I hated when Uber passengers took all day to come to the car. I glanced at my phone honed in the dashboard holster to see how long I'd been waiting on him and it had been 2 minutes. Just a few more seconds and I'd be able to cancel his ride and still get paid for it. I hated waiting on these busy streets through all this chaos. One would wonder why I bothered driving Uber at night because this is the shenanigans you had to put up with. But it was either the bubbly night time bar crowd or the arrogant and angry working people during the day who were cheap as fuck and chose UberPool but had the audacity to want to huff and puff in the back seat when they felt you were taking too long to get them to work.
A tall slim brown skinned guy with a sandy brown unkempt afro walked hurriedly to my car. I took it this was Jason. I was not used to picking up black Uber passengers as I mostly worked on the North side because that's where it stayed the busiest. Besides, whilst I loved my people, they were not good tippers and wanted so much for very little of nothing. When he got in and I swiped the pick up, I noticed he stayed in the Chatham area not too far from me. I'd plan on driving another hour but I figured this must be a sign from God that it was time to take my butt in the house. An hour prior I'd witnessed a huge car pile up on the Kennedy expressway and now I'd had a passenger who stayed in the same community as me who I was taking home. I decided to make him my last ride and carry my butt home, I'd worked 5.5 hours and I made $150 so I decided that I cleaned up well in addition to my pay from taking this last fellow home.
"Good evening" I turned around and greeted Jason. "You're going to 7301 Dobson right" I verified with him.
"I am. Wassup with you" Jason returned the greeting giving me a lingering stare.
"Nothing much, thank you for paying me to go my butt home" I joked.
"What you mean shawty" Jason asked confused. Something about when a man calls me shawty just did it for me. It made me feel so effeminate and inferior to dudes when they called me pet names normally reserved for women.
"I mean I was going to drive a little longer but you don't stay far from me so I'm taking my ass home."
"Oh word?"
"Yep"
"That's wassup. Glad to help" Jason joked back.
I turned the radio on and took North Avenue until we got to Lake Shore Drive. I used to love driving down Lake Shore Drive as to me it was undoubtedly the most scenic place to drive in Illinois. It normally made me feel peaceful, hopeful, and just chill to take the drive down Lake Shore but since I started driving Uber part time it was like another damn street to me. As I geared towards Chicago Avenue I couldn't help but steal a glance through my rearview mirror at Jason. My heart fluttered when I realized he was glancing back at me. Jason had that thug nerd appeal about him that always gave me a hard on. You ain't lived life if you ain't been dicked down right by a slim thug nerd. We kept stealing glances at each other ever so often til I almost killed us when coming around the curve on the Lake Shore Drive past Grand street. I somehow managed to discreetly swerve back into the center of my narrow lane calmly before side swiping a pearl white Infinity truck. I made sure that I didn't look nervous or flushed about the face as you never wanted your passengers to think you couldn't drive or that you'd almost killed them.
"So how long you been driving for Uber?" Jason's baritone voice interrupted my thoughts.
"Oh...about 5 months now." I answered.
"Do you like it?"
"I do for the most part. It has its days like all gigs but I like it though."
"I know you be getting some crazy people in here" Jason chuckled.
"Believe it or not I only drive at night and for the most part my passengers cool as hell. Most are bubbly and talkative or sleep." I joked.
"What's the craziest thing you had happen to you since you've been driving." He asked.
"Honestly nothing. I get weirdos both men and women who've had too much liquor that flirt with me but nothing too crazy yet."
"Yeah, I can see how someone would flirt with you. I don't care how handsome and manly you look, you have a submissive side to you with some seductive ass bedroom eyes so I won't lie, if I were drinking I'd flirt with your sexy ass too" Jason commented boldly. I was taken aback. Yes I knew we'd exchanged glances but I wasn't used to DL men being so forward with me.
"Well thank you. I wasn't expecting that." I commented as I peered at him through my rearview mirror. I noticed he put his hands between his leg and rubbed over the bulge in his nylon black joggers which was obviously hard and huge from what I seen. He was torturing me and I was having none of it. I gave him a lingering stare through the rearview mirror as I licked my lips seductively and picked up speed circling the 57th drive around Cornell.
