How the Spontaneous Friend-cation Turned into the Fuck I Never Expected [FM]

This sex-venture took place about three years ago. I recently traveled (not ideal during a pandemic, I know) to the same general location it happened. It provided some welcomed memories for a lonely night lol

I’m a wordy motherfucker, so skip to the *** if ya know… you need to get things going quickly.

It’s also very long and potentially includes some typos. Bear with me.

So, about three years ago I was roped into one of those impulsive friend-cations. One of my best friends from high school and I remained good friends through college and still are quite close. For our purposes, we’ll call him “Joe.” After high school, our friend group evolved to include Joe’s older sister. She had only been a year ahead of us and they are quite close as siblings. It also helped she had very attractive friends. One of which, let’s call her “Jenn”, Joe was downright infatuated with.

I can’t really blame him. Jenn was (and is) a smoke show. Back then her hair was long and very blonde, and all kinds of curly. She is beautiful and thick, with big tits, big thighs, and a little extra everywhere. She has this “cannot be bothered” attitude and is just effortlessly hot.

Then there was his sister, “Em.” Emy is the sweetest. Even when she was a popular senior and we were obnoxious juniors, she was really nice to us. She always looked out for her brother and that included me often enough. And she’s is every ounce as hot as Jenn, albeit quite different. You know the kind of girl that makes the most conservative outfits unbearably sexy? That’s Emy. She’s pretty tall with straight brown hair and a few freckles. She is skinny all over and very defined. She was a cross country runner for all of high school and kept up with it as an adult just for herself.

One time, I was at their house swimming and just happened to glance at her while she climbed out of the pool. She did that thing where she pushed her whole body out of the water with her long muscular arms. The weight of the water dragged her bottoms down just an inch or so. But I was staring at the way her flat stomach transitions to the smooth tight skin of her waistline. She had a hard tan line and the light danced on the almost invisible peach fuzz of her skin. Jesus.

Well fast forward to when this story took place and Emy had lost a few inhibitions in adulthood. Her body was still tight and her legs seemed longer than ever, and she enjoyed showing them off. The attraction I feel for her is this mixture of the caring older sister, girl next door, and out of my league older woman. All mixed together. I get butterflies thinking about it tbh.

The final character I need to introduce you to is “Kate.” I was not crazy about Kate. She was close friends with Emy and Jenn but didn’t show up until about a year before this story. She was just kind of… idk, annoying? I know that sounds judgy. But she was that girl who always had to try and change the plan, who always had something that needed to be said. She had none of Emy’s quiet kindness or Jenn’s oozing sexuality. She was just Kate. And she often killed the mood.

That being said, she was objectively cute. Nothing I would have written home about (again, judgy I know :/ ) But still. She had short, maybe collarbone-length hair. It was brown, but borderline black. And she had short, hipster bangs. Hipster-ish was kinda her whole thing. But it was done with way too much effort, you know what I mean. She had some cute Pinterest tattoos, did lots of “thrifting” and always had to tell us exactly why the song we all liked meant the most to her, personally lol.

She also had a fucking dump truck. I mean, it really didn’t make sense. She was the shortest in the group and had a very soft body. Soft like, just a little squishy, but honesty you’d still call her skinny. She had small, very round boobs and a slim waist. But then an ass that’d swallow up a pair of high-waisted cut-offs like they owed it a gambling debt. If there was one thing I really did enjoy about Kate hanging around, it was to watch her leave.

If you really need a description of Joe and I, then fine. But only for the sake of equality. He was way taller than me and rail-thin, but very athletic and did his best to build muscle. Just cursed with the blessing of a light-speed metabolism. He has straight brown hair like Emy and a hell of a jawline. He’s honestly cute af lol

I’m nothing special. Average height, average weight, with no serious physical impressiveness. I do have very nice dark hair, and people seem to think I’m very confident, though I don’t often feel it. Me and Joe bonded in high school because we were both floaters that everyone liked, but no one really included if that makes sense.

