Anal Sex & Toy Problem

Q. I have a dilemma; my boyfriend and I want to start having anal sex but it doesn’t fit and it hurts so bad when he even tries. What can I use or do to ease the pain and have him be able to fit? Also, I decided to try to break myself in with my silicone dildo which went in quite painfully and came out discoloured. Now I can’t remove it; I tried soap and water which is what I usually wash it with. I’m embarrassed and afraid my boyfriend will see, or that I might just have to throw it out and explain why. The dildo is kind of lifelike, rubbery and flesh toned. How can I get this out?

A. Your experience with Anal Sex will be directly related to how confident you feel with your partner. If you can’t be open or ask for what you need, it’ll make it virtually impossible for you to have anal sex with him.

Getting comfortable with anal play doesn’t happen overnight. You had the right idea of experimenting with a dildo in order work your way up to penetration by your boyfriend. It helps that you integrate it into regular practice and it is of great benefit to start using smaller Anal Sex Toys like anal beads or tapered butt plugs. If you’re boyfriend wants to be part of the journey, ask him to help you get really aroused, and I mean really turned on. Next, have him pleasure the rim of your anus with his tongue (Analingus), or very gently with Anal Fingering. While you keep your clitoris “busy” using your fingers or a vibrator, have him penetrate your anus with a toy slowly, and inch by inch.

As you get accustomed to your rectum being penetrated, you’ll be able to relax the sphincter muscles that customarily trigger the tightening response. This enhanced control should in turn greatly relieve the pain your feel when your back door clamps shut. When the two of you decide you’re ready for his manhood, go slow and be very, very vocal about what you need him to do to make it a satisfying for you, e.g. “keep rubbing my clit”, “go really, really slow”, etc.

As for the stain on your toy, during anal play it’s not unusual for tiny bits of fecal matter to adhere to it. Soap and water usually do a good job of cleaning silicone, but if the device doesn’t have any electronic components, you may want to boil it then wash it. Check out our articles on Sex Toy Materials and Care for more information. To avoid this from happening to another toy, restrict anal play to a material that doesn’t stain such as glass, or go for a darker color; alternatively, cover your pleasure object with a Condom.