Category Archives: Sissy Stories

Exposing Sissy Tara

You may find that woman stunningly attractive. But you aren’t having images of wooing her. Are you? You aren’t picturing being that perfect man in her life. You would much rather walk up to her and strike up a conversation hoping that she notices your fresh set of nails you just had done earlier. You want her to ask you about your nails, ask you about the attire that you have on – did you get a new dress? Who did your hair today? That is a fantastic pair of shoes!

You want to have girlie girl conversations while looking and feeling like a girlie girl. You want to BE one of the girls.

This high that you get from wearing and looking like the perfect sissy – needs to be…permanent. That feeling that you get when women are asking about your mannerisms and about your clothing choices and about your overall sissy style, look and feel – needs to stay. Not just a ‘boring Friday night’ kind of feeling.

For Sissy Tara of Chicago, she is the epitome of what a sissy should be. Look at her poise, look at her grace. She takes time and actually walks the walk. She does live a double life. Wearing panties and thongs under her ‘man clothes’ during the work day and donning lipstick and playing with dildos at night.

On special occasions, she will get herself dolled up and go get profession photos done of herself. Living life as a sissy. Out in the open. Knowing that those pictures may not always stay a secret. Honestly, why keep them a secret? Sissy Tara is FANTASTIC and NEEDS THE SPOTLIGHT. She needs to put on her highest heels and scream from the roof tops that she is a fabulous sissy and loves

being a sissy.

You can tell in the photos how fantastic she feels. She really…opened her self up…in a few of them as she bounced up and down on a bright red dildo.

Sissy Tara is probably one of the most genuine sissies that I have had the pleasure of speaking with, and now the pleasure is all mine to shine that spotlight on her and give her the exposure she so rightfully deserves.

She is around twitter, I know I’ve seen and retweeted her pictures in the past. If you see her pop up, retweet it. Show her off and expose her. There will be no hiding in the shadows, not any more and certainly not for this sexy and fun little sissy.

Show yourself Tara, be a loud and proud sissy!

Season of the Sissy

Spring is in full swing and before we know it…it will be summer! I always say that the summer is the season of the sissy.

Summer time is when you get to see the tiny little shorts, the pretty sun dresses, the sexy little bikinis. There is such a variety for sissies and fembois to look at during the summer that they feel a surge of the urge. The inner sissy becomes overbearing and you will feel that all too familiar sense of femininity.

What would you give to sit poolside in a slinky little bikini sipping on long island ice teas just sprawling out in the sun while real men gather around you for some…extra fun in the sun…and defining Sex on the Beach.

You can feel the urge, and now it is time to feed the need. Giving in is the only way to calm it. Although, it is a double-edged sword. Feeding the need grows it…but ignoring it makes it stronger as well. Best to feel some relief while you grow the urge to be feminized and sissified. Your Sissy Trainer Mistress will help urge you…FORCE FEMINIZE you if necessary. It is absolutely what is best for you.

Why not go and get that mani/pedi, go paint your nails and shave your legs. Go prep yourself for the most fem-chic season of the year.

Have you been feeling a little extra feminine lately? Have you bought a new shade of lipstick or a new outfit? Show it off below and I’ll be sure to tweet it out!

  • Post your picture in the comments below and tell me how much you love the season of the sissy. Include your twitter tag where available, and if you added to your collection or pulled out an old favorite let me know 😉
  • *Must include a sign that clearly states Summer Sissy fun @Mistresslillith .  Without the sign your post will not be acknowledged. A face picture is great but not necessary 😉 *
  • Don’t send me a link to a website with a slew of pictures. Only new/current ones that follow the rules above. Deadline is the end of the summer season 😉

This Sissy LOVES Red Lipstick

How many of you sissies enjoy slathering on that smooth, creamy, lipstick. For some of you that is your absolute FAVORITE part of getting all femmed up.

For my sissy, Jessica Michaels, red lipstick is her absolute favorite.

While so many girls and sissy girls clamor over the 50 shades of grey…THIS sissy falls over 50 shades of RED. This is what she had to say about her red lipstick:
red lipstickI really love putting on and wearing women’s lipstick. It feels so smooth and sexy on my lips. The way is glides across them creating a slippery, shiny coating. It can never be a light shade, it always has to be a dark slutty color. The kind that stains my lips when I’m wearing it so I might not be able to hide it the next day.

