An Education for Wayward Sissies – Contributing Author Jennifer Duchowy

I agreed nervously to meet with Anya after several email exchanges and phone conversations.

After arriving, I was instructed to go to the bathroom and get ready. To my surprise there was a school girl outfit which included a plaid mini skirt, white collared button down short sleeve shirt, white leather wrist length gloves, a black women’s cross over tie and black mary jane shoes. The lingerie included a silky white bra that had holes in the nipple areas, matching full cut panties, garter belt and white stockings. I noticed that there was a box with a note on it that read OPEN ME LAST. I got dressed then opened the box. In the box there were two small pad locks and a few pieces of bra straps with a two notes as well as a pink chastity device. Opening the first note, there was this picture… with the message LOCK INTO BRA AS SHOWN THEN LOCK INTO CHASTITY. BRING OTHER NOTE WITH YOU – SISTER ANYA, HEADMISTRESS. I did as instructed and looked at the other note in the box. The note was folded in half and handwritten. The outside had a large heart drawn on it with FOR YOUR EYES ONLY written inside it. Opening the note it read HEY SEXY! WANNA GET TOGETHER LATER GET DRUNK AND SEE WHAT HAPPENS?? XOXO SISSY JANE. I shrugged and made my way out to the room. There was a large desk with a wooden chair just in front of it.

Sister Anya was sitting impatiently waiting for me. She was dressed in a normal nuns outfit. “It is about time you got here to my office!” she said. “Yes sister Anya” I said. “That’s Headmistress Anya! Remain standing!” “Yes Headmistress Anya”. She stood up and approached me and held out her hand. “Let me see that nasty note!” “Yes Headmistress Anya” I said. She took the note from me and opened it up. A look of disgust flashed across her face. “You know the penalty for passing notes in class is severe”. “Yes Headmistress Anya” I replied with a smirk. “Wash that smile off your face!” Anya shouted. I immediately stopped smiling and concentrated on a neutral facial expression. “What am I to do with you? Passing notes is one thing but alcohol is strictly forbidden in my school!” I bowed my head shamefully. “Sit down!” said Anya. I quickly sat down in the chair legs straight out. Anya grabbed a ruler off her desk and smacked my left thigh “You will sit cross legged as a proper lady as you have been taught”. I flinched from the pain then crossed my legs as instructed. “Stand up and bend over my desk to receive your punishment” Anya sternly instructed. I stood up and bent over the front of the desk. Anya pulled up the back of my skirt and placed her free hand on my pantie covered left cheek, gently caressing it. “A shame, such a nice little ass you have. But I must have discipline in my school!” She removed her hand then smacked me on the left cheek with the ruler. I flinched from the pain. She smacked me again for total of five times. She then switched to my right cheek. I flinched on each hit, secretly loving the growing heat I could feel from my punishment. My sissy cock was growing harder each smack. As it swelled it filled the chastity device and felt uncomfortable. I could feel the precum starting to form and start flowing from my tip. Anya paused and pulled my panties back. “Not red enough yet.” She continued until she seemed satisfied with her handiwork. “Stand up straight!” Anya said. “Let me get a look at you, turn toward me”. I turned toward Anya fully knowing my panties were wet with cum. I was embarrassed and felt my face get flush as I turned toward her and clasped my gloved hands behind my back. Anya lifted up my skirt and again looked disgusted. “Look at you!” Anya said. “You have soiled your panties!” She gently poked at my panty covered caged sissy cock with the ruler. “I see my punishment has had a different effect on you. Since you seem so excited to be a student in my sissy finishing school, I am forced to speed up your training. Sit down and stay still!” “Yes headmistress Anya” I replied and sat down and quickly crossed my legs wanting to be a good pupil. Anya put the ruler down on the desk then slid behind a folding partition so I could not see her. I heard sounds of clothes sliding off then the sound of snapping and cracking like bubble wrap. When she emerged she was dressed head to toe in latex rubber. My eyes traced the heavenly visage of the full latex nun headmistress from toe to head. She wore spike heeled thigh high boots that opened to smooth sexy thighs. I knew she meant business when my eyes stopped a second at the sight of a strap on cock then up her corseted waist and perfectly rounded shiny latex covered protruding breasts. She wore a latex cape attached at her neck, around which also was a spiked collar. I ended my scan with her tightly covered shiny face. Her eyes seemed darker and lips redder. On her head she wore a latex nun habit. My eyes had opened wide and my heart started to race in awe of the sight I now beheld. Anya was a now a latex nun headmistress. I started to wonder if she was really a she-devil in disguise. I caught a glimpse of a sly smirk as she said “You did not think you were going to get off that easy did you?” as I again nervously eyed her protruding cock. She smiled and grabbed a bag from behind the partition and laid it on the desk. She extracted a pair of size 10 black ballet boots. “Put these on” she said. She sat on the corner of the desk and impatiently waited. I sat down on the chair, took off my shoes and slipped on each boot one at a time. I then laced each boot up tightly. Anya smiled evilly and then grabbed a few things from her bag. She had a black latex mask and some other pink mask with raised bumps on it. “This is a Japanese Kaomomi beauty mask” she said as she smiled wryly.… “It will help make your face more feminine”. She then walked behind me and said “Sit up straight and don’t move!”. I did as she asked and she attached the mask to my face. It was cool to my skin and felt rubbery and tight . Kind of felt like the opposite of an octopus had grabbed hold of my face and instead of sucking was pushing against it. She tightened the straps then slid the latex mask over top and zipped the back closed. I felt like a rubber mummy but the feeling was oddly exhilarating. The smell of the rubber latex was wonderful. Anya slid back in front of me and put her latex gloved hands into the bag. Out she pulled a penis gag that had a long tube attached to the front. “Since my gurls should be seen and not heard” she giggled as she moved behind me. “Open wide!” she said. I complied obediently. In slid the penis gag. It was so big I almost gagged. “You had best get used to having a cock in your mouth my dear, after all you are a gurl in training!” Anya exclaimed. She tightened the strap and then moved back in front of me. “I bet you are wondering what the tube is for?” she cooed. I nodded unable to mutter hardly a word. Her gloved hand darted inside the bag once again and produced a slim silver tube. “You are a very lucky gurl. I have been practicing with this urethral sound and am able to quickly bring myself to a squirting climax. I am am going to attach that tube of yours to the top and if you are lucky, you may be the first of my students to taste your headmistress!” Anya sat spread eagle on the desk in front of me. She moved her large cock to the side and lubed the sound then her already wet pussy. She inserted the sound with a cooing noise then started her dark ritual. As she stroked the sound in and out she rubbed her taught latex covered breasts and then her pussy with her free hand. “Mmmm, yes!” she exclaimed as she picked up the pace. “Ummmm, oh yes! Ahhhh!” she said as she was clearly approaching climax. “YES! YES! OH FUCK!” she exclaimed as brought herself to an amazing climax. I felt my sissy cock bulging in its cage yearning to be freed. Cum was dripping out soiling my panties even more. “Ooooooo!” Anya yelled and she thrust her hips as she rapidly slid the sound in and out. “OH SHIT I’M CUMMING TASTE MY JUICES YOU BITCH! she yelled. Then I tasted it. It tasted like nothing I have ever had before. There was a sudden rush of liquid into the back of my mouth. It was a bit sweet and viscous but watery. I had to concentrate on swallowing to avoid choking. “Mmmm, yes! That’s it my dear. Swallow your headmistresses juices!

