[MF] An old friend from high school and my first creampie

I tend to ramble quite a bit so this will probably be long. I’m writing this more for myself as an exercise in story telling and also to relive some fond memories. On top of that I tend to think the more I understand someone when I read these, the more enjoyable it is. I might do a series of stories if this picks up any traction so I’ll just get all of this out of the way in the first post. In any case, there’s probably more detail and context than you might care for and if so, feel free to skip down to the ********* for the action.

A bit about myself before we really get started: My name’s Raj- I’m a 27yo Indian living in Chicago. I’m about 6’0, 175lb, broad shouldered and recently for the first time in my life – fairly muscular/cut. I work in biotech for a household name firm – previously as an engineer until last August when I got a fairly large promotion over to the business side for a director level position. This came with a 55% raise pushing me well into 6-figures. This large of a raise may sound unrealistic – but I was fairly underpaid to start and this position was a counter offer to keep me from leaving for a dream position at an admittedly risky start up. I didn’t expect my employer to beat it, but they did so I was all the more happy to stay ¯\_(ツ)_/¯. All of this is to say – I was feeling pretty good about myself for a change. This promotion was a sigh of relief.

“I made it”, I thought.

I didn’t always know if I was going to make it. I don’t want to come off as shallow or elitist for thinking this is the bar for “making it”, but that’s my personal reality.

All my life I’ve been fairly successful – straight A’s in high school taking every single AP subject and graduated with honors with a dual degree in engineering and biology from a top university, but despite all that I know deep down I never really applied myself. I feel like I always did the bare minimum to meet the bar, but that bar had to be exceedingly high because of my extremely successful siblings who I love and look up to AND the fact that I’m the son of upper middle class immigrants who came here from nothing. What the fuck kind of schmuck am I if I can’t succeed after being gifted this fortunate of a start?

At heart I’m a perfectionist trapped in a lazy persons body. I know I’ve worked hard in life, but I’ve also always known which fraternity brothers could bail me out if I couldn’t get to a homework assignment once in a while. Come exam time when I was on my own, I could always cram enough to get an A, but a few weeks later that mastery of the material would fade. I wanted the A on paper only – I didn’t want to work hard enough to truly be that A student. I think I didn’t want to find out if I had it in me or not to be that person. I really wondered if I’d squandered my potential.

When I graduated I had the grades but nothing else of substance to land a top tier job. I was on the bottom end of great. I ended up with my current company as an intern thanks to a recommendation from someone who knew me at one of the harder working phases of my life. Without that I probably wouldn’t have made it here. There’s probably a good deal of imposter syndrome going on here, but for once, with this promotion – I felt like I really earned something on an elite stage.

This story begins a few months later on a crisp, cool, lazy fall Sunday morning in November of last year. Enveloped in my down comforter enjoying the cool breeze from the cracked window, I scrolled through Instagram to find that Jessica, an old friend from high school that I hadn’t talked to in over 6 years, just posted from a brunch spot a couple miles over. A quick run down of Jessica: she was sort of my girl next door – 5’5 brunette with hazel eyes, probably 110lb, very athletic and slim with a firm round ass and perfect little tits that are just the right handful.

Jessica and I go way back to the first day of freshman year back in high school – we were seated next to each other in English first period. I’d just moved to Arizona the month prior not knowing a single person at this school which was literally 15x bigger than the one I came from back in Minnesota. I’d been nervous about the thought of having to make all new friends in this big of a setting. Not only was I reeling from the massive culture shock from Minnesota to Arizona – it just felt like everyone already had their cliques and had so much history together – most knowing each other since kindergarten – I didn’t know where I was going to fit in. Jessica and I became close friends over the years – best friends at times, a bit more distant at others, depending on which social circle I was floating in at the moment. Jessica was part of the cooler crowd. I could hang with them at times, but I always felt like an outsider. Deep down I knew this bothered me and hurt my self confidence, that I didn’t fit in with the cool crowd, but there were just other groups I was more comfortable with, like the band kids. All that said I’d consider Jessica a close friend – even without the rest of the popular crowd, we hung together one-on-one and with her older sister pretty often.

