I’m 21 years old, and have not had much experience with sex, and most of it has not been very enjoyable. I would really like to explore my sexuality much further—I am a fairly shy and modest girl but get me in the sack and I can get pretty wild. I want to try and open that side more, you know, be ‘freer’ if you will.

Anyway, I was bored one night, so I decided to post an add in casual encounters on craigslist, basically explaining this need of mine—just for shits, to see what would come up. It was practically a joke, because really I just expected to get a bunch of iphone photos of dicks in response. Not to mention I’ve always been against the internet thing, because you never really know who they are, and it always seemed kind of stupid/desperate to me. Hell, I didn’t even plan on responding to any—it was kind of a spur of the moment, probably change my mind about it tomorrow, kind of deals.

Most responses were just creepy or dumb, (fun to laugh at though) all except for one. Didn’t see it coming. This guy seems genuinely alright, is in school for massage, has sent several pictures (of his face) and not to mention in all of the “hey what kind of interests do you have” he completely blew me away and ended up basically explaining my interests, dreams and goals back to me before I even got the chance to. We also seem to have a good understanding of each others needs and ground rules.

We’ve sent some emails back and forth for a couple months now, and he’s invited me to get coffee and the like recently (however I missed it, that’s what happens when your only form of contact is through email, which I don’t check too often anyway) and I would like to, but there’s also that part of me thinking “Oh hey, what if I get stabbed?”

So I guess there’s really a couple questions here I’m trying to get at. Is the internet thing somewhat legit? If so should we try and make an actual meet up plan through email, or should I just pass him along my phone number?

And like I said, I’m a pretty shy and modest girl. Cautious with strangers, not so much cautious with the rest of life. I’ve never done anything remotely like this before (part of the reason I want to, I suppose). Never met up with a stranger like this, and I’ve certainly never fucked a stranger. How do I meet up with this guy and (if it works out) turn him into a fuck buddy in a non-weird/awkward (or less-weird/awkward) way?

Don’t give him your number. Get his. Call him when you’re ready. If there’s still chemistry after a phone conversation, feel free to plan a meet.

Choose a very public place, and make sure a friend with discretion knows where you’re going. If you’re feeling particularly cautious, pick a place where he doesn’t see you park. I don’t know what kind of town you live in, so a generic recommendation would be a shopping mall or an outdoor restaurant.

If the meet goes well and you’re in the mood to fuck, get a room. Don’t go to his place. Don’t take him to yours. This shit only goes down in a hotel. A nice hotel. Get a fucking suite if he can afford it.

Since this is your first time, plan ahead and have a couple of hotels in mind that you know and trust. It’s fine if you want to chip in on the room, but it’s his name that goes on the room. It’s his drivers license and credit card that goes on file. No exceptions.

Make sure you get your own room key card. I suppose it’s an extra bit of safety, but personally, I like to keep them as a souvenirs. At this point, I could tile a bathroom with all those little fuckers.

Be safe and listen to your gut. If it ever starts to feel weird, just walk out the door. You may want to check in with your friend before the hours start slipping away, but other than that just do whatever hot nastiness you like.

Happy fucking!

(Oh, and if you make it this far, write me back and I’ll tell you how to turn him into a regular fuck buddy.)

Is it ever acceptable to use the phrase “you’re too big” or is it just a shitty excuse for a job poorly done? I consider myself to be at least halfway sexually adept but I’m no porn star. How can I still maximize his pleasure without getting my throat fucked raw multiple times a week?

Once upon a time, a blow job was a rare and special gift reserved for birthdays and anniversaries, and if on such a momentous occasion you were capable of suppressing your gag reflex to swallow his cock for even the briefest of seconds, he would crown you a deep-throat queen and throw diamonds at your feet.

Those days are gone forever. I blame the internet.

Our men have been raised on a steady diet of cheap and readily available gonzo porn with an ever hardening core. It’s not enough to start out with an oral sex scene anymore. Now every run-of-the-mill porn starlet has in her repertoire the ability to unhinge her jaw for a throat fucking so violent she ends up shooting vomit out of her nose.

Expectations have been raised. Standards have been lowered. Having one’s face aggressively cock pounded for twenty asphyxiating minutes is now just an average blow job.

I respect that you want to maximize his pleasure, but perhaps it’s time to change the game.

I suggest you move to a wet two-handed technique where you work the shaft like a traditional lubricated hand job. You only keep the head of his cock in your mouth, which allows you easier breathing and much better use of your tongue.

The trick here is plenty of lube (and/or spit) on your palms so that your hands become an extension of your mouth. As with all good blowjob advice, don’t forget to tickle his balls.

Are there any tips you can give a girl on how to be less of a doormat? I let people walk all the fuck over me, and I have pretty much my whole life. I know the response I’m going to get is probably something like “Well cut it out, tell people to fuck off.” I know it should just be as simple as that but it’s really just never been that easy for me. And if that’s really the only way, then cool, but I thought I would ask anyway.

Telling people to fuck off is easy. That’s not your problem.

Your problem is you’re terrified that they actually might go and fuck off.

