That time I [M] fucked my girlfriend and my boss [F] in the same day [MF, MF]

This ones long, but I hope worth it.

I’ve written about [Isabelle](https://www.reddit.com/r/gonewildstories/comments/ahio0g/that_time_i_fucked_my_girlfriend_at_a_sex_club_mf/?st=JRTPSZSR&sh=4c9f22c7) before. She was beautiful with a pixie haircut, a round face, and the slim body of a someone who loved the gym. Basically she looked like lots of the girls I date, except she had the most disproportionally sized tits you’ve ever seen. I don’t know sizes, but let me just say it took two hands to hold one. I’ve been with lots of women and to have breasts like that on such a slender frame was incredibly rare, and super fucking hot.

So that was Isabelle. We lived together for awhile and had a modified open relationship. Monogamous in town, but anything goes when you’re out of town. This, for the most part, worked well, but it also lead to times like these, where I got to fuck her, and another woman, in the same day. (Same thing held for Isabelle. I can think of at least one instance where I joined her on vacation and I knew she’d been fucking this other dude pretty recently, but that’s another story).

This time, I had to go to Vegas for work. I was working for a boutique firm that was owned by a completely crazy little heiress. Let’s call her Mandy. Mandy was five feet nothing, with bleached blond hair and an eating disorder. She was hot, in a hot mess kind of way. The kind of girl you fucked during a coke binge and then pretended to loose her number.

Anyway, we’re in Vegas, for work, and a bunch of us are drinking, heavily. Mandy is getting sloppy, and she starts this combo of dissing my work, and then hugging me. She gets pretty nasty about my work and some of my coworkers get uncomfortable and leave. Eventually I try to leave too, and Mandy says, “oh I’m only kidding, you know I just say that ‘cause I like you.”

Eventually after far too many drinks the last few of us head up to our rooms. My coworkers get out of the elevators one by one till it’s just Mandy and I. I’m on like the 17th floor but she’s in a penthouse. When it’s just the two of us she leans into me and says “you’re not mad are you?” And grabs my ass.

That’s all the encouragement I need to grab hers and say “are you going to make it up to me?”

We start making out in the elevator, then the hallway. There’s only like two rooms on Mandy’s floor, but it still isn’t appropriate that I have her dress up around her waist and my fingers inside her, but whatever.

We get into the room and she immediately drops to her knees. I take out my cock and she starts going at it, lustily taking it deep in her mouth. I strip while my boss gives me a sloppy blow job, and then I pull her to her feet and strip off her dress and panties.

She’s super thin, with very small breasts, and completely shaved. I lean her over the bed and start fucking her, hard, doggie style.

Generally this is my favorite position, but she was so thin I didn’t feel like I could really fuck her. Instead I did a slow grind kind while running her clit that I know drives women crazy. When I felt like she was getting close I pulled out and positioned her so she could suck my cock while I fingered her. This worked, and she and I came pretty much together. She swallowed every drop.

It was four in the morning, by then and Isabelle was scheduled to arrive and join me (on Mandy’s dime!) the next morning for a weekend in Vegas.

“I should probably go” I said

“Yeah you should” Mandy replied. And I picked up my clothes, and got dressed.

The next morning I wake up to a text from Isabelle, “Landed! See you soon!”. I shower, order room service breakfast and have a big ol pile of bacon and eggs in me by the time I get the text “what room are you?”.

Isabelle arrives and unloads her stuff. She feels gross from the plane, she tells me, and she wants to take a shower before we hit the pool. She showers and comes out wearing a two piece bathing suit that’s just preposterous. It’s a modest cut, boy shorts that hug her tight ass, and a top that covers her enormous tits, but it also just accentuates how incredible her proportions are.

“You look gorgeous” I say, moving toward her and running my hands over her ass. We kiss, we embrace, I pull her top off and caress her breasts while sucking gently on her nipple.

She starts to walk toward the bed and I pull off my shorts. Before she gets to the bed, I come up behind her and lead her to the wall length window that overlooks the pool and the Vegas strip. I push her up against the window, pull her shorts off, and plunge into her from behind.

She’s soaking wet and soon reaches down between her legs to massage her clit while I fuck her. Her enormous tits are knocking together and her hand is between her legs and all of this is visible to anyone at the pool who has very good eyesight or a pair of binoculars.

I loved the idea of showing off Isabelle (see my sex club story) and I think she loved it too. We didn’t last long. With one final stroke I jammed myself deep into her and came. The second woman I’d come inside in less than 24 hours.

The rest of the weekend was a blur of sex and partying with Isabelle. We barely saw Mandy, but when we did it was like nothing happened. I’d end up fucking Mandy a couple more times before I left that crazy job, but never in such close proximity to fucking Isabelle.

Source: reddit.com/r/gonewildstories/comments/anxxm1/that_time_i_m_fucked_my_girlfriend_and_my_boss_f