+60 SILLY sexytime roleplaying scenarios

In my book for men, I spill the beans on a bunch of relationship hacks to keep coupled life hot and sexy — and weekly sexytime roleplaying is one of them.

My fly lady and I have been together for half a decade now, and we still go at it like rabbits on Viagra, red wine, and chocolate on the regular so there must be something to this roleplaying thing!

This is a custom we began in 2020, check out my original listicle of awesome, ridiculous, inappropriate roleplaying scenarios. 

Without further adieu, here are the roleplaying scenarios — let the sexytimes roll…

For tonight’s roleplay, you will be the enthusiastic winner of a date with the world’s foremost “expert on women” — you’ll be an extremely wu-wu young lady, who has recently been released from prison, an animal rights anarchist who “freed” animals from the zoo.

For our next roleplay — I was thinking we could be caveman and cavewoman. I’ll start a fire then you’ll enthusiastically mount my “speer” 😉😎😘

So for tonight’s roleplay…
I’ll be the eccentric owner of a fashion boutique store — with a mom who bosses him around — who just can’t seem to meet a nice girl! And you’ll be a young shop assistant interviewing 🤣😍😘

For tonight’s roleplay, I can be a gym owner (frustrated because everybody keeps getting fatter!) And you’ll be a new (very sexy) trainer starting who has some very strange ideas about fitness… 🤣😘😅

For tomorrow's roleplay… I will be a podcast host interviewing YOU, you’ll be a famous world traveler and author… And the sexual tension will be UNDENIABLE 😉

For tonight’s Roleplay
I will be a guy from Texas who has a TV show searching for ghosts 👻👻👻 and things in the woods 👾👹👻. I’ll be interviewing YOU as my cohost/sidekick 😉 you’ll be a “very spiritual” young lady BUT it turns out that you have an alternative motive… You have a dating app 📲 for ghosts that you want to promote 🤣

For tonight’s roleplay…
Let’s say that you are a young, sort of naive heiress to a fashion fortune.
I will be a male underwear model that you met at a photo shoot in Italy who is trying to convince you to waste your money on RIDICULOUS things… 🤣😂😍 sound fun?

For tonight’s roleplay…
Let’s pretend that you’re a naive exchange university student, I’m the lifeguard of a cruise ship. And I’m trying to recruit you into my casino robbery scheme… 😎😍😘🤣😃

For tonight’s roleplay…
We’ll say that you are an Australian bikini model, we’ve met on Tinder, and I’m a Scuba instructor and a conspiracy theorist WHO DOESN’T BELIEVE IN AUSTRALIA 😎😍😘🤣🤣🤣 Sound good?

For our roleplay tonight… I suggest that I be a crazy “Florida man” 🤣 who is renting an apartment off Craigslist from a landlady with A LOT of pets 🐕🐺🐧 I don’t have much money for rent BUT I have all sorts of talents to offer… 😘😉😗

For tonight’s roleplay…
Let’s say that we’re going on a first date; you’re a college girl studying animal husbandry with weird problems and I’m a “nice guy” from Nebraska who is always trying to save people from their problems 😂🤣🤓😍

Hey babe, for tonight’s roleplay…
I’ll be a male feminist boat repairman and you’ll be an anti-feminist houseboat owner who is sailing to Australia. You’re interviewing me because you’ve just inherited the houseboat. Sound good? 😎

I got (an outrageously) good idea for tonight’s roleplay… I’ll be an elite banker dude, trying to convince you to be my date to an “Eyes Wide Shut” party. You’ll be a small-town beauty queen competition winner who has just arrived in New York…

For tonight’s roleplay, we’ll do something a little different… We will be two people meeting again after years apart. We were teenage sweethearts 💑 that grew up together in Durango. I’ve returned to Durango for my special government job of studying aliens and ghosts. And you are a small-town girl that everyone wants to date, but you have a dark secret… 😎😍😘 sound good?

