Amateur Threesomes vs Professional Threesomes

By Kendra Holliday | May 6, 2022

The other day, a friend I’ve known for years texted me out of the blue:

“Hi Kendra! After years of celibacy, I’m finally having sex again! He’s amazing. We want to experience many things together, can you give me advice on hiring a sex worker for a threesome?”

Pay attention.

I was so excited for my friend! I let her know about these sites they could explore together, as well as searching twitter using keywords, such as #STL #GFE #datestl, (be sure and click on “latest” tab at the top):

Eros.com  

https://www.eroticmonkey.ch/ 

https://skipthegames.com/ 

https://www.escortdirectory.com/

https://privatedelights.ch/

https://www.theeroticreview.com/

https://tryst.link/us/escorts 

I told her that if a couple is looking to hire a sex worker, it’s better for the woman to initiate contact, as that shows the worker she’s involved in the process and not being “dragged along.” I advised her to read the website instructions, and expect to be screened and pay a deposit.

They should think about what kind of experience they wanted – did they want the man to be the King in the middle? Did they want her to be able to explore her bisexuality? After all, if they’re paying for an experience, they should try ensuring everyone is on the same page.

They had a lot of fun exploring the sites, but later she came back to me and asked, “Would you be willing to play with us?” She felt safe and trusted me.

I said YES, I’d be honored!

Later that week, my friend and her new man came over. My friend is about my age, and this man was at least 10 years younger, very sexy and sensual. My friend was so giddy and nervous, glowing over her new beau and resurrected sex life.

I asked, “Is this your first threesome?”

They said no, they actually had a threesome the night before, with an acquaintance of theirs. I asked, “How was it?”

They said it was mostly hot, but sometimes awkward, and ended on a sour note. I didn’t get too many details, but it sounds like they hooked up late at night, it was somewhat spontaneous, there was pressure to go through with it, drinking was involved, and toward the end, my friend felt left out as she watched her man have sex with their “special guest star.” After she left, he passed out, leaving my friend craving cuddles and reconnection. She felt so bad about it, she thought about cancelling our time together, but decided to push through her ambivalence and go through with it. I’m very glad she did! It’s not often you get to experience an amateur threesome and a scheduled, professional threesome back-to-back!

I asked them if they had anything on their “wish list,” and what their limits were. I advised them to finish together, and make time for aftercare and reconnection.

She exclaimed, “Ohhhh, that’s why I felt so bad last night!”

They very much appreciated my experience, compassion, and intuitive skills in structuring an organic erotic scene that was emotionally and physically safe and sexy. One thing I notice when playing with couples is they learn better communication skills in the bedroom.

It was so hot seeing my friend in a sexual context – she was so beautiful and passionate, and of course her skillful loverboy was in heaven!

I’ve experienced hundreds of threesomes – my first was when I was 17 years old, my most recent now, at age 49. I know very well how the right context and combination of people makes all the difference.

I’m telling you – 3 is my lucky number!

Comments

GenericUsername 2022-05-06 12:11:20

There’s just something that hits different with threesomes. It sounds obvious, of course. But when there’s the mutual “we’re all in this together, for each other” there’s just something about being the center of attention by two others showing you total attention vs concentrating on your actual partner with someone new vs exploring someone new with your partner. You get the best of three worlds. There’s something to be said about you letting your partner enjoy themselves fully with someone else. Akin to an open relationship – of course sex is good, feels great, and you get the upmost pleasure from it so why not let your other half have that pleasure. You both go home from a well orchestrated threesome happy and with great memories AND with the excitement of “oh, I can’t wait to do that again…!”

Good post.

Reply

    Kendra Holliday 2022-05-06 14:09:19

    I agree! Somehow in a threesome, you don’t get twice as many hands and tongues and touches, it feels exponential. Magical energy!

    Reply

      GenericUsername 2022-05-10 15:04:12

      BUT! There’s a flip side….when it’s done wrong or taken the wrong way, man, can it ever go sour. Hurt feelings are the minimum of what happens, I’m sure. I’ve been fortunate enough to never be on the bad side of a threesome because everyone was always on the same page. Not that it’s happened dozens of times but the handful of times it was all just positive. I hope you’ve never been put in the awkward position to have been involved in a relationship turmoil due to one. I don’t envy people who have.

      Reply

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