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All videos in category First Anal Date (58 videos) - page 2

  • The dude was getting ready for an exam when he realized he was too tired to continue. He called one of his girlfriends who was also preparing for the same exam and offered her to unite their efforts. Sure, they forgot about the exam once they were left alone and focused on studying new sex games.

  • When they only started making sex, they did not have any ideas that it would end with their first anal experiment. They enjoyed several positions and ways of satisfying their sex hunger when the dude thrust his dong into an asshole of his girlfriend instead of her pussy and then creamed her back.

  • This blonde teeny has been waiting for her first anal date for too long and when it finally happened she was ready to get fucked in the ass with no lube cuz her chocolate hole was totally ready. No candles and stuff, she was thinking about hard anal all the way while sucking and riding her boyfriend's cock and when he drove it deep into her welcoming ass she felt the first wave of orgasm run through her body. Can you believe this dirty anal slut is a teen first-timer? Absolutely amazing!

  • When a chick starts the foreplay placing her hand on your thigh and shamelessly touching your cock through the jeans you know this date has a chance to be special. Fuck reading the book when she signals she's ready for anal sex and this guy got it all right slowly working his erect cock down his girlfriend's tight chocolate hole after she gave him an absolutely fantastic blowjob. It was even better than he could hope for, the best ass he's ever fucked, but she'll never know that cuz he told her she was the first one he tried anal sex with. Naive slut!

  • This guy was patient at night licking his teen girlfriend's pussy to orgasm and fucking her gently without even a hint on backdoor sex and his patience paid off when the happy chick was the one who initiated anal play in the morning. When a beautiful girl wakes you up with a kiss and says she wants to try anal sex right now you know it's your day and the lucky dude enjoyed every moment of it fucking his honey's tight and warm butthole and having her ride his cock balls deep. A must-see!

  • If you want to fuck a chick in the ass just give her what she wants, an intimate romantic moment like reading a book together in bed, and she'll give you what you want, full access to her sweet chocolate hole. That's what this guy did and got fully rewarded when his girlfriend finally let him explore her tight anus with his tongue, fingers and cock. Going from a deepthroat blowjob to taking hard anal in just a few minutes that's what you call a perfect date and these teens got theirs captured on cam. Wow!

  • I knew this date would be special when my girlfriend kissed me and whispered I'm ready into my ear which meant she finally decided to make our anal fantasies a reality. I started with giving her rosebud a good finger massage applying lube all over her pink anus. I felt her ass squeeze my finger inside and knew she was ready for my hard cock. The very first penetration almost made me cum, but I froze for a while and continued moments later fucking my lovely gf with all the passion in the world. It was amazing!

  • I had a bet with a buddy of mine who just broke up with this shy teen chick he knew from college. She'd never let him fuck her in the butt and I told the guy I'd go anal with this kitten on a very first date. Little did he know that not only would I fuck his ex-girlfriend ass to mouth on a day we met,but she'd also let me give her a nasty anal creampie and rub the sperm into her anus like extra lube. Yeah,that's what happens when you are a sweet talker you get the best teen ass in town and load it up with your sticky white jizm.

  • This teen cutie has always been afraid to take dick in the butt cuz she thought it would be really painful, but when she finally let some lucky guy explore her tight chocolate hole with his fingers and cock she felt nothing but pure pleasure. Those new deep sensations made her cum so hard that she immediately asked for more anal sex taking cock ass to mouth and getting her pretty face showered with hot sperm. That was her very first anal date, but definitely not the last one cuz now she knows what she's been missing.

  • Oh,darling,you are so charming today. Wanna fuck in the ass? We have no idea why,but the dumbest line ever really worked for this lucky guy and his sexy girlfriend finally let him explore the welcoming smoothness of her tight chocolate hole. Taking relationships to a new level? Screw that! He just wanted to fuck the bitch in the ass cuz his buddy told him it felt even better than fucking a hot dripping wet pussy. Now he knows how it feels and he wants more just like his slutty gf.

