Day 8: 01/14/19 - "CHASTITY INSTALLATION HIJINKS"

Last night I did my best to slip my little sissy clittie into it's new 'MicroBON4' chastity cage. I took a long, oily bath, and also ran my bathroom's space-heater for over half an hour to ensure that the room was toasty enough for my testicles to properly discend. Unfortunately, it was a prolonged struggle during my first attempt installing the device. As a result, I had to do a lot of jostling with my genitals to get them to fall into the proper position. All of this undue friction caused my helpless peenie to erupt (it really doesn't take much stimulation - if any - for this to happen). I captured the accidental violation on video and have provided several screenshots as evidence for Auntie to rule on. Despite my failings, I did eventually get the device on in the end, but it came at the cost of getting 'spurtie stains' all over my pretty pink ruffle-butt panties. Oh, I do hope Auntie is merciful...

Day 6: 01/12/18 - "CUMMING FOR AUNTIE"

For this diary entry, I will share my response to Auntie after she granted me what is to be my final orgasm before I embark on my new life in chastity (for this I have ordered the new Bon4Micro Cage which should arrive today - I shall write about it in my next diary entry).

My bond with Auntie has grown significantly over the past week, as she has essentially become my 'sissy guardian', embracing me as her weak-willed poppet. Over the past weekend things got even more personal after I shared visual documentation of my final orgasm with her. We proceeded to exchange several back-and-forth messages, during which Auntie shared some rather steamy details about her enjoyment over seeing me ceremoniously soak my panties for her.

And so, without further ado...

Dearest Auntie,

I am still buzzing from the events of the past 24 hours that had been set off like a chain reaction from the warm, titillating message you last sent to me.

Mesmerized after reading it (and re-reading and re-reading it over again), I suddenly became faint and had to lie down, overwhelmed by visions of your dampened panties. For hours, naughty thoughts percolated though my sissy brain as I fantasized about putting your soiled panties over my face, inhaling their sweet fragrance while my tongue probed for just a hint of succulent 'Auntie Juice'. I confess that I even dreamed about wearing them to encase my little peenie and ballies in the warmth of your divine wetness (*I do hope that these decadent admissions do not offend you).

Of course I was touched and overjoyed to learn of my 'special reward' for being a 'good boy' (thank you for such utter kindness!) Realizing the gravity of this (soon-to-be rare) opportunity, I wanted to do my very best to make it special, as well as to express my immense gratitude for such a treat. And so in addition to picking out my most sissyish pink lingerie, I was also compelled to make myself even more effeminate by first trimming away 'all' of my unsightly male body hair, and then applying girlish shades of make-up to my quivering face. I then promptly set up my bedroom to serve as the ceremonial location for my panty soaking.

Here is the result of my joyous (albeit brief) orgasm:

Day 5: 01/11/18 - "FROM DIAPERS TO PANTIES"

Overall Auntie was pleased with the progress I made last night, since (for once) I did not make any 'diaper squirties' in my sleep. She also confirmed it was indeed her intention all along to test my resolve by ordering me to spend another night in Vaseline and cream filled diapers.

Perhaps most importantly, she did not view my toilet seat dribbling as a violation since it was an 'involuntary' response, adding, "Aunties understand that sometimes little penises have a mind of their own and leak at the most inappropriate times."

Of course, this is not to say I received a perfect overnight grade as she did call me out for my frisky bedtime wriggles, which in her mind were a clear indication that I was attempting to appease my beckoning libido. She asked that I work on this 'weakness' and do a better job of avoiding any unnecessary stimulation going forward.

For tonight, Auntie promoted me from diapers to 'panty'-status. She first asked if I owned any especially silky ones (a question she already knew the answer to) and I confessed to having many pairs.

She then instantly teased, "I just knew you were a 'panty boy'!"

My heart flutter in submissive ecstasy as I read this. In a very short amount of time, such shameful elation has become a regular occurrence for me, especially since Auntie has clearly stepped up her authority by incorporating more and more such emasculating remarks.

She next personally picked out the color I was to wear ('white'), adding, "We both know you would probably prefer 'pink' but Auntie controls the color of your panties from now on too."

Smitten in ways only a true sissy could understand, I humbly complied with her request, taking care to wear a pair of white, waist-high granny panties under my long johns and pajamas.

*UPDATE: Auntie will be happy to know that there again were no incidents to report, although I did struggle with many satin-induced erections throughout the night (apparently my return to chastity cannot come soon enough!) Aside from the inopportune arousals, I also experienced numerous panty ride ups between my fanny cheeks, no doubt a byproduct of my tossing and turning. At first I continually pulled each one back out again, but eventually gave in, surrendering to their inevitable return (such is the life of a 'panty boy').

