I was in my late 20s when this happened, and lived (still live) in Chicago. I was in grad school for filmmaking. I should note that I was a rather arrogant and self-centered person at this time, and I engineered these qualities in a way that I felt attracted women. To a degree, I was correct. I did get laid often enough. But I was also quite lonely. Also drank too much. So yeah, there I was.
The first woman was Lauren. She was a 27 year-old African-American woman who had just moved to Chicago and worked from home as a marketing associate for a bra retailer. I swear I am NOT making that detail up. She and I met on OkCupid, exchanged a handful of messages, and talked by phone soon after. She asked me what I was looking for and I sensed she wanted to hear that I wanted a relationship, so that’s what I said.
Our first date happened at a lunch spot near her apartment. She was a little late. She had thick forearms, hair up in bangs and pudgy thighs. She had sent me a picture of herself before I arrived. There was nothing scandalous about the picture, but it keyed me in to the idea that she probably would not be too hard to get into bed. After talking for a while – during which time it seemed we did not have that much in common, really – she sure enough asked if I wanted to come back to her place and hang out. So I wouldn’t seem to eager, I pretended like this was moving a bit fast for me. She apologized and said she understood. In reality, I had a condom in my pocket. I pretended to reconsider, and said I suppose I could come over for a bit.
She had a nice studio in a nice neighborhood. We sat on her couch and drank wine and the conversation gradually became more sexual. I remember her saying something about giving head and me saying I didn’t like blowjobs. She also said that I seemed like I’d been with a lot of women. One thing led to another and eventually we were having sex on her bed. She called me *daddy* as I moved in and out of her. I’m not sure what was up with that. She was a little surprised but not deterred to realize I had a condom in my pocket.
I did not spend the night. Over the next week, as I edited my thesis film, she started texting me. This is when things started getting a little weird. She first said that she couldn’t believe she’d slept with me on the first date, and that was not like her. Then she would text, “want you between my thighs.” There was some emotional confusion going on with her, it seemed, and that turned me on. On Thursday she asked if I wanted to come over and I turned her down. On Friday we were going to hang out again. Before I took the train over, she texted me that she felt like we shouldn’t have sex this time. We should just hang out and get to know each other. I texted sure, but felt fairly certain that it would be otherwise.
I arrived with a bottle of wine. She asked me to take my shoes off. Those were the two things we did have in common: red wine and OCD tendencies. We drank wine and watched reruns of Friends. I gradually sidled closer to her. I put my hand on her leg at some point. She did not pull away. I put my arm around her. I kissed her cheek. She tasted like too much makeup. This wasn’t something she’d done for me; I guessed that she always wore tons of eyeshade and makeup. She told me to stop it because I was making her horny. She said she didn’t want to do what I was making her want to do. I pulled away completely and lay my head back on the couch. I told her whatever, it was up to her, but that I wouldn’t feel ashamed of natural human impulses. I glanced at her after a short time and saw her looking at me. I either asked if I could kiss her, or I just leaned in and did it. Either way, she reciprocated.
This led to me giving her head on the bed – her labia was large and purple, and felt sort of sticky against my tongue, possibly with blood residue. She had mentioned just finishing her period. She kissed me after I finished going down on her and laughed and said,
“I taste myself.”
Then I fucked her. This time I hit it raw. I believe she was cool with this because it was the end of her period. It had been a while since I’d had totally unprotected sex. I loved it. I pushed her legs back as far as I could and she bobbed up and down on her pillows and called me daddy again. And again. And again. I moved fast and the bedsprings squeaked. I felt her wetness and warmth and came inside her without even trying to pull out. I remember wiping sticky female stuff off my cock in her bathroom and wondering a) why I didn’t see any blood and b) If I’d gone too far. But I had fun. We cuddled on the bed and had sex one more time. I left once again without spending the night. I took the rest of the wine I’d brought but left my watch. She informed me of this via text message as I rode the train home.
I did not consider the ethics of how I was treating her. I did not consider how she might have felt about not wanting to have physical intimacy with this guy who she might form an actual relationship with, only to get rather sleazily seduced by him. I just felt proud of myself.
(This is just part one. There will probably be three or even four parts. Let me know if you want to read more).
Source: reddit.com/r/gonewildstories/comments/vhmndv/two_girlfriends_in_two_weekends_lauren_mff