How a MILF at a softball game wanting cock saved my marriage (LONG – x-post from r/truebigdickstories) [MF] [Cheating] [Group] [Swinging]

I’ve been posting on r/truebigdickstories and it was suggested I post here.

Long story short, I’m 47, a widower, and fighting cancer these days, and I’m recalling my previous experiences, focusing on the big dick centric stuff b/c of that sub. But I was kind of a slut in my younger years, having slept with 100-ish women, and being endowed (9 inches or so) played a role in some of that. Most of it had nothing to do with that, but whatever. Anyway if you want to see more, see my post history.

And I know I’m wordy — I’ve tried to go out of my way to make it short. It’s still long though — I tried.

Before I get to it, I need to explain how my wife and I got together.

When I was younger (high school and mainly college), I slept with way too many women. Over 30 or so… I can’t really keep track. I had lots of girlfriends (call me a romantic, but most of the girls I slept with were girlfriends). I tried not to sleep with random girls who weren’t girlfriends though it did happen 10 or 15 times, sometimes on accident and sometimes for sport. But I did go through girlfriends like water, I’ll admit.

[MF] in the pool, and what came later

This happened on my honeymoon with my second wife. If you need details: I’m 6′, a big guy, shaved head, beard. She’s 5’8, shoulder-length brown hair and light green eyes, curvy (spectacular boobs and amazing hips), and unbelievably sexy. She brought two wonderful bikinis on our honeymoon, although this story happened on our second day while she was wearing a (relatively) chaste strapless one-piece. At this point she was 30 and I was almost 40.

My wife is a bit of an exhibitionist — we’ve had semi-public sex, as well as done BDSM play in public which included her having multiple loud orgasms — but that stuff had fallen off in the past year or so as our lives got more complicated. Still, we always touch each other casually, and have a lot of intimacy.

So anyway. We’re at an all-inclusive resort somewhere outside of America, and the weather is warm and sunny. We have an early breakfast, and then go down to spend the day at the pool. We claim a spot for our stuff, get some towels, and then get in. It’s pretty dead there — maybe ten other people in the entire area — although the pool is surrounded by buildings full of rooms, and at any time someone could see us.

Consequences [MF] Teacher catches a student cheating

Consequences for Our Actions

“There she goes again, looking at her neighbor’s paper! She is so obvious. She has to be the worst cheater ever. Now she is looking at me and acting nervous. If she looks at Shelly’s test again, I am taking her exam away” Joe thought to himself as he sat at his desk, pretending to grade the previous period’s final exam. Hailey, the student in question, was sitting a mere three rows back and her nervous eyes kept darting to, and then staring at her neighbor’s paper.

Out of the corner of his eye, Joe saw Hailey check to make sure he wasn’t looking, and then obviously look at her neighbor’s desk while and feverishly copied down Shelly’s answers.

Joe stood up, buttoned his jacket, calmly walked over and grabbed Hailey’s paper without saying a word. He then walked to the back of the classroom nonchalantly. He could feel her angry stare on the back of his head.

He stopped at the back of the room, turned on the heel of his black leather dress shoe and surveyed his class. Forty or so high school seniors were sweating to finish their chemistry final exams. He saw Hailey slouched in her desk, twirling a strand of her long, wavy red hair while with the other hand she defiantly scribbled on her desk.

Sweet Tooth [Ageplay] [MF] [Oral]

Well I don’t really know how to start this story so I’ll just fill you in on the basics first, my name is John. I guess I’m what many girls would call a silver fox, or at least that’s what I’ve been told. I’m 47, I’m no Greek God by any means but I’m in shape. This story isn’t really about me though, it’s about my girlfriend Emily. Now she is a beauty, kicker is she’s only 18. How I ended up with a beautiful girl like her is beyond me but I’m not going to complain in the least. She is the daughter of a friend of mine and after she turned 18 she decided that she wanted a older man in her life and I fit her just fine. The first month or so of us dating went great, hell the sex was amazing but then something happened that really drove me crazy.

[M]y [f]irst time. Virgin story.

I am twenty eight and my first time was during this past weekend. I have always had difficulty with meeting new people, I can have pretty bad social anxiety. Over the course of the summer I tried various dating apps: OKCupid, Tinder, Bumble, and many more. At first I was simply looking for someone to build a relationship with. After two months being stood up multiple times a week I just gave up on dating apps and decided to check out craigslist casual encounter ads; nearly all of the ad’s on craigslist are fake or the poster is looking for a pornstar bull.

