Fucking Day: 1,001 Sexcapades To Do If You Dare 🌭

Daring fuckventurers! Bold spelunkers of holes! Today our minds make love with knowledge! We are reading 2008’s 1001 SEXCAPADES TO DO IF YOU DARE. IF YOU DARE! By Bobbi Dempsey.

Like any sex book that starts with a number, 1001 Sexcapades to do if You Dare is not an instructional manual so much as it’s a psychological experiment to see how long it takes the author to suggest you go fuck in a bowling alley. It’s the vaguely horny remains of thought after all knowledge and wisdom has been juiced from a human brain.

Bobbi Dempsey is not like the other one-note sex authors featured here on our illustrious 🌭 website. She is a true Renaissance woman, writing books for dummies and idiots on a variety subjects like acupuncture, saving money in college, reading the minds of your enemies, Philadelphia, making your own ice cream, and of course, fucking. And here’s something weird, she gets her professional headshots done by the same guy who did your 6th grade class photos:

Every entry in 1001 Sexcapades to do if You Dare is rated by Bobbi herself from one burning heart (“Sexy, but low-risk”) to five burning hearts (“It doesn’t get any wilder”). These scores are never referenced and mean nothing. Penetrating a stranger to completion might be worth one burning heart and buying garlic bread might be worth five. Is it some kind of code? Did her Wordstar floppy disk come to life and this is how machines beg to die? Or does she… my God, does Bobbi not know how to fuck? No, impossible, this is the author of The Complete Idiot’s Guide to Homemade Ice Cream‘s second comprehensive guide book to all sex. She simply must know how to fuck.

It’s hard to truly look at ourselves and admit our flaws. But when you set out to write 1001 ways to fuck and after only 21, with 980 still to go, you are already suggesting “Go rent a video on how to fuck, and also try not to fuck,” this task is beyond you and you have to know that. Just get out, Bobbi! It’s not too late! This is entry #22! It’s not even close to too late!

So here we are 16 entries later and Bobbi’s tip for the sexually adventurous is to READ ANOTHER, ANY OTHER, INSTRUCTION MANUAL ON FUCKING.

So here we are 23 entries later and Bobbi’s tip for the sexually adventurous is to READ ANOTHER, ANY OTHER, INSTRUCTION MANUAL ON FUCKING.

Now that you’ve bought several other books and learned what sex is, maybe consider not having it? You know, “on purpose.”

By the way, if you’re wondering if it’s unusual for a sex tip book to tell you three different times to go learn about sex somewhere else and then tell you to stop having it, yes. It’s very unusual. Especially since, holy shit, we’re still in the fifties?

Sex expert Bobbi Dempsey has told you 97 different pathways to wild sex. She suddenly remembers something. “Oh my god, have you ever tried jerking off? It’s sort of like sex, I think, but alone. Let’s see… what else, what else? Oh! You could look up ‘intercourse’ at the library!”

In the first sex book written for virgins, Bobbi suggests buying a “fake vagina” and fucking it. Think of it like “an artificial vulva.” A type of “imaginary mons pubis,” if you will. In many ways, it’s similar to a “cubed section of corpse pelvis.” At three burning hearts it’s less adventurous than masturbating without one (four burning hearts), but it’s sometimes nice to slow things down and ejaculate into a gaping rubber hole.

“Didja hear this one? Didja hear about this? They have fake holes now that come in, get this, butt. That’s right, and this is real, there’s a new opening hitting the market and they’re calling it ‘anal.’ Hey, you know maybe if Bill Clinton had one of these, Monica Lewinsky could have taken a break from sharing cigars and gotten back to her cardio. Ya seen her? Ya seen Monica lately? I don’t want to get in trouble for animal cruelty, but the next blue dress they collect for evidence is gonna have to get filed as a circus tent. Must be her high sodium liquid diet. The filthy fat cocksucking monster.”

This probably hasn’t occurred to you, but Bobbi says while you’re masturbating into a butt, you can imagine it was the butt of someone famous…

… or not famous! You can think about having sex with any attractive person. Oh, and here’s an advanced Bobbi Dempsey tip– use some discretion before telling your husband you want to fuck the gardener’s face.

