Thebriefcasepimp
@windycityxxx • 16,748 subscribers
Exclusive & Classic amateur adult videos. I don’t just talk the talk. I walk the walk. AS SEEN ON TV. NO PAID ACTORS. All content is owned by me.
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1:19
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Petite Latina spinner getting fucked hard 😈 Had her legs spread wide open, pounding that tight little pussy deep. Her tits bouncing and she’s moaning every time I go all the way in. This tiny Latina takes the dick so damn good. My little Latina knows how to get wrecked. #PetiteLatina #LatinaFuckedHard #PetiteLatinaFucked #TinyLatina #LatinaSpinner #RoughSex #PetitePussy #NSFW petite latina fucked hard, petite latina rough sex, tiny latina pounded, petite latina takes big dick, petite latina destroyed, petite latina doggystyle, petite latina missionary, petite latina creampie, latina spinner fucked, tiny latina fucked hard, petite latina gets wrecked, latina pussy pounded hard
Thebriefcasepimp56,111 views • 21 hours ago
2:57
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Fucking the shit out of my petite Latina spinner from behind during makeup sex 😈 Had that tiny little spinner bent over, pounding her tight pussy hard from the back while we made up. She was taking every deep stroke like a good girl. Brought to you by The Briefcase Pimp #PetiteLatina #LatinaSpinner #MakeupSex #FuckedFromBehind #PetiteLatinaFucked #RoughSex #Spinner #NSFW petite latina fucked from behind, petite latina spinner, latina makeup sex, petite latina doggystyle, fucking petite latina hard, petite latina gets fucked hard, latina spinner from behind, petite latina pounded, tiny latina fucked rough, spinner latina fucked from behind, petite latina makeup sex, latina spinner doggystyle
Thebriefcasepimp96,188 views • 6 days ago
5:28
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My Hawaiian BBW friend needed to get pounded by a real cowboy, she works for a crooked insurance company called SOCIETY insurance, but she still likes to take a lot of dick #NSFW, #BBW, #SSBBW, #BigAss, #PhatAss, #BigTits, #HugeBoobs, #DoggyStyle, #Backshots, #Creampie, #RoughSex, #HawaiianBBW, #CurvyHawaiian, #ThickAndCurvy, #Pounded, #BigBooty, #BustyBBW, #DoggystyleFuck, #NSFWTwitter
Windycityxxx388,215 views • 1 month ago
1:27
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College athlete shows up to the house party looking all innocent… by 2am she’s bent over my bed getting her tight little pussy absolutely destroyed from behind. Had her moaning so loud the neighbors probably heard. Flipped her over, pinned those legs back and wrecked her in missionary until she was shaking and squirting all over the sheets. Ended it by slapping my cock across her pretty little face while she giggled like a total slut. Athletic college girls always take the hardest poundings 🔥 #NSFW #RoughSex #DoggyStyle #Creampie #CollegeSlut #PoundedHard #SluttyGirls #RoughFuck college slut, athletic coed, rough sex, doggystyle pounding, creampie, missionary, college party slut, tight pussy, loud moaning, face slapping, amateur rough sex, young athletic girl, slutty college girls, hardcore fucking, 2026
Thebriefcasepimp59,169 views • 10 days ago
3:10
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Had my little busted baby over one night, Petite Ebony beauty with that beautiful fat ass challenged me that night and lost. Bent her over the edge of the bed, fucking her hard from behind, teaching that tight little body exactly how to take dick while her big booty bounced hard 😈 petite ebony, fat ass ebony, big booty ebony, bent over bed, fucked from behind, ebony big ass, teaching her to take dick, petite black girl, busty ebony, ass bouncing, little busted baby, ebony beauty, doggy style ebony big dick interracial amateur homemade
Thebriefcasepimp140,158 views • 1 month ago
39:38
