Is it Russian?

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Conversion (Poster)

The other side of this is sissies that throw out all their girly things when a moment of doubt washes over them. It's wasteful and you'll regret it - don't do it!

You're Out!

Of the dating pool.

We seemed to be a bit low on forced feminization and cocks, so now I've addressed both those deficiencies in one go. I think this might qualify for the first cuckolding caption as well!

Slipped On, Slipped Out

Regina is coming, but in the meantime more from me (which might help you fulfill her mandate).

This would be the first instance of a magic-oriented caption on the blog. The girly aura of an enthusiastic sissy is also pretty magical, but not quite as fanciful.

I wonder if that's a fair price? I think I'd take it.

Preparing for Regina

I'll be gone for a while in the next couple weeks, but I've lined up a special surprise for you sissies for when I'm gone. Hopefully you'll give her your undivided attention.

(Regina uses beautiful Scarlett Faye as her avatar)

Early Bird Catches

Wait, I know this one! "...the sissy."

I'm not sure how popular the captions or links or anything else is. I'm not so sure my presets, captions or even roulettes have permeated all that much of the online sissy community anyway.

The lack of any feedback at all is pushing me inexorably closer to just making things for myself and not bothering to go to the effort of putting them on the internet. So if there is something you like or want to see more of just click on the reactions (even for past postings).

Diligence (Poster)

Of course, what you practice will depend on what kind of sissy you aspire to be.

Nailed It! (Assignment)

Today is pedicure day!

To help keep you honest after playing with your clitty we're going to help make sure you can't immediately undo all of your precious work. You'll need a box you can lock with a padlock (not a combination lock). A simple bicycle lock will work.

Make sure all the nail polish remover in your house fits inside the box. Find a large plastic or paper cup (if you don't, try a convenience store coffee cup). Fill the cup with water. Connect some string to a toothpick and tie the other end to your key so that you can hang the key right in the middle of the cup. Put the whole thing in a freezer and get started on your pedicure!

Pedicure's work best if you have a whole set of skin and nail care products, but today you can get by for this assignment so long as you have a clear nail polish that can work as a base coat and a colored nail polish. If you'd like to go for the whole shebang, you could start with a basic pedicure guide online - like here or here.

There are a few basic highlights. Soak your feet and clean them well; spot cleaning is best done with nail polish remover, which can help remove oils - as well as its intended purpose removing nail polish. Clip your nails so that they don't extend beyond your toe. Cut them straight across. Don't try to put the clippers between your toe surface and the nail at the corners; this can lead to a type of in-grown nail.

With that pedicure prep out of the way, you can start on your polish. Put on a clear base coat. Let it dry completely. Wait a full hour if you have to. No stroking; I'd hate for you to accidentally lose heart half-way through.

Now it's time for the colored polish. And it should be colored. No nudes or half-tones. If you pick a flesh-toned pink it ought to be shiny or glittery.

Most girls have a multitude of nail colors, I'm sure you can find something. Red is the traditional option, but it's also not particularly popular for normal wear for most women. I suggest a shimmering pink, light metallic blue, or dark maroon or purple.

You only need to apply one coat, but depending on your polish and color you may want to apply a second. If it looks exceptional then you're ready for the next step. If it's streaky, bubbly, smeared or in any way not immaculate...well, then you'll have to use that nail polish remover and start all over again. Clean any polish from your cuticles if you happen to color outside the lines. Make sure you don't accidentally foul your pedicure polish cleaning up.


You want to be able to make it perfect not only so it looks excellent on you, but also so you can more quickly and reliably apply it in the future.

Toenails looking stunning, sissy? Great! Now it's time to take that nail polish remover and lock it away. You may only play with your clitty once the key is encased in ice.


You should keep that polish on for 3 days. If you have the urge to remove it after playing with yourself then take the key out of the freezer and let it start thawing (I'd hate to see you lose or damage the key breaking the ice apart...). If at any time before it thaws you get excited again you should put the key back in the freezer. You must also put it back in the freezer before you go to sleep.

