This got incredibly long with some back story up front. Skip down to asterisks of you want to really just read the sexy stuff…
Many years ago in college, I worked as a bartender/server at a chain restaurant and bar, and my coworkers and I would get together just about every night after work to drink and blow off steam after our shifts. Anyone who wasn’t closing would typically stay and have a couple drinks at work, then head to a nearby dive bar to keep things going or a house to afterparty. Summertime was another story, as every night was a chance to drink too much, hook up with each other, and do it all over again the next day. It was a glorious existence.
The best thing as a young man about working in a restaurant was the amount of stunning women I worked with as a bartender/server. They all knew they could make a ton of money by wearing tight tops, flashing their smiles, and laughing at bad jokes. They were all very attractive and fun girls, and smart enough to know how to use it.
At this point I should mention that I had a steady girlfriend who didn’t work with me at the restaurant. I really tried to be a good and faithful, as I really did like her and we had been dating for almost a year. I partied with all of these beautiful women and my buddy coworkers, but didn’t partake in the debauchery. I mean, I flirted with all of them, and was pretty charming, but was seen as pretty harmless since I was taken. My girlfriend was not that excited about my coworkers, but most were really nice to her and told her not to worry about me, cause I was a “good one”. I’m not some crazy great looking guy, but I was attractive enough with a pretty good personality and ability to make people feel important (Probably why I did so well on tips).
I was at a summer party late one night with a mix of people I worked with and friends of friends who were all having a good time hanging out and drinking way, way too much. We were dancing in the living room, playing drinking games, and laughing at the expense of our customers and coworkers.
I seemed to be talking to “Julie” a lot that night. She was a really cute short brunette girl, and one of the younger ones like me (both of us just turning 21, and most of our coworkers are 23-25). She had dark olive skin that matched her italian last name, with a strong athletic build (she was a runner, but not a waif – think almost gymnast style body) that highlighted her strong, round ass and medium breasts. She actually didn’t flaunt her body nearly as much as the others, but her cute smile and innocent face really had me thinking about her in different ways lately. To top it all off, Julie had also been married right at 18, but divorced at 20. She was probably a little more reserved when we first met since she was married so young, but had been opening up lately after being divorced for almost a year now.
We kept talking and laughing and flirting throughout the night. We also danced a couple times in the living room, and probably were up on each other a little too much for me having a girlfriend and all, but I just chalked it up to innocent fun. The party started to dwindle down as I’m sure it was 3 or 4 in the morning now, and I was wiped out and pretty drunk. I went to retire to a couch, but everything was occupied with others who passed out earlier.
Did I mention we were at Julie’s rental? She was one of 4 who shared the house together, 3 of them working together at the restaurant, and one being a coworker’s friend. Julie looked at me trying to figure out what to do and said ” c’mon, you can share my bed. No need to sleep on the floor!”. I had actually passed out on her bed before when she wasn’t there, but never in bed with her. Warning signs flashed all over, but alcohol, tired, and she was just so fucking cute that I couldn’t say no.
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We go to her room and she runs to the bathroom to change. I slip of my pants and keep my boxers and t-shirt on, and just sit on the bed. Julie comes back in with short shorts and a tank on. I can see her round ass just pushing the limits of those shorts, and her soft, perfect handful-sized breasts outlined snuggly by her tank. She was also nipping out, but I tried not to stare to be polite.
We get into bed and are just chatting drunkenly before falling asleep and we were talking about her significant others and I made some silly comment about “how it would be fun to be wild like everyone else at these parties sometimes, but you know, trying to stay good.”
Julie laughs and says “Well, if you ever want to make a change, let me know first. ”
Fuuuuuccck me. I kind of nervously laugh and get a little silent. She says she is tired and rolls away from me, but reaches back and grabs my hand and puts it on her waist. “Thanks for a fun night and keeping me company.”
I just say something dumb like, “yeah, of course” and slowly massage her sides and hip. I started running one finger up her back over the top of her shirt, and she moves her body forward to make it easier to touch her back. I then start to run my whole hand up her back, and slide under her shirt this time, not really sure what I am doing. I feel her push back against my hand, and she seems to enjoy this sensation. I moved down her sides, gently grazing her side boob, still playing innocent, but pushing the limits. I’m starting to get a little hard myself, but not spooning her to let her feel anything from me. I worked my way down her back to the top of her shorts and rub right along her back dimples (which really started to get me going) and then did the old brush my fingers under her waistband, softly touching the top of her ass. I even sort of got my hand under there before I suddenly stopped when she moved. I didn’t know where this was going and got scared and thought of my girlfriend.
