Mx Female Craving Wholesomely Smutty Ugly Bastard Roleplays (NSFW Images)

HeartOfTheDarkness

Promise Nothing, Deliver Less
Joined
Jun 8, 2012
Hello. I assume this is a bit of a stranger craving, but I've been wanting to do some smutty roleplays involving an ugly bastard in a more happier setting. For those of you unaware, ugly bastard is the tag used in hentai where the girl has sex with an ugly man, usually in a rape and/or NTR story. They're usually the villain, but I've seen a few doujins where things are more wholesome. The girl has a thing for uglier guys, maybe the guy saved her and she fell for him, or maybe they're childhood friend. So I wanted to do a roleplay like one of those, where I play the ugly bastard against a girl in a more consensual pairing. I'll give a vague idea of the type of character I'd like to play, and I'll list various girls/plots to pair my character up against. Before we start though, let me go over some rules.

Rules:
1. I'm a straight male. I'm looking for female characters. I don't care what you are in real life, but my character will be paired up against a woman. That's just what I'm into.
2. Please have a decent grasp of the English language. I don't mind a few errors here and there, we all make mistakes. However, if I can't understand what you sent me, I'm not going to respond.
3. I don't have a post length, but please give me something to work with. I understand we can't always give multiple paragraphs, but if you send me one sentence and barely give any effort in forwarding the story, this roleplay isn't going to last very long.
4. I'm very ditch friendly. I'll apologize ahead of time in case I accidentally ditch you. Sometimes life gets busy, I work a job where a lot of people get pissy at me over things outside of my control, and I get depressed. I'm super awkward talking to people, even when just typing messages to them. So sometimes I just won't respond. I'm trying to get better about it, but I'm sorry if it happens. Feel free to just send me a reminder if you don't hear back from me after a while.
5. I'll likely do the same. I don't mind if you just disappear, but I might send you a message after about a week of silence, see if you're still interested. Especially if I was looking forward to the roleplay.
6. I prefer using drawn/anime images for our characters. I don't mind real people, but I just feel more comfortable using fictional characters for our fictional story.

Now for the kinks and dislikes. My F-List is super out of date, so I'll just list the basics. Feel free to ask about anything I didn't list. If it's not under dislikes, I'll probably be fine with it.
Likes: rough sex, messy sex, cosplay, big boobs, lots of cum, condom play, videotaping/streaming sex, milfs, gyarus, harems
Dislikes: scat, watersports, vomit, vore, feet, death, extreme violence, hardcore BDSM, bestiality, yaoi, futa

The Ugly Bastard
Now for how I plan for my character to be. I envision him as a fat loser otaku. Kind of creepy looking, and a bit of a pervert. He likes his anime and video games, he's often the target of bullying, girls tend to look at him with disgust. That being said, he's not a bad guy, despite his appearance. While he was a bit more miserable in his younger years, he's now come to accept his lonely existence. He's not meant to be with a real woman, or really have much in the way of friends. Instead, he has his 2D girls from his favorite animes and video games, they won't look at him with distain, they won't betray him. He's fine with being alone, at least until YC comes around.

This is just a basic description of him. I plan to have his age somewhere around late teens to early twenties. Everything can be changed to better fit your preferences. Appearances, personality, whatever. As long as he remains an Ugly Bastard, and this is a more light hearted story. And now onto the potential girls he may meet...

The Girls/Plots (These images are placeholders, feel free to suggest your own appearances)
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The Childhood Friend
A girl that grew up alongside him. When they were kids, they did everything together, it was even assumed that the two would one day get married when they grew up. That was years ago, and people change as they get older. While she got prettier and began hanging out with different people, she still remembers her old childhood friend fondly, even if he's not quite the type of guy she'd imagine marrying. Still, there's something about him that she desires. Maybe he's still friendly with her, maybe they still like the same things, maybe she thinks she can fix him.

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The Popular Girl
She's the hottest girl in class, maybe in school/campus. She could have any guy she wants, and unfortunately that's kind of her problem. She's had a lot of unfortunate experiences with men in the past. She's dated and slept with all sorts of guys, and they're all pretty much the same. They see her as a piece of meat, they're only looking at her tits and ass. While she's very proud of her assets, nobody seems to care about getting to know the girl with these assets. Randomly coming across some stuff online (pictures, doujins, manga, hentai, ect), she gets an idea. She's only dated hot guys, and hot guys are assholes. What if she tried going the opposite direction? Go for an ugly guy, and hope he's a sweetheart. Can't really say she's known for her brains, but the loser she chooses won't complain.

