MY PATHWAY INTO THE LIFESTYLE
from Lilly

Dear Auntie Helga,

I’ve been reading Petticoat Discipline Quarterly for many years, and I am always eager to read each months offering. I am getting old now, but I’d like to share my pathway into this lifestyle.

As a child my parents were fairly conventional. However, it was the late 60s when many young men grew their hair out over their shoulders, and my parents did tolerate that although they didn’t approve. I used to love taking care of my hair, shampooing, conditioning, blow drying it and brushing it. I also had a fascination with panties and other women’s clothing, but I was very secretive. I think my mother knew, but she didn’t confront me. Instead she sometimes fussed with my hair, and occasionally made obscure comments about my behaviour being different from other boys. My sister used to say that I spent way more time with my hair than she did with hers. My father was away a lot and was not very engaged with the day-to-day happenings in our house. Around girls I was a shy admirer. To me they were angels, and I longed to enter their world, but I was too shy, clumsy, and introverted to do so.

After graduating from school, I decided to work for a year before entering college. However, I had a hard time finding a job in the small town where I was living. My parents started to pressure me. They told me that my long hair was an impediment in my job search. They told me to cut it off, and try harder. I wasn’t in the habit of defying my parents, but I made the decision to leave home and try my luck in the big city.

I stayed in a sort of low-cost hostel for a while, and I soon felt discouraged. Job opportunities were scarce, and I was quickly running out of money. Maybe my parents were right about my hair. It was getting long and unkempt. It needed some attention, and I decided that rather than cutting it, I would go to a salon and get professional help. I phoned up and in a quavering voice, I made an appointment for later the next day. The receptionist didn’t seem at all surprised to get a request like this from a man.

As my appointment approached I almost chickened out, but I managed to make it through the door, and I was ushered through to the stylist. Her name was Sandra and she was about 45 and dressed in a stunning fashion. She wore a very short billowy dress in a bold colourful design in the style of that era.She was very friendly and put me at ease. She washed my hair and asked me what I wanted, and I didn’t really know what to say. I told her I just wanted it to look nice.

I told her I liked the way she was dressed, and she gave me a beaming smile.

“Thanks sweetie, I love my women’s life. I couldn’t imagine being a man. You know, honey, you have beautiful hair. Lots of girls would be jealous.”

I basked in the attention she was giving me, and when she was finished, I was stunned by how good I looked. I was in what I would now describe as sub space.

By this time, it was getting late at the salon. Many of the people in the shop were leaving at the end of the day. Sandra asked me if I’d like to come home with her for supper, and I quickly agreed.

Back at her apartment, I helped her make supper and we talked. She told me that I was really cute. She said that she really appreciates submissive, feminine men, and she blew me a kiss. However, she also said she likes confident guys that know how to take control of a woman. I suddenly felt some shame because I didn’t fall into that category. We talked a lot that night. I was able to talk about things with her that I had never admitted to anyone else.

In the end she said I should go home.She ran her fingers through my hair, and she gave me a kiss.

The next day I received a phone call from her. She said that she had talked to her friend Jane, a fifty-something year old woman that owns and manages two large well-known shops that specialize in women’s clothing, especially lingerie, hosiery and even some BDSM costumes and paraphernalia. She sometimes hires effeminate males, and she agreed to give me an interview. Apparently many women like to be served by submissive, feminized, obsequious men. She warned me that if I get the job, Jane will encourage me to become more and more feminine in my attitude and appearance.

Anyway, I took the interview, and I got the job. Jane and I got along very well; she took charge of my submissive nature. She became my mistress, and I became her devoted sissy. I am very thankful that things turned out the way they did, but my life with my mistress is another story.

Respectfully,
Lilly


How delightful to hear from you Lilly, thank you for being a loyal reader and for describing the path you took to arrive at this lifestyle and sharing it with us. Your long hair must have been challenging to maintain while at the same time indulging in your fascination for panties and other delicate items. I would guess your mother probably knew, she allowed you to explore those feelings.

Success at you job hunt and then on to fulfilling your propensities to dress as a woman, must have felt right and good. I will share your story with my readers soon and thank you again for sharing.

Auntie Helga

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