Masculinity Lost

Story Info
How a straight guy was forced to become a sissy.
2.7k words
4.43
59k
76

Part 1 of the 17 part series

Updated 04/26/2024
Created 02/03/2024
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Introduction:

Hi yall! This is my first attempt at a story so I would love and appreciate any feedback! I'm making this up on the fly so I'd love thoughts and ideas on how we can really humiliate young Danny Stewart! I prefer my stories be based in reality (crossdressing, padding for breasts and hips, hormones and surgery vs magic or scientific machines) and heavy on the feminization and humiliation aspect! Let me know what you like and I'll do my best to incorporate it into the story! Thanks boys and girls!

Love- Jessica :)

Chapter 1

Danny Stewart was a typical 21 year old college student. He went to class and did fairly well. While very bright and intelligent, he was able to do above average in class with minimal effort into studying and class work. What he spent the most time on was carousing around campus, partying with his frat buddies, and most of all flirting with all the pretty college girls he could find.

Danny had boyish good looks. Longish brown hair that fell past his ears, bright blue eyes, and a hairless face that was just on the line of between handsome and pretty. While not overly tall for a man at 5'6" and a skinny 140 lbs athletic body built by a lot of cardio, he had a prominent bubble butt that the girls on campus were jealous about. Girls would constantly tell him they wished they had his perky booty, with surprisingly wide hips for a boy. His butt was a source of pride and shame as he knew a boy wasn't supposed to have such a feminine rear but the compliments he got for it from girls made up for it.

There was even a time at his frat party where his buddy Kyle, a big hulking brute who played linebacker for the school, drunkenly slapped his ass while saying "damn girl, you got the best ass at this party! Show it off for us honey!" before stumbling off. While Danny was incredibly embarrassed and disgusted that his friend thought he was a girl, and a hot one at that, there was a small part of his drunken brain that was appreciative of the slap (and also liked how the hard masculine slap made him feel submissive and feminine). He quickly shook his head at the thought and continued his game of beer pong without another thought.

Danny was able to get past his rather short frame and effeminate features and was fairly successful with girls at school. He had several girlfriends and hook ups with girls of the school who loved his boyish charm and pretty features. While these girls wanted to stay with him, Danny never stuck around long, not wanting to be tied down. While not mean to his previous girlfriends, he left them wanting more from their relationship, souring them to Danny especially when seeing him the next weekend at a party chatting up and making out with another pretty coed.

This all came to a head at the spring party right before final, where Danny and his frat are throwing a "Halloween" party. While throwing it as a last hurrah for the year before finals and students go there separate ways for the summer, the Halloween theme is to get girls in skimpy costumes (typical frat boys).

Danny had just broken it off with Jessica Smith, a brilliantly smart blonde sorority girl the looks to match, the week prior and was looking forward to hitting it off with a new girl at the party. Danny thought he broke it off amicably with Jessica, leaving them as friends.

Jessica had over a 4.0 GPA and dreams of becoming CEO of her own company. As a cheerleader for the school, her 5'5" body was toned from years of athletics. Jessica didn't dress like sluts at her school, but she always left little tidbits showing off her amazing body. A button or two undone to show off her D cup breasts. A skirt riding the line between appropriate and slutty lengths. Her dresses fitting perfectly tight to show off the ass years of cheerleading helped build. But Jessica was smart. She knew how attractive she was and used it, combined with her intelligence, to get what she wanted. When Danny broke it off with Jessica, she was pissed. Little did he know the 5'5" blonde would have other plans for little Danny.

Chapter 2: Danny's at the gym

It was a Tuesday night in May and Danny was finishing up at the university gym. While the rest of his frat brothers were benching, doing bicep curls, and deadlifting, Danny was on the treadmill, cooling down from his leg work out.

He tried doing the heavy upper body weight lifting with his buddies, but shifting the bench press from 300 lbs with heavy 45 lbs plates on the side, to just the bar with little 5 pound plates was just a hassle. Plus, the jabs and jests from his buddies about lifting "girl weight" and "maybe you should go do Pilates with the Kappa Zeta sorority next door, I bet they have a pair of yoga pants and a pink sports bra to lend you hahahaha" was getting to Danny. So Danny focused on what he did well, working out his toned legs. While Danny couldn't bench those heavy weights, he could squat and leg press very heavy, adding to his feminine bubble butt even more.

Danny was cooling down on the treadmill from a heavy squat session. His longish hair pulled back into a low ponytail, a tight blue matching workout tank top and short athletic shorts. He'd been meaning to get new shorts, as his workouts lately have been so heavily butt and legs focused that the shorts were very tight against his heart shaped ass.

