Dear Playboy Advisor: Questions From Men and Women to the Advice Column of Playboy Magazine (39 page)

A friend told me that if you want to make sure a prostitute isn’t a police officer, you just have to ask her if she’s a cop. She has to answer truthfully because it’s illegal for the police to entrap you. He said hookers can ask potential johns the same question but that it has to be phrased a certain way. You can’t simply ask, “Are you a cop?” Any truth to this?—M.D., Aurora, Illinois

None. It’s an old hooker’s tale. Undercover cops can lie about their identity; otherwise, they’d rarely be able to make arrests, and in some situations they’d find themselves in danger. The belief stems from a misunderstanding about what constitutes entrapment. Legally, a police officer can’t lead you to commit a crime that you would not have otherwise committed. But if you’re arrested for soliciting a decoy, you’ll have a tough time arguing that you were suckered. For entrapment to be considered, the policewoman would ostensibly have had to cajole and somehow convince you—the choirboy who had no intention of doing anything illegal—to give her cash for sex. Another fallacy is that money has to change hands, or that clothes have to be removed.

Let’s say I pay a woman to let me suck her toes. Can I get into trouble with the law?—M.L., East Chicago, Illinois

As long as she removes only her socks, we’d call it a massage. It would help your defense if you didn’t climax.

I’m dating a prostitute

A friend introduced me to a woman who works as an escort. I used her services several times and we developed a nonpaying sexual relationship and friendship. I am falling hard for her, and she has expressed the same feelings for me. My question is, in a relationship like this, will she expect fidelity?—E.S., Los Angeles, California

Why wouldn’t she?

Do you still have to pay?

If you hire an escort whom you don’t find attractive, and you send her away without doing anything but saying hello, do you still have to pay her?—J.H., West Liberty, West Virginia

We’ve heard of customers offering a third of the fee, gas money or nothing. But that was in the days before the Internet. Today many services post photos of their contractors online, which makes it difficult to claim you didn’t know what to expect. If the escort is not as described or doesn’t resemble her photo, stop her at the door before she has a chance to get comfortable.

On the prowl

I want to spoil my husband but am not sure how to go about it. Pink lacy panties, ass fucking, role playing, strip joints—they’re all getting old. What I have in mind is getting a five-star hotel room on the Vegas Strip and hiring three call girls to be there for us. I don’t want sloppy women; I want servants who will wait on my husband from the moment we arrive. I want them to pour him drinks, bathe him, massage him and so on. I’ll slip out and come back later so we can all fuck. How much would a night like that cost—$10,000? That may be a lot to spend on sex, but material items can be overrated, and experiences are forever. Can you help me put this together?—S.R., Las Vegas, Nevada

Let’s see: Five-star suite: $1,000. Champagne and room service for five: $500. Ten-pack of condoms: $13.99. Trio of escorts for a four-hour shift: $5,000. Coordinating three concubines and wife for “spontaneous” spa treatment and orgy: expensive, complicated and likely disappointing. Although prostitution is legal only in certain Nevada counties outside of Las Vegas, finding escorts online for a party is easy. But locating three strangers who are instantly comfortable with you, your husband and one another will be difficult. Your best bet would be to hire one experienced escort and ask her to bring two friends. The problem there is that you’re not choosing them, she is, and there’s no guarantee you’ll find them attractive. That’s one reason the call girls we asked didn’t like the idea of hiring three women, especially for your first time. Having four women in the room puts a lot of pressure on your husband to perform, and most men want their wife involved from the beginning. (Three women giving him a bath is hot, but three women giving him a bath while his wife supervises is hotter.) Based on their experiences with couples, our sources suggest you experiment with a threesome. If that works, then try adding a fourth.

Co-ed strip clubs

Do you know of any strip clubs that have female and male dancers on the same stage? I enjoy going to clubs, but my husband thought it would be nice for me to have a male dancer to look at.—C.F., Chicago, Illinois

Your husband is a considerate voyeur, but tits and balls are not a combination many guys will pay to see (except perhaps on the same person, which is a discussion for another time). The closest thing you’ll find are clubs such as the Masters in Myrtle Beach, the Sugar Shack in Lake Geneva, Wisconsin, Olympic Gardens in Las Vegas, PT’s Showclub in Denver or Cleopatra’s Viewpoint in Portland, each of which have female and male dancers performing in adjacent rooms or on separate floors.

Cut to the chase

I’d like to ask some girls I know to blow me for $50. How would you approach this? I don’t want a relationship, just head. Is it illegal to ask a chick to blow you for money?—D.K., Chicago, Illinois

Generally, it’s considered rude to offer a woman $50 to blow you. Technically, it’s also illegal, but it seems unlikely that asking people you know would get you arrested for solicitation. If you spend $50 buying a woman wine at dinner and she then blows you, that’s okay. A relationship will cost you $50 many times over.

PENIS

The long and short of it.

Are erections larger under a full moon?

My wife told me that my erection appears larger on nights with a full moon. I didn’t believe her, so she measured me every night for two months. And, sure enough, on nights just before, during and after a full moon, I was half an inch longer. Have you heard of this before? Does it have anything to do with the moon’s gravitational pull?—R.J., New York, New York

That’s a new one. Does your pubic hair get thicker, too? We don’t doubt your penis grew, but the only moon that has any influence on it is your wife’s ass. You both expected it to be larger in the moonlight, which influenced how aroused you became when she prepared you and took measurements. That could easily account for that half inch. Under controlled conditions, there would be no difference. The moon does not move the blood or water in your body as it does the tides, and its gravitational pull is a function of its distance from the earth, not its phase. Nevertheless, your wife should continue to stroke and examine your erection regularly.

