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Wife has set me a challenge with a surprise for me at the end - but makes me nervous!!

Posted: Sat Oct 25, 2025 9:16 am
by ohtobecucked
Wife out with bf this weekend and has sent me two orders to follow, there’s also a ‘surprise’ if I do both.

The first is that when I’m indoors I can only wear her underwear, so not hugely kinky (for me anyway), we've done that loads, so meh..



The second is the one Im more nervous about - she wants me to go naked either tonight or tomorrow and then take pics of me outside playing with myself, but I have to cum while I’m out, too.



Now, I personally think it is her bull who has suggested these and I’m fine with that too, as long as they’re building up their relationship to how you’d want it to be. Especially as her dominant side really comes forward.



But the main thing?? I desperately want to know what the ‘surprise’ is - are they going away for a weekend together?? He gets her anal virginity?? So many things I wish were true.

, that’s definitely enough to push me on, naked and alone and her being fucked by BF and I’d don’t know what’s coming after.

Also it is freezing here - so wish me luck!! :-)

If I do it, I’ll take pics and show them here to whoever wants to see it.

Re: Wife has set me a challenge with a surprise for me at the end - but makes me nervous!!

Posted: Sat Oct 25, 2025 9:39 am
by D+D
ohtobecucked wrote:
Sat Oct 25, 2025 9:16 am
Wife out with bf this weekend and has sent me two orders to follow, there’s also a ‘surprise’ if I do both.

The first is that when I’m indoors I can only wear her underwear, so not hugely kinky (for me anyway), we've done that loads, so meh..



The second is the one Im more nervous about - she wants me to go naked either tonight or tomorrow and then take pics of me outside playing with myself, but I have to cum while I’m out, too.



Now, I personally think it is her bull who has suggested these and I’m fine with that too, as long as they’re building up their relationship to how you’d want it to be. Especially as her dominant side really comes forward.



But the main thing?? I desperately want to know what the ‘surprise’ is - are they going away for a weekend together?? He gets her anal virginity?? So many things I wish were true.

, that’s definitely enough to push me on, naked and alone and her being fucked by BF and I’d don’t know what’s coming after.

Also it is freezing here - so wish me luck!! :-)

If I do it, I’ll take pics and show them here to whoever wants to see it.
You will do it. You will do about anything because it excites you. You are a cuck and it’s only natural for a cuck to do cucky things to humiliate himself for a dom wife and her Alpha boyfriend. I well know.

Re: Wife has set me a challenge with a surprise for me at the end - but makes me nervous!!

Posted: Sat Oct 25, 2025 9:44 am
by ohtobecucked
D+D wrote:
Sat Oct 25, 2025 9:39 am
ohtobecucked wrote:
Sat Oct 25, 2025 9:16 am
Wife out with bf this weekend and has sent me two orders to follow, there’s also a ‘surprise’ if I do both.

The first is that when I’m indoors I can only wear her underwear, so not hugely kinky (for me anyway), we've done that loads, so meh..



The second is the one Im more nervous about - she wants me to go naked either tonight or tomorrow and then take pics of me outside playing with myself, but I have to cum while I’m out, too.



Now, I personally think it is her bull who has suggested these and I’m fine with that too, as long as they’re building up their relationship to how you’d want it to be. Especially as her dominant side really comes forward.



But the main thing?? I desperately want to know what the ‘surprise’ is - are they going away for a weekend together?? He gets her anal virginity?? So many things I wish were true.

, that’s definitely enough to push me on, naked and alone and her being fucked by BF and I’d don’t know what’s coming after.

Also it is freezing here - so wish me luck!! :-)

If I do it, I’ll take pics and show them here to whoever wants to see it.
You will do it. You will do about anything because it excites you. You are a cuck and it’s only natural for a cuck to do cucky things to humiliate himself for a dom wife and her Alpha boyfriend. I well know.
Haha, yeah, you get it! I know I'm going to, I just have to gee myself up first. Would be amazing if the surprise after was her getting fucked outdoors (something I've never done with her).

Re: Wife has set me a challenge with a surprise for me at the end - but makes me nervous!!

Posted: Sat Oct 25, 2025 10:15 am
by mbanthony
You gotta do it. For obedience sakes but more importantly to find out the surprise.

Re: Wife has set me a challenge with a surprise for me at the end - but makes me nervous!!

