Dear Lili,

Hi, this is so embarrassing to be asking this in such a public way but I don’t know where else to turn. My boyfriend and I have been going out for a while. Everything has been going great but recently he’s been getting a little fresh. The other night he tried sliding his dick in my butt without asking. I was so offended that he dared to try that without asking me. I mean I get it, when you’re in the moment things can get hot with all that dirty talk under the sheets but I still feel like that’s a huge deal. Things calmed down a bit and he asked me politely the other night if I would be open to trying anal for the first time and I didn’t know how to answer him. I don’t want to feel pressured into this because I’ve heard horror stories of girls assholes being torn open because the guy was too BIG down there. I’m not trying to bleed profusely and end up in the emergency room so the doctor can tell my father I’ve been ass fucking my boyfriend all night. But on the other hand there’s a crazy side of me who wants to feel what it’s like to have your man up in there…I’ve seen porn movies and it looks like it would hurt like a bitch but maybe I’m just overreacting…

Should I give this a go and see where it goes (no pun intended) or, dare I say it, should I be worried that my boyfriend is turning gay on me with this butt sex fetish?

Anal Virgin


Dear Anal Virgin:

I’m glad you came to me with this question. First off let me say that your boyfriend is not turning gay on you because he wants to try anal. Anal is something that fascinates most men because of its “taboo.” Men want what they can’t have, especially if it means a tighter grip around their penis.

It’s not cool that he tried it without asking but the fact that he put his tail between his legs then approached you with this topic in a polite manner, means that he knows what he did was wrong and wants to discuss the possibility with you. I say listen to your crazy side and explore the idea of having your man up in there. Having your asshole torn open is something that shouldn’t be an issue if you approach anal correctly and he doesn’t have a massive dick.

Tips before the tip goes in

  • Relax! Light candles, start by having him give you a full body massage, and put on sexy music to put your mind at ease. If you are tense, body parts will be tense and it will be harder for him to enter.
  • Liquid courage. Have a drink or two to loosen you up (literally and figuratively)
  • Lube is your best friend. Find a lubricant that you are comfortable using and have it on hand.
  • Start small. Have him start by applying lube to his fingers and spreading it around your asshole. Just like fingering your pussy, have him finger your asshole to stretch you out a bit. Add another finger slowly the more comfortable you get.
  • Take your mind off things. Don’t think too much about it. Have him focus on kissing you, rubbing you all over, and be sure to be in a comfortable position (on your knees on the bed or on your stomach)

The Main Event

Comfort is key and so is using plenty of lube. Have him go slow and at a pace you are comfortable with. If at any time you want him to stop, speak up. When trying something new in bed it is important to be communicative. That being said trying something new can bring you closer together sexually and even if it doesn’t go as planned you can have a good chuckle at the attempt.

So give it a go, you just might end up liking it!




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