Much older coworker [F] recognized [M]e

This is a 100% true story, aside from the lady’s name. For the sake of privacy, let’s just call her Flo. I was 28 years old at the time.

I work a blue collar job but every now and then we’re required to attend onsite classes, most of which are safety oriented. One such class was conducted by Flo, an older woman I had never seen before. At least not in person.

Flo was thirty years my senior, a 58 year old redhead who most people would describe as a BBW. Average height but definitely plus sized, including wide hips and a very ample bosom. She wasn’t unattractive but she didn’t exactly ooze sexiness, either. I took notice of her but not much, not initially anyway.

Part of the class had Flo standing up front and speaking, going over a power point presentation and the other portion she dimmed the lights and played a series of instructional videos. During this portion she took a seat in an empty chair in the back of the room which – either by fate or design – happened to be right next to me. A couple of times I could feel her eyes on me but I didn’t think anything of it.

Helping [M]y much older coworker [F] celebrate her birthday

Dana and I had been coworkers for a couple of years when this story takes place. I was 21 and she was just turning 43. And to be honest, she was WAY out of my league.

Physically speaking, Dana was around 5’4″-5’5″ with medium short dark brown hair and green eyes. Her face closely resembles the actress Mena Suvari, if you’re familiar. And body wise, Dana was on the thick side. Not a BBW, but thick. Her breasts weren’t huge, a small C cup at most, but her ass was out of this world! Like the true definition of a badonkadonk.

As far as our work relationship went, we got along great. She was an office worker and I was a blue collar guy, but we shared the same break area and would often talk during lunch. I had developed a bit of a crush on her and as time went on I got a little bolder.

I was young and dumb and as such I became a huge flirt. Dana, however, just laughed off all my advances telling me more than once that I was too young. Still, though, we remained friendly.

[MF] She told me I was too young

Belinda and I met online. I saw her dating profile, sent her a message, and to my surprise she actually responded! That was the good news. The bad news was that she wasted no time in letting me know that I was far too young for her.

She was right, of course. Belinda was 55 at the time and had children older than me! I was undeterred, however, and tried my best to keep our conversation going. She was exactly my type!

Latina, about 5’5″ with medium length dark brown hair and brown eyes. And while she wasn’t a BBW she wasn’t skinny, either. Big heavy tits and wide hips. Perfect.

Luckily she seemed willing to at least talk. And, as we got to know each other via the dating app, she began returning some of my flirtations.

Just as an aside, if you’re a single guy on a dating site my advice would be just keep the conversation light, ask a lot of questions (nothing invasive), and show some genuine interest. After about a week of daily back-and-forth messages we were really hitting it off so we exchanged numbers and started texting.

[MF] My First Time Giving A Facial

She was 50 – nearly twice my age at the time. A divorcé who was left with an empty nest when her son joined the military.

We met online and although she initially said I was too young, we kept talking and ended up really hitting it off. Within a few days we exchanged numbers and our texts got flirtier and flirtier until we were just outright sexting. We ended up talking on the phone – a 3 hour conversation that culminated with us masturbating together. By the end of that week we had came together over the phone three times and made plans to hook up over the weekend.

Physically she’s what most would consider a BBW. A curvy black lady with a caramel complexion, dark hair, dark eyes, wide hips, thick thighs and HUGE breasts.

When I showed up at her place we made small talk for a bit before we began making out on her couch. And it wasn’t much longer after that when she took me to her bedroom. The mutual attraction was strong and we both stripped out of our clothes as quickly as we could and hopped up in her big comfy bed.