MY SISSY JOURNEY
from Lexie

Dear Auntie Helga,

I hope you are doing well amidst the current pandemic. My name is Lexi or Alexa and I am a sissy. I am writing to you upon my Mistress Victoria's orders. We have been reading the stories on your website for months and are really big fans of your website. She has decided to oversee my writing of this letter detailing how she turned me into the super feminine sissy I am today and also asking your advice for what we should do in the future. We apologize for the length of the story but I included only what Mistress deemed necessary. Mistress has also selected a photo of me from our brief trip to Canada to include in hopes that they will be appropriate for your site and this letter. I spent the entire trip serving as her sissy maid and playing dress up, we barely left the Airbnb.

My petticoating started in high school when I got in trouble for making inappropriate sexual comments to a few girls at school. The principle told my mother and she put a stop to that right away. As soon as I got home that day I found a pile of my sister Nikki's old clothes laid out on my bed. I was ordered to strip down and get changed unless I would rather wear her clothes to school tomorrow. I was told to come down for a family talk as soon as I was changed. I reluctantly stripped down and began putting on her clothes. First a pair of yellow panties and a matching bra. After about twenty minutes of finagling with the bra I slipped on the white summer dress she had laid out for me along with a pair of matching white heels. I was embarrassed wearing such a short dress and high heels but knew I had better get downstairs quickly. I was greeted with an hours-long talk with my mom and sister about respecting women and trying to see things through their eyes instead of my own. At the end of the talk, I was instructed to pose like a sexy model for a few pictures in my new dress as insurance that this behavior would not happen again. And it didn't happen again, I was never caught doing anything deserving of petticoating again throughout the rest of my time in high school but was constantly threatened.

Three years later I was in college and dating a beautiful girl named Victoria. We live on the same floor of the same dorm building so we hung out every day. She naturally took charge in our relationship and especially in bed, at the time it intimidated me but I was too in love and enthralled with the sex to complain. One day my mother decided to randomly send me one of the pictures from my petticoating in high school for "old times' sake." Mistress Victoria saw my phone before I did and began hysterically laughing. When I saw the photo my stomach knotted up, it was me in a white gingham dress holding the hem of the skirt out to the side with my pointer finger and thumb in one hand and blowing a kiss with the other. I had completely forgotten that picture even existed!

After I explained the context of the picture and my one-time punishment to Mistress Victoria she decided that if I wasn't still a sexist I would have no problem dressing up again, otherwise we were done because she wouldn't be with a sexist. Eager to prove I was not a sexist, I put on a pair of her panties and bra quickly and then stepped into her denim mini skirt and white hello kitty tube top. She snapped a few pictures, again saying that if I wasn't a sexist I had nothing to be embarrassed about and that she wouldn't send them to anyone. That night she took charge like never before in the bedroom and I had the best sex of my life. I was told to change into a cute purple nightie afterwards and hop back in to bed with her. I asked what if her roommate came back tonight and she said not to worry that she was staying at her boyfriend's. This started a cycle that went on for a couple of weeks, a cycle of her asking to dress me up and calling me a sexist if I refused. Once I was dressed we would always have the most amazing sex and then I would change into a nightie for cuddling or sleeping over. During our time together, I began to like dressing with Vicky and how she really took charge while I was in girl mode. She eventually set aside a ton of clothes for me in one of her drawers that I would go to immediately upon entering her room.

One day when I got to her room I was surprised to find her talking with her roommate, Miss Cynthia, since she was almost always at her boyfriend's. "Hey baby, I was just telling Cynthia how much you love dressing up in my clothes. We were thinking it would be fun to give you a full body makeover! Won't that be awesome?" I immediately protested and began explaining to Cynthia that I didn't liked dressing like a girl and that I just did it to show Victoria I wasn't a sexist. Victoria cut me off, showing Cynthia a picture of me laying seductively in a sky-blue nightie with a big smile on my face.

"You see Cyn, he loves being a girly girl. Alex, unless you want me to text your mom and send her these pictures to let her know that you've started up your old hobby again, stop being such a b*tch and let us make you over. Would you rather get dressed up for us or your mom and sister? Either way you're putting on a dress, princess." Realizing that seeing me in a dress again and thinking I liked it would make my mom want to put me back in dresses for good, I reluctantly agreed to be made over though I asked Mistress Victoria not to call me princess again. I was then told to go take a shower and shave my body, face, and legs. I didn't have much hair body and barely any on my face but it still felt strange being so smooth all over. When I got out of the shower I dried off and put on the bra and panties they had sent me into the bathroom with. They were both made of a delicate pink lace that felt so feminine hugging my now soft and smooth body. Next I wrapped a towel around my upper body so that it would cover my bra and panties from anyone in the hallway.

