rant · moment 12 of 22
Ray's Craigslist Hooker Story at the Marriott
from Seeking Arrangements (with Wendi Starling) · #47
Audio-only archive episode — no video to seek.
2 minRay recounts losing his virginity to a Craigslist sex worker at a Marriott for $150, including an awkward moment where she wouldn't reciprocate oral sex, and a separate story about a hooker who kissed him.
- 39:00Ray describes finding a woman on Craigslist who was chubby and mostly just laid there.
- 39:27Ray explains that sex workers on Craigslist always hint at GFE—girlfriend experience—but don't actually deliver it.
- 39:39Tim notes that one Black woman hooker actually kissed Ray because he was sweet and nice to her.
- 39:52Ray recounts asking her to blow him, but she refused and asked him to go down on her instead.
- 40:07Ray admits he didn't reciprocate at the time but says now he would eat her asshole without hesitation.
- 40:19Tim suggests Ray should have locked her down after they both came, while he's in better shape now.