So, back to the story at hand. The impulsive friend-cation. Emy, Jenn, and Kate had planned a trip to a very fun city in the middle of the country. Their plan was to let loose for a weekend, maybe do a little bit of drugs, and venture out for some epic outdoor activities. They booked a cool hotel room, close enough to downtown bars to enjoy that scenery as well.

Just a couple days before they were leaving, Joe, Em, and I were grabbing dinner. She explained how Kate had just lost her job and was stressing about the trip. Apparently, she had booked her own room for some dumb personal space reason. Always the extra. Emy begged us to take Friday off and join them so we could pay for the second room and Kate wouldn’t have to stress all weekend.

Joe was hesitant, he just wasn’t the spontaneous type, nor was he really the activity type. Emy turned to me and begged. Like literally, she folder her hands and dropped her elbows on the table. She did a pouty face and said, “pleaaaaase come for me.” Oof. She pushed her elbows together and accentuated the little cleavage she had. I couldn’t believe she was trying to tease me. It was very out of character and I was just the little brother’s friend. But it did the job. My jaw slackened slightly and my little companion stood tall and proud.

I nudged Joe and said, “C’mon let’s just do it! You know Jenn will be grateful too.” He cracked a smile and did a Halpert-esque head turn. “Fair enough,” he said. “Alright, lets do it.”

Em was ecstatic and text the girls right then. In fact she started a new thread with all five of us on it.

“I got ‘em ??” – Emy

“Yaaaaaaassssssss bitch” – Jenn

“radical! I was seriously so anxious. Ugh. But I have so many great things planned u have no idea. Ur all gonna love it ?” – Kate

“Jesus Christ,” I mumbled with a sigh as I read Kate’s text. Emy aimed a sharp but playful kick at me under the table. “None of that!” She said. “Seriously, give her a break, she’s so upset about her job.”

“Fine, but if she tries to play one damn ‘record’ for us…”

Emy laughed but again shot her foot beneath the table. This time she slowly dragged her toe up the inside of my shin and back down. “For me,” she smiled.

Wtf? Was Emy really starting to come onto me? This stupid trip might be worth it after all.

Skip forward to the first night in our centralized city hotel. The rooms were next to each other but not adjoining. We had only checked in a little bit ago but decided to hit the ground running. Immediately we went out for some over-priced food and a bit of alcohol to really wake the vacation mode.

Joe and I each showered and put on some simple “stylish” (I use that term extremely loosely) outfits and were ready to go in about 20min. The ladies needed an additional 40 or so. And zero judgment here. A fresh t-shirt, jeans, and not-sneakers passes for dressed up for us. They on the other hand were contenting with an infinite number of strappy things and a horde of products.

We decided to hit the hotel bar and pre-game after a bit of waiting. 1 and a half drinks in, the three ladies arrived in the lobby and good god almighty. I can’t describe the vain pride I was suddenly stuck with when I realized I would be out on the town along with this trio of killers. Joe on the other hand was staring like and idiot at Jenn. She didn’t seem to mind one bit.

Jenn was wearing a high waisted skin-tight jean with little black booties. She had a satin crop top that was doing its absolute best to hide her tits. It was a valiant effort but alas, futile. The inch or so of exposed tan skin between her jeans and top was just so much sexier than it should have been. She also had big hoop earrings with her blonde curls that were the finishing touch.

Emy had on this barely-there dress with little-to-no shape. It allowed her runway figure to announce its existence quite loudly. Her legs were infinite.

And Kate honesty looked incredible. She had on a skirt pulled up high with a zipper running the length of the front. And one of those tiny ribbed t-shirts that Rory Gilmore probably owned. Her ass was liable to just tear through the skirt. The way she walked, from behind, you’d think you were on a ship at sea. She also had one of those little plastic chokers on. Like wtf, how are those such a turn on? It’s not right.

