Now, before you start there might be some things that you can do to make this more enjoyable for her.  For instance, make sure your nails are smooth. We don’t need you boys ripping our vag walls with your un-kept nails. Also lots of lube, the more the better. Slab it on your hand, her ass or pussy, and make sure to get it all over and around your fingers.

When starting fisting know that it will not happen all at once. This is a process. Ripping can occur and that is why I cannot stress enough to take it slow and take signs from her to know when to stop. 

Take one finger and start fingering her. You know you like feeling her wet hole so this should not be an issue. Once you have got her wet enough to take five fingers *now pay close attention this is vital info* slip the knuckles inside and fold your thumb inside your fingers. INSIDE YOUR FINGERS!!!  You do not need to clench your hand down because your hand should form a natural fist.

Boys the only other thing you need to know is if she clenches up stop, and don’t pull out until the contraction stops. You can seriously hurt someone if you pull out mid contract and could damage mussels. If this happens as well it means you have reached your limit so give her a break. She has been a good sport; maybe go down on her to show her your thanks!

“I’ve been trying, unsuccessfully, to get my girlfriend to have anal sex for sometime. For girls who enjoy anal sex, do you let your man finish in you or have him pull out?” (David, 23)

 Ms. Zombie says:
Let’s just say every girl is different and will have their own preference and you should ask her about this. However, personally I do not care. Both have their ups and downs. If you have a condom on, it really doesn’t matter. If you are doing it without a rubber, cumming in the ass is way, way sexier but can leave a sticky mess hours down the line. Pulling out doesn’t get the full experience of the ass tightening up around your cock, but seeing your cum spread over her ass is pretty damn cool. Mr. Zombie once took a pic with his phone after and I have to admit it was hot. I repeat though, ask your chick! She knows better then me.

Lady Love says:
Definitely ask your lady. I’m not talking about sitting her down over coffee and discussing whether or not you’ll cum in her during anal. Timing is everything here. I’m talking about wait until the heat of the moment, when you’re almost ready to burst and in a hot, sexy tone ask her where she wants it. Don’t assume anything because she’s the one who’ll have to deal with the gravitational pull of your cum inside her ass, and believe me, unless she asked for it she wont be too happy. You don’t want to get on her shit list after some good anal, right?

Madam Cougalicious says:
Really?! Try something for me David, stick a cucumber up your ass and then eat it.

If you do, you’re one sick fuck.Might as well join the circus, you freak.

If you don’t or won’t, then don’t ask your lady. The thought to cross contamination comes to mind and not so much for you as for your partner. Some things are better left for gay porn.

One reason might be because they are scared of something new or it’s a homophobic thing. Either way, relax! Anal play can be a boys best friend too. I am not saying taking a 12 inch dildo and shoving it up your ass raw, but let the fingers graze it, maybe a tongue if she is willing to try that. Some times during sex I like to have him laying diagonal on me that way it lets me play with his balls and his ass a little, and you know what it brings… more stimulation, which equals better orgasm. And let’s face it that is what we are really aiming for.

After you relax a little and you feel comfy with the grazing and licking and rubbing, maybe you’ll realize you want a little more, then a finger can slip in and bam! You got prostate stimulation or the male g-spot. You wanna cum hard? If she, or yourself press upon it while jacking, fucking, or sucking you will cum harder than you have ever in your life. Also try a pocket rocket because also a little vibration never hurts and they are small so you don’t have to worry about stretching your ass out.

Guys there is nothing wrong with ass play! Your chick won’t see you as gay, and you will be in heaven. Just remember the lube!!!