Sissywannabe2 Self Chastity journal

sissywannabe2

sissywannabe2

Member
May 16, 2021
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Australia, Queensland
I have been drawn to Female Domination since I was a teenager. Back then in the early 80s porn was hard to come by but when I was exposed to BDSM porn in magazines I was hooked.
Even before I even knew what sex was , in 3nd grade even, I liked girls clothes and photos of princesses and pretty girls. But I was also a boy who played football, macho games etc. Enjoying wearing my sister's clothes was confusing and embarrassing.
25 years ago, while asleep next to my wife, she was touching me .somehow her hand reached my bottom and me, half asleep, reached back took her hand, directed it to my hole and whispered "please fuck me". She did, at first gently but as I grew more excited she went harder and rougher. I loved it.
Thus the cat was out of the bag. I felt I could allow my fantasies and desires out. So I started buying sexy women lingerie and clothes, on my way to becoming a cross dresser.
My wife allowed it but was far from happy about it. It was tolerated and sometimes we would spend an evening with me dressed and feminised. We even went out together with me as Sharon , my sissy personality.
I was very much into female domination and hoped to get her to dominate me, if only occasionally in the bedroom. We had a couple of whips and a strap on. Although she used those on me it was obvious it was done just to please me and that she didn't enjoy it. Of course thus defeated the whole purpose.
Around that time (15 years ago) I met online a dominant woman who wanted me to lock myself in chastity as part of a sissification she and I wanted me to go through. She lived in a different country so we used plastic locks with numbers and I sent her photos of me locked so she could see that I was locked and have not removed my cage.
It did not go well. I was using CB3000 and it had two problems. 1: I was able to free my cock out of the cage by making it very limp and small, thereby cheating. 2: I was so aroused with all the sissification, porn, nighties and lingerie that I was hard every night several times. I could not sleep and could not function at work.
On top of that, my wife was VERY against it. Disgusted to be accurate.
So, after just 2 weeks or so, my chastity came to an end .
5 years ago I stopped cross-dressing completely. Threw away all my female clothes, shoes, make-up, wigs , toys. Put it behind me .
Two months ago something happened and I found myself craving sissification in a very deep way. One of the first things that caught my attention and fantasy was chastity and it's affect and importance to a submissive sissy mindset.
I decided to go first with a small, flat and simple chastity cage. In the following post I'll describe my initial experience wearing it.
 

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After experimenting on and off for few days, I thought I could try denying myself orgasms just by not Cumming. You see I am fascinated by the idea of a sissygasm: reaching an orgasm or at least ejaculasion by anal penetration alone. I was video's of sissies and femboys doing that and it appeals to me very much. Apparently it requires a lot of practice but also orgasm denial for weeks if not months
So I tried to masturbate without orgasm. Just edging . A LOT of edging! It was all good and well but every few days I'd fail: it was either a ruined orgasm and all the cum built up in me would just pour out, or my edging would be a bit too much and I'd have an actual orgasm. It became clear that of I wanted to work towards sissygasm I had to be locked.
So, a week ago I put my small cage on again. It only comes off for cleaning.
Few things I like about it:
1 . It is relatively small and not bulging under my clothes. If I wore a dress or skirt now, it would not be noticeable.
2. It's design is simple- just 3 parts including the locking mechanism.
3. It's all round so hardly and pricking or pinching of the skin.
4. It is very comfortable to wear. I even exercise wearing it, doing squat jumps, burpees and all sorts of moved while in chastity. Never a problem (AND I have a butt plug in too!).
5 . It was cheap so it was a good choice for experimenting and familiarising myself again with 24/7 chastity.

The things I don't like so far:
1. Urination is messy. I sit down and pee and it goes everywhere including my balls sack. After I wipe myself clean and stand up, few more drops come out.
2. I could take my cock out and cheat if I wanted too. Even though I got the smallest one they had.

