Tiffany's 2019 Chastity Journal

Time to get my chastity challenge started

Card drawn: 7 of Clubs

Draw 6-10 - Card Draw Challenge - Start with 1 week of chastity. - Every day Tiffany draws a card. If the value of the card is 7 or higher, a day is added to the chastity sentence. If a Queen is drawn, add 3 days of chastity.

Looks like I'm starting my year in chastity with at least a week without orgasm.

Hope Lady Luck doesn't keep me locked for too long ;)

Since January 1st 2018

I have been locked up for 248 Days - 74% of the year so far.

Longest Time Locked: 61 Days!

Today’s Status: Annoyingly Horny!

It’s only Monday and I can tell this week is going to really drag.

November 18, 2018 - Since January 1st 2018

I have been locked up for 236 Days - 73% of the year so far. 

Current and Now Longest Time Locked: 49 days and counting…

Desperately hoping I get to cum on the 1st!

Today’s Panties are Purple

Sexy Librarian: Part 2...

"How was your week?" she asked as she gestured towards my crotch.

7 days had passed since the Sexy Librarian punished me for my boisterous behaviour.

7 days since she locked me in chastity.

7 days of hard pink plastic squeezing my cock and tugging painfully at my balls any time I became aroused.

Unable to achieve relief, enduring my little pink penis prison was torture. I was constantly horny. 

A whiff of perfume, a glimpse of cleavage, the sight of a shapely thigh; The slightest stimulation was all my lust needed to punish me with an attempted erection.

I couldn't bring myself to answer. I looked at my feet sheepishly and whimpered.

She stepped close to me and gently rubbed my chastity through my trousers.

"That's a Good Boy. Don't worry, you'll get used to this eventually."

Smiling she undid a button on her top, turned around, and walked back to her desk. She took a seat on the edge, picked up her ruler, and let out a giggle.

"Remember Mr. Ruler? How would you like a chance to escape your cage today?"

Still smarting from my spanking last weekend, I instinctively rubbed my sore bottom.

"Still smarting from last week?" she asked, laughing. "Well don't worry, I'm not paddling you today."

"Drop those trousers and I'll unlock you."

I nodded and said "Yes Mistress" as I unzipped.

The Sexy Librarian removed a gold chain from her neck, slowly drawing a small key from the depths of her milky cleavage.

Observing the key make its languished journey across her soft breast was all I could bear. I grimaced, feeling my little cage assert its control over my growing lust.

"You boys are so easy" she said smiling, "I'm going to unlock you now. No touching until I tell you."

I put my hands behind my back and nodded.

"I felt a little bad when I laughed at your little penis last week.”

“It was definitely a bit cold in here and maybe you're a bit of a grower instead of a shower."

"I want you to get hard for me and well see if you can satisfy Mr. Ruler. If you can measure up, I might even let your cock enjoy a week of freedom."

With that suggestion, my already hardening cock stood to attention.

"My, my. Somebody's eager! Now, let's see what you're working with."

She reached down and took a firm grip on my cock. "Don't you dare cum!" she said as I stifled a low moan.

She knelt, putting my cock at her eye level. Holding the ruler along the top of my shaft, she leaned in close enough that I felt her hot breath on my balls.

Examining the markings on the ruler, she pronounced "Well, Well, Six and a half inches. Not too bad."

"Do you think that's enough for Mr. Ruler?" she asked, feigning a frown.

"I'm not convinced. I think I'm going to need a little more data. Stroke for me."

After a week locked up I didn't need any further prompting. I took hold of myself and started masturbating.

"Go slow now. I want you to tell me when you start to get close."

I worked myself for her; slowly at first but then gradually increasing my pace. She watched intently, a wry smile on her face. Like the cat who caught the canary, she had a devious look about her.

She slowly reached up and undid another button on her blouse, giving me generous view of her ample cleavage. Pushing her arms in she squeezed her luscious breasts. This simple action amplified her glorious cleavage even further.

This wonderful sight was all I could bear. My breathing quickened and I let out a moan of pleasure.

"Getting close?" she asked.

I nodded in confirmation as I my passion built toward's its impending climax.

"Good. Hands Off!" she ordered sharply.

Her words hit me like a slap; my hand immediately released it's grip. I whimpered softly, lightly humping the air in a vain attempt to achieve release.

Pulling a small cooler from behind her desk, the Sexy Librarian reached over and opened it.

"Congratulations, your cock is just long enough to satisfy Mr. Ruler!"

My erection still raging, the librarian gave it a little tap.

"I'm a bit of a Size Queen though and I’m not Satisfied. Time to lock you back up!"

She reached into the cooler and pulled out an ice pack. She swiftly pressed it against my throbbing penis.

"But I didn't get to cum" I complained as I squirmed from the painful chill spreading through my groin.

"That's your lesson for today. It's simple. Good Boys need permission to Cum!"

She looked into my eyes wickedly as she locked the cage on my shivering limp dick.

"Today, You don't have my permission.”

“Put your pants on."

I quickly got dressed and she led me out the door.

The chastity file from this series is great.

😳 🔒Day 45🔒

At least 16 more to go.