For tonight’s roleplay…
I’ll be corrupt customs officer Roselandenburger and you’ll be an Instagram influencer trying to import your ridiculous wardrobe of fancy clothes from Italy… You’ll need to be very PERSUASIVE to get your beloved packages… 😎😍😘🤣

For tonight’s roleplay…
I’ll be a sexy lifeguard boy who has recently been promoted to yacht captain. You’re going to be a fashion magnate (with way too many pets) who is hiring me to captain your boat around the Mediterranean… 😎😍 sound sexy…?

Let’s say that I’m a cowboy and you’re a snap chat star/influencer that is shooting a TV commercial in Montana 😎😍😘🤣

For tonight’s roleplay, we’re going to do something new — changing our races! I will be a dorky Asian guy and you will be a black girl going to university to become a TV sexpert 😂😭😎 We’ve met via Tonder, but I make the mistake of admitting that I am… A DOGECOIN MILLIONAIRE. You then proceed to try to talk me into spending my money on ridiculous things…

For our roleplay tonight…
You’ll be a gorgeous Italian model with an extreme sense of self-esteem that I’ve won a date with through a contest. I will be a high school boy who is a virgin and a bit nervous 😎🤣 sound good?

Ok for our roleplay tonight… We’ll say that I’m a traveling wu-wu cult leader guy, and I’m interviewing you to be my cult leader executive assistant. The cult is about aliens, cryptocurrency, and saving the animals 😂😘😍🔥 I will turn out to be a very insecure cult leader in need of validation. You’ll be Miss Manitoba, beauty queen and animal rights extremist from Canada 🇨🇦

For our roleplay tomorrow…
I’ll you’ll be a TV starlet, an actress in the hit show “The Courtesan of Monaco” and I am a cryptocurrency gangster that has kidnapped you. Now we are on the run from the government 😎😉😘 sound good?

Hey babe, ok for our roleplay tonight. You’ll be a celebrity astronaut going to colonize Mars and I’ll be interviewing for the position of being your impregnator — so we can repopulate Mars… 😘😂👩‍🚀🧑‍🚀

For our roleplay tonight…
We shall be on a first date but we will play reverse roles of the people we were when we met…
You’ll be an American digital nomad chick/YouTube health “influencer”
And I’ll be a virginal Bulgarian boy from Dyanovo
Sound interesting…??? 😲🙄😎🤓

For the roleplay…
Let’s again say that I’m a cowboy character from Montana, a momma's boy and you are a national reality TV sexpert who is sent to help me finally get a date… 😍🔥😎 sound rowdy?

For our roleplay tonight, I’m going to be a television ghost hunter and you’re going to be a famous Instagram bikini model who buys all sorts of ridiculous luxury items — including a mansion in Italy that turns out to be haunted 👻 I’m supposed to be investigating the haunting, but I get distracted investigating YOUR BODY 😍🔥😎😉

So for tonight’s roleplay let’s say that we are two travelers who have met on a flight to Australia, I’m a serious business guy 🤵and you’re a crazy party girl 👠 — we’re stuck in the same hotel because of an outbreak of dangerous dingoes 😉😍🔥

So for tonight’s roleplay…
You’ll be a rich woman from New York who has a fortune from selling overpriced kitty clothing, I’ll be an IRS tax auditor prime to get your money to pay for retarded government programs. You’ll have to employ your feminine wiles to avoid paying taxes… 😎🤣 sound good?

For our roleplay tonight I’ll be an American guy, a construction worker from Texas. Who has been robbed by aliens who abducted him, stole his money, and then left him as a refugee in your European county. I must do some male performances to make money… 🤑🤑🤑

For tonight’s roleplay I will be a VERY NAUGHTY doctor 👨‍⚕ you’ll be an eager-to-impress medical school student interviewing for an internship 😘😍🔥😉 sound good?

So for tonight’s roleplay…
Let’s say that I’m a famous romantic fiction author. You are a “fitness instructor” from Las Vegas in Dubai who is secretly my greatest fan. You have read my entire 27-book series about Wanderlusting Wendy finding love under foreign skies in the beds of foreign men… 😂😁😎🔥😘 Sound titillating?