"So what you about to get into after this?" He asked me and licked his lips.
"I have no idea to be honest. Nothing to get into really" I said letting that sit with him. I decided to put the ball in his court.
"You should come chill with me for a second since I'm your last ride." He offered never taking his eyes off mine. "It's just me and my roommate so you won't be uncomfortable or nothing" Jason assured me.
"You sure your roommate won't mind you having company over. Especially another dude" I asked giving him the raised eyebrow.
"Trust me bro. My roommate is just as chill as me. You good" He assured
What the hell. I agreed. I pulled up in front of the brown stone two flat on 73rd and Dobson. Jason got out and I did the same and followed close behind him. My stomach was in knots as for all I knew Jason could be some homophobic serial killer that had 10 boys with baseball bats and other weapons waiting to rob and torture my faggot ass. So my stomach was in knots but my hard dick and wet booty overshadowed any fear I had for what my fate might be as I followed Jason up the stairs to the second floor apartment. I loved when a guy who I was hanging out with lived above someone else. Because if he decided to wig out on me and get crazy I would stomp, jump, and make as much noise as my tiny frame would allow me to so I could wake someone up. Most guys were cautious not to be a homophobic maniac anyway when they had a first floor tenant so I felt more at ease as I entered Jason's dimly lit apartment. His apartment was huge as I looked down the hallway. It seemed like there were many rooms down that long ass hallway that you could've turned into a damn runway show.
The sound of someone getting it on interrupted my thoughts as Jason lead me to the couch and offered me a beer which I happily accepted. A beer would calm my nerves. Jason rolled up his white owl, fired, puffed, and offered it to me which I again happily accepted. The euphoric feeling took place just in time as the sex sounds got louder in the 2nd room down the hallway and it became clear that Jason's roommate wasn't watching porn or a scene from a movie, this nigga was in there fucking.
"Your boy getting it on." I commented.
"Yeah, this what we do. We bachelors who work hard, make money, and smoke and fuck" He replied and grabbed his dick. And glanced at me and then suggestively glanced back down at his dick. I knew what this meant. The sounds of sex from the room and the weed and alcohol made me want to get my hole stroked. I reached over and massaged Jason's dick through his pants. He looked at me and licked his lips. I then went to free his thick dick from his joggers before the bedroom door down the hall burst open and I heard another deep voice say in an angry hushed voice
"Why you always do this shit yo? You get a nigga all horny and shit and as soon as I start hitting that shit good you want to moan bitch and complain about I'm hurting you. You know how I like to fuck and ain't shit changed about me in the four months we been fucking. But it's cool. I'll see you later ma. We'll try again...hopefully" the roommate complained as he let the chick out who luckily headed straight out the door and didn't notice Jason and I sitting on the couch. After the roommate closed the door I felt awkward as he gazed in our direction trying to figure out what we were doing. I really panicked internally when I realized that I was so high my hand was still on Jason's dick print.
"What's going on ma dude" Jason called out to his roommate.
"Same shit my nigga" he came over and dapped Jason up with his dick still hard and semi exposed through his blue checkered boxers that looked like he bought them from a gas station. Jason's roommate was another tall slim thug nerd looking dude except he was light skinned with his hair braided to the back. I was loving how the French braids were making their way back after over a decade of taking a hiatus. Jason and his roommate was chatting it up – never mind that dude was standing there talking to Jason practically naked and his dick was still hard and literally pointing at me and Jason through his boxers. The roommate kept eyeing me while he and Jason made small talk.
"Aye yo, this was my Uber driver tonight – his name Antwan" Jason introduced me. The roommate stepped closer to me and stuck his hand out for dap. But his dick was closer to my face than his hand was. I dapped his hand. I could smell the faint smell of sweat from his bare feet which were so pretty. I swear I had a weakness for masculine thugs who had nice feet - It didn't help matters that they smelled as if he'd just taken his gym shoes off.
"Nice meeting you" I said
"Gratitude" He said to me studying me. "I'll let yall chill I won't stand in yall way. You mind if I hit that though before I go back to my room" Jason's roommate asked him and nodded at me.