Since January 1st 2018 I have been locked up for 231 Days - 73% of the year so far. Longest time locked - 48 days. Current time locked: 44 days.

Notable Erection

Cause: Lovely Redheaded woman on the bus.

With her braided hair and glasses, she is the image of the Sexy Librarian.

The sight of her set my mind wandering and sparked the following fantasy while my lust strained against its cage.

"That's Enough Young man!"

My friends and I had gathered at the local library to work on a school project. We'd been getting sidetracked all afternoon and the librarian was sick of our noisy outbursts.

Playing for a laugh, I exclaimed “What are we being too loud for the books? We wouldn't want to hurt their delicate ears!”

"Oh you're not bothering the books, you little twat! You've disturbed the concentration of the people trying to read them."

The librarian reached over and grabbed me by the collar.

"I think I need to teach you a little lesson about respect."

She dragged me out of my seat with surprising force. Stunned, I sheepishly followed behind her.

She pulled me into a back room and locked the door behind her.

"If you insist on being loud, this is the perfect room for it. It's fully sound-proofed so our book-binding machine won't disturb our patrons."

The librarian took a seat next to a desk and picked up a ruler off of it.

"Come over here and take off your trousers."

“What?!” I exclaimed, incredulously.

"I said: Take. Off. Your. Trousers! Unless you want to call your Mother and have her come down here. What's more embarrassing? Dropping your trousers for me here in this private room or being a grown boy who needs his Mommy to come pick him up because he's been a naughty boy?"

Having quickly considered my options, I unbuckled my belt and let my trousers drop to the floor.

"Good Boy. Underpants too"

I looked at her, pleading "Really?"

She nodded sternly.

With a sigh I hooked my thumbs in the waistband of my underpants and quickly slid them off. The room was cold and I hurried to cover my quickly shrinking manhood.

She slapped my hand with the ruler. "No, no, Silly Boy. Hands behind your back."

She poked and prodded my penis with her ruler.

"That's it?" She laughed mockingly. "You don't really measure up do you? There's hardly enough there to even call it a cock."

My hips jumped back as she gave the head of my penis a little slap with the ruler.

"Alright. Time for your punishment." She slapped her hand with her ruler.

"Turn around. Bend over and keep your hands on the table. If you lift your hands I'll have to start over, Understand?"

I nodded meekly, turned, and placed my hands on the table.

As soon as I put my hands on the table I felt a sharp sting as the librarian struck my bottom. I jumped, my hand instinctively reaching back to caress the hurt.

She shouted "What did I say? Hands On The Table!" and smacked my ass with the ruler again.

Smarting, I had no choice but to put my hands down and comply.

"Good. Now let's try this again"

*Smack*

*Slap*

*Whack*

She started to work up a steady rhythm, varying the intensity of her strokes.

After a couple of minutes of striking, she grabbed me by the hair and whispered in my ear "Repeat after me"

*Thwack"

"I'm A Naughty Boy!"

“I'm a naughty boy!”

*clap*

"I was Loud and Disrespectful!"

“I was loud and disrespectful.”

*Wham*

"I deserve to be Punished!”

“I deserve to be punished.”

*Pow*

"I need to be Trained to be a Good Boy!"

“I NEED to be trained to be a Good Boy.”

*Smack*

"Please Train Me Mistress!"

“Please Train me Mistress!”

*Slap*

She relented, her assault on my backside finally finished.

"Good Boy. Turn back around and keep your hands behind your back."

She turned to her desk and rummaged through the drawers. She pulled out a little pink piece of plastic and a small brass lock.

"From now on you're going to call me Mistress. This is a chastity cage. It's going to help me teach you how to behave properly. You're going to wear it from now on."

She turned back to me and quickly slid the cage over my still shrivelled cock, locking it on before I could become aroused by her touch.

I inquired "How long do I have to wear it for?"

"I haven't decided yet. I expect your complete obedience and a marked improvement in your behaviour before I'll consider unlocking you."

She tugged at the cage and patted my balls.

"Now get dressed. You can come back next week for more training"

“You mean I have to stay locked until next weekend!”

"Oh sweetie! I said come back in a week. I never said I'd unlock you!"

She pushed me out of the book binding room and hollered before closing the door behind me "Be a good boy for me! I'll see you next week."

Since January 1st 2018

Mistress you're my Crush The personification of my Lust My mind turns to mush, When I dream about your Bust

With the goal of maximising my frustratingly horny fun times in chastity, I aim to spend every day of 2019 locked up, with only the briefest of releases when I'm permitted an orgasm. On this blog I plan to post my pledge, and track my progress throughout the year.

Rules:

This chastity pledge is designed to help Tiffany feel submissive at all times.

By violating the terms of the pledge, she would cheat herself.

On her Honour as a Good Girl, Tiffany swears she will self report any rules violation and request a punishment.

Tiffany must always be wearing her cage. She may remove her cage she has been permitted an orgasm, but she must put the cage back on immediately after orgasm is achieved. Tiffany is permitted to remove her cage as needed for shaving and cleaning, but she must seek to minimise manual contact. If Tiffany becomes aroused while cleaning or shaving, it will be considered unauthorised masturbation and she must report for a punishment for not following orders.