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Met this petite young Black Ebony princess at the Rock & Roll McDonald’s… she had that pretty face and fat ass combo that instantly had me hooked. I shot my shot right then and there — and it paid off. Took her straight back to my condo and fucked the absolute shit out of her. She took this dick like a champ — bent over, legs spread, every position I wanted. Tiny waist, phat ass, and the wettest pussy. Chicago nights hitting different 🔥 Brought to you by The Briefcase Pimp #EbonyPrincess #PetiteEbony #BlackGirlMagic #ChicagoHookUp #RockAndRollMcDonalds #EbonyPussy #PetiteAss #BigDickEnergy #Interracial #NSFW petite ebony princess fucked hard, young black girl rock and roll mcdonalds, petite ebony condo sex, ebony princess takes big dick, chicago ebony hookup, petite black girl bent over, young ebony fucked at condo, tight ebony pussy pounded, briefcase pimp ebony, shot my shot
Thebriefcasepimp35,825 views • 16 days ago
6:26
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My last busted baby is playing house down in Atlanta .She got knocked up by some dude and had his kid. It’s cool. I always got love for her. Wishing them nothing but love. Now I’m breaking in the new one — 23 year old petite Black beauty with a perfect face, a fat juicy ass that won’t quit, and a mouth that stays hungry. This tight little thing is about to get properly trained: throat fucked till she gags, that pretty ass clapped daily, and turned into my personal fuck toy project. She already knows her place — on her knees, back arched, taking as much as daddy can give her. Fresh young pussy + eager slut energy = the perfect replacement. Who wants to watch the training sessions? 😈🍆💦 #PetiteBlack #BlackGirlMagic #PAWGWaitNo #PetiteAss #EbonySlut #YoungBlack #BussDown #BlackTeens #ThroatGoat #FatAssEbony #PetiteEbony #BBCTraining #BlackAndPetite #NewSlut #HotwifeReplacement #BreedingSlut #NSFW
Thebriefcasepimp77,871 views • 1 month ago
2:25
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Fucking this petite Black dancer hard from behind and she was screaming her head off 😈 Had her bent over taking every inch deep while she screamed and moaned like crazy. That tight little pussy was getting destroyed from the back. I wonder what my neighbors were thinking hearing all that noise… No pussies were hurt in the making of this video 🔥 Brought to you by The Briefcase Pimp #PetiteBlackGirl #FuckedFromBehind #ScreamingInPleasure #DeepStroke #PetitePussy #RoughSex #NSFW petite black dancer fucked from behind, petite black girl screaming, deep stroke from behind, petite black girl moans loud, black dancer doggystyle, petite pussy pounded from behind, screaming during sex, tight petite pussy fucked hard, petite black girl takes deep dick
Thebriefcasepimp29,580 views • 14 days ago
6:50
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Friends with benefits hit different when your best friend is a young blonde PAWG with a fat ass like this 😈💦 We said “just friends” at first but that lasted about as long as you reading this, every time she came over my first order of business was to make her cum with my tounge Best friend privileges: cum on her face or up her ass whenever I want and she still acts normal the next day 😂 Who else got a PAWG bestie they’re destroying on the low? friends with benefits, fwb sex, blonde pawg, young blonde fat ass, pawg best friend, mixed dick, interracial fwb, fat ass white girl, blonde pawg doggy, thick ass clapping, best friend creampie, pawg destroyed, young pawg fucked, homemade fwb, secret slut bestie, blonde pawg interracial, big booty blonde, pawg getting pounded, fat white ass, best friend hookup
Thebriefcasepimp67,490 views • 1 month ago
1:48
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Fucking the holy hell out of Fiona from behind 😈 Brought to you by The Briefcase Pimp. Had Fiona face down ass up screaming in pleasure while I fucked her senseless from behind. That pussy was creaming and gripping so tight she couldn’t even talk — just loud moans and screams every time I slammed deep. She was taking every inch like a good girl. Drop a 🔥 if you love watching her get destroyed #FionaFucked #FuckedFromBehind #ScreamingInPleasure #DoggyStyle #Creampie #BigAss #NSFW fiona fucked from behind, fiona screaming in pleasure, fiona doggystyle, fucking fiona hard, fiona gets destroyed, fiona creaming, fiona takes big dick from behind, fiona moaning loud, fiona fucked senseless, fiona ass up face down
