Mistress Sara and Her New Sissy Boyfriend A Story of Chastity

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sissy boyfriend

My new mistress girlfriend has taken control of everything I do when I wake up, what I eat, what I wear and when I go to sleep. I am her new sissy Boyfriend now. She also tells me when she wants sex, or more importantly, when she wants an orgasm and how I am going to give it to her. Sex is rarely an option since she has decided to keep me locked in chastity. I usually have to achieve this with my tongue, a dildo strapped to my face or, if she really wants to humiliate me, she will have me strap on a dildo around my waist and fuck her with my rubber cock while my useless caged member is pressed against my body never receiving the pleasure I hope for.

One evening Sara returned home from work as I was making dinner, I was preparing the meal she had requested that morning. She walked in and I greeted her by getting to my knees, help remove her shoes and kissing both of her feet. As per the usual, she pushed her foot hard against my face as I kissed it and rubbed it all over then stuck one of her perfect toes in my mouth and had me suck it as she laughed at me.

Welcome Home Mistress Sara

She was carrying two bags and placed them on the ground after she took her toe out of my mouth. I stayed on my knees until I was told to move.

  • “One of these bags is for you.”

She said as she watched to see if I would move like an untrained puppy looking at a treat.

My eyes glanced at the bag then back at her, she knew I loved getting presents from her and I was excited to see what it was.

  • “Good puppy, now go get your treat, yours in the light blues ones.”


  • “Thank you Mistress Sara.”


I said as I crawled over to the bag and saw a very light blue bra and panty set. It was a beautiful soft material and the panties were my favorite hi-cut style.

  • “Thank you so much Mistress, what do I owe the honor”


  • “You have been a good boy lately, I decided you should be rewarded.”


She said as she walked over and put her foot against my chastity device.

  • ‘Yes Ma’am, thank you Ma’am.”

I said as I started to lean over and kiss her foot again but she moved it out of the way.

  • “No need my pet, I just like to make sure it is still on and you have not betrayed me.”


  • “No Mistress Sara, I would never even think..”


  • “I know. Now put on your bra and panty set right now and let me see you in it. Then I want to eat.”

Sissy Gets A Present


  • “Yes Mistress,”

I said as I quickly undressed and folded my clothes neatly and placed them on the steps. I carefully stepped into my new panties and felt the cool, smooth material slide up my legs and rest on my hips. The outline of my chastity device was prominently pressed against the fabric of my panties. Much more than my tiny penis ever was. I then slid the straps of the bra over my shoulders and clasped the hooks behind my back. I adjusted the bra until everything was in place then did a dainty spin for my Mistress.

  • “Great!” she said as she clapped her hands together.


  • “Thank you Mistress. I love them.”


  • “I know slave, now I am ready to eat.”


  • “Yes Mistress, let me go get your dinner and I will meet you,” I said as I ran of into the kitchen with the new fabric moving against my skin as I trotted away.

After dinner Mistress told me to meet her in the living room when the dishes were done. I rushed to get them done so she would not have to wait for me. When I entered the living room she was sitting on the couch with nothing on except her giant 9inch strap hanging between her legs and resting on the couch cushion. Sometimes she would wear this and make me suck it just to humiliate me so I quickly ran up to her and got to my knees and started to massage her rubber cock.

Mistress Sara’s Sissy boyfriend

  • “Not tonight slave, tonight you will be the girl.”

I knew this day would be coming; she had never entered me from behind but had said it would eventually happen.

  • “Yes Ma’am, what should I do for you?


  • “Get on all fours bitch”


  • “Yes Mistress, of course,” I said as I quickly dropped to my hands and knees and turned so my pantied ass was facing her.


  • “This may hurt slave, but it is supposed to the first time.”


  • “Yes Mistress, I understand.”

She stands up and I feel the tip of the cock rub against my ass as she positions herself behind me. Then I feel her fingers press against my hole and it is cold.

  • “I am going to lube you up to ease the pain a bit and because it is safer this way.”


  • “Thank you Mistress.”


I say as my eyes close when she presses her finger into me and rubs around my entrance.

I then feel the tip of her cock placed against my ass. Then I feel the push as it presses through and into me, first, it is just the tip then it is slowly taken out. It is a painful experience as she pushes more into me and slowly moves out. My mouth clenches and my eyes close tight. Then I feel her press into me one more time but she does not pull out and I feel her hands grip my hips and she presses deep into me until our hips touch. I let out a gasp, the pain, and the pleasure mix when I feel her skin against mine and know her cock is filling me up.

What A Good Girl!

  • “Mmmmm, Good girl” she says as she hears me gasp. “Just relax and take what I give you.”


  • “Yes Mistress. I will.”

She moves out about halfway and then starts to thrust and fuck me with her strap-on. I feel the tip of her rubber cock press up against my prostate with every thrust and the feeling is intense. Her momentum increases and she pushes down on the back of my head.

  • “Head down, ass up bitch. I am going to jackhammer your pussy.”

My head gets pushed to the floor as I feel her angle change as she fucks me. It almost feels like she is gettering deeper and deeper with every thrust. Every thrust brings a primal squeal from her and she starts smacking my ass as she pounds me. The pressure against my prostate is making my cock feel full at the same time.

  • “Who owns your pussy you little bitch?” She says in a commanding voice.


  • “You own me Mistress, my pussy is yours,” I say with my face turned and pressed hard against the ground.


  • “I do own you. I own your cock, your pussy, and your pretty little panties. Don’t I, you slut?”


  • “Yes Mistress, I belong to you, I am your property.”


  • “Good, now I am going to cum in my property.”


She said as she thrust hard into me, deeper than I felt through this whole experience and I could feel her body quiver on top of me. As she orgasmed on top of me I felt my cock dribble cum through my chastity device.

Now Thank Your Mistress

My eyes widened as I felt the cum drool out of me and I didn’t know what to do. As my Mistress pulled her cock out of me she walked around and pushed it in my face.

  • “Kiss my feet and thank me.”


  • “Yes Mistress Sara, of course.”

I kiss her feet and thank her as instructed and I tried to hide the cum that came out of me.

  • “Did you cum bitch?” She says as she points to the spot on the floor.


  • “Yes Mistress, I am so sorry, I didn’t even know I was going to, it just happened. I would never come without your permission. Please forgive me.”

She laughed as I begged for her forgiveness and said,


  • “My little bitch is a squirter, that’s fantastic. Now clean that up and put your panties back on. You are no longer my boyfriend, you are now my girlfriend and I expect you to dress the part. When you get this cleaned up and dressed come upstairs and we will get you some makeup tips and a new set of rules for how to dress and what I expect from my new girlfriend.”

My cock pressed against its cage hearing this. I quickly licked up my mess and pulled my panties back on. I ran upstairs to get started on my new life.


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2 thoughts on “Mistress Sara and Her New Sissy Boyfriend A Story of Chastity”

  1. I really enjoy this type of humiliation. Its a turn on always to make my slave my bitch for a first time. They seem so lost and then they love it!!!

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