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The Straight Girl's Guide to Sleeping with Chicks



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About The Book

From Jen Sincero, author of the New York Times bestseller You Are a Badass, comes a deliciously sexy how-to guide for any woman who sleeps with chicks (or just is curious about it)!

“You can’t swing a dead cat at a bridal shower without hitting a straight chick who’s slept with another woman, who’s thought about it, or who’s ready to make the move as soon as someone breaks out the booze.”

Such are the incisive pearls of wisdom to be heard from straight chick and girl-on-girl dabbler Jen Sincero, author of You Are a Badass. A deliciously sexy how-to guide, it gives curious straight women the complete inside scoop on girl-on-girl action—from pickup lines and virgin jitters to threesomes, techniques, and toys. Drawing on personal experience and hundreds of interviews with straight girls who’ve slept with lesbians, straight girls who’ve slept with straight girls, lesbians who’ve slept with straight girls, and straight girls who’ve done both or neither, Sincero covers the A to Z of the experience including:

-Obtaining a visitor’s pass to the girls-only club
-The super-huge importance of sticking your hand down your pants
-The straight girl’s starter kit—from nail clippers to cocktails to get her in the mood
-“Gettin’ Some 101”—positions, techniques, and instructional photos
-“And Boy Makes Three!”—how to have a threesome that’s fun for all
-Suggestions for further viewing and reading and much, much more

Packed with expertly toned advice that is at once laugh-out-loud hilarious and fundamentally practical, The Straight Girl’s Guide to Sleeping with Chicks is ideal for any woman looking to spice things up with a boyfriend, break the ice with a best friend, or simply add a few just-in-case items to her sexual menu.


introduction: The Joy of Sex with Chicks

I think my first sexual encounter with a member of the same sex happened when I was seven. My friend Wendy and I would spend hours playing with these little plastic Fisher-Price people who came with cars and houses and villages and stuff. We'd make up stories about them, have them go to work and cook dinner, and when they were bad we'd send them off to The Big Ween. "Uh-oh, Sally didn't do her homework again," Wendy would say, kicking off her panties and lying on the floor. She'd hold terrified little plastic Sally up in the air and announce to the entire Fisher-Price community that "Sally was bad and must go to The Big Ween," then slowly lower the toy between her legs. I'd watch mesmerized as Wendy rubbed Sally around and around, stopping only when Wendy's My First Pussy had gotten its fill. Inevitably, moments later, my own Mr. Smith would wind up telling a lie or robbing the Fisher-Price bank and my panties would go flying across the room. "Uhhhh-ohhhhhh!"

I'm not sure if this counts as sex, since there were actually two The Big Weens, Wendy overseeing operations at hers and me at mine, but I do know that for me it wasn't all innocent play. I was a really sexual kid who started masturbating at around five years old, and who was constantly getting sent to my room for greeting company with my hand down my pants. So I find it kind of surprising, since I was such an early enthusiast and a curious person in general, that it took me until my thirties to really get down and dirty with another woman. I'd done my fair share of dabbling, made out with a few drunk friends, and groped the occasional boob here and there, but nothing all that intimate ever happened. It was usually the result of being wasted and figuring that if there were no cute guys around I might as well pin Sharon to the couch. And it never went beyond that until my thirties. Maybe I was too uptight or too immature, or maybe all my friends were just uglier back then -- whatever the reason, it took me a couple decades before I found myself face to face with The Big Ween again. And much to my surprise, just like little plastic Sally, I got sucked in by it.

At the risk of never getting laid again, I decided I'd write a book, because my experiences with women affected me in such a radical and positive way I had to make sure other women knew about it. I wanted everyone who's ever thought about it to try it. So what if I repelled future lovers, terrified that their most intimate secrets might wind up somewhere on page 84?

It was like I'd learned a whole new language that suddenly allowed me to communicate with members of my own gender in a way I never had before. As if sex wasn't already fabulous enough, I'd just doubled my fun by transforming the other half of the population into possible bedmates. It did incredible things for my confidence as a woman and as a sexual being, and whether or not I ever meet a woman I want to sleep with again, I'm really grateful I've done it. Several things in particular about the experience really struck me, because they were so remarkably different from being with a guy:

1. When you're with another chick, the roles can switch back and forth in a much more equal and fluid way than they do with a guy. You can be the butch one, totally in control, throwing her around in bed, and then switch to being submissive and girly. It obviously depends on who you're sleeping with, since many women identify with being more dominant or submissive and aren't up for flippy-flopping, but if you get with someone who hasn't chosen sides you can switch back and forth and feel fully in either role, which I find incredibly hot. This is not to say that you can't do something similar with men -- I've been with some stunningly open and experimental guys -- but even if you put them in a dress, strap them down, and make them call you Daddy, they still have a dick and you still have a pussy, which automatically makes them more masculine and you more feminine. Without that biological reality, you're totally free to be whatever, and I found it incredibly liberating and exciting to really feel one hundred percent on both sides.

