My wife/keyholder has recently decided that I am to have a “milestone” chastity period. Specifically: 90 days, no milkings (she has never done them), and NO unlocking. I am admittedly a bit scared.

My previous best was 37 days but that allowed for occasional releases from the device for hygienic reasons and convenience. There was no cumming, but I was able to get fully erect once in a while during those 37 days.

I heard of one Mistress who would have her chaste male place his penis in a bowl of ice while she milked him from behind, to be sure that the result was more healthful than it was sexual for him.

i have noticed that during the two years work of monthly chastity play, i already have shrunk a bit. I was nearly 6 inches when chastity training began, and now i can only must about 4.5. Of course, this is not much of a concern as my days as a “stud” are long gone.

the longest Mistress Michelle has commanded that Her cock slave cks(j) remain locked is 153 days straight with out any release, from chastity device, or successful self induced and commanded prostrate milking, approximately 5 plus months.

four of them were punishment beads so ive felt the belt, the cane , nipple clamps and my mistress strap on.
Saturday we were out with friends and because i have been good and taken my punishment well , i was allowed release for the night, …. big mistake.
on our return we were both drunk and while in bed i made a move on my mistress she didnt reject so i had a great fuck [its been ten day since i last felt pussy around my worm] and i came inside her [something im never allowed to do ]
I was imediately locked up and made to clean my mess. Mistress then informed me that i had taken advantage of her and would be punished severely soon.

1.) you are to call Me Mistress or Maam when you are wearing your collar. (this has evolved to whenever we are private with or without the collar…also when we are IMing or emailing)
2.) Kneel when I am putting on your collar.
3.) I will find you a collar to My liking for you to wear everyday, you are never to take it off. (for a long time this was a leather cock ring, now it’s my CB3000…i also wear a leather and chain bracelet…if anyone asks me what it is i must tell them that i am a slave)
4.) Never say No to Me
5.) Never pass Me in longitude or latitude without kissing Me.
6.) you shave every morning and every evening, whether we are together or not.
7.) Talk with servants to order for Me, My drinks, My Meals, and My wishes. Restaurants, flight attendants, everyone. If I have to answer or speak to them, you have failed.
80.) Always pull My chair out for Me. I will stand until you do, but if you make Me wait, you have failed. If the servants do it before you, you failed.
9.) You are never to start eating before Me and never finish before Me.
10.) Shave My pussy everyday we are together. (shaving always ends with pussy worship. Mistress is multi-orgasmic and comes many times! this is by far my favorite activity and i would spend my entire life with my face between Her legs if i could))
11.) Always walk, sit (or across from Me), & sleep on My left, to protect Me from what I can not see.
12.) You are to protect Me from other Men. I want no contact unless I choose it. I will tell you if I do.
13.) My glass should never be empty unless I tell you no more, regardless of what I am drinking.
14.) Hold My hand while we walk in public. If the walkway is too narrow, you are too follow Me with you hand on My shoulder
15.) Earl grey tea every morning,
16.) Prepare all our Meals.
17.) Erotic email and / or text Message every day.
18.) you drive when we are together
19.) you are responsible for all our wash and dry cleaning
20.) Keep Me warm, especially at night
21.) Never Cum without My permission
22.) Open My car door every time and must assist Me in exiting the car. you must escort Me to the car door and assist Me in entering the car.

Can do without Permission
Prepare our Meals
you can call Me terms of endearment

Must ask Permission to
Put on or take off you collar without Me. I will always put it on and take it off.
Touch My nipples, My pussy, or My feet. you can touch everywhere else on My body.

Punishments

1. Spanking, hairbrush, paddle, riding crop, leather flogger, leather, paddle,
a. Depending on the severity and as we grow in Ds & comfort, may be public.
2. Whipping Leather whip, Leather flog, rope
3. Denial of pleasure Not related to your orgasms, but denial of service to Me and My wishes
4. Orgasm Control & Teasing When we are separate you must beg and ask permission to cum
5. Chastity belt
6. Humiliation & Reprimand
7. Gagged, forced nudity, & bound, and watch your Mistress and smell My pussy

Mistress always cums first. also, since i moved to FL i keep the house organized, run all the errands and do all of the shopping.

i am always rock hard during punishment sessions but during intense moments i will go soft due to the intensity of the pain. i can take the flog for a long time but crop and paddle can be excruciating and the cane is just pure pain. after punishment sex is out of the question for me.

She is still silent the whole time. now, however, when i am finished with Her shave i beg, “please Mistress, it would be a great honor for me if you would grant me the privilege of worshiping Your Pussy.” then Mistress will say, “you may worship Me, slave.”

i am collared and spend lots of time on my knees massaging Mistresses feet and worshiping them. i also shave Mistress every weekend and then bring Her to several orgasms with my mouth and tongue. at that time i am also punished for my transgressions from the week which i am required to record in my “Book of Transgressions”. Mistress has flogs, canes, whips and paddles. i am tied to the bed with leather restraints and chains and i am frequently punished for an hour or more until Mistress and i am exhausted. Mistress loves to watch me squirm and listen to my cries. She comes frequently during O/our sessions. W/we both love checking my ass for bruises and watching the colors change.