All posts by Lillith

Sissy Diary Entry: Kaycee in Chastity

This is the posting of a sissy diary entry made by Kaycee. Edited for clarity, some names withdrawn from the posting ~ No pictures submitted with this diary entry.

Dear Sissy Diary:

I am in the chastity phase. I need help. Begging for a Mistress to help train this novice sissy slut.

i am wearing a pink dress, nude pantyhose with white ankle sox. My ass is stuffed with an 8″ realistic dildo. I am locked in a chastity cage under my silky pink panties.

Please Mistress Make me your bitch. I suck- I mean I’ll do anything for you.

My mind and body are yours if you’ll take charge of my life and free me from decisions.

I am easily hypnotized with a wide assortment of trigger phrases. “CUNT FACE NOW” is my current trance. I am lying on my back with my left leg up over the back of the couch.

I picture you pounding me as I thrust my beautiful dildo in and out of my ass.

My last Mistress reprogrammed me in one weekend. We drove 3 hrs north to a little beach town. It was known for its private beeches where anything goes.

We got adjoining rooms and Mistress took the bigger suite. I accepted Her directional nod and went to the bathroom.

“Take a shower”, she said. I heard the TV come on as I took off my clothes.

I thought I heard the door close again and asked” Miss”? “Yeah, toss me your clothes”. I threw my shorts, sox, underwear and t shirt out-side the bathroom door.

I was about to turn off the shower when the shower door opened and my Mistress entered.

“Stand against the wall with your arms out kay. I’m going to let you use my moisturizer” I smiled slightly remembering the sweet odor.

Mistress said “this kind has a delayed reaction. It smells bad until it gets rinsed”

She lied of course.

I guess this sissy seems to be slightly desperate for a mistress to serve. The best place to find cries for help is in a diary. LOL. Also seems as though this story may be missing a few parts. The moisturizer…was it a soft scented moisturizer or was it nair? The part about the delayed reaction and a bad scent until it is rinced had me believing that it is NOT moisturizer, but nair. Removing the body hair from you.

Hairless sissies are always much better ~ Hope you had a good trip to the beach sissy!

Interested in sending in a submission to possibly be posted on Sissy Diaries? Click here (make sure to read/follow the rules or it won’t be posted)

Exposed: Sissy Cumslut colton

Being a sissy cumslut is a dirty job. Best to NOT do that in the proverbial closet.

It’s always a good idea to clean out the closet whenever you get a chance. For one, I’m a bit of neat freak and two…there is so much more room for all things sexy and femme in your closet once you remover yourself from it.

Colton here is on the right track. She claims she is a closeted sissy but the truth is, she is going to be expelled from said hypothetical (And possibly literal) closet. It makes me giggle that she goes through her Fiancé’s closet for the best outfits. She is choosing date night outfits for herself because obviously she is meeting up with random men she finds online and via different apps. I wonder what outfit her fiancé would choose for her? I bet her fiancé regularly picks out her own outfits to go meet real men to hook up with too. Clearly they have some common ground. LOL

Sissy Colton even admitted to stealing and dressing in her Mother in Law’s panties and dresses – then would go out and fuck men, bare back. Colton is the poster girl for sissy cum slut whore. Im not sure how she ever thought she could really hide in the closet, but It’s my privilege to expose her for the true sissy she was meant to be.

Some of her fondest memories are of her in your Mother in Law’s lingerie, dancing and prancing around the room playing with that clit stick and masturbating. She shared some other dirty deeds too but some a little too naught to share here. (involves tampons, I’ll let your minds wander with that)

Colton was never a real man and really has always been a cum slut sissy. How else could she explain being fucked by more men then women? Hell, the number of men she has fucked is less than the number of women she has kissed. She says her Fiancé doesn’t know…but…I’m willing to be she knows. Oh, she knows.

She knows what a cock sucking cum guzzling dumpster slut of a sissy you are. She’s probably just waiting for you to admit to it so she can exploit you more and probably cuckold you with real men…or perhaps even share a man or two.

