Out of Pocket

Rediscovery

       I started going out more with my group of girlfriends who were fellow moms, they suggested I download Tinder, but I wanted to meet someone more organically. I had met my late husband through a mutual friend. Perhaps I could try speed dating. No matter, one thing was certain: I did not want to be married again. One marriage was enough for me. I wanted to casually date only and leave my options open. I was excited to start my search for potential partners. I lived in a college town so there were plenty of younger men available. When I went to bars with my girlfriends, I felt like a kid in a candy store. I started watching porn as well in order to figure out what I liked sexually and so I was eager to make my requests known. I also wanted to try being a sub, but nothing too crazy. I am always used to being in charge, but I knew I wanted someone competent who would know how to do the scenes I had in mind, understand my boundaries, and take the reigns from there so to speak.

    That was when I say him, a man in a loose white T-shirt and black jeans. He wore glasses, had a scar on his chin, and thick blonde hair. He was so hot, I thought to myself. I noticed he was talking to the husband of one of my girlfriends and it was all too perfect. I asked my friend to see if her husband would introduce me and maybe we could all play a game of pool. I met him and his hand felt good in mine as he told me his name, which was Mark. His eyes were a deep blue, his jaw could cut glass, and he was 23 years old. It turns out he worked for my friend's husband building houses part-time, but he was going to the local university for engineering. Smart, handsome, and strong, just what I wanted. We played pool, drank, and talked all night. When it was time to leave I gave him my phone number and told him to text me.

    A few days go by and I receive a text from Mark while I was at the gym. He asked me if I would like to go out to dinner and of course I said yes. I went home and was so nervous. I hadn't been on a date in a long time. What would I even wear?! He was taking me to one of the nicer places in town and then afterwards a speakeasy. I decided to put on a trendy black skirt, a fitted V neck T-shirt, and nice shoes. I tried to dress like the college girls in town so I wouldn't show my age too much. I looked good despite the Hell I had been through a year ago. I was ready. He picked me up and I was so nervous, I felt the infamous butterflies that I remembered from my late teen years, in my stomach. The music he played was pleasing to my ears and the overall vibes in the car were immaculate as the saying goes. I got chills of excitement.

   We get to the restaurant and started with some wine. I got straight to the point of what I expected and he was a bit shocked, but eager to fulfill my needs. I told him I wanted to try a Sub/Dom relationship for I had never been in one and I wanted to see if it was something I would like. He thought the idea of me wanting to be a submissive a bit odd since I am older than him, but I told him we could switch roles at any point. He told me he thought my boldness was hot. He liked that I knew what I wanted unlike the younger college girls who played games according to him. He also liked that I was more mature and that me being a MILF was alluring. He always wanted to be with one. I was delighted by this as it gave me more confidence. We finished our dinner, went to the bar, and this is where I told him the scenes I had in mind, the props we would need, and when and where our first scene was to take place. We continued drinking and he wanted me badly. He kissed me and placed his hand up my skirt while we were sitting at a private booth. He smelled so good, his lips felt amazing on mine, and his mouth tasted minty from the mojito he shared with me. He also didn't smoke or vape, which was a huge turn on. He pushed my panties to the side and I felt his thumb stroke my clit as he placed one of his fingers inside me. I moaned in his mouth and gripped his finger so he could feel how tight I was. It had been so long since I had someone touch me in this way. He started moving his finger in and out and found my g-spot while still rubbing my clit, then he placed two fingers inside me and rubbed my clit with the bottom part of his palm. He went faster and faster while I was trying to stay quiet, but I moaned in his ear and then I came all of over his fingers. He felt my strong contractions and whispered that he couldn't wait for me to do that on his dick. I smiled and told him maybe after our next date, then I asked to be taken home. He sucked my cum off his fingers and we walked out of the bar.

When we arrived at my house, we made out to the music playing in his car for a good 10 minutes. I wanted to do more and so did he, but I didn't want to have sex just yet, I wanted to wait and build a stronger emotional connection with him first, which he agreed with. He was so understanding and not offended, I was shocked. He told me as I went to leave that he would be thinking about me and my tight grip on his fingers for the rest of the night, which I did not doubt. I grinned, said goodnight, and went inside my house. I felt completely reinvigorated and happy as I showered off and climbed in bed thinking about my next encounter with Mark.