I am 18 and all participants/characters must be 18

Disclaimer: Please read all the way through. I'm only looking for creative and active participants that I can vibe well with to really bring this roleplay prompt to fruition.

Also, let me say this now. I am located in the Midwest of the United States, timezone being Central Standard Time (CST/UTC-6). The closer you are to my time zone, the more compatible we'll be as far as active partners in this prompt goes.

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Dressed Up And Discovered

[B4T] \ [CD/TF4M]

I always tell my staff that there’s nothing wrong with taking a much needed break from the day-to-day grind, even engaging in a little escapism from the stressors of reality. The irony of me saying that isn't missed on me because up until now, I haven't treated myself to some much needed time off from work in nearly two years. Being a Public Relations Manager for a small PR firm, I'm quite the workhorse around the office. I always filled in for others when they needed to call off or spend more time with their families or significant others. But this time though, I think I dropped a bombshell when I announced that I would be taking quite a bit of time off. Three weeks in fact. Believe me, this stallion needs a break.

Yeah, there's nothing wrong with taking a much needed break from the trappings of life and enjoying a little escapism. I know this first hand, though my sense of escapism is rather different than most would expect from a guy such as myself.

At only 34 years old, I’ve already managed to achieve more than half of what others around my age have done. My personal philosophy is simple: work smart and play harder. I'm already a high-ranking professional with a great career and own my own home in a very nice neighborhood. Having no kids and being a good looking single bachelor also doesn't hurt me in any departments as I'm quite popular among the ladies. All that said out the way, I'm not without my own share of secrets.

My secret has a name: Jocelyn. My female persona. Yeah, I'm a crossdresser and a pretty damn good passable one at that. Not to toot my own horn, but I would fuck me if I could if I saw myself dolled up from head to toe.

I only started crossdressing about 8 years ago after an ex-girlfriend I was dating at the time got me to do so for her for a Duo Halloween Costume Contest that she originally was going to participate in with one of her friends until they had a falling out. They were supposed to enter as cheerleaders from the Clovers cheerleading squad from the first Bring It On movie. I wasn’t initially keen on the idea but after some tantalizing persuasion, she won me over and spent over a month prepping me on the basics. Long story short, we won the contest and enjoyed a nice Miami vacation that winter as a prize. Though she and I would break up that following summer, I came out of that relationship with something that had been either instilled or awakened within me. I found myself essentially pulling a Lewis and Clark with exploring this newfound territory of myself, leading to me learning new things about myself but also developing exactly who Jocelyn is from the ground up.

I even found myself curious about having sexual relations with men, something that I did follow through on though only after being treated to a nice romantic evening. None of the men I've been with were guys I knew from my personal life and I typically didn't keep contact with them after a while thanks to both sides not really looking for anything serious. Besides, that’s only something I find myself going after when I’m expressing myself en femme. Outside of that, I’ve continued enjoying having sexual relationships with women.

I can’t say if it was a hobby or a desire, but I found myself wanting to further explore and experiment with femininity and its many aspects. In a way, it became something of an escape from the stress and masculine trappings of my day-to-day self. With all the different terminology these days, it’s pretty hard to narrow down exactly what I am, though I will say I’m content with my assigned gender. I’m just very fluid behind the scenes with it. Unlike some guys, I got no qualms stepping outside of my comfort zone of masculinity and swimming in the deep end of the pool of femininity if that makes sense.

Which brings me to now. Three weeks off from work to enjoy all by myself. I thought of going on vacation out of town, but I'm staying in the city instead. Hey, sometimes a stay-cation is the more suitable option than paying airfare or gas to go somewhere for a vacation.

I've informed my team of employees at work as well as my clients that I'm taking a personal two weeks off. I’ve been a workaholic for a while now, so I’m sure many of them are surprised that I finally caved and requested some time off. To quote my own boss when I told him the news, “You’ve been burning the candle at both ends for too long around here. Get out and learn to live a little. Everything will be fine around here.”

He’s right about that. I have been shouldering the burden of the workload long enough at my job. It’s been way past time for me to live a little and that’s exactly what I set out to do for the next two weeks. The thing though is that these two weeks will be well enjoyed by me but with an interesting twist. This is more than a vacation from work, but will also be both an experiment as well as a personal sabbatical, even a little experiment for myself to engage in. See, I’m not going to be spending my time away doing things as I would normally. In fact, I’m not even going to be Quentin Rutherford for the duration of my time off.

Like I said, I have no qualms with swimming in the deep end of the pool of femininity. And three weeks of being Jocelyn 24/7 will be the testament to that.

It’s an understatement to say that this will be interesting. Still, I’m ready to dive head first into this. You only live once, right? Most in my position would be asking themselves what could go wrong.

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Hi everyone!

I’ve dug deep into my personal well of RP prompts and ideas, found this old gem and given it a revamp. Now with my own newfound interest for this prompt, I’m looking for those interested in participating in it.

