In the mirror, Taylor saw himself. He looked smooth and feminine, with silky long legs, his little cock squeezed into the tiniest pink chastity cage you could imagine. He couldn't believe how good he felt. Watching him was Veronica, a woman he had known for a little longer than 24 hours.
He had bumped into her the day before at the store. She had asked him to reach up and get her something of the shelf, then they had begun talking. It was surprising that she was 46 years old -- she could have passed for late 20s, though looking more closely, she did have signs of maturity. She had a pretty face, with straight shoulder-length blonde hair that stopped as it reached her large, full tits. As they parted, she asked for his number, and he gave it to her.
She had messaged him pretty soon after, starting with regular questions and a few compliments. Then she had asked if he was single. Taylor said he was, and she told him that she was married and had been for 15 years. "I don't sleep with other guys and my husband doesn't sleep with other women." Then, having established her situation and showing a kind of flirty confidence, she started asking him more questions. She asked about his sex life, and his preferences.
"Are you submissive? :P do you like guys?"
"Noo I'm not into guys. Yes, I guess im submissive sometimes >.<"
"Have you ever wanted to be the girl?"
"What do you mean?"
She sent him a picture of a near naked body, feminine and smooth, hot, but up its little skirt was a tiny pink chastity cage. His body reacted to the image, he flushed and then grew nervous.
"Oh my. Not sure about that lol."
"Would you want to try it?"
"...maybe.."
She changed the subject, and later she invited him to come over the next day. Taylor went over. Her house was brick, tidy with a neat garden and traditional style. They had a coffee and bonded with chemistry of a teacher and a student, and Taylor listened as she told him that she used to be a lawyer but had retired early. Her husband worked in some senior construction role and spent a lot of time away, but they were still very close and happy together.
"But" she said, "I have a lot of time on my hands. And I like making friends. By the way, you've got a great body, you know. Your legs are amazing."
"Oh.. thanks!" Taylor said awkwardly.
"I love a good set of legs. Although... I think they're way hotter when they're nice and smooth. Have you ever thought about shaving them?"
Before he responded, she casually pulled off her tight long-sleeved shirt, and her tits popped out the bottom one by one and rolled and settled. Her skin was subtly freckled, her sweet pink nipples slightly enlarged as a mature woman's are. She went on talking as she took a smaller top, a small white singlet, and put it on casually as if she had just decided to change clothes as the temperature rose. It really wasn't much of a top -- her tits were mostly still visible.
"You know, I was being serious when I asked if you ever wanted to be the girl. I think you would make a really good one."
She began to explain that she had a kink for this kind of thing. Veronica and her husband had done everything together throughout their long marriage, but since they were highly sexual people, they needed to experiment to keep things interesting. One day, she stumbled upon the realm of feminisation. She loved the idea of dressing up a younger guy and watching her husband take him up the ass. Her husband loved it too -- he had his desires, she said, but their values meant he wouldn't sleep with another woman. Letting him go to town on a sissy girl was a perfect solution and risk-free. They had tried it a couple of times, but it was hard to find the right kind of person for the role.
