Sunday, June 22, 2014

Sun, Swimming and Sissy (Assignment)

Photo from
It's summer, sissy! (At least for the northern hemisphere, where most sissies are—sorry southern sissies). You know what that means? Going outside to enjoy the nice, warm sun. Showing a bit of skin with tight, short clothing. And outdoor swimming to tone up your butt, keep you sleek and show off your feminine curves. What's the point of shaving your legs, painting your toenails and toning your body if you're not going to show it off, sissy?

Let me stop you right now and tell you that this assignment is best done on a warm (75 °F/25 °C), sunny day. If you're an unfortunate sissy living in a rainy, overcast-laden locale, wait for a good day before reading and doing this assignment. But if you're a lucky sissy blessed with good weather, carry on!

Now, you might have worn a women's swimming suit before or you might not have one yet. Today it won't matter.

I've espoused my love of the one-piece before (sure you can show off more of your body with a bikini, but there's nothing that screams "I am girly" like a form-fitting one-piece you can't escape or hide like a bikini bottom.

Your assignment today is very simple, sissy: Go play in the water like a girl. First, don your girly swimming suit. One-piece, two-piece (even an amazing three-piece where the bikini bottom ties together!), the specific suit isn't that important. Now get in the water. Done.

(Needless to say, sissy. You shouldn't be cleaning off any nail polish or makeup you might be wearing.)

If you're one of those sissies in denial that hasn't come to terms with the fact she shouldn't be buying men's clothing and all you have is gruff, ugly male swimming trunks, you will have to "make" your own swimming suit. Grab a permanent marker and draw the outline of the suit you are supposed to be wearing. That's right sissy - the line under your breasts, the fabric patch covering your nipples, the straps to hold it in place, the strings of your bikini bottom. You will draw your suit on everywhere you can reach. Finally, as punishment for not accepting your true nature, you'll also write "I am a sissy" on your tummy in big, legible letters. That way, when you buy your one-piece to cover the writing, you can go out and no one will know what a bad girl you've been.

Backyard pool, busy beach, secluded watering hole. The location doesn't matter, as long as you're wet from head to toe. Feel the added weight of the water soaked into your suit. Cherish the gentle caress of your sopping wet suit clinging to you in all the right girly places.

Of course, for more house-bound sissies (or sissies living in deserts), it can be a bit difficult to find a bathing spot. In that case, you can use your bathtub. Fill it up, splash around, and enjoy yourself. Then quickly pull on your (white!) overshirt and shorts if necessary, throw on your sandals and head out to check the mail or walk around the block. No dillydallying, sissy—you'd better me wet in all the right ways when you get outside!

Now that you've taken your first dip into the summer, it may be time for a bit of tanning. Or just lounge around and enjoy your girly attire until it's dry and then put it away for next time. Time to start enjoying the summer, sissy!

Thursday, June 12, 2014

Bending and Breaking

Press a sissy long enough and she'll give in...

Also thanks to the sissies who submitted nail polish pictures!

Even though I forgot to throw up a new June picture in the Sissy Schedule (hey, it's barely June-like weather over here!), everything should be better now.

Saturday, May 31, 2014

Summer Reading

Photo from
The more feminine-nature of many sissies means they often have a more feminine appetite for erotica. Most manly guys love videos or pictures as their porn of choice, while many women settle on erotic novels or erotica. No wonder that many sissies crave a good captioned pic, then! But there's an abundance of free literature to excite your aching clitty.

 Other than sourcing some juicy erotica, it's important to consider what type of story you're looking for. Scientific, magical or mystical transformations? Forced feminization? True tales of sissification? Mind control? Your options are truly limitless. As a budding selection of favorites from a variety of genres:

 The Setup by Superfry

 A guy is troubled by his lost ex as she returns after dumping him and tries to make him suck cock. Features blackmail, semi-forced feminization, crossdressing and manipulation.

 Nymphomania by Edward Miller (and the sequel Help!)

A freshman college students is experimented on, becoming going from normal guy to hyper-aroused slut; her body proportions and arousal grow as she reacts to cum. "Scientific transformation, lots of sex, mind manipulation.

Bike Shed Rendezvous by Tomsparty

A 2nd person tale of how you're lured to the school bike shed and tricked by one of the popular girls. Crossdressing, manipulation, co-erced sexual acts.