Tiffany will report for a punishment for any unauthorised orgasm.

A good girl cleans up after herself. Tiffany must swallow or collect every drop of cum she is allowed to spill.

A daily dose of Porn. Tiffany is to watch at least 30 minutes of porn before bed every day to keep her horny and help her have pleasant dreams ;)

Tiffany will listen to chastity encouragement audios during her daily commute.

Tiffany will keep a chastity journal. Tiffany will keep track of videos watched for her Daily Dose of Porn. She should keep track of attempted erections (cause, duration, nature of arousal, description of fantasies conjured). Tiffany will share notable / humorous excerpts from the journal on her Tumblr.

Tiffany will keep and update chastity stats. Will be included with journal updates on Tumblr. Tiffany will also post stats at end of each chastity sentence (Days locked, Days since last orgasm, orgasm count for 2019, Longest Lock-up record).

Additional Goals

In 2018, most of my play has been chastity focused. Since I generally enjoy enduring chastity play, I pledge to train regularly do develop my submission in the following areas:

Anal Training

Monday, Wednesday, and Fridays - Wear a Butt-plug while watching daily porn.

Saturday or Sunday - 15 minutes of Dildo Fucking or 15 minutes riding prostate stimulation attachment of Magic Wand vibrator.

Cum Eating

Tiffany enjoys the fantasy of eating her cum, but rarely partakes. To fix this naughty behaviour, Tiffany is expected to swallow every last drop of her cum in 2019. She will eat her load immediately after orgasm unless she has been instructed to collect it for future consumption.

Sissyfication Tiffany really enjoys her feminine side, but hasn’t been indulging it as of late.

Tiffany pledges to get fully dressed and made up at least once a month.

Tiffany will plan and host a Sissy Tea party for other submissives on the Jennifer in Control platform.

Tiffany will buy new panties or lingerie in person at least once this year instead of online.

Tiffany will take a photo of herself fully dressed and outside.

Special Events:

A Sissy Birthday Celebration

Tiffany is to dress up girly to celebrate her birthday and pose for a photo to share on her Tumblr. Photo should be birthday party themed (Party hat, decorations, etc).

Tiffany is allowed to enjoy an orgasm on her special day.

Locktober

Tiffany is expected to be locked up from 23:59 September 30 to 23:59 October 31.

Tiffany is to participate in any Locktober festivities organised on Jennifer in Control.

No Cumming November

Unless Tiffany earns a post Locktober orgasm, She is not allowed to cum in November.

Tiffany is allowed out of her cage for 30 minutes each day for edging.

No orgasms are permitted. If Tiffany cums, She must report for punishment.

Determining and Administering Chastity Sentencing

Tiffany will be tracking her chastity activities using the Jennifer in Control platform.

Jennifer in Control (JiC) provides a Mistress A.I. system that is supported by Real Mistresses and a Mod Team. This system can automatically dole out punishments, and can help with verification of tasks.

On Jennifer in Control, Tiffany submits to Mistress Natasha.

To keep administration of the pledge easy for Mistress Natasha and the JiC Mod team, Tiffany will play a game of chance any time she needs to select a new chastity sentence.

To get a new sentence she will type “Get Card” in JiC to draw a card.

The card selected will correspond to a premade chastity sentence.

I’m still working on ideas for premade challenges. Ideally up to 13 different possible fates would be available. Challenges should generally last 3 to 5 weeks. I’d love to hear any suggestions.

Potential Chastity Sentences

Draw ? - Earn Your Freedom

Tiffany must start an Earn Your freedom chastity game and earn X number of points.

Tiffany my not earn more than Y points a week.

Tiffany may spread her work to earn points at her leisure. She may try and earn all of her weekly points in one day if she desires.

Unearned points towards the weekly limit do not carry over to the next week (not doing her work makes her chastity last longer).

If Tiffany inadvertently exceeds her weekly points limit, she must select “Punish for Not following an Order” in JiC.

Tiffany is allowed 1 orgasm on the completion of the sentence.

Draw ? - Random Sentence - Card Draw Challenge

Start with 1 week of chastity.

Every day Tiffany draws a card.

If the value of the card is X or higher, a day is added to the chastity sentence.

By default X is 8, but Mistress Natasha can specify another value.

If a Queen is drawn, add 3 days of chastity.

Tiffany is allowed 1 orgasm on the completion of the sentence.

Draw ? - Frustration Challenge

Start with 3 weeks of chastity

At end of 3 weeks, Tiffany must ask the JiC A.I. “May I cum please Mistress Natasha?”

If denied and given another day, Tiffany must serve another week in chastity before trying again.

Draw a Red Jack - Horny Girl Challenge

Cum once every 3 days for 21 days (7 periods of 3 days). Immediate cum consumption.

Draw a Black Jack - Horny Girl Cum Swallow Challenge

Cum once every 3 days for 21 days (7 x 3 days). Collect all loads. Drink Up on day 21 (verify somehow).

Draw a Queen - Set a New Personal Best

Time to push Tiffany’s limits.

Tiffany’s sentence will be set at her current personal best.