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Browse the featured first anal photos and videos by real people like you. Only the best sex uploads make it here, selected exclusively for your viewing pleaure.

We are trying anal for the first time

we are trying anal for the first time

Her first anal sex

her first anal sex

Another pic getting that tight hole ready for her first anal

another pic getting that tight hole ready for her first anal

First anal plug

first anal plug

first anal night

first anal night

Some footage of our first anal session. Damn I'm a lucky guy.#analvirginnomore :)

some footage of our first anal session. damn i'm a lucky guy.#analvirginnomore ...

Silver Foxes first anal creampie.

silver foxes first anal creampie.

Her first anal n I couldn't help not cumming in her ass

her first anal n i couldn't help not cumming in her ass

Ahhh...first try at anal vid...too dark and big balls in the way...then batterys died duh...oh well I hope someone likes.

ahhh...first try at anal vid...too dark and big balls in the way...then ...

Stranger cock in my ass! First anal with lover... fuck behind!

stranger cock in my ass! first anal with lover... fuck behind!

First she has a bit of anal play, then stuffs herself to orgasm

first she has a bit of anal play, then stuffs herself to orgasm

Convinced her being 18 years old into trying her first full blown anal session with great succes

convinced her being 18 years old into trying her first full blown anal session ...

Nothing spectacular, my first successful anal :). Light and view angle are not flattering me :), but I hope it may please some of you... I love feeling Gian's cock in my ass. I will continue working on it, with butt plugs :)... should I? kiss...

nothing spectacular, my first successful anal :). light and view angle are not ...

My first time using an anal vibrator...and loving it.

my first time using an anal vibrator...and loving it.

chat play with my love. while i always wear his buttplug when we play, this was our first anal play (but won't be the last).

chat play with my love. while i always wear his buttplug when we play, this ...

Bbygrl’s being a dirty little anal whore showing me the cum still leaking out of her used asshole hours later. I love fucking her asshole first thing in the morning

bbygrl’s being a dirty little anal whore showing me the cum still leaking out ...

First time anal, screaming with orgasmic pleasure

first time anal, screaming with orgasmic pleasure

using toy to help for her first anal

using toy to help for her first anal

documenting our first anal adventure

documenting our first anal adventure

My first anal vibrator

my first anal vibrator

first anal sex picture with wife

first anal sex picture with wife

A hot, quick, sexy missionary fuck. Just to warm up for the main event (her first time anal). Man, I will never ever forget that sepcial day my cock finally enter her nice, big, juicy ass! Her pussy feels amazing too! So a little warm up is awesome :)

a hot, quick, sexy missionary fuck. just to warm up for the main event (her ...

Close up - her pussy has just been fucked whilst using anal beads for the first time - her idea! She loved it!!!!

close up - her pussy has just been fucked whilst using anal beads for the first ...

her first anal

More picture of wife's first anal sex experience. Butterfly vibrator on her clit. Egg in her pussy. Sliding in and out of her incredibly tight ass! Trying not to blow my load too soon!

more picture of wife's first anal sex experience. butterfly vibrator on her ...

My first anal experience

my first anal experience

Aleesha's first anal video in she loved it

aleesha's first anal video in she loved it

i absolutely love mature women. this was my first anal experience and it was fucking amazing,

i absolutely love mature women. this was my first anal experience and it was ...

before her first time at anal

before her first time at anal

Another photo from my first photo session outside, where we live. My ol man has a knack with a camera and for turning decent, well respected women into cum sucking anal sluts!

another photo from my first photo session outside, where we live. my ol man ...

We are training her ass for anal play. First time she was able to get the entire strand of beads in her arse. Doesn't she has the cutest pussy? Love the barbell in her clit. We both enjoy sucking on it.

we are training her ass for anal play. first time she was able to get the ...

Her first anal! She couldn't wait! It was amazing and she took it like a pro! She loved it and we did it a lot after that special day I will never ever forget! I love her ass too!

her first anal! she couldn't wait! it was amazing and she took it like a pro! ...

First attempt at an anal video. Sorry for the poor shooting and the slow mo, not sure how I did that lol

first attempt at an anal video. sorry for the poor shooting and the slow mo, ...

Girlfriend first time anal very tight asshole

girlfriend first time anal very tight asshole

Rita was just about ready to attempt her first anal experience.

rita was just about ready to attempt her first anal experience.

Wife’s girlfriend wants to try anal for first time. She is taking two fingers easily. Wife is running camera

wife’s girlfriend wants to try anal for first time. she is taking two fingers ...

my first anal toy

my first anal toy

Suck fuck anal dildo dp A2m spanking Pt3 - In part three, more sucking my cock while I fill first her pussy and then her ass with dildos, then she sits on my cock and gets another dildo in her ass. Enjoying the series?

suck fuck anal dildo dp a2m spanking pt3 - in part three, more sucking my cock ...

This is the first half of a video of just us doing anal doggy style. The next video will show her asshole while it's still pretty tight.

this is the first half of a video of just us doing anal doggy style. the next ...

first anal night, i cant beleive she took it all the first tme

first anal night, i cant beleive she took it all the first tme

gf first bbc and first anal that night at a hotel

gf first bbc and first anal that night at a hotel

thick ebony bbw from my previous vids warms up her ass to get ready for her first anal fuck with my cock

thick ebony bbw from my previous vids warms up her ass to get ready for her ...

Lingerie, fucking, anal, A2M pt 1 of 4 Part one has a dildo, some fucking and some anal, Part 2 is mostly anal and part 3 has the first A2M. 40 minutes in total, I must be getting old, I don't think I could last that long now :-(

lingerie, fucking, anal, a2m pt 1 of 4 part one has a dildo, some fucking and ...

First anal fuck and creampie

first anal fuck and creampie

First anal ever take it easy but then pound it hard and fast. Who is next?

first anal ever take it easy but then pound it hard and fast. who is next?

More picture of wife's first anal sex experience. Butterfly vibrator on her clit. Egg in her pussy. Fucking her incredibly tight ass as I blow my seed in her ass!

more picture of wife's first anal sex experience. butterfly vibrator on her ...

My neighbor friend came over and let me take closeups of me sticking my finger in her hot tight virgin butthole. I dropped a huge hot load in her virgin butt later that night. Her first anal cream pie!
Three fingers deep!!!

my neighbor friend came over and let me take closeups of me sticking my finger ...

Our first filmed anal and first hard session where she opened up for me.

our first filmed anal and first hard session where she opened up for me.

SADick took my anal virginity, It was sooo sore! Guess his dick was too thick for my first time. I think he also destroyed what was left of my virgin! LOL Rewarded me with a Pussy Creampie, see it starting to drip out.

sadick took my anal virginity, it was sooo sore! guess his dick was too thick ...

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