the dock. He was hardly recognizable to me. He'd grown a moustache and had his hair as long as a rock star. He told me exciting stories of Japan that were frankly hard to believe, while I told him of my boring stories about university. Being overly shy, I hadn't even gotten laid there, which was unbelievable to a guy with Joey's charisma and a penchant for the ladies.

"Don't worry about that, Tommy. I got your back," he said cryptically. "That virginity of yours is going to end very soon, and in a way that you'll never forget." What he meant by that, I certainly did not know. Surely he didn't mean what he was insinuating. But he'd been like a brotherly mentor growing up and had never misled me, so I let the comment slide.

As we walked up the dock, we spotted our mothers who literally ran into our arms, kissing us both a hundred times. While I found it a bit embarrassing, it was not so with Joey. He lifted both Auntie Jill and my mom into the air, kissed them both on the neck, then tossed them in the lake. They were both fully clothed, spluttering while threatening revenge. As Auntie Jill came out of the water, my eyes couldn't have been wider. Her wet clothes were as tight and see-through as if they'd been painted on. White was definitely the best colour for Summer. The cold water displayed their her nipples dramatically and I had trouble looking her in the eye. To a horny teenage boy, it was awesome. Auntie Jill's nipples were eye magnets, longer than I'd ever seen, even in porn.

The two moms had always been like opposites in the past. For me, this wasn't the first time Auntie Jill's tiny body had been a revelation to me. I'd always had a crush on her as a teenager, ever since she caught me checking her out at our swimming pool. She had curly, fiery red hair, and had seen me staring at the crotch of her swimsuit. Was that what I think it was? Busted, she winked at me as she briefly parted her legs wide for me, revealing pubic hair peeking out of her bikini bottoms. The carpet definitely matched the drapes. Ever since then, she been the star of my spank bank. But, to see her soaked on the dock, revealing her large bra-less breasts clinging to her as if she was naked, well, took me to a whole new level. Her white sleeveless sheer blouse left nothing to the imagination. I admit I was staring as she winked at me once again, just like when she'd purposely shown me her bright red pubic hair back at our pool. Her pink nipples were as hard as diamonds due to the cold water and, I swear, stuck out at least a half inch. Through her oversized arm holes, the swell of her side boobs instantly made me hard. My spank bank now had another deposit.

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My mom crawled out of the water, equally bra-less and impressive. I'd never noticed her tits before because, well, she was my mom, but there she stood with small but thick nipples crinkled onto hard peaks. While Jill was short, my mom hard the hard body of a swimmer, tall and slim. Holy shit! Mom was hot! The fact had not been lost on Joey, and as he leered unapologetically straight at her boobs until she blushed.

"Well, ummm," she stammered, clearly flustered. "Come on. The girls are waiting onboard." Auntie Jill giggled as she jumped up, clamping her legs around her son Joey all the way to the boat. It was the first time she'd seen him since he'd left for his Japan.

As they approached, Jeanine and Alice were lazing on the top deck. I am not shy to admit, they had clearly grown up since I'd last seen them. Gone were the little girls of my youth, replaced by two beauties who would not look out of place on the fashion runways of Milan. They hopped down on the dock to greet us. My sister Alice hugged me as Jeanine greeted her brother, Joey. When they switched, Jeanine pressed her breasts into me with a twinkle in her eye that made my already half mast cock pointing towards the sun. Realizing I was at risk of displaying the tip of my penis, which was now peeking out above the waistband of my short,. I quickly picked up a piece of luggage to place onboard, hiding my excitement behind it.

As for my sister Alice, she had sprouted some very impressive breasts since I'd last seen her, which she now pressed firmly against our cousin Joey, who did nothing to hide his obvious hard-on, pressing it against her belly. All four women became visibly flustered.

"Alright," said my mom, clapping her hands together, "Let's get cruising. Do you boys have anything else to bring onboard?"

"Yes, we absolutely do," Joey answered. He and I headed back to the car where we stacked five 24-packs of beer, coolers and ciders, which Joey tipped back on a dolly. There was one other fairly large box, which I lugged back to the boat.

My mom started a line, passing each case from her to Jill to Jeanine and to Alice, who then stacked them in the galley. Mom chided us for the plethora of booze, announcing that they'd already brought wine and Bailey's.

