Written for GFH by Luna Matatas

Are you up for an anal adventure? If you’ve been exploring with beginner butt pleasure for a while, you might be curious about trying more advanced anal pleasure techniques and giving anal sex toys a try.

But, how do you know if your butt is ready for more? Sometimes our eyes are bigger than our butts and you might be eyeing a longer or bigger sex toy, but your body simply isn’t ready and you’re met with butt resistance. You might have reached a limit or you might need more time to practice.

Anal training is a practice where you slowly stimulate the butthole and the rectum with vibrators, fingers, and small butt plugs to help the anus slowly relax and open up to penetration. If you’re not sure if you’re ready, read 10 Tips for Pleasureable Anal Sex.

When you’re working up to more advanced anal pleasure, it’s still important to warm up the butt with external (e.g. rimming) and internal stimulation techniques (e.g. vibrating butt plugs), and use LOTS of good quality and long-lasting lube. The anus isn’t self-lubricating, so try a silicone lube or a thick water-based lube. 

Fingers are great tools for helping to warm up the anus and train it for advanced anal sex. After a lot of build-up, try two lubed-up fingers inside of the anus and instead of aiming deeper, try:

• Making circles with both fingers together
• Separating two fingers gently inside of the anus stretching the rectum horizontally and vertically
• Rotating a thumb side-to-side, gently stretching with each half-circle motion

Working your butt up to bigger dildos

You can explore anal pleasure through stretching with dildos that are girthier like the Tantus They/Them Dildo. Generally, try to choose a dildo that is slightly bigger than the one you are already comfortable with. Some people also enjoy going for depth—taking longer dildos like this 8 inch dildo. A good way to work your way up to longer dildos is to explore anal beads. If you’re aiming to explore deeper anal pleasure, then flexible dildos are important to work with the natural curves of the rectum.

Get started with your bigger dildo with these tips:

• Add more lube, and keep reapplying as you move your dildo in and out.
• Instead of pushing the toy into the butthole, try bumping, grinding or gradually lowering your body onto the dildo.
• Adjust your body position—what feels good for smaller butt sex toys might not be what feels good for larger toys. Try the fetal position with your knees up to your belly to lengthen out your rectum.
• Try stimulating other parts of your body to increase full body arousal (e.g. nipple clamps, vibrators).
• Inch the dildo into the anus instead of going for one big thrust.
• Once inside the anus, hold the dildo still and give the rectum a chance to adjust to the fullness.
• With bigger dildos thrusting might feel good or it might be overwhelming. Explore rotating the dildo, angling it towards prostates for P-spot pleasure, or focusing on the sense of fullness in the body. 

Remember to breathe and take it slow. It’s important not to ‘force’ your anus to open up if it’s not ready. The anal tissue is delicate and it’s easy to create injury to the tissue, like anal fissures, if your anus isn’t well-lubricated and warmed up. If you haven’t penetrated your anus recently, it may have tightened a bit and you may need to approach it slowly even though you know you’ve done it before. 

Trying different textures of anal sex toys

Girth and length aren’t your only options for advanced anal pleasure. Exploring different materials and shapes of sex toys for anal play:

• Smooth dildos are great for anal pleasure for beginners. If you’re already comfortable with smooth dildos, try a textured one.
• Glass sex toys are very firm and can feel uncomfortable for newbies. Their smoothness combined with lots of lube can create a great texture for moving a toy in and out of the anus. Glass dildos can be put in the freezer to explore anal temperature play. 
• Stainless steel sex toys let you play with gravity and weight for anal pleasure. The weightiness of stainless steel butt plugs or The Steady can give extra stimulation to the many nerve endings around the anus.
• Double-ended dildos can be used for double anal penetration or simultaneous vaginal and anal penetration.

Always choose sex toys with a flared base for anal sex to keep them from getting lost in your body. 

Creating different anal sensations

Exploring different anal pleasure might mean using your sex toys in ways you never thought of for anal sex or it might mean shopping for something totally new. Here are some anal sensation sex toy options:

• Rimming butt plugs allow your ass to feel penetration from the top of the butt plug, while the neck of the butt plug rotates and vibrates to stimulate the nerve endings of the butthole. Feels like you’re getting your ass eaten!
• Try using a powerful wand style vibrator against your butt plug or dildo while it’s inserted. 
• Get curious about suction dildos to allow you to get into different positions for penetration, like squatting or bent over or even in the shower.

There isn’t a hierarchy of anal pleasure—bigger and deeper isn’t necessarily better. You might just be looking to try some new ways of experiencing anal pleasure. Get curious and get lubed, and you might just discover another way to get turned on by butt stuff!