Hi. I’m a longtime Reddit lurker and it’s time for me to participate. This is essentially an account of an affair. My wife and I have an open relationship on paper. In reality, she doesn’t want to hear about me with other women, so we agree that although the relationship is open, we act as though it’s not. The way it works is that she has occasional vacations where she lets loose and hooks up with one or more men, then comes back and lives an ordinary life, while I had one discreet affair. I’d like for us to be more open with each other, but we’re not there yet. So although I have license to fool around on paper, in reality it feels and works exactly like good old fashioned cheating. With that stage set, here’s the story of my affair. Note: I know this reads at some points like erotica, but it is real. I’m just leaning in to the parts that I really enjoyed.
In March 2018, I began investigating how to initiate a discreet affair. I was 35 and living in a major east coast city (I now live in the southwest). Also: I’m a 6’ tall slim middle-class white guy. I have never been the type of person to pick up a woman in public, so I signed up for AM and bought some credits. My first two dates were weird and sorta fun, but didn’t lead anywhere. Then I started corresponding with a woman I’ll call R. She was a tall, skinny, gorgeous black woman about my age. Her AM photos were racy, which should have tipped me off about her intentions. It quickly emerged that she was looking for a sugar daddy, as many women on AM are. I made it clear that I wasn’t looking for that, sorry for the confusion, etc. But we had clicked by then, and just kept talking via text. So after a few days of constant texting, I invited her to meet for brunch, just to hang out. So I met her at a popular brunch place in her suburb and I have to tell you, she absolutely blew me away. She was better looking than her profile pictures, and just exuded energy. I loved that even though she was tall, she wore high heels, accentuating her tallness. That day, in addition to the heels, she wore tight jeans, a flowery blouse and a black leather jacket. We were at the restaurant for four hours, ordering random things off the menu and sampling every cocktail they made. It was so much fun. She was a totally opposite personality than me, which I found thrilling at the time (it created a fair amount of drama later on). She somehow talked me into getting into getting the wait staff to re-make her food, even though there was nothing wrong with it. The whole think was such a trip. I drove her home, we sat talking in the car. She gave me a hug, leaving me smelling like Chanel No. 5, which I had to get rid of before going home to my wife.
I texted her the next day saying how much fun I had. She told me that she knew she was going to try to fuck me as soon as we met at the restaurant. I didn’t have to be her sugar daddy, but we could hook up as long as I took her out to dinner and generally paid for stuff when we were together. Of course I was elated. We made a date for the next weekend. My wife was out of town. I made dinner reservations at a restaurant near R. The restaurant’s tables were really close together, so it was hard not to overhear adjacent conversations. R and I were pretty infatuated with each other, but after a while we noticed that the two women at the table next to us were paying pretty close attention to us and were having a hard time hiding their judgment. Who knows why. We were in a fairly conservative area, so it could have been that we were an interracial couple, but it was probably more likely that they were picking up on the thinly veiled sexual tension and references to adultery. R texted me to point them out (I had noticed already, but was more focused on R). I texted back saying I hoped they were enjoying watching us and if only they knew what was going to happen later. R asked what was going to happen later (all still texting). I told her I was taking her to a hotel, and that I had a persistent erection in anticipation. R blushed, began acting very embarrassed. I texted her again that maybe the ladies next to us could see my erection and were shocked. R was certainly shocked and had a hard time keeping it together after that, so she ordered another drink. I realized she was stalling our exit from the restaurant, but let her take her time. She was nervous about the whole affair and hooking up with a new person. I found it amusing that she would be the type of person who was looking for a sugar daddy online, and was sexually experienced, but would still be nervous about hooking up with a new guy. But she was and I found it endearing. So we had a few more drinks and succeeded in forgetting about the ladies at the next table. After, we walked around the downtown area and browsed an upscale lingerie shop. We’d been holding hands up to this point, but now I became a bit more handsy. I came up behind her, held her by the waist, and pushed my bulge into her ass. I don’t think we’d even kissed yet. She told me how naughty I was, playing around in public like that. I said something like, oh that’s nothing, and reached up under her dress to grab her ass. She was wearing the classic little black dress and I could feel that her panties were lacy. So eventually we got back to my car and went to the hotel I’d gotten a room at. We parked and she wanted to start making out. So we did that for quite a long time. Again, I realized that she was stalling. So I asked her if she was having second thoughts, was she uncomfortable, etc. She said no, she was just nervous. So I grabbed our things and took her up to the room. Lots of foreplay, groping, making out, etc. I took her dress off, she pulled my cock out of my pants. She exclaimed how big it was and said she was nervous to take it. I tried to calm her down by saying we’d take it easy, don’t worry, etc. She sucked it a bit. We got naked, I put a condom on, we took it slow. She was very vocal, with lots of moaning and would make a loud “uh” sound every time I pushed into her. I couldn’t get all the way in, so when the tip of my cock would push against her cervix, it was a bit painful for her. When she moaned in pain, it turned me on even more, so it was a struggle not to pound her as hard as possible. Her pussy was a bit more open than I was used to, and it felt amazing. My wife has a pretty tight vagina, as have my other previous sexual partners. I had no idea that what I was missing until I felt R’s vagina. I was in heaven. Long story short: we had sex for hours. I came four times in her. By the last time, my cock was not as hard as it started out, so it was more pleasurable for her not to have me ramming her cervix so hard. She wanted to spend the night together, but I had to get home to let the dog out, so we checked out of the hotel at like 3am and I dropped her off at home.