Enjoy being expelled from the closet and exposed indefinitely!

Exposed Sissy: Becca the CUM GUZZLING SISSY SLUT

I will forever feel like an exposed sissy is a re-birthed sissy. Once something is posted out there on the internet, it is forever. Even if someone were to pay a removal fee – that never guarantees with 100% certainty that those pictures will be hidden forever. You never know who is reading sites and deciding to lift photos. My removal fee is for my time and for your hope – but…my hope, is that I never have to remove these in the first place. Id much rather an exposed sissy remain an exposed sissy … indefinitely.

Like this sissy, Becca.

According to her she has hidden her secret crossdressing, sissy desires for 10 years. But, I’d be willing to be that she has had these urges LOOOOONG before that. Maybe it was 10 years ago that she admitted it.

Becca has admitted how much of a cock sucking cumguzzling cum dumpster she is. When she is dressed up and forced to her knees to worship a big fat meaty cock – she is at her happiest. She finds her sissy faggot clitty dripping and drooling while being treated like the whore she is.

She did tell me that it was scary to be outted. It can be scary and it can be exciting – and that is all the more reason to do it!

So here is Becca.

Becca likes to suck cock.

Becca is a sissy slut.

Becca is a sissy whore.

Becca wants to suck a cock, have to wipe the cum off of her chin as she smiles and says ‘Thank you Mistress, may I have another?”

Becca is exposed – always and forever. Stop by and say “hi” to her. Show her what you got, she’s sure to show you a good time 😉   


Skeletons in the closet are NOTHING compared to a sissy crossdresser in the closet just DYING to jump out and be exposed to the world. For some sissies, the longer they are in the closet the stronger their desires grow  — the desire to bust down that door while wearing their high heels and sexy sissy attire.

Shawna SissyToes is feeling that urge.

She is ready to come out from underneath her rock and scream what a pretty little girl she is. (yes, that pun was intentional).

Hello Mistress. This is Shawna SissyToes, a closet sissy living in Rockland Maine.

I have been secretly crossdressing since I was very young, now I’m almost 31!!

I love to look and feel like a pretty, little girl soooooo much!! I have a very small cock that fits perfectly in my little, sissy panties!! I have a feminine, girlyboy ass that craves and aches for real men’s cocks and even women armed with a strapon cocks!!!

I used to be straight, but now I’m a sissy girl and sissies love cock, so now I love yummy cock!!

I want to be fully feminized from wig down to my painted tootsies and suck on real dicks, as well as taking them up my tight, sissy fag bum!!

Mmmmmmm…. I wish to be exposed for being a cock loving sissyboy!!

It turns me on and I have been wanting to escape my sissy closet for years now!! 


I can PERFECTLY PICTURE shawna singing – “I feel pretty” in a mirror with her lingerie and brightly colored lipstick singing into a dildo microphone. An encore song of ‘Im coming out, and I want the world to know’

I want the world to know about Shawna Sissy Toes and I want Shawna Sissytoes to truly experience life as a cock sucking crossdressing sissy. I can feel the excitement in her typed confessions and when chatting with her she is over flowing with anticipation of sucking cock and being exposed. Time to raise your sissy flag Shawna!

Enjoy the spotlight sissy! The light looks good on you!

Exposed Sissy: Brittanny the Panty Thief

I LOVE hearing from my panty thief sissies. This one will find herself in some serious trouble if she keeps stretching her wife’s panties out.

Good morning Mistress!

Thank you for giving sissies like me a place to expose ourselves. I have always needed a place to tell my story and to be exposed without really telling my secret to a lot of people close to me. I have to keep my secret because I am married with kids and I don’t think my wife would like to know what I do.

The real reason I work at home is so I can be who I want to be.

I worked in an office and always wore my wife’s panties.

