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  • — If The Boss Only Knew —
    Straight Male / 45

    I've been working for Mr. S for 15 yrs as a maintenance mechanic at one of his 4 large production companies. He is very wealthy and then two years ago he divorced his wife leaving her a luxurious estate in northern New Jersey. I got divorced 6 years ago so when he offered me the job of managing his wife's estate close to 2 years ago I jumped at the chance. Not only was the salary good but I live on the estate in a private cottage at the rear of the 22 acre property. I supervise 5 other employees who are the grounds keepers and pool help but am the only one living here. The boss's X-wife Doris is 57 years old, fairly attractive and a pathetic alcoholic. They have two kids, a son and a daughter who are both married and live in New York but visit often on weekends. Doris lives like a queen, has two daytime house keepers and seldom leaves the property. When she does go somewhere she always has a town car service. She is at her pool a few days a week but never uses the tennis court that's at the side of the house. She does use the pool year round since its enclosed and heated just outside the back of the house. She was annoying as soon as I started working there calling me a in the evenings or nights to fix something extremely minor or didn't exist. After a month or two she began having me sit and listen to all her problems telling me personal stuff about my boss and her kids. Some nights she was so drunk I had a hard time understanding her. After awhile it was like I was her confidant and she began telling me everything from her wealth to her sex life. I already knew she had a nice body since seeing her at the pool many times. For a woman her age she can still wear a bikini and the main thing I always thought was all she need was a nose job. I sit a talk to her, mostly listen, for an hour or more and she often had her night clothes on and some very revealing. There was never any interaction between us but then one night, in a drunken stupor, she told me she had constipation trouble. My first thought was why the hell would she even tell me something like that. I not positive what I said but remember telling her to try a Fleets enema or some kind of laxative or something. It was three nights after that she called me around 7 pm asking me to come to the house. Drunk as usual she showed me the three Fleets Enemas her housekeeper picked up for her. She had me read the directions for her which explained how to insert it. She sat silent for a moment and then said she can't do that. I had only known her by that time for a few months and after all the years working for my boss only remember seeing her one time. She looked me straight in the eye and asked me to do the enema for her and I almost fell off the chair.


    I was flabbergasted that she asked me that and I mumbled something like "if you really want me to I will". The next thing I knew she led me up to the master bedroom and into the bathroom. I was nervous by that time and she asked me what to do and all I said was she had to bend over and pull up her night gown. She bent over holding on to the toilet seat pulling her nightgown up but had panties on. I then said she had to take them off and she did with no sign of embarrassment. She leaned back over again and I just pulled her cheeks apart telling her I was putting it in her and saw her vagina and anus for the first time ever. Once I emptied it into her I told her to sit on the toilet and I left the room. I must have stood outside the bathroom for about 15 minutes hearing the toilet flush a few times before she asked me to come back in. She was still sitting on the toilet and to my disbelief asked me to help her get into the shower. She said she felt dirty and now it was a situation where she obviously was so drunk she didn't care if I saw her naked. She began pulling her nightgown up and I helped getting it over her head right away seeing she had no bra. I'd seen her in her bikini but now realized how nice her body really was and right away got a hard on. I turned the shower on for her and she asked me to leave the room. Again I stood in the hall until she was done and when she called me back in it was to get her a towel. I watched as she dried herself then took her into her bedroom and put her to bed. That was it and I locked up and left. That night is what encouraged me to take advantage of her drunken naivety. I not only supply and give her a Fleets Enema every four or five weeks but have persuaded her to let me give her a massage once or more each week. She has never shown any signs of being embarrassed and willingly undresses in front of me. I didn't masturbate her right away but over a few months she began letting me finger her and rub her breasts. She orgasms often and I if she don't know by now I'm screwing her she is more of a drunk than I could imagine. I never get on top of her but am able to have her stand bending over and do it doggy style. She has never told me not to and I often think she is unaware of what I am doing. There are times I have anal intercourse with her and even that she never objects to. I never have to call her because she manages to call me for something a few times a week. I always ask if she wants a massage and there are times she don't which makes me think she didn't drink a lot that day. My boss only stops by a couple times a month just to check up on things making sure the property is in good shape. He always thanks me for doing a good job but I wonder what he would say if he knew how his X is so free with her body. He asks if she bothers me much but I always tell him she keeps to herself most of the time. I still can't believe this all started over constipation.

    #41838 — Comments (0) — Oct 11, 2018 at 12:29 PM — That's Juicy! (7) Remove This.

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