[MF] Sex with older, former co-worker

During and after college, I worked at my neighborhood supermarket. After I graduated, it was a much more miserable experience, but you bond quickly with other employees. One of which, was a middle aged single mom that had some similar interests as me. Those interests included sex.

Off the bat, she wasn’t a cougar. Pear shaped body with a sizeable ass, not bad looking, but not exactly pretty either. She was about 17 years older than me. We shared a love of science fiction and fantasy, so we had that go on when we had smoke breaks together. She also had a really blasé attitude towards sex, and would speak casually about it when brought up.

Eventually, I got a new job, and I promised I’d keep in contact with everyone, which was a lie. She friended me on Facebook, and said to hit her up some time. She then would message me randomly, and it became apparent quickly she wanted to fuck. I always had a thing for older women, and it had been a while, so I thought, hey, why not.

[M]y Best [F]riend was determined to make me cum

Hello all, I’m back to share another story of myself with my friend Elena. After so many people seemed to like my previous stories, I meant to put this one up but life got a little busy anyways onto the story!

[First story](https://www.reddit.com/r/gonewildstories/comments/560je4/the_night_i_had_sex_with_my_best_friend_mf/?st=1Z141Z3&sh=ab64d5b1)

[Second story](https://www.reddit.com/r/gonewildstories/comments/5631r6/watching_porn_with_my_friend_mf/?st=1Z141Z3&sh=ab64d5b1)

So this story actually takes place roughly a few weeks after my first story. Elena and I had been having sex fairly frequently and while the sex was great, there was one slight problem…I wasn’t really able to cum. At first it wasn’t a big deal, but as we kept having sex and well I kept not cumming, Elena started taking it a little personal. No matter how many times I tried to assure her it wasn’t her she still would feel like it was something to do with her. Little did I know this frustration she felt would lead to probably one of the best nights ever.

It was roughly a few days after she had her period, and Elena’s behavior after her periods vary but she is usually either really short tempered or she get’s really horny…I’m sure you can figure out which it was this time. But during that week Elena had been relentlessly teasing me with skimpy outfits that barely covered her ass, and doing various things to get me hard and then she’d leave me. That week was hell.

Late 40’s [F] and the college boy [M]: A first for both of us

Just discovered this subreddit recently and I’m a total nube to writing about my experiences–so hopefully these won’t be a waste of your time. Please be gentle!

Should probably start with a little explanation. As I was growing up I was tall, gawky, had glasses and an overbite. Then I was a wrestler throughout high school, got contacts, and dental work fixed my alignment to where I’m actually a pretty good looking guy (I’m told I look like the senior in Sixteen Candles), but I still have the perception of myself as a gawky kid with glasses and can still be somewhat shy until engaged and alternate between overconfidence and no confidence.

I remember hearing my dad and his buddies laugh about how ridiculous and unrealistic “I can’t believe it happened to me” letters that were in Penthouse (or Playboy? Both?) and that’s kind of how I feel about the experiences I’ve been fortunate enough to have–I don’t consider myself overly sexual or deviant, but I’ve somehow managed to have a lot of encounters that, upon reflection, are large in volume (everything from college girls to probably an unusually high amount of milfs/cougars) and kind of unusual (in semi-public rooms, fingering under the covers in front of the girl’s family, threesomes, with food, tying up, and so on) and seem like bs.

The time I realised we really werent exclusive part 2 – AKA Shame, sloppy seconds and almost anal [MF]

A continuation of this: https://www.reddit.com/r/gonewildstories/comments/58yu30/the_time_i_realised_we_really_werent_exclusive/

We went to have drinks with some of her friends in a shitty student flat that night. She’d warmed up a bit, but was still annoyed. Drinking games ensued, so it didnt take long for everyone to get drunk. At some point some random lanky guy arrived. After rolling a spliff that almost knocked me out, he said something about “needing some help” and she got up and followed him. I thought nothing of it.

And then, a few minutes later one of her girlfriends, Fiona, said something. “It’s cool that you’re so cool with it”. I smiled and said thank you, stoned and confused, wondering what I was cool with but accepting the compliment anyway. And then another dude appeared and asked where Darren was. Fiona casually replied “getting his rocks off… they’ll be done soon”.

All the pieces fell in place like a satellite crashing back down to earth. Darren was the sex god in her phone book. Darren was the lanky dude who “needed help” with something. I was apparently cool for being cool with my lady fucking another guy while I sat around in the other room. My head spun. I played it as cool as I could because I wanted to compliment to stick, but it wasnt easy. About twenty agonizing seconds later I excused myself to look for the bathroom.

The time I realised we really werent exclusive AKA someone else’s cum inside her [MF]

First post ever. There might be more. Who the fuck knows?

We werent exclusive. It bothered me, but not enough to not want her. I always wanted her. Sometimes I’d fly over to see her, sometimes she’d fly over to see me. We’d do normal relationship shit and fuck like bunnies and then we wouldnt see each other for weeks. Sometimes months.

I had a free week and a bit of cash, so I flew over to see her. We met in a pub by the train station and had some drinks with a few of her people. I’d try to guess which of her friends and friends friends she’d fucked. A couple were obvious… a little to gropy on the kiss hello, some cheeky grins and leery glances. It annoyed me, but at the same time, I knew that while I was around she was mine, which I could tell annoyed them. I couldnt help but imagine her fucking other people, and I hated that it turned me on, but it did.

How a Weird Cute Girl Cured my Depression. [MW] [Fdom] [mast] [reluc] [voy]

Call me Steve. I’m an average-looking, although lean, 26 years year old male.