If for some reason you break down and can't follow these directions you should do the assignment again - adding in a manicure with polish for good measure. And this time either pour out your remover or bury the padlocked box - it's for your own good, sissy.

Lowering on the Bar

Certainly not lowering the bar. You should always strive to be the best girl you can be! But of course sometimes you'll have to decide: up or down; in or out?

Photo of Kimber James

How do you get yourself into such precarious situations, sissy? :D

You're a Star!

If only it were so simple (or we could all have such beautiful voices). But don't despair, sissies - every one of you is a star for expressing your femininity.

I also checked the site settings and comments required a log-in (which even affects reaction voting). That doesn't fit the chan-board inspirations for this site or my free spirit. So now you can be a star here anonymously, too!

(Plus links are hopefully easier to see now that they're not 'grey' and 'slightly different grey.')

Truth or Dare

We certainly can't play spin the bottle or strip/dress-up poker, but we can play Truth or Dare! So which will it be, girl? Truth or dare?

Truth: Why do you love dressing like a girl?

Tell the truth - you love dressing up like a woman. You love panties and dresses and skirts. So, why?

Some sissies are 'forced,' most sissies do it voluntarily. It could be from the feel of soft, gentle fabrics like silk and lace that men's clothing just don't have. Maybe you're just indulging your own autogynephilia. You could have a master or mistress you're just eager to please who loves you in frilly pink. Only you can know for sure, and now you can tell someone else.

It wouldn't be much of a truth if you kept it to yourself; post a short explanation somewhere with a little permanence - something that will be around for at least a day. You can do it anonymously, just write it somewhere. "I love dressing like a girl because..." You can even post it here if you can't find chan board or forum or website that suits you.

Dare: Buy some tampons

Go to a convenience store or department store and purchase a box of tampons for yourself. Oh, but it's not that simple, sissy. You must wear some makeup, you cannot use a bag, and if anyone asks you must tell them that they are for you.

You don't need to wear heavy makeup. In fact, it can be barely visible if you want. But you must wear some eyeshadow and some lipstick - however nude or thin they may be applied. If you're extra daring you could try to buy them dressed completely en femme. If you're offered a bag you'll politely refuse. If the clerk asks anything about them ("Errands, huh?" or "Wife had an emergency?"), you'll tell him, "These tampons are for me."

When you get home use one of your tampons (hopefully you bought size-appropriate tampons). You can leave it in for a few hours or take it out right away. Of course, if someone comes over and asks about them you'll have to tell them that they are for you.


Boring (and potentially gross), but informative safety information: Some sissies (and girls) have concerns about toxic shock syndrome from tampons. TSS stems from the build of toxins released by bacteria where it can enter the bloodstream (not necessarily the tampon material, but more absorbent tampons means more moisture). The bacteria can grow in warm, moist areas (which is why it's better to store your tampons in a hall medicine cabinet instead of a bathroom); TSS in relation to tampons happens from the collection of menstrual fluid and the heat of the human body. You can decrease your already minimal risk by washing and drying your hands before inserting, using less absorbent tampons (although there really shouldn't be much fluid to absorb from your rectum, sissy - I told you it could be gross), and changing out your tampons frequently.

Hypochondriac sissies may substitute a buttplug for their tampon.

Shock (Poster)

That's "astonishment" and not "electrocution." Although I'm sure electric shocks could help some of you with your training...

Vitamin pills posing as HRT drugs...now where have I seen that before...

Training in Trainers (Assignment)

Hopefully you're a sissy that prides herself on her healthy lifestyle and positive attitude. If not, today you can start on a path to fitness; if so, you can continue your good habits.

Running is one of the most effective forms of cardiovascular exercise - that just happens to burn calories well and improve muscle tone in the butt and legs. Perfect for a sissy! Well, anyone, really.

Of course, you won't just get out and run - you might do that already.

Tomorrow you're going to go at least one mile (about 1.6 kilometers). Heavier or older sissies may need to work up (or down, as the case may be) to actually running. You may walk or run, but either way you're going the distance.

