Dear Playboy Advisor: Questions From Men and Women to the Advice Column of Playboy Magazine (3 page)

We’re sure T.G. isn’t listening.

Can my husband be friends with an ex-mistress?

My husband fell in love with another woman and left me and my children. A week later he said that he shouldn’t have left and moved back into the house. The woman has moved to another town, but I know they talk on the phone. He argues that they were friends before the affair so they can be friends after. What should I do?—R.R., Cambridge, Massachusetts

Your husband is confused. A mistress is not a college girlfriend. If he’s serious about saving your marriage, then he’ll hang up the phone and talk to you instead. Your husband can’t just move back to the house. He has to move in.

Desperately seeking permission

While drunk, my girlfriend admitted to her best female friend and me that she had a dream in which her friend and I were having sex and she didn’t care. After she sobered up I asked her if she actually would care. She said, “Not really.” I think her friend may like me. Would it be okay to have sex with her?—M.T., Shippensburg, Pennsylvania

Sorry, but that wasn’t enough of a yes—and we have pretty low standards. But you have a good line on a threesome.

Meet me after class

I’m a dance student and part-time instructor. Whenever I dance I get incredibly horny. After class I always end up staying an extra hour to fuck the teacher while my boyfriend waits outside. Even when I teach, my student ends up in me somehow. Is this called something? Is there anything I can do to hold out?—C.T., Bayside, New York

It’s called a lack of self-control. Try dancing with your boyfriend. At the very least tell him to pick you up an hour later so you’re not wasting any more of his time.

Brotherly love

My husband put an ad on the Internet without my knowledge. It has all his data—height, weight, profession, favorite quotes—but a photo of his brother. He swears it’s an ad for his brother, who is in prison, but I didn’t know they were even in touch. My husband says he meets women through the ad and gives them money. He says they are interventions but won’t explain what that means. He went to Vegas to meet one of these women after telling me he was going to a different city on business. I found out only after he totaled our car. I am convinced he is cheating. He refuses to discuss it and says he is working on getting someone else in the family to take over his brother’s ad. What do you think?—K.C., Walnut, California

Not only is your husband cheating on you, he’s doing it badly, which is no tribute. You can probably do better for yourself without walking more than 50 feet in any direction.

My dad is cheating with a hooker

I’ve learned that my father is cheating on my mother with a hooker who meets him at his office. This could ruin not only my parents’ marriage but my reputation (“There’s the guy whose father cheated on his wife”). What’s the best way to end this before my mother finds out?—P.R., New Orleans, Louisiana

Could you pay the hooker more than your father does? Confront him, then mind your own business. (Your concern about your reputation is overblown.) Your father may be scared straight, but it’s more likely he’ll become more discreet, to the point that you’ll no longer know whether he’s cheating, which is the way it should be. One of the unfortunate side effects of adultery is that it draws others into the lie.

Wife wants to visit her “best friend”

My wife’s best friend is a man. They grew up together and had a couple of intimate moments but never dated. He lives in California. When she e-mails him she begins with a “Hey, baby” and ends with “Love, your girl.” This makes me uncomfortable. We call each other baby and I thought she was my girl, legally and emotionally. I haven’t asked her to stop because I don’t know if I’m blowing this out of proportion. She wants to fly to California to spend a week with the guy, whom she hasn’t seen in 10 years. Please help.—C.G., Atlanta, Georgia

You’re right to be suspicious. It’s okay for your wife’s best friend to be a guy, as long as that guy is you. You can’t stop her from going to California, or flirting with her old buddy, but you can let her know it’s damaging her marriage. Then she’ll decide.

Advisor, your response was too harsh. I’ve had several strictly platonic relationships with women. In each case, once the boyfriend or husband found out, every one of them became jealous, and the woman and I had to break off the friendship even if we’d known each other for years. If the reader can’t trust his wife, the trouble is on his end, not hers.—G.M., San Jose, California

Fair enough. But how many of your married female friends write you e-mails signed “Love, your girl” and visit you for a week without hubby?

ANAL

It’s the new oral.

Anal 101

I’d like to try anal sex with my wife, but she says it would be too painful. If it’s painful, why does anyone do it?—L.J., St. Louis, Missouri

With the right preparation and care, anal sex can provide immense pleasure for a woman. The anus and vulva share major nerves, and penetration may provide enough indirect pressure to stimulate her G-spot. “Anal sex shouldn’t hurt even a little bit,” says Tristan Taormino, author of
The Ultimate Guide to Anal Sex for Women
. “Start with your pinkie and a lot of lube. Then work up slowly. Try a finger, then two, then a slim butt plug. This progression doesn’t have to happen in one night.” Plus, she says, “Anal sex can also build intimacy. The woman might find herself thinking, We worked up to this and I trust this guy. As for men, it’s in their best interest to make sure their lovers experience only pleasure from anal sex. A woman’s butt will remember pain for a long time.”

Emotional breakdown

I’ve been with my boyfriend for eight months. The relationship is wonderful and the sex is awesome. The other night we engaged in anal sex, which we have both done before, but this time I had a total emotional breakdown. My orgasm was accompanied by a crying episode so intense it took us both by surprise. Everything was great and I didn’t experience pain, but the tears came in buckets. Can you tell me if this is a normal reaction or why it happened?—T.G., Memphis, Tennessee

It’s nothing to worry about. We carry more stress than we realize in our sphincters. Penetration requires the muscles to relax, and the tension can dissipate in ways that surprise us. Annie Sprinkle calls this emotional release a crygasm. “I’ve talked to so many women who tell me that when making love or having an orgasm they have a little cry at the same time,” she says. “It feels so good.” There was a time when lovers were expected to cry. “Eighteenth century novels are full of scenes that suggest or, in a few cases, represent orgasm with tears as the most sublime experience possible,” notes historian Tom Lutz, author of
Crying: The Natural and Cultural History of Tears
. “Weeping in love was considered the norm, and a lover who couldn’t weep wasn’t worth having.”

