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Chapter 31
by
Dayeandknight
What happens next?
Natalie realizes who "the woman" is (by Vanilla Thunder)
Natalie looked into the woman's eyes and suddenly, things clicked into place. She was extremely shocked and was speechless for a moment.
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"Nat?" Jamie asked.
"Jamie... I..." Natalie started to reply. "I hardly recognized you..."
Jamie was confused until he remembered what he was wearing. He looked down and saw the exercise pants and t-shirt.
"Oh, yeah, the outfit. That's cause my apartment burned down and Linda, Mark's sister, was good about lending me something to wear." Jamie said.
"Right..." Natalie replied, trying to piece together what was going on.
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Natalie wondered, it had been a while since she had seen Jamie, a few weeks at least, but he never said anything about wanting to be a woman before. She'd never have guessed, but based on how she was acting with the guy, she guessed that was Mark, that this must be what Jamie wants. Why else would he be dressed like this in public? She entertained the notion of **** or a bet, but the way that Jamie was acting with that man... he was enjoying it. Natalie was certain of it. And if this is what her friend wanted... she wasn't going to judge. Male or female, Jamie was a friend.
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Jamie was so relieved to finally see a familiar face. He was also happy that Natalie didn't seem to be judging the strange way he looked. She was a good friend like that, not going to say anything to embarrass him.
"Do you need money or anything?" Nat asked.
"Not right now, I've got some savings." Jamie replied. "But I just wanted to make sure that you'd know I was okay, in case you had heard. Feel free to tell anyone else that asks about me."
Only seemed fair to let her give the news, in case a mutual friend reached out to her if they couldn't find him.
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Natalie surmised that he must be out of the closet, if he's not asking her to keep quiet. And good on him... her, whichever it was. She certainly didn't expect this when she saw the couple, but she's happy for Jamie.
"Anyway, I've got to get back to Mark, but it was great seeing you. Feel free to reach out." Jamie said as he got up and walked back to his table.
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Mark smiled when Jamie returned to the table.
"How's your friend?" Mark asked.
"Good, I think. Seemed a bit weird at first, but I think it was just my outfit." Jamie replied.
"I don't think you look that bad. Bit of a lazy day look, but I like it." Mark laughed.
"Oh, stop it." Jamie giggled and playfully slapped Mark's arm.
What happens next?
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Crossdressing Stories
A collection of separate stories that all involve guys ending up in dresses
A collection of separate stories that all involve guys ending up in a dresses
Updated on Feb 22, 2026
by Dayeandknight
Created on Feb 1, 2018
by Dayeandknight
- 5,859 Likes
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- 384 Chapters
- 73 Chapters Deep
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