My fascination began with escorts known back then as street walkers during a time when the internet was in its infancy.” Written by Jay Nelson

I’ve been involved in the hobby for over 15 years and I will admit it has been an enjoyable experience. It all started when I moved to Washington DC for my first real job. I had no immediate family, hardly knew anyone and was single, so why not? When dating slowed or strip clubs left me unsatisfied, I’d cruise the track. It was the excitement, as this social taboo gave me quite a rush. As the internet progressed and internet escorting became the norm, I thought, do I want to continue hobbying? One day I’ll want to settle down (or so I thought back then) and I don’t want my escapades to come back and haunt me. Already, I recognized that whatever goes online stays online. Forever.

Til this day, I apply the same rules of thumb whenever I choose to see a companion. While these rules may not work for everyone they’re a good set of basic guidelines to enhance your enjoyment with the wonderful companions you will meet.


Don’t get caught up in the fantasy world of hobbying. Too many gents get lost in this existence, paying penance with their jobs, wives, families and lives. I have a very busy life outside of the hobby. At times, my schedule does not allow me to meet with an escort but I maintain that focus. Keep a healthy perspective by remembering that the hobby serves only as an indulgence away from work or other stress factors in life.


Set some principles and stick with them. If you devise a budget in an effort to organize your finances but don’t stick with it, what’s the point? The same thing is true here. If you make rules about how you’re going to play, stick with them. Discipline is the key to total enjoyment.


After you get your feet wet, decide what you want and set some realistic goals:

  • Do you want to see a lady once a week
  • Every other day?
  • Twice a month?

Think about these things as they will give you an idea on how to plan and prepare for your hobbying. Of course, if you’re independently wealthy this need not apply but I know number of guys who have nearly bankrupted themselves due to lack of planning.


Lack of preparation can land you in a precarious situation. You may think it’s okay to stretch your lunch hour to two or three until you return to find your boss suspiciously looking for you. Or, your significant other drops by to surprise you and there you are, wreaking of sex, or better yet, radiating the remnants of floral perfume that she recognizes is not your scent.


When dating, privacy is key and getting intimate can present a delicate balance. While ladies need to be able to trust you with their safety discretion is reciprocal. Mind your tongue when sharing your endeavors as loose lips will sink ships.

Written by Jay Nelson, Hobbyist & Guest Author for Geisha Diaries