If you haven’t already , you should explore your anus with your fingers before you even consider a toy. Get to know the area a bit before you start putting stuff up there!
Any toys that are going into your butt need to be thoroughly cleaned before (and after) penetration. Hot water and soap are usually sufficient, but you can also find antibacterial sprays specially formulated for sex toys. Some toys can also be sterilized by boiling them (or even putting them in the dishwasher); check your toy’s manual for specific instructions (and ya know, maybe don’t toss your dildo in the dishwasher if you have roommates around).
For your first foray into anal sex toy land, think about whether you want to be the one holding the toy, or if you’d like your partner to do it. If you’re nervous, I’d suggest being the one to hold it, since you’ll have more control. A partner has the advantage of being more dexterous, but you’ll have to make sure to communicate with them about what feels good and what doesn’t.
Next, find a position that gives you good leverage. The arm that’s operating the toy will need to stretch further than you usually do when you masturbate. Sitting up in bed with some pillows propped behind you is usually doable. If you’re with a partner, they can sit between your legs. You want to be relaxed and turned on before venturing backdoor. One of the challenges of using anal toys is getting your muscles relaxed enough for penetration,so do whatever tickles your fancy: put some fingers up there, masturbate, get your partner off, watch porn, fantasize, you know the drill.
Make sure you have your trusty lube nearby. If you’re using a silicone toy, you’ll need to use a water-based lube (silicone lubes can break down the silicone in your toy). If you’re using a stainless steel toy, you can go for silicone or water-based lube.
Next, whoever is wielding the toy should pick a designated butt-hand. You want to be careful not to get fecal bacteria in your other orifices, so use just one hand to touch your asshole, and keep it off-limits from any other activity. Put a nickel-sized amount of lube on your fingers, and apply the lube to your anus. You can push your fingers in a few inches to get some lube inside and prepare yourself for the toy. Then thoroughly saturate your toy with lube. You want it so lubed that it practically slips out of your hand. Lube is your friend when it comes to anal, and you really can’t use too much. For peace of mind, you can put a towel under your butt to guard your sheets against lube spillage.
Holding your toy in your butt-hand, press the tip of the toy against your anus as you continue masturbating. Just hold it there for a few moments while your body adjusts to the pressure. When you feel ready, gently push the toy in about an inch or less, then hold it there. If this feels painful or like there’s too much resistance, slowly pull the toy out. Hold it against your anus while you keep masturbating. You can also add a little more lube if you feel like the toy is tugging at your skin or not gliding smoothly. If all systems are go, slowly slide the toy further in, an inch at a time, taking breaks to hold it in place and keep masturbating. Once it feels like the toy is fully inserted, try taking your hands off of it. Some toys will stay in place snugly, while others may get pushed around a bit by your sphincters. If it feels like your butt is pushing your toy out, just hold onto it to keep it in place. If your toy has a flat base, you can sit up a bit so the base comes in contact with your bed and keeps the toy inside. You can keep the toy stationary, and enjoy the sensation of fullness it creates. Or try moving it in and out or around in circles.
When your orgasm, your muscles will contract, and will attempt to push the toy out. This is where having a towel beneath you comes in handy! You can let your body do its thing without having to scramble to catch the little plug being shot out of your butthole. The sensation of the toy coming all the way out of your asshole can feel a little bizarre, so just take a deep breath. If it doesn’t come out on its own, ease it out slowly. You may be tempted to pull it out quickly, but doing so feels a little too similar to pooping, so take your time.
If you’re using a toy with a partner, you may notice that the anus stays agape after the toy has been removed. This will be especially noticeable if you used a girthy toy. Don’t worry, your butthole will return to its usual puckered state in just a few minutes. Just pretend it’s saying “WOW!”
Wrap your toy up in your towel or in some Kleenex, and take it to the bathroom to clean and sanitize it. Don’t forget to wash your hands with soap and water, especially before touching other parts of your or your partner’s bodies.
Congratulations, you’ve now leveled-up in your anal adventures!