Family Vacation Pt. 01

[It should be noted this is kind of a softcore story. There’s any sucking or fucking in this chapter, and probably not the next one either. If a slow pace isn’t your thing, I recommend turning to other stories.

All persons are over 18.]

I met my family at the airport. A short 2 and a half hour flight from JFK in NYC to Miami. Clean. Comfortable. Affordable. I love a good early morning flight. I arrived at the gate to see my cousins Maggie and Mike, Aunt Jen, and her girlfriend Alice waiting for me at baggage claim.

I didn’t get to see them that often being in college now, so I didn’t complain when Maggie called me up and asked me to accompany them on their bi-annual family trip down to Miami. See, they live in Jacksonville, about 4 hours away, and every other summer, the last week of the summer, they always take a trip down to Miami for a little getaway. Maggie was supposed to bring her boyfriend, Sean, I think his name was, but they broke up shortly before the trip. She explained to me that they now had a wasted hotel reservation, and since 1 of their 4 plane tickets already went down the shitter, they didn’t wanna waste any more money. I hadn’t the slightest idea why she’d ask me, her cousin, to accompany instead of one of her female friends, but again, Miami...beaches...drinks...free hotel stay -- why complain? Especially since Aunt Jen offered to at least cover my arriving flight. There was 10 days left until I started my junior year at NYU so fuck it, I thought, make the best of it.

Even though, I had seen them all of them -- except Alice, whom I’d never met before -- last Thanksgiving, somehow they all looked different. Slightly older. Maybe it was the Florida heat. Aunt Jen, who just turned 50, looked great -- a slim build, broad shoulders, wearing her hair long, and a nice tan. She wore a bathing suit top underneath her thin black Def Leppard t-shirt and smooth white capri. It was definitely 97 degrees outside, as my phone had told me. Her girlfriend, I was surprised to find was significantly younger, probably in her mid to late 30s. She had an average body, but a decent size chest, a pretty face, but her hair didn’t even go below her ears. Of the two lesbians in front of me, one of them was clearly “the man” in the relationship. She wore camo cargo shorts, flip flops, and a bathing suit top under black wife beater.

But of the three woman, Maggie was the one that caught my eye the most. I have to admit I always found her slightly cute growing up, and me being 23, her 21, we have a lot in common as members of the same generation. We were even born 3 days apart in the month of January. Sometimes when we were kids we celebrated our birthdays together. In high school, she was one of those girls that filled out...should we say...better than most. In spite of being only 5 foot 4 inches, her breasts became absolutely, positively humongous. The kinds of breasts that are so big that they’re the first thing you notice about them when she walks in the room, even if she’s wearing a sweater.

Take into consideration that my aunt and her girlfriend dressed for the heat at the airport, as did my cousin Mike who simply wore board short and a green tank top and crocs, and Maggie wore jeans with a simple black band tee that covered all of the upper body except her arms. Her shoulder length black hair was tied in a ponytail. As noticeable as her body always was, she was never one to show it off. I always remember back in the day at family BBQs and pool parties she would always wear a one piece bathing suit. It still showed off her absolutely gargantuan globes, but she was the definition of a modest dresser. She just happened to have completely unbelievably huge milkers.

I gave all my family hugs and greetings. “It’s nice to see you,” everyone said. Likewise.

My aunt introduced me to her significant other. “This is my girlfriend Alice. She’s gonna be with us for the trip this year.”

Alice and I shook hands firmly. “What’s up, man?” she greeted me. Her personality was definitely not very woman-like, compared to my aunt, who no one in a million years would ever think is a lesbian.

They were already one day into the vacation, so my settling in wasn’t gonna hinder their plans. We gossiped while we waiting about 20 minutes for my single suitcase, and off we were.

As soon as we got my Aunt’s van, she said “Matt, we were gonna go to the beach this afternoon. Do you wanna go to the hotel and drop off your stuff first or do that later?”

“Hotel first.” I replied. “I wanna see where I’m staying and get changed.”

So it was. 20 odd minutes later we got to the Holiday Inn in Miami. There’s lots of Holiday Inns in Miami, but this one was stacked. Even in the lobby, I knew this vacation must have cost them in arm and both legs.

They had checked out 3 rooms. One for Aunt Jen and Alice, one for Mike, and one for Maggie and her boyfriend.

