Sissy Cuck Humiliation
The In-Laws (part 2)

The In-Laws (part 2)

My father-in-law did in fact hit it off quite well with Don. They sat in the living room and talked about things that were foreign to me. I had never gotten along especially well with Steph’s dad. But in Don he finally had someone he could relate to when he came to visit us.

I timidly continued serving snacks and drinks, spending as much time as possible in the kitchen away from the eyes of Steph’s parents. I knew better than to dilly-dally too long though, so I spent a lot of the evening quietly kneeling close to Don and Steph’s feet awaiting instructions as they talked and laughed.

After a few beers, Steph’s dad was ready to ask some more detailed questions about our arrangement.

“So, has the maid had some kind of surgery or something? You know, to make her into a trans-whatever they call them?”

Steph looked at Don, choosing to let him answer. “Well, not exactly” he replied. “She still has her little parts, but they’re kept locked so she can’t play with herself.”

Steph’s dad tilted his head, not sure if he understood. “What do you mean, locked? You mean like some kind of chastity belt from the middle ages?”

Don just smiled “Crissy - show the nice gentleman how your little device works.”

I only hesitated for a moment, but I could see Don taking mental note of it and I shuddered.

I stood up in front of my father-in-law and lifted my skirt and frills with one hand, and pulled down my panties with the other.

The laughter and knee-slapping was horrible. I didn’t dare move. I just stood like a deer in the headlights, wishing I could be anywhere but right there having to show off my horrible little clit cage.

Finally he motioned for me to go back to where I was. I was very close to crying as I fell back to Don’s feet, pulling my panties back in place.

“So where are the keys for the little tube?” Steph’s dad asked. Don smiled and pulled his keyring out of his pocket, jingling them for a second before putting them back. Steph’s dad just leaned over and gave him a congratulatory fist bump. “Talk about total ownership - I didn’t know it was possible to own somebody that bad.”

Steph could see that I was on the edge of tears. “Now sweety, no crying over a little show. You know we need to be able to show off our little maid, don’t you?”

I nodded. At least her tone of voice was gentle.

“But look at the clock hon - it’s getting well past your bedtime.”

Steph’s mom looked at her, slightly confused.

“Oh, bedtime for maids is nine o’clock every night. They say it’s best for them to have strict patterns so they can keep their silly little heads straight. Isn’t that right, sweety?”.

I nodded again.

I also knew what this meant. I hadn’t thought of it until just now. I would have to take my bedtime discipline in front of my in-laws. The dread in my stomach turned in knots. How good had I been that day? I stretched to think of times I had gone above and beyond expectations in my duties.

But then I realized that tonight wouldn’t be just about that. Don would thoroughly enjoy displaying his authority over me as he administered my bedtime discipline. I stood up and requested permission to leave the room for a moment, knowing what I needed to do.

I came back moments later with both the leather strap and the wooden ruler. I walked over to Don and knelt, offering him the cruel implements. “Please Sir, I have been hesitant in my obedience to you Sir, and I have been lazy in my maid duties. If it pleases you Sir, I would be honored to have fifty strokes with the strap to my bare bottom, and ten swats to my balls with the ruler for my lack of immediate obedience.”

The in-laws just sat back, taking in the show…not sure exactly what was going to happen.

Don nodded and told me to bend over and pull my panties down. I didn’t try to hide anything - I knew what he would want. I turned so my ass would be towards Steph’s parents as I bent over, exposing my bare ass.

Don took his time, welting my ass good all over. As usual, I howled and jumped and cried and whimpered. But I demonstrated just how obedient I was to him as well, never trying to protect my red and blistered ass from the rain of heavy blows.

But the real show came when he told me to present my balls for punishment. I bent over further, pushing my balls back between my legs, making an easy target for the ruler.

The neighbors could undoubtedly hear my feminine squeals as my little nuts were pelted with the hard stick.

I was hardly able to stand and pull my panties up by the time the tenth blow was struck. As I stood, Steph started clapping, and her parents joined in. Don smiled. I curtsied and thanked him for my discipline. I knew it was an enjoyable moment for him.

Steph pointed to the stairs, and I made my way to bed.

i wish you updated more often. :c

Working on that :)

Part of it is that I try to avoid boring reblogs, so my content is a lot more time-consuming to create.

do you have a owner sissy?

Yes. You can visit his blog at

The In-Laws (part 1)

Here’s part of a new chapter I’ve been working on in the New Master series:


I should have known better than to think that having Steph’s parents in from out of town would somehow be a reprieve from the frustrated helplessness of being a submissive maid in what used to be my own house; and yet somehow I was surprised when she told me that her mother already knew about our new situation and couldn’t wait to see it for herself.

