Amanda | Emily | Rachel | Sonjya

So, the most recent time I cheated was with Melissa. By recent, I mean seven years ago. One of the things I learned about cheating long ago was you have to be patient. Sometimes you go for years because the right opportunity doesn’t present itself. Melissa gave me some of the best sex I have ever had in my life, and I was very tempted to make it a longer-term ongoing thing. But that just wouldn’t work in reality, and geography kept our visits infrequent.

I met Melissa over a dating app when I was out of town for work. I was attending a conference and had a room to myself. It had been a bit since I got to enjoy someone new, so being far from home, I knew this could be fun. She was just a couple of years younger than me, divorced a few months earlier, and wanted to play. She was a mom, so it was only the second time I was with a MILF (the other is a story for another time). 

Melissa was a pretty active lady, so in shape but still with those thicc curves that do their magic on me. She had dirty blonde hair and light freckles on her cheeks. C cups, a very smackable ass. Just that little bit of a tummy that I think is very cute. We talked over a day while I did work stuff, and by evening, it was clear what we both wanted. Drinks at a nearby bar led to a cab back to my hotel. Inside the room, the clothes came off quickly. She wanted to shower, having not had one since she got off work. With it being one of those nice hotel showers, I joined her. I don’t want to get too bogged down on this first encounter because it’s the next one that has become lodged in my memory. We had sex at the hotel, and it was terrific; we kept texting after I went home. I wasn’t sure if we’d hook up again; I had to wait for the right opportunity. 

That came in the summer. Melissa lived in a neighboring state but told me she would visit my state every other month or so because of extended family. She let me know when the next trip would be, and I scheduled a day off for when she was passing through. My wife was out of the house for work and wouldn’t be home until late. I told Melissa where to park so it wouldn’t be immediately apparent she was visiting me. I also told her I’d be keeping her panties as a souvenir of this visit, so make sure to wear something she didn’t mind me having. 

The morning came. Wife left for work. I showered and prepared. Melissa arrived around 10am. She was dressed very casually - a T-shirt and shorts. Those shorts came off seconds after I closed the front door. After our hotel visit, she’d go on and on about how good I ate her out. Sounded like her ex-husband stopped after they had kids, likely one of the reasons for the divorce. I was happy to give her what she’d craved. Melissa chose to wear a pair of red lacy booty short panties that showed off those cheeks I couldn’t keep my hands off of. 

I took her to the bedroom and had her lay back. Panties joined the shorts, and I devoured her. She was so vocal and loved sliding her hands through my hair as she licked and sucked that sensitive clit. Melissa sat just on the edge of the mattress, ass hanging off the bed just a bit. I was kneeling down between her thighs. From our previous encounter, I remembered exactly how Melissa liked it, so it didn’t take long until her legs were shaking and she was crying out, my chin wetter. 

When we had first hooked up, I hadn’t brought up the breeding kink, but in the texts that followed, it found its way into our conversation. It hadn’t been something she’d thought much about, already having two kids, but I guess I worded it the right way because she loved playing out the fantasy on the phone and said she wanted to in person when she visited. She would even tease me, saying, “I may just forget to take my birth control pill the day I come to see you.” She also had two daughters and would say she wanted me to give her a boy. When she found out my wife and I didn’t have kids, she’d talk about having my child before my wife did. She knew abso-fucking-lutely everything to say to a guy with a breeding kink, which clearly had become one of hers now, too. 

After she came from oral, I was ready to give her another one with my tongue. Melissa said, “Give me your cock.” I wasn’t going to argue. I slid in, and she was so perfect - warm, tight, and wet - it felt like two puzzle pieces snapping right into place. Long, deep strokes while we talked dirty about me getting her pregnant, how I’d have to hide it from my wife, how Melissa would have to come up with a story to tell her friends. Those strokes were some of the best of my life, she knew how to work her hips back as we fucked in missionary. I told her I wanted to look right into her eyes as I filled her womb up; she responded through moans, telling me to give her my baby, please give me your baby. I thrust deep and emptied everything I had inside her.

We weren’t done, we had the whole day after all. A short break and a chat. We couldn’t keep our hands off each other. The break consisted of lots of long, lingering kisses. Bodies pressed together, legs interlocked. Melissa just felt fucking good to be naked in bed with. We kissed and touched enough that the hardness and the wetness didn’t take long to reappear. She moved down the bed and started sucking my cock while fingering herself. I told her I wanted to taste her again. She brought her slick fingers from her cunt and slid them into my mouth. Like heaven. 

This time, she wanted to ride. I laid back, she straddled my waist and eased herself down. Melissa rode cock better than any woman I’d ever been with. Her pussy was clenching me tight and working itself up and down the shaft giving me an insane challenge to keep from cumming right away. My hands each held an ass cheek, squeezing and helping guide her. With my cock entirely enrobed in that pussy she ground her hips, leaning down so we could kiss. Her breasts brushed across my chest. I wasn't going to last much longer. Another warm load with Melissa moaning and saying, “It’s all mine, daddy.”

The rest of the day was a repeat of this type of thing. Fucking until I came inside her, then a rest, going again. Around 3pm, we decided she should probably head out. I wanted her back at home safe before dark. She had me wishing she lived next door. When we parted ways, it was a test of self-control; we devolved into sloppy, hungry kisses. Her clothes came entirely off again at one point, and I fucked her on the sofa. My cock wanted to make sure this woman was carrying my child. By the end of our time together, I had cum inside her five times.

We kept texting for a few more months with phone sex when we had the chance. Eventually, she started dating someone who lived in her town, and our schedules weren’t as in sync as we had hoped. I went cold turkey with her when we cut things off. I still lust after her and wonder how she’s doing. I may have had opportunities to cheat since, but my mind & life were focused on other things. 

That’s where my cheating stories end concerning the present date. There were some one-night stands from the LDR period of my life that I might write down sometime.