Libby and I agreed to meet a few days after we'd hooked up at Allison, Derrick and Holly's party. This was our 'first date'.
We met at a local diner for coffee.
"I think I'm more nervous now than I was at the party..." she admitted. Since this was only the second time I'd attempted to meet with a woman socially in more than 10 years, I completely understood.
I immediately noticed two things about her that I didn't catch in the dim lights at the party: (1) she's a lot 'prettier' than I remembered, and (2) she had freckles. I could only imagine what she was noticing about me in the daylight.
After several minutes of having to lower our voices in a public space, and 2 cups of really bad coffee, we decided to take a walk over to a nearby park and speak more freely.
"So what's your thoughts on your first 'swing event'...?" I asked as we settled in on a bench with no one else around.
"I have to admit that I was so fuckin' turned on...!" she shyly admitted making the mildly annoying giggle again. "I was still horny when I got home that night...I played with myself until I fell asleep..."
"Anything in particular stand out for you...?" I teased. I could fell myself getting hard.
"I mean, my first woman...my first...black...dick..." she blushed, "all in the same night...I was still wet the next day..."
"Whoa! First 'BD'...?" I acted surprised, although I wasn't. "Hope I represented my people proudly..."
"Oh, don't worry, Toni," she assured me. "You did just fine!"
This time I blushed.
Libby then proceeded to share more of her personal story: married her college 'sweetheart' who was only the 2nd person she'd had sex with; which led to a limited and non-existent sex life (they didn't have sex the last 3 years of their marriage). She spent a lot of time fantasizing and masturbating.
"I couldn't bring myself to cheat..." she said rolling her eyes. "Friggin' Catholic upbringing...!"
"Tryin' to make up for missed opportunities...?" I grinned.
"You better fuckin' believe it...!" she said proudly.
She'd shocked me with her response.
"You go girl..." I smiled giving her a mock applause.
"So..." she started sheepishly. "Since we are already...kinda...you know..."
I feigned innocence, wanting her to 'spell-it-out'.
"Are you still interested in...helping me out some more...?" Libby finally continued.
I intentionally allowed for a long awkward pause.
"It will be my honor and pleasure to keep providing you with all the guidance and assistance you need..." I smiled.
"Thank you, thank you, thank you...!" she squealed. She surprised me with an unexpected bear-hug.
We continued to chat and took a short stroll around the park. Libby invited me over for dinner that evening so I went back home to change. I arrived at her place around 6 with a bottle of red wine.
Libby answered wearing a long, floral sun dress and sandals. This was also the first time I'd seen her wearing full make-up. She looked really nice. We sat and had dinner and shared more stories. I mostly told her about the adventures that I'd had with Cassidy, and Libby continued to ask more questions.
"So what should we do next...?" She asked as we cleared the dishes. "Do you know about any more parties?"
"Are you wearing underwear, Libs...?" I said, completely out of left-field.