Your fear of abandonment outweighs your need for a little respect, and so all the assholes that worm their way into your life tend to stay there because you’ll put up with their shit when other folks won’t.

Deal with your abandonment issues. Overcome your fear of losing people and replace it with the realization that your life would actually be better if all the assholes were out of it.

You have to be willing to lose people before telling them to fuck off has any weight behind it. Otherwise, an asshole will call your bluff every time.

This isn’t about being a hard ass. It’s about having self respect. No one else will ever respect you if you don’t first.

If someone disrespects you, let them know. Allow them to apologize. Do not turn the other cheek. If they fuck with you again, simply cut them out of your life.

Pretty soon, you’ll no longer need to tell people to fuck off, because you’ll be surrounded by good people who don’t treat you like a doormat.

I kind of have a crush on you, and not just because my tumblr dashboard tells me I do. You seem like an interesting, confident, forthright woman of the sort I should be associating with more frequently, which leads me to two questions:

a) are you like this all the time, or does your online persona (with the benefit of anonymity) differ significantly from the person I might pass on the way to the bathroom at, I don’t know, Area or somewhere?

b) I need to start hanging around better women. I live in a city with a vast population of well educated, attractive women that outnumber their male counterparts by at least 2:1. Up to this point, I’ve relied on two tactics (if you can even call them that), dating friends of friends and sitting in bars waiting for girls to hit on me. Friends of friends is fine, I’ll keep that up, no complaints there. But strangers, interesting strangers, are tough if, as I said, they haven’t approached me. The thing is, girls come up to me just enough of the time to make me kinda lazy, and I’m somewhat shy anyway, so what I could really use from you is a pep talk, or even just an anecdote or two from situations where you were approached by somebody non-shitty and came away feeling something other than socially violated. Something along the lines of “they’re just as afraid of you as you are of them” but for girls instead of snakes.

much appreciated,
shy barfly

a) I am like this all the time. If you passed me on the way to the bathroom at Area, I would be at one of the long white tables in the far corner where they let you smoke. I would be high as a fucking kite and talking all kinds of shit to a chorus line of douchebags in bedazzled jeans and Affliction shirts. Oh, and it would be Thursday night in 2006.

b) Nobody approaches me unless I want them too. If someone forces their way into my personal space and refuses to leave, I fuck with them unmercifully. Trust me, I can crush a man’s ego with the exhale of a cigarette. You don’t need to worry about a girl like me ending up feeling socially violated.

Then again, that’s why you’ve got a crush.

Speaking on behalf of all interesting, confident, and forthright women, let me say how much we enjoy the respectful attention of an interesting, confident, and forthright man. It’s programmed into us. We love it, and if you can string a sentence together without telegraphing your shallow intentions to fuck us that very night, you’ve already bested most of the competition.

Based on your note, you already seem to know what you’re doing. You opened with a healthy compliment in a slightly clever and self-effacing tone. You followed up by expressing interest in me with an honest question that got me talking about myself.

Do that in a bar, and you’ve got my attention.

Go get ‘em, tiger!

(Was that pep-talky enough?)

Do you ever wonder why your here? And your purpose? Or if you’ll ever find true love? I think about these things every once in a while, and although its great being single and wild, these thoughts come and go. What about you?

As an existential nihilist, I have a problem with folks who indulge in grandiose wonderings about a greater purpose to life.

Anyone with the slightest sense of scale recognizes that nothing we do matters. In a universe so infinitely vast, our lives are entirely without meaning. The trick is being able to laugh at the abyss because you recognize the freedom it affords you.

Pondering your purpose is philosophical masturbation, and the only way you can make yourself cum is by surrendering rational thought to religious doctrine.

No thank you — I don’t need god. I already have a clit.

I’m perfectly cozy with the cold hard knowledge that I’ll die never understanding the nature of the universe. In the meantime, I’ve carved out my own little corner of paradise and filled it with all kinds of love, none of which I would insult by deeming any one more “true” than the other.

That’s another thing — I can’t stand it when grown-ass women use the word “true” as an adjective for something so important as love. There is no such thing as true love. Only love.

Going through life with the expectation of some fantastical form of uber-love is childish wish-thinking that would be silly if it weren’t so damaging to adult relationships.

Sure, I like “The Princess Bride” as much as the next gal, but fairy tales are lies we tell to children. Still, the myth of Prince Charming manages to sneak past Santa Claus and the Easter Bunny only to worm its way into our romantic expectations.

We don’t write letters to the North Pole anymore, but somehow we’re still waiting to be swept off our feet.

Again, no thank you — I don’t need a prince. I just need a guy who can find my clit.

You seem to have a basic understanding of the world and a fucking great attitude about it. I read your blog for a reality check, it’s great. As much as this ass-kissing is genuine, I have a question. Do you know how I could get into the fashion industry?

The easiest way into the fashion industry is to have been conceived in a bathroom stall at Studio 54, but I’m guessing you’re not fortunate enough to be the bulimic offspring of a former model or aging rock star.

