This is a continuation of our sissy story, The Sissy Bet.
“3…2…1… and the Buccaneers are world champions!”
My shoulders slumped even more as I did the dishes while overhearing the TV in the other room. I opted to start my chores early rather than watch the rest of the blowout of a game. I was really excited to have a sex-filled night with my wife, but I lost our bet and would now have to be her chastity slave. As if I wasn’t already.
She didn’t even bother to watch the game. She decided to go shopping by herself and I wasn’t looking forward to her coming home and having to tell her the outcome of the game.
As I finished the dishes I heard the front door creak open and saw my wife walk open with a handful of bags and a big grin on her face. “Hey slave, take these up to the bedroom,” she demanded as she dropped the bags on the floor.
I groaned as I trudged over to her and picked up the bags. “I’m guessing you saw the score?” I asked.
“I didn’t have to. It was all over the radio about how terrible the Chiefs looked and how badly they were losing. I bet you’re glad you watched instead of going out with me, huh?”
I rolled my eyes as I turned to head to the bedroom so she couldn’t see. “Well, it looks like still you had a good time shopping without me so it worked out for you.”
She followed me towards the bedroom. “I definitely had fun shopping. Especially shopping for you, my new little sissy slave. Put the bags on the bed.”
I did as I was told and stepped back, wondering what she had bought for me. She walked to the bed and started going through one of the bags. It was a tall, pink Victoria’s Secret bag.
“First, we have your new underwear,” she said as she pulled out some small, black items from the bag. “I was nice and got you all black to start so people won’t notice if they’re showing. I got you a few different styles so you can figure out which you like best…”
“Wait… You actually want me to wear women’s panties?” I butted in.
“Of course, that was a very specific part of our bet. You lost and now you’re my sissy slave and a good sissy wears panties. Don’t pretend like you don’t want to do it.”
“Well, I guess I’m pretty curious to try them. I’m just surprised that you want me to,” I explained as I started to blush.
“Hunny, we’ve been together for awhile now and I think I know you pretty well. You may have lost this bet and may be pushed into doing things you’re uncomfortable with, but I’m certain that in the long run you’re going to love it all. I’ve come to peace with it and I want you to also.”
“Come to peace with it..? What are you talking about?” I was very confused now but also intrigued and slightly aroused. It had been over a year since she had started locking me up in chastity and I still was getting aroused by every little tease, especially the longer she kept me locked up. I had been locked up for over a week at this point and this mystery that she was unveiling really had my horny mind running wild with possibilities and my penis was starting to throb in its small cage.
“You will find out over time. Just trust me for now and let me enjoy my process. I did win our bet after all so I do intend to have fun with my plan to make you my sissy slave.”
“Umm… ok, sure,” was all I could muster in response as my brain was flooded with sexy ideas.
“Good. So back to the panties. I expect you to wear these every day that you’re caged. If you’re not caged then it’s optional, but you’re going to be caged more likely then not so you might as well plan to always wear them. When you figure out which you like best let me know and we will go shopping for more of that type and maybe even get you some cuter colors.”
I could feel my penis filling up my chastity cage now. Go shopping for panties to wear with my wife? That sounds so naughty. “Can I pick out some for you to wear when we go out?”
“Ooo! I love it. It’s a date!” She looked genuinely happy. “Second, it’s time for an upgrade of your chastity cage… or downgrade maybe? Whichever, it’s time for you to wear a smaller cage.”
She went to her bedside table and opened the top drawer and took out a small chastity cage in the same style that I normally wore. “I’ve been saving this for the proper time and this is definitely it,” she explained as she handed me the cage.
I wasn’t nearly as thrilled with this as I was with the panties, but I figured I would at least try it so I took it from her. “Ok, what else?”
“Is that not enough for you? What an eager sissy you are!”
I cringed a little every time she referred to me as her ‘sissy’ knowing there was extra meaning behind it that I wasn’t yet understanding.
“This is all for now. Let’s get you adjusted to the tiny cage for your tiny penis and your new panties first and then we will start phase two.”
To be continued…