It makes me feel sexy and at the same time, completely humiliated.

To be a man wearing tons of bright red lipstick is embarrassing and exhilarating. But the feeling of it on my lips, the smell, the taste. Makes my heart pound in my chest.
photo (9)The latest one, a color called “Tempt” is long-lasting, but also has some lip plumper in it. It makes my lips tingle as they become more pouty and the color sets into my skin.
Mistress Lillith loves making me put on tons and tons of it, making me ask repeatedly for more and more until I can not take it anymore. Then she makes me add more still.
I love that she is turning me into a helpless sissy lipstick addict for her amusement. I can’t resist the feeling when she tells me to “put on LOTS more”.
I fear my future as a lipstick slut, but I also can’t help but love the idea of having constantly red and shiny lips for everyone to see what a naughty little lipstick slut I have become for Mistress Lillith.

So now I ask all of you sissies…what color lipstick is YOUR favorite? What is your favorite part of dressing up?

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Justen — Sissy and Tranny Fantasies

Affirmations are something that EVERY sissy should do. When I start my 12 step sissy school camp, they ALL start off with affirmations, but each one has a different SET of affirmations tailored to every sissy’s need. I have said this numerous times but I don’t believe in fitting anyone into a box. Perhaps you are a sissy slut that loves the frills and lace, or maybe you are just a man that enjoys wearing women’s panties but don’t refer to yourself as a sissy. While there may be CATEGORIES you fit into, you won’t fit in PERFECTLY because you have your own individual set of needs, wants and desires…THAT is what makes you perfect, not the box.

I have been enjoying the torment that Sissy Justen has been enduring as of late. Here are her latest sissy diary submissions:

7/15 I did my affirmations this morning when I woke up, when I closed my eyes I saw me putting on girlie clothes in front of a mirror. There were a few girls there, and they were helping me. Today I had a salad for lunch which I was good, there wasn’t anything special about it though. Honestly I was thinking if I was cool with people not knowing this side of me, and I found out that I am, the only person I’m cool with sharing this side of me is my partner whoever they may be a mistress or a girlfriend or wife, doesn’t matter who they just need to be able to accept me for me :)!

Mistress Commentary: It is always wonderful to have that person you can truely, honestly connect with. Be it a mistress, friend, or significant other. I also wanted to add, that perhaps this vision of putting on your finest sissy maids uniform or sexy negligee could in fact come true! I could find another sissy training mistress to watch you, perhaps for your graduation? 

7/16 Today I did my affirmations while my eyes were closed I saw myself as a maid servicing woman and trannies which turned me on a little ;).

I edge after that and didn’t cum. When I finished I took my shower and today I felt like I smelt really good. I went to school then went to a friend’s house and listened to her as she talked about her boyfriend and how he was coming back this week. I don’t like her boyfriend he is a dick but she likes him so I just listen. When I got back I was in the basement with my family watching a t.v. Show and I saw this woman, she looked so hot I wish I looked like her and had a girlfriend, mistress or whoever like her she was amazing :0.

Mistress Commentary: Ahhh A bit of a Tranny Fantasy Huh? We will be having some fun with this one. Nothing more exciting than being able to be with an Exotic woman. A girl with…Something EXTRA. 😉

7/17 today when I got up I saw that my parents were not home so I gathered a pair of panties a garter belt and stockings and went to the bath room. I shaved my legs half way before I took a shower. I hate shaving I am always worried I’m going to cut myself :(. After the shower I put on my panties and other stuff and walked into my room and started doing my homework. After a couple hours my parents came home and I put on some pants over my girl clothing. They left so I took off my pants then I did my sissy affirmations and saw myself as a sissy school girl with long black hair the outfit I saw myself wearing was hot!! I went downstairs after my affirmations and watched a little t.v, after that went up stairs and read a book. Today was a good day, kinda boring but I needed to stay home.

