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Mae is flexible, but not in the standard way. She can't exactly do a split, but her tiny pussy and asshole can stretch to fit huge cocks. This was actually her first time doing anal, and she handled it like a champ! "I didn't even use a toy in my butt beforehand. I just wanted that cock in my ass so bad that I didn't have any trouble taking it in. That's the key to anal, I think. You have to be really horny and really relaxed."

See More of Mae Olsen at 18EIGHTEEN.COM!

Lives: Denver, Colorado; Occupation: Earth sciences student; Age: 20; Born: May 1; Ht: 5'10"; Wt: 140 pounds; Bras: 36B; Panties: Thongs; Anal: Love it! BJs: Swallow; Diddle: Sometimes.



"Some girls go skydiving for thrills; I wanted to fuck a stud," said Nicole. "I forgot about the age difference as soon as I saw Jack's big dick and started suckin' it. I've heard girls say that having an older lover who knows what he's doing is the best. I totally agree now! I had a huge orgasm while we were screwing and another while Jack was screwing me in my ass. That had never happened before: I hope other guys will do my ass as good as jack did so I can cum that way again in the future. That was probably the best sex I'll ever have... but I hope not." Check out the photos, too.

See More of Nicole Ryder at NAUGHTYMAG.COM!

The video could have been titled "Turnabout Is Fair Play." It's about a 52-year-old woman--we'll call her Trinity--who discovers that her husband has been cheating on her...and right there in his office. "It's so humiliating," Trinity says to Tony, looking as if she's about to tear the jezabelle's panties to shreds. Poor Trinity. Stupid husband. What a big dope, cheating on a piece of ass like Trinity. And probably with a young secretary who's nothing more than a head-sucker. Tony tries to console her, tries to show some real feeling for her situation, and wouldn't you know it, she feels his hard cock through his pants. "I think you just gave me an idea how I can fix this," Trinity says. "The bastard cheated on me. I'm going to cheat on him."

Great idea! She hands Tony her address and says, "Bring a friend."

The friend is Asante, and Trinity gets back at her husband by taking their cocks in her mouth, pussy and asshole. Yes, her asshole. Because there's revenge and then there's Revenge, and everybody knows that Revenge is a dish best served with anal.

See More of Trinity Powers at 50PLUSMILFS.COM!

Holly, what does a guy have to do for you to consider having anal sex with him?



"First he has to fuck my pussy right. Because if he can't fuck my pussy right, then he probably isn't going to be able to fuck my ass right. Inexperienced guys need not apply here. I also have to have really good chemistry with him, too. 'Cause what girl wants to do anal with some guy who doesn't make her horny as hell in the first place? So if those things are there, then all I need is a bottle of lube and I'm ready to go! When I find a guy who I vibe with, it's awesome. When that happens I can almost feel my ass tingle 'cause I know we're gonna do anal."




We don't see too many girls your age who do anal. You're a rarity! Please tell us what it was like to get your booty cherry popped.



"At first I was really nervous, even though I had been wanting to try it for a while. The guy and I had sex for a while first, then I told him I was ready. He spent some time licking and fingering my ass to get me ready, and I remember thinking that it felt really good. That helped me to relax. He put some lube on my ass and started to put it in really slow. I remember when his cock first popped in my ass. It wasn't like anything I'd ever felt before. I felt like there were fireworks going off back there. He went slow, and it was just right. Now I'm hooked!"

See More of Holly Love at 18EIGHTEEN.COM!

Lives: Orlando, Florida; Occupation: Theme park worker; Age: 22; Born: July 4; Ht: 5'3"; Wt: 135 pounds; Bras: 34DD; Panties: Lace; Anal: Sometimes; BJs: Swallow a bit then spit; Diddle: 2-3 times a month.



"For the last year or so, I've been screwing a FWB who I've known since we were six," said Araya. "We've said for a while it was time for us to move on and, in fact, I set him up with the girl he's now dating. We were just getting into butt sex--something new for both of us. I wanted to screw a stud to experience having sex with a well-hung guy who knows what it takes to fully pleasure a girl."

See More of Araya Sun at NAUGHTYMAG.COM!

Lives: Orlando, Florida; Occupation: Theme park worker; Age: 22; Born: July 4; Ht: 5'3"; Wt: 135 pounds; Bras: 34DD; Panties: Lace; Anal: Sometimes; BJs: Swallow a bit then spit; Diddle: 2-3 times a month.



"For the last year or so, I've been screwing a FWB who I've known since we were six," said Araya. "We've said for a while it was time for us to move on and, in fact, I set him up with the girl he's now dating. We were just getting into butt sex--something new for both of us. I wanted to screw a stud to experience having sex with a well-hung guy who knows what it takes to fully pleasure a girl."

See More of Araya Sun at NAUGHTYMAG.COM!

"Are you ready to fuck this sexy MILF," 52-year-old divorcee Cheryl Conner asks big-dicked Johnny at the start of this scene. She's wearing practically nothing. Her tits are already out of her bra, if that's what you want to call it, and her G-string is slicing up her butt cheeks, and soon, she's gonna have a cock slicing in and out of her horny asshole. But first, she has to get his cock in her mouth. Then she has to get her stockinged legs up in the air so he can fuck her tight, slut, MILF pussy. And only then does she get fucked in the ass, which is a pretty impressive thing considering how little Cheryl is. And she takes a hard, anal pounding, too! Remember when we told you that Cheryl was nervous when she walked into our studio? Well, obviously, a cock in her ass calmed her nerves. Cheryl, by the way, is not a porn star. She's a saleswoman from Las Vegas (born in Philadelphia, Pennsylvania), and she said, "At my age, I have done it all. I've been around the block a few times. I've had twosomes, threesomes, foursomes. But I've never had anal sex on-camera."
There's always a first time. Well, almost always. Most 50somethings do not get their asses fucked on video by guys less than half their age. But Cheryl is not most women.