Im bigger than her so they are always a little tight and give me the cutest, round bubble butt. My butt likes to eat those panties and I found myself picking them out of my butt all day long. It was so embarrassing. I am the reason that her panties get stretched out. I would often rush home to do the laundry before she got there and put the panties back so I wouldn’t have to worry about her smelling me on her panties. I buy her panties all the time, she thinks they are for her, but they are really for me.

I was happy when my company downsized and let a lot of us work from home because now once my wife goes to work, I rip off these clothes and slip into her panties and my bra. I bought my own bra because my wife is D and all I can fill is a B.

I keep the bra hidden underneath my side of the mattress at home.

I take care to not let her see it. I am the only one that makes the bed and cleans the room. I think I might like doing house work too. It is really hard to do house work wearing heels that don’t fit me. She is a size 8 and I am a size 11 (in man sizes. the only thing about me that is man size.)

I can’t post a picture this time, but maybe I can find the courage soon.

Thank you mistress

Thanks for your submission Brittanny! Seems to me like you have nearly the perfect set up.

I DO wonder what you would do in the event you are gallivanting around the house and your wife surprises you by coming home for lunch.

LOL. Maybe rather than stretching her panties out, you should get some that actually fit you – maybe you won’t be digging in your ass –unless of course, that is something you get a naughty thrill from then dig away little panty thief!

Be careful though, a hidden mattress bra could have some ramifications if discovered. Out of curiosity – what would you say? Would you come clean? Have you fantasized or thought about being caught in your wife’s sexy ‘unmentionables’?

Who is up next to be an exposed sissy?

Exposed Sissy: Sissytoes

A brand new sissy diary entry ~ Sissy Toes can be proud of her exposure since she is the first sissy exposed on my sissy website for the year of 2019.

I am SissyToes. I am a 30 year old closet, sissy crossdresser. I have been secretly crossdressing in women’s clothes and heels since I was 15. A good female friend of mine, whom I used to live with, introduced me to crossdressing when I was in my teens.

We were bored sitting around her house one day when she looked at me, with a big, mischievous smile and asked me if I would model some of her clothes for her.

I said yes and agreed to be her little model for a bit. I wore lots of her sexy clothes, including dresses, skirts, camisoles, nighties, leggings, swimsuits, panties and bras, and lots of feminine footwear (high heels, sandals, and girly flip flops).

She knew I enjoyed it A LOT! the proof was in her panties and there was no denying it!! I was more erect and turned on then I had ever been! I was leaking in her panties while I sashayed around for her, fully dressed like a girl!

My friend loved it and laughed so hard, which made me even harder and more aroused!

Ever since then I have secretly worn girls clothes. I have bought a decent amount of girl clothes and heels, but its more fun secretly raiding other women’s wardrobes and prancing around in their clothes and heels!

This is me secretly crossdressing and posing in the house of that same female friend that talked me into it all those years ago – here I was, years later…in her newer house(we no longer live together unfortunately).

She was away from her home, so I snuck into her clothes and secretly posed in her bathroom. I was very turned on, and felt extremely girly, and gay!! I have worn her clothes on more than one occasion, but never got caught. I kind of wish she had caught me and “forced” me to be her little sissy bitch boy!!!

Thanks for reading. Kisses to all, MUAH!!!

Xoxoxo ~ SissyToes

There is something exciting about playing with fire a bit. Being so close to being caught. I’d wonder if your friend would have the same reaction now as she did so many years ago. Tread carefully my dear.

Continue embracing your little sissy bitch boy self!

Diary Entry: Real Changes and a Sissy-gasm

There are real changes happening.

I noticed them Sunday night as I put my 5″ stilleto high heels on. I thought I would manage okay in high heels, but I couldn’t really walk, and I couldn’t control myself sexually either. That last one bears repeating.

I couldn’t control myself sexually in high heels.

Mistress Lillith had me purchase a chastity device and had been making references to sexual frustration and compliance in some of her messages, which sounds both fun and a little scary.

Prior to Sunday, I had been chaste since last Thursday. I had a pink ribbon tied around my clit.

