My wife, Sharon, had just brought up an idea for how we can spice things up in the bedroom. She was talking about chastity play, where my dick is locked up and she is the keyholder. Now, I was a little skeptical of this at first; I mean, wouldn’t this technically be less sex for us? But she argued that it would build up horniness for me, leading to more passionate sex whenever I’m unlocked. So I agreed to trying it out, and she was ecstatic.

Since I gave my permission, Sharon purchased a metal chastity cage online. Once it arrived, she was very quick to stick my dick into the cage and lock it. It felt a little tight, despite me being soft at the time. She decided to test it out by doing some foreplay. We made out and fondled each other like we normally do before having sex. However, this time, my dick was unable to get hard due to the cage. The feeling of horniness was definitely still there, but all I could do now was please Sharon orally. She loved this and came many times throughout, but when we finished, I was still left feeling horny and unsatisfied. I really questioned if this was going to be a good thing for me.

The next weekend comes around (still locked up) and I am so horny that I can’t stand it. I begged Sharon for us to have actual sex, and she agreed, laughing at how much I was struggling. She unlocked me and we began to have sex like normal. It did take me a bit longer to get hard, as my dick had already become used to the cage. After a few more minutes, I reached climax and came harder than I ever have before. I don’t think I’ve ever seen that much cum at once. Both of us feeling satisfied, Sharon locked me back in the cage.

This routine continued for many weeks. Sharon would unlock me for a few minutes during the weekend, we’d have sex, then it’d be back in the cage. Although I was loving how intense my orgasms were now, me being horny throughout the week was starting to affect my work. I expressed my concerns with Sharon, asking if I could be unlocked a little more often. She looked a little disappointed, but asked if I would consider other alternatives. Puzzled, I questioned her about what alternatives there were.

She pulled up some info on her phone about prostate play. The site said that a man can get sexual pleasure by stimulating his prostate. I’m not a prude by any means, but I wasn’t sure how I felt about having something inside my ass. Sharon pointed out that you can stimulate the prostate externally, not just internally. It probably wouldn’t be as pleasurable, but it could still give me some satisfaction to hold me over. I accepted that logic, so she found a vibrator on Amazon that matched her own. She also added a prostate massager to the cart, just in case I changed my mind about having things in my ass.

The items arrived in the middle of the week, and they couldn’t have arrived soon enough. I was feeling extremely horny and could barely focus. I took the vibrator, brought it into the bathroom, and locked the door. I quickly stripped off my clothes and laid on the floor, getting into the most comfortable position. I turned on the vibrator and pressed it on the area between my balls and anus. I felt a slight bit of pleasure, but continued to search for more. Once I found that sweet spot, euphoria washed over me. The pleasure was more intense than I’d ever felt. I sat on that wave of euphoria for what seemed like a long time. I never actually came, but it left me feeling less horny and more satisfied.

As the weeks went on, I didn’t need to be unlocked as often. Sharon and I still had plenty of sex (both with and without the cage), but I rarely felt extremely horny, like in the earlier days, because of the vibrator. I was able to my sexual frustration out whenever I needed to, and I could still enjoy sex with my wife.

One day, while Sharon was still at work, I worked up the courage to try out the prostate massager. I used a generous amount of lube and slid it inside me. I gasped at how it felt just entering me. I then turned it on, and immediately, the pleasure amped up all the way to 10. It was as if I was having a constant orgasm. The massager kept moving against my prostate, making me moan a little each time it did so. I let this last for a good half hour before I decided to stop. I noticed that, despite it feeling like I was having such a long orgasm, only a tiny bit of cum had come out of me.

The months passed by, and this had become our normalcy. We talked it out and agreed that I wouldn’t be unlocked unless Sharon really needed PIV sex (which ended up being a rare occurrence). I didn’t mind, as I had both the vibrator and the prostate massager to satisfy me now. We also integrated these devices into our regular lovemaking, which made things more pleasurable for the both of us.

After one of our great lovemaking sessions, we were getting redressed, and I decided to put on Sharon’s panties on impulse as a joke. They were a red pair with some lace along the edges. Sharon saw me wearing them and practically pounced on me.

“Woah, what’s going on?” I yelped, surprised at what she was doing.

“Mmm, you just look so sexy in this thing, I couldn’t resist,” she cooed.

