Introducing Ms. Peggy

In July 2012, I introduced my boyfriend Mr. Cock to this blog. Now, exactly four years later, it's time to introduce my new girlfriend - Ms. Peggy.

It all started last year with Mistress Lascivia's encouragement to poke a finger up my butt. I tried poking my finger up my hole in the shower a few times, but never got more than the tip in. I couldn't get over feeling dirty down there. One day I thought it might be easier to get over the dirty feeling if instead of my finger I used something else. I searched online and picked out a small pink butt plug.

After I got the plug, I opened the package and was surprised by its size. Even though it was the smallest plug I could find, it was bigger than my finger. A little nervous but excited, I read online the instructions on inserting the butt plug. I spread a towel in the bathroom, lubed the plug and got ready. I got down on all fours, put my face down to the floor, ass all the way up and gently poked the plug in. My butt shut tight and didn't budge beyond an inch. After struggling for more than a few minutes, I gave up.

After resting for a few minutes, I decided to give it another shot. This time, I lay down on my back, bent my knees and lifted my legs up and wide. I couldn't help but notice how obscene my pose was and a sense of utter shame washed through me. That made my peanut get excited and drip precum. I once again lubed the plug, lubed my hole and started again. Slowly but steadily, I pushed the plug in, pausing frequently. Finally, after struggling for close to 30 minutes, I sensed my butt pulling the plug in as soon as I got the widest part in. And just like that I had lost my anal virginity to a toy. As the plug sat tight, I felt full and a little stretched. I felt proud that I persisted and didn't give up. With my legs still up, I noticed that my raisins had shrunk and my little nub was all shriveled. As excited as I was, my peanut was utterly limp, lifeless and useless. It looked absolutely ridiculous.

I spent the next hour plugged. I wore my heels and pranced around. I setup my camera and took some pictures. I diddled my little weewee and made some silly little squirties.







After squirting, I wanted to get the plug out. As I tried to pull it out, my greedy little butt didn't budge. It was holding on to the plug tightly and didn't let go. Having made squirties, I didn't want the plug in. I wanted it out immediately. The harder I pulled though, the tighter my butt held on. I started panicking and wondering if I had to get help. I thought about getting to the ER with the plug lodged in my butt and worried about being exposed as a sissy bitch to everyone. Fortunately, after multiple tries, I managed to calm myself down and slowly pulled the plug out. 

After getting it out, a sense of relief and an overwhelming sense of shame took over. I cried for being such a sissy faggot and in that moment of utter shame decided to throw all my sissy stuff away. I dumped all my sissy clothes and shoes in trash. I gathered Mr. Cock and the butt plug and threw them away. I gathered my hair removal items and trashed them away as well. After clearing away all my sissy possessions, I drove down to Target and bought some boxers. I shut the blog down and vowed that I'll never be a sissy again.

That didn't last long though. A few miserable months later, I went back and bought some panties. I also bought a new Mr. Cock. Even after reverting back to my sissy ways, I thought I would just keep my sissy life secret and not revive the blog. But, Mistress Lascivia has made me realize that no matter how shy and ashamed I might feel, I need to continue posting and sharing my humiliating sissy lifestyle with the world. Following her instructions, I just got a new pink butt plug. She's my girlfriend and Mistress Lascivia has named her Ms. Peggy. 





Comments

  1. omg i felt the same way the first time i penetrated myself, but it also felt so so good and so right. i dribbled out my cum and never even got close to hard before i creamed myself.

    ReplyDelete
  2. Good girl sissyjoy -- finally you've done something to earn a tender pat on the butt rather than a hard, stinging smack on the ass! ;)

    I'm very pleased with how thoroughly obedient you were with this post. You did exactly what I told you to do in my email. Maybe you really have finally learned your place once and for all.

    From now on all of your posts should be this fulsome and thoughtful. No more lame stacks of pictures with no personal notes about how you felt while you were taking them and what fantasies they provoked. Do you understand me, sissyjoy?

