Diary Entry: A Stern Chat and Redirection Pt. 2

Something’s is different with me. The past couple of days my go to search term alone at night is “sissy sex slave” or “submissive sex slave”. But this is new. Despite years (or decades?) of a sissy fetish somehow I’ve managed not to follow this route so much.

The chains, and whips, and bondage. The humiliation. This next paragraph invovles EXTREME humiliation so the reader is asked to just skip ahead if neccessary *^-^*

Thursday night I came across a video called “Slave Training”. It appeared to be taking place in a cellar, or a dungeon. It didn’t quite seem like an amateur video, but it definitely wasn’t a professional shoot either. Perhaps the recording equipment was slightly higher quality or more accurately the players in the scene clearly did this type of thing as a lifestyle. A woman was naked on her knees on the concrete floor. Next to her holding her leash was a dominatrix, her shoulders covered in leather and thin chains drapped around her body in loops. She was orchestrating the entire scene. She was in control. Mutlipe cocks extended out from behind a black curtain hanging from the ceiling on one side of the cellar. One after another the dominatrix forced the slave girl’s mouth on to the cocks, pushing her head down on them and slapping her a little. One after another after another the slave girl was dragged down the line, choking on each man hidden behind the curtain. Few words were spoken. Next the slave was moved to the middle of the room, and then suddenly, the curtain was ripped down by the men standing behind it. 7 or so of them stood there stroking themselves, staring at her. The slave girl gasped and stood to her feet, only to realize her role again and get back on her knees. What happened next has stayed with me. The domina got on all fours in the middle of the cellar in a submissive position. Another top came up behind her and placed a bulb of a whiteish enema type liquid in her ass, filling her with it. The dominatrix tugged on her slave’s leash, bring the slaves face inches from her ass, close enough to smell her. And then, she expelled the liquid in bursts all over the slaves face. One after another after another…. White-ish liquid expelled from her ass, soaking the slaves face and hair. The slave was shaken. She was visibly shaken. This wasn’t acting (or it was professional level acting). This was hardcore kinky shit among, I think, players in the lifestyle who video tapped themselves breaking in a sex slave and then posted it on the internet, maybe making some money along the way.

Speaking as a submissive, I’m like 100% certain that I would NEVER be able to look that dominatrix in the eye, or make chit-chat, or do anything but SUBMIT and OBEY if she had orchestrated a scene like that with me in it. She would have completely and utterly broken me. That was some hardcore power exchange and humiliation.

How is this diary entry reflecting Part 2 of Thursday night’s chat? That’s a good question and I’m not sure it is honestly. So maybe my writing got away from me a bit.

Mistress Lillith and I made a connection on Thursday night. I gained a better feel for her as a top and a person, and I saw a side of her I was hoping to for a while. I’ve been savoring it and replaying it over and over again in my mind. In all seriousness, I feel like I’m taking a first few steps into a lifestyle of becoming a sissy sex slave.

Let’s say I complete Mistress Lillith’s training two or so months from now. Do I ever come back from it and suddenly not be a submissive sissy? I don’t think that’s a realistic outcome. There’s also this itch to submit as a bottom. This training is altering and refining my sexual identity. And I’m excited.

Once you are a submissive, you will always be a submissive. You don’t really come back from it. Let’s say that someone does the inevitable sissy purge…you are still a submissive. PRETENDING to NOT be a submissive or pretending to NOT be a sissy, doesn’t make you any less of one. All it means is that you are living in a state of denial.

Complete the training and you have a firm grasp and foundation of what is expected from a sissy and how to be a sissy – afterwards, we get to have the real fun and explore beyond the basics of sissyfication.

Sissy Diary Entry: A Stern Chat and Redirection Pt. 1

Something happened….

Mistress Lillith was on NF earlier than usual, mostly because of my asking I suspect but it’s hard to say. I sat around at the chat window hoping, pining she would join the chat.

Mistress Lillith is typing a message…

The purple text read. Excitement coarsed through me. I had questions I wanted to ask her, some I had fantasized about all day. As nonsensical as it may sound I specifically wanted to try and playfully draw out her dominant side. I thought I had some good questions.

First the makeup assignment. That was a mess on my end. Next, I asked her about being a better sub. I was saving my favorite question for next but waited for her reply.