A few months ago I moved to Sydney after completing my engineering degree and – let’s face facts – after my girlfriend, Jai, dumped me for another guy. Apparently, I was always studying and not being attentive to her needs. Her “needs” often centred on her interests, her friends and, well, shopping. I’m not bitter about her choosing somebody else, in truth, I did make my studies as a priority, but also I did love that girl, and I was depressed as hell for losing her. Moving to Sydney and into a tiny little inner-city flat while I looked for work didn’t help. I did low paying intern work during the day, and at night watched TV and moped.

It was a Tuesday night about 6.00 pm when there came a lazy rapping on my door. I sighed as I was about to do something and didn’t wish to be interrupted. But, as I never got visitors I was curious as to who might be knocking at this hour. Please don’t let it be religious nuts.

[MM] My first and only gay experience

One night I was looking to get with this girl who I’d been wanting for so long. We were both pretty drunk and when the club closed, we went to her gay friend’s house with some other people. She and I were cuddling and all of a sudden she just started crying in my arms. Her girl friend called her a taxi and they got out of there. I was bummed, but plenty of people were still hanging around so I thought I might as well stay. I got talking to the gay guy that was renting out the place and we ended up talking for a good hour. When we paused for a moment, I realised everyone had left. We started asking each other sexual questions and I was beginning to get turned on. I had never been with a guy, but I had jerked off to gay porn. He was a twink with bleach blonde hair. It must have been obvious that I was checking him out. All of a sudden I said “I’ve only ever thought about kissing a guy once before, but I can honestly say that I could probably kiss you right now”. I had never been so forward in my life, I rarely ever made the first move. He smiled and asked “Well why don’t you kiss me?” I started shaking, I was so nervous and turned on. I came closer to him and his lips met mine, first softly, then we had our tongues intertwining. He asked if he could give me a blowjob. I became nervous once again, I had never shown another guy my cock. He didn’t wait for me to answer and unzipped my jeans and pulled out my penis. Before I could drunkenly object, his mouth was around me. It was pure bliss. I’d been blown by plenty of girls who thought they were good, and I thought they were good, but this guy was an expert. After a while, we got up and went to his bedroom. “Oh my god” I thought to myself “Am I going to fuck him?” We laid on the bed and kissed passionately again, he played with my cock. I thought I should stop being greedy, and I unbuttoned his jeans, and pulled out his penis. It was about the same size as my own, an average size, but I remember feeling it, thinking to myself that it felt silky. It felt good. He pulled away from me and brought his mouth to my cock once more. Again, I began to feel greedy and so I pulled his mouth off of me. I didn’t fuck around, I wasn’t nervous any more. I popped his cock in my mouth and tried my best to imitate his earlier performance. I swirled my tongue around his head and went up and down on his shaft without trying to use too much teeth. I felt him moving around and thought he was going to cum soon. To my surprise, he was merely adjusting himself so as he could suck my cock while I was sucking his. We 69’d for a while, both enjoying each other, both in drunken bliss. Eventually we stopped. I was so horny, but I was really tired and drunk. We kissed a bit more and touched each other’s penises. He wanted more but I was becoming really disoriented. He put his back to me and we cuddled for some time, my cock resting just near his ass. He grinned against me, wanting me to fuck him, but I was exhausted. Eventually he relaxed, sensing that I was done. We fell asleep with my arms around him. I woke up around 5:00 am. Not much of a sleep. I had sobered up a lot however, and I realised how much I smelled of rum and horny sweat. Feeling of embarrassment started creeping into my psyche. I got up and began to get dressed. He woke up and asked if I was going. “Yes, I should go home. I have to work soon” I lied, “thanks for letting me sleep here, and thanks for everything else. I had a good time.” I hugged him and left. I called a taxi and went home. I felt so confused. Was I supposed to be ashamed? I thought I was straight. Yet, I had kissed and sucked a guy and enjoyed it immensely. I got home and slept.

[Group][MFF] Glow Party Orgy

I’m very new to the sub and an absolute beginner at telling stories, hell, straight up newbie being in an orgy but I’m going to use this medium to describe the best night of my life.

I have been living in Calgary off and on for the past three years and through that time have met some really amazing girlfriends that I have no strings attached relationships with. Without getting into too much backstory, I have introduced each and every one of these 4 women individually to a sex club in the city. I must be the luckiest guy out there or have a talent for finding them but each and every one of them absolutely jumped head first into the lifestyle. Needless to say, I have had many fun nights at the sex club but in all previous instances I let the girls play while I watched or I was lucky enough to have solo fun with them in front of an audience.

Well, last night all that changed.

Tale of a batshit crazy size queen [x-post r/truebigdickstories] [MF] [cheating I suppose] [public] LONG

You all are just swell with how you received my first story, so I’ll x-post another.

Same disclaimer from my other post: I’m 47, cancer, widower, but recalling my tales is a lot of fun. I slept with 100-ish women and I’m well endowed, so lots of stories in there. Check my post history for more. And I threw an r/NSFWIAMA out there just for shits and grins. And I’ll take requests if you got something that vaguely lines up with something I’ve done.

Sorry, it’s super long. I’m a writer by trade, hence I’m a wordy mofo. Too long for the shitter, friends. And very very cock-centric since I originally wrote it for that crowd, picking out stories that focused on that. Sorry if it sounds hokey.

======

This is a story about the most cock-obsessed woman I’ve ever known. It was a girl in college named Lindsey and, sweet baby Jesus, she was something else.

It was in my third year in school. I went to a little state school in the midwest. Let’s just call it Southern Western Northwest State. It was a small school (maybe 5,000 enrollment tops) and I was in the Humanities School, studying media and English.