Discovering my best friend’s sister with her college FWB at the beach [FFM] [Very Long]

Hey everyone! I just wrote this in a 4 hour marathon, and have only done cursory editing, so please forgive any mistakes. Just wanted to relay the experience as accurately as I could. If you’re in a rush for sexy stuff to start and spending the time to build the juicy tension, just scroll down to the partition line. I will write more about this if there is any interest

I grew up in a mountain town that was nearly always covered in a blanket of snow. Naturally, it made sense for people to vacation in warmer weather. My parents inherited a beach house in one particularly quiet town, right on the water. We would visit my grandfather there in the summers and there was usually enough room to bring my childhood neighbor and best friend Alex with us. Our families had been tight for as long as I could remember; my father was a dentist, and his, an orthodontist. It being a small town, they certainly sent each other some business in their working years.

When my grandfather died in the summertime two years ago, I had just turned 21 and finished my second year of college. Alex had just finished his third year at another school and wasn’t exactly excited to spend his summer in our hometown, so he offered to come along and help us sort out my grandfather’s belongings and get the house cleaned up.

One afternoon, Alex and I were hauling yard debris to the curb for pickup when we noticed a realtor arriving at the neighboring home to give a tour. Alex joked that he should let his parents know about the house being for sale, as they were desperate to get out of town for the summer.

I snapped a photo of the realtor’s sign in front of the house and sent it to our inter-family group text, saying “want to be vacation neighbors, too?”

As we were finishing up a long, tiring day of yard work, moving boxes, dusting and sanitizing, Alex’s father responded to the group text to let us know he and Alex’s mom had scheduled a tour of the home two days out. So they drove down, we put them up for the night, and the next day, they closed on the house.

As we finished a grueling week of cleaning up my grandfather’s old home, it came time for me to head back to the city I was working and going to school in. Alex decided to stay in town for another week or so to help his parents get their new vacation house set up.

The night before I left, Alex let me know that his younger sister Melissa would be arriving sometime in the morning to “help out,” i.e tan on the beach. I hadn’t gotten along with Melissa well as she was 3 years younger and honestly kind of annoying when were kids. But, I hadn’t seen her in a year or two at the point, and she had just finished high school, so I reckoned she had matured.

Melissa arrived at their family’s beach house the next morning, and I woke up to a selfie of Melissa and Alex on the beach at sunrise saying “join us!” I stole a second glance at the photo to admire Melissa in her bikini, and I remember how strange I felt being attracted to her for the first time.

Melissa was always pretty, but she was becoming a confident woman, and it showed. Melissa was nearly a foot shorter than me, and I could tell by the photo that hadn’t changed. She had small, firm breasts and a butt worth taking a second or third look at. She had blue eyes, a beautiful smile, perfect teeth thanks to her dad, big lips thanks to her mom, and adorable dimples. In her photo she was looking like an Italian sun goddess with her raven hair blowing in the wind.

I hopped into a swimsuit, grabbed my sandals, and headed out for the beach. I spotted Alex and ‘Lissa immediately and waved to Alex. I saw him get her attention to tell her I had arrived as she sunbathed face down in her skimpy red bikini, and watched as she bolted up and across the beach with a beaming smile to greet me. Maybe I was remembering our relationship growing up, but she seemed very excited to see me.

On the topic of me, I’m not anything special, really, except for two things; I have been told I have a “very thick cock” and am “the best” at going down on a girl. When we were horny kids, these things spread around high school like wildfire and often made one the subject of discussion.
Alex’s friends would often “tease” me about these things when we would hang out at his house, and he would become fairly angry when they were said in front of his sister.

Melissa ran to me and jumped into my arms without warning, wrapping her legs around me and forcing me to give her a kind of spinning hug before setting her down on her feet. She jumped up and down and excitedly said hello, and how she missed me, and that our summers would be amazing from now on given our families’ new vacation homes.