Thebriefcasepimp25,323 views • 15 days ago
5:25
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Met this tall biracial stewardess on the flight home from Vegas… instead of letting her book a hotel I told her “come crash at my spot” 😈💦 Flipped her over and destroyed that big juicy ass. Pounded her tight hole so hard she’s still walking funny. That fat biracial booty was bouncing and clapping while I went balls deep. Stewardesses really do make the best layovers… Who else turning flight crew into personal fuck toys? ✈️🍑 tall biracial stewardess, flight attendant hookup, biracial pawg, big juicy ass, vegas flight, flight crew slut, interracial stewardess, fucked senseless, ass fucked sore, big ass creampie, tall thick girl, biracial booty, hotel alternative sex, 2 night fuck session, anal destruction, thick ass clapping, flight attendant fucked, layover sex, homemade flight attendant, big booty stewardess, pawg ass pounded
Thebriefcasepimp61,759 views • 1 month ago
42:18
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One of my original classics from back in the day and one of my personal favorites. The goal was to give her the best deflowering experience that she would never forget and we had a lot of fun making a series of videos with her before she moved back to China. Young Chinese exchange student loses her virginity to a well hung American cowboy with a massive dick in this classic vintage homemade video. Tight Asian virgin gets stretched and ruined – she will never be the same after taking that huge cowboy cock. Retro amateur deflowering sex tape. #ChineseExchangeStudent #AsianVirgin #VirginDeflowering #BigDickCowboy #WellHungCowboy #SheWillNeverBeTheSame #RuinedByBigDick #PussyRuinedForever #NeverTheSameAfter #VintageHomemade #ClassicAmateurPorn #RetroSexTape #InterracialVirgin #ExchangeStudentFucked #CowboyTakesVirgin
Thebriefcasepimp63,620 views • 1 month ago
2:51
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My pocket-sized 4'9" Latina friend with the biggest, fattest, juiciest booty walked in and I couldn't believe how tiny she was. Got her face-down ass-up on my bed — her little body looked like a doll under me — and I fucked that massive ass so hard the bed was shaking. Her fat booty was rippling and clapping with every deep thrust while her petite frame took the pounding. She was moaning "papi" in Spanish, gripping the sheets, legs trembling as I destroyed her tight pussy from behind. By the end her 4'9" body was spent, that huge ass red and marked up, and she could barely stand. Tiny Latinas with dumptruck booties love to get wrecked 🔥🍑💦 #NSFW #FaceDownAssUp #4ft9 #BigBootyLatina #Petite #RoughSex
Thebriefcasepimp55,499 views • 1 month ago
2:58
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Fucked the shit out of this petite Ebony stripper 😈 Tiny body, tight pussy, and she took every inch like a good little whore. #PetiteEbony #EbonyStripper #PetiteBlackGirl #EbonyPussy #StripperFucked #NSFW petite ebony stripper fucked, petite black girl sex, ebony stripper pussy, tiny ebony fucked hard, petite ebony hardcore, black stripper takes dick
Thebriefcasepimp24,307 views • 21 days ago
0:37
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Why my best friend is better than yours 😈 Brought to you by The Briefcase Pimp. My best friend sucks my dick, lets me fuck her ass anytime I want, and takes this dick like a champ. Her only requests? Don’t spank her too hard, don’t shove it too far down her throat, and don’t stretch her out too much. Other than that… she’s down for whatever. That’s why she’s the best. Drop a 🔥 if your best friend ain’t like this #BestFriendGoals #BestFriendWithBenefits #DickSucker #AssForDays #NSFW best friend sucks my dick, best friend lets me fuck her ass, best friend with benefits, best friend takes it in the ass, best friend deepthroat, best friend anal, why my best friend is better, best friend sexual, best friend creampie, best friend throat goat
