The bartender told me I could fill her ass with cum

I’m in my earlyish twenties when this happened. I just finished graduate school. I moved to the big city and had no job lined up. Fuck it, I’ll get a job at the local coffee spot I says. I was actually pretty stoked about it bc it was a really cool grungy type coffee/wine place that was always playing alternative or punk music. My favorite. I got hired as a barista and worked down stairs where the coffee was. Upstairs was the bar where you could order wine and/or beer. I didn’t know much about the upstairs at first. I started off working morning to the afternoon, so the bar was only starting to open when my shift ended.

Anyway, the first few days I met all the coffee people… then I finally met the bartender - a super hot alternative looking girl who was always racing up/down the stairs getting shit together for her shift. I couldn’t help but notice her tits jiggling when she did that. She introduced herself as Elena, a name that I immediately forgot.

Elena was basically my age. She was about 5’6, had dirty blonde hair, brown eyes, a Medusa piercing, nose rings, and tattoos. She was thin, had pretty normal sized boobies but knew how to show em off… like always wearing shirts that were too small so you could see her nipple piercings. Oh yeah, Elena had a reallllly really nice ass. I was instantly attracted to her. She just screamed sex appeal.

A little bit about me: 6’4, brown hair to my shoulders, ears pierced, skinny, but i was toned. I always wore pants and some band t shirt that was too big. Below average skateboarder but my friends were good so I got street cred by association LOL

Now Elena and I didn’t have much interaction at first. Like I said, our shifts barely crossed over. Plus, she was intimidating. She was like the ultimate alt girl. So as dudes do, I told my friend/roommate about her. “Bro, Ben… you gotta meet my coworker. She’s so hot and I think her nipples are pierced” lol. I still couldn’t remember her name. I thought it was Brianna or something. She was just the hot bartender when I talked about her to Ben.

Ben and I decide to go upstairs to the bar Friday night before hitting downtown. The day before, I tell Elena “Yo I think my friend and I are going to stop by Friday night for some drinks. You’re going to be working, right?” (I knew she was. I had the schedule). Ben and I link up Friday and end up chatting with her for about a hour. Elena was so sweet I couldn’t believe it. Her personality did not fit the way she looked (I know, I know. Don’t judge a book by its cover). She was also really funny. For someone who walked around the bar so confidently, she had such a goofy sense of humor. I don’t know, it just surprised me. I wasn’t attracted to only her looks anymore. I actually liked her. I had lil a crush.

A couple weeks go by and i start working later shifts. Fuck yeah. Now I start sticking around after I get off and go upstairs to the bar. Elena and I talked and talked. I definitely considered her my friend. I knew a lil about her childhood and her family. Turns out she was a pretty good painter, too - Thats hot. She told me all the tea about her regulars. I felt pretty cool. I asked her a few times if she wanted to grab a drink with me down the street after she closed, but she always said she didn’t really go out after work. She had a dog to go check on. Finally one day, a group of us coffee folk decide to go out for drinks once we close. We invite Elena and she says yes. Fuck yeah. She was wearing a sexy dark green mini skirt, a black polo shirt that probably fit her in 6th grade, and black doc marten boots. We all having a good time. People start to go home and before you know it it’s just me and Elena. Yeppp we were drunk. I was obviously into Elena but I wasn’t necessarily trying to speed run things and try to bang her that night. Did I want to? 100%, but I was old enough to realize that we were coworkers and being the new employee that creeped out the hot bartender wasn’t exactly the reputation I wanted. I also didn’t wanna make her uncomfortable. Well lucky for me, I didn’t have to make the first move.

The bar started getting crowded and Elena asked if I wanted to go outside for some fresh air. We go outside and she eventually started talking about how she was always happy to see me when she got into work bc that meant I would be upstairs at the bar later keeping her company. One thing lead to another and she invited me over to her house. Fuck yeah.

We got to her house and she wasted no time getting comfy. She took her skirt off. Elena was wearing some really adorable panties. Idk what they’re called… it wasn’t quite a thong, but I could clearly see most of her bare ass, which was juicier than I imagined. Anyway, they were white with red cherries all over them and a teeny tiny bow tie up top. Elena was just always so fucking sexy. She didn’t know she was going out that night. The hot outfit and hot panties were on bc that was simply who Elena was, all the time. She sat down on her bed and turned on the tv. She fucking put scooby doo on. For some reason that kinda turned me on. It was cute. I’m still standing there, fully clothed with a boner pressing against my jeans staring at her. Her extra small shirt still on, sitting criss cross applesauce. I could see the cherry panties giving off a slight outline of her pussy lips. “Are you coming to bed silly?” She says.

I take my shirt off and we start making out. I slowly start rubbing her pussy over her thin cherry print cotton underwear, then I slip my fingers underneath to start fingering her. Elena got wet pretty quickly. She started taking off my pants and as I stood up to finish the job, she sat up and stared at me with these sexy puppy dog eyes. I knew what she wanted to do… slob on my knob. It quickly became very messy. She’s spitting on it. Rubbing my hard, wet cock all over her lips. Half her face is glistening. I’m getting fired up. I grab the back of her head, gripping her hair and pulled her face forward to me until my dick disappeared into her mouth. Her hands grab onto my thighs. Back and forth her head went. I couldn’t help but moan. I had never had head like that. Elena was so enthusiastic about me stuffing my penis down her throat until she gagged. I laid down on the bed. Elena continued to suck me off. Her ass was sticking up in the air. Saliva everywhere. It was on my balls, literally dripping down my taint. “Am I going to get to fuck you?” I said smiling.

