Day One
The Beach House
“Anna?” I called up the steps, panting and already covered in sweat. Tropical vacations were fun, but lugging your stuff up several flights of stairs sucked.
“Yeah?!” she yelled back.
“I can’t carry this cooler by myself, can you help me please?”
Her response was to trot quickly down the deck stairs to help me, her blonde pony tail bouncing behind her. Together, we hauled the cooler with food for the week up the wooden steps. Once at the top I took a moment to catch my breath and take in the view.
“Wow,” I breathed, watching the waves from our elevated position crashing into the shore. Her vacation house was stunning, set high on stilts right in the dunes overlooking the water. It had an open and airy floor plan with a wrap around deck that had cushioned chaise lounges and a patio table, all setting the scene for what I was hoping would be a perfect vacation.
She smiled at me. “Beautiful isn’t it?”
“It’s insane, thank you so much for inviting me.”
Anna shrugged and brushed off my thanks.
“I get lonely by myself, so really, you’re doing me a favor,” she said. “Let’s get the rest of the stuff inside and put away so we can relax!”
I nodded eagerly and we got to work. We laughed and joked along the way, gossiping about the office once in a while. Anna and I were co-workers and over the years we had developed a strong friendship despite our age difference. While I had just turned 32, Anna had hit the big 5-0 last year.
She did a little shimmy shake to the country music playing on the Bluetooth speaker and I couldn’t help the small laugh that came out of me.
“You’re too funny,” I said, putting away the last of the White Claw in the fridge. “What the heck are we supposed to do with all of this alcohol?”
Anna looked at me, her brows furrowed in confusion.
“We’re on vacation Parker – we’re drinking.”
“Oh, I don’t usually drink that much,” I said, a little embarrassed.
In response, she popped the top of one of the hard seltzers and poured it into two glasses full of ice singing “It’s five o’clock somewhere!” in a horribly off-key voice. She handed me one and clinked hers with mine.
“To vacation!” she cheered, taking a drink.
“Vacation!” I yelled back and took a small sip.
“Okay, let’s get changed and go down to the beach,” she said and went upstairs to her room.
The house had two bedrooms, the master upstairs and one in the back of the main level off the kitchen. Since I was the guest in her house, Anna was in the master. My room had two full sized beds crammed into the space, only about two feet between them. It wasn’t the most comfortable setup, but I got it. It was a vacation house after all and sleeping capacity increased the ability to host more guests. Anna rented it whenever she wasn’t using it herself so more beds meant more value for her.
I unpacked my clothes for the week and put them away in the dresser, leaving my favorite one piece bathing suit out with a tasteful matching coverup beside it. I shut the door so I could change and made sure to lock it. I didn’t think Anna would walk in without knocking, but you never knew.
I changed quickly and adjusted my breasts in the suit to make sure they stayed put. As large as they were, sometimes they got a little unruly outside the confines of a real bra. Having double D’s my whole adult life had been both a struggle and a blessing. I liked them, after all they were mine, but they made shopping for tops and swimwear difficult. I took a quick glance at the mirror above the short dresser and saw that the chilly air of the air conditioning had made my nipples stand out through the thin fabric. Mortified, I tried to rub them warm to get them to calm down but it had the opposite effect and my nipples pebbled almost painfully tight at the stimulation.
“Crap,” I whispered and threw my coverup over the plain, dark grey strapless suit in hopes to hide them until we were outside where it was warmer.
I met Anna on the deck outside, surprised to see her in a two piece at her age, but I had to admit – she looked darn good. Her breasts, while not quite my size, were large, rode high on her chest and filled out the navy bikini top nicely. Her belly had a couple of stretch marks from having her daughter, but otherwise it was flat and you could see she was in good shape. I looked down at my own curvy figure and the small pooch of my belly.
She wolf-whistled when she saw me, wagging her eyebrows and making me laugh self consciously.
“Where have you been hiding those bazungas?” she asked, opening my coverup so she could eye me up and down.
I blushed at her inspection and batted at her hands ineffectively.
“And look at that itty-bitty waist!” she squealed.
“You should talk Miss Bikini,” I sassed back. “Your legs go on forever.”
“Meh,” she said, finally letting go of my coverup. “I’d kill for your hourglass figure, I’m straight as a board.”
“Well, I wish I was skinny like you,” I murmured but she heard me.
“There will be no body shaming this week,” she said to me sternly. “You are beautiful and men would be salivating to get their hands on your curves if you had more confidence.”