Since you’ll be starting at the bottom, the first step is move to New York with a pocket full of dreams and a copy of the September issue of Vogue.

Next, get an internship in whatever area of the industry fascinates you. Do your best to find an underling position with one of the industry’s many narcissistic megalomaniacs. Spend at least a half decade slaving away for little to no pay in one of the world’s most expensive cities.

Since you’ll quickly discover that New York is no fun without hard cash, during those first few years I strongly recommend a secret life as a high priced call girl. Escorting will do wonders for your shoe collection, and it will help turn your soul into rich, supple leather in preparation for the upper echelons of the fashion world. Either that or marry into a wealthy family.

If you think I’m joking, please just stay in your hometown and thumb through the pages of that September issue.

Best of luck!

Here’s the deal. I met this guy not to long ago, over the internet . Blahblahblah to that, I have no problem with meeting people online. He is hot. Damn good looking And I usually go for the nerdy lanky boys. HOWEVER, this boy is gorgeous. On with the story. We talked for the first time last week on the phone, around tuesday or wednesday. We ended up having phone sex. I have NO idea how it even got to that point but it did. And I feel kinda weird about it because I do not do that with guys I have just started talking to. I like to keep some kind of respect for myself. He wants pictures of me sans clothing now. And I don’t know how to say no. Because let’s face it, I phone fucked the guy the first time talking to him. And after that, how do you say no to something as simple as pictures? Part of my thinks I wouldn’t mind, but part of me would like to save some kind of whatever dignity I may have left. I’m not quite sure what to do here.

Ah, the perils of 21st century whoredom. Every last one of us has a few naughty pics floating out there in the digital ether, and nowadays the American teenage experience includes making your first sex tape before getting your drivers license.

Billions of little red record buttons, so simple and ubiquitous, make it far too easy for boys to do what boys like to do — point and shoot. It desensitizes girls like yourself until you’re asking ridiculous questions like, “how do you say no to something as simple as pictures?”

Simple as pictures? Are you fucking kidding me? The legal and emotional consequences of turning a camera into a sex toy can be staggeringly complicated and more permanent than an STD.

If every iPhone shipped with anal beads instead of a camera, would you still be asking how to say no to something as simple as assplay?

You’re not sure what to do here because you seem to have devalued this part of your sexuality. Take a moment to reflect on the levels of trust and intimacy that are required to safely share naked photos with someone, and hopefully you’ll see that I’m not being facetious when I compare this to taking it up the ass.

Posing for pics can be incredibly hot, and shooting a wildly creative sex tape can be one of the most intimate things you do with your partner, but the decision to let anyone other than yourself control that content is a serious one.

Don’t kid yourself — the second you email naked pics to a phone-fuck buddy you met online less than a week ago, you’ve effectively posted those pics to every amateur porn site this side of Chatsworth.

Just tell the guy no. If he presses you, turn the tables on him — insist that he be the one to send raunchy pics. If he backs down, that’s the end of it.

If he follows through and sends you pics, tell him they aren’t raunchy enough and that he has to send more. Never promise to send any in return.

Demand that he send you dirtier and dirtier pics of himself until he either backs down, grosses you out, or gives you so much blackmail ammunition that there’s no harm in sending him a naked pic or two.

If you do ever decide to send him something, make sure he’s familiar with the doctrine of mutually assured embarrassment, and let him know that you’d go nuclear on his ass if he ever stepped out of line with your pics.

Be wild and have fun, but take this shit seriously.

Where/how did you get so wise? I don’t mean that ironically. In concrete terms, please.

Well, it sure as fuck wasn’t in church.

I’m not quite sure how to answer this really, because accepting the premise of the question makes me kind of a douche. Not that I’m one for false humility. I’ll admit that my IQ is probably higher than my credit score, but wisdom and intelligence aren’t the same thing.

Part of my charm comes from the fact that I grew up ugly and poor in the dirty south and now I’m cute as a fucking button on the west side of paradise. That contrast alone keeps me sharp. Plus, unlike the 85% of Americans who don’t even have a passport, I’ve seen a bit of the world.

But that’s the cheap answer. The real one is a bit more fucked up.

Whatever genuine wisdom I have comes from having faced my own mortality at an age when all my friends were preoccupied with sorority rush. I was forced to contemplate the very real likelihood of my own death without the benefit of having lived a full life, and I had to acknowledge some cold, sticky truths about the meaning of it all.

At first, all I did was freak myself out. Peering into an infinite regression is some scary stuff. Eventually though, I grew comfortable with my utter insignificance in an unimaginably vast universe, and I found that I had no need or desire to supplicate myself to a higher power. We are tiny specks of talking meat on a wet little ball in the middle of nowhere, and I’m perfectly okay with that. The pursuit of happiness is enough.

It’s a difficult concept to communicate, but all the athiest soldiers and godless cancer patients out there already know what I’m talking about. There is a freedom that comes from letting go, after you’re forced to completely jettison your ego. You can’t fake it, and if you’re lucky enough to live, it always stays with you.

All right, enough heavy shit. I’m off to the pool.