TL;DR A pushing 60 year old widower tells you about a recent event where he slept with a long-time female friend of his.
Disclaimer: If bareback i.e. “raw” sexual tales bother you then stop reading now. If drunkenness bothers you then stop reading now. It MIT bothers you then stop reading now.
I’d had a series of very shitty relationships, and make no mistake: a huge part of the years of epic failures was on me. Heck I even slept with an ex while she’d been married to someone, the father of their multiple children. Until I met my late wife I was a man who was kind of in the middle of the ocean on a deflating life raft.
I’ll never forget the day I’d met Jan (not my late wife) though. I’d been an up and down student in high school but did well enough on the SATs that I got a second look from some of the better schools at the end of my freshmen year of college. I ended up getting an admission to MIT and the first year was rough. Really, really rough. I was almost retaking my freshman year classes 100% and as you would expect the collective intellect and workload there was way more challenging than in the typical college. I almost returned to my state university as I was having a ton of problems hacking it. Plus tons of male students joined fraternities in their freshman years. I wasn’t really into joining a frat but at the same time I didn’t have those close connections and not a soul pinged me about joining a frat when I appeared at school. Thankfully I made it through the first year and then the second (technically I should’ve been a senior in college when this took place). By the end of my second year there I started to build some confidence and my grades were starting to be competitive. I was certain that I wasn’t going to royally fuck it up anymore. I just wasn’t sure that I was going to be any good, but I suppose that’s a story for another time. Actually, it’s not a story for another time, well, not unless there’s a goneboredstories here on reddit (heh heh?).
Suffice it to say that male:female ratios at MIT were way, way off. Jan walked gently through the classroom and sat down. I spotted her immediately. While I have always been partial to blondes (because of having more fun and all), as a brunette and with her funky sense of fashion (she obviously cut her own hair, and badly, but still… it was super hot) I was hot for her. Actually I’m sure that all of my classmates were hot for her as well. Her being 5’8″, super quirky, with a mousy voice, a strong point of view, a right leaning libertarian, the vintage heels she wore, and even though she sucked as a bassist in the band she played with — well, you get the picture. She was every nerd boy’s dream, and as a nerd boy myself let me confirm.
As a Boston guy I hung out with Boston people that I knew. It was inevitable that (a) we’d start a band and (b) that our band would be called something along the lines of Yoko B’oner. Yoko B’oner played a drunken gig on a Saturday night at one of the haunts in Cambridge and who would I see in the crowd but Jan. “I really liked your band,” she said after having tapped me on the shoulder following our set. “You were really fucking weird. And drunk. You’re drunk, right? You looked drunk. Oh, and let me introduce you to my fiancee, Tim.”
(a nuclear explosion happened in my head)
Tim was a completely normal guy and in her own drunken state Jan was hanging all over him. I envied that poor fucker, to be honest. I say poor fucker because I was a guest at their wedding the following year. Her tears were those of regret. I knew it. It’s not like she’d been pining for me. It’s just that she knew she’d married the wrong guy. It happens.
It was no surprise to me when I’d received her email about 10 years later. Actually, I’d have expected to have received her email a lot sooner. They were getting divorced. They would be the closest of friends. They would raise their cat babies in this loving partnership. It was all bullshit. I’d been long aware of these kinds of emails because at that point in my life I had seen them a million times by that point. Okay, so maybe I’d seen them 6 times. But still. Trends.
They’d lived outside of DC. She moved to Baltimore. I had been doing this daft defense contractor work and happened to be in town. So I asked her for dinner. We’d been to dinner before, but this time I had an agenda. I was going to tell her that we should be together. I’d seen all of those movies. Yes, simply by being honest I would win her love and affection and the sex would be unmatched in its sheer passion and regularity. Right before we considered dessert I laid it on her. She reiterated her fondness for me then promptly told me that we shouldn’t fuck with that by getting involved. That’s before I understood Womanese, so I did what any neophyte would do and set out a plan to Make Her Mine. But then again, that’s when I believed in romance. I used to think that you could move mountains with that shit. No, really. I used to believe that. But you can’t.
After that fateful night, when I’d gotten super drunk and after having thrown a bunch of dollars all over the table, staggered to the street to find a cab to get me the fuck out of there, Jan and I didn’t speak for ages. It wasn’t until this fateful night when I was playing with another Boston band, but this time in DC. Our band name? Well, that doesn’t fucking matter now, does it? We’d gone on the serious route this time, so it was nothing like Yoko B’oner. It was more like Mirage or Steelosophy or some shit like that. Two of my bandmates had been in Yoko B’oner, and yet here we were playing this weird adult contemporary jazz shit in DC.
We finished our set and I was enjoying a sparkling water. I’d gotten really fat in times past, given all of the drinking and all, so I mostly abstained. “Hey,” said the female voice after she tapped me on the shoulder. “I really liked your band. You’re surprisingly not that weird and you all should be commended for your apparent sobriety.”
I turned and grabbed her in a hug. I’m a huge guy and I lifted her off the ground.
As fate would have it our band didn’t have a place to stay that night and she invited us to stay with her. Jan and I stayed up all night chatting and laughing and I almost invited myself into her bed. But I didn’t. I was married after all, and although my own situation at home wasn’t that great, I just couldn’t pull it off. The following morning we walked through her neighborhood in the city as we sipped our coffee. She divulged that she’d been seeing a new guy and that she’d thought it was serious. At some point as we walked she took my hand and we held hands as we walked. I didn’t do anything except to go with it. In the following months she invited me to engineer some tracks with the band she was working with, and I gladly did so.