It’s constant rubbing causing very mild irriation. I was wearing panties occasionally, and I dutifully listened to my mantras prior to bed–playing them on repeat with Mistress Lillith’s subspace hypno goodie as I fell asleep.

Sunday I had some alone time for the first time since … Thursday.

My shoes and cut-offs arrived on Saturday.

I put on the cut-offs with my tank top and thong underwear. WTH, size 31 is never tooooo big for me. I didn’t realize they would stretch so much. Okay that was a little disappointing.

How about the shoes?

Oh my gosh, perfect fit. The strap tied around my ankle, locking them in place. (The strap was surprisingly hard to lock and unlock!) I tried standing: my butt and chest instantly pushed out in opposite directions. Whoa, weird… and interesting. I took a few wobbly steps and realized I didn’t know how to walk in 5″ heels. “I’d better sit back down,” I thought.

Mistress Lillith’s twitter feed had showed some unusual NF activity for her on a Sunday, especially a holiday weekend. I thought there might be a chance of contacting her. I even tried reaching out to her on Skype, which I’ve never used before. No luck.

I purchased a tease and denial dice game video instead.

Stroking. Slow and fast. Alternating styles. It was clear there wouldn’t be a chance to orgasm at the end fo this video. On the last 5 of the dice rolls Mistress Lillith had me edge the number of times as on the die.

Pausing the video… stroking… staring at my shoes. Edge… Breathing… Again… Fuck, my shoes. A tiny pink ribbon bow sticking out from cut offs that were now riding up my ass. Edge. Again.

I was pulsating and twitching. An extra five dice rolls were granted, more stroking but ultimately denial. Staring at my shoes as I stroked… Oh no, I’m cumming. I tried to stand and to make it to the bathroom, but I COULD NOT WALK. ERUPTION. I collapsed in my chair. I completely lost control. Lost control of myself, of my feelings, of my arousal. I hardly recognized the view of my legs… a pink ribbon… a sticky mess… my shoes.

I completely lost control. Wow that was an intense orgasm. Shades of my teenage self. There are real changes happening to me sexually.

Diary Entry: Sissy Shopping and Thoughts

During part of the training, there is shopping that happens. That seems like a ‘DUH’ kind of expectation – but, with a new sissy you, you need a new sissy wardrobe.

Here was the diary submission for that week


The shoes from Yandy didn’t ship with the rest of the items Mistress Lillith assigned me to buy.

They were to come separately but there wasn’t a tracking number. I contacted customer support with the order number and inquired. A customer service rep named Linda, who had a girl in lingerie for her profile picture, emailed me an apology:

“Robert, the tracking number for *your shoes* is…” Size 10. My shoes. A thong string bikini and leather and chains were the other part of the order.

Kind of humiliating.

A review on for the leather and chains outfit was from a guy: “My wife looks great in this.”

Uggghhh… Super humiliating.

I asked Mistress Lillith for a little more time on this week’s assignment. She agreed immediately. I wanted to tease her as a pushover but didn’t have the nerve. I guess I did here.

I wonder if she’ll really push me and my boundaries. This is already as far as I’ve gone. I think I could probably cum just thinking about intense pyschological domination… Being told

“No. Get it done bitch.”

Yep that would make me cum.

This was a crazy week at work. A really positive, memorable one. But still one that sucked up everything from me. I wasn’t sure I could juggle everything I had going on. By some fortuitous circumstance I found myself alone for an hour. I could hardly believe it. “Okay, now or who knows when.” I thought.

Need to shave. Foundation. Eye shadow. Damn I messed it up again. Pink blush. That looks better. Hot “cocksucker” red lip stick. Mascara. 20 mins in. Makeup takes forever.

Slave 4 u by Brittany Spears played in the background and her music video was on my TV. I fumbled as I tied a string bikini for the first time. It didn’t cover anything downstairs! I set my cell phone up to record and walked, posed.

Next outfit: the leather and chains one. Oh my gosh. I kneeled. I got on my hands and knees. Whoops my balls made it in the shot. Now the black dress.