“I only put them on as a joke. Do you really like it?”

“Fuck yeah, I do. It really suits you, sweetie. You should wear my panties more often.”

“Well, I have to admit, they are pretty comfortable. I guess I can give it a shot.”

From there on, I began to wear women’s panties almost 24/7. Some were Sharon’s, while others we got online specially for me. I tried many different styles, all feeling much better than my male underwear ever did. Upon that conclusion, we ended up throwing all except one pair of male underwear away (just in case of emergencies).

As we were going to bed one night, Sharon made a comment about my nightwear. I almost always just wore old ratty t-shirts that had holes in them, along with some boring sweatpants. She practically threw one of her nightgowns at me and begged me to just try it for one night. And so, I did, and I practically had the best sleep of my life. It was so comfortable, both because of the material and because of the fact that my body was not restricted at all. Sharon was quick to make another purchase to get us matching sleepwear, and I was geniunely happy that she was doing that. She also secretly added some sexy nightwear, which we ended up using a few times when we had sex.

A few weeks go by and we are sitting on the couch, in matching pink nightgowns and watching one of our shows. Sharon decides that she wants to paint her nails as we are watching the show. She picked a light red color that I always thought looked good on her. After about 20 minutes, both her finger and toe nails sported the color. She then turned to me and asked if she could paint my toenails to match hers. I initially hesitated, but figured that it wasn’t any more girly than what I was already doing, so I agreed. And soon enough, I had red toenails, and I had to admit that they did look nice. Noticing that I liked them, Sharon gave me a pair of her open-toed slippers so that I could see my toes whenever I want without being barefoot.

One Saturday morning, both of us ended up in the shower together (I don’t even remember how anymore). We were both handsy with each other, and I made note of how silky smooth her skin was. She then said, “You know that you can have skin like this, too, right?” and handed me her razor and shaving gel. I figured it was worth a shot and shaved the entirety of my body. Touching my skin afterwards was like euphoria, I never knew that my skin could feel that way. After the shower, Sharon made sure that I moisturized myself to avoid any skin problems, and as a plus, it made my skin even softer. It didn’t take long after this morning for full-body shaving to become a daily routine for me.

Another couple of weeks passed and Sharon had just finished painting both of our toenails in a hot pink color. We were laying on the couch, and she had her head on my shoulder. She kept feeling my hair brush up against her and got a little annoyed. Granted, I hadn’t had a haircut in who knows how long, so it was getting a little wild. She took a look at my hair and asked if she could cut/style it in a more feminine way. I thought about it for a moment and initially declined.

“Unlike the rest of the stuff we’ve been doing, people would actually see that part of me. Won’t they question it?” I asked Sharon.

She came back with, “What people, strangers? Our family is thousands of miles away. Our old friends have gotten too busy raising families. You also work from home and don’t get on camera. Nobody but us will see or care about it.”

I couldn’t help but accept that logic, so I let her take control of my hair. She made a few snips here and there, added some curls, and she was done. I looked in the mirror and was stunned at what she was able to do so quickly. There was no doubt that it was such a feminine style, and while I did like it, I was still unsure about going in public with this hairstyle. But Sharon did assure me that it could easily be put into a ponytail in case it was necessary, and nobody would be the wiser. That definitely made me feel better about, and soon enough, we were back to relaxing on the couch together.

The hair situation led to Sharon to being more insistent on me being feminine most of the time, since she felt that the “nobody cares” speech has gotten through to me. She convinced me to wear blouses, pencil skirts, and pantyhose while I worked, which I have to admit was thrilling and enjoyable. She also began to introduce me to makeup, which took a bit of convincing on her part. But after some practice, I was putting on lipstick, mascara, etc. like a pro, and it became a part of my morning routine. She was also super excited to be able to paint my fingernails, as I kept my nails fairly long and she wanted both our fingernails and our toenails to match.

In regards to our sex life, things were definitely changing. Sharon decided that I needed a smaller cage, as my penis was practically soft 24/7. She chose a pink one that was completely flat and kind of made it look like I had female anatomy. But anyways, in the bedroom, we were practically two women having sex. I almost exclusively pleasured Sharon orally, as I was pretty much never unlocked anymore. On my end of pleasure, I’ve been conditioned to only enjoy prostate play. So this led to us getting into pegging, and I’ve got to say, I love it more than I did normal sex. We also found ways to keep things spicy while we were away from each other, like her using the prostate massager’s app to tease me while she’s at work.

