Diary Entry: Getting Trained as a Sissy

*This entry is from one of my newest Sissy Camp Trainees* 

This past week has been filled with intense eroticism. I’ve savored every written word from Mistress Lillith. Reading and soaking them in over and over again.

“[Just] like I’ll have your sissy ass worked with a dildo at some point ;)”

My mind ravenously extending the idea into a full blown fantasy, building on the suggestion and filling in all the missing details. In one instance a cam session at my house. Another, Mistress Lillith in tight red latex is standing there next to me. A slow motion video with me as the protagonist plays on an endless loop. Orgasm… The mind is the most powerful errogenous zone.

“…if you over step a bounds or are in need of discipline…I never shy away 😉 you will find yourself learning how to treat and respect a Mistress.”

Thoughts of the impending loss of control, and in some instances, the present loss of control, overwhelm. Drifting slowly into sleep and twitching back out again as I hear a mantra: “I am sissy… I enjoy all things feminine…” “Oh my gosh I’m being trained!” The thought jolts into my head suddenly like something akin to panic.

These are deep, powerful emotions of lust and eroticism being drawn out after a lifetime of being largely unfulfilled.

How can I serve Mistress Lillith? I can be obedient and respectful. But is that really adequate compensation for the experience she’s giving me? Anyway, that’s more the process of serving, not actually serving itself. Our setup does not faciliate physical servitude. I can’t clean her house or mow her lawn, and if I could–creepy factor aside for a moment in this fantasy–it’s still nowhere close to proportional for her unwrapping these deeply held, occasionally repressed, incredible feelings inside of me.

And who is enjoying this more? No doubt a lifestyle pro domme like Mistress Lillith finds some mild enjoyment or amusement in this. How else can one explain the photo shoot in a corset and Darth Vader helmet? She also may be more callous to the novelty of it all. I mean there are probably thousands of Niteflirt subs–all with one thing on their mind–and all who act and behave almost exactly the same. She’s seen this before. Again, who enjoys this more? Let’s just say our play together is almost certainly not borderline changing Mistress Lillith’s sexual identity!

What is the best way to serve Mistress Lillith? Money is the best way. It allows me to pay to have her lawn mowed, or have her house cleaned, or whatever else *she needs*. It allows me to be a useful, helpful servant. I will be obedient and respectful and always pay well for taking up any of her time, and to express my gratitude for her offering me an opportunity to explore this kinky lifestyle and introduce me first hand to femdom.

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!

Being a Sissy Housewife

Are you the Sissy Housewife Type?

Sure you can watch your tv shows of the Real Housewives of ‘whatever city’. Gorgeous women, with luxurious lives. You, my sissy, can be a gorgeous sissy but your luxurious life will be much different.

The lifestyle of outtings and parties is for the enjoyment of your Mistress. SHE is the one that regularly attends A-List social gatherings…and you as the sissy…if you are lucky – will get to join her as her servant.

You are the housewife Sissy. Your duty is to serve.

You could see this as a sissy maid type role but I see a sissy made as someone with a uniform and one that would sleep in separate quarters.

The housewife would actually get to sleep in the house and even though there would most certainly be a separate bed situation going on.

Your duties as a housewife are similar to that of a sissy maid. You do the cooking and cleaning, the chores and make sure that your Mistress comes home to a glass of red wine and foot massage, on especially hard days, an already drawn bubble bath.

Your hair must ALWAYS be in tip-top 50’s style shape and you must always be prim and proper. You DON’T look like the maid, but you certainly have the duties of one.

When you’ve done your chores you only hope that the latest soiree so that you can be shown off as a top Sissy Housewife by your mistress.

And yes, just like a housewife is expected to perform certain marital duties – you will have those as well.

Let’s just see how you fair as the housewife first. This is another way that you differ from JUST the sissy maid. A Sissy Housewife has extra privileges that a sissy maid, may never encounter.

If you are a prim and proper Sissy that is devoted to your mistress in a special way, perhaps you would fit the roll of a Sissy Housewife. You are an Owned and Kept Sissy Housewife. Your Mistress doesn’t have to lift a finger when you are around, you are hopelessly devoted to her and you are going to look fabulous while doing it – you don’t get to be an ugly housewife.

Don’t worry dear, if you are new to the housewife sissy duties, Mistress Lillith is here to show you the way.

Once a sissy ALWAYS a sissy: Return of Sissy Tracy

There are people that purge their sissy attire because they feel as though they can rid of it once and for all, and never again go back to their sissy loving ways.

