A MILF surprised me [M] in the shower and then rode me on her bed

This story happened right after I moved to one of the many cities I’ve lived in. Soon after I got to town, I joined a dating site to see who the area had to offer. I’ve had a thing for older women for a while so I set my age range pretty high and ended up matching with a woman in her 40s. At the time I was in my late 20s.

She had the ideal mom bod. Big, luscious breasts. Wide hips. Thick ass. Her pictures made my dick jump. If you look back in my other stories, I love, love, love mom bods.

After sending messages back and forth, we decided to go for a swim in her community’s pool. I thought it’d be a perfect chance to see what she was working with, especially after she agreed to wear a bikini. It was public so she felt safe. I was game.

I showed up and she was sexier than her pictures. Thick in all the right places, blue eyes and blonde hair. Total MILF. Definitely the type of woman I would’ve flirted with. I told her I couldn’t stay too long because I had to meet up with some friends for dinner. In reality, I had another date with a nice looking blonde that was more around my age.

I [M] fucked a waitress the day after she served me

About a decade ago, I was out to eat with a few friends at an asian restaurant while on a road trip when the waitress walked up to our table. I was instantly taken aback. She wasn’t just pretty. She was hot. She was curvy, thick, great chest. Later I saw she had a terrific ass.

She did her usual introduction and took our drink orders. I was in one of those don’t-give-a-fuck moods because I was in a different city and knew I would never talk to her again. Or so I thought.

I started flirting and shooting my game. It was kind of working at first. Then she kept dropping by our table more and more, so we kept talking more and more. It turns out we randomly had some mutual friends in common from a city she used to live in years ago and then she said she was going to be running in a race the next day that one of my friends from that city was going to be running in also.

“Come by the race and cheer me one,” I remember her saying.

I [M] had first-date sex in a parking spot outside of a bar

I’m just a dad who’s working from home in an empty house and it’s given me time to reminisce about the good, old (read: single) days. I thought I’d write down some of my greatest hits to share with all of you. Hope you enjoy.

Before I met my wife, I used to love online dating. It was like shooting fish in a barrel or, better yet, online shopping for women. I used Tinder a lot and all the online dating sites. It resulted in lots of conversations with women, which turned into lots of dates and plenty of encounters. I always knew I wanted to settle down but I also knew I wanted to have as much fun as I could before that, and I knew if I’d know when I met the right woman.

When I was single, my approach was simple: I knew – and still know – that every woman has an inner slut. It was a matter of getting them to show it. Men, listen up: Women are like onions. Keep peeling back their layers and they’ll eventually peel off their clothes. And I also knew that I needed to use my words to start turning women on. Not just send them dick pics. I used my words carefully and wisely. It worked.

A single mom blew me [M] twice in a mall parking lot the first time we met

About a decade ago, I started talking to this single mom in her late 20s who lived about two hours away through a dating website. We quickly hit it off and found out that we weren’t just two horny people but we were very sexually compatible. We both liked the same kinks. Both enjoyed the same stimulation. We were two slutty people.

We almost met right away. She was supposed to come to my city because her dad was in the hospital down the street from me but it never happened, so we just continued to text. Very, very quickly the texts turned dirty. And I mean raunchy dirty. She told me how she loved to be peed on. We went into detail about how and where I’d cum in and on her.

And she sent me any picture I wanted any time of day from any place she was. It was incredible. At work? It didn’t matter. She’d take pictures at her desk, lifting up her dress to show me her panties and then pulling them down to show me her shaved pussy. In the car? She’d show me her panties and pull them aside to show me her wetness. I’m talking hundreds of photos. I, of course, reciprocated, sending pictures of my cock whenever I was free. I sent her precum pictures. Action pictures of me cumming. Videos. Ball shots. Pictures of cum shot all over my stomach. It was glorious.

I [M] fucked an older woman in the ocean but she forgot she had a tampon in

I had a big thing for older women when I was in my 20s, so when I scoured the online dating websites, I focused on those women who were 10 years (or more) older than me. I started talking to one who lived about an hour away. She was a single mom with sexy eyes, dark curly hair and a great mom body. If you read my previous stories, you’ll see this is a huge turn on for me.

We exchanged messages for a few days and then shifted to texting, where I slowly started feeling her out to see how dirty she was. I was a walking boner in my 20s, jerking off multiple times a day, but I also knew women in their 30s were in their sexual prime – so, of course, I took advantage of that.

We agreed to meet at a local beach and see what happened. By then, we were exchanging pictures and sexting more often than we weren’t. On the day we met up, she picked the parking lot and the beach. I remember it being warm and partly cloudy. She was waiting in her SUV when I texted her that I arrived. She said she had to change into her bathing suit, and I said I had to, as well. She told me to get into her car and we’ll change there together.

I [M] fingered 2 girls in the same day at 2 different bars in Nashville

It was one of those bachelor parties that was just wild. There were something like 20 of us dudes partying around Nashville, drunk for three straight days. I walked around with a pair of fake glasses with a big dick as the nose (Dudes, let me tell you, it sounds weird but I talked to so many women because of that. It was the best ice breaker).

Yeah, one of those bachelor parties.

The first girl I fingered was a blonde bombshell. I was sitting on the opposite side of a u-shaped bar from all of the other dudes. We were yelling across the bar, being obnoxious and drunk but having a great time when two girls squeezed next to me to belly up to the bar. One was brunette and the other was blonde. The brunette stood behind the blonde, who made a comment about my glasses and we started talking. I offered to move back a little so she could get a better spot at the bar and she moved in between my legs. I remember distinctly that she had on a long, thin skirt — it could’ve been a maxi skirt but I was just drunk enough to really pay attention. It was busy so she was waiting for a bartender for a while. Because of where she was standing and because I was a bit daring, I put one hand around one side of her waist in front of me. She didn’t move away so I waited a moment and then started rubbing the waistband of her skirt. I remember the skirt was a lighter color and her short-sleeved shirt was a darker color, and it showed a little of her navel. I was rubbing her stomach, even tickling her belly button — hey, why not?. And she kept responding in positive ways, like putting one hand on my knee while the other was trying to order drinks.

I [M] fucked a woman in the back room of her family’s store

Once summer when I went to visit my parents for a few weeks, I, of course, got incredibly horny. I wanted to spend a lot of time with them and not chase women all over the city but, alas, my full balls told me it was time to unload them.

So, I did what I always do: I went on a dating website and flooded the market. A woman responded who was incredibly intriguing. She lived about 45 minutes away, out toward the rural part of the state, and had a perfect face. Turns out she used to be a beauty queen. She didn’t really have any pictures of her body posted which was an instant red flag for me. After emailing back and forth for a while, we took it to texting and I was able to convince her to send over some full-body shots. She had definitely grown into her body. Wide hips. Big boobs. Flat tummy. I responded with a picture of something else that was growing: My cock.