For a few glorious moments Joe and I took it all in. I never wanted to stop looking at Emy’s legs, but I found myself stealing glances back at Kate more often than I wanted to admit. But in no less than 5min the magic was gone. Of course the hip one would not settle on a choice of venue. Something about a list of “actually cool” bars she had found on the most obscure of travel blogs. Even after two whiskies I was visually frustrated. Which is likely why when we finally did settle, Emy pushed to the back row of our ride next to me. Jenn nuzzled up to Joe in the second row, lucky bastard. Kate sat up front to make sure poor driver knew what bar she had specified.

I rolled my eyes and looked to Emy. To my surprise she was already staring at me, so that our faces were just inches apart. I quickly looked back forward, but she leaned in even closer. He hand slid up my thigh to give it a firm squeeze. “Relllllax,” she whispered. She elongated the first syllable and I could have sworn I felt the faintest flicker of her tongue on the tip of my ear lobe. I goddamn near fainted.

The rest of the ride I couldn’t think of anything else. She had turned her body towards me so our knees pushed together and she was gently tickling the back of my neck just at my hairline.

— People, if you have a partner, do this. They will love you with the undying fire of a thousand suns. —

By the time we arrived, I was really only interested in being with Emy. Was not interested in the city, new places, meeting anyone, or even really drinking. Just wanted to get as close as I could to her. So you’ll understand , why I was so fucking frustrated to see that the place Kate had insisted on. It was hyper crowded, too loud to to talk, and full of these tiny high-top tables. No booths, no dance floor, and they served their food one like reclaimed stop signs or some shit.

We didn’t last long there, thankfully. We ordered a round of drinks and appetizers and took off. I was more frustrated than ever with Kate, she was making the whole night more difficult. But we overruled her and chose a little club within walking distance of our hotel as our next stop. I tried to relax and just think about what kind of sweet moves I could bust out to get Emy to touch me a bit more. Oh yeah, I’m a fucking phenomenal dancer*.

*no not really.

So anyways, we arrive and stand in line for a few. The girls of course get pulled up the to front and Joe and I awkwardly follow behind. Jenn pushes to the front and smiles with her gigantic tits while the they check ID’s. She then grabs Joe by the hand and pulls him in. The bouncer gave us other three a half-confused grin, it was hilarious. Kate step in front of Emy and I and I found myself hypnotized watching her walk a few paces in front of us.

Each one of her ass cheeks is taking turn bouncing up and down, side to side. It’s like a choreographed display sexual energy, dancing behind a thin veil of fake leather. Truly a sight to behold. I’m brought back to earth when I feel Emy’s hand grab the hem of my shirt and pull gently closer. We settle into a little booth and order drinks. Jenn orders a round of shots for everyone and wastes no time. Kate passes on her’s as she had “a trauma surrounding tequila.” Dear lord. So Jenn does her’s too and then gets up to the dance floor. She turns back at all of and slaps he round ass while walking away. I look to Joe and tip my glass. He does one of these ? and then just sits there lol

I tried to shout over the music, “Go on! Get out there!”

We all look and Jenn is staring back at our table doing unspeakably smooth and sexy things with her spine and/or hips. Like fucking hell, no human ought or be able to make your lower stomach ache like that in such a short amount of time. Still, the bastard hesitated. I know he hates dancing and is very insecure, but at the same time, he really has to do nothing. Again, guys have it very easy. We can just stand behind a woman and do vague humping motions called dancing. While they are expected to like, have rhythm and flexibility, and shit.

“C’mon! Let’s all go,” says Emy. She grabs Kate’s hand and they go join Jenn. “Let’s go.” I lovingly but firmly shove Joe’s shoulder. In no time, Jenn is practically absorbing Joe. He looked like a helpless puppy, yet a puppy having the time of his life.

A whole sea of sharks covered in Axe body spray moved in surrounding our group. They were trying to mask their primal hunger as relaxed dancing but were failing at it. They were looking for an opening to shove behind any of the girls, especially Jenn. But she did not give them one.

She was bent over and looking back at Joe while her stunning breasts were falling out in front of her. He excitedly, yet with reservation, rubbed his pantsed dick against her ass. She started to laugh and reached back for one his hand and placed it on her butt. He was finally in the zone. He grabbed her hips and started to actually find the beat of the song. They honestly looked so good, I was getting turned on and proud of my friend at the same time.

