Message: Anal Looks Like It Feels So Good But I’m Scared

Anonymous: My boyfriend has a huge anal fetish and wants to try t so badly but every time I think of trying I get scared. I love the idea of anal too but I’m so scared it will hurt too much . I want so so badly to make his fantasy come true and become his anal whore but I’m too scared to even get started 🙁 please help. I see the girls taking dick up their butts and wish it were me, looks like it feels so good

Take your finger, put some lube on it, and slowly massage your finger into your butt while you rub your clit. Masturbate to orgasm that way. The next time, try two fingers, then three. If it starts to hurt when you go up in size, stay a little bit longer with something smaller before trying again. Make anal play like this while you masturbate a standard thing—make sure to have something up your ass whenever you masturbate.

Once you can regularly and comfortably fit a few fingers in your ass, get yourself a nice buttplug or two. Something around 1.5″ diameter at the widest, like a Tantus Ryder or similar size, is a good starting plug once you’ve already done some pre-plug preparation with a few fingers. Use this plug during masturbation or even some sexual activities with your boyfriend.

Once you feel ready to try it with your boyfriend, wear the plug for a while beforehand to help warmup, then lube up his cock and your ass, have him lie on his back, and lower yourself onto him so you can control how fast and what angle and depth for the initial penetration. Push out as if going to the bathroom to help relax your anal muscles and let him in more easily. If it starts to hurt, pause and hold in place and wait for it to fade before you continue. Once he’s all the way in, pause again a moment and get used to having him inside you, then start moving. After you’re used to it for a few minutes, you can try changing positions and letting him take more control, but make sure he’ll listen to you if it starts to hurt and stop or give you a break.

The key takeaways are: use lube, introduce anal sensations to yourself at your own pace first and alongside pleasure sources you already enjoy and associate with pleasure like clit stimulation, work up in size gradually, and stop and relax before continuing if something starts to hurt—pain means you aren’t warmed up enough or aren’t quite ready for that size yet, but if you do things right, it shouldn’t hurt!

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