Secretary sex

[Yarris]

For many years I had the most wonderful secretary/PA: super competent at her job. fabulous legs and butt, attractive if not conventionally beautiful, gorgeous medium sized breasts which I would often view as she leant over my desk when wearing a V necked and mini skirted suit or through a semi sheer blouse and, last but not least, a wonderful witty and insightful personality. I loved and desired her dearly and so wanted to fuck her. But I never did. I know she was very fond of me but I believe, not in a sexual way, and despite my desires I believed that I had far more to lose and the potential for huge compications. The nearest I got was a full body hug lasting at least 30 seconds when my wife and I visited her at her home the day after her husband died suddenly due to medical negligence..

Do I regret failing to make a move at any point? Not a bit, I have the warmest memories of her and still have the ability to fantasize with dick in hand. Twenty odd years on I still see her occasionally when she is clearly as pleased to see me as I am to see her.

It would be interesting to hear of others who have faced these sorts of relationships and what they did about them. For those who developed a sexual relationship, how did it pan out and, looking back was it worth it?

 

[maxlow999]

I had a very similar desire to fuck my secretary about 20 years ago. She always turned me on but our relationship was purely platonic.

My last secretary had the same effect on me. She had a luscious ass and she knew how to strut just right.
One Saturday, I texted her asking her if she would like to go for a walk with m. She declined and ended up quitting 2 weeks later. She said that I made her uncomfortable. She cut off all contact with me.
Then 2 weeks ago, she texted me and we began to chat a bit

WTF is up with that?

 

[mikendel]

I have had sex with 4 bosses. It started with hubby telling me it must be hard for guys you work with to have to look at you everyday because of my outfits. He told me that they jack off thinking about me in the men’s room at work. I told him he was crazy but the thought of it made me wet. He would encourage me to dress extra sexy and flirt a little and see what happens. I did and they started flirting and I would flirt back. Finally my boss asked me to come in at the end of the day and I text hubby and told him today might be the day. He asked if I was ready and I replied very ready. The boss talked about work at first then switched to needing advice about his home life. He said his wife wasn’t into sex anymore but he didn’t want to get divorced. I said that must be tough because sex is important to a man. I finally just said well I can help you with the sex part. I was a little nervous but walk over to him and sat on his lap. He went straight for my boobs and I knew then hubby was right. He didn’t last long but it was fun and exciting. Had many more late meetings after that. Since then I have added 3 bosses and several co workers and clients.

 

[OldFred65]

Back in my working days we had a secretary that always traveled with the boss and I when we attended meeting, conferences, etc. We always got a room with two beds and never a separate room for her, she just alternated sleeping with one of us each night. Our wives and her husband all knew about it but didn't care. probably because her husband was alternating fucking our wives each night while we were away.

 

[EdEc]

I had a very similar desire to fuck my secretary about 20 years ago. She always turned me on but our relationship was purely platonic.

My last secretary had the same effect on me. She had a luscious ass and she knew how to strut just right.
One Saturday, I texted her asking her if she would like to go for a walk with m. She declined and ended up quitting 2 weeks later. She said that I made her uncomfortable. She cut off all contact with me.
Then 2 weeks ago, she texted me and we began to chat a bit

WTF is up with that?

Perhaps she's had a change in her personal life and is looking for someone to spend intimate time with.

 

[maxlow999]

Perhaps she's had a change in her personal life and is looking for someone to spend intimate time with.

It's possible. I'm not sure how to approach any opportunity that may be there since she rebuffed me last year

 

[meflash]

I have had sex with 4 bosses. It started with hubby telling me it must be hard for guys you work with to have to look at you everyday because of my outfits. He told me that they jack off thinking about me in the men’s room at work. I told him he was crazy but the thought of it made me wet. He would encourage me to dress extra sexy and flirt a little and see what happens. I did and they started flirting and I would flirt back. Finally my boss asked me to come in at the end of the day and I text hubby and told him today might be the day. He asked if I was ready and I replied very ready. The boss talked about work at first then switched to needing advice about his home life. He said his wife wasn’t into sex anymore but he didn’t want to get divorced. I said that must be tough because sex is important to a man. I finally just said well I can help you with the sex part. I was a little nervous but walk over to him and sat on his lap. He went straight for my boobs and I knew then hubby was right. He didn’t last long but it was fun and exciting. Had many more late meetings after that. Since then I have added 3 bosses and several co workers and clients.

WOW!! a true HOT WIFE!!

 

[txfuncouple]

I have had sex with 4 bosses. It started with hubby telling me it must be hard for guys you work with to have to look at you everyday because of my outfits. He told me that they jack off thinking about me in the men’s room at work. I told him he was crazy but the thought of it made me wet. He would encourage me to dress extra sexy and flirt a little and see what happens. I did and they started flirting and I would flirt back. Finally my boss asked me to come in at the end of the day and I text hubby and told him today might be the day. He asked if I was ready and I replied very ready. The boss talked about work at first then switched to needing advice about his home life. He said his wife wasn’t into sex anymore but he didn’t want to get divorced. I said that must be tough because sex is important to a man. I finally just said well I can help you with the sex part. I was a little nervous but walk over to him and sat on his lap. He went straight for my boobs and I knew then hubby was right. He didn’t last long but it was fun and exciting. Had many more late meetings after that. Since then I have added 3 bosses and several co workers and clients.

Wish my wife would do this. Her riding my face as I licked her clean and she told me about what was going on would be hot.

 

[Shi_One81]

It literally just hit me - I’m going to be sort of a secretary in my new job, let the games begin!!!

