Anal Training for Sissies
For a man, being penetrated by anything is the ultimate taboo. Masculinity is associated with fucking, and femininity with being fucked. That’s why anal play is one of the cornerstones of the sissy fetish: because it makes us feel like a girl.
Besides the feminization aspect, sissies also know the truth most men don’t know: anal play feels incredible when done properly. Unlike taking a cock in your mouth, anal play and anal sex for most people requires preparation and practice. This guide to anal training for sissies will help you get started feeling a whole new type of pleasure.
What You Need to Start Sissy Anal Training
Required:
- Your Fingers
- Lube
- A sissy mindset / being horny
Optional, But Encouraged:
- Butt Plug(s)
- Dildo
- Enema Kit
Sissy Anal Training Preparation
Yes, your boy pussy is both an entrance…and an exit. While it’s important to accept that sissy anal can get messy, it doesn’t have to be. If you’re a fairly regular person, you’ll likely have no trouble doing short amounts of play without any issues. If you’re not, you may want to try adjusting your diet and staying away from foods that cause you issues in the day or two before anal play.
First, you’ll want to make you are clean so shower and be sure to clean up inside your sissy hole. If you haven’t shaved yet, carefully make yourself hairless, especially around your ass, so you will feel feminine as possible. Be sure to also either cut or file your nails to make sure there are no jagged edges.
When you get into more advanced anal play and longer sessions either with yourself or with a partner pounding you, you may want to look into enemas. They should be used sparingly and carefully as they can cause injury, but if done properly will clean your insides and help prevent accidents.
Starting Small With Fingers and Lube
While some sissies, particularly the bimbo sissies and sissy sluts, may want to jump right into taking giant monster porn cocks, it’s best to start small. Fortunately, you don’t have to buy a ton of sex toys to start if you don’t want to. All you need is some lube. If you’re just starting out, the KY or Astroglide you’ll find at most pharmacies will do the trick. Coconut oil also works very well as a backup if buying lube makes you anxious or if you need to be more discreet at home.
Make sure you’re horny and relaxed. If you’re not and haven’t already gotten dressed up and in your best lingerie, go for it. When you’re ready, get into a comfortable position and start gently rubbing your fingers against the outside of your sissy pussy. Do this while rubbing your nipples and your clitty to get yourself in the mood.
Now, gently lube up a finger and slowly try to push it inside. With the lube, you shouldn’t feel any resistance, but take your time and relax. Continue touching yourself elsewhere and fantasize about getting fucked. You should start to feel less resistance as you continue to slide your finger in and out. If you still feel some tightness, apply more lube. For anal virgins, it may take more than one attempt so don’t feel discouraged if this isn’t your time.
When you’re ready and feel loose enough, apply more lube and try to insert two fingers to start feeling like a naughty anal slut. Continue to explore your body and pay attention to the signals it is sending. Stop if you feel pain and never try to force yourself to go further than what your body currently is allowing. Anal takes practice and dedication before you can start taking the big cocks.
Butt Plugs
Next to chastity cages, butt plugs are a sissy’s best friend. Butt plugs deserve their own post, but on the most basic level, a butt plug helps to create a sense of fullness when worn for extended periods while also helping to relax and stretch open the butt for a real cock or dildo. Here are a few things to keep in mind when deciding on a butt plug:
- Size: start small and don’t overestimate what you can handle, or you may wind up hurting yourself or with a toy you can’t use right now. For beginners, there are special anal training butt plug sets you can buy with plugs that increase in size.
- Material: silicone, steel, and glass are a sissy’s best options because they’re easy to clean and sanitize compared to the many rubber plugs out there. Silicone tends to be cheaper and squishier, so it’s probably the best bet for beginners. If you choose silicone, only use water-based lubes as silicone lubes will break down silicone toys over time.
- The Base: especially for extended wearing, you want a larger flared base that won’t be uncomfortable and press harshly on your butt, but at the same time can’t easily be swallowed up inside.
- Jeweled-Metal Plugs: most sissies will buy a cheap metal plug early on because they’re super cute and sexy. Like, how hot is it to spread your cheeks and see a hot pink jewel there? From personal experience, the base of these plugs isn’t big enough and it can be easy for your body to suck up the whole plug. No one wants to be the sissy in the emergency room for losing a butt plug inside them. I also don’t find them that comfortable after extended use.
- Patience: butt plugs take time to insert and it may take a lot of sissy anal training for you to get to a bigger size. Always go slow, be patient, and listen to your body. If you feel any discomfort, take a breather before continuing to avoid hurting yourself.
Dildos
While many sissies will wear butt plugs almost constantly, I mainly wear them to help prep myself for taking dick or riding a dildo if I’m by myself. Compared to a butt plug, having a dildo inside you provides a greater sense of fullness and also makes you feel like a naughty slut, especially if you buy a realistic-looking dildo.
I will write a separate dildo post in the future, but for sissies new to dildos there are only a few key differences to consider from butt plugs:
- Length: a slutty sissy will no doubt want to find the largest, longest dildo she can, but like butt plug width it’s better to start with a dildo that’s between six and 8 inches long. The p-spot is only a couple of inches inside most men so you don’t need anything 12 inches, which will probably just feel unpleasant.
- Base: like butt plugs, you want a flared base that won’t get lost inside you, but I’d recommend you also look for a starting dildo that has a good suction-cup base. That way you can easily ride your first cock like a slut or put it on a wall to practice your deep throating!
- Shape & Stiffness: many sissies may prefer a dildo with a slight bend to it that helps to hit the P-spot. For beginners, I would also recommend finding a dildo that is slightly squishy with a firmer stiffness in the center. If it’s too squishy, the dildo will be harder to control while a dildo that’s too hard may be uncomfortable (and also doesn’t feel like a real cock if that’s what you’re going for).
Are You Ready to Take a Real Cock?
There are so many different types of anal toys you can try from inflatable plugs to anal beads that a sissy’s anal training is never complete. After playing with yourself for enough time, it’s time to ask yourself are you ready to take the next step and take a real cock from a man or get pegged by a femdom?