[MF] booze, coke, anal. fucking my 60 year old boss

So this happened when I was working in the mailroom for a big real state firm. I was 22 years old. I worked in retail and hospitality ( waiter), but this was my first “real job”. I come from a lower middle class family. There was never any money for continuing my education so I bounced around shity job after shity job to help fund my associates degree.

The mail room had four full time employees including me. The building we worked in had four floors and we were in the basement. Each one of us had our own floor that we were in charge of. I had the top floor, this department basically dealt with rentals. Listing available apartments, collecting rent, showing apartments. The busiest time for me was the end of the month when all the fucking rent came in ( this was 06-07, digital payment was not what it is today). Anyways, I had to individually place all the rent checks in these file folders, then give the files to the manger. She would always make me sit at her desk and read the checks out loud to her as she entered them into her computer… It was a long process.

I love being used [FM]

One more story I want to post tonight!

Last week I went on yet another tinder date, but the guy ended up being a drip. To be clear, I use tinder mainly to find people to fuck. Luckily, earlier that evening, I had been dirty snapchatting a previous fuck – let’s call him Sam. He’s Australian, and being American myself, I find him super charming, despite him being an obvious fuck boy. I hadn’t seen him (read: fucked him) for 4 or 5 months, but I had definitely sent him pictures of my ass since then. As my mediocre date was ending, I messaged him.

me: Are you going to invite me over now?

Sam: Depends. Are you going to suck my cock?

Me: obviously. Just let me get this guy to leave

Sam: just a warning. Im going to use you however I’d like

Me: sounds perfect give me 20 :P

I smirked to myself and tried to hide my phone from view from my date- but at this point I didn’t really care. It was already almost 12:30am on a work night, but I was determined to get laid – I had shaved, put on my favorite lacy underwear, and my ass looked great in my skirt.

Outdoor breakup sex [FM] [public]

I posted this 2 years ago on a different alt account, but I love this story and, being the anal (lol) person I am, I want to consolidate my sexy accounts…here we go:

After getting over the initial shock of this encounter, I realized this would make a very sexy story since I haven’t stopped being horny from it for the past 2 days. My [22F] (ex)boyfriend [26M] and I had been dating for about 2.5 years. We have always been semi long distance – we were both in school and 2 hours away from each other. This made it so when we did see each other about every 2 weeks, we typically fucked like bunnies.

A Birthday present I really didn’t expect [MF]

So I never expected anything else worth writting about would happen to me again after my annonymous motel fuck… I was sooo wrong…

This all started on March 10th at my Birthday party but the day before my actual birthday. I turned the big 3-0. One tradition among my friends is for your 30th you have to do an “on the spot”… this means you sit in a chair and everyone gets to ask you a question you cannot not answer “truthfully”.

Well after my birthday dinner of course I was plonked down on a chair and the names went in a hat. Everyone’s name goes in plus 2 that say follow-up… if that gets picked the previous person gets to ask another question. The subject is liquored up a bit before hand of course…

So the first couple questions immediately go to sex…

“How old were you for first time?”

“16”

“Ever been in a threesome?”

“Yes”

“Who in this room have you had sex with?”

“Carol” (A friend who Id known since highschool… and dated for 2 years)

When Work Gets A Little Messy [MF] [oral] [anal]

Sam was working behind the bar on a slow Tuesday and was just starting to close up when this beautiful, bodacious woman walks in and asks for a drink. Sam had seen her before and chatter with her, but tonight seemed different. She was wearing a strapless, black and white, thick striped dress that ended a few inches above her knees and a small black and white purse about waist height. It stretched around her curves making them seem impossibly bigger than usual. She sat down at the bar and started to sip her drink.

 

Yes Sir [MF][FF][MFF][Mdom][anal][oral][bd][long][Final Part]

Later that day we are eating lunch and talking. “Are you happy?” I ask.

“Of course.” she kisses me quickly.

“Because I was thinking about our promises and I want to make sure I’m holding up my end. Are you sure you’re happy”

“I’m so sorry about the mess. I’m happy but…You’re great in bed”

“You’re happy, BUT, I’m great in bed?”

“You’re great but sometimes I want more.”