For tonight’s roleplay…
Let’s say that I’m a CRAZY mental patient convinced that he is “The Prince of Australia” 🤴 and you will be my sexy therapist 👸 sound good?

For tonight’s roleplay…
I will be the boss pet kidnapper and you will be a celebrity pet breeder/pet sexuality empowerment coach — we will be meeting to discuss business 😎😉🔥 sound good? I have a dark secret — It turns out that I’m a gigantic momma's boy!

For tonight’s roleplay the theme is… time travel ⏳
I’ll be a TV talk show host from the year 1999 and you’ll be a very glamorous teenager from 2021. We’ll meet for dinner in a timewarp 😉 sound good?

For tonight’s roleplay… I’ll be the world’s ultimate NERD and you will be an Instagram women’s spirituality guru/cult leader with a camp in Tahiti that I’m hiring to help me lose my virginity FINALLY 😘😍🔥 sound good?

For tonight’s roleplay something spooky… I’ll be a real estate agent selling houses with ghosts (with odd personalities) and you’ll be my client who has just inherited a fortune…

For tonight’s roleplay…
A magneto-storm has occurred — the internet has gone down mysteriously and pets are rebelling against their owners.
We are both (SEXY) scientists meeting to discuss the cause… And I have a disturbing secret… 😘😍🔥 sound good?

For tonight’s roleplay…
A first date — we’ve met on an airplane. I’ll be a traveling UFO documentary filmmaker and you’ll be a sexy circus performer/acrobat who is “finding herself” 😉😂🔥😎
sound good?

For tonight’s roleplay, we’ll be two people going on a first date. We’ve met at Costa Rican self-help sex cult AND both have WILD New Years' Eve resolutions…
Yours must involve: property in Scotland, a pet pig named Pete, a sailboat
Mine must involve: Socks, sports car, weed

For tonight’s roleplay…
Will accompany our Anthony Fauci’s Misadventures serial — You’ll be a TV News Reporter and I’ll be a local “Florida man” who is trying to save his baby alligators from Dr. Fauci’s experiments 😜

For tonight’s roleplay…
You’ll be the daughter of a wealthy swiss banker that I have kidnapped on my old sailboat because I want money to open up a sex toy shop in Dubai.. 😘😍😎🔥 sound fun?

For tonight’s roleplay…
You’ll be an innocent 👼 young college girl (from an alpaca farming town in Maine) trying speed dating for the first time — I’ll be a VERY PERSISTENT wu-wu psychologist who makes it his mission to woo you 😉😘😍

For tonight’s roleplay: We will be MODELS…
You’ll be a fitness model and I’ll be a male underwear model who trying to seduce you by getting you to come to the most ridiculous party (on a yacht) 😘🔥😍😉

Tonight’s roleplay: Let’s do a situation where I’m interviewing you to be a news girl in “Placidville” — the most boring town ever. I’ll be the boss of the local news station that needs a sexy new news girl for his fake news agenda 😘😉 sound fun??

For tonight’s roleplay…
We’ll be investigating a mystery together in the Bermuda triangle. I’ll be a Russian oligarch's son, his yacht has disappeared and you’ll be an American bikini model. Sound fun?

For tonight’s roleplay…
I’ll be a man on a mission to end… LUMPINESS. I’ve been traumatized as a child by lumpiness and I need a sexy psychologist like you to share with 😎😉🔥 you’ll be a naughty therapist.

For tonight’s roleplay…
I will be a gigolo that has just “serviced” you, a wealthy woman, and you’re buying me dinner.
You’re going to give me tips on how to begin a new career as a pet shop owner in Japan. Sound good? 😘🔥😍😎

For tonight’s roleplay…
I’ll be a gigolo to a wealthy woman, you’ll be my secret lover, and we’ll be planning all the naughty times we can have together on a cruise ship 😘🔥😉😎

So for tonight’s roleplay…
I’ll be an eccentric billionaire with a plan to escape Earth and I’m interviewing you to be my space wifey to repopulate humankind. We met via a form on my website.
You’re an innocent girl that thought you were filling out a joke form (as I foolishly made the announcement on April 1st) — you’ll discover that you’re the most eligible candidate… 😘🔥😎😉

For tonight’s roleplay….
We’ll pretend to be two travel vloggers on a cruise ship. You’ll be an insta-hoe-ish travel vlogger from California and I’ll be a guy that explores creepy places 😉 sound good?

