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Happy to teach you all about using a sissy butt plug

Do you have a sissy butt plug?
sissy butt plug Experienced Mistress Olivia 1-800-721-1962

Listen to me talk with you about getting a sissy butt plug.

I have all kinds of tips for being the best sissy.  Being a full-fledged sissy is more than just wearing cute clothes.  I want you to be prepared to pleasure men with your lips and your sissy hole.  That means you need to learn to be an anal slut.  I’m going to add anal play to your sissy training lessons.

I met a FABULOUS sissy recently.  She is delightful in so many ways.  I was surprised when she said she had only used dildos in her fuck hole.  I sent her out for a shopping assignment and she came back with a butt plug!  What a good girl!

Put in the butt plug cupcake

At first, she said, “Oh oh it feels like it’s slipping out.”  This Mistress knows anal and I coached her into making sure the plug is all the way in and seated correctly.  It shouldn’t slip out.  You will know when it’s IN.

Her reaction when her sissy hole is filled

I just love this special cupcake.  She is such a slut!  She squealed:

“OH OH OH that feels so good!  ~gasp~ ~panting sounds~ Ohhhhhhhhh it feels so good to be filled!!!”

Difference between a dildo and a butt plug

I love sex toys.  Different sex toys make you feel different sensations and emotions.  She volunteered this review:

“A dildo is like getting fucked.  When the butt plug is in there, I think it’s to make you feel like a sissy.”

The squirming sissy slut with big boobs

I love a big titted sissy and sissy Ashley has enormous bouncy boobs! Big tits are the hallmark of a sissy bimbo.  She is going to get a lot of use out of her new butt plug.  I’m always happy to teach you how to get and use new sex toys!

Your Experienced Mistress,

Ms Olivia

43 comments to Happy to teach you all about using a sissy butt plug

  • Emily

    I love my plug . But how long can it be worn ??

    • Olivia

      Short answer — it depends on many things. This question is actually a GREAT question — I’m going to turn it into a blog post, so stay tuned sissy!

  • Sounding Boy

    I’ll wear mine as long as you tell me to.

  • Sounding Boy

    Only about 30 mins. Usually before having a call with you to help me prepare. I haven’t tried longer when I have enough time, but I’ll try to next time if that’s your wish.

  • Alex

    My wife loved this blog post. She turned to me and asked, ” Its like shes talking to you isn’t it?”

  • Princess

    I have enjoyed the feeling of fullness associated with being plugged. I view it as training for fucking more than actual fucking. It’s wonderful how it stretches one to more easily acxomdate the thickness of a real man….but of course, mostly it serves to keep us in a sissy and submissive state of mind! Great post

  • Slutp

    Ooooh. I know I will LOVE wearing my butt plug for You Mistress Olivia! The only issue I suspect I will have with it is that when You are inside me like that, I doubt I will be able to get any work done… but I have a feeling I won’t care. 😬

    • Olivia

      TODAY TODAY TODAY! Mmmmmmmmm put the internet controlled butt plug in at 10:30 am …. ohhhhhh I’m going to have a good time with you today!

  • Dena

    I want to hear myself squeal like that!

  • TeasedM

    Mistress Olivia,
    Once again, the pictures that You post of Your slutty friend are driving me crazy.
    I would love to have You devise and direct my meeting with Her.
    Looking at Her makes me feel slutty and hungry.

    • Olivia

      ~grins~ How MUCH am I driving you crazy? Hmmmmmmm …. oh yeah she males are HOT!

      • TeasedM

        SO MUCH that I have even been thinking of You directing Your own personal porn movie of me meeting Your friend for the first time and being introduced while I am on my knees.

        Yes, this would be the first for me! You drive me so crazy I would do a great job just to please You.

  • Sounding Boy

    I used to have an inflatable plug that I pumped up once inside to as big as my fist. Then I pulled it out without deflating it. What a stretch. I need to get another one, preferably that vibrates too. The vibrations really help me relax my asshole.

    • Olivia

      I’m doing a blog about the internet controlled long distance sex toys … I would LOVE to control yours while we play! OMG OMG OMG can you even imagine? Think about it.

