Best of Sex Advice: What’s Your Problem, Buddy?

Let's face it: we've all got problems. But no matter what your problem is, those of other people are almost always more interesting, unless you're one of those arrogant pricks who loves the sound of their own voice and can't shut up about your own problems long enough to care about anyone else's. (In which case, that's your problem.) The rest of us will keep checking out the rest of the world's issues in our latest Best of Sex Advice roundup: this month's dilemmas include personal grooming techniques, the geometry of strap-ons, the 48-year-old oral sex virgin, and why you shouldn't tickle your stepmom, even if she's hot. (By the way, virtual voyeurism is not a problem as long as people keep putting themselves out there for us to gawk at them. As soon as they stop, then we've got a problem.)

- - -

· Pucker Up Forums: Sex Advice (puckerup.com)

How did you get your wife to put on a strapon?

I thought it would be an interesting question. Unless she was the one who instigated anal play, how did you approach the topic of having her put on a strapon dildo and fuck your ass with it?

- - -

· Dear Rachel & Claire (babeland.com)

My girlfriend and I have just got a dildo and two-strap harness, but embarassingly cannot figure out how to position ourselves to use it.

- - -

· All Sex Advice (allsexadvice.com)

Probably a very common question but what are some ways a guy can teach himself to last longer? Sometimes it can last 15+ minutes, others maybe 2 or 3...what are some ways to prevent the disappointing 2 or 3 minutes?

- - -

· Sex Project: Sex Questions (sex-project.com)

I have ingrown hairs from genital shaving. ... I have no idea why or how I still get them. Its ridiculous. I know I dont want to wax. What could I do?

- - -

· Savage Love (thestranger.com)

I'm a 17-year-old male with a tickling fetish ... Six months ago, my dad married a 29-year-old woman. A few months ago, I tickled her armpit when she reached up into a cupboard. She didn't pull away and seemed to enjoy it. Surprisingly, she also has a tickling fetish on the opposite end. She loves it when a man tickles her. She now walks around the house barefoot and with skimpy clothing so that her stomach and ribs are exposed so I can tickle her whenever I want.

However, we always do it behind my dad's back. I would NEVER do this with my real mother (that's sick). But with a stepmom, is it okay? I'm starting to feel guilty about doing this without my dad's knowledge.

- - -

· Andrea Nemerson's alt.sex.column (altsexcolumn.com)

I'm in my first sexual relationship; there's been a lot of lovely hand and mouth action, but no penis-vagina intercourse, because I can't maintain an erection with a condom on ... Assuming that we don't get married, my sex-life looks pretty bleak if I can't use condoms. Any ideas?

- - -

· Ask Xandria (xandria.com)

I would like to try oral sex with my partner on our honeymoon, but I don't know how or what to do.

How do I approach his penis and don't hurt him? I want to surprise him. Is there a book to teach me? I am 48 yrs old and I've never did this.

- - -
· Love Bites (eye.net)

I have been pondering getting into the sex industry for a while, but I want to be informed about the ins and outs, at least a bit more than I am ... Do you have any words of wisdom for a novice tranny boy wannabe hooker?

- - -

· Dear Amy (dearamy.net)

Over the course of three years, every now and then I notice a liquid on my girlfriend's vagina. To be honest, it looks like cum to me. When I asked about it one day, she said she didn't know what it was. I never accuse anybody unless I know what's going on, but to me it looks like she creamed right before she came to see me - or somebody just came inside of her. Can you please help?

* * * * *

Previously: Best of Sex Advice Archive