Best Of Sex Advice: You’re On Your Own

Seeing all the people who turn to advice columnists for help with their freaky problems, and reading about the various crazy scenarios that threaten to bring down every relationship imaginable, it's any wonder that anybody wants to date another person ever. Never mind trying to find someone who would return the favor. Sometimes it seems the only alternative is to give up and assume a life of neverending celibacy ... or more likely, masturbation. Or get yourself thrown in jail and eliminate the other options! That's the situation one writer finds himself in this week, so we suppose there are drawbacks to that plan as well. The prison porn library probably leaves a lot to be desired.

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· Get Naked (timeout.com/newyork)

The brain in this noggin is filled with filth. I'm a porno hound. I'm a slave to porn mags and videos and I'm comfortable putting dating and relationships on hold, in favor of daily wanking. I'm a 50-year-old guy who's been serving time since I was 44 (I get out when I'm 58), and I've been daily wanking since I was 39. I lived in NYC for eight years and once wrote in to an advice columnist. I explained that I was "stuck in a rut," unable to choose between jerking off, pursuing love or pursuing lust with whores in Mexico. She suggested that I try to "reach my full potential," which I assume she meant as a jerk-off. So now, when I finish my time do I: (a) get a life and date women, find a girlfriend/soulmate; (b) buy a ton of porno mags and videos and keep living the jerk-off's life; (c) find a young whore and marry her; or (d) go into porn in my old age and document for the world to see how good I am acting as a filthy, nasty geezer? Thank you for your feedback.

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· Dr. Dick's Sex Advice (drdicksexadvice.com)

My wife is gonna get a gang bang for Valentine's Day. Shes like a total sex freak. I want to get something to bump it up. We tried a blindfold in the past, but it kept slipping down or up when things got heavy. I was thinking about a hood but what kind should I get?

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· Love Bites (eyeweekly.com)

How effective are cock rings at maintaining an erection longer? I have also heard that they can offer a different pleasurable feeling than going au naturel -- is this myth or truth?

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· Sex Project Forums (sex-project.com)

So today my GF and I decided to have sex for the first time ... The only problem with this was that my erection was only about half of what it usually is when i masturbate, and though her touching me felt very good i had a hard time maintaining what little of a boner i had. ... I generally dont have a difficult time getting a firm erection when I masturbate, but I read that over masturbating can cause weak erections, which i am probably guilty of since I've been doing it 1-3 times a day lately.

I didn't feel nervous really, just kinda annoyed that my dick wouldnt cooperate when i needed it to work its magic

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· Dear Prudence (slate.com)

My son is in his last year of high school, and he will be 18 soon. I recently discovered that his girlfriend of less than a month has sent him many nude photos of herself. She took the pictures with her cell phone and sent them to his phone. You can see from most of the photos that she took them while standing in front of the mirror. The other photos are close-ups of her parts.

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· Open Up: The Pucker Up Forums (puckerup.com)

However, I have been wondering how many men out there love dropping a load on their womens faces. Also, how many women love getting a load exploaded on their faces. If you enjoy it, why do you, and what was your first time like.

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· In & Out (timeout.com/chicago)

I've never been with a guy who refused sex during my period. I know it's messy and a little inconvenient, but do you have any insight to this aversion?

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· Savage Love (thestranger.com)

My new guy is not happy that I have a collection of toys or that I watch porn, have been to strip clubs, etc. He likes "regular" sex and he refuses to use toys or do anything in the adventurous realm. How do I even talk with him about what I like without scaring him off? I love being tied up and spanked! Plus he has never done oral and doesn't even want to try! HELP!!!

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Previously: Best of Sex Advice Archive