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The Slut
A bit more of a simpler premise. A slut with very low standards in men she sleeps with. If he finds her attractive, she'll do no it, for a price. Seeing a certainly gross otaku on the streets, she figures she'll give him a try. Surely a loser like him wouldn't say no to her. Perhaps she likes something about him though. Maybe he's good at sex, maybe he's got lots of money, maybe he's just nice to a slut like her. There's something about him that leads her to want him again.

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The Perverted Otaku
She makes a living drawing erotic art, maybe even does doujinshi. She doesn't have much of a following, but there is one fan she's particularly fond of. He's always complimenting her work, mentioning how he enjoyed it, sometimes leaving a few critiques on how she could improve. Eventually they started chatting, talking about the games they play, the shows they watch, waifus they'd love to lewd. They have fun talking to each other, maybe they even play games online together. One day, they learn that they don't live too far from each other, and one of them suggests meeting. When they meet, he's not quite what she hoped for, but he's still the same guy she's been talking too. He's still her fan, her friend, maybe even more than that.

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The Admirer
She doesn't care that he's a gross otaku. She doesn't care that he's a waste of space. She doesn't care that me might stink, that me might look like a creep, that he's attracted to anime girls. She wants him. Why? Who knows. Maybe he helped her out in the past, and she decided to become the perfect woman for him. Maybe he saved her, and she feels indebted to him. Whatever the reason is, she wants this loser. To her, he's her dream man.

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The Single Mom
She's neighbors with the ugly bastard. While she was initially cautious around him at first, her young child seems to get along with him quite well. There's multiple times he's babysat her child while she was busy working one of her multiple jobs. He's honestly been a huge help in raising her kid. And it's been so long since she's been with another man. He may not be a stud, but he's so good with kids, maybe it's time for a new man in the house.

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The Mess
She hasn't really had much of a fortunate life herself. She's been through multiple messy relationships, abusive boyfriends, cheating lovers, may even a rough divorce. Now living one, she's miserable, feeling like her life is going nowhere, that she'll die alone. Hardly ever leaving her apartment, she eventually has a chance encounter with the ugly bastard. Maybe a package accidentally gets delivered to the wrong house, maybe she needs to ask her nextdoor neighbor for some help (lost power, there's a spider, ect). She feels strangely comfortable around him, maybe it's because she doesn't feel any sexual tension, he's polite to her. It starts with them just occasionally chatting whenever they see each other. Then they start become friends, meeting up to hang out. As she gets more comfortable around him, her mood starts to brighten up. Maybe her life isn't so terrible, she isn't completely worthless. And it's all thanks to this ugly bastard.

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The Servant
What off the ugly bastard came from a wealthy family? A family with servants, and he had his own personal maid? This maid was trained to serve their master, no matter what. No matter who they were, no matter what the request is, they must always strive to please their master. Does the ugly bastard do anything dubious with his maid? No, he treats her like a normal person, maybe even as a companion. When it was time for him to live on his own, she accompanied him, vowing to continue to serve her master. Despite him currently living off his parents' money, she still enjoys spending her time with him. However, she does notice he seems lonely. He doesn't have much in the way of friends, and he's never been with a girl. Perhaps there's some way this lowly servant can help her master gain some experience in satisfying a woman, so that he can one day claim a wife and continue the family bloodline.

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The Girl From Another World
One day, a girl from another world gets isekai'd into our world. The ugly bastard happens to come across her (or maybe she appears in his room), and he offers to help her. Being in another world, no way to return home, and no idea what's going on, she can't really pick and choose where here help comes from. And no matter what world they're from, everyone knows it's best to repay a good deed. While she has no money, she's staying with a man, she can easily provide some form of compensation. Bonus points if sex is part of her culture.
The dark elf is just a default option. Feel free to suggest another race, or she could still be human.

I'll add more over time. Feel free to suggest any ideas as well. Hit me up if this catches your interest and we can discuss more details. Hope to hear from you. :)
 
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