What’s the strangest sex request a hooker ever heard?

When I see math problems I automatically think of my work in the sex industry. I had a client who was a psychologist living a double life. He catered to addicts because he was one himself. Usually people with troubled backgrounds say they want to help others follow in their overcoming footsteps Not him. He wanted clients who could get him dope, inject him (seriously, true story), turn tricks with him, or serve as debt collectors. Every client had to participate in his game, help him get that next high. The threat of him causing a patient to return to prison due to a bad report to a probation officer from him was real but unspoken. I was not a person prone to being intimidated by others, but even I felt vulnerable. I understood why there are rules against people in power forming relationships with subordinates.


He knew I was smart and complimented me when he said I was nearly intelligent enough to comprehend his writing. He got off on showing me reports that he wrote to parole officers about his patients–for his amusement. He would write, “patient relapsed today,” but wouldn’t say the person relapsed with him. Those reports were like trophies he kept to relive the victimization with some tangible reminder. I know about psychopaths and their souvenirs from watching Forensic Files.


He find my perceived intelligence appealing in his tole as a trick. I saw him once a week and each time he had something new for me. He liked to watch me and whisper encouragement in my ear while I sat at his computer…and took I.Q. tests. A different type each week to measure different abilities. He wanted to see if I maintained my scores through my using.A sample question is

A is to 1


C is to 3


E is to ?

When I chose the correct answer and marked the proper multiple choice selection, he loved it. “Five! Yes! The answer is five!” he would cry in delight as his hand worked below his belt. After he always whispered,

You are so…so… smart. And cheap, too. I’m a lucky guy.

I liked the visits. I always enjoyed praise, even in the form of backhanded compliments. I also liked getting high during the date rather than waiting til after. I never told guys I was a user if they didn’t know. Drug use freaked out normal people. And the guys paid less for goods even more damaged than they thought.


He is dead now. Suicide by hanging I heard. I also heard overdose. Who knows? Revenge killing perhaps. Maybe he sent the wrong person back to prison by getting high with him then ratting him out.




Secret Keeper/Secret Teller
I tell hidden personal truths while maintaining perfect confidentiality so you may see secrets you share!

Clients confided in the Ivy League educated hooker–me. Why? I was smart enough to understand anything they shared. Equally important, my status as social outcast meant even if I told their secrets few would listen to me. Of those who listen, few of that small number would believe me.  Almost no one would care what a woman of ill repute had to say. I understood their secrets and kept those precious gifts safe since I couldn’t tell on them even if I wanted to!  Of course, I did not want to unlock the vault and violate trust.  I said nothing and remembered what I heard.  learned that many men lived in shame BC of the erroneous belief that they were different than others. They did not know that their confessions had been echoed by others. I had a friend who lived his whole life never fully accepting himself BC he thought he was uniquely weird. He was wrong. His alienation was unnecessary pain. If he knew what I knew his life could have been happier. The only way I can form a community out of shared secrets, mostly sexual, but not entirely, is to tell the secrets while maintaining perfect confidentiality. My blog tells of my experiences with the emotions and musings of people in the sex industry now, and in my past (up to 15 years ago). The purpose of every post is to comfort to at least one person with the assurance that someone else felt/thought the same way. The feelings and thoughts are true, the people and events combine interviews, personal experience, and fiction. You cannot meet Caroleena bc she does not exist beyond this site. But she speaks truth. Sometimes your truth. You are not alone with your secrets. Come, let me show you.