Dear Playboy Advisor: Questions From Men and Women to the Advice Column of Playboy Magazine (33 page)

Buy me a jet plane

Is it possible for a civilian to buy a ride on a military fighter jet? I think this would make a great Father’s Day gift.—M.R., Brooklyn, New York

Come on, don’t be a cheapskate—buy the whole jet. You can pick up a decommissioned Soviet MiG these days for as little as $30,000, though the fuel costs might bankrupt you. Defanged fighter jets can be flown in U.S. airspace only for exhibition or pilot proficiency, so rides can’t be sold. But there are any number of collectors willing to take a passenger who agrees to split the cost of fuel, which runs a few hundred dollars an hour. For leads, contact the Classic Jet Aircraft Association at classicjets.org. Depending on your budget, you also might get in touch with Space Adventures, which for $20,000 will strap your dad into a MiG-25 at a Moscow military base and take him up 80,000 feet and down again to pull tricks at Mach 2.8 (call 888-857-7223). Many companies and a few museums offer less costly rides in World War II-era trainers such as the T-6 and T-34; you’ll find a list at warbirdalley.com. And for $995, Air Combat USA will send your dad up for six simulated dogfights in an Italian-built prop fighter-an experienced pilot handles the takeoff and landing, and your father is equipped with a parachute, a helmet, a flight suit and a few combat tactics. The firm is based in Fullerton, California but has a road show that travels the country. Phone 800-522-7590 or visit aircombat.com.

ONLINE

Brave nude world.

Digital snoop

Years ago I suspected a girlfriend was cheating. Although she denied it, I installed monitoring tools to capture her instant messages and e-mails. I was amazed at how convincing her lies had been. Since then I have monitored other women I’ve dated, either by shoulder surfing to get their e-mail passwords or by installing software. Anytime I suspect deceit, I obtain the truth. Perhaps this isn’t ethical, but it has saved me a lot of time and heartache. I don’t want these tools to ruin my integrity as a boyfriend or spoil my ability to trust a good-natured woman. But it’s hard to establish that trust when you have seen firsthand how two-faced some people can be. What does the Advisor think?—N.E., Detroit, Michigan

We think the spying is getting you off. When you love a woman as much as you love the technology, maybe she’ll be loyal to you.

Porn with a familiar face

I found a collection of porn photos on my boyfriend’s computer. I don’t mind that he looks at porn, but he put my sister’s face on the photos! I’m not sure what to think. What does the Advisor say?—J.C., Portland, Oregon

Look on the bright side—it could have been your mom. It doesn’t surprise us that your boyfriend fantasizes about your sister, given that he’s attracted to you. But pasting her face onto porn is further than most guys take it. You need to have a talk.

Do not enter, do not pass go

Most adult websites include a disclaimer that says you shouldn’t view the site if its content is illegal in your state. How do I find out what’s legal? Have people been prosecuted for visiting adult sites?—K.P., Los Angeles, California

Unless you’re downloading and sharing child porn, the police won’t be knocking on your door. Can we imagine cases where images stored in your browser cache could get you in legal trouble? Yes, but every instance is far-fetched.
The disclaimers are there for the benefit of the adult site, not its visitors. In the unlikely event that an ambitious prosecutor takes a digital porn palace to court for violating local or state obscenity laws, the site figures it can point to the disclaimer and say, “We warned them not to come in.” That argument won’t take them very far, but it’s better than nothing.

What to do with nudes?

What is the protocol when you find nude photos of a female acquaintance online, at a site she apparently created? She’s someone I know fairly well and would like to bang. My hours of porn surfing haven’t been a waste after all.—J.W., Kansas City, Missouri

Are you sure that it’s the same woman? We haven’t seen the site, but we’re guessing it’s a fantasy created to make money and not reflective of her personal sluttiness. Rather than being indiscriminate about who she “bangs,” you may find her wary, and weary, of your interest. Ask her out, but let her make the first mention of her business. If you come across as another one of her drooling fans, the only way you’ll see more of her is with a credit card.

I’m an escort with a website, and having people I know find me online is the biggest risk I take. I went to a new doctor, and the next day I got an e-mail from him through my site asking if we’d met the day before. It was a more honest way to do it, because if he’d asked me out in person I never would have told him I work in the business and he wouldn’t have told me he fancies online companions. I would never tell a date what I do, because who I am as an escort is much different from who I would be as a girlfriend. I get paid to always want cock, always have great hair and never reveal my PMS. I wouldn’t want to date a guy who is okay with what I do, and I also wouldn’t want to live a lie—so dating is not something I do. My guess is that the woman that reader found would prefer to keep her two lives separate.—C.S., Minneapolis, Minnesota

Wouldn’t we all.

