I [M] fingered my date under a bar as a waitress watched

I had matched with this beautiful older woman on a dating app a couple years before I was married, and we quickly hit it off. The more we talked the more we just enjoyed each other’s conversation. We didn’t really talk dirty at first but I flirted enough to know there were some embers of an inner freak there.

One of my favorite parts was that she was a lawyer – which was sexy as fuck to me because I love when women with high-level, high-pressure, corporate jobs are closet freaks.

We had agreed to meet for drinks one day after work at a nicer restaurant. In the days leading up our date, she had told me she had fake breasts. A lawyer with fake breasts? Are you kidding me? I was in heaven.

The night before our date I had one request: Wear a pencil skirt. She wouldn’t commit to it but I was hopeful.

We met in the lobby of the restaurant and she was better than her pictures. Tall, dark hair, great figure, great body. Her tits looked perky through her white button-up shirt. Her hips looked delicious in her pencil skirt. She wore it. Later she said, she was just playing hard to get. She wore it just for me. When we hugged hello, I could feel my cock start to swell in my jeans. I’m sure she felt it, too.

I had booked another date for dinner that night because, first, you never know how a first date is going to go, and, second, she said she plans that night, too. But the more we talked and drank, the more we laughed and laughed. We had some crazy connection and an intense attraction. We got some appetizers and were just enjoying ourselves.

Then one of those moments happened, when we looked at each other and just started making out. Not furiously or inappropriately or anything like that. Just passionately but subdued. While we were kissing, I rested one of my hands on her inner knee. When she parted her legs, my mind went nuts and my cock got stiff.

I started to slowly reach my hand up her skirt but it was more of a grabbing-her-thighs-when-we-kissed type of thing. We pulled away, our gazes lingering – I’m not kidding, it was like something from a movie – and took a sip of our drinks. The bar was pretty empty so we didn’t mind being a little handsy. But I knew my window was now.

As we kept drinking, her legs kept spreading and my hand kept going further up her skirt. We eventually turned our stools to face each other and she put her legs between my legs. I just went for it. I reached all the way, trying to be as nonchalant as possible. I reached her lace panties and the heat coming from them could’ve warmed an entire house. I, slowly and subtly, slid them to the side and felt her wetness for the first time. I almost came in my pants. She was bald under her panties. I was in heaven. We kept our conversation going, taking sips in between. At one point I had my fingers buried deep inside her and looked around to make sure no one was watching, and a waitress was. A good looking, young, blonde waitress was staring like she couldn’t believe our eyes.

That was our cue. We closed out our tab. Took an uber to her house and we naked within seconds of walking in the front door. Her body was the perfect 40ish body. I was in heaven. I explored every inch of her. I ate her out for what seemed like hours. She took her in her mouth fully. I refused to cum in her mouth, well, that time at least.

Finally, it was time. I got on top and my tip rested on her slit. We both looked at each other with so much anticipation, I nearly shot my load all over her waiting pussy. I started to push in but she told me to get a condom. I did. She slid it on – which I think is the sexiest thing ever – and guided me in. I didn’t last long, but she knew that was coming – no pun intended. We recovered and snuggled. We fucked again. She said I didn’t have to sleep over but was I really going to let a night of being next to that naked body go to waste? Nope.

We woke up the next morning, Ubered back to the restaurant, got our cars and went to work.

Source: reddit.com/r/gonewildstories/comments/p2ginl/i_m_fingered_my_date_under_a_bar_as_a_waitress