First time with an older woman [MF]

This is from late last year after I had broken up with my girlfriend. I had a very vanilla sex life with my ex so I was excited to get out there again and have an open mind. I’m unsure why but I set my Bumble account from 18 – 50, I was 27 at the time.

I matched with a lady called Jenny. She was 43, blonde, looked slim and pretty although her photos were a little hard to tell a lot about her appearance. Now, of course, she didn’t look like a girl my age and smoking hot but this isn’t one of those false stories of getting with a supermodel.

She started talking to me and we had a bit of general chit chat before she got straight to the point. She asked why I was on Bumble and if I realised I was talking to someone 16 years older than I was. I very well knew what I was doing and how old she was. She ended up telling me that she thought that I was cute and that she hasn’t been married, doesn’t have kids, doesn’t intend on having kids and also just wanted some casual fun. As soon as that message came though I thought I had hit the jackpot although I wasn’t sure where to go from there and if I would go through with it.

So we settled on a night to get drinks close to her place. She just wanted to have a chat and see what I was like in person and later mentioned that she didn’t have sex on the first date. I wouldn’t be truthful if I said I nearly bailed on the date but in the end, I decided to go through with it.

She told me what table she was sitting at and it was at a cool small little bar that was quite intimate and had its privacy. I walked all the way to the back and there she was. She was a lot more attractive than her photos made her out to be. She was really beautiful and had a glow to herself. She didn’t have massive boobs or anything but a really nice petite body with a beautiful smile. She was wearing a black dress, not a skin-tight one but a sundress type one where it was a little loose that went to just above her knees.

We started talking about life, travelling, relationships (especially about my ex) and of course her relationships and what she was looking for in a guy. We were working our way through two bottles of wine and by that time there was some touching going on, brushing of each other arms and hand, legs rubbing up next to each other. She told me that after meeting me and our ideas aligning that she was keen to give it a go and keep seeing each other with an NSA vibe.

At that moment she put her hand on my thigh underneath the table and started to squeeze it a little. I followed and put my hand on her thigh as well. Her dress was revealing a lot of skin by sitting down at this point. Her thigh felt so soft and warm. I could see her bite her lip a little while I moved my hand up and down in slow motion. We continued to talk like this for a little bit while being extremely close to each other, hands on each other’s thighs and talking about fun things we could do.

In the heat of the moment and with the wines going down well I moved my hand high up her thigh and underneath her dress. I could feel the warmth coming from her pussy. I stopped and teased her for a little bit rubbing the inside of her thigh, getting awfully close to her panties but never close enough to touch them. She started to squeeze my thigh a little harder and whispered in my ear how much she wanted me to be inside her pussy at the moment. I went a little higher this time and felt the outside of her panties with a slight touch. Her panties were soaked, enough to be worried about the chair and if it would go through the dress but at the time all I could think about was feeling and potentially being able to taste her sweet pussy.

I started to rub the outside of her panties with enough force that I could feel her pussy underneath. It felt so good. She lent over and gave me a kiss. Our tongues connected in a passionate way that we didn’t want the kiss to end. I slipped one of my fingers underneath her panties and had my first touch of her pussy. I did need to change up my arm a little though as it was hard to get access. After a brief shuffle, I slipped my finger under again but this time due to how wet she was my finger slid straight in and before I knew it my full finger was inside her pussy. She had to stop the kiss as she started to hold back a moan that would have been too much for the bar. I decided to tease her a little bit more and took my hand back a bit to her thigh. I moved my fingers all the way up and down, spreading the juices from her pussy all over her.

The timing was incredible as a waitress came up and told us that they were closing up the bar and we could leave after we finished our drinks. Jenny then asked me if I’d like to come back to her apartment which was just down the road.

Source: reddit.com/r/gonewildstories/comments/j75u1q/first_time_with_an_older_woman_mf