Throw me a line

I’ve been surfing chat rooms, looking for a booty call. Is there a way to avoid all the small talk without sounding like a pervert?—T.W., New Orleans, Louisiana

Once you accept your essential pervertedness, you’ll be more comfortable being blunt. The FBI agents and guys pretending to be women will appreciate your candor.

Photos of the ex

I’ve seen sites on which guys post nude photos of their ex-wives. Is that legal? What are the repercussions if the exes find out?—R.S., Randolph, New Jersey

These sites are designed to make you believe that the “ex-wife” in question is being humiliated, which is a turn-on for some guys. In reality, she’s a model. We’re sure a few former husbands have posted nudes of their exes without permission, but after the lawyers get involved we’re guessing they won’t do it again—especially men with children.

Can you ask a woman out by e-mail?

Is it acceptable to ask a woman out by e-mail? If she says no, I don’t want her to see my disappointment.—F.L., Boston, Massachusetts

It’s best to ask in person. If she declines, it’s okay to be disappointed.

My horny co-worker

On a new co-worker’s computer I came across a chat room she visits while at work. I suspected that if she knew I was in the room, she wouldn’t be herself, so I signed in using an alias. During the first session she offered me a blow job and told me she liked to masturbate at work. That’s when the administrator of the room revealed that she and I had the same network address, so she knew it was somebody at work. She freaked out and signed off. I e-mailed her later, explaining that I had just been trying to see the real her. Needless to say she seems embarrassed and a little creeped out. Of course I was turned on by her dirty talk and want to make a move. How can I release her sexual side?—C.J., Louisville, Kentucky

It sounds like you already did, but you blew it by being sneaky. How did you happen to be on her computer? After you’ve both been fired, maybe you can commiserate over a beer.

People often act very differently when they believe they have anonymity. Just because that woman wrote things online doesn’t mean she will say or do the same after she signs off. If a guy pursues her in the hope that she will follow through, he may be in for a rude awakening.—S.D, Phoenix, Arizona

Boyfriend is trolling

My boyfriend has posted a profile on a dating site. When I asked him about it, he told me it was completely innocent. He said that because I am frequently out of town on business, he wants to find “artsy” people to hang out with. His online profile indicates that he’s single. When I asked him about that, he said he plans to inform any woman he meets about our relationship “when and if the topic arises.” How can I convince him that posting this ad is disrespectful?—M.N., New York, New York

Deranged is more like it. Your boyfriend is reluctant to admit that you exist because otherwise he’d be fishing without a line. He may not be planning to cheat on you, but he doesn’t want to miss any opportunity that presents itself. (As Chris Rock says, “A man is basically as faithful as his options.”) Unfortunately for your Don Juan, that’s not how the game is played. Your boyfriend needs to update his profile or he won’t need to update his profile—you know what we’re saying?

ORAL

Giant sucking sound.

My girlfriend won’t stop sucking

My girlfriend loves oral sex. The problem is that she won’t stop, even after I come. I usually have to make up an excuse to get her to quit (my back aches, my leg is asleep, etc.). Do you have any suggestions to bring the festivities to a close without hurting her feelings or lying about it? Things get painful after a while.—G.H., Baltimore, Maryland

If you want a woman to stop sucking your penis (egad—did we just write that?), give her something else to do. Tell her, “I’m so turned on; let’s make love,” or “Your turn,” or “Come up here and kiss me.” In the meantime, remember: A few haunted souls can’t get blown even once, and right now they hate your guts.

Her blow jobs are “just all right”

My boyfriend and I have been together for a year. We were kidding around and he told me my blow jobs were “just all right.” I decided that the only way to prove otherwise was to let him see for himself. I told him to get blow jobs from three women I didn’t know and report back to me. Just as I expected, he came back and told me how good I was and how much he appreciates what I do for him. I wanted to let your female readers know that if you trust your man and are secure in your relationship, you should dare him to compare. He’ll return if you’re better than “all right,” and he’ll be incredibly grateful.—J.S., Middle Island, New York

You make it sound like your boyfriend was gone for an hour. This is risky business, but you seem cocksure. Now, tell your boyfriend his tongue is “just all right.”

She has a ticklish clit

I like to perform cunnilingus on my girlfriend. There is one small problem. Every time I start to touch her or go down on her, she says, “Ooh, my ticklish clit!” and I have to stop. How common is ticklish clit and how can I work around it?—P.B., Oxford, Ohio

Do just that—work around it. Many women don’t enjoy stimulation of the clitoris until they’re thoroughly aroused, but you can play with it indirectly. Caress, spread and kiss her labia, finger her anus, massage her mons. The wetter she becomes, the less you’ll hear about the tickle.