See More of Cheryl Conner at 50PLUSMILFS.COM!

52 year-old brunette divorcee Cheryl Conner came all the way from Las Vegas to cum and learn the ways of the 50Plus MILF. She was nervous. "I've never done this before, but I'm really looking forward to it," Cheryl said. She did look a little anxious. "I've never had sex on-camera, but I'm looking forward to getting fucked hard by one of your hung studs." And that's exactly what this attractive lady did her first time in "Nervous Newcomer Cheryl Fucks The Nerves Right Out Of Herself!" By the end of that coupling that included Cheryl's ass getting finger-fucked, Cheryl was lapping up a cum-spewing cock like she'd been in a nunnery for five years. But Cheryl was not quite finished. Now that she's busted her on-camera cherry, as it's delicately called, it was time to have Cheryl take an even bigger and thicker cock in all three holes. There's little time for formalities and romantic gestures as Cheryl is stripped down to her black stockings and fed her first course. She's practically inhaling his balls as he fucks her face on the bed. This horny divorcee is quite the deep-throater and an apt pupil. This time, Cheryl's new fuck partner adds her sexy butthole to the menu after he's filled and crammed her pussy-hole. She gets that cock in deep and to the hilt! Her pussy clearly likes young fuckers. When she is finally ready for the testicle-sauce after being pounded, drilled and hosed, JC blasts a full nut on her face. Now that Cheryl's been fucked and fucked hard by two studs not much more than half her age, will she be able to settle back into her earlier sex life? Or will she go on the MILF rampage and become a 50+ fuck toy in search of more, and bigger, man-meat? Ms. Conner has a sexy, slim, trim body so she is sure to get plenty of indecent proposals back in Sin City. Especially when the local horndogs see this.

See More of Cheryl Conner at 50PLUSMILFS.COM!

Holly Halston is known for two things: Big tits and great fucking. In fact, she is one of the reigning queens of big-tit fuckery because of her commitment to getting the job done right. She knows all the ins and outs of how to rock a cock with her huge jugs. So it's only natural that this diva be the one to show you how to pleasure her tits while slamming your rod between them. That's right, Holly wants to teach you a fucking lesson...as in a lesson on how she likes to be fucked, of course. Do you have an apple of the teacher? That's great because she wants to give you her cantaloupes. And with a little HARD work and some extra one-on-one time with Holly, you could just go to the head of the class...or ram your head in her ass. Either way, it's a win-win situation. So sit back and soak it all in, buddy, because she is about to teach you how to soak her tits in nut-juice.

See More of Holly Halston at BIGBOOBSPOV.COM!

Even if a teen girl isn't a cherry, her ass usually is. But not Paola's. She takes it in the butt, but that's not the only reason she's special. She likes to have something plugging her ass and her pussy at the same time. "Whenever I know I'm going to have sex, I bring a dildo with me so the guy can stick it in my ass while he fucks my pussy. It helps my little asshole get ready for his cock, too. I haven't had two guys inside me yet, though. But it's my ultimate fantasy."

See More of Paola Vega at 18EIGHTEEN.COM!

"I love anal. It's my favorite thing," Paola says. Looks like this teen isn't innocent and she doesn't waste time proving it, either. She spreads her sweet butt cheeks right away. She fingers her ass for a bit before letting this guy take over. Then he buries his finger and tongue into her cornhole, preparing it for his huge cock. These two horny toads take a break from the ass-play so Paola can suck his cock and get her pussy fucked. "Ay que rico, papi!" Paola says in Spanish as he slams her doggie-style. Her fuck buddy then further preps her bunghole by sticking a dildo in her ass while continuing to fuck her. Now it's time. Paola's tight starfish gets filled to the hilt with man-meat and she loves every inch of it.

See More of Paola Vega at 18EIGHTEEN.COM!

Lives: Great Falls, Montana; Occupation: Student; Age: 20; Born: September 23; Ht: 5'2"; Wt: 120 pounds; Bras: 34B; Panties: Thongs; Anal: Definitely; BJs: Swallow; Diddle: Most every week.



Holly was going to pose solo for her long-time boyfriend who's a naughtymag.com fan, but he dumped her for an 18-year-old who, he claimed, is better in bed than Holly. So she had a rethink and decided that she still wanted to be on the website, but she wanted to screw a SCORE Group stud. "I haven't been fucked by even a decent-sized dick before (ouch!) so I want to treat myself to sex with a guy who knows what he's doing (ouch, again!) and is really well hung," she said.

See More of Holly Love at NAUGHTYMAG.COM!

Lives: Great Falls, Montana; Occupation: Student; Age: 20; Born: September 23; Ht: 5'2"; Wt: 120 pounds; Bras: 34B; Panties: Thongs; Anal: Definitely; BJs: Swallow; Diddle: Most every week.



Holly was going to pose solo for her long-time boyfriend who's a naughtymag.com fan, but he dumped her for an 18-year-old who, he claimed, is better in bed than Holly. So she had a rethink and decided that she still wanted to be on the website, but she wanted to screw a SCORE Group stud. "I haven't been fucked by even a decent-sized dick before (ouch!) so I want to treat myself to sex with a guy who knows what he's doing (ouch, again!) and is really well hung," she said. Check out the video, too.

See More of Holly Love at NAUGHTYMAG.COM!