The sessions were okay, I guess. The band played kind of meh no matter my prodding. The end results were better than I had expected and Jan laughed when she told me how good I’d made them sound. I suppose that was brutal honesty. When I flew back home, and at that time my future wife and mother of my children was only recently in my life, I’d not gotten Jan’s voicemail on my cell. I listened to it as I waited for my new partner to pick me up at the airport. Jan’s voice was soft as she told me how much she’d enjoyed seeing me and that she hoped that we could do it again real soon.
Time passed and I didn’t hear much from Jan (nor she from me) via email. When things got sad and sick at home I didn’t reach out to most people. When I became a widower that kept me more inside.
I reached out to Jan a year or so after this all took place at home and she said that we should meet up for dinner next time I was in town. She was living in New York City then, working as a writer at one of the well known publications. As she knew all of the best hole in the wall places to eat in any city I let her pick the place. When I arrived early through a ride share I’m certain that my jaw dropped when I saw her. Her body was every bit as shapely as before, but the black dress and high-heeled boots she was wearing along with the amount of cleavage she was showing (this was new!) and the fact that she didn’t dye her hair to make it seem like she wasn’t graying had me hooked. Plus she had expertly used either a very subtle perfume or some kind of body wash and she smelled amazing. I love visiting NYC, but when you make something smell good on the streets there then that’s simply a master stroke.
We laughed a lot over dinner and while she had apologized for both having not attended my wedding(s) and for not having sent a sympathy card, I got it. She’d never remarried and as she explained she never got back on track with relationships. Dinner was done surprisingly early and when she asked me if I’d like to see her apartment in midtown I said that I would. We walked many blocks through the city as it was an amazingly beautiful night. She’d taken my hand again. I was walking through midtown with a visible erection. NYC is such a magical place where you can do shit like that all day and all night.
Her apartment was super nice and with an amazing view of the city. As we both hadn’t been drinking anymore we shared cheers over clinking our glasses of sparkling water.
“So,” she asked as we stood near the wall outside of her kitchen. “Do you remember the sessions you did with my band back in the day?”
“I remember.”
“Do you remember anything else about them?”
My mind raced back to the night when I ran my mouth at the restaurant as I’d professed my love for her.
“Well,” I replied. “Outside of your band sucking it long and sucking it hard, I remember that you were pissy when I left. Why was that?”
“Fuck you,” she laughed. “Why would you even say that?”
“Say what? That your band was phoning it in?”
“No, about the pissy part.”
“Well, you were. If I didn’t know better, and maybe I’ve never learned, but if I didn’t know better I’d think that you’d wanted to fuck. I mean, you didn’t come to my weddi-”
She didn’t say another word at that time. She just grabbed me in a hug and held me tight.
I snapped my right hand up and forced it between her legs. I could feel the heat coming from her pussy.
“Oh my god, what are you-” “Ohhhhh”
I couldn’t have written this Harlequin Romance shit better myself. This was real life.
I got a finger inside of her. “Fuck my finger!” I told her. “That’s it.”
The heels of her black boots clanked on the floor as she fucked my finger. Right before she came she grasped my right forearm with her fingers and held on tight. There was no squirting and without apologies I will tell you that a woman squirting turns me on, but when she came down from cumming she turned and told me to unzip her. She grabbed me by the hand and pulled me towards her bedroom then shoved me on to the bed. Her dress fell to the floor and she ripped at my belt buckle and zipper. I was hard and precum was pouring out of me. She slapped at my hips and then pulled my pants down around my ankles.
She jerked me a few times and then got on top of me. She’d not been wearing panties and I knew that already. Instead she was wearing nothing but boots and her bra now. She gyrated her hips and I was inside of her almost instantly. We both gasped. Thank goodness we weren’t in DC. There would’ve been a congressional probe about her screaming by now. #nocollusion #bitchesgottascream #justkidding
As she deliberately rode me, she snapped her bra off. Both of her nipples were pierced and were adorn with a couple of barbells. She wrapped her arms around my head as she fucked me as her tits were smashed into my face. I nibbled at the barbells as I was able. She loved it.
“I’m sorry I missed your wedding,” she told me, driving her pelvis down into mine. “Ohhhhh”
We literally had this conversation that we should’ve had years ago as she slammed herself on me. Now I’ve never fancied myself as a porn star lover, but this is one of those times when I was able to fuck and fuck and fuck. I pushed her off me and got on top. One hand was around her neck, and I guided our pace then from on top.
Then I started my own conversation. What the fuck was going on here?!
Her legs were over my shoulders when I’d finally had enough. I didn’t even ask for permission. I just seeded her. I hadn’t had sex for two years and I’m sure that the volume was high. I just kept pumping and pumping and pumping. She probably couldn’t get pregnant anymore but still… your mind plays tricks on you. A younger me would’ve become aware that he’d seeded a fertile woman. This was different though.
For the next 4 hours (4! See also: star, porn) we fucked and fucked and fucked. The next day we repeated. It was fucking magic. 3 times in my life (3!) I’ve had sexual chemistry like this with a woman. My late wife was remarkable and we shared this chemistry as well. What I’m saying is that I’ve been lucky is all.
Source: reddit.com/r/gonewildstories/comments/bf3o0x/mf_because_i_changed_my_mind