After a few months of this having become our norm, Sharon asked me if we could do something a little daring that weekend. I then asked her what she was thinking, and she said that she’d like for us to go on a date night while I’m en femme.

Now, after she asked this, a million thoughts went through my head. What the hell was she thinking? I wasn’t ready for this. There’s no way I could go out in public like this, I’d look ridiculous. But before I spiraled out too hard, she quickly tried to comfort me.

“Look,” she said, “I know that it’s a lot, and I’m sorry if you aren’t ready for that. But I personally think that you are ready. You’ve been dressing like a woman for a while now, and I’ve got to say, you are really killing it. With how you look, and even act sometimes, it was almost as if you were born a woman. And even if you don’t seem that way to others, then big deal! It’s 2025, and trans people have become commonplace, so I doubt anyone would really care that much. If you’re really not comfortable with it, though, then we don’t have to. I was just throwing out an idea.”

I began to think about what she said, and honestly, she was right. I’ve gotten so far in the short of time that we’ve been doing this. I looked in the mirror and agreed that it was hard to tell that I was a man with the way that I looked. I’m pretty much a woman at this point (other than the rare times I’m going outside), as I’m dressing like, acting like, and doing daily routines like most women do. I guess the next step truly is to go out into the real world like this version of myself. And so, I said that I would do it, and Sharon was ecstatic.

That Saturday, we prepped ourselves to go out to a nice dinner. I reshaved the entirety of my body as closely as I could. I curled my hair and turned it into a nice wavy style. We painted each other’s nails in a cherry red color, and did our makeup as fancy as we could. Sharon got us matching outfits, which included a lacy bra/panty set, a black dress, and 2-inch open-toe heels (which I had become comfortable walking in). Once we were ready, I took a big breath to mentally prepare myself, and we were soon out the door.

As we walked into the restaurant, the hostess greeted us as if we were two women. We were escorted to our table, and nobody paid attention to us. That helped me become more comfortable, as it made me realize that either I passed as a woman, or nobody actually cared. We soon put in our alcohol and food orders, and were able to relax a little more and enjoy ourselves. We hadn’t had a true date night in a while, and it was nice. It almost felt like we had gone back in time to before we were married. We chatted as if nothing was amiss, and everyone probably just saw us as either a pair of female friends or a lesbian couple.

After a couple of drinks, our food arrived and we began to eat. I made note to be careful in my eating as to not mess up my lipstick. Regardless, the food was delicious, possibly the best I had in a long time. We chatted a little more as we ate, and I could tell that Sharon was happy that I had made this decision. Once the end of the meal came, I ended up having a good amount of leftovers due to me having to eat so slowly. We got a box for the food, paid the check, and left. Since it was a nice day out, we took a little walk in the nearby park before we headed back home.

When we pulled into our garage, Sharon began to make out with me like there was no tomorrow. She then said that she had a surprise for me once we got inside, for being a good sport about tonight. I was a little puzzled, but didn’t really question it, so we kept making out. We stripped off our dresses as we walked towards the bedroom, leaving us in our bras and panties as we continued to passionately kiss each other. Once we reached the bedroom, she quickly went into the closet and pulled out her surprise: a fuck machine. My eyes widened as she prepped for it to be used on me.

To get ready, Sharon bound my hands to the bed frame, knowing that being tied up was one of my kinks. Since I was laying on my back, she had me prop up my legs for easy access to my asshole. She then got the machine into the right position, lubed it up, and turned it on. The new toy entered my hole and I gasped. This was definitely bigger than what she’s pegged me with before.

Sharon began to make out with me some more as the machine fucked me silly. Our red-stained lips touching was such an erotic sensation, something I never felt as a regular man. With every thrust of the fuck machine, I moaned with delight into her mouth. She also teased my nipples a little, which had become more sensitive lately, and that excited me even more. I was practically in heaven at this point. I lost count of how many times I orgasmed that night.

That night solidified my new life. No longer did I live as a man; the world never saw me as anything but a woman. I wasn’t trans (so no surgeries necessary), but rather, something had awakened in me that fateful day so long ago. And it was all because of chastity.