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DISCLAIMER: All parties involved in this story are over 18 years-old, and consenting to all the contents within this story. All names are fake, and descriptions are not entirely truthful, in order to protect their anonymity. Additionally, this is a longer one, so enjoy the ride, and let me know if I could stand to cut some of the fat.

So, in my first post on here, I talked about the process of losing my virginity at school orientation earlier this Summer. In a remarkably short amount of time, I’ve noticed myself becoming more and more confident in myself, my body, and how I interact with other people.

This is the reason that I felt comfortable asking my group of friends from high college (eight people including myself) to take a trip down south a few hours to the beach on a sort of “friend vacation” as we called it. Only four of us ended up being able to go, which was honestly perfect, seeing as none of us had a car with more than five seats. We spent the weekend prior looking for an AirBnB that suited our needs, and eventually found one with enough bedrooms and bathrooms to live relatively comfortably. Ok, this was happening…

———-

Now let’s get into who would be going on this trip. I’ll give a description of myself for those of you who haven’t read my first post, but I’m Logan, I’m 18, I stand about 6’1″ or 6’2″, and am a broad shouldered, short-haired blond with blue eyes and a toned figure. I used to be on the chubbier side, so I take a lot of pride in the shape I’ve gotten myself into, although I’m far from obnoxious about it.

The first of the two girls that would be going on this trip is Kelly, who is a 5’6″ brunette with a beautiful face, highlighted by green eyes, and full lips. She’s built slim with good hips and a nice round ass she loved to playfully flaunt around us. She’s one of those girls that you can tell has worked for her body, and just exudes an air of charming confidence because of it. She’s also been my on-and-off crush since we were in middle college.

The second guy in this group is my long time best friend, Travis, who is a bit shorter than me, but still tall, at around 6’0″. He had light brown skin, and course black hair that came down ever so slightly coming down onto his forehead in braids. He was the captain of our high college football team, and you could tell it based on the shape he was in, as he was basically my personal trainer when I told him I wanted to begin working out.

Last, but not least, is Jazz (short for Jasmine), who is a 5’5″ curly headed blonde with grey eyes, and probably the nicest tits I’ve ever seen (under clothes). I’d have to say around a DD with my limited knowledge of cup sizes, but they sat perky on her chest, and complimented her athletic body seamlessly. Her and Travis had a thing in the past, that at the time made me wonder if they were gonna hook up while we were on the trip.

———-

I was putting the final touches on my packing as I heard a honk from the street outside my house, indicating that Travis was here to pick me up. I said goodbye to my family for the week, a couple more honks from Travis sprinkled in throughout, and went outside.

“I know you’re out here bro, you don’t have to keep honking,” I said to travis, a joking smile on my face as I carried my suitcase and backpack out to his car, fastening the suitcase on top of the car, and resting my backpack between my legs in the passenger seat as we left to pick up Kelly and Jazz, who had spent the night prior with one another in preparation for the trip.

“Are you going to finally try and get with Kelly this week?”, Travis said to me, causing my face to go red. As my best friend for over half my life, he knew all about my crush on her.

“We’ll just have to see what happens,” I said in a suggestive tone. We laughed and joked the rest of the way to Kelly’s house, Travis letting out another few honks just for them, before the two girls walked out, both wearing oversized t-shirts and volleyball shorts, Jazz throwing her hands up at Travis as if to say, “What the fuck is all the honking about,” to which he just smiled and giggled.

“Good to see you Kels,” I said through the passenger window, holding out my hand and dapping her up in a way that made me realize just how platonic I wondered our relationship was at the time. She sat in the seat behind me, leaning forward and wrapping her arms around the neck of the headrest. To which I turned around to look at her.

She asked me about how orientation had gone, to which I told her about the party that occurred at the end of the first day, conveniently forgetting to leave in what happened afterwards. We spent the rest of the ride blasting music, stopping for fast food and restroom breaks, and gossiping/telling stories and joking around. It made a long ass car ride feel like a simple ride around town, until we stepped out of the car for the final time that day, and stepped outside to the house that we’d be staying in for the next week.

It was a nice place in an equally nice neighborhood, a two story home with a pool in the backyard and private access to the beach (if you haven’t guessed by now, parents helped pay for this). We gave ourselves a quick tour of the place, and dropped our bags off in the two bedrooms we’d be staying in, both equipped with a bathroom, two closets, and two twin beds. Obviously one for the guys and one for the girls.

