*This story is a work of short(ish) fiction, and despite the tribute that I would like to pay to the real people these are based off of, their names have been changed. Chicagoland area residents will recognize some of the places despite the name changes.*
Part 1:
Sheridan and I have been partners at the Wesley Avenue Police District for something like six years. We’re part of a larger group of six: Me, Bonds, Martinez, Sheridan, Maurice (the only one who uses his first name) and Woodard. Officially, we’re known as the patrolmen on the night shift in Lakeview, but the brass calls us the "Hooker Squad." The people we arrest, however, call us the "Tranny Chasers" a term I hate and Sheridan just laughs at. Bastard.
I should confess here that I have an overwhelming attraction to t-girls (which sadly, Sheridan does not share) and that while I do not enjoy arresting the girls, I do enjoy the show they put on, although to anyone outside the squad I pretend like it’s funny. Sheridan, however, is my second best friend on the squad, and before we leave to go on our shift (from 8:30 to 8:15) he looks at me and says "well, time for another trip to Trannyville." Then he laughs.
Martinez doesn’t find it that funny because he’s actually dating a T-Girl and they’re talking about marriage. Every time he brings it up I change the fucking subject because…well, here’s why:
May 16th. Sheridan’s out sick (got a bad case of the "hung the fuck over" flu) and so Martinez, needing a few extra bucks, volunteers to partner up with me for the shift. Nodding because I know Martinez, my actual best friend on the f***e, understands and shares my attraction to TS women, I say "Let’s start over on Vanderbilt."
Vanderbilt is the main street if you want to find a transsexual. Sadly, most of them are hookers, which distinctly lowers the quotient of fuckable girls. Not a judgment, but most of them, while they might give you a blowjob to get out of an arrest, aren’t interested in you otherwise because of the badge. Martinez and I did an experiment six weeks ago (just when it started getting warm in Chicago) where we took a night off and hit on a couple of girls named Miranda and Jessi at Waters’ bar. We were going gangbusters, and I had just moved Miranda’s hand down to my cock, which was standing in sharp relief, when she asked me what I did and I said "I’m a cop."
Fucking stupid. It was like a block of ice landed in the middle of the dance floor. Then I realized Miranda had poured her drink on me. Normally I would have arrested her, but I couldn’t really blame her. Jessi stood up and dumped Martinez as well, and they were gone at the speed of light. Martinez shook his head at me and said "T, you’re a douchebag."
So, not in a good mood because of the constant reminder of this, we rousted girl after girl after girl, some of them I was inclined to actually cop a feel on, but restrained myself. At 4:30 AM, a Latina girl was stopped on Kent and Wesley, and although I was inclined to run her in, Martinez was out of the car first and began openly hitting on her. At least, that’s what I took it as. He was solicitous, but when he found condoms and lube in her purse, I rolled my eyes and said "Lady, do you think we’re stupid? You’re hooking. You’re under arrest."
Her face trembling, long blonde hair swaying in the breeze, she looked at me and said "I’m not a hooker. I have a boyfriend who likes to fuck me and he tries to hurt me when he does."
Fuck, I thought, a sob story. In spite of myself, though, I started feeling sympathetic to her. So, instead of going into full asshole cop mode (one that I do very well, apparently.) I gently asked her "Okay, what is your name?"
"Connie." She sniffed. She was already near tears. I just nodded and said "Okay, look. For your own safety, we’re going to have to take you to the station and hold you until six AM." At this point, I started taking her in. She had nice breasts and a sweet looking bubble ass, but I swear, my intentions were honorable. Yeah, yeah, I know, I’m full of shit. Anyway, the next two hours passed in a blur and when I actually decided to cut my shift short at seven AM, Martinez said he was staying the full shift (and picking up an hour of OT) so he’d be in til 9. I left the station and noticed Connie sitting on one of the bus benches, and assumed she was going home. However, she waylaid me as I walked toward my apartment in the tall building at Irwin Park and Clarence. "I just wanted to thank you for being so nice to me." she began. I nodded but as I began to turn, she reached down and grabbed my crotch. I was actually stunned for a second, because I’d never been so directly accosted without knowing it was going to happen. As I looked at her, down into her clear brown eyes, I realized I was losing my grip on myself. So to speak.
"How old are you, anyway?" I asked, searching frantically for something to say. "I’m 32." she said. "And before you ask, I transitioned 12 years ago." "Well, that…that’s good." I said, but then she leaned up and kissed me. Her 5’4 inch frame somehow brought my 5’10 inch one down to her height. I felt my brain start clouding and my eyes hood, and started kissing her back. Suddenly I grabbed her by the wrist and fairly threw her into a cab, because I couldn’t have walked if I wanted to, I was that hard.
