At this time in my life, I was a burista at a small coffee shop by my house (college grad working at a coffee shop, surprise surprise).
I became really good friends with Lisa, one of the managers there. She was 37 and married, and also my *boss*, so it was strictly platonic, but we had a lot in common (movies, music), so through that, we became close friends outside of work.
She was one of my closest female friends, and I had no problem talking openly with her about my sex/dating life. She gave me advice when and where I needed it, and over time, became a great wing woman for me. In total, she helped me fuck 5 different women throughout the course of our friendship, simply by introducing me to them, and putting in a good word for me. It’s why I can’t for the life of me understand men who scoff at just being friends with women. But I guess that’s another story.
Anyway, the first of these women, was Kathy.
One night, I got a text from Lisa out of the blue.
“Hey dude! Random question, buuut, how do you feel about tall, recently divorced, older women???”
“Lol? That sounds oddly specific. But you know me. I don’t discriminate.”
“Sooo, would you be interested in maybe hooking up with one?”
“Is…there one looking to hook up???”
“I’m glad you asked! Why yes! Yes there is.”
Kathy was one of Lisa’s friends. They, like Lisa and I, were pretty open about their sex lives – or, in Kathy’s case, a lack of one.
The backstory was that Kathy had recently divorced her husband, and was in serious need of dick. That’s where I came in.
She didn’t want to use a dating app because it felt weird and unnatural, she wasn’t much of a bar hopper, so picking someone up there was out of the question, and every other man in her life was older, and/or married.
“I need a nice young stallion,” she told Lisa. “Those guys can fuck.”
She sent me a picture of Kathy, and I almost couldn’t believe it. She was a goddess of a woman. Tall and hourglass shaped, with a light tan, wavy, auburn hair, and piercing green eyes. She looked like a model.
“Dude are you fucking for real???”
“LMAO. I am! Like what you see??”
“Uh, *fuck* yes?”
Once Lisa confirmed I was down, she was off and running. She went back and told Kathy she knew just the guy to snap her little dry spell. She sent me a screenshot of their conversation.
“There’s this guy at work. Young, fit, knows what he’s doing.”
“Any pictures?”
Lisa sent her a link to my Instagram.
“Ohh he’s a cutie.”
“Right? I already told him about you. He’s down if you are!”
“Well there it is then! Let’s do this. Give him my number.”
“Okay! Sending right now. I think you’re gonna like him.”
“Oh, I think I’m gonna *break* him.”
Little did I know, she’d be right.
Like with quite a few sexual experiences in my life, things escalated quickly. Lisa had texted me about Kathy on a Thursday night, I started sexting with her the next day, and by Saturday evening, I was driving to her house to fuck – though not before fucking one of my regulars. I know. I had a problem.
Anyway, Kathy lived almost an hour away from me in an upper class suburb. I pulled up to the huge house and knocked on the door, half expecting a butler or someone to answer it.
She opened the door in a form-fitting red dress and heels, and immediately I felt underdressed and intimidated. I hadn’t even thought about what I’d wear (since our clothes weren’t gonna stay on long anyway), but the difference was stark. I was in a plain white t-shirt and chinos, with Converse sneakers. We looked ridiculous together.
“Hey! Come on in!,” she exclaimed, hugging me at the door. She was taller than me by like half a foot because of her heels. I had no problem with women being taller than me, but I had also never been with a woman *that* much taller than me. More intimidation.
She lead us into her living room which was right out of a magazine. Fireplace, black leather couch, glass coffee table with a bottle of wine and two empty glasses on it. Was I here to fuck, or was I early for a book club meeting?
“Sit, sit,” she said, rubbing my shoulders as I sat on a love seat across from her, the coffee table separating us like a desk at a job interview. In some ways, it *was*.
She poured herself a glass of white wine.
“So. This is, kinda crazy, huh? Haha.”
“Uh, yeah haha. A little bit. I feel like, underdressed.”
“Oh, no! I’m sorry, that’s on me. I just love dressing up. You’re fine.”
“*You* look fucking amazing.”
“Aww thank you! So sweet.”
She swirled the wine around in her glass and took a sip, locking eyes with me as she drank.
“So!,” she continued. “Talk to me. How are you? How’s Lisa? You like working with her?”
“I’m good. She’s good. Gotta thank her for this, haha.”
“Hahaha. Absolutely. Well, let’s talk about it! I mean, you know *my* story, but tell me about yours. Lisa says you’ve been…having some fun?”
I didn’t know how much of my sex life Lisa told Kathy, but I *do* know that Lisa pretty much knew everything, and I assumed she told her whatever she needed to, in order to really seal the deal for me.
“Ha. Well, trying to, yeah. It wasn’t always that way, so. Trying to enjoy it.”
“What do you mean it wasn’t always that way?”
“Didn’t really do anything until after college. I was kinda nerdy…shy. I mean, I still feel that way now sometimes, but—
“No! Look at you! If I was your age and we went to college together…ha…*believe me.*”
“Haha. Well, thanks.”
She took another sip of wine and smirked at me.
“So, you’re here to make up for lost time…”
“Absolutely.”
She put her glass down and slowly walked over to me.
“I think I can help with that.”
Source: reddit.com/r/Erotica/comments/12og2il/journey_to_100_women_brians_sexcapades_part_9