Office stuff?????

Vman55

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I own a small company. My top assistant and office manager has worked with me 20 years and she has been divorced for 19 years. Im 58 married and she just turned 60. We are basically family. Over the years you can imagine the conversations we have wondered into. I have seen many times with other owners that this has gotten their ass in a heap of trouble when it lead to having sex. She is living with her 90 year old aunt and has NO life. She reads alot and her outlet into the public is me. She refuses to date anyone because she does not want drama. She hasnt been touched in over 2 years. She has told me she wishes to just get laid sometimes and thats it. This is a small town and the only single guys around she would not touch in a thousand years.

On either side of this fence what would you do?
 
I own a small company. My top assistant and office manager has worked with me 20 years and she has been divorced for 19 years. Im 58 married and she just turned 60. We are basically family. Over the years you can imagine the conversations we have wondered into. I have seen many times with other owners that this has gotten their ass in a heap of trouble when it lead to having sex. She is living with her 90 year old aunt and has NO life. She reads alot and her outlet into the public is me. She refuses to date anyone because she does not want drama. She hasnt been touched in over 2 years. She has told me she wishes to just get laid sometimes and thats it. This is a small town and the only single guys around she would not touch in a thousand years.

On either side of this fence what would you do?

She has told you she wants to fuck, you will not get a better invitation. Do I see a business trip coming up?
 
If you're both open to the idea and are honest as to what this is, it simply fulfilling each other's needs without the risk of either of you getting overly emotionally involved then I see no problem.

The opening is certainly there and it seems like she trusts you, so I would take the opportunity...
 
In the past we discussed it and she said she didnt know if she could do it because Im married and she knows the wife.
 
In the past we discussed it and she said she didnt know if she could do it because Im married and she knows the wife.

Will only work if you're both 100% on board, otherwise could cause problems afterwards...
 
Im not sure.........I do know that she is extremely private and I believe she would like tp but she is afraid to try and I dont push here.
 
It's your wife that needs to come onboard...

Will only work if you're both 100% on board, otherwise could cause problems afterwards...
In a most non-threatening way, mention in passing as part of sharing your day with her, that your admin dropped another broad hint about getting laid.

You can mention that this isn't the first time she's flirted, but now she seems serious enough that you wanted to share this with your wife for your wife's information/perspective.

Without pushing, tell your spouse that you can see where the admin is coming from. Living with just her old aunt, no social life, no local men available/acceptable, you're a known quantity known for a long time, no drama desired, and that the admin regrets that you're married.

Avoid even the slightest hint that you're asking permission. You can see that your admin is lonely, and wonder if your wife might reach out to her.

If you wife asks you if you're trying to set something up or get her permission, reassure her that you're loyal, trustworthy, and have never gone where she has told you not to go. (I trust you can say that truthfully...)

Your goal is just for them to learn about each other. If they click as friends, fine; if not, that's OK too.

With the groundwork laid so your wife has personally learned where your admin is coming from, you can assess the situation to see if your spouse has enough compassion to share.

The best outcome is that each of the three of you independently decide contact with your admin is viable. Next are the tricky negotiations where your wife decides what will happen -- Three way, Clothes never off, Date night, Only out of town, Don't ask/don't tell; PIV/no PIV, Overnight, ...

Should all the stars align, you can tell you admin that your spouse would allow ... to happen, and they should talk.

Good Luck!
 
I own a small company. My top assistant and office manager has worked with me 20 years and she has been divorced for 19 years. Im 58 married and she just turned 60. We are basically family. Over the years you can imagine the conversations we have wondered into. I have seen many times with other owners that this has gotten their ass in a heap of trouble when it lead to having sex. She is living with her 90 year old aunt and has NO life. She reads alot and her outlet into the public is me. She refuses to date anyone because she does not want drama. She hasnt been touched in over 2 years. She has told me she wishes to just get laid sometimes and thats it. This is a small town and the only single guys around she would not touch in a thousand years.

On either side of this fence what would you do?

Do you see this as doing a favor to her or are you attracted to her. Don't even think of her if you are ever going to have the thought that you came into her life because she was lonely. She'll ultimately resent you for it, even if you don't voice the sentiment.

Another thing she's been divorced for 19 years and only been celibate for two. That clearly indicates that she doesn't see you in that light. She may have mentioned the absence of an active sex life to you because she's comfortable with you.

from what you have shared I don't see her showing any interest in you.
 
hey

I own a small company. My top assistant and office manager has worked with me 20 years and she has been divorced for 19 years. Im 58 married and she just turned 60. We are basically family. Over the years you can imagine the conversations we have wondered into. I have seen many times with other owners that this has gotten their ass in a heap of trouble when it lead to having sex. She is living with her 90 year old aunt and has NO life. She reads alot and her outlet into the public is me. She refuses to date anyone because she does not want drama. She hasnt been touched in over 2 years. She has told me she wishes to just get laid sometimes and thats it. This is a small town and the only single guys around she would not touch in a thousand years.

On either side of this fence what would you do?

If I were.you I would tell her about THIS guy in the Detroit area that is willing to travel within reason to get a taste of her lust and leave her thoroughly satisfied with ZERO drama.
 
Danger! Danger!

sexual harassment!

You seem to have more to loose than she does.

I know you are going to tell me that she "isn't like that" and "would never" but things and people change after time.

Just beware!!!

P.S. I hope you two become FWB's and enjoy a great symbiosis with no repercussions! Good Luck!
 
Do you see this as doing a favor to her or are you attracted to her. Don't even think of her if you are ever going to have the thought that you came into her life because she was lonely. She'll ultimately resent you for it, even if you don't voice the sentiment.

Another thing she's been divorced for 19 years and only been celibate for two. That clearly indicates that she doesn't see you in that light. She may have mentioned the absence of an active sex life to you because she's comfortable with you.

from what you have shared I don't see her showing any interest in you.

Good point
 
Danger! Danger!

sexual harassment!

You seem to have more to loose than she does.

I know you are going to tell me that she "isn't like that" and "would never" but things and people change after time.

Just beware!!!

P.S. I hope you two become FWB's and enjoy a great symbiosis with no repercussions! Good Luck!

Maybe, maybe not. We have worked together for 20 years.
 
If I were.you I would tell her about THIS guy in the Detroit area that is willing to travel within reason to get a taste of her lust and leave her thoroughly satisfied with ZERO drama.

LOL. Thats a long ways to go
 
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