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Tools For Strap On Training

It's a rare sissy boy indeed who has never at least thought about being fucked by a strap on before. It's a train of thought that makes a lot of sense, actually. If you're going to dress and, in some cases, act like a girl, why not try out being fucked like one?

Before jumping right into being fucked by your strap on femdomme of choice, it's always a good idea to prepare yourself with some self-administered anal training. Preparation is always good, and making sure that your anus can accept objects that are approximately the same size as your Mistress's strap on dildo will make you feel more comfortable when the opportunity finally arises.

With that in mind, let's discuss the items you'll need to begin your sissy strap on training!

First of all, hold your hands up and take a look at your fingers. Are the nails closely trimmed with no sharp edges? If so, your fingers will be the best tools you can possibly have for training your ass to take your Mistress's strap on.

If you have a nice manicure that you don't want to sacrifice for your anal training, another option is to buy gloves to wear on your hands. Sterile latex gloves are best as long as you don't have a latex allergy. If you do, try some synthetic rubber gloves instead. No matter what type of gloves you use, be sure that they're sterile! Only use the gloves once and discard them after using them.

Gloves are a good idea even if you have well-trimmed nails with no sharp edges. Because the gloves are non-porous, they don't absorb your lube like your bare fingers do, which means your lube will last longer. Lubed gloves also glide along surfaces like skin better than do bare fingers.

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Sissies Will Need Lube For Their Anal Training

Speaking of lube, this is the other thing you will need to start with. There are three types of lube: water-based, oil-based, and silicone. Each one has its advantages and disadvantages.

Water-based lubes, such as Astro-Glide and KY, are the most toy-friendly of the three types of lubes. They are compatible with toys made of any material. The main disadvantage of water-based lubes is that the water in them quickly absorbs into the skin and/or evaporates, causing it to degrade and become sticky. This makes it necessary to reapply water-based lube very often.

Oil-based lubes, such as massage oil, cooking oil, or certain manufactured lubes, degrade far more slowly. They don't evaporate like water-based lubes, and they don't absorb so readily into the skin. It's also quite likely that you might have an oil that you can use as a lubricant at home, thereby eliminating the need to go out and buy lube.

Unfortunately for the sissy phone sex boys out there, oil-based lubes cause latex barriers to disintegrate. This is not a huge deal when you're playing by yourself with latex gloves, but it is a big deal if you ever decide to be fucked by a real cock or by a strap on dildo that has not been properly sterilized. Oil-based lubes should never be used with condoms or other latex barriers. Since you should always use a condom when playing with others, oil-based lubes are best reserved for self-play and self-play only. Another, lesser, disadvantage of oil-based lubes is that they can be messy to clean up.

Silicone-based lubes are the third option. These lubes are superior to both water-based and oil-based lubes in that they do not degrade with use, and the body absorbs them very, very slowly. Generally, one application will be plenty, unless your anal training sessions lasts for several hours! The main drawbacks of silicone-based lubes are that, like oil-based lubes, they can be messy and ruin fabrics. They are also not compatible with sex toys made of silicone. Silicone lube can ruin your silicone toys, so always keep the two separate by using water-based or oil-based lubes with your silicone dildos and butt plugs.

When purchasing silicone-based lube, make sure it's pure silicone. Often, lube manufacturers will put a tiny bit of silicone into a water-based lube and call it silicone lube (while bumping up the price accordingly!). The added bit of silicone does not keep the water-based lube from degrading, so these types of "silicone" lubes are truly no better than water-based ones. Let the buyer beware!

Other Items For Sissy Boys' Strap On Training

In addition to the necessities--fingers, gloves, and lube--some sissies are curious about the use of sex toys during their anal sissy training. Toys can be an excellent addition to your training regimen, but they are by no means required.

If you're one of those sissies who desperately wants to try out sex toys, a good place to start is with a small dildo. Most sissies want to go for the biggest toy there is right out of the gate, but that's not a good idea. If your ass has not been properly trained, you won't be able to use that huge toy without hurting yourself! Since we want you in one piece, let's start with a smaller toy. If you just have to have a larger dildo, go ahead and buy it along with the smaller one. It'll give you some inspiration to work your way up to it! You may even want to buy three--a small one, a medium one, and a large one.

Other good toys for anal training include butt plugs, anal beads, and insertable vibrators. Again, with these toys, you should start out small and then get larger as you become more accustomed to taking objects inside your body.

When choosing sex toys, try to choose toys made of silicone or glass (in the case of dildos). These toys are more expensive, but they will last longer than cheaper toys. Both silicone and glass toys are nontoxic, unlike the so-called "jelly" toys. As an added bonus, silicone toys can be sterilized in boiling water that is less than 500 degrees Fahrenheit.

Once you get all the items you need to begin your strap on training, you might want to check out our sissy anal training guide, which will walk you through all the steps of training your ass for your Mistress.

Happy ass-fucking!


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!