Adventures at the LiLy Academy

Sissy Life 101 (Open to All, pls PM first)

This topic contains 33 replies, has 5 voices, and was last updated by  slave stacey 2 months, 2 weeks ago.

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    I enter a fairly large classroom. I have my notebooks and pen in hand. Inside my purse is a note that says “Ask for Miss Akan.”
    I close the door behind me and there are a couple of students my age in the room.

     (R)Owen(a) Hero 

    It tried to ignore what Miss Akane was saying… I already knew I wouldn’t like it. But just after Hatsue pull out she must have realised I wasn’t listening because all of a sudden she smacked me 3 times on the bottom… then stuck her finger inside me.

    “Ah,” I gasped at this one.

    Do you think my finger is better than tongue of this sissy? Do your pussy wants Mr.Hanson’s cock in? No Nick anymore… Mr. Hanson… a sissy always addresss her Master as Mr. or Sir, no lick name. REMBMBER THAT

    She wriggled her finger inside me with a level of expertise that rivaled the chastity belt rear module… why had I let myself go without it today… I knew the offer had to be a trap.

    O! Tina, your facial expression tells Us you are frustrated. Why?Tell the class why you feel frustration. No lies or your SissyLink will give you a good lesson.

    “I’m frustrated because I can’t stop it and it won’t end,” It came out as something of a whine.

    Dealing with this woman actually brought a twisted thought to mind… during my educational dry spell before coming here I had tried to teach myself a few new skills, like 3D modelling… sewing and Japanese… I admittedly didn’t learn much on the first of those, the second I did well, but I’d had mixed success with the third.

    One thing that was coming to mind though was that I never learned the word for stop, there were plenty of words I didn’t know, SO many in fact, but right now I just wished before coming here that I had learned how to stop… of end… or finish or enough… maybe if I could use one now the teacher might respect that I’d learned it and actually back off… Of all the things to get stuck in my mind now was the lack of knowing the Japanese word for stop… still it was better than thinking about Nick. Fuck Nick… and now that was in my head, except I was the one getting fucked… Great, I had to ruin the magic mental distraction.


    A dildo lands on the floor in front of me and I look around the classroom. Every head is turned towards me. In some look at me with anticipation, others with pity. I feel a shock from my belt, and Miss Akane says some bullshit line about being lazy. I do my best to ignore it but still grit my teeth in anger. I know better than to say anything, so I pick up the dildo and bring it to my mouth.

    Before I can start however, I feel another jolt and drop the dildo to the floor again. Without a word, Miss Akane pulls two lengths of black coreless rope from her desk, and walks behind me. she pulls my arms behind my back and ties my wrists tightly together. The second length of rope is used to tie my elbows together, bringing them close together in a very uncomfortable way. The secondary effect of this bondage is that it pulls my shoulders back, and forces me to stick out my already ample breasts. At least Miss Akane has the decency to set the dildo upright as she walks away so that it isn’t laying on the ground.

    I approach the dildo as best as I can while on my knees and with my arms behind my back, and start to lower myself toward it. I’m nearly at it when I feel myself starting to lose balance. These fucking tits are shifting my center of weight forward and I realize that this task is going to be much worse than originally thought. I catch myself just before I fall flat on my face and shoot an angry glare at Miss Akane. The bitch must have known this was going to happen.

    I take a deep breath and lower myself back toward the dildo. This time when I feel my balance shifting too far forward, I open my mouth as wide as I can and let gravity do the rest. I fall and the dildo slides into my mouth, all the way to the back of my throat. I gag and splutter for a minute as I attempt to stabilize myself, and eventually find a way to use the dildo to push myself up from the ground. I don’t go up too far though, and quickly fall back with the dildo in my throat again.

    This process continues for several minutes. I push myself up, away from the dildo, only for my own weight to force the thing back, deeper than before. The only saving grace of this whole situation is that while I’m bent over so far, my long hair cascades around my face, obscuring it from view, at least no one will see this awful display.

    After several painstaking minutes bobbing up and down on the shaft, I feel an eruption of fluid in the back of my throat. At this point, the head is so deep in my mouth that most of the fluid is forced down my throat and I have no choice but to swallow it. The remainder of the cum dribbles out of the corners of my mouth as I sit up fully again, leaving the dildo on the ground, and take several large gasping breaths. I close my eyes in relief as I can finally breath normally again, without a giant obstruction in the way.

    I look up to Miss Akane and say “I’m finished” then, remembering the last of my task, I grit my teeth to brace myself as I continue, “It felt so good to have that dildo in my throat, and its cum was just so yummy. I feel like such a lucky sissy for getting to demonstrate to the class. Thank you.

     slave stacey 

    I think Miss Akane has forgotten me, as I seem to have been so long kneeling here in the corner of the room. I am drooling from the time Tina’s panties have been in my mouth and wish I could return to the class…

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