Dear Playboy Advisor: Questions From Men and Women to the Advice Column of Playboy Magazine (60 page)

It’s not a courtesy, it’s a contract. If J.T. felt the terms were unfair, he was free not to accept them. If his wife then had sex without his consent, it would be cheating and a problem for the marriage. That works both ways.

…And then he began to sob

Last weekend I went out with a friend and his girlfriend. They’ve been together for five years. We had a lot to drink and ended up back at my place at 4
AM
. I suggested they sleep over, and we crawled into my bed. After a few minutes, my friend’s girlfriend said, “I know what you guys are hinting at, so let’s do it.” The next thing I knew we were all going at it. She and I hit it off, and I think he noticed the sparks. He climbed out of bed, sat in a chair and began to sob. After a little fussing, she managed to calm him down and they left. I have spoken with her only once since that night, and she assured me everything was cool. Do I have a chance to get back into her pants, and how should I go about it?—J.M., New York, New York

Threesomes would be much simpler if they didn’t involve so many people. Your friend had probably daydreamed about countless threesomes, but none involved watching you fuck his all-too-eager girlfriend. When the fantasy hit the fan, he wasn’t prepared. You can ask this woman to return alone, but don’t be surprised if she declines, at least for now. You were all drunk, she loves her boyfriend, it was a misunderstanding, etc. Chalk it up as one of life’s little tragedies.

My friend wants me in the room

A friend of mine is a virgin. I suggested to another friend that she take care of him, and she’s up for it. He said he’d do it but only if I were in the room and did whatever he did. I told him that was sort of weird, but he says he’s just nervous. Should I go along?—S.D., Weehawken, New Jersey

Are you going to hold his hand during the train? Set these two lovebirds up on a date and let nature take its course. She can explain what to do as easily as you can. You’ve also overlooked the fact that while your friend may be up for deflowering a virgin, she may not be so enthusiastic about a threesome with a virgin and his handler.

My husband wants to go down with me

My husband has a fantasy that turns me off. He wants the two of us to perform fellatio on another man at the same time. The thought of my dear husband going down on another guy is too much for me. We tried fantasizing about it during sex, but it shuts me down. How can he enjoy this without my doing it or hearing about it?—A.T., Sudbury, Ontario

We find it interesting, first, that your husband, knowing the reaction most women would have, had the confidence to tell you this fantasy and, second, that you didn’t ask if we think he’s gay. We don’t necessarily—many people aren’t so easily labeled. But both observations tell us you have a relationship that is stronger than most. So we suggest this: Let your husband go down on you—while you’re wearing a harness and a dildo. That way he’s not sucking another guy’s dick, he’s sucking yours. The idea is to make this fantasy less about what your husband does and more about you playing the man. That may help you past the initial shock. Or it may just be beyond you. That’s okay, too. At the least you may pick up some new techniques.

Years ago my wife and I were using a dildo when she told me to lick and kiss it. When she saw how much it turned me on, she bought a strap-on. We did 69s, and now she sometimes demands that I fall to my knees and service her. She also gives me an ass pounding two or three times a month. I imagine these two letters will open a lot of eyes.—R.S., Lewisburg, Pennsylvania

You bet. One couple with experience in this scenario, M. and B. in Chicago, wrote to say that our suggestion that the reader use a dildo to fulfill her husband’s fantasy missed the mark. In their view, he found the idea of giving a blow job exciting simply because it involved his wife having sex with another guy. “He wants to share the pleasure she feels,” they wrote, “and also feel the other man’s pleasure as his wife sucks him. His wife, not the guy, is the focus of his desire. If he just wanted to suck a cock or receive anal sex, he could do that without her.” Which is a good point.

A birthday surprise

My wife turns 40 next year and I want to do something special, so I told her I would take her to Las Vegas. She loves Vegas but gave me a look that said, What’s so special about that? Then I told her I want to watch her pick up a stranger at a bar and screw him. I don’t think I could stand watching, but if she wanted me to join in I’d be willing. How can I convince her? She hasn’t said no, but I could tell from the look on her face that she is less interested in the idea than I am. Do women who’ve been with only one guy all their life get curious once they hit their 40s? My wife says no, but I disagree.—B.V., Los Angeles, California

It doesn’t matter if other women get curious in their 40s; your wife may not be. Besides the fact that she would be doing all the work, these things are messy, especially when you involve a random barfly. We suggest you ask your wife what she wants for her birthday.

THREESOME STORIES

Because so many readers write the Advisor to ask how to arrange threesomes, we wanted to find out how they come about, for better or worse. So we asked readers to submit their real-life threesome stories. Below are a few of the hundreds of responses.

