My first MILF [MF]

Memory lane – My first MILF [mf]

I, (m, mid 40s) had a good bit of fun before settling down. I love this subreddit and visit it frequently. This is my first attempt at posting here. Also, this happened nearly 20 years ago so this is from memory. Be gentle.

It’s the early 2000s and I just moved to a new city for a job. I was in my late 20s. Since I did not manage my money wisely before the move, I had to make some sacrifices like only having internet but no cable TV. Cell phones were not smart yet. So, I did what any single & horny guy did, I spent a lot of time on Yahoo messenger looking for hook-ups.

One evening after work, I received a message from a woman saying that I looked familiar. We chatted a bit and figured out why she recognized me. As the chat continued, we discovered that we lived in the same apartment complex! We talked for a few hours that night. Near the end of the conversation, we got on the topic of football. We made a bet, whoever wins the upcoming MNF game, we would meet (win/win for us both).

The next day, I went to her apartment. I was nervous because finding someone’s picture online was not as easy as it is today. It was later in the evening because she had 2 younger children and they had to be in bed first. I knocked and she opened the door. She was 36, about 5’6”, shortish brown hair. An average but nicely shaped body for having birthed 2 children. She admitted she was also nervous and had been drinking wine since she got home from work.

She handed me a glass of wine and we sat on her couch and started talking. The wine helped to relax us both. When the conversation hit a lull, we looked at each other and she asked, “So, now what do we do?” Not wanting to be too forward I said something that I thought was clever but I’m sure sounded more like, “I don’t know. What do you want to do?” She said hold on, and got up to make sure her children were asleep. She came back and we started kissing. Things escalated quickly as she straddled me and started grinding her hips on my already hard cock. She decided that she wanted to suck me so she slid off and went to work on my cock. I enjoy a blowjob but it takes a lot for me to cum from one. What she did felt great but was not going to get me to climax. I told her to lay down on the living room floor. She wanted to check in her children one last time before we went any further. When she came back, I pulled down her shorts and panties in one motion. She tasted amazing! I licked her like I hadn’t eaten in days. She came on my tongue and I moved up to kiss her. My cock head pressing at her opening. She said she wasn’t on birth control and neither of us had condoms. She said to be sure to pull out. That’s all I needed to hear and I slowly slid inside. My favorite part of sex is entering the pussy and feeling it engulf my cock. I stayed still enjoying her pussy for the first time. We kissed and I began to move. I need to divulge that I had been on a 6 month dry spell so my performance was, shall we say, short lived. After about 5-10 minutes, I tell her that I’m going to cum. I pull out and shoot on her belly. We lay there for a few minutes before cleaning up.

After that, we kissed goodnight and made plans to get together again very soon. Apparently, my poor performance did not scare her off!!

This is the first of many stories with my first MILF. I know it was pretty “vanilla” but it does get better. If there is interest, I’ll write more about her and another I had fun with. Thanks for reading!

Source: reddit.com/r/gonewildstories/comments/nwrf1d/my_first_milf_mf