Chastity Diary - Day 01

It is now over 24 hours since I first locked up my pathetic penis and handed over the keys to my wife, and I have agreed to write a diary for each day of chastity that passes for as long as I am caged.

But first, a little context. My wife, Stephanie, and I, have been married now for 8 years and in a relationship for 16 years. I am in my early 40s and she her late 30s.

When we first met, Stephanie had no idea of my kinks or fantasies, and indeed it wasn't until many years in to our relationship that I first plucked up the courage to begin telling her.

It started with small penis humiliation, about 4 or 5 years into our relationship. I had been into the idea for a long time, but had not broached the topic with her or any previous lover. One day though, lying on a sofa, I went for it, asking her if she thought my penis was too small.

"That's an odd question," she said, "Why are you asking me that?"

I explained that I'd done some research and that it seemed I was very much below average.

"What is the average, about 5 inches or so?" she asked.

"More like 6," I replied.

"Have you measured yourself?" she asked incredulously.

"No," I lied, "but I know I am a lot smaller than that."

She looked at me quizzically for a moment and then said, "So, how big is it?"

I said I guessed it was more like 4 inches (a deliberate exaggeration). "Well that doesn't sound too bad," she said. "Show me."

I pulled it out as instructed, and was already throbbing and dripping pre-cum simply because of the fact we were discussing this after such a long time wishing we would.

"Wow, he's really turned on today isn't he?" she said, "Why's that?"

I admitted then that I had a massive fantasy for being told how tiny I was, and how it wasn't big enough to satisfy her.

"Well it is pretty small" she said, and I groaned in pleasure. It wasn't much, but it was the first time anyone had said something like that to me in person (not including on webcams), and I just knew I would explode before long.

"Do you want me to measure it to see what we are working with?" she said, totally surprising me that she seemed to be okay with this so soon.

"Yes please," I said with obvious gusto, and she rose and went over to the desk, from where she retrieved a small ruler.

Without any further word, she placed the ruler on the underside of my rock hard penis, and began to look at the measurement, but I stopped her and stated that from my research I understood that you had to measure it on the top side and positioned the ruler for her.

"Okay, so what's that?" she asked as she tried to gauge where the tip of my cock fell on the line. "4 inches?" she said, "Is that all?" She had actually rounded me up as it was only just over the 3 1/2 inch mark, which I pointed out to her.

"Well that does sound very small," she stated, "What was the average again?" I reminded her that it was 6 according to my research.

"Okay, so it's official, you have a tiny penis," she said, and began running her thumb over the soaking head.

"How does it compare to your other boyfriends?" I asked.

"Well I never measured them, but...," and she proceeded to tell me that her first boyfriend was bigger, probably more like average. "So if he was average, that would make him double my size?" I said, visibly flustered at this point. "Yeah I guess it would," she said, and then I asked her about her last boyfriend. "Oh he was way bigger," she said, "And thicker too."

"Do you like being told how small you are?" she asked deviously, knowing the answer full well by this stage.

I was fully on the brink of orgasm and I said that I did. "Have I ever made you cum?" I said breathlessly.

She looked at me with a cruel look of contempt and simply said, "No", and before I knew it I was cumming.

It had gone just as I fantasised it would, as have many, but not all of my kinks with her over the years, but for many years, small penis humiliation was the limit of it, and I remained too nervous to take the next step.

Eventually that happened during sex, when as she often does, she was telling me that she couldn't feel it, and that I needed to push harder. On this occasion though, I tried to push it off in a different direction, telling her she should find a real cock to fuck, one much bigger. She rolled with it, and by the end was telling me how she needed a big, fat cock to make her cum, that my dick was useless and so on.

In time, this led on to further roleplay, and then many years later I finally decided to go for the kill and ask her whether she would cuckold me and fuck other guys for real.

As has been documented elsewhere, Stephanie had many objections to making this real, but we began to incorporate it even more into occasional roleplay. The pinnacle was probably the day a few years back where she booked a hotel room for a few hours and sent me a text, supposedly meant for a lover, and then afterwards inviting me to come watch her with him. She told me a hotel and room number, and I strolled up there, and was surprised that the door was open, given that she didn't know how long I would be and that she was lying naked on the bed covered in "cum" (a fake cum lube I had purchased for this very scenario). She went on to describe what he had done to her, how big he was, how she wouldn't be able to feel me at all. I was made to lick her "cum-soaked" pussy and breasts, and with so much lube she definitely couldn't feel me when I came inside her.

