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The Sissy Dildo Guide

sissy dildo

I am a firmer-than-firm believer that a sissy’s top priority should be to do whatever it takes to emasculate herself. That would include stifling her waning male-like sexual urges, which are neither feminine-like nor appropriate for a sissy.

The overwhelming majority of sissies do not have the intestinal fortitude to quit the nauseating and nasty habit of male masturbation. That is a fact. That’s why they make chastity devices.

Once a sissy’s so-called “clitty” is securely locked away, then the next logical step in the sissification process is to begin developing and stimulating her new erogenous zone.

Her sissy pussy!

Sissies certainly shouldn’t be going without sex. But sissy sex is different than manly sex. A lot different!

sissy sex is better sex

A sissy has voluntarily relinquished her role as a sexual penetrator—at least with her now limp and useless sissy clitty. She is now a bonafide sexual receptive.

That’s one reason they make dildos. To help transform a sissy into the ultimate sexual receptive. She learns to provide and receive pleasure by use of either her mouth or her ever-escalating-erogenous sissy pussy.

This sissy dildo guide will expose you to the many different types of dildos that are available so that you can practice and refine your new and improved sexual role as a sissy.

What Material Should Your Dildo be Made From?

sissy dildo materials

Here’s a list of the most popular materials that dildos are made from. Note: not all of them are necessarily safe or recommended!

  • Silicone
  • Stainless Steel
  • Plastic (as in hard, ABS)
  • Glass
  • Ceramic
  • Rubber
  • Jelly
  • PVC

Dildos made from silicone are popular because, although stiff, they’re still somewhat pliable—like the real thing. They are non-toxic, non-porous and not stone-cold-hard (like metal, glass, hard ABS plastic and ceramic are).

Silicone, because it’s a high-quality material, also tends to be more expensive than other dildo materials on the above list.

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Dildos made from metal, like stainless steel, can be nice—and heavy. They’re non-toxic and non-porous, but unlike silicone, they are rock-hard.

Glass, ABS plastic and ceramic dildos are also too hard for many sissies. They do have their place however. Because of their non-toxic and non-porous characteristics, they are also considered safe materials for dildos.

The last three materials on the above list are not considered safe. That’s because, more-often-than-not, they contain a toxic chemical called phthalates. Rubber can also contain chlorine, which can cause a rash. Also all three are porous—which means they can harbor harmful bacteria.

The reason rubber, jelly and PVC dildos are manufactured at all is simply because these material are cheap. There will always be a market for cheaply made, inexpensive, albeit potentially dangerous dildos.

My recommendation would be to avoid sex toys made from these three materials. You want to always honor your sissy pussy. One way is by keeping your preferred and precious sissy sex organ safe from harmful chemicals and bacteria.

What Type of Dildo Do You Want?

sissy dildo types

Now comes the fun part: deciding on the best type of dildo for you. Eventually you will want to have many types so as to expand your sissy sexual pleasure. But… the best place to start is with just one.

Here are the main types of dildos:

  • Penis shaped or phallic
  • Realistic (like the above but textured with veins, etc)
  • Straight (keeping the penis-like-look to a minimum)
  • Suction cup (for hands-free operation)
  • Double ended
  • Vibrating
  • Strap-on

There are other types of dildos for sure, but the above are the main varieties.

Most penis shaped dildos will typically have a slight natural curve to them. This is important to a sissy as it will enable the tip of the dildo—when positioned properly—to engage with the prostate, or P spot.

For the sissy who is legitimately in love with cock, a realistic dildo might be the proper choice. If you just want something cock-like up your sissy pussy, then a straight dildo would be more than adequate.

Double ended dildos are appropriate to use with a partner. Picture two sissies butt-to-butt, ass fucking each other. Or perhaps a wife, instead of a strap-on, using a double ended dildo to peg her sissified husband.

sissy dildo types

Speaking of strap-on dildos, a wife or GF of a sissy is, sooner or later, going to demand penetrative sex, something that her sissy—especially if caged—can’t provide. That’s where a strap-on shines.

All of these types of dildos can come in the vibrating variety. This of course adds an extra dimension to your sissy-pussy erotic play.

too timid

No matter what type of dildo you’re looking for, TooTimid.com will most likely have it. You can check them out right here.

Lastly, but most definitely not insignificant, are suction cup dildos. If you find yourself horny and alone, which can often be the case, a hands-free dildo can come in quite handy. So much so that I’ve appropriated and entire section on ways you can use dildos that come with a suction cup attached.

Suction Cup Dildos for the Sissy

sissy suction cup dildo

It’s so much easier to simulate real-live-sex with a dildo when you don’t have to use one hand to hold or guide it. Hence, the suction cup dildo.

