Sex Advice From An Uncomfortable Guy Who's Afraid Of Sex And Blows It Every Time (Volume 3)

 
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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. Sex Man,

I've been dating my girlfriend for years. Her dad wants me to propose. Should I do this while "doing it"?

— Doer From Dover

 

No. I tried it once. I was having, you know, sex, with this girl I liked and I wanted to marry her and I said, “Will you marry me,” but the only thing that she heard was “Mary,” because I was thrusting and out of breath and probably drooling. Anyway, Her name was Claire, not Mary, and she got really mad. A second later I tried to propose again but by that time she was in the bathroom cleaning herself up, and she thought I proposed to my flaccid, um, you know, my penis. She left because I blew it. 

 

 
 

Dear Dr. Sex Man,

Dear Dr. Sex Man,

I love my boyfriend very much, but I'm a very sexual person and love to please. Unfortunately, my boyfriend’s is 55 going on 56 and I’m 47. We only have sex once a week, if that. His testosterone levels are extremely low and I've suggested he see another doctor since the current doc feels like a man his age shouldn't be having a lot of sex. What should I do? Also, how can get I him to go down on me nicely without his "EGO" getting hurt? Sexual conversation is not an easy convo with him. HELP!!!!!!

— Sexually Frustrated 47-Year-Old sent from my iPad

 

Oh, man, that’s great that you have a boyfriend at that age! And I guess it’s also great that you are still having, you know, sex. I’m hoping that when I reach that age I will no longer hyperventilate when the word "sex" is even mentioned out loud in a PG-13 movie. 

But wait a second, he has a doctor who doesn’t think a man his age should be having a lot of sex? Is that something doctors say? Will he have a heart attack? I usually trust doctors, because they tell me when I've swallowed too many coins or when I can start lifting houseplants again, but this sounds strange. Sex is something to be feared because it is terribly frightening and embarrassing and I blow it all the time, not because it is unhealthy. 

If you are competing with the doctor, maybe you need to turn your boyfriend on in more ways. Why not try incorporating something men of his age are into? Dressing up like a boat, or barbecue, perhaps? Maybe temporary tattoo the New York Times crossword on your back or tummy? This sounds weird; I think I’m blowing it right now. 

As for your final question of many, Ms. My iPad, I would suggest yelling “Keep Going!” while he is going, you know, downtown on you. That way his EGO will be more encouraged than intimidated. Just don’t yell, “You look so funny from up here,” “Is your tongue made of uncooked bacon?”, or “Leaning against a purring cat is more effective than this.” All of those will make him feel bad, and you’ll blow it. 

 

 
 

Hi Dr. Sex Man,

I was wondering: why do men like it when girls arch their backs during doggy style? And which is better, when a girl is on her hands and knees, or on her elbows and knees?

— Doggy-Gone from Des Moines

 

Holy Moly. Okay, so doggy style is when you are, you know, having sex with a girl, and the man is standing or he’s on his knees, right? And the girl is on all fours, er, she’s pretending to be a table. So the guy is having sex with the girl pretending to be a table, right, and you’re asking why men like it when girls arch their backs during that time? I’m going to assume you mean arch the back down, like a ‘U’ shape, right? And men like it more? They do? I guess since I’ve only had sex with a girl while she was in that kind of table-pretending position one time, I don’t have an opinion, personally. I’m not sure if she did anything with her back, to be honest, because I couldn’t stop thinking about tables, and that she was a table, and then I pictured a coffee table book on her back and then I thought how that’s a mean thought because coffee table books are so heavy, and then I thought how hard it would be to balance a cup of juice on her back, and that makes her a bad table, and then I thought it’s weird to think of a girl you like as a bad table, so I blew that one. 

Maybe guys like the arched back because then the girl doesn’t remind them of tables so much? So if we are sticking to this table logic, maybe being on the elbows and knees is a more-preferable position, because then you won’t look anything like a table, ladies. Not even close. 

 
 

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