In the hallway by our rooms, we all went our separate ways. “We’re gonna grab a couple of things and head down to the lobby.” Aunt Jen said. “Meet you guys down there?”

“Sure thing. Be a few minutes.” Maggie replied.

Mike, Aunt Jen and Alice all entered their rooms and Maggie turned to me before opening the door. She looked nervous.

She spoke: “Matt, I’m so glad you can make it on this trip to fill in for Sean, but as you can probably see, my ex-boyfriend and I were gonna share a room.”

“What’s so bad about that?” I replied.

She opened the door and we walked into the enormous hotel room. I was curious why there was so much blank space, until my cousin pointed out...

“Only one bed.”

I chuckled. “That’s okay. We’ll make it work.”

“I know that’s gonna be really awkward, but I feel like you wouldn’t have come on the trip if I told you this in advance. Do you want money for a separate room?”

“No, cuz, I think we’ll be okay. We’re both adults.”

“Alright, as long you don’t care that much.”

We chit-chatted for a bit before I changed in the bathroom. A couple minutes later and the 5 of us were off to the beach.

I sat next to Maggie in the back on the van and even through her baggy shirt, I noticed every single we went over a bump or jolted to a stop, her tits jiggled up and down. We talked about college, music, and of course, her ex, Sean. I don’t why they broke up but whatever he did, he must of wronged her awfully. Whenever she mentions him her face just sinks into a semi-permanent frown.

Finally, we arrive at the beach. We carried our chairs, and all the towels they had brought all the way up the piping hot sidewalk, even further up the even hotter boardwalk ramp, and onto the sand. A couple more minutes of walking and we found our spot on the beach. A perfect distance between the edge of the water and the fence at the back of the beach.

Aunt Jen set up all the chairs, and laid down her and Alice’s towels, and almost enthusiastically, was the first one took take off an article of clothing. Without any hesitation, she picked her shirt up over head, revealing her neon pink bikini top. For a woman of 50 with an average sized chest, her breasts stuck out quite prominently in this top the exposed quite a bit of the middle area of her chest.

Alice followed soon after, taking off her tank top to reveal her bikini-clad handful-sized breasts. She too looked good in her half-dressed manner, for a woman who I initially thought looked quite manly.

Mike and I took off shirts at the same time by chance. He had bulked up quite a bit, developing a six-pack, a sight to see compared to my quite average build and somewhat saggy belly. I begun slipping off my sandals when I noticed that Alice and Aunt Jen had already stripped down even further. Alice wore men’s boards shorts, but my aunt wore a purple bikini bottom. When she turned around and bent over to put her clothes in her bag, I got a good eyeful of her buttcheeks hanging loose from the folds of her bottoms.

That left only Maggie. For the moment, she was standing still on her phone typing away.

“Maggie, put the phone down for one minute please. Enjoy the beach!” my aunt said.

“Hold on, I’m texting dad about something.”

Uncle Jay had been out of the picture for a long time. Once my Aunt Jen discovered she was a lesbian, she became distant. Two years of separated preceded divorce, and since both Mike and Maggie are adults, they never really see Uncle Jay. I have no idea what she could be texting him about.

Finally, she put her phone down on her chair and slipped her shoes off. She started unbuttoning her jeans, and I tried my hardest not to let anyone see me stare.

She shimmied out of her jeans to reveal a white bikini bottom, sides tucked tightly in her groins, back half exposing just the right amount of cheek.

She looked around for a minute, as if surveying the area, then wrapped her fingers around the bottom of her shirt. Almost in slow motion, she lifted her shirt over head to reveal her watermelon-sized breasts in a white and pink, flowery bikini top. They flopped out of her shirt with force, bouncing against her chest multiple times like basketballs on a trampoline.

She sighed and bent over to put her clothes in her bag too, and when she bent towards me I got such an eyeful of cleavage I thought I would get an immediate tent in my shorts right then and there. Her tits were practically falling out of her top. Ginormous mounds, not fit at all for her tiny body, flailing about helplessly, barely contained by the thin multicolor fabric. These had to be the biggest pair of breasts I had ever seen in real life, and what luck it was that she finally worked up the courage to wear a two-piece. The tiny amount of chub she had developed on her belly only made it hotter for me. Cousin or not, this was my type of woman. I was gonna enjoy this vacation like a motherfucker.

“Where’s the sunscreen?” she immediately said as she bent over again and started rummaging through her bag. Her breasts bounced around some more as she moved her arms around in the bag, until finally she found the bottle of sunscreen.

