TL;DR: thank god for whisper.
I was scared. Sexually. Still a virgin, religious upbringing, but wildly sexual. I had such a fascination (uh, kink) for MILFs and, back in its heyday, Whisper was a saving grace.
We met on whisper. She and I were talking for a week or so and I found out I was gonna be in her town. She was tall, red hair, described herself as being thin but perfect tits and ass. I couldn’t believe it until, well, this one night.
She said her husband was having a friend over so she could get out, but it’d have to be at a public place. So we went to Ralph’s at like 11pm. She pulled up in a nice car and texted me to get inside.
Our chemistry was electric. We made out in the front seat for a while before she pulled my hand under her shirt to show me she wasn’t wearing a bra. I moaned while she kissed my neck. She giggled. Then she pushed my hand under her shorts to show me she wasn’t wearing panties.
“Wanna go somewhere a bit more private?” At this point my heart (and cock) were beating harder than, uh, ever.