Overtime

Keith has a job that affords him quite a bit of overtime, and occasionally he'll tell his wife he's working overtime, and come work on me instead. Yesterday around 7 Keith rang me to ask whether I'd be able to give him any overtime work at about 11pm. I'm always ready for that. He wanted role play, and gave me instructions on where to meet him to start.

At 10:45 I left my apartment wearing a sweater coat wrapped tightly around me, along with black patent stilettos. I walked a few blocks to our designated meeting spot, heavily made up and wearing a thick coating of red lipstick. As I got to the spot, I took my sweater off and slipped it into my little backpack purse. Also in there were condoms I was instructed to buy on my way to the meeting place. I stood on the dark corner in my stilettos, a micro mini skirt with no panties on, and a bustier that barely contained my tits. It was so low that my tits usually fall out of it if I wear it during sex.

A minute or so after I arrived, Keith rolled up in his car and rolled down the passenger window. I could see there was someone in the backseat as I leaned into the window and asked if he was looking for fun.

"How much to blow my friend back there while I drive him home?"

I grinned wide. "$50 and a ride back for me."

"Get in." He handed me a wad of cash that I put into my bag as I got in the back seat. I was immensely turned on and really into the role. I smiled and thanked Keith and began to rub his friend through his jeans. "You have 20 minutes to make him cum." Keith barked from the front seat as he pulled away.

I opened his pants and he helped me pull them down a bit, along with his shorts. His cock was completely hard and impressive. He was also uncut, which is my favorite. I pulled the skin over his head and played with it for a bit until he began to push my head down. I sucked it for a moment then stopped and went in my bag for the condoms. As I tore one open Keith barked, "No condom, cunt." from the front seat. I was instantly wet. I had no idea if the friend was in on the secret or not, but it made me feel so dirty. As I put the condom back in my bag, the friend slipped me another $40.

I began sucking his cock like a good little whore as we drove through the streets of Brooklyn. I could see my lipstick smearing all over his cock as I sucked and slurped at his throbbing cock. His foreskin was big enough that even though he was fully hard there was plenty to play with, and he gasped and moaned every time I nibbled on it or stuck my tongue inside it. His balls were tight and twitching, and I knew he was close. He kept pushing my head down and bucking up against my face.

"Two minutes bitch. Finish or we leave you here." Keith ordered from the front seat. I began to suck furiously. Moaning and stroking the base of his cock as I massaged his balls.

"Oh fuck I'm gonna blow." the friend hissed. "Eat it, whore." His cock throbbed and hot creamy cum filled my mouth. I pulled his skin back as I paused to swallow, then slowly sucked him from base to head to suck up every drop of cum. The car stopped in front of an apartment building and the friend got out, thanking Keith, and not even saying a word to me. I felt so used... and sexy. What a rush.

After he entered the building I got into the front seat with Keith, and he grabbed me and kissed me long and hard, tasting the remnants of his friend's cum. I had known that Keith wanted a hooker roleplay, but no idea that he was going to involve anyone else. The best part? The friend had no idea that I wasn't really a prostitute. Keith had said that they'd been talking about hookers earlier in the day and the friend said he'd never been with one but was curious about it. So, Keith told him he'd hook him up with one he'd used before, and I got to play that part. Very fun.

During my enthusiastic sucking my tits had slipped out of my top as I'd predicted, and I was now sitting in Keith's front seat with my nipples rock hard from the cool night. He reached over and began to knead my tits and twist my nipples. He asked if I was bare under my skirt as he'd instructed, and I showed him that I was. "Good girl. Now lean back against the door and play with yourself so I can see." I happily complied, leaned back, spread my legs, and gave him quite a show. I rubbed myself to orgasm 3 times before we got back to my place, so easy because I was so turned on from sucking cock.

As we drove down my block I put the sweater back on, not bothering to tuck my breasts back into my top, enjoying the rough material on my sensitive nipples. I was wiping the lipstick off my face as we pulled into the little drop off area in front of the building. When we went inside, Keith gave the doorman $20 and told him he wouldn't be too long but to buzz my apartment if he needed to have the car moved.

Once upstairs, Keith went down on me right away. I was quick again to cum, all over his face. We went up to the playroom where we spent the next 2 hours fucking in all different positions, me still in my hooker getup. As we both lay there spent, his cum oozing out of my pussy and my stretched asshole, he called his wife to tell her he was just getting ready to leave work, and he'd be home soon.