Uncomfortable Asks, Advice, Sex, Oral Sex, Blowjobs, How To, Porn Star, Escort Hiring, Rentmen, Virgin, First Time, Rentboy

Uncomfortable Asks: Advice on Escorts and Bad Blowjays

Because I’ve probably seen more dicks than most people, and I know some things, too!


I’ve always been hesitant to offer any sort of practical advice column here, even though I get more than a few emails and tumblr submissions asking my opinion on a particular situation or problem. It’s not that I don’t know some stuff, or have lots of opinions. The thing is, most people don’t seem to bring me regular “how can I save more money on laundry soap?” sorts of questions. I’m not Marilyn Vos Savant, after all.

But you know what? Let’s talk about that stuff anyway. Let’s talk about the weird, gross, unpleasant, difficult stuff that comes with sex and escorts and all of our weird bodies. Some of the most popular posts on this blog have been about things that people are googling for but are afraid to talk about in any real way. Let’s look at some Uncomfortable Asks.



I was wondering if you had any thoughts about [hiring]. I’m in my 30s and sadly a virgin with guys and I want to change that. I watch alot of porn and think I might be ready to hire a pornstar who has advertised on rentmen that he’s going to be in [my town]. But I’m nervous and don’t know what to expect and thought you might know best.

-Anonymous Submit via Tumblr


I do! Well. No. I don’t know if I do “know best.” But I do know some stuff. And certainly have some thoughts about your situation.

Firstly, I think it’s great that you’re doing at least a little bit of research and asking people what they know about the situation. A great way to end up disappointed is to go into a situation with high hopes and zero information. So you’re on the right track.

My advice, is to maybe not make a porn performer your first hire. There’s a lot of reasons for this, but the main point in my mind is that it sounds like you need somebody who’s going to take a bit more care of you, since it’s your first time. The idea of pornstar sex is endlessly enticing and appealing and the fantasy of having a big-dick’d stud take you all night long does sound magical. But first time sex can be tricky and bring up feelings or questions or doubts that you weren’t anticipating. And it might be good to have somebody with a bit more of a sexual/emotional toolbox in the event that stuff happens.

That isn’t to say a “pornstar” isn’t capable of being empathetic and in the moment with you during your time together. More that this isn’t the type of sexual encounter many performers are accustomed to having. Being fetishized and worshiped for their sexual prowess and appearance is more the game of a traditional pornstar slash escort. And that doesn’t sound like the sort of night you’re looking to have, necessarily.

If you went to a restaurant known for their giant burritos and demanded a plate of spaghetti bolognese, they could probably figure that out. But it might not be as good as if you went to a place known for their delicious fatty pasta dishes in the first place.


Beyond that, communication is everything. If you’re not ready to talk about what you want, then you’re maybe not ready to have the kind of sex you’re imagining. Conversely, if the person you’re communicating with can’t find a way to hear what you’re saying or talk about what you like, he (or she) might not be the best fit for your first time.

I hope it’s exactly what you want, bro! Sincerely. And if it isn’t, try again. Sex only gets better the more you learn and the more you do it.




Hi Tyler. I’m dating a guy who is bad at oral. He does it like he doesn’t enjoy it and always needs constant validation about how he’s doing. I usually can’t stay hard the whole time and almost never cum this way. I’ve tried manually moving his head or fucking his mouth and he always tells me to stop and goes right back to what he was doing.

The thing is he’s written articles about sucking dick and even taught classes (mainly to women) about how to give great head. But he’s awful. Is this something we can discuss without him getting upset? Should we?

“-Matt” via email.


Yiiiiiiikes. I am very familiar with this. Maybe we’re getting blowjays from the same guy without realizing it. It’s totally spooky how similar this is.

I haven’t ever understood who those classes and articles about giving blowjobs are really for. I have to assume, like the Cosmo Sex Quizzes, they’re for people who don’t really do the thing, but still want to be titillated about it, and seem enlightened and sexy to their peers or partners.

You know how you learn to suck a good dick? You suck as many goddamned dicks as you possibly can. And you TALK to the dudes those dicks are attached to. That’s it. That’s the mystery. There’s no practicing on a banana, or pretending it’s a popsicle. You aren’t going to learn from classes or articles. You have to DO it.

And to the people running those classes or writing those articles: you gotta get real. You’re not going to give someone enough “tips” to get good at it. That’s like giving people “tips” on how to ice skate, or how to paint. People get great at those things by doing them. In my understanding, people are good at things like that because they fucking love to do it. I LOVE sucking dicks. All of them. All the time. It’s fucking great. And I have a lot of experience, because I love to do it!

But people who aren’t into it, and still think they’re awesome at it because a gay guy teaching a class in the basement of a sex shop told them to remember to “tickle the balls,” aren’t ever going to be good at it. And the people teaching those classes might not be that great at it either.

Experience is how you learn to be good in bed, whatever the activity is. It’s possible that you could really focus on giving this guy great head, and doing all the things you know you like and he isn’t doing. I’ve learned to read what guys want based on what they do to me.

But it’s also possible that in telling him he isn’t good at this one particular thing, you’re going to hurt his feelings and bruise his sexual ego a bit. You have to decide if that will help him learn, or create a rift you won’t recover from.

It’s important that you don’t hold onto this idea and throw it in his face when you’re angry or fighting. Either you bring it up to help the situation, or you resign yourself to mediocre suck jobs and try to be grateful that you’ve got someone who wants to pleasure you, even if he’s not as good at it as he thinks.





If you’ve got an Uncomfortable Ask, about anything at all, drop me a line.  If you want to stay anonymous, use my Tumblr Ask Hole, or the form below:



“There’s no such thing as a stupid question” (is an incorrect thing a lot of people say) but if you don’t ask, you’ll never know. And that seems worse than asking a stupid question.




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  • james
    Posted at 10:31h, 07 March

    There are really places that teach classes on blowjobs?

    • tylerthebadwolf
      Posted at 15:17h, 08 March

      There are. I’ve attended a few. It’s not as salacious as it sounds, though. There’s nobody giving live demos or anything. And more giggling than I think is useful during the ones at which I’ve been present.


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