Dear Playboy Advisor: Questions From Men and Women to the Advice Column of Playboy Magazine (59 page)

That’s not a bad setup to get yourself invited. The reason four married guys would last longer is that they’d each be thinking, I better take this slow, because it’s never going to happen again.

Obstacle course

My wife and I are friends with a couple who are swingers. One night while drinking and playing cards we all engaged in masturbation and oral stimulation. As we played, my wife pushed my hand or head away several times to clear a path for the others. Should I be concerned that she doesn’t find me attractive or satisfying?—J.B., Allentown, Pennsylvania

Let her know how you feel, but don’t jump to conclusions. Your wife saw an opportunity to enjoy the sensation of unfamiliar fingers and tongues. She was less interested in having sex with you while others watched. Whatever her motivations, this wasn’t a good move on her part. There’s a difference between swinging with your partner and leaving your partner swinging. That’s why it’s smart to discuss these situations before they occur, to avoid surprises and hurt feelings in flagrante delicto.

A single guy in swinging

How does a single guy get into the swinging scene?—R.T., Santa Barbara, California

The few clubs that welcome single men (and their entrance fees) typically do so only on certain nights, so you end up with a crowd of mostly guys. Fun! Traditionally, single women have been admitted for free to balance the ratio, but gender-discrimination laws are putting an end to that. (In fact, the North American Swing Club Association had to revise its own guidelines to specify that it admits only male-female partners to its events after a gay male couple that was refused entry threatened to sue for $1 million.) NASCA president Robert McGinley says allowing too many single men drives couples away. “You always get single guys who argue that couples love having spare men around,” he says, “but even at couples-only parties there are lots of guys who will happily fill that role.” He also says the presence of single men can irritate swingers who value the honesty of the lifestyle. They assume the guys are alone because they’re cheating on their partners. If you do attend as a lone wolf, don’t be too grabby. A breathy play-by-play or shouting “Move over, Rover, let Jimi take over!” is not the best way to introduce yourself.

A free pass

For her 10th wedding anniversary my wife’s best friend got a pass from her husband to do anything or anyone she wanted for a week, as long as it happened far away from home and he didn’t learn any details. She immediately booked a beach trip and called my wife to invite her along. That was fine with me. As long as my wife returns with videos and photos, I will forgive her anything. The idea turned me on even more after my wife mentioned that a 40-year-old woman will do things to a 20-year-old guy that a 20-year-old girl can’t imagine. How can two husbands who would allow such adventures be so different? When I mentioned to him that the most erotic thing I had ever seen was my wife having sex with another guy, he looked as if he might cry.—M.E., Philadelphia, Pennsylvania

He’s making a sacrifice, and you’re making an investment. We’d bet this wasn’t his idea, which makes us wary of endorsing it. Guys who get off watching their wife get fucked usually have a lot of confidence about whom she’ll end up with at the end of the night or the week. You benefit twofold here because both women will want to share details, and you’ll be the only one listening.

THREESOMES

When four is a crowd.

What we learned

How can I persuade my wife to have a threesome? And if I do, how should I arrange it?—B.F., Atlanta, Georgia

After reading through the hundreds of e-mails we solicited from readers, asking them to describe real-life threesomes and how they came about, here’s what we gleaned:

(1) Don’t beg. You don’t want your partner to do this as a favor, because that breeds resentment. It should come up as part of a discussion about fantasies. If she’s curious about being with another woman, encourage her. If she isn’t, back off. You may have planted a seed. Or it may not be in the cards. As Hef notes in his
Little Black Book
, “It’s foolish to squander the tomorrows that exist in a relationship for a momentary adventure. It’s not a smart way to live your life.”

(2) Don’t bring this up unless you have a strong relationship. Threesomes have been known to cause serious damage. That’s why it’s crucial, if your wife agrees to it, to establish ground rules. Can you kiss the other woman? Can you have intercourse with her? Does your wife want to have sex with the other woman? Will you use a condom? How about a dental dam? It isn’t prudent to negotiate during the encounter. Regardless, your wife should command your full attention, particularly during the first experience.

(3) Many threesomes develop when a guy finds himself alone with two horny, intoxicated women (the women must kiss before anything else happens). Most threesomes begin tentatively as the participants grow comfortable with the extra body in the room. If you blurt out something like “I can’t believe this is happening” or “Yeah, baby!,” you risk making the women feel that they have been cast in your personal porn movie. It also implies that you’ll be blabbing about it to your buddies for the rest of your life. Play it cool and make the experience about their pleasure. As one reader pointed out, “You have to be in the right place at the right time with the right women.”

(4) There are two kinds of women you can approach: known and unknown. For the former, your wife should invite an open-minded friend for dinner and drinks. Once everyone is cozy, either (a) invite the friend to your bedroom straight-out (“We’d like you to stay”) or (b) bring up the topic more casually by recalling past adventures, how men and women have different approaches to sex, why guys are turned on by women kissing, etc. Your wife will need to make the first move, usually by massaging her friend’s shoulders or otherwise getting touchy-feely. There is a risk that the friend will react badly. That’s why it may be better to recruit a stranger, preferably an escort, who doesn’t expect anything but an envelope of cash on the dresser. You should budget $500 or more an hour. Some couples compromise by making fast friends in the swinger community, which has no shortage of bisexual women.