Posted: Sat Oct 25, 2025 10:22 am
by ohtobecucked
mbanthony wrote:
Sat Oct 25, 2025 10:15 am
You gotta do it. For obedience sakes but more importantly to find out the surprise.
99.9% there. I asked if I can watch my censored porn (no tits or pussy for me!!) to get myself in the mood - i'm allowed but only for 1 minute. Being horny will definitely help me do it.

I'm not sure WHERE I'm supposed to go - I live in a quiet street and thought I'd just do it there, but I don't know (i've messaged her to ask but I don't want to bother her too much while shes with BF).

I hope she doesn't want me on a busy street or near shops :-(

Super excited but nervous too.

Re: Wife has set me a challenge with a surprise for me at the end - but makes me nervous!!

Posted: Sat Oct 25, 2025 10:25 am
by mbanthony
Maybe the backyard. You mentioned outside. Perhaps doesn’t require public.

Re: Wife has set me a challenge with a surprise for me at the end - but makes me nervous!!

Posted: Sat Oct 25, 2025 10:33 am
by ohtobecucked
That would be my preference!! I'll need to be able to setup my phone to take pics /video quickly, too - not to mention it should leave me more time /less panic when I'm trying to cum.

A thought came into my head just then and I don't want to follow it for the time being - what if the surprise is that's she pregnant? They usually use protection but these things happen, obvs.

Welp, we'll see...

EDIT: it's a shame that all of her 'toys' are now at her BF's, would have been even more exciting / terrifying!

I've taken some massive toys in (HUGE!!) in my teens and twenties, but got lost in a move. I would have loved riding one of them outside on cam for them. :up:

Re: Wife has set me a challenge with a surprise for me at the end - but makes me nervous!!

Posted: Sat Oct 25, 2025 10:51 am
by ucaneffher
While these challenges sound fun, they are more specific and catered towards someone's special kink. They wouldn't be necessarily something that would appeal to me or my then hot GF but I want to believe that's it's moreso for the act of being "obedient" that makes it hot and interesting.

You mention her getting fucked outdoors being an awesome surprise. Let me tell you, that is one of the hottest things a cuckold can find out his gf/wife is doing with others. Mine did a lot of public sex acts with her other men and it made her extremely horny... I could never bring myself to fuck her publicly but she was okay with that because she had guys bending her over in building emergency stairwells, bent over her lover's car in industrial/commercial area parking lots while traffic drove by normally, riding her other lover to completion as he drives on the highway, not to mention the countless blowjobs in traffic.

The most notable being her usual quickie/blowjob in her lovers car at night parked outside our home when he brought her home. It was suspicious enough that My neighbor mentioned the black SUV with tinted windows always outside every night for 45 min before my GF getting out adjusting herself. The dark windows helped but he was onto her and always mentioned it to me.

If you find it hot, suggest it to her! In the meantime, worry about finding a spot to masturbate publicly without exposing yourself. If you have a a backyard, go out at night in a corner of the yard and go to town. Good luck!

Re: Wife has set me a challenge with a surprise for me at the end - but makes me nervous!!

Posted: Sat Oct 25, 2025 10:58 am
by ohtobecucked
Fantastic reply! Yeah, it’ll definitely be in our garden, makes so much sense.

To be clear, I have NO IDEA what the surprise is, just putting 2+2 together given this has never been brought up before.

From a recent topic of mine, I would love it if this brings out in her BF, the desire to let me serve him, too.

Again - nervous and excited in both aspects.

Re: Wife has set me a challenge with a surprise for me at the end - but makes me nervous!!

Posted: Sat Oct 25, 2025 11:37 am
by ucaneffher
Sounds like you have some bi curious desires to also be involved with him. Is her boyfriend also bi curious? Is your wife aware of and in favor of your curiosity?

Your wife has a BF and is preparing a surprise for you. You are lucky. meanwhile my GF isn't a hot GF yet and I wish I would receive the surprise that she has a boyfriend or a lover and wants us all to get on the same page.

I can't wait for those times where I get to stay home alone for hours because she is out spending time with a lover or boyfriend. You're very lucky to already be in a position where your woman is going out and spending time with him.

Re: Wife has set me a challenge with a surprise for me at the end - but makes me nervous!!

Posted: Sat Oct 25, 2025 11:42 am
by ohtobecucked
My wife, yes - harder to persuade her BF.

