Straight Male / 26
I've been an Actuarial Analyst for almost four years, Over that period of time, a woman named Linda has been my manager. She has been with the company a long time. She is in her late forties. I know a little bit about her. She is married to a guy who looks about sixty. He's fat, bald and looks like Alfred Hitchcock. Supposedly he was a big wig at a research hospital but was let go years ago. As far as I know he doesn't do anything now.
She is one of those women you know would be attractive if she wanted to be. When I first started, some of the older guys talked her up, telling me about what a great ass she has and what nice tits she has. You could see something there but she was such a conservative dresser she just gave off rare glimpses of her potential. She's a tall blond with blue eyes who always wears her hair up.
After I'd been there a year or so she started complimenting me on my work and taste in suits and asking me about my social life. She was very forthcoming in advising me on my career and on life in general. I never thought much about it. I just thought she was a good boss.
Over time, I noticed that she tended to gravitate towards me at company functions and employee weddings and gatherings like that. I'm only talking about four or five times a year but I often found myself on the dance floor with her or in a corner sipping drinks and talking. I noticed that after a few drinks she got awful touching feely. I really didn't know what to think. At a charity ball thing I had to go to, some guy I didn't know told me I was "in". I said "what??' and he said, with that "blond babe". He told me to make a move and warned me against ever passing up "older pussy". I thought the guy was nuts. I figured I'd get fired if I made a move on my married boss.
A few nights ago, myself and another guy on my team were working late to finish a project. Our boss was there too. she picked-up dinner and helped us along. When we were finished, my co-worker was anxious to get home so my boss told him to take off and said that she would help me out. There was very little left to do after he left so I told her I was all set. She massaged my shoulders and told me what a great job I'd done. Now I must admit, I was thinking about what it would be like to have sex with her at that point but never thought it was possible. She told me to finish and to be sure to check in with her before leaving.
When I knocked om her office door she said come in. I walked in and she was standing at her office cabinet holding a drink. She was almost nude. She was wearing white pearls and black stockings, high heels and nothing else. Her hair was down. It was dirty blond and cut just below her ears but she had done something with the bangs that made her face look beautiful to me. She had a very light tan with just a hint of tan line at her breasts and bikini lines. Her stockings went right up to the top of her thighs. Her legs were crossed so I couldn't see her pussy but I could see she was shaved bare. She had nice wide hips and the type of stomach where you could see the outline of her upper abs and rib cage. Her breasts were big but not huge. Probably C-cups but they had just a slight sag to them that showed off her long nipples which were just sticking straight out right at me. I took one look and wanted to bite those things.
She seductively waved me over with her finger and handed me a drink. It was a capt & coke which is my drink. She smiled and said I deserve one. I stood there like a fool drinking my drink while she told me what a great employee I was and how she saw a great future for me. We talked for almost a half hour. The whole time we were talking she was standing there nude. I was very nervous. I didn't know what I should do. I've never been a big ladies man and this situation was knew to me. She gave me a second drink and gave me a kiss on the cheek.
I knew she wanted sex but even though she was standing naked in front of me I just didn't know what to do. She asked me if I had ever been with an older woman before. After I said no, she asked me if I had ever been with a married woman before. I said no. She said that she was upset with me. She said it wasn't right that I had been leading her on and not making a play for her after I'd gotten her "all hot and bothered". I was speechless.
She smiled and told me to relax. As I composed myself, she came over, took my drink, put it down and started kissing me. I stood there as she did so. She took my hands and put them on her ass. Her skin was soft and cold to the touch. She told me to squeeze her ass so I did. I loved it. I was squeezing her cheeks like a mad man. I'd almost always dated women who had either tiny asses or no asses. This woman had a real ass. A meaty ass. I could squeeze it and massage it and never run out of it!
While we were kissing and I was killing her ass, she said "suck on my tits" god yes. I went wild on those beauties. Sucking and squeezing. Her tits were incredible. I beat those damn things. She loved it. She started rubbing her pussy. Her own! I'd never seen that before. She had finally spread her legs giving me a view. She was beautiful down there. She had this line across her abdomen that just highlighted her shaved mound. I could see her lips peaking out as she played with herself. She kept at it as I sucked her tits until she started breathing fast and whining. She was going to make herself cum. My fucking boss!
This was so awesome. After she came she got wild. She started kissing me, right down to my pants. She hurriedly unbuckled and unzipped me and pulled my pants and underwear down. She was so anxious but I wasn't hard yet. She didn't seem to care. She went after my cock like a mad woman. She dropped right to her knees and started feeling my balls ans my cock. She said something like "don't be shy" and started kissing my cock and sucking my balls. As she worked me I felt myself growing hard. She popped my rod in her mouth and started this weird sucking motion right on my head. No woman ever did that before. It made me start getting harder and harder instantly. Once I was stiff she complimented me on my cock! She said it was "very nice."
She kissed and sucked it She started taking it deep. She was stroking and sucking at the same time. As I watched her lips sliding over my cock head, I could see her wedding ring on her hand stroking my cock. I could feel the band on my cock. It fascinated me. In no time I felt an orgasm coming. She was sucking so well. She found just the right spot and tempo. I told her to be careful because I might cum and she kept on and on. When I was close I said fuck it and grabbed her head and started face fucking her. At the last second I grunted and shot a load in my boss's mouth. She swallowed it right down like nothing. She kept sucking until there was nothing left to suck.
Afterward, we talked for awhile. I had pulled my pants back up. She was still nude while we talked for at least an hour. I kept sneaking glances at her pussy. She explained how things were going to be. She was going to help me with my career and I was going to have sex with her occasionally. She was clear that I didn't have to and it wouldn't hurt me but also made it clear that it's good to have a friend in higher places. She also explained that if I met someone special, I could let her know and she would stand down. She was clear that discretion on my part was mandatory. She told me that we would take it slow and that next time she wanted me inside her. At this point I don't give a shit about the job. I just want to get inside her pussy.