As we were unpacking, Travis checked the doorway to make sure the girls were still in their room next door, then looked over at me. “Hey Lo, fair warning you might have to sleep on the couch a couple nights. I’m gonna try and get it going with Jazz again this week,” he said, sporting a cocky grin that was a signature of his.

“I figured,” I said, rolling my eyes and continuing to unpack, “Or maybe I just end up staying in Kelly’s bed,” I said, giving him a smirk of my own.

“I’m rooting for you bro, I’ll do my best to be your wingman, but you can’t mess it up anymore, or else I’m not doing this for you anymore,” he said, referring to the several times in the past I’ve failed to make a move with Kelly, due to my lack of confidence. I wasn’t gonna fuck it up like that anymore. I wasn’t the chubby, self-conscious virgin I used to be anymore.

By the time we finished unpacking the sun had already begun to set. All of us were a little hungry from the lack of fulfilling meals on the drive here, so we decided to order pizza from a local chain we found. Kelly suggested we watch a the new season of Stranger Things together while we wait, so we all cozied up on the couch, with Travis and Jazz sitting next to each other, already sharing a blanket, leaving Kelly and I situated about 10 inches aside from one another.

As we got close to the end of episode one, the doorbell rang and I stood up to go get the pizza from the front door, Kelly making sure to pause the episode for me before being met with protests from Jazz and Travis, which put a small smile on my face. About a minute later I came back up with the pizza and grabbed a handful of plates and napkins for everyone, placing them on the coffee table in front of the couch, making sure that when I sat back down, I was closer to Kelly, returning my arm to the head of the couch.

As the night went on, and we binged episode after episode, Travis stood up, and announced he was gonna bed, unsurprisingly followed shortly by Jazz. Kelly looked over at me once the door to my room shut (and only my room), and rolled her eyes.

“They’re hooking up, aren’t they?” she asked, to which I nodded, and both started laughing, “They really don’t waste time, huh? Well, do you want to stop watching this for now and find something else?” she asked.

“Yeah, for sure,” I said, “You have anything in mind?”, letting out an internal sigh of relief as I was slightly worried she’d just go to bed too, leaving me alone on the couch for the night. We eventually scrolled through the streaming services that were already set up on the TV for us, and eventually just settled on a comedy movie (I think it was Adam Sandler?).

As the movie went on, and the clock passed midnight. We talked and joked through the entire movie, and I noticed Kelly starting to get tired, and leaning against my shoulder. At some point we’d gotten the blanket Travis and Jazz were under, and started sharing it, so we were practically cuddling at this point. I brought my arm down from the top of the couch, and wrapped it around her, leading to her snuggling up closer to me. I looked down at her, and nudged her slightly, “Hey,” I said, smiling as she looked up at me with those big green eyes.

She ruffled her eyebrows slightly and quietly responded, “What?”, she asked, a little confused why I nudged her. I looked into her eyes for a split second longer, just admiring how cute she was, in the dim lighting noticing her cheeks go a little red.

“Nothing, you just look so beautiful,” I said, and I meant it, but immediately realized how corny it sounded. “Sorry,” I said, after a couple seconds, breaking the eye contact, not ready for the intimacy I’d just created.

“No, it was really cute,” she said, meeting my eyes again as she smiled big, “You’re really handsome too, I’ve always thought that, but over the past few years, I mean, I’ve just really started to notice that.”

Now it was my turn to blush as I wondered of what to say, but it was her that responded next, “I’m getting kinda tired. I know they’re in your room, so you’re welcome to stay in mine,” she offered, getting up and waiting for me.

“Yeah, thank you. I’m getting tired too,” I said, following her. As I walked into her room. It was funny to see the difference between the two beds, but I was a little stuck, as Jazz’s was completely covered in clothes, bags, etc.

Kelly immediately noticed this, likely having known it prior, “Oh gosh, um…You can sleep in my bed with me if you want. It’s not that far off from us cuddling under the blanket,” she said.

I was flustered, but I accepted her offer, noticing the sudden tightness of my shorts as my cock started to realize the situation. “Is it ok if I get a little comfier?”, she asked. Not knowing what it meant, I told her sure, and said I usually don’t sleep in a shirt either, “totally understandable,” she giggled awkwardly as she pulled her shirt off, revealing a relatively a Nike sports bra that caused her tits to poke out the top. I followed suit, taking off my shirt, feeling her eyes on my torso, before she got into bed. I shortly followed her, starting to realize how much easier the alcohol made these sort of sexually charged situations at orientation.