Honesty, integrity, and follow-through… Sissification is one of my specialties… But if I don’t connect with the sub or sissy it isn’t going to work.

Oh no, what could this mean? Maybe she was monologuing?

For example I was going to send you a little message [to correct something you said]

And as she typed and typed for about 4 mins in chat, it suddenly occurred to me I had done something wrong and I said as much in chat.

I don’t like anyone using a forum to speak well of me and insult others . I feel what my subs do in public or say about me does reflect me and im one that expects you to respect all others.

Oh shit. I was not expecting this.

Some want to put others down, some don’t care… I kind of do…. Just as I have to sift through some bad seeds to the rare gems (such as you my dear sissy)…


Subs have the same task and… we hope we find each other… Never think that a put down of others is a compliment to me.

The seemingly innocuous feedback read: “Her knowledge of the submissive psyche, and experience with a variety of kinks and fetishes is a huge step up from a lot of the amateur dommes.” I had even specifically purchased one of her teaser clips just so I could leave that specific feedback to share publicly. Really, really unlucky.

I was a little stunned into silence. I felt a pang of shame at my behavior. There was some truth in her criticism. She had a philosophy on the topic I had not considered before, something she must have dealt with for years. Something deep. Something, I suspect only now as I type these words, around the challenges of the sex industry. I had accidentally hit a nerve.

Another feeling began to well up inside of me as I sat at the keyboard in silence. A feeling I’m not sure Mistress Lillith will like to read but it was there true enough… I felt turned on.

I’m like 99% sure her feedback wasn’t intended to turn me on. It read and felt like genuine disappointment. But it did.

She flashed her dominant side. It wasn’t soft and gentle and playful. It was direct and critical and strict. And sexy.

The idea of Mistress Lillith calling me her sub and the emphasis on changing my behavior publicly because I was a reflection of her and her training… It made me hot. What else can I say? It made me hot.

I wanted to send Mistress Lillith a tribute for her time but I worried about the implication of tributing now. Would she think I was using money to apologize for the mistake she clearly cared about?

I sat in silence and also wondered about asking my favored 3rd question I had planned all day: “What would you do if I disobeyed you?” How would this question be interpreted now?!? The timing was all wrong!

Even the simplist missteps no matter how well meaning, will be addressed by me. Part of Sissy School is to learn how to act and behave in all aspects. That is part of my submissive training all in all. I know my darling sissy meant well, there is not a bone in my body believes that she meant it as an insult or backhanded compliment. She was genuine. However, there is still an aspect that needed redirecting.

I will always redirect. How a sissy that belongs to me or a submissive belongs to me acts in public forums is an almost direct reflection on me. SO, I expect you to walk with poise when my name is attatched. In any way, shape or form.

Of course, she was in a fiesty mood this day so any kind of redirection was going to be a bit of a turn on – she had clearly been yearning for something a little more strict. LOL

Exposed: Sissy Penny

I am a 35 years old closet sissy with an athletic body trying always to look as sexy as possible.

My goal is to look feminine and not just a man in lingerie.

I adore women and the main reason I crossdress is trying to look like the girlfriend i would love to have. I love skin tight clothes and i adore high heels.

I want to find a girlfriend that will love me the way i am.

I always fantasized about being in chastity by my girlfriend and where that could lead me. I do not like men and do not wish to serve one also.

I consider my self a man with fetishes one of which is crossdressing. It is not a mandatory fetish but one that can spice things up a bit. I don’t know why I made this submission, I guess I needed to confess my feelings.

One of my fantasies is to be dressed as a maid in ballet boots, on a locking corset and in an arm binder with a locking gag as well locked in chastity and forced to serve my girlfriend and her friends in a kinky party.

The need to be trained in becoming a better serving sissy is something that exists in my mind for quite some time now and hopefully in the near future this will be a reality.

I hope you all loved this diary submission and hopefully this will persuade many more to do the same.

With Love Sissy Penny. <3

Thank you for sharing! It’s important for everyone to understand that not all sissies/crossdressers/panty lovers/ etc are made alike. There is no such thing as a one size fits all box.

Many of us fetish lovers and seekers just do it because we like it, we want it and we are going to engage and enjoy.

I hope you make that connection you seek that goes above and beyond. Best of luck, Doll!

