Ask me anything, AMA, Reddit, Questions, Answers, Tylerthebadwolf, Escort, Companion, Rentboy, Sex, Watersports, BBC, Raw, Bareback, Treasure Island Media

Tylerthebadwolf: Ask Me Anything

Seriously! No holds barred.


I’ve been collecting questions on my tumblr for a little over a month now (I once used until they started forcing people to log in to ask, eliminating the anon aspect, and ruining the whole premise as far as I’m concerned) and I’ve got some good ones ready for you today!

If you have a question for me, but you’re embarrassed to ask in the comments, or in an email to me, here’s a link to the ask page of my tumblr, which is totally and completely anonymous. I think it’s so cool that you guys wanna know more about what I do or more about jackin it or things that I’m interested in, and I’m totally pleased to have this forum to talk about this stuff! I’ll update this post with new questions as they come in, so bookmark it and check back.

To the questions!


Was it my imagination or did you post a picture of you on twitter using a bathmate and then deleted it?


Nope. I did do that. It’s still here, though. Not deleted.



Versatile, top, bottom? How do you decide in any given situation?


I’m of the belief that this kinda shit depends entirely on the chemistry and situation. My natural tendency to be the aggressor is completely reversed with the right kind of take-charge daddy. But for the most part, I prefer topping because I’m not that jazzed about getting fucked. But the short answer really is chemistry.



Watersports and diapers – yay or nay?


Watersports, YAY! Diapers… ehhhhhhhhhhhh. Probably not for me.



Do you ever find that you want to be friends with clients (not boyfriends, just friends). And real friends, not the “I like all my clients” kind of friends?


Absolutely. I have several guys that I would consider very close friends who were or are clients. The important thing I always suggest about things like this is that we stay mindful that our friendship doesn’t interfere with our professional relationship. I’m lucky that it’s never really been an issue, and I’ve kept seeing most of them professionally as well as occasionally off the clock.



What are you wearing right now?


A Hanes $6 Old Man’s Undershirt, and my first cockring from high school.



Are you a good kisser?


I am. But it’s not bragging when it’s just facts. I’m also a real spitty kisser so if you don’t wanna get soaked, I don’t recommend getting in there.



What do you think about bareback? Is it hot?


Bleehhhhh. I think a lot of things about it. I think there are ways to do it smartly, to keep yourself and your partner safer. I think we’ve come a long way with PrEP understandings and misconceptions, and I think it’s a choice that adults gotta make for themselves.

It’s not for me. I’ve personally never had unprotected intercourse of any kind. I’m a believer in condoms and regular testing.

I also have some deep suspicions and resentments of entities like Treasure Island Media that would use the threat of infection as a marketing ploy. I think it’s a significant slight and disregard for the many thousands of men who suffered and ultimately lost their lives to HIV/AIDS before we had the medicine and treatment options we do now. If you knew men who died because of sex they had, it should hurt your heart to see the risk of infection pushed as tantalizing or edgy. It’s neither.

I think if your drive to raw sex is to feel closer to your partner or because it genuinely feels very different and more serious to you without a condom, that’s one thing. I think if the rush is that you’re courting life-altering danger, you should spend some time with those thoughts and figure out what’s going on there.



Who is the most famous client you’ve ever had? Or what did they do if you can’t say names?


Come on now… I can’t talk about that. Not even what they do. That is how we end up places like this.



What do you do if a client isn’t hot? As in theres’ just no way it’s gonna happen. Do you leave?


You know, it’s never come up. I find that I’m usually so drawn to what a man is, and the way he relates to his penis and to me that his “hotness” just isn’t significant. It’s not significant in my personal life either, really.  Sex for me is about something else most times. Not about how hot I find someone to be. I’ve said some stuff about that here.



Can see ur ass ?

You put a question mark at the end of this like it was a question, but I’m suspicious you’re just telling me you can see my ass.



I always find myself admiring you for your confidence and openness to discuss sex and other things so openly. How did you get to be so confident and comfortable?

Wow! Thank you! That’s kind of you to say. I really do try to do those things! I wish I had a profound answer for you now. It’s really just that I grew up in a naked house and was really raised not to be afraid or ashamed of sex and sexuality. And probably more importantly to ask questions and look it up when I didn’t know something. It seems like a given, but so many people wander around all their lives with wrong or missing information and I think that affects how you look at and engage with others (sexually or otherwise). Knowledge is power and all that.



Advice for a first time bottom? I tried it once and It fucking hurt like hell; also, embarrassingly, I don’t know the first thing about douching. It scares me a bit tbh lol

Fear is good. Fear is your friend. It will help you understand your limitations better and keep you from doing reckless stuff with your butt. That’s why experts recommend never using desensitizing gels and creams because you’re less likely to know when you may have injured yourself. Pain is an indicator something may be wrong.

With all of it, I believe that research is your bff. Do some googling. You need to read some stuff about what you’re doing and do some dry runs in anticipation. I’m a fan of BryanBoy’s guide to Douching 101, and I own the shower shot (because I live alone and it’s good for things other than ass cleaning).

I’d practice douching 2-3 times before I ever planned to put a dick in there, and Bryan’s guide is right about wanting that water to come out crystal fucking clear. It takes time, and practice, but it’ll happen and eventually that will become just like washing anything else.

Not everyone does this, but the best bottoms I know are mindful a day or so in advance about how much and what sort of things they’re eating. I know that seems like a lot of planning, but Chipotle today means probably not bottoming tonight/tomorrow. For most people.

Lastly, there is literally no such thing as ‘too much lube.’ Use and demand as much as you need and however often you need it. Look into a lube injector so you can even start out juicy.



Why are you so obsessed with bulges? Maybe some guys just don’t want to show off that way.

Bulges are cool. So, it’s mostly that. But they also represent a confidence and bodily comfort that is really lacking in a lot of people today. That lack of confidence and understanding about your own body causes a lot of internal complications you may not even be aware of until they spring out in other arenas.

If you’re a man with external genitals, I think it’s important that you acknowledge that fact and stop trying to pretend something else is going on by smashing everything flat. It may not necessarily seem important to everyone around you, but it is important to you.

Allowing your clothes to display the outline of your genitals should not be a shameful thing, and when you see someone doing it, it’s because they’ve gotten over the idea that penises are something to be afraid of.

That said, nobody has to do anything. If you are most comfortable with your D&B smashed up against your body because underwear manufacturers live in a fantasy world about how men’s bodies look, then by all means! Get ur tuck on!


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