‘first time anal’ stories

He's too big for her tight backdoor, but just the tip...

Hot sister is too much to resist, but mom...

A poker bet puts Jackie's tight ass in the pot.

A costume party leads to first time, anonymous anal sex.

Sneaky daughter gets more than she bargained for--in her ass.

He joins his lesbian Mother and her gf in a threesome.

Prom date reveals how naughty she really is...

Problems and Firsts with the magic dick.

My girlfriend puts her ass on the line.

A shy IT guy meets someone.

She thinks they're just friends. He proves her wrong.

Relaxing naked is one thing, but with company...

A woman becomes a submissive slut.

Naïve housewife gets screwed repeatedly.

He loses a bet & his girlfriend lose her anal virginity.

Diana gets the first part of her graduation present.

Home for the summer, Laura is confronted by a childhood foe.

Secretary gets trained for her new (anal) position.

Daddy isn't too happy after work and gets really rough.

A princess is ravaged by orcs & enjoys it.

Virgin student's summer job search lands her in a porn film.

My brother's bachelor party leads to me wanting my cousin.

Jeannie and Charlene get rear-ended.

She loses her anal virginity (on film).

Couple experiments with first time anal sex.

I join my well-endowed lady in the next room.

My Step Dad fulfilled my fantasy of losing my cherry to him.

Can a bi-guy seduce his gay roommate?

Her ass wasn't for sale. Or was it?

Ashley treats Brian to an unexpected night with her friends.

You would not believe the weekend I had!

Katherine's first anal experience.

My first steps into gay anal sex and enjoying being a slut.

Married cocksucker has crazy submissive night including anal.

Sheila catches me with her dirty panties.

Man takes on his first real cock.

Evie and Dana become unwilling party sluts.

Guy finds sex, love and happiness with a wealthy widow.

Escort abuses a client with large strapon.

Rick loses his virginity to his new older lover.

First time anal with fat girl on beach.

The story of the time I lost my anal virginity to BBC.

A man moves to a new town and becomes the neighbor's sissy slave.

College roommates of circumstance learn from each other.

She wants his money and her boyfriends.

Daddy catches his daughter masturbating!

The awakening - it's not over yet for Freddy & Carolyn.

Sexy college crush turns out to be more than a lady.

Bikers take advantage of another man's woman at concert.

Sex therapist helps a wife explore unique pleasures.

Visiting an old friend, she makes a new one.

They enjoy their roller coster ride of a summer together.

Roommates explore anal sex with a Doctor’s cock.

Two teens join a super team with a big secret.

Can straight Texan jock lust for a pesky feminine activist?

Denise convinces him dress as her twin for Halloween.

Alyson's friend and her boyfriend show her the joys of anal.

Daddy finally takes my ass, but he doesn't have permission.

Changing his perspective.

Coed submits to track coach to stay on team.

Her loving sister arranged the anal meeting.

Taking cheating ex's butt cherry, he gets a surprise.

Stephen is dominated by a married couple.

A virgin is initiated as a slave at the mysterious Palace.

A woman is attacked while walking home from a night out.

A harem recruiter gets to test run the Sultans concubines.

The first real test of the twins' relationship.

Neighbor teaches banker about backdoor deposits.

Forbidden friends reunite for her first anal experience.

Mature lady introduces young man to anal sex.

How much is her body worth?

Two men take her by force at a bar.

A young woman fucks her passed out boyfriend's best friend.

Lisa gives him her flower.

Jenny's fantasy is fulfilled.

College game reluctantly leads to extravagant humiliation.

Bossy boss knows how to get what she wants.

Straight guy learns more from gay neighbor.

The week before the wedding; a sister joins them in bed.

First time.

I watched my wife cheating on me with a complete stranger.

The man of my dreams invades my bedroom and my body.

The story of my first (and only) experience with another man.

Disgruntled employees turn the tables on their boss.

Morning coffee makes everybody crazy, including the author!

A conservative housewife discovers the joy of anal sex.

A wife is held as assurance until his debt is paid.

Victorian Master takes charge of his prim and proper wife.

The church prepares a girl's anus for her boyfriend.

Young man discovers a way to seduce his mother, or is she seducing him?

Handsome landlord shows young mommy the pleasures of anal.

Son and Father make a D/s Sandwich with Mom.

Playing with my straight-laced GF's ass soon escalates.

A mature married man finds his true calling.

A story of wife sharing, first time anal, and interracial.

Sex-starved guy gives in to gay colleague's desire.

Monty finally gets Chase’s ass… and his heart.

How couple got started in anal sex.

Heartbroken guy finds a new lover. She finds his prostate.

Sometimes a wife needs a good belt.