Dating 101: Alexis Penney

Why She Knows: Alexis Penney is a tranny, hooker, and party hostess from San Fransisco. I’ve interviewed Alexis previously about his fabulous life as punk hustler, which you can and should read HERE. When I started Dating 101, I originally said I was only going to be interviewing women. However Alexis is a woman sometimes (when he wants to be), and realistically it’s about time we enlisted someone who has a dick who also sucks dick to teach us how to give a good BJ. And I’m pretty sure Alexis gives a good BJ, considering he gives them (and gets them) for a living.

PLEASE, teach us how to give head.
A friend of mine once said that the trick is to slip a “pink in the stink” aka a finger in the ass, which I think can be true. Also, unless the guy is just super into deep-throating, a blowjob is going to feel best when there’s a hand used in conjunction. And seriously, watch the teeth! Like figure out how to keep those fuckers back, because there is literally NOTHING worse than a toothy blowjob. Honestly though, I’ve hooked up with slutty gay guys in their fucking 30s who still can’t figure out how to give a good blowjob. It’s like, did you miss that day or what?! Like some guys will go super fast and crazy, but it’s best to do it kind of slow and rhythmic. If you are trying to just get it over with, come up almost all the way off the head each time and follow your mouth with your hand, while keeping a medium rhythm. That’s how I get guys off if I want them to cum soon or if I’m bored. Oh and if your mouth is dry, fucking drink some water! A cotton-mouthed blowjob can also be really gnarly.

Do all guys like to be fingered in the ass though? How do you work out if a guy wants that?
Honestly, no. I used to bottom like a pro but don’t really anymore, and I almost hate it when somebody fingers my ass, because I’m like dude, I am probably pretty dirty down there and your finger is kind of harsh and pokey, etc. But that’s just me. A lot of guys actually love it, but I think there can be some psychological shit if the guy is straight, and even with some gay guys too. But I think you can usually tell. Like a bottomish dude will get really crazy and give you moany signals if you get down by his house, and the same with a straight dude, especially because some of them may not be used to being touched there, so you can usually hear it or see it in his mannerisms if he’s into it. I think it’s always good to try for the ass at least once though, just to see.

What is your number 1 dating tip?

CHILL OUT. I think a lot of people get in relationships and the intensity of the emotions makes them crazy! I’m constantly over-thinking shit with guys, taking things too personally, planning out our lives years in advance and nitpicking when they do something I don’t like. But it’s better to just relax and enjoy it and don’t trip about the future, or who likes who more, because then you just turn it into some gross mirror of your parents’ marriage or something. Blech!

Is it a bad idea to have sex on the first date if you think you could potentially really like the person?
No way! I think it’s a good idea. If I don’t have sex on the first date I assume it wasn’t even a date, unless we at least make out. I can’t even think of someone in a relationship context until I have sex with them, because what if he wants me to shit on him? Not that that is necessarily a deal breaker, but you know what I mean.

I agree that it’s not a bad idea, although I do think dating can exist without sex. But I think it can be bad to wait too long. Like what if you wait until after marriage and then you find out the guy has erectile dysfunction, a la Charlotte in Sex and the City? Nightmare!
Yeah I can’t fathom a relationship or love without sex, how inane and weird! Normal people love to set themselves up for failure, haha.

Do you have any default moves you pull in the bedroom, or foreplay stuff you do, to turn a guy on?
Hmm, not really. I guess I’m always joking at least slightly in the bedroom, which some guys like and some don’t. I hate when guys take it super seriously like it’s all SO hot and we’re like being filmed for a porno or something. I’m like lighten up, because really sex can be pretty gross and dumb, and I’ve been filmed doing it and I don’t look that good, so I like to keep it light.

Yeah, I love sex–have since I was a little kid–but sometimes when I over-analyze it I’m like “Eww! What’s going on why am I do this? Gross!” But I think that’s a totally normal feeling, which is why it’s good to maintain a sense of humor about it.


In your opinion, what should a girl wear on a date?
Whatever you feel the most confident and attractive in. I don’t think there’s anything too slutty or too anything, as long as it makes you feel good. I think the biggest mistake can be trying to be casual. It’s like, you’re not going to yoga class! You should dress to reflect well on yourself! But that’s just me, and I’m in make-up and heels like 75% of the time, even in the most inopportune moments, so I have kind of a skewed perspective about how to dress. I say just be yourself, don’t try to look like anything that you’re not, and whatever you wear, sell it. It’s pretty easy to tell if someone isn’t confident in what they’re wearing, so you better own the look.

So do you ever fuck straight guys? Is it normal for straight guys to “experiment”?
Yeah I’ve actually fucked a ridiculous amount of straight guys. I don’t know what it is; I think that straight guys, like animals and children, respond to me because I don’t judge anybody and I’m really good at presenting a blank slate to project on. If I’m in a room full of straight guys, the one that is questioning his sexuality will almost always seek me out, it’s actually kind of ridiculous. I’ve had guys proposition me at posh 30-something dinner parties, when their wife and kid are in the next room, it’s nuts. But after sleeping with and being in relationships with some crazy straight/bi guys I kind of got over it, because I’d rather be with someone who’s not conflicted about who they are. I think all gay guys have a straight guy fetish, but I just don’t want to deal with that. That being said, I had some guy come home with me after my club asking to “experiment” like a week ago, so it’s not like I’m above it. I mean if you get right down to it, nobody is really as straight or as gay as they say–that’s a societal thing, not a sexual thing. I’m the fucking gayest queen I know and I’ve messed around with girls, whatever! People are people.



9 Replies to “Dating 101: Alexis Penney”

  1. I agree with Don, I'm loving your blog entries lately! Even though the Dragon guy a few entries ago was really weird and WTF, but totally entertaining. Here is a different perspective on sex on a first date if you feel like reading: I am not a virgin, but my boyfriend is. We've been dating for almost 16 months now and he's the most awesome person I've dated. He is really funny/smart/gentlemanly/dresses well and attractive. We're not at a point in our lives where we can commit to each other for a lifetime because we are in school, but regardless I would love to spend the rest of my life with him. In the beginning I thought it was so weird that he was waiting for marriage, you want a test ride before you buy it, right? I was fascinated with sex at an early age too, although I didn't lose my virginity till my late teens. However, boyfriend and I do a lot of other things that don't involve penetration and it's obvious I get him really hot, so I know that if we were to marry and have sex then it would be really, really good. He also gives good head and tells me my vagina is the most beautiful lolz (he's seen quite a few because he's in med school). I don't know too many guys who are waiting until they marry, but it's a personal decision he made and I'm willing to respect that. Of course, I may have felt different if he wasn't willing to touch me at all, but that's my thing.

  2. "I'm the fucking gayest queen I know and I've messed around with girls, whatever! People are people."this line is amazing haha. your blog is kicking ass at the moment, i was wondering where you'd take it once you moved back to new york, but i am loving what you've done!

  3. oh man, of course there is a comment froa girl wanting to be friends with the gay guy. they may as start selling them at the mall next to forever 21 and the food court.

  4. Best way to figure out if a guy is game for a finger in the ass is ASK HIM! I know I would love it but it's something you want to prepare for so there is no dirtiness.

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