This is not a Sissy Station assignment; it's one that I wrote some years ago in imitation of them. Logically it follows the fifth assignment, since it refers to the cock sucking task of numbers four and five.
I wrote it because I felt that the Sissy Station assignments didn't explore the anal sex side of sissy submission as much as they could have. IIRC, they involve wearing a butt plug for longer and longer periods of time, but that's about it. I thought that much more could be done on the subject.
I have some thoughts on more assignments - in fact, I think that may have written a follow-on to this one, but I can't find the source - but any ideas are appreciated!
And, of course, any comments from those who try to carry out these assignments are more than welcome!
Anal Sissy Assignment
Time to continue your attitude adjustments, sissy girl.
It may be hard to believe, but even now, when you masturbate, you wank too much like a Real Man. Even though you have a little boyclit instead of a real cock, and you may only cum once for every ten times that you practice cocksucking (and, when you do, you must eat your cum), you do have direct control of the action - you can take matters in to your own hands, quite literally.
That's about to change.
It's time to shop for another dildo, and I think that you can guess what this one will be for! Why can't you just use the one that you have been sucking on? There are many reasons: a shape that is good for sucking may not be optimal for, well, other things; there's the hygene factor (although we may address that concern in a later assignment); but, most importantly, there may be times that you will be filled at both ends!
This dildo need not be realistically detailed, nor should it be as large. (Was that a sigh of relief, sissy? Or something else?) But it should have a head that's bigger than the shaft, and it should be curved, like a rampant erection, the better to find your sissy G-spot.
Put the two dildos together and examine them side by side. Measure their girth by wrapping your hands around each of them in turn. Take the new one into your mouth to get a sense for how it compares to the first; as you suck on it, imagine how large it will feel in your boypussy.
Start on your back, with you legs spread and your knees drawn up slightly - whatever feels comfortably relaxed. Slide a pillow under your ass to make it more accessable. Accessability - that's an important and recurring point, sissy. Put a large dollup of lube on your finger and spread it on and around your sphincter. Does that intimate contact make you a feel little apprehensive, sissy? It should.
Spread another dollup inside. Does that feel good? How did your boyclit react, hmmm? Put some lube on the head of your new friend and spread it around. Then some more - it's important to use lots of lube. Now for the moment of truth. Holding your dildo with one hand, use the other to spread your ass cheeks and guide that missile to its little puckered bulls-eye.
Your sphincter will probably resist this bulbous invader at first. Be patient, but persistent. Rub the head around your anal ring, first pushing it in a little, and then retreating. Try to relax your sphincter muscle in response to these advances. Finally, you will have pushed the head in far enough to get past the ring, and your greedly little sphincter will close tightly behind the head, thereby pulling the dildo in deeper. Did that make you gasp? That's it - your last defenses have been breached. You've been deflowered; you might as well relax and enjoy it - your boyclit appears to have!
Pause a moment and get used to the feeling of that cock inside you. Move it a little, in, out, and around, experimenting. Aim that monster at your belly button and try to find your sissy G spot. Now pull it all of the way out - your sphincter is reluctant to let it go, isn't it? Relube and slide it back in. It goes in much more easily this time. You're getting used to this, you little slut!
Start to fuck yourself slowly, with long strokes in and out. All of the way in, and then almost all of the way out. Let your body move in response: thrust your hips upward to meet the instroke, and roll them back on the oustroke. When you used to wank your boyclit, it was just your hand doing the work; now your whole body should be in on the action. With your free hand, play with yourself. Stroke your skin, fondle your nipples, rake your belly with your fingernails. You may touch your boyclit, but only enough to keep it perky! Try varying the tempo, or how far in or out it goes, or where the head is aimed, and note your body's reactions.
While continuing to fuck yourself, reflect on this. There are several purposes to this exercise; the first one being to move your focus for sexual gratification from your boyclit to your boypussy. To that end, you will never again touch your boyclit to bring yourself to orgasm. You will only cum from being fucked in the ass. Oh, it's possible all right, although it may take a while for your body to learn how to do it. It will be a frustating time, I'm sure. But, you say, real women touch themselves when they masturbate. Yes, but the feminine ideal is to be fufilled - to achieve orgasm - through penetration alone, and your goal is to be ideally feminine, isn't it, sissy girl?
