£1,000 for a night…

[Gambino1726]

So, a friend of mine has asked me to ‘help him out’. We’re very good friends of 20+ years. We’ve occasionally fooled around (no sex), but we’ve mostly been the best of mates, and definitely not boyfriend material.

We were joking around one night, drunk, and he asked me to peg him (erm, basically put a dildo on and give him anal sex) and to make him feel humiliated. I jokingly said ‘yeah if you give me a grand (£1,000)’ and he said yes, ok. I was a bit taken aback… initially I was thinking no, but the idea of £1k for a few hours work doesn’t seem like the worst idea.

Tax declaration reasons aside, would you put on a poker face for 3-4 hours ‘work’ to do it in exchange for that much money? He knows I wouldn’t go all the way and doesn’t want sex with me (I know he would respect my boundaries), he just wants me to humiliate him and dominate him.

🙄your 'holes'?

If that's how you think about yourself, then yes, I agree, go ahead and make that grand. It will be easy, it is not involving you being penetrated or indeed using any part of your body apart from your hands, to hold on. I would set a time limit. Frankly 3-4 hours seems v generous. I'd have thought 30 minutes should do.

You mention having for years degraded him. Ok. So this seems to be already a thing between you two. So just take it a bit further, I suspect you don't have to be in any way professional, the guy will like it whatever.

The joke isn’t funny though. You’re saying that a woman is a prostitute regardless of the amount of money you pay her?

I think this is a cheap way to “put a woman in her place” make her feel worthless and bound to the expectations of old fashioned society.

theres a difference to a woman who sucks c*ock for £10, and a woman who charges £100000 to be slept with or to dominate a man. A huge difference. I see that distinction clearly, and if you don’t, well, that says more about you.

most of us have slept with men for free. Whether after one dinner date or 10. But if I man or woman wants to put the money on the table for sex, and no one is being exploited, then what’s the issue

I know. vulgar choice of words. I apologise.
I have a lot of self respect, I promise 😂

You seem to be saying that you wont do it for free (for an alledged friend) but £1000 is OK why don't you for ask for more then and see what price you agree on..

Ssounds like the film Indecent Proposal

theres a difference to a woman who sucks cock for £10, and a woman who charges £100000 to be slept with or to dominate a man. A huge difference. I see that distinction clearly, and if you don’t, well, that says more about you.

Just FYI there's a good deal you've said on this thread that says a lot about you too, but it takes all sorts and I'm certainly not going to lecture you.

But if you're going to go ahead with this then plan it out so that you (1) get the best possible outcome for yourself and (2) you ensure your safety. I reckon what you should do is start off with the £1,000 but make it absolutely clear it's for half an hour and what's going to be included and what isn't going to be - he will likely enjoy you doing this, the assertiveness/domination doesn't have to just be in the bedroom and you'd also be setting boundaries which will be important for your safety.

Then go ahead and do it in such a way that he's left wanting more. You could then continue to extract money from him in the longer term (make sure he can afford it, so you essentially become a service provider that he can accommodate into his budget). It's even possible you'd find yourself a new and lucrative career path so you could retire early and go on lots of holidays etc.

If you felt bad I think you could easily justify occupying this morally grey area by saying something to yourself like 'men have taken advantage of women forever so what's with with me doing a bit of it in return'.

Thank you for some logical and worthy advice. Indeed a lot to think about and not doing it anytime soon. He doesn’t live around here. But will visit in the new year.

id only ever consider this with him, because I know him so well. I doubt very much I’d turn this into a career. I’m too long in the tooth, and have other ventures I focus on passionately.

I don’t feel I am taking advantage of him whatsoever and don’t have to justify it to myself. Like mentioned, he is extremely wealthy, the money means nothing to him, or me frankly. However I do think about the other people in my life and the money would be of use to them.

There is no moral reason you shouldn't do this if you want to. But you should be aware that there's only a few ways this will pan out:

1. Afterwards you can't be friends anymore.
2. Your friendship continues but having got what he wants he's always looking to get you to do more, do something else, or do it again for a less 'exceptional' price.
3. (probably the best outcome) You both catch feelings and have a sexual relationship. But it will be almost impossible for you to charge him even market rates let alone £1,000 a time in the future.

@Gambino1726

“Gift” “favour” 😂 why would I do it for free or for a favour? What the hell sense would that make, and what is the favour you propose I ask from him in return? 🤦🏽‍♀️"
He’s minted. Money means nothing to him.

What I am saying is that if he is "your best friend", why would he have to pay you??!'
If I help out my best friend, or vice versa, I would never accept money from him. That's not what friends do. And he certainly wouldn't expect any favour in return! Or maybe it's different with your friends? Whether he is minted or not should be irrelevant. Do you generally charge people to be your friend?

This is the most ridiculous feedback I’ve had to date. Friendship is free. Obviously. And has been for the 20+ years.

asking for service comes at a cost.

look lady, if you want to do it for free and feel justified to do so, then do so! But here you’re coming across as a sexually frustrated grouchy old lady. Get off my back and have a talk with yourself in the mirror.

👏🏻🎤⬇️
Well said OP

He's rich I'd make this a common thing between you.

Give up work do it 3 to 4 times a week sorted. Demand more he will love it.

Call him every name you can think of, ram it in as hard as you can shove it in his gob to clean up afterwards, baby wipe it down pop in a bag, get your cash and go.

Where do I sign up?

I think it's the best answer so far. Anyone who engages in anal sex or BDSM should educate themselves on the safety aspects (including emotional safety), but since you would be the one topping and getting paid for it, there is a bigger responsibility on you to do your homework on those practices.

If the OP had said that she'd been invited for a romantic weekend away with a close friend and was expecting a night of hot sex I doubt it wouldn't raise an eye brow. It's a transaction all the same, it's just this one is brutally honest.

I hope the conversation wanders back to the narrative: did you take him up on it? If so, how did it go?

Dear Rudeboy, I won’t be feeding back about the evening. The details of which would remain private. 😘