I pushed her over, threw her legs over my shoulders and guided my dick in her warm wet pussy. “Elena, I’ve been wanting this so bad.” She started to hold onto her tits and play with her nipple bars as we were rocking back and forth. Her eyes locked with mine. I really start to pound the hot bartender now. Her mouth was wide open as if she was trying to talk but all I heard were short moans. It was pretty obvious she was into rough sex. Then… I notice a lil blood on my dick and I say something. She started her period! I’ve had period sex before and I was fine with it, especially with how horny I was at that moment, but before I say anything Elena goes “You can put it in my ass if you want?”

Hollllly. Fuuuck. Holy fuck. I couldn’t believe it. I had only dreamed about anal sex up until that day. I straight up told her that I had never done anal. I could tell she got a little excited knowing she was going to be my first. But she was not as excited as me. Elena got on her stomach. I started playing with her ass. I spit right in the center and slowly rubbed her asshole with my wet finger until I could poke my finger in. I saw Elena’s tight little hole slowly open up after my finger went in a few times. I gave her ass a quick kiss and I was ready for the show.

“Start slow.” I lubed my cock up with some jelly she gave me and followed her directions. Assholes are so fucking tight. I had no idea really. I didn’t think I was going to be able to fit. I slowly kept poking my dick through until her back door finally opened up wide enough to get an inch or two in. I was actually in this girl’s ass. I felt Elena quiver and say “Mhm that feels good.” I ascended into heaven. I could feel every part of her with every tiny movement. Her sexy moans made me feel like a king. I added some more lube and kept going a little deeper. My cock was getting SQUEEZED. I loved spreading her cheeks with my hands and watching myself go inside of her. Her hole was barely getting big enough to house my cock. I could see her little asshole gripping my dick like a suction cup as I moved in and out. I was finally able to fit all of me inside of her. “Fuuuuck I can feel you stretching me out” Elena said. Her bootyhole was literally gaped from my dick. I felt more comfortable going faster now that her ass was broken in. Elena felt so amazing though. I knew I wouldn’t last very long. I flipped her over. I wanted to fuck her anally while in missionary. I wanted to see Elena’s pussy while I was stuffing her ass. I wanted to see the facial expressions she made. I get off the bed and stood up. I pull her to the edge of the bed and give it my all. I put my hands out and grab her near her shoulders for leverage, almost holding onto her neck. I got back to it. I was fucking her like a slut and I knew she loved it. Her hair was moving in motion with my hips. Her moans got louder. Her face scrunched up. “FUCKKUHH FUCK… Fuck my ass! I’m cumming, I’m cumming!” Elena’s practically yelling. We’re both red and sweating at this point. I knew an anal orgasm was a thing but holy shit I couldn’t believe she was doing it. I really felt like I was in a sex dream. I was also glad she got off just then, because I was at my end. My dick was so swollen. Every dick nerve was getting stimulated by her inner walls.

I quickly blurted out “Ohhhh im about to bust.” “You can cum inside” she told me. I didn’t even respond. The point of no return had built up. Every part of my body tensed up. I didn’t know what to do with my hands so I grabbed onto her arms and squeezed them. My ass cheeks clenched together. My thighs started trembling. My abs were flexing . At last, my dick erupted. I felt my thick cock flexing up and down, twitching, pulsating while filling up Elena’s ass with warm sticky cum. I was breathing deep, still grunting. I stared at her, probably with a crazy looking smile. I was dumbfounded. That was the best sex i ever had. “Ahhh my god Elena that was soo good.” I realized my hands were still squeezing her poor arms like I was ringing out a wet sponge.

After I came back to planet earth I hear her say, “Mmmm thank you sir”, then playfully slapped me on my chest, smiled, and said jokingly “I hope you didn’t get me pregnant.” She is so awesome. She got up and walked a few steps to her bathroom to clean herself off leaving the door open. Now this might be gross to some people, I totally get it, but I found it incredibly hot… I could hear Elena pushing my cum out of herself. The noise being made while my load was coming out of her ass just did something to me. She had no shame. Why should she? I had literally rammed my penis into her butthole until I filled it up with cum. It had to come out eventually. I was turned on. “Oh my god dude, this is like a lot” i heard her say, almost in a serious tone. Hehe that made me proud.

We cuddled all night and fell asleep watching scooby doo. Insane. I loved it.

Elena and I hooked up for a few more months. Always having fun with it. She was such a slut and I mean that in the hottest most respectful way possible. Elena loved to fuck. It was almost like her safe place, her escape. It was wonderful. She was the most in-tune with her sexuality girl I have ever been with and taught me a lot about what I like and how to please a woman. I owe her a lot and im grateful for her. I really liked her, but we pretty much stopped talking once I left the coffee place. It’s a whole other can of worms that doesn’t really belong here, but shortly after this experience I found out she was married to some dude in Europe. She lived there for a year right after college. Got married pretty young. I never really understood the full story, but they didn’t consider themselves together anymore. I believed her. I didn’t feel like a home wrecker, but I liked Elena and simply wasn’t going to get serious with her if she was married. It made no sense to me. Every once in a while we will check in, but yeah, she is beginning to be a distant memory.