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.