I found Cassandra on Match.com, right around the time I began my online dating rampage. I asked her on a date after a few emails and we agreed to meet at a bar downtown. I added her on Facebook and called her a few days before meeting up. I don’t remember too much about the conversation, but she was easy to talk to and we confirmed the date. We met at a fancy lounge downtown. After ordering drinks, we sat on a couch next to each other. I told her I had plans later and was leaving in one hour.
She was short and thick, with giant tits and a round ass. She was borderline, but not fat yet. She had pretty, white skin and big, dark brown eyes. Here hair was straight and brown, but cut in one of those stupid bob cuts that American women like to get. Her nails were done properly and her teeth perfect and white. She was 29 years old, the upper age range of what I prefer.
Cassandra was a smart and successful girl. Her degree was in business and she worked a high-paying corporate sales job. She was well dressed and wore expensive jewelry. I could tell right away that she was a slut. And I was right. She confirmed this within the first 15 minutes of conversation:
“I was a slut in high school,” she said, proudly.
Yeah, no shit! I thought to myself. She was comfortable talking about sex so I kept that line of conversation going for a while. I touched her heavily. She was receptive and touched me back. After one hour, we left and walked down the block. I gave her a hug and she kissed me on the cheek. Then she aggressively kissed me on the mouth. I was not planning to kiss her yet and this took me by surprise. Of course, I kissed her back. Then I went home.
I waited about 20 hours before texting her again. She came over for dinner and a movie a few days later. I escalated quickly. I was expecting to get laid that night. We made out and I stripped her down to the waist.
“I want you to suck my cock,” I said.
She looked a bit shocked. She was not expecting me to be so blunt about it. Then she sat down on the rug between my legs and swallowed my dick. She was a pro and gave a killer blowjob. She used no teeth, kept it rhythmic, cupped my nuts perfectly, the whole thing. She almost made me cum but I stopped her before exploding in her mouth.
I tried to take off her yoga pants but he was on her period. She was such a slut that she was down for anal sex instead. I put the tip of my dick on her asshole, but then I just let her finish me with her mouth. She came over for the third date later that week and we finally fucked. She was down for anything and gave me full access to all three of her holes.
I stupidly let Cassandra spend the night on the second date. Then she began spending the night every time. This was a mistake. Cassandra was a fuck buddy at best; she did not deserve to sleep over. One evening I got tired of her. I told her she could not stay over that night. She did not raise much drama, but she did not like it at all. She began to pull away from me. This was our last text conversation:
MF: still on for 8:30?
Cassandra: hey can’t see you anymore. i started seeing someone else and would hate to date you both at the same time
MF: Ok, good luck :)
She married that guy a few months later.
The last time I checked her Facebook, she was pregnant and living in a different state.
So I was Cassandra’s last ride on the cock carousel.
She thought I was her soft landing, but she was mistaken.
I seem to attract provider hunters, former sluts looking to settle down.
Everything about me screams provider.
Women see my suburban neighborhood and (former) corporate job; they think they have hit the jackpot.
Unfortunately for them, that is not the case.
Total Cost: $17 (First Date)
Time Spent: 65 Minutes (First Date)
Lessons Learned: Never let fuck buddies spend the night.