A Box Full of Secrets

My husband is a closet sissy. He hides his extracurricular lingerie and toys in the top of his closet where he thinks I won't find them. Unfortunately for him, last year he was on a work trip and our difficult old grumpy cat got stuck up there somehow and wouldn't jump down. The cat had dug itself into the back corner of the top shelf behind some old uniforms and jerseys of my husband's youthful days and I was forced to get a step stool and clear the shelf to retrieve the needy cat. Just before I threw the clothes back up and made it my husband's problem to rearrange, I noticed a box slightly purposefully wrapped in an old t-shirt that was now visible through the neck. Never knowing my husband to keep anything up there, I joined the cat in his curiosity and climbed up the stool again and retrieved the box.

I assumed this was maybe his trophy box of girls past with pictures and trinkets from ex girlfriends that he didn't know how or was reluctant to discard even though we had been together for more than a decade. Being his wife and sharing vows so many years earlier that had the cheesy line of "what's yours is mine and what's mine is yours" I decided to see what was in 'my' box.

To say I was shocked would have been an understatement. Inside was panties and bras and an assortment of dildos and a few pieces of makeup to match the mostly red lingerie. I knew my husband preferred red, as most of the gifts over the years he's gotten me usually come in the bold colour made of lace or silk. But as I went through the box I noticed all were the same size....and the right size for my husband. At the bottom of the box was a list of websites and passwords.

Being the amateur IT investigator I am (based on the numerous times I caught ex's of my own cheating on me by finding undeleted sent emails) I decided to go for a spin on the World Wide Web to see what my husband had obviously been hiding. Logging on to the first site hit me like a ton of bricks. By the third site, I didn't need to see anymore (right now). I copied all the information, put everything back including the box inside the t-shirt and decided not to tell my husband about the dumb grumpy cat's escapades or my discovery. Instead I decided to do my research.

Sure I've now read countless stories of women being mad and feeling betrayed by their closet sissy husbands, but as I sat that night alone at home, I thought about how I could have my own fun with his secret life. And that night I decided to set a plan in motion. I spent hours over the next year watching his internet use by logging into all his femdom and sissy humiliation accounts to see his comments and likes. Our 10 year wedding anniversary was 6 months after my discovery and 6 months prior to his next big work conference. I decided to use this occasion to set my plan in motion.

We went to our favourite restaurant for a fancy dinner and it was there I decided to get the ball rolling. After our main course before dessert I surprised hubby with my gift. A pink 1" chastity cage. He opened it right at the table and when he ripped the wrapping paper off he had nowhere to hide the packaging. I tried to calm him down and discreetly opened the box and removed the cage and lock. I also pulled out a small tube of vaseline from my purse in case he needed some help getting the cage on (I had read it helped the first time getting it on) and told him I loved him as much as our wedding day (and then I lied) and said a gf at work told me about chastity and that it sounded like a fun time and I hoped he would trust me enough to give it a go.

With that he told me he loved me and had no idea I would be into something like that. I laughed and made a joke about who knows what kind of kinks I'd been hiding from him. I could see him get even more red and begin to show a little anxiety. I told him it was all in good fun and we could talk more about it on our way home but first I'd like him to get locked up right now. He looked around nervous the patrons around us could hear about his penis being locked away but I just shhhh'd him and asked him again if he wanted to give it a try. He said "of course I'd love for you to be my keyholder but" and then abruptly stopped himself clearly using lingo he thought I wouldn't understand and showing his cards a little more than he wanted.

I jumped at the opportunity to explain "oh of course I want to be your keyholder. I already own your heart, why wouldn't I want to own your cock? Now if you want to experience something new and fun go off to the bathroom and lock it up missy!" This time it was me playing fast and loose with my cards, but I figured I was safe to just laugh about the pink cage being girly if push came to shove. Finally he agreed and ran off to the bathroom.

