Sissy Gets the Cane

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Punishment and lingerie give him a stiffy.
884 words
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Dear Reader,

My stories are usually about gentle loving relationships between dominant ladies and weak pantywaists. However, some readers have asked that Mistresses punish their sissies. So, this tale is a little harsher. I hope you like it

Sincerely,

Whippet_Darling

---

I lost my erection when Mistress straddled me.

"What's wrong, Darling?" she asked.

"I'm sorry Mistress," I replied fearfully, "but you don't turn me on anymore."

She slapped me hard across the face and scowled.

"Don't you dare talk to me like that, Sissy!" she screamed. "I am your goddess and I've treated you more lovingly than any pantywaist deserves!"

"I know Mistress. I'm ashamed and you ought to punish me."

I had been craving a good whipping. That was how our relationship began before we fell in love and she began treating me tenderly. Now I wanted the thrill of hard core female domination again.

"I haven't beaten you in a long while but it's about time. Don't move!" she said.

Mistress returned with her cane and a pair of handcuffs. She fastened me to the bed frame and turned me on my stomach with my rear in the air.

"This is for your own good, Sissy!" she said.

Her cane whistled through the air and landed squarely across my butt with a loud 'whack'. I cried out in pain but held back my tears. Mistress checked my wiener and found that it was still limp.

She struck me harder the second time and even harder the third. Tears poured from my eyes but my wiener still wasn't stiff enough for screwing.

"Sissy, I need your hard cock between my thighs!" she yelled. "What's wrong with you?!"

I stopped sobbing long enough to blurt out "I want to get fucked like a pretty girl!"

Mistress and I had been having sex almost like a normal man and woman. It's true that she was always on top but had we had stopped wearing sensuous lingerie months ago. Now we were both naked and I couldn't face such boring sex anymore. Sure, her pussy was warm and moist but it just wasn't the same without feminine apparel.

"Why didn't you say so, Dear?" she asked.

"I didn't dare, Mistress" I replied. "I'm your property after all."

"Okay, we'll dress up and I'll give you a good reaming," she answered agreeably.

Mistress unlocked my handcuffs for dressing. I felt girlish thrills of anticipation welling up inside me!

She chose Natoria crotchless garter panties for me. The satiny pink knickers featured a rosebud print and a cute little a ribbon bow centered on the elastic waist band. She drew the sensual undies up my smooth legs. My hardening weenie poked through the open panel. The soft cup bra from La Perla had dainty lace embellishment on the side panels and it matched the pink panties.

Mistress selected a black lace Chantelle bustier for herself. The firm tummy panel was embroidered with a lovely floral design, and the underwire cups lifted and separated her beautiful breasts. Her wonderful shaved pussy was proudly on display between the garter straps.

Finally, we both attached Wolford nylon stockings to our garter clips. She was the hottest Mistress I had even seen and I felt like a fairy princess!

Female domination would not be complete without bondage. So, Mistress handcuffed me to the bed again. Then she strapped on a dildo and put the tip to my sissy hole.

"Beg me not to rape you, Sissy," she said.

I desperately wanted to be violated but I played along.

"Please don't ravish me!" I begged. "I'm just a helpless girl!"

"You are not a girl at all!" said Mistress scornfully. "You're a pathetic ninny and I'm going to bugger you whether you like it or not!"

With that she pushed the silicone dick against my derriere. I clenched my sphincter for as long as I could but when the muscle eventually relaxed the slick dildo entered me. I felt wonderfully full!

I wanted to cry and play the part of the abused victim. However, I loved being under Mistress's complete control and my true feelings overwhelmed me.

"Fuck me harder, Mistress!" I begged joyously.

"Oh, so you're liking this," she said. "Let's check that dickie again."

She turned me over and saw my raging boner. Now I was face up with my weenie sticking straight into the air. My lingerie clad goddess was poised above me like a lion over a lamb and I couldn't have been happier.

Mistress wasted no time in straddling my thighs and engulfing my dick with her moist vagina. Erotic girlish sensations overcame me and I nearly climaxed prematurely. However, Mistress punched me in the eye before I spurted.

Then Mistress clamped her thumb and forefinger firmly around the base of my rod so that I couldn't cum before she did. She had five shrieking orgasms before releasing her grip. I felt like a joyful bride on her wedding night and spurted my sissy cream inside Mistress' hungry pussy.

Mistress collapsed on top of me and whispered, "I hope you realize that I'm going make you my pretty girl and rape you every night from now on."

"Yes, please Mistress," I replied eagerly, "and please don't forget to whip me, too!"

The End.

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Whippet_DarlingWhippet_Darling5 months agoAuthor

Dear woodeaves,

Thanks for your comments.

Sincerely,

Whippet_Darling

woodseaveswoodseaves5 months ago

Yes, your sissiness is not complete without the pretty, delicate sensuous lingerie. I think it was Mistress' frustratration that made Her be so severe with the cane. A good thing you and She made up.

I love it that She made you hard again with a good rape, Her hard silicone cock forcing its way inside you so you could give give your Mistress the satisfaction She merits.

Whippet_DarlingWhippet_Darling5 months agoAuthor

Dear Sissy Lucy,

I will put more caning in future stories.

Thanks for you comment.

Sincerely,

Whippet_Darling

AnonymousAnonymous5 months ago

Mmm heaven, beat me to pleeeease. My master uses a riding crop and before he beats me he teases me stroking my bare bum with it and it makes me so horny. I hope you continue with the story x sissy Lucy

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