The Hot, the Horny, the Hilarious

For one holiday issue in the late Fifties, Playboy poked fun at Ann Landers and Dear Abby. We reprinted letters from their newspaper columns, along with the marriage-happy responses, then provided alternate answers as a knowing bachelor might pen them. Hef found the piece amusing, and it inspired a monumental idea. "We should do our own advice column, for men, every month," he said. The Playboy Advisor debuted in September 1960, promising to answer questions on a wide variety of topics of interest to the urban man--from fashion, food and drink, high fidelity and sports cars to dating dilemmas, taste and etiquette. This month, the column celebrates its 40th anniversary. During his four decades of service, the Advisor has personally replied to more than 350,000 letters, 5618 of which found their way into print. A few of the best questions and responses are remembered here.

In the Beginning was the Bachelor ... [September 1960]

I'm sure other bachelors have been troubled by this problem--one that I've never been able to solve satisfactorily. Whenever I'm entertaining a young lady à deux in my apartment, it seems that the phone rings and at the other end of the wire is invariably another young lady wanting to talk. What's the best way to ease out of this situation, without letting either girl in on it?--J.B., Chicago, Illinois

When you escort a young lady into your apartment for an evening of your own design, nothing should intrude. Turn down the bell on your phone (in both the bedroom and the living room) in advance so it doesn't jar you or your companion. And if it rings, just gaze at the girl and murmur, "No matter who it is, it can't be more important than you," and don't answer it. The miss you're with will be delightfully flattered. The chick doing the phoning will think you're out, so she won't be bugged by visions of you and a competitor in an intimate situation. Wherever you are, including the bedroom, when the bell tolls, don't let it toll for thee.

Hef's Playlist [February 1961]

My bachelor apartment is stereoequipped. I must admit immodestly that the feminine traffic is heavy. Usually, we mix a few drinks, I put some music on the rig and, well, one thing leads to another. My problem is this: I don't own any complete LPs* that are first-rate mood builders. The record makers seem to feel variety's a virtue (which it may be, under other circumstances), so a mood track is often followed by jump stuff that puts me right back at the starting line. Either that, or I have to pop up every few minutes to hunt for a fresh sound. Should I let the records keep playing after my favorite mood-sustaining specials are over, or continue with what I'm doing, or what?--H.W., New York, New York

Get yourself a tape deck and tape your tempting tracks in sequence. Use the 3 3/4 or 1 7/8 inches-per-second speed, which should give you enough fidelity to suit your divided attention and enough time to unfreeze any woman. As an alternative, pick up copies of discs designed for those cozy hours. On the pop vocal side, try Frank Sinatra's Only the Lonely, No One Cares or In the Wee Small Hours, Peggy Lee's Pretty Eyes and Julie London's Around Midnight. On the pop instrumental slant, sample the Jackie Gleason ork sides--several with the glowing trumpet of Bobby Hackett featured--or the Paul Weston discs, including Music for Dreaming and Music for Romancing.

Oh, Behave [September 1964]

Is it proper to remove a girl's fashion wig before making love to her?--S.L., Baltimore, Maryland

On informal dates, country weekends and any time before five, untressing is permissible--if your date consents, of course. But under no circumstances should yon move to remove your partner's wig if you suspect (1) she's not wearing one or (2) she's bald.

Oops [March 1965]

It may seem silly, but things have reached a stage where I'm really getting worried. My daughter, who is 14, and a number of the other kids in the neighborhood have formed a real cult over the Beatles. They have built an altar in one girl's bedroom and they burn candles and recite Beatle prayers. Now their project is writing a Beatle Bible, which starts out "In the beginning the Beatles created the rock and the roll." If they weren't so darned serious about this, it would be funny. But when she doesn't go to church with us because they are having their own service in their Beatle church, I start to worry a little. Worst of all, we have to listen to that awful music over and over. What should we do?--M.D., San Francisco, California

"And this, too, shall pass away," said a sage about another plague at another time. We suggest you keep cool until the Beatle bugaboo likewise passes away, as it most assuredly will. In the meantime, when your daughter plays her records, do your listening with earmuffs. Yeah, yeah, yeah.