It’s been nearly. 12 years no pussy for me (in fact, it might be very very soon) and that was what I was prepared to do to chase this lifestyle.

Don’t give up, carry on telling her all the pros - I wouldn’t change my life now for the world.

Meanwhile - Going to wait until a bit later but I’ve got lotion so my hand feels more ‘pussy like’ and hopefully it won’t take me long to cum - will try and get video and pics as proof.

Re: Wife has set me a challenge with a surprise for me at the end - but makes me nervous!!

Posted: Sat Oct 25, 2025 11:44 am
by ohtobecucked
My wife, yes - harder to persuade her BF.

It’s been nearly. 12 years no pussy for me (in fact, it might be very very soon) and that was what I was prepared to do to chase this lifestyle. But you’re right, I DO feel very lucky, especially as their relationship becomes noticeably stronger when I ask my wife for details.

Don’t give up, carry on telling her all the pros - I wouldn’t change my life now for the world.

Meanwhile - Going to wait until a bit later but I’ve got lotion so my hand feels more ‘pussy like’ and hopefully it won’t take me long to cum - will try and get video and pics as proof.

Re: Wife has set me a challenge with a surprise for me at the end - but makes me nervous!!

Posted: Sat Oct 25, 2025 12:15 pm
by ohtobecucked
Wife just messaged to see if I’ve done it yet, but sounded a bit breathless… because she just got fucked for 25 minutes in the shower 😻😻

I have NEVER been allowed to do that. Since we went heavy on the denial she only lets me see her get changed from the back if at all. They’ve both been completely naked all evening.

I love my life!!

Re: Wife has set me a challenge with a surprise for me at the end - but makes me nervous!!

Posted: Sat Oct 25, 2025 12:30 pm
by ucaneffher
ohtobecucked wrote:
Sat Oct 25, 2025 11:44 am
My wife, yes - harder to persuade her BF.

It’s been nearly. 12 years no pussy for me (in fact, it might be very very soon) and that was what I was prepared to do to chase this lifestyle. But you’re right, I DO feel very lucky, especially as their relationship becomes noticeably stronger when I ask my wife for details.

Don’t give up, carry on telling her all the pros - I wouldn’t change my life now for the world.

Meanwhile - Going to wait until a bit later but I’ve got lotion so my hand feels more ‘pussy like’ and hopefully it won’t take me long to cum - will try and get video and pics as proof.
I will assume that 12 years no pussy is synonymous with being in the lifestyle at least 12 years? If so that's awesome!

I'm with you 100%, while I absolutely love pussy, if the ONLY thing keeping my girlfriend from becoming an active hot girlfriend and her only condition to become a hot girlfriend was me accepting to become pussyfree, I would struggle with the decision for a few days but I know that I would prefer to be her pussy free cuckold for the rest of my life instead of being in a vanilla relationship even if I get pussy.

While pussy free is not my ideal arrangement, being a cuckold to a promiscuous partner is by far my ideal arrangement. Like you, I wouldn't change that for anything in the world, either. I'm trying not to be pushy with my gf but I do remind her and encourage her once or twice a year. Sometimes she'll throw little shade and jabs about going off with another MXN and I get instantly hard.

She knows she has a permanent hall pass just ike my ex did and I know that when the right man comes in the picture, this wanna be talk will be a thing of the past. I want to believe that it's only a matter of time before I'm dealing with a flirty and promiscuous girlfriend again, dealing with first world problems of packing her overnight bag with lingerie and sexy clothes for her sleepover. Or dealing with covering for her Every time people see her with different men.

Those are the types of problems that I'd like to be dealing with in my daily life again. Or even the ever so frequent pregnancy scares that we had every month for many years especially when I was already PF, maybe this time I might experience the inevitable and have to accept seeing her belly growing courtesy of one of her lovers. Again that wouldn't be ideal either but I wouldn't be opposed to becoming the cuckold baby sitter while she's back in bed with her lover.

Re: Wife has set me a challenge with a surprise for me at the end - but makes me nervous!!

Posted: Sat Oct 25, 2025 12:33 pm
by ohtobecucked
Thanks for the great reply. Will answer in more detail soon.

Re: Wife has set me a challenge with a surprise for me at the end - but makes me nervous!!