We spent the morning at the beach talking when Alex mentioned that the sun was nearly at the middle of the sky, which made me realize it was almost noon, meaning I had a flight to catch in a few hours. Melissa lamented that I had to leave right when she arrived, but I reassured her, saying there was “always next summer.”

I packed my bags and caught a ride to the airport. As I sat in the terminal awaiting my flight, I noticed a message from Melissa. We didn’t usually message each other directly outside of our families group text, so having received a few messages from her in one day was unique. I opened the message to see a photo of her sitting on her sink in the same red bikini, turned around at the waist and facing the mirror, making a silly face and flashing a peace sign.

It was clear she was showing off her ass, and making it seem a little more innocent than it was. I’m no fool, so after two bikini photos in one day, I started to get the picture(s). I responded with a sort of innocent and supportive “looking great!”

So as the seasons changed I went back to school and work. Things were going well, and I had kept up small talk with Melissa more than before. We chatted about her first year of college, my third year, our friends and hobbies. She decided to attend the same school as Alex and didn’t want to live in a dorm, so Alex let her stay in his apartment’s spare bedroom (previously his game room, bless him.)

In this time, I had a short relationship with a girl who turned out to be scarily clingy. I didn’t talk to Melissa much during this time but one winter night when my girlfriend was staying over, Lissa sent me a video of herself and her friend Stephanie jumping into the snow in their bikinis and uggs. A friend had filmed it for them, and had zoomed in on their butts as they jumped, exclaiming “bootayyy!” for the camera.

My girlfriend saw the notification, asked who “Melissa” was, and demanded to see what it was. She was very jealous right away and asked “why do you have girls sending you videos showing off their asses?” I explained that the video was perfectly innocent and part of a trend that people were doing back in my hometown, where it was always snowing. Maybe not the “bootayyy” part, but still.

Long story short, that was our last night together, as she demanded that I delete all non-familial females from my phone, which I wasn’t having. Melissa messaged me the next day and as we caught up a bit, she asked about my girlfriend. I let her know we had broken up the previous night, and she called me right away, answering with a consoling tone, and pressed me for a reason. I eventually gave in and told her what had happened and she began to apologize profusely. I just laughed and said not to worry, I had probably dodged a bullet thanks to her.

Melissa started to lighten up, and she said it was crazy for my girlfriend to think I’d even be interested in her like that with our families’ histories. I chuckled and let out a sheepish “haha.. yeah” to which she responded “or maybe you are?” before abuptly changing the subject. She didn’t press me on it, but she could hear it in my voice. I was already interested.

A couple weeks later, our families had begun to plan dates for summer vacation. Both sets of parents were retired and were going to spend the entire summer at their respective homes, so it was up to me, Alex and Melissa to plan a week that we could all get together there. We committed to a date, shared it in the group text and Alex’s father surprised all of us with round trip tickets. My father appreciated this but was privately a little annoyed that he would feel socially obligated to return the favor next year.

Melissa messaged me directly about how excited she was to see me and how great of a week it would be. She also let me know that with the money she had saved from not having to pay her own way, she was going to be bringing her friend Stephanie along with her, as she had just had a breakup of her own and needed a getaway.

In the weeks leading up to the trip, she sent me a snap with a picture of herself and her friend Stephanie in a changing room trying on bikinis. She captioned the photo saying “Which should we buy?” as they stood with their arms around each other’s backs, looking lustily at themselves in the mirror. Sexy would be an understatement.

Melissa was definitely of a healthy weight (thicc?), and had incredible curves. Her silky black hair draped below her waist, in the traditional sideways-stance pose to show off her butt. Her perky tits filling out her black polka-dot top. Not to mention her friend, Stephanie. Stephanie was probably an inch taller than me, blonde, legs for days, and round hipster glasses to match her personality. She had very small breasts and honestly that was part of what made her look practically like a supermodel. She wore a dark blue webbed onesie bikini that left very little to the imagination, and was definitely as cute as Lissa in her own way. They were definitely even cuter together, however.

