There were rumours about a guy when I was working in Toronto that he was a crossdresser. No one knew for sure. I decided to ask him directly. He smiled and said, “Sit down and I’ll tell you all about it.”
First though, a related topic. A few years before the pandemic there was ‘Ladies Spring Tea.’ They asked the Blackhatters to put on a fashion show while dressed in female attire. About seven of us agree. We wore wigs, makeup and jewelry, etc. I even found a pair of high heels at Value Village. We all began on the stage and introduced. When a particular song played by DJ Ernie Thomas (mine was Sexy Eyes by Bette Davis), we left the stage and did our bump and grinds around the tables before returning back to the stage to be judged. The best was chosen but every participant was appreciated.
Back to Jerry who was in his late twenties. He began, “Ever since I was a kid, I have been intrigued by female clothes, especially dressing secretly in my sister’s outfits. I tried to break the habit with limited success.” Later I met this formidable girl Nancy. We began dating and knew we were made for each other, so moved into an apartment together.
She worked in a pharmacy and I worked as a freelance designer. Most of the time I was working from home, also admiring Nancy’s cute clothing. One morning I woke up late. Nancy had left for work. I noticed her bra and panties in the bathroom and was compelled to put them – my entire body was trembling with excitement. Soon I was diving into her lingerie cabinet when she was at work and trying on her latest lingerie. I almost got caught twice and that was quite scary.
I thought about telling her about my crossdressing many times but I was afraid she might break up with me after knowing. I decided not to keep it a secret hoping my desire to cross-dress would fade out. However my interest in women’s lingerie grew instead. I was addicted to the feeling of wearing my girlfriend’s undies and cute dresses, walking around the apartment and taking tons of photos of myself.
One day, I picked a black mini dress and one of her sheer pantyhose. Pulling up the pantyhose, it unexpectedly ripped, making me very nervous that she would find out. After a few days I decided to try on some lingerie again. Sauntering around, I couldn’t stop admiring myself in the mirror. Suddenly the front door opened.
Nancy was home early. I was petrified with horror so rushed to the bathroom to hide. “Jerry, come out. We need to talk!” My heart was pounding. I was in trouble and too embarrassed to face her. Nancy finally said, “I knew something was up so I installed a hidden camera.” She then showed me a few of the videos of myself going through her clothes.
”Jerry, I will give you a second chance. I have a perfect plan,” she said looking quite serious. ”I will do anything for your forgiveness.” I replied.” Tomorrow you will spend an entire day as my girlfriend, even going shopping. Do you understand?” she said.
Next day, Nancy gave me a full makeover. First she made me wear her padded bra and lace panty, a white top, black mini skirt and black sheer pantyhose. After I was dressed, she brushed my hair, added some hair extensions and tied it back. She applied makeup and painted my nails too. I felt quite uneasy but equally excited. Heels were next, taking a little time getting used to.
I hesitated to get into the car and head to the mall. My heart was beating like a drum the whole time and I felt nervous with my new appearance. In the mall I felt like everyone was just staring at me.
After stopping at a few shops, I begged to go home. It was hard to believe I was partaking in such a situation.
Nancy fully accepted my crossdressing. We now have an arrangement where we go out with me dressed as her girlfriend. It was always so thrilling for me.
As for the Blackhatters in the fashion show, none were tempted to ever cross-dress again – as far as I know!
