For full disclosure I'm M playing M/F/T. I hope that's not an issue for you! Here's my DPP Profile!, most of my old prompts are still up for discussion if they take your fancy more, and I'm up for discussing other prompts/ideas with similar themes to my own! If you see this prompt, it's probably still open, so feel free to send me a message!

The below text is more a writing sample to help set the tone than anything definitive, all details are up for discussion!

You aren't the most experienced of young men. I don't say that as an insult, mind. You're handsome, funny, clever, talented, have a tonne of friends both male and female. You're the sort of guy who will make the right woman just swoon. It's just... whenever you find yourself getting close to a woman in a more romantic way you shut down. Your hands clam up, chest goes tight. You'll leave messages on Tinder unread for a week, long enough for girls to think you aren't interested. You can get a girlfriend, no doubt about it, you just can't take that last step from just friends to something more.

Now, were I a proper big brother I'd have a few different responses to this. I'd sit you down, reassure you that you're enough of a man to pull any girl you set your mind to. I'd recount my past experiences, reminisce about the times I got girls I really had no right to or the times I messed up what should have been an open goal. I'd take you out to a bar, try and catch the eye of two single ladies and act as your wingman for the evening.

But I've never been much of a big brother. We've always got along, of course. You're only a few years younger than me and we bonded over computer games and other hobbies. But I've always been a lot more effeminate than you. From a young age I surrounded myself with female friends, though rarely found myself having romantic interest in any of them. I never tried out for the football team, preferring hockey and tennis or just sitting around with my friends in the library chatting. Even my body, with narrow shoulders and wide hips and a bottom thicker than it has any right to be, looks a lot more like a woman's than a man's.

And that gave Mom an idea.

Mom too has witnessed your struggles, but she's come up with a solution. It's not a secret that I have certain other hobbies. Though I insist it's just part of an elaborate in-joke with my friends, I've found myself going out to bars and clubs more and more dressed like a woman. Tight dresses which show off my silky legs, high heels that make my butt look even rounder and fatter than usual, and make-up done with heavy eyeshadow and thick lipstick. And Mom knows other things too, knows that in the privacy of my bedroom I wear more than just skimpy dresses and high heels, that I put on lingerie and naughty outfits and entertain myself until the early hours.

And so she's asked me to share that with you. While I was a little reluctant at first, what Mom said made sense. You need more experience around pretty women, she said, to get acclimatised to the smell of their perfume and the way their hips sway in such an enticing way. And who better than to help with that acclimatisation than me? I can teach you how to talk to a woman first hand, what to say and how to act. I can go through some roleplays with you, pretending like I'm a girl you met at a bar or on Tinder. I can help build your confidence, get you used to all those subtle little things you have to remember.

Yet while she hasn't said it to me, Mom also has other plans. Because there's a lot more for a young man to experience than just flirting. He needs to know how to kiss, how to touch a woman's body, how to take her into the bedroom and ravish her. And who better to teach you than your new big sister...?

Hey there, I hope you enjoyed my prompt! In this one I'd like to play an effeminate older brother who, at Mom's request, commits to spending the next few weeks as your beautiful older sister. Although this would initially be under the pretences of helping you get used to being around a young woman, soon we'd realise that Mom has other ideas for us, ideas we have no intention of rejecting...

I have a lot of different ideas for this RP, but most things are up for discussion, so don't take anything as set in stone if you'd like to suggest alternatives. Collaborative storytelling is always more fun!

Your character is totally up for discussion! While I suggested they are inexperienced in some respect I'm open to tweaking or changing the prompt based on your views (it's your character, after all)! However, I would prefer that you don't play the character too extreme, either too confidence or too shy. Somewhere between those two poles would be perfect, but otherwise I'd love to hear your thoughts.

I'm also up for discussing my character's appearance. While I'd like to start the RP as a very feminine looking guy who, in make-up and dress, looks indistinguishable from a woman, and while I'd like to get proper breasts at some point in the RP, I'm not super fussy on my character's body shape, ethnicity or general appearance. I thought it might be fun if I was taller than you though. Let me know what you think!

As for Mom, I was imagining that she wouldn't be involved with us sexually, but would instead act as more of a matchmaker. She sets us up, slowly pushing us together, occasionally using her motherly authority to brush aside any reluctance. As you can probably tell from my post history I really like the idea of Mom using both the carrot and the stick to get us together, though things will always remain wholesome. I imagine we'd both control Mom's character, though we can discuss that further in PMs.

For the story itself, I'd like a combination of both smut and storytelling. I don't want this just to be about sex, I'd like to explore the growing romantic feelings between our two characters. And to facilitate that I'd really love to hear from partners who enjoy writing about their characters thoughts, feelings and emotions. I'm imagining this RP would take place over a number of different scenes, something we can discuss in more depth in PMs.

My main kinks are romance, feminisation, incest, cumplay/bukkake/gokkun, D/s (with me as the s), outfits and lingerie, build-up, free use, taking orders, name calling (feel free to call me a slut or a whore, especially out-of-RP if you're so inclined ;) ) and group sex. My limits are u18s, excessive pain, non-con and skat/watersports. Not all these kinks need to be included in the RP, but this should give you a good overview of my likes and dislikes.

I try to respond at least once per day or two, although sometimes real life will get in the way. I write in the first person present, and generally try to write detail, liking around 3 paragraphs per response (although of course that fluctuates). In your response, I'd like you to include a little bit about the character you would like to play, your kinks, and how you imagine this RP developing. The more detail you can include the better, the first message is super important to me, and short or detail-lacking messages are a bit of a turn-off. I usually leave prompts up a little while before replying, so don't feel the need to rush your response. I'll try and reply to everyone, but short messages which don't give me much to work with probably won't get a response. Also please keep everything to Reddit PMs, thanks :)

I look forward to seeing your responses!