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 little step-bro gets too big for his britches. Sam thinks that Carmen will be into him now that he has made a little money, even though she used to give him wedgies all the time. Sam quickly goes from hitting on Carmen to begging her not to dress him in his old tighty-whities for more wedgies.

Part 2 Carmen Makes Her Little Vacation Sissy Eat PussyCarmen Valentina is part of a group of girls that have always hung out with Sam's step-sis and t...

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 little step-bro gets too big for his britches. Sam thinks that Carmen will be into him now that he has made a little money, even though she used to give him wedgies all the time. Sam quickly goes from hitting on Carmen to begging her not to dress him in his old tighty-whities for more wedgies.

Part 2 Carmen Makes Her Little Vacation Sissy 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 little sissy Sammy would still obey any request from her, no matter how embarrassing.

Part 3 Sissy 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 ass 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 little 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 orgasm his "itty bitty wee-wee" has ever experienced.