For many moms, it was always difficult to see their sons turn to another woman. And for you, it was no different. Zoe was nice. More than that, she was hot. Extremely hot. Co-ed girls were something else nowadays, that was for sure! But she was nice. She stayed for dinner and even talked with you. But the next week, when you asked your son where was, the only answer was a disinterested shrug and returning a text to Amanda. Who you met that night. And never again. Then it was Rachel. And Isabella. And Dani. And then Rachel again, and you thought that this one might have stuck... but no, it's actually Rachelle. Not that it mattered. Eventually they all stopped mattering, for one reason or another, and all you can do is watch the parade of nameless sluts traipse through your home and fuck your son, who was so ungrateful to his mother that he couldn't even respect women enough to know their names.

So when he came home with some of his friends, a darling girl following him after, it shocked you when, with a dulcet baritone, he asked where the bathroom was. He. You looked for a moment. And then at the boys all playing Xbox. And then at him again. He laughed. A friend of a friend. It clicks in your mind. Of course. Your frat-bro son would never... Not that you had ever instilled those sorts of... Sigh. Let's just say he took after his father. A bitter mouthful if you've ever had one. And after many an unsatisfied night... You certainly have.

But this girl... boy... Unlike every other femme-presenting person to walk in with your son, this one had a name. It was cute. It was charming. It was the name of someone you could feel comfortable with. Someone who ate your cooking with glee and asked about recipes. And knew that there was the perfect little store in the Village that sold the best cute-looking donuts. And there was just something about his large smile, his cute little purse, his skirt that was lifted in just the most darling...

Woah.

Whoa!

WHOA!

Okay. There was no denying manhood now.

But something was off. The way he stared at you, the way his eyes drank in your form, the large, oversized, heaving breasts, the trim waist that even his slim arms could wrap around, and the large, bubbly, shelf that adorned your rear were all held under his gaze. And you couldn’t help either. From the way way his skirt tented when he sat down, how he wore it to hide himself from you, to make it clear that he wasn’t staring when he so clearly was. He was just a little bit into, you think, and no matter how many times you caught his friends staring at you or staring at… him, your eyes always met his.

Hi there DPP! I'm feeling a bit in a femboy mood today! A bit of a rarity, but I definitely caught the femboy bug. And I want to share it with everyone! Not really. Wear a mask, stay safe, people.

Now a bit about the prompt! I would really like to play a femboy who starts as an unwanted 1 in his friend-of-friend's friendgroup to... Well... To fucking the host's unbelievably busty mother. Preferably in a dominant position, but I'm a bit of a total switch, so either way is fine! Personally I would like to start the roleplay a bit of the ways into the relationship; they've met, they've confessed, perhaps they've even shared an wee touch or two, but haven't really gone too physical yet.

As with every other prompt I write, I need to make this extremely clear: THIS PROMPT HAS UNREALISTIC SIZES and this is NON-NEGOTIABLE! If this doesn't make you comfortable, that's totally okay! But if that is the case, do not try and talk me out of it. Having 36DD is not 'good enough', nor is 'just imagine them being big' work either. And while I do have limits to my sizeplay and unrealistic size fetish, trying to lower those standards to 'normal' is not appreciated. This also includes femboy cocks and femboy balls! They really shouldn't be fitting into my skinny jeans. They should be struggling in my skirts! My girl's boyshorts should be giving me a wedgie they're stretched so far in front of me! I'm exaggerating... But only slightly. Unless that's what you're into...

And while I would never push my partner into doing anything that would make them uncomfortable (consent is sexy, after all), I really do like to get to know my partner personally. Perhaps not as personally as knowing IRL details or names, but just having someone to chat with, someone to enjoy time with and not just fuck raucously. To put the penpal in DirtyPenPals, so to speak. Of course, I wouldn’t say that without being able to offer some insight into who I am as well. As an individual, I think that I could be considered fairly nerdy. I like games (video, tabletop, and card.), cooking, writing (obviously), and I've been known to dabble in other hobbies from time to time. I've got a degree I'm English Literature, and I'm working on getting my MA, but that's a different kind of adventure. And not a particularly fun one. I would probably be labeled a conversationalist, though NOT talking has never been one of my strong suits, and I love to get to know my partners (in a consensual and non-intrusive way, of course) outside of roleplay. So while this is less of a requirement, I think that forming a relationship outside of roleplay can be fun and exciting and allows us to break up the constant smut.

While there are a lot of kinks and fetishes baked into this prompt inherently, I also have a laundry list of other kinks and fetishes as well,

• Cumplay
• Outercourse
• Cheating
• Skimpy outfits
• Romance (This one is huge, actually. I love this.)
• Cuddling
• Aftercare
• Ballplay

These are just a couple of the things that I would really like to indulge in, just off the top of my head, but I have plenty more! Not to mention a fairly open mind, so as long as your suggestion doesn't conflict with my limits, I would love to hear it! Or at the very least be open to considering it. And, of course over-the-top lewd imagery is much appreciated... so much so that it should probably be on the kink list.

On the topic of details...

I don't expect perfect quality, not from myself and not from my partners. There are always going to be awkwardly written sentences (paragraphs, even), short responses, spelling errors, and grammar issues. And that's okay! However I do expect, at a minimum, at least a basic handle on the English language, grammar, and spelling, as well as a modicum of effort. While I tend to write multiple paragraphs, I do like to go with the flow, sometimes they'll be shorter, sometimes longer, so don't expect me looking for a word count from you! The main thing that I prefer is description. I want to hear, practically see the look of our bodies and how they move, how they struggle to hide beneath the limits of our clothing, how they press together in moments of passion, how I struggle to kiss you over the sheer size of your bust keeping us apart until I finally manage to smush them down, sliding between your cleavage to meet your lips... All of that is really important to me! I love love love detailed writing and I hope that you do as well!

I didn't really have a transition, so lets talk limits. Everyone has them, just a fact of reality.

• Heavy BDSM and torture
• Gore
• Snuff
• Scat
• Incest
• Non-con
• Blood
• Pegging

In terms of what this roleplay (and it's participators) would entail: a detail-oriented prompt, with a focus on femboys and MILFs (both with completely unrealistic proportions), preferably long-term, with a fun-loving guy who just wants to wear cute skirts. Thanks! Hope to hear from you soon!