Posted: Sat Oct 25, 2025 1:00 pm
by ohtobecucked
THAT WAS SO COLD AND WINDY!!!!! I couldn’t finish, the weather just made it impossible to get hard and stay there. I have sent my evidence anyway, I tried my best! :-)

Hopefully I’ll get a message back but tbh, it’s likely they’ll either be fucking or asleep - I’m too impatient to wait that long.

Re: Wife has set me a challenge with a surprise for me at the end - but makes me nervous!!

Posted: Sat Oct 25, 2025 2:18 pm
by Long Lurker 34
ucaneffher wrote:
Sat Oct 25, 2025 12:30 pm
ohtobecucked wrote:
Sat Oct 25, 2025 11:44 am
My wife, yes - harder to persuade her BF.

It’s been nearly. 12 years no pussy for me (in fact, it might be very very soon) and that was what I was prepared to do to chase this lifestyle. But you’re right, I DO feel very lucky, especially as their relationship becomes noticeably stronger when I ask my wife for details.

Don’t give up, carry on telling her all the pros - I wouldn’t change my life now for the world.

Meanwhile - Going to wait until a bit later but I’ve got lotion so my hand feels more ‘pussy like’ and hopefully it won’t take me long to cum - will try and get video and pics as proof.
I will assume that 12 years no pussy is synonymous with being in the lifestyle at least 12 years? If so that's awesome!

I'm with you 100%, while I absolutely love pussy, if the ONLY thing keeping my girlfriend from becoming an active hot girlfriend and her only condition to become a hot girlfriend was me accepting to become pussyfree, I would struggle with the decision for a few days but I know that I would prefer to be her pussy free cuckold for the rest of my life instead of being in a vanilla relationship even if I get pussy.

While pussy free is not my ideal arrangement, being a cuckold to a promiscuous partner is by far my ideal arrangement. Like you, I wouldn't change that for anything in the world, either. I'm trying not to be pushy with my gf but I do remind her and encourage her once or twice a year. Sometimes she'll throw little shade and jabs about going off with another MXN and I get instantly hard.

She knows she has a permanent hall pass just ike my ex did and I know that when the right man comes in the picture, this wanna be talk will be a thing of the past. I want to believe that it's only a matter of time before I'm dealing with a flirty and promiscuous girlfriend again, dealing with first world problems of packing her overnight bag with lingerie and sexy clothes for her sleepover. Or dealing with covering for her Every time people see her with different men.

Those are the types of problems that I'd like to be dealing with in my daily life again. Or even the ever so frequent pregnancy scares that we had every month for many years especially when I was already PF, maybe this time I might experience the inevitable and have to accept seeing her belly growing courtesy of one of her lovers. Again that wouldn't be ideal either but I wouldn't be opposed to becoming the cuckold baby sitter while she's back in bed with her lover.
UC
- So the possibility remains? It's MAYBE an If and a WHEN? :o :shock:

Re: Wife has set me a challenge with a surprise for me at the end - but makes me nervous!!

Posted: Sat Oct 25, 2025 3:20 pm
by ucaneffher
Lurker, she knows it's undisputably my deepest and most desired fantasy. She knows and has no doubt that I would by far prefer to send her off to other men every weekend than say having 2,4,5 women for myself every weekend lol.

Not only is she aware but She has tested the waters by dipping her toes more times than I can count. She has confirmed time after time that that any time she talks to men anytime we've gone out, I back off and let her take charge and run off to spend the rest of our outing with the other man that she just met/flirted with.

She has confirmed countless times that I'm 100% down for it by engaging in various dating platforms including swiping on tinder in front of me when it's supposed to be us time both at home and on dates. Instead of me criticizing her for looking for other men during our time, I accept it every time. We have literally been out on dates and we are at the restaurant or bar completely silent as my girlfriend is sitting across or next to me swiping left and right looking at men. I approve that behavior and she has confirmed it.

She has gone mamy dates and sees I haven't gotten cold feet. She's had me drive her to dates and pick her up. She has even done the cheating girlfriend thing behind my back. She told me she was going out with her girlfriend and instead she had me pick her up at 3am from some guys condo looking like a total slut and drunk. I even got to watch them kiss from afar and listen to her tell me he was feeling her tits and ass through out the night and she allowed it.