3. It slips down my genitals. Although it will never fall off, I adjust it upwards few times a day which I don't like.
 
I switched to a different chastity device : it's a pink plastic CB6000 small size. It is not an original CB6000 but rather a cheap one I bought on ebay. Since I am still in my early days of chastity exploration, this will do. I attached photos of myself in the previous and current cages.
This one is comfortable to wear. It is bulkier and bigger than the metal sphere one so it is noticeable if I wear tight pants or dresses when sissified . It is a lot more hygiene, I can exercise with it and there is no pinching. I does not slide down my shift (I am using the medium size ring).
I've been locked since 31/5/2021.
 

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A photo of my pink chastity cage under a frilly sissy skirt I bought today . I love the combination. I am working on completing the outfit with white stocking, white high heels, pink crop-top, pink collar, white or pink bunny-tail plug, make-up and wig.
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My wife has serious objections to me wearing a chastity. She is very threatened by my renewed desires and activities . To apiece her, I take my cage off on nights we share a bed (some nights we sleep separately because we are both bad sleepers or because one of us is working late).
I lock myself up 1st thing in the morning or if she gets up and move to another room.
We've had sex few times since the clash about the chastity but I orgasmed only once . I satisfy her mostly with dildo or orally since my elections are weak and short.
 
I am trying a smaller ring with my pink cage. Just to see how it feels compares to the previous one.
I'll be going on a long international trip soon. Many flights and security checks no sure what to do...
 
The smaller ring was too small. My sack turned blue and was pinched .
The chastity came with 5 rings in different sizes. I started with the largest (5). Tried 3 but too small. I am now using number 4 and it seems to fit well. Not too tight and holds the cage high enough and without it slipping down.

Locked since 31/5/21. Butt-plugged since 18/5/21.
Last sex orgasm: 6/6. Last masturbatory orgasm (ruined) 26/5.
 
I've noticed that during anal play there is more cum dripping out of my pink cage. It is not constant and probably not more than a teaspoon during the entire play, but it's definitely more than the few drops hanging on the edge of the cage I used to get 2 weeks ago . I hope this trend will continue!
I don't know if I will achieve sissygasm, but dripping and milking are most welcum
I got a little pink pussy-cat collar.. bow and bell. The ringing of the bell together with the clicking of the lock on the plastic cage are music to my ears
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I'm so happy that I can do my workout routine while caged and plugged! Normally my routine is 20 rounds of 40 seconds work, 20 seconds rest of HIIT bodyweight exercises: burpees, jump squats, jump lunges, push ups, crunches, mountains climbers etc. Iwork out at home.
I was concerned about pain in my groin ,ass, testicle. Even of the plug popping out. But I'm happy to say I've had no issues. The only time i remember I'm in chastity is when I do pushups or burpees and my cage touches the floor.
I'm very happy I don't need to change exercises or unlock myself! Chastity forever!
 
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I have moments of sexual frustration now, which I guess is a good thing. I have been locked for 15 days but did have an orgasm during sex once 8 days ago. Nothing else though.
I have moments, especially at night in bed, when I want to touch and stroke. I reach down and hit metal instead of flesh. I try touching the uncaged parts hoping to feel good but it is not satisfying at all.
I try to focus my attention to the plug in my ass and that helps a little because it reminds me that as a sissy my pleasure is not supposed to come from my sissyclit but rather from my holes being used.
I am in a constant sexual arousal to the point my work suffers. I consume a lot of porn, I shop or windows shop a lot for sexy outfits, shoes and dildos. Photos of sexy models on seductive poses make me almost drool (have you seen Whitney Paige Venable??? OMG!!! ).
I used to masturbate and cum once or twice a day. Just before I locked myself up I practiced edging, sometimes even 10 times a day! The orgasms from masturbation help relieve my sexual obsession, now this pressure release valve is closed.
I keep my wife awake or disturb her sleep because I constantly want to make love to her but when we do I am even more horny because she orgasm and I don't.
This is after just 2 weeks. What will it be like in 2 months???
 
I unlocked myself on 17/6 before travelling overseas. Glad I did that too, I would have hated going through body screening and metal detectors 4 times in 3 different countries.
Locked (+plugged) myself again once I arrived today. Should stay locked and denied until end of July , when it'd time to travel back.
 
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To my disappointment and pleasure I orgasmed today while caged . I was watching something hot (wife teading her caged husband's dick in his clear chastity). One thing led to another and without unlocking myself or "escaping", I came. Hard.
 
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