I thought I’d share a little story I had from one of my prospective clients the other day. I interview all my private clients before deciding whether they are worthy of my attention. I have to satisfy myself that they are suitable for my services, that I will feel comfortable working with them, and that my service will indeed improve their life. With this in mind I invited young Mathew, a 23 year old Software developer, to my studio to for an initial appointment. I think you’ll find his interview of interest.
My first question is usually about when the person started crossdressing, and we see where it goes from there.
“I remember it quite clearly,” said Mathew, a quiet confidence in his voise.. He was sitting crosslegged on the floor, and I listened to him in my comfortable chair, enjoying a cup of Early Grey.
“My aunt would baby sit me. I was about 7 at the time. She was an unusual woman, and the previous year her own daughter had got up one day, packed her things and taken off. She disappeared for several years.”
“I see,” I said, “and your aunt liked the company of a child?”
“No. It was more than that,” he said guiltily.
“I think you should tell me all about it, don’t you?”
“Yes, Mistress. She would make me dress in her daughters clothes. Not at first. It started out as a punishment. I’d fallen off my bicycle, and when I cried she told me not to be like a little girl. It hurt like hell, and I couldn’t help it. After she’d put a plaster on it she told me I’d have to change clothes. I didn’t know any better.”
“So, what did she make you wear?”
“Well, that first time there were no other boys clothes, so while she soaked my trousers to get the blood out, she made me wear a skirt.”
“And you liked that?” I asked.
“No! Not at first. But she said I looked rather pretty. And the next time I came over I found that if I did anything that was against her she’d force me to wear something of her daughters. Of course she told me not to tell anyone. By the time I was 9 I was wearing her daughters clothes most times I went to see her.”
“I see. I guess you really were a very naughty boy.” I murmured as I sipped my tea.
“Not really, Mistress. She’d make up things. Like, she’d say I should water the garden, then later She’d call me to her and say I had missed part of the flower beds. She was very strict about that. But I know I hadn’t. The punishment would be to wear something she’d laid out in the spare bedroom. . I didn’t mind though.”
“No, I guess you didn’t. I think your behaviour was well established by then,” I mused. So many crossdressers have a path established long before they realise it’s going to happen.
“Yes. That was when she’d start to reward me for good behaviour. She’d let me watch as she dressed herself.” His voice was slightly more animated now. I could hear the excitement in it.
“I see. A little boy watching his aunt. How very odd.”
“Yes,” said Mathew. “She was a strange woman.”
“When you say ‘was’, whatever happened to her?”
“My aunt died three months ago.” He said sadly. His downcast eyes reflected the loss.
“Well, I’m sorry. Were you very close?”
“I lived with her from the age of 16, Mistress. I miss her.” I could see his eyes tearing up.
“Now, now, Mathew. There’s no need for tears. Don’t you worry. I’m going help you out.” I spoke soothingly, to comfort him.
“Thank you, Mistress.” He said quietly.
“I’m sure your aunt appreciated you in her own way,” I said to calm him.
“Yes, Mistress. I believe she really did.”
“Very well, I will see you on Friday afternoons at 3 pm. Alright, Mathew?”
“Yes, Mistress,” he said his face a picture of relief and gratitiude. “Thank you!”
“And Mathew,” I added quietly, leaning close to him. “You may call me ‘Auntie Meg’.
I am very particular with my personal clients. However, I’d very much like to see you advance along the Path Of Submission a little further. With this in mind, if you’ve not already done so I’d like you to sign up for my premium program. I’m sure you’ll appreciate my tender touch.