‘roleplay’ stories

A health scare leads Doctor Swift to take care of Cole.

His girlfriend uses a friend to humiliate him — or does she?

Dressed as a mermaid she discovers new sexual highs...

A third party puts a strain on the relationship.

Andi's afternoon at the pool doesn't go as she expected.

Detention time, and lessons learnt.

The only thing stopping her was herself.

Latina MILF Jo's initiation to skype sex with strangers.

Mrs. Officer.

Jay and her boss make up and make plans.

The Sophomores meet Mr. Harding and his devious machines.

The continued adventures of Kevin, Bill, and Chris.

She reports to headmaster for her punishment.

Convention Cosplay Time!

Transcript of a bro-sis role play I did here on literotica.

Abbi has a sexy encounter with the history teacher Ms. Ford.

Kai and Amanda's V-day date doesn't go as planned.

Diary of a Secret Slut - Seducing Doctor Full Examination.

Angela is a sexy librarian with a dungeon in the basement.

A class in endurance, and discipline…

A phone call gone naughty…

Power, morality and sexual release.

Mia masturbates to her hotel porter.

Bed hopping antics in the dead of night.

Dressed as Minnie Mouse niece Ally squirts for uncle.

Rob and Sandy's third date.

Deborah Ann Woll and one of her players have fun postgame.

Late Night Drives Turns Into Fuck Session w/ a Stranger.

Unexpected guests arrive.

Patrick stumbles into a bar and encounters a succubus.

Lindsey and Sam, who is a teacher, roleplay in his classroom.

It's about my Queen and my Cocubine.

Hank is down on his luck, but a strange object changes that.

A different city, a different place, a different experience.

Trip to the bookstore ends in wild threesome surprise.

Friends with benefits, D/s, roleplay and public play.

Teasing her girlfriend was fun. What came next was better.

... and the Double-Glazing salesman.

Corporate woman returns home to her pet.

"A wife contacts a therapist to improve her sex life..."

Taylor Swift becomes Miss Americana for the night.

The wife's pink pussy was just too good not to share...

D&D cosplay becomes roleplay.

Ash's boyfriend buys him a pair of pretty panties.

Jack teaches Alexandra that he's not what she thinks.

Kelli's roleplay with her boyfriend continues.

Husband gets captured by his wife.

Loving wife gets rough treatment from a stranger.

Jim has a plan to get what he wants, whatever he wants!

A road trip to Deanne's ass.

Husband and wife roleplay from each of their perspectives.

Taylor Swift as a cheerleader, need I say more?

Student and teacher fall into their roles.

A DD/lg story.

Super Krissy and Her Nephews

Elsa Hosk, Stella Maxwell, and Romee Strijd get fucked.

She's ready to let her BFF take her to bed.

Can he wait for his lesbian best friend to fall for him?

Master brings fruit to submissive teacher.

Miss Christy buys her boi a toy.

May the Fuck be with You.

Abbi has a sexy time with her tutor Mr. Cleveland.

I really need to come.

Strapon play in a church. Guy/girl fun with humiliation.

A roleplay of a 3 vs 3 orgy duel.

A familiar voice has some delicious ideas in store for her.

Jim has a plan to get what he wants, whatever he wants.

An evening with wine.

A boss needs to tackle an employee's under performance.

I get invited to MILF Poker Night!

The party doesn't go according to plan.

Their marriage takes a lover, the girls stay home and play.

Pretty Woman, Risky Business.

She lets Him have His wicked way at the hotel.

Will this brat break the no nudity rule?

She gets off easy... this time.

Gina and her sexual fantasies for a desperate need for sex.

Abbi has a hard bondage and caning session with Coach Carter.

Girlfriend surprises you with something different.

A whispered ramblefap roleplay.

It's California's favorite sex-themed game show!

Lizzy and I play sexy cops and robbers

A couple tries some roleplay.

He's invited to enjoy a public fantasy to help cure his blue

An unexpected roleplay sees Lola being arrested - and taken.

Real life femdom roleplay inspired series - enjoy!

They meet in bar, but do they know each other?

Ann becomes Queen for a day.

Their romantic and erotic relationship deepens.

Joanna becomes Mark's whore for the night.

A couple has fun with a whip.

Jenna plays the shoplifter scene.

Based on my actual first time with a man.

Pennie recalls first interrogation & meets Officer Claude.

She wanted him and she got him.

A different kind of visit to the Agency

Jim has a plan to get what he wants, whatever he wants.

Sabine and Charlie’s relationship gets more involved.

Sean fucks Lola Bunny, Patrick goes to a frat party.

A quick quiz for exams leads to Anal.