First Time Crossdressing For A Man [TM]

Hello everyone,

This is a crosspost r/gaystoriesgonewild. I’ve been a lurker here and have a few stories of my own that I could share but never have. I got a pretty good response on the above sub so I figured I would post here too! 😋 what follows is copied from the original post:

Now I know that the whole sissy fetish isn’t for everyone in this sub, or even really that accepted in the gay community at times. That being said, for me, the appeal to the sissy fetish is much more about the humiliation aspect of the kink than anything else. As this story will explain, I never knew how much I really enjoyed being so submissive.

What follows is entirely true, and I will never forget it:

A little about myself. I was 20 years old in college at the time. I was about 165 lbs and 5’9. I had always enjoyed dressing up from an early age. When I was much younger, I vividly remember stumbling upon transsexual porn and becoming instantly infatuated. I found myself wanting to dress up and wear sexy lingerie. When I finally moved out of my parent’s house at 18, all bets were off. I had roommates, but would almost instinctively close the doors to my room every night and slip into some sexy clothes and play with myself. I went to local sex shops and bought tons of outfits over time, dildos, heels, pink chastity, the whole gambit.

School Bus [mf] [fDom] [exh] [huml] [reluc] [shoe]

I had been late getting ready this morning. Classes started too damn early in high school.

Bags under my eyes, hair wet, with my thick glasses, long sweatshirt, and tight jeans, I took a window seat in the middle of the bus. The popular kids walked right on by as I blew clouds onto the chilly, clattering window. I didn’t want to talk to anybody this morning. I hadn’t had time to masturbate, and this early break from my routine had already put me on edge.

The seat warmed under my body and yet more jocks huddled in the back, as yet more nerds sat solitarily in front. I liked a few from either crowd, but didn’t fit in with any groups. I was a drifter, no center of attention yet not unwelcome either, and the middle seats were the fringes where I roamed. But while I wasn’t part of any group, I wasn’t totally alone, either.

Su[mm]oning an Incubus Ch. 2, A Night of Lust

[Chapter 1](https://www.reddit.com/r/eroticliterature/comments/9xffec/summoning_of_an_incubus/)

“Excellent work Jesse, top marks.”

The brightly lit classroom held a small cluster of students, all seeming as bored and uninterested as any other class in the world. At the front, a familiar green eyed young man gave a small smile to his teacher. The board in front of him had been filled with a series of runes and symbols, almost gibberish to the untrained eye. But to a student of witchcraft, it was a rather hefty accomplishment of memorization. Jesse gave a nervous laugh.

“Thank you Miss Jetta. It’s really nothing.”

The teacher shook her head, standing up from her desk. “No Mr. Murphy. You’ve improved greatly over this past month, and I am genuinely impressed.” She smiled. “This is your last year, and it finally feels like you’re taking your study seriously. Now go sit down, and let’s finish the lesson.”

[M]y first submission to a [F]emale happened at Burning Man

y first experience submitting to a female dominant makes a good first story. It happened at Burning Man several years ago. I was riding an art car, this one was a large bus with one of the long sides completely removed so people could hop on. All the seats were removed and replaced with pillows and blankets.

I saw one girl being … admired .. by two guys. It looked like a couple amateurs trying to submit to a seasoned femdom. Granted, I didn’t have much experience with male submission to compete with them, but by this point had plenty of experience in BDSM and Dom/sub activities in the reverse role (it had simply been much easier to find partners or girlfriends that wanted to submit).

I made my way to her, and made some confident sounding soundbite — I don’t remember exactly what I said but the gist was I thought I knew I could outperform the current guys. She suggested I try worshipping her, starting at her feet, and within a couple minutes she dismissed the other two guys.

The Timestop: Chapter 2

2 years ago i started a series called “The Timestop”. Unfortunately the last two years have been very hard for me and, despite having a lot of the main story completed, I was unable to publish anymore of the story. The last few months have been a lot easier and i am now pleased to say that a lot more content is on the way. I plan to publish the next few chapters of The Timestop before introducing a new series along side it. Chapter 2 is not as long as the last chapter but I had to restructure a lot of the story and so this is a compromise I have had to make. I hope you enjoy and I promise chapter 3 will be far better.

The Timestop Chapter 1: [https://www.reddit.com/r/sexystories/comments/5116xd/the_timestop_str8_fm_school_anal_huml_cuck_nc/](https://www.reddit.com/r/sexystories/comments/5116xd/the_timestop_str8_fm_school_anal_huml_cuck_nc/)

Chapter 2:

Mrs Carter sprang back into life as I unfroze time

“Now girls-“ she said before stopped mid sentence. Her eyes had suddenly gone wide and her jaw started to slack.

“Time…time…I…” she muttered as her hips started to gyrate and her hands dug into the desk. i could see her knuckles going white as she found to keep herself composed, her look of shock turning into confusion.

