The first time I (30M) had sex with two women on the same night. [mf] [mf] [long-ish] [not hot] [some hahas] [some not so hahas] [some scumbag behavior]

>My old assistant manager recently got a hold of me to talk about old times and I’ve had some writer’s block lately, so I figure this’ll be a good exercise.

This is probably going to be pretty vanilla compared to a lot of GWS. I mean, hey, yeah, I fucked two women on the same night, just not at the same time. I don’t think I’m ever going to get to fuck two women at the same time but my current partner breaks my dick off, so…

This happened, Christ, eight years ago. Names, places, most anything that could identify anybody has been changed.

I ran a hotel in the midwest for about five years. You could tell the place used to be upscale but now it was a dump. The owners possessed all the design sensibilities of Eastern Bloc architects. They dreamed of flat concrete grounds and blank white walls. Over the five years I worked for them they slowly managed to rip every tree out of the ground and also ripped out the retaining wall around the perimeter so whenever it rained, the sidewalks were covered in mud. If it rained in winter, the sidewalks were covered in ice. Everything was a hazard. God, I shake my head remembering those dumb cheap fucks.

Anyway, one day, this gal checked in while I was on front desk. I’ll call her Edna. I gave her tour of the lounge / kitchen before showing her to her room. She made a few nervous jokes that I didn’t get. I don’t remember how long she checked in for but I know she extended her stay a few times. She had a hooked nose and pretty eyes, pretty mouth, long blonde hair. Probably five eight. Average body. Joey Lauren Adams’ from the nineties voice. Wearing a really sharp pantsuit. Like a fucking powersuit. If I had to guess at the time, I would have assumed she worked in finance or something.

Now, I did alright with the guests. Hell, my assistant manager (woman) and I almost made a game out of who could fuck more guests. But this one? I wasn’t feelin’. Just something off about her.

A couple days later, she comes downstairs, passing the office, dressed casually. Half her goddamned hair gone. And not in a good way. It is fucking chopped up. Totally crooked. And her face… Her skin is all blotchy. “OK,” I think to myself, “she drank to the point of alcohol poisoning and gave herself a haircut.”

But no. She’s proud of it! She comes to the office and asks if I like her hair.

I don’t remember what I said to her but I probably lied to her.

Let’s fast forward a bit.

I’m sitting on the back patio with my guy, Carl. (I have some stories about Carl but they’re more like striking-out-at-t-ball stories.) A couple guys who were in town for their buddy’s wedding come back from the reception, they’re pretty chill, one guy rolls a joint and passes it around. Edna comes out back to join the fun and we’re all talking and at one point she mentions that she’s been told she looks like Cameron Diaz. I don’t see it but what am I going to say? It is late, I am drunk, I am high, I’m not going to start shit.

She gets up to go to the bathroom and once she’s inside, the groomsmen start talking shit. “That chick looks like Cameron Diaz?”

“Man, nobody’s ever told her that.”

“That fuckin’ hair?”

It got a little cruel but what do I care?

Carl’s out of beer, asks me if he can have one of mine. I tell him sure, hold on.

I get up, go inside, and bump into Edna. She asks me how I’m doing, if I’m having fun, what am I doing right now. I tell her I’m grabbing a few beers and – because I’m fucked up – ask her if she’d like to come down to see the staff quarters. (The assistant manager and I lived on-site.)

She comes down and I show her my room and, next thing you know, we’re on the bed. I mean, fuck Carl. It’s *my* beer, he can wait.

So we get our clothes off and she asks if I have a condom and I say, “Yeah, right here.” It was right there. It was on top of the alarm clock. Such was my youthful self-assuredness that I just kept a johnny right there.

She says, “Skip it. Fuck me in the ass.”

>Brief aside: I would later tell my guy Lil Tommy about this and he yelled while we were sitting at the bar, “Those aren’t just about babies, you wear one so you don’t catch a fuckin’ disease!”

Back to the story, I go with it. I’m not a big anal guy but I go with it because I’m drunk, high, and hard. She just kind of lays there, letting me fuck hell out of her ass. I tell her I’m about to cum and I ask her where she wants it. She tells me to cum on her face. I’m not a big facial guy either but I feel like I’ve been swept into a porn universe, so I oblige.

I tell her to hold on a minute while I grab a towel from the bathroom and I turn around to see her wiping her face on my pillow. I say, “I’ve got a towel right here!”

“Oh.”

“OK, well…” I put the towel back on the sink. “Hey, we both know what this was, right?”

“What?”

“Just two people… Having some fun…”

“What’s that mean?”

“Uh, you know, we can’t do this again.”

“OK.”

OK, easy enough.

