£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.

Also, if you would, then any tips for a complete novice to dominating/humiliating? This is a very light touch and I’m not wanting to go mad if I do.

Pegging for 3/4 hours you will kill him !!!

I’d shag someone for an amount but not into pegging.

It's Sex for money...
are you seriously contemplating it?..
could you live with yourself afterwards?
how would the relationship be after you have done it
There are lots of professionals who would do it for him instead of you...

That's weird. If he's into paying for sex I'm sure there are plenty of experienced sex workers who would happily relieve him of less than a grand for a bit of pegging and humiliation. So this isn't really about the sex acts, it's about you. He specifically wants you to do it

This will change your relationship; in fact, I think just asking you has already changed it

Not this man.

But this way you don’t have to have sex with your body. I mean, they won’t penetrate you

It may be. I’ve always enjoyed humiliating him for fun. Just a lot of banter, dark humour, I know what makes him laugh and make him feel degraded. He’s always liked it, but only now we’ve talked about it and he says that level of degradation has started to turn him on (with everyone). I suppose I am a safe space for him as I don’t think he’d feel comfortable with a stranger

I'd never do this with a stranger but with DH absolutely!

This should be in the "stories and fantasies" section. Lol.

Oh I didn’t know there was such a section. Right back later ahem!!!

@Gambino1726

If you think you could do it why not just do it for S&G’s see how it feels, takes pressure of making it worth a grand and chalk it down to a lived experience. If you find your a born Dom then it’s all good.

Maybe get him to book a very expensive spa hotel or the Sex room at the Hotel Peliroco.

If a large part of it is about the humiliation, why not take his £1000 and then give him a really unsatisfactory experience.

That would be pretty humbling 🤔

That is a good shout findom or financial domination is an actual kink. He may well have both making his terrible experience amazing!

It times like these good old fashioned vanilla seems so appealing 😂

Well, he’s a funny one! Sometimes the more banter and cruel I am with him (two decades I’ve known him) the more he thinks it’s hilarious. So, maybe I just go to town, let out my frustrations and use it as some therapy for me too 😜 😆

not a stranger, a best friend I’ve known 20+ years.

No offence to you logic, but I’ve fucked shitty guys for free. At least this would be £££ with someone I know, and not using my holes…!?

I’d tried very carefully if neither of you have done pegging before. The idea that you’ll just bend him over and thrust a strap on up his arse is a bit ridiculous.

Has he used anal toys on himself in the past? Do you know how best to penetrate him? Clue- it’s not just to use lots of lube and tell him to relax! Are you prepared for a bit of poo? What position is going to work best for both of you? You probably want to see her face so you can both easily communicate and read expressions.

If he likes to be humiliated, you need to be really clear what that looks like. There’s a big difference between you praising him for being a good little boy who takes it all and you telling him he’s a disgusting pig with a tiny cock!

Any humiliation scene needs aftercare. You can really fuck someone’s self-esteem without taking the time to reassure them afterwards.

You're gonna charge your good mate of all those years money, £1k?!?! Nice friend you are. Either do it as a favour/ gift or not at all. It could all get a bit messy, in more ways than one.

Reminds me of the old joke

Would you sleep with me for £1000000?
Answer comes back - why yes
Would you sleep with me for £10
Answer comes back - no what do you think I am
We know what you are we are just haggling over the price...

As opposed to do it for free like you do? Get a life. Stop twisting mine.

I wouldn’t do that for money

I was joking around with an old friend who said he would feel my tits for £200 for 10mins

I joked & said you must have PayPal

he then told me to check my account. I did end up letting him have a feel but nothing more

Test

“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.

Well said. Let me guess that comment was written by a man who thinks he's entitled to sex and women are there just to be used for his own pleasure. It's actually disgusting when you think about it.