I received another photo before I could send a fumbling response. Lissa captioned it “dO tHeSe mAkE My BuTT LoOk bIg?” In large, bold text. It took me a moment to see through the text that she was completely bent over in a yellow bikini in front of the mirror, with her friend Stephanie leaning over her back and getting a handful of her sweet, plump ass. I couldn’t see her frontside, but a matching yellow top to her bottoms was hanging on a hook in the changing room.

For the first time, Melissa was making me hard, whether she knew it or not. I mulled over how best to respond, when another snap arrived. This time, a video. They were wearing thin, matching white bikinis and laughing wildly, as Melissa steadied the camera and said “okay, okay, this time, hold still” and stuck her tongue out to flick Stephanie’s nipples over her bikini, instantly revealing their hardness. The girls laughed like crazy and the video ended abruptly.

At this point, I was wracking my brain considering how Alex would feel about me receiving these kinds of photos from his little sister. I stopped opening the snaps and decided to jerk off and clear my mind.

At the end of my session, I texted Alex with the intention of somehow bringing up his sister organically. After a good, long period of me beating around the bush, he beat me to it, and said he wanted to talk to me about something, and that it could be weird. I encouraged him to tell me and that I would respond appropriately. He asked if he could call, as it was too much to text about, so I called him.

“So uh, I never really wanted to discuss it, but it seems like Melissa hasn’t really grown out of her crush on you.”

Shellshocked. Crush? On me? “Grown out of?” This was all news to me. Alex went on to explain this was sort of a running joke privately in his family, and that his parents would regularly tease her about it saying things like “oh your boyfriend is on his way!” when I would come to their house as a kid. This apparently infuriated her as a kid, especially after Alex once caught her cutting and pasting a picture of me from his yearbook into a picture with her, and we shared a laugh about it.

“Dude, I had no clue.” Alex scoffed at my denial. I genuinely didn’t know, but Alex, to my credit I suppose, thought I could never be so clueless. “Well, at any rate man, you don’t need to worry about anything, of course she’s off limits.” I choked on my words.

Alex asserted a bit of a gruff tone and began to speak in a laying-down-the-law sort of way. “Look man, she’s my sister, so like, it’s weird but we’re all adults.. We’re gonna be spending a lot of time together, so all I’ll say is this – unless there’s a serious relationship, I don’t wanna know about anything that happens, okay? I don’t want to be a dick and stand in the way or anything consenting adults want to do but I don’t want to have to think about you nailing my sister.”

“Whoa, whoa, dude, who said anything about nai—”
He cut me off.
“No one did, no one, it’s cool, I’m just saying.. I don’t know man. We’ve been friends forever. We’re all adults. Just don’t do my sister any harm and we’ll be fine.”

My heart raced as we ended our conversation. Had she pre-empted him? Did she mention something about the snaps in the last couple hours??

Oh, wait, the snaps! It had been a couple hours since she sent the first one and I never responded! I rushed to my phone to find a couple more videos and a single message from Melissa. I opened the message first, which read “Sorry that was probably too far.”

I couldn’t open the videos fast enough. In the first one, the two girls were still in the changing room, dancing to trendy music in their matching white bikinis when Stephanie quickly untied and snatched away Melissa’s bikini, exposing her bare breasts and her quarter-sized dark brown nipples.

She quickly covered herself with a handbra and an embarrassed and feigned indignant expression, but, continued to film as she snatched the string for Stephanie’s bikini bottoms, exposing her perfectly shaven pussy. As Stephanie covered herself with her hands, Lissa uncovered her chest and used her free hand to spank Stephanie, who scurried away.

I returned to the home screen and noticed there was still a notification for another video I hadn’t watched, from Melissa. Not being able to resist, I opened the app again. Still topless, shamelessly so in this clip, and filming herself and a bottomless Stephanie in the mirror, Stephanie pointed to the ceiling and said “spider!” as Lissa looked up in alarm. This was the perfect diversion for Stephanie to snatch Melissa’s bottoms as well, ending the video series at the very brief moment where I caught a glimpse of Melissa’s perfectly smooth, delicious looking pussy as her bikini dropped at her ankles.

