I moved into my apartment building in early 2019. I could tell the property manager (let’s call him Dean) was super nice and helpful right away. He was a pretty average looking white guy—brown hair, green eyes, in good shape, around 5’10”. But there was something I liked about him.
Since I was just moving in, I had a bunch of packages being delivered with stuff for my new apartment, and a lot were pretty heavy. One day, he saw me trying to move a huge package and asked if I needed help. I laughed and said yes. “I’m always here if you need help with packages,” he told me. I thanked him and said I’d probably take him up on that offer. From then on, he helped me with many packages. I was furnishing my apartment from scratch so there were a lot. We made small talk, and he was really fun and easy-going.
I don’t know exactly when, but at some point it seemed like Dean was starting to flirt with me. But it was pretty subtle and more like teasing since now we’d gotten more comfortable with each other. Regardless, I started to flirt with him a little too. We got to know each other a lot over the course of those many walks from the mailroom to the elevator to my apartment. Whenever I got a notification a package was delivered, I got excited because I knew I’d get to spend some time with Dean.
After a few months, our flirting and teasing had escalated. I couldn’t deny that we had chemistry and sexual tension. I found myself fantasizing about fucking him. I caught him checking out my tits multiple times so I had a feeling he found me attractive. I really wanted to make a move. I was so scared but decided to shoot my shot.
One day, I went down to Dean’s office. We chatted about random things, and as I was about to leave, I said, “hey I have a question…would you ever want to go out for a drink sometime?” He just stared at me for a second, clearly surprised by my question. But he snapped out of it and was like “yes, definitely.” We exchanged numbers. I left and he texted me after work. We planned to meet for drinks at a nearby bar that coming Friday. I was actually surprised he said yes but was really excited. I knew it would be so satisfying since the sexual tension had built up over a few months.
Friday night finally came. We ordered some IPAs and settled into a booth in the back. It was a little awkward at first but once the alcohol kicked in, we were talking and laughing and I had a really good feeling. He told me how beautiful I looked, and I said he looked quite handsome himself. I saw his eyes dart to my tits quite a few times (check out my profile and you’ll see why ?).
After our second round of drinks, he came around to sit on my side of the booth. Being so close to him made my heart race. He put his hand on my knee and started rubbing it. I put my hand on his knee too and started slowly inching my hand a little higher up his inner thigh. He looked at me, and I just gave him an innocent little smile and shrug. He started moving his hand up my inner thigh as well. I was getting so wet in anticipation. My hand was about to reach his cock when I stopped. I whispered in his ear, “hey I’m going to the bathroom…wanna join me?” We had both been to this bar before and knew they had those large, ADA-accessible, individual bathroom stalls. He nodded and followed me, but not before adjusting himself down there ?.
Once in the bathroom, we locked the door. Dean wasted no time. He pushed me up against the bathroom door and kissed me. There was a sense of urgency to the kiss. Our tongues explored each other’s mouths hungrily. All the build-up finally culminated in one of the most intense makeouts I’ve ever experienced. It was electrifying. Our hands were all over each other’s bodies. I started to feel his cock over his jeans and he was rock hard. I broke off the kiss and turned him around so his back was against the bathroom door. I dropped to my knees. I unzipped his pants and pulled out his hard cock. I knew we had to be fast to not hog the bathroom. I sucked him with all the passion and vigor of an incredibly horny and drunk 21-year-old who loves cock. His sighs and moans were turning me on so much. I was able to deepthroat his entire throbbing cock and he was loving it. I really know my way around a cock, and it didn’t take long for him to tell me he was going to cum. Soon enough, there I was, on my knees in a bar bathroom, swallowing my property manager’s huge load ?. Truly a high point in my life. I stood up to kiss him as he zipped his pants.
“Should we get out of here?” Dean whispered in my ear. I nodded and we left the bathroom. We walked back to the apartment building and I took him up to my apartment (roommate was out of town). We made out again on my bed and started to strip down. I had to tell him unfortunately that I was on my period ?. Curse you, universe, you royal cock block ??. I know people have period sex but I didn’t want our first time to be like that. “Next time,” I promised. We made out some more and I eventually gave him another blowjob. This time I let him finish all over my tits. It was glorious. He left and later texted me that he had a lot of fun and hopes we get to finish what we started sometime soon.
This was going on towards the end of my junior year of college. I was busy with finals and we never got a chance to have that second date before I went home to visit my family for the summer. When I came back for my next semester that August, I was hoping Dean and I could pick up where we left off. But something had changed. He wasn’t flirting with me anymore and was being very professional. I asked him if I did something wrong and he said that I didn’t but he had started dating someone and that he couldn’t continue with me. I was pretty upset ?.
Well, from then on I avoided him for the most part unless I really needed something from the office. I went home again last summer (2020) after graduating from college, but returned to my apartment in late August. In talking to Dean now, I noticed there was a similar flirtatious energy again. I started coming up with excuses to go down to his office and talk to him. We teased each other a lot and even had some inside jokes going over the next few months. It felt like that old spark was back. By November of last year, I thought that maybe enough time had passed since our first encounter (about 1.5 years) that I could make a move again.
One night I texted Dean: “hey, I was thinking about that fun night in the bar last year. Would you ever want to finish what we started?” When I finally saw my phone light up with a text from him, he replied that he was flattered but that he’d had a bad breakup a few months ago and was not in the headspace to jump into anything. I said I understood but to let me know if that changes. He said he would.
I’ve let it go for the most part but it still bugs me that we never got the timing right. I am moving out of the apartment in a few months and had this idea that maybe I should say something to him before I leave like: “so I’m moving out and you’ll probably never see me again…last chance to fuck me…” Lol obviously not those words exactly. Should I make one final move? Serious suggestions on what to say to him are welcome!
Source: reddit.com/r/gonewildstories/comments/l6hev9/when_i_was_f_21_i_blew_my_apartments_property
Yes tell him anything you say would be good just make sure the stars are right this time lol