At one point I might’ve had a crush on her – at least I told her I did just before heading off to Chicago for college. I don’t know if I actually did – I was pretty confused back then – I didn’t know what feelings were, I was just bummed I graduated high school a virgin despite having several relationships that just never crossed that final finish line. In hindsight I cringe about being so focused on this, but hey, I was a 17-year old hormonal teenager. I’m going on too many tangents. Writing is hard. Nothing came of me professing my feelings to her – I did it via text after I left her house for the last time before I flew out like the wuss that I was. She responded in a friendly sidestepping manner and that was that.

After we split for college, we met up once or twice platonically during the breaks we coincided being back in Arizona for, but by the end of sophomore year that had all ended. We both were living year-round in our respective cities and our lives had moved on. She became just an old friend from high school that I occasionally passed on social media…until I saw her most recent Instagram post.

I didn’t really think anything would come of it – I just commented on the brunch post with a wave emoji. I was pretty sure she knew I lived here, though I then realized I wasn’t sure where she lived. We’d been out of touch for long enough that I wasn’t offended she hasn’t messaged, but a part of me was also surprised she hadn’t. Our history started loosely coming back to me.

“Shit, this is the girl I randomly told I had feelings for her like a coward”.

I hadn’t thought about any of this in so long. I think I’d blocked that out of my memory. Oh well. A few minutes later I get a notification she commented back

“Shit I forgot you lived here. Are you in town aaaaaand are you by chance watching the NFL games today?”

She was always a bit of a tomboy. She was a kickass soccer player in high school and college and is a huge Cardinals fan like her dad. Before I can respond, a few seconds or so I get a text.

“This isn’t possibly still your number is it?”

“Hah – it is!”, I respond. “Just saw your response on Instagram – I am in town! I have a few errands to run but should be free after 2/3ish? Where are you planning on watching the games?”

She had friends with her in the Instagram photo so I figured she was going to be at a friends place or a bar.

“Wow! So funny, I totally blanked that you lived here! I’m totally free but my friends are on trains at like 2/3 and my flight is at like 10 tonight. Feel like entertaining me for an afternoon? Haha feel free to say no, Jessica I have a life”

Ah so she’s got nothing better to do. I’m not offended, still a cool opportunity to catch up with an old friend. I tell her I’m in and that I’ll check in once I’ve wrapped up the few things I had to do that day. I go do some boring shit like drop my old modem off after cancelling Comcast and get my cars oil changed. I get a text that she’s at a dive downtown just as I’m finishing up so I head her way to pick her up.

It was surreal to see her. I felt like a totally different person all of these years later from when I last saw her – a better version of myself. Not only had I grown from earning some success, but I’d been through some shit that made me a more self reflective person. I confronted my flaws and came out of it a more confident person. I was proud to show her who I was and eager to catch up on her journey as well.

We hardly watched the games that day. Despite us both having changed so much, our dynamic was the exact same as it had been 10 years ago. Conversation flowed like we were still kids aimlessly driving around town with the windows down jamming out to Dave Matthews Band (I regret DMB more than I regret destroying the environment aimlessly driving…just…what the fuck?). I learned she had grown into a successful career in journalism after taking a chance on herself out in Manhattan after college and I got to tell my story as well.

With her flight not till 10, we decided to grab dinner and I knew just the place. There’s a small wine bar with small plates around the corner from my apartment that I frequent with friends, family, and often dates. I know all of the bartenders and staff – it’s just got a nice homey vibe, and part of me wanted to show off my regular status. I know it’s not going to lead to anything – she’s got a flight in a few hours – but I still wanted to confidently enjoy my redemption arc.

