Her First Anal Sex Pictures

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!

Busty beauty Nadia Styles knows she can take a big dick, but in her ass? That's a whole other story....a story she sure the fuck wants to know the climax to! We get this sexy slut all warmed up and ready to go with a cock in her mouth and another in her pussy, before lubing up her tight virgin ass for some anal devastation ...

Heidi was outside the pool hall looking for a ride. With a nice rack like hers she had no problem getting a ride from us! We lined up our cue sticks to her back pocket, but did we make the shot? Cum in and find out.

Tory Lane has been fucked six ways from Sunday, but has never...and we mean ever...had her ass breached by a boner until now! With one cock to keep her wet pussy and pouting mouth busy, we stuff another one up her tight tushy-hole, pounding at her sphincter until it splits!

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!

Melissa Lauren was just plain bored, she needed something new to come into her life and spice things up. Well Melissa, would you take something new cumming in your ass?! On cue to cure Melissa's blues, Alec and Mikey show up to stretch her virgin sphincter until this bitch's butthole snaps!

Taylor was outside the courthouse sorting out some papers we thought she might be in trouble so we went over to help her out. Turns out she practices law but tonight she is going to practice some ass fucking! Her ass is in session and this week has a verdict that you wouldn't want to miss!

Jessica couldn't stop thinking about her stalker ex following her around, so she decided that the best way to get her mind off things would be to get her ass cherry busted by thick swingin' dick! It was a tight fit at first, but after a few slow strokes, Jessica ends up going all "crazy cowgirl" with the colossal ...

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!

Mark and Alan have been staking out Beverly Hills who's been accused of impersonating a porn star for dressing sexy and fucking guys on camera. Mark and Alan aren't fooled, but when they make their move to arrest her, she insists that she IS a porn star. She's got a lot of convincing to do with these cops on the ASSault!

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 play with our dipsticks!

Aubrey may be a petite blonde with itty bitty titties, but she has a full round ass and a perky puckerhole willing and ready to take a massive meat-mallet for the first time! After getting her pussy pounded to pulp by a colossal cock, she gets her sweet sphincter stabbed by the daunting dick and loves every painful minute ...

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 our bait-- hook, line, sinker and ass-stretching pole! She's gonna have to look far and wide to find another pounding like this!

Kelly Wells is as famous for her screams of pleasure as she is her love of swallowing spunk, but one thing she isn't known for is taking a cock in the slit and another in her sour second hole...which she is more than happy to do when two thick-dicked fanboys show up at her doorstep. Talk about living the dream, these two ...

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!

Brandi isn't sure that her petite little body can handle a massive mutton mallet in each hole, but she sure is willing to give it a well-lubed try! Brandi winces in pain at her first anal sex, but screams with pleasure while the depths of her virgin asshole are tunneled deep and then filled with gobs of glandular guy gravy!

Vivian got careless, and now her ass is ours! Joe caught this skank cheatin' on her boyfriend and got it all on tape. It's the perfect way to blackmail our dicks right into her tight little bum! Grab a crowbar, we're goin' balls deep in this harlot's rear!

Missy's a hot young nympho who's never had a cock in her ass, but want's it really bad! She invites two of her friends over and lets them know what she's in the mood for with a little striptease. But they're gonna make her beg to get her wet holes filled up with their two huge cocks - On her knees!!!

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!

Otto and Alec never really thought that a classified ad for sex would work until the day they came home to find little nympho Audrey waiting (with her fingers in her cookie jar) for them to fuck her silly. She dropped to her knees and they knew she wasn't playing and neither were they... After she came it was their turn ...

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!

Taylor isn't too happy that she constantly needs to clean up after her roommates, so these two studs decide to make it up to her by scrubbing her AWESOME ANUS with their huge cocks! This anal amateur bends over and takes it like a pro, with her ass being stretched by one thick dick, and her mouth being stuffed balls-deep ...

We gave Lexi a ride from her work at the tattoo parlor. She snuck off with one of our guys for a little skin pounding. So we followed and snuck up on her with another cock and she ran with it! Cum in and watch as we stuff her ass for her first time!

Inviting ingenue Dana had waited her whole life for this audition, so when she was told to open her anal aperture up wide and take a cumbersome cock up her quick quivering ass, she was more than willing let the director shove his man meat into her strained sphincter!

We knew a girl this cute would never agree to givin' up her butt for a boyfriend... but what about us? She sure did cringe when we pulled her pants down and went trompin' where the sun don't shine! Can Michelle's tiny pink knot take the thick, veiny punishment?

The Magnificent Mina had always been the star of her own slutty show, but only recently had been fantasizing about becoming an anal acrobat. She carefully selected her two assistants from a collection of willing cocks and soon after she was in the spotlight once again, perching on one cock with her spread sphincter and ...

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!

Talon is headed to his brothers pool house to train for his swimming competition. Riley Evans is house sitting and was supposed to clean and turn on the heat for the pool. When Talon finds out the water is cold as Ice, he decides to swim in something else to make up the workout he missed. What a way to make a splash.

Jack overheard his girlfriend and her friend Amy talking. Amy had brought up that her fantasy is two men at once and she has never tried anal. So Jack's girlfriend is out and Amy's sleeping on the couch - time to wake up to a fantasy fulfilled!

Anal virgin Amber was having a bad day, so she decided to relief some stress and satisfy herself by stuffing her sweet pussy with a beer bottle. Before she could get into it though, these two studs show up to teach her what real penetration is like, with some tag-team dicking in her pussy and ass!

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!

After listening to Mark complain about his aching back, Jerry calls his favorite massage therapist for an emergency house call. She strips off all of her clothes and Mark's pain begins to drift south... Into his throbbing cock. After she massages it with her mouth they take turns seeing how good of a massage her ass gives ...

We spotted Mia outside the clinic after a colon cleansing. Little did she know she was preparing for an ass pounding of a lifetime! See us squ`eeze into the cleanest, tight virgin asshole ever and give her an even better cleansing of our own!

We were in the mood for Asian, but instead of General Tso, we got some Tia Ling! This eastern hottie had a tight body and a tight ass to go along with it. We knew we needed to break in her sample-sized asshole so we spread open her tight puckery anus and plunged a thick meat rod in it! It didn't take long for this anal ...

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!

Desiree may have fought for her country but she was more than willing to surrender her ass for some first time hardcore ass fucking anal sex. Our two good old boys show this girl their gratitude by giving this sexy vet a place to stay and a couple of hard dicks for her puckery hole!

We spotted Mia outside the clinic after a colon cleansing. Little did she know she was preparing for an ass pounding of a lifetime! See us squeeze into the cleanest, tight virgin asshole ever and give her an even better cleansing of our own!

It's Audrey's job to negotiate, it's just that she usually negotiates price rather than, um shall we say - services! When we came to the open house she thought she might make a sale, but all we had in mind was parking our hot rods in her backyard. Of course we didn't buy the house, but we did foreclose on her ass! Tune ...

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 stretch her puckered little anus out for maximum ventilation!

We couldn't have asked to meet Staci under better circumstances... She was browsing the anal porn section of our favorite video store! The horny slut loved the idea of coming back with us for a real Ass Fuck!