Young Couple Exploring Chastity (First 9 Months Summary)

It has been a while since I have posted a journal entry but things have changed so much since my last posting that I thought it’d be a good idea to update. Many details will be left out, otherwise it would take forever to write this post. I am attempting to show the progression of just our chastity use, but a few other kinks have come into play during this time.

Our first discussion of chastity happened a couple months before we actually took any action on it. When I brought it up to her she seemed to not be against it but was also not jumping at the chance to lock my dick up.

One night we were shopping online for sex toys and came across a chastity cage and she suggested we buy it to try it out. It was surprising to me, and I had lost some interest in trying it by that time, but I agreed and we bought it along with a dildo for her to use for herself.

The cage we purchased was a very cheap, grossly oversized one from “ManCage”. When we received it we decided to try it on just before we had sex just to give it a test fit and see how everything worked. It was overly complicated and confusing, and the instructions didn’t help much. We finally got it on and while it was uncomfortable, we both were intrigued by it at that point. She then took it off and we had sex as normal then left it in the box for the next couple weeks.

One night when she was going to work she had me lock up and leave it on over night while she was going to be away. After that night I was hooked. The whole night I was just pouring precum out of the cage and was feeling so aroused. But the cage had caused some chafing due to poor fit so we never went longer than over night with that one.

After a couple of times doing the over night play with that cage, I asked her if I could order something that fits better and would be more comfortable and she agreed. I ended up purchasing the Kink3d Cobra N+. When it came in the mail she made me wait to open the box until she got home. When she arrived she opened the box and then we test fit everything and she loved how it fit, looked, and how simple it was to put on versus the previous cage.

We did the over night game a few times to make sure it was comfortable, and it was perfect. Not too tight, not too loose, no chafing, a really good fit. After she saw that I could wear it comfortably for a while she started having me locked only when she would be gone at work, and on weekends while we were both going to be home all weekend. She still didn’t want me to wear it out of the house at this point.

Over the next few months we went through many relationship issues, so the chastity play stopped for quite a while. During this time she discovered my masturbation habit and hated it. She was hurt that I would think sexually about other women and masturbate at a minimum of once a day, even when she was at home.

After our relationship began to heal from the many issues we were facing at the time, she agreed to bring the cage out again. This time she took to it a little more.

We continued with the nights/weekends schedule, but now she allowed me to leave the house with it on but only to places like the grocery store or to pickup dinner, not at work or when we will be around family. She would tease me, edge me, have me make her cum, then lock me back up for the night. Things continued like this for a few months.

This takes us up to about 3 weeks ago from today. She seemed to finally make the connection that when I am chaste I am a much happier person, and a better partner in the relationship.

One day when she got home from work and I was getting ready to leave for work, instead of taking the cage off like we have been doing for months, she told me to leave it on. It would be my first time going to work with my cage on and I was slightly panicking that someone would notice it. I was worried about it all morning but then that started to ease as the day went on and nobody seemed to notice at all.

Since that day I have been locked constantly with the exception of when she wants to have sex or tease me. If we have sex and she lets me cum, she usually allows the cage to stay off the rest of the night. If she teases me without me having an orgasm then she has me put it on before we fall asleep.

She seems to have really grown into her role within these last 3 weeks. She has become significantly more dominant, and seems to be loving it. I wouldn’t say we are in a full time D/S dynamic, but she has definitely been making it seem like it might become that at some point.

During that first week when I was locked full time I told her about all of my fantasies that I hadn’t really mentioned to her before. Things such as cuckolding, being humiliated, sph, etc. She already knew that I enjoyed her pegging me and that I liked when she was dominant towards me.

After the first week of being locked she told me she was going to let me cum if I did everything she asked that day. As I had work, our day together didn’t really start until around 5pm when we went to dinner. Before we left the house she said “I want you to put this in and wear it while we’re at dinner and then you can take it out when we get home” it was a relatively small butt plug. I had barely every used butt plugs, and never had one in me while I was in public.

On the way to the restaurant we hit several sets of train tracks and she would laugh as she saw me wince in pain from the butt plug being pushed up as we hit the bumps.

When we got to the restaurant my anxiety grew because they only had hard metal stools, and they were having a live band play which a crowd of people were watching, and our table was behind the band in direct view of the entire crowd of people. I have never been in view of so many people while wearing my cage, nonetheless a butt plug and a cage.

Our waitress was this very attractive blonde woman and my girlfriend began subtly flirting with her and she was subtly flirting back and wasn’t really talking to me at all. My girlfriend ordered a couple drinks while we were there and this really loosened her up for the rest of the night.

On the drive home she made jokes about how she could have brought the waitress home and had sex with her but that the waitress wouldn’t even show me any attention. She also started telling me about this “really tall hot guy” that she flirts with at work and how she wants to know how big his dick is and what she imagined sex is like with him. It was very arousing and humiliating because we never really engaged in any conversation like that, the cuckold stuff was only recently discussed.

When we got home she had me take the butt plug out and take a shower. After the shower she told me to lay down on the bed and she unlocked my cage and had me remove it. She edged me a couple times then waited for my erection to go away then had me put the cage back on. She then handed me a pair of her panties. I have never worn feminine clothes and I was visibly uncomfortable at her request. She said “I am going to go to the bathroom, and when I get back they better be on or I’ll make you wish you did” so of course I put them on. My balls were sticking out of the panties and it was very humiliating to look at even while I was alone for that brief moment. When she came back I was covering my face with one hand and my crotch with the other. She said “awe, you’re shy my sweet little boy.” Then she proceeded to put on her strap on. She laid down on her back on the bed and said “if you want to cum tonight, I want you suck this dildo like your life depends on it. I want to be impressed at how good you suck it” and she knows how it is humiliating for me to do that and the times we’ve done it in the past I did a poor job. She pushed my head down on it making it go to the back of my throat many times and then I started really trying and she really liked it and made herself cum with a vibrator while I sucked on the dildo. After she came she told me to lay down on my stomach and then she pulled the panties down around my knees. She lubed up the dildo and began fucking me with it slowly and only to about 3/4 of the length. While going slowly she told me to say that I am a little dick cuck and I couldn’t get myself to say it. She then rammed the whole length of the dildo into me and said “say it” and so I told her I am her little dick cuck. She then fucked me harder and faster with the full length and said “I imagine this is how a real man would fuck me, not like you who can only last 10 seconds” Then when she was satisfied with fucking me she had me lick her pussy to one final orgasm and I never got to cum despite doing what she asked.

The progression the last 3 weeks has been insane to me. It’s scary but exciting. Humiliating yet exhilarating. I love the dominant energy she has been giving and she seems to love it also. We did have a discussion about the cuckolding thing and I told her I love the fantasy but I don’t want to jeopardize our relationship by actually doing it. She said she likes the fantasy but also doesn’t want to actually go through with it. So we have just been playing with the fantasy between us and agreed to not bring anyone else in.

We have been super close and happy together since she started really getting into this kind of sex and I am very excited to see where it takes us from here.

 

We got engaged in December haha