Sissy Training: Top 5 Sex Toys for Anal Play

By iHeartGuys · Updated

Sissy training ranges from being sexually submissive to influencing your lifestyle.

But wouldn’t you admit sex is the most exciting part? – Masturbation habits are just as important as outfits, behavior, and grooming. That means a sissy needs a couple of anal toys or a lifelike dildo for stimulation.

Every dominant woman agrees it’s a key piece of the puzzle to feminization training. So listen to your mistress by picking out a few naughty novelties. Make it known how much you prefer riding dildos instead, then maybe she’ll let you go down on her too!

With a collection of sissy toys, you’ll be one step closer to a handsfree sissygasm.


Our list of the best sex toys for sissies:


Read all the way through the guide! Near the end, there are a couple of bonus adult products that might surprise you. Also, we’ll go over our best recommendations to complete your sissification.


1. Impulse (6-In. Dildos)

Impulse Dildos are sissy toys that you’ll use in every training session. It’s a way to start off slow, then loosen up for a bigger cock to penetrate yourself with later. Whether you keep reading or not, Risque Fetish has anything you’d ever want for anal play.

As a store with submissive toys, this brand does a good job of categorizing the best sissy dildos. Regardless of your level of feminity, Impulse’s are an essential part of sissification.


“Look through the collection of realistic dildos and you’ll find sex toys between 4 to 10-inches. Available in a variety of colors like pale, tan, and brown, there’s an option for all submissive adults.”


Here are a few of the sub-categories too:

  • Uncut Dildos
  • Attached Balls
  • Double-Ended
  • Squirting Models

And many more kinds of dildos for sissy training!

Overall, we recommend you sort by best-selling to see the brands that others prefer. Plus, you’re even able to narrow the results by color if you only want to browse pink ones, for example.

Shop for Sissy Dildos


Pros:

  • Most popular dildos
  • Several lifelike colors
  • Starter sex toy for sissies

Cons:

  • Won’t totally fill you up
  • Sometimes out of stock
  • You’ll want a bigger one too

2. Lovers (Butt Plug Kits)

Lovers Plugs are full sets of anal toys that deliver sustained stimulation. Since they stay firmly and comfortably in place, you’ll have no issues with extended wear.

Whether it’s to loosen up for a dildo or just prolonged play, butt plugs are a key part of sissification. No matter the purpose, the kits from Risque Fetish are the best to wear long-term. Now squeeze a toy into that tight ass, and dedicate yourself to sissy training!


“Imagine a cuckoldress kneeling behind you as it sparkles, watching as you blush and throb. Seeing how much of a sissy you’ve become, she gives a dominant, yet satisfied smile.”


When you writhe in anal pleasure, a mistress will know her sissy training works.

Or perhaps, try taking a revealing mirror selfie with your back arched and booty popped out. Then the flash of a camera makes its jeweled-base gleam elegantly.

Just make sure to tuck your tiny sissy dick between those plump thighs too!

Shop for Anal Toys


Pros:

  • Best sissy butt plugs
  • Cute, yet elegant designs
  • Sparkly sex toys with gems

Cons:

  • No vibrations on most
  • Difficult to figure out sizes
  • Could have more pink toys

3. Beyond (9-In. Dildos)

Beyond Dildos seem so much like the real thing when you grasp them. Well, aside from the sheer size, at least! As a matter of fact, it’s the closest thing to having a real cock ready to penetrate you anytime you’re horny.

In that case, you might want to keep it within arms-reach at all times! So if your sissy fantasies involve taking a huge dick, then this sex toy will deliver like none other.


“On a side note, the Beyond sissy dildos are bigger than they look. So these models stay as a specialty anal toy for those who crave a true feeling of being filled up.”


Beyond’s are compatible with strap-ons and harnesses too.Do you have a femdom wife or girlfriend?

A brand-new dildo could be just the right thing she needs to peg her sissy’s deep spots. On the other hand, if your mistress craves a pounding, you can strap it on and give her the thick dick she deserves.

Instead of your tiny clitty, of course.

Shop for Sissy Dildos


Pros:

  • Filling you entirely
  • Strap-on compatible
  • Best dildos at 9-inches

Cons:

  • Slowly working up to it
  • Limited colorful models
  • Experienced sissies only

4. Satisfy (Prostate Toys)

Satisfy Massagers will take you to a whole new level of arousal. Due to the fact that it hits a sensitive P-spot, they’re the best anal sex toys for actually getting a sissygasm.

Combining vibrations with pressure, your eyes will roll back as it goes to town on your sissy pussy. Simply put, prostate toys overwhelm you with a sweet, pleasant feeling of euphoria.


“The look of a prostate massager isn’t as tempting as a dildo with realistic attributes. But they make up for it by giving sensations like no other anal toy.”


If you ever want to have a real sissygasm, you must refrain from rubbing your clitty.Feeling ambitious?

Whip out a Satisfy sissy massager for handsfree anal stimulation! All of them are USB rechargeable too, meaning no annoying batteries to deal with.

After all, it’s a buzzkill to have a vibrator turn off right on the brink of cumming. Unless it’s a sissy training routine that includes a skin-tingling ruined orgasm!

Shop for Prostate Toys


Pros:

  • USB cable included
  • Best for sissygasms
  • Charges within minutes

Cons:

  • Anal play only
  • Many are non-phallic
  • Some can be expensive

5. Depth (8-In. Dildos)

Depth Dildos have everything you’d expect from a real cock, such as veins and a hot mushroom-shaped tip. With a suction cup base, they attach firmly to almost anywhere.

So stick it to the floor of the shower and ride to your heart’s delight while warm water rains down! Even though these dildos have a bit of weight to them, they’ll stay secure in any horizontal position too.