That is wrong…you will ALWAYS come back…you cannot escape being a sissy.

I often tell my sissies to fight the urge to purge because a sissy purge is always so drastic and always so expensive later on – because you will want it back, and will have to start your collection over.

I don’t know that this particular sissy purged anything but, I have exposed this sissy a time or two in the past and a few years later here she is being exposed again. This time in a full sissy exposure kind of way. Why? Because once a sissy, always a sissy.

At the time Sissy Tracy didn’t want to be exposed but followed the rules of the exposed sissy assignment and was ultimately exposed.

If you want to read her old post from 2014 check out Sissy Tracy’s Exposure.

And here we are…3 years later…and Sissy Tracy is just a feminized as ever.

“I am a crossdresser, to the point now that I cannot think of anything else most of the time.  I love looking at pictures of feminine women all dressed up….especially anything vintage and pin up related, and I imagine myself like that.  Women were so much for feminine and dressed like it all the time back then.  Almost every waking hour I am thinking of dressing up and acting like a woman….with all mannerisms like posing with bent wrists.  I even dream of going all the way with acting out as a woman by meeting with men and 

sucking cock to make me feel as feminine as I can.  “

She has zero fear of being exposed now, but it seems as though it is time to rev up her sissification and feminization journey. She already walks the walk and looks the look…it’s time for her to find a real man to treat her like the sissy slut she is. Who wants to lend their big meaty cock to this sissy slut for you to show her your moves?

 

Say hello once again to my Sissy Crossdresser from New Jersey. She’ll be on craigslist if you want to find her and give her a taste of your scrumptious cock.

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 😉

Pop Sissy Kelly’s Cherry

Time to pop a new cherry on an exposed sissy!

The best thing about exposing sissies is that once their information is out there on the world wide web, even if for just a few moments – it can be out there forever. From people right clicking and saving to use it themselves, to it being saved on the wayback machine and internet archives. You just never know.

Some sissies like being completely exposed, while others want to hide in plain sight. I think Sissy Kelly is one that likes to hide in plain sight. Those that are closest to her could tell the body type, and would just KNOW.

I have a feeling that Sissy Kelly is one that people wouldn’t be surprised if they discovered her naughty little crossdressing secrets. Just one of those people that you KNOW something is off…so when it is all exposed, they have an ‘ah-ha! Told you’ kind of moment.

“I am sissy Kelly.  I have been wearing women underthings cent I was (of a very young age). I started with my mother’s and sisters panties. I live in Clinton, Tennessee.  I want to be outted so am forced to take that next step in being sissy and pop my cherry”

As a girl who loved her panties I always knew if a pair went missing. Im willing to bet mommy and sister knew you were perving through their panties and wearing them. Makes me wish I could be a fly on that wall to listen to the stories they had about you!

Well Sissy Kelly, your cherry is sort of popped. We would consider this a ‘finger banging’ kind of sissy exposure. Why not take a bigger step into the spotlight. I think I pulled your email and phone number. Guess I need to go onto craigslist and post all of that info and see if someone really IS willing to pop that sissy ass cherry!

Free Sissy Task

I don’t do free sissy tasks assignments very often…so when I do, you need to complete. Doing so tends to inspire me to possibly  put more free sissy tasks out a little more often.

And besides, it is the holiday season. So … Enjoy ~

Specifications

I am doing a compilation video of 12-days of sissies. You can take more than one day but, no more than 3.

~This assignment requires that you record a clip, that shouldn’t be any longer than a few seconds.

~No Nudity. You are a sissy. You should be dressed up 😉

~Id prefer you in panties or with lipstick on or completely dressed in the clip — but you do not have to show your full face nor have any distinguishing marks that would identify you.

~Look up the tune of 12 days of christmas and you’ll know the tune to sing your line in.

Once I’ve received all the submissions I will organize them into the full song and post it on my sissy site, and a link to it from twitter — I will send you the video as well.

DEADLINE: Once I give you your line(s) you will have 2 days to get the recording back to me before I reshuffle the line back to assign to others. This assignment is only good until December 10th, then no more submissions accepted 🙂

Please feel free to send me a message if you have any questions or for more information or if you would like a line or two to record. (If you tell me a short summary about you I can give you a line that is best suited for your personality)

You can send me a message on Niteflirt, Skype: mistress.lillith or send me an email madamerotic @ gmail for your lines and how I want it done.