To this day, there hasn't been a repeat of that afternoon, but to say it was amazing would be an understatement. The cum lube is still in a draw somewhere, and I hope it gets used again at some point.

This all takes us to this week when after having had a cheap chastity device in my possession for a few years, I finally suggested that she lock me up. And that same evening I handed over the keys.

The device isn't great. The tube is way too big for me when soft, and I am able to achieve a full erection in it. Meanwhile the ring is on the small side, so my balls feel crushed, even after only 1 day.

The first evening we talked a lot about it and what I wanted her to do to me whilst I was caged. This did stray off again into discussion of her really having sex with another man, but that was not on the cards, although I did remind her about the cum lube which she had forgotten about and so the roleplay may be possible.

Anyway that first evening, she had me lick her to two orgasms, and of course left me extremely hard and bulging in the cage.

The first full day I had sent her some links to games that keyholders can play, which she didn't actually read till later that evening although I referenced them during the day.

Initially, she had asked me how long I should wear the cage, and I had suggested 3 days. One of the games I made reference to was one where I am given tasks to do and then given a score out of 10 for satisfactory completion. For every score below 10, that number of days is added to the time locked up. I didn't tell her that bit, but when she gave me a 4 for a task during the day, I said to her, "Thank God you haven't read those links I sent you yet in that case."

I was given scores for a number of jobs during the day, mostly 9s or 10s, but even so it would have added considerable time on to the agreed 3 days if we had been playing the game.

When she finally did read the links that evening, she said "Oh dear, looks like you have what, at least another 8 days to be added on." I said that maybe since she hadn't read it at the time, we could let those ones go, and she replied, "Maybe. But this was your idea and I think you want me to be mean don't you?" I had to admit I did. Nevertheless, she let me off those misdemeanours.

That evening I was made to give foot rubs, and back rubs mainly, before she decided to use a toy in front of me, which I was later required to clean.

Again I was throbbing when she had finished, and extremely uncomfortable in the device.

Back in the very early days of our relationship, I had admitted to enjoying having my nipples twisted and on one of those occasions, I somehow managed to cum from that alone. It was the first and only time that had ever happened to me.

Whilst she wasn't going to release me, I pleaded with her to try that again to see if I could cum with the cage on whilst she tortured my nipples. She hasn't yet read about how I should never ask or beg to cum, so I wasn't worried about consequences.

Nevertheless she was very reluctant, explaining that the whole idea was that I wasn't allowed to cum until the cage is removed. I was so lost in lust though that I persisted, and eventually she stated that she would do it for 30 seconds in return for 3 additional days locked up, whether I came or not. I was convinced I was so close that this would be enough and eagerly agreed.

She started the timer on her phone and began twisting them both hard, and I could feel myself about to explode in the cage. I was right on the edge, when the timer went off.

"Nooo," I said, "Just a few more seconds please!"

Smugly, she refused and explained that I now had 5 more days till my release, and that this is what I had wanted. Again, I begged, saying I would do anything, she can even add more days if she would just do 10 seconds more.

"10 seconds more for another 3 days?" she suggested.

"Yes, god yes, please," I said, and she reset the timer and began twisting again.

This time I knew I would cum, for only the second time ever from just nipple stimulation. I was already on the edge, and it would happen, but it didn't happen. The timer went off.

"Noooo," I said again. "That's your lot," she said. "What a shame! I'm going to sleep now. Off you go." I skulked off, still throbbing, to sleep on the sofa and to try and compose myself.

As I write this at the end of that first day, I know I have to control myself more, otherwise I may never get to cum again. I now have 8 days ahead of me and more would certainly be added. She has stated that the 10 score game will take effect from tomorrow, so that's almost certain to add more days, and she has also had me dig out a 20 sided die for one of the games, which could take me up to a month or more.

It has only been 24 hours, but already I am desperate to cum, and writing this diary as required is not really helping.