Two Girlfriends in Two Weekends (True Story)

[TJ2800]

A few years ago, while in grad school, I was going through a sort of--how else to put it--sleeping-around phase. I wasn't too interested in commitment. I was more interested in seduction. Which I had been lousy at earlier in my life, because I had no clue about women or myself. But in my late 20s I'd gained confidence and was less afraid of women.

In the spring I started seeing this one woman I met on OKCupid. She and I had already spoken on the phone prior to our date. While this was only a date, I still brought a condom. She gave me a vibe of someone who was somewhat lonely and chiefly interested in sex (like me). We went out for coffee and lunch and did indeed wind back up at her place and had sex. On the first date. The next weekend was similar. She had been sending me dirty texts throughout the week, but had also asked that we not have sex and just hang out the next weekend. I brought a condom again, because I still planned on seducing her. We watched T.V, I got close to her, put some moves on her, at first she rebuffed me, I persisted and she decided otherwise. I know I was being sleazy, but I will also say I persuaded her to a point that she genuinely wanted it. We had sex. Later on that evening, we fucked again, this time without protection. It was the end of her period and she felt okay about it. So yes, I raw dogged this woman on our second date. I went hard, because when you're bare, it's easy to do so. She called me "daddy" a few times over. She contracted on my cock. I came inside her.

The next evening I took a break from working on my thesis to get a beer (also drank a bit too much at the time). Again; there was a part of me that didn't plan on hooking up, then there was the part of me that saw a woman sitting at the bar and sat next to her. She was with a guy, but he turned out not to be her boyfriend. She started talking to me first. One thing led to another, and eventually we went to another bar, made out, went back to her place and had sex, twice. The first time she dug her nails into my back and scratched me nape to buttcrack with each stroke. The second time was after being woken up at some early morning hour by her cats. She rode me and stiffened up and bucked her thighs and yelped. After that, she started riding me real hard, her face close to mine, her hair flying in her face. I couldn't cum. I guess my dick was exhausted after the last 48 hours.

She was about ten years older than me and had just gone through a divorce, I would find out. We cuddled and she mentioned that it looked like she'd drawn blood on my back. I joked about the lyrics to You Oughta Know by Alanis Morissette. That was how she found out that I was ten years younger.

Anyway, I made plans to hang out with both of them the next weekend. Me and the older woman went to a movie, came back to her place, talked for a while and then she sat on my face. The next morning I ate her out again and fucked her again.  She creamed in my mouth. I was under her sheets, feet poking out the back of her covers, fondling her tits with my hands. All the while licking her. I stuck a hand above the covers and fanned my fingers out on her mouth and she sucked on them. Still licking. At some point I moved my tongued up to the area of her clit and ran a hand down her body and around her thigh. She was making a good deal of (muffled, to me) noise by this time. I slid a couple fingers inside her. I could not feel anything tangible. Just liquid. Like sticking your fingers in a warm puddle. I swished my fingers around, touched her thigh (which felt already wet), licked her clit in faster circles. Her legs jolted upwards and her thighs seized. She shifted backwards on the bed just as I was moving my face down into her hemorrhaging fluids. Afterwards, we had sex and she kept asking me to go harder and harder. 

Then I washed up at home, went to see the other woman in the evening. She had once again said she wanted to just hang out that day and I once again had planned otherwise. We had a picnic, went back to her place and I once again managed to sweet-talk her into fucking me. I went down on her first. I noticed a filmy white gob dangling from her right labia as I spread her legs. Other guys would maybe pack up and head out at that moment. I just pressed right in there and gave her a good long pussy lick, top to bottom, and lapped that shit up. Yes, I swallowed a yeast infection. And kept pleasuring her for perhaps ten more minutes.

Afterwards, I fucked her sideways on her bed, against the wall. I had trouble getting in at first and asked her, "how does this feel on a 1-10 scale?" She said, sassily, "Three." Almost right after, I jammed all the way in, balls deep. She said, "Ten." I did use a condom this time. I didn't spend the night.

The next day I felt both sexually fulfilled and prideful but also had a stiff neck and a sore throat from all the cunnilingus/yeast infection. I planned on keeping things going with the older woman, because she and I actually had a lot in common and I wanted to keep casually seeing her. I essentially dumped younger woman. I just did not text her anymore. But then older woman dumped me via text not long after. At this point it started to occur to me that maybe my behavior had been kind of fucked up and wrong. I wondered if maybe I was a borderline sex addict. 

I'm engaged now, to a wonderful woman, but sometimes I think about this "dark side" of me, so to speak. How troublingly promiscuous was my behavior? Should I be concerned that I keep thinking about it? Share thoughts in the poll and below. Thank you.