I don’t put free sissy assignments out often so enjoy it while it lasts. 😉 If you want other sissy assignments sign up for sissy training. Yes this particular assignment involves a little bit of exposure but it’s minimal.

 

Exposed Sissy Crossdressor

Having been a sissy creator for as long as I can remember, and having done it professionally for a number of years now – I always find it fascination when I see some sissies, and expose some sissy crossdressor

exposed sissy christinaBy day they walk around, A-type personalities, rough and rugged. They have deep booming voices and strong macho type personalities.

You could almost say that they are the masters of disguise – or perhaps sissies of disguise.

I say sissies of disguise because their outward appearance is just a façade. Their day to day actions are the real disguise.
The minute they get home and undo that tie – they slip into something a little sexier. A little more feminine.

That burly man you work next too, or you see at the store…is really a sissy crossdresser. Just like Christina here. You can see that masculine mustache but is anything about what she wears masculine? HAHA absolutely not.

sissy bimbo slut exposedIt is fun to reveal and expose not-so-manly, manly, sissies.

Just like Christina stated:

The secret I would like to reveal is that I am a sissy crossdresser. Not this super manly man everyone thinks I am. I love high heels, makeup, nylons and other girly things.

I am a sissy boy who likes to dress up as a bimbo.

And Christina certainly isn’t the exception to the rule. The longer I train sissies, the sissies I expose and uncover – the more I realize this is the NORM. ~or not…normal is so vastly underrated anyway.

Impregnating My Sissy

What could possibly be more humiliating than a sissy that was (1) forced into frilly feminine attire and (2) forced to service the big black cocks that mistress makes you suck and fuck and now you find out that you are a pregnant sissy.

Having to endure and go through the motions of a full on pregnancy.

This isn’t what you wanted is it sissy? But you didn’t have a choice.

I ushered you down into my play room and began your daily punishment rituals. I dressed you in shimmering outfits that took your ‘sluttyness levels’ up and beyond. I made you slather your body in baby oil for that smooth, sleek look and feel.

Pulled your hair back and out of your face and applied a deep shade of ruby red lipstick, then spritzed you with a floral/fruity perfume.

You had gotten ready like this before, but something different was in the air. You were getting a little nervous…weren’t you sissy?

Then the real men came in…12 of them. Quite a few for such a special occasion don’t you think?

They took their turns on you sissy. Each one pumping their delicious, thick load of cum inside of you. Riding you raw—

And Each Time I made you stay in the gay ostrich position I had taught you. (head down between your knees, ass up and cheeks spread with your finger tips)

Their cocks were huge, their cocks were thick, and their loads were unlike anything you had seen before.

When they were done, you were forced to remain in that position for several hours until I came back in—

3 weeks later — You know what that special little occasion was all about.

I wanted to impregnate my sissy and that is just what I did. Your belly will swell, your nipples will become sensitive and your tits will grow. MMM…this will be quite a journey for you my little sissy slut slave…You will walk around for a long time as my pregnant sissy.

Sissy Hygiene Check

Reminder to my Sissy Girls Regarding Sissy Hygiene 

There is always a special way that I expect my sissies present themselves whenever I summon them. Some have specially selected ceremonial outfits, and others have a variety that change.

Then again…there are still those in training that are expected to come to me in nothing but a pair of panties and stockings.

Reason being: Hygiene check

You want to be a sissy girl right? Therefore there are certain standards that you must abide by in order to receive the privilege of labeling yourself as one of Mistress Lillith’s sissies.

I LOATHE when boys claim they want to be a sissy, and be trained and turning into a girl, and can’t follow simple steps like hygiene and cleanliness.

What does Mistress Look for?

~NO HAIR—No hair on your legs, chest, arms, face, or groin area. Hair on your head is fine, but nothing unsightly. If you are one of those hairier boys…you’d need to shave or wax your back, neck and ass as well. I DON’T want to see hair.

Its funny how much of a fuss some silly sissy sluts make over having to shave. But, that is where you make your intentions known. Either you want to be a sissy, or you are just playing dress up.

~A smooth finish—Use baby oil to lube up your newly smoothed skin to make it shine and sparkle

~Fingernails—cleaned, polished, kept. They don’t HAVE to be long, and I don’t always require nail polish. Hopefully if you are training with me, you understand the difference between polished nails and nail polish. You need serious training my dolls, if you do not.

This is is among the many things Mistress Lillith looks for when training sissies.