My attention turned back to Jenn and Emy while I’m two-stepping like an idiot. Elbows at 90-degrees, fingers snapping. You know the move. But good lord, they were killing it too. Emy did this thing where she put her feet close together and slowing bent down with her hands on her knees, pointed out. Her little dress rode up her thighs and I could see her tight ass poke out. A thin lacey strap dividing it. I was transfixed.

But then Kate like, bent her knees and slowly gyrated her hips in front of Emy’s face. She softly grabbed the back of Emy’s head and pushed it to towards her pussy. I couldn’t believe my eyes. It was one of the hottest things I will ever witness. Both girls laughed and Emy stood back up. They pushed their bodies closer together.

Immediately the sharks started to close in, so Emy pulls Kate back over to me, as I step towards them. The three of us were all just kind of a blur or bodies. They were grinding on me, on each-other. I’m feeling lips, hands, tightly covered tits brush against various parts of me. The alcohols had really set in by this point and everything feels really loose and really good. My reactions are so delayed it takes me a minute to realize that Emy is behind me humping me like our roles are reversed…

— side-note, this is an fucking fantastic idea to do your partner as well, ladies —

And Kate is directly in front of me doing her very best twerk. Which is honesty fantastic. I can feel her ass clapping around my dick. I might have cum right there had it not been for the whisky. Fuckin take me back, please.

Well the music slows and all 5 of us are out of breath. We’re a sweaty, sexy mess. We go back to our booth. The cocktail waitress comes by with some waters and we are exceedingly grateful. She waits to take a drink orders. Of course Kate starts asking about everything not on the menu… my euphoric horniness for her and her ass are quickly dying away. I’m distracted though as I feel Emy’s hand slide up my thigh again. This time she sneakily brushes over my dick as she reaches across me to grab Kate’s arm. She nods up and we all look to see Jenn with her legs across Joe’s lap and the two of them making out like freshmen. Lucky bastard.

The waitress comes back with our drinks. We all begin sipping quick. I was eager to recapture my liquid courage for another round of dance-like activities. The hip one takes a sip of her custom-ordered beverage and makes a face. Here we go.

“I don’t think this is right. Are you sure you asked the bartender to spin around in circles counter-clockwise while mixing? It tastes like they were spinning clockwise.”

“Yes, I’m sure.” The waitress replies, annoyed.

“Well do you think you could ask them to remake it?”

“Jesus fucking Christ!” I blurt out. “This has to be why you got fired right??”

Jenn and Joe stop kissing and stare at me. The waitress stares at me. I feel my stomach drop. Emy looks at me, ice cold daggers.

Kate stands up, grabs her clutch and is already wiping tears from her eyes as she legs it towards the door.

“Well?” Demands Emy. “Fucking go after her.”

I stand up and catch up with Kate just as she is stepping out the exit.

“Kate, I’m so sor—“ I try and say,

“Fuck off.”

“Wait, just…” I reach for her shoulder.

She turns and slaps my hand away. “No! I’m fucking sorry I like what I like and you don’t like anything!” She snaps back.

We’re still walking fast back towards the hotel.

“Look I never should ha—“

“You’re just so laid back and cool but you just a fucking uptight as me!

“I know, I kn—“

“You act too cool to like anything that might be hip but you’re fucking full of it!”

“You’re right, I’m sorry, that was so fucked—“

“But you fucking liked it when you had your dick on me! You like my ass when you smacked it on the dance floor. And fucking staring at it all night.”

By now she’s storming through the lobby towards the elevator. I couple people glance up at the sounds of her rather vulgar accusations.

“Fuck, be quiet!” I whisper shout.

“NO!” She smacks the elevator button.

But she she stops talking all the same. She folds her arms and waits for me to push the button inside. We silently ride up to our floor and walk down the hall. With frustration she digs through her clutch for her hotel key.

“FUCK!” She shouts and stops. She folds her arms again

“Did you—“ I begin to ask but she glares at me.