Stress was washing away somehow.

45 mins in. Time is getting tight, need to clean up. Rushing. Double, triple checking things–yes, all put away. Unbelievably I finished, mostly. Still have my shoes and cutoffs that haven’t arrived yet.

My body hair is growing back slowly. I really like my nude skin better than being a wookie. Waxing is expensive and painful but who knows. I have a week or three to think more about it.

I missed my mantras twice this week. Just completely forgot. I’ve tried to make up the time here and there.

I had a sissy dream on Monday.

These are RARE for me. In it my hands and legs were bound in purple blocks. My headphones were on and I was being forced to listen my sissy slut mantras.

Work meetings have been different too. I’m admiring women’s makeup and how they do their hair. That’s NEW.

I’m tired and still having fun.

Now you know why women are sometimes exhausted. It’s a lot of work looking so perfect! 😉

Diary Entry: Sissy Waxing, Part 2

My male ego NEEDED that blush.

That was a lot of femininity to absorb and that shot in the arm toward the end helped me recover a little.

There’s of course another possibility–one that is deeply erotically humiliating–but I still suspect my gut instinct interpretation was correct.

My legs and chest feel different. Actually super weird is more apt.

It’s the strangest sensation but I swear I feel like my legs are wet all the time, like I’ve just gotten out of a pool. Does hair soak up moisture or something? Actually I think what’s happening is in the past when dry, the hairs protruded a bit and on contact with something they would trigger the nerve. Previously when getting out of water the hair would be weighed down by the weight of water and pressed flat against the skin, and wind or something else would trigger the nerve. Now without hair, any brush against the skin is triggering a sensation has historically been associated with wet hair and my mind is confusing the two. At least I think that’s the explanation but I’m not sure. I keep reaching down to brush water off my legs but they are dry and smooth. WHAT IS HAPPENING!?

The strangest, most surprising thing I still quite can’t get over though is my stomach. It’s like I don’t even recognize it. I look down but I’m still not quite convinced it’s my stomach and my belly button. I can hardly keep my hands off of it, feeling the smooth foreign skin over and over again.

For the first 18 hours a red bump appeared in place of every single hair that was ripped out.

Jessica assured me those would recede and they did.

I have smooth hairless skin from my neck down (okay, my arms still have some fine hair and i didn’t have my armpits waxed or my bikini line).

While my shoulders are a little broad, I don’t quite have the physique of a masculine male… Not many muscles anyway.

I look feminine with my hairless skin. Dressed, I would look quite feminine. Dressed and from behind I would be indistinguishable from a female. I look like a sissy.

I’m acting and behaving girlier too: getting waxed, chatting about skin care with a pink haired girly girl, shopping for girly skin care products.

I’m acting like a sissy.

Something that’s kind of turning me on too is that the mantras feel different now. They feel … more effective and more real. Something about looking girly and doing girly things and having it repeated in my head is powerful.

I am a sissy.

It’s been a deep, erotic fantasy of mine for more than two decades to have hairless legs and a hairless chest. Always fantasized, never realized. That limit has just always been too far and out of reach. Until now.

My legs, chest and boobs look so much better too.

Thank you Mistress Lillith!

It’s amazing what can happen when all the sissy puzzle pieces fall into place.

Diary Entry: Sissy Waxing Part 1

I believe in Feminine Rituals. I am female, and I do engage in said feminine rituals on a regular basis. I believe that sissies must learn these rituals and complety them daily in order to live their sissy lives. How can you call yourself a sissy if you DON’T engage in these rituals?


Mistress Lillith’s rituals assignment is due in 1 week and I needed to get started early.

I searched through a few local salons–one that was super pink and girly and another that was more gender neutral–and settled on the gender neutral one. I called to book an appointment.

“Hi, I’d like to come in and have my legs and maybe areolas waxed.”