I couldn’t help myself. I unwittingly initiated an emoji conversation that went a little like this.

Me: ??

Lissa: ??
??

Me: ?

Lissa:???

Me: ??

Lissa:??????

I couldn’t believe it. I’d known her so long, I just never considered anything like this happening between us. So many thoughts ran through my mind – What if it went wrong? What if this fucks up our families?

The thoughts from my brain didn’t overcome the thoughts coming from my now rock-hard member. I caught myself stroking over my sweatpants at the thought of her anticipating a picture of my manhood. I rose from my bed and walked towards the bathroom, heart racing.

It had been a while since I had done this. I spent about five minutes trying to get the best angle possible and finally decided to send her a teasing picture instead, of my thick bulge showing through my grey sweatpants.

Sent. Sweating. No turning back now.
Bzzz. Nearly immediately, a returned snap. A picture of the bottom half of her face as she bit her lip. A caption that simply read “more.” So I took another photo with my bulge showing through my briefs. Precum had obviously started to soak through them.

Sent. Calming down. She’s literally asking for this, Alex is cool, why am I worried?
Bzzz. And there it was. /r/godpussy material. A perfect pelfie taken as she sat on the floor. And that same damn caption again. “More.” At full mast now, this wasn’t an issue. Snapped and sent.

I decided to be devilish and replay her snap. I softly masturbated to it and stopped in shock as I noticed someone else’s leg in the background of her photo. A smooth, long leg. Who was she with??

I messaged her to ask. She nonchalantly replied “oh, that’s just Stephanie, don’t worry ” and I replied “lol okay, did she see anything?”

“Not unless you want her to!”

Was this a test of some kind? Had she actually already shown her the photos?
“I suppose if she wants to see them that’s alright with me then haha” I responded.

Not sure how this was going to go, I fluffed myself in preparation for either consolatory masturbation or a glamorous photo shoot.

“send us a video? ? :)”

“lol are you serious?”

Bzzz. A video. I scrambled to open it. Melissa recorded from overhead as she and Stephanie lay back on what I assume was Stephanie’s bed, piled on top of a mountain of particularly feminine pillows and stuffed animals. Both girls winked at the camera and stuck two fingers in their mouths before reaching to the other girl’s pussy and rubbing her clitoris in slow circles. Lissa’s camera work was top notch and showed me she may have seen more porn than I had.

So, she was serious. I began to masturbate to the mental image, which probably would have been enough, before I received another message. This wasn’t a disappearing photo, but one sent via the messaging client and saved for posterity. She followed the image with a text that said “some material ”

It was a double pelfie of the two girls, side by side, with legs intertwined, both two fingers deep inside the other’s pussy.
A risky move, I decided to sign into snapchat on my work phone so I could pull the image up and film myself cumming to it, which took a solid 30 seconds.

“Ooooommmmggggg ????”

“Did you two like that one then? ? ”

“We literally can’t wait for vacation!! ? ”

“One more week! ”

And what a long week it was. We continued exchanging dirty pics/vids and I asked about her relationship with Stephanie. She said she was “probably just bicurious if anything” and wanted to experiment in college. She explained that Stephanie was a good friend and was very open sexually and while they were attracted to each other, they didn’t want to be in a romantic relationship beyond fooling around and hanging out.

She asked me about our age difference and I said it didn’t bother me if we’re both in college and I’m not really one for bars anyway, which was probably a Freudian slip implying my desire to spend time with her one on one.

She told me she had lost her virginity in high school in a supremely disappointing experience that left her feeling embarrassed, like she wasn’t hot enough or fit for sex, and that the guys she had fucked in her first year in college didn’t do much to change that. I was looking forward to having a chance to show her not all guys are super selfish in bed.

It was almost time. 7 days with Lissa, Stephanie, Alex and both sets of parents. How were we supposed to get any kind of private time with everyone else around?

And so, three days before departure, a melodramatic disaster struck for Alex’s parents. Their sump pump from their mountain home’s basement had failed overnight and had flooded the floor by about a foot, meaning Alex and his father would need to tend to the damage immediately.

