Former Coworker
In 2017. I had been working at a casino for nearly a year. During the time I had been working there, I had gotten to know a few women, particularly those who issued the player's cards. Three of them had enjoyed talking to me. Two of them I knew liked me, but I was always one to keep it professional since I didn't want to get a talking to from the strict manager. One of the two flirted with me openly. She looked like a slut and I knew I could get far with her, but nothing came of it because I rarely saw her. The other, we flirted with each other. She had a good set of breasts and a good looking ass. There was a third, Stacy, who talked to me in a professional manner. She never gave off the impression that she felt anything towards me. When she saw me, she would say, in a bored tone, "The other two are always talking about you."
Now, Stacy was a woman in her early twenties, about 5'6". She had a somewhat meaty body, but her uniform made her figure look amazing, especially her black dress pants. Those pants squeezed her ass just right. When I say that Stacy had a perfectly round ass, I mean that she had a perfectly round ass - I've seen a lot of asses and hers was easily top five. I know a lot of guys (workers and guests) who stared at her ass, I always stole a look often, too. I had a coworker who kept telling me he wanted to fuck her so badly. I told him to take a chance and ask her out, but he said she looked too stuck up and she never really talked to him when he tried talking to her. I agreed, because she seemed very professional.
Fast forward to 2019, I had been out of the casino job for about a year and a half. I was in a relationship that had run its course and I was already looking for someone else. I'm at home and I get a message and it's from Stacy. She asks how I've been and I tell her that I've been fine. I ask her what she's up to and she says that she is at her brother's graduation in New Mexico. We talk a bit more and just catch up. It's kind of late and I'm just watching tv, and I ask her what she's up to. Then she says, "I'm just in the hotel room by myself and lying down. I wish you were here lying next to me and holding me." I reread the message over and over again, not sure if she was joking. Deciding to take my shot, I replied that I would like to be in bed holding her, but that we wouldn't get much sleep. She laughed and said, "Oh really? What would you do to me?" I proceeded to give her a small, discreet description of what I wanted to do. She replied, "Well, I better hurry up and get back there."
About a month later, she and I are still messaging back and forth. Meanwhile, I'm still fucking my girlfriend at the time, but it's becoming less and less. So Stacy and I are talking about getting together to hang out; we both know what for, but we never say it. We also talk about how all of it came about. I asked her how long she's wanted me for and she said since we started talking. Told her that I didn't think she did, but she replied that she did and just didn't know if I wanted her. She then asked if I still had a girlfriend; I told her not anymore - a lie. I asked her to send me a naughty picture of herself. She sent me a picture of her wearing a bra, and I was amazed to see that her breasts were big. Only because, from what I remember, her work uniform covered it all up. We had tried to get together on two occasions, but we could never get a day where either of us were free.
One night, I was home and decided to message her. I asked her if she was busy. She messaged back right away and said that she wasn't. So, I asked her if she wanted to come over. She said she would be able to and asked for my address. I gave it to her and she said she would head over. It was about 25 minutes later when she messaged me and told me she was outside. I texted my girlfriend and told her I was going to sleep; she told me to text her in the morning. I went outside and greeted Stacy. She was wearing a black shirt and jeans, and her black hair was down. We went inside my place and sat down. I asked her if she wanted to watch a movie; she said yes and we picked a movie, but then we decided to change it to a horror movie - The Strangers 2.
She and I sat (her to my left) watching the movie for the first 15-18 minutes. We talked about the movie then about our work. During this time, my cock is rock hard, but I'm trying not to focus on it. We continue to talk, but she knows why she came over and I know why she came over so I decide to put my arm around her waist. She puts her hand on my leg and continues to watch the movie. A few seconds pass and I can't take it anymore so I turn her face to me and I kiss her. She immediately kisses me back and she even shoves her tongue into my mouth. I run my hands over her body, squeezing her breasts, which were big in my hands. I then put her on her back and she pulls me down with her, continuing our kissing. I move my hands to unbutton and unzip her pants and I pull them off, along with her panties. I then take my pants and boxers off. She pulls my shirt off and I get on top of her. I pull a condom out from under the pillow (put it there before she arrived) and I put it on. I rub my cock up and down her pussy, teasing her clit. I then shove my cock into her and she moans. I fuck her in a steady rhythm and pull her shirt up. We stop for a few seconds as she takes her bra and shirt off. Her breasts look even more amazing up close. I continue to fuck her, while sucking and nibbling on her breasts. She pulls my face up and kisses me. I then put her legs on my shoulders and pick up the pace. It's at this time that she says, "You didn't tell me you were this good." It's at this point that I'm trying to keep from cumming. I stop and kiss her for a few seconds, allowing my buildup to go down. I then continue, reaching around and grabbing her nice ass as I keep pumping into her. She's moaning and grabbing on to me, while breathlessly saying my name. During this time, I'm looking down at her, my cock pumping in and out of her pussy, her breasts bouncing, and I still can't believe I'm fucking her. I suck on her breasts again and she runs her fingers through my hair. I then feel the buildup again, but I don't fight it this time. I tell her that I'm close and she wraps her legs around me. I feel my cum shooting into the condom and I make sure I keep pumping, enjoying the sensation. She pulls me to her and kisses me again.
Once I've calmed down, I pull my semi-hard cock out of her and I lay next to her. She faces away from me and reaches around to grab my arm and put it over her. I take the condom off and toss it on the floor and I put my cock between her ass cheeks. We both lay there catching our breath. As we lay there, we continue to watch the rest of the movie. When it ends, we want to go again, but it's late and she says she has to work in the morning. So we get dressed and I walk her back to her car. We kiss and she heads home.
To this day, she and I still message off and on. We have yet to get together again. I still have the picture she sent me; still cum to it, too. If I could include the picture with this confession, I probably would (face cropped out, of course). I'd only be ..(continue confession)