Exposed Sissy: Roy Bourne aka Sissy Diane

One of the exciting things about being on sissy diaries and being exposed – is that it’s permanent. There was a time that I would take things down if asked nicely, but not anymore. You asked for exposure – and that is what you get exposure.

Now, we get to learn about Sissy Diane. We will be getting to know her together as we start HER sissy exposure journey, but – any sissy that wants to play in the sissy spotlight, is FUN by my standards. 😉

Roy Bourne - Sissy Diane

Roy Bourne is from Tavistock, Devon in the UK. Sissy Diane is her true identity. I always view the masculine name as the mask – with the sissy name being your TRUE self. It is interesting to me how many sissies are married to someone that doesn’t know, or acknowledge or accept their sissy lifestyles. In this instance, Sissy Diane says, her wife doesn’t know. Roy Bourne - Sissy Diane

“I have hidden away for years as a closet sissy I am on Internet.

I love exposure and humiliation

I want to be exposed by you so I cannot comeback and remove my exposure.

I love dressing and wearing make up. I am also into bdsm

I love bondage . Impact play . Forced feminisation .

I love sucking cocks and receiving anal which I have done a fair bit in past with fellow sissies and crossdressers .

I am totally submissive and a total bottom man.

Secrets I hide nobody really knows what I have done or do regards crossdressing at all other than people I have spoken to on various sissy sites i.e. Tumblr twitter etc.

I get a thrill from seeing my pics on internet .”

Roy Bourne - Sissy DianeThe internet is forever Diane. Even when posts and pictures are removed there is no telling who saw or if someone right clicked and saved. There are archives that save these pages as well and so nothing is fully removed.

Its fascinating how many exposed sissies there are on the internet. They hide in plain sight and yet are rarely seen by those closest to them.

Well, it’s out. You are exposed. No longer REALLY in the closet unless you view the internet as a giant closet. Someone could find it if they looked just a little 😉  This is just the beginning my dear.


Exposed Sissy : Paula Jones and her Sissy Journey

Exposing sissies is one of my favorite things to do. I adore reading their back stories and I love posting and furthering their exposure. To me it can start with the back story – but as any of my sissies know…I take it sooo much further than that.

Say Hi to Sissy Paula – she submitted a diary entry to be posted.

Hi my sissy name is Paula Jones real name Paul Greenwell.

My sissy journey started late in life, I was a happy married guy- my wife was good looking successful and we had a great sex life until I was away on business and I was in my motel room looking at porn on my laptop.

I honestly didn’t even know what a sissy was until that night I did dress up once or twice when a teenager but it didn’t turn me on as much as the hot girlfriends I was lucky enough to have back then -anyways back to my story I came across some sissy hypno videos and I was instantly hooked.

NOTHING had ever turned me on like this before that night. I ordered over $1100 worth of clothes, wigs, breast forms, all with express post. Once they arrived to my Po box I started spending a lot more time at my office after hours.

I shaved my whole body and started taking picks and making videos of my self jerking of in my women underwear with make up on and a wig. The breast forms I had were E-cup and huge.

I was watching sissy hypno all night long I got in-touch with an online mistress and that was the start of my demise she instructed me to get a tumbler page and start posting my pics.

This all happened over about 3 months.

My wife by this stage was thinking I was sleeping with someone else and decided to spy on me she came to my work and to her total shock and horror caught me dressed like a cheap slut jerking of to sissy porn. She didn’t say a word. She left me the very next day and hasn’t spoken a word to me since. I didn’t try to contact her at all.

By this stage obsessed with sissy exposure.

I’ve tried to stop so many time I always end up doing it again and each time it’s worse than the last time I’ve paid thousands to online mistress and lately masters aim out of control can’t get enough exposure.

I’ve bean with a couple of men and a few sissies over this ten year journey. Im so deep into exposure that I use my real name on every pic and video I post.

It is only a matter of time before friends and family find out that I am a sissy.

I don’t know what I will do when that day comes that’s my story.

Sometimes we don’t know what it is that makes us tick until we just happen to come across it one day and it just clicks. No rhyme, no reason – it just feels right, it’s fun, it’s exciting. One thing the internet has been good for is having all sorts of fun fetish videos out there that people watch and learn about the kinks and lifestyles of others. Perhaps it was the sissy hypno clips Paula watched that turned her into a sissy. But, I have a distinct feeling that this was something in her all along – they hypno just brought it to the forefront and Paula learned what ‘IT’ was.