Here’s another secret no other sexcapade book will tell you– you can masturbate to the thought of anybody, even the ugly and loathsome! If I can get real here for a second, I don’t think I’ve ever seen an author stop what they were doing to nakedly reveal the strangest part of themselves like this. This is weird as fuck. Jerk off to someone you hate, even though it will be annoying, and don’t tell your wife because she’ll think you’re masturbating to her because you want her!? It’s like a radical treatment your therapist would give you right before they show you their penis and tell you they killed your therapist.

Oh no, Bobbi.

Bobbi, that’s maybe enough.

Bobbi, you absolutely have to stop.

I honestly thought I knew what “sexcapades” meant from context, but I was very wrong. How am I even supposed to joke about this, Bobbi? You sure add the “ault” to sexual ass? There’s no funny way to say, “I beg your pardon, you’ve written a list of ways to rape.” I guess it can’t get any worse.

Oh my god.

Ugh, her idea was “roleplay as an annoying person” and she called it “FIND OUT IF BLOWHARDS GET BLOWJOBS?” I know how this is going to sound, but Bobbi, maybe go back to the rape stuff.

I have a feeling your readers are going to nail this one, Bobbi.

You may have noticed, or assumed, that a lot of these 1001 authors will squeeze extra entries out of basically the same idea. However, most of them at least try to hide it a little bit. Gregory Godek will put a few hundred entries between “buy her a pizza” and “put a note on a pizza that says you’ve got a PIZZA my heart.” Bobbi doesn’t have the guile for that. She types every single variation right in a row. She’ll be like, “#244: Eat Ass! #245: Eat Stuff Out of Their Ass? #246: Eat That Ass When They Don’t Want You To. #247: Eat Nonconsensual Ass in a Bonnet. #248-#267: Different Colors of Unwanted Ass-Eating Bonnets.”

This woman has given herself a puzzle– say 1001 things about sex, and we’re simply witnesses to her “solving” it in the goddamn stupidest way possible.

I like this version of Bobbi’s recurring “go look it up somewhere else” sex tip because she put in a little extra effort. Although if you’re telling readers to go research sex toys, you should really put a spoiler alert before you explain dildos. Actually, hey, why did she tell me to go read about sex toys in a different book and then prove she’s perfectly capable of explaining sex toys? This is like delivering a map to someone’s house with directions on how to get to your house to pick up a dildo. It’s also maybe worth noting that Bobbi thinks browsing an adult catalog for purely academic reasons (3 burning hearts) is 50% wilder than snorting cocaine out of your lover’s ass (2 burning hearts).

It looks like Bobbi found some fun stuff while she was looking up dildos.

Have you guys heard of pornography? Check it out at your local library if you haven’t, but it’s videos of sex and get this: not everyone who makes it uses a union cinematographer. Try watching some!

Sometimes I’m sort of impressed at the meaningless chatter Bobbi manages to add to each entry. I mean, “watch amateur porn” isn’t much of a sex tip. It’s, in fact, nothing. But it is a complete thought. There’s nothing to add to it. There’s no person alive who needs Bobbi to elaborate on any of these, and yet she does. I just want you to appreciate how much mediocrity it takes to consider “amateur porn is porn made by amateurs” to be a fact worth sharing.

So if I’m understanding this correctly, Bobbi (in 2008) thought her readers had never heard of “amateur porn,” but knew exactly what gang bangs were and where to find VHS tapes of them.

While you’re picking up your gang bang tapes, maybe buy all the other porn? Maybe watch all of it in a week and pretend it’s an adult film festival. Maybe invent your own rating system? Maybe hold a pre-masturbation gala with your cats? Maybe draw a face on your rubber asshole and interview it on the red carpet? “Who are you wearing, Anal Opening? Haunting wet fart sound? Fabulous. And now back to me for the complex review of Forced Milk Guzzling 4 Hours of XXX Squirt-Hating Studs. It’s three Milky No’s way up!”

I doubt anyone predicted how much of this sex adventure book would be jerking off alone in the dorkiest possible ways. If you asked Bobbi Dempsey what qualified her to write this book, she might actually say, “Most of my experience is theoretical, but I have almost gotten Jenna Jameson’s top off on my IBM PC compatible personal computer. And I’m founder and host of the My Mom’s Guest Room’s 7-Day Erotic Film Festival.”

Here’s a wild suggestion! Have you tried asking a dildo clerk which dildo is best? If you ask them for “the real shit” they legally have to take you in the back and just destroy all your holes.