Not 5 minutes after we sit down she gets a notification her flight has been delayed to 11:30PM. All of that extra time quickly translated into another bottle of wine and the night rolled on. A couple of my Chicago friends roll through for a drink, my closest friend Gita who has been like a sister to me since our time together as kids back in Minnesota, and her friend Jamie. I introduce them to Jessica and the 4 of us hang for a bit and chat. Jamie also has to catch a flight that night and is also delayed till around 10PM. As soon as Jessica goes to the bathroom Gita is grilling me on what’s going on with Jessica and I.

I genuinely thought she was seeing what she wanted to see. There was nothing there – there never was. Jessica and I have always just been friends. I downplay it and tell her she’s crazy but she insists there’s something there, and gives me her approval of Jessica that I didn’t ask for, but still appreciate. Jessica comes back and it’s time for Jamie to head to the airport. Jessica decides she’ll chance it and leave a bit later given her delay so Gita and Katie peel off, leaving Jessica and I both fairly tipsy and alone at the bar with a half bottle of wine left.

All of a sudden I sensed what Gita was getting at. The way she was looking at me. The way she was touching my leg/arm/chest as we talked. The way sh— oh, wait – what? We’re kissing?!

Out of nowhere she went for it and kissed me sitting there at the bar. Our lips parted and I look straight into her eyes with a slightly confused look on my face as she smiles back at me. I kissed her back pulling her closer into me a bit for a second before parting again.

“How badly do you need to get on that flight tonight”, I ask.

Apparently “not very” because a quick phone call later and she’s gotten herself on the first flight out in the AM. Mark the bartender already knows what’s up and has grabbed our check and slid it over and corked the wine for us to go. I quickly pay with a generous tip for my friend and we speed walk the short 3 minute walk back to my place.

I’d be lying if I said this wasn’t my usual move. Back in HS I was always a little flabby and average, but over the last year I’d really focused on getting back in shape and I felt pretty good about myself – another new thing I finally felt I’d worked for. This coupled with my career trajectory over the last few years since joining this company had given me the confidence to get out and date more on apps. Girls loved the wine bar, and when we get back to my place – it’s always the same reaction. First they’re impressed I have my own place and then by how well decorated it is. The bar is generally pretty low for guys in their mid 20’s and I sort of lucked into a reasonably priced place that I struggled to afford until recently and I managed to decorate well with things slowly accumulated over years of traveling. I’d had a bit of success in the dating pool recently so I wasn’t surprised by her reaction. It was all this new found confidence. I down played it and we settled in.

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

We poured the rest of the wine from the bar that we definitely didn’t need so it worked out great that we didn’t touch it. As soon as we set the glasses down and we hit the couch it was on. Jess threw her leg over my lap and straddled me sitting up on her knees, both hands on my neck and face as she pulls me towards her. We made out like this for a while, exploring each others bodies with our hands and mouths with our tongues. She ground her pussy onto my rock hard dick bulging against the confines of my jeans. I slipped my hands into the back of her jeans and grabbed her firm ass and pull her into me as she grinds.

It took me until oddly late in life to realize that I actually have a decent sized cock. Guys have a weird perspective looking down at it and as a result of that I historically had never thought it was anything but average. I was never unhappy with it, but I didn’t think I was impressing anyone with it. It doesn’t help that I have fairly big hands so it proportionally doesn’t look particularly big. Turns out when I started dating and got more sexual experience I found partner after partner that struggled to fit me and seemed genuinely be shocked by it. The first few times I thought the girls were just being polite. I decided to measure it and found out that I’m about 7.2 inches long and 5.5 inches around. I looked through some data online to see where this placed in the population and was shocked. I guess when I lost all that weight and didn’t have as much fat at the base I uncovered more than I’d realized. I’m barely used to having a positive self image and now I find out my dick is big? How dumb was I to not notice these things earlier? I could have been this better more confident self years ago. Anyways, back to the story.

Source: reddit.com/r/gonewildstories/comments/dqv0nu/mf_an_old_friend_from_high_school_and_my_first