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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More Sex Advice From Dr. Sex Man:

Sex Advice From An Uncomfortable Guy Who's Afraid Of Sex And Blows It Every Time (Volume 2)

 
DrSexMan,jpg

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 adore my boyfriend, but whenever he goes "downtown," if you know what I mean, he seems a little lost and confused, and my mind starts to wander more toward ‘should I start washing the dishes tonight or can I leave them until tomorrow?’ What can I do to help him on his way a bit?

— Pantieless from Portland 

 

Okay, wow, so you are a woman and you aren’t wearing panties, and you are writing to me. Holy crap, that’s great. And you have a boyfriend, too? Great. Are you wearing pants, or just crotchless? Sorry that’s insensitive and none of my business. 

First off, I would just do the dishes first. You’re going to think about them no matter how much pleasure you are having, because, let’s face it, they ain’t going anywhere!

So the dishes are done, you’re on a bed, or on the floor, maybe, and your guy is going “downtown,” you know, um, licking your vagina with the goal of inducing pleasure, and you are not into it. How is he blowing it? Sometimes I blow it by just drooling and coughing a whole ton. Sometimes I’m all lips and forget to use my tongue at all. Also sometimes I have bad breath and I worry that you’ll be able to sense my bad breath through your vagina and you’ll be turned off. Is that a thing? Also, once, when I had a cold, I wasn’t thinking and I blew my nose into a woman’s vaginal hole. What’s weird is that she liked it, but I couldn’t repeat it and I just ended up making a bunch of honking noises. 

Sorry, so, you want to help him out. Personally, I like it a lot when a woman tells me what to do, because then there’s less a chance of me blowing it. Tell him what you like and what you don’t like. Say, “Do that more,” or, “Move over there,” or, “Try that. Yeah, like that." Just don’t scream those commands or say them in a deep man voice. That will scare a man right out of your vagina, and you’ll blow it. I’ve done that before, but, you know, in reverse. I screamed “TOO TOOTHY” once and before I knew it, I was alone in my room, staring at my plant, boxer brief–less and without pants on, too. 

 
 
 

Dear Dr. Sex Man,

I want to ask my partner if he would be into me fucking him. What's a good way to go about that?

— Strap-On Sally from Lawrence, KS

 

Heh heh, oh jeeze. Wow. That’s a loaded one. There’s A LOT GOING ON in this question. So, you, um, you want to, uh, “fuck," your man? And I take it from your name, Strap-On Sally, you are a girl? So to, uh, fuck your man you would, um, holy crap, you would put a short stick, or dildo, up his, um, you know, his butt? Wow. 

But your question is how to ask your partner for permission to do this? Okay, well, I don’t have any experience in this, but I guess I would try and be honest. First I would sit him down and say, "I like sex, but I would rather do sex to you, and mainly to your butt.” Then I guess I would say, “I want to explore your, um, your butt, with, you know, a long, penis-shaped device that I would buy or fashion out of what’s lying around the house.” Then I would pick up a, um, I don’t know, say you have a long candle sitting there, I would pick up the candle and say, “Like, take this candle. I promise I won’t light the candle, but I would like to pretend this candle is a, you know, a big long penis, and I would like to kind of push it in and out of your butt, if that’s okay. I don’t know for how long … um, until something happens, I guess. Maybe until the candle melts?”  

You know what, it’s starting to feel like I would blow this conversation. Maybe just get him drunk, throw the fake penis on, and say, “Is this gonna happen or what?” Holy crap, that sounds bad, too. Good luck. 

 
 
 

Dear Dr. Sex Man, 

When I'm having sex with my boyfriend, he says he wants me to moan more ... Be louder ... But I don't feel comfortable ... Or sexy ... Being loud ... What do you think? Should I just let it all out like he wants and risk feeling stupid?

— Whispering in Wisconsin

 

Whoa, okay, so I think that’s great. You are having sex already, and now it’s just about tweaks. Well, I say let it out. It just depends what you are moaning. Whatever you do, don’t loudly moan the following words or phrases while you are, you know, having sex (trust me):

“Frog people, froooooog people.”