“Got it,” I mumbled inaudibly as I dig into my wallet and pull out my room key. I open the door and push it open for her. She steps past me and walks in. I stand at the door and like a completely cave man, immediately watching her ass again. She turn and sits on the bed, locking eyes with me.

“Seriously?” She says with as much sadness in her voice as anger. She puts her face in her hands and starts to cry. I’m not sure what to do.

“Do you want me to g—“

“No,” she said behind muffling tears.

I stepped in the room. Honestly at this point I’m passing from the drunk-to-sober, back to drunk-ish confusion. I grabbed two glasses of whisky from the bottle Joe had brought.

“Ugh, I don’t—“ Kate starts.

“Just shut the fuck up and drink it.” I said as kindly as one can say such things.

She does. We sit in silence for a few.

“Kate, truly I’m sorry. I should have never presumed to know what happened at your work. Or blamed you. Or brought it up at all. It was such a shit thing to say.

“It’s fine,” she said coldly. She wiped the tears from her eyes and took a big breath. “You’re a little bit right, to be honest.”

I wasn’t expecting that. “Well, you’re a little bit right too,” I said. “I’m way too uptight and try not to like anything too much, especially ‘hip’ things.”

“Doesn’t that make you a hipster too?” She sneered.

“Huh,” I chuckled. “Touché.”

“Was I right about everything?”

“What do you mean?”

*** sexy fun time ***

She shot the rest of her whisky. “Did you like rubbing your dick against my ass?”

She said it coldly. I sat there dumbfounded. Very confused and growing increasingly hard.

“Did you like you like the way my ass felt when you smacked it?”

She sat her glass on the floor next to her, then leaned back with her hands stretched out behind her on the bed. She took no care to cross her legs.

Now I was gawking at her. He tight skirt was riding up. I could see red panties peeking between her legs. Her thighs, her throat, her brow were all still covered in a thin sheen of sweat from the club and angry walk back.

“Did you like the way my phat ass bounced up and down when I walked in front of you all night? Did you want to fuck it?

I set my glass down too and tried to regain some composure. “Did you want me to?” I asked.

“I do now.”

She turned over, onto all fours and crawled toward the head of the bed. She was arching her back like a fucking leopard. She kicked off her boots and sat up on her knees. She crossed her arms and peeled off her tiny shirt. Underneath was a red lace bra to match the thong I spied. She reached back to unhook it.

I began walking towards the bed taking off my shirt. And fumbling with my belt while I kicked off my shoes. Kate unzipped her skirt, still with her back to me, and unwrapped it like a towel. I stopped to stare at her fucking massive ass, in all it’s nearly naked glory. Her white cheeks were pressed together in precious claustrophobic unison. Her red thong just barely escaped out the top. The center section nowhere to be seen. She looped her thumbs in inside the waist band and began to peel it down. I got on my knees behind her but sat up tall. I gently reached around her throat from behind, my palm pressed against that stupid plastic choker.

“Leave them.” I ordered, looking down at the top of her head.

She looked straight up, locking eyes with me. “Yes, daddy,” She breathed out.

I felt the words rush past my fingers as they escaped her throat. I placed my other hand on her waist, arching her back even more. I leaned down and led with my tongue. She opened her mouth and met me with hers. She licked the underside of it, tilting her head back further to lick my lower lip and chin. With one hand she pulled mine up from her wait onto he small round tit. The other shot between he legs and played with her clit.

Her moans traveled along her tongue and soon she looked back down to my hand squeezing her breast. Her nipple was so hard against my palm. She pulled my other hand from her throat and smacked it hard against the other tit. I was squeezing both hard now, pressing them together. I was waiting for a sign to squeeze softer but it didn’t come. She breather out, “yes, yes.” As I played with her nipples. One hand was still between her legs, the other now reached back fumbling with my cock.

I took my hands off her tits. One shot back to her hip, one to her shoulder. I pushed and pulled, shoving face down onto the pillow. She turned her head to the side and moaned loudly. Her enormous ass was high in the air. She had he panties pushed to the side and two fingers inside her pussy. Her thighs were slick with her wetness.