I pulled my hand away and rolled onto my back when I didn’t hear anything back from Julie. But not 10 seconds later, she rolls over towards me and immediately puts her hands under the sheets and grabs my semi-erect dick without warning. I sort of freaked out, and moved away, and Julie laughed and said “What was all that teasing about then?” and before I could answer, she slips under the covers, pulled my boxers down, and took me in her mouth.
To say I was shocked would be an understatement, but everything flipped from caution to passion in a moment’s notice. I could feel her soft, full lips taking all of me in, her tongue circling around my shaft inside her mouth. I instantly was full throttle despite all of my worry and the booze. She started to move her head up and down my cock, sucking and licking, and moaning that muffled moan of someone enjoying the giving.
I sat up and took my shirt off while she was still sucking, then ran my hands down her back and pulled her tank towards her head. She stopped long enough to sit up and take it off, and went right back to focusing on my dick, holding the base with one hand, playing with my balls with the other. She licked and circled the tip of my cock like I hadn’t felt in a long time. I rubbed her back down to the top of her ass, and reached underneath her to feel her breasts. Her nipples were hard and bigger than I expected, even after seeing her nip out before.
I all of a sudden felt way to close to cumming already, so I pulled her head up and kissed her on those same lips I was just feeling down below. She sat up, and I instantly reached to put my hands down her shorts to start returning the favor, and give myself a break. I went straight down her muscular torso, brushing past her pubic stubble, right to her lips and rubbed the outside for a moment to warm her up. She was already wet to the touch, so I slid a finger right through her lips to her clit, and started to rub slowly but firmly. She moaned into my mouth as we both kissed on our knees. She stopped me to quickly take her shorts of, then came right back to me in embrace.
With her shorts off and her kissing me deeply with her whole mouth and tongue, i really worked her pussy into a wet, warm, throbbing state. I had two fingers deep inside, rubbing the front of her pussy and the palm of my hand grinding her front hood. She meanwhile was working my full mast shaft with her hand, pulling hard front to back and occasionally adding in a twisting motion. I then for some reason focused on using my fingers in a curved move, and my ring finger grazed her ass cheeks. To get a good hold, my fingers ended up just under her ass, driving back and forth until I brushed the edge of her asshole (which also just had the slightest peach fuzz). Julie moaned a little deeper again and really started humping my hand. My fingers were a little wet from being in the area, so I just went for it and rubbed her asshole on the outside, and when she didn’t object, I started to push my finger in. It was tight, warm and made me even harder somehow as she tensed up at first, then slowly loosened her get to let me massage her from the inside.
Julie was just going wild rubbing up against me at this point with fingers in two holes, and pushed me onto my back on the bed. Because we were still semi drunk and horny, we didn’t even discuss protection and she climbed right on top of my rock hard dick. Her hips and ass just started moving back and forth, keeping me as deep inside of her as she could. I put my hands up on her breasts and squeezed them, pinching her nipples and circling them with my fingers. Her stomach was really toned and it was so fucking sexy to run my hand up and down her hard body (which was in much better shape than mine)!
I knew I wouldn’t last long, and sat up started kissing her again while she rode me deep and ever faster. I could feel her tightening up which I took to mean the big o was on the way, and reached around her, grabbed her ass, and pulled her in rhythm back and forth against me. I reached down and even rubbed her asshole one last time which sent me instantly over the top and I let burst what had to be one of the biggest loads of my life as Julie grabbed me tighter and just moaned the deepest sexiest sounds I had heard in forever. She sat on me slowly grinding now, and I swear I could feel her pussy pulsating around me.
We both laid down in silence. I instantly panicked and blurted something about birth control and she laughed at me and said she was on the pill. We both slowly got up and went to the bathroom to clean up. I went back to bed, boxers and clothes on and we both feel asleep instantly.
The next day, it was amazing how not awkward things were. Because we had been friends for a while, and she knew about my girlfriend, she just let it go and would randomly talk about that party with a glimmer in her eye. We never hooked up again, and I never cheated on my girlfriend again (we mutually broke up the next semester), as I definitely felt terrible and guilty for a long time. I attended a lot of other work parties, and Julie rarely slept around, so I just must have caught her on the right night. But clearly it left an impression on me that I never forgot!
Source: reddit.com/r/gonewildstories/comments/qwt5ev/hooking_up_with_a_21_year_old_coworker_f_when_i
Very hot! Loved the spontaneity of that session.