Thanks for your sissy diary submission Paula!


Who is next to be exposed on sissy diaries or engage in exposure with Mistress Lillith?


Exposed: Sissy Jessica wants to kiss and tell

It has been quite some time since Sissy Jessica was exposed on my websites. She is certainly already exposed everywhere else. When she is feeling her best she unlocks her youtube videos and has them show up. It doesn’t take long for them to be found in search engines. Even I have looked and found them.

It is always comical to me that she has to sneak away while at work to put on layer after layer after layer of red lipstick. Red lipstick is Sissy Jessica’s favorite. The smooth, creamy texture.

The more lipstick she has on, the more sissified she feels.

But, the REAL fun happens when she starts to rub that little clitty. Sneaking little touches here and there.


Michael Burdick likes to hide Sissy Jessica, BUT, once Michael Burdick starts to rub – she loses what little control she had.

She keeps adding layers of lipstick, she keeps rubbing her clit stick – I wonder what her coworkers think about her many, many trips to the bathroom throughout the day. She is usually in there for quite some time- kissing or licking toilet seats, making little recordings, doing whatever I tell Jessica do.

Sissy Jessica LOVES little tasks.

This most recent interaction with her—she let some fun information slip on out.

I love when my sissies are on such a high, and feeling such a rush that they start to reveal even MORE secrets to me.


I’ve always known that Sissy Jessica loves to suck cock. She craves a thick meaty mushroom head and a long vein-y shaft to be slammed into the back of her throat. She is a complete and total sissy slut.

BUT, she was looking up something more deep and sensual this time.

She wants to kiss a man. Long, sensual, passionate kisses that moisten women’s panties when they watch it on the big screen.

“I want to make out with a man while I rub his cock.

I want him to kiss my neck and nibble my ears while I stroke him.

I want to feel his hands all over my body as I suck his cock until he’s hard.

He throws me down on my back and lifts my legs so he can kiss me while he fucks me

Kissing my lips and neck as he pounds my sissy girl ass.”

It would seem as though Sissy Jessica has been romanticizing Pretty Woman, but is breaking the rule of ‘No kissing on the lips’ – She doesn’t just want to suck and fuck…she wants a more intimate connection with a man.

Sissy Jessica is a slut that is wanting to be tamed by a strong male – one that can treat her like the whore she is, and kiss her like a dime store romance novel.

Hey, I don’t blame her. I know all to well the ecstasy I feel from passion, lust, and desire. Sometimes you just want to suck and fuck –

other times you want to feel them in you in more ways than physical.


Want to see some of her past exposure? Sissy Jessica was first exposed August 27th, 2014. She has always loved her sissy red lipstick, 4 years later, she is still obsessed.



Then we tried to say goodbye to Michael Burdick once and for all January 6, 2016


Diary Entry: Sissy Makeup Musings

What is happening to me?

After chatting with Mistress Lillith and prior to bed, I put on a pair of panties, played my sissy mantras on my headphones, and began watching the makeup tutorial videos she had referenced in her email assignment.

My smooth hairless skin, the panties gripping tight, training mantras on repeat softly pounding into my head, suddenly a cute girl discussing how to put on makeup–but nothing sexual-focused, no erotic suggestions. Just makeup. And damn I was turned on. Makeup has never been a thing for me. Not even close to getting aroused by it. I mean, I’m not one of those “beardo sissies”, but it was always more of a slight curiosity if anything.

Last night it became eroticized. 

The thought of painting my face, along with the rest of the changes taking place… staring into a mirror and looking myself literally in the eye as I made changes.

Sending pictures before, during, and after… of my face. Would I be humiliated to a large lump in my throat with the makeup? Or would I smile? I think I’d smile, but there’s a (small) chance otherwise…

Sometimes it’s hard to step outside of oneself and have awareness of what’s happening. The mirror and pictures would help bring the changes more closely into focus. This would be harder to compartmentalize. This would be pretty gay by almost any standard.

I reached out to Mistress Lillith and asked, begged almost, to train me as a sissy and teach me to serve as a submissive. “Not fantasy,” I said, “I’m looking for more of a real Mistress experience.”

