Stumbling over the decades

Jue Meili Olaes · 2021-02-07T13:00:44Z

My transitioning journey I will be 73 in May 2021. Reflecting on my long journey, I still recall vivid memories of my childhood, of my yearnings to become a beautiful female. Reflections of hiding in a closet I will be 73 in May 2021. Reflecting on my long journey, I still recall vivid memories of my childhood, of my yearnings to become a beautiful female. Back in the 50s, when I was 6 or 7 and nobody was home, I used to sneak into my Aunt’s room to wear her strap sandals, feeling an intense femininity as I stepped into them. When I was a young teenager in the early 60s and nobody was home, I tried on my Mom’s underwear, silk stockings and shoes. The dreamy caress of silk on my body was surreal. Once, I even wore my Mom’s bra under my clothes to go to church on Sunday and prayed to become a woman. In Junior school, I was drawn to a boy by his femininity, seeing myself in him and wanting to hold his hand. Other boys would make fun of him, calling him a queer, that scared me away. As I grew up, I was especially fascinated by stiletto high heels, but not the platform type. My rich uncle used to take us in private cabs to go to the beach on the weekends. There was this lady driver who had a pair of black pumps with stiletto heels, which she kept under the car seat. I so wanted to touch them and wear them but dared not. My stern father sitting next to me would frown upon such tendencies. Family and peer pressure persisted in the ultra conservative society in the 50s, 60s and 70s that drove me to hide my feelings and yearnings. It's effect made me feel so couped up in my shell. I felt so helpless. Even after marriage and starting a family in 1971, I used to keep my ex-wife’s torn stockings that she wanted to throw away, wearing them under my pyjamas to go to sleep at night. I secretly bought some high heel pumps to wear when nobody was home. Once, she helped me put on make-up at my request; I was thrilled when I looked into the mirror. Somehow and to my disappointment, this was never repeated again. I put on some of her perfume before going to work, where I would overhear whispers behind my back, so I stopped. I was distracted by and looked longingly at the sexy high heels of my colleagues at work. So much peer pressure. I cannot refute having my share of extra marital affairs, but I believe this was another challenge to my gender identity. I wanted to get close to other females to identify with them. I really wanted to be like them, to be a woman. I remember taking home a cheong-sam dress from one of my mistresses and wearing it under my pyjamas to go to sleep at night. After just over 20 years together, I separated from my wife in 1992, eventually becoming divorced. Immediately after my separation, I started a relationship with my girlfriend that lasted for 27 years. I must admit we were very happy together because she dressed up in sexy outfits and high heels to please me, but I still had these suppressed urges of femininity. I admired her sexy body and wanted so much to be like her, to be a woman. I still kept a small collection of high heels, and would wear them to sleep at night, or even on some occasions when we made love. Subtle leanings towards transitioning My girlfriend and I used to go shopping in Buffalo shopping malls when the Canadian dollar was stronger than now. During one visit in 2005, I got my ears pierced so that I could start wearing earrings. I took a pair of her earrings to wear every night, telling her I did not want the pierced holes in my ears to close up. I still have those special earrings which gave me so much comfort that I still continue to wear them to go to sleep at night. Whenever we travelled to go shopping in the States or to go on Caribbean and Mediterranean cruises or to Hong Kong, I would bring along a pair of her open high heel sandals to wear to go to sleep at night. We took up ballroom dancing in 1995 and would go dancing every Friday and Saturday evenings. The dance clubs had Halloween Masquerade Balls every year. In 2017, a man dressed up as a woman at the Halloween Masquerade Ball; he did not look very feminine and it was clear that he was a man, but he won one of the top prizes. I said to myself, I could do better than that and told our dance friends that I would dress up as a lady at the next Ball. It was time for the 2018 Ball, I went dressed as a tall slim sexy old lady. I wore my girlfriend’s evening gown, corset, panty and bra with high heels from my collection, topped with a cheap silver wig and Masquerade mask. Sadly, I did not win a prize as the judges did not realize I was a man, I was too convincing as a woman. The Manager noticed that I was a Transgender woman and awarded me a consolation prize. My girlfriend did not like me dressed as a woman, I felt some relationship pressure. I had grown my hair long and dressed again as a woman to go to the 2019 Ball. This time my daughter, who used to work in a beauty salon, helped me with professional make-up and ha...

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Barbra Heaps

Copper

March 22, 2025 4:45 am

(@barbra)

Trusted Member United States of America, Ohio, Toledo

Joined: 8 months ago

Thank you Jue for writing about your life a lot of us have similar story's. I grow up in the 60s & 70s with a strict Catholic up bringing. I knew I was different at the age of 5 would pray to God to make me a girl. I was that effeminate boy in grade school who was called a sissy,fairy and queer consonantly bullied.Life some times is just not fair to make a long story short I will skip the next 5 decades to present day. I have accepted who I am and have been in therapy 1 1/2 years. I have this month started HRT and hope to become that Woman I was meant to be!

Hugs Barbra

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