Part 1 Wedgieboy Gets RejectedCarmen Valentina is in town for her bestie's wedding but the weekend gets off to a rough start when the bride's l*ttle step-bro gets too big for his britches. Sam thinks that Carmen will be into him now that he has made a l*ttle money, even though she used to give him wedgies all the time. Sam quickly goes from h*tting on Carmen to begging her not to dress him in his old tighty-whities for more wedgies.

Part 2 Carmen Makes Her L*ttle Vacation S*ssy Eat PussyCarmen Valentina is part of a group of girls that have always hung out with Sam's step-sis and they have always bullied Sam. The group was so close that they still get invited to the fam vacations and on their latest trip, Carmen gets the hilarious idea to make Sam go sightseeing in yoga pants and a sports bra.. She wants to show off to the other girls that l*ttle s*ssy Sammy would still obey any request from her, no matter how embarrassing.

Part 3 S*ssy Bikini Bottoms and Face Sitting HandjobsOn the last day of vacation Carmen yanks down Sam's swim trunks the moment she sees them and quickly explains that he has to wear bikini bottoms to the pool. She lets him cover her *ss in kisses while begging to wear shorts but still decides he has to wear the skimpy tie-side swimsuit. Carmen sits on Sam's face to slip him into the bikini when the l*ttle loser pops a tiny boner. Carmen agrees to help him get rid of his erection before taking him to the pool but she makes sure it is the most embarrassing *rgasm his "itty bitty wee-wee" has ever experienced.

She t*rments him with painful wedgies while rubbing his face in all the most embarrassing memories the two of them share. Carmen wants to make sure he does not forget that he is still just a silly l*ttle wedgie boy so she strips Sam out of his CK boxers and puts him in some tighty-whities from his old bedroom. Sam went from h*tting on Carmen to begging her not to make him take more wedgies in schoolboy underpants before she even unpacked from her flight.

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