Illustrious_Weekend, Author at NSFW story

FWB Who Turned Out To Be Doing Porn [MF]

Random story: when I was about 23, I used to hang out with this single mom in her early 30s, nasty divorce in progress where he had been banging his secretary and ran off with her. She was broke, delivered packages part-time and juggling child care, but when her daughter was with her husband every other weekend, I’d bring a pizza over and we’d hang out.

She was very pretty, but we didn’t have much of a connection. Nice soccer mom type blond with C or D cups, but she was very vanilla and church-oriented, and honestly, not the brightest bulb in the chandelier. She didn’t want to get emotional anyway, so it worked as a FWB situation. Catch up, watch a movie over pizza and beer, fuck, and go our separate ways.

One weekend, I can tell things are a little different with her, and while we’re hanging out she mentions that she’s been getting hassled by debt collectors. She’s $3,000 in the hole from shopping online too much and her only credit card is maxed out, and it’s true, she’s bought some frivolous crap around the house, but that’s none of my business. It was really indirect and circuitous, but I can see the writing on the wall I’m about to get hit up to help her with money. Read more »

Our First Night With The Neighbor [FMF]

Last time I posted about this relationship, someone said they hoped I’d post about the first session. I couldn’t get to it then, but finally had some time free to bang out a draft.

The backstory to this is that about a year ago, our neighbor a couple blocks over, “Sarah”, kicked her husband out and filed for divorce. Sarah and my wife are well-acquainted. A busy professional, she wears her hair bleached blond and short, not quite as tall or curvaceous as my wife but likes to stay fit, too. I’d call her slim and perky, the type who wears athleisure outside of work and is generally pretty bouncy in conversation. They had little cardio-and-brunch girl dates going every few weeks, and after the drama with her divorce they started getting dinner and drinks at a local pub so Sarah could vent and get some moral support. Read more »

Loaned the wife out as a birthday present [FMF]

Kind of a convoluted story about how we got to this point, but about a year ago, our neighbor a couple blocks over gave her clown husband his walking paper. We’ll call her Sarah. Sarah and my wife are well-acquainted. Wears her hair bleached blond and short, also tall and fit like my wife, but with a slimmer, less curvaceous figure. She’s cute and perky. They do cardio-and-brunch dates every few weeks, and after the drama started getting dinner and drinks so Sarah could vent and get some moral support.

After a while, a lot of that girl talk started coming back to sex, because Sarah was happy to be single again and living her life, trying the things she didn’t while she was married. She’s a busy professional and jumped on some dating sites, and got a nice rotation up and running for herself pretty quickly, including another professional across the border in Montreal who is crazy about her but keeps it casual. We’d seen him in her driveway a couple of times. Read more »

The Disgusting Bar Bathroom Handjob [MF] [Cheating]

I’d just turned 22, moved to this college town and was getting settled in my new apartment. Making the rounds on MySpace and managed to friend a very attractive local girl who was working at some pub I didn’t recognize, managed to make a date for her that Saturday night. I was feeling great about that.

Friday night rolls around and after work, a few coworkers want me to join them at some place downtown, turns out it’s not exactly a great spot. Retro themed place with sawdust on the floor, a VW Bug in the doorway, and a wrestling ring in the middle, I don’t know what the hell was going on but I played along.

Then, two or three beers in, I’m wrapping up the night, come back from the restroom and some girl, not my type at all, we’ll call her Katie, stops me drunk. She’s slurring her words and puts her arms around me, starts looking at my teeth and asking if we can “just fuck and that’s it”, and if I can come hang out with her and her friends at another bar. Read more »

Fucking While Her Boyfriend Was Outside Looking For Her [FM]

I’d been seeing this Puerto Rican girl, we’ll call her Mia, for almost a year, on-and-off. She was a good looking woman, short with a round ass, dark skin, long, kinky hair and a sense of humor. Single mom around 29 or so, I was about 24. It was nothing serious, no real “dates”, but some nights when her ex-husband had her kid she’d just come hang out and then we’d go out for coffee in the morning.

We’d met on our commute, had taken the same train most mornings, she liked to talk but when I asked her to get a drink after work she’d blown me off with the “I live with my boyfriend” thing.

Then, when I quit that job, we lost touch but a married friend of hers had developed on me through MySpace. The next time that friend drove to visit Mia, she ended up messaging me and spending most of the next two weeks fucking like crazy.

