[MF] That night in Miami

As I find myself with another night and nothing better to do, I decide to get started on the telling of the sequel to “Raj unexpectedly hooks up with friend from high school”. This is going to be the story about unexpectedly hooking up with one of my best friends from college, Emily.

I forget exactly how Emily and I became friends. I *think* we met at my 19th birthday party, sophomore year of college, thrown by one of Emily’s sorority sisters who happened to be dating one of my fraternity brothers at the time. Truth be told this party was only thrown because my buddy asked his girl to. I was in this fraternity, but hadn’t been able to shake my shy shell and didnt really have this extended social network. My buddy’s girl invited her entire sorority and basically made it a mixer centered around my birthday. My buddy was a great friend.

At some point Emily and I met and connected the dots between some mutual friends predicated on the fact our Greek organizations tended to go in on events together and realized we rolled in some of the same circles. This is going to sound strange, but I’ve always known Em to be attractive in an objective sense, but we’ve always just been friends on both ends. We hit it off from day one and just become each others go to person. We talked about school, work, family, personal shit, and we gave each other shit and yelled at each other when we were being idiots. She was a friend – there was never anything sexual to it. That said, it’s worth describing her. Em is about 5’9, slender and athletic as hell. She’s always been thin as hell but works out as if she were morbidly obese to chase this crazy chiseled physique. I always laughed at how hard she worked out despite always being in phenomenal shape. I respect women going after whatever body they want, and Em wanted this, but personally I’m not into the super ripped look and luckily Em didn’t have the best discipline, so I appreciated the fact she had just enough body fat to still look genuine. This wasn’t ever something I consciously thought about, but always knew. She was hot.

Senior year she began to date a different best friend of mine, Joe. Joe was one of the few guys tall enough at 6’3 to really tower over her enough to make Em feel small which she really appreciated. They were a great couple. They made sense – both came from the same kind of traditional salt of the earth white people families in suburbs of major US cities – they just understood each other and got along really well. We all were part of the same friend group that lived together after college so Em and I never grew apart, our individual friendship always sustained this bigger group dynamic. After graduation Em’s wanderlust got the better of her and caused her move on, taking on some humanitarian cause in South America, I honestly forget what it was.

Em was gone for a couple years, bouncing around South America from job to job before coming back to live at home on the Cape while she tried to get back into the US job market. We kept in touch all the while, keeping each other as up to date on our lives as we were when we “lived” together. We met up for a fun weekend one summer when I was out in Boston from work, but otherwise, we were just long distance friends.

Em’s job search continued and eventually brought her down to Miami where oddly enough, Joe now lived too. He went down after they broke up for a change in scenery and ended up loving it down there. Despite being back in the same city together, Em and Joe never even met up to see each other, they’d both agreed the past was behind them and they weren’t apart of each others futures. The rest of our friend group had been kind of fragmented anyways since everyone split up (except me, I stayed in Chicago) so this wasn’t a major disruption to anyone.

About a year after Em moved down to Miami I found myself scheduled to be in her neck of the woods for a week for work. I had a pretty rough schedule with clients throughout the week, but I knew I’d have the weekend to let loose. The problem is, with Em and Joe’s split, I had to designate an night for each. At the end of the day, Joe is indeed a closer friend, I mean we were brothers, so I decided I’d see Em Fri night and crash with Joe on Sat and Sun till I flew back to Chicago.

The way it worked out, I had a few coworkers hanging around on Fri night before flying out Sat AM so in the interest of team bonding which my company is big on, I invited Em to join us for team drinks. Em bounced around from mediocre hourly jobs and never really settled on a career, so I knew she’d be super down to jump in on drinks we were expensing (reminder, I work in the corporate side of Chicago-area biotech). I also figured at some point we’d ditch my coworkers and go off to catch up on our own, so we both agreed thus was a reasonable way to start the night.

Em came to meet us at our hotel before setting off for a bar. It was so good to see her. It had been a year since I’d seen her for that weekend in Boston last time I was over that way and we just missed each other. Another reminder for folks: a lot has changed for me over the last year. All my life I’d been a pretty average dude – not quite pudgy, not quite in shape, smart, but too shy and quiet, generally not super confident. A lot has gone right for me lately, I settled into a great career, I found the work life balance to get into actually good shape, and I did a lot of self reflecting on my personal outlook and attitude and had become a more confident, genuine person. This was the first time Em was seeing the new and improved me.

(A reminder for newcomers and those who care: a bit about myself – I’m a 5’11, 175lb pretty cut/muscular Indian guy with a surprisingly solid dick that I’m still getting used to the realization about – at around 7” long and 5.5” around

The first thing she said as soon as she saw me was “Holy fuck, Raj, what the fuck, you look great! What have you been doing!” Em, always loved to let the expletives fly. She was no dainty girl. We always enjoyed swapping health tips so she genuinely wanted to know what I’d been up to. She always supported my efforts to get in better shape which were reasonably successful back in college (ultimately limited by my love for beer and food). With my love of science, I always balanced out her constant ADHD with fad diets with an appropriate dose of scientific reason and skepticism. She also knew I’d gotten out of shape hitting this rough patch a few years ago so I could tell she was really proud to see me looking objectively good.

We gave each other a hug to the sound of a thud as our bodies hit each other so forcefully and pulled each other in as tight as possible, half-jokingly trying to show each other how strong we were. We made some quick introductions with the rest of my coworkers and set off for the night on the town. We bopped around a handful of beach front bars with live music, just enjoying the sights and sounds that Miami had to offer. Em was my biggest fan – she loved seeing how successful I was, how much of a big shot I looked like expensing drinks during a night on the town with older coworkers despite the fact is was just a pretty boring week of corporate training with some middle aged nerdy coworkers – nothing glamorous. That’s just the way she saw it though. I could tell she was particularly impressed with me that day. I was still getting used to my own semblance of self confidence, so all in all, I was just enjoying the night. My coworkers had planned to turn in pretty early which jived with my original plan to break off with Em. Not only were my coworkers older, in their late 30’s to mid 40’s – but they had 8AM flights back to Chicago so they weren’t supposed to be long for the night.