The Sadler School Sissy by Slave 23

A new addition to a school finds out he's forced to take on a role to 'relieve' all of the other jocks in school. Transformation, forced feminization, co-erced/forced sexual acts.

Remember: There's no punishment for printing one out so you can lounge out by the sea reading your sissy erotica!

Wednesday, May 14, 2014

Sissy Body Art (Assignment)

Perhaps you may be up for some more sun-baked sissy body art. Unfortunately, many sissies are still faced with sour weather. Plus, suntans have a lack of fidelity. They can also be difficult for many sissies to apply. Fair-skinned sissies often risk sunburns and dry skin; ebony sissies may have trouble getting their art to show up at all.

Luckily there's another option: drawn-on body art. (And for the sissies that have already taken the next step and gotten an actual feminine tattoo: Way to go girl! Your dedication to girliness is an inspiration!)

Find a fine-tipped permanent marker (or my favorite for that extra feminine touch for a sissy: a lipstain) and pick out a design you like. For sissies with limited artistic experience, a simple shape will work best (the shoulder star like Bianca here, a Venus symbol, a bow). In a pinch, a short word also works well. Capital letters are easier to write neatly - even if you've been practicing your girly handwriting, writing on yourself may be difficult. If you can't think of anything else, labelling yourself SISSY would be just perfect!

 But you don't want to hide your art away!

You have to show it off, sissy. If you're not quite brave enough to go with a fully bared piece of body art, you're going to go as close as you can: Your shoulder/upper arm, lower thigh or ankle (hidden, but just barely). No need to worry if you have concerns about your drawing skills - you've got plenty of places elsewhere on your body to practice where no one will see! You can try to draw or trace a pattern in pen and then fill it in with a more permanent solution later on. Or try free-hand if you're a bit more confident (short strokes will work better as you flesh out your design, the marker will naturally bleed over a bit into the surrounding skin).

Once you're done, you'll have a neat little girly reminder that's just a wrinkle or ruffle of clothing away. A raised sleeve, a lowered sock and you'll be able to show off your girly art!

Most permanent ink will wash off within a few days (depending on your marker, it may become much less visible after just one wash - feel free to touch it up as you see fit). If you have sensitive skin, test out a marker first to make sure you won't have any unfortunate rashes or uncomfortable events to ruin your artistic experience.

Most importantly - have fun and express your inner sissy!

Wednesday, April 23, 2014

Sit back and relax

Maybe listen to a little something...

Sorry about the slow updates! Also, thanks to the handful of people that vote and comment!

Sunday, April 13, 2014

All You Could Want

...and right where you want it.

(Photo from Sexi Lexi's tumblr).

I recently discovered Sexi Lexi and her stuff is fantastic. I know I've got a bit of a cum fetish, so I'm happy to see she has a few choice shots. I feel like sissies are just a bit too eager to swallow (which is good for the sissy, but bad for the show!), so it's nice to see a t-girl show off a bit. It doesn't hurt if she has tons of pictures where she looks great, either!

Monday, March 31, 2014


But is it really blackmail if you're so willing to do it, sissy?

Besides, sissy, you can be sure anyone who gives you print blackmail photos already has plenty of digital copies squirreled away waiting to be sent off if you're not careful.

Thursday, March 20, 2014

I bet...

Remember sissy: Never bet anything you can't afford to lose.

The flip side of that coin is the old adage, "You can't win if you don't play."

Wednesday, March 12, 2014

Trap Quest (Game)

Trap Quest is a fantastic transformation roguelike made by aika (a roguelike, for sissies not in the know, is generally a turn-based role-playing game with randomly generated levels and loot).

The development thread is at TFGames.

You've won a chance to play a new virtual reality game where you can win a fabulous cash prize. It's every gamer's dream—making money for playing a engrossing, realistic game.

Moments before you load into the game you're told that the effects in game will be changing your body in the real world. That doesn't sound terrible—albeit a bit dangerous and unexpected. It starts to seem a bit weird once the game starts and you find yourself in a room with a pink motif filled with a closet of girly things. You can't venture out and about naked though; so you decide to throw on the tube top and a pair of panties just for some semblance of modesty. But right after you put on the tube top you can't help but stand up straight and push your chest out...and for some reason you can't bring yourself to take it off. Curses!

