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

wife enjoying her first anal toy.....just need to fill that pussy
wife enjoying her first anal toy.....just need to fill that pussy
first anal night
first anal night
about to do anal for the first time
about to do anal for the first time
dildo first, then anal plugged at the same time, and then cock in the mouth, very fulfilling, check out the forthcoming vids !!
dildo first, then anal plugged at the same time, and then cock in the mouth, ...
Our first anal and ass to mouth
our first anal and ass to mouth
Another pic from the first time she got double anal.
another pic from the first time she got double anal.
my first video :)...me and my ex doing some anal an pussy fucking...coments please!
my first video :)...me and my ex doing some anal an pussy fucking...coments ...
First time anal winker.   Hope you liked it.  Want to put anything in there?
first time anal winker. hope you liked it. want to put anything in there?
first anal
first anal
The first of two anal compilations
the first of two anal compilations
our first Anal vid with cumshot :)
our first anal vid with cumshot :)
first anal night
first anal night
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.
Hili I've known for a while I gave her alot of her first...she never thought I could make her orgasim from anal though. But then again I am the doctor;)any other students?
hili i've known for a while i gave her alot of her first...she never thought i ...
This is her first time trying anal and I manage to get in all the way in after a few minutes
this is her first time trying anal and i manage to get in all the way in after ...
First time anal with Mrs. CC.
first time anal with mrs. cc.
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
our first attempt at anal sex, and from the looks and sound of it she loved it...
our first attempt at anal sex, and from the looks and sound of it she loved ...
Chatelus Table 2 pt 1 of 4 - Another series with her tied to a table.  The first 3 1/2 minutes of pt1 are mostly scene setting so you can skip that if you want, then it's mostly some dildos.  Pt2 has fucking, sucking, anal, A2M and DP with a dildo :-)
chatelus table 2 pt 1 of 4 - another series with her tied to a table. the ...
my first anal, yuo like it ?
my first anal, yuo like it ?
Christy tied up during her first anal session...
christy tied up during her first anal session...
Chatelus Table 1 pt 3 of 3
The last part of the first movie with her tied to a table. In part 3 there's a tiny bit of anal, she gets cramp and I cum in her mouth :-)
chatelus table 1 pt 3 of 3 the last part of the first movie with her tied to a ...
I've had a few requests for pictures of my ass! YES I do like gentle anal, all the way up to your balls :)
Which would you take first, my pussy or my ass?
i've had a few requests for pictures of my ass! yes i do like gentle anal, all ...
Eager to try her first anal, Justine wanted to take baby steps...
eager to try her first anal, justine wanted to take baby steps...
My slut girlfriend has decided to let me post a few pics of her so here is the first one. She is the best fuck I ever had.  And she loves kinky sex and hard anal. Tell me what you all think and if you want to see more.
my slut girlfriend has decided to let me post a few pics of her so here is the ...
first time doing anal!!!
first time doing anal!!!
her first anal..please leave your comments!
her first anal..please leave your comments!
morning after sex filled night. this was only a small part of one hot weekend. she sure knew how to handle a cock. and tit fucking her....OMG. Straight after this was our first anal fuck. what would you have done next????/
morning after sex filled night. this was only a small part of one hot weekend. ...
my first anal with may ex GF
my first anal with may ex gf
these are the first time we have done this on line, she dos`nt know how hott she is,I have vidieos of this sexy thing doing anal if the response is good
these are the first time we have done this on line, she dos`nt know how hott ...
omg first time i fuck anal and i like it. it was so tight damn...
omg first time i fuck anal and i like it. it was so tight damn...
First time double anal for her,oh yeah she really enjoy it.
first time double anal for her,oh yeah she really enjoy it.
This was our first time doing anal had to use alot of lotion just to get it in her tight asshole
this was our first time doing anal had to use alot of lotion just to get it in ...
I've a sore butt this morning. Always do a MILF a favour and finger her ass, or use an anal plug first :)
i've a sore butt this morning. always do a milf a favour and finger her ass, or ...
First time anal, screaming with orgasmic pleasure
first time anal, screaming with orgasmic pleasure
Her first anal fuck
her first anal fuck
Reverse anal Part 2 of 2
Just a little more ass fucking and then her pussy. Not as good as the first part, dull finish, sorry.
reverse anal part 2 of 2 just a little more ass fucking and then her pussy. ...
Her first time anal kinda anal. She did great. Very proud of her. What do y'all think?
her first time anal kinda anal. she did great. very proud of her. what do y'all ...
Guys when you fuck a helpless MILF, please insert a anal plug first. Leave it in when you finish fucking her. That way if you fuck her in the ass later it doesn't hurt! I've a sore butt this morning :(
guys when you fuck a helpless milf, please insert a anal plug first. leave it ...
Cumshot to her tight butthole and a bit of anal probing afterward (sorry no picture...yet). This was very exciting for both of us and a new first! We are excited to try new things. Any suggestions?
cumshot to her tight butthole and a bit of anal probing afterward (sorry no ...
youngozboy pushing his dick deep into my ass...our first real anal pic!
youngozboy pushing his dick deep into my ass...our first real anal pic!