The basic premise here is nothing out of the ordinary. My character decides to spend their two-weeks off from work as a chance in-a-lifetime to secretly live 24/7 as their female persona, the drop-dead gorgeous Jocelyn. Whether by happenstance or not,this decision will result in them being discovered which will lead to a wide variety of events and escapades happening that they'll will be pulled into. Just exactly what do I mean by that? Well, there will be a CYOA (Choose Your Own Adventure) element incorporated into this prompt that can be explored and further built upon. After all, I’m all for creating new pathways for the story to take its share of twists and turns, even switch up the tone momentarily or semi-permanently.

Though we all know exactly what subreddit we’re in, my intention for this is to be a story-driven roleplay with about 70% storytelling and character development as well as 30% eroticism/smut told in 1st person perspective. I’m okay with this being a short-term thing but I prefer finding partners I can vibe well with with the intention of making this into a long-term roleplay.

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As I mentioned above, this slice of life RP will have a CYOA approach to it with you having options on how this roleplay prompt can go. The CYOA options you can choose from are...

Choice A - Neighborly Dealings: This angle presents me being watched and discovered being Jocelyn by a next-door neighbor or someone else on the block who decides to approach me with whatever intent he has on his mind. With this, you can be either type of neighbor:

*The noisy (maybe overly sheltered and socially withdrawn) neighbor on the block who works from home and keeps tabs on everyone's comings and goings, sometimes to the point of secretly using surveillance tactics.

*The new neighbor on the block that seems cool and keeps to himself while working on various renovation projects in and outside of his house, allowing him to get glimpses of me as I come and go.

*The cordial longtime neighbor who always interacts with my character and who also conveniently has an upstairs window that looks directly into my bedroom windows.

Choice B - Forgotten Spare Key: With this angle, there's an unexpected visit from your character after you've decided to make an unannounced visit courtesy of a spare house key that you have. Your character could be either one of the following:

*One of my best friends stopped by to hang out or maybe vent about his personal problems. (job issues, problems in his marriage, etc.). Perhaps I once let you stay with me while you were going through hard times or had you house sit for me, which would explain how you have a spare.

*The brother of an ex-girlfriend or her current boyfriend stopping by to grab the rest of her things that she had left when she moved out months ago but never gave back the key she had.

Choice C - Out and About: Your character eyes me out in public somewhere whether shopping or out having a drink at an upscale nice establishment. Your character can be one of the following:

*Either some close friend or a random average Joe (whether either one behaves like a total gentleman or a completely obnoxious horn dog with an inability to accept rejection is up to you) looking to shoot his shot with the cutie he's been eyeing.

*My direct supervisor/boss from work looking for a casual fling outside of his marriage or newly divorced looking to mingle with the beauty who he's smitten by only to discover it's me (or maybe not he doesn't find out…).

*A former classmate, bully or rival who is now older, matured (or somewhat matured) is checking me out as I'm out and about.

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If you’re interested in participating in this roleplay, please be aware that I’m solely looking for those who know how to be detailed and active participants.

I tend to do two-to-three detailed paragraphs per response, sometimes more than that depending on what I’m establishing in the scene. I don’t need novella-size responses from you, but I do expect that you match me and show the same amount of detail and care as I will. If all you can produce is one or two lines, then we aren’t going to mesh well. Anything low effort and not literate is a hard no for me.

I also am looking for partners that know how to be mature and respectable enough to communicate with me when they’re going to be busy or when they need to take a break if needed due to IRL. There’s nothing more I hate than planning and staging with someone for them to only just drop out without any word or warning. If you know you’re this kind of person when it comes to RP, just stay away.

In any case, if you can adhere to my requests and are still interested then hit me up via chat or DM. In your message, please include the password I put in this post and include the following:

State what time zone you’re in - Again, I residue in the region of the United States that’s in the Central Standard Zone (CST), so I heavily prefer someone either in said same timezone or in a timezone that’s only a few hours ahead or behind.

Discord handle - That’s the only platform that I RP on. No exceptions.

Info about you - Actually tell me what grabbed your attention and interest in wanting to participate in this prompt.

Initial Choice of Start - Choice A, Choice B, or Choice C.

Character info - Provide a brief detailed intro of your character as far as their names, age, physical description, personality, occupation, marital status, etc.

Kinks and limits - Shouldn’t need any explanation.

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Kinks: Crossdressing, feminization, bimbofication, flirting, passion, foreplay, anal, assplay, gentle sex, rough sex, forced sex, being bred, oral, facefucking, facesitting, possessiveness, frottage, body modification, big dicks, ass worship (receiving), dancing and twerking, groping, grinding, getting fingered, getting rimmed, kissing, spanking, straight-to-gay, romance/forced romance, secret romance, cheating, dirty talk, spanking, risk of getting caught, dubcon, noncon, blackmail, recording, exposure, public play, porn logic

Password: Fluid3

Limits: Piss, scat, fart, bad hygiene/odors, hyper, feet, spit play, death, blood, gore, vore, vomit, incest, mpreg, raceplay, political play, using anime/illustrated refs, anthro/furry/animals, sounding, chastity, cbt, one liners, Bad RP, deciding my IC actions without my permission.