Does size matter?

One night about a month ago my new girlfriend and I got to talking about her previous partners. She told me her first lover had a huge penis but that the sex had been painful. My penis is 6.5 inches erect, and she has told me I’m a perfect fit. She also says I’m the first guy to get her off every time. The problem is, I can’t stand the thought of her having been with someone so much bigger than I am. She has no clue this bothers me, but I once went soft inside her thinking about it. I keep wondering if she ever thinks her old boyfriend could “fit” her better now. She says I’m the best she’s ever had, but she also says that size does matter. Help!—J.B., Atlanta, Georgia

If you want to stay hard during sex and you’re not bisexual, don’t think about penises. You have a Goldilocks cock—not too small, not too big, but just right. That’s a good place to be. Your penis will “fit” with a wider variety of women, most of whom are content with large enough. Only the first few inches of the vagina have nerve endings, and a woman’s pleasure during intercourse comes as much from your penis girth (which helps stimulate her clitoris indirectly as you thrust) as length. While an extra-large penis might feel great to some women, just as many will find it uncomfortable. Besides, the vagina isn’t a gaping cavern. Its walls stretch and tightly grasp whatever is inserted—nature doesn’t discriminate. With your large-enough erection, you’ll also enjoy things that big guys miss, such as being deep-throated. We mention all this because your girlfriend is trying to tell you something: She likes your cock because it’s attached to you.

My entire life I have been coping with the size of my penis. It’s not the problem you’d think. I’m endowed to the tune of 10 inches. This has always been a terrible inconvenience, especially when I try to conceal my penis under clothes, and I dread climbing out of a pool. It also cramps my sex life. Several lovers have said sex is uncomfortable or painful, which makes me feel brutish. (I usually have to spend half an hour massaging their abdomens afterward.) Some women have refused to have sex with me after I’ve taken off my pants. My current girlfriend is five feet tall and weighs 88 pounds. It is almost impossible for us to make love. I would like men who consider themselves inadequate to know that there is nothing glorious about being huge.—C.A., Virginia Beach, Virginia

You’re not the first guy with this problem. In the 17th century, a French doctor recommended that the well-endowed man wear a doughnut-shaped piece of cork at the base of his penis to keep him from bumping his partner’s cervix. Given the present-day shortage of cork doughnuts, you may have to experiment instead with different positions. Your girlfriend may enjoy femoral lovemaking, in which she climbs on top of you and rubs her labia along your well-lubed erection. The woman-on-top position also allows her to control the depth of penetration. If necessary, place pillows under her knees to elevate her. Or use pillows to raise her hips as she lies on her back, which allows your penis to follow the curve of her vagina. In some positions, you can place the tip of your erection into the space below the cervix known as the posterior fornix. Some couples report that this allows several more inches of penetration.

A bump in the night

In an attempt to stimulate the G-spots of his lovers, a friend inserted a six-millimeter plastic bead under the skin of his penis. He used a sharp toothpick to make the opening, then let the wound heal (it took about a week). Have you ever heard of this? Does it work?—L.S., Loretto, Pennsylvania

A bead won’t do anything except make your penis swell from infection. And after all that effort, your partner might think it’s a wart. Penile inserts are most common in southeast Asia, where tribesmen have traditionally implanted bells, stones, jewels, ivory, gold, pearls, balls and shells in their shafts or gland. According to a book called
The Penis Inserts of Southeast Asia
(really), some objects are the size of a small chicken egg. “As many as a dozen might be inserted,” the authors note. “Kings might remove one of theirs to bestow it on a person deserving great honor.” In India, where inserts may have originated, prostitutes sold gold, silver and bronze bells to teenagers to sew into the skin of their penises to impress lovers. Japanese mobsters insert beads out of machismo—each represents a year spent in prison. One mobster’s ex-lover said she could feel his 13 “pearls” but that they didn’t make the sex any better. In fact, she described the bumps as “hokey.” If that sort of feedback turns you on, at least hire an experienced piercer to do the job right.

Molding your penis

I’d like to mold a dildo for my girlfriend from my own penis. Can you suggest ways to do it? Is there a kit I can buy?—D.S., Orlando, Florida

We wanted to cast our penis, but the cement truck never arrived. Yes, there are kits. Typically, you fill what looks like a Big Gulp cup with alginate, slide in your cock and balls and remain aroused for about five minutes. Once the alginate has hardened, carefully remove your frightened member, pour wax or rubber into the hole, let it stiffen for about 24 hours and—presto—a backup unit, complete with veins. Here are a few places that sell molding kits (you may want to order extra alginate, as most guys don’t get it right the first time): (1) The life sculptors at Artmolds.com offer a standard kit for $50. (2) CastingWilly.com has varieties such as a version with a handle for $85, or a $395 bronze casting. (3) CloneYourBone.com sells $30 wax molds that come with wicks so you can make candles. And who can’t use penis soap-on-a-rope? Buy Match Your Snatch at the same time and save 10 bucks. (4) For $80, CreateAMate.com provides an alginate kit with three chances to make an impression.