Thebriefcasepimp18,446 views • 16 days ago
3:45
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She Lost The Bet, Now She Has To Take As Much Dick As She Can Handle 😈 Brought to you by The Briefcase Pimp. My little Latina spinner lost a bet… so I fucked the absolute shit out of her. I destroyed that tight little pussy, pounding her tiny body senseless until she was creaming and shaking. She could barely handle all this dick. Drop a 🔥 if you love watching petite Latinas get wrecked #SheLostTheBet #LatinaSpinner #PetiteLatina #LostTheBet #LatinaFucked #SmallGirlBigDick #NSFW she lost the bet, latina spinner fucked, petite latina destroyed, latina takes big dick, little latina fucked hard, petite latina creampie, tiny latina wrecked, latina spinner destroyed, petite latina hardcore
Thebriefcasepimp21,188 views • 19 days ago
1:27
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Another favorite classic clip. An athletic college co-ed showed up to my house party looking innocent AF. By 2am she was bent over my bed getting her tight little pussy absolutely pounded from behind .She was moaning so loud the neighbors probably heard. Flipped her over, pinned those legs back and destroyed missionary style until she came so hard she was shaking. Finished by cock-slapping her goofy little face while she giggled like a slut. Young athletic women are the ones that always take it the hardest 🔥 #NSFW #Creampie #DoggyStyle #RoughSex #CollegeSlut #PoundedHard #RoughFuck #SorePussy #SluttyCollegeGirls
Windycityxxx44,228 views • 1 month ago
1:26
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Fucking my dark Ebony sexy hairdresser from behind 😈 Her ass is absolutely perfect — round, fat, and bouncing while I pounded her deep. This beautiful dark-skinned hairdresser took every inch like a pro. Brought to you by The Briefcase Pimp #EbonyHairdresser #DarkSkinEbony #PerfectAss #EbonyAss #FuckedFromBehind #BigEbonyAss #NSFW dark ebony hairdresser fucked, ebony hairdresser from behind, perfect ebony ass fucked, dark skin ebony big ass, ebony hairdresser doggystyle, beautiful ebony ass pounded, dark ebony perfect ass, ebony hairdresser sex, dark ebony girl fucked hard, ebony ass bouncing
Thebriefcasepimp12,734 views • 11 days ago
0:58
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Brought to you by The Briefcase Pimp. The real OG of this game 😈 This video was shot back in 1998 — me fucking my sexy Egyptian classmate. She had giant tits and such a beautiful ass. While most dudes were still trying to figure out how to talk to girls, I was already deep in the game. Drop a 🔥 if you respect the OGs #TheBriefcasePimp #RealOG #EgyptianGirl #BigTits #BeautifulAss #OGPimp #nsfwtwtًًً #1998 1998 egyptian classmate, egyptian girl big tits, egyptian beautiful ass, briefcase pimp 1998, egyptian classmate fucked, giant tits egyptian, beautiful egyptian ass, 1998 sex video, og pimp 1998, egyptian girl fucked 1998
Thebriefcasepimp16,078 views • 15 days ago
1:01
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Brought to you by The Briefcase Pimp. Tiffany swore she’d never take it up the ass when we first met… now look at her 😈 Watch me fuck this PAWG in the ass hard from behind. She went from “never” to taking every inch like a pro. Drop a 🔥 if you love watching girls get turned out #TiffanyAssFucked #PAWGAnal #AssFuckedHard #FirstTimeAnal #PAWGAss #AnalTraining #NSFW tiffany takes it up the ass, pawg anal from behind, tiffany ass fucked hard, pawg gets ass fucked, girl who said no to anal, pawg ass training, tiffany anal creampie, pawg anal destroyed, first time taking it in the ass, pawg gets turned out
Thebriefcasepimp16,155 views • 15 days ago