Walking on the treadmill, sweat pouring down his body, and his ass jiggling with every step, up and down. His heavy workout made his hips move a little differently, so his ass swayed side to side with a rolling motion like a stripper in high heels working the stage. His tanned legs shined from the sweat, and with such fine body hair, combined with the sweat shine, they looked freshly shaved with oil to make them gleam

With his headphones in, Danny couldn't hear the Uber masculine guy trying to get his attention. All the sudden, Danny's workout playlist of Dua Lipa's music was interrupted by a tap on his shoulder.

Danny turned, shocked cause he was so exhausted and locked into the feminine song he was listening to, looking at a massive hulk of a man. A masculine handsome face with 5 o clock shadow sat on a 6'4" frame that looked like he should be on a NFL field rather than a local gym. His biceps bulged and his pecs and abs showed through his soaking wet workout tank top.

"Excuse me, Miss? I was wondering how much longer you had on the treadmill?" The hunk asked little effeminate Danny. Danny was so shocked that he just stared at the man, dumbstruck by how masculine and manly he looked (something Danny always hoped to look like but genetics wouldn't allow).

"Hmmm... a couple minutes?" Danny whispered, his voice tight in his throat from his exhausting workout, plus the confusion of being called Miss made the sound come out soft and feminine.

"Oh alright I'll just find another one then. I'm John by the way, I haven't seen you around. I just transferred from Northeast State to play football next fall and I know next to no one. What's your name?"

Coming to the realization that this big man thought you were a cute little gym bunny coed, you had to set him straight that you were a guy!

"Hi yeah I'm Danny, I'm actually..."

"Dani, that's a cute name for a cute girl! Oh, my teammates are heading out so nevermind about the treadmill. But hey, we should get together sometime. I heard there's a "Halloween" party this weekend. Would love to see you there. Here, let me give you my number"

John quickly interrupted little Danny and reached for Danny's unlocked phone on the treadmill. He typed his number into your contacts and sent himself a text "So I have your number too. I'll text you later to set something up. Looking forward to seeing you and getting together so we can... get to know each other better" John said as he looked up and down Danny's tight, feminine body. John left, not before putting his big hulking hand on the small of his back, brushing the top of Danny's ass as he did so.

As Danny, completely thrown off by the encounter, just stared dumbfounded at the big back of John. He was completely humiliated that he looked so girly and feminine that a man (another man, damnit I'm also a man!) hit on him and asking him out! Was he really that girly looking? And why did Danny's 4 inch dick twitch when johns hand brushed his ass? He really needs to get new clothes.

But these thoughts were brushed aside as a next text dinged in his phone. The text was from Jessica...

Chapter 3: Halloween Party Deal

Danny opened up the text from Jessica:

"Hey Danny. Have you figured out what you're gunna dress as for the Halloween party?? I have some ideas if you haven't figured it out yet. Why don't you come over to my place at 8 pm and we can talk about it, ;)"

Danny, with his masculinity taking such a huge hit from his dealings with John, got a huge boost of confidence from the text. Danny and Jessica broke up on amicable terms (or so he thought) so he didn't think anything odd about the request.

With no plans for the party, and no other girl on the list to take as a date, he thought it wouldn't hurt to go with Jessica. As lazy as he was, this would take the work out of figuring out a costume. He probably would have waited until the last minute and shown up in an old jersey, which would be a bad look to impress the girls at the party. Plus, if things don't work out with a new fling, from her winky face at the end sounds like he could get lucky again with Jessica for one more go around.

Danny left the gym and headed to his apartment. He walked into the 4 bedroom he shared with 3 of his frat bros. A modest apartment with a kitchen and laundry in the unit with a big living space with a 65" flat screen to watch sports. With four frat bros, the place was a pigsty. Beer cans, old take out containers, a bong and ashtray strewn around the flat spaces and floor. Danny looked around with disgust at the place and walked to his room to take a shower before meeting Jessica.

Danny stripped out of his sweaty work out clothes, his tight shorts taking some work to wiggle out of over his big girly ass. With the apartment empty, Danny put on his secret favorite music, girly pop music. His bros would make fun of him forever if they caught him listening to such girly music, but he loved to listen to it in private.

With Taylor swift bumping in the bathroom, Danny turned on the shower and looked at himself in the mirror. His almost shoulder length brown hair framed his pretty, boyish face. His face still smooth even after not shaving for over a week. His toned, but soft, upper body was also mostly hairless, besides a thin tuft on his chest. His chest, while thin, had a small layer of fat that just wouldn't go away, giving the impression of small breasts that was even more defined when pressing his arms together making visible cleavage.

His thin, girly arms had almost no muscle definition from lack of weight lifting. Thin waist, from years of cardio, was nice and tight. While he worked out abs constantly, it always bothered him that he couldn't get visible abs. Instead, a soft belly lead to his wide waist and hips, giving almost an hourglass figure.

