Carmen 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 got the hilarious idea to make Sam go sightseeing in skimpy, girly workout gear. After some initial disagreement he agreed to wear the outfit that day and also panties under his clothes for the rest of the trip. When Sam gets pantsed by Carmen in his swimming trunks and she does not see panties his excuse is that they are going to the pool so no need for underwear. Carmen quickly explains that their deal obviously means 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.

Is it worth having your old bully teasing and humiliating you in public again if she gets off with you first?  Your old crush/bully, Juliette March, finally gave your little boner some attention over the holiday break and now she has even agreed to a real date with you. Only if she can make you wear a really embarrassing outfit for your night on the town, though.  Juliette makes sure to keep one hand teasing your tiny cock while she presents the three potential outfit themes-Wimp, Sissy, or Baby. You have to choose between getting pantsed in public with a tighty-whitey wedgie or wearing a girly thong that barely covers anything or in a diaper!   Once you choose your humiliating outfit then Juliette is going to give you a little treat by using her vibrator while she straddles you. As close to making a woman cum as a wimpy sissy baby like you will ever manage. 

From the earliest days of the Girl Bullies Universe- SQ and Ella Nova trick a perverted professor into becoming their little plaything.

Siouxsie Q is back as the ruthless Homework Boss! One of her pet nerdlings has shown up for his monthly orgasm but Siouxsie is a little behind on some of her own school work. Of course she is more than capable of humiliating the little loser, making him cum and catching up on her reading all at the same time!