Message: Girlfriend Ready to Try Anal

ilyjokesMy girlfriend is ready to try anal but I want to go about it properly so eventually we can join the Anal only lifestyle. What are the materials and techniques needed to do just that? The help and advice is very appreciated.

You need lube, butt plugs and patience.

Don’t try to have anal sex for a while, start experimenting with anal play on a small scale first. You have to work up to it for it to be enjoyable and pain free. You should also encourage her to explore her own ass on her own time (during a shower is a good place to start, and then during masturbation as well) to become familiar with it, what it’s capable of, and what its current limitations are.

Start with just a lubricated finger (trim and file your nails!) very gently inserted into her anus while stimulating her in another way she really enjoys—whether it be fingering her or giving her oral or using a vibrator on or rubbing her clit. (Or she can be in charge of the clit stimulation while you finger her ass.) Have her tell you if anything hurts at any point. When she tells you, stop moving your finger in her anus and hold it still until the pain fades. If it still feels too intense for her, pull it out partway until she’s ready for you to continue. Once you’ve fully inserted your finger, gently start moving it in and out. Continue other stimulation throughout all of this. Ideally continue until she reaches orgasm.

Do this regularly. Make it a part of your routine. After doing it a number of times, try inserting a second finger. Every time you do an increase in size like that, use the same precautions as the first time—go very slowly and make sure to stop if it hurts. By inserting a little bit until it’s uncomfortable, then waiting and trying again a few moments later, and repeating, you can easily increase the size that can be comfortably fit. It just takes practice and patience.

Eventually, once she can fit a few fingers in, get a butt plug about the same diameter as your combined fingers that she can fit inside. She should wear the butt plug during masturbation sometimes, and during oral, finger, vaginal sex, etc. It will help her on several levels: she’ll learn to associate having something in her ass with pleasure, she’ll become used to the sensation in general, and she’ll gain more conscious muscle control from having the butt plug inserted and over time will be able to consciously loosen up more easily for sex. When training for anal it’s often good to wear a butt plug for a while each day even just when doing other non-sexual activities, just to start getting used to it and getting loosened up a bit to make future sex possible.

Eventually, once she feels comfortable with a butt plug for a reasonable amount of time per day and can fit three or more fingers easily, she might be ready to try actual anal sex. When you do this, let her be the one in control for the initial penetration and first few minutes. There are several positions that work well for this, but I’m fond of the girl on top squatting over your penis and lowering herself onto you. This position naturally relaxes and loosens the anus a bit to begin with, which also helps. Once you’re fully inside, she should pause a moment to adjust and then slowly move up and down. Once she’s more comfortable, you can try changing positions and take some control as well. But still go fairly slowly at first until she tells you she’s ready to go faster!

Always use lube. Always warm up. Always be careful and go slowly when training and trying to increase size. Stop if there’s pain and wait before trying again. Don’t ever just push through pain and keep going. If it hurts, you haven’t warmed up enough yet.

Good luck!

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