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I want to orally pleasure my boss

Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
in Sex & Relationships
Hello. I am a 26 year old guy who is working for an attractive, strong woman in her late 40's. I am incredibly attracted to her. Something about her just really turns me on. She has a really nice body for an older woman, beautiful hair, and a very commanding personality. She is just so pretty and sexy!

Anyway, I have this huge fantasy about servicing her orally under her desk in her office. I really would like to make at least part of my fantasy come true but I am unsure how...or if to proceed. I mean, I certianly don't want to approach her at the office and ask if she would like me to lick her p*ssy!

My real problem is that due to my age and our work situation I am afraid she would find any kind of sexual relationship completely inappropriate.I have the feeling that she knows I am attracted to her. I am sure she has caught me checking her out from time to time. (She has great breasts and lovely feet. I can't help but glance at her painted toes) I am not sure how she feels about this. She has never mentioned but I don't think it is completely unwanted either. I would love to say I think she finds me to be an attractive young man but my judgment gets clouded when I am this infatuated.

How should I approach her? I am interested in a sexual relationship outside of work. I really don't care if she becomes emotionally attached to me. I just want her to use my tongue for her pleasure. She doesn't even have to do anything but allow me to masturbate while I service her.

Any advice on this matter would be much appreciated. It has become so bad that I actually have to use the men's room at least once a day and masturbate to relieve my tensions. Men and women please respond. Thank you.

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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    relationships with people at work don't work generally...i'm not sure if this is a healthy obasession you have...try talking to her about your feelings, though without saying "i wanna go down on you"
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    I have had relationships with women I work with in the past. Everything worked out fine. The only difference is this woman is my boss. Of course, I would have to tread more carefully. I would like to let her know I am interested but not so obviously that it would put my job in jeapardy. I want her to make the move that finalizes the sexual relationship.
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    That could be werid. My boss came on to me and I had a boyfriend at the time and was very turned off by it and things were never the same. I would say the best way to go about things is flirt with her and then depending on her response go from there. If she doesn't react favorably then i don't thinks would go much further. Your first concern should be your job .. vuz it was horrbile when my boss did that to me i left and we don't speak anymore
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    Wow, scary one that.

    I wouldn't make any move that could jeopardise your job or your position there. So don't say anything that could backfire, or freak out your boss if she isn't interested.

    You could just start by mentioning you are going for a beer after work one day )perhaps even with friends) and would she care to join you. That way, you can get to know here better, and test out how she feels before making a move that could potentially damage tyour relationship with her, and more importantly your career!

    Just take it easy, and start with basics, get to know her and you never know, she might like you too. You never mentioned if she has a partner or not - or yourself for that matter. If you are getting into affair territory, it would be a different story and I'd steer well clear.
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    This is just a fantasy of yours. Do you REALLY see it going anywhere or in the manner which you seem to imagine? C'mon. We all fancy people that are out of reach from time to time but we realise that it is just a fantasy and live with it.
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    :yes:
    The thing with fantasies is that they should stay just that - fanmtasies. the minute it becomes reality the excitement fades - and then where would you be? Looking for another job, probably.
    You don't say if this woman is attached or not either - if she's married with kids, for example, do you really want to get involved and risk ruining people's lives?

    Take a read of this article about relationships at work and think it through carefully before making a move.
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    Make sure you have another job lined up 1st and then ask her . If she says yes , turn down the new job , if she says no , quit . :confused:
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    personally i think this could be a fantasy that you may want to keep a fantasy. This could Danger all work prospects you may have now and in the future. is the woman married? or is she single? have you asked around the office to see if they know anything about her
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    I strongly believe that most fantasies should just stay as fantasies. Cos when you start acting fantasies out, they turn out to be nothing like what you thought they would, and you end up disappointed.
    Plus in your case, your job may be in danger too.
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    Blairx0 wrote:
    That could be werid. My boss came on to me and I had a boyfriend at the time and was very turned off by it and things were never the same. I would say the best way to go about things is flirt with her and then depending on her response go from there. If she doesn't react favorably then i don't thinks would go much further. Your first concern should be your job .. vuz it was horrbile when my boss did that to me i left and we don't speak anymore

    Agree here if your serious about it try some harmless flirting but read the signs!

    And its sounds like more of an obsession now than a crush?Which wont work out, sounds bit fetish like almost going ajcking eon of about it.
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    creamedjeans wrote:
    I have had relationships with women I work with in the past. Everything worked out fine. The only difference is this woman is my boss. Of course, I would have to tread more carefully. I would like to let her know I am interested but not so obviously that it would put my job in jeapardy. I want her to make the move that finalizes the sexual relationship.

    If you're not bothered about your job, or you won't be embarrassed if she doesn't go for it, then you've got fuck all to lose.

    Is she married? Have you flirted with her?
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    She is divorced and has a daughter. I feel that my age may make more of a difference than our work relationship when it comes down to it. I am not obsessed with her. I am sorry if it sounded that way. It might be a little bit "fetishy" but I wouldn't say I have an older woman or Domme fetish. It is a turn on but not something I am all hung up about...

    As for jacking off in the men's room, the lady just drives me crazy. She is so damn sexy that it is hard not to fantasize about her at work. I do my best to not let it distract me and find that a quick stroke job in the bathroom helps me out considerably.