    Now, I must say that the last picture you posted (before the portrait of the lovely Ms. Peggy) is the ideal self-image for you now -- naked and hairless, down on your hands and knees with your sissy ass up in the air, your high-heeled feet up, toes pointed like a little ballerina, and a pink buttplug shoved up your boipussy filling you up like you could never fill a woman. That is you now, sissyjoy, understand? You're not a virgin anymore, there's no going back, and there's no more pretending you can.

    You're a sissy faggot now and your new girlfriend is going to fuck you ALL THE TIME. When you come home, she goes in. You'll strip naked, lube up and slide her in -- in and out, in and out -- while you diddle yourself to the edge -- the EDGE. Then hands off! and you go about your normal business, prancing about, dancing like a stripper, sashaying around while you feel Ms. Peggy inside your boipussy, filling you up. She only comes out when you leave the house, or for obvious reasons. And you have to have her fuck you -- in and out, in and out -- whenever you take her in OR out.

    You're a fuckable little sissy faggot now, sissyjoy. You have to loosen that boipussy up. ;)

    Do you understand me, you little slut?

    ReplyDelete
    Replies
    1. Yes Mistress, I'll try to be a good little sissy faggot Mistress.

      Delete
  3. amore sei bellissima docile e sexy anche senza lingerie sei una gran bella figa curatissima...sei una piccola trav dalla pelle meravigliosa e liscia...adorabile col tuo plug rosa ti dona moltissimo...d'altronde è il colore delle femminucce...!! sei molto ben fatta e il tuo piccolo peperoncino è magnifico così moscio da angioletto...!!! baci baci baci

    ReplyDelete
  4. And by the way, sissyjoy, you should know that you're on bare-ass probation until you restock your sissy supplies.

    Your panties are only for when you go out of the house, to wear under your boy-costume to remind you that you're a sissy even when you're trying to pretend that you're not. You have to go completely naked at home until you get some acceptable sissy gear to wear.

    Your first priority has to be new sissy shoes -- VERY heels -- heels so high it will be a challenge for you learn to walk in them. But you won't just learn to walk in them, sissyjoy. You will learn to strut, sashay, prance, dance and mince in them with daily practice -- because you will be wearing them AT ALL TIMES when you're home. Do you understand me, my little sissy?

    Next you need to stock up on slutwear: thigh-high stockings -- fishhets, in lots of bright, sassy colors; and sissy lingerie -- babydoll nighties, teddies, corsets. And you have to model each piece for us on your blog, including full explanations of what you like about each item and how it makes you feel to wear it.

    Only then can you start wearing any clothes at all when you're home. Do you understand me, sissyjoy?

    (And fyi, it's not a rhetorical question, you peanut-pricked slut! When I give you an instruction and ask if you understand, I expect a swift and affirmative answer!)

    Mme. Lascivia

    ReplyDelete
    Replies
    1. Yes Mistress, I understand. I took all my clothes off and went butt naked as soon as I saw your comment Mistress. I look so silly with my peanut sticking out. I've closed all my windows and now I am going to finish the rest of my chores around the apt - laundry and ironing, cooking and cleaning - all naked.

      The first sissy items I've ordered online are high heels and sissy ribbon Mistress. They'll be getting here sometime next week. I can't wait to prance around in high heels. Until then, I'll remain bare-assed as you've ordered Mistress.

      Delete
  5. Good girl, sissyjoy. I can't wait to see you in them -- and to see what you say about how feminine and slutty they make you feel. ;)

    Mme.L

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  6. Hi Sissyjoy. I have to say that I felt the same way many times throwing away perfectly good sissy clothing and toys. Than my mistress wife helped me find my way to being not only a good gurl but happy satisfied gurl. Once she had me satisfy a real man's cock and I heard his appreciative words I knew I found my way to a sissy lifestyle that I would finally enjoy. Love you and your shoes.

    ReplyDelete

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