I went back to the apps and eventually discovered an app called Feeld (formerly 3nder), the purpose of the app is to help connect people for threesomes. A threesome is something that seems exciting and worth trying out. After a few weeks of swiping I finally got matched with a girl who had just gotten out of a long term relationship and was looking for no strings sex. Her demands where that I be rough and that I go down on her, things that fortunately I was very interested in doing. We spoke for a day and made plans to meet but her schedule got busy. A few weeks passed and she contacted me and we met that night. She was hanging out in a college town, we wanted to get a hotel but it was expensive due to a home football game.

A hot night with our sexy Columbian friend (MFF, bi)

A few years back my husband and I had a very good friend, let’s call her Adriana, who we had been spending a lot of time with. Adriana was stunning. Long dark hair that fell to the middle of her back, beautiful tanned skin, big brown eyes that a girl could just get lost in, a tight, fit little body and some very expensive tits that I struggled to keep my eyes off of. And her thick Columbian accent had me working very hard to keep my composure.

But Adriana was monogamous and my husband and I were not. She wanted a family someday, had a guy that she’d been casually seeing for a few months and we settled on just staying friends. I watched a very tender and intimate friendship grow between her and my man and I would often wish I could see him buried deep inside of her. This man could easily have walked off the set of Magic Mike- At 6’6, he towers over my tiny frame, with striking blue eyes, and the perfect amount of muscles to fit his frame, not too much, but enough to have women staring when we’re out in public.

That night with my naughty Columbian and my big man (MFF, bi)

A few years back my husband and I had a very good friend, let’s call her Adriana, who we had been spending a lot of time with. Adriana was stunning. Long dark hair that fell to the middle of her back, beautiful tanned skin, big brown eyes that a girl could just get lost in, a tight, fit little body and some very expensive tits that I struggled to keep my eyes off of. And her thick Columbian accent had me working very hard to keep my composure.

But Adriana was monogamous and my husband and I were not. She wanted a family someday, had a guy that she’d been casually seeing for a few months and we settled on just staying friends. I watched a very tender and intimate friendship grow between her and my man and I would often wish I could see him buried deep inside of her. This man could easily have walked off the set of Magic Mike- At 6’6, he towers over my tiny frame, with striking blue eyes, and the perfect amount of muscles to fit his frame, not too much, but enough to have women staring when we’re out in public.

Rough sex with a hometown fuck buddy (m/f)

I recently visited my hometown for a few days, and while I was there I made sure to meet up with a fuck buddy of mine. The last time I was in town he and I fucked four times in one week, and while I was away we were constantly snapchatting and sexting each other. We would describe what we wanted to do to each other, and send photos and videos of us masturbating. By the time I was actually able to go to his place, we were desperate as fuck, and knew exactly what we wanted to happen.

Having some fun with coworkers (MFF)

This is my first GWS so please bear with me for any formatting mistakes. This story happened back in January of 2010 but luckily I was keeping a journal at the time and wrote out the events of this night in pretty good detail, this story is edited from that journal entry.

At the time of this story I was working a job that required a lot of out of state travel and a large number of coworkers spent weeks at a time staying in hotels. Most people stayed at the Holiday Inn and so did I, but this time I had decided to try out the La Quinta. With about 20 people, most of whom were between the ages of 22 and 35, staying in the hotels at any one time there tended to be a lot of after work dinner, drinks, and hook ups.

I [35M] Get Message Tuesday Afternoon From Horny [18F] Redditor While At My Office. It Was A Great Taco Tuesday. (With Pics) :}

Hello Everyone. I had another great Redditor experience that happened the day before yesterday.
My previous post about the 19 year old and Grandmas was met with rave reviews again, so i am happy to post this story.

I was sitting at my office Tuesday afternoon around 1p. I was already day dreaming about a chilly margarita and taco after work, but little did i know, what i was about to find in my inbox.

I see the magic orange envelope that says i have a message. Thinking it could be a response to a girl i messaged, i opened it up expecting to see the usual “thanks” or “you are such a naughty boy”. It definitely wasn’t that. It went something along the lines of, “Hi Daddy- I was reading through the GW Stories a couple of weeks ago when yours was on the front page and it was really hot. The fact that we live in the same city really turned me on but I was too shy to message you right away. Having not been able to get it out of my head the past couple weeks, i finally feel brave enough to say that i live about a 30 minute drive from you and would like to talk. I am 18, and the oldest guy i have been with was 29. Do you have Kik so we can chat further?”