Day 4: 01/10/18 - "BACK IN DIAPER-CHASTITY"

There was no diary entry for yesterday (Day 3) since Auntie continued to have me hold off on resuming chastity until she's absolutely convinced that my scrotum no longer has any redness or irritation. While she has mothered me by being overly cautious in this regard, she did express distinct disappointment about the accidental 'squirties' I made just 2 nights ago.

Last night I actually forwent applying additional ointment and, in lieu of diapers, returned to my traditional sleepwear consisting of underpants and pajamas. I had a sound slumber and wrote to Auntie this morning to inform her that I felt ready to resume my chastity again. To my surprise, she insisted that I once again apply cream to my privates and return to diapers for yet another night.

This news gave me immediate cause for concern, since as previously stated, I've never in fact been able to make it through a whole night in diapers without succumbing to the intense temptation to wriggle around until my padded crotch is left plastered in a sticky goo. It crossed my mind that Auntie is not only well aware of this fact, but that she perhaps prescribed another round of 'diaper-chastity' to serve as her first true test for me. Further supporting my theory was the following stern warning which concluded her message:

"You are to wear your diaper and NO squirties or there will be consequences...."

As I again prepped my loins with powder and diaper rash cream, I pondered why Auntie was so disheartened that I'd made 'squirties', and why it was so important to her that there not be a repeat offense. It then occurred to me that since she had assumed responsibility of my genitals, they now essentially no longer belonged to me, thus making my unauthorized ejaculation a blatant misuse of 'her' property. It was in that moment that I swore to myself to keep this in mind for the rest of the night, as I sealed Auntie's 'property' into the quilted confines of my princess pink Pampers.

*UPDATE: It is now morning and I officially survived the night from making cummies in my Pampers. I 'think' Auntie will be pleased to hear this, although there were indeed a few close-calls.

One of the conditions of our chastity relationship is that I provide Auntie with confessions to any and all wayward behavior. Although I went to bed with the utmost intention to remain celibate from any masturbatory tendencies, I once again found myself intermittently rubbing my diaper crotch against the bedding and pillows beside me. I was conscious enough to know that I was flirting with danger, especially since it is quite clear that I lack self control in the face of even the slightest penile stimulation.

A bigger offense came in the morning while I was doing my daily 'business' on the toilet. As the usual pressure in my bottom was applied to facilitate things, my penis unexpected began dribbling a puddle of pre-cum onto the front of the toilet seat. While technically not an orgasm, I do wonder if Auntie will see this as an infraction since my nighttime thrusting had undoubtedly been the most likely catalyst.

Day 2: 01/08/18 - "HEALING & PAMPERING IN DIAPERS"

Auntie was very understanding and concerned about the unfortunate setback that occurred on my first overnight in chastity. She assured me that she is not cross and she wants me to be 100% healed before we start again with my regimen. The goal, of course, is to eventually be able to stay locked up long-term to the point where the chastity cage feels as natural to my daily existence as possible.

To help with the healing process, Auntie agreed that it would be a good idea for me to pamper my genitals with generous amounts of ointment (I used baby Vaseline and diaper rash cream) and then spend the night in diapers to allow it all to soak in overnight. Being that I am a closet sissybaby, I appropriately picked out one of my Rearz Princess Pink Nighttime Diapers with a pretty pink and white onesie to hold the diaper in place from any eventual sagging.

Although the babying sensation was wonderful, I did have a close call while applying the rash cream to my testicles and nearly ejaculated in the open air before sealing up my diapers. Sensing this would be very much against Auntie's wishes, I took a 'time out' to allow my eager penis to settle down before snugly taping my diaper in place.

 

I went to sleep with the mindset that this diaper session was strictly to allow my boy bits to heal and was not an opportunity for me to make 'Naughty Number 3'. Truthfully and despite my best efforts to avoid it, anytime I've ever attempted to wear diapers overnight it has always ended with me succumbing to the irresistible urge to crudely hump my pillow (for usually just a few seconds) until I promptly spurted naughtiness into the slippery confines of my padded encasement.

Unsurprisingly, this same inappropriate occurrence did rear it's ugly head again, but I think Auntie will understand (and may even be proud) in how I handled it. You see, I tend to toss and turn in my sleep. Last night, while in a semi-conscious state, I turned over and found myself instinctively and unknowingly wriggling my hips into the bedding next to me. I became fully conscious at the cusp of a release, and although a flooding of ejaculate did result, I fought through the orgasmic spasms and forced myself (and my penis) to lay entirely motionless to avoid the ecstasy of a full fledged release.

