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Sissy Anal Training

Now that you have your tools for strap on training, it's time to put them to good use! Aren't you excited? Being fucked by a strap on is a very common fantasy for sissy boys, so it would be quite unusual if you weren't really happy about beginning your strap on training.

Of course, many sissies are understandably a little nervous about the idea. The thought of being on your hands and knees having your little ass used by your Mistress can be daunting, especially if you're a complete anal virgin. The good news is, there are ways to make the experience a lot less scary for you. Read on if you'd like to learn more!

The Very First Thing You Should Know About Strap On Training Is That There's No Hurry

Always take your time, sissies! Going too fast could be dangerous, but going too slow (if there is any such thing) can only be sensual and erotic. The journey is far more important than the destination, in this case.

With that in mind, let's begin your training. Your strap on Mistress will be so pleased that you've taken the initiative to train yourself, rather than expecting her to do all the work for you!

The first thing you'll need to do is gather together all your materials--lube, gloves, and any toys you may have. Then, make your way to a nice, quiet place where you won't be disturbed and remove your clothes. You may leave your cute panties on if you want, but this might make things a little more difficult, at least the first couple of times. Lie down on your back somewhere that's comfortable. The lying down part is important. Your body is more relaxed when it's lying down than when it's sitting, and being relaxed will make your anal sissy training much, much easier.

Once you get nice and comfortable, you can begin! If you have gloves (and we highly recommend that you do have them), go ahead and slip those on. You can just wear a glove on one hand if you prefer to leave your other hand bare to stroke your cock as you play.

Now, get out the bottle of the lube of your choice. Lube your hands well and then apply some lube between your cheeks. You do know which set of cheeks we're talking about, right? All right, good! It's time to start stroking. Grab your cock and play with it. It's probably already gotten hard, just from the anticipation of what's to come, but let's make sure it's really hard before we go any farther. The more aroused you are, the easier the following steps will be for you.

As you stroke your cock, let your other hand massage your balls to get you even more turned on. Then, as you continue playing with your dick, let that hand trail down farther and farther. Once you reach your little puckered hole, massage the outside of it gently with the index finger of your gloved hand. This will relax your outer sphincter to prepare yourself for penetration and will also give you a little more lube in the appropriate area.

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Prepare For Your First Sissy Anal Penetration

If your lube has dried on your body or on your gloves, be sure to replenish it before trying to penetrate yourself. Once you're sure you're plenty slippery, take a couple of deep breaths. You may continue stroking your cock, or you may focus all of your attention on your anal area. This is entirely up to you. Bear down a little and then very gently, ease the tip of your index finger inside your ass. If you feel pain, STOP! If the pain doesn't cease after you stop pushing your finger inside you, then slowly remove the finger and try again in a few minutes. This type of play should not be painful!

Give your body a few moments to get accustomed to this intrusion. You may find it helpful to go back to masturbating while you adjust to having your finger inside you. When you feel comfortable, slip your finger in deeper, very slowly and very carefully. Take as much time as you need and stop as many times as necessary to allow your body to adjust to the foreign object inside it. Again, if you feel pain, stop for a bit, then start again. If you feel as if your finger is getting "stuck," you may need more lube.

Once you have your finger in as far as you can get it, take a deep breath and concentrate on the feeling of that finger in your ass. How does it feel? Do you feel electric sexual energy coursing all through your little sissy body? Give yourself time to bask in the feeling of your very first anal penetration. You might even try curling your finger upwards, toward the ceiling. This is the way men are able to find their prostate glands. It's a small, walnut-shaped bump that can give you lots of pleasure when massaged with a finger or toy.

If you feel comfortable, you can move your finger (slowly and gently!) inside yourself with an in-and-out fucking motion. Fucking yourself while jerking off will probably be a very intense sensation, so if you'd like your session to last longer, you may find it useful to bring yourself to the edge, then stop, to give yourself a chance to calm down before you start again.

Some Sissy School boys have told us that they were able to work in a second finger during their first anal penetration. You can try this if you want, but it's not necessary. You'll have plenty of time to try it later!

You can easily modify these instructions to use time and time again. Start with one finger, then work your way up to two. If you have toys, choose the smallest one you have. You'll want to use it several times before going up to the next-larger size.

Another idea is to use anal beads (as long as they are large enough at the bottom that they can't slip all the way inside you accidentally and get lost) or butt plugs to train your ass passively. If your anal toys are made of silicone, you can wear them for short periods of time. As with everything else concerning anal play, you'll want to start slowly. Begin by wearing your toy for no more than 15 minutes at a time. After a couple of days of this, you can try to wear it for 30 minutes. If you go up in 15-minute intervals every few days, you should eventually get to the point where you can wear plugs or beads for extended periods of time.

Just remember to take your time! Your strap on femdom will thank you when you come to her with an already-trained ass!

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For sissification and feminization phone sex sessions, visit us at Sissy School, or call us Toll Free from the UK at 0-800-014-8421. We look forward to helping you bring out the Sissy inside!