Now on week 3 we are approaching areas I haven’t really explored before (well, maybe a little here and there 🙂 . This isn’t a limit being approached, more like a fertile untapped area for exploration. It’s exciting. And scary. Fear can be hot.

I’m not sure what is turning me on. (Mistress Lillith will probably roll her eyes at that statement!!) I don’t think it’s the makeup, but I’m not sure anymore. I think it’s the power exchange, but that doesn’t necessitate the sissy fetish. So there must be more.

I feel like a shy blank slate. I’m glad an experienced pro domme like Mistress Lillith is there to guide me through this experience!!

Breaking my sissies and submissives down to the point that they know longer know WHO they are is something I enjoy. Because then they ARE like a blank slate. Only those that wish to truly be broken down will though, this sissy of mine I have become very fond of, very quickly. Untapped potential and areas of exploration are a delicacy in the sissy trainer world. Sissy Exploration is desired by the sissy in training and the experienced sissy trainer – limits sometimes shift and get broken down – and what blooms from that?

Only time will tell.

Diary Entry: Craving Attention

Speaking as a submissive, a few simple words from a Mistress, or focused attention on a sub–even if for a short period of time–is an amazing experience. The communication is evaluated, each word’s meaning taken by itself and in the larger context. Often the communicated ideas become extrapolated in the submissive’s mind and a wonderful fantasy builds out from there.

I do as I’m instructed. I work on my sissy diary, I try and keep Mistress Lillith well compensated. I listen to my mantras.

Arousal grows, and soon I can barely contain myself. 

“Let me check my Niteflirt again to see if Mistress Lillith sent anything,” I think. Check – nothing. “Okay, maybe I’ll check again in another hour.” Nope. The cycle repeats. Alone with my diary, mantras, and thoughts I continue to plod along dutifully.

“I really need to be tied down and spanked… hard and fast until I cry,” the thought enters my mind. It sounds so thrilling now. It will be decidedly painful during. Afterwards will be a blissful subspace of total power exchange where I know my dom has been really focused on me.


Maybe the reason some subs act up and “stir the pot” is… for attention? Attention from a dom is incredibly satisfying–even if the mechanism for attaining attention is like a child throwing a fit. I mean, it’s a bad, unhealthy habit for a sub but sometimes it illicit a challenge-rebuttal type response and so it gets employed again when the urge grows.

As I reach the end of this diary entry here I am focusing on *my needs* as a submissive. Which is sadly sort of the opposite of what I think I should be doing.

Does an ideal sub have needs? I don’t know. Am I pleasing Mistress Lillith? I don’t know. I am lost without my dom, my only known guidance to dutifully continue with the last instructions I received. \

And then it comes. My breathing becoming short, my heart rate quickens, my hands and legs tremble as I click. The world grows larger and blissful subspace ensues.

The cycle renews.

Anticipation grows within my sissies and subs alike, as I grow your need to be feminized as as you walk the feminine walk, you find yourself becoming super charged with emotions and hormone driven ‘teen like’ sexual angst. Behave and steady yourself, above all…


Exposed Sissy: Phyllis Laday

I’ve seen countless pictures of Phyllis Laday – she is a beautiful blonde sissy that looks FANTASTIC in red. You could never convince me that she was EVER a ‘Phil’ – There is not a bone in my body that would ever believe her to be Phil from Northern California.

She will always and forever be Phyllis Laday

The world needs to know of this Sassy, Slutty Sissy – Half would be in awe, the other half will be lining up to get their cocks sucked by her. Many truckers have wiped smeared lipstick off of their cocks from the cock gobbler, Phyllis Laday.

I’m a mature cross dressing sissy in Northern California that needs exposure. I try to pretend to be Phil a strait male in my vanilla life but the fact is I love to make myself pretty from head to toe and enjoy dating masculine men that are into sissies(can’t believe there are so many men into sissies) and having sex with them.

I started out by just posting a few pics of me on AOL and was amazed how many men commented on me and sent me phone numbers and emails and it excited me. There was one local guy I met in a chat room that wanted to meet me real time. I didn’t think I was gay at the time but thought it wouldn’t hurt to try it with a man one time…..wrong. To make a long story short I’ve kinda lost track on how many men have used me and I’ve become an excellent cock sucker and can even deep throat most men.