I held my hands up in defense. “Okay, okay.”
“Now get your generous ass down to the beach and relax!” She emphasized her statement with a swift slap on my ass and I squeaked in surprise.
“Anna!”
She laughed and walked down the wooden stairs to the short boardwalk that led to the sandy beach. Grabbing my big floppy hat and drink, I pushed my shoulders back and joined her.
————————————————————————————————————————————
A few hours later we were climbing back up the stairs sun-kissed and slightly waterlogged.
“I can’t believe your tits,” Anna said swaying a bit as she walked.
“Anna!” I scolded, frantically looking around us to see if anyone was outside on the decks of the neighboring houses. Beachfront real estate was a prime commodity and the houses on this part of the island were stacked fairly close together. If you talked loud enough or listened hard enough, privacy wasn’t guaranteed.
“What?!” she hiccuped. “They’re hot as hell!”
“Anna!” I tried again. “Shh!”
“Everyone saw them Parker, relax! No one cares if I’m talking about them when they saw the show firsthand.”
“Oh my god,” I whispered, embarrassed beyond belief, and rubbed my hand against my forehead.
The wind had whipped up the waves today, making the Gulf rougher than usual. Although I had grown up on the beach, even the occasional strong wave knocked me over. On our second trip into the ocean a wave had hit me so hard that my breasts had popped out of the top of my suit. Before I could think, I had the choice of either not drowning or not flashing anyone. I chose life over modesty, but now I was re-thinking my decision.
She finally got to the top of the stairs and leaned against the railing, more than tipsy from all the sun and drinks she lugged in the small cooler down to the beach. She stretched her arms out in front of her and made grabbing motions with her hands towards my chest.
“Honk honk!” she giggled.
“Anna please!”
“Pssh don’t be so uptight,” she said, waving me off and opening one of the sliding doors that lined the front of the house. “You’ve got grade A tits, you should be proud to show them off.”
She made a sucking noise and I looked at her, horrified.
“What are you doing?”
“That’s the sound people will make when they suck on them for you,” she said, giggling as she opened the fridge to take out the chicken we had defrosting. “I love having my tits sucked, ugh, it’s the best. It’s the best part of my day, so relaxing,” she sighed.
“I wouldn’t know,” I said stiffly.
She slammed her hands onto the countertop.
“Seriously?!” she said, her eyes wide with shock.
“Yes, seriously,” I said primly and shook some spices out over the chicken before sliding it in the oven.
“I’ll let you try my machine tonight, you’ll love it,” she said casually.
“Your machine?” I asked her, turning around to look at her.
“Ya,” she said, twisting her long blonde hair up into a bun. “My pump.”
She said this as if it was the most natural thing in the world. I was baffled.
“Your pump?”
“Yeah for my side hustle,” she said as she took out a knife and cutting board to slice the vegetables.
I nudged her aside and took the knife to chop them for her. I didn’t think her blood alcohol level and knives went well together.
“Anna,” I said exasperated. “I have no idea what you’re talking about.”
She giggled. “How have we not had this conversation?”
“I have no idea.”
“I sell my milk online.”
I set the knife down carefully and looked up at her.
“Pardon?”
“I sell my milk online,” she said again. When I kept staringre at her with confusion written across my face she continued. “After I had Georgia, my tits never stopped producing milk. There are lots of people that look for breast milk out in the world and so I started selling mine to a milk bank online.”
“Like for women who can’t breastfeed?” I asked, curious.
“Sure,” she said as she carefully pressed buttons on the oven I had forgotten to start.
“That’s very noble of you,” I said. “That must be quite a hardship. Georgia is what now, 21 or so?”
“22 this upcoming August,” Anna said with a mother’s pride.
“Wow, so many years of donating,” I commented, chopping again. “I’m in awe of your commitment to helping others.”
She shrugged and pulled up a barstool to the island counter to sit.
“I only have to pump twice a day now, when I wake up and before bed. Like I said, it’s the best part of my day and it feels fucking fantastic.”
“Oh but you’re drinking,” I said, eyeing her row of empty cans by the sink. “That’s not good for your milk right?”
She nodded. “Yep, this week will mostly be a pump and dump unless someone wants to drink it from the tap.”
“Drink if from the tap?” I said, confused.
She laughed loudly and stood up, ignoring my question.