Adventures in butt-kissing

I’ve been licking women’s asses for more than 30 years. It started with my wife. We were in a 69 and I found her cute ass inches from my nose. Later we became swingers, and I tongued dozens of women. (A buddy once persuaded an uptight librarian he was dating to let him try anilingus; before long she was showing up at all hours saying, “Get on your knees, you disgusting pervert, and lick my ass like a good boy.”) When licking a woman’s ass, it is important to be as hygienic as possible. Use an antibacterial soap to prepare, and never lick her ass and then move to her pussy. After you’ve finished, wash your mouth with antibacterial soap, then gargle with mouthwash and warm water. For best results, put a bit of Vaseline and a mild skin rub that contains menthol on your tongue (but again, don’t go near her pussy). If you want to see something erotic, watch women lick each other. We were at an orgy once when one woman bet another that she couldn’t lick her own pussy. She lost the bet and, as a result, had to lick the woman’s asshole. They put on quite a show. The other females oohed and aahed. The men were mostly silent.—W.R., Lehigh Valley, Pennsylvania

You know you’re at a hot party when anilingus is the icebreaker.

Shit doesn’t happen

I haven’t been able to nuzzle up to a butthole since my undergraduate studies in microbiology (I’m now in med school), when I learned that one gram of feces contains 100 million bacteria and that fecal matter is 60 percent bacteria. In addition, hepatitis A and other nasties are commonly transmitted via oral-fecal contact (which doesn’t necessarily mean ass licking but rather eating contaminated food, such as from a salad bar, but I suppose with anilingus one bypasses the salad). To the old coot who wrote to boast that he had given his old lady anilingus for 25 years: Think about all this the next time you kiss your grandchildren.—B.N., Lincoln, Nebraska

Rimming does have risks. When you lick an anus, even an enema-clean anus, you may ingest trace amounts of feces. That’s the reason God created barriers such as dental dams, plastic wrap, unlubed condoms cut lengthwise and the fingers of latex gloves—she wants us to stay safe while enjoying the amusement park of nerves around the butthole. “With rimming you’re not going that far into the rectum, so sticking a soapy finger up there before your anal date is going to take care of most of the fecal matter and bacteria,” says Tristan Taormino. “Lots of people have been licking lots of buttholes for lots of years, yet we haven’t seen widespread E. coli outbreaks. This student is joining rimming and fecal matter when the two don’t necessarily happen at the same time.” We’d add that your comment about the “old coot” is too judgmental for us or for the medical profession in general. By your reasoning, you shouldn’t offer your hand to shake if you’ve ever wiped your ass with it.

Does anal sex make you gay?

My wife and I were in a 69 when she began to lick my asshole. I was a little surprised, but it felt great. She told me to position myself on all fours while she retrieved her vibrating dildo. What could I say? After teasing my balls and anus, she pushed it slowly into my ass. As she pushed it in and out, she began giving me head. She asked me what I thought of being butt-fucked; I had to admit I loved it. Does this mean I might be gay?—E.C., Sacramento, California

Sliding a finger, sex toy, corncob or any other object into your butt doesn’t make you gay. Being gay makes you gay. Write again if you start fantasizing that Tom Cruise is holding the dildo. When we receive letters like this, we recommend the instructional video
Bend Over, Boyfriend
(goodvibes.com, or 800-289-8423). Its producer and star, Carol Queen, points out that anal play is a great way for a man “to explore the various ways he can be sexual and climax without his cock being touched.” During one of the film’s demonstrations, she tells her antsy partner, “Wait a minute. I want to fuck you, and then you can fuck me back.”

Does anal sex make you loose?

My husband’s anal techniques are beyond wonderful; the sensations he provides me are becoming an addiction. There’s one problem: I think my sphincter is getting loose. After intercourse it feels relaxed for about an hour. This never happened in my early anal days (I can’t believe I just wrote that). Can you help?—N.A., Tucson, Arizona

No need. What you’re feeling is normal. You’ve had enough experience with anal sex that you’ve learned to release the tension we carry around in our butts. An hour sounds about right for your anus to return to its naturally puckered state.

The male G-spot

I received an e-mail that promised to reveal the location of the male G-spot for $25. My husband is chomping at the bit. Is there such a spot and how do we find it?—M.E., San Ramon, California

Save your money. The male G-spot, better known as the prostate gland, is a mystical place beneath your husband’s balls. To find it, insert your index finger about 1.5 inches into his anus and make a come-hither motion against the front wall of his rectum. He may have had a doctor do this during an exam, but it’s quite a different sensation when you’re highly aroused, the finger belongs to your wife and insurance companies aren’t involved. Suzi Godson, in
The Sex Book
, offers further instruction. Have your husband lie on his back. While stroking his cock, press gently but firmly on the area between his balls and anus to stimulate the prostate from the outside. As you slide your latex-gloved, lubed finger into his anus, his sphincter will twitch. This may feel uncomfortable for your husband, but after about 30 seconds the spasms will stop. Caress his prostate gently. He may feel the urge to urinate (but won’t). If he can speak, ask him what motions feel best. As he approaches orgasm, his sphincter will tighten and the gland will swell. Because it supplies part of the fluid that makes up his come, the gland will contract as he ejaculates. When you remove your finger, your husband will deflate.