It's a Small World, a Sugarbaby Story

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Qster

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Once upon a time, at a different city, I worked for the Frenchman; he is a fun guy to be with at the bar but you need to count your fingers after each handshake with him, he is vicious at business. He is actually not French but because he is fluent, that's my nickname for him. The Frenchman has a smoking hot wife, a total MILF, late 40s with a body that 20 year olds dream of. The rumour is that she loves to swing, I have heard of many stories about booze-filled orgies at his place in the country, complete with an indoor swimming pool (this fact is important later). Never had a swinger girlfriend myself so I can only imagine what their couple parties are like. On top of that, he cheats on his wife all the time when he is on the road; THAT, I had seen first hand.

Despite the fact that I hadn't worked for him for over 10 years, I still have many friends who work with him. One day, one of these friends received an notification from a notable sugarbaby site. In one of the teaser pictures, the sugarbaby has mouse ears etc, a little obscured but definitely familiar. Like any horny sugardaddy would do, he paid and gained access to the sugarbaby's secret album. Surprise surprise, the girl was posting in her bikini at the Frenchman's swimming pool. She also worked as a temp at the Frenchman's office a couple of summers ago; why not, she is the Frenchman's niece. My buddy messaged her and her asks are high but, like her aunt, she is smoking hot with many things to offer. Our little gang are having a great time chatting about what to do next; she would definitely recognize the Frenchman's employees at a date, but she has never met me. It will cost me a bit of money but I would be lying if I say I am not tempted; if only there is no pandemic and travelling is easy. I am seriously curious as to what the Frenchman would do if he finds out what his niece does for play money. Or would I even tell him? That is also one thing all of the Frenchman's employees are talking about, should one of them tell the Frenchman.

The irony of a swinging boozing cheating millionaire uncle having a smoking hot sugarbaby niece open for "business" has not eluded me. I have had a couple of sugarbaby arrangements before but nothing close to home like this. What would you guys do if you find out that your ex-boss's hot niece is working as a sugarbaby/escort/masseuse.

The moral of the story, it is a small world after all.
 
Something not too far off of your situation I've had to deal with myself. In this case it was the boss's daughter. She's in her 20's, has worked in the office off and on. One day I see her face on LL, along with a post on CAF about her. The tattoos on her shoulders confirm it's her even if I could have mistaken the face. Honestly, I didn't do anything when the ad was up; she took it down within a week. I did bring it up to her in person when we were alone, recommending that she edit out her tattoos and face in the future if she's going to put up the ad again if she didn't want to be recognized.
 
Once upon a time, at a different city, I worked for the Frenchman; he is a fun guy to be with at the bar but you need to count your fingers after each handshake with him, he is vicious at business. He is actually not French but because he is fluent, that's my nickname for him. The Frenchman has a smoking hot wife, a total MILF, late 40s with a body that 20 year olds dream of. The rumour is that she loves to swing, I have heard of many stories about booze-filled orgies at his place in the country, complete with an indoor swimming pool (this fact is important later). Never had a swinger girlfriend myself so I can only imagine what their couple parties are like. On top of that, he cheats on his wife all the time when he is on the road; THAT, I had seen first hand.

Despite the fact that I hadn't worked for him for over 10 years, I still have many friends who work with him. One day, one of these friends received an notification from a notable sugarbaby site. In one of the teaser pictures, the sugarbaby has mouse ears etc, a little obscured but definitely familiar. Like any horny sugardaddy would do, he paid and gained access to the sugarbaby's secret album. Surprise surprise, the girl was posting in her bikini at the Frenchman's swimming pool. She also worked as a temp at the Frenchman's office a couple of summers ago; why not, she is the Frenchman's niece. My buddy messaged her and her asks are high but, like her aunt, she is smoking hot with many things to offer. Our little gang are having a great time chatting about what to do next; she would definitely recognize the Frenchman's employees at a date, but she has never met me. It will cost me a bit of money but I would be lying if I say I am not tempted; if only there is no pandemic and travelling is easy. I am seriously curious as to what the Frenchman would do if he finds out what his niece does for play money. Or would I even tell him? That is also one thing all of the Frenchman's employees are talking about, should one of them tell the Frenchman.

The irony of a swinging boozing cheating millionaire uncle having a smoking hot sugarbaby niece open for "business" has not eluded me. I have had a couple of sugarbaby arrangements before but nothing close to home like this. What would you guys do if you find out that your ex-boss's hot niece is working as a sugarbaby/escort/masseuse.

The moral of the story, it is a small world after all.

I say, Just Go For It. Firstly, it's an ex-Boss' niece. Secondly, chances are this niece wants the excitement even more than money. A form of self-worth affirmation. I would be obliged to affirm it.


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Interesting story.

