‘anal first time’ stories

A Principal disciplines a stuck-up hot bitch cheerleader.

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

Couple experiments with first time anal sex.

Nerd dominates bitchy MILF and takes her virgin asshole.

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

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

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

A tale of love and lust in the Caribbean.

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

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

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

He takes her anal virginity.

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

Young nurse is helped over her fear of anal sex.

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

Threesome with husband and her sexy best friend.

Mark & his cousin share many firsts.

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

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

Four men have fun with Erin over a long weekend.

Youthful aunt introduces nephew to anal pleasures.

Katie's anal experience.

Young woman sleeps with best friend's father.

She teaches a few friends how to take it.

Curvy cougar loses ass virginity to young muscled swim coach.

Watched by her mother, Mario takes her virgin ass.

Tessa has an amazing surprise for Nick...

He overcomes her reluctance and takes her virgin ass.

His girlfriend's twin sister has a weird request.

The night continues.

He gives her a new experience.

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

From an anal virgin to an anal slut.

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

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

Straight teacher is turned by two ex-students.

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

Mom had a special request I was happy to fulfill.

First time sex with a cousin leads to anal exploration.

Loving siblings wake up to a dream come true.

Michelle and Tyler get much, much closer...

A mature woman knows what she wants and what she needs.

Account of a trip with my mother in law.

Drunk Samantha is way naughtier than sober Samantha.

18 year old gives up her virgin ass.

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

She felt like a dirty, dirty girl – and loved it.

A tale of longing, insecurities and sibling love.

Bi neighbour introduces her lesbian neighbour to anal sex.

Zelena has her first anal sex.

Jaded 22-year-old has his fantasy fulfilled.

Coach gives her a pleasure she won't forget.

He finally asks his wife for what he really wants.

A wife's first time.

An erotic coming of age tale of sexual awakening.

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

One couple's first anal experience.

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

Alicia loses her innocence to a much older man.

Nicole begs for reconciliation by offering her Anal cherry.

Master takes her anal virginity.

Husband takes wife's ass in preparation for three-way.

Grandpa fucks grandson.

Desperate for sex, she gets unexpected help.

chelsea's Master takes her into "virgin" territory.

Beth enjoys her first anal experience.

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

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

Patient introduces doctor to the delights of anal sex.

I finally take her anal virginity.

Teenager discovers good sex and loses her anal virginity.

Jill seduces dad with a little help from Jim.

Training for anal intercourse.

Jess learns anal pleasure.

Tommy fucks Gina's ass for the first time.

How she learned to accept a cock in her ass.

Husband finds pleasure in spanking his new wife.

My anal awakening.

Angelique's first anal experience.

A young lady asks an older man for a favour.

I promise to be gentle.

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

BBW wife Sandra lets him explore a new frontier.

He takes her ass for the very first time.

This may be Audrey's first time, but it won't be her last.

Babysitter gets caught with her hand in her pants.

My BFF and me get our anus stretched.

Seamus takes his best-friend's virginity.

Bella loses her anal virginity

Chet gets to deflower Bailey's virgin ass.

Shelby gets more than she bargained for at the chiropractor.

How Jen lost her anal virginity.

A short foray into anal.

Young couple's first time with anal sex.

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

He helps Caribbean beauty with her first anal sex.

Liz was a 18 year old virgin bride with a bright future.

Slut takes it for money.

Female athlete auctions her anal virginity online.

I want you to take me, there...