Hello, our story, and seeking advice starting slow

Hello and thanks for the warm welcome. I am here looking for some guidance and advice from the sage community here. Mine/ours is probably not a unique story, and I’d bet I’m not the first person to ask this question… maybe even today. That said, it strikes me everyone’s journey is different, and therefore, generic advice is not super useful past a certain point. I figured, the way to get specific advice and guidance is to be specific with my inquiry.

I originally posted the story below on reddit. The story below, and subsequent updates are all 100% true and unfolding in real time.

Important context:

So, my story is an involved one. I’ve been cuck-curious since like high school. I’ve been honest about it (to varying degrees) with the girls I’ve dated over the years, and was up front with my now wife on our like third date that I’m a bit of a freak in the bedroom, and explained my kink. Having been together with my wife now in total for over 10 years, we have had many many conversations about these topics in and outside of the bedroom. And, my kink has evolved… well escalated. I got into some bi-cuckold stuff, which led me to some sissy husband content, which led me to where I am today - a successful man by day, a sissy cuckold wannabe when I find the rare moment of alone time in an otherwise full and busy life.


So, because so many of us keep these thoughts and feelings and impulses from our partners, I want to be clear what my wife knows.

1. She knows I want to watch her with another man - a larger, dominant, better performing man.

2. She knows I also want to get with said man

3. She knows I have tons of sex toys and chastity devices.

4. I’ve talked to her about chastity and explored her interest in the past. She said she “didn’t get it, and wasn’t into it.” (And this bit may be me in denial, but that moment in time was admittedly not a good life moment to explore a kink like this with young children stresses around - hoping the curiosity and willingness is different this time around a few years later).

5. She has played with me in sissy mode and has even purchased me some panties, and a top. (Half because she loves and supports men, and half because she wanted me to stop stretching out her stuff lol)

6. We have both masturbated with dildos next to one another while kissing, imagining we were both getting fucked side by side.

7. She talks dirty to me sometimes - including bisexual, cuckold, sph themes.

8. She knows i chat with people on reddit as fantasy, but that she trusts me not to betray her trust or our relationship.

9. She knows and has consented to me sharing pictures of her with guys online as long as they are not identifiable.

10. …and probably most importantly, through the descriptions above and below, its important to remember that my wife is a relatively quiet, shy, vanilla person in general. Kink isnt her go-to. She enjoys it when we play around and its happening, but rarely is it her idea, and when it is her idea, its likely in service of my pleasure rather than hers. We have a young family, and as such don't have a lot of alone adult time to talk, play, explore, etc,


The Story:

Ok, so to begin the actual story… i was chatting with this hung guy the other day on r/wifepictureswapo and i was showing him some pictures of my wife. Faceless, of course. That’s when he started doing some tribute-type stuff with my wife’s pictures. He had her pics on his phone and had another phone from above recording him jerking to her picture also in the shot. HOT. Then, he started sending me videos of him talking about her while jerking to her pics. Finally, he asked me if i wanted a tribute, and i said yes. He then said, “tell me her name so i can say it when i cum…” when i picked my jaw up off the floor, i told him. And now, i have like 15 videos of this really nice guy with a great cock jerking to pictures of my wife wile voicing his intentions with her and us.

I’m naturally super super turned on at this point, so i did what any self respecting member of this community would do - i went and put a cage on. I wanted to stay horny as i contemplated telling my wife i had these videos. They were so hot. And the kicker is, i really thought she would think they were hot.

So yesterday evening, i pushed myself to do the thing 1000 guys on reddit have asked me to do. This will be familiar to many of you who share These fantasy themes - getting peppered with questions from guys online like “did you show my cock to your wife dude? What does she think of my cock, man? Let me chat with her bro!” and 999/1000 its an eye roll and a click of the proverbial “next” button. But this time, I actually wanted to show her on my own. He didn’t ask me. I wanted to actually tell my wife about him. And i did it. I told her.

She didnt want to see the pictures and videos. She wasn’t mad, but she didnt want to see them yet. But she knew they existed. The seed was planted.

Flash to the next day… Not sure what happened but in my changing clothes, i forgot the key to my chastity device in my other pockets. My wife was starting a load of laundry and checked the pockets and discovered the key (she knows what it is and what it goes to). So, i walk out of my office, and she was walking up the stairs in her panties holding my key between her fingers. She looked at me and said, “careful, or you’re going to get locked forever,” in reference to my losing the key, with a subtly smirk at the corner of one side of her mouth. At that moment, I’m not sure what came over me but ash she extended her hand to place the key into mine I said, “can you hold onto it? Just till tonight?” She looked at me with a quizzical look and then realized what i was asking. She put her hand on my cage and said, “only if you watch the video of that guy jacking off to me.” I said, you mean the video i told you about last night? Right now? You want to watch it now?” She says, “no. I want YOU to watch it. I’ll hold your key if you watch it right now. I’m not ready yet.”

So, naturally, I’m beyond straining against my cage, when i realize the reason i came out of my office was to pee. So, i said as much, and she said, “wait, you can pee with that on?” “You dont make a huge mess?” I said, no, and she says, “show me.”


