Trophy Hunting

I moved out on my own before graduating high school. I was 18, working fifty hours a week on top of going to school. I was dating a thirty two year old single mom who I saw every other week and was having an affair with my twenty-six manager on the side. I worked with both women and they knew I was fucking both of them. I didn't like drama. What I did like was sex and lots of it.

Elaine was the single mom. She went through a messy divorce and was dating a guy her own age before we hooked up. She was short 5'6" very slender, tan skin with bikini tan lines, curly shoulder length brown hair and brown eyes. We began seeing each other one night after closing together. I went to her two bedroom apartment we hung out watching TV. She asked me to stay the night because she didn't like sleeping alone. I told her I preferred to sleep naked and asked if she had a problem with it. Elaine also liked sleeping nude. What started out as cuddling soon turned into a passionate night. I memorized every inch of Elaineundres. We only had sex one time but it was slow, methodical, and amazing. She enjoyed it so much that she broke up with the she had been seeing. We agreed to not see each other on the weeks she had her son living with her. I still got to see her at work which worked for us both. It was low pressure and we both understood it wasn't long term. Elaine's only request was that we spend the nights together when she was alone.

Janet, was my manager. She and I had butted heads from the start. I was a bit cocky and always thought my way was better and Janet also thought her way was better. We had several heats arguments over the course of working together for three years. It all changed on fateful evening at work when she accidentally started a fire in the backroom. I immediately grabbed the fire extinguisher from the wall and told a very hysterical Janet to call the fire department. Even though the fire was growing fast, I somehow managed to stay calm thanks to Janet screaming at me. Janet was grabbing my shoulders and jumping up and down. I used the extinguisher to put the whole fire out just before the fire department arrived. Luckily no one was hurt. We had to close early. Janet was so elated that the building didn't burn down. She asked to come over and see my apartment. It was very odd how she lingered around after I showed her my one bedroom place. It wasn't anything special, the shower was just a curtain with a drain, the kitchen was very small. The living room was long and narrow. I had a cheap leather couch, a TV, a VCR, and a few movies. My bed room was a piece of carpet over a concrete floor with just a mattress and a dresser with a tiny closet. My apartment was in the basement so there were no windows. It was around 10pm when Janet sat down on my couch and a flood of emotions came out of her. I really wasn't listening and wondered when she might leave. Then Janet opened up about her relationship with her husband. They had been married for almost eight years. He struggled to keep a steady job and he had a drinking problem. Then she went on to say her sex life was non-existent. She looked at me and flat out asked to have sex with her. I was stunned and aroused by how direct she was. I started to get hard. Janet had specific rules though. She must of put a lot of thought into it and later she confessed I was her target from the start. The rules were, no kissing, she refused to perform oral on me but was open to me doing oral to her, she insisted I pull out before cumming and she wanted unprotected sex, no anal, no doggy style, and I wasn't to tell anyone at work. She stood up and we both began to undress. Janet was about 5'8", very pale like ghost white skin, she actually had a nice body, very lean and muscular, very small tits her nipples were extremely tiny, she was neatly trimmed down and when she stood with her legs together there was a small triangular space between her upper thighs and her pussy was...which I found very sexy. When Janet saw me naked for the first time she blurted out, "how the hell did you hide that thing!" as she pointed to my extra thick seven inch cut cock. I followed to my mattress on the floor. She laid down and opened her legs. I think I surprised her when I dove face first down into her pussy. Janet yelped and began breathing heavy. There were things she enjoyed from my oral assault and things she didn't like. She was very vocal. I was somewhat put off by her negative comments and demanded that she direct me to what she did like. I told her that I really wanted to please her. Janet froze and went quiet for a minute or two. Then she looked at me as I rubbed her clit. She spoke in a much kinder tone and gave me the secrets to getting her off. It took a while but I did manage to get her off. Janet had to pinch and twist her nipples while I my tongue swirled over her sweet spot. Janet then let me take her. I moved up between her legs and she guided my throbbing cock into her premoistened hole. Janet moaned very seductively. Which aroused me even more. I went slow per Janet. She was very tight. Her pussy seemed to tighten and clinch around my flesh stick. I went slow but she actually preferred it fast and a bit rough. I leaned over more. She raised her legs upward and more open showing off her flexibility from being a gymnast years earlier. I basically was drilling deep and down into her. Our flesh smacking against each other. It was slightly odd that I couldn't kiss her but she did let me suck on her neck and ears which she did comment on how it made her feel. I felt the urge rising but held out as long as I could. Janet sensed I was close as I slowed down from my jack rabbit pace. I pulled out. Janet reached down and jerked me hard. I exploded shooting a large load up her chest and onto her face. Janet hadn't expected this and made a sour face with her mouth open. The second load was just a powerful but not as heavy. My cum went directly into her mouth and up her nose. Janet choked as the third plopped onto her tint breasts and the fourth filled flat stomach and filled up her belly button. Janet let go of me as I jerked all my juices out onto her. She actually needed up swallowing some of my cum. Janet commented on the bitter taste as she snorted it out of her nose and wiped it from her eyes and face. I rubbed my body against her with the lubricant I had produced between us. At first Janet began to object but the way I looked at her now seemed to soften her. I wanted to kiss her cum stained lips so bad but refrained. Janet got into it and even grabbed my ass. She openly stated how nice of a hard bubble butt it was. She even spanked me which I liked and she smiled. It was rare to see her smile and she actually looked kind of cute in that moment. Janet had to get cleaned up and we took a shower together. I took the liberty to wash her hard toned body with soap. Janet liked it for a while but got defensive when I reached around her aggressively pulling her soapy body back into me and I fingered her. She told me to stop but I was too turned on. I Janet didn't really try to move as my fingers entered her. She even placed her hands over mine slightly grinding. When my cock was moving up between her soapy ass, I had dipped down a little too far and found her forbidden hole. Janet quickly broke free, turned around and smacked me hard across the face. The sound was just as alarming as the act. I was in shock! It didn't hurt as bad but the suddenness of Janet's hand slapping me in the face was. She looked surprised and covered her tiny breasts and her pussy with her hands like suddenly being aware she was naked in front of me. A million thoughts raced through my head....should I hit her back...should I fuck her right now. Instead I did nothing, we rinsed, toweled ,got dressed and Janet left without saying much.

Working the next day with Janet was awkward. She was short and bitchy with me. Co-workers picked up on her hostility towards me. What really sucked was that we were closing together which made for an extreme long evening. I tried to trade my hours with another employe