After a nightmare of a logistical conversation in the families’ group text, it was decided that Alex and his dad would stay behind, and get their flights moved by a couple days. They hired a helper to ensure it was done quick enough for us all to be together for at least a few days at the beach.

It was also decided that Lissa, Stephanie, and Alex’s mom would still come as they had planned to. Alex’s mom ended up driving out to Alex and Melissa’s apartment and letting him drive the car back to their home. Like I said, logistics nightmare.

My mother and Melissa’s got along wonderfully and would often end up drinking wine and sharing stories well into the evening. I thought my father would be less entertained without Alex’s around, but he enjoyed his quietude during the days, reading in the beach home’s attic made to resemble a lighthouse, and joined the other parents at night to “party.”

Mine and Melissa’s flights were leaving from different locations but landing in the same place, of course, and we were both in the air at the same time, sending snaps back and forth from the plane wifi. Around halfway through the flight, the conversation became suggestive and she sent me a message saying “*nsfw*” which didn’t make sense until I got her video.

She was filming from overhead in the plane bathroom as she posed and positioned the camera at her backside and slid her yoga pants down a bit in the back, exposing her gorgeous ass as she wiggled it from side to side. She panned the camera around her hips to her front, as she pulled her yoga pants down to her knees and rubbed herself over her cute, lacy panties. She quickly pulled her pants back up as she giggled and switched to her rear camera, filming herself in the mirror while giggling and fondling her breasts before blowing a kiss to the camera.

I sent her a slew of suggestive emojis when she responded with the classic ” ?” she had used on me nearly a dozen times at this point. I knew this would be no issue given how worked up I was and went into the airplane bathroom, filming myself as I shot ropes into the sink. (I know, I’m a monster; I’d like to make it clear that I did clean up after myself with sterile wipes)

I sent the video and returned to my seat. Less than a minute passed. Bzz. A message.

“I’m sitting in between Steph and my Mom and I tried to show Steph that snap lowkey and idk if my mom caught a glimpse of it ?”
“Or anyone else on the plane for that matter ” I responded.
“Honestly idc I’m so ? right now. lol Steph wants me to say she is too. We’re both dying for it tbh ?”

Being on this plane knowing what was waiting at my final destination must be what the trip to heaven feels like.

So we landed in paradise, and I caught up with my Father by baggage claim. I asked if he had seen Alex’s family yet and he informed me, to my surprise, that we’d be picking them up as well, and they would land an hour after me. So I waited in a privately tense anticipation for some time for the ladies to arrive, when I heard Alex’s mother call out my father’s name. Before I could turn around, I had a petite set of arms wrapped around me from behind.

I turned around to greet her, but she kept a tight grip and twirled around with me. My eyes met with Stephanie’s, as I was taken aback seeing her for the first time. She was tall, with an indescribably sexy figure. I reached to give her a hug, saying “yeah, let’s make it a group thing!” as Lissa relentlessly embraced me from behind. I went to give Stephanie a half-hug when she pulled me in close, with our bodies pressing and Melissa’s interlocked hands between our torsos. My father and her mother were completely oblivious, lost in conversation and watching for their bags to notice us.

In our embrace, as these two fire-hot rising college sophomores giggled in my ears, Stephanie turned and kissed my cheek lightly as she let her hand discreetly travel down my chest, over Melissa’s hands, and further to graze over my now semi-erect cock. “It is *very* nice to meet you,” she whispered in my ear. In this instant that lasted 5 seconds but felt like eternity, Melissa’s hand also fell slightly to my crotch and Stephanie took notice and pulled me in for another hug, placing both of their hands firmly, if not briefly, on my thick bulge.

We stood watching for baggage and made nice, talking with our parents about our lives and pretending we hadn’t spoken much. Their bags came ’round the carousel, we collected them, and headed for open waters.

