Chastity Sissy Boy Is Turned Out By Mistress

| |

An Evening My Chastity Sissy Boy Will Never Forget

chastity sissy boyAfter my soon to be chastity sissy boy returned home, I looked at his browser history and understood what he wanted. As he walked into the living room, I was sitting on the couch, wearing some hot lingerie, I was so horny that my tits stood firm and my matching thong made him stop and stare. I was almost giddy as I knew what I was about to do with him.

He glared at me and I told him to undress, “Now drop trow!” I said to my future chastity sissy boy and I could see he was hard as he dropped his pants. I stood up and circled around him. His eyes shot down to my ass and I said abruptly, “Look up.” He was shocked by this as I circled him in my heels, “You like what I am wearing?” I asked, “Actually I know you do, your pathetic excuse for a prick is hard. But that’s not a dick, that’s a sissy pussy, you just forgot our Femdom rules.” I could see him getting nervous.

I’m Your Goddess Now

“What rules Mistress?” he asked. I slapped his face, “No talking, you refer to me as Goddess now,” saying this as I smacked his hard cock. I quickly reached over and grabbed a box from the counter that held his present. Pulling out his present, I saw his eyes go wide, “This is where I will have your pathetic prick locked, in this tiny little plastic chastity device. You see you don’t get hard without me saying so, I make all the rules now.” His dick was still hard but I had a solution, “Hands behind your back, NOW move. Perfect,” As I clipped handcuffs to him and attached him to the exercise equipment pull-up bar, he could not get loose and was standing there with his dick hard.

Adopt your sissy

I didn’t blame him: I looked so hot in this outfit. I grabbed the ice water and sank his hard cock in the ice water. His dick went flaccid as he screamed. “Shut up, you baby.”  I took some lube and snapped the chastity cage in place. I took the key to his cock and put it around my neck as I moved my hair. Turning around, I pressed my perfect butt onto his stomach with the chastity cage right between my cheeks. I wanted to tease him because he shrunk so much and wanted to see his lust as his dick grew in the chastity cage . “Oh chastity sissy boy, want me to drop my panties? I hope you aren’t thinking about fucking me?”

I Want To Fuck You Goddess

“Yes, please, just let me down and out of my cage Mistress.” I turned around quickly and was eye level with his dick. I could see it worm it’s way until the tip came in contact with the end of the short little tube. This was thrilling as I looked up I could see my boyfriend trying to look down my bra, “Oh what, you like these?” “Goddess please let me out my dick hurts so bad, I can’t get hard…”


Sissy Slut In Sissy Clothes

“You don’t deserve to get hard like a real man, because you are just a pathetic chastity sissy boy. This is what you wanted isn’t it.. for your girlfriend to have all the power in this relationship, right? Well, now I say when your dick gets hard.” He looked unsure as I  smacked his chest hard and stared in his eyes.

“Wait here,” I said laughing as I ran upstairs and came down again. “A chastity sissy boy has to wear sissy clothes.” I pulled out a pair of blue lace panties and thong and came back downstairs. I pulled them up his thigh, then I put a little mini skirt and my Velcro halter top on him. It fit him nicely. Then the final touch, a wig that had been sitting around and a little make-up. I hardly recognized my boyfriend, he looked like such a pathetic bitch. “Mistress, since I have been so good, will you please let me fuck you?”

sissy chastity

We’re Going To Have Some Fun

“Fuck me,” I said, as I lifted his skirt to reveal his cage covered by the panties, “I don’t see anything to fuck with, all I see is a pretty sissy pussy from a sissy chastity boy.” I leaned into my boyfriend and stuck my hands down to his ass and pushed the top of my sloppy wet cunt on him. I rolled my head on his shoulder and coldly said, “I don’t get off with girls sweetie, only big veiny, man dicks. I like to ride it nice and hard.” I massaged my clit with his chastity cage as I could feel the plastic inside my pussy and the warmth from his cock inside the cage. “This is a sissy dick and I will never, ever, ever fuck that pathetic thing again….”

“But Mistress,” I cut him off, “But nothing.” Now, we are going to have some fun”, I said as I stood inches from his face. I could feel the tip of his dick enter me. “You wanted to fuck, we can fuck.” I went to the counter and got a box. From inside the box, I pulled out a belt and wrapped it around his waist. I reached in the box and said, “Honey, since your pathetic prick is way too small to please my pussy, I got something that will satisfy me,” I saw him blush as I pulled out a large black dick.

No Pleasure For You

I brought it to his face, “See, this is a man’s dick,” I said as I held it near his cage. “This is what a woman needs to get off on.” I inserted it into the ring under his skirt. “Now we are going to fuck!” Grabbing his leash, I unlatched his restraints and went to the couch. I imagined he looked pretty pathetic wearing a dress with a rubber man-sized dick strapped to his waist. Putting the lube on his dick, I pulled the head close to me, “You do what I say,” my pussy was so wet, I don’t think I even needed the lube.

