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TG Caption: Bad ideas (#2) Getting in her tights Published: Nov 11, 2018
Are you really this stupid? I thought for sure you would have learned something from last time www.deviantart.com/frommisogyn… . Doesn't your face just say it all.
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Some men never learn. Perhaps tonight after being “used” a dozen or so time he may learn to be less of a pig and more of a gentle kind solel
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Caught- TG Caption Published: Jan 3, 2021
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“I only meant to try it on for like 10 minutes until you got home from cheer practice, Kenna. Don’t tell anyone, please”
“Who would’ve ever thought that, James, my little brother, likes to dress up in girly clothes? If I’m being honest, you don’t look bad at all in that bikini. You can keep it for all I care”
“Do you really mean it? Thank you, Kenna. I’ll literally do anything you want now. You don’t know how much this means to me”
“Well, now that I think of it, we have a spot on our cheer team open right now because a girl got sick. You seem to know what you’re doing with this whole “thing”, Jessica. I can barely tell you’re a guy. Would you be interested in taking her place?”
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Just long enough to give the boys a chance to rethink their preferences… then exit.
Some people know from birth. Others take a little extra push…
No, they’re not easy at first. But trust me, they get easier.
They’re just clothes, right? What could be more natural than wearing clothes that match your outlook?
“Good news. The nice young man at the shop gave me a discount.”
“Do you… do you still want me when you’re like this? Or is my brother more your type? I’m just not sure if I’m ready…”
“My London Fog coat and knee-high stiletto boots, of course!”
“Don’t be like that! You had a little fun, right? Especially when that last guy was reaching up your dress! If I didn’t know better, I’d say he slipped something into your panties! He didn’t give you his room key, did he?”
“So tell me… how far did you go? And is this new look going to be a regular thing?”
Two chapters down… time for a break! Let’s see how the barista in the Commons reacts to the new you.
Sometimes, a guy just has that fantasy, and other times that fantasy takes on a life of its own.
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