I spread her ass with my hands and began kissing it all over. I dragged my tongue across it. I reached up and brought my hand down with a SMACK on one cheek.

“YES!” She cried out.

“You like that?” I asked with my huskiest of voices.

She moaned a long and low reply. I knelt down lower and began to brush against her wet lips with my tongue, right up against her fingers.

“Ohhhhhhhh”

I licked all around and sucked at her pussy, fighting her hand for space.

“Fuccccccck”

I drove my tongue in behind her fingers as far as I could.

“Ohhhh my god, oh my god!”

I pulled it slowly out and dragged it back and up, right over her ass hole.

“FUCK!”

She began to tense and arched her back. I smacked her ass again while she came.

“Oh fuck, oh yes, fuck, yes…” she trailed off with heavy breathing.

Finally she laid flat down on her stomach, her ass still reaching high above the rest of her body. She breathed slowly. And I bent over her. I kissed her shoulders, her neck, he ear, all the while pushed my dick against her ass. She began pushing back, twisting back and fort. He cheeks spread and wrapped around me. Everything was wet and warm.

Then she seemed to come too. She pushed up on her elbows and looked back at me. He face was a rosy mess. There was lipstick on the pillow. She grinned sinfully. She clapped her ass cheeks around my cock.

With one deft motion she reached up and shoved me onto my back. I went along easily. Then she swung her leg over me and mounted me in reverse. At first she just played with me.

She place her hands on my thighs, she twerked on my dick. Her pussy was still wet, and getting all over. She reached back with one hand and massaged my balls, coating them in pussy juice. Then she expertly dragged her nails up from the base of my shaft and gave my head a squeeze.

“Pleeeeease” I groaned out.

She threw her head back and laughed.

“Please what?” She asked.

I grabbed her wrist and her hips firmly, stopping her gyrations. She looked back down at me.

“Turn around and put my cock inside of you.”

“Yes, daddy.”

She slowly turned around. I saw her flat stomach and tiny waist lead up to her round tits. Her nipples were still hard and pink. Her tits were red and splotchy. She got up on her knees. She reached between her legs and grabbed me. She guided me in. She lowered herself down to my balls.

“Fuccccccccck you’re big.”

She lied right to my face. I grabbed both her hips and began thrusting hard and fast. She pushed down on my stomach.

“No,” she whispered, “let me.”

Then slowly, she started moving. Up and down, side to side, she was dancing on my dick. She picked up speed. Faster, and faster. She leaned forward with her hands on either side of my head. She shoved her tongue in my mouth. She twerked on my cock. The sound of her ass smacking together was deafening.

“Grab my tits!” She shouted.

I listened and smashed them back together. I leaned up and sucked on them. Biting them. Licking roughly across them.

“Grab my ass!” She cried as she threw her head back.

“Of fuck I’m gonna cum!” I shouted.

Immediately she jumped off my cock. She slid back over my body. With one hand she jerked me off, hard and fast. The other pressed one tit against my shaft. She stared down hungrily at it.

“Yes, yes, yes,” she cheered. “Cum for me daddy!”

That was it for me. I grabbed the back of her head with one hand while the other pushed against the head board. My legs tensed hard and my toes curled back as I came. It felt like it lasted forever. Her jerking slowed to match my rhythm. She milked my cock completely. The head was covered in cum. So were her fingers. And I could feel it drip down my hip. It tickled.

She pushed up to her hands and hung her tits over it. She leaned down and brushed them across the tip. I was so sensitive and groaned out loud when I felt one hard nipple flick across the head. She giggled. She pulled her hair to one shoulder and gave my cock my one long lick, kissing the tip. Then she crawled back up my body and kissed me. I wrapped my arms around her, filling one hand with ass. My tired cock pushed against her pussy as she wrapped a leg around mine.

We laid there for some time enjoying the come down… until we hear the rapid knock at the door.

Source: reddit.com/r/gonewildstories/comments/pagvz9/how_the_spontaneous_friendcation_turned_into_the