A boring summer job turns into the most titillating sexual initiation April could ask for.
Around the same time that Sex and the City made New York and the Hamptons seem super-glamorous, I was living there in a decidedly not-so-glamorous way. Back then, I was a “scholarship kid” at a prestigious university in the city (a dual English and Political Science major), and once spring semester ended, I was always left in a lurch while my more affluent classmates jetted off to Europe or some Third World country where they allegedly did charity work to puff up their resumes.
Meanwhile, my family lived on the opposite coast, airfare was expensive, and the jobs didn’t exist back in our small rural lumber town. As such, it was always a struggle to fund my summer living expenses and figure out logistics — especially when every company out there merely offered those swell “unpaid internships.”
However, the summer between my sophomore and junior year, my old roommate’s stepdad came through big time with an offer to let Mary and I live rent-free in the beach house that he got from his divorce — so long as we got jobs and kept the place clean until he and Mary’s mom got back from Germany. Even with the moratorium on using the place for parties, we felt like we’d struck gold.
We moved in to our summer cottage in early May, and I managed to pick up a job as a seasonal hostess at one of the esteemed local restaurants while Mary worked for a specialty foods store. It was perfect.
“Thank your stepdad again for me, Mary,” I said once I got home from work one night. “I would never actually get to keep any of these tips I make if I worked in the city and paid for a dorm room.”
Mary was the epitome of preppy chic — a cute, leggy brunette with tiny boobs and a penchant for J.Crew and Ralph Lauren. She smiled at me from her spot on the couch, where she was flipping through the latest issue of Cosmo. “Don’t worry about it. I mean, I’d be really bored house-sitting by myself.”
“Did Dale call you?” I asked.
Mary shook her head. “No, but I’m not worried. Remember — you and I are going to that bonfire this weekend, so if he doesn’t have his act together, I’ll find someone else to be my summer boyfriend.” She shrugged and looked very matter-of-fact about the whole thing.
I admired how cool and collected Mary was when it came to guys — her breezy, preppy confidence. Back then, I was insecure and also way more emotionally invested in sex than the guys I was usually with — so it was a genuine recipe for disaster.
Mary yawned and stretched. “Good, because I think you need to think less. These ‘bonobos’ in their twenties aren’t worth the scholarly analysis, April. Just enjoy a nice hard ride if you happen to run across a cute one — and keep it at that, hmm?”
I nodded. “I know… I wish I could find a real boyfriend, though.”
Mary smiled. “Well, maybe you will. Out here in the summers, lots of totally eligible, decent guys are looking to party. But on the whole, I would suggest you just enjoy your tips and have a good time.”
“Oh, trust me,” I giggled. “I plan on ‘enjoying’ anything and everything.”
I went upstairs to take my shower and took a good look at my body in the full-length mirror. I had bigger boobs than Mary, but a relatively petite frame, with hazel eyes and long, ash-blonde hair. I was totally doable. I turned on the shower and started lathering up, letting my hands rove over my curves. It had definitely been too long since I’d gotten laid. Even the thought of seeing a naked guy and sucking him off was making me excited. I reached down and started touching myself. Just as I was getting into a nice rhythm with my clit, Mary knocked at the door.
“Hey, April?”
“Yeah?” I called out while sighing to myself in frustration.
“I forgot to tell you — the fan is broken, so you’ll probably want to open a window when you run the shower to let the steam out.”
“Oh, okay, no problem.” At that point, I finished rinsing off and turned off the water. I wrapped my towel around myself and then opened the bathroom window. The ocean breeze smelled wonderful. I reached up to the window to pop it open and something outside caught my eye.
The house next door had lights on upstairs, and from our bathroom, I could make out the figures of the couple next door. They were on the bed making out and he was taking off her dress.
I knew my bedroom window lined up with theirs perfectly, so I hurried down the hall to get a better look.
The couple next door consisted of this lady with long red hair and really big boobs — at least D-cups, but maybe bigger. She slipped off her lacy thong to reveal a little landing-strip bush and a great ass. She had a centerfold’s body.
He, on the other hand, was dark-haired and smooth-shaven. He had a toned but slender build and a huge cock that she sprang loose from his boxer briefs. I watched as the redhead got on her knees and began sucking him. Mesmerized, I let my towel drop to the floor and resumed touching myself as I watched the hot, unexpected peep show from my darkened bedroom.
She sucked him off for a while before getting on the bed. And then I watched as she spread her pink pussy lips and got on top of his huge dick. As she rode him, her tits bounced up and down as he grabbed her nipples in his mouth every chance he could.
I pinched my own nipples with a free hand while the other kept stroking my clit. I climaxed before they were near finishing. I pulled over a lounge chair and sat down to enjoy the remainder of their “show” while getting myself revved up all over again.
The second time I came, I must’ve fallen asleep after, because I woke up naked in the chair with the morning sun pouring on my face. The bedroom next door had the curtains closed, and the car in the driveway from yesterday was gone. I got dressed and ready for work as usual and met Mary downstairs for breakfast.
