‘first time anal’ stories

Couple experiments with first time anal sex.

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

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

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

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

My girlfriend puts her ass on the line.

Ashley treats Brian to an unexpected night with her friends.

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

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

Naïve housewife gets screwed repeatedly.

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

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

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

Newfound friend gives her what hubby won't.

Daddy catches his daughter masturbating!

First time anal with fat girl on beach.

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

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

Mature lady introduces young man to anal sex.

Escort abuses a client with large strapon.

Lisa gives him her flower.

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

She wouldn't give it up, but he wanted it.

Two anal virgins want to do it together.

Problems and Firsts with the magic dick.

How couple got started in anal sex.

Denise convinces him dress as her twin for Halloween.

Secretary gets trained for her new (anal) position.

They enjoy their roller coster ride of a summer together.

He gives her a new experience.

Man takes on his first real cock.

A shy IT guy meets someone.

Wife asks him to do her a favor...

Neighbor teaches banker about backdoor deposits.

Jeannie and Charlene get rear-ended.

Diana gets the first part of her graduation present.

Ass fucking Shelly.

College game reluctantly leads to extravagant humiliation.

Coed submits to track coach to stay on team.

Indian Maid gets a lesson and anal.

She loses her anal virginity (on film).

Making a deal with the girlfriends Mother is rewarding.

Prom date reveals how naughty she really is...

Married cocksucker has crazy submissive night including anal.

Jimmy & friend's mom teach each other.

Lisa gets fucked next to her sleeping boyfriend.

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

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

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

First time.

Her boyfriend lets loose deep in her ass.

Slave learns to enjoy a man in her ass.

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

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

Stepdaddy introduces her to anal sex.

Two men take her by force at a bar.

Losing her virginity takes awhile - & an audience.

Melissa asks him to take her gorgeous ass.

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

Sheila catches me with her dirty panties.

An initial experience with anal play.

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

Playful wife fulfills husband's anal fantasy.

Can a bi-guy seduce his gay roommate?

She helps boss to introduce wife to first anal.

Master takes his new virgin for a ride.

Police officer loses her anal virginity.

Visiting an old friend, she makes a new one.

Katherine's first anal experience.

Victorian Master takes charge of his prim and proper wife.

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

She decides to explore anal sex and teasing.

She has a fantasy to be used. He MAKES it come true.

A woman becomes a submissive slut.

Bossy boss knows how to get what she wants.

Roommates explore anal sex with a Doctor’s cock.

College roommates of circumstance learn from each other.

Sweet Nineteen and never been reamed.

Sex therapist helps a wife explore unique pleasures.

Nicole begs for reconciliation by offering her Anal cherry.

An anal awakening.

Mike notches up two more firsts.

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

Katie is true to her word and then some.

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

College virgin finds BBW coed anally submissive.

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

Mature woman agrees to shoot scene.

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

Left by boyfriend Jodie seeks solace.

A sweet and sexy anal first.

Some secrets are just meant to be shared.

She takes Paul's cock for the first time.

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

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

A girl asks her best friend to take her anal virginity.

Changing his perspective.

She wants his money and her boyfriends.

Middle-aged good wife goes bad - with husband's blessing.

Respectable lady decides to pep up her sex life.