Ask GayDemon Blog

My mom's new boyfriend keeps asking me awkward questions about my sex life. I'm 19 and he's been with her for about two months. Should I freak out?

-Private Privates

Yes, totally freak out. Right now! Go ahead. Do it. Make it count. Freak the fuck out.

Are you done for now? Okay, great! Now here's the deal. Why are you qualifying them as "awkward" questions? Wouldn't any question about your sex life be awkward? I can see questions about your dating life being non-awkward, like if he's just trying to show some interest in your life and trying to prove to your mother that he's not a homophobe. Assuming you're gay that is. Which I guess I can't assume, so I'll ask.

My best friend is straight and I'm totally head over heels in love with him. Every time he gets a girlfriend, I get so depressed and can't wait until he gets bored of her. What can I do?

-Pining for Penis

Don't you mean "heels behind head" in love? Because that's sure the way to keep a guy happy. But seriously, you're fucked, or unfucked as the case may be.

You've got a double whammy. When he has a girlfriend, he spends less time with you (of course) and you semi-lose your best friend. Plus his dick is in your ass and his tongue is in your mouth (and every combination therein) exactly zero percent of the time.

So I'm talking to this guy on a app. And he's really cool. He always answers back. I want to hang out for our first time. He also told me that he was playing with himself and he told me about it. Should I ask to hang out and how?

-App Curious

So you're asking me how to use a hook up app to hook up? By tapping your smartphone screen in various combinations until you end up with dick in your mouth or your dick in his mouth or everyone's dick in everyone's mouth.

Do you have any recommendations for lube? I've been using the free sachets handed out in clubs but they don't work very well. I need something that lets me play longer, wider and harder!

-Dry and Unboned

You want to play wider? Like how wide? Two dicks? Three? Twelve? I want you to play wider too. I just don't know what the hell it means, so I"ll have to imagine. If you're a top, I'm thinking it means you want to come at it from different angles, move the guy around in different positions, while keeping your dick in. Kind of like if someone offered a bottom 500 bucks to fuck himself with a cucumber at a 45 degree angle. You'd want him to be able to take it.

I just found my boyfriend's profile on a fetish site. I joined yesterday as I was curious and I saw that he's into a heap of stuff we have never explored. Should I ask him about it?

-Fetish Finder

Oh, you "just found" his profile on a fetish site you "joined yesterday" as you're "curious"? How "fatefully" "surprisingly" "splendidly" magical an occurrence. My virtual fingers are now getting tired from ironic air quotes.

Help! I can't cum and it is very embarrassing when I meet a really hot guy in the bar, go home with him, and have the best fuck but I just can't get there.

-Frustrated Fucker

Hahahahahaha! Hey squirt, that is a problem. You're a squirt who doesn't squirt. Hilarious! Any of the guys you hook up with laugh at you after dumping their load? Maybe a couple of them have laughed and cum at the same time, which is like sneezing and chewing gum at the same time. Or the oh so challenging full-split handstand ejaculation which ought to be an event in the homosexual olympics.

I've been fucking my sister's boyfriend. I feel really bad for her but we totally connect and I can't stop meeting up with him in private. Should I fess up or is it okay to carry on behind her back?

-Sneaky Sibling

So you're looking for moral and ethical absolution by asking "is it okay" yet you "can't stop" so it's really beyond your control, right? That's like asking for absolution for being a natural blonde. If you confess to your sister, then you'll almost certainly lose the whole thing where you fuck her boyfriend because he'll be super pissed. And your sister won't disown you or anything. She probably should but if she's stupid enough to leave her gay brother alone with her slutty boyfriend while she's out potentially doing horrible things of her own, she's stupid enough to not disown you.

I'm 20 years old and only into older guys. I took a 54 year old home to meet my parents after we were dating for a few weeks but my mom won't accept the age difference. What can I do to convince her I just like older men?

-Son with Two Dads

Two dads isn't enough for you? You need a mom, too? How greedy! Don't you know there are even 19 year old guys dating 55 year old guys who don't have a mom to bring that older guy home to? Acceptance isn't possible when there's nobody to accept something in the first place.

I'm 32 and have only ever fucked girls, but I find men more attractive than women. Does this mean I'm gay? When I'm watching straight porn I think I'm watching him more than her.

-Confused Fucker

Isn't sexual disorientation grand? Without needing to know anything more about you, I can definitely say your dick is straight and your mind is gay. So as long as you keep your mind out of it, you can keep on fucking women with your dick and that dick of yours (plus the vaginas and female anuses and mouths it penetrates) can be none the wiser as to all the supergayness inside your head.

Guys are asking me a lot on Grindr if I'm cut or uncut. I don't know how to tell the difference. How do I know if I am cut? I think there's some foreskin there but I have no idea for sure. Please help me!

-Curious Cruiser

"Cut or uncut?" is one of the age-old Grinder questions, like when the horny salesman at Patagonia asked me "Turtleneck or mock turtleneck?" Yes, ever since the non-abstractly named Nearby Buddy Finder, LLC launched Grindr in 2009, guys have wanted to know as much as possible about the dicks their future (and mouth and hands and ass) may hold.

I'm taking chems when having sex. I've found that they make me so horny and go for the whole night, if not days! But they make my cock floppy so I bottom more than I want to. What can I do?

-Open for Business

There's a strap-on with your name on it. Since neither the natural sexual power of love (if you're wired that way) nor the sexual power of genuine desire keeps you going for the whole night, even days, you're going to need some man-made assistance. Pardon me while I attempt to not laugh picturing your floppy dick below a long, thick, perma-hard strap-on. The guy on the receiving end can say with pride that you "one and a half dicked him good."

Everytime I get fucked I feel like I need to pee. Is this normal or is there something wrong with me and how can I stop it from happening?

-Naked Niagara Falls

Are you saying you don't look good in yellow? To be fair, it can be a tough color to pull off. So you might consider wearing some dangly fluorescent yellow earrings to bed to complete the look. If you get fucked in toilet stalls, then wear dangly non-fluorescent yellow earrings because when you're getting fucked in a toilet stall, mall security could walk in at any moment and you don't want to attract attention to yourself with the whole fluorescent thing.

I've been with my boyfriend for 6 months and we don't fuck anymore. He watches a lot of porn and I started to watch more recently, too. Am I unattractive to him?

-Fuckless Fella

Yes! Next question.

Wait, that was heartless of me. And you're already fuckless so you don't need heartless. Because without fucks and without heart, what do any of us have? Just our stupid brains. Well, mine's not stupid, but you get the point.

I'm a versatile 18 year old guy. I have been fucked many times before and sometimes I cum (without touching my cock) very fast before my partner is finished. How can I make sure that it will take a longer time for me to cum every time?

-Confused Cummer

Ah, the myth of the simultaneous ejaculation. The idea that sex isn't sex unless both guys squirt at the same time, otherwise someone is letting someone else down. Isn't it enough that you're both guys? Do you have be twins in your ejaculation timing? With you holding out long enough for him to unload a millisecond before you do? As I'm sure his pulsing, thrusting cock would put you over the edge. What's next, Mr. Twin, wearing matching outfits to the gym, right down to the pink socks?

I've been seeing my boyfriend for 6 weeks and I still can't take his cock. He's around 8 inches and it's a really big girth too. How can I make sure I can bottom for him?

-Too Tight in Tukwila

First of all, congratulations on coming to the right advice columnist for this one. If you'd asked Miss Manners, she would have suggested polishing the silver. If you'd asked Ann Landers, you wouldn't get a response at all because she's dead. And if you'd asked Dan Savage, he would have talked about himself and his 40-something wannabe twink husband.

Now on to your asshole.