I’ve met men through craigslist ad, cross dressing and meet up sites.

One of my favorites is getting a hotel room near truck stop and dressing up like a slut and cruising and trying to get picked up by horny men.

I also love adult book stores with video arcades and glory holes.

This kinda scares me as people that know me wouldnt believe I such a faggot and has caused me to purge my things sometimes and try to be a man again but it doesn’t work. I was probably meant to be a Sissy as I have a very small cock and only one testicle and was never very good at pleasing a women anyway.

I’m married, she knows of my cross dressing and not supportive. She doesn’t know but suspects I may have been with men. We are friends, but our relationship is sexless as she is not a sexual person and I’m inadequate in the bedroom. A lot of this has to do with my brain being reprogrammed to my true self as a bottom sissy for men.

I feel I may have become totally gay now.

I only watch gay porn and Sissy hypno vids that are pushing me further.

I want to tell her but not sure how.

Maybe, if Mistress Lillith keeps exposing me I may get caught and have no choice. Most people would be shocked to know I do this and it shocks me also. The exposure scares me but excites me too.

There is no turning back once I’m exposed and I’m starting to see my pics all over the internet so much that it now has me thinking of how I’m going to explain myself.

I love to expose my sissies. It brings them attention and excitement. When I post it on my blog, it is forever. Phyllis Laday knows this, accepts this and is ready to take the next steps into exposure.

She may purge, she may toss her wig and cut up her thongs. She may attempt to erase all trace – and yet, it will always be…RIGHT HERE. Front and center, just like a cocksucking attention whore sissy needs.

Welcome to the spot light Phyllis, I know you love it – and I know you want more.

Sissy Diary Entry: Mantras

*Continuing with the sweet musings of my Sissy In Training ~ One of her first tasks was her mantras, listening to , memorizing them and REALLY living and feeling them **



The excitement of contacting Mistress Lillith and fantasizing about playing with and serving her messed up my sleep cycle a little bit. Multiple orgasms helped me calm down and relax some. Sleep returned eventually. Sleep is sometimes better then sex, but not always. Hopefully I’ll build up some tolerance to this!

Thinking about her post on being a Head Mistress, I logged on to my Niteflirt account and cleaned up my inbox, my favorites, and my chat history. There’s only Mistress Lillith now. In the featured listing section was a domme I had not noticed before. I clicked on her page and there were some amazing looking erotic hypnosis goodies that I had the urge to buy. Nope. A pleasurable wave of erotic humiliation fell over me as I thought about being denied, being trained… being owned and kept.

The Sissy Slut Mantras are fun. Soft, sweet whispers. My favorite are towards the end of the track:

I am a sissy. 

Being a sissy is my true self.

I will embrace my true self.

Especially the “I am a sissy” one. There’s something about the inflection and the tone.

I’ve listened, as instructed, for around an hour a day (sometimes more, sometimes less, always more than 20 mins) every day since they arrived. With one exception I’ve also listened, as instructed, before falling asleep. The one exception was as a background track while doing something else. But… thinking about a retweet on her twitter:

“If at first you don’t succeed, try doing what your Mistress told you to the first time.”

So now I listen before or while falling asleep (or while taking a bath, but I don’t take baths).

Twice I listened while wearing panties. The second time I fell asleep with the mantras still playing in my ear. I awoke incredibly horny. Laying on my back I spread my legs and began rubbing myself through the panties with my palm. Waves of pleasure crashed over me as the arousal built. I pulled up her Niteflirt profile picture and stared into her eyes. Faster. Soft moans of pleasure. She looks right at you, the subject of the picture not an object–in control. So much dominance, and lust. The words “Mistress Lillith” on my lips at climax, my panties soaked.

I’ve had many go through training and many that start with decent blog entries, so far, this sissy in training has had the most thoughtful responses thus far. Let’s see if she can make it through the bulk of her training or better yet — all the way until the end. 

There is a method to my madness…it is to build a foundations. Sissies like to purge, and while that is another post itself, my goal is to build a foundation so when the inevitable purge happens, and you inevitably go BACK to your sissy self (you’ll never purge indefinitely, you will always go back) – you’ll have your foundation to build from. It wont all be lost. The Sissy Mantras are the first step in building an unbreakable foundation.