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Suggestions About How To Pay a Debt

Posted 03-27-2023 at 09:29 AM by cariadferch
Updated 03-30-2023 at 02:46 AM by Butterfly

I need help with coming up with an idea on how to pay a forfeit.

I lost a game of battleship to roadrunnerkc17 and have to do, and then report, on some sort of sexual payment. His kinks, according to his profile, are: Cross-dressing, anal and masturbation.

When I asked him which of the three he would want me to do to myself, to my relief, he didn't choose anal, however, to my surprise, he went with cross-dressing.

Now, I love an erotica/literary challenge. However, I have no idea how to respond to this challenge. Wearing men's clothing is no big thing for a woman. I love t-shirts and jeans. So, this got me thinking: Why are some men into the cross-dressing kink? Is it "getting in touch with their feminine side"? A sense of elegance? Submission? Humiliation and shame? I really don't know.

So, does anyone have any suggestions on how I can pay this wager? If someone comes up with an interesting forfeit I might be willing to "owe you one", or even go find my "sister" if you're into that kind of thing.

Dan eich bendith,
Amy
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Comments

  1. Old Comment
    Interesting, and while I am not into cross dressing the idea of a female cross dressing is appealing. My thoughts went to remove as much of your femininity as possible for this challenge.

    First I would suggest binding those lovely tits so as to remove as much curve as safely possible.

    Next make your hair as masculine as possible, I wouldn't go as far as suggesting a crew cut for a one time dare but you get the idea. If you have fancy nails they need to be cut and stripped for this task.

    Clothing, again we need to remove all traces of you as a female. This would mean all men's clothing, boxer shorts, t-shirt, socks, shoes, pants and shirt. I would suggest dress / casual clothing so no t-shirt and jeans for "this guy". No jewelry or perfume and if possible men's cologne.

    Finally, this wouldn't be good if you just paraded around at home. You need to go out as a male and act the part, somewhere that would mostly be guys. Ideally somewhere predominantly male such as a rest room or perhaps a strip club. Both of these places should indulge your humiliation fetish. I can imagine you getting a nice lap dance already.

    Does this give you any thoughts?
    Posted 03-27-2023 at 11:25 AM by tzzzr tzzzr is online now
    Updated 03-27-2023 at 11:27 AM by tzzzr
  2. Old Comment
    lotusdriver81's Avatar
    I think it would go deeper than just jeans a t-shirt. It should include the underwear too. I would perhaps even suggest you simulate a penis somehow. When you go out make sure you stand up to pee, as a guy would.

    It is a rather interesting twist on cross dressing where it is acceptable for a woman to wear mens clothes but not the other way round, but thats another debate. For me it is the enjoyment of being feminine and girly and also the unusual feeling of the underwear and skirts etc.

    The biggest challenge for a guy would be going out and being seen so for you that should be the same for you. Don't shave so your legs are hairy etc (might take a while depending on how fast your hairs grow) Wear boxers/briefs etc (actually know a few women who find them quite comfy)

    Hopefully a few ideas for you.
    Posted 03-27-2023 at 12:29 PM by lotusdriver81 lotusdriver81 is offline
    Updated 03-27-2023 at 12:42 PM by lotusdriver81
  3. Old Comment
    Anakin's Avatar
    Clearly you will need a pornstache. Stick-on or drawn.

    Posted 03-27-2023 at 03:44 PM by Anakin Anakin is offline
  4. Old Comment
    cariadferch's Avatar
    Quote:
    Originally Posted by tzzzr View Comment
    . . . suggest binding those lovely tits so as to remove as much curve . . . hair as masculine as possible . . . nails they need to be cut and stripped . . . all men's clothing, boxer shorts, t-shirt, socks, shoes, pants and shirt . . . No jewelry or perfume and if possible men's cologne . . . go out as a male and act the part, somewhere that would mostly be guys . . . a strip club.
    Thank you! Those are some excellent suggestions. I'm not sure about the last one. Going to a strip club as a women would be embarrassing enough but dressed up as a guy? Would I get beat up?
    Posted 03-27-2023 at 07:31 PM by cariadferch cariadferch is offline
  5. Old Comment
    cariadferch's Avatar
    Quote:
    Originally Posted by lotusdriver81 View Comment
    include the underwear . . . simulate a penis . . . stand up to pee . . . For me it is the enjoyment of being feminine and girly . . . Don't shave so your legs . . .
    Thank you, especially for the mental insight. Not just acting like a guy but trying to feel like a guy. I'm not good at burping, however. ;-)
    The suggestions are interesting - Again thank you! I appreciate the creativity. I won't be doing the bathroom stuff (one of my nevers). Going out with hairy legs might be a bridge to far, I will have to think about it - It would be humiliating but maybe in a bad way. However, simulating a penis might be an interesting challenge. How you guys walk around with those things is beyond me.
    Posted 03-27-2023 at 07:38 PM by cariadferch cariadferch is offline
  6. Old Comment
    cariadferch's Avatar
    Quote:
    Originally Posted by Anakin View Comment
    Clearly you will need a pornstache.
    Brouhaha!!! That is hilarious.! I love the word "pornstache". However, no. Just no.
    Posted 03-27-2023 at 07:41 PM by cariadferch cariadferch is offline
  7. Old Comment
    lotusdriver81's Avatar
    I'm glad yo uno have a few suggestions. Hopefully more will be along with other creative ideas. I hope you let us know how you get on.
    Posted 03-28-2023 at 09:25 AM by lotusdriver81 lotusdriver81 is offline
  8. Old Comment
    Anakin's Avatar
    Quote:
    Originally Posted by cariadferch View Comment
    Brouhaha!!! That is hilarious.! I love the word "pornstache". However, no. Just no.
    Awww... I only get rejection after rejection from you... :cwy:
    Posted 03-28-2023 at 11:44 AM by Anakin Anakin is offline
  9. Old Comment
    jjjks's Avatar
    A good way I believe you can pay the water is by getting a outfit of male clothes and like said in a post above simulate having a penis, I believe doing that would add to the risk and embarrassment, while you have those clothes you should go for a walk in public and just try doing some everyday things hoping no one will notice your fake penis

    The main reason I think cross dressing is done is because of the feeling of embarrassment and risk of being noticed and just letting a feminine side out.
    Posted 03-29-2023 at 12:00 PM by jjjks jjjks is offline
 

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