"Yeah nigga I don't care." Jason answered and looked over at me. "hand him the blunt bro" Jason said.
I was dumbfounded as it took me a minute to realize he wasn't talking about fucking me, he was talking about the blunt I'd grabbed from Jason a moment ago."
I handed the roommate the blunt and he accepted and gave me a knowing smile. He took a few pulls before handing me back the blunt and giving me another long lingering look before dapping Jason off and taking himself and his hard dick back to the bedroom.
"So where were we?" Jason said when his roommate disappeared as he released the monster out his joggers and his stood up thick and tall. Dammit his dick was so black and big. I didn't bother to hesitate as I leaned over and started slobbering on his dick like I was a homeless man who hadn't been fed in days. His dick tasted as good as that chocolate muther fucker looked. I almost chocked myself a few times as it was too big for me to be trying to deep throat without me taking my time. I'd gotten into a nice rhythm and was enjoying bobbing up and down on his dick that got harder the more my slick mouth went up and down. The better I got at deep throating his shit, the harder he got in my mouth and his moans had started to fill the living room and I was worried that his roommate would hear. I was high and felt so good sucking his dick that I let a few moans escape me too. Jason's precum was leaked down my throat as I bobbed up and down the shaft of his thick meat. I was going for gold and I was going to show this nigga that he picked the right Uber to get in that night. I'd almost had Jason where I wanted him before I felt someone slowly pull my jogging pants down from behind. I turned around to see Jason's roommate had come out of his room and was straddled behind me with his thick dick which was a few shades darker than the rest of his body – a beautiful peanut butter colored dick. I turned around to face Jason who was giving me a seductive smirk. He licked his lips and looked past me at his roommate who forcefully took my shirt off me.
"Turn around and finish sucking my boy's dick yo. This what we do. We share niggas and bitches." His roommate whispered in my ear. Then he kissed on my back. His lips were so wet and soft. He kissed on my back and then gently bit down on my shoulder. I almost lost it when he did that. Being the submissive dude I was, I did what I was told and started sucking Jason's dick again as his roommate spit on my ass and ate it. Jason started moaning loudly as I got back into my rhythm and sucked him off. Moments later I felt his roommate roughly enter me from behind. His dick was literally stretching my hole and it hurt like hell but I didn't care. It felt amazing at the same time. He started pumping into my hole while I sucked on Jason. After a few minutes, Jason stood up, kicked his timberland boots off, yanked his joggers off and pulled me to my feet. He turned around and headed towards his roommates room. His roommate grabbed my waist from behind and gently pushed me toward the room Jason was headed to. In there, they instructed me to lay on my back in the middle of the bed. Jason left the room and seconds later came back with a bottle of lube. He gently applied to my asshole and then straddled over me. He grabbed my legs and put them over his shoulders and roughly entered me. His chocolate dick hurt my insides as he stroked me in the missionary position with no mercy as his head was buried next to mine in a pillow. After a few moments, his roommate gently tapped Jason on his shoulder giving him the signal that it was now his turn. His roommate was no different. He entered me and stroked me with no mercy too. This tag team match that Jason and his roommate had going on lasted the next hour or so. They were both tag teaming me in countless positions. My body had gotten so sore and tired from all the positions that I ended up back where I started. On my back with my legs in the air. The only thing I still had energy to do was moan from pain and pleasure. Jason and his roommate knew they were hurting me. From the missionary position I could feel both their energy as each time either one of them entered me they pumped into my hole with a vengeance like they were trying to hurt my hole. They both were fucking me like I was a piece of meat and what was weird, although the sex hurt a bit, I couldn't help but notice how wet I was and how much I liked being fucked and treated like a sex doll. I was almost disappointed when after another ten minutes Jason's roommate fucked me and I felt him bust deep inside me. When Jason saw this, he hurried up and entered me after his roommate pulled his flaccid dick out of my wet dripping hole. Jason fucked me with a fury until he too ended up busting inside of me moments later.
I had the audacity not to feel ashamed after I'd showered, dressed, and headed to my car with my swollen sore asshole in tow. Funny thing is, I never found out Jason's roommate's name. I was so wretched. SMH