Try the yab yum pose? What the fuck does that mean? I get this book is for nerds, Bobbi, but I doubt any of your readers speak fluent Ewok.

First “yab yum” and now “woman on top?” No one knows what these words mean, Bobbi. You’re not making any sense.

What the goddamn fucking milk-squirting fuck!? We are only just now having an orgasm!? Bobbi, did you think we pounded off into our silicone butts for a week and nothing came out!? And wait, whoa, wait– did you give this orgasm one burning heart!?!? I’ve been building to this climax for 441 entries! I might turn the fuck inside out when this thing goes off.

Buy more adult games? What? Bobbi’s readers are the only people who have never heard of adult toys, intercourse, or masturbation, yet also have a collection of erotic board games they’ve played to death, yet also need someone to suggest “buy more of the thing you clearly have a lot of interest in!” Oh, and Bobbi says “you and your partner can pick out a certain number of games each.” That’s great writing because a certain number means certain fun!

When I read the title 1001 Sexcapades to do if You Dare, I sort of figured it would be a list of places where it’s unsafe to bone. But to her credit, Bobbi waited until the 500s before she started doing that. This is obviously a virgin nerd’s idea of a scheme, and she sort of gives it away by rating it one burning heart. She thinks risking suicide-by-cop for an adrenaline-fueled fuck fest in a police station is exactly half as wild as going online to replenish your adult board game supply. I’m not saying Bobbi has never fucked. I’m saying Bobbi has never even smelled someone who has fucked.

Anyway, we’ve got to be coming up soon on “fuck at the bowling alley.”

There it is.

It’s almost cute how she rates the pros and cons of banging at the mini golf course versus a regular golf course as if she would know or expect any living person to take her advice. She literally cannot conceive of what mini golf sex would be like other than one out of five on the wild scale and surrounded by children and the elderly.

By raw numbers, 1001 Sexcapades to do if You Dare suggests more sex crimes than any book ever written, and it does it in the most casual way. This isn’t outrageous– this is someone who has no sense of consequences because their only hobby is playing against themselves in pornographic board games.

“Go fuck near kids, maybe on a slide. I don’t know, I haven’t tried it. One star.” – Bobbi Dempsey

I think that’s enough locations to get us started. Let’s skip past this part of the book.

Sure, liquor. Another great idea, fuck machine.

Have you heard of “Thai food?” It’s a rare cuisine from the mystic Orient. You don’t fuck in it or anything. Eating Thai food is the entire sexcapade, and precisely as erotic as Sex in a Funeral Home.

Use donuts, I don’t know. Put them on your dick, maybe stick them on a titty. You’ll figure it out.

Bobbi is in the mid 700s and she can see the finish line. “Basically ram some vegetables up your vagina” is sex book author for “Oh God I don’t know if I have any more of these in me.”

If your advice is to cheat on my wife with John Oates, I’m way ahead of you, Bobbi.

If your advice is to not call John Oates “Daryl Hall” during sex, I’m way ahead of you, Bobbi. 

Oh hell yeah. I have no notes. Sweet sexcapade, Bobbi, and I’m not even being sarcastic. There probably aren’t a thousand ways to fuck anyway, so we might as well start listing our favorite Poison songs. You took mine, so I’ll say “Nothin’ But a Good Time.”

Seriously, what a legend to finish out her book by just naming random things.

Amazing. Amazing.

Hahaha this incel dingbat is buying a margarita like she’s a fucking anthropologist.

I’ve never seen anything like it. She is putting every remaining thought on the page no matter how vaguely related it is to sex. She just told us to fuck a pie like in the movie!

Bobbi knew the risks, but she was running out of time and knew she had to have sex at least once before she finished her sex book.

Bobbi, I think your readers knew this was how their journey was going to end.

Holy crap. Can we maybe slow it down a little, Bobbi?

Perfect. The same as all her other tips, but a little bit less lonely. I really mean it when I say this, Bobbi: this was breathtaking. Never has anyone written less about a subject they were more unfamiliar with, and I will think of you every time I call my silicone butt by the wrong name.

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This article was brought to you by our fine sponsor and Hot Dog Supreme: Michael Lehr, who did something worth five burning hearts and now the cops won’t stop searching for him until he finds a garage.