“I’m going to shower and get changed out of this suit. I want to get in comfy clothes for dinner.”
I nodded, still trying to figure out what she meant. “Okay, I’ll wait until you’re done to do the same.” The place only had one full bathroom on the main floor with a half bath in the master.
“No need,” she said, waiving me off. “I’m going to use the outdoor shower.”
“But two sides of it are open, someone might see,” I said, concerned that she wasn’t thinking clearly with the hard seltzer coursing through her veins. The outdoor shower was on the lower deck below the house and was meant for showering off the sand and salt from the ocean. In fact, if you were on either of the neighbor’s decks you could see straight into it and our main deck looked down directly over it.
She winked at me as she headed to the stairs that led to her room. “I certainly hope so.”
“Oh my god,” I whispered to myself, shaking my head.
————————————————————————————————————————————
Later that night after dinner, since it had cooled off so nicely, Anna opened all of the sliding doors. We could hear the waves slapping onto the shore as we settled in on the couch beside each other.
Her living room was beautifully arranged and welcoming. A three person couch was bracketed by a loveseat and an oversized armchair on either side to make a U shape facing the opened doors. The three pieces of furniture were all leather.
“Easy clean up,” she had explained with a wink and it made sense, sand slid right off of it.
“I love that all of these doors open up right on to the deck, the view is amazing,” I commented as she turned on the television tucked away in a corner.
“Oh I know,” she agreed. “Tomorrow I’ll show you my deck upstairs, you can see halfway down the island from it.”
“Oooo-wooow,” I said and giggled at the sound I made. At dinner we had shared a bottle of bubbly that somehow turned into two. She kept refilling my glass and we toasted to the first night of vacation – a lot. Now, I was pretty tipsy and glad to sit still on the couch where the room wasn’t whirling.
“Do you care what movie we watch?” Anna asked as she flipped through channels at an alarming rate that made me dizzy.
I shook my head no.
“Oh I looooove this one!” she squealed and selected something before I could read the description.
“Okay,” I said, not really having an opinion and pulled the light throw blanket from the arm of the couch over me.
“Do you mind if I pump while we watch?” she asked me, pausing the movie at the opening credits. Big Girl, Big Love stood frozen on the screen.
“No of course not, go right ahead.” I had seen nursing mothers feed their babies discreetly before and I was relatively familiar with what a breast pump looked like so I assumed this would be something similar.
Anna reached over to the coffee table and picked up a zippered, medium sized bag. Out of it she pulled out a breast pump with two milking cups and the attached hoses and bags. To my surprise she tugged her shirt off over her head and started pinching her nipples. I quickly turned my head to give her some privacy and looked anywhere but at her chest.
“They’re just tits Parker, relax,” she joked. “Besides, I’ve seen yours, now you’ve seen mine.”
“Okay,” I whispered and could feel my cheeks flushing. I couldn’t help but see her massage her breasts and nipples in my peripheral vision. Just as I suspected earlier, they were plump and looked like C cups with thicker, dark nipples. Now I knew that they were full of milk. Without the support of her bikini, they sagged slightly from her age. For 50 though, they were still lovely.
She fit the cup over one breast and groaned slightly as it sucked her nipple into the cone. Once it had sealed itself, she let go and did the same with the other, another moan slipping from between her lips as it latched. She sighed and settled against the back of the couch.
“Feels sooo good,” she said closing her eyes.
I could see the attached, clear baggies filling with a milky white fluid as it alternated sucking one nipple and then the other.
“It must be a relief from the pressure, right?” I said politely, still trying to avoid looking directly at her and her naked chest.
“Sure,” she murmured, her eyes still closed. “But it’s also a turn on, ya know?”
“Um, yeah, sure,” I said uncertainly, wanting to change the subject. “Ready for the movie?”
She opened her eyes and grabbed the remote. “Absolutely, you’re going to love this one.”
“What’s it about?” I asked as the names of the actors and actresses scrolled on the screen. I didn’t recognize any of them but I trusted Anna’s judgement. Maybe it was one of those ensemble casts where you didn’t know their names but recognized all the character actors once you saw them.
“It’s a romance.”
“Oh, like a Hallmark movie?” I asked. That made sense then for me not to recognize any of them by name.
“Sure,” she replied and tugged half my blanket over her lap, making sure that her breasts were still uncovered and her tubes didn’t get tangled.
