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Masturbating the Boss

Posted by: SoloTouchArchive Author: Jack Age: 66 Posted on: 24 May 2022 7 comments
9 likes 1051 views Category: Masturbation Male-Female Tags:

A girl in my company has been masturbating me regularly for several years. She makes me happy, and enjoys the security of an older man.
Oh, my, Marie, your story about the blind gentleman, and how you 'have made a living off of him' struck a chord with me. Some people might think that you took advantage of this gentleman, but I know you have not, for something similar has blessed my own life.

I am in my sixties, and have a small business where I'm able to employ three to four young women at any time. Only one girl has stayed with me, the others have left to further their careers or perhaps to find another boss. I have to admit that I often find the girls who work with me sexually arousing, but of course, I cannot make advances, and, because I'm older, they would not be interested. But every night I masturbate thinking of one or another of them. Of course, I feel a little ashamed and humiliated at this, but that's how it is.

Or was. One girl, Sherry, had worked for me for three years when suddenly, we got to know each other better. She told me much later that she had noticed when she first started working that I enjoyed looking at her nipples and breasts on days when she didn't wear a bra (she has small breasts but big nipples), and she began to go bra-less more often. Especially when she knew other girls wouldn't be in the office, and we'd be alone, she would wear more revealing clothes than you would expect in an office. I noticed, when she did that, that she always talked and flirted a little when she came in on those days, and would stretch her arms above her head, or invite me to look at her work and bend so that I could see her nipples down her blouse.

Of course nothing was said about this, but we both knew that it put me in a very good mood, and we would smile a little when we remarked that the other girls wouldn't be coming in. Sometimes she brought very sexy clothes with her if she was going out after work, and would change into them, then wait for a boyfriend to pick her up. She knew she was teasing me horribly, and I was both jealous of her boyfriend, and eager to masturbate as soon as she left.

Then one day we had to drive a long way to visit a client, and in the dark of night, on the way back, she began telling me about her sex life. Just as she was reaching puberty, her father became handicapped, and, because her mother worked, she had to spend most afternoons after school at home, taking care of him. He was confined upstairs, and she had a girlfriend come over one day, and they began kissing. One thing led to another, and soon they were having very hot girl sex every chance they got, which was most afternoons. Now and then she would pull herself off the couch to answer her dad's call.

She had to bathe him regularly, and saw his naked body often. She felt both attracted and repulsed by it, and especially by his helplessness. One day she saw her mother masturbating him, and although she was intensely curious, and wanted to bring relief to her father, she could not bring herself to do more than fondle him while washing during baths.

She was seventeen before she had sex with boys, at first she didn't like it much, and instead of fucking them, she masturbated them, which turned her on. She had three brothers, and was used to boys, and when they hit on her for a hand job, she usually complied. Often, she would masturbate a boy and then rush to have sex with her girlfriend. Then she met an older boy who was very experienced, and she submitted to his rough sex, and had a new, awesome kind of sex.

She obviously knew a lot about guy's masturbation, and somewhere in the conversation she told me she figured that I masturbate tons, and some of the other girls thought so too. She even mentioned a couple of times when I'd gone to the toilet during work to jack off. She was laughing that I was so surprised she knew! She told me not to worry, it was really no big deal for her, and it was natural since I didn't have a wife or girlfriend or anything. She told me that most nights when she wasn't going out, she would masturbate slowly for a long time.

I was getting pretty hot under the collar by then-turned on, and also confused about what to do. This wasn't the kind of conversation to have with an employee, and also I was feeling helpless and kind of humiliated with how she pegged me as a masturbator. I got pretty quiet, and I think we didn't talk much for the rest of the drive. When I got home, I masturbated dreaming of her doing it to me..The next day she had the day off and all I thought about was her masturbating me. I was petrified to ask, though.

That night, the phone rang, and it was her. Her voice was soft and sexy, and I immediately knew that she was probably naked on her bed, masturbating.

'Hey boss, I was thinking, and you know I told you about how I used to give a lot of hand jobs? Yeah? Well, I was thinking that I always wanted to masturbate my father and you're kinda like that for me, so if you ever want me to, I'll give you an awesome hand job, and I won't call the cops or sue you or anything-I really want to do it.'

She had it all planned out: the other girls would be in the office, but if she comes in late, she has a reason to stay late, and when they leave, we would be alone. That day, she wore very proper clothes, with not a hint of titty showing, and she behaved very 'officially', something that became a pattern on days when she would offer me special services. As soon as the other girls were out the door, she took charge. She locked the door and checked it, and told me to take my pants off, fold them and put them where I could reach them. I was suddenly very shy, and she prodded me until I was naked sitting in her chair, which she said was a better height.

Then she pulled lube out of her purse and set it on her desk, and then pulled up her blouse and sweater revealing her breasts, totally. I already had an erection, and I almost came before she even smeared me with lube. I was putty in her hands!

I have many girls wanting to work for our company; we're in a competitive business, and it's an excellent opportunity. My 'special assistant' is not the best compared to others in the field, but has security, and can set her own hours, and I give her extra pay that the other girls don't know about. She's been with me twelve years now, through recessions, expansions and, for her, a series of boyfriends. I know about them all because she often talks about them while she's masturbating me, or when she calls from her apartment when she's masturbating, and lets me hear her orgasm, but she's never done it in front of me.

She teases me, then unzips my pants and teases me some more. I can't get enough of it. Many people would say that she's taking advantage of an older man. She never has sex with me, and she does use me to get things she wants. She has definitely 'made a living off me' just by undoing a couple of buttons of her blouse and using her hands.

We also have a tender and kind relationship, based on mutual understanding of needs. She confides in me, often about sex, but also about her life, and cries on my shoulder. From the outside, she might appear to be the most professional of 'masseuses'. Yet we are bonded in the most intimate way, and have shared this intimacy while other relationships have come and gone. The woman who wrote 'Years of Masturbation with my Uncle' said, 'The two of us have a very unique relationship and I am so happy that we do. He is always there for me when I need him. He is my shoulder to cry on if I need one. I love him very, very much. 'I feel the same way.