Three Former Sex-Trade Workers Share The Strangest Requests They Ever Received From Men.

I interviewed three former sex-trade workers, asking them to tell me the weirdest, wildest, even creepiest things they were asked to do during their time in the industry. They didn’t disappoint. I went into the interview expecting our talk to be exactly like when my girlfriends and I get together to talk about gossip and hookups. I was so very wrong. Here are three jaw dropping stories and a little advice from the femme fatale.

  • All names have been changed to former trade names so as to not reveal their identity.
  1. Playing Dress Up 

I sit next to Crystal on her couch and feel just a little inadequate. She is tall, thin and gorgeous, and answers the questions I ask, laughing the entire time.

Can you tell me about the strangest request you have ever received from a man?  

Sure, so a guy asking you to dress up is a normal thing in this line of work. Most of the time they want to play out basic fantasies like nurse, teacher, cheerleader, maid. Those kinds of requests just come with the job. A few times I was asked to wear a animal costume. Nothing major it was just some cat ears and a tail, that was a little strange but it still didn’t compare to one gentleman that came in.

What did he have you wear?  

He came in with a black duffle bag and put it on the bed. I used to go by another name but he asked me if he could call me Sarah. I said sure, and then he started pulling items out of the bag. He’d say, “Okay Sarah now go put this on”. It was just everyday clothing you would see a woman wear out on the street, right down to the bra and underwear…very plain. In my mind, as bad as it might sound, it’s my job and I was getting paid, so I really didn’t care. He obviously wanted me to be someone very specific, he had even brought a wig and perfume.

Do guys want you to be other people often? 

It depends. I find most guys really do just want the company. There’s definitely role-play but being asked to embody “Sarah” was a whole new thing.

What is one piece of advice you would give women out there when it comes to sex and dating?  

I would tell them women have a lot more power within the relationship than men want them to believe. Own it, and don’t put up with any form of mistreatment. It’s all you baby girl.


2. All About The Boots 

I met with Jade just outside her up-town apartment and she invited me in for tea. She looked like your average 20-something, cute, innocent and stylish, which made what she had to share with me all the more surprising.

What is the one thing you were asked to do during your time in the sex-industry that shocked you the most? 

I was with one man who was really into watching me strip and so every time I would be with him I knew I would have to give him a show. It would just be a strip tease with different forms of lingerie and then we would have sex. The last time I was with him I had just removed my lingerie when he said, “leave the boots on”. I had these great leather high-heeled boots, they were my favorite. I used to wear them everywhere. Anyway, he had me lay on my stomach and stick one foot up in the air, and then he got on top of me and proceeded to stick the heel of my boot up his butt. He basically had sex with my boots and got off…I never wore them again after that.

Did you know he was into that kind of thing? 

No, not at all, it just happened. It was very strange but I mean…all in a days work.

Do you have any advice for women your age that are dating or sexually active?

When a guy treats you like he doesn’t care, believe him. Don’t stick around waiting for a man to change because you’ll only be hurting yourself. The same goes if a guy treats you well, know your own worth and be able to accept someone who treats you with kindness and respect…and leaves your shoes alone.

3. Shoe Strings Aren’t Just For Tying Shoes

Serenity met me in a small cafe’ and we talked about men over coffee. It was so normal at first that when she began telling me her wildest request I had to look around to see if there were any other listeners. It was so outside of anything I had heard before, she had my full attention.

Tell me about the weirdest request you have received while working. 

Um, the weirdest thing that I have ever had asked of me or even to take part in, would have to be when a guy asked me to take my shoe lace out of my shoe and wrap it around his balls. When I did he kept saying, “make it tighter”. I remember wrapping it so tight that I was afraid I was cutting off any circulation, they were really red. That’s not the worst of it though. Once I had tied them up tight enough he asked me to smack them really hard. He wanted me to beat the crap out of his balls. It was by far the weirdest thing ever; I don’t know what he got out of it.

After hearing her answer I was in shock and thankful none of my boyfriends had ever asked me to reenact Rocky on his genitals.

Can you share some advice for women who are dating currently? 

Be safe, that’s number one. Always meet a guy in a public area; especially if you met on a dating app. Tell one of your friends where you are and if you feel uncomfortable leave. Always listen to your gut instinct…and of course use protection.

After each interview I thanked the women for their time and for sharing their stories from another side of life. I would be lying if I said I wasn’t fascinated and at the same time grateful for my own sex life.


Carlee Lloyd

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