For tonight’s roleplay…
We’ll be doing a job interview, I’ll be a dramatic politically incorrect guy that owns a petting zoo. I’m hiring you to be my PR agent that helps me with all my petting zoo scandals 😂 sound good?

For tonight’s roleplay I’ll be a New York Times reporter (who is secretly a virgin) interviewing YOU — recently awarded the title of Sexiest Cowgirl in Colorado by Modern Woman Magazine. Sound good?

For tonight’s roleplay…
We’re in a mental asylum where I am a delusional patient, The King of… Something 😉 and you are a young medical intern who is very curious about me for your thesis paper on the allure of delusionally confidential men 😎

So for tonight’s roleplay…
You’ll be an experienced digital nomad bro and I’ll be an inexperienced and naive digital nomad ho. We’ll be having lunch hungover after we just hooked up the night before at a skanky couchsurfing meet up in Phuket, Thailand 🇹🇭 sound fun??

For the roleplay…
We’ll do a scenario where I AM a customer service representative DEMANDING verification selfies (showing some skin) from you to access your million-follower Instagram account. And now I need you to join me for dinner and drinks to “verify your account” 😉😂

For tonight’s roleplay…
I’ll be interviewing YOU to become a co-host of the “Glamor and Glitz” podcast. In the podcast we will be two rich kids who brag about wasting money and complain about our #firstworldproblems 😉 sound fun???

For today’s roleplay…
You will be a sexy lady (a soap opera actress — but aspiring to greater roles) strolling the boulevard who I daygame approach 😎 I’ll be a vagabonding animal documentary filmmaker visiting Bulgaria. You’ll be initially resistant but will SUCCUMB to my offer of sushi 😉

For tonight’s roleplay: I’ll be a very NAUGHTY tour guide/surfer dude that you’ve met in Panama just asking a few INNOCENT tourism questions. You’ll be a mysterious woman visiting Panama to do a little business 😉

For tonight’s roleplay…
We’ll be detectives in Spain who are having an affair and conspiring together to become politicians of the town BUT I have an unhealthy relationship with my mama I need to ask her permission for everything and you are sick of it!

For tonight’s roleplay…
You’re going to be an “influencer”/Instagram skank who was “canceled” for being politically incorrect — making fun) of the Chinese. You’ve lost your social media accounts and now for a job — you must be my babysitter 😂😂😂 I’m a “very mature” 17-year-old teenage boy excited to have such a hot babysitter.

I think we should do a follow-up on the naughty teenager and the babysitter who was a social media influencer… A few years later, I’m now a DJ in a college who is trying to throw a festival/sex cult meetup in Panama. And you will be the sex goddess of the cult. Or at least that’s the scheme I’m recruiting you into… 😎 sound good?

For tomorrow's roleplay: we met on the internet and will be going on a first date AND one of us will have lied about EVERYTHING on our online profile. Sound fun? 🤣😂😘

And most recently, I did a not-so-sexy three-way roleplay with my mom and wife…

Hey mom y wife, for tonight’s roleplay…
You two will be a team of scammers, Connie will be a veteran scammer and Gergana the apprentice scammer. Connie can be her charming southern alter-ego and Gergana can be a California girl. I’ll be John R. John a wealthy, yet-quirky, author of the “Wanderlusting Wendy” book series about a young lady finding love under foreign skies in the beds of foreign men.
You’ll have stalked me onto a cruise ship, where I’ve gone to escape my crazy ex-wife, and pretending to just be fans who have just randomly run into me. We’ll get dinner together and you’re going to try to scam me into giving you all my money so that you can make a movie with Gergana playing… Wendy!

I hope you and your partner get lots of laughs and sexy times out of these roleplay scenarios!