Women have to wear panties and a bra while running. You will, too. Find a pair of simple panties (we don't want you to ruin your good lacy, frilly or silky panties). If you have a sports bra - great! Otherwise pick out one of your older bras; it will be your new running bra.

If you don't have a bra (or you don't want to potentially ruin or soil one) don't fret, girl! Find some tape, breathe in and wrap up your breasts (hopefully you don't have any chest or back hair, sissy!). Make sure it's not too constrictive, you still want to be able to breathe easily.

Some sissies are a bit closeted and don't even have panties! Those ladies may either buy a pair of panties by tomorrow or wear a pair of gross male underwear (preferably tighty-whities). But if you do wear male underwear you need to take a black marker and write "Panty Girl" on your ass first.


To prepare yourself you may want to listen to this. If you have a music player you should also set up a proper playlist. Perhaps you have some Shania Twain, Lady GaGa, Avril Lavigne, or maybe even some Lily Allen. Up beat music helps keep you energetic for running, and slower stuff is nice for a cool down at the end.

Of course, if you don't own any of those songs (maybe you should) find something appropriate to express your femininity while running. If nothing else you can run to that hypno file.


You should do this once every two or three days until you can run a mile in under 8 minutes, but the assignment is only for one day.

But do you really want to leave your inner girl cooped up like that?

Cherry's Delight

Cherry's mistress seems to have an excellent training regiment.

Good Girl, Natalie

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Rolling for Femininity (Game)

Alea iacta esto! Not up on your Latin (or English idioms)? "The die has been cast" - what Julius Caesar supposedly said as he crossed the Rubicon and invaded Rome to seize power. That's a bit dramatic, but today you'll get to seize a bit more femininity for yourself.

Find a six-sided die. Now you get to do some simple rolling for a task that any sissy can complete at home. Iacta cubum (roll your die, sissy!).

Put on a simple dress (or just panties if you don't have a dress). Relax on a couch or bed - laying on your side with your knees together. Watch the girliest thing you have available - this could be Oxygen or Lifetime if you have cable, a cute anime on DVD or a romantic comedy (Hulu has some stuff if you have no other ideas). Enjoy for at least one and a half hours.

Perform some simple nail care; file and buff your fingernails. You're aiming for a nice elongated oval shape. Nails don't always cooperate and you might have to content yourself with just well-rounded edges. Trim your toenails as well (make sure there's no gross dirt beneath them). If you have nail polish put on at least one coat. You don't need to keep it on, but maybe you should, sissy.

Wet down your groin area with warm water. Wash it thoroughly (take a shower if it's easier for you). Carefully shave everything beneath your clitty. If you want to keep a bush make sure you trim it properly (a simple triangle or cute heart of short 1cm long hair would be pretty). You don't need to shave your legs too, but hopefully you're already being a good girl and keeping them smooth.

Practice improving your penwomanship for 30 minutes. Look here if you need some inspiration. Sign your (female!) name until you can do it comfortably. Try writing a short autobiography (surely something in your life must have led you to sissydom!). I'm sure you can find a pretty pink pencil (well, I'm sure you can find one at home where the eraser is pink, anyway) and some paper.

Practice speaking with a female voice for 30 minutes. Try starting here if you're lost. As an alternative quick method you can try: Breathe deeply, gargle with your voice until it's as low as you can go without having it crack or skip, repeat "Wicked Witch of the West" thirty or more times while trying to speak like an old man or old lady. Hold a pillow or towel over your face if volume is a concern.

Draw a heart on your body with a sharpie. Write "SISSY" inside of it. The letters should be easily legible and at least 1cm tall. Draw the heart first and then write; if it ends up too small fill in the heart and try again. Your first try can be in red ink, but each subsequent try must be black or blue ink. Write anywhere but the soles of your feet.

Most of the visitors are from the US and use imperial standards. You don't need to run off to find a metric ruler; a half-inch will do fine, ladies.