"Well, we're going for a week, aren't we? We might have to stop for more. Do we have ice for the coolers?"

"I think that we'll be fine, Joey. There's 3 full of ice, and the galley has a full size fridge." She caught him leering at her chest again, so ducked inside. "All aboard. The lake awaits."

The houseboat was a dual pontoon style, which slept up to 10 bodies. Everything onboard looked brand new, with all of the perks of a normal kitchen. There was even a large flat screen TV.

"Get your stuff stowed," ordered Auntie Jill. "I'm afraid there's only one cabin left, so if you'd rather not sleep on the couch or the dinette, you better stake a claim. The girls have put dibs on the overhead bedroom. April and I have taken the largest stateroom with the double bed, so you guys are stuck in the aft cabin, which has 2 bunks." As the boys toted their packs to their cabin, they walked by Alice who was climbing the ladder of the overhead cabin, which partially stuck up above the upper deck. 'Oh my God,' I thought to myself, 'my sister has grown a world class ass.'

"Would you do the honours, Joey? I turned on the blowers when you got here. They clear any gas fumes away from the motors, so we should be ready to sail. Alice, Jeanine, do you want to untie the rope lines from the dock, please?"

The motor started on the first turn of the key and the houseboat eased away from the dock. "Which way?" the helmsman asked.

"Whatever way you want. We just have to find a beach to pull onto for the night."

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The boat cruised at a pretty good clip but dusk set in, as it always does, as Joey eased its bow onto the beach. Alice and I tied off the ropes to nearby trees, going from the stern on a 45-degree angle for stability.

As we got back aboard, the moms were already at work in the galley. "Tommy, how about you start up the barbie?"

"What's for dinner, ladies?"

"Surf and turf. We thought we'd have a nice meal, seeing its the first time we've had dined together in a long time. So, we'll need you to broil up these steaks and those giant prawns."

When dinner was ready, Jill and mom topped the steaks with the giant prawn and asparagus, covered in a Hollandaise sauce. They placed a large spinach salad on the dinette table and called the crew for dinner. I realized just how hungry I was, having not eaten since morning, before picking Joey up from the airport.

As I prepared to sit on the dinette's bench, Jeanine snuck in behind me to get in first, patting the cushion for me to sit beside her. On the other side, Alice had sat closest to the window, with Joey beside her. The moms sat last to get anything they'd forgotten from the galley.

"Whoa," I said. "It's a little snug with 6 people in this dinette." I felt Jeanine's hand reach high up on my inner thigh, pulling me tight to her side. Auntie Jill had to hip check me to fit in on the cushion to the other side of me. Joey gave me a knowing smile, wedged between my sister and my mom. I noticed that neither mom had changed out of their revealing blouses. Talk about distracting! As we scarfed down the amazing meal, the sunset beamed its orange glow through the window. We were all so happy to be back together again.

"Oh crap," complained my sister, Alice. "I forgot to bring a fricking bathing suit."

"How did that happen?" Mom asked. "How can you forget a bathing suit for a boat cruise?"

Jeanine offered, "Not to worry, cuss I've got a spare you can use. And it's stretchy for those big boobs of yours."

Joey teased, "Now, what would you need a bathing suit for with a body like that, oh cousin of mine?" Alice yipped and her eyes went wide for a quick moment before recovering. Apparently, there was a bit of groping under her side of the table, as well.

It was dark by the time dinner was finished. Joey said he was headed for bed after his long flight and jet lag, and the moms agreed and slipped off to bed themselves. Jeanine and Alice had offered to do the dishes, so I headed up onto the top deck to watch the stars.

I drifted off to sleep and had the best dream ever, filled with female flesh. There was a sharp knock from the window of the girls' loft cabin that jarred me awake. Only a couple of feet above the deck, there was a window facing me. Apparently, Jeanine and Alice noticed the results of my dream with my sister pointing out my very, hard cock sticking out the bottom of my shorts. Both were giggling away before I saw Jeanine push a bare breast against the glass. My God, it was beautiful with very dark nipples. I refocused my eyes to see if I saw what I thought I saw, but the window drapes were quickly pulled closed with another bout of giggling from within.

I was the last one awake, so off I headed to my berth, thinking of Jeanine's beautiful breast.

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