Venturing further you stumble over a trip wire that brings down a tiny syringe that injects a strange fluid into your leg. Moments later you feel your nipples tingle and absent-mindedly wonder if your chest is looking a bit too poofy. A few rooms later, when you've accidentally activated a sprinkler that's changing your hair and making your face look more feminine and trying to fend off an animated blow-up doll trying to force its way into your ass, you wonder if you may be a bit over your head.

Hours later and you're strutting about in 6-inch heels, weakly trying to stave off thoughts of sex and submission. By now you've developed formidably sized breasts and are wearing a provocative outfit consisting of a skimpy dress, overly tight bra and a string of a thong—just so you can try to ward off the next fiendish sex-crazed monster you see. You've already passed out once and briefly awoke in the real world to see that your body has indeed changed and your figure in the outside world is becoming girlier and more sexualized. No matter, all you have to do is reach the exit before your mind breaks under the humiliation and constant stream of sex-crazed monsters, slutification and feminizing traps...

Now that doesn't sound too terrible, does it?

The game runs in Gargoyle (an interactive fiction engine that uses text-based input—but don't worry, there's plenty of pictures for you more visually oriented sissies). There's also a wiki to help you out (if you want to know a quick list of commands).

It's a fantastic game that has surprisingly tight focus on sex while still maintaining a semblance of gameplay with actual goals (even if it doesn't have an ending as of Release 6. So if you're interested in vicariously living out your fantasies of being trapped in a world where everything is out to feminize you and turn you into a slut while questing for your freedom and safety (yeah, I think we know that's not happening, sissy), then you will likely enjoy Trap Quest.

(The game can be downloaded through the development thread here.)

Thursday, March 6, 2014

Courage (Poster)

In case you've been looking for a little something inspirational to hang on your wall.

Now would be a great time to do something girly you've never done before, sissy!

Friday, February 28, 2014

Deep Undercover

A core tenet of espionage: Always have a contingency plan.

Of course, for some sissies, sucking cock is the contingency plan.

(Unrelated to this anachronistic KGB-filled cappie: thanks to all the new people for visiting and leaving comments! I probably spend more time browsing other people's pages than I really should, but often neglect to leave any comments, even if their stuff is awesome. Way to go for not being like me :D )

Friday, February 21, 2014

More and More Patience

Good things come to those who wait. Even if you might not look forward to them at first.

Maybe a bit like this caption :D

Friday, February 14, 2014

With Love from Sissy (Assignment)

Happy Valentine's Day, Sissies!

Hopefully you've gone and handed someone you fancy a valentine signed with your girly name (if not, there's still time!). There's no better way you show your appreciation than to make your feelings known.

But Valentine's Day is about love, so it's a great time to show your love for your girly side, too.

And what better way to show your love for your sissy side and your special someone than by practicing your girly voice while singing a love song? Time to serenade the love of your life with an appropriately girly tune (or at least practice). Not much practice talking like a girl? You should really remedy that, sissy.

You're the only one that can know the perfect song to represent your feelings, but there are tons and tons to choose from. Maybe you're a bit addicted to that person you love? Or they're the fuel for your flame? Or maybe you're just hoping they'll make the first move

Find your girly voice and try to talk out what you love about being a girl and your special someone. Make sure you've got your voice nice and solid in your girly range (no accidental squeaking or falling back to your dull male voice). Then practice your song a few times (since some of you sissies cheat and don't follow through: that's 3 practice tries, sissy).

Then it's time to belt it out like a sissy diva. Extra bonus points for doing it properly dressed and in front of your beloved (but don't worry if you're too shy to openly profess your love of being a sissy and your love of that special someone).

Saturday, February 8, 2014

Nail Polish Appreciation (Assignment)

I will admit it: I loooove nail polish.

Lots of people have foot fetishes, I have a hand fetish. A well-manicured hand with the perfect color is fantastic. It's another aspect of style that women get to tailor to their wardrobe. Some sissies have sort of mannish nails (but don't worry, some girls have short stubby nails, too). In that case, it's probably time to make sure you're growing your nails out enough that they are longer than they are wide.

Being a sissy is great, and it's time to celebrate the girly benefits for beauty. Tight pants may have become in vogue for women and men. Some men can get by with a slight bit of make-up. With the right form, they can even pass unnoticed wearing a woman's shirt. But bright, shiny, long nails? Only for girls. Men are stuck with the dregs of short, stubby nails with - if they're lucky - black or dark blue nail polish as part of some punk theme.

