The Sissy Bet: Part 4

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

As I walked in the front door of our house, shopping bags in hand, I felt my heart start racing again. My wife and I had just bought each other bras and panties and she wanted us to model them for each other. I had been wearing panties for the last week since I lost our last bet, but she hadn’t seen me wear them, they’ve always been underneath my clothes. I was excited to see her in the new panties I had picked out for her however.

My plan was to keep calm and casual, to not seem eager about modeling. While I was eager to try on my new bras and panties, I wasn’t all that eager about dressing up for my wife and because I didn’t want to get turned on thinking about my wife wearing hers. After being locked up in my chastity cage the past few weeks, it didn’t take much imagination to get my penis to fill up and push against its cage and I knew this was going to be a painful tease.

I walked into the kitchen and set the shopping bags on the counter then went to the refrigerator to grab a drink. “Want anything?” I asked as she entered the kitchen.

She gave me a smirk as she said, “yeah, I want to see you try on your new bras.”

“Hah, right to that, huh? Why are you so eager to see me wearing a bra?”

“Because I think you will like it and it will be cute seeing you in your new matching sets.”

“Won’t you think less of me as a man seeing me wear them?”

“Hun, we’ve been married long enough for me to know exactly how much of a man you are. Now stop stalling and take those bags to the bedroom.”

I took a sip of my drink and shook my head in defeat. I think she bought my performance.

“Alright, let’s get this over with,” I said as I walked back to the counter to collect the bags. When I got to the bedroom I set the bags on the bed putting my bags on my side and my wife’s on hers. “How do you want to do this?” I asked.

“I’ll break the ice,” she replied as she kicked off her shoes and started unbuttoning her pants. “I’ll model a pair for you and then you can model for me.” 

She wiggled out of her jeans then started pulling off her top. Soon she was wearing nothing but her matching pink floral bra and panties. Then she began to take those off, too. First unclasping the back of her bra and then removing it to uncover her ample breasts then slowly sliding down her pink thong. I felt like I was watching in slow motion. I was so horny and seeing my wife naked in front of me was already driving me crazy. I could feel my testicles tug as my penis tried to get erect in its small cage.

“Let’s see, I think I’ll try these purple ones on.” She picked the purple set out and put them on. The panties were a cheeky cut with straps at the top; the bra was lacy and slightly padded which really gave her some amazing cleavage. Once they were on she laid down in bed and said, “now it’s your turn. You should try on your purple ones, too.”

I felt my self shaking a little both with nerves and arousal. I took off my shirt and then pulled down my pants and the panties I was already wearing at the same time, becoming completely naked.

“Oh, wow, someone’s excited!” She exclaimed as she reached over and gently stroked my cage.

“Well, yeah, seeing you naked always gets me excited.” I replied.

“Mmm, good. I’m excited to see you in your new outfit though so put them on.”

I let out a short sigh and did what I was told. I first took retrieved the purple panties from the bag. They were the same panties that she was wearing; we both liked them so we decided to both get them so we could match on occasion. Of the panties she had previously bought me, the cheeky were one of my favorites and I enjoyed the feeling as the new ones slid up my butt crack and hugged my cheeks. I tucked my chastity cage down the best I could as I had come to learn that was the most comfortable way to wear women’s panties.

I then pulled out the matching purple bralette from the bag. I stared at it for a moment, trying to figure out how to best get it on. In the end I figured to just put my arms through and put it over my head like I would a t-shirt. I did so and pulled it down over my chest. It fit well, a little snug but it fit my chest well. I wasn’t out of shape, but I wasn’t in great shape either so I had what some might consider to be small man breasts and the bralette cupped and supported them.

“Look at you, my little sissy, in your matching bra and panties. I’m so proud. How do you feel?” My wife asked as she looked up at me from the bed. She had turned onto her belly and was looking up at me, propped up with her arms as her legs where kicked up and crossed behind her.

“Uhh, pretty silly to be honest.” I replied as I turned around to check myself out in the mirror.

“There’s nothing to feel silly about. It’s just clothes, if it feels good then you should enjoy it. Plus, your wife is telling you to wear it so have some fun with it.”

“A-alright. I guess you’re right. It’s just clothes.”

“Exactly,” she started as she sat up in the bed. “Want to try some more clothes on?”

“Sure, how about the red ones next?”

“No, no. I think you should keep the purple ones on and try something else.” She got out of bed and walked towards her closet and started digging around. She grabbed a couple items then turned to show them to me. “Here, try these on.”

In her outstretched hands were pantyhose and a short black skirt.

“You want me to wear more women’s clothing?!” I asked in surprise.

“Oh come on, it’ll be fun. Just put them on and do a little swirl for me. You will enjoy it, trust me.”

“Ok, fine.” I said as I reached forward grabbed the clothes. I quickly slipped on the skirt which was very short, barely covering my butt cheeks when I had pulled it up to my waist. After noticing me stare at the pantyhose for a bit, she came over to help me get them on. I have admit that they felt very good. So silky and soft.

“Ok, now you look silly. You need a top. I have some old blouses in here somewhere.” She said as she began to dig through her closet again. “Here we go.” 

She pulled out a white button up blouse and handed it to me. I put it on and buttoned it up as much as I could but as I got up towards the chest it was a little tight so I stopped.

“Don’t worry, us girls never button those ones up,” she said as she suppressed a laugh.

I turned back to the mirror to see myself wearing all women’s clothing. “Now I feel very silly.” 

“Silly, but you like it right?”

“I mean, it’s alright. It’s a little tight but not uncomfortable or anything.” I replied as I turned back to look at her.

“Well I think you look sexy in it. Like a sexy little school girl in your little pleated skirt.” She walked up to me then softly kissed me. I couldn’t suppress my horniness any longer and quickly put my hand around her head and started kissing her back passionately. My penis throbbing in its cage.

As we continued to make out I lowered her on to the bed. Me still wearing her clothes and her still in just her bra and panties. I mounted her and started grinding my cage on her, still making out. She moaned as she broke away from my lips and elongated her neck. As I began to kiss the length of her neck she moaned more.

“I bet you want your little dick unlocked so you can fuck me, don’t you?”

“YES!” I roared.

She put her lips next to my ear and whispered, “too bad. Your dick stays locked up, sissy.”

Her words of denial sent waves down my body. Her control over me was so hot and I just couldn’t take it anymore. I felt my penis explode as I orgasmed. It kept pumping and pumping. More than I had ever felt it pump before. “Oooh!” I exclaimed.

“Did you just cum?!” She shouted as she propped herself up on her elbows. 

“Yes…” I admitted.

“Naughty girl! Wow, you must really like your new outfit. I think you should keep it on as you clean up your mess and go make us dinner.”

I rolled over onto the bed next to her and let out a deep breath. “Wait, what?” I let out as I realized what she had just said.

“You heard me. Go clean yourself up and go make us dinner. You’ll need a new pair of panties I presume, find something that’s close to matching.” And with that she got up and started to put her clothes back on. “I expect dinner to be ready in an hour.”

To be continued…

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