When I got to their room the girls rushed me and yanked away my towel, leaving Miss Cynthia squealing and breaking down hysterically laughing. "Oh my god, you look adorable! I never knew a boy could look so cute in panties. You are so lucky to have such a naturally feminine body, you need to show it off more proudly, girl." Mistress jumped in, "Yeah baby show off those girly curves and strike a pose." Used to posing for Mistress alone and beat red from embarrassment, I did my best to mimic what she had showed me in the past. I shifted my weight to one side and put both hands on my hips, shyly looking down at my feet. "Wow you look so good sweetie, but next time don't forget to pout your lips and bat your eyelashes like I showed you. Now sit down at the vanity so we can do your makeup and make you nice and pretty." Each girl took one of my hands and led me to the vanity chair and sat me down. Cynthia showed me how sit with my legs crossed at the thigh and told me to always sit that way or with my knees together when dressed. My shaven legs rubbing against each other was a new sensation that strangely enough was turning me on. I recrossed my legs to make sure my growing member was well hidden in my lacy panties.

It had just dawned on me that with my now hairless body I would also need to cover up my legs on campus. Nothing I could do about that now, I waited patiently for Miss Cynthia to finish up my makeup. Half an hour of powdered foundation, blush, eyeshadow, eyeliner, mascara, lipstick, liner, and lip gloss later I looked like a complete sissy. My short hair and flat chest gave me away as a boy but I had the face of a teenage girl ready for a night out. My pouty pink lips, rosy cheeks, sparkly blue eyes, and long fluttery eyelashes made me look like such a fairy. "All finished, Vicky look how pretty your boyfriend is. you better watch he doesn't find a boyfriend of his own with lips and an ass like that." Mistress Victoria laughed and asked me if I would like that. I frantically argued that I don't like guys at all and that I would only ever be with a girl. "Sure you don't cutie," said Miss Cynthia with a wink and a smile, "now let's get you dressed." Mistress went into her drawers and after a few seconds of rummaging took out a flowy floral mini skirt and matching crop top.

I eagerly turned around and put them on desperate to hide my erection from Miss Cynthia. Unfortunately for me, the skirt barely covered my butt and the crop top left my bellybutton and half of my stomach exposed. Next they helped me slip on a pair of white open-toed heels that had to be strapped on. The girls then told me to pose for some pictures curtseying, blowing kisses, and finally, holding up my skirt to show my panties. I argued against doing the last pose but Mistress asked if I'd prefer to lift my skirts for my mother and Nikki. Knowing I had no other choice, I lifted my little skirt exposing my bulging panties and Miss Cynthia again burst out laughing. "OMG that is so cute. Even hard it's like half the size of Matt's, how do you you ever cum with that little thing?" Mistress Victoria laughed, "Aw stop, Cyn, he's good with his tongue, and besides, I think it's cute." I blushed brightly and hung my head in shame and humiliation looking down at my lifted skirt as they snapped pictures laughingly. I wanted so badly to stop this but was afraid Mistress would keep her promise of telling my mom. After a few more teasing comments from the girls about my small member, Mistress came up behind me and yanked down my panties.

I quickly dropped my skirt and bent down to pick up my panties. I was met with a firm smack on my rear and a stern reprimand from her, which had never happened in front of others before. "What do you think you're doing little miss? Drop your panties and pick up your skirt this instant sissy!" I immediately did as I was told, though I hated that Miss Cynthia was seeing me like this too and getting such a kick out of it. I held my skirt up and waited until Mistress Victoria said to drop it and pick up my panties. She told me to look down at my feet and slipped a beautiful blonde wig over my head. "Grab your keycard, we are going to your room." I immediately refused, stating the obvious that people would see me. "Either a few random people on the floor can see you in your pretty outfit and wig and probably not know who you are, or I can send all these pictures to your mom and your friends. I think Mike and Greg will find you adorable." I again hung my head in defeat realizing I had no other choice.