    I know...I'm a bit of a freak...

    Anyway, I told her that she looked really attractive today. She seemed a little shocked that I said anything but recovered quickly. She wasn't embarassed or anything. In fact, she seemed slightly flattered after the initial shock. As I said, she is a bit older than me and is just not use to me saying things like that to her. I have mentioned things like her hair, etc. but nothing about her body.
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    creamedjeans wrote:
    Anyway, I told her that she looked really attractive today. She seemed a little shocked that I said anything but recovered quickly. She wasn't embarassed or anything. In fact, she seemed slightly flattered after the initial shock.
    Bloody hell, that's extreme. One of my bosses is a woman. A group of work colleagues were out one night, I said to her "you look amazing in that top". She blushed, I blushed. I'm not making that mistake again!

    As for masturbating in the toilets about her, this is worrying. We've all heard about shagging the boss, but this is ridicilous. Ever thought of going to another job? You could pursue her then without any perceptible conflict of interest. ;)
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    She invited me to go swim in her pool this saturday. :yippe:
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    creamedjeans wrote:
    She invited me to go swim in her pool this saturday. :yippe:

    Winner!
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    I am pretty hot for it. I will let you know what happens.
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    creamedjeans wrote:
    I am pretty hot for it. I will let you know what happens.

    Be careful. I had a bit of a snog with my slightly older male boss and it made everything so very awkward afterwards, despite the fact that we both wanted it at the time.
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    It rained this weekend. She called me and told me her daughter would be home so we would have to do it another time.
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    Damn I thought the 3 day no post was a sign on success, I guess that she her daughter was going to be out is a good sign :D
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    Ok. I was talking to my boss while my officemates were out this afternoon. She was looking real hot. She had just had her hair done so it was a light sandy blonde. Her toes were painted and she was all tan. Damn she is hot!

    Anyway, she invited me to her pool this weekend. Let's pray it doesn't rain. :naughty:
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    Well, it happened. I went to her house Friday evening and made my move. She was looking so hot in her bathing suit that I could hardly contain myself. I was at half chub the whole time and I knew she had to notice. I waited for the right moment in conversation and basically Itold her that I found her incredibly attractive. I said she was hot and that I had a bit of a crush on her. She enjoyed the compliments and was not at all embarassed. She laughed a little and told me that she was old enough to be my mother. I was a little embarassed...especially after that comment...but felt as if she was not turning me down but stating a fact..as if she was comptemplating what to do. So, I told her that she was just really hot and everything about her was a major turn on. I played it off as if I was complimenting her and that I thought nothing of saying these things. In other words, I wanted to be able to play the innocent card if she became offended. Anyway, she gave me this smile. It was one of those smiles that a woman gives a man and the man knows things are locked. She asked me to put lotion on her back....and well..things progressed.

    I basically told her that I really wanted to go down on her. She wasn't really keen on the idea at first but I told her that I loved to give oral and that she wouldn't have to reciprocate. She was more worried about the condition of her nether-regions than sucking my c*ck...I think..but that put her at ease. God she had a delicious p*ssy! It was trimmed a little but otherwise a nice full bush...dark in color and still good and wet. I ate her and jerked off. She came several times and I do believe she fell in love lol The day finished with a nice handjob as she made me cum on my belly.

    Dreams do come true!
    :yippe:
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    HAHA well done.
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    creamedjeans wrote:
    Well, it happened. I went to her house Friday evening and made my move. She was looking so hot in her bathing suit that I could hardly contain myself. I was at half chub the whole time and I knew she had to notice. I waited for the right moment in conversation and basically Itold her that I found her incredibly attractive. I said she was hot and that I had a bit of a crush on her. She enjoyed the compliments and was not at all embarassed. She laughed a little and told me that she was old enough to be my mother. I was a little embarassed...especially after that comment...but felt as if she was not turning me down but stating a fact..as if she was comptemplating what to do. So, I told her that she was just really hot and everything about her was a major turn on. I played it off as if I was complimenting her and that I thought nothing of saying these things. In other words, I wanted to be able to play the innocent card if she became offended. Anyway, she gave me this smile. It was one of those smiles that a woman gives a man and the man knows things are locked. She asked me to put lotion on her back....and well..things progressed.

    I basically told her that I really wanted to go down on her. She wasn't really keen on the idea at first but I told her that I loved to give oral and that she wouldn't have to reciprocate. She was more worried about the condition of her nether-regions than sucking my c*ck...I think..but that put her at ease. God she had a delicious p*ssy! It was trimmed a little but otherwise a nice full bush...dark in color and still good and wet. I ate her and jerked off. She came several times and I do believe she fell in love lol The day finished with a nice handjob as she made me cum on my belly.

    Dreams do come true!
    :yippe:

    :eek2: Seriously...what the...hell.
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    Wow!
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    groovechampion wrote:
    :eek2: Seriously...what the...hell.

    Yeah...

    It's stories like these that make me question reality and wonder if this is hell.
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    The older woman thing doesn't do much for me, but fair play to you, and you've got what you wanted. Good luck, and let's hope it doesn't end in tears. Enjoy. :thumb:
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    how was it going back to work?
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    wow ! good job - pun intended ! Next time your in her office drop your pen under her desk :naughty: ! Ever see that movie 'The Secretary ' with James Spader ? You should rent it !
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