A Condition that Predates Sex [April 1969]

After an hour or so of heavy petting, I often find myself in substantial pain in the area of my testicles and lower abdomen. I have tried, with no success, to correct this by using different types of undershorts. Can you tell me what this is, how common it is and, most important, what can be done about it?--O.L., Ithaca, New York

We've been told by medical authorities there is no scientific name for the pain you mention, but it is fairly common and is called blue balls in slang. Dr. William Masters said, in his Playboy Interview (May 1968), "When the male is sexually excited and approaching ejaculation, the testicles increase in size; the average size increase may be as much as 50 percent over the unstimulated norm. A young male who is forced to maintain this degree of local vasocongestion for a period of time--without release--may well develop some pain and tenderness." The problem comes not from your shorts but from your longings and can be prevented or eliminated by ejaculation.

Deep Throat Techniques [June 1973]

My husband and I were inspired by the feats of fellatio that we saw in Deep Throat. We watched in awe as Linda Lovelace took into her mouth and throat all of a penis that must have been nine inches long. An article in Playboy mentioned that she shared certain skills with sword swallowers. I was under the impression that sword swallowers used collapsible swords. What is the secret?--R.C., Burlington, Vermont

A professional sword swallower, who swallows real swords, says: (1) Throw your head back as far as it will go. This opens up the throat and allows you to accept an elongated object without gagging. (Lying on your back with your head over the edge of a bed is the most comfortable way to maintain this position.) (2) Hold your breath. (Impractical in this context: We suggest that you breathe through your nose. Linda Lovelace says she breathes around the penis on the outstroke.) (3) Practice with a blunt object before you attempt the real sword. (Linda says it took her three weeks before she believed that she could eat the whole thing.) A collapsed sword is the end. and not the means, of this particular trick.

Tale from the Crypt [December 1973]

Glancing through a magazine recently, I noticed that one of the models had no nipples. I asked my boyfriend what had happened to them. He looked at me and said, "You mean you still have both your nipples?" He told me that a woman's nipples are often removed by a man in the heat of passion and that one person he knows used to have a whole jarful. They looked like dried apricots. I told him that this was ridiculous, but because my experience is limited, I'm not sure. What do you say?--F.R., Iowa City, Iowa

The model whose picture you saw may have been the victim of a careless airbrush or an overreaction to a Supreme Court decision. Possibly, she had inverted nipples. Tell your boyfriend that one erogenous zone is as vulnerable as the next and that you (continued on page 172)40 Years(continued from page 118) know a girl who has a jar full of what appear to be mushrooms. That should make him bite his tongue-in-check.

The Chinese Basket Trick [February 1974]

Every now and then, I get a letter from a friend of mine in the merchant marine. The last one came from Hong Kong and contained reference to something called the Chinese basket trick. He assumed that I knew what it was, and I don't. Can you give me details?--S.K., Hartford, Connecticut

Sure. Lovers suspend a basket from the ceiling of their bedroom with a block and tackle. The woman climbs into the basket and lowers herself until her genitals come into contact with her partner's. (By the way, the basket should have a hole in it, and the trick doesn't work quite as well with the man on top.) Some couples have the man raise and lower the basket, while the woman plucks the ropes as if they were the strings of a harp; the vibrations can be delightful. Other lovers twist the ropes before the woman gets into the basket; the gentle unwinding motion adds a new dimension to the phrase "getting turned on." We've heard of several variations of the Chinese basket trick. Persons concerned with birth control attach the basket to a catapult. When the man feels the approach of an orgasm, he tugs a second rope to ensure a rather dramatic form of coitus interrupt us. Also, single men sometimes combine the basket with a Chinese finger handcuff (one of tubes of folded palm fronds that drove you crazy as a kid) for a unique form of masturbation. If you would like to experience the technique and don't happen to have beams in your bedroom, try the Chinese picnic-basket trick. Toss a block and tackle into a basket and find a secluded wood where the tree limbs are fairly thick. Make sure your equipment is secure and never raise your friend higher than you would like her to fall.

