The Sissy Bet: Part 7

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

“This is your reward,” she said as she stood in front of me, wagging a dildo attached to a strap on harness that she was wearing. “Now turn around and bend over.”

“What do you mean this is my reward?” I said indignantly.

“I’m going to give you a new experience that you’re going to love, trust me.”

“I don’t think I can trust anyone wielding a penis in front of my face that says to trust them. What new experience?”

“I think it’s pretty obvious. I’m going to fuck you. Don’t you worry though, I’ll be gentle. I’ll just use the tip to start.”

“What? Ok, no. This has gone too far. The bras and panties are one thing, but having me dress as a maid and then wanting to fuck me?! That’s just too much.”

“Oh, but dear, don’t you remember our bet? I said that if I won, which I did, you would be my sissy slave.” She paused as she took a step towards me and gently slapped the dildo against my cheek. “And everybody knows that a good sissy, dresses like a girl and gets fucked. Don’t you want to be a good sissy and honor your bet?”

My body was a melting pot of emotions. My brain was telling me to run but my penis was pulsing hard in my chastity cage and clearly very into the scene that was playing out.

“I… I… I don’t know.” I finally mustered.

“It’s not like it’s a real dick. Feel it, it’s fake.”

I looked up at her and grabbed the dildo to appease her. I figured it would buy me time while I sorted through my feelings. It was of course very fake as there’s no way she magically grew a penis since the last time I saw her naked.

“I know it’s fake, that doesn’t change the fake that you want to fuck me with it.”

“Come on, don’t be silly. Your already wearing women’s clothing so if you’re worried about it being ‘gay’ or something, get over it. Not to mention that it’s me, your wife, wanting to do it. It’s not gay if the wife says it’s ok.”


She put her hands on her hips, looking like she was starting to get annoyed. “I have a lot of girl friends that do anal play with their guys and they love it. The guys practically start begging for it to happen again. You men really need to get over the stigma of it.”

“Eh, I don’t know, it just seems so wrong.”

“Well, if you want to go back on your bet then I guess we can just stop with this whole chastity thing and go back to our normal old life and normal old sex life…”

“No! I don’t want that. I like our life how it is?”

“I know you do. You love it that I make you wear your tiny little cage over your tiny little penis. You love that I make you clean and cook and do all the house work. You love that you only get to cum when I allow it. You love being my servant and you’re going to love being my sissy.”

I felt like I was being hypnotized by her words. Our eyes were locked and I was speechless. I couldn’t deny anything she was saying.

As if my lack of denial was affirmation, she smiled and said, “Now be a good sissy and turn around and bend over for your master.”

I stood up and started to turn around. I didn’t quite know what I was doing or what was about to happen, but I felt powerless and could no longer resist. I bent over, putting my forearms on the bed, and closed my eyes. 

“That’s a good girl,” she said as she pulled down my pantyhose and panties. I heard her squirt something into her hands then felt a cold, wet touch on my butthole which caused me to flinch. “It’s ok, it’s just my finger with some lube. I said I would be gentle.”

She rubbed the outside of my butthole and then I felt her slowly start to penetrate it with her finger. I jumped forward when I felt the slightest entry.

“Ok, I’m not going to be gentle if you’re going to be a bitch,” she said with clearly annoyed tone.


Suddenly I felt her whole finger enter my butt. I was shocked. It didn’t hurt and it didn’t feel good, it was just weird. She slowly started pulling her finger back and then pushing it back in, rhythmically. It was starting to feel… ok.

“See, it’s not so bad, right?” She asked.

“No, I guess not.”

She pulled her finger all the way out and applied more lube on it then penetrated me again. The extra lube was nice and I could tell she was going deeper as I could feel the back of her other fingers on my butt cheeks. The deeper she pressed, the better it felt.

“Oooh!” I let out. I was immediately embarrassed by my moan but she wasn’t stopping and I couldn’t suppress it anymore. She started pressing in as far and as fast as she could and I moaned louder.

“That’s right, you like getting fucked, don’t you, sissy?”

“Yes…” I sighed out between moans.

“Are you ready for a real fucking with my cock?”


She pulled out her finger and started covering the dildo with lube. What did I just agree to?! Before I could reconsider I felt the tip of the dildo touch my butthole with pressure and then suddenly it popped in. I gasped as the tip entered me.

She started slowly, just pushing it in a little bit and continuing a rhythmic motion. It wasn’t enough, I needed to feel it as deep as her finger was. It went deeper and felt better. 

“You’re such a good little sissy slut. You’re fucking yourself!” She said.

That’s when I realized that I was pushing back on the dildo to make it go deeper. I didn’t care, I needed more if it inside of me. I kept going.

“That’s right, take my cock, sissy. Push back on it. Make it go deeper.”

My chastity cage felt like it was ready to burst. My moaning was in rhythm with the dildo thrusting inside of me. I felt like I might cum.

“Ok, sissy. I think that’s enough for tonight.” She said.

I felt a panic consume me. “No! I’m so close, keep going!” I begged.

She pulled out the dildo and said, “if you wanted more, then you shouldn’t have forgotten to clean beneath the dining table and you definitely shouldn’t have questioned my reward in the first place. If you ever want to be fucked again, then you better not question me again. Is that understood? You’re to do everything I tell you.”

“Yes, I understand.”

“That’s a good sissy.”

To be continued…

Leave a Reply

Your email address will not be published. Required fields are marked *