The Sissy Bet: Part 5

This is a continuation of our sissy story, The Sissy Bet.

Getting used to wearing a bra on a regular basis was definitely taking some effort. I had to find the right strap length so it wasn’t too tight or too loose and having something snug around my chest, offering support for my slightly flabby chest was a very different feeling.

My wife, who had required me to wear these new bralettes that she bought me, let me start slow by wearing them every other day and only while I was at home, but I knew that she would eventually change that rule as she seemed adamant that I would be required to continue to wear women’s underwear and these bras.

The panties I was quickly getting used to and starting to quite enjoy. They never rode up like my old boxers and were so soft. Not to mention that I was liking the feeling of a thong in my butt cheeks. Not sure what it was exactly but it made me feel… sexier.

I still wasn’t sure why she wanted me to wear women’s clothes, but I knew I needed to respect our chastity bets if I wanted to continue to have them and if I ever wanted to get my chastity cage off. And as far as bets go, wearing some lacy panties was far from a bad punishment for losing so why complain. So I continued to do as I was told until my wife decided to change things up again…

“Hun, this house is a mess. You’ve been really slacking on your chastity chores!” She said.

“It’s not that bad! There are only a few dishes in the sink and that’s about it.” I replied in defense.

“Not that bad? The floor has dirt everywhere, the house is covered in dust, the bathroom sinks and toilets are covered in grime, and the bed sheets haven’t been changed in weeks. Just to name a few things. You need to clean all of that today.”

“Ugh, seriously? It’s Saturday, I was hoping to relax.”

“I think you forget our arrangement.” She reached into the top of her blouse and pulled out a necklace which contained my chastity key. “If you want to see these again then you had better start cleaning.”

I felt my penis start hardening. I loved it when she would get dominant. “Alright, alright.” I said as I got up from the couch and stretched a little in preparation of a long day of cleaning.

“Good. But I’m pretty upset that you would dare question me.” I turned to look back at her. I could tell she really was upset by her posture and the frown on her face. She stood up, right in front of me and continued saying, “Because you questioned me, you need to wear a special outfit. Remember what you wore when you were modeling your new bras and panties for me? You need to wear that.”

“You want me to wear pantyhose and a skirt while I clean?”

“You’re not questioning me again, are you?”

“Uh, no, no. Of course not.”

“It will be fun and if you do a good job… well, remember what happened last time you wore that outfit?”

My mind quickly flashed back to us making out on our bed and me orgasming in my cage while wearing that outfit. “Oh, ok, yeah. That does sound fun!”

“Well, then go get dressed and get started. I think I’ll stay here and relax.”

I had a new found excitement so I hurried upstairs to get dressed and get started. I dug through her closet and found the same top, skirt and pair of pantyhose she had me previously wear. I got out of my clothes, just leaving my bra and panties and put the new clothes on. I really enjoyed the feeling of the pantyhose; I rubbed my legs afterwards to feel how soft and smooth my normally hair legs felt. The skirt was short and really let my nether region breathe. After wearing it for just a short amount of time I wondered why men don’t wear them.

When I was dressed, I went downstairs to get started. As I rounded the corner into the kitchen, my wife was waiting for me.

“I have one more thing for you to wear,” she said as she pulled something out from behind her back. It was a white apron. “Turn around and I’ll put it on.”

I turned around as she instructed and raised my arms as she tied on the apron. When she was done I turned back around to face her.

“Look at you! You look like a proper maid.” She exclaimed.

“Oh, I see what you’ve done. So I’m your maid now?”

“Well, it wasn’t my intention, but I like that this is how it turned out. You’re going to be my little sissy maid for the day. You’re going to clean the house and serve me snacks and drinks at my beck and call.”

“Yes, dear.” I said with a dash of sarcasm.

“Remember, if you’re good then you may earn yourself a reward. However, if you do a bad job or give me attitude, then I’m going to have to punish you and you will be locked up for at least another week.”

“Uh, ok.” Those are some harsh terms, but I saw it like a bet. I was betting on my ability to clean up and please her today.

“Time to get started, sissy.”

To be continued…

One thought on “The Sissy Bet: Part 5

Leave a Reply

Your email address will not be published.