Double Agent [March 1981]

About a year ago, I met an attractive Oriental girl. We went out a couple of times. Eventually, we went to bed. I really enjoyed myself with her. Eventually I moved in with her. Everything was going great. One day I got snoopy and started to go through old pictures she had stuffed into a box in the back of a closet. I ran across an envelope, on the cover of which was the name of a reconstructive-surgery clinic. I opened it and found documents of name changes, Social Security-number changes, work records and birth certificates. What it came down to was: The girl I had fallen in love with had had a sex-change operation. I didn't know what to do. I didn't let her know I knew about it. Gradually, I enjoyed sex less and less with her. I left her, needless to say. Since then, I haven't been to bed with any girl. I almost find it hard to even talk with one. Is it wrong for me to think so badly of her? Is there any way for me to get over this?--C.H., Denver, Colorado

Life, as the man says, can be a bitch. And silence can be a breeding ground for pain and confusion. Maybe you should at least talk this over with your friend. Maybe not. When a relationship disintegrates, you should go out and have an affair or four or five. You need to liberate your sexuality from the details of the immediate past, to assure yourself that your arousal is not dependent on your former partner. As the years pass, you'll look back on this as a great war story for those times when your children ask you, "And what did you do in the sexual revolution, Daddy?"

Hall of Fame [December 1984]

For more than a year, I have been seeing a ladyfriend who is very beautiful, has a great figure and, in her 40s, passes for 30. She is obsessed with fellatio. It's not that I object. However, I believe she prefers fellatio to normal intercourse. Whenever we begin foreplay, she will go down on me immediately. At times she becomes very tenacious and goes at it as if she were a starving animal. She moans and groans and makes weird noises and tries to take my entire penis into her mouth. Once she has started, there is no stopping her until I climax. She takes advantage of the situations in which intercourse is not possible, such as while I am driving or in a theater, where she will insist we sit in a remote and dark area. She fondles my penis until it is erect, then says, "I can't leave you like that," and goes down on me. She tells me her late husband loved fellatio and that she sucked him constantly, sometimes four or five times a day. They had no children, which is understandable. There have been evenings when we stayed at her home to watch TV. We would sit on the couch and she would make me comfortable and then lie across the couch in such a manner that she could view the TV and at the same time suck me. She has spent hours doing this, and when I have an orgasm, she becomes very aroused. At the completion of each orgasm, she runs her fingers down to the base of my penis and drains every drop, and never once has she made a spot on her or on my clothes. How do you describe a female--either clinically or with a slang expression--who prefers oral sex?--S.R., Atlanta, Georgia

A real find.

Condom Consciousness [July 1987]

I'm worried about contracting a venereal disease during sex. What should I do? Also, I suffer from premature ejaculation. Any suggestions? And, finally, I would like to increase the size of my penis. What do you recommend?--J.W., New York, New York

Here are the answers to your queries: (1) Wear a condom. (2) Wear two condoms. (3) Wear three condoms.

How to Talk Dirty [July 1987]

My lover wants me to talk dirty to her in bed. I don't have the faintest clue as to what I should say. Can you offer any hints?--T.S., Detroit, Michigan

Talking dirty can get you into the realm of the imagined and forbidden; it can be a great turn-on without being threatening. If you're fucking in one position, tell her how much you'd like to get her in a different one. Tell her how she'd feel. Tell her what she looks like with her pants down and her legs spread. Tell her how good she feels, how good she looks. Tell her you're, going to tie her up--it's not necessary to do it, just tell her about it. Tell her you know how much she secretly wants to tie you up. Tell her how good she is with her mouth or how good you're going to be with four mouth. Tell her you have fantasies about her in class, at the office, that only you know what a sexual animal she is. Tell her that she's in control. Tell her to rub your cock with her pussy. Tell her that her pussy's on fire. Get the idea? Shock value is erotic. Don't try to clean up your act; if you're going to talk dirty, talk dirty.

Hard Bodies [February 1993]

My girlfriend and I were on a secluded beach. After swimming in the ocean, we went back to our blanket to towel off. While doing so, I rolled my towel into a rat tail and, though I intended to give her just a love tap, I managed to produce an audible, crisp, whiplike snap. The towel barely kissed her muscular ass, but that was enough. Her entire body went taut, she turned to face me, her eyes squeezed shut, her lips puckered small and tight; she felt the pain. I stood there. I didn't know what to do. Then her lips curved slightly upward at the corners and she whispered in a challenging tone, "Didn't hurt." Her defiant statement earned her one on the other cheek. It had the same effect. She drew a long deep breath through her nose and said, "Take me home." We packed up, drove home in silence and took showers. When I stepped out of the shower, I was confronted by my smirking girlfriend in her birthday suit. She rolled the towel she had in her hands and tried to whip me with it, but it only wrapped around my knee. She giggled and tossed the towel at me and said, "Your turn." She then turned around and placed her hands on the door frame, legs spread apart. I repeated the action that had taken place on the beach earlier, leaving matching marks below the ones already there (being a college lacrosse player, I am well practiced in such locker-room antics). She took the towel from my hands, put it around my neck and dragged me into the bedroom. She pushed me onto the bed and began sucking my cock like a champ. At times she had my entire cock in her mouth--she'd never been able to do that before. While she was doing this I spanked her. The harder I spanked, the more enthusiastically she sucked me. By the time I came I was spanking her so hard my hand was hurting. She swallowed every drop of come she could suck out of me. This is a girl who repeatedly told me she would never swallow, that it was too gross to even think about. So what gives? Why did the pain turn her on? Is it psychological, biological or just physical?--S.E., Chester, Pennsylvania