The second purpose is to externalize the source of your sexual gratification. You are no longer self-contained; you will be dependent on penetration from a cock in order to achieve orgasm. You will probably start to find phallic shapes very intriguing! How humiliating! A Real Man would not swoon over the shape of, say, a banana, wondering how that would feel inside him. But you aren't a Real Man, are you, sissy girl?
The third purpose is to open you up (literally), to make you feel more vulnerable, more... accessable. Real men are too controlled, too tight, too rigid. As a sissy, you must become more reactive, more pliant, more... submissive. Accepting that alien invader now burrowing deeply within you is a step in that direction. Can you imagine a Real Man fucking himself in the ass with a rubber cock? Of course not.
Your boyclit is probably leaking precum all over the place by now. You must not waste any. Scoop it up off your belly with your fingers and then lick them clean. But don't touch your boyclit! Instead, tighten and release your anal muscles around that dildo, and feel how it makes your boyclit perk up! So, only touch your boyclit when you need to; otherwise, milk that dildo.
It's probably time to try a new position. Keeping the dildo inside you (unless you really were looking forward to the feeling of reinsertion!) roll over and get up on your knees. We want both hands available, so you might need to put a big pillow under your breasts to be comfortable without having to hold yourself up. I bet that your ass looks really cute, waving around in the air like that. Does this position make you feel more accessible, more vulnerable? Imagine that Real Man has surprised you and wants to have his way with you. Given your... position... all he has to do is to grab your hips and plunge his charger deep inside you. But don't worry, there aren't any Real Men around here. smirk
Next time have a plate handy to catch all of that precum that is leaking down onto the sheets. You'll know what to do with it.
After fucking yourself doggie-style for five minutes, try another position. It's called "Sissy Cowgirl". (This is a good time to relube that cock, if you haven't done it recently.) Take that pillow and fold it or bunch it to provide a firmer support, and drape a towel over it. Set your dildo on it and hold it upright, pointing to the sky. Your job is to impale yourself on it. This time, instead of guiding the cock to you, you're going to guide yourself to it.
Kneel with the pillow between your legs, and with that cock a little behind you. Without looking, but with your free hand spreading your ass cheeks in anticipation, lower yourself toward that cock. Your free hand will have to help guide you to the right spot. It may seem awkward, but don't worry, practice will make it perfect! When you've reached the target, lower yourself onto it. There! I'll bet that made your boyclit jump!
Since the pillow keeps the dildo in position for you, largely but not entirely immoble, your body movements are key to maximizing the sensations that you feel. Try rocking your hips slowly back and forth. Rotating them, first one way and then the other. Let your body tell you what feels good.
Your hands are free to do things like cup your breasts. Grab your buttocks. Support your weight as you experiment with different angles. Scoop up that never-ending supply of precum. Next time, set up your cock-sucking mirror so that you can watch yourself squirm as you ride that cock. Or had you thought of that already?
If you can reach orgasm without touching your boyclit, congratulations! You've scored! (Of course, you remembered to catch your cum. You're so well trained!) But if you can't quite get there, don't worry - there's always tomorrow. Because I want you to fuck yourself daily. Do it first thing - that way, you can wonder which of the women you'll see that day also got fucked that morning.
Keep up your cocksucking as well. What's that? Can you combine sucking and fucking, do them both at the same time? Sissy, you're such a slut sometimes! Well, if it adds an extra note of excitement to feel one cock up your ass while you're sucking another, or to have your mouth filled with cock while you're fucking yourself into ecstasy, then more power to you. But you should still spend time concentrating on each activity individually. You'll just have to wake up that much earlier!
Your assignment is to fuck yourself every day for a week. Three positions, at least five minutes in each. Can you dream up new ones? How about: sprawled back in a big easy chair or sofa, with one or more legs draped over the arms or back? Don't forget to put down a towel! Or, can you think of ways that you can brace your dildo against something while on your back or in doggie-position, so that you won't need to use your hands?
If you are able to cum just from penetration, feel free to do so as often as you are able. (Enjoy it while you can. smile) If you can't, don't worry. Maybe your dildo just isn't big enough - although you did buy one that was as least as big as your boyclit, didn't you? (Think about that for a moment.) You'll have a chance to rectify that possibility in the next lesson. grin
Yes, I have fucked myself with my dildo and have not touched my boyclit to make myself cum