She is one of those women you know would be attractive if she wanted to be. When I first started, some of the older guys talked her up, telling me about what a great ass she has and what nice tits she has. You could see something there but she was such a conservative dresser she just gave off rare glimpses of her potential. She's a tall blond with blue eyes who always wears her hair up.
After I'd been there a year or so she started complimenting me on my work and taste in suits and asking me about my social life. She was very forthcoming in advising me on my career and on life in general. I never thought much about it. I just thought she was a good boss.
Over time, I noticed that she tended to gravitate towards me at company functions and employee weddings and gatherings like that. I'm only talking about four or five times a year but I often found myself on the dance floor with her or in a corner sipping drinks and talking. I noticed that after a few drinks she got awful touching feely. I really didn't know what to think. At a charity ball thing I had to go to, some guy I didn't know told me I was "in". I said "what??' and he said, with that "blond babe". He told me to make a move and warned me against ever passing up "older pussy". I thought the guy was nuts. I figured I'd get fired if I made a move on my married boss.
A few nights ago, myself and another guy on my team were working late to finish a project. Our boss was there too. she picked-up dinner and helped us along. When we were finished, my co-worker was anxious to get home so my boss told him to take off and said that she would help me out. There was very little left to do after he left so I told her I was all set. She massaged my shoulders and told me what a great job I'd done. Now I must admit, I was thinking about what it would be like to have sex with her at that point but never thought it was possible. She told me to finish and to be sure to check in with her before leaving.
When I knocked om her office door she said come in. I walked in and she was standing at her office cabinet holding a drink. She was almost nude. She was wearing white pearls and black stockings, high heels and nothing else. Her hair was down. It was dirty blond and cut just below her ears but she had done something with the bangs that made her face look beautiful to me. She had a very light tan with just a hint of tan line at her breasts and bikini lines. Her stockings went right up to the top of her thighs. Her legs were crossed so I couldn't see her pussy but I could see she was shaved bare. She had nice wide hips and the type of stomach where you could see the outline of her upper abs and rib cage. Her breasts were big but not huge. Probably C-cups but they had just a slight sag to them that showed off her long nipples which were just sticking straight out right at me. I took one look and wanted to bite those things.
She seductively waved me over with her finger and handed me a drink. It was a capt & coke which is my drink. She smiled and said I deserve one. I stood there like a fool drinking my drink while she told me what a great employee I was and how she saw a great future for me. We talked for almost a half hour. The whole time we were talking she was standing there nude. I was very nervous. I didn't know what I should do. I've never been a big ladies man and this situation was knew to me. She gave me a second drink and gave me a kiss on the cheek.
I knew she wanted sex but even though she was standing naked in front of me I just didn't know what to do. She asked me if I had ever been with an older woman before. After I said no, she asked me if I had ever been with a married woman before. I said no. She said that she was upset with me. She said it wasn't right that I had been leading her on and not making a play for her after I'd gotten her "all hot and bothered". I was speechless.
She smiled and told me to relax. As I composed myself, she came over, took my drink, put it down and started kissing me. I stood there as she did so. She took my hands and put them on her ass. Her skin was soft and cold to the touch. She told me to squeeze her ass so I did. I loved it. I was squeezing her cheeks like a mad man. I'd almost always dated women who had either tiny asses or no asses. This woman had a real ass. A meaty ass. I could squeeze it and massage it and never run out of it!
While we were kissing and I was killing her ass, she said "suck on my tits" god yes. I went wild on those beauties. Sucking and squeezing. Her tits were incredible. I beat those damn things. She loved it. She started rubbing her pussy. Her own! I'd never seen that before. She had finally spread her legs giving me a view. She was beautiful down there. She had this line across her abdomen that just highlighted her shaved mound. I could see her lips peaking out as she played with herself. She kept at it as I sucked her tits until she started breathing fast and whining. She was going to make herself cum. My fucking boss!
This was so awesome. After she came she got wild. She started kissing me, right down to my pants. She hurriedly unbuckled and unzipped me and pulled my pants and underwear down. She was so anxious but I wasn't hard yet. She didn't seem to care. She went after my cock like a mad woman. She dropped right to her knees and started feeling my balls ans my cock. She said something like "don't be shy" and started kissing my cock and sucking my balls. As she worked me I felt myself growing hard. She popped my rod in her mouth and started this weird sucking motion right on my head. No woman ever did that before. It made me start getting harder and harder instantly. Once I was stiff she complimented me on my cock! She said it was "very nice."
She kissed and sucked it She started taking it deep. She was stroking and sucking at the same time. As I watched her lips sliding over my cock head, I could see her wedding ring on her hand stroking my cock. I could feel the band on my cock. It fascinated me. In no time I felt an orgasm coming. She was sucking so well. She found just the right spot and tempo. I told her to be careful because I might cum and she kept on and on. When I was close I said fuck it and grabbed her head and started face fucking her. At the last second I grunted and shot a load in my boss's mouth. She swallowed it right down like nothing. She kept sucking until there was nothing left to suck.
Afterward, we talked for awhile. I had pulled my pants back up. She was still nude while we talked for at least an hour. I kept sneaking glances at her pussy. She explained how things were going to be. She was going to help me with my career and I was going to have sex with her occasionally. She was clear that I didn't have to and it wouldn't hurt me but also made it clear that it's good to have a friend in higher places. She also explained that if I met someone special, I could let her know and she would stand down. She was clear that discretion on my part was mandatory. She told me that we would take it slow and that next time she wanted me inside her. At this point I don't give a shit about the job. I just want to get inside her pussy.
- That's Juicy! 23
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