“I’m so excited to finally get a nice tan going this year.” she said.

“Me too,” my aunt replied. “It’s a shame you were so sick last year and couldn’t come.”

Mike chimed in. “The water looks so much bluer this year.”

Myself and everyone else all got settled in on our towels and chairs. I played around on my phone as a motivation not to give myself an erection staring at my relatives.

Maggie started lotioning herself up first. She rubbed her arms, her legs, her belly, her neck, everywhere she could reach. She passed the bottle to my aunt and her and Alice did the same. Then my aunt laid down on her back on undid the straps on her bathing suit top. “Get my back, babe,” she told Alice.

And so Alice gently lathered up my aunt’s naked back with sun tan lotion. Looking at her bare back I noticed once again how good a figure she had for a woman who just celebrated her 50^th birthday. A bit of sideboob stuck out from underneath her torso.

By now, I had noticed that Mike, ignoring the opportunity to tan had set out for the water. Alice turned her head to look at him. “I’m gonna join Mike in the water. Be back in a couple minutes.” she said to my aunt. She took off her hat and sunglasses and jogged over to join Mike for an adventure into the ocean.

I looked back at Maggie as she was grabbing the bottle of sun tan lotion from the ground by my now resting aunt. She shook it up as she looked at me. “Can you do me?” she asked.

“W-What?” I nervously replied.

“Get my back.”

“Oh! Oh yeah, sure.”

She laid face down on her towel and her ass perked up to the sky. I had never noticed how perfectly round it was before now. I wanted to grab it and jiggle it.

“Thanks so much.” Maggie said as she adjusted her position to rest her head on her folded arms.

I didn’t hesitate. I squirted a decent-sized glob of a lotion onto my fingers, rubbed my hands together, and started massaging my cousin’s back.

“You want the strap off?” I asked.

“What?”

“Do you want to remove the strap to your top? So there’s no tanline.”

“Oh yes, yes please.”

Her wasn’t a simple string strap like my aunt’s was. Her top was hefty as it had to hold her weight. It functioned more like a bra with a buckle similar to an airplane seatbelt.

I fussed with it for a second, unsure of it’s mechanics, before finally unhooking the top. The large connecting flaps fell wayside and a huge amount of bare skin lit up my eyes like a delivery of gold bullion. Beyond the plane of pale skin there lied two enormous balloons, pressed underneath the weight of my cousin’s upper body. Circumference-wise, at least half of each breast poking out to the side like dog ears. It would prove difficult not to touch them as a I continued.

I rubbed a little bit more lotion in my fingers and kept on the mission. I rubbed up and down, side to side, all along the curvy surface of my cousin’s back. Gradually, I felt a little growth under the thin surface of my swim trunks. I couldn’t help it.

I had to start a conversation. “You know, cousin, hope it’s not too out of line to say but I’m surprised to see you wearing a bikini. I always remember you at pool parties wearing one pieces.” I said.

“Yeah, that’s for family. Here it’s different. I don’t know anybody here. I don’t care if they judge me.”

“Judge you? What would they judge you for?”

“I don’t know, maybe it’s hard to not to notice when the girl with pumpkins under her shirt walks on the beach and starts taking her clothes off.”

I only responded with a chuckle. I looked over at her opened bikini strap to check out the cup size out of curiousity. 54J. WOW. They really are like watermelons on a Barbie doll.

“My sides are lonely, cuz. Make sure you get them too.” Maggie said.

“Okay, sorry, haha.”

I rubbed a tiny bit more lotion on my hands and dived in. Getting her sides inevitably meant rubbing on the sides of her huge tits more than once. And I did.

At least ten times, on both sides, the tips of my fingers or the sides of my palms grazed against the slippery undersides of my cousin’s breasts. I have to admit in all the times I thought about Maggie as kind of cute, I never, ever imagined this situation.

She said and did nothing to my grazing of her mammaries. No reaction. She must have been expecting it. I finished up my covering of her back with some slow brushes down both sides of her torso -- she thanked me.

I sat back down and started putting lotion on myself. I looked back and forth between my cousin and her mother. It’s to my benefit that they’re both lying face down, otherwise they’d certainly notice the teepee in my bathing suit. I had to crouch, sit, lay in ways that would disguise the shape. It was difficult, but I was good at it.