“Tooo muchhhhhh sooooouuup.”

“Buckets of belts and plenty of welts.” 

“2003 Mitsubishi Ecccccclipse.”

“Is this an Eye Store?” 

“Imprrrregnate, imprrrrrregnate.”

“Looose Fleshhhh.” 

“Penis Tuggers.” 

“Burgle me. Burgle meeeee.” 

 
 
 

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

 

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. If you have a, you know, a sex question, feel free to email me at drsexman@funnyordie.com. I'm here to help!

 
 
 
 

Dear Dr. Sex Man, 

My girlfriend wants me to rub her chest but doesn't want me to touch her nipples. Is this weird? 

- Nipless in Nebraska

 

Wow, okay, I guess we’re jumping right in to nipples. Well, first off, that’s awesome that you have a girlfriend. That probably means you can kiss her all the time and she won’t get mad, unless she's in a meeting or something. Also I imagine you guys get to do a lot of activities together that aren’t even sexual. Just, like, spend time together. That’s great.

Full disclosure: the last time a woman told me she wanted me to touch her chest I kind of freaked out and said, “Okay, let me wash my hands first because I was eating a lot of peanut butter earlier, and I don’t want to get any on your tix.” 

I blew it in a lot of ways there. First, don’t go wash your hands unless you know they are covered in a bad disease. Second, don’t even bring up peanut butter if you know what’s good for you, and third, don’t call tits ‘tix.’ They won’t like it. Also don’t call them ‘Brauts.' I know that kind of sounds like breasts but it’s really more like a sausage, which is another word for, you know, your um, your penis. 

So there you are, rubbing her chest, with desire and permission and everything, which is great, but she doesn’t want you to touch her nipples. I don’t know, that’s pretty standard for me, especially since my hands are often covered in peanut butter or worm guts (I fish).

If your hands are free of nut butters and she’s still not into it, have you asked her why yet? Maybe if it hurts her or something (I know my nipples hurt a lot, but that’s from my work pals giving me twisters whenever I jam the puzzle cutter) you could try coming at the nipples from a different angle. Try pushing them in like an elevator button, even say something dirty like “69th floor, please.” Oh! Maybe try throwing some thick leather gloves on and then touching the nipples. That’s all I got. I hope you don’t blow this. 

 
 
 

Dear Dr. Sex Man,

I’m a woman who is uncertain how to move when I am on top. Do you have technique advice? 

- Straddling in St. Louis

 

Oh my God. First off, it’s awesome that you would even email me. I can’t believe this. This is great. Okay, let’s jump in, sorry. So, when you are on top, you say? So that means you’re already having sex. That’s juicy stuff. 

So there you are, having sex, on top of a guy, and you’re probably naked, and that’s, you know, that’s great. But now you’re wondering how to move around up there. Well, this one time I had sex once, and I was on top. I would get tired and fall across the body of the woman I was plowing love into. I got a cramp and, trying to get off, dug my elbows into her rib cage, which made her scream in pain. I thought that was an orgasm, so then I orgasmed, and then it was over. I blew it big time there. Just don’t do that.

I think as long as you’re not flailing your arms all over the place and sticking your fingers in his nose, you should be okay. Another thing to avoid is holding your stomach and saying, “Too much soup.” I learned that the hard way. 

 
 
 

Dear Dr. Sex Man,

How can I tell that my girlfriend really had an orgasm during sex? 

- Anxious in Arkansas

 

MAN, I wish you didn't ask this, because I really blew this one recently. I had, you know, sex, I think, and I finished fast and got worried she didn't, um, orgasm, so I accidentally yelled "ORGASM, YOU DID?" right in her ear, in a shrill Yoda voice. Then I started sneezing, and I couldn't stop. I sneezed all over her until she left. Then I cried a lot. 

So I think just live life hoping she did, because there's too much room to blow it.