No better time like NOW!

Anya said. Anya recovered quickly from her orgasm and detached the sound. Little did I know what was about to happen next. She placed the sound on a towel and ordered me to stand. She started unbuttoning my shirt and opened it to expose the bra with my bare nipples down inside the bra holes. She then walked around the partition and grabbed what looked like a book bag. She again flasheed an evil smile as she put the bag down on the desk and opened the zipper. She took out two clear plastic funnel looking objects. She lubed the inside and the marched out in front of me. With a big smile she said “Your little titties need training too. This is part of a breast pump. We are going to sensitize and enlarge those sissy titties of yours.” She slid the cups inside the bra poking the tops out the bra holes. The cups were cool and hard. She made sure the bra was extra tight to hold the seal. Next she grabbed another sound out of the bag. This one has small ribs along the length of the hollow tube. Now I got very nervous. Anya then said “You did not think that gurls only get to taste real women did you? I’m going to put this sound in your sissy cock and attach it to the tube while we pump your breasts and I fuck you in your sissy pussy.” Anya grabbed a small key out of her bag then squat down and unlocked my chastity device. It felt wonderful to finally be free but I quickly cut my enthusiasm short as I knew what was coming next. She lubed the sound and gently pushed it into my shaft. It felt uncomfortable at first but I noticed I was quickly getting rock hard again. “Good” Anya said as she attached the tube to the top of the sound. She now attached the breast cups to the breast pump and turned it on the maximum. I instantly felt a pulling sensation on my nipples. It hurt a bit at first but again I quickly got used to the relentless pulling of my nipples and it aroused me even more. Next she lubed her cock and moved around back of me. “Bend over dear” she said, Get ready to lose your sissy pussy virginity!” She pulled my panties down and inserted the cock in my tight ass. As the shaft penetrated and slid into my cavity I uttered a muffled moan under the fullness of the penis gag. Anya began to thrust in and said “This pussy is mine! I am your headmistress and you worship only me!” My mind was swimming in thoughts of pain and pleasure. I could not respond. I was beginning to become lost in the moment but I could feel a climax surging in my groin. Eventually I exploded into the sound with a good measure of measure of pain but pleasure mixed between. My body shuddered and I felt a gentle squirt of a salty liquid splash inside my mouth. I was tasting my full load of cum! I again struggled to swallow to avoid gagging. Anya let up her pumping and pulled out. “Now lets get you cleaned up. You have been a good gurl and taken your punishment in stride. You will be rewarded in the future and I will recommend you fully to your teacher for further training!”