‘first time anal’ stories

Eloise.

Gay Teammate offers Anal to First Timer.

A wife gives her arse to her husband on their wedding night.

I finally have gay sex with my college friend.

Alice is caught trying to escape her imposed chastity.

Amelie's summer rendevouz comes to a close.

A macho hetero boy on holiday get used.

Jake and Ethan's movie scene rehearsal goes off-script.

I wanted it, and I got it.

Joanie gets relief and goes out to celebrate.

She is forced to violate her own untried hole in retribution.

RESCUING SWEET OLIVIA 02.

Anna faces her own sexuality and her risks.

Gina gives Joey a makeover, turning him into Julia.

Gary gets a big surprise morning after pool party with Al.

Mandy turns me into my sister.

Realtor& friend, take CD’s virginity.

Joe's bed has a surprise guest.

A 90's, transsexual, sci-fi, mystery romcom.

A 90's transexual, sci-fi, mystery romcom.

Johnny gets caught on nanny cam in a french maid dress again.

A massage turns into something more.

My Ex visits and sexual sparks fly.

Matt & Odessa go dark on Halloween with first time anal...

A sick man finds he has really good insurance

He fulfills her deepest fantasy of being tied down and taken.

Rebecca has her second round of group sex.

A whole new experience with the nameless stranger.

Ariel wants to try something new.

Straight guy ends up liking having his ass eaten.

At our next meeting Lisa and Scott surprise me.

Aoi gets a job and her dynamic with her friends evolves.

Newlyweds discover anal sex together.

The fun continues.

Caitlin is keen to have a threesome.

Happy birthday, Dominic.

Amy gets mad at me but sets me up with my first man, Mike.

Evie and Dana become unwilling party sluts.

Boyfriend comes home from university, takes her anal cherry.

Ros meets her husband's friends and makes them feel at home.

Looking after her customer’s needs.

A conservative housewife discovers the joy of anal sex.

You're prey. The sooner you accept it, the less it will hurt.

She surrenders her ass, her last unused hole.

10 Yrs Later - My Ultimate Threesome Comes True.

What had he done?

An 18yo gets wrecked by 29yo and 45yo.

Troy and Colin ae inseparable. What about Toby?

Role playing comes with a cost. We need to talk.

Tending to an Expanding Flock.

Logan takes Sebastian's 18 yo cherry ass, Jeremy joins in.

Consoling my bf after a tough loss.

All's fair in love, war, failing marriages and business.

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

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

Inexperienced girl seeks gay guy for anal initiation.

Christmas Day has arrived for the Martins and their guests.

Harry and Sam have a night out on the town.

Can straight Texan jock lust for a pesky feminine activist?

A widowers love of crossdressing leads him to find comfort.

Jake gets a mysterious call from a stranger.

As Annie makes up her mind, I remember becoming Master.

Sensual Sunday stroll down memory lane.

Becoming more comfortable with Herman.

MsV and Anna take Harry, as Harriet, shopping.

Our narrator goes to Ali's for dinner and goes further.

Molly and Sara get some new toys.

The best three day fuck fest of my life.

Doctor stretches the new novice's anus for advanced anal.

Stephen is dominated by a married couple.

You would not believe the weekend I had!

A Hollywood producer's greatest Christmas memory.

Nate and Marianne's mundane sex-life gets upended.

My girlfriend puts her ass on the line.

A young man and his older neighbour.

Tony takes my anal virginity.

Online posts about first fuck, first oral and first anal.

Lisa is fucked in the arse at a hardcore casting.

After years of waiting, Klaus finally gets his red lips.

Romantic get away turns into a loving wife opening up.

Julia and her Boyfriend go to their first swing.

Brad introduces Michael to some of his jock buddies.

Continuation from Chapter 2, buttsex (finally) ensues.

Another meeting with my hookup, now in school locker room.

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

Brandi plays with toys and decides she wants the real thing.

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

Humiliating first time anal experience.

Continuing my sexual education with HS teacher's roommate.

Jeff and Shelia are joined by her best friend.

With Maggie's turn complete, Taisha puts Sam in his place.

Unlocking an older woman's anal desires.

I give all of myself to him for the first time.

An unusual adventure when I was a young man.

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

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

She wants his money and her boyfriends.

Invited to my airport hotel room.

A girl accepts a strange offer online and finds her calling.

New coach gets gangraped by his seniors for their graduation.