Diary Entry: Sissy Bottoms Should Never try to Top

During week 2 of Mistress Lillith’s training she had something come up IRL that rightly required her attention. They were a difficult 7 days for me. I was new to her training and felt like I needed a lot of instruction, boundaries, a lot of structure. I remember watching several videos of female subs being flogged by dommes and other tops (most subs are females, it now occurs to me). Strangely, it had a deeply soothing and reassuring effect on me. I vividly remember watching some of these videos and reading about d/s relationships and thinking “I just need to wait patiently for my Mistress.” But this was all being created in my own mind and I actually have little experience with this type of relationship and so doubt crept in.

How should I be behaving?

In week 4, after completing a particularly arousing assignment, I lost my composure. I was pining hard for Mistress Lillith. She is more experienced than I am and has a better understanding of our relationship and what is objectively happening.

I am less experienced and it’s easier for me to confuse our relationship and get carried away by some of the most powerful feelings a person can experience.

I had expectations and made demands of Mistress Lillith.

I think my reaction was a typical pyschological one. But it was not acceptable for a sissy bottom. And I have goals to be a better sissy bottom.

“You are the submissive. I am the Mistress. You came to ME with a need. Follow my lead. Period.”

Yes Mistress. It’s what I needed to hear.

“You belong to me.” “I’m okay releasing you should you feel the need.”

Ownership. Consent. Thank you Mistress.

OMG Mistress Lillith sent me a personal video too (what an amazing domme!!!).

“I am your Mistress. You fucking belong to me. You want to be my bitch? You want more of me? I hope you’re ready.” “You serve me. Not the other way around.”

Yes Mistress.

Sometimes when a newer sissy is going through sissy school and training with me, they will have new and intense feelings that will overpower them. Think of renewed hormones, thing of that teenage angst. It is very similar to that.

Yes, it is important to understand that Dommes, Mistresses, your Sissy trainers, they are people too- there are lives that we have and live outside of our sessions – be it online or in person.

While the feelings can be very intense, and you can have a very strong connection with your Mistress – and right then and there she may be your whole world – understand there is more to the picture. I don’t always share with my subs and sissies the ongoings of my personal life – in this instance I was taking care of an elderly family member that had been hurt. Why do I share this? Simply to say – don’t act as though you are the center of the world or the one and only thing that she is focused on. You could actually damage your relationship with your Mistress by making demands and assumptions.

Here, this sissy was learning. Im slow to anger and adore this sissy – she just needed some redirection.

I am the Mistress, I am the Sissy Trainer, it is I who will be obeyed and I who make the demands. NOT the other way around. 

Exposed Sissy: Lisa

Sissy Diary Submission from Sissy Lisa – aka MARK

My sissy journey started at a young age, when I raided my Mums panty drawer. The obsession started and I fell in love with the feeling of soft feminine items.

All these years later and now I wear panties 24/7 and wouldn’t have it any other way.

I love slipping in to a nice dress and matching them with tights and sexy heels.

We girls deserve to feel great and look amazing.

I regularly go for long walks at night dressed in sexy outfits, always with tights. It’s my dream to be able to go out on these walks during the day.

I love exposure and humiliation but always come back to my Twitter account and delete it, this allows me to be exposed and I can’t do anything about it.

That is such a wonderful feeling and one I crave so much. After years of dressing I decided I needed to get out and meet guys, I wanted cock so bad and I’ve had my fair share. So far I’ve met 14 guys and enjoyed a mouthful everytime.

I want a boyfriend one day who I can snuggle up to and suck off at will.

I would love everyone to share my exposure and love have sissy chats with others.

I used to think this was just a phase and I would go back to women but I guess being a pathetic sissy means I’m totally gay now.

Thank you Mistress Lillith for allowing me to submit my exposure

When you mentioned that you would ‘go back to women’ I snort laughed out loud. No one is going to accept you as some ‘macho stud of a man’ – there is no going back my dear. 

Once a Sissy, Always a Sissy

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