Sex Advice From An Uncomfortable Guy Who's Afraid Of Sex And Blows It Every Time (Volume 5)

 

HI! I'M DR. SEX MAN

I've been provided a column to answer all of your, ah, your sex questions, which I'm really excited to do. The questions below have been provided by actual readers. If we didn't get to yours in this round, stay tuned, and as always, keep the questions coming to drsexman@funnyordie.com.

 
 

Dear Dr. Sexman, 

My deployed boyfriend likes it when I send him sexy pictures, but never sends any of himself to me. How do I get a dick pic from him?

—Down for Dick in Delaware

 

OK, wow, that’s great that you send him sexy pictures. They’re of you right? Because one time a girl asked me for sexy pictures and I sent her a photo of Penelope Cruz riding a horse. 

I feel for the guy, to be honest. I’m fairly certain a photo flash would send my, you know, my penis, scurrying back to the safety of its ball nest, toot suite. It’s also probably hard to become, uh, erect in the bathroom while surrounded by squatting men, and I think a, you know, a dick pic should be of an erect penis. 

If you want a, you know, a dick pic of him you should text him in a way he can’t refuse, like “Send dik pic or no tit pic,” “Dik pic or no bjs for 6.5 yrs,” or “Send dik pic or I kill ur dog.” Actually don’t send that last one.  

Or, to give him an idea, send a, you know, a dick pic of someone else’s dick, and say, “send me one of these.” Wait, no, I take that back. That’s a pure “Blow It” situation. 

Oh, and what do the captions of your photos say? If they said things like, “Can’t wait to see yours via picture,” or “A photo of your penis would be great,” that might send some good hints. Stay away from captions like, “Your dick makes me sick,” or, “All the new porn out there has been really satisfying, huh?” You’ll blow it.

 

Dear Dr. Sex Man,

My boyfriend has a very strange sexual fantasy: He wants to fuck me with a popsicle?! While this would make him hot, it would make my pussy extremely cold (not to mention messy, sticky, and with a possible infection of some sort). Is this something other men fantasize about? P.S. He also puts a fruit roll-up on his dick during oral sex.

—Icebox in Iowa

 

OK so, um, yeah, I, um, I don’t, well, but you could, yeah. I’ve never fantasized about putting a popsicle up a woman’s vagina, but then again I’m not a big cold-foods guy. 

The most I’ve fantasized sticking up a woman’s vagina is a tampon, just because I wonder if after all these years of hearing about it I could step in and do it if someone really needed it. I guess the only time that situation would come up is if a woman was handcuffed in an evil dungeon and I just found her, but I couldn’t free her yet or else the bad guy would know I had infiltrated his lair and our plan would be ruined. Plus she’s on her period, but she has a tampon on her. You know what, that wasn’t a very good situation. A woman trapped in an evil lair would probably have other things on her mind. 

So yeah, I think just tell him that he didn’t blow it but that it's not happening, and I hope you at least enjoy the, um, you know, the fruit roll-up! 

 

Dear Dr. Sex Man,

I'm very aggressive in bed and I like to role play every now and then as the naughty little girl who needs a good spanking. The problem is the man I'm seeing is very much the opposite, and the idea of spanking me turns him off.  Should I stay and just have boring sex or move on to someone else?

—Spank Me In Spank Louis

 

Why doesn’t he like spanking you? I think he may just be nervous that he doesn’t do it right. I spanked a girl once by grazing her buttocks with my knuckles. Another time I was scared and got my hand just to the tip of her butt cheek and yelled, “Big slap!” I also told a lady I didn’t believe in that form of discipline and made her stand in the corner for 15 minutes instead. In all those instances, I blew it. 

Maybe ask what he likes? Perhaps he secretly wants something weird done to him, like having the inside of his nostril licked, or maybe he just wants to wear a belt while completely naked. If you find his special need, maybe he’ll understand supporting yours. 

Oh! Maybe he just has sensitive hand skin and just needs to wear a goalie glove or something! Next time you see him just ask if his hand skin is thin and weak. Or don’t … maybe you shouldn’t. 

 

Dear Dr. Sex Man,

My husband hasn't and won't have sex with me. We were last intimate on Christmas Eve 2013. Any time I try to initiate or seduce him I am turned down. He's afraid I'm going to have an affair, but jerks off to porn. I'm a catch, and he says he loves me and it's "just him.” What's wrong with me?

—Sexless in Seattle

 

As a guy who blows it all the time and is afraid of sex, I can tell you there’s nothing wrong with you. Your husband is just blowing it at a Hall of Fame level. Sometimes, when I’m blowing it, I need to be leveled with — once a stranger on the street told me I was blowing it big time with this girl and everyone knew, and that struck a chord with me. 

If I knew how to stop blowing it I would have in a second. But I kept blowing it until it blew up. I hope that doesn’t happen with your husband. It left me sad and so alone that my new best friend was a box of unused condoms I named “Spunky."

 
 

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