Listen, I’m not perfect, I don’t even pretend to be. We all get caught slippin’ from time to time and before we know it, we got, got (for my non-urban subscribers that means to be hoodwinked or in your slang “had”). So, here’s another story real dudes MAY be able to relate to. If not, screw you. Don’t judge me, you are not here to judge, just enjoy the story.
I was fresh on the eligible bachelor list after a break up and I was past what us men go through and we will call “depressed” phase. Not really depressed, something like it, but whatever. Anyway, this was about 8 years ago, I was a 21 year old boss. Fresh to death every day, own loft apartment downtown, own car, probably went shopping every weekend. Living life, the American dream as some would call it. I was wild and young. I was “dabbling” in a few women at the time, I didn’t want anything serious so I made it clear to them and for the most part they just wanted to be affiliated.
Now on one of my many days spending money like an idiot, I go to pick up the homies and head to the mall. We were going out to party later so something new was in order. I parked my car at a central location which happened to be Lord & Taylor’s just so no matter where we were in the mall it was never fully in the exact opposite direction of where I wanted to be and when I’m ready to go, I’m ready to go. We walk through Lord & Taylor’s and begin our day of shopping. Sneakers, Shoes, shirts, Pants, the Jockey store etc. On my way out I realize I didn’t purchase a belt so I look around in Lord & Taylor’s on the way out and I spot this thick, chocolate goddess whose name is Tracey. Well I ask Tracey to point me to the belts and she does, I give her the flirtatious “Thank you baby” instead of the regular “Thank you babe” and look at belts. While I’m doing so she brings over a shirt and says you “You should buy this shirt, I think it would look good on you.” In my opinion that opened the door for me to flirt. I purchase the shirt and get her number and tell her I plan to see her later that night before I go out. She said “Ok, we’ll see if you call Mr. Philly” in her JAMAICAN accent. Yes, I found out very quickly 2 things. 1. I’m attracted to and possibly attractive to Jamaican women, and the greatness of Jamaican Pum. That night her and I went out to dinner, simple Outback Steakhouse dinner. Chopped it up and I told her I’d see her another time she left in her car, I left in mine.
She worked in retail so her schedule was very irregular, however we consistently spoke on the phone and I finally said “Fuck it, you know what; after you close the store tonight come straight to my place.” She complied. She arrived at my place at about 11:00pm. I was just showing the homies the door as she was walking up and in unison they said “Daaammmnn, wait, this is lil mama from the mall. OH yeah, we see why we gotta go now.” You cot-damn right. She walks in my place, I tell her to have a seat offer her a drink and we proceed to watch a movie. Around 1am the movie ends and she notices the time so I tell her don’t worry about the hour because I’d like her to stay. She agrees I give her a t-shirt and towel and then I say “Get naked” and she complies. Body was amazing, I grip her naked ass and imagine all the shit we’re about to get into. She goes and shower after her day at work and come back in just my t-shirt. Not long passes before I’m all over her. Typically I wouldn’t believe any man can go hours UNTIL I was in her. Now it wasn’t one long ass session. However it was a definite “all nighter”. The oral sex on the couch was dope, actually pretty good. I’m thinking, ok this might be alright. Mind you she was down, but she was just taking my lead. Not aggressive in the least until about round 3.
Round 3 we end up in my bed. She actually takes initiative and polishes your boy off until he’s ready to go and then she gets on all fours and put that arch in her back. That glorious ass was looking at me and I did what any man would naturally do, I WENT IN. I’m in there goin’ to work on her and then just as I’m maybe 2 minutes from takeoff (ladies and gents, the moment when the dude speed up, tense up or give you other signs he’s about to ejaculate) She invokes her kegel training. Now, I’ve dated women with a good grip before, yet this was different. This was monumental. While I’m ready to “Bust” my 3rd nut, her vagina proceeds to give me a hand-job. YES, her muscle control was that amazing that it felt like I was getting pussy and the greatest hand-job on earth. All I remember is looking down at her pussy to make sure there wasn’t another person in there and then I did what any normal dude would do: I kept pumping and screamed like a bitch as I bust’d one more time. After that was over roles reverse for a split second I swear I said: “Damn baby, what you tryna do to me?” I entered the realms of heaven two more times before calling out of work and sleeping in til 3pm. When her and I finally awoke we went to her place and on the way her car didn’t sound quite right and she told me the issues it had. We arrived at her place and she performed her magic a few more times before then heading back to my place that night for her to stay the weekend at my place. When the weekend was over. I wrote her a 3k check to get her car fixed. Fuck you, I know what you’re thinking and you might be right but what kind of man would I be to lay up in that box all weekend and not helping a lil bit. That fling lasted about 2 months because she was on hiatus from her man. They took a “break”, I guess he wanted the summer off. Now according to MY OWN guidelines, I was trickin’, she wasn’t my woman. I was just getting the pussy and having fun with her. I was investing in someone else’s stock. She probably had the best 2 months of her life that summer. I personally had the best sex I ever had that summer.
I’m not sure if she had a plot to get me or what. I’m just grateful her man cut her leash early in the summer and I’m grateful for her. I mean, I didn’t go into the situation thinking. “Imma splurge on this broad”, it just happened. Do yall think I should consider it trickin? I’m not sure, I’m not a professional trick. I just got caught up once. Let me know. Like I said in my other story Jamaican pussy should come with warnings, instructions and a moral to the story. I guess the moral to the story is: Never say what you won’t do, because there’s some pussy out there that will make you a liar. – Aesop (I’m sure he said that before)