“Do you know any of the neighbors here?” I asked her.
“Other than Jon and Celeste down the street, really no one,” she said. “Why?”
“And then I watched as she spread her pink pussy lips and got on top of his huge dick.”
I smiled a little. “Uh, just curious. Is it mostly renters here in the summer?”
Mary shrugged. “I mean, even the owners come and go during the summer.” She paused. “Did you see something?”
I must’ve been blushing. “Well, there was this redhead and some guy and they were going at it pretty good last night.”
Mary giggled. “I can’t say I’d recognize them, but duly noted — and good for them.”
I nodded. “Yeah, no kidding. Well, I’m off. See you later.”
“Have a good time at work. If Dale calls, I might not be here when you get home, but I’ll call if I’m going to be super late.”
“Okay, cool.”
I headed off to work, and it was a pretty normal, busy lunch rush at the restaurant. We had our lull between lunch and dinner, so I took a break to touch up my make-up, eat a little, and get ready for a long but hopefully lucrative night ahead.
We were packed thanks to the holiday weekend coming up, so I had lots of people gunning for spots on the waitlist and even trying to bribe me. Just as the sea of hungry patrons was starting to recede, I was stunned to look up from my list and see, up close and in person, my naughty neighbors.
The redhead smiled at me. “Hi, we were wondering how long the wait is for two?”
“Oh, yeah.” I could feel the blood rushing to my cheeks. “Sure, let me just take a look… ”
I wanted to bury my face in the clipboard. Meanwhile, the guy was obviously checking me out, and he went on the offensive.
“Hey, I think I recognize your face. You live on First Street, right?”
I nodded — or at least I think I did.
The redhead flashed me a knowing smile. “I think we’re your neighbors.”
“Wow,” I stammered.
“I’m Eric,” he said, extending his hand.
“And I’m Brianna.” She smiled wider.
“Hi — I’m April.” I shook both of their hands, feeling more awkward by the second. Did they know I watched them? Did they happen to see me naked in a chair by my window? These questions and more raced through my head as I blurted out: “Um, I can actually get you in at a booth over by the bar, if that’s okay? You won’t have to wait.”
“Great,” Eric said. “Thanks so much.”
“Yeah, talk about being a good neighbor.” Brianna giggled. “Thank you, April.”
I smiled and nodded. “Right this way,” Once they were seated, I wished I could disappear into the wall, but no dice. A couple hours later, Brianna and Eric paid their bill and greeted me again.
“We really appreciated you taking care of us tonight, April,” Eric said. He slid me some folded dollar bills.
“Oh — wow, you don’t have to do that — ”
“Shhh,” said Brianna. “I used to work in a restaurant, too, so yes, we have to.” She smiled.
“Thank you both,” I said, pocketing the money.
“I’m sure we’ll be seeing each other again soon,” Brianna winked at me and took Eric’s arm.
I was stupefied until after they got in their car and left. And then I looked at the bills and found a napkin in the middle of the stash.
I pulled out the napkin and saw scrawled in blue ink: “Midnight tonight, same place as last night.”
At once I was both mortified and aroused as I recalled the facts: They were a hip, attractive couple — and they knew about me watching them. They’d seen me naked too, probably, and they wanted me to somehow participate again. In less than twenty-four hours, my summer was taking quite the turn. I had no idea what this meant or where it was going, but in the spirit of what Mary told me, I figured it would be fun.
We started closing around 9, so by 11, I was home. Evidently Mary was with Dale, so I had the whole house to myself. I showered again and put on a little eyelet cotton slip. I climbed onto my bed and waited for their bedroom lights to turn on.
“I pulled out the napkin and saw scrawled in blue ink: “midnight tonight, same place as last night.”
Sure enough, Brianna came in the room first, already naked. I watched as she took toys from the bedside drawer and began using them on herself. I moved the chair over to the window and began playing with myself, too.
Eric came in the room next, obviously fresh from the shower. He let his towel fall to the ground and climbed on the bed. I watched him tonguing Brianna’s pussy — and over the roar of the ocean, I could make out the faintest moans of satisfaction. Tonight, Eric took control. He put Brianna’s legs over his shoulders pile-driver style and pumped her full.
I waxed sentimental and jealous — that had been my favorite position with my ex. But I wasn’t going to let the past ruin the incredible moment unfolding before me. I put both of my hands to work, with one rubbing my clit and the other pumping fingers in my pussy as fast as I could.
Just as Eric took Brianna over the edge, I made myself squirt, leaving a gooey puddle in the middle of the cushion.
As I caught my breath, I watched Eric pull out of Brianna and her eagerly licking up her pussy juices from his huge shaft. She titty-fucked him and eventually he finished all over her boobs. While Eric rolled over to fall asleep, Brianna surprised me by getting out of bed and coming to the window. Looking right at me, she smiled as she drew the blinds.