Just a quick story on a rainy day. Hope you enjoy!

When I’d gotten into Folsom University, it was the happiest moment of my life. Both my parents were alumni, and my older sister was already attending.

I had a scholarship, an old Ford truck my dad and I fixed up over the summer. I’d saved up some spending money working at the Loomis mill. I was ready for college.

What I wasn’t ready for was dorm life. I hated it. Dealing with people daily I would prefer to punch in the mouth. I hated the close quarters of the dorms. My entire life there was a washing machine that I could use whenever and the units on campus were shared.

By the end of the first week, I was thoroughly homesick and I hadn’t seen my sister at all.

Saturday’s in the dorms were lively. It was my first time being anywhere co-ed, and as any young men would be, my roommates were excited. The door to our room was constantly open and every so often a young woman would walk by and if she was only wearing underwear it was all the better.

[F] I was a slut on vacation

Sorry if I wrote too much.

Just a bit of back story about myself. I am single now, but I was with my ex for 4 years during which I became extremely submissive to him. He pushed my limits, exposed me, shared me on some occasions, got into rough sex, some humiliation play, and I shared really enjoying it and slowly addicted to it.

I went on vacation with two of my friends, for a week in Cuba. Full inclusive and all. Lots of guys were flirting with me at first but I want particularly interested at the beginning. On my fifth day there, I was at the pool bar sipping drinks with my friend, and two guys approach us. We hit it off, and my friend and the other guy got out of the pool to grab a bite to eat.

I stayed at the pool, relaxing, drinking, and chatting with my guy. We stayed there for about an hour, and I was getting pretty tipsy, and I could feel his hands all over me. He kept pushing his hands between my legs. I liked the attention, and I was getting pretty horny myself. We decided to go to his room, and rest.

Sabina the Not-Yet Twenty Witch: Part 3 [MF][Sex][Mast][Exh][FDom][MC][Voy[[Magic]

**Note:** More is coming from The Neighborhood. Editing for Reddit (formatting) is not a simple task. Enjoy the filler stories in the interim.

**Chapter 6: A Chat, A Cat, and Sabina’s Black Patch**

After her roommate left for the morning, Sabina called Jackson, telling him the whole sordid vampire story.

“She made me come for an hour straight.” She said, angry.

“Like, one giant, long orgasm or—.”

“Like, thirty in a row. I feel like I was doing cross fit all night. Every muscle is sore.”

“Well, just to clarify, she didn’t make you do that, not really. She likely used a Heart’s Desire curse, which basically means giving someone too much of a good thing. It all happened in your mind, if that makes you feel any better. I mean, if you really like cupcakes, you would have probably felt like you were eating too many cupcakes and thrown up a lot. So, apparently, you just like sex…a *lot*, though. Let’s be honest, it wasn’t a hard guess for an initiate witch.”

“You don’t have to sound so amused, Jackson.” Sabina said.

Sabina the Not-Yet Twenty Witch: Part 2 [FF][Sex][Mast][Exh][Huml][FDom][NC][Magic]

**Chapter 3: History or Herstory?**

Sabina’s morning class was Early American History, colonization stuff covering everything from Canada to the Caribbean. It was interesting to hear the human side of the story, though the witches knew there was a lot more magic behind the scenes that made the lands inhabitable by Westerners. The indigenous people had strong magic, but they made some bad deals with the spirits of the world, many of them becoming corrupted, and the humans only exacerbated that with their introduction of technology and things like iron and steel.

She sat in the third row. It gave her good line of sight to the exits, not that she was ever that worried about threats at the school, but a little safety went a long way. Her friend Vera dropped down in the seat next to her.

“Nice top.” Vera said.

“Thanks.” Sabina said, straightening it a bit.

“You know you can see your bra through that.” Vera added.

“But not my tits, right? Just cleavage?” Sabina asked, cupping her bare breasts through the sheer fabric to convey the illusion.

“Well, no, of course not. I’d let you know if that was the case…after I enjoyed the view.” She grinned.

Yoga Instructor turned Hotwife and Whore [MF]

On the outside, my husband and I live a normal life. We have ordinary goals, dreams, aspirations, fears. I portray the girl next door – the girl you probably grew up with all your life. We live in New York City. He has a stable career in HR, I’m a Yoga Instructor. If you’ve seen a cute woman walking in yoga pants, that may have well been me. We are your typical 20s/30s young urban professionals, but without the entitled wealth or pretentious importance.

However, hidden deep down, people would be shocked at our perverted, sexual thoughts. My husband first introduced me to the role of a Hotwife. This world of kink, of objectification was something that I fell in love with. My husband, my mentor, my Dom, shared his love, support and confidence that allowed me to find my trophy slut role.