Chapter 2: A Glimpse Behind the Pink Curtain

Bill and I met through a popular online dating site. We met at Starbucks, which seems to be a popular first date venue used by the online dating crowd. We started at Starbucks in the early afternoon and ended at my house in bed before 10 p.m.

The sex was fiery hot, physical, and without the slightest inhibition. There was none of the usual awkwardness people often experience the morning after first sex. Bill hung around until Noon the next day, staying for breakfast, a dip in the pool with my dogs, and long conversations about our jobs, our past, our interests, and where things might be headed between us. It was the perfect ending to an incredible first encounter. There was nothing unusual about that first sexual encounter, but I noticed that Bill shaved his legs, chest, armpits, genitals – his entire body was devoid of hair except for his head and a trim goatee. I noticed but didn’t think much of it.

There was instant chemistry between us from the moment we met in person. It was clear to both of us that we were not going to take things slow. Some call it love at first sight or crazy stupid, but whatever you call it, we had it. From that first date, we were inseparable.

Within days of our first date, Bill began testing my acceptance of certain things he was drawn to, including what my appetite was for his particular variety of sexual interests. While Bill wore traditional men’s boxer shorts the first time or two we slept together, he quickly tested my tolerance for his preferred underwear of choice – thongs.

He started by asking subtle questions over text messages such as “Boxers, briefs, or other?”  Confused, I replied, “Other?” and his response was “Thong.”  When I replied, “Sexy!”, I never saw the boxers again unless he went to the doctor or worked out at the gym. At first, he wore a collection of mostly black and blue thongs designed for a man’s anatomy that were not at all feminine. They were much smaller than a speedo bathing suit, but you get the idea.

The testing continued with a question about toe rings.  Mistakenly, I thought the reference was whether I wore them, but he corrected me and asked whether I minded if he wore toe rings. I replied no. The next time I saw Bill, he had one silver toe ring on each of his middle toes. I had never seen a man wear thongs or toe rings before, but I didn’t think it was so unusual that I would never want to see him again. However, these subtle and quirky situations were making me more curious by the day.

The inquiries to test my tolerance started innocently enough with underwear preferences but quickly escalated to sexual desires and fantasies. Within a week of our first date, Bill bravely asked me over a text exchange if I ever tried ‘role-playing’ or ‘pegging[1].’ I played along and it led to a very steamy, blow-by-blow account where I described in detail restraining him to the bed, strapping on a dildo, and slowly pounding his ass until he exploded. He was quite thrilled with my erotic story, which was soon recreated in real life when Bill brought out some of his adult toys, including a strap-on harness and an assortment of dildos, butt plugs, and restraints.

Bill made it very clear that he liked to be dominated by a woman and to be in a subservient role during sex. He had a deep desire to be humiliated, spanked, and called dirty names. While he had not yet revealed his crossdressing, his submissive role during sex quickly became the norm when he described that “man on woman” intercourse “never did anything for him.”  Again, I had knowledge but no understanding of how that declaration would impact and change my life.

Bill had given me just a glimpse of what was behind the curtain, but there was so much more backstage I had yet to see and experience.

[1] Pegging is a sexual practice in which a woman performs anal sex on a man by penetrating the man’s anus with a strap-on dildo.