 

[haventdonethat]

I was the PA.
Unexpectedly brought in from the warehouse and told I was the PA to assistant manager of the office (a male). My cubicle was across the aisle from a recent widow, six or seven years my senior, two steps above me in the chain of command. Good morning was all we spoke.
A few months later I was told I was her vacation relief. After an hour or two with her getting up to speed on her job, I knew it was bad news. I knew she also knew.
After her vacation we had the occasional lunch together. Then drinks after work.
Then I went to her house. There was glorious sex.

It was love. And I mean R E A L love. For both of us.

People in the office suspected. If the manager knew, we could have both been fired.
It ruined my first marriage.
Eventually she could not take the sham any longer and quit her job as an easy way to end the affair.
I was crushed.

So, to me, secretary sex is something I would never contemplate again. And sometimes wish it had never happened.

 

[AsiaRoamer]

Edited

 

[Yarris]

I was the PA.
Unexpectedly brought in from the warehouse and told I was the PA to assistant manager of the office (a male). My cubicle was across the aisle from a recent widow, six or seven years my senior, two steps above me in the chain of command. Good morning was all we spoke.
A few months later I was told I was her vacation relief. After an hour or two with her getting up to speed on her job, I knew it was bad news. I knew she also knew.
After her vacation we had the occasional lunch together. Then drinks after work.
Then I went to her house. There was glorious sex.

It was love. And I mean R E A L love. For both of us.

People in the office suspected. If the manager knew, we could have both been fired.
It ruined my first marriage.
Eventually she could not take the sham any longer and quit her job as an easy way to end the affair.
I was crushed.

So, to me, secretary sex is something I would never contemplate again. And sometimes wish it had never happened.

I fear that sort of outcome is all too common. Despite, throughout my working life, serially falling in love with women I have worked with i have remained happily married. There have been periods of agony but we are still together and tell each other we love each other (and mean it) at least every day. So my infidelity has remained in my head and hand. She had a brief afair but couldn't handle the guilt and confessed. I forgave her, not least because it was my neglect that led to it happening. Hope you are happy now.

 

[Yarris]

Years ago i used to see a girl as a fb who was a junior PA to a guy at a big bank, often when I picked her up from work and she gave me a quick hello kiss before we drove away I would be able to taste her bosses cum on her tongue and in her mouth. A few times as we got onto the highway as I changed into top gear she took my hand and out it up her skirt or dress between her spread legs and i'd be able to feel her bosses cum on her thighs and oozing out of her pussy still.

That's HOT! Lucky you.

 

[Funnbrandy]

Secretary

Been tempted before...but other than the odd client I've managed to avoid it, drama is bad enough but drama at work, rarely does it turn out good! Lol

 

[AngelaBaby]

Paralegal

I am a Paralegal and not a Secretary, but I had sex with partners and other attorneys in the office. Spending so much time with them there is attractions and it just need the right time and right mood.

We flirt around and sometimes they *accident" bump into me or rub against me. But having sex at work or doing travel is always hot. Its like a taboo.

 

[Crownvic]

I am not Paralegal and not a Secretary, but I had sex with partners and other attorneys in the office. Spending so much time with them there is attractions and it just need the right time and right mood.

We flirt around and sometimes they *accident" bump into me or rub against me. But having sex at work or doing travel is always hot. Its like a taboo.

It can be edgey...but it is so exciting....to me it was worth it...

 

[LupusDei]

For a short while I worked for a guy whose money apparently had legs in Russian mob, or at least the image he maintained was one of a nicely dangerous thug. It was no secret he had four women on parallel, it was part of his image.

One of the girls he used as office decoration (two others worked for him in limited capacity, but kept lower profile and much more professional appearances). She was gorgeous in a very pretty and very very cute way, very sweet, very helpful to anyone generally, and walking sex. She didn't even needed to dress provocatively, even in a classic business costume it was impossible to look at her and not get hard. The only flaw, if that's a flaw for such a girl, she was unbelievably stupid. I don't know, I even suspect wasn't it just an masterful act, because it's seemingly impossible to be that stupid and remain functional.

The best joke I have no way to tell here because it involves technical slang in Latvian and Russian besides badly transplanted English and other potentially lengthy explanations for the full context, but the short was, she once refused to accept papers from a tech guy because the only interpretation she apparently knew of the phrase he had used for describing cable installation was that of a sex act. The guy knew none better, and was actually in the right, and then he tried to describe what he had done in detail, what only confused the girl further. The discussion grew in volume quickly, and the genius (but utterly mean Russian nazi) marketing guy come out and went on a humourous drivel on how it is impossible to not talk about sex in Latvian. It's sort of true, a lot technical slang just as anything else has subtle and not so subtle sexual innuendos in Latvian, just a curse of ancient language, especially in hands of true artist.

Well, no explicit sex in that episode, but that's the air there was around that girl and it was rumored she's easily available for any asker for the relatively little price of getting beaten up by the boss, all part of the show.

 

[shmily]

in the past I have had sex with a few of my "Bosses".
Once working at a bike shop, I was his 3rd. He was married, had a girlfriend on the side and I worked for him at the shop. I knew about them, they didn't know about me. It was actually accidental the first time it happened. We had worked late, the other guys had left the shop, I was still cleaning up the shop, he came in from the office and was complaining of a back ache. I offered to give him a massage. He pulled my van (it had a bed in the back) into the shop and shut the doors down. I had him take his shirt off and began his massage. That was the first time, it didn't happen often, but as he explained I was safe - he could escape the wife & GF.

Not sure what started another boss. He was older, attractive. He hired me on faith, I was just getting back to work after being off for 2 years after the birth of my son. He divorced during the first year of me working for him. I worked for him about 5 years, even after we quit - "dating" - he wanted to marry and talked of sending my son off to boarding school. I said no - he accepted that and I did work for him another few years until he decided to retire and closed the business.

 

[AAnderssen]

A sexy as a secretary can get!
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