His muscular thighs, covered by a thin layer of fat, looked perfect framing the thigh gap between them. While somewhat self concious of his 4" penis, the girls he was with never complained (to his face at least) and what he couldn't get done with his length he made up for with skilled tongue between a girls thighs. Danny turned to look at his prominent ass. While worried about how girly it was, he took a lot of pride in how he built it to where it is now, and the strength that came along with it.

He stood up on his tip toes and slightly arched his back to get a better look at his peach, proud of how it looked. His legs, covered in fine hair, would look perfect if shaved on a cheerleader or covered in stockings and a tight skirt. His small feet for a guy, size 6, got a lot of ridicule from the guys, but he tried to cover his shame with a joke "the big feet thing isn't always true guys!" But knowing his small dick didn't make that true, but the guys didn't need to know that.

Danny, with the shower warmed up, lathered up his body with body wash as he hummed along to Olivia Rodrigo. His phone pinged and he reached out of the shower to see the text. John's name popped up:

"Hey Dani. Sorry I had to run earlier but wanted to see what you were up to on Thursday? We're going to a bar and I was hoping we could meet up before the party to talk about matching costumes. Can't wait to see what you look like in a sexy costume girl!"

Danny, again stunned this guy thought he was a girl, just stared at his phone with shame and humiliation going through him. He had to tell this guy off and set him straight, that he was a STRAIGHT guy not some girly bimbo!

As he was typing up his response that he wasn't going to the bar with him, his skin started to burn. Scared, Danny jumped back under the water to soothe his burning skin. As he washed off the "body wash" he saw his body hair going along with it! Shocked, Danny grabbed the bottle he used, realizing his mistake. Jessica had left some Beauty products at his place and he had used her hair removal cream instead.

Washing off the last of the cream, Danny got out of the shower and looked again in the mirror. Gone was the soft tuft of hair on his chest and the fine hairs on his arms and legs. Instead was smooth, tanned and slightly pink from the cream, skin, making him look like another girly coed on campus! In horror, Danny saw his soft cock start to get hard looking at his definitely girly body!

Danny, still slightly sensitive from the cream, grabbed Jessica's body lotion to soothe his burning skin. Covering his body from neck to toes, Danny realized this lotion left his skin gleaming and shiny. His tanned, toned legs now looked like they belonged to a Victoria's Secret model or some playboy bunny!

Danny, still humiliated, contemplated hopping in the shower, but another text came through from Jessica confirming 8 pm tonight. Danny looked at the clock and saw it was already 730, so he needed to hurry. Danny sent the text and then saw he had sent another text earlier to John. Being scared by the burning of his skin, Danny realized he had mistyped his text and what he actually sent to John:

"Hey John, yeah I am a cute girl. I'll definitely see you on Thursday at the bar!"

Danny wanted to fix the text but needed to hurry to get over to Jessica's. Wrapping a towel around his waist, Danny headed to his room to get dressed.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
23 Comments
Badboy1616Badboy16163 days ago

Great starting story! It’s brave to write one on here. Most of the people commenting have never even attempted a story especially the haters so don’t listen and just do as you do! I have just started to wear panties and love how they feel on my smooth legs and ass. I hope to see this in the next few chapters. However, I just can’t make up my mind on wether to continue this way. I love wearing them out in public though. It’s a thrill to know I have them on especially the pink thongs! I’m not really sure what step to take next. Anyway, I see there are a lot more chapters to read and please keep writing! You have a real talent!!! The start of this series is hot! I hope you see this comment.

CdslavejessieCdslavejessie10 days agoAuthor

Sewblon, hair removal cream has worked for me! Sorry it didn’t work for you. I know it’s not the most effective but there’s a little suspension of disbelief in some stories. Not going for a NY times best seller lol but I do appreciate your feedback! And I know the text error was wonky and not good writing but it was my first chapter of my first story! You can spank me later for it ;)

SewblonSewblon11 days ago

Hair removal creams have never been effective for me or anyone I know. But like Sweetbobbi said, the text error seems rather contrived.

Martin594Martin594about 2 months ago

So far, so good. Hope it gets hotter.

AnonymousAnonymous2 months ago

Writing in the 3rd person robs the story of the protagonist emotional and physical experience. Thus removing the readers opportunity to imagine themselves in their place and relate to those feelings.

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

The Man That Converted Me A young man is snowed in & turned out on a mountain getaway.in Transgender & Crossdressers
Dream Girl Pt. 01 Get the girl... or become a girl for BBC.in Transgender & Crossdressers
Party Slut Never fall asleep at parties!in Transgender & Crossdressers
Feminized by BBC Friend Ch. 01 My BBC friend slowly feminize me.in Transgender & Crossdressers
The Deal Freddy's wife convinces him to dress up and go clubbing.in Transgender & Crossdressers
More Stories