After that we were texting nonstop. She sent me lots of sexy selfies and nudes. We talked on the phone several nights a week. Our conversations often turned dirty. Her big fantasy was for me to fuck her bare (without a condom) and having my cum in her pussy. This was super hot to me, so I played along on the phone. I said it couldn’t happen, which made her want it more. She also wanted to be submissive. I had never explored being dominant before, so it was almost like she was coaching me. We had the chance to get together a few weeks later, so I got a hotel room and was able to spend the night. I’d been mentally preparing to practice being dominant. So after dinner we got to the hotel room and I experimented with ordering her around. Pretty mild stuff really, but it was a big step for me. I don’t remember the details now exactly, but it was more or less along the lines of: She went to take off her shoes, but I told her to leave them on and go sit in the chair in the corner. I stood in front of her, pulled my cock out and told her to suck it, which of course she did. After a bit of that, I told her to go kneel on the bed, with her ass up in the air and her feet hanging off. I pulled her dress up around her waist and her panties down to her knees. I can still get off thinking of the sight of her bare ass pointed up at me, her pussy visible between her thighs. She had the type of vagina where the interior lips protruded through the exterior lips, which I love. So I put my condom on and fucked her in that position. Afterward, she kept telling me that she wanted me to fuck her bare. I let my dick think for me, so I agreed, but that I wouldn’t cum in her. So I fucked her bare and it was the best feeling my cock has ever had. When I got close, I pulled out, put a condom on, then went back in for the finale. We slept together that night, which was nice, had a bit more sex in the morning, showered together, etc.
In the interim after that, during our phone conversations, she just kept pressing me to cum inside of her the next time we had sex. She told me that after her son was born (she had a young son, btw), her gynecologist told her she was unlikely to be able to become pregnant again. She eventually wore me down and got me to agree to cum in her, which we explored in our phone fantasies for a while. Eventually I got a free weekend and booked an airbnb in a rural area for us to spend the weekend. As usual, we fucked like bunnies but this time I came in her repeatedly. She was obsessed with the idea of my cum in her, which turned me on. After one particularly heavy load, she wanted me to take a picture of my cum dripping out of her pussy so she could see what it looked like. I wish I still had that picture, but I deleted it to avoid getting caught by my wife. I kept it on my phone for months, and looking at it always got me hard instantly. We played around in public that weekend, which was fun. At the end of dinner that first night, she went to the bathroom when we were about to leave. I told her to take off her panties before she came back. She was expecting to leave the restaurant, but I told her to sit down. She was confused, but I explained to her that as she prepared to stand up from her chair, she should open her legs wide and expose her pussy to me so that I could see she wasn’t wearing panties. She was nervous, but there was only one other couple in our section of the restaurant, and they were older so I was sure they wouldn’t notice. So she did it and I loved it. Later, on a stroll around a neighborhood in the small town after dark, she got on her knees, pulled my cock out and sucked it for a bit there on the sidewalk. What a thrill!
I only once came in her mouth. We were driving down a stretch of rural highway and she said she wanted to blow me while I was driving, but worried it wasn’t safe. I told her it was totally safe and she should do it. She gave an amazing blowjob.
The following weekend, I didn’t have much time, but was passing through her town (she lived about 45 minutes away from me). I picked her up from a friend’s party. We didn’t have a place to hook up, so she asked a friend of hers if we could use her place. When we arrived, her friend’s twin sister was there. R explained that her friend had given us permission to use their friend’s apartment to hook up. The sister seemed annoyed but agreed. It was a smallish apartment, so the friend’s sister just went in the bedroom and close the door. R and I fucked briefly on the couch in the living room. That time she was standing up, bent over the couch, with one leg up on the cushions and the other on the floor. I penetrated her from behind. The friend’s sister could surely hear everything. It was almost exhibitionistic fucking in such a flamboyant position in a stranger’s living room.
The last time we hooked up, my wife was out of town and R came to my apartment in the city. We had sex in the apartment and I drove her home later that night. I parked on the street outside the house she was staying at with a friend. She wanted to fuck one last time (for the weekend; we didn’t know it would be our last encounter), in the car, but I was nervous about having sex in public like that. But of course I did because I was crazy for her and it was thrilling. So she pulled off her panties, hitched up her skirt and mounted me in the driver’s seat. Although I had come in her several times earlier that day, it was pretty hot and I managed to come again. At one point, a car pulled into the next house over and the woman got out and walked into her house. I was turned on by the idea that if she looked over, she would see us fucking in the front seat of my car. The lady would have just seen our clothed torsos, but I knew that my cock was inside R, and that woman would too. It was dark, and I don’t think the woman looked.
That was the last time I saw her. The whole thing lasted four months. As a bit of a post-script, I always wondered if she wanted to explore watersports, but I was too nervous bring it up. The reason I say that is because when we would stay at hotels together, she never closed the door when she went to the bathroom. I would hear her peeing from the bed, and enjoyed it. I wondered if she wanted me to walk in on her while she peed, or if she was just super casual about the bathroom door. Also, that last night when I was driving her home (as described in the previous paragraph) she had to pee really badly, but it was late and we were in an area with no obvious place to use the restroom. We were still about 20 minutes away from her house (and also she had plans to fuck me one more time, which I was unaware of). She told me to just pull over. She opened the passenger side door, swiveled her legs out, braced herself with her one hand against the lower door jamb and her feet on the ground, pulled her panties to the side and peed onto the side of the road. I was fascinated by this, but I still wasn’t sure whether she was just casual about peeing or if she was testing my limits. If we’d kept seeing each other, I suppose I would have figured that out.
As the relationship progressed, R became more and more upset that I wasn’t more committed to her. She was single and wanted a real partner, which I couldn’t fulfill. Soon after that last encounter, she began dating someone and we didn’t see each other again. I’ve left out a ton of details, mostly because I wanted to reminisce about the sex. Feel free to ask questions if there’s anything you want more detail about.
Source: reddit.com/r/gonewildstories/comments/lfnue5/mf_story_of_an_affair_long_read