It’s been a few months so figured I would update if any still read this.
We are doing great. Chastity wise I am getting a new cage today. It’s a ringless device that doesn’t trap the balls. Interesting and curious if it will be small enough to fit when flacid or big enough for when I get hard. There are two theories on these types of devices…1. That it should be tight enough to prevent any erection and your body will adjust. 2. Eave enough room for slight erection, and it will be comfy and still caged. I went for the 0 erection narrow theory. Actually I am not really worried about that, I am more worried about it being either too long and making it pull on my piercing when super short, or it being too short and allowing too much penis behind the cage exposed enough to cum. Even if it’s not perfect I hope it is something I can wear when my real cage starts giving me those blisters.
Serving her has been fun, lately it hasn’t been dresses and the whole 9 yards, last night it was my favorite pair of Capri jeans and a cute top. Didn’t really matter, I felt like me again and was able to focus on her. Cleaned up around the house, cleaned the tub, made dinner, gave her a bath, a full body massage and some erotic fun after. She even let me out of my cage with an orgasm…unbelievable!
I truly cannot describe the feeling of being inside her after some time locked up. The moment I was in her I pushed myself in her as far as I could to get that feeling as much as I could. Part of me wanted to just stay there and enjoy it, the other part of me wanted to thrust in nd out of her as fast and hard as I could. Of course I started thrusting into her like I was trying to reach the back of her. She could probably sense my urgency and told me to slow down and get doxi(the wand). I retrieved the heavy duty pleasure machine and handed it to her. I hovered just over her, I wanted to slide into her as she used the machine but I couldn’t reach her entrance without her removing the wand from her clit, so I just touched, fondled, and tried to enhance her experience. After her O I slid back in to her as far as I could, oh my that feeling again! Totally encased by her flesh, hot wet and wrapped around me, made even more sensitive from being kept in its steel cave. Within seconds I was ready to blow and told her I needed to stop. She whispered that I could finish and I blew. I was clenching and moaning and I could hardly describe it in words, only that for 10seconds I had nothing in the world matter but the moment.
After we cuddled and had ourselves a moment. It made me think of some things that have changed. It’s not necessarily good or bad, just different, will have to ask her one of these days her opinion on them. I assume it’s the way it’s supposed to be because she’s in charge.
1. Clean up. She hasn’t told me to clean up my mess in some time. Maybe it’s something she doesn’t enjoy me doing. I of course do not remind her, after a full orgasm, the last thing on earth I want to do is that. I know I get into subbie mode right away if I’m told to do so, but it’s not something I can do on my own, mostly because it’s about doing as I’m told…like it or not. Of course I would not want her to doing anything that she doesn’t want so I will continue to follow her lead on that.
2. Ruined orgasms. She used to give them to me quite often, as kmuchbas they were maddeningly frustrating, and really the only time I’ve really begged during all this chastity play, they are still fun and although I don’t get to cum, her touching my penis and getting the sensations is still plenty sexy.
3. Punishments. She hasn’t spanked me in I don’t know when. She can if she wants to, she just hasn’t. This is something that used to excite her, it must not anymore cause she hasn’t, and find it hard o believe it’s because I’m so darn good lol! At one point she had even said she was going to make a maintenance schedule.
4. Cock and ball torture. This one I have a catch 22 feeling on. I crave and desire it, I want to feel the pain and throb of truly withstanding it for her, yet it’s obviously pain. I don’t know, she did a little a few times and it makes me super hot to take it from and for her, but it’s not something that must interest her for she only did it a few times and wasn’t too serious about it. I bought a humblr that she could even lock on me, I think the ball tortore is the hottest, but I think she feels like it’s too much and that physical pain isn’t sexual. Ever since she tried it on me I have been craving her firm physical control, it may be something she outgrew.
5. Anal play. She at first was game for milking me(finger in my bottom to milk my prostate till cum leaked out without orgasm). She tried pegging me a few times as well. I had not seen any demands made for this to happen again so I assume she wasn’t into it. Before you ask, no there was no “accident” or poo issues, whenever she was near there I had always cleaned inside and was ready if need be, I still do just in case. Pegging isn’t something that I look forward to its mostly something that makes me feel controlled, an act of submitting so it’s not something to miss or not miss, Although I would love to have an orgasm through pegging, ultimate in sexual submission. I have tried and have gotten close, I just can’t do it by myself so have stopped trying…my arm gets tired right when I almost get there lol. Milking actually feels good so that was something I miss, but when she did it when she touched my cock I would always get close to cumming really fast and had to stop her very early.
Its weird how sometimes things just seem to slip away. I’m not sure if it is a deliberate omission, or more like outgrowing a pair of shoes. As long as she is happy so am I!
I cannot believe how happy I am. I never knew how empty I felt inside and how depressed I really was until someone let me be me, the real me. Is it normal for a real boy to be happier when he’s a girl? No, I guess I’m not normal. Cause the bright side of my life are the days when I’m wearing clothes that belong and I’m serving her. I don’t feel like I’m gross, I don’t feel like a giant lie, and I don’t feel like I’m a mistake that shouldn’t be. I put on my “real” clothes and I open up, I want to hug her and hold her and thank her for letting me be myself and not being alone. It shouldn’t matter, it’s just clothes right? But it does, cause instead of hating myself when I look down, I see the real me, even if it will always be in short doses. It means so much to me that she is in this with me and that I’m not alone. The other day when I was getting ready for serving her I had chosen my casual outfit instead of the more formal dress (which I love), she asked me “no dress today?” I had thought about it, but had already did most of household duties buck naked and formality was about over at this point, so went with some casual clothes. I loved that she was asking, interested, and involved. It would break my heart if I thought she actually hated the real me and put up with it because she loved the lie I put out to everyone else in life.
Sex wise she still pushes all my buttons, teasing me about my size, I still don’t know why I get so turned on by it yet here we are. Maybe it’s brutal honesty that lets me know that I see you and I still love you. A new one is the cuckold stuff which is more recent than others but still some of the hottest things she has said. We both know she isn’t interested in actually finding someone else, but that doesn’t change that when she tells me what she wants, or wants me to do, or what she going to do, I get so turned on I can physically feel precum start to leak out of me. Actually all of her verbal teasing has been the most erotic thing in the world to me. Whether it’s telling me what to do, telling me what she will make me do, or even telling me what I’m not going to do lol, her involvement and verbal or physical demand over me has made me melt.
So that’s where we are now, sexually and emotionally.
So almost 2 years together and going strong, here’s to 30 more!