I waited for the girls to fix my wig and give me a quick spray of fruity perfume, and then we were off. Except for one super giggly girl, there was nobody in the hallway. As I opened my door I prayed my roommate, Mike, wouldn't be there and thankfully he wasn't. Mistress Victoria and Miss Cynthia quickly went through my underwear drawer and began throwing them all in a garbage bag and replacing them with my newly amassed collection of panties and bras. I was then told to drop to my knees and listen. "Look princess," exclaimed Miss Cynthia, "You have been living more like Victoria's sissy these past few weeks than her boyfriend and you seem to like it. Now she's decided that it'll be more official, from now on you will answer to her as Mistress or Mistress Victoria and you will refer to me as Miss Cynthia. You are going to be put in chastity and will only earn release as a reward for good behavior. You will also wear your panties and bra underneath your clothes every day and as soon as you are done you are to report immediately to our room and change into your girly clothes. Do you understand sissy?"

Ignoring Miss Cynthia, I sprung up towards Mistress Victoria and started begging her to reconsider. She grabbed me, bent me over my bed, lifted my skirt, and began spanking my rear again as she once more reprimanded me. "You are going to be a good little girl and listen to us otherwise you will be punished severely. From now you answer to Lexi, Alexa, or just sissy. You are not a man anymore and you must learn to accept that or things are going to get very difficult for you little girl. Now, unless you want everyone to know what a little fairy you are, I suggest you do exactly as we say." As my spanking came to an end I found myself fighting back tears of intense fear and humiliation. After my spanking, I dropped back to my knees and apologized to Miss Cynthia for my rude behavior. Since that day, my life has been completely changed.

I now wear a pair of panties and a bra everywhere and shave and moisturize every day. I also now use feminine toiletry products and perfume exclusively. I have been taught to speak, move, and act like a sissy at all times as well as apply makeup which Mistress Victoria still coaches me on every day. I spend most of my time with my Mistress Victoria and Miss Cynthia now, sometimes dressed like a girl, sometimes like a sissy, and occasionally serving them and their friends as their maid. The only time I am allowed to wear boys' clothes is for class. As instructed, I have spent almost all of my money on makeup, toys, and pretty clothes for my training. I am kept in chastity 24/7 but am usually given a weekly or bi-monthly release in front of Mistress Victoria and Miss Cynthia, depending on my obedience and feminine behavior. Also, Mistress Victoria and I have not had sex in a little over three months which brings me to our first question. Mistress Victoria says that she needs a real man to please her which I do not think is fair since I am still technically a guy. I keep trying to tell her that if she lets me out of chastity I could please her again but she's doubtful now that I'm so feminine. She has already started talking and flirting with other guys but has not been on any dates yet. This makes me feel super insecure and like I can't compete with those guys.

Mistress Victoria wanted me to ask you what we should do about this. She says unless you give us a good reason not to she will soon be dating and sleeping with other guys. Another thing she wanted to ask you about is how far to go with my exposure. Mistress has already decided that I will return home next break in a dress and makeup to greet my family but is still deciding what to do about my friends. She thinks its in my best interest to out me as a sissy to them. I have repeatedly begged her not to this but she says that emasculation and humiliation are important parts of being a sissy. Her plan is to find me a really pretty formal party gown and have a coming out party for me at our dorm and invite all of our friends to meet the new me. Again, she has demanded that I ask your advice on this matter. She has told me that unless you say otherwise she will proceed with her plans to out me to my friends.

Auntie Helga, please tell her not to do this. My friends will lose all respect for me and will never think of me as a man again. Mistress has also decided that in order to dissolve what remains of my fragile male ego, I will start going on dates with boys so I can see what a sissy I am compared to them and learn what it's like to be with a real man. Miss Cynthia says that a sissy like me needs male attention, but I respectfully disagree, I have never liked boys at all! Please help me Auntie Helga, I have already resigned myself to being a prissy sissy for Mistress Victoria and even my family, but I can't imagine how humiliating it would be dressed girly around boys, especially my old friends. I also really don't want Mistress Victoria to be with other men, I love her and it'd hurt me and what's left of my fragile ego so badly to see her with another man especially since she hasn't slept with me in months. She thinks that you will agree a sissy like me needs to be exposed and needs boys in her life. She is also certain you will agree she deserves a "real man" in her life.

Please help, Auntie Helga, I really hope you agree with me.


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Lexi


Thank you for your letter Lexi. What a wonderful start with your loving mother and thoughtful sister to bring out the sissy in you, and then your special Mistress Victoria to help you with your training. I would answer that since she is in charge of your relationship its her choice to fine a masculine provider for her natural needs, that said, while exposure to family is an obvious choice, to strangers and your previous male friends seems a bit over the top right now, take that slow.

Auntie Helga

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Letter 10