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  • Taboo and Detailed

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    Jim Ross
    • Partcipate in Private Roleplays: I do private roleplays
      Preferred Grammar/Spelling Competence: Fairly Competent
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    Alright bit of background about me. Been roleplaying for a few years now. The roleplays I enjoy are contemporary, or 'slice-of-life' as I've seen them referred to here. Male in his early 20s looking for a female partner who can play as a mature woman i.e. 35-42 years of age. I absolutely love the "mature woman - younger man" dynamic, or the "MILF" dynamic as it's more crudely referred to. Doesn't mean I'm not open to playing with same-aged characters, but age difference is something I absolutely relish! Here's a condensed list of kinks that I enjoy :
    1. Ageplay/Age Difference (obviously)
    2. Cheating / betrayal / forbidden couplings
    3. Flirting/teasing
    4. Revealing/provocative outfits
    5. Being a dom in the bedroom
    6. Breastplay

    I always roleplay in 3rd person, if you do too that's a plus. Nothing excites me more than a wall of text for a reply, hence detailed writing is a criteria that is required in my partners. At the very minimum one or two solid paragraphs per reply. I try to add as much color to the setting of the roleplay in the form of extensive character background and motivations and the conflicts that arise with other characters. I'd prefer it if we're both writing in real-time back and forth rather than with hours or days elapsing between each reply.
    Note : I hate, absolutely hate the PM system for roleplaying. It feels cumbersome and slow...like we're sending emails. Hence I typically roleplay off-site, typically through a shared Google Doc or Chatzy even.

    Below I'll list one roleplay setup that we could explore but do bear in mind that the second thing that I enjoy more than having a "mature woman" in my roleplays is a partner who takes the initiative and is not afraid to take my ideas and propose something new, or suggest to tweak certain things. I could not be more open to thoughts and suggestions.

     

    Sexretary 

    So in this my character would be similar to Mr. Grey from 50 Shades, young, rich, charming and somewhat withdrawn. However his Anastasia is not 20 something but rather 38. His assistant is moving to San Francisco to chase her dreams of becoming an actress and his new assistant could be a more mature woman. Your character is a capable replacement but certainly was not expecting the level of involvement required to be Jim Ross's assistant. The work is incredibly demanding, the hours are gruelling, there's non-stop travelling and it would all be rather brutal were it not for the unparalleled luxury that accompanies it all. Her normal life begins to feel odd when she's regularly taking a helicopter to attend meetings or going on dinners that cost as a much as a mortage down payment. Of course with time she gets to see more of her boss's personal life too. Truth is that her boss has a phenomenal sexual appetite. It was all put to a halt for the time it took for your character to get up to speed in her new job. Now he wants to restart it all and he wants your character to manage it all. Discretion is of paramount importance, the revolving door of women that Mr. Ross beds cannot be allowed to sully his reputation. Lastly, he's a busy man and careful scheduling is required. Now as she's scheduling Miss Colombia for 'dinner' at Mr. Ross apartment, or finding the time for him to 'interview' the new pair of twins interning at his company, I wonder if she ever gets curious about it all. She's ushering women in and out, hearing their moans and their cries of pleasure, what it would be like that for once she be the one to test the sturdiness of his desk?

    And further below there's a few other options for our roleplay setup :

    Main Woman

    In this setup, my character is college-aged, a fairly popular and charming young man. Your character is in her mid to late 30s or even early 40s, typically divorced, has a son or daughter and they are entirely focused on them. However meeting my character, sparks a change in her life. Her duties as a mother begin to take a backseat to her needs as a woman and thus an affair is formed. Now from here on out it can go a few different places :

    Romance 

    I love to play with the taboo nature of a relationship involving a younger man and a mature woman, especially if said young man is her son's friend for example. They enjoy each other, but they are realistic, they know there's no future in it. He's not going to marry her or anything, it's just fun. Incredibly dangerous fun, but though they try to stop, they cannot. Maybe there's other obstacles too, he's a manwhore, used to sleeping around. She hates it. Maybe he comes to hate it too and gets more attached with her, hates himself for being attached to a woman that he has no future with. Maybe things come to a head as their friends and family find out about their affair. They're ostracised by everyone or she's beaten down and forced to submit to social norms, giving him up. Defying everyone he returns to her life. They try to make it work, try to escape and become a couple, it goes great, then it goes terribly. They try to separate, but then she finds out she might be pregnant...
     

    Romance with a Harem 

    This is for the versatile partner. In this case, we explore more Jim's promiscuity. Maybe we roleplay a few other characters that he sleeps with, but he always comes back to his main woman. Will he realise that she's worth more to him than all the other vapid sluts and give them up...or realise that he'll never be able to settle down?



    I guess there's a few others, might add them at a later time, but that's all I'm going to put down for now. This should give you a good idea of what I'm into and hey, if some of this sounds like fun, feel free to PM me.

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