Upon his return I had my present I bought for myself from him waiting on the table. He came back and gave it an odd look and I put my hand out flat looking for him to give back the key (the spare I had taken before wrapping and left in a similar box of his in the top of my closet -- cheeky I know) and as I closed my fist I said "Oh you shouldn't have" and quickly unwrapped my gift to myself opening up a brand new Tiffany's chain. Like a seasoned Vegas act, I slipped the key on the chain as I went to put it on. I asked "How does it look?" And his mouth dropped to the floor when he saw his key to his freedom dangling in my cleavage. Before he could close his mouth I replied "I'll take that as you like it".

We finished dessert and hubby couldn't sit still with his head spinning around looking to see if he could see anyone he knew and if anyone would notice his key dangling between my breasts. We went home shortly after without a comment or a second glance from anyone about my new jewelry. I had to admit, it was making me very wet seeing him in such a state. When we got home we talked about the rules and came up with a list we were both comfortable with. Anytime he felt uncomfortable and wanted to be unlocked to check I would allow it under supervision. We agreed to weekly cleanings, but I would ultimately now be in charge of his orgasms.

He agreed to all the terms and I pulled out a contract I had found on a chastity cage site and we both signed. Step 1 complete!

The next few steps were all going to be around getting him comfortable with his cage and then ultimately a big coming out party at his work conference being the final hurrah. Throughout the next 3 months, I would unlock him and provide a blowjob or have sex when I was really horny every week. Then every two. By the third month I unlocked him the first week then the last day of the month.

Over the next three months I didn't let him cum once. I spent almost every night with my hand somewhere on his groin or in his pants and very few nights I would remove the cage to edge him for an hour or so just to lock him back up. He was such a wonderful husband and took every direction so well I felt terrible I hadn't found this earlier on in our relationship.

While all this time was passing I was also busy preparing for his work trip. I had him tell me daily about his work day and about all the people he met with and what they were like. I'm sure by the end of the 6 months I was good enough to sell his product lines as well as him. I knew all the vendors he liked and didn't. I knew the ones he thought were good technically and the ones who just sold based on the amount of cleavage they showed or how short their skirts were. I knew their names, their companies, their locations and from my IT investigative skills I found all the lovely female reps he liked and didn't like personal social media accounts.

Through my online "stalking" I found out which ones were married or in committed relationships and who was divorced or single. Some had their age posted and others I would be able to ballpark based on length of careers on LinkedIn. Finally I was able to land on 5 lovely ladies to give my hubby a coming out experience of a lifetime.

As these were work associates of my hubby, they were spread out all across the country. We were currently in the central time zone which helped me find ways to connect with each lovely lady individually. I would find the site they were most active on and then send them a DM. Felt very mischievous sliding into all this attractive ladies DMs but at least I wasn't there to send them dick pics (well at least not yet. I might have to send hubbys caged dick to prove I was serious but figured I didn't need to start that way).

I started off sly and just connected with the ladies trying to come up with a surprise gift for him at the conference and wanted to see if they would be willing to chat with me in secret so I could set something up. 3 of the ladies jumped right on it saying how much they loved my husband and had heard so much about me (making me blush and love him even more). The other two I knew would be a tough first interaction. But I figured once I shared my plans, knowing the level of distaste my husband had for them, they'd probably be the easiest 'yes', I just needed to get past their gates and lay out my plan.

Over a few weeks I took my shots. The three ladies who loved my hubby, I had set up needing help on a gift. And once on a call I built a quick rapport with them then finally confessed to them about me finding the box and not knowing what to do then starting down this rabbit hole then acceptance and wanting to help my hubby be happy. By the time I finished the story, all three ladies individually asked the same question "what do you need me to do?" And were completely in once I completed sharing my devilish plan.

The other two I went in a different direction. I DM'd them saying I had heard my hubby on the phone with them and I wanted to clear something up. I said we lived in completely different states and I wasn't accusing them of anything, I just needed to talk. Finally they both agreed and I went in for the kill. As soon as we got on the phone I started my well thought out speech. "Look I know my husband and you do not like each other personally or professionally. But that is exactly why I am calling you." And then I went straight into a quick story of finding his stash to having him now locked up to eventually explaining my ask of them. Both of them gave me a resounding "Yes, I'm in!" Upon my asking the final question. And with the ladies all in, the plan was in action and the stage was set.

