My Awkward Sexual Experiences – Real Sex Worker Stories – Part Deux

Nina’s Leone’s Story

In my time as an escort, I once had the honor of deflowering a 33-year old virgin. He was a sweet, slender, geeky-looking type who was socially awkward and so very self conscious. We booked an hour-long session, and when he arrived he was nervous and tense. He wouldn’t let himself relax into the moment, and so I went into hospitality-mode and did everything I could think of to help him unwind. I offered a massage, I tried flirty conversation, I reassured him that it was okay to be nervous. But his emotional walls were firmly up and he didn’t want to let me in.

Next, I tried to reach him through gentle touch. I held him close to me, placed his hand on my heart, and then ran my fingers and hands up and down his back. He tensed. He resisted. He held his breath. He suppressed his body from responding. I became confused. I sweetly said, “you don’t have to do this, honey.” He insisted that he wanted to do this – that he needed to lose his virginity. It was long past due. He couldn’t wait anymore.  But his body betrayed his words. His penis refused to stiffen. He cursed and swore at himself, judging himself harshly. I could glimpse the depth of his self-hatred.  

I began to understand that there was a very good reason he was still a virgin at 33. He needed to learn to love himself before he could surrender to the intimacy of sex with a partner. He requested to skip through the foreplay to get to the deflowering/intercourse part of the session. With empathy, I agreed.  But again, his body would not respond to the moment. He soon got angry and we ended the session. He left feeling defeated, depressed, and deeply ashamed. I never heard from him again. I feel sad for him. His lack of connection and intimacy is self-imposed, and I hope he figures a way out of his own private emotional prison. 

LESSONS LEARNED

I learned that specialty clients, such as virgins, need more attention than a single one-hour session can offer. For the next one, I would have a 3-date courtship and take things more slowly – similar to real dating. It would be a multi-sensory experience that unfolds in an un-rushed atmosphere.

I also realized that some clients have mental health issues that my caring companionship simply cannot resolve. I need to set healthy boundaries and expectations for myself and others.