That, I guess, caught Mia interest. She’d kicked her boyfriend out and I think it bothered her that I’d been interested but ended up in bed with her friend. The first time she came over for “dinner”, she’d made a point of telling her friend where she was going – and telling me she’d told her, with a little smirk. Read more »

Wifey’s Busiest Weekend [MF] [MF] [MF]

Quick story about the first time we had sex. When we met, we’d initially just started out as friends, first exchanging a few emails and texts then meeting for coffee at the shop a block away from my place to talk on Sunday mornings when we were both free. We’d flirt a little and had had a couple of lunches but nothing that seemed like it was going to lead anywhere, just general chat about life and career, she felt that oral and intercourse should be for monogamous relationships. I wasn’t down with that, so we were “just friends”.

Background is that she had divorced an idiot she married young and was trying to figure out how to enjoy life after a traditional and conservative upbringing in a Catholic schoolgirl uniform, but wasn’t really loving her options. She could see that I was having a good time being single she liked bouncing ideas about life off of me, but mostly she was stuck with two pseudo-boyfriends who were in a hurry to get married. One was a dull ex she’d had to give the “let’s see other people” talk but who was still trying to lock her down, who she’d mainly kept around for occasional sex. The other guy was aggressively interested but they weren’t really on “dates”, and she didn’t know what to think and kept it to making out and heavy petting. There were some real dates with others here and there, but having only had a few partners, she was against racking up numbers. Read more »

Train Trip, Part 2: One Night in New York with Finance Exec [MF]

Not sure if Part 3 of this will get written or not, since that encounter is hard to make a good story out of, but wanted to get this one up:

After making it out of Chicago on time ([https://www.reddit.com/r/gonewildstories/comments/adhz2d/train_trip_part_1_one_day_in_chicago_with/](https://www.reddit.com/r/gonewildstories/comments/adhz2d/train_trip_part_1_one_day_in_chicago_with/)) my trip was feeling pretty worthwhile so far. I spent the evening making small talk with a Russian woman who worked in “massage”, then fell asleep for the night before hanging out in the lounge car the next morning. We were running hours late. I was told that at least in those days, every freight carrier had priority and we had to stop to let each one pass, so what should have been an early afternoon arrival with plenty of free time turned into sunset.

Still, I made it. On the way out of Penn Station to Maria’s place in Chelsea, I decided to stop for a bottle of wine as a gift. I wasn’t sure if that was the right move or not, but it’d been a year since we’d really talked, and it felt important to make an impression on an accomplished older woman. I texted her to let her know I was on my way, then rang the buzzer when I got there. Read more »

Train Trip, Part 1: One Day in Chicago with Suburban HotOrNot Sub [MF]

When this took place, it was the summer after I’d just turned 21. I was still living in the tiny rural midwestern town I’d grown up in, at a job with two weeks of paid vacation that had to be taken separately, because they couldn’t afford to let anybody go for two weeks at a time. Sucked.

I was still hooking up with my high school sweetheart, a year older, from time to time, and occasionally meeting a blond from the Chicago suburbs I’d found on HotOrNot, a year younger, who was happy to drive to meet me so we could both be away from our parents and she could get treated the way she liked, which was mostly getting fucked like I hated her. I’d been the first guy she hooked up with after she dumped the high school boyfriend who took her virginity, and we had a thing going on where we talked a little almost every day while we went about our separate lives, but connected when we could to experiment. Read more »

Train Trip, Part 1: One Day in Chicago with a HotOrNot Slut [MF]

So this is going to end up a trilogy. When it took place, it was the summer after I’d just turned 21. I was still living in the tiny rural midwestern town I’d grown up in, and was working at an office with about six employees. I had two weeks of paid vacation that had to be taken separately, because they couldn’t afford to let anybody go for two weeks at a time. Sucked.

Either way, I was still hooking up with my high school sweetheart, a year older, from time to time, and occasionally meeting a slim blond from the Chicago suburbs I’d found on HotOrNot, a year younger, who was happy to drive to meet me and split the cost of seedy motel so we could both be away from our parents and she could get treated the way she needed. It was weirdly romantic, fucking her like I hated her made her feel loved and she was addicted to it, and we’d both been enjoying trying some things out on each other for a couple years now. Read more »