This same tactic is essentially aligned with the cuckolding principles of a practice known as 'milking' and/or a 'ruined orgasm'. By definition, it is the intentional actions of a dominant to bring their submission to the brink of an orgasm only to prevent them enjoying it's pleasurable finale. It is normally employed by the dominant to drain their submissive's testicles of built up sperm while still keeping them at a heightened, albeit frustrated, sexual state.

Day 1B: 01/07/18 (Overnight) - "AN UNAUTHORIZED UNLOCKING"

During the first few hours of my chastity imprisonment, I went through a number of different experiences:

(1.) After struggling to keep my erections at bay during the initial lubrication and assembly, I was finally able to get everything into place by filling my mind with ordinary, unrelated thoughts as I quickly slide the 'cage' over my unsuspecting, and still flaccid, penis. This effective 'trick' reminded me of how I deceive my cat by I luring him into his carrier only to immediately close the door behind him before he realizes what has happened.

(2.) The first clicking of the lock gave me a profound feeling of helplessness as I next sealed the chastity keys into an envelope bearing an old picture of Auntie with the words "PROPERTY OF AUNTIE HELGA" on the front, and "DO NOT OPEN UNTIL AUNTIE SAYS SO" on the back.

(3.) Although excited and eager to please Auntie right from the beginning, I got the sense that things did not feel quite right early on. Although I'd previously worn my chastity device in the past, it was always usually for just a short while during the warmer months of the year (spring / summer). The temperatures on such days would be much higher than it is now. These warmer conditions would directly affected how my testicles hung. Specifically, my scrotum is apt to sagging much more as the sac's skin itself is thinner and much more pliable. That being said, I was ill prepared when I decided to slide the ring of my chastity device behind my testes last night. In hindsight I should have taken a long, hot shower to allow my testicles to descend, but instead I rushed things and it led to an improper and uncomfortable installation.

(4.) I continued to re-apply lubrication around my scrotum but it did not prevent my skin from feeling irritated. As the condition intensified, I ultimately held out as long as I could before arriving at the decision to break my chastity commitment. Unfortunately, I had to do it without Auntie's permission since it was in the wee hours of the night. I felt rather contrite about it since I had such a strong desire to make Auntie proud that I was able to make it through my first night without incident.

(5.) After removing the ring, I quickly realized what the problem was. It became obvious that despite having my testicles properly through the ring, the scrotum itself was only half-way through. The skin of the part that was inside the ring was very tender and red, and there was an obvious mark around it. I applied aloe to the affected area in hopes that it will feel good enough in the morning (after a shower) to be put back into chastity.

(6.) I remorsefully messaged Auntie to confess about what happened. I am hoping she is not cross with me as this was not the first impression I was hoping to make!

Day 1A: 01/07/18 (Daytime) - "PRE-CHASTITY ANXIETY"

This is the first entry of my online activity log (or 'diary') chronicling the thoughts and feelings I experience during my first time under enforced chastity.

Today I am very grateful that 'Auntie' has so graciously agreed to help me with my training. She understands that as a closet sissybaby, I frequently have trouble keeping my hands out of my panties and crinkly diapers. Aside from the obvious (that sissies ought not to be touching themselves at all), I'm also a chronic premature ejaculator so, when left to my own devices, the risks of having a forbidden orgasm are quite high.

At around noon today, I emailed Auntie to ask if she intended for my chastity regime to begin upon my return home from work. Without hesitation she firmly replied, "YES, I feel you should get started right away."

As soon as I read this response, I was immediately filled with nervous anticipation. For the next several hours I found myself consumed by thoughts of my impending sentence. Aside from playing dress up with my chastity device on for several of my sissybaby photo-shoots, I've never actually been put under a mandatory restriction before.

The day dragged as I counted the seconds. My entire body buzzed with exuberance. Not only was my prostate involuntarily stirring, but I also experienced a strange twitching of the sphincter muscle in my anus. Admittedly, I had several long and rather throbbing erections at my desk while trying to work, as if my poor penis knew this was it's final chance to get in any last minute arousals before being locked away for an undetermined length of time.

***

I was officially locked in chastity at 8:30 pm tonight. I took a photo for Auntie and included her 'code word' as proof that the picture was recent. We shall see how sleep goes tonight...