r/SissyChastity • • 15h ago

Trans i'm gonna keep going after locktober... can i convince you to keep going as well? ๐Ÿฅบ NSFW

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923 Upvotes

r/SissyChastity • • 9h ago

Learn from my mistakes (True Story) NSFW

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467 Upvotes

This is a repost since my last post was removed

I posted this on r/FemboysChastity and the community seemed to enjoy my situation. I hope you do as well. Happy locktober sissies

I've been using chastity for years now but never for more than a day or two. I mostly use it when I put on a little skirt, play with my ass and fuck myself silly. I use a timed lock box to put my keys in so I can't unlock and focus on my ass. I've never gone long without giving in and unlocking but the more I saw of locktober, the more I wanted to push my limits.

I'm currently travelling for work and thought it would by hot if I brought my toys, some girly outfits, chastity and lock box along with me. By day I work and by night a horny, locked up ass slut.

My first night at my hotel I put on my cage, locked my keys for a few hours and fucked myself until they unlocked. I hit that right spot, and the entire time felt like one giant orgasm build up, but to no avail. I couldn't cum. I thought a few nights chastity and working my prostate I could get there.

In peak frustration, as soon as the box unlocked, and feeling the spirit of locktober. I thought it would be hot to lock my keys in the lock box for my entire 3 week trip. BOTH KEYS. I knew the lock box had an emergency opening feature and if I really needed to unlock I could get access at any time.

The first week was incredible. Everyday I got closer and closer to the edge. I would wake up in the night with my cock throbbing in my cage and overwhelmingly horny. This was my record for the longest I have ever been locked. Finally on day 8 I came. No playing with my cage or a vibrator. A pure prostate orgasm and 100% the best orgasm of my life.

In the clarity and bliss that followed I realised how stupid it was to force myself to be in chastity for the entire 3 weeks. I decided to use the emergency feature to open the box and get my keys. I had saved the manual and instruction for this very occasion. I began the unlock procedure holding down the buttons and to my surprise nothing happened. I thought maybe I was reading it wrong and tried again. Nothing. I panicked. I googled options and how to open the box. I check the manufacturer guides and followed the exact instructions. Yet again nothing happened. One of the buttons must have been damage at some point. Perhaps in my luggage while I travelled.

I was left with two options. Break open the box or spend the next two weeks in chastity. As I lay on my bed defeated, I felt so comfortable in my cage. The cage that had brought me to the greatest orgasm of my life. I thought to myself maybe locktober was achievable. I decided to embrace my fate and challenge myself.

Its been a week since then and I have loved every moment. I've been getting hornier and hornier by the day. Every night I play with myself pushing closer to that sweet release.

NEVER lock away all of your keys. Always have a key in case of emergency. I'm lucky, and if I wanted, I could break the box and be out of this cage. I choose not to. I hope some of you can get some joy out of my predicament but please learn from my mistake.


r/SissyChastity • • 11h ago

OF In Bio Clits, corsets, and cages oh my! NSFW

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319 Upvotes

r/SissyChastity • • 3h ago

a quick peak behind the cageโ€ฆdonโ€™t tell anyone NSFW

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298 Upvotes

r/SissyChastity • • 8h ago

1st time doing a small cage NSFW

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216 Upvotes

I had a supporter get me this outfit; first time in heels like these and 1st time in such a small chasity cage. Watcha think?

Yes, they into feet as well , hence the angle of pic


r/SissyChastity • • 20h ago

Iโ€™ve been told the flat cage isnโ€™t a punishment, but it sure feels like one NSFW

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182 Upvotes

r/SissyChastity • • 14h ago

OF In Bio Edging my caged clit with my mini vibrator is melting my brain ๐Ÿ˜ตโ€๐Ÿ’ซ๐Ÿคค NSFW

167 Upvotes

r/SissyChastity • • 7h ago

Squirting while taking it it up the ass. There's no going back for me ๐Ÿ˜ญ NSFW

155 Upvotes

r/SissyChastity • • 5h ago

Just because I'm caged doesn't mean I can't cum NSFW

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139 Upvotes

r/SissyChastity • • 12h ago

Pussy parade ๐Ÿ‘๐Ÿ”๐Ÿฉท NSFW

136 Upvotes

r/SissyChastity • • 3h ago

Fem being caged is driving me crazy๐Ÿ˜œ๐Ÿ’• NSFW

104 Upvotes

r/SissyChastity • • 6h ago

OF In Bio Caged, plugged and feminized NSFW

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84 Upvotes

r/SissyChastity • • 10h ago

Well, I did it again, I added another sissy wife to the harem ๐Ÿ˜› She even shares the same name as my British one. Everyone, please welcome Jess from the US, my other lovely wife ๐Ÿ˜‡ NSFW

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69 Upvotes

r/SissyChastity • • 12h ago

Fem I was aiming for sweet and innocent, but I think a little attitude slipped into the photos. ๐Ÿ˜ˆ NSFW

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60 Upvotes

r/SissyChastity • • 3h ago

Trans When my roommate took my keys I knew there was no way back NSFW

62 Upvotes

r/SissyChastity • • 9h ago

Trans First caged cumshot this locktober~๐Ÿ–ค๐Ÿ”’๐Ÿ’ฆ NSFW

59 Upvotes

r/SissyChastity • • 6h ago

Is my skirt too revealing? NSFW

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49 Upvotes

r/SissyChastity • • 5h ago

What outfit suits the cage best? NSFW

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33 Upvotes

r/SissyChastity • • 6h ago

Fem Never been in a relationship safe to say i never need to take this off then NSFW

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36 Upvotes

r/SissyChastity • • 9h ago

OF In Bio I look so cute in my cage ๐Ÿ’…๐Ÿป๐Ÿ˜๐Ÿคญ๐Ÿ‘ธ๐Ÿป NSFW

32 Upvotes

r/SissyChastity • • 11h ago

Fem I was a top when we first got together :( NSFW

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31 Upvotes

I never wouldโ€™ve imagined this is where Iโ€™d be in just a few months..

18 & 19 :)


r/SissyChastity • • 7h ago

OF In Bio Ive just recently gotten into plapping. So hot! ๐Ÿ˜ NSFW

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30 Upvotes

r/SissyChastity • • 7h ago

Trans Sheโ€™s gotten so obedient, now sheโ€™s eagerly showing herself off for your entertainment NSFW

28 Upvotes

r/SissyChastity • • 4h ago

Fem which one do you prefer?๐Ÿฅบ NSFW

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27 Upvotes

r/SissyChastity • • 13h ago

Trans Day 22 of Locktober and Iโ€™m so leaky, horny and eager ๐Ÿ˜‹ NSFW

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20 Upvotes