‘anal first time’ stories

A Principal disciplines a stuck-up hot bitch cheerleader.

His roommate is sweet, cute and she's into butt stuff...

Nick and Mia's passion for anal sex inspires Ashley...

Straight guy goes into a shemale bar and is forever changed.

She's his neighbor, his best friend and so much more...

Nerd dominates bitchy MILF and takes her virgin asshole.

Weird consequences of his girlfriend's fight with her twin.

I thought I was in love... then I met her little brother.

An older man takes a willing first timer all the way.

My sis finds out she likes butt stuff, and I lend a hand.

His girlfriend's twin sister has a weird request.

Threesome with husband and her sexy best friend.

Michelle and Tyler get much, much closer...

Young woman sleeps with best friend's father.

Straight teacher is turned by two ex-students.

Loving siblings wake up to a dream come true.

She needs a date, but he wants something in return.

Couple experiments with first time anal sex.

The night continues.

Curvy cougar loses ass virginity to young muscled swim coach.

She gives her grandfather her virginity - all 3 of them.

Mark & his cousin share many firsts.

He overcomes her reluctance and takes her virgin ass.

Tessa has an amazing surprise for Nick...

A tale of longing, insecurities and sibling love.

Drunk Samantha is way naughtier than sober Samantha.

Babysitter gets caught with her hand in her pants.

Youthful aunt introduces nephew to anal pleasures.

An erotic coming of age tale of sexual awakening.

Four men have fun with Erin over a long weekend.

He takes her anal virginity.

Lyla and Mike have a talk, and more.

A gay roommate uses his straight roommate.

She teaches a few friends how to take it.

Plans for the summer and a new experience for the siblings.

Sisters, Amie, and Beth's last hole - what a night.

Katie's anal experience.

After some unfinished business, Jason finally bottoms.

Young nurse is helped over her fear of anal sex.

18 year old gives up her virgin ass.

Kidnapped right from her bed, Princess Mera learns about sex.

Phil and Ben help Linda keep her chastity vow, technically.

this is a story about how I fucked my girlfriend's daughter.

Master takes her anal virginity.

No one told her she was required to gape for the camera!

Love between and older man and a young woman.

First time sex with a cousin leads to anal exploration.

My first time; a 25 year old bear cub fucks me.

Bella loses her anal virginity

He loses his virginity to his friend's hot mother.

Richard and Buddy go deeper, at last.

I wondered what it would feel like to be fucked in the ass.

My BFF and me get our anus stretched.

Married guy finds his bi side when wife's back is turned.

Mom had a special request I was happy to fulfill.

Training for anal intercourse.

Ben is left alone with Bella. And with her ass.

Unexpected visitor gives a cd her first time with a man.

Young man discovers anal sex for the first time.

A tale of love and lust in the Caribbean.

She wants to try anal, but why should her pussy miss out?

His first time being, well, fucked with a strap-on.

Jill seduces dad with a little help from Jim.

Account of a trip with my mother in law.

An older man teaches Yuuka what she likes.

A hitman is surprised by his attraction to his target.

Nicole begs for reconciliation by offering her Anal cherry.

Bi neighbour introduces her lesbian neighbour to anal sex.

She delves into the joys of anal sex.

She's new to anal, and she gets a surprise on her brithday.

Jaded 22-year-old has his fantasy fulfilled.

A wife's first time.

An erotic space adventure romance.

Our delectible neighbor has a request.

I finally take her anal virginity.

There's a first time for everything.

I promise to be gentle.

A short foray into anal.

He finally asks his wife for what he really wants.

From an anal virgin to an anal slut.

Jess learns anal pleasure.

AnnaSophia Robb asks friend to take her anal virginity.

Ethan introduces Grace to anal play.

Angelique's first anal experience.

A husband's back rub turns into something unexpected.

A first time pegging story

Young woman gets a glimpse of her new life.

Carl gets my anal cherry and Mary watches.

Asian girl wants to be taken by a white stud or does she?

19-year-old's stranger takes her final prize.

Hot blonde tricked into foursome by possessed garden gnome.

Patient introduces doctor to the delights of anal sex.

His birthday wishes come true as my ass stretches around him.

Grandpa fucks grandson.

Desperate for sex, she gets unexpected help.

Pleasure, punishment and first-time anal

My anal awakening.

Shelby gets more than she bargained for at the chiropractor.

I'm ready, please be gentle.

Teenager discovers good sex and loses her anal virginity.