Where you decide to stick your new sissy-sex-partner is entirely up to you. Other than requiring a smooth, flat surface, you’re only limited by your imagination. Following are a few ideas to get you started.

On The Floor

The easiest and most comfortable way is to just sit back on your knees and ride your dildo. You can also squat down with your feet on the floor.

sissy floor dildo

If you prefer to wear heels while fucking the shit out of yourself (like I do), then some sort of small but sturdy box—or even a thick book—to raise the dildo a few inches up off the floor is useful until you develop sufficient suppleness (while wearing those heels) to get your ass lowered down far enough to achieve proper penetration.

sissy heels dildo

On a Wall or Headboard

This type of attachment works well when in the doggie style position. Just get on your hands and knees and back-up to the waiting, wall-mounted dildo. Alternatively, you can lay on your back with your legs raised straight, resting against the wall.

You can also approach the dildo on your knees while facing it and practice your sissy sucking skills.

Attached to a Mirror

Being able to see your sweet sissy-ass while in the above mentioned positions can serve to spice things up even further. I wouldn’t try it with a ceiling mirror until you have learned how to hover.

sissy mirror dildo

Simulating a Threesome

If you and your partner would like to experiment with a third person, but that 3rd wheel isn’t actually present (yet), then a dildo with a suction cup can be the answer to your menage-a-trios fantasy. All you will need is the dildo and your kinky imaginations.

sissy threesome dildo

How About a Chair?

Never overlook the obvious. Using a wooden chair as a dildo-sticking-base can provide a full penetrative experience, if that’s what you’re looking for. Just don’t forget to remove the toy after you’re done satisfying yourself. The next person to sit there may not be looking for the same dining experience as you.

In the Bathroom

Lots of hard, flat surfaces makes the shower a perfect place to stick your dildo. Fasten it to the wall and then back right up to it. Place it on the floor of the tub and then squat or sit on it.

sissy tub dildo

Since you’re in a slippery, soapy environment, be careful while playing. Oftentimes, soap will be the only lubricant needed.

Don’t forget the toilet either—or more specifically, the toilet seat. The flat, hard surface is an ideal place to stick a dildo. Also a toilet is lower than the typical chair so it might be a more convenient and comfortable place to give yourself a thorough sit-down fucking.

Strap-on Dildos

sissy strap-on dildo

Most all suction cup dildos will work seamlessly with a dildo harness. This is important for sissies since a sissy should ideally be either perpetually limp, locked in chastity, or both.

When a sissy’s female partner desires/demands penetrative sex, there is more than one option. While caged, the sissy simply dons a dildo harness, with an appropriate sized dildo attached, that’s positioned just above her caged clitty. Her female partner can now receive a satisfying and proper fucking—something that her sissy can’t provide.

Alternatively, a sissy can wear a hollowed-out dildo that fits directly either over her chastity cage or her limp and useless clitty.

sissy hollow strap-on dildo

Hollow strap-ons also come configured with an integrated strapping arrangement so that no separate dildo harness is necessary. Regardless, any sissy living with a cis woman should have some sort of strap-on dildo on hand. Unless of course she doesn’t mind being a cuckold sissy.

How Big Should You Go?

sissy big dildo

It’s common to get over-enthusiastic when it comes to dildo diameter size. While “bigger is better” might be a true statement for a GG, that’s NOT necessarily the case for a sissy such as yourself.

Your sissy pussy will have to be gradually stretched out. Dildo training is the process of doing just that. You start off with something manageable, then progressively work up to something bigger.

When it comes to performing oral, your mouth and throat will also have to become accustomed to having a dildo or dick inside of it. If the dildo is initially too big or too long, you will gag. You will need to train yourself to never gag as it’s extremely un-lady-like.

Depending on how much anal experience you have, a general sizing guideline would be to start off with something 1¼ to 1½ inches in diameter (34mm to 38mm). It should be a size that will hurt just a little at first but something you can quickly adapt to.

Dildo Decision Time

sissy dildo decisions

As a sissy, you absolutely need a dildo to further your sissification process! Proper sissy-sex requires a penetrative device. The only question to ask yourself is, which dildo should I buy? Hopefully I’ve been able to provide you with some ideas so you can make the best decision for your unique sissy situation.

too timid

No matter what type of dildo you’re looking for, TooTimid.com will most likely have it. You can check them out right here.

You can’t go wrong buying a dildo from TooTimid.com. They have been in business since 2000, ship items quickly and discretely, and have a a hassle-free return policy. Yes, I do have an affiliate relationship with them but beyond that, I purchase my own personal sex toys from TooTimid because they are pleasant people to do business with.