  • Emily

    I would love to wear it for you mistress

  • yvonne

    Hi Ms

    After reading this blog and thinking about it. This would be something we could do during my time of the month. You could insert a vibrating plug with a remote control. and periodically during my time you could switch it on to keep me flowing and soaking my maxi pad.


  • JohnMistre

    Mistress Olivia, I had a chance to look at your pictuess. I especially love the close of your beautiful lipsticked lips, drives me wild at the thought of doing my lipstick just like yours on that photo. and speaking of butt plugs and dildos. I walked into a store and bought a vibrating dildo and i wore red lipstick. I had to return to the store because i couldnt get it to work. they happily showed me that it actually did work and was I ever humiliated.

  • YES!! There IS sooooo much difference between a butt plug and a dildo…huge! I love the three pack butt plugs to start training . This way all cupcakes can graduate to experienced rump riders in no time. Beautiful Ms Olivia 🙂

    • Olivia

      ~laughs~ the phrase RUMP RIDERS makes me laugh! Oh yes, the 3 pack butt plugs are perfect for the start of any anal training program.

  • Ms. Olivia,

    You’re sissies know what this leads to, right? Give a sissy a butt plug, and she’s going to want a dildo. Give a sissy a dildo and she’s going to want… a big, thick, throbbing cock! as we both know, once you start them down the road to anal pleasure, they won’t be able tog et enough!

    • Olivia

      YESSSSSSSSS …. a little “taste” of pleasure for the anal pussy leads to more and more ass pussy cravings! Mmmmmmmmm … that’s the route to go for any sissy!

  • Ms. Olivia,

    Your sissies know what this is going to lead to, right? Give a sissy a butt plug, and she’s going to want a dildo. Give a sissy a dildo and she’s going to want a big, thick, throbbing cock! As we both know, once you start a sissy down the road to anal pleasuer, she’s just not goign to be able to get enough!

  • Slutp

    Hello Mistress! I soooooo can’t wait to do that again!!!! My little fuckhole needs to be used by You badly on a regular basis and is puckering in anticipation of our next session!!! OMG please fill me up Mistress!!!!

  • Ms.Olivia I have been looking over some of the Butt Plugs in the adult book stores I go to every Friday & Saturday (best & busiest days for sucking cocks there), and I am thinking of purchasing this Anal Butt Plug Trainer Kit, it has 5 different sizes of Butt Plugs, from very narrow, to very wide. Perhaps it be just what You might approve of for my Sissy Anal Butt Plug Training? ~sissy winks~ 😉

    “Butt” (pun intended) I have had me little sissy gurl pussy pounded fast, hard & deep by some fairly good sized cocks in my years of being a little sissy gurl slut! I even have a 10″ X 2″ Vibrator that I can take 9″ deep in my sissy pussy, and work it in and out, over & over, again & again! ~sissy smiles~ 🙂

    • Olivia

      Sounds like you don’t NEED sissy pussy training … why get the anal training kit?

      • Ms.Olivia then at Your recommendation, I’ll not purchase the anal butt plug training kit! Perhaps some dildos might be a wise choice for me to purchase? I do also have the 8″ X 4″ dildo with the suction cup on the end to hold it in place as I sit on it! It’s wonderful to mount on the wall in the shower for a little sissy gurl bath time fun, as well as great for sucking to keep my little sissy gurl cock sucker happy and filled with cock (even if it’s just a dildo) as often as I can!! ~sissy smiles~ 🙂

        • Olivia

          Sounds like your sissy pussy is already trained! ~laughs~ Right?

          • Ms.Olivia Yes Goddess Olivia my little sissy pussy has been very well trained! ~sissy winks~ 😉

            My sissy pussy does get used by a few of the men in the adult book store movies booths. There are the times when I am in same movie booth with him, bent over, sissy panties pulled down by him to my sissy gurl knees! I’ve already fluffed his cock nice and hard, he wants to hear me squeal like the little sissy bitch that he (and You) both know that I am! ~sissy blushes~ 🙁

  • Sounding Boy

    Dear …SissyFaggot:

    Given how well trained your are, it sounds like an inflatable / vibrating butt plug or dildo would be great. You could inflate it as much as you like and pull it out without deflating it to get an awesome stretch.

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