JennSome's Chastity Journey

Discussion in 'Journals and blogs' started by JenniferSometimes, Apr 3, 2024.

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  1. JenniferSometimes
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    JenniferSometimes Life-long sub and crossdresser, love chastity.

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    Note: I posted these first few entries in Chastity Thoughts on this site, but it seems to be turning into a Journal, so I'm reposting here and will continue here only.


    March 18, 2024
    My use of chastity has ebbed and flowed over the past few years, but there's been a recent turn of events. My lady has become accustomed to me wearing a chastity device when I chose to do so. She even thinks it was hot, and likes to see me in it. I have suggested on several occasions that I'd like her to be my keyholder, but I didn't want to push the subject.

    Well on 03 March she took me up on the offer. She has been my Keyholder for just over two weeks now. The results so far. We're having more intimate time, just being close to each other. We also have more sex and she is climaxing a lot. I think she's had eight since my lock up, and I've had zero since then. That's nine for the month for her and one for me. We both love how it's going so far in this new arena.

    March 24
    Today ended three weeks of teasing & denial (T&D)* for me. Let's just say we each had a big release today. I was back in my "armor" as she called it less than 30 minutes later. I hope my refractory period doesn't last too long. Our ratio for the month so far is ten for her, and two for me. It'll be interesting to see how long she has me wait for my next one. I think she'll ask for my input before she decides. I do think she's really liking the whole chastity thing.

    * - I know T&D (or TD) is obvious to > 90% of the folks here, this is for the other < 10%.

    April 2
    We passed four weeks of nearly full time chastity on Sunday (there were two short breaks for soreness). My lady and I are settling into some standard behaviors.
    1. I don't ask to be unlocked since I learned to shower effectively with my cage on.
    2. I don't ask for an orgasm. I anticipate that they will be infrequent. I had two in March, counting the one just before she took the keys. My lady had eleven.
    3. I am expected to make her breakfast and pack her lunch, and I am happy to serve her in this way.
    4. I am eagerly doing more things to please her, in intimate and more ordinary ways. She has given me domestic assignments a few times so far. More to follow, perhaps.
    5. She casually checks for my cage whenever she pleases, and enjoys rattling the keys in front of me.

    We both love that I am locked and under her control. We're still very early in the game. It is exciting to think about how this may develop.

    Thanks for reading.

    Jennifer Sometimes
     
  2. Spankuuuu
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    Spankuuuu Long term member

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    Good luck on your journey. It is awesome. Has changed a lot of things for Mistress and I.
     
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  3. LesterBallard
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    LesterBallard Long term member

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  4. MVincent
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    MVincent Active member

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    Sounds like you two are on a good path! Have fun!
     
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    little_dude Active member

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    Sounds exciting!
     
  6. anasyrma
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    anasyrma Long term member

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    A great start, what things do you do to please her, both intimate (if you want to share) and more ordinary?

    I self lock and my wife likes to see me locked and in panties, but she hasn't taken the keys yet.
     
  7. madams-sissysub
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    Thanks for sharing.
     
  8. Barry/desiring/chastity
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    Thank you for sharing
     
  9. JenniferSometimes
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    JenniferSometimes Life-long sub and crossdresser, love chastity.

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    i have been keeping a detail journal offline, mostly because i'm sure it isn't interesting enough to post here or on my Blogger site. Here's a summary of what's been happening.

    my chastity has been a bit interrupted by skin irritation. It's not serious, but needs time to resolve. In the meantime, i have avoided masturbating to keep my energy high for Mistress. i love pampering Her when She comes home from work. i am back in my device as of this morning, at least for the rest of the day.

    We have had a few pegging sessions. It is getting more enjoyable for both of us. Last weekend's session was particularly fun. Preparation is the key. i can't be relaxed unless i am 100% sure of cleanliness. Oh, and lube. Lots of lube.

    Our orgasm count since the beginning of March is 16 for Mistress, and 2 for me. i hope to be able to get her to 20 before she requires me to have my third.

    Thanks for reading.

    Jennifer

    * - Reminder (as I say in my bio) that my avatar is an AI altered picture of me while crossdressed. i promise you that i don't look that pretty in reality. i would be so happy if i did.
     
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  10. JenniferSometimes
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    JenniferSometimes Life-long sub and crossdresser, love chastity.

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    Hello everyone. Here's an update on our journey.

    Since my last post, Mistress has achieved five more orgasms, while i have had zero. As of yesterday, it is 30 days since my last. Our ratio since the start of March is 10.5:1 (21 for Her, 2 for me). After yesterday's session, i thought She might grant me a release, but She said that She likes me in the condition that i am in (horny, submissive, eager to please Her in any way i can), and She doesn't want that to end. i see this as a bit of a watershed moment. Heretofore She has been very willing to encourage me to climax. Now it seems She has taken a quite different stance; one that i have encouraged Her to take and am rather thrilled to see.

    My lock-up time has been spotty due to ongoing irritation issues, but i am now back in the cage all day every day. i am still unlocked at night, which due to uncontrolled nocturnal erections is when we think the irritation starts.

    Thank you for reading.

    Jennifer
     
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  11. Stephplayswithyou
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    Stephplayswithyou Long term member

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    Sounds like the two of you are on the same page as to how things are going. Irritation issues are the worst, and deal with similar at times myself. You're doing great and wanted to just say, thank you for sharing insights into your journey with us.
     
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  12. JenniferSometimes
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    JenniferSometimes Life-long sub and crossdresser, love chastity.

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    Hello everyone,

    Here's a brief update on our status. We finished April with eleven orgasms for Mistress and zero for me, giving us twenty-two and two, respectively since the start of Her keyholding in March. i think we are both very happy with how it is going. i love being teased and denied. Mistress uses my body for Her climaxes, and then we stop when She is done. i go back into lock-up. i feel closer Her, more dependent on Her, and more attentive to Her needs and desires. i think She feels the same from Her perspective.

    i have a stronger sense that chastity is a state of being at least as much as a physical constraint. There are times that i have not been caged due to irritation, but i have never felt free to masturbate or climax with Mistress' explicit permission. i think it is my being under Her control and bending to her Her will that has energized us.

    That isn't to say that the device itself is not important. It definitely is, both as a practical deterrent and as a symbol of my surrender to Her. i know that I can not control my sexual urges indefinitely and at all times if i wasn't locked, based upon on a lifetime of experience. i also very much enjoy wearing a cage. i am reminded of my submission to Her when i feel the cage, or when i use the restroom. It brings me comfort to know that She loves me enough to care for me in this way. i know that Mistress enjoys feeling it on me, and holding the key. She said she reaches into her pocket during the day and holds it, knowing that i am Hers.

    May is expected to start of with a bang. Mistress plans to peg me and wants me to climax while She does. i am very much looking forward to it.

    Thanks for reading,

    Jennifer (sometimes)
     
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