She follows me into the bathroom and watches as i sit down, with panties around my ankles, my cage hanging between my legs, with my wife who up until 10 minutes ago showed no curiosity and at times active disinterest now laughing at me cause I’m too “hard” in my cage to pee in front of her. She says, “ok ok i’ll leave you to it.” And she left the bathroom.




UPDATE 1: no update. Let me explain. It’s been 5 hours now with not asmuch as a nod nor a reference to what took place earlier. I hope she remembers! I hope she forgets! Speaks to how little she actually thinks of my penis on a day to day basis. Win win. This is so hot


UPDATE 2: The next day. She didn’t forget. But it was anticlimactic - sort of. Last night like moments before we went to bed, and I was sure she had forgotten, she reaches over and just touches the cage through my shorts and says:

Her: you still have that thing on?
Me: yea
Her: you are gonna sleep with it on!?
Me: I don’t have the key…
Her: wouldn’t that hurt?
Me: I don’t have the key
Her: we’re you just not going to say anything?
Me: yea I was kinda hoping you’d forget lol.

She hands me the key, and watches as I unlock myself and my clit hardens immediately and fully locking myself with the base still around my balls until I could get soft again.

I did tell her that the earlier exchange outside my office was the single hottest moment of my sexual life to reinforce the behavior and ensure she knew how appreciated it was.

And that was that. But as we were drifting off to sleep, she did say, “with all this stuff, I’m nervous to leave you alone in the house this weekend.” (In reference to the fact that I’m a bisexual hornball that is craving my first cock, and that she and the kiddos are heading out of town for the long weekend). I’d never actually cheat on her btw.

I said, “well you can always lock me up ”

She said, “be careful what you wish for - that might actually make me feel better”

UPDATE 3: It’s Friday night and she remembered. I took a fine gentleman’s advice in the comments section and and put a dish out in our bathroom where I’d keep my key. I never mentioned it. But she knew what it was and that it meant if it was in there. Literally not a word about my cage, my key, the dish, nothing since update 2 above. And then I get these texts after she left with the kids - it was so unexpected that it took me a minute to catch on to what she was even talking about. Her texting from her Apple Watch in the beginning didn’t help my rapid comprehension either. Here’s the text exchange below. Apologies in advance at how thick I was and slow to pick up on what was actually happening. Goes alto show you real life is a bit messier than fiction. (Parentheses are my commentary and explanation)

(This takes place as she drives to a vacation house with the kids leaving me along for the weekend)

Her: I stole your key

Me: (this is out of the blue enough I had assumed she was talking about my car key. I don’t really respond as I don’t need my car key to her car this weekend as she has her car - obvi)

Her: (10 minutes and many texts later…) watch the video again and I’ll give you one clue where your key is hidden.

Me: (again, I don’t catch on, still thinking she is talking about my car key - thinking that the car key was visible in a video she had just sent me. And again, I don’t care where my car key to her car is)/.

Her: (5 minutes after that…) The one that you have! The one that I haven’t seen yet ;-)

Me: (at this point I have no idea what is going on or what she is talking about. But I’m also not 100% paying attention so I say…) “I’m not sure I follow…”

Her: do you have your cock blocker on? (So adorable she doesn’t know what to call it!! ❤️❤️)


Me: OMG! (I finally get what is happening)

Her: I hid your key
Her:

Me: I love you so much. You have no idea. Thank you

Her:

Her: omg watch the video. You can’t sleep in that thing!!

Me: I’ll watch the video, but I don’t want a clue

Her: you also have to use the purple one (in reference to my 7” long, 6” girth dildo.

That’s all so far.

A few reflections and the help I need:

1. She referred to the video as the one she hadn’t watched YET. My wife plans to watch the video of this hung stranger tributing her. Hot AF

2. If you had asked me a year or two or 5 ago when I first tried in a pair of her panties in secret whether I’d ever have a wife who locked my chastity cage, left for the weekend, instructed me to watch a video of a huge cock cumming all over her pictures, and then instructed me to fuck myself with the dildo matching said cock’s dimensions, I’d have said you’re crazy. Dreams really do come true…

3. This all sounds like a TON of progress, but it feels tenuous at best. I’m keenly aware that I should and want to take this VERY SLOW - at her pace. And, i dont know what slow looks like from a chastity perspective.

Question: How can I give her enough guidance on what I like, and what there is to like about this dynamic from her perspective, while at the same time not biasing her entirely and eliminating spontaneity.

Question: Are there resources that feel credible on safety of wearing a cage? I think she has concerns about safety and alleviating these would go a long way I suspect.

Question: What other resources - on the psychology, sociological, sexual, dynamics of chastity can I share with her? It feels like for the uninitiated, pointing her towards any online community generally would be a recipe for disaster in terms of perception of “taking it slow.” Porn, reddit, forums - dont feel quite right to share with her as an entry point or context setting.

I’m sure I’ll have more questions as this unfolds, but as I say, i cant be the first guy to navigate this slow and delicate on-ramp. Any advice would be greatly appreciated!

-Penny