After a short drive to the coast, we helped the ladies unpack at their house before unpacking our own bags. My father invited Melissa’s mother to our house to hang out with my mother while he grilled dinner. This left the girls and I free to go directly for the beach.

I waited for them for 30-45 minutes in the sandy strip between our homes after we agreed to go for them to get changed. Stephanie came down first, in a baywatch-esque backless red onesie. Sexy, but conservative enough to not catch any flak on the first day vacationing with a friend’s parents.

**********************

And then Melissa emerged. Stunning in her blue striped bikini tied with bows. “Close your mouth, you’ll catch flies” she said with a wink. Was I that obvious?

I walked with the girls until we reached a comfortable spot on the other side of the beach dune, no long visible to the row of homes. We arrived at night, and were in the early season, so the few that had visited the beach that day had already cleared out. We laid out our towels, and I got comfortable in between the two of them as we watched the stars begin to reveal themselves.

My phone buzzed, a message from my dad. Oh, shoot, time to go to dinner, I thought. A picture of several burnt hamburgers and hot dogs and a caption – “gonna try again, dinner in an hour ”

I shared the message with the girls and we shared a collective sense of relief that we had a little bit of time in some kind of privacy. We laughed and as we all began to lay back down, I stretched out both arms to invite the girls into them.

Suddenly, it was real. All that time, all that tension, and now, I had these two on my arms. I was most excited about being intimate with Melissa but Stephanie was so objectively beautiful, and clearly fun; and of course, Melissa wanted her to be a part of it so, y’know, bonus.

They cuddled up to me, as I pulled them in by their shoulders and they rolled towards me with Melissa on my right and Stephanie on my left. They both run their fingers up and down and chest and stomach, lacing fingers and holding hands on occasion, as they giggled and stared at me. Their chests pressed against my sides, both with a draped leg over mine, I could feel their warmth on both of my thighs. I couldn’t take it anymore.

I moved my right hand from Melissa’s shoulder to the side of her face, brushing her hair back with my hand resting on the side of her temple. I turned towards her and we locked eyes as she looked me over almost desperately, biting her lip. Both girls moved their hands to my thighs, grazing over my now raging cock trapped by my trunks, being sure to press down with intent with each pass.

Melissa closed her eyes and pulled me in with her lips. Her soft kisses as she moved her hand from my crotch to my neck and face were the kind you can only get after years of pent up passion. Stephanie had dropped pretense as Melissa and I explored each other’s mouths with our tongues for the first time and began to grip me firmly over my trunks. Dissatisfied with the lack of range of stroking motion through the cloth, she slid her fingers under my shorts, and was the first to lay a hand on my thick length.

She stroked me gently and began to firm up her grip as she laid delicate kisses on my neck, chest and shoulder, while I kissed up and down Melissa’s neck. I ran my fingers through both of their hair at the base of their scalps and pulled gently, eliciting moans as their eyes rolled back. When they seemed satisfied with that, I moved on to squeezing their breasts as they writhed against me, pressing their perfect, tight pussies against me.

These two gorgeous women worked in tandem to undo the laces on my shorts as we kissed and I reached both arms down to firmly grasp both of these beautiful girls perfect asses. Melissa guided Stephanie with a single finger under the jaw to kiss me, and we shared a few slow, hot, kisses with just a little bit of tongue as Melissa kissed my neck and jaw. They leaned up to free my arms as they pulled my shorts down enough to free my throbbing penis from its prison.

As soon as it sprang up, the pair pawed my balls, shaft, and rubbed their thumbs and palms on the head of my cock. I began to rub them both over their bikinis as they writhed and moaned, both working me with a single hand. We laid in ecstasy, feeling and pleasuring each other, staring at the stars, finally able to share in the release we all wanted.

Stephanie humped my hand diligently and impatiently pulled the crotch of her onesie to the side before firmly grabbing my two middle fingers on my left hand and guiding them to her opening. For symmetry’s sake, I did the same for Melissa, under her striped bikini. Both girls began to grind into my hands with varying intensity as their soaked, tight, shaven pussies quaked. They both passionately worked my erection, occasionally spitting on their hands and switching who was on shaft vs. ball duty.

