Here's one for ya'll
After having been in rural California for a year, living on couches and tents, I ended up back in Boston for about a year. I'd been in the woods for a minute and now had a room in a nice apartment, a flip phone, and internet access via my Google Nexus tablet. I figured it was time to use that tablet to my advantage and hit up OkCupid. There were some crazy nights and awkward stories. I'm not sure I feel comfortable sharing all of these but I might go further in the future.
So I met this girl Kat via OKC. She was pretty cute. Blonde hair, kinda chubby cute, couple years older than me (I was 29) had a bad wilderness scene tattooed on her upper arm, like whiskey, and could banter pretty well. So one night I ride my bike from Brighton to JP, to meet Kat at this tapas joint, Tres Gatos. I'm pretty new to the city life and had never had tapas before, so I didn't realize it was just overpriced, small portion appetizers and drank two beers on the way over. We meet up and banter over a couple drinks, and eventually order food. the food comes out and I realize 4 or 5 deep and not getting a real meal. Oh well, she's drinking as much as me. We finish up the tapas and she asks me to go to a party that her coworkers from planned parenthood are having up the road. We're getting along well so I figure it's all good and pedal my fixie alongside her walking up Centre St for a mile or two until we get to the house party. It's in a big old 3 decker on the 2nd floor, filled with a bunch of hipsters, artists, and all that stuff. I'm feeling a little out of place but keep drinking beers and what not. I ended up running into this other girl that I was talking with on OKC and ended up being a colleague of Kat. Definitely crossed that one off the list, but that's not part of this story. I'm not sure how long we're at the party for at this point but Kat asks me to go on the porch/balcony with her. She gets out there and lights up a cig, looks at me, goes to gimme a smooch, drops the cig, and straight pukes on my brand new brown vans. Mind you, I'm pretty wasted but home girl is next level wasted. Being a drunken gentleman I offer to walk her home. This ends up being a long walk, almost to Roslindale. She invites me to stay and despite being pretty bummed, I'm zonked and decide it's an ok idea. Turns out she's living with her sister, whose a minister, and her sisters wife, but she says it's not an issue, we just need to be quiet. We get up the creaky ass old winding wooden staircase and make it into her bedroom where she just passes out in the center of the bed. (you might ask why I didn't call an uber- I was a bum jamming OKC with a tablet, telling girls my flip phone was vintage back in 2015) I crawl on into bed and to no avail try to sleep as Kat steals the blankets and starts snoring away. I ended up sleeping a bit because at some point I saw the sun outside and figured it was time to make my exodus. Well, Im shuffling around and start getting my pants on when Kat grabs my hand and says "you're such a nice guy. thank you for getting me home. come back to bed." I'm not trying to do this but I'm a sucker so I get back to the bed. She's trying to get me hard and it's just not happening. Visibly frustrated, she says "just lay with me, I want to do something for you" and starts playing with herself, moaning and making a bunch of noise. All of a sudden she grabs my arm and moans "oh my god. I'm fucking coming" and straight squirts across the room. I'd never seen anything like it. Straight shot squirt across the room. She finishes and says "do you like that?" It didn't do anything for me but I hang for a bit longer before getting up to leave. I get dressed, walk out the bedroom door, and sitting at the dining table eating eggs are her sister in the minister garb and her wife. I just had to say "hey, y'all have a really nice house." and did that ride of shame home.
Topic: Awkward Sexual Experiences (Read 462600 times)