OK, America, are we hot yet? We don't think we need to touch on the basics regarding sadomasochistic behavior--your letter pretty much covered them all. A partner, thrilled at being a sexual outlaw, led you both into new territory. She set the pace, directed the action and you both enjoyed the result.

Home Improvement [August 1993]

My nipples are one of my major erogenous zones, second only to my clitoris. I can almost climax from stimulation of my nipples alone. The problem is, my nipples are rather insensitive to light or normal touch. I like to attach clips to my nipples or twist them hard, burn them lightly with candle wax or rough them up with sandpaper. I found that if I do this prior to having sex with my husband, my nipples are so sensitive I can feel every touch and suck. The next day they're still so sensitive I can hardly keep my hands off myself. Am I doing permanent damage?--K.C., Portland, Maine

Years ago we got a letter from a guy who masturbated with sandpaper. He asked if he had a problem. We said, "Yes, but not for long." Apparently he consulted a sex therapist who cured him of the habit by switching In lighter grades of sandpaper, velvet, then a real woman. He still gets a hard-on every time he passes Ace Hardware. You are abusing your body, but so does every person who runs a marathon, mounts a Stair Master or plays tennis. Are sexual injuries the same as athletic injuries? All you've done is found a dramatic way to amplify the signals to the brain.

The First Lesson of Cybersex [September 1994]

For my first online sex adventure, I looked for a woman who would do anything I asked. To my surprise, one appeared. The first thing she said was, "So, what would you like to do?" We immediately started doing the nasty, and I mean nasty. After we had finished, I asked her what she looked like. She answered, "You'd be disappointed." I wasn't sure what to say. The first thing that popped into my mind was, Is this a man or a woman? I asked, and she turned out to be a guy. I was furious. Was I wrong to get angry?--Z.T., Houston, Texas

Here are a few observations. If a call name is overtly sexy (e.g., Sindy Luvtolick) or if a c-sex partner refers to her vagina as a cunt, you're talking to a guy. If she gives her cup size, you're talking to a guy. If she says she's 18, you're talking to a teenage guy or a postal inspector. If she won't switch to phone sex, it's a guy or a married woman. Don't let one bad experience stop your c-sex escapades. You can learn a lot. We all have sexual scripts, and saying them out loud or to a keyboard is an eye-opener. Bold lovers who would never think of stopping real sex for a midcourse correction can stop the momentum of a phone call or online session to say something like, "You always do that. You don't have to be so gentle. Does the phrase 'Suck the chrome off a trailer hitch' mean anything to you?" Our point: Cybersex is just sexual information. The thrill comes from the anticipation, waiting to see how another person reacts to the baldest, nastiest script you can come up with. Of course, you don't need a computer to capture that interactive mood. A dinner date works fine. Plus you get to see with whom you are playing, and if it works, you get to go to her place.

Sex vs. Fucking [November 1995]

While reading Advisor responses to questions about sex, I was surprised at your use of the word fuck, which degrades the writers' sexuality and makes you appear cheap. It seems that you don't know the difference between having sex and fucking.--G.R., Tempe, Arizona

We're well aware of the difference. You fuck when you're sweaty; you have sex after a shower. You fuck in a cheap motel room; you have sex in a master bedroom. You fuck on a hardwood floor; you have sex on carpeting. You fuck on a swing set; you have sex on a porch. You fuck in the woods; you have sex on the beach. Or vice versa on any of those, depending on your mood. The difference between fucking and having sex is between your ears, and everyone's love life should have a little of both.

*An LP is a flat disc with grooves, once used to play music.