Connected to one of the premier starlets in the industry, when do you think anal sex should be introduced into a relationship when it takes sexual flight? First encounter of intimacy? Second? Etc.? This is to seek advice with respect to statistics, as it seems the male always wants it, but the female doesn't, usually, so when do you feel it's a safe time for a man's approach? Thanks.

Sincerely, Without It For Too Long

If you have to over-think it so much with someone, then it probably isn't appropriate. If you are on a first date with a girl and you're like, getting down and dirty, and you're like, “Man, I really wanna put it in her ass but I don't know if she'll be into it”...then she probably won't be. You will know when you are with that special someone who wants it in their ass on the first date.

You know when Joanna was in college, she was not a porn star. She was a regular girl who was in college, and from my point of view, I saw the same four or five penises go in and out of her pussy all the time. She wasn't some sexual deviant until later on in life, and then I went from being ignored, to being over-used. I know for a fact that anal sex with her college boyfriend was very much her idea, and not his...and like I said - she wasn't some freak of nature. There are lots of girls out there who want to have anal sex...they just don't talk about it as much as guys do. Females in general, tend to have a little more um...tact.

Anyways, I am not sure what else to say. There is no right number of dates or hours you need to spend with someone before anal sex is appropriate, every situation is different. You know when you were like, in 5th grade, the thought of just kissing a girl seemed daunting? I mean, knowing when to make a move was one of the most stressful things a kid in elementary school faces...and then as you grow up...you just know. You only have to think about whether you should lean over and kiss someone for like, five minutes, instead of five weeks. As you go through life, you just kinda figure things out. This will happen with anal sex eventually...maybe it just hasn't happened to you.

Alright Joanna, I've got two really serious questions. First question: I'm in kind of a spot with my girlfriend. I love her to death; am probably going to pop the question one day, and everything about our life together is great, except when it comes to the sex. When we first started dating, everything was great, and even when we go at it now, it's still a shit-load of fun, but it just doesn't get me off anymore. She gets hers - no problem - but it's rare that I get mine. I mean, I've tried everything, we've switched it up, gone through every position we can find and even some we made up!, the girl does anal and she even gives me a threesome once in a blue moon. The threesome is about the only way I get anything cause I got someone different to play with. Can you help me, give me tips...any advice? And question number two: would you come out to Maryland and have a threesome with me and my girlfriend? The only girls she ever agrees on are always fuckin' gorgeous and inked. She won't settle for anything less, so I figure I should fuckin aim high...and that's you.

- Unable-To-Cum-With-Sweetie

Well Unable-To-Cum-With-Sweetie, since I am just an ass, I don't have a driver's license. I know - it's totally messed up, but the DMV wont even let me take the test. I have to depend on Joanna to take me everywhere, and she's pretty busy. I don't know if she has the time to fit a Maryland threesome in her schedule but, I'll see what I can do.

About your problem...I don't think you should pop the question until you have this issue figured out. You don't want to be one of those married couples that never has sex...now do you? You'll just wind up hating each other and cheating on each other and shit will just get ugly. This whole thing sounds pretty depressing. You should try watching porn together, maybe experiment with some role playing games, or I dunno...maybe you should try, like, banging a dude. It sounds like you have a pretty amazing girlfriend that other guys would die for. I have an idea...why don't you let me date your girlfriend for awhile and you go and like, find yourself?

Dear Joanna's Ass, I'm a nymphomaniac inkaholic with a problem. I'm about to do the unthinkable for most girls and get my pussy tatted. Now, I know with tattoos, you're not supposed to fuck around with them during the healing process, which means no getting my snatch pumped nice and hard for a couple weeks or however long it takes to heal. Any ideas on how to get around this dilemma? I'm guessing just take it up the butt for awhile and suck off as many guys as I can, but what if the urge for cock is too strong for my twat to resist? I really want my pussy tatted, but don't know how long I can hold out. Please help!
Sincerely, Out of Order Pussy (O.O.P.)

Yo, reading this question kind of turned me on. Miss O.O.P., you are awesome. *Smack* HI FIVE!

Ummm...I know sex is a bad idea when you get your pussy tattooed but I think dildos are ok? I think? I am not a tattoo artist but I think, like, a glass dildo or something should be OK. It might be healthy for you to take a cock vacation and pleasure yourself for a little while. Think of it as, like, a master cleanse-type deal for your pussy. It might suck while it's going on but...afterwards, you will feel so refreshed. Don't you know how shitty it feels when your tattoo is healing? I mean, it hurts - I can only imagine it hurting even more on your pussy...I know this might sound outrageous, but you might not be as horny as you think you will be after you get it done.

I dunno. Go get the tattoo...I think it will suit you. You need that pussy tattoo, you will be doing the world a great disservice if you don't get one! You'll be OK. Just breathe. You can do it.