Both girls were primed to cum as I began to fingerfuck them more intensely. Stephanie was the first to tighten up around my fingers. She bit into my shoulder and cried out in pleasure, when Melissa let a sharp cry out and abruptly pulled my fingers out of her vagina. She whimpered something in a kind of pathetic way that sounded like “please eat my pussy” and I didn’t need to ask her to repeat herself. I motioned for her to come sit on my face, as Stephanie sat up to accommodate.

Melissa spread a leg over my chest, steadying herself on her knees, and readied her dripping pussy over my face, pressing her pretty little clit to my nose a few times as she cooed. Stephanie faced her on her knees as they shared kisses and locked their fingers together on my cock as I began my oral assault.

The top strategies I had in the pussy-eating playbook certainly didn’t seem to disappoint as she bucked on my face, swirling tongues with her friend and letting out the sexiest moans I’ve ever heard. Stephanie used her free hand to rub Lissa’s clit, whispering presumptively dirty things in her ear that I couldn’t hear.

As the girls kissed, Melissa removed her hair band and wrapped Stephanie’s hair behind her head. She whispered something to Stephanie, and gave her a quick peck. Seconds later, as Stephanie bent over behind Lissa and out of sight, I felt her warm, wet mouth engulf my length. She dauntingly pulled my foreskin back and swirled her tongue around my cock head before swallowing me whole.

I continued to eat Lissa’s perfect, delicious pussy until she came on top of me, squirting on my face as I rubbed her clitoris. She abruptly hopped off my face, and took a quick, quivering walk about five paces and back again to regain her sanity.

This left me with my first view of Stephanie
sucking my dick as she looked me right in the eye, and winked. Lissa found a similar position on my opposite side and gripped the base of my shaft as Stephanie took my entire length down her throat for the second time.

Lissa guided Stephanie for a kiss just as she had before, with a finger under the jaw, and brought her off of me as they began to swap saliva, and the indirect taste of my manhood met Lissa’s tongue for the first time, leaving her curious.

I pulled her hair to the side as before, and leaned up to kiss her and her friend alternately as they eyed and stroked my cock. They pushed me back down by my shoulders with devilish smiles, and for the first, glorious time, Melissa wrapped her big, red lips around the head of my cock.

She swayed her jaw from side to side as she slid my length down her throat like she was born to do it. She competently grasped my balls from the underside and gave the perfect squeezes while stimulating my cockhead. She made room for Stephanie to suck on my balls as she continued to blow me. A frenzy of tongues lashed on my throbbing head as they occasionally switched duties.

Eventually, Melissa repositioned herself between my legs, laying down on her stomach, supported by her elbows as she fellated me. This view of her stunningly cute, thick but still somehow little butt in the prone position was overwhelming.

Stephanie must have agreed, because she laid on her stomach as well, but with Lissa’s ass in her face. As a bonus, I could see her ass in the sane position which wasn’t as big as Lissa’s but definitely top tier /r/cutelittlebutts material. She spread Melissa’s cheeks and ate her holes while Melissa worked my cock.

A man can only endure so much. I take pride in my stamina but after they had both been satisfied, I was dying to be drained, and Lissa could tell. “You’re close, aren’t you?” She asked quietly, and with a smile. I nodded, pathetically. “Do you wanna cum in me?” she asked nonchalantly. “Oh, god yes, please swallow me” I replied, causing them both to giggle.

Melissa rose up to her knees as Stephanie did the same and rested behind her, massaging my legs, gazing at Lissa admiringly. “No, silly, cum *in* me.” She straddled me with one knee at a time as I brought my legs together apprehensively.
“Are you sure? But are you, like, on the pill, or..?” They both laughed at my naivete again and pointed to their biceps, reassuring me by knowingly whispering “IUDs.”

I grinned the dumbest of grins and gripped Melissa’s waist as my cock flopped against my stomach and she glided her tight pussy against the shaft. “Are you absolutely sure?” I asked one last time. She smiled and gyrated her hips on my cock, and said “I’m sure. Now cum. In. Me.”