I was talking to two women when one said, “Friends who play together stay together.” We started making out while her friend slid her hand down my pants. When we got to my place, they asked what I wanted to see. I told them to fight over me. So they gave me head while bickering over whose turn it was. It was fantastic.—M.F., San Francisco, California

The last time I had anything close to a threesome was two years ago. My wife and I watched
Eyes Wide Shut
while her friend blew me. Now I have blue balls because my wife says those days are over. She says she has grown up and that I should too.—D.P., Kansas City, Missouri

I was hosting a frat party when I noticed two girls flirting with each other. I told each girl that the other had asked to meet her upstairs in my room. I waited a while, then went up to see how they were doing.—M.C., Parsippany, New Jersey

It’s happened three times, all with my current girlfriend: (1) We invited a waitress back to our hotel. The next morning, as we were checking out, the manager kept saying, “You had two girls!” (2) We were on a cruise. A blonde asked if I was single. I told her I could be single if she wanted and took her to meet my girlfriend. (3) We were playing golf. A woman playing alone caught up with us. I asked, “Do you ever get hit on by other golfers?” She said, “All the time.” So I asked, “Do you ever get hit on by couples?” We’ve had other prospects, but it usually happens when we least expect it.—R.W., Phoenix, Arizona

This chick at a party asked if she could sit on the arm of my chair. Some guy bumped her and she fell into my lap. We talked and started making out. Five minutes later I opened my eyes and 30 people were watching us. Another chick said, “This shit is making me horny.” Everyone cheered as the girls led me away. I always thought a threesome would be confusing, but I didn’t have to do much.—P.L., St. Louis, Missouri

My date pushed me against a wall, crouched down and unbuttoned my jeans. That’s when I saw her roommate. It turned into an up-and-down swap. The key is to let the women be in control.—G.C., San Diego, California

My fiancé introduced me to his ex. I suspected he wanted to sleep with her one last time, so I organized a threesome. I had two ground rules: He couldn’t kiss her, and he had to give me most of his attention. But they tried to slip in a kiss, and he fucked her four times and me only once.—A.T., Provo, Utah

My wife and I had three-ways with her friend. Things were great until I decided to fix up the friend with a co-worker. He told her he would love to swing with her. She was pissed. I had no idea he’d go for the gold within 15 minutes of meeting her. I learned the hard way not to screw and tell.—W.W., Chicago, Illinois

My girlfriend and I did it doggy style while her friend stood over her back and pretended she was riding a mechanical bull. No matter how much you fantasize about a threesome, you’re never ready for it.—B.T., Milwaukee, Wisconsin

My buddy and I met this adorable girl at a club. We all went back to his place. He asked her, “What do you dream about?” She said, “I don’t know.” He said, “Close your eyes.” She closed them, and he asked, “Do you dream about this?” and kissed her. Two hours into the lovemaking, she asked, “Can I open my eyes now?”—J.K., Limbazi, Latvia

The best part of my threesome was watching the women get dressed together in the morning. I wished all my guy cousins and dead ancestors and all the male friends I ever had were there to witness it.—M.O., Los Angeles, California

I stepped outside a bar for some fresh air and spotted two women making out in a car. The car door swung open, and a co-worker called to me. She asked me not to say anything to her husband. Then another co-worker poked her head out and said, “When was the last time you had two women suck your cock?”—M.L., Philadelphia, Pennsylvania

My girlfriend and I double-dated with two cops. We went back to my date’s place, and he and I started kissing. My friend started to pout, so her date joined us. Four cop hands and two cop mouths all over my body! The real fun began when they used parts of their uniforms. Batons, cuffs—oh, man! My suggestion for a threesome is to double-date with two cops and a flop.—S.B., Dallas, Texas

Our newly divorced neighbor came to dinner and kept saying she wanted an alternative relationship. When she began rubbing my wife’s shoulders I moved the massage in an alternative direction.—J.K., St. Louis, Missouri

My wife’s sister, who was renting our upstairs apartment, wanted an air conditioner put in. After I installed it she sat on my lap and wiggled until I got hard. Then there was a knock on the door. It was a friend of hers who needed a place to stay. My sister-in-law said it was up to her landlord. Her friend said to me, “I’ll give you whatever she’s giving you.” I am divorced now, and sadly enough the only thing I miss about my marriage is my sister-in-law.—A.L., Tampa, Florida

My girlfriend asked me if I thought one of her friends was cute. I said, “Sure.” She said, “Great. She’s your birthday present.” I tried to play it cool later at the hotel, but my girlfriend got impatient and said, “Get over here and fuck us.”—J.T., Milwaukee, Wisconsin

I live a few blocks away from a club, so my girlfriend and her friend decided to use my bathroom rather than wait in line. I found the two of them on my couch. “Don’t be mad,” my girlfriend said. I still call it my holy weekend.—J.T., Los Angeles, California

While thumbing through a magazine I came across an article on threesomes. Two days later, I found the magazine on our coffee table, opened to the article. I asked my girlfriend what was up, and she said she and our new (female) roommate had read the article together. The next morning I woke up to a kitchen full of sex toys, champagne, whip cream, cherries, a kiddie pool filled with hot water and bubbles—and two horny women. Never underestimate what your girl will do for you.—M.T., Phoenix, Arizona

When I was in college, I dated a radiology technician who I met while having a barium enema—no kidding. He asked me what I wanted for Valentine’s Day. I told him I’d always wanted to make out with the girl next door. We visited her. My boyfriend told me to leave for a few minutes. When I came back, he had her shirt off. I enjoyed the experience but prefer to give a partner my full attention.—A.L., San Antonio, Texas