Lo and behold, of course I underestimated Em’s charisma. She has this infectious personality that people can’t resist, they just want to party with her. She’s great at peer pressure when it comes to drinking and convinced my coworkers to amend their plans to include something like 6 cocktails and several shots of tequila. As we get drunker, we start playing some games. I forget what the exact game was, but it was something that vaguely involved being able to dare people to do things (no it wasn’t truth or dare, I’m not that dumb). A lot of the dares landed Em and I close to having to go make out with rando’s and shit like that, but we managed to dodge each one. Me personally, I’m just not in to random stuff with drunk chicks and it felt especially weird around Em who’s such a platonic friend it she feels borderline familial. For her…it was odd. She knows how hot she is. She’s usually one to enjoy the opportunity to flaunt that to 1) let my coworkers know she can get it whenever but 2) she just loves to get it whenever.

It was what it was, eventually we all were drunk enough to head back to our hotel. Em had planned to drive back to her place but clearly was in no shape to do so after all her alcoholic peer pressure. It was obvious to both of us, she was going to crash with me and head home in the AM. We hadn’t shared a bed before this or anything, but it also wasn’t a weird concept to think about. Again – the platonic nature of thus friendship was the hallmark of it from the get go. We drank some more with my coworkers some more outside one of the conference rooms, taking turns pulling from a bottle of whiskey we picked up along our way back. We were reminiscing about random college stories, entertaining my two older coworkers who at this point are clearly fantasizing about that era of their lives where they did fun shit like this. Or maybe not, both seem happiest married with kids – that shirt seems dope too.

Eventually everyone agreed it was time to turn in. As soon as Em and I get to my room, she insists on one more shot of whiskey just before making a bee-line for the bathroom. Regretting that shot, I mosey over time the suitcase I’ve been living out of for the last week and grab a pair of athletic shorts and a sleeveless shirt to sleep in out of courtesy given that I was sharing my bed with Em. I get changed quickly and hop on the king bed and just sort of splay out. Em comes out of the bathroom, her jacket tossed aside in just her black tank top and high waisted jeans that made her legs look like they went on for days.

Without a single hesitation, Em climbed into bed and snuggled up on my chest, nuzzling into my shoulder under my arm while she wrapped her arms around me. Again, we hadn’t explicitly cuddled before, let alone in bed, but still this didn’t feel weird. I love her, it’d been a while since we’d seen each other and we’d both been through hell since then so it was just kind of nice to hold each other.

Then she looked up at me. It took me a second to recognize that look. I was still getting used to my newfound confidence and how women reacted to the new me. Then I recognized it was the same look Jess has given me that night back in Chicago last December. Before I knew it Em lept up and kissed me. I pulled her in closer and just went with it, still not in an entirely sexual context, I just loved her as a person.

Things quickly turned and the tone was explicitly sexual. Clothes started flying off until I found myself naked, peeling Em’s blue lace thong off. Of course she was wearing a blue lace thong. I started to notice weird things I’d never noticed before…because I’d never looked at her this way. Nothing gets me going more than a flat stomach, which Em had, but I also somehow never noticed she had a crazy nice ass! I guess all those squats she did in the gym actually did something ¯\_(ツ)_/¯

I had to give it a solid grab, so I did. I had to imagine this was super weird for Em too. I genuinely never expected her to have ever thought of me in a sexual context either. Not only was I not her type back in college, being a bit out of shape and quiet, but we just genuinely were friends. It was clear, though, that Em was attracted to my new body and confidence to boot. This wasn’t necessarily premeditated – she just saw the opportunity and was feeling it so she went with it – that’s all.

I decide if we’re going to do this, I want to leave her with a good impression, so I decide to get to my favorite part of sex – eating her out. I slide down and get to work, probing the entrance to her skit with my tongue, gliding up and down before moving in to lightly suck her clit. I start to pay more attention to her clit, sucking harder and starting to use my upper lip and nose to rub against her pelvis for added Sri stimulation, letting her gyrate against my face. I can tell she’s enjoying it as she lets out a few shy gasps and grinds harder and harder into me. The thing is, I don’t think she’s used to being treated this way. Joe is my best friend but all in all he’s kind of a meathead who’s the kind of guy you expect to be just a dude with a big dick who gets by on that. Sexually though he’s just a vanilla/macho dude despite otherwise being a loving/caring dude when it came to her.

Em continues to writhe about – but the thing here is – Em is the kind of girl who appreciates a guy like Joe who’s just down to business. After a few short min, she’s tapping me on my shoulder asking “Why aren’t you in me?”

“Fuck you, Em!…wait, I am” I thought haha. Far be it from me to let her question me so I decided to remedy the situation ASAP. I climb up on to her in missionary and slide between her legs. I reach down and feel how wet she is both from my saliva and her own juices that were flowing when I was going down on her. I grab my dick and rub it against her opening up and down to tease her a bit. Like I said, Em is one who likes to get down to it so she takes it upon herself to push on to me and slide on to my dick. I have no idea if I measure up to Joe or not – never saw his junk – but I can tell she’s appreciating what she’s experiencing so that’s enough for me to be happy.

CONTINUED IN COMMENTS

Source: reddit.com/r/gonewildstories/comments/eba0g9/mf_that_night_in_miami