Her First Anal Sex Pictures (Page 6)

We have 317 Anal Sex Pictures for Her First Anal Sex.
Displaying Pictures 201 - 240.
Her First Anal Sex Katie Lane
Katie was out on college campus studying on a bench. We swindled her back to our studio to study up on some cock! See how well this lovely co-ed takes it in the ass!

Her First Anal Sex Vixxxen
This Damsel was in distress; her car was broken down in the middle of nowhere. Turns out she never had her oil checked before so we took her back to our place and let her check her play with our dipsticks!

Her First Anal Sex Mia Freak
We're taking Mia on a full tour of our favorite Los Angeles attractions. And our schedule just happens to include a side trip up her butt! Watch her squirm and moan as we take in the sights only a virgin asshole can provide!

Her First Anal Sex Carly Parker
We spotted Carly walking out of the music store needing tickets for the concert tonight. We had a better idea in mind: To stick our backstage passes into her tight little ass! Watch us play her far better than we could any guitar!

Her First Anal Sex Barbie Cummings
Petite, blonde Barbie had no change for the payphone. We invited her to come back to the pad to use our phone-- while we direct dialed her pretty little asshole! Anal sex calling! Do you accept the charges?

Her First Anal Sex Mia Knight
This country chick's far from innocent, but she's never let a farm boy up her back forty. We'll change that! Cum watch us till the forbidden butt soil she's been saving all these years! Mia's a perfect candidate for our ditch diggin' crew!

Her First Anal Sex Aline
When we saw Aline, we knew she'd be perfect for our so-called "documentary." We told a little white lie and got her into bed-- then we broke out the surprise buttsex! A few thrusts later and we'd expanded her tight little poot chute to its prime diameter! She's gonna be limpin' come tomorrow!

Her First Anal Sex Gabriella Romano
Just minutes into our donut shop stakeout, the adorable Gabriella wandered into our sights. We knew what she had behind that pink frosting: a sweet hole that begged for our sprinkles! Cum get a taste of her creamy cakes as we give her the whole baker's dozen!

Her First Anal Sex Diana Prince
Won't you take our survey? We were trying to find out if hot girls like anal sex... and Diana's virgin butthole had an opinion of its own! Luckily our thick, meaty pole-sters are keen at persuading tight little sphincters to open up and share the love!

Her First Anal Sex Maoja
This broad was a long ways off from the runways of Paris. But we knew what she'd excel at: getting rammed in the pooper! Maoja had never aspired to be an anal slut, but now she's well on her way! Our career counseling works yet again!

Her First Anal Sex Holly
We cast our butt bait, leaned back with our rods and waited for a bite. And we reeled in a whopper! Holly's visiting from Europe and she's never done anal. Just wait 'til we've got her splayed and filleted! Come smell the catch of the day as we harvest the depths of her anal reef!

Her First Anal Sex Tabitha
Darling lil' Tabitha got snared by our ad for a music video shoot. She took the train in from the suburbs... but a few minutes later she was takin' our diesel locomotives right up her caboose! Toot toot! We're drivin' a spike up that tunnel!

Her First Anal Sex Allison
This chick wanted to be part of our "reality" show, but Allison didn't know it was gonna be anything like this! We got her to play along and soon she felt us knockin' down her back door for the very first time. We had a feeling she'd play along "in the end!"

Her First Anal Sex Vivian
This lassie's boyfriend got caught cheatin'. Vivian needs some counselling! Good thing board-certified Anal Therapist Joe Friday is on call! This poor girl was so broken up that it took the filling sensation of anal insertion to mend her heart!

Her First Anal Sex Rachel
Poor little Rachel's boyfriend was cheating on her. It's time for revenge! And what better way than giving up her butthole virginity to another man? That's one cherry her stupid boyfriend ain't gonna pop. We stretched it good!

Her First Anal Sex Angeline
Angeline was starstruck! She'd never met any real life porn stars before, and we didn't wanna let her down. So we gave her the full tour. She got to experience a porn star dick in her mouth, pussy and-- for the first time ever, her ass! What a lucky girl!

Her First Anal Sex Devon
It's time to kick in the brown door and paint it white! When we told Devon that she was gonna get the butt-shaft, Richard promised to take it slow. But after feeling the grip of her tight chute our assman couldn't help give her the anal pounding of her life!

Her First Anal Sex Rebecca
This chick wanted to be in our swimsuit calendar, but all we wanted was to plow her tight, virgin ass! She thought it would hurt... and she was right! We didn't come here to make promises about feelin' good or gettin' her off: we came here to plunder her ripe rectal cherry!

Her First Anal Sex Michelle
Her First Anal Sex Michelle - Hot Anal Sex Picture

Her First Anal Sex Jocelyn
Sex therapy? Jocelyn was definitely down with that suggestion. But while her pussy longed for a good hard fuck, our "MD" asked her to bend over and say "ouch"! Watch this skank's adventure into the pleasure and pain of gettin' the shaft right up the butt!

Her First Anal Sex Jayna
It was a scorching hot day in LA when we spotted Jayna gettin' some liquid refreshment at the C-store. We knew what she was really craving-- two big 'ol dicks! Our boys whipped out one for her to suck on like a icicle and the other to strech her puckered little anus out for maximum ventilation!