“More sex”

“Yeah” she says embarrassed, “I know you’re tired and…”

“Sore?” I offer

“Sorry” she says more embarrassed. “It’s just sometimes I’m so…hungry. I’m masturbating like twice a day”

“Maybe I could help with that?”

“You’re going to help me masturbate?”

“Sure. Like the other day in the shower.”

Yes Sir [MF][FF][MFF][Mdom][anal][oral][bd][long][PartII]

“Where are we going now?” She wants to know

“We need to hit one more place and then we’re going home to drop all this stuff off and then we’ll get some dinner.” I take us to a little strip mall with a very special store. When we get inside she’s all giggly because the walls are lined with displays of dildoes and strapons, rope and leather, and all kinds of naughty delights. This is my favorite sex shop. I get the attention of a sales clerk, a girl with short cut hair and a bevy of tattoos. We go over the different vibrator options and select two, a rabbit and a smaller bullet vibe that kinda looks like a tongue. I ask for advice on lubes that would be good for anal sex and Claire blushes deep red. I buy a bottle of a water based lube in case we want something toy safe and silicone based one for longer anal sex sessions. I also get a set of silicone anal plugs in stepped sizes.

Yes Sir [MF][FF][MFF][Mdom][anal][oral][bd][long]

I’m an automation expert. I tell people I work on big expensive machines that make stuff. I get to travel to interesting places sometimes but mostly I wind up in little armpit towns. It’s good work though, it pays well and I get to be my own boss. I have a standing order to run a six month overhaul at a plant a couple hours away. This place is a real shithole and I hate coming here. There’s only one fleabag motel in town which is the only place to stay while i’m there. I keep thinking about dropping this client but the last time I went there was this girl. She works the desk at the motel. She’s probably 19 or 20 years old. She’s got long frizzy dirty-dishwater blonde hair that she lets fall across her face to hide her pale blue eyes. Her face is pimply but pretty. She’s the kind of girl you’d probably forget five minutes later if you didn’t look beyond her plain looks and dull demeanor. I have a day off and I hang out in the lobby and talk to her to kill time because there’s nothing else to do. She’s had a rough life. Her dad died when she was a baby in a motorcycle accident. Her mom is in and out of jail or rehab. She lives with her aunt and uncle who treat her like shit. She isn’t particularly pretty or smart or interesting. She has a way about her though. I can’t explain it and I can’t get her out of my head. Her name is Claire.

[MF] An ice Valentine’s Day

I am 22, she is 21. We’ve been together for almost three years now. We have extreme amounts of passion for one another, great dedication to each other’s satisfaction, and a fairly dormant knack for exhibitionism – one that pervades our fantasies and conversations, but which hasn’t surfaced much yet. A small step towards establishing it is this story.

It goes without saying that we are really fucking proud of how our relationship works. We have great communication and really kinky sex in the college age of people falling apart for dumbest reasons. We consider ourselves lucky and generous. This story starts on the eve of Valentine’s Day, where we had a fairly hilarious and slightly drunken conversation with some of our online friends that basically ended up suggesting that Valentine’s is only judiciously spent on a nice dinner, a movie, and then brutal anal on the couch. There is trust in inflicting pain, no?

I took some of the suggestions tossed around by said friends, on their sexual escapades, and it all went into this little plan.

[MF][Cheating] Destroying my engagement with Molly

Hello again GWS! All of the positive feedback I got after submitting for the first time here last week has me all excited to share again. I don’t have a *ton* of sexcapades that are actually worth sharing, but I have been around the block a few times and would love to share as many as possible! It was kind of a toss-up whether I share what happened when I ran [into Staci](https://www.reddit.com/r/gonewildstories/comments/602lrg/mf_staci_gave_me_the_best_going_away_present) again, or a story about how I was an idiot in my early twenties, cheated on my fiancé with a stripper, and ruined my engagement. A change of pace is always good, so I’m gonna roll with the stripper story this time around. This happened many years ago, and it’s *still* difficult not to beat myself up over how much of an idiot I was when I think back on it. Oh, and apologies if the build-up to actual sexy time is too long here…I kind of can’t help how I write these.
_____________________________________________________________________________________

**Relevant Background**