A lot of sissies are keen on bright red and french manicure (naked + white tips) styles. Those can be great, but I feel like they're a bit old-fashioned (and it's important that sissies keep up to date with fashionable trends). My favorites are actually blues. Maybe it's the irony, maybe it's the fact that light blue used to be a color for girls, but it's always been my favorite (and what guy would wear metallic sky blue nail polish?). Although, pink is close second.

Whatever your favorite color: It's time to show your fingers a bit of appreciation.

Time to pick out your favorite nail polish (or time to get a 'gift' for your 'sister' if you're a bit of a closet sissy).
Now you're going to give yourself an immaculate manicure. Wipe off the brush as it comes out of bottle, dab it at the back of your nail so the polish spreads to your cuticle and then swipe the brush out to the tip. Do it for every nail on both hands. A lot of nail polish looks a bit 'translucent' with just one coat, so make sure they look perfect. Make sure you have amazingly smooth nails with no residue on your cuticles or the skin around your nails. I'm sure you've done this plenty of times before, sissy. 

Now the actual assignment: You need to take a picture of your nails and post it online or share it with someone. 

There's no reason to be afraid, sissy. No one will recognize you by your hands (of course, you can include more in the picture if you want). You can share it with someone you know or anonymous people online (or even with me). If you don't have an actual camera, then it's time to be a bit more daring and use the camera on your phone or a webcam screen capture. If you don't have any of those things, then it's time to take a stroll outside wearing your nail polish; its the 21st century, sissy and you have the internet—there's no reason you shouldn't have a camera.

Show the world your beautiful, feminine nails, sissy!

(Remember sissy: By e-mailing me a picture you are giving me irrevocable consent to display it, so don't be surprised if it shows up here.)

Wednesday, February 5, 2014

An Early Start

Sometimes a little push in the right direction is all you need.

Even if it takes a bit encouragement, getting started on sissydom early can pay off in the end. So follow the age-old advice: Don't put off until tomorrow what you can do today.

Tuesday, January 28, 2014

Promoting A Sissy

I find most sissies are always looking forward to a new position.

But is it workplace discrimination if a sissy loves it so much?

Saturday, January 25, 2014

Ending the Addiction (Sissy Lifestyle)

It's a sad fact that many sissies just have not embraced the comfort, variety, beauty and femininity of panties as everyday wear. Some sissies choose to go each day wearing gross tighty whiteys or unflattering boxers. You are girly and feminine and beautiful—You deserve to wear panties, sissy!

Unfortunately, switching over to panties in one fell-swoop is not feasible for most sissies. Male underwear is an addiction you have to break, girl. And just like smoking, going cold turkey usually ends with poor results. Some sissies have a fear that people will notice, some start too lavishly and can't find panties to wear every day (ironically named boyshorts are perfect if your clitty is being bothersome!). And some sissies have to contend with snooping roommates and family members—so it can be important to go slow.

Needless to say, if you don't even have any girly underwear, your first step is going to have to be buying panties (I recommend using packs of underwear to help build your wardrobe at first).

Now to get on the road to recovering from icky men's underwear. Naturally, if you're here, you should already be wearing a pair of sleek, comfortable, girly panties.

Now gather up all your inappropriate male underwear. How many pairs do you have sissy? That's how many weeks you'll be working on your assignment. Grab a permanent marker or a scissors. It's time for your weekly ritual. And remember: never touch yourself before you complete your assignment.

Start by repeating this:

I promise never to buy men's underwear ever again. 
I am a sissy that deserves to wear women's underwear.
Panties make me confident, sexy and feminine.

Good girl! Repeat as many times as necessary.

Image from Shemale Yum
Now look through your old, stale men's underwear. Find any that have holes or tears and get rid of them. Write "NOT FOR SISSIES" with your marker or simply cut them to pieces. Then throw them out. Think about it sissy, why do you have these tattered clothes? There's no good reason to keep them around.

If you carefully handle your clothes and have a suitable dainty lifestyle (or you're on your second week), you may find that all of your bland male underwear is in tip-top shape (at least in terms of fabric quality). In that case, take your most stained, dirtiest or frayed underwear and get rid of it the same way as before.

Once your old male underwear is tattered remnants or properly marked, throw it in the trash where it belongs.

This will be your weekly endeavor. Set aside a day each week and do it like a good girl. You will slowly wean yourself off the unnecessary habit of wearing men's underwear. As a bonus: more room for awesome girly panties or other clothes in your wardrobe.

