Three Days With "Philly's Finest": A True Story

[TJ347]

About five years ago, hanging out on South Street in Philly, I met up with a girl I'll call "Pam", who called herself "Philly's Finest", and physically speaking, was probably right in doing so. Anyway, we'd kept in touch regularly and developed a good relationship, so I didn't think anything of it when two years later she asked me to stay with her for a few days while her roommate (a GG if you care to know) was out of town, as she explained she simply didn't like to be alone at night, and really enjoyed my company.

I got there around 4pm, and for hours we talked about this, that and the other, before things drifted into all things sexual late in the evening. Pam was a tall black woman, plus thick in all the right places, and had a face highlighted by big, brown bedroom eyes and juicy lips that made me think more than once about some things I shouldn't have been thinking about since we were just friends. At any rate, she was already well aware of my interest in tgirls, as we had talked about that early on, and now half-jokingly questioned me as to what I specifically liked to do with tgirls sexually, and what things turned me on in general. I felt a bit strange talking about my sexual tastes so personally with someone I wasn't having sex with, but in the course of replying to her query let her know that one of the things that turned me on was her, to which she simply replied "Oh, really?", a look of false surprise coming over her face, making me more nervous by the second.
"And what about me turns you on?" I covered my face with my hands, finding it surreal that we were really having this discussion, which was similar to a dream I'd had repeatedly about us hooking up, and how it might happen if it ever really did. "Does this turn you on?" I uncovered my face and looked to my left to see the tip of her dick sticking out of the top of her sweatpants, as she slowly pulled them down to her knees. She smiled, tilted her head back and sighed, and began jerking off, occasionally looking over at me, biting her lip, and giving me a come hither look. After a few minutes, she stopped and pulled her sweatpants off around her sneakers, then threw one leg over the top of the couch and laid back. "Come here, T... I want to... give you a little something" she said giggling, and I had no doubt what it was. I took off my shirt (it felt like I was on fire!) and laid my body across hers, her dick burning against my stomach like a hot piece of metal. I moved to get into a better position to kiss her, but she wasn't interested in any of that... she was all about getting her dick sucked, and quickly putting one hand on the top of my head, moved me into position. Up to that time, I'd never been in that position mind you, so I was a bit shook up. However, when I looked up and saw her smiling devilishly, her eyes dancing in anticipation, I knew that regardless of any apprehensions I had, I was gonna be sucking some dick that night, period. She whacked it against the side of my face a few times before pressing the tip against my lips, at which point I tentatively opened my mouth... Before I could figure out how I felt about what I was doing or anything else, she'd pulled my head down, to where her dick hit the back of my throat. I shot up coughing, and hadn't even been sitting up for two seconds before Pam pushed me back and straddled me, placing a foot on either side of my thighs. I'd hoped to at least catch my breath for a minute, but she pushed my head back and stood up, pressed her dick against my lips again and hissed "Open up!", immediately trying to dislodge my voicebox again the second I opened my mouth. "Oh! Ungh! Motherfucker... Suck my dick! Ugh!"... And on it went for about the next ten minutes, and if not for moving my head to the side regularly I might have suffocated. Pam suddenly pulled out, smacked her dick against the side of my face again a few times, and stepped off the couch, leaving me confused as to what had just happened and wondering what, if anything, she planned to try next. I felt drunk for lack of a better word; I certainly wasn't in the state of mind where I should've been making any critical decisions. However, I knew for certain that if she tried to fuck me in the ass... Well, that wasn't happenin'. That much, I was sure of. What I wasn't so sure of, because I'd never thought of it up to then, was how I'd feel about tonguing some ass, and since that's what I wound up doing a few minutes later, I guess even then I was more or less cool with it so long as the girl was as clean, cute and as cool as Pam was. No doubt realizing in short order that I had no idea what I was doing, Pam quickly began giving me instructions, and was soon giving me her own form of encouragement, repeatedly saying things such as "You ain't really new to this, are you? Unh, unh... not the way you're eatin' this ass out you ain't!" (I noticed that when I circled her asshole slowly, she'd let out a loud moan and her whole body would shiver, where when I stuck my tongue inside her asshole, all the muscles in her body seemed to tighten up and she'd let out a slow, quiet whimper. Just wanted to share that...) She jerked herself off as I continued to slowly lick away, soon expanding the territory I covered to include the entire length of her asscrack, right up to her balls. In between moans, "You motherfucker!" and "Ungh!", not too much was said for a good long while as far as I can recall, right up until she finally lost her load all over her chest. She then went and cleaned herself up, said goodnight, and disappeared into her room. I was still sitting on the couch trying to fully comprehend what had just happened as I noticed the light in her bedroom go out as I stared at the gap between the floor and the bottom of her bedroom door, though it didn't immediately register, as my mind was a million miles away.

And so ended my first sexual experience with "Philly's Finest"....

[johnnyshemalelover]

Wonderful! Got me hard...

[TJ347]

Thanks for the compliments, J! And all the help.




For those who really give a damn:

1.) This story is true. All of the stories that you will ever see me write are true.

2.) The only thing that may not be "true" about my stories is that things may not have actually happened in the sequence that they do in the stories and that some things may be left out.
Regarding things that may be out of sequence: Please understand that I am recalling these events entirely from memory (I have never written them down prior to putting them up here), and over time, people tend to remember things slightly differently than they actually happened (and no, I'm not remembering things more than slightly differently).
Regarding things that may be left out: Please understand that some of the things I leave out, I've left out because they are unimportant to the story, while I have left other things out so that the people I am talking about in these stories cannot be identified.

[TJ347]

Continues as "Three Days With 'Philly's Finest': Part 2".

[trapmasta]

this is just such an excellently piece
you fit years of explanations in just one sentence without rushign the story or decreasing the ever hiegtning sexual tension. just an amazing read.

[TJ347]

this is just such an excellently piece
you fit years of explanations in just one sentence without rushign the story or decreasing the ever hiegtning sexual tension. just an amazing read.

Thanks again, Trapmasta.

[TJ347]

BUMP

Just because...

[Clind]

i m jealous ,i never been with an experience like this ,never a shemale has cum and never was reallly horny because of me any t-girl