[M]y first of many hookups with my boss[F]

Alright, this story is about the first time I hooked up with an my boss 3 years ago, and the 2nd relationship I had with an older woman. She was actually my manager at a supermarket I worked at for a year while finishing college.

We’ll call her V. She was a total milf. Mid 30s, pale skin, long black hair, pretty face, wide hips, 5’3, fattest ass I’ve ever been with, I’m talkin dump truck booty. Not the biggest breasts but they’re nice, can get a nice handful of them. She was also covered in old school style and horror themed tattoos.

So we ended up working the night shifts together all the time. I was instantly attracted to her because of her looks but we started to get a long really well after I recognized the music she was listening to. We found out we had a lot in common so we kinda hit it off from there.

We always hung out while at work, there was always something for us to talk about whether it was music, live shows, partying, whatever. The flirting didn’t start until after a couple months though. We had gotten really comfortable with each other to the point where we would talk about our hookups we had the previous weekend and stuff like that.

The first bit of flirting I remember came after she caught me watching her walk away. She had a huge ass and every time I saw it I would always imagine how cool it would be if I could just stuff my face in it. Anyways she catches me checking her out, and she kinda double takes me but smiled really big after she realized I was looking at her ass.

Fast forward a couple days, I was listening to music and singing this part that goes “come a little bit closer, come a little bit closer to me” and I hear her say “okay!”, with a smile and wink. So I knew it was on, but wasn’t sure because I wasn’t her type, and she even told me before I wasn’t her type. She likes big, burly men, and I’m a 5’9, lean 145 pound, 22 year old dude.

Later that night, just before we’re clocking out, she asks what my plans are for the weekend and that she’s having a little kickback at her place with friends that weekend. I was seeing a girl around my age and already had a date set up for that weekend so I had to decline. But she then asks “what’re you doing tonight then?” And I didn’t have an answer so I agreed to hang out with her that night.

We go our separate ways to change into street clothes and meet up at a local bar to have a few drinks. After about an hour of shooting the shit, listening to her complain about her baby daddy, she says she wants to smoke some weed. I had some at my place so I invite her over. We get there, smoked, and just talked on my porch.

While sitting outside on the steps of my porch, she starts to get handsy with me. Touching my thigh, arm, and even starts biting my shoulder. I ask what’s with her and she just grabs my face and we start making out. She was wearing denim cut off shorts so I slid my hand under to get a handful of cheek. She then climbs on top and starts grinding. At this point I’m already hard so it was almost painful lol. I say “let’s go inside” and we head to my bedroom.

She makes fun of my action figure collection as she starts to undress, I say “haha just take your clothes off” and she replies “oh, it’s like that?” And she shoves me onto my bed and starts stripping for me. First she takes of her top, revealing a lacy black bra underneath. It was see through so I could see her nipple piercings, which were hot. She takes that off and then slowly slides her shorts down and she’s wearing a black lace thong. She turns around and gives her ass a little shake, (holy fuck the way it jiggled) and then climbed on top of me again. We’re making out and she starts unbuckling my pants, she slides them off and then turns around so we are 69ing. She had a PHAT pussy and I absolutely loved eating her out. So we’re blowing each other, I’m grabbing her ass and pressing it to my face, just trying to suffocate myself with her pussy and ass cheeks, she’s deepthroating the fuck out of my dick, all the way to the base, gagging and all. I’ve never had a sloppy bj like that before and it was amazing. She then moves on to my balls and I’m just trying to shove my tongue as far down her pussy as I can.

After about 5 minutes of that, we decide it’s time to fuck so she gets on her hands and knees for doggy, but I knew with her ass I wouldn’t last a minute so I tell her flip over. She lays on her back and I slide in raw. I stare at her pretty face as she’s biting her bottom lip, then look down at my dick going in and out of her slippery pussy. She tells me to go harder so I lift up her legs and start jack-hammering. She starts saying “that’s it! That’s it! Oh!” until she squirts all over my cock, down my legs to my wooden floor. I suck on her tits and kiss her stomach for a bit and she says she wants to ride me.

So she’s on top, bouncing on my dick, you can hear how wet she is and the sound of her ass crashing into my pelvis and she starts choking me with her hand. I’ve never been choked during sex before and I thought it was hot as fuck. I start hammering her from the bottom and she slaps and squeezes my face. I tell her to do it again but harder and she does. Here I am getting rode, choked and slapped by someone’s mom and I loved every single second.

After that we moved to doggy, and holy shit it was glorious. Even better than I would have ever imagined. Every stroke that thing would move like a wave pool. I’d stop every minute or two just to bury my face in it. She must’ve enjoyed it more though because as soon as I went in she let out a moan louder than before, and continued to moan as I kept fucking. After a few minutes she says “oh fuck, oh fuck, fuuuuuck I’m cumming!” And I don’t slow down, I’m pounding that ass like I was about serve life in prison. I say I’m about to cum and she tells me to cum inside her so I did. I pull out and play with her ass cheeks while she’s trembling, and my cum slowly drips out of her pussy.

We lay there, breathing heavy. She’s laying on her stomach, still shaking a bit. I’m laying on my back next to her, still jiggling her ass around. After a few minutes I ask if she wants to smoke again but she says she has to leave. We get dressed, and she left her thong off and said I could have it.

We walk outside and she asks if we can do that again sometime, and I say “fuck yeah, of course”. We make out for a few seconds and then she takes off.

So that was the first time we hooked up. We would hangout and fuck two to three times a week for about a year and a half before I got a big boy job in a bigger town about a couple of hours away. We still keep in touch, not very often though as she’s been dating other guys. But we still chat every now and then and have hooked up a few times in the past year when I would visit. But I’m moving further away soon so it’s about to come to an end, which I’m okay with. I’m was never really emotionally attached to her as I have been with other women in my past, her wild personality can become tiresome. But yeah.

That’s it! Hope you liked it. Might not be as interesting as my other story since it wasn’t something we had to hide, but it was fun. I have another milf story about a family friend I randomly ran into at a bar, and I guess I could tell some other stories like about losing my virginity to my friends older sister, my first threesome, and some other fun hookup stories. Let me know! Thanks for reading.

Source: reddit.com/r/gonewildstories/comments/o1ychi/my_first_of_many_hookups_with_my_bossf