(For secretive sissies: other people, like family members or a wife are still allowed to buy underwear for you. You are not allowed to ask them to do it. And you're still going to have to do all the weeks you set forth at the start.)

Wednesday, January 22, 2014

Hands Free

Unfortunately, kissing still counts as touching.

As well as something many sissies love that goes a bit beyond kissing.

Saturday, January 18, 2014

2014 Resolutions

It's still January, so you still have time to decide on a sissy resolution for the year. There are plenty of good ones. If you have the hair for it, growing it out is always a great option. Getting a little bit more femme by plucking your eyebrows also provides a good long-term investment in your girliness. But here are some other ideas to help with your feminization and sissification:

 1. Give up the sugary drinks and snacks.

Nothing is harder on your figure than soda, sweetened tea and super sweet energy drinks. They're a lot of empty calories you don't need and prevent you from looking your best. So start replacing your drinks with water, (soy) milk, coffee or tea (fennel or spearmint tea in particular might be useful for sissies seeking a little "enhancement").

Giving up soda cold turkey can be difficult; you may need to ween yourself off of the sweetened drinks by allowing yourself a treat when you complete a goal (or just one for the weekend). Not buying the drinks in the first place is the safest way to make sure you don't accidentally relapse. But if you can hold off completely you'll be on your way to a slimmer, healthier body for your inner sissy. And of course, the money you save could go to a nice dress or that perfect pair of shoes...

 2. Buy a chastity cage.

A chastity cage for your clitty is a great investment. It lets you play risk/reward games with yourself and, more importantly, helps you avoid the unwarranted shame and doubt that often creeps in whenever a sissy cums. As a bonus for cum-loving sissies, holding off on masturbation for 2-3 days will make sure you have a nice big surprise waiting when (or if :D ) you do get the chance to cum.

It may be difficult to wear a chastity cage for prolonged periods at first, but after a few times for a couple hours and then a couple days you'll be on your way to a hornier, girlier you. If you don't have someone to hang onto your key for you, freezing it into a block of ice always helps keep you honest.

3. Start wearing a bra for the whole day at least once per week

That's right - lift and support. From the start of your day until you hop into bed, you'll wear a bra for the whole day at least once per week. The kind of bra is up to you (it is your resolution after all): wonder bras, sports bras, push-up bras... Your choice of style is almost as limitless as your choice of color and material.

Still got most of your sissy-ness hidden away in a closet? Unless you're wearing white shirts and planning on getting wet you've got nothing to worry about (especially with a slim, tight fitting sports bra). In terms of "easy to hide", most sissies think panties or pantyhose are the safest option. But ask yourself this: How many plumbers cracks have you seen on an average day? And compare that to how many bare shoulders you have seen. Unless you're spending an awful lot of time at the beach, you'll notice that you never really see anyone's upper chest or shoulders. Even if you're hesitant, you've got nothing to fear. Except for maybe the trips to the lingerie store.

4. Perpetual pedicure

If a bra seems like it's too much, perhaps it's time to go a bit lower? Keep your toenails in tip-top shape the entire year. Make sure they're polished at least 24 days per month (keep in mind that darker pigments can lead to discoloration, so you may want to just go clear and shiny every once and a while). By the time you get to summer, you might be so disappointed no one gets to see your handiwork that you'll want to wear sandals just to show off!

As with most resolutions, it's best to set a schedule so that you develop a routine you can follow (for example, make Sunday pedicure day where you clean up and apply a fresh, new color).

Remember that your resolution should push your boundaries but not exceed them. If it's a resolution you can't keep it's not much of a resolution. Cutting out sugary drinks or only cumming once per week are good budget resolutions any sissy can do without worry.

Time to get out there and show your resolve to be a better, beautiful sissy in 2014!

Friday, January 17, 2014

Nothing to it...

...Except maybe 18 months or so. Lots of exciting and not so exciting stuff taking up loads of time.

Hello again sissies! Not that I frequent a ton of places online, but I was surprised to see that I have any semblance of a fanbase. Thanks for the support and thanks for visiting (even while I'm away)!

I'm afraid I can't really promise any sort of consistency, but I'd hate to leave all of the sissies around to just stare at videos and listen to erotic hypnosis all day long. There's so much more you could be doing to help your inner sissy flourish.