Head over Heels

Reads 144,329
Votes 537
Parts 50
Time 2h 14m

Reads 144,329
Votes 537
Parts 50
Time 2h 14m

boytogirl crossdress crossdresser crossdressing dress dressed femboy feminization romance texttospeech traps

The story revolves around a heterosexual man who chooses to dress up in feminine attire as part of an experiment, but finds himself in a challenging situation as he continues down this path.All Rights Reserved

boytogirl crossdress crossdresser crossdressing dress dressed femboy feminization romance texttospeech traps

Table of contents

50 parts

#15dress

Content Guidelines

You may also like

In a fit of rage, Pravin accidentally hurts his sister. She becomes upset with him and stops talking to him. In order to make her happy again, he fulfills his sister's desire and gives her a birthday gift worth remembering by becoming her younger sister for a day. In that process, he learns a few lessons about himself, falls in love with someone he never expected. Writer: Priyanka The story deals with the subject of cross-dressing and transgender fiction.

A story of a guy who meets a girl and falls in love with her and goes through a journey of discovery of his feminine side. He journey from a normal boy to an elegant and successful woman involves hard choices and tough times but at the same time gives him eternal happiness.

Oliver/Olivia: Blackmailed Sissy by lilywritesMTF

(HEAVY SUBMISSION THEMES, 18+!!) Oliver, a sophomore at Westbridge University is a bit of a creep and finds himself irresistibly drawn to the girls' volleyball team at his college, particularly their captain, Jessica. Oliver attends games mostly to ogle the team in their tight spandex uniforms. However, Jessica soon catches on to his lecherous behavior and decides to teach him a lesson. With a wicked sense of justice, she embarks on a mission to punish him-transforming him into her personal pet project: Olivia. Olivia must navigate an entirely new wardrobe and an entirely new college experience completely changed and completely controlled. How far will she go under Jessica's watchful gaze and,,, is there such thing as too far?

An 18 year old guy, on his last day before going to college, agrees to take his brother and sister to an event, dressed as a girl. But little did he know that, many events and adventures are waiting to get unfolded which will lead to chaos and fun... ***Credits to Gardiana for writing this story***

My Whispers : A Journey of Self-Discovery" by DifferentGirl_Sz

A shy boy becomes fascinated by femininity through his female relatives. Secretly adopting the persona of a girl, he experiments with dresses and accessories. As he navigates his dual identity, he faces challenges keeping his secret from friends while exploring his true self. The story is a journey of self-discovery and acceptance.

A summer break as one of the girls by LadyIwi

It's a story about young boy (Eric) who by chain of unfortunate events have to spend his vacation pretending to be a girl (Erica). During this crazy week, he will learn that being a girl isn't that bad. The main theme of the story is something I would call mild forced feminization. Protagonist is forced to pretend to be a girl, but there is no humiliation, BDSM or homosexual encounters. There is however the girl named Wendy that will make Erica feel buterflies in her stomach.

By the wife's gracious favour and an offer he can't refuse he agrees to do something, he usually won't prefer. Read ahead to find out the kinky side of the couple. *** Credit to Freethinkers32 from fictionmania tv ***

Because of a accident in the lab at school Aiden have to go with his mom to work.That's when his life change for the better

Ben has always known he was different from the other boys, but when his school uniform gets swapped with his sisters, his entire life changes into something he had never expected. WARNING: This story contains some transphobia, assault, and some scenes that are sexual in nature. There are no descriptions in the intimate scenes, however it's obvious what they're doing.

"I mean, you like wearing my panties, you must be a little bit of a slut. I'm sure you'd love to wear bras, miniskirts, dresses, heels, and makeup too." "Luna! No way." "Hey, if you steal something of mine, you're gonna have to suffer the consequences, babe."

Jordan has one week to find a job or his best friend, Eric, he has been mooching off of for months will throw him out. Eric will do anything to help his friend. Jordan wants to be a rock star with women throwing themselves at him, yet he hasn't had a gig in several months much less a paying job. Now with a week left to come up with even the promise of rent money he is stuck between a rock and a hard place, sell his keyboard or take a job where everyone thinks he's a woman. ***Credits to Nicegent42 for the story*** Pics from Pinterest

Short story of a submissive male being humiliated by a female work colleague. Five parts The protagonist is based on a person I used to work with, though names have been changed. The story however, is a work of fiction. Not sure if there's any interest to warrant it being continued? Let me know in comments

Eric comes home to find a delightful surprise where he gets to meet his 'mother' in a new avatar and role!!! A delightful crossdressing tale of a amab daughter and mother who go through an emotional as well as individual sexual journeys... ***Credit for the story goes to Jilly from fictionmania.tv***

My Billionaire Master: How I Ended Up Marrying A Disabled CEO by Sandhya_sss

"Will you marry my Disabled son?" "Oh! Fuck No! I am a straight guy, I cant marry another man" "I will pay you 10 million dollars for it💰💰💲" "Do you want me to wear a Lehanga or saree at my wedding?" It was a simple choice for Ishan, a financially struggling guy in his 20s burdened with family responsibilities. He would do anything to be rich.. Even sacrifice his sexuality and masculinity in the process. !!!!Warning!!!! The story contains some mature elements which are marked with 🔞, which have minor impact on the overall story. Please skip the chapters if you don't like smut.

Becoming Her Desire: A Story of Feminization and Transformation by AshleySLord

Lily has a passion for fashion. She's always dressed impeccably, and that's one of the things that Alex loves the most about her-her creativity. However, unbeknownst to Alex, Lily was forging a plan to reveal her deepest and darkest secret to him. She wanted to share her love of feminine clothing with him. Becoming Her Desire follows the story of Alex and Lily as they explore their love for each other in new ways. When Alex is ready for a romantic date night with Lily, he's shocked when Lily asks him to wear a dress that she specifically picked out for him. This event sets them down a long, romantic, and sexual path that eventually transforms Alex into Alexandra, when he becomes her desire. 🥇 #1 in Clothing 🏅 #2 in Lingerie 🏅 #3 in transgender Note: This novel is for Mature Audiences ONLY. It does contain explicit, erotic scenes of sexual encounters and explores themes like feminization, domination, threesomes, and many more unorthodox sexual activities.

After Charlie's mom dumps him on his aunt to take a job in Japan, he finds himself in Galeton, a tourist town were everyone cosplays like it's the 1800s. He starts working in a historic hotel with three girls, and they gently coax him (or should we say her?) out of the closet.

Justin has been getting in to trouble .so as a last resort his mother tries to feminize him.

The transformation story of Michael, whose life would never be the same after one fateful Monday morning.

Fake Family for a Halloween by CuteMente

My daughter and her friend made an unexpected request: "We want to dress as a full-fledged family for Halloween!" But the problem was that, to fulfill this request, I would have to pretend to be a woman. The story is about the relationship between a single father and his daughter, the struggle to come to terms with the loss of a loved one, and the search for a new self and the warmth the characters of the story are lacking.

Bryan is chosen to conduct a study, but he is required to assume the identity of a girl for a whole year. As his new persona, Heather, he encounters various situations that he never imagined.

Birthday Gift

In a fit of rage, Pravin accidentally hurts his sister. She becomes upset with him and stops talking to him. In order to make her happy again, he fulfills his sister's desire and gives her a birthday gift worth remembering by becoming her younger sister for a day. In that process, he learns a few lessons about himself, falls in love with someone he never expected. Writer: Priyanka The story deals with the subject of cross-dressing and transgender fiction.

More details