2. The way women orgasm is so different from the way guys do. We don't need to stop and recharge before starting up again, so we can go on and on till the break of dawn without a time-out. I've never in my life had nonstop sessions like the ones I had with girls. It's crazy! It can bring you to a state of prolonged excitement that's almost unbearable. There were times when I seriously thought I was going to have a heart attack.

3. I found that every time I did something to her, I could imagine I was doing it to myself. So much so that I could practically feel it even if I wasn't touching myself at all. The combo of watching her get off and imagining exactly what it must feel like could bring me to orgasm.

4. Women's bodies are unbelievably soft! They're like the softest pillows in the world. This has made me totally understand why men go apeshit over us. It also made me aware of my own body's softness, and it made me feel incredibly sexy in a way I never had before.

5. Lastly, because we live in a society that has a large stick up its ass, and also because my sexual hometown is Straightyville, sleeping with someone I wasn't "supposed" to made me feel kind of kinky. This turned me on like nobody's business. I felt a teeny bit nasty, dirty, and queer, and I think this helped inspire me to step outside my sexual box more than I ever had before. I did stuff with girls that I'd always wanted to try -- we went to sex clubs, tied each other up, dabbled in S&M, and enjoyed the wide world of sex toys. I attribute a large part of this to the fact that I was with like-minded kinky and adventurous souls whom I trusted and who I was sexually compatible with. But also, the fact that they were women broke the dam of my usual sexual behavior and opened me up to a flood of new experiences.

The whole thing was so inspiring I immediately started handing out surveys and interviewing other people to hear their stories and to get all angles. The more women I talked to, the more I learned that sleeping with chicks was either on the majority's to do list or already crossed off. Even the people who really looked like respectable, take-yourself-and-your-filthy-questionnaire-off-my-property types were game. And I have to say that the majority of them gave the whole experience an enthusiastic two thumbs up. They couldn't wait to spill the beans to me -- in graphic detail, I might add -- and I couldn't get over how inspiring it was to learn that all these women are out there fearlessly pushing the sexual envelope. Girls are curious. Girls are hot. Chicks dig 'em!

When looking for people to survey, I cast as wide a net as possible. Tons of different factors go into determining how we approach sex in general: religion, age, parental influence, general uptightness, tequila shots...In the fifties you saved yourself for marriage, while today everyone's starting to screw at an age once associated with hopscotch and noogies. Asking the same questions of people from different planets resulted in a wide variety of answers. And I'd like to say I represented all groups equally, but I'm afraid I didn't -- most of the women in the over-seventy-years-old demographic whom I dared approach treated me like a filthy whore, so I wasn't able to get as wide an age range as I would have liked.

I spoke with straight chicks who've slept with straight chicks; straight chicks who've slept with lesbians; straight chicks who've done both or neither or were too drunk to remember; lesbians who've slept with straight chicks; bisexuals; undecideds; and my mother. I put up flyers on college campuses, online, in bars, and in the lobby of a nursing home. One underlying theme kept repeating itself: women connect with women. We can talk to women easily, relate to their issues, process our "stuff" and provide emotional support on a level that suggests a deep spiritual connection. I know this is a big fat generalization -- certainly there are women I'd rather kick into an empty pool than talk to for three minutes -- but in general there's an emotional language specific to women that creates a certain bond. And when you take the leap and bring good old sex into this equation, it can really make your hair stand up. Whether you're slamming Mary in the bathroom stall or picking out china patterns with Tiffany, you stand to touch on something deeper than you may have counted on.

This fact kind of tossed a monkey wrench into my plan. I'd set out to write a funny, sexy, sassy book that people could give as a gift or leave on their coffee tables to liven up a cocktail party. Something that people could flip through, laugh at, and slap their hand over their mouths, squealing, "Oh my god, my husband and I tag-teamed our nanny, too!" I do believe I accomplished this, but really delving into the subject of sex with chicks made me realize that there's a whole lot more I needed to talk about. Sex is heavy, and sex with women can be as deep as it is liberating. It allows us to break free of heterosexual roles and expectations and explore sex in a whole new way. We get to experience a similar body that'll give us incredible insights into our own. The fact that I'd overcome my inhibitions about being with women opened me up to trying things with them that I was too shy to try with a guy. It made anything possible, and I know I'm a better lover today because of it.

Another thing that may take some by surprise is that it's possible to become attached even if you're "straight." If your experience lasts longer than a happy hour, it can have the added extra weight of the aforementioned female bonding. If you're having hot sex with a chick on a regular basis, chances are very good you're also connecting with her emotionally, which can totally screw up the free-and-easy "I'm not hungry, I'll just pick" position we straight girls can go at it from. In fact, it's not at all uncommon for straight women to get into committed, monogamous relationships with other women. "It was total addiction from the get-go," says Carrie, 41. "We were madly in love. I felt a certain connection and understanding with her that I never got with any man. When we broke up, it was more for personality reasons than the fact that she was a woman."