“We can do that. Are you looking for a brazilian? We can’t do brazilians for men, is that okay?” the receptionist asked. “That’s okay, I just need my full legs waxed.” “Okay, let me check with the beautician to see if she can fit you in today. Hold on.” “Okay, are you able to come in this afternoon?” “Yes, thank you.” And I booked the appointment. But…

2 hours later I received a call from the salon… “Hi Robert, I’m sorry, I’m new at this salon and I’m afraid the beautician isn’t comfortable waxing the entire leg. We do have another staff member that will wax your full leg but we would need to wait until tomorrow.” 🙁

… And the appointment fell through.

Needing a backup I called the super pink and girly and intimidating (but highest rated Yelp) salon in the area and booked an appointment. Everything was set.

Immediately after booking I received a call from the first salon’s manager. “Hi Robert, I’m sorry for the mix-up. We can get your full leg waxed today at a discount if you’d still like to come in.” Lol.

I think I might have inadvertently caused quite a stir.

This part of the story almost got deleted from the diary but made it in because–without passing judgement–I think the reaction caused by crossing gender boundaries is interesting.

The super pink and girly salon turned out to be super pink and girly. The entire area oozed femininity. Next door was a bridal shop. I entered the salon and approached the receptionist. There were a few women sitting in the fluffy pink and light green chairs and couches, staring at their glowing rectangles.

I was handed a new client form to fill out and given a bright pink glitter pen.

I was in foreign territory.

After finishing the form I handed it to the lady who would do my waxing: a young, cute bouncy, bubbly girl, who obviously cared about her makeup. Her dark green eye shadow extended out far from her eyes and then cut off sharpy at a 45 degree angle. Glitter shined from parts of her face. Her hair was HOT PINK and was pulled tight into a scrunchy that sat at the crown of her head, from there her hair flowed outward above her head like the stem above a carrot. This was Jessica. I was deep in foreign terriotry.

“Follow me,” she said. And we proceeded through the facility into the waxing room. “Take your clothes off. Leave your boxers or underwear or whatever you got on down there on. Lay down on this bench with your head on this end and I’ll be back in a few minutes.” I did as I was told. She entered after a few minutes and I meekly asked for a vanity towel and was obliged.

Something hot was being spread on my leg. “So why do you want to get your legs waxed?” the pink haired girl asked. Hmmm… How to answer this? … … My Mistress is feminizing me?

Probably not a great answer. I began to sputter something about my hair and being unsatisfied with it and suddenly in the middle of my sentence my lungs gasped for air and my speech was cut short as sharp pain shot up through me like a lightning bolt. “uuuuuuggghhh…” I ended my answer prematurely.” Jessica giggled.

HO-LLE SMOKES. Waxing hurts. A. LOT.

I had read reviews about it being bad but I was genuinely surprised how much it hurt. Jessica and I made chit-chat the entire time. She was young, not married, into music, gave me tips on skin care and exfoliation, had 3 male clients and blah blah blah. I was constantly having my speech cut short by sharp pains as hair was ripped out my skin.

My nerves were on fire. “Maybe I can’t handle BDSM pain,” the thought occurred to me.

It was hard to stay focused on what was happening and not daydream about why I was here getting waxed. Fortunately I managed to stay soft and OH MY GOSH am I thankful for that. Finally after two hours it was over.

As I was paying the receptionist and getting ready to leave Jessica came to the front desk and reminded me: “Don’t shave it when it starts to grow back. Let it grow for 4 to 6 weeks and then come back and see us. It won’t hurt as bad next time. Use an exfoliater tomorrow and moisturize afterward.” For the first time since arriving I looked her in the eye and thanked her. Something curious happened next.

Jessica turned bright red as she smiled, looked at the ground suddenly, mumbled a thank you, and then hurried out of the room.

Jessica blushed hard! I wonder… (to be continued)

This part of the training always cracks me up. Obviously I don’t expect ALL of my sissy trainees to get waxed, there are work around and other rituals. But the ones that DO go out and get a wax, are always in for quite a sissy adventure.