The Sissy Bet: Part 8

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

As I remained bent over our bed with my wife still standing behind me with a dildo attached to her strap on harness I felt desperate for more. She had just stopped pegging me right before I was about to orgasm and said that was all I would get because I missed a few spots when I cleaned the house earlier. But I was so close to cumming and couldn’t do anything about it myself since my penis was still locked up in a chastity cage and she had the key.

She had also just made me promise to do anything she said and to never question her again which I had agreed to in my desperate state, hoping that she would have some pity for me to let me finish.

As she started to walk away I stood up and turned to her. “Please, let me cum. I’ll do anything you say. I’m so close and need release so badly.”

She turned back to face me. “You just agreed to do anything I say, why is this any different?”

“I-I don’t know. Look, I’m begging here.”

“Wow, you really are desperate to cum, aren’t you? You got that turned on from me fucking you?”

“I guess so… all I know is that my balls are aching.”

“You know you’re breaking the number one rule of chastity, right? Begging to orgasm? I should give you a really big punishment for this. Maybe another week or two without orgasming.”

“Shit! Uhh. You’re right. I’m sorry. Never mind, I’ll just try icing my balls or something to get them to relax. Forgot I asked.”

“It’s a little late for that, but I’ll tell you what… if you agree to be my sissy maid from now on then I’ll forgive you and even let you cum.”

“Your sissy maid? What does that entail?”

“Well,” she began as she slowly started walking towards me. “I’m going to buy you a little French maid outfit with a black dress, a fluffy petticoat and a cute little apron. Not to mention the thigh high stockings to match the bra and panties that you already wear. You’re going to wear all of that every Saturday as you clean the whole house and wait on me.”

“Seriously? You want me to dress up as a maid again?”

“Don’t tell me you didn’t like being dressed up and fucked like a girl. You’re literally begging for more right now.”

“Will I get rewards like today?”

“Hmm… yes, if you do well enough. But you will also get punishments when you don’t.”

“Alright… sure. I’ll be your maid.”

“I knew you would.” She suddenly pushed me back onto the bed. “Now lift up your legs.”

I lifted my legs up as high as I could. She got on the bed, kneeling between my raised legs as she grabbed my ankles and pushed them back more, lifting my butt up off the bed. She released one leg and used her now free hand to grab the shaft of the dildo and aim it at my butthole. Then she scooted forward, pushing the dildo into my butthole until it pushed in.

I groaned as I was penetrated once again. She move closer as she continued pushing the dildo in, until I felt the balls touch my butt cheeks. My dick started throbbing again. She then started fucking me again as I tried to grind on the dildo at her same thrusting rhythm. 

“I knew you would love getting fucked. You have cock whore written all over you. Tell me how much you love my cock.”

“I-I love your cock.”



“That’s right, slut.”

My abs were starting to burn as she continued fucking me with my legs up. I tried to adjust but she had ahold of my legs and just started going harder.

“No getting out of this, slut. You’re getting fucked until you cum.”

I felt my penis pulsing hard again and I knew I was close. I closed my eyes and bit my lip then felt my penis burst as I cam. I felt liquid hit my face as I opened my eyes and lifted my head up. My penis was continuing to pump cum out onto my chest and belly and some had already hit me in the face and was on my cheek. I melted back into the bed with a sigh. I had never had such a large orgasm in my life. It felt amazing.

With the dildo still inside of me, my wife leaned over me and with a finger she swiped up the semen off of my face. “And now a little treat for my sissy,” she said as she stuck the finger in my mouth.

I tried to spit it out but she put her hand over my mouth. 


I did my best to swallow without gagging then she released her hand from my mouth.

“Good girl.”

She leaned back and removed the dildo from my ass as she climbed out of the bed.

“I hope you enjoyed that. That’s probably the last time you will cum for a while. At least you now know how you will be orgasming from now on.”

“You mean we won’t have sex anymore?!”

“We may, but you won’t be cumming inside of me anymore. The only way my sissy will cum is from anal penetration. Is that clear?”

“Yes, dear.”

“From now on, call me your mistress.”

“Yes, mistress.”

“Expect to have your new maids outfit by next weekend. I look forward to watching you clean and serve me.”

“Yes, mistress.”

“Now clean this mess up.” With that she unhooked the strap on, dropped on the ground and walked away.

I guess I’m my wife’s maid now.

To be continued…?

2 thoughts on “The Sissy Bet: Part 8

  1. I wish that was me I have been a cdslut all my life and I love sucking cock and eating pussy that has been fucked hard. With lots of real man cum inside I am a total subcdsissy now and I am looking for a Dom couples to serve as there cdsissy I know I can be very good little cdsissy dress me up and I will do everything you say fuck me hard and make sure you cum in my mouth I will beg you for more please let me have his cock

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