Sex Advice From An Uncomfortable Guy Who's Afraid Of Sex And Blows It Every Time (Volume 4)

 

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,

What do you do if your boyfriend wants to watch you have sex with other people?

- Polygamous In Peoria 

 

Holy Stained Sheets, that’s a tall order. Not only are you having sex now, but you’re also starring in a one-viewer porn. That’s a ton of pressure for me. A lot of what I do is based on the other person only being able to see a small percentage of the terror going on below. Also, someone accidentally saw me having sex once and they said I looked like a beluga whale trapped in a net, fighting for its life. 

Do you want to have sex with other people? I don’t think you should do this if you don't want to, unless he’s also offering to pay you a lot of money. Wait, I take back that last part. You should do it for free, if you want. It might give you a nice chance to see what it’s like with other, you know, men’s, um, personalities. 

Maybe you'll like being watched, but you don’t know it yet. I didn’t think I would like having my hair shampooed by another man, but it was great, and I only accidentally coughed on him a little bit. 


 

Hello Dr. Sex Man,

I am almost a 40-year-old virgin. I have had some luck with women, but have never gone all the way. I am congenial enough, and most find me funny and friendly, but I don't know how to make the transition to intimacy and ultimately, sex. My question is, should I move to the Himalayas in shame and disgrace?

- Not Steve Carell (yet)

 

Don’t move to the Himalayas. The weather is pretty bad, and it’ll be even harder to have and do sex with others. And it’s already so hard. It’s harder than training a dog to smoke a cigarette in front of your friends. 

Not having sex is just fine, and way less stressful for me, because sex is horrifying. Though I understand wanting to see what all the fuss is about. I myself didn’t lose my virginity until after all my friends, and it was scary because I blew it so bad: It ended with me yelling, “Someone’s coming!" and quickly standing up, grabbing a book, and pretending to read, as if we weren't just having sex, even though I’m naked, still wearing a condom. Nobody came, and I mean that in every way. 

I wish I knew how I went from blowing it with masturbation (for a while I thought you were only supposed to use your knuckles) to blowing it in sexual situations. I don’t know what changed. All I know is that even after you start having — you know, sex — with people, how to have sex without accidentally kneeing your lover in the stomach becomes a much bigger issue.


 

Dear Dr. Sexy Sex Man,

Do girls like it when you pee on their face? 

- Holding It in Honolulu

 

Whoa. You ask as if I pee on girls' faces all the time. That sounds like the single most horrifying way I could blow it with a girl. 

I think you need to eventually ask the girl, maybe over ice cream or while having dinner at her parents’ house, if that’s something she would be into. When it comes to kinky stuff, I don’t think you should ever assume. I once assumed that a girl I was, you know, having sex with, would be cool with me firing spit wads at the cat as we "did it." Ten minutes later she was driving away with my cat and I blew it. 


 

Dear Dr. Sex Man, 

My boyfriend gets a hard-on a lot when he is sleeping. I love giving oral sex — I lay there and watch this hard-on thinking about should I or should I not, if you know what I mean. Lol. So my question is, you know, should I or should I not? And if so, do I wake him up first, or just go for it? :)

- Sucking in St. Paul

 

Ha. Wow. That’s a sensual letter. Jeeze. Well, my heart says “yes" but my experience says “no." A girl did that to me once — she went, ah, she went down on me while I was sleeping. At the time, I was dreaming about antelopes who had the flu. In my half-awake haze I thought a sick antelope was suddenly felating me, so I freaked out and slapped the antelope away, screaming, “I DON’T WANT YOUR DISEASE!” 

Let’s just say I blew it. 

 
 

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