Her First Anal Sex Leah
This hot little piece of ass was scoutin' the car lot for a rich man to sink her claws into. We sunk our dicks into Leah's fine, tight butt instead! This little gold digger took out bait-- hook, line, sinker and ass-stretching pole! She's gonna have to look far and wide to find another pounding like this!

Her First Anal Sex Camille
Push it to the limit-- and beyond! Precious Camille was begging to get naughty on camera, and we weren't gonna let her down. But she had no idea how far we were gonna take her ass! We split that virgin starfish and blew a huge load on her throbbing, blushing ass cheeks. No pain, no gain!

Her First Anal Sex Kinzy Jo
Sexy mallrat Kinzy Jo met up with the Ding Dong duo to offer a little fashion advice, but ended up getting a tight ass makover from duo's meaty members! Watch Kinzy Jo get some much needed rectal resizing in this episode of Her First Anal Sex!!

Her First Anal Sex Bianca
Crazy from the heat, pretty little Bianca hitched a ride with two tall strangers for some brews and fun! This little slut knew what was up when her horse donged escorts dropped trow and deep dicked her tight little ass! Watch Bianca expand her "horizons" in this episode!

Her First Anal Sex Carrie
Out in the So-Cal heat our sex starved butt pirates met pretty beautician Carrie and decided an anal makover was in order! With more meat than Sam the Butcher, the dong duo skewered pretty Carrie ass and gave her more than one reason to walk funny! Donnnng!!

Her First Anal Sex Jasmine
Ah the cutthroat world of porn! Our two Boner Buccaneers plundered some FINE booty from the scurvy Interavid lads, and this bonny lass wasn't leaving without a good assfucking! Watch these pirates give pretty Jasmine's ass no quarter in this episode!!

Her First Anal Sex Sammie
Hola! K-BUTT in the morning here and we had a trip to the Bahamas for one lucky ho, but what will pretty Sammie do for em? Slobberin' on knobs was easy but when schlong hit asshole there was a whole lotta moanin and groanin! Bon Voyage ya' sore-assed slut!

Her First Anal Sex Ricki
Swing-a-ding! Here comes duo to blow more o-rings! On this fine day we found pretty Ricki (and her hot ass) alone in the So-Cal sun and invited her back for some "fun"! She may have been no stranger to fucking but watch the duo super size her pretty holes in this one!

Her First Anal Sex Candace
Liquor is quicker but the key to this slut's heart is a nice fat cock! Cutie Candace was no stranger to a good deep dicking but she's never been a backdoor baby! Will Joe succeed and give his fat cock a nice wet home in her pretty little ass? Tune in and find out!

Her First Anal Sex Nakia
Be they ever so humble, they're no girls like ho's! To break in our new bum banger, Joe snagged pretty damsel in distress Nakia for a little "distress" down below! Watch as the anal invaders give Nakia's cute little ass some hard rectal rootering in this episode!

Her First Anal Sex Lana
Fashion conscious Lana was a sexy asian with an ass ripe for fucking! A few lies later and our boy was eating poon sushi raw, and after he unleashed his 50 foot monster she got her first anal invasion! Watch this gorgeous slut get her tight hole stretched wide in this one!

Her First Anal Sex Giovanna
King donger goes mano-a-butthole with sexy italian Giovanna and he couldn't be happier! This spicy honey may have been swayed by his charm and class but his footlong made for a very sore ass! Watch this honey sample our boy's spicy meatballs and get her first rectal rooter!

Her First Anal Sex Sasha
Camera lovin' Sasha saw us and BEGGED to be in our little production! It was Sasha Gone Wild as she stripped and paid our cocks a little lip service! Then we pile drived that cute ass with our monster meat! See these rectal rooters make another Her First Anal star!

Her First Anal Sex Mia
Assman's java jones led the Duo to sexy Mia, and you don't need Juan Valdez to know that a fine ass beats a cup o' joe ANY day! Ditching the coffee, they went to work on that tasty pussy and widening her sexy tight ass! Watch this java junkie get a jones for fat cock!

Her First Anal Sex Tori
Sexy little girly-girl Tori was sugar and spice, but that ass was NICE! We got this snooty cutie for the price of trendy footwear and pocket change! Watch the fearsome twosome shoehorn their massive meat in this mallrat's pretty ass for Her First Anal Sex!!

Her First Anal Sex Tobi
Tight, toned, and ready to model our "clothing line" perky Tobi ended up on her back, ass a-quiverin' from the anal assault delivered by the DD squad! Watch Assman and Throbbin venture into uncharted territory and give this honey Her First Anal Sex!

Her First Anal Sex Sativa
Sexy Sativa was on the rebound and ready for a grudge fuck! She may not mind a hot pussy pounding, but this spicy latina wasn't cool on deliveries in her rear! Watch our lone wolf harm that hot heiney and give this cutie a sore ass to remember her first anal sex!

Her First Anal Sex Cindy
Workin out on a friday afternoon Chris snagged gym bunny Cindy and invited her back for a "special" workout! We pulled out our equipment to stuff that pretty ass and pump some iron! After doing the clean and jerk we gave this honey some cockade for her cool down!

Her First Anal Sex Vixen
Braving the cold, the duo went huntin' for warm tight spaces to invade, and stumbled upon red-haired (and red hot) cutie Vixen! As things heated up they moved from that hot ginger minge to all things dark, tight and stinky and expanded Vixen's 'horizions'!

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