So as you can see , over the years she has tested my level of seriousness and has always been met with acceptance and encouragement. She was on a steady roll and having fun until with many different guys until we had some relationship hiccups and she altogether stopped her extracurricular activities as a way to not put strain on our relationship during that rough period. I thank her for that because she did explain that it would be unfair to me if she was with a new man or men with a clean slate with her.

Over the last 2-3 years our relationship has gotten more solid than ever, probably as strong or stronger than it has ever been. Based on this, her knowing it is my ultimate fantasy, and the obvious fun that she had engaging with other men on dating platforms, going on dates, and flirting and dancing with men in front of me..I want to be optimistic and believe that it's only a matter of time before her curiosity spikes again, especially if a good candidate comes into her life. I still believe that she will be the one to cuckold me and have a full blown long term boyfriend on the side, partly helping with her sexual needs or possibly taking care of her sexual needs entirely.

So yes, I still believe that she will have a boyfriend on the side one day.

Re: Wife has set me a challenge with a surprise for me at the end - but makes me nervous!!

Posted: Sat Oct 25, 2025 3:21 pm
by ucaneffher
Lurker, she knows it's undisputably my deepest and most desired fantasy. She knows and has no doubt that I would by far prefer to send her off to other men every weekend than say having 2,4,5 women for myself every weekend lol.

Not only is she aware but She has tested the waters by dipping her toes more times than I can count. She has confirmed time after time that that any time she talks to men anytime we've gone out, I back off and let her take charge and run off to spend the rest of our outing with the other man that she just met/flirted with.

She has confirmed countless times that I'm 100% down for it by engaging in various dating platforms including swiping on tinder in front of me when it's supposed to be us time both at home and on dates. Instead of me criticizing her for looking for other men during our time, I accept it every time. We have literally been out on dates and we are at the restaurant or bar completely silent as my girlfriend is sitting across or next to me swiping left and right looking at men. I approve that behavior and she has confirmed it.

She has gone mamy dates and sees I haven't gotten cold feet. She's had me drive her to dates and pick her up. She has even done the cheating girlfriend thing behind my back. She told me she was going out with her girlfriend and instead she had me pick her up at 3am from some guys condo looking like a total slut and drunk. I even got to watch them kiss from afar and listen to her tell me he was feeling her tits and ass through out the night and she allowed it.

So as you can see , over the years she has tested my level of seriousness and has always been met with acceptance and encouragement. She was on a steady roll and having fun until with many different guys until we had some relationship hiccups and she altogether stopped her extracurricular activities as a way to not put strain on our relationship during that rough period. I thank her for that because she did explain that it would be unfair to me if she was with a new man or men with a clean slate with her.

Over the last 2-3 years our relationship has gotten more solid than ever, probably as strong or stronger than it has ever been. Based on this, her knowing it is my ultimate fantasy, and the obvious fun that she had engaging with other men on dating platforms, going on dates, and flirting and dancing with men in front of me..I want to be optimistic and believe that it's only a matter of time before her curiosity spikes again, especially if a good candidate comes into her life. I still believe that she will be the one to cuckold me and have a full blown long term boyfriend on the side, partly helping with her sexual needs or possibly taking care of her sexual needs entirely.

So yes, I still believe that she will have a boyfriend on the side one day.

Re: Wife has set me a challenge with a surprise for me at the end - but makes me nervous!!

Posted: Sat Oct 25, 2025 8:34 pm
by ohtobecucked
Woohoo! I couldn’t be happier with my surprise!! It is half term this week here and my daughter is going away for 3 days with her grandparent - so my wife has invited BF to stay here for those 3 days!!

I get the spare room, they’ll obviously take our bed. I am beyond excited!!

She also tried her first anal (beads) yesterday and said she loved it, which I never managed to persuade her to do.

She’s asked me to order lingerie for the special occasion (not that I’ll see her in it!) and lube, so I’ll sort all that so they don’t have to.

This has ALWAYS been a dream of mine - it’s the perfect surprise for me. I’m going to be able to hear him pounding my wife from the room next door… heaven!!

If he manages to finally get her to try actual anal while I’m next door I’ll probably pass out there and then! 🤣

Not sure they’ll let me see - maybe leave the door ajar, but IF I could watch her get plastered in his cum, again, something I’ve never done with her…

So excited!!

Re: Wife has set me a challenge with a surprise for me at the end - but makes me nervous!!

Posted: Fri Nov 14, 2025 6:28 am
by pmate
So how did it go? Was it everything you had hoped?