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

My wife has asked me how I might feel if she enjoys it so much that she decides she wants it to become a recurring thing and I’ve said in my head that’s how I want things to pan out. She really enjoys sexual pleasure. Also I would say I’m pretty alpha in my life also, this seems to be a common theme in the lifestyle

There is another post on here, different thread, from a husband who hasn’t had sex for three years, a number of reasons, but one was that they had an open relationship a few years ago following which it seems she just fell for another man, It’s a situation that needs careful consideration on both parts, yes most men do fantasise about partners and another man especially if they’ve had other sexual partners wondering how they compare etc, is this a fantasy shared by women?but for most it’s a fantasy and turning it into reality may work for some but clearly destroys relationships for others, personally I’d fit in the it being a thought about how it was for her with previous partners and absolutely not something I’d want to take further, good luck if you go ahead and hopefully it doesn’t damage your relationship

She generally keep it to “one night dates” but has subsequently settled with a regular lover and are, with the agreement of all concerned, going through a period of exclusivity with her current boyfriend.
There are are other aspects that help but it seems to be working for them.

I’ve noticed lots of people carry this out with people that they both know or that the wife knows. This would be a big no no for me as it sounds far too messy and a recipe for disaster, feelings could easily come into play and marriages could easily fall apart I’m sure! This way works for us as it’s on foreign soil and the guy is a professional working, it’s literally about the sex, he is quite literally a sex toy for us is how I’m computing it.

I am not a jealous person at all. Found the experience to be quite exciting and fun.

Don’t think they knew before hand as he lives a few miles away, although she may have done through her work.
The build up, preparation, chastity, submissiveness and exclusivity to her lover is all part of scene for them. She’s told me she always ensures after her husband has helped her prepare she leaves him some domestic chores to keep him busy lol

Yeah I’m also given more than my fair share of domestic chores! I’m fine with this, all part of the fun. Our build up follows a similar pattern, just without a permanent guy.

Judging by the comments and interest in the post it’s obviously something we either talk about or fantasise about I appreciate it’s not everyone’s thing I personally find it very erotic , not from a watching point of view I get very aroused thinking of giving someone pleasure whilst there partner takes a passive role .

My partner and I previously had threesomes and foursomes. About 20 years ago. Wouldn't do it now looking back just a bit of fun, early days into our relationship. It was good and bad, no jealousy from our side just the women got upset with their partners when we had foursomes. But then my partner went on to cheat. I think he felt that as we'd done all that together he could or wanted to do it privately too. Big difference. Good luck to you though, every relationship is different.

Yeah in no way should a partner assume it’s ok to have sex outside of a relationship because u take part in these things! That’s bang out of order. I have no interest unless my partner is involved, it has no meaning. Massive airport delays and cancellations may be halting our plans this time around!! Fingers are firmly crossed at the airport

When is it?

Good luck. Hope you get there OK and you are all happy with the outcome. Keep us posted

I think openness and honesty are the key, the point about cheating above is well made.

Caribbean per chance ????

No not Caribbean, but then not anywhere now, flight cancelled 😢 off to go and grab the kids instead. Very disappointed

What will you do now then?

Unfortunately all flights are fully booked for the rest of the holidays, looking like March may be the next chance we both have time off work. Really gutting, we had a proper good weekend planned 😢

Fucking fog

Wasn't ever really planned was it? Apart from in your head.

If you are genuine about this, you don't have to wait until March. Plenty of very capable and willing men out there. Many of which will be within driving distance of wherever you are.

Apps, websites, reddit etc.

Yes, was a complete fairy tale for a couple of days of fun on an internet forum. This has made my year, I may start another one soon, keep your eyes peeled

I am genuine, we also live on a small island, otherwise I would agree with you. Probably willing men around but also very likely to know someone that knows one of us, it’s not practical.

Bit rude. You know nothing about him

Ahh, that is challenging. Good luck!!

Something I'd be interested in trying out as a guy too. Fascinating thread