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Dress Like a Girl: A Gradual Feminization Story
What happens when you enter a bet you can’t back out of? And what if that bet involves dressing like a girl?
Twenty-three-year-old Taylor Holmes knows he needs to take things more seriously. And just in time! It’s his first day of graduate school at Elkhorn University, and an amazing post-grad opportunity has just been announced. But in trying to establish himself as a serious candidate, he makes a foolish bet with his academic rival. A bet that, unfortunately, risks him dressing like a girl. What may not be a big deal to some, to Taylor — with his long brunette locks and already-feminine tendencies — dressing up just once might send him down, shall we say, an “eye-opening” path...
Twenty-three-year-old Taylor Holmes knows he needs to take things more seriously. And just in time! It’s his first day of graduate school at Elkhorn University, and an amazing post-grad opportunity has just been announced. But in trying to establish himself as a serious candidate, he makes a foolish bet with his academic rival. A bet that, unfortunately, risks him dressing like a girl. What may not be a big deal to some, to Taylor — with his long brunette locks and already-feminine tendencies — dressing up just once might send him down, shall we say, an “eye-opening” path...
129 pages, Kindle Edition
Published September 23, 2025
About the author
Jennifer Sweet
16 books55 followersJennifer Sweet is a California-based author who passionately pens novels and novellas about boys finding their feminine sides -- anywhere from the sweet and innocent to the steamy and seductive :)
All of Jennifer's work can be found on Amazon. Visit her website for more, and sign up for her newsletter for the latest updates on upcoming books.
www.jennifersweetbooks.com/newsletter
www.jennifersweetbooks.com
All of Jennifer's work can be found on Amazon. Visit her website for more, and sign up for her newsletter for the latest updates on upcoming books.
www.jennifersweetbooks.com/newsletter
www.jennifersweetbooks.com
Ratings & Reviews
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Community Reviews
Displaying 1 - 8 of 8 reviews
September 27, 2025
aaaaaaaahhhhggggg!
Jennifer, you are killing me! I hope there is a second book coming in this series. I want to know what happens next…
Seriously, this was a fun story, but then again all Jennifer Sweet’s stories are fun. This one just felt too short. I really thought it could be longer. There is definitely more of the story to be told. Please, please, please, give us more stories soon.
Jennifer, you are killing me! I hope there is a second book coming in this series. I want to know what happens next…
Seriously, this was a fun story, but then again all Jennifer Sweet’s stories are fun. This one just felt too short. I really thought it could be longer. There is definitely more of the story to be told. Please, please, please, give us more stories soon.
October 2, 2025
Trying to dress like a girl
This is the story of a guy in college losing a bet to wear a dress at photo day and in the process going out on the town dressed as a girl and kissing a another guy while being drunk and then getting it shown out in class by a another class mate that didn't care about someone feelings till it was to late for himself. This is for anyone who has tried to understand what being a girl is like or enjoys dressing like a girl for there own personal experiences in their life and in their lifestyle of being who they want to be in life.
This is the story of a guy in college losing a bet to wear a dress at photo day and in the process going out on the town dressed as a girl and kissing a another guy while being drunk and then getting it shown out in class by a another class mate that didn't care about someone feelings till it was to late for himself. This is for anyone who has tried to understand what being a girl is like or enjoys dressing like a girl for there own personal experiences in their life and in their lifestyle of being who they want to be in life.
September 25, 2025
This was a Win-Win book for anybody with a nice open mind.
I thoroughly enjoyed this wonderful story. You definitely need to stay the course to see if Justice is served.Professor Kendall is awesome and gave Taylor a good jump start. Ella turned out to be rock solid as a friend. I would have loved to see all the girls gets follow on story.
I thoroughly enjoyed this wonderful story. You definitely need to stay the course to see if Justice is served.Professor Kendall is awesome and gave Taylor a good jump start. Ella turned out to be rock solid as a friend. I would have loved to see all the girls gets follow on story.
February 21, 2026
Jennifer Sweet is an excellent author…
Not only is she able to construct a coherent narrative but she has a way putting forth sound moral reasoning. She reminds me a lot of Daring Diane, who is also an excellent author…
🧍🏻💃🏻 Excellent 💥 Read 🧞♀️🧍🏻& 💃🏻
Not only is she able to construct a coherent narrative but she has a way putting forth sound moral reasoning. She reminds me a lot of Daring Diane, who is also an excellent author…
🧍🏻💃🏻 Excellent 💥 Read 🧞♀️🧍🏻& 💃🏻
October 13, 2025
Taylor lost a bet to Nate can dress as a girl for picture day. It was pretty predictable.
November 13, 2025
Loved this
Bets are the best way to get us into our girlie selves. Looking forward to see what Tay will be up to in the next book.
Bets are the best way to get us into our girlie selves. Looking forward to see what Tay will be up to in the next book.
August 15, 2026
Weird book
June 26, 2026
This was just okay for me. I wish it was fleshed out a bit more
Displaying 1 - 8 of 8 reviews