-------

It was a few days before my hubby flew to the long awaited conference. He always enjoyed the trip but I think this year was going to be on a whole new level. I had decided around month 3 of him being caged that I would find my way there and surprise him during the magical night I had planned. I knew he was too good of a man to cheat on me but I had a whole plan to get him in the situation I needed him. And with my best friend spotting me a flight on her credit card that I'd promise to pay her back after my surprise trip (which she was just to surprise hubby with hotel sexy time) I had explained I didn't want him to check the statements and see the charges so I would pay her back as soon as the cat was out of the bag.

He was flying out on the early morning flight and I would be in the early evening. I had booked a room in a hotel across town (again with help for my bestie). Just before he was about to leave he came up to me and said "Ummm, I don't ahhh...could I get the cage removed before I fly?" A valid request and I kinda laughed wondering how many times he rehearsed it. And snapped a quick reply saying "No, but I will change out the metal lock for this plastic one and a numbered tag." I had done my research and even called the TSA hotline and asked a lovely woman who died laughing when I asked if my husband's small locked dick would set off any alarms or get him sent to Gitmo. She informed me as long as there wasn't any metal he would be good. If there was it would set off the alarms and it could be up to security personnel's discretion if they would let him board. So after some research I had found the lock adapter for travels that was metal detector proof.

With the lock changed out I made a scene of recording the numbered tag telling him I'd be asking for pictures throughout the conference to make sure it wasn't tampered with. Then made another scene about what would happen if he did tamper with it or if some hot number he hooked up with at this yearly incursion ripped it off. He assured me there was no one like that at the conference making me giggle a bit before replying with "oh ok there big boy!" Shortly after he jumped in his car and drove to the airport. I quickly packed my bags and once I knew he was in the air I called an Uber and made my way to the airport.

He landed and I called him to tell him I was going to the movies to see the latest romcom with my girlfriends and then we'd be going for dinner and drinks after so I would text him when I got home. Figured it was a great cover for not being available to chat while I was in the air. The flight went by quickly and for once I wasn't anxious about flying, I was solely focused and anxious about my year long plan of exposing my sissy husband and giving him the best night possible.

The conference was a 3 day affair and for the first 2 I planned to get all my ducks in a row with the last night being the big show. Upon checking in to my hotel I started a group message with my helpers. All 5 quickly connected who one another were and all 5 were still extremely committed and excited about the plan. Over the next 2 days the ladies planned to tease, flirt and make it extremely difficult for my husband to not be extremely frustrated by his cage. Even the two ladies who particularly despised my husband (mostly due to deals gone bad or a deal or two my husband beat them out on I eventually found out) were all in on the tease. If they had meetings with him, they would make sure to unbutton a button or two from their blouses or wear short skirts with pull-up stockings and garters that when they would sit next to him, would ride up relieving more than would be considered slutty professional.

Waking up on the final day I texted hubby and asked how he was and asked for a cage check. He responded with "Tight. Very tight" and a picture proving he wasn't lying. His meat was being pushed through every gap in the cage. My favourite sight. Before I quickly flipped the picture to the ladies group chat commending them all for a job well done and hoped they all sleep well as tonight was going to be a barn burner and hoped everyone was ready to bring their 'A' games I lined up my very last duck.

The text to hubby read "One final request so I can feel confident you aren't going to slip out of your cage and show your little man clit to any of those gorgeous sales ladies you've told me about. Hidden in your suitcase lining, there is a special addition I'd like you to wear today. Please put everything on before suiting up. You will be required to send me pictures throughout the day so don't add any extra layers. This way I will know you will be thinking of me and only me all day. Complete today's challenge and your keyholder will reward you with the wildest night of your life where all your fantasies come true."