When the elevator door to the sixteenth floor opened I actually dropped my keys because I wanted her that badly. Finally I got the door open and she fucking tackled me and we started kissing like crazy people. Then I stopped. Voice hoarse with desire, I said "Clothes. Take them off. Slowly." Although I’m not a super muscular man, I’ve got a good shape, and I wanted to see hers. Slowly she stood up. She pulled her button down shirt off just as slowly and I had my lips on her nipples immediately. I wasn’t playing around with her because it had been so, so long since I had satisfied my desire. Then I stopped. "I’ll do this part." And I peeled her jeans off, noting with gratitude that her ass was as bubbly as I thought it was. At this point, I hadn’t even gotten my uniform shirt off, but I finally did, nearly tearing it off. Turning her back to me, she peeled her white cotton panties off and stood with her head bowed. Pulling her to me, I kissed the exposed globes of her ass, which had a great tanline. She turned to face me and something hit me directly in the face. "holy moly." I whispered, not knowing what else to say. Her cock was a thing of beauty, small, thin, and already leaking. In a very matter of fact tone, she said "if you start sucking, I’ll blow right now." Leaning forward, I actually kissed the head and said, "well, we don’t want that yet." Then, turning her around, I slowly began licking her ass. I was trying to make this last, but she started literally-gently-pushing her ass back against my tongue. That’s my second biggest turn-on. And she immediately looked back at me and said, in a breathy, Monroe-ish tone. "I want to sit on your face, but if I do, I will cum." My cock was already out to it’s full 7 1/2 length, and when she said that it actually did one of those pulses that make it hurt. "Fuck" I grunted, not knowing what else to say.
Then she made the decision for me. She pushed me down on my back and that amazing ass crashed down onto my tongue over and over again. "unh" she grunted, and when my tongue actually went into her ass like a cock, I felt pulsing on it as she shot all over my undershirt, moaning like a madwoman the whole time. "Damn it," she moaned, "I didn’t want to cum yet." Connie stood up and started walking to the bathroom, but I pulled her back onto my tongue. "No" she moaned, but she didn’t mean that, because she was instantly erect again. "That’s never happened to me before." She grabbed my dick and looked down at it. "I wonder what would happen if I sat on this thing," she mused. "Would you bust inside me if I did"? "Keep talking like that and I’ll bust right here and we won’t get to find out." I responded. "I’ve never ridden a black man’s cock before. They’re all so big and they hurt." "Gee, thanks," I growled.
"This one is big, too, though," she mused. She looked around until she found the lube and slathered both her hole and my dick. She turned to face me, and sank down, sheathing the whole length inside her bubble booty. "Mmmph" she yowled, trying not to scream. She began moving her hips rhythmically on me, and as she did, a ropy loop of precum went directly onto the top of my head. I didn’t notice until later. As she increased the speed and started going faster and faster, I felt my eyes roll back in my head as I fought the urge to shoot inside her. It was going to be a losing battle, however, but I was determined to hold out until she did. Suddenly she stopped, and without touching herself shot the first two squirts of her second load directly into my open mouth. She actually did choke off a scream. Then she started riding again…and got yet another erection. "This fucking girl," I thought to myself "is a fuck-b**st." Then I realized I was actually calling her a fuck-b**st. Like Popeye eating his spinach, my cock started to regain its resistance to being rode to orgasm until she whispered to me "Go ahead, daddy, fuckin shoot into my box. Give me your juice. Impregnate me." "AW, SHIT!" I screamed in response, and then was overwhelmed, unlike Popeye eating his spinach, as I burst deep inside her, feeling my cock flexing like one of my arm muscles. As I did, she growled like a cougar and shot her THIRD load, hitting me directly in the eyelid, then in the mouth again. She pulled herself off of me and fell into bed next to me as I looked at her, then, realizing what hadn’t happened, dove onto her softening girl-prick and coaxed yet another sexy load out of her, her legs trembling, and her growls turning me on until, without touching MYSELF, I actually blew my second cloudburst of seed all over both of us. Then we both passed out.
Six weeks later, Martinez told me he met the girl of his dreams while I was on vacation. When Connie walked in, and we made eye contact, I believe an electric shock rolled through me, and I barely heard Martinez say he had been dating her for five weeks…or one week after that fateful night. However, something happened during vacation that completely changed the outlook on any future relationship I could have had with Connie. I met ANOTHER girl….
End part 1.