Back about 20 ish years ago my boss of a large company while we were slow would get me to pick up packages, run errands and even go to his house to clear snow on his driveway and sidewalk. On a couple occasions his daughter a very large breasted east Indian gal invited me in to warm up gave coffee etc.

As time passed and we got more familiar with talking she asked if I needed to have a shower after so much hard work. I obliged and to my surprise she joined me in the shower. The first time she tit fcked me next time blew me. And finally we went all the way. I certainly think she would have done it all to start but I was always saying that your father would kill me if I fcked you. So she would give me everything but. After the snow stopped cumming I stopped cumming as well. Boy those were the days.

Baller

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you shoulda kept on balling her...
:D
Interesting story.

Back about 20 ish years ago my boss of a large company while we were slow would get me to pick up packages, run errands and even go to his house to clear snow on his driveway and sidewalk. On a couple occasions his daughter a very large breasted east Indian gal invited me in to warm up gave coffee etc.

As time passed and we got more familiar with talking she asked if I needed to have a shower after so much hard work. I obliged and to my surprise she joined me in the shower. The first time she tit fcked me next time blew me. And finally we went all the way. I certainly think she would have done it all to start but I was always saying that your father would kill me if I fcked you. So she would give me everything but. After the snow stopped cumming I stopped cumming as well. Boy those were the days.

Baller

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Approaching sex workers in public is incredibly unprofessional, tacky and a violation of someone's boundaries.
Next time just dont.
This is something sex workers hate and often get black listed.
 
Dated a stripper turned escort turned drug pusher .
She screwed her doctor
She screwed her landlord
She screwed her boss
She screwed her pharmacist
She screwed her cousin
She screwed her home renovator
She screwed her FWB
 
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I dated a parttime stripper too, she was one of the sweetest graduate student I had ever met; I was an undergrad back then. She gave me plenty of warning that our relationship is temporary. As soon as she graduated, she literally packed up, left the country and was never seen again. Unfortunately for me, I think I was truly in love with her.

As for the Frenchman's niece, I think all of us came to the conclusion that it is not worth the effort or potential trouble to do anything. Just not worth it to get in trouble with the French mafia. If her family finds out, they will have to find out on their own. It is just that this world feels so small with the internet and social media these days.
 
I dated a parttime stripper too, she was one of the sweetest graduate student I had ever met; I was an undergrad back then. She gave me plenty of warning that our relationship is temporary. As soon as she graduated, she literally packed up, left the country and was never seen again. Unfortunately for me, I think I was truly in love with her.

As for the Frenchman's niece, I think all of us came to the conclusion that it is not worth the effort or potential trouble to do anything. Just not worth it to get in trouble with the French mafia. If her family finds out, they will have to find out on their own. It is just that this world feels so small with the internet and social media these days.

Kind of supprised how many girls put their face photos up on sugar sites, I've seen 1-2 faces I know IRL on these sites over the years. Obviously just booked those and moved on. I don't put my real face on the public pictures for the same reason.
 
I dated a parttime stripper too, she was one of the sweetest graduate student I had ever met; I was an undergrad back then. She gave me plenty of warning that our relationship is temporary. As soon as she graduated, she literally packed up, left the country and was never seen again. Unfortunately for me, I think I was truly in love with her.

As for the Frenchman's niece, I think all of us came to the conclusion that it is not worth the effort or potential trouble to do anything. Just not worth it to get in trouble with the French mafia. If her family finds out, they will have to find out on their own. It is just that this world feels so small with the internet and social media these days.
I've dated sex workers, and I've been in the Lifestyle for some time. On top of that, I've recognized a co worker's relative on LL, as she had helped out around the office on occasion. It was an ad that was up briefly, but as I recall she showed part of her face and left her tattoos unblurred. There's no need to bring drama into work, much less something that could ruin a career.
 
I dated a parttime stripper too, she was one of the sweetest graduate student I had ever met; I was an undergrad back then. She gave me plenty of warning that our relationship is temporary. As soon as she graduated, she literally packed up, left the country and was never seen again. Unfortunately for me, I think I was truly in love with her.

As for the Frenchman's niece, I think all of us came to the conclusion that it is not worth the effort or potential trouble to do anything. Just not worth it to get in trouble with the French mafia. If her family finds out, they will have to find out on their own. It is just that this world feels so small with the internet and social media these days.
Probably worth the effort if she is that hot.....but the yang is not worth the trouble. Don't need the stress, that if her family or friends find out and decide to make your life a living hell. Been there and done that, believe me it can turn your life upside down.
Fast forward to today, been tempted a few times but I walked knowing that if this goes sideways. No telling how it plays out. Tough sitting down after the fact wondering what if, but knowing I made the right decision. Especially difficult when a sexy married lady throws herself at you.
Done the swinging lifestyle off/on over the years. That can be exhausting being a single guy to make connections but great when works out.
 
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