The Best Head EverbyIkay©
This is a true story. It actually happened to me! It's pretty short so bear with me.
Our boss, the Editor of an entertainment magazine, informed her staff, me included, that she had no intention of releasing us till we had finished the layout of the third edition. This meant us staying overnight in the office, working till daybreak to meet the 12pm press deadline. We didn't complain. We didn't complain because complaining was futile. Our boss is a classical bitch with no trace of human empathy. She couldn't care less how we felt.
I'm one of the three graphic artists working on the magazine and I love my work. Working overnight wasn't a problem but after a few hours straight in front of the computer my mind began to fuzz. I needed a break. The time was 2:30am and I wanted to stretch my legs. I found two other colleagues who shared my needs and we left the premises.
We walked over to an all night store to buy some soda and grab a few smokes. At this time of the night hookers lined the street. They were mostly interested in the occupants of big cars that cruised the circuit like slow moving sharks. A few did offer their services to us but we just wanted the sodas and the cigarettes. However as we walked back I was having a change of mind. I haven't had sex in three weeks and I was as horny as hell. My nuts felt like golf balls and I badly needed relief.
As we were passing one particular lady, she asked me for a cigarette. I gave her one and lighted it for her. She wasn't really that pretty and her breasts were too small but she had this perfect bum that looked enticing in her tight blue jeans. The blouse she was wearing was see through and I could see her lace bra clearly. I looked her over and considered propositioning to her. She caught my roving eyes and smiled slyly.
I have never had sex with a hooker before and I wasn't sure if I wanted to start right now. I had this prejudice against prostitutes: why pay for sex when I could get it for free? I had a number of female colleagues that I could screw easily, all I needed to do was ask nicely, but I decided I would do it just for the hell of it.
I asked her how business was going and she said it was going fine. I told her I wanted a blow job. She smiled and told me she wasn't very good at sucking cocks. My colleagues stood nearby, shaking their heads and sniggering. I ignored them.
She then told me that she would do her best for me and took me by the wrist. Dragging me a little way she asked me how much I would pay her. I mentioned an amount and we haggled for a while. Eventually we reached a price that we were okay with. She said I was free to squeeze her bum as she sucked me. I certainly agreed with that.
I signaled to the other guys that I would catch up with them as she led me to a dark corner. I was slightly apprehensive: she could very easily lead me to a trap and I could get beaten and robbed. When we were finally alone she started to peel off her jeans which I considered odd since it was only meant to be a blow job. However who was I to complain?
I unzipped and pulled down my jeans as I appreciatively appraised her panty clad bottom. She reached for my already stiff rod, and taking it in her hands, squatted down. The feeling of her hot moist mouth enveloping my dick was a sensation I wouldn't easily forget. She immediately began to run her tongue all over my shaft. I leaned against the wall and braced myself.
She made loud sucking noises as my dick moved back and forth in her mouth. I reached my hands down to caress her hair and cup her chin. Her eyes looked up at me and I stared back at her.
I bent slightly over her and she raised her bum. I reached down and grabbed her cheeks. I kneaded and squeezed them while she continued with the job at hand. I slipped my hand into her panties to touch her crack and moved down to her pussy. She made small muffled moans as I fondled her. I didn't know whether she was making those noises for my benefit or whether she was really enjoying it. I didn't care anyway.
Eventually she came up for air and got to her feet but kept her hands on my dick. She stroked it vigorously and I reached out to squeeze her small hard breasts. A few seconds later she went down again and put my cock back in her mouth. As I rubbed her bum again I considered stepping up my game and turning her around so I could plug into her from behind. However I was trying to avoid penetration because that would make her increase the charge and also I wasn't a big fan of condoms. I had no intention of skin diving a hooker.
I was taking my time coming. Blowjobs aren't usually enough to make me come and I didn't think she would want to continue indefinitely. However she really worked hard at it and I was impressed with her determination to give me full customer satisfaction. Once in a while I would direct her hands to my balls and she would gently squeeze and caress them. Eventually I grunted and stiffened and she immediately withdrew but kept jacking me off till I blew my load.
She gave me a napkin to clean up with and after we had dressed up we walked out back into the street again. I paid her the money and actually tipped her for a job well done. I left her and went to join my friends who were still waiting for me. Understandably they were green with envy. As for me I smiled like the cat that just got the cream and we strolled back to the office.