Doing freak nasty stuff with white women is more exciting to me than hanging out with The Girl Scouts of America unsupervised is to R. Kelly.
Even though it’s been over 24 years since I first became sexually active, I am still somewhat surprised when someone gives me pussy. I know that’s a limiting belief, and some is remnants of old self esteem issues. But sex felt so impossible before it happened, that some mental residue remains.
This is why I remember every conquest, including the date that each initial encounter took place; it mattered much more to me. What follows is a list of my 5 favorite flings — so far. There’s only two rules to this list: first off, I am not including any of the women with whom I’ve been in an official relationship, or close enough to the ladies that it was practically one.
The second rule is that I am only including women with whom I’ve had either vaginal or anal sex with. In other words, blow jobs, making out or foreplay situations won’t count if they didn’t include actual sex. This list is only in chronological order, and I ditched names and dates for obvious reasons.
1. Purple Thongs Chick
This fling is one of my all-time favorites, while also being my most asshole moment. We only saw each other once — but wow! It’s not that it was over the top wild and earth shattering, but the circumstances of how we met and came together was wonderful. I had met “Purple Thong Chick” online in the summer of 2001 when she was 19 and I was 24.
We always had explicit conversations and she established quickly that she was naughty. I was eager to meet in person, but for many reasons it didn’t happen. The key issue was that she lived more than two hours away. But — two years after we first spoke online and the phone, the stars aligned and she was open to meet me.
There was a sizable snag, though: I was engaged with a new baby on the way in less than two weeks. Being the shameless cunt chaser that I was, I invited her over to my house for some early afternoon fun. And by “my house,” I mean, the place that my fiancé and I shared.
She was at work, nine months pregnant and I was about to finally unwrap this young woman whom I nicknamed, “the tigress.” I made us a vodka drink and within a few minutes, we went from freaking on the couch (where she masturbated as I snapped photos) to racing up the steps to the bedroom. I was so overcome with lust, that I didn’t much care how foolish and ill-advised this was.
Once I got her in the bed, we went through a cycle of hotness. I ate her from belly button to asshole and everywhere in between. She sucked my cock, and of course I fucked her. Throughout this entire process, I took several photographs to document this awesome encounter with a gal that I had coveted for two years!
I was relieved when I successfully got her out of the house without anything unforeseen taking place. The jerk way in which I handled detailing this encounter to my fiancé is another story. But make no mistake, this fling is on my list of gratifying conquests.
2. The Screamer Chick
This broad was such an incredibly shameless slut that, 16 years later, I still want another crack at that ass! I met her on a telephone chat line a few days after my 27th birthday and I was hooked on this bitch from the word go. That first night on the phone, she told me that she’d had a 28-person orgy, and that some of the participants were guys!
I convinced her to play with herself over the phone, which wasn’t difficult at all. She had a super hot tendency to scream when she hit that climax note, which blew my freakin’ mind. I was used to moaning and whimpering from chicks, but screaming orgasms was a first.
So, one day she used a shampoo bottle to get herself off while on the phone with me. When she went into her “scream,” I nicknamed her “Screamer.”
This woman talked a real good game and because of that, she seemed too good to be true. Anyone can say whatever on the phone. It took about two and a half months to actually meet her in person, partly because she lived 60 miles away and my car needed to be repaired to make that drive.
As soon as I walked in her house, I commanded her to masturbate so I could find out if she was the freak in person that she was on the phone. She had done that a lot, but this was the first time in person that I witnessed it. I was impressed. I brought her back to Cleveland where she proceeded to display her enticing submissiveness to me, while being a shameless ho bag.
I ended up fucking her doggystyle in my aunt’s basement, and she actually squirted for me (I’d never seen that before). More than anything, her willingness to do whatever without objection was mind blowing. We had an actual fling that lasted about a year. I would stop by her place in Canton, Ohio and spend a bit of time there, converse and fuck.
My one regret is that I didn’t take full advantage of her true kinkiness. She had a sex swing, and was completely down for having her mouth pissed in! She was even down for a group of guys to fill up on beer, then unload gallons of bubbly piss into her throat! I really need to find that sick fuck again!
3. The Lost Job Chick
The biggest reason that this woman is on this list is because of what took place months before. In April 2009, I showed up at her job with my video camera and began filming an impromptu interview with her. This was for inclusion in a web series that I was producing at the time, and she ended up getting fired for allowing me to do that.
Naturally, I did not want her to lose her job, and I was genuinely surprised 11 months later when she was still out of work. She had already sent me several infuriated messages on MySpace, which fueled my desire to get her on another episode. The sheer audacity of asking a woman to be interviewed for my show after she lost her job doing the same thing was a surprising turn on for me.
I was able to convince her to do it fairly easily and she actually made herself look worse! I also talked her into having sex with me, just because I could. Given the context, this became about nothing more than achieving a massive ego boost. I enjoyed having control over her and persuasive powers given how I supposedly “ruined” her life.
The sex was little more than a footnote to actually getting her in another episode, but it was actually hot. I had never before experienced a woman repeatedly switching actions and positions after just a few seconds. That brought a different element to sex that I found to be hot, otherwise, there was nothing exceptional about this broad. She was really just a standard issue slut, and one of my favorite flings — so far!
4. Chunky Country Chick
I met this chunky country tramp online and smooth talked my way from inside her Facebook messenger to inside her panties. She lived in a very White, rural area about an hour from me and had a wholesome disposition initially.
It didn’t take long to realize that she was extremely easy and actually had a craving for black cock. We flinged about three or four times sexually, but that first night is what I’m most proud of. This was simply because I convinced her to visit me and to let me hit that pussy. I was hammered as hell, and I might have gotten a bit carried away with the kink factor.
Either way, getting the pussy on the first night is always a great achievement, especially for me. I loved the fact that her community was largely racist, her brother was definitely racist, and yet she an indiscriminate ho bag around black guy me! Near the end of our fling, I convinced her to give me $200 to assist with my rent, which of course ended up being another ego boost.
5. Face Smearing Chick
This woman is my most recent conquest, and I enjoyed her sense of humor. I met her online and even though she’s a few years older than me, she is still a nice and enticing sexual being. What makes her one of my favorites is her shameless, prideful obsession with being a cocksucker.
She told me from the very beginning that her favorite source of pleasure is actually administering head to guys. It’s one thing to hear that and a whole other thing to receive it. She gave me that the first two times that I saw her, and the sex waited until our third encounter.
But, while her head game is extraordinary, it’s what she did multiple times after I climaxed. I was so full of cum that it gushed out everywhere, and she proceeded to grab it and smear it all over her face and neck like with gleeful pride like it was Cherry Blossom wiener lotion! That was such a beautiful sight to behold and it blew my mind. Her sheer brazenness and thirst for black nut continues to bring a smile to my face.
I look forward to adding more amazing flings in the future to top all these! What flings have you had and been proud of? Let me know in the comments!