When She Called Me Into Her Office, I Hurried In, Not Wanting To Keep Her Waiting. She Was A Demanding

I’m glad you like it!

If he's taller than you, tie his hands as high as you can manage (HOT TAKE: Make it even better if you have a dungeon and he rigs some pulleys for you) then slip way to put on a sexy outfit and OBSCENE high heels or platform footwear- shiny black boots, maybe- so you're as tall as he is all stretched out. It's harder for him to cum standing, easier to stay hard with his arms elevated, and it's surprisingly restrictive without much else, so edging and re-locking can be a piece of cake ♥️

Ana De Armas

Lady Anne is always so thoughtful. Letting you watch her get ready, as she heads out with her latest gentleman friend.

Perhaps she’ll tell you all about it later.

Family Matters - Part 4

You were awoken by the pressing of the boot heel on your cage. Stepmother stood over you, her blonde hair pulled into a severe ponytail, her blue eyes bright and cold…..she was wearing her favourite leather skirt and silk blouse. Months had passed since Father was taken to Romania, under the special care of the Aunts and you were left to serve Stepmother. Your primary role was to keep the house and do anything Stepmother wished. Her punishments had become more cruel and she was now taking sexual advantage of you. Now, usually caged and plugged, wearing some form of silky or lacy panties. You were permitted to wear normal clothes when out in public, but at home, it could be anything Stepmother demanded. This morning, it was your favourite red split crotch silk French knickers. Your ankles and wrists were loosely cuffed as you lay on the floor by Stepmother’s bed, mouth muzzled by the ballgag you wore at night.

“Time to awaken, my sleepy boy. You were busy last night weren’t you?” indeed you were a busy boy. Stepmother had you performing chores in your sissy maid outfit and then you had to shave and shower before bedtime. Stepmother didn’t approve of your facial hair, especially as she face fucked the dildo gag for what seemed like hours. She reached down and unbuckled your ball gag, stroking your face.

“Still nice and smooth, that’s good. Because you know what I want you to do now.” You nodded and reached for the dildo gag. But she stopped you and raised her leather skirt up over her hips. She wasn’t wearing any underwear and her freshly trimmed cunt was glistening…….you trembled…..as she gently grabbed your head and directed your mouth toward her clit…..you licked, kissed and flicked your tongue around her warm, wet pussy. She tasted like a goddess and you continued, as if your life depended on it. She started to thrust her hips faster as she began to orgasm, her Romanian accent now in its natural language…..that’s how you knew you were doing a good job. She exploded and you lapped up her squirting juices as she sat back on the bed, breathing heavily….the twitching from her orgasms still washing over her. After a moment, she regained her composure and handed you a white box.

“For being such a good boy…..I have the second part for you later.” You opened the box and he gasped at the contents. A glossy pair of black latex maid panties, with white bows and trim. Your caged cock swelled painfully as you touched the material and the aroma of the latex filled your nostrils.

“Do you like them?” You spluttered a thank you and Stepmother leaned down and kissed you, tasting herself on you. “Now, we are going away for the weekend, but you will still be working hard. I have a little cottage holiday planned and we will be joined by some guests. As usual, you will be performing whatever duties are required.” You nodded as you buckled the ball gag back in.

With the long journey made even more difficult with a caged, hungry cock and stretched ass, you were relieved to reach the cottage. Stepmother waited until you opened the car door before she regally stepped out of the vehicle. You grabbed the luggage and went inside. It was a charming, rural place. Nobody around for miles it seemed. Stepmother’s high heeled boots thundered on the stone floor as she surveyed their lodgings.

“It will do…..plenty of room for fun and games, Thomas. That box there is your second part of this morning’s present. An upgrade on what you wear at home.” The box was opened and you lifted out the magnificent black latex maids dress. It was full length, adorned with the frills and there was a maid hood, long gloves and leather boots. Stepmother ordered you to strip and as you stood naked except for the cage, she helped you dress. The maid panties were slipped on first, you groaned as you leaked in chastity. Next, the dress, gloves and boots.

“You look amazing, my sissy maid. But there is one thing we need to do further. Let’s go to our room and complete the look.” They went upstairs and you saw yourself fully in the outfit……you were overcome with arousal, but you knew that Stepmother wouldn’t entertain that nonsense, especially as you were now being made up……mascara, lipstick, eye shadow. Once the latex hood was placed on, you barely recognised yourself. The transformation for the weekend was complete and you had work to do. You felt that it wouldn’t be the last outfit change and your lipstick would definitely need to be reapplied……

Pro-tip: When he's locked in chastity but fucking you real good with the strap on, say something like... "feels so good I'm never letting you out again!" for the absolute best fuck of your life. Drives all his desperation straight into your orgasms.

I've got to admit, I can't seem to stay away from your blog (That seems to be a reoccurring theme around here.) Keeping a boy on an academically tied release schedule sounds like the perfect way to keep college students in line (And just what I need 😅). Have you kept any other boys on unusual schedules before?

I’m very pleased to hear it! Come! See! (Just don’t cum.)

I’m sort of constantly setting “goals” for chaste boys. I don’t always put a ton of thought or planning into it. I just dish out assignments as I think of them. Let’s see. So, just off the top of my head, within the last couple days:

 I gave one married man an assignment to make dinner every day for the next 14 days.

 I told one young chap that his orgasm depended on the outcome of a cricket game. (I know next to nothing about cricket so we’ll see what happens.)

I made one guy roll a pair of 12-sided dice to determine the number of days until release.

I checked in on a student whose orgasms are tied, not to grades, but to the number of social events he attends. He’s a veritable hermit and he needs to get out and make friends. This is one of my favorite things to do, by the way.

I implied a man might be getting out if he sent me flowers. The flowers arrived and I sent him pictures of me entertaining guests with the flowers in full view. A small key was nestled into the arrangement. No release, though. Woops!

I checked up on several men in weight loss chastity. That’s always ongoing. It’s fun to watch the pounds melt away.

Played the most dangerous guessing game: Guess the date I’m thinking. Guess too low and you get punished by adding double or triple the difference. Guess too high and, well, obviously you are prepared to do that many days. You can keep that date.