Chapter 23
by
Baranda
What happened next?
3 days passed
The next day at school, John was once more the center of attention. Everyone was shocked to see him wearing high heels, a short skirt and a woman's top. He answered the question why he was dressed like that either with "Because it's stylish.", "I like these clothes." or "Have you forgotten I always dress like this?". Some teachers even warned him not to wear such sexy clothes, above all not as a boy. But John didn't cared. He continued dressing like a woman.
On the third day after he began dressing like that, John decided to go with a special outfit because after school he had his next appointment with Dr. Valentine. For his underwear he picked the third set of a lacy thong and matching bra, followed by the purple stockings. Over that he put the black dress, a slim belt emphasizing his slim build. On his feet he put the most stylish pair of shoes he had, the black overknee-boots. He loved how they looked and felt on his stocking-footed legs, and a lot of boys in school seemed to love them too. In the past days he got whistled sometimes, but that day it was even more. In just a few days they seemed to have forgotten that the womanly dressed figure, who was the first person in the four years John visited that high school wearing overknee-boots, was a boy. For John that felt both disgusting and good. He liked the attention and that they recognized his style and beauty, but he didn't wanted them to treat him like a girl or woman, because he wasn't one.
...
In the afternoon John met again with Dr. Valentine. She was a little surprised seeing him dressed like that, but hid it. "You look good, John. Very stylish, if not to say sexy."
"Thanks, Dr. Valentine." John replied after greeting her with the usual two air-kisses. "I too think I'm looking stylish and sexy." The last was new for John, but he added it to his mindset without a problem. John walked over to the couch and sat down on it. The heels of his overknee-boots **** him to bent his legs to the side in a very feminine way.

"I must say, you look very much like a woman, just like you want to." Dr. Valentine finally **** the thought of looking like a woman on the boy.
"Yes, I so much love to look like a woman and not like the boy I am." John said.
"That's good. That's one more step for you to become more confident." The therapist said with a smile knowing that the boy wasn't too far from her goal.
What happened next?
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Sex therapist
Sexual healing, or sexual breaking? You decide.
Choose to be a boy or girl who goes to see a therapist with unusual methods.
Updated on Mar 23, 2026
by Pawnshop56
Created on Sep 1, 2016
by qaz
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