“As a considerable size increase, it’s a good sex toy for going further into sissification. Beautifully designed to look and feel lifelike, the Depth sissy dildos are truly a work of art.”


Delivered to your doorstep in discreet packaging, there’s no reason to hesitate.

Risque Fetish has a list of FAQs and privacy guarantees clearly laid out for customers. With shipping as fast as Amazon too, that means you’re able to play with your new sex toys in no time!

As a sissy, you can feel confident about where you’re ordering from.

Shop for Sissy Dildos


Pros:

  • Realistic sissy toy
  • Best dildos for anal play
  • Must-have as a size upgrade

Cons:

  • Stretching out first
  • Only a few squirting dildos
  • A lot of size for some sissies

Bonus: Sissy Chastity

Chastity Cages are an essential training item for sissygasms. If you want a handsfree orgasm, then suppress the urge of touching your clitty!

Although it may take days or even weeks of training to rewire a cock to only cum from anal play. So that’s solely up for you to decide if the commitment to sissification is worthwhile.


“If you’re going to wear a sissy cage for an extended period of time, then buy an adjustable one. Otherwise, it’ll either be too tight or slip off easily. After about an hour, you’ll also notice a bit of pinching if a device isn’t designed well.”


The downside of cheap chastity cages is how they’re not adjustable.

Don’t waste money on an uncomfortable one that’ll poke and pinch you. From experience, we know it’s worth splurging for a long-lasting, premium device.

Trust us because you wouldn’t know this until you’re already locked up!

Shop for Chastity Cages


Pros:

  • Desirable sissy accessory
  • Most reliable chastity cages
  • Comfortable, yet secure too

Cons:

  • Confusing to wear at first
  • Often sold out of pink cages
  • Might be too pricey for some

Bonus: Cuckold Fantasies

Cuckold Toys go hand-in-hand with being a sissy. Actually, it’s pretty common for cucks to slowly dive into feminization if they love the fetish.

After all, each involves submissiveness and a passion for big cocks. Regardless, cuckolds in training will enjoy exploring their sexuality with anal toys too.


“Have you ever fantasized about being pegged by a girl with a strap-on? Now try taking a thick, black dildo and imagine a woman dominating you from behind!”


If you’re a sissy who has a girlfriend, would you like a threesome with a guy?

Let him fuck your mistress while you lay beside them, watching in awe. As she throbs and orgasms on another man’s dick, he pulls out of her pussy, looks at you, then says, “Your turn, femboy.”

For our single sissies, this could be a good training activity to consider!

Shop for Cuckold Toys


Pros:

  • Cuckold training toys
  • Variety of adult products
  • Perfect for dominant wives

Cons:

  • Have to use sorting filters
  • Also includes masturbators
  • May not be a fetish for you

Bonus: Risque Lingerie

Fetishwear is precisely what you need to become a submissive sissy. That’s why Risque Fetish’s lingerie section has plenty of fishnet bodystockings.

From hip-hugging garters to intricate lace and ribbons, there’s a lot to browse. After squeezing your curves into an outfit, all that’s left to do is tuck that clitty back so there aren’t any bulges!


“Just like a cake tastes better with frosting, a sissy will feel naughty wrapped up in lingerie. And when it’s crotchless for easy toy access, you can do your anal training while wearing the sexiest attire.”


Crotchless lingerie makes sissy play a breeze with dildos, vibrators, or prostate massagers.

Risque Fetish Toys tailors the fetishwear to draw out all of those feminine desires. For anyone striving toward full sissification, it’s a mandatory accessory.

Don’t forget to pick up a pair of sissy training panties too!

Shop for Fetishwear


Pros:

  • Many crotchless options
  • Sexy and revealing designs
  • Diverse collection of lingerie

Cons:

  • Must use filters for sizes
  • Overwhelmed with choices
  • Some outfits in panty section

Bonus: Thigh-High Socks

Thigh-High Socks are a must to complete any self-respecting sissy outfit. It’s as easy as sliding up a pair of stockings to instantly appear cuter and more feminine.

Sissies will love the submissive feeling of knee-highs tightly hugging their legs. Plus, they’ll remind you how lucky girls are to get to dress like this all the time!


“At Risque Fetish Toys, there’s a huge selection of affordable nylon socks. Simply being able to buy a dildo, BDSM toys, lingerie, and thigh-highs all in one place is unheard of for a sissy shop.”


If you don’t understand the appeal yet, it’ll be crystal clear once you’re wearing them.

Choose from striped, sporty socks or lace thigh-highs with ribbons and bows. Then take a peek in the mirror to see how it’s truly the cherry on top of a sissy’s outfit.

Add a pair into your cart along with a brand-new sex toy now!

Shop for Thigh-Highs


Pros:

  • Affordable, yet well-made
  • Quick and easy sissification
  • Different styles of stockings

Cons:

  • Hard to make a choice
  • Be sure to sort by your size
  • Could use more product pics

Sissy Recommendations

Risque Fetish Toys has everything you need to fulfill your submissive fantasies.

And they’re even featured as part of a full guide to becoming a sissy. – So it’s pretty worthwhile to see the official shop’s product recommendations.

That’s why our team reached out to ask about sissification…


“Realism has a key role in a submissive’s satisfaction. It’s important that your dildo appears and feels lifelike. Not to mention, shopping for these adult novelties can be sexually exciting in itself.” said a RisqueFetish.com representative. “Don’t forget to look over our lingerie too. At least one pair of panties is a necessity for undergoing sissy training.”


Complete your feminization! – Browse a dedicated collection of sissy sex toys chosen by Risque Fetish now.

Visit Risque Fetish Toys