I fell asleep deeply aroused but still confused. Would this “live show” become a routine? I didn’t have to wonder for long, because the next night at work, Brianna and Eric showed up again. My boss was standing there while I turned twenty different shades of red.
I tried to play it cool. “Can I get you two a table — or would you like the booth you had again?”
Brianna smiled. “Either is fine.”
I stood there staring off into space, picturing her bouncing tits underneath the tank dress she was wearing.
“Hey, April — ” My boss poked me with menus.
I laughed it off. “Sorry — right this way.”
Eric grinned. “No worries — I’m feeling pretty slow myself after a long day today.”
They had their dinner, and not surprisingly, I received another cash tip — with another note inside. But this time the napkin read: “Pajama party at our place when you get home.”
When I got home, I showered and put back on the eyelet slip. I assumed they liked how innocent it made me look. Mary was out for the night again, so there was no need for me to hide as I crept out the back door and went over to the neighbor’s porch. Before I knocked, Brianna opened the door and greeted me. “I’m so glad you came,” she beamed. “Wine?”
“Wine’s good,” I chuckled nervously.
Brianna was in a sexy black satin kimono. I couldn’t tell if she had on anything underneath, but she was a bombshell with her red hair in long, loose waves.
“Eric’s upstairs. I thought you and I could get a little better acquainted, if that’s okay?”
“Sure,” I nodded. “I mean… this is definitely a surprise… ”
Brianna laughed. “Well, it’s a surprise for us, too. But a really, really happy one.” She handed me a glass of wine. “See, Eric and I do like to put on a show — and sometimes we do it in public. But we’ve always wanted a captive audience — and I’ve always wanted to play with a ‘third.’”
“Oh,” I nodded and took a sip of liquid courage.
“I had girlfriends back in college and I miss them.” Brianna giggled and put her hand on my leg. “Have you had any girlfriends?”
“No — I mean… no.” I laughed nervously. “Guys always want girls to kiss at the club and stuff. But I’ve never done anything with another girl before.”
“Well, would you like to try tonight? I know Eric wants to have you, but I want you, too.” Brianna reached over and ran her hands through my hair. “You’re just a vision, April.”
The blood rushed from my head to my clit as I felt her lips on mine. Before I knew it, Brianna and I were eagerly making out on the couch, and she’d slipped her hands into my panties. I was soaking wet and probably could have come right there with her touching me.
But that’s when Eric showed up, fresh once more from the shower: “Hi again, April.” He cleared his throat loudly. “Bree… honey. Are you going to hog her all for yourself?” he teased.
Brianna looked up and giggled. “No, no, I wouldn’t dream of doing that to you. Come on, let’s all go upstairs.”
“I had never felt so turned-on or desirable before.”
As we arrived in the bedroom, Brianna lifted my slip off and kissed me again. “See how perfect she is, Eric?” The two of us got in the middle of their king-sized bed.
“And you two are even more perfect together, mmm.” Eric let his towel drop and stroked his bulging erection. “April, would you like Brianna to eat your pussy and make you nice and wet for me?”
“Sure,” I said, suddenly feeling bold. “I want to play with her tits, too.”
They both started laughing and Brianna undid her kimono. “Go on, feel them. Everyone thinks they’re fake, but I promise, they’re real.”
I looked incredulous and squeezed Brianna’s tits, letting my fingers circle her nipples. “Wow.”
Brianna guided my mouth down to her nipples and put one of my fingers right beside her shaved pussy. I didn’t know what I was doing, but I began playing with Brianna’s clit while sucking her nipples — and she moaned and got wet.
Eric stood there stroking himself, pumped and primed for action.
Brianna tilted my chin upward and kissed me again. “Good job so far. Now let me taste you.”
She spread my legs wider than they had ever been spread, so that every inch of my pussy and ass was exposed to the room. And then, without mercy, Brianna’s tongue began its delicious torment. My eyes were mostly closed while I moaned, when I opened them, I could see Brianna’s face also contorting in pleasure as Eric pounded her from behind.
Just when I thought I was headed for the brink, Brianna stopped and stood up. “She’s ready for you now, babe.”
Eric stepped over, and I was a little nervous wondering how that fat cock would fit inside my tight pussy. But the minute he entered me, it was nothing but toe-curling ecstasy. Brianna sprawled out beside me and alternated between rubbing my clit, licking my nipples, and kissing me. I had never felt so turned-on or desirable before. When I hit a screaming orgasmic peak, Eric pulled out and let Brianna finish him off with her mouth and tits again.
Brianna and Eric were in the Hamptons that entire summer — so by August, my sexual repertoire had grown above and beyond anything I could have imagined — or even attempted with the average “dudebro” at a party.
Even all these years later, my wild “first time” with the two of them still goes down in my sexual history as one of the best episodes of my life — although the following summer when I became Brianna’s assistant at a publishing house, the steamy “after hours” sessions we had on our own are a close runner-up!