Humorous Hobby Experiences -- Have You Had One?

I've had several, but this one's my best:

About 20 years ago, I formed a couple of partnerships for the purpose of investing in properties owned by the RTC and by REO departments of busted banks and S&Ls (of which there were many in the late '80s). In connection with that, I had the occasion to meet with the CEO of a small, closely-held company in Dallas who was eager to invest in distressed properties. I'll call him Jerry (not his real name).

Jerry had a very attractive thirtyish administrative assistant whom I'll refer to as Deborah. She and I had a couple of friendly chats when I was waiting to meet with Jerry, who tended to be tied up with phone calls and late-running meetings. We talked about local events, movies, restaurants, etc. She even told me about a place she was dying to try. I thought she was trying to give me a little "hint, hint", but wasn't sure -- and, in any event, just to make both of us more comfortable, I wanted to wait until my series of meetings with her boss were over before asking her out.

About the time I had my last meeting with Jerry, he told me that Deborah had asked whether I was married. She also told him she thought I was very good-looking.

[Short intermission to allow any ladies who have actually met me to stop laughing.]

Having been given some obvious encouragement, I decided to call this very attractive and personable young lady and ask her out. As I recall, it was a Tuesday afternoon around 4 when I placed the call. I intended to ask whether she would care to try out the previously-mentioned restaurant Thursday night.

The person who answered the phone told me Deborah was on another line and would call me back within a few minutes. When she did so, I was on the phone and my assistant took a message. By the time I returned Deborah's return of my initial call, she had left for the day.

In the meantime, I was an occasional customer of what might be described as an upscale UTR agency. The owner had recently told me about a new girl she described as gorgeous, 32, 5' 6", 120 lbs., brunette, all-natural C-cup, well-dressed, personable, and intelligent. Sounds perfect, I thought. So I made an appointment for 9 p.m. that Tuesday night; the very day I had tried to get in touch with Deborah.

Finally the clock struck 9.

Guess who showed up!

Needless to say, we were both rather surprised. Deborah almost looked like she was ready to faint. After a minute, she asked whether I wanted to go through with the appointment. I said, "Of course!"

I had an absolutely great time and saw her many times over the next year or two.
atlcomedy's Avatar
Great story...I recently started a thread called something like "close calls" or something like that...

I guess the difference between a "close call" (as in "oh shit") and a good laugh is time. Twenty years in the rearview mirror make us see a lot of things differently.
CajunGent's Avatar
Oh yes. About two years ago, my company ran an advertisement for an opening as my private secretary. She did not know my real name, and I certantly did not know hers, but when I entered the conference room for the job interview, I think that both of our jaws dropped to the floor.

A very interesting interview, tactifully handled by both of us.
atlcomedy's Avatar
Oh yes. About two years ago, my company ran an advertisement for an opening as my private secretary. She did not know my real name, and I certantly did not know hers, but when I entered the conference room for the job interview, I think that both of our jaws dropped to the floor.

A very interesting interview, tactifully handled by both of us. Originally Posted by CajunGent
Was she looking for a legit administrative position?

A lot of times "private secretary" and "personal assistant" (for "dynamic entrepreneur...") etc. are often code words for "ISO of Sugar Baby"
Oh yes. About two years ago, my company ran an advertisement for an opening as my private secretary. She did not know my real name, and I certantly did not know hers, but when I entered the conference room for the job interview, I think that both of our jaws dropped to the floor.

A very interesting interview, tactifully handled by both of us. Originally Posted by CajunGent
But...you didn't says whether or not she got the job!!!
CajunGent's Avatar
Altcomedy, she was looking for employement as a secretary/administrative asst.
  • Suzel
  • 02-02-2010, 02:08 AM
There is a guy on craigslist adult jobs/industry that keeps asking for this. I'm sure he hasn't found one because he says

she has to do all this work, know all of these computer applications, be on time, work just like everyone else and play with him as well.

For $20/hr 8 hours a day.

UM LOL?

I feel like writing him and saying "let me get this straight. I will come in and do a monotonous boring secretary job for 8 hours and then I have to "play" with you all for $160/day.

WOW. $160 would not even cover an hour session with most women.




A lot of times "private secretary" and "personal assistant" (for "dynamic entrepreneur...") etc. are often code words for "ISO of Sugar Baby"[/QUOTE]