We get dressed, I grab two beers out of the mini-fridge, we head back up stairs and out to the patio and Carl’s giving me a look. The groomsmen are kind of exhausted, high. I hand Carl a beer and Edna sits down next to me and we’re all just talking, quiet, low key, it’s late.

The backdoor opens and we look over and this redhead with an upper arm sleeve in a tank top and jeans comes out, trips down the steps and face-plants into the patio. The six of us all get up and rush to her aid and she sits up and she asks if any of us know where to find the manager.

That’s me.

She needs help getting back to her room and Edna says she can help her and I say, “I got her. I’ve got the master key ring.”

I take the redhead, Leighann, inside and I go to the office, grab the master key ring from the desk and come back out. “Where’s your room?”

She makes a hand motion and says, “It’s like up and around?” I think I know exactly what room she means so I take her up to the third floor and ask her which one it is and she says, “No, it’s on the second floor.”

So we go back down and we find her room and I go to unlock it for her and she stops me and we start making out right next to the door. I ask her, “You want to fuck?”

Mister. Fucking. Smooth.

“Yeah but I don’t want to disrespect my roommate.”

I tell her to come with me and we go back down to the staff quarters. I put some fuck jams on the stereo and she says, “No, put on something faster.”

I don’t know why but the first thing I scrolled to in iTunes was *Mclusky Do Dallas*.

She undoes my belt, pulls down my pants, gets on her knees, and starts blowing me and I SWEAR TO GOD that I had forgotten that it had been less than ten minutes since my dick was in another woman’s ass. She didn’t seem to notice and if she noticed, she didn’t seem to mind. Doesn’t matter. I am drunk, I am high, I came ten minutes ago. My dick is deflated. This isn’t happening. Doesn’t stop us from getting on the bed. I jokingly say something about fucking her in the ass and she says, “It’d be real cute if you fucked me in the ass right now.”

I remember that to this day: “It’d be real cute if you fucked me in the ass right now.”

What proceeded to happen was I ate her out for at least an hour while I pulled myself, trying to get hard. When I finally got hard again, I lined myself up, prepared to fuck her in the ass (cutely) and, instead, I slipped into her pussy.

“Uh, that’s not your ass.”

She nodded and smiled.

We fucked for I don’t know how long. I want to say it wasn’t long but everything was taking forever with me so it was probably a while. Decent amount. I felt myself on the edge, pulled out, and shot a couple thin ropes across her abdomen, up to her tits.

We fell asleep.

We woke up about nine and she sat up with a start and looked at my alarm clock – you know, the one under the rubber I never used the night before – and she said, “Well, I think I lost my job.” She gets up and starts getting dressed.

I’m still in bed. “It’s Sunday.” (She was also traveling but I don’t know how her job works.)

She buttons her pants. “Yeah, I was supposed to be there at seven.”

“Oh, shit.”

Her hair’s a mess. She starts working it with her palms and stops. “Hey, if you find a pair of earrings…”

“Yeah, yeah, of course.”

She leans down and kisses me and smiles warmly. “Thanks.” She points at the door. “Just out there and up the stairs?”

“Yeah.”

“OK.” She turns to leave and stops. “We should get together tonight.”

“Definitely.”

I wanted to, I really wanted to. She was a fucking smokeshow. Red hair in a pixie cut, about five ten, athletic build, freckles over a button nose, almond eyes. Goddamn, I wanted to.

HOWEVER, while I was fuckin’ all night, my assistant manager, who is epileptic, drank all night. By the time Leighann got back from the thing she wasn’t fired from, I’m busy talking to a pair of EMTs about the grand mal seizure my assistant manager is recovering from. I wind up taking her shift for her.

In the end, Leighann left the morning after that. She gave me her business card and we friended each other on Facebook and for a few months, she casually told me to come out to San Francisco. I never made it because I wasn’t allotted any vacation time because the shitty owners. God, I would have loved to have fucked her sober.

A year went by, communication ceased, she had a baby. Happy family pictures, all that.

Edna kept cutting her hair shorter and shorter, kept dressing sloppier and sloppier. We fucked again a week or so after Leighann left. She got me drunk and high and she pulled out all the stops, almost gave me some kind of pill. That was the last time we fucked before she checked out.

A couple months after she checked out, dead of winter, Edna comes to the hotel and asks if we have any mail for her. Her hair is so short, there are red patches on her scalp. She’s wearing a green parka and pink sweat pants. Her complexion is bad. I tell her no, no mail, sorry.

I ask her, “You OK?”

“Yeah! Yeah, I’m good.” She then turned around and walked away. The last image I have of her is burned in. She’s walking along that icy sidewalk, midday, the sun reflecting off the ice-capped snow like a fucking mirror.

I closed the door and went back to whatever I was doing.

Source: reddit.com/r/gonewildstories/comments/b7k20o/the_first_time_i_30m_had_sex_with_two_women_on