  • Starting a date with a cup of tea in a kitchen gets this cutie relaxed and makes her wanna suck her boyfriend's cock deeper than ever before. The guy responds with some great pussy pounding and when this juicy pink slit gets enough of cock he switches to the tight chocolate hole he always wanted to fuck. A few gentle penetrations are followed by deeper ones and soon the guy is drilling his girlfriend's ass with no mercy making her moan of pleasure. The very first anal experience as it is!

  • This cute teeny told her bf she'd let him fuck her in the ass if he could make her cum two times without cumming himself. Her pussy felt so welcoming that day and the guy could hardly resist the temptation to fill it up with hot cum,but when the second orgasm ran through his girlfriend's body he knew it was time for a special anal dessert. Fucking that tight virgin ass hole was fantastic and he even made the chick cum again,this time with his cock deep in her anus delivering never before felt sensations.

  • For any teen chick first anal sex is a big deal,but this cutie just got tired of waiting for the right moment. Once she felt she was ready to explore the new sensations she just led her boyfriend to caressing and fucking her tight welcoming ass and it was the most amazing experience ever. The combination of some pain and deep rectal pleasure made her cum harder than ever before and as her butthole adjusted to cock it was nothing but pure anal joy for this sex-crazed teeny.

  • This guy had to really bring his A-game to talk his beautiful teen girlfriend into having anal sex for the first time ever. He set it up perfectly: the flowers.the candles.the candies and after the most romantic date they ever had she finally said Yes to his dirty anal proposal. That virgin ass was more than worth the wait. The lucky guy just couldn't stop fucking that desired chocolate hole cuz it felt so smooth and tight at the same time and his girlfriend's moans of painful pleasure made hi.

  • This guy always thought his pretty teen girlfriend was too shy to have anal sex.but as it turned out she was the one asking for him to go backdoor. She was just so happy after a great date she didn't even want to do it in bed – she started sucking his cock right in the kitchen and after some hard pussy drilling warmed her up enough she told the shocked guy she wanted him to fuck her in the ass. What a moment! That virgin chocolate hole felt so smooth and tight and doing it right on the kitchen.

  • This beautiful teen brunette knew from the very morning this day would be special cuz for the first time in her life she woke up with an irresistible desire to feel a hard cock in her tight chocolate hole. Her boyfriend has been begging her for anal sex for months and she was finally ready to let him explore the welcoming smoothness of her pink anus. Some hesitation.some gentle caress.a little bit of pain and more pleasure than she could even imagine.

  • Her previous boyfriends were trying to talk this sex-crazed teeny into having anal sex.but her first time happened with a total stranger she met in a social network. She just couldn't say NO to a handsome ebony stud like this and the lone thought of feeling his cock deep in her chocolate hole made her all wet and extremely horny. No wonder she ended up getting buttfucked after their very first date and loved it from start to finish. A big black cock in a tight white ass.

  • This guy welcomes his girlfriend back from a long party trip with their first ever anal sex and she is so hungry for his dick she lets him do it despite a bit of pain in the beginning. His hard pole feels so big inside of her tiny chocolate hole,but once she fully relaxes and gets used to new sensations she cums almost at once,harder than ever before. Now she wants more and he gets back to drilling her ass again before she climbs on top of him for some nasty anal riding and another mind-blowin.

  • This teeny knew her boyfriend was up to something when he got all charming,gallant and stuff at the end of the date. He's been dreaming about anal sex for months and the idea of feeling his hard cock deep in her tight ass made her extremely horny. Man,she gave the best blowjob she was capable of that day and took cock ass to mouth like a good slut swallowing a big load of cum and making her boyfriend scream of pleasure. That's how you give an inexperienced teeny her first ever anal!

  • This guy was coming back from a summer trip and when his girlfriend met him on the stairway two floors below their apartment to give him a blowjob right on the stairs he knew this day would be special. Two weeks without sex and she's ready for anything just to feel his cock inside,even let him fuck her in the ass for the very first time. She was so horny she almost didn't feel the pain and ended up enjoying a fantastic anal orgasm after getting buttfucked in every position possible.