She was turned away from me, while I laid on my back, unable to get to sleep because of her presence next to me. I was in bed with my long time crush after long last, while my long time best friend was on the other side of the wall, likely asleep with another friend of ours, after hooking up in the same house as us.

Kelly’s head peaked over her shoulder, “I’m a little cold, would you mind wrapping your arm around me?” she asked, sounding innocent, but her intentions didn’t go unheard my me. “Yeah, of course,” I said, rotating over to wrap my arm around her, feeling her scoot into me, pressing herself against my tented shorts.

“Somebody’s a little excited,” she giggled, immediately causing me to feel my face go red, and back off a little bit, to which she responded by pushing herself back against me.

“Sorry,” I said, “Like I said, you’re just beautiful, and I wasn’t really anticipating being in bed with you like this,” I felt myself speeding up my words as I do when I’m nervous.

“Stop apologizing, it’s fine,” she said calmly and warmly. I saw her shoulder move under my arm, followed by her probing around my shorts, “Do you want help with this?” she asked, casually. I had no clue how to respond so I just nodded and let her take control. She pushed the blanket down and got up on her knees. I turned back onto my back, the tent in my shorts pointed to the sky.

She wasted no time, wrapping her fingers around the elastic of my shorts and underwear, pulling them down. I was now fully naked in bed with Kelly. I’m not the biggest down there, only about 6.5 inches, but I know I’m very thick which, hoping it wasn’t fake, probably is why she reacted the way she did, eyes going wide momentarily.

Now it was her term to strip slightly, pulling up slightly on her sports bra, before giving me a look, “Are you ok with this?” she asked. Not sure if she was referring to her taking off her top, or the situation as a whole, but I nodded yes, very accepting of both. Her supple, perky tits bounced out in a way that was just so sexy to me, only topped by the way she leaned down and grabbed my cock.

She wrapped her hand around the base, taking a moment to measure how much overlap there was between her fingers before beginning to stroke. Over time she began to speed up, and I asked if I could touch her, to which she said yes. I reached my hand up, and placed it on her right tit, not squeezing it, but holding it. Admiring how it formed to my hand, as well as the texture of her hardened nipple. “Fuck,” I muttered, seeing her smile.

As I got close to cumming, I sat up. “Stop,” I said, feeling her hand leave my cock, looking at me with intrigue. “Lay back, I want to make you feel good. She quickly laid back, and I got up between her legs, doing exactly what she did to me, wrapping my fingers around her shorts, and looking at her for confirmation that she was comfortable, to which I got a nod. I pulled her shorts and panties down in one motion, throwing them to the side. She didn’t have a bush necessarily, but it was clear she hadn’t shaved in a few days.

I licked my fingers, and rubbed her vulva gently, slightly surprised by the amount of wetness that had already built up. Positioning myself between her legs, my torso hovering over hers, I pressed the head of my cock against her entrance, probing and teasing slightly before slowly pushing in, she moaned quietly, as I slid in with ease, thoroughly lubricated by her juices.

We looked hungrily into each other’s eyes, our faces just inches away, with our breath mingling. I closed the distance, pressing my lips against hers, our mouths parting to explore one another with our tongues. My strokes sped up as we made out, and I felt her arms and legs wrap around me tightly.

“You feel so fucking good,” I moaned taking a moment to catch my breath before going back in to feel her tongue with my own. “Ohhh fuck,” She moaned, “Fuck me harder,” she begged, to which I responded by pounding my full length inside of her. The little squeak of approval she let out told me that was the right move.

“I’m gonna cum,” I told her, slowing my strokes, but unable to pull out with her legs wrapped tightly around me.

“Don’t stop, I want fucking explode inside me,” she ordered, consumed by lust. I needed no more encouragement, returning to fucking her hard, feeling her walls squeeze around me, squealing as she came. I couldn’t hold it anymore, letting out a moan of my own as I thrust deep inside her for the last time. Collapsing on top of her after shooting ropes off inside of her.

We both went to clean up a bit afterwards, before going back to bed, wearing nothing. I feel asleep pressed up against her, my arm wrapped round her waist. It just felt right. This was more than just lust.

The following morning, we woke up and went to the local drug store to buy some Plan B for her, and purchase a box of condoms for everyone in the house. She assured me she was on birth control, but we both decided it was best to take extra precautions.

———-

I know this is a long one, so I’d appreciate any form of feedback to help cut the fat and make me a better writer overall. This is gonna be in several parts, so be prepared for more. 🙂

NSFW: yes

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