First time cuckold this week

[Southsiderunner]

Hi
ive been with my wife for 25 years, married for 16. We have 2 kids 14 and 9. Since I can remember I’ve had a fantasy involving my wife and other men, I believe this fantasy has always helped keep the bedroom spark alive.

for the last 5-6 years we’ve really enjoyed roll play with larger toys and my wife has started to enjoy fulfilling my submissive side. I had asked a few random times before about trying another guy for real and without flat out saying no, she just said she doesn’t think she would like it, until a couple of months ago. I just randomly dropped into a convo that we should have a shopping trip away and hire a male escort for a treat which she replied to with a “yeah sounds good”!
fast forward and we’re 4 days away and the guy is all booked up. He’s very well endowed and comes highly recommended, he says he regularly does porn shoots and knows what he’s doing.
i guess my question is for first timers, male and female, any advice for the night and also any thing that you didn’t enjoy that u thought u would or did enjoy that u thought u wouldn’t? I’m trying to cover all angles in my head so things run smoothly.

I know my wife loves me so any jealous feeling I’m sure I can cope with, im also a confident man and think I can cope with this guy giving my wife a better time in bed than I can, I’m not deluded. Anyone felt like this but was proved wrong?
what are your regrets if any?

thanks and merry christmas

Have you considered your wife might back out? Are you thinking you might get involved and it becomes a threesome?

I think there’s a chance both of us could back out, every now and then I think how mad this all is! But we are both excited rn. There is no chance I will join in as an equal partner, I would be far too excited and it wouldn’t end well

Is posting here for women's reactions part of the thrill?

Not at all, and neither is men sending dms for kicks fyi…..
any other negativity on the public thread and il jus pull the post. I’m not here for hate, il find out my answers in due course watever happens
ty

This is the sex board. His wife is happily involved. There are people on this board who have experience of this. Why shouldn't he ask these questions?

Thanks for the defence. I quit all social media’s years ago now because of how toxic it is, so I’d like this not to become a mess 😂 I’m very happy leaving. Some men are actually alright.

It was a genuine question. It's not beyond the realms of possibility, is it?

I don’t think it was a genuine question, but at the same time I understand these forums probably attract a certain type so I won’t take it personally. X

Just be aware that once you’ve crossed that rubicon there’s no going back. Are you really going to live happily ever after with no issues after your wife has been shagged in front of you by some porn star?

Id take her a rubber ring for the way home 🥖🐱🔥

Jealousy is obv a concern, but I reckon I can take it. We’re looking at it as an extension of our sex toy repertoire, a real life sex toy perhaps. Our toys out perform me and I’m fine with it, I get this is a whole different level but 🤷‍♂️. I’m fully aware this guy is going to be good, that’s why I’ve chosen him. Is this a topic u have any insight on or does it completely shock you? Thanks

It doesn’t shock me, people do and always have done all sorts, though I suspect it’s been conditioned a lot more recently by porn. But don’t think it will be uncomplicated, because it likely won’t be.

I respect your opinion. I would agree on the porn conditioning, it is definitely something that has shown up on sites and magazines since my youth and defo triggers something in me. But I imagine if this wasn’t a kink someone had, it must seem unimaginable to carry out, whereas for me, In a controlled environment im hoping it could be really fun. I appreciate you time in replying. Really hoping for some real life experiences and advice

Where did you find him?

Why did you keep bringing it up after she said she didn't think she'd like it? What exactly has made her completely change her mind? I can't see anything that's changed other than you harassing her. You sound like a grim sex pest and I feel really sorry for your wife to have been coerced into this. Grim.

The poor woman sounds worn down, not an enthusiastic participant

I imagine that after paying a man to have sex, and after having her husband willingly 'let' another man have sex with her (a man who has no regard for her, it's just a job).... she might feel pretty sordid and wonder if you really have her best interests at heart when you suggested and set this all up

Please make it very clear to her that she can change her mind, before or even during this encounter. There's a real risk she'll go along with something just to avoid causing a fuss and could well feel very unhappy, violated even, once this is over

I think unless this is something she has always wants to do, it's likely she's said yes to this to please you or because you kept asking. Please put her feeling ahead of your fantasy.

I've met a lot of couples for threesomes. Hotwifes you may call them. Cuckold involves humiliation. I've not seen this in the couples I've met. Completely different.

I would urge some caution here , firstly I would probably start with an erotic massage sensual and intimate touch on both sides , definitely set out very firm and strict boundaries ie absolutely no penetration penis / vagina on the first meet up your wife will hugely appreciate that and there is no pressure.
i have given these types of massage before and can assure you three people in a room naked with a massage table some wonderful oil watching your wife being touched in the most intimate way will be a huge turn on , you will most likely masturbate watching. This gives you time to think about the experience and if you want to take it to the next stage . Watching another man placing his penis inside your wife can potentially be upsetting no matter how much you think you want it to happen, just take it one step at a time . I do have some experience feel free to message me

A grim sex pest, wow. I can assure you “the woman” is not worn down. “The woman” is happy healthy and very successful and capable of making her own decisions. I believe these assumptions are based on your life experiences. I can assure you we are both excited about this, I think my wife may want it more than me at this point. Can we please all assume a happy relationship and stop the horrible stuff and be helpful with advice on an adult topic. To the helpful humans in the dms, thank you.

The truth is that this is most men’s absolute fantasy, seeing there wife or partner sexually aroused by another man , asking them about past sexual experiences is a huge turn on , however lets not confuse fantasy with reality and after all this is a sex forum , we should be supporting or constructively helping someone explore not judging…..
I have previously said on this subject there is a half way house
You don’t run a marathon on your first ever race , what happens on a 5K 10 k decides weather you want to run a marathon..

We got into this 5 years ago. Started as a mfm thing and moved on to more just her and the guys, as I watch. No direct and overt humiliation. It has become something we really enjoy. We both get quite excited by it.

Good luck.

Fully agree, I can’t think of anything hotter than the woman I love being given pleasure I couldn’t provide, pretty nuts if u try and pick it apart 😂. Thanks for your advice, ive shared your side with my wife and we agree it makes sense, although seems we are both excited about the full deal now. We have both got full rights to pull the plug on it at any time if either of us feels they aren’t into it. We have really gone into detail on how we feel and wot ifs etc. there is no pressure on either of us and the trust is there. We are both pretty laid back and are pretty robust so I really do think it’s going to be a good experience, it’s just the not knowing that’s scary

How was the jealousy for you? We’ve talked about doing it as an mmf but I know I wouldn’t last the course and it would be weird afterwards, I’m ok with this, and the mrs understands. Glad you guys enjoy it

Women are sensual beings, they like pleasure in all its forms.

I indulge in a side script of this fantasy with my platonic companion. Slightly different as it’s always been so but I do know another couple who do exactly this and have done for years.
Outwardly they are the perfect couple and he appears an ultra alpha male.
Secretly he absolutely thrives on the aspect and humiliation of his wife enjoying lovers as and when SHE chooses, and I think that’s the difference here and the most important part.