I blushed in horror, wondering what she already knew, and what she would soon find out.

My clever wife was prepared for the stream of protests that was about to come from my mouth. As I started to complain and stomp my heels, she held up a ball gag and motioned for me to turn around.

I stomped one last unsatisfying little protest with my heel as I spun around and opened my mouth. I hated that gag. I hated all gags.

The little lock clicked shut behind my head and I was given a swat to my tush. “Back to your housework, sissy. I want this place perfect when my parents get here.”

I was grateful at least that Don wouldn’t be there when they arrived on Friday. It sounded just devastating to be ordered around and have to be perfectly obedient to the new man of the house in front of them. The thought of how horrible that would be made the reality of having to serve them in my maid outfit somehow less horrifying.

Friday afternoon came far too quickly. I had spent an embarrassing amount of time on my makeup. For some reason I felt like if I was going to be utterly humiliated in front of my wife’s parents, I at least wanted to look as presentable as possible.

I politely swung open the door, lowering my head, my face incredibly flushed as they walked into the house. I didn’t dare look at Steph’s dad. I knew he had to be holding in laughter as I stood timidly and tried to will my little skirt to be much much longer. I did catch a glimpse of her mom’s body though. She was attractive for her age, with sandy blonde hair just a little darker and longer than her daughter’s. The slacks and blouse suited her. I felt a little twinge under my panties and blushed even more.

I had anticipated this moment to be incredibly awkward, and I couldn’t have been more correct. Thankfully, Steph bounded down the stairs, as cheery and beautiful as ever. It was still painful seeing how much happier she was now that I had been relegated from husband to maid, but at least the silence was broken

After hugging her parents, she took a little moment and grabbed my hand. “Mom, Dad…I know this is going to take a little getting used to, but it’s just like we talked about on the phone. Don’t think of Crissy as my husband any more, or even really as a normal friend. She begged for years to be allowed to be just a servant, and now her wishes have come true.”

The words sank in like bitter pills. I really had brought this all on myself. I shuffled a little bit as she continued.

“Don’t feel like you need to be sensitive with her. Anything you want or need, just tell her to do it. It will feel like you’re being mean at first, but I promise that it’s really wonderful once you get used to it.”

To demonstrate, she smacked my ass and told me to fetch them all some tea. I curtsied and said “yes Miss” as I scurried to the kitchen. At that, Steph’s dad could no longer entirely contain his laughter. I couldn’t think straight. Like a silly dunce, I tripped over as I hurried to exit the room. Everything went in slow motion as I felt myself falling in a mess of frills and apron and stockings onto the hard floor. The laughter became even louder. I sniffled and rushed out, wishing there was some way I could escape from the relentless humiliation.

As I returned and served the tea, I walked into the middle of a conversation about Master Don. After hearing his description, Steph’s dad seemed interested in meeting him. “Seems like my kind of guy” he said.

“Well dad” Steph piped up. “You’re going to get to. He’s coming into town later tonight!”

I froze, sinking to my stocking-covered knees.

In case you missed it, part 5 of the Sissy Sisters chapter has been added to the New Man of the House story series! 

And if you enjoy the story (becoming a short book really), please donate! It all goes directly to Master Don - I never get to see it.

How to Let Your Sissy Cum

Tie your sissy’s hands behind her back so she isn’t tempted to do anything disobedient. Unlock her caged little dicklet, maybe giving it a few swats for good measure.

Now have her bend over the bed with her legs spread a bit. Situate yourself behind her on the floor, with a ruler or similar implement handy.

With one hand, firmly grasp at the base of your sissy’s clit and balls. With the other hand, start giving her the stroking along her short little rod. Her desperate moans should be fairly entertaining. Allow yourself a little laugh.

Now comes the tricky part. Chances are, your little slut is going to want to spurt her tiny load pretty quickly, so you shouldn’t have to wait long. Watch for her ass cheeks starting to clench involuntarily. As soon as the first signs of her sissy orgasm start, immediately stop stroking her shaft and switch over to the ruler. 

With your grip with the other hand still firmly holding her genitals in position, start giving firm swats with the ruler to her unfortunate little balls as she spurts her gooey mess. If you time it correctly, she should experience an almost perfectly ruined orgasm, as the shooting pain from her testicles overwhelms the sensation of cumming.

And then of course, she must lick up her mess, get cleaned up, and clitty cage goes back in place.



Hey baby, you have quite the cute little tush - how about some shots of you in a short skirt & no panties?? And some of your sweet little love hole - bet it looks good enough to eat ;) Ronny xoxo

Thank you Sir. That’s very flattering. I haven’t had many chances to take any good photos, but I hope to soon.