Actually Julius Ceasar most likely said, "anerriphtho kybos" (in Greek), but understanding Latin and classical Greek are not necessary for you to become the best girl you can be. Unless you aspire to be a domina in ancient Rome.

Caption Selection

I know my captions are all over the place. Sometimes I'm in a slutty mood for cocksucking training and "forced" HRT. Other times I feel like a princess and enjoy captions of acceptance and supportive feminization (or even coercive "in your best interest" feminization). But I know some people like it rough and some people like it gentle, so I figured I'd point everyone to some other caption resources that they might enjoy.

SissyLouisa (the only one so far to leave a comment) has The Dirty Mind of a Wimpy Sissy, which has an abundance of forced feminization - and even more BBC worship (that is 'Big Black Cock' for those out of the loop) captions. But As a sissy I don't think you should be picky about color or size :D

Michelle's Feminine Place Caps has an assortment of forced feminization, 'caught dressing', and persuasive crossdressers captions.

Club Sissy has a section dedicated to captions from a variety of authors (I know Michelle above is one of those authors, for instance). The content can be hit or miss, but there's surely something for any sissy. Unfortunately Club Sissy does require registration to view the caption library.

Sissy Kiss has a "captioned piccies" gallery of user-made content. Sissy Kiss' audience favors ABDL (that is Adult Baby/Diaper Lover), so most of their captions trend towards incontinence, being forced to wear diapers (although often with frilly pink dresses over them) or girls who are still young at heart.


And to end today, here is one of my favorite captions. Have fun, sissies!

(I'll also point out that neither of the captions in this post are mine; I'd hate to imply credit for other people's stuff)

Disbelief (Poster)

Alright, I hesitate to actually call this inspirational except for the most imaginative of sissies, but it was part of the poster set I made.

Because what sissy would really be in disbelief? I'm thinking most of you girls would be in ecstasy.

Practicing Alone (Assignment)

There are sites with sissy assignments hidden all over the internet. Sissy Station is probably the most prominent, but there are an awful lot of forums where you can request simple assignments.

But today I have just one simple one for you (if your girly personality is old enough). Get a shot glass and follow the instructions in this video (or download it from here). Follow them to the letter.

If you don't know what ruining an orgasm is: if you stop jerking or rubbing your clitty an instant before you cum you'll still cum, but it will just sort of flow out and you're usually still horny.


The Sissy Spot has had its 1,000 visitor yesterday. Thanks for visiting, sissies!

(I think that puts our comment/reaction-to-visitor ratio at about 1:1000 :D)

A Flowering Girl

Being a girl is - naturally - rarely about sex.

Of course, most sissies miss out on a glorious girlish childhood (unless they managed to occasionally squeeze into a sister's adventures). So take a moment to imagine how excited you would have been to have a guy pick you up to go to prom; the fun and joy of a sleep over; or the beauty and spectacle of being a bridesmaid for your friend or cousin.

Hypnotism

Hypnotism can be a great means of unlocking your inner girl's potential...or just an immersive form of erotica.

We've already covered subviewer, but there are many other types of hypnosis-related stuff. I've also mentioned Anna Malice's Sissy Self Hypnosis - which has daily sissy hypnosis videos from various places on the web (as well as regular porn and fetish videos).


Warp My Mind has an extensive collection of hypnosis files - along with inductions and other hypnosis-related things. The file browser has categories that cover a variety of stuff, but since you're at Natalienne's Sissy Spot I would guess the Feminization files would be the most appealing. The site requires registration, but with that registration you can download all the free files you want.

I'll recommend the Little Miss Squidgy or one of its continuations. Can you pass her test, sissy?

If you'd like something with a more human voice (although the text-to-speech in the LMS files is intentional and doesn't sound too bad) I would recommend Elena McIvor's cock conversion mantra to go with the actual file (hidden away on a different site).

Allison In Love doesn't seem to be active any more, but her files (which are less sexual in nature) are also available.

Anguish (Poster)

In some cases not being caged could be worse than being caged - if a sissy is obedient and trustworthy like a good girl.

She could, of course, cum without using her hands.