She rose up, and Stephanie guided my cock by the base, aligning my swollen head with Lissa’s drenched pussy lips. Lissa steadied herself with her hands on my chest and I gently lowered her onto me by her hips. She let out a slow, quiet, melodic “oooooooooooooooh” as I entered her tightness for the first time.

She gyrated, twerked, bounced, and loved on my dick. Stephanie leaned down to kiss me, and then guided Melissa with a finger under the jaw, stealing her move, to bend over and kiss me as she rode me. We embraced as tightly as we could as we kissed and I began pumping her harder and harder, nearing the point of no return. She kissed my forehead, gripped the sides of my head, put her nose against mine, and said the magic words again. “Cum. In. Me.” as I nodded hurriedly and kissed her deeply.

Pure bliss. Rope after rope of semen shot deep into my best friend’s little sister. My hips bucked into hers as her perfect, tight pussy milked me as she came for a second time, tightening up like a vice grip. I didn’t even notice that Stephanie was eating Lissa’s ass until she began to suck my balls as I was draining them in Lissa’s pussy.

Stephanie rolled over, letting out sighs of exasperation and contentment. I stroked Melissa’s hair, curling it behind her ear as we beamed at each other with goofy smiles. We kissed again, as she alternated between by forehead, cheeks and lips, slower, and more lovingly this time, stopping only to gaze deep in each other’s eyes.

Bzzzzz. Bzzz. Phone. Fuck. Time. I forgot about dinner. “Steph! Could you..?” I pointed to my phone, nearest to Stephanie.

Sounding sobered up from the encounter, Steph answered it. “Hello? Yeah this is Stephanie. No, Stephanie. Lissa’s friend? Yeah, I’m just answering because they’re swimming and I just got in. Yes, *Stephanie.*” She giggled to herself, almost embarrassed. “Haha.. is everyone okay? Fire? What? 4 bottles? Sheesh.. okay, yeah, pizza, got it, thanks, I’ll let them know.”

“What was all that about?!” I asked, bewildered.
“Your guys’ parents were so drunk they burned dinner twice so they ordered pizzas instead. Sounds like they’ll all be passing out at your house, so, they said Lissa’s is free for us tonight, but ‘no parties.'”
We all smiled at each other, exchanging glances, and laughing.

Lissa kissed me once more before finally lifting herself off of me, still dripping from our passion. “Maybe a quick dip to cool off and maybe uh clean up a little before going back?” she suggested.

Stephanie darted for the water, still more energized than us. Melissa and I got ourselves together and walked to the water hand in hand to join her friend.

“This is going to be a great fucking week,” I said.

“Literally,” she laughed.

Source: reddit.com/r/gonewildstories/comments/fg8s1d/discovering_my_best_friends_sister_with_her

17 comments

  1. I gather the only reason you haven’t been upvoted to oblivion is that it’s quite long – but damn it’s good. Please keep it going!

  2. Please keep the stories coming, that was insanely hot. Love these long Stories! You must have a lot more stories form that week, or even just that one evening and id love to hear every single one of them!

  3. Absolutely fucking hot. You gotta share the rest of the stories from that week! The writing is great, and I’ll gladly come back for more!

  4. I was concerned at first with the length of this, but my god was it worth it.

  5. Great story! Very well written. Can’t wait for more. But I couldn’t get past two issues: Alex’s parents toured the vacay house for the first time and closed on the sale the same day? Did I read that right? Also, IUDs don’t go in the biceps. Semantics I know, because other forms of birth control do go in the arm, but IUD stands for Intra-Uterine Device and by definition goes in the uterus.

  6. Incredible story! As hot as they sex was with two gorgeous women and all the leadup might have driven you nuts, I can’t even imagine how long Lissa has dreamed of this moment. Finally kissing you, finally touching you, finally feeling you stretch her out and erupt your love inside her. All since her teenage years likely

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