I dropped my panties and looked at the horrified look on his face while letting him inside of me. The feeling of it entering me was invigorating while I pulled on his leash while he was inside of me. I turned around and grabbed his chastity cage and said, “This pathetic fucking sissy pussy getting hard hun, it’s too bad you get no pleasure sissy chastity boy, dressed like a sissy slut pleasing your mistress’ pussy like this. So close to fucking me, now fuck me.” He stroked, there was a plastic sound, I couldn’t believe it but it was his caged dick hitting my pussy as he stroked, “You are such a fucking pervert, fucking your Dominatrix in a dress.

sissy pegging

Love Being Humiliated

What kind of man are you? You’re not a man your a sissy chastity boy.” I felt a rush as I said, “I can hear the noise of the plastic of your caged dick bouncing on my pussy. What would you do if I took you out and let you be inside me? I bet you wish I would let you fuck me like a real man, not like this in this pathetic way? Dressed as a girl, dick locked away?” I moved back slowly into the dildo. “Huh, Sissy?’ “Anything Mistress, anything to fuck you”

“Anything you say,” I continued to grind on the dildo. “Well fuck me good now, and you might earn it.” He grabbed me and started to thrust and it felt so damn good. I said to tease him more, “You are no real man, you are my little sissy, no real man would ever agree to this level of humiliation, your just a fucking pervert sissy slut.” I couldn’t take it anymore, I got on top and grabbed his face and came hard. I stopped and took the dick off his waist and put it around my waist, “Okay time for us to fuck.” He complained and pleaded, I slapped his ass and made him bend over.

His Point Of View

I have been worried about me being exposed as Mistress’ sissy chastity boy. I act like her boyfriend, but she not only wears the pants in the relationship but the balls as well. She has been talking about this for weeks, her plan to fuck me in public. I can’t say no, she’s the gorgeous dominant one in our relationship. Ever since she put me in chastity, she hasn’t let me cum naturally in a month and hasn’t unlocked me in weeks.

Sex is all I think about, but she teases me with her body and then puts her pussy on my face and makes me give her an orgasm. I am so horny I can barely think. I imagine sex in different places, any woman that walks by I immediately get hard. Well, that is until my dick reaches the end of my chastity. I’ve been so close to her, my goddess, but she only uses my body to get herself off. She even made me fuck her with a dildo strapped above my chastity cage. She dresses me like a girl and she has my ass whenever she wants.

Fucking In Public

She wants others to see how we actually fuck, her dick up my ass, my dick locked in chastity. I love it, it’s our secret, but I have no choice, she wants to do this and as a sissy bitch what happens in our relationship is her decision. Until we arrive at the sauna, I plead to her that I don’t want to be exposed here, but this is thrilling for her and the fear of getting caught in such a kinky way lights her up. She drops my towel and you can see through the plastic cage my dick wants out. She smiles and tells me to turn around and sit in her lap. I plead, but she grabs my face and sternly says “Now, sit on this dick.”

I turn around I am sweating watching the door, my legs together, I feel the hugeness of her dildo. My muscles can’t relax. It scares me and she smacks my ass. “Bounce on it bitch,” she says. I try to grind on the dick and it’s so deep I have to close my eyes as she thrusts and I feel her so far in my ass. Hearing the door open, I see two hot women walk in topless and just start laughing, “Wtf is going on here!” they say in unison. The women approach and my Mistress ignores the gorgeous women and I can’t take my eyes off of them. I’m going to cum right in front of these gorgeous women with my dick in chastity. But I need my Mistress’ permission first.

Embarrassed In Public

“Mistress, may I cum, please?” The women look on speechless. Mistress then stops fucking my asshole but keeps it in my ass while I sit naked on her lap. “Ladies, she says, “this is my chastity sissy boy and this is how we fuck.” They look confused. She continues, “See he’s my little cum slut and that plastic cage he’s wearing, only I have the key, I haven’t let him cum for a month. Look you can touch it.” Mistress makes me stay as they both touch my chastity cage. I’m so close to cumming and I’m still sitting on her lap with her cock up my ass.

They giggle and say, “What kind of man is this?” I’m so embarrassed as the two women laugh. “He is a sissy chastity boy, I’m his Mistress, this is a female led relationship.” One lady speaks up and says, “But how do you get off then?” “Good question,” Mistress says. He eats my pussy and he’s so desperate to fuck me from his chastity that he does a great job.” The women look shocked and their nipples harden. “Want to try?” The girls hesitate, but one girl drops her towel to reveal her nicely shaved pussy. Mistress smacks my ass and commands the girl to sit on the bench and spread her legs. She tells me to bend over and lick, then moves my head to her cunt, but keeps her cock in my ass. The stranger moans as I lick her.

Doggy Style In The Sauna

“This is amazing. I’m going to cum.” She orders me to stop as she pulls out another strapon from her bag and ties it around my waist above my chastity. The stranger doesn’t miss a beat as she moves in a doggy style position. I need to be out of chastity now! “Mistress, may I please be released from chastity?” Mistress says, “Absolutely not! Now fuck the nice lady.” The is horrifying, I move the strangers’ hips to my strapon dildo and hear her moan as my chastity smacks her pussy. Mistress says, “One more thing,” and she starts fucking me in the ass again.

Join Femdom.Dating



male toilet Slave for Femdom Dominatrix

The Enjoyment of Small Cock Humiliation


1 thought on “Chastity Sissy Boy Is Turned Out By Mistress”

  1. Excellent ! i have always liked public humiliation stories, whether they have sex in them or not. Try other words or euphamisums for the chastity device; ‘male jail’, ‘cock cage’, ‘faithfulness enforcer’, ‘erection killer’, ‘bound boner’. Write more – as a new story or a continuation of this one.

Leave a Comment


Do you need discipline?

Click here to begin >

No, thanks!