I’d like to do my date—and his brother

I have been on a few dates with a guy and think we’ll have sex soon. I’m also interested in his brother, and I’d like to do both of them at once. How do I ask if they’d be interested in a threesome?—J.K., Columbia, South Carolina

This may sound prudish, but we usually wait until we’ve slept with a woman at least once before asking if we can invite her sister (twice before we ask about her mom). Don’t package your fantasy as a threesome with his brother. A threesome involves a guy and two women, always. You’re thinking of a gang bang. After you’ve been together a few times, gauge your boyfriend’s reaction by presenting it as your curiosity about having two men at once. If he’s agreeable, ask him who he would suggest for the third. Then grab for the ring: “Okay, this is completely wild—and maybe too wild—but what about your brother? I’m not sure I would feel comfortable with any of those others.” Don’t be surprised if he says no—men generally don’t invite family to their fantasies. Then again, he may one-up you and reveal he has two brothers.

You wrote that a threesome always involves a man and two women, and that a woman and two men is a gang bang. That’s ridiculous. My husband and I have had threesomes with another man. Why is it that two women and a man gets the wholesome tag of “threesome,” while a woman and two men deserve the crude “gang bang”? Your answer reeks of sexism.—M.Z., Cincinnati, Ohio

We like your idea of wholesome. If anything, our answer reeks of heterosexism. When you and your husband arrange a threesome, do the men have sex with each other? Probably not. That makes it a gang bang—i.e., one person having sex with two or more partners simultaneously. Technically, a three-way could involve two men and a woman, three men or three women. We just don’t fantasize about those scenarios—except for that last one, and it always ends up as a gang bang.

Does my fiancée want two guys at once?

My fiancée always sucks my thumb during sex. Does that mean she wants to have sex with two men at once?—S.S., Fort Lauderdale, Florida

Hard to say. When a woman sucks your finger it’s usually a preview of what she plans to do with your cock. If your fiancée is curious about having two men, we suggest you shop together for a dildo. It’s an extra penis that doesn’t require an invitation.

My husband got angry when I kissed a woman

My husband and I went to a bar one night, and a female friend of ours hit on me. Later, my husband wanted to know why I hadn’t let her continue so he could watch. A few months later we ran into the woman at a party. This time, I had enough wine in me to let her kiss me. I glanced over and my husband looked shocked. Suddenly I felt dirty, like a pervert. My husband said he was upset because of all the people there who might have seen us. I thought I was fulfilling a fantasy for him. Can you explain?—T.B., Youngstown, Ohio

Your husband prefers to keep his fantasies behind closed doors, or at least in the relative anonymity of a bar. He likes to watch, but he doesn’t want to be watched while he’s watching. If he hopes to see you with another woman, he didn’t play his hand well.

The mother-daughter duo

I’m a bodybuilder, age 23, who makes ends meet as a personal trainer. My two favorite clients are a drop-dead gorgeous mother-and-daughter exotic dance duo. I train them together at their home. Both women are voluptuous and muscular. They act more like sisters. We had always flirted, but for professional reasons I never acted on it. One day I joked that it would be fun to shower together. To my amazement, they agreed. I found myself pressed between mother and daughter as they soaped my body. They did things with their hands and mouths that were beyond belief. After the shower, they led me into the bedroom. The daughter rode my cock while her mother kissed my mouth, nipples and stomach. Then I fucked the mother doggy style, with the daughter hugging me from behind. While this wasn’t the first time I’d been with two women, the fact that they were mother and daughter enhanced the eroticism. Now I’m dating both. How common are mother-daughter threesomes?—C.A., Houston, Texas

They’re common—as fantasies. The “exotic dance duo” is a nice touch in yours.

My wife only lets me watch

My wife and I have threesomes with a friend of hers, but I am only allowed to watch. The friend has told me she wants me, but when I ask my wife, she says no way. Is this fair? The frustration of having to remain on the sidelines leaves me not only wanting her friend all the more but yearning to have sex with other women as well. I’ve tried the “gentle approach” but get no game.—J.T., Dallas, Texas

That’s rough. You need to attack from a flank. Your wife’s friend should bring up the idea privately with your wife, who will certainly suspect you encouraged the idea. But she may be more receptive to rounding up from two and a half to three if it’s presented as a favor to a friend rather than an indulgence for her husband. You also could attempt to ease yourself into the situation. Volunteer to hold the vibrator. Or wait on the women as their slave (candles, wine, whatever they need). Or perhaps your wife would like her breasts kissed and fondled while she’s receiving oral sex. If she says no to any or all of that, well, you’re out of luck. Having sex with the friend or anyone else without her okay is trouble. One more bit of advice: Don’t complain too loudly to your buddies about how you only get to watch.

You ignored the inherent unfairness of the situation: The wife is allowed to have sex with another person, but the husband isn’t permitted the same courtesy. Let’s say J.T. had written: “My wife and I have threesomes with a friend, but I only allow my wife to watch. Am I being unfair?” We both know your answer would have been different. For starters, you would have ridiculed him for his male privilege.—J.K., Chicago, Illinois