The movie started off by introducing us to the female main character, Betty, who was a big and beautiful woman who was shy around attractive men in her office. The story continued with a typical meet-cute with her new boss, Damon. I was surprised when it moved tohowed a pretty racy scene where Betty masturbated on her bed thinking about Damon later that night. It showed her full body, completely naked, as she touched herself between her legs. Usually late night TV showed the occasional side boob or butt crack but not full breasts and what appeared to be a very wet vagina. I cleared my throat and shifted on the couch uncomfortably, my head still a little foggy from the champagne.
“Hot right?” Anna murmured from beside me.
I cleared my throat again. “Um yea, sure. This is on regular cable?”
“Mmhmm,” Anna replied and we went silent again to keep watching.
The movie progressed, showing more and more tension between the two main characters. Damon was hot, boasting a set of impossible abs and scruff on his jawline. He seemed way too hot to be with Betty. In my experience men that looked like that didn’t look at women like me. But it was a rom-com after all, so I let it go. Soon they finally made it to the bedroom and I couldn’t help the little gasp of shock that escaped my mouth when Damon took his pants off to reveal a very hard and very large penis.
“Oh my god,” I whispered and I heard Anna chuckle softly beside me.
“Keep watching,” she said quietly. “This is one of the good parts.”
I watched, transfixed, as they had what appeared to be real, actual sex on the screen. I heard Anna shift next to me but I couldn’t tear my eyes off of Damon’s butt thrusting on top of Betty. It was mesmerizing and I could feel my nipples tightening at the scene.
“They’ve done some job with this simulation,” I murmured as they zoomed in on a close up of his penis pumping in and out of her.
“Oh Parker, that’s not simulated hun – they’re fucking,” Anna corrected, her voice sounding breathy.
I glanced over at her and my eyes widened at what I thought was her hand moving under the blanket.
“Anna!” I whispered, shocked at what I thought I was seeing. “Are you…?!”
“Mmm,” she moaned and rolled head back against the back of the couch with her eyes closed. “Fuck yes I am, feels so good.”
I couldn’t tear my eyes away from her as she played with herself between her legs. Thank goodness it was under the covers and I couldn’t actually see anything, but she made it very clear what she was doing.
“Should join me,” she said lazily. “You’ll feel better.”
I coughed, uncomfortable, my brain racing now with what was happening. My still tipsy mind couldn’t seem to comprehend what to do so I just sat there, my eyes going from the sex on the screen to my friend touching herself next to me. All the while, her nipples continued to get milked by her machine quietly.
The movie continued, less and less time passing between sex scenes until it was just the two main characters naked the whole time. I could feel myself getting wet and I was ashamed at myself for squeezing my thighs together once in a while to try and relieve the pressure there. Soon, Anna started moaning more frequently and I could hear the wet noises coming from under the blanket.
“Oh fuck,” she moaned as she watched a particularly dirty scene where Betty was having sex with two men in the office.
I couldn’t believe what I was watching.
“Parker I’m gonna cum.”
“What!?” I gasped as her hand moved more rapidly beneath the covers.
“Watch me cum Parker,” she groaned. “I want you to watch me cum.”
“Oh um-” I started, not knowing what to say.
“Oh fuck yes, I’m so wet,” Anna panted and I could hear her fingers pumping in and out of her body. She stared me in the eyes and moved her hips a little in time with her hand. “Watch me Parker. Okay?”
I froze, unable to move or do anything but hold her gaze. I could feel my own clit throbbing between my legs and I felt myself nod ever so slightly.
“Oh good girl, watch me make myself cum. Fuck yea, here I cum,” she grunted. “Ugh! I’m cumming!”
She wailed and undulated on the couch beside me as she came, her eyes never leaving mine. Her cheeks were flushed and her breasts bounced with her movement, milk still streaming from her reddened nipples. After what seemed like forever, she sighed and sagged into the couch, sliding her hand out from under the blanket. In the low light of the television I could see her fingers were coated with her arousal. I closed my shocked mouth and looked away as she started to unhook her breasts from the pump.
“That was great, I really needed that,” Anna said, wrapping the hoses up to tuck them back into the pouch. “Thanks.”
“Oh um, you’re welcome, I guess,” I stuttered.
“Maybe tomorrow night you’ll be brave enough to do something about your own needy pussy too,” she said with a wink and stood up to pour the bags of milk in the sink, not bothering to put her top back on. I flinched at the crude word she used.
Oh my goodness, I thought. What kind of vacation was I on?