As for my own experience with dating women, I was more confused than committed. I'd never had crushes on women, never done my signature calling-and-hanging-up routine, never turned down a piece of chocolate cake because thoughts of Amanda had filled my stomach with butterflies. Then, all of a sudden, I found myself with an incredible woman who got it and me, and the sex was hot as hell, and before I knew it I was in a relationship. I'd never connected with anyone the way I did with her, and that definitely articulated itself sexually as well. She listened to me as no guy ever did and she totally knew where I was coming from. If I was weeping at a commercial, instead of looking at me as if I was insane she'd grab me a tissue. She understood my mood swings and my feelings, and could fully articulate her own. I felt nurtured and safe and understood. But -- unfortunately -- I wouldn't/couldn't/didn't get all the way in. Because although there's no questioning that I loved her, the feeling lacked a certain tug I was used to feeling for guys. Granted, I've felt that tug for guys who live in their cars and refuse to hold my hand in public, but I need the tug. It marks the difference between someone you're crazy about and someone you're in love with. At least, that's what I kept telling myself. Was I using the tug as an excuse because I was scared to be with a woman for real? Was I tugless because she just wasn't the one? Am I just a big fat dick-lovin' whore and that's that?

It didn't help that I was constantly being bombarded with questions along the lines of "So, like, are you a lesbian now, or what?" It's the first thing that everybody asked me when I told them I was seeing a chick, and it brings up a question that needs to be addressed. What the hell does it mean to be straight or gay or bi or whatever? And why does it matter?

Labels are indeed for cans and for lazy authors, and for people who are generally uncomfy without everything being put in neat little boxes. Labels are hopelessly pointless. I know several women who were out and proud and fully lesbian identified for decades who are now allegedly Mrs. John Straightypants. Then there are women who were once staunch straights who are now shacking up with chicks. There are bisexual women who like fucking gay boys, gay men who like fucking women who used to be men, people who dress up like stuffed animals and fuck each other, and on and on and on. It's murky out there in sexland. Humans have been screwing anything that'll hold still long enough since the beginning of time, and trying to figure out what and why in order to catalogue it all is a big fat waste of time.

But I have a book to write here and I need to identify people somehow.

Ideally this book would be titled A Guide for Women Who Usually Have Sexual Relationships with Men and Who Would Now Like to Explore Sexual Relationships and/or Brief Encounters with Women. Instead I'm going to be a hypocrite and fall back on using the standard labels I so enjoy looking down upon. I hope that everyone who reads this assumes the definition in my ideal title is what I'm talking about when I say "straight" (I also refuse to put quotes around the word "straight" for the duration of the book). This may sound nitpicky, but the world of sexual identification is a vast and political one that most heteros are completely oblivious to, since we haven't had to go to battle with popular opinion over our sexual preferences. Those of you who decide to step over the heterosexual boundaries may get an unexpected taste of how the other half lives. You may suddenly be challenged by the heterosexual, bisexual, and homosexual communities to define your sexuality, and chastised when you don't adhere to certain rules. You may also find that you're suddenly demanding some explanations from yourself.

For the majority of women I spoke with, however, leaving the warm, secure confines of Hetero World was totally worth it. "You get to have this thrill ride with something taboo," one experienced dabbler explained. "It's like a secret weapon that ups your sexual confidence. It made me feel really powerful. And tingly. There's something really sublime about connecting with another woman that way." "There's something about a woman's body that's just so sensual," another wannabe said. "It seems kind of safe and terrifying at the same time." I spoke with women who fantasize about sex with women but have no interest in making it happen, those who only want to do it to please their boyfriends, and one experienced lady who said: "I'll fuck anything when I'm drunk."

Whatever your reasons may be, you certainly have nothing to lose by trying it. For me, sleeping with a woman was like taking a superhero pill. It inspired interesting discussions with friends, family, and a slew of strangers. It opened me up to the incredibly diverse world of sexuality that I'd only dipped my toe into before and which I'm now fascinated by. As with anything else in life that intrigues you, you'll feel a lot worse for never trying it than you will for trying it and having it not work out. Why die wondering?

Copyright © 2005 by Jen Sincero

About The Author

Photo Credit:

Jen Sincero is the New York Times bestselling author of You Are a BadassBadass Habits,The Straight Girl's Guide to Sleeping with Chicks, and the semi-autobiographical novel Don't Sleep with Your Drummer. At the moment she lives in California and can be found on the web at

Product Details

  • Publisher: Touchstone (February 1, 2005)
  • Length: 320 pages
  • ISBN13: 9780743258531

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