Mistress Commentary: Shaving is a hassle for boys and girls. Mistresses and Sissies. I am somewhat of a masochistic myself and LOVE getting them wax. One day I will go and get the laser hair removal on my legs but we’ll see. As far as nicking yourself…It will happen. It seems to happen LESS with me when I shave using hair conditioner or lotion and then right after putting baby oil on my legs. (there is a nice little sissy shaving tip for you all to enjoy)

7/18 this morning I took a nice long bath, it felt so good. I had my laptop in and had the mp3 for the affirmations and listened to it a couple times. I really enjoy listening to it.

While I listened I saw myself sucking a girls cock while other girls watched, I was wearing nothing but a bra and panties.

It made me get horny so I edged after the bath. After I edged I did a little yoga in my panties the put on pants and helped my parents move furniture so my mom can paint. I went out after and saw skyfall which was boring. I went home and them played a couple video games with my friend and talked to my other friend who went to basic training. Then I went to bed… I have school tomorrow 🙁 I wish I had it off!!

Mistress Commentary: To bad you cant compare notes…His Basic Training to your Sissy Training I bet they can be equally intense physically and mentally. 😉

That was the weekend of Justen and Next week I’ll post her next sissy diary submissions. She seems to be enjoying the training and slowly but surely seeping into this new lifestyle and way of life.

There still is the issue of NAMING my sissy~ I think we have narrowed it down, and the naming ceremony will commence very soon! 🙂

Justen — Sexual Frustration is Rising

Here are more of Justen’s Thoughts as he continues his 12 week sissy training process. How do you think he is faring? Feel free to comment below with suggestions, comments and/or questions:

7/13 Today I didn’t have to go to any classes so I stayed home for awhile and took a long bath.i love taking baths the heat feels so good, I love closing my eyes. After I did the affirmations I closed my eyes and saw myself next to a blonde girl we were cuddled in the bed both wearing corsets and stockings she had her arms wrapped around me. When I got out of the bath I put on some pink panties with hearts and walked around since I was home alone.

I felt pretty horny so I tried orgasm edging…then got worried that I was going to cum so I stopped.

I left the house wearing the panties and did a couple things, and went to my school. When I got back home I said hi to my parents and went to my room and did a little homework and then edged again. I feel so horny all the time! It sucks 🙁 I want some release please, pretty please!?

7/14 OMG  today felt so good outside!! Today I went to school and sat through my boring classes :(.

When I got home I did my affirmations, while my eyes were closed I saw myself wearing guy clothes but under it I had on panties, a garter belt and stockings.

I was walking arm and arm with a girl. I had a butt plug in my butt, and the girl knew that I had the plug in. when she knew that there wasn’t anyone was looking would rub against my but reminding me that it was there. I think the easiest habit or thing I can do is take a shower using feminine soaps and stuff since I take a shower every day, and now I’m using feminine soaps. I also tried doing some yoga again :)… But I’m not flexible yet so it’s all really hard to do :(.

I haven’t came yet, this whole edging is hard by the way.

I am really looking forward with the buying girls stuff, I don’t know what items I should buy which is what I need help doing or like a list of stuff I need.

Justen- Forming Ritualistic Female Habits

My Sissy Justen is in his 2nd almost 3rd week of Mistress Lillith’s 12 step sissy training program. He seems to be progressing along nicely.

During his first week, he had affirmations to repeat daily. Words are very powerful and the more he recites his personal affirmations, the more he believes them and gets into that sissy subspace of a mind.

This week he is prepping the feminized body in a few different fashions as well as setting up some ritualized feminine routine.

As girls we do have daily routines that we do to keep our selves chic, sleek, and sexy.

Part of his requirement is to write regularly in a diary and have it submitted here for all to read, and so HE can keep track of his progress.

Here is one of his submissions:

Justen Said—“Today I took a bath using the feminine soap I bought and at the end I said my affirmations. Since my body was loose because of the bath I tried to do a little yoga, which I find hard because I have no flexibility at all! When I finished I laid and calmly slept. After that I talked to my Mistress which I enjoy, she is the only person I can talk this stuff to. I asked her to if she can give me a name and she said to give her time. Then I told her about myself so she can have an easier time with my name.”

Naming my sissy isn’t something I take lightly. This training is an intense 12 week course that is designed to get you on a long term path to feminization and sissfication. I am working on a name for naming Justen and it will be a ceremonious day when his new hame is revealed and HE becomes a SHE.