Classic Sissy Assignment Series 47 – Your Butt Fitness & Food

I had one sissy mention that she was starting to settle into her little schedule. I think that’s a good sign that it’s time for assignment number five…

If you’re new to this site, and you want to get involved as a sissy in training, go to the first assignment and work through that assignment before you move to the next one. Most importantly, if you want special attention, you will demonstrate that you are worthy of it by creating a blog here on blogger and keeping it up-to-date.

As for your ealier assignment regarding the gloss, it does seem difficult to find a Clear Matte Gloss, but if you look hard, they are there.

Until you find it, it is NOT ok to simply use a chapstick. You will simply have to do with tinted, or shiny gloss, which must be on your lips at ALL TIMES.

I want my sissies to put out a fresh face to the world. I want you to have eyes that seem to pop. Part of that can be accomplished with mascara, but mascara is a bit further than I want to take you at the moment.

It can be distracting if it’s not done right, and we want people to see your beauty, not makeup. Instead of mascara, I want you to invest in a good lash tint. A good lash tint won’t clump up your lashes or look like you’re wearing a bunch of makeup, while emphasizing how pretty your eyes are.

Now I don’t think all of my sissies are ready for tiny clutches and handbags, but it’s high time you bought a few nice messenger bags. I saw some excellent ones at Target, particularly a pink and brown plaid one by Mossimo next to the purses.

I wouldn’t mind if instead you got a tote bag, but it just seems like the messenger bag is so much more functional for my sissies. The one in the link is also very acceptable, but I don’t want you to buy a black one, you should really look for several in different colors to coordinate with your outfits.

Once you have one, you should have it with you EVERYWHERE you go, except work (unless appropriate for your work). They are so handy you’ll find you won’t know how you lived without it!

Finally, now that we are done (for this lesson/assignment) with the outer sissy, we’re going to work on the inner sissy.

You need to buy a dildo (as lifelike as possible), preferably made from cyberskin, though if you’re on a tight budget, a cheapo will do.

But if you’re really taking this seriously, you’ll get a cyberskin one, because it will make your experience much more realistic, which is what we all want, right sissies? 😉 Here’s a hint as to what’s coming: you’ll also need flavored lube.

Now, every week for 30 minutes, you’re going to simulate oral sex with this dildo and a few drops of the flavored lube reapplied as frequently as you like. You will spend five minutes at least attempting and learning to deep throat it.

You will masturbate with a condom on your little clitty while you practice making love to the dildo with your mouth. You will practice until you cum, or until the 30 minutes is up, whichever comes LAST.

Then you will take your condom full of your cum, and spill all of that cum on the head of the dildo or inside your mouth, and suck the head with your pretty fingers around the shaft as if it just came inside your mouth.

The cum should still be warm as the cock you’ve been sucking is warm from your throat and the cum should be warm from being in the condom on your clitty. So now you are eating cum you have sucked from the cock, and you notice how good it tastes.

You want to spent at least a few more minutes sucking that head until you know you’ve sucked all the cum down.

If you get turned on again by finishing the job, tough luck baby, slip your little clitty back into your panties and savor your turned on state.

You are not allowed to cum again for at least another hour. Why am I not letting you cum again? Think about it and let me know why you think I’m doing that to you.

Now for your rules (maybe you should print them and put them on your fridge or keep a copy with you):

1. If you cum, you must swallow it, all of it, and with a clear voice verbally thank me your master for allowing you this freedom. When you have your dildo, you must cum with its head in your mouth, and you must consume your cum from the head of the dildo (unless it is too copious, in which case, use your mouth to catch the rest of it!)

2. You must keep your body hair off with an epilator and trimmer, keeping absolutely smooth your hands, feet, thighs, underarms, chest, butt, pubic area, etc… trim your calves and arms to a #1 1/2. When you go to a hair stylist, inform them to be careful to give you soft and tapered sideburns “like a girls’ cut” and to do the same in the back.
3. You should now be wearing only panties, thongs, and short boxer briefs. If you have loose and baggy clothes, begin replacing them with fitted clothes that fit your body (Banana Republic, The Gap, H&M, Zaras, all have fitted clothes. If you need bargains, go to TJ Maxx or Ross.)
4. You should be tanning your sissy butt and posting your progress on your blog.
5. Use a black lash tint at least every three days. Tweeze, trim and shape your eyebrows. Use a concealer to cover blemishes. Have a lip gloss for everyday (all the time!) use and tinted gloss for special occasions, like every time you go out for dinner. Whiten your teeth. If you wear glasses, find a more feminine/delicate pair if possible or switch to contacts. I want you to have facial features that stand out in a good way when you enter a room.
6. Use a femininely scented lotion regularly to keep your skin smooth and silky. Use a stone or something to get rid of callouses. Push back your nails cuticles and keep your nails smooth and buffed.
7. Your goal is to stretch your pussy so it can take a real man’s penis. You will spend at least an hour twice a week stretching your pussy with a butt plug. If your current one is too small to have an effect, move up a size.
8. If you break the rules, your punishment is as follows: Set a timer for 30 minutes. Go put a penny on the wall at shoulder height and hold it there with your nose. Keep your legs straight, and keep your hands above your head and not touching the wall or your head. Keep in this position until you hear the timer go off. I am serious about my rules, and breaking them will bring humiliating punishments that will not be fun or entertaining.
9. Keep a blog to document your journey into becoming a sissy. Document everything, including sexy close-up pictures of you (face optional, but not skanky, or shitty, but sexy, because the idea is to humiliate you, not me), and maintain it at least monthly (if you want me happy, post a blog weekly). If I catch you letting it go, I might just give you a punishment that will leave you crying and wishing you had never done this in the first place, and I don’t care how masochistic you might be, you won’t like it. Post a link to your blog in the comments here.
10. You are to be exercising and counting your calories!
11. Take a cute, colorful, or light colored messenger bag with you everywhere! (You might want to keep your gloss, concealer, and lash tint in it!)
12. Practice your cocksucking skills as described above at least once a week.