It now occurred to me that there’s was no one to put lotion on my back.

“Alright, that’s not fair. I have to no one to do my back.” I blurted out.

“Sorry, cuz”, Maggie said through the echo of her armpits, “You’re just gonna have to wait for Mike or Alice to get back.”

I turned to my Aunt. Silent, completely still. Maybe she’d fallen asleep by accident.

Forget it, I thought. I’ll make them pay for it next time. I sat in my chair and relaxed with some music in my ears.

30 minutes later. I hear Mike and Alice coming back from the water. Alice’s white board shorts had become completely translucent from the heavy water. I could see was wearing white lace panties underneath, and her nipples began to poke through her black bikini top. Now she was a woman.

My aunt sat up on greeted up as she came back to the spot. Her bikini top was still unstrapped, and it fell forward as she sat up, but she grabbed it and held it against herself before anyone could see anything. Damn. Close call.

Mike did his own thing as usual. Dried himself off, ate a sandwich from his bag, and sat down to cool off with his towel draped over his shoulders.

The rest of the day was standard family vacation. We went to a nice restaurant, played some games at the arcade in the hotel, and caught a movie at the end of the night. All day I couldn’t stop reminiscing about when my fingertips ran along the smooth surfaces of my cousin’s underboob. I remembered too, during the movie, that Maggie were sharing a space for this entire week.

At the hotel, we all dropped our bags with exhausted hands in our hotel rooms. As soon as I got in the room I flopped on the bed face first.

“Do you wanna shower first or can I?” my cousin prompted. I didn’t know either one of us was showering at all.

“Uh, you can go first. I think I’ll take one in the morning.”

“Nuh,uh. I am not sharing a bed for a week with someone who doesn’t shower beforehand. No, sireebob.”

She started taking of clothes again. Suddenly she was standing before me in our hotel room in her bikini. I suppose it doesn’t matter. I saw her at the beach. What the difference in location?

“Okay, I’ll go right after.” I said.

Minutes later, I heard the shower running. I broke out my laptop to play some Smite while I waited for my turn.

Suddenly, I hear my cousin calling. “Matt! Matt!” I got up to investigate.

I knocked on the bathroom door. “Yes?!”

“Can you bring me a dry towel? I forgot to grab one!”

I went into the little cubby by the hotel room door and grabbed a towel.

“Should I come in, or...?” I asked.

“Yes, just put it right on the sink. I’m gonna be done in a minute.”

Slowly, I creaked open the bathroom door, hoping to catch a glance. As I took a giant step in the bathroom and placed the folded towel on the bathroom sink, I got a brief glimpse of my cousin’s asscrack through the gap between the shower curtain and the wall.

I said nothing except “There you go!” She thanked me and I exited with a hard dick once again.

Moments later my cousin exited the shower and back into the room with a towel wrapped around her. Her tits are so massive, so voluminous, that it became impossible for her to wrap the towel around her torso by her armpits. The towel sagged low, just above her belly, where the sheer mass of her breasts forced it to be. Even more of them were on display now than in her bikini. Even still, she stretched her arms up in the mirror when she exited, making her chest burst outward. I would do anything in this moment to make that towel fall down if it wouldn’t ruin the rest of our stay.

I quickly got in the shower before I convinced myself to do anything irrational. To prevent further disasters, I pleasured myself in the shower. I thought about that afternoon when I rubbed lotion all over my cousin, and when I saw my aunt almost lose her top, and about all the future things I might see on the rest on this family vacation.. I busted a big, fat, sticky load right into the drain.

I didn’t want to make things too awkward, so instead of just my underwear like I usually sleep in, I put on a white tank top over it. I emerged in this attire, to which my cousin Maggie had no reaction. She sat on the bed brushing her hair in pink booty shorts and white spaghetti strap shirt that did nothing to hide the size of her gargantuan chest. I wasn’t sure of whether or she was wearing a strapless bra underneath, but I didn’t think so.

“Hey.” I said.

“Hey.” she replied.

I started putting all my belongings that were scattered on the table into my bag. “So, uh, you an Sean.”

“What about it?”

“What really happened between you and him? I know at dinner you said you guys just drifted apart but I’ve known you since we were kids and I can tell when you’re fibbing.”

“Yeah....”

“So...”

I zipped up my bag.

“What happened?”

“You wanna know what really happened? But you can’t tell Aunt Jen because she’ll flip.”