Christy tied up during her first anal session...
christy tied up during her first anal session...
using toy to help for her first anal
using toy to help for her first anal
Buried balls deep in her ass. For my first time doing anal sex - was amazing!
buried balls deep in her ass. for my first time doing anal sex - was amazing!
tight butthole here for anal....looking for someone that will suck it first, if you love asian only.
tight butthole here for anal....looking for someone that will suck it first, if ...
One of our first times having anal sex. She used to do it with her ex, but she said I'm a lot bigger then he was, so that's why she's moaning so much! ;)
one of our first times having anal sex. she used to do it with her ex, but she ...
first anal fuck after long time
first anal fuck after long time
Christy tied up during her first anal session...
christy tied up during her first anal session...
Christy tied up during her first anal session...
christy tied up during her first anal session...
started out fingering my pussy and wanking cock. tried to get his cock up my ass but its so tight it took a few goes before he fitted in. fucked my cunt a bit between tries then fingered my ass with some lube. hurts at first but still love anal creampie.
started out fingering my pussy and wanking cock. tried to get his cock up my ...
I will try the anal fucking for first time tonight
i will try the anal fucking for first time tonight
Who wants to be my first ?? Anal virgin here.
who wants to be my first ?? anal virgin here.
First part of a 60 minutes orgasmic fuck fest after not seeing my girl for 2 months, its started with a eating her pussy, then a 69, then she rides me, then I flip her over and make her squirt multiple times, then DP anal,
first part of a 60 minutes orgasmic fuck fest after not seeing my girl for 2 ...
my first anal, you like it ?
my first anal, you like it ?
From the very first video we ever made.  Scene 3 - The missionary (with anal vibe as a bonus, and bonus it WAS!)
from the very first video we ever made. scene 3 - the missionary (with anal ...
First time with anal beads.  4 Left to go in!
first time with anal beads. 4 left to go in!
Chatelus Table 1 pt 2 of 3 - More of the first movie with her tied to a table, In part 2 there's anal and A2M and more anal, you need to wait for part 3 to see me cum in her mouth :-)
chatelus table 1 pt 2 of 3 - more of the first movie with her tied to a table, ...
Salve bent over the bed just prior to getting a good ass smacking. She also got her first anal that night.
salve bent over the bed just prior to getting a good ass smacking. she also got ...
Rita was just about ready to attempt her first anal experience.
rita was just about ready to attempt her first anal experience.
first time anal picture
first time anal picture
A goth girl I've been fucking for awhile now.  This was her first anal...
a goth girl i've been fucking for awhile now. this was her first anal...
This is right before that  BJ video, I had to get my punishment first, for being naughty. Spanking gets me sooo wet. see my anal tail I love it,
this is right before that bj video, i had to get my punishment first, for ...
First attempt with anal
first attempt with anal
Slipping cock inside awesome Russian pussy and ass...this was honestly her first anal plunge - and mine!!!
slipping cock inside awesome russian pussy and ass...this was honestly her ...
After her first anal sex..:)
after her first anal sex..:)
thgis was my first time anal...
first I had a toy...and later...liked it
would  love to try two cocks
thgis was my first time anal... first i had a toy...and later...liked ...
First time posting and want to see my comments.  Let me know what you want to see, I'll do anything you want to see solo including anal.
first time posting and want to see my comments. let me know what you want to ...
Hubby's cum on my then still virgin asshole a couple of years ago. I was too nervous up until just a week or two ago. We found our anal groove and I took hubby's cock for the first time. I got off too! And he pumped what seemed like an endless load in me.
hubby's cum on my then still virgin asshole a couple of years ago. i was too ...
Another pic getting that tight hole ready for her first anal
another pic getting that tight hole ready for her first anal
First time anal..........it felt so good for both of us but still scares me a little.  Any of you girls like this?  Do you let your man do it to you?  Or would you let mine!
first time anal..........it felt so good for both of us but still scares me a ...
First try anal
first try anal
First anal pic
first anal pic
this was my first ever anal sex pic
this was my first ever anal sex pic
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 ...
Our first anal sex we video'd.    Any ladies cpls wanna join???
our first anal sex we video'd. any ladies cpls wanna join???
first anal night
first anal night
Balls Deep anal. First in her pussy then listen to her cum with Cock in her ass.
balls deep anal. first in her pussy then listen to her cum with cock in her ...
incredible but her first anal sex after using dildo to prepare...great sex
incredible but her first anal sex after using dildo to prepare...great sex
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 ...
Garage Bondage Pt 1 of 4 A four part series with her tied up on the garage floor, the first part is some oral. fucking, a dildo and some anal...
garage bondage pt 1 of 4 a four part series with her tied up on the garage ...
She absolutely loved anal. She's the one who asked for it first. Such a good girl :P
she absolutely loved anal. she's the one who asked for it first. such a good ...