I sat back and waited for some kind of reply telling me no or negotiating the request. But all I got was "Yes ma'am 😘". I replied quickly and said once he had his surprise pieces on I required a picture before he completed dressing. Again I waited. Within 5 minutes and no other complaints or pushback, I stared at my phone which now had a picture of my hubby with his head cropped out of the pictures standing in front of a full length mirror dressed in only a sheer red g-string (that you could clearly see his pink cage through), matching sheer red bra and finished by completing the set with a garter and stockings. I had done it! A whole year of planning and now my hubby truly stood virtually before me completely exposed as the sissy he dreamt of being.

I replied with a simple "Good Girl!" Before sending a second text allowing him to wear socks to not completely out him today but he was not allowed to wear boxers or an undershirt beneath his pants and white dress shirt. He again responded with "Yes ma'am" and with that I told him I would check in with him later and told him I loved him.

I then sent the piece de resistance to the ladies group text; my sissy hubby's mirror selfie. Their response proved that today was going to exceed all my hubby's fantasies. Then after a few jokes and laughing emojis, the ladies and I all agreed to meet for a quick coffee off the main strip so as not to be seen by anyone in my hubbys group. As I got to meet all the ladies in person for the first time I was extremely impressed at my husband's restraint of never straying with one of the bombshells. I wasn't sure if by the end of the night I wouldn't hook up with one of them (even though I know from multiple jokes and one liners over the years how much my hubby would love to see that -- hmmm that is a good idea...put that in the back pocket).

Nice lady 1 - Candice was from California. Tall and long legged. Bleach blonde long straight hair and a body that could only be that toned from multiple weekly workouts or a completely active lifestyle. Her butt and breasts just seemed perfect in all the ways you know that photoshopped model isn't but looks as if she is on the cover.

Nice lady 2 - Natalia, a smoking hot Latina with a heart of gold. The woman who you just knew would be an amazing friend and give you her shirt off her back if you asked. And if you did get her shirt off, you'd be staring at beautifully full DD cups no more than a 34 band. She was tight and fuluptious all at the same time.

Nice lady 3 - Ashley, a bombshell brunette that I'm sure guys would just want to dive in head first. She had such an innocent demeanor, but I knew from our group chats that she loved to be a Dom in the bedroom. She had even admitted her last two relationships had ended as the guys she had dated didn't like her taking charge in the bedroom and telling them how to fuck her.

Mean lady 1 - Brittany is a bitch. And she owned it. No fucks to give anyone. I really liked her but I could instantly see why her and hubby clashed on the battlefield. She wasn't going to bow down to anyone and being from a little firm I'm sure my husband swung his proverbial dick around during negotiations. I couldn't wait to see what she had planned to play out.

Mean lady 2 - Jackie is another brunette with a male chauvinist chip on her shoulder. And not just that, but my husband had beat her bad on a deal. They were competitors in the industry and on a very important tender bid my hubby played some dirty pool to win the deal. It wasn't illegal, but it wasn't the most ethical business move (but I do remember the week long Hawaiian vacation the bonus paid for and I love the pool it bought us at home). She was coming for hubby and I figured her payback for the deal she lost would make up for him lying to me for all the years of our marriage.

The stage was set. The players were all here and ready. As we left the coffee shop that morning I had faith the ladies could pull this master plan off. The plan was simple, the ladies were just going to go about finding a way for hubby to expose his red strings one way or another and then convince him to follow them to a secluded room for them to discuss their terms or they would expose him to the whole conference and yada yada yada. The ladies were all in on the fact 1) it was his fantasy he wanted but unwilling to accept and 2) his smoking wife (aka me) was willing to go through all of this to see her sissy husband truly happy and 3) what woman doesn't like to emasculate a "alpha" male ego once and a while just because she can.

The day seemed to crawl by but the ladies were sending me play by play of the teases and passing comments they were giving my hubby. As the day went on I got wetter and wetter waiting to finally see my husband dressed to the 9's in some of the best lingerie money could buy that the ladies had helped me pick out.