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Chapter 65 by ShimoDragon
What's next?
Mentor and Muse
Elaine went through the motions of her lecture with a bit less enthusiasm than usual. It was such a minor change that her students would never be able to tell but from her perspective it was a world of difference. She was hung up on the distraction sat directly in the middle of her class, wearing a skirt that was just a bit too short.
GirleyRiley.
She had been thinking about her non stop for the past few days. Thinking about her private content. Thinking about how she wanted her to stay in her class. Thinking about how to elevate her.
Yes, Riley had a positively magnetic aura to her that even Elaine could not deny, but her obsession with the girl didn't end there. The more she watched Riley's content the more she could see just how much of a diamond in the rough she was. Riley was attractive, certainly, but her understanding of fashion was base level.
The girl knew how to put together an outfit, sure, but to make a true statement and stand out amongst the drabble she would need help. Elaine would be that help. She knew that Riley could be so much more with her guiding hand.
After a near sleepless night plagued by thoughts of Riley and her untapped potential, Elaine had an idea. It wasn't particularly ethical and she would be at risk of loosing her job if anyone realized what she was doing but that was a risk she was willing to take.
"... and that is what your final project will be all about." Elaine began wrapping up her lecture as she turned to address the room. She struggled to keep her eyes from stopping on Riley for any longer than a second. "To recap, you will all be randomly assigned a partner and the two of you will need to put together a report on a significant development in the history of fashion as well as design an outfit to highlight your chosen development."
Her students began whispering to each other. Friends were wondering if they'd be lucky enough to be paired together, obviously, but the most prevalent question on everyone's mind was who would be GirleyRiley's partner?
Elaine spoke again, silencing her class. "Unfortunately, we have an odd number of students this year. This means that one of you will be without a partner. In light of this, I have decided that the odd one out will receive a different final project. This person instead shall become my assistant and model a number of lecture relevant pieces at my instruction and select one to write a report at half the length of the standard."
The whispers had evolved into excited chatter now. Each and every student wanted what Elaine was offering. An easier final project with direct help from the professor was an unheard of hand out from the notorious Elaine Merriweather. Elaine allowed the edge of her lips to curl. They were all too excited by the news to realize how out of character this was for her to do.
"If you all would turn your attention to the projector you will see each and every pairing, and before any of you ask I will not be accepting any requests to swap partners."
Elaine didn't bother looking at the list. She already knew who her assistant would be. Riley would become her muse and she would teach her all she could. The rest were random as promised, but she had made sure that Riley would be all hers.
As most of her class groaned at the fact that they'd need to spend the next semester working with a stranger, Riley's eyes met hers from across the lecture hall. The girl smiled and gave a polite wave. Elaine's heart skipped a beat. Even such a simple movement was saturated in seductive grace. It made the older woman image the girl in a handful of deliciously complimenting outfits.
She pictured Riley in a piece reminiscent of Juli Lynne Charlot's work. A 1950s poodle skirt would compliment the girl's legs gloriously. On top of that, the style made Elaine imagine Riley wearing a Stepford housewife outfit for one of her more explicit streams. The thought stirred butterflies of excitement in the depths of her stomach.
In her decades of teaching she had never had a student that made her so eager to mentor. She had never had a student that made her feel this way before. It was addicting and freeing all at once.
It was like she was a little girl again, and Elaine had found her new favorite doll to play with.
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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
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