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For full disclosure I'm gender queer 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! And I'm sure this one would work just as lovely with an Aunt as it would a Mom.
Mom's lonely.
You try to put a brave face on, of course, but it's been obvious for a while now. The way you look longingly out of the lounge window, thoughts in a far away place until you notice I'm there and force a smile. That hint of disappointment in your voice whenever I say I'm going out for the evening, not mad at me but downcast that you don't have something similar to look forward to. I've known you far too long to ignore it, and it feels wrong for me to pretend otherwise.
It isn't surprising you feel this way. After the divorce a few years ago you've struggled to get yourself back onto the dating scene. All your friends are married, and are too busy with work or kids to go out to bars and pick up guys like you did in your younger years. These new dating apps and websites aren't much better, too many people looking for a one-night-stand or an affair instead of a serious, committed relationship. And I can tell it's affecting your self-confidence. The fridge has become increasingly occupied by dieting products and health foods, despite my reassurances that you look stunning just the way you are. And you've become increasingly reluctant to go to family get-togethers, lest you have to deal with the incessant questions of 'have you met someone yet?'
And that's why I've decided to help.
But sitting on the couch, hands resting between your thighs, you're still not sure what form that help will take. I asked you to clear your schedule for this evening, something that wasn't particularly difficult, but other than that an assortment of bangs and crashes from upstairs have been the only indication of what exactly I've got planned. Sitting back, running your hand through your hair, you hope it isn't something silly like a blind date. While you'd trust my judgement, meeting up with a stranger following a recommendation from your son sounds like a recipe for disaster.
Then all of a sudden you hear it. My bedroom door opens in the distance, the first time in what feels like hours. Footsteps begin down the stairs, but as you listen they sound... different. Mine, obviously, but not. And as I reach the hall, the reason for that distinction becomes clear. Gone is the usual soft patter of my sneakers or socks, and in their place are... are...
... heels...
And as I emerge in the doorway you suddenly see the reason. Looking me up and down, you lay eyes upon your son. Except in my current attire, son hardly feels like a fitting word at all. Strappy high heels, long silky legs, a tight dress which seems almost painted onto a surprisingly svelte and curvy body, and a face which is... is pretty, beautiful, enticing. I smile, my lipgloss glittering in the light, putting my hand on my hip and allowing your shock to abate before finally speaking.
'So... yeah...' I say softly, voice about as feminine as my appearance, taking your surprise for granted. You've always known I've liked dressing up, and that I've crossdressed a few time with friends from University. But this?
'I know you've missed going out to bars, but I thought it would be a bit weird if you went out with your son,' I continue, a cool calmness to my voice, even if I do feel more than a little nervous myself, 'So how about a girl's night out instead? What do you say, Mom... let me be your wingwoman?'
Hey there, I hope you enjoyed my prompt. This evening I'm looking for a lonely Mom (or maybe an Aunt) who has been down on her luck when it comes to dating. Divorced for a few years, and hitting her 40s without any sign of a stable and loving relationship on the horizon, she's beginning to wonder whether she's too over the hill for love. However, when her son, a young man who has been increasingly questioning his own gender, offers to be her wingwoman for the evening, things will all change for the better. I'm looking to play out the very wholesome, romantic and raunchy relationship that follows.
As you can probably tell, I'm looking for this RP to focus on two characters who slowly come to accept themselves. Your character has become increasingly self-conscious about their body and place in the world, and through this new relationship comes to accept how sexy and deserving of love they are. My character is unsure about their gender identity, and soon finds they are most themself when they're a woman.
The specifics, however, are totally up for discussion. Maybe Mom is a career woman, someone who has been too busy in her high-flying career to date until my character intervenes. Or perhaps Mom is more of a housewife, staying at home and feeling increasingly isolated because of it. Perhaps Mom is a bit more dominant in the bedroom, yearning for a time where she can pull out those toys hidden deep in the back of her wardrobe. Or maybe she's a bit more submissive, inexperienced after only being with my character's Father, and therefore needs to be brought up to speed by her more worldly and lustful new daughter. Or maybe something completely different! There's a bunch of different ways we can play it, so as long as it hits the basic themes I'm open to any of your suggests or thoughts. Let's make something wonderful together!
In a partner, I'm looking for someone who enjoys long-term and gradual RPs with lots of sexual tension and romance. In particular, I really like writing with people who express their character's internal thoughts, feelings and motivations. I would like this RP to take place over a number of scenes, slowly ratcheting the tension. Let me know if you have any ideas for different scenes! The above piece of writing is just to set the tone, so we can start this one off however we like!
My main kinks are romance, feminisation/feminization (but not the mean or forced kind), incest, cumplay/bukkake/gokkun, D/s and switch dynamics, 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 meanness, 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!
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