Anna says "We should play a game with the little guy."  Cali says "Good idea but what should we play" as they move to the living room with Anna still holding on to Jack and they sit on the couch.  

Anna continues "Maybe we can come up with a game that also helps train the little guy.  Maybe we can come up with challenges for him to do.  They should be difficult but possible for him to complete.  If he completes one we give him a point but if he fails then he loses a point.  If he gets to three, he wins and gets a reward but if he gets to minus three first, he gets a punishment."  Cali says "I like that.  Should we take turns giving him challenges and since you are my guest, you can go first."

Anna thinks about the possibilities and thinks she wants to really belittle Jack more than what Cali has done, make sure he loses the game and that she gets to help punish him.   Anna lowers Jack to the floor in front of her bare feet and says "I think we need to start by testing his obedience.   Squeaker, be a good boy and lick my feet clean."  Cali laughs at the idea and says "You are so mean but it's a good idea.  Come on Squeaker don't keep Miss Anna waiting."

Jack doesn't want to lick his ex's sisters feet but the punishment for losing could be far worse.  He could refuse he'd already has a point against him and things could get worse.  He approached her foot as she flexed her toes. Anna says "Get to it now or you lose."  Jack approaches her foot and tries to kiss it on the side.  "Oh no little foot boy.  Do it between my toes.  Lick up all that dirt."  Jack complies and it makes him want to vomit but he keeps going.

Anna looks down at him with a smug look.  She never liked Jack when Zoe dated him.  He seemed a bit cocky and so sure of himself like he could get away with anything.  No anymore.  Now he's barely fit to clean her foot."  She spreads her toes and says "Get in between, Squeaker."  Jack sticks his head between her first two toes and she clenches them trapping his head and says "Don't stop licking, Squeaker."

Anna releases him and he fall down but he gets back up and starts licking again.  Cali says "OK enough. I think he proved his obedience.  It's my turn."  She picks up Jack and places him on the coffee table in front of them Cali takes a bottle of water she has and pours a bit in the cap for Jack to drink.  Jack drinks trying to get that horrible taste out of his mouth.  Anna complains "You are babying him, Cali."

Cali responds "No I need him to recover a bit because my challenge will be a test of endurance.  She put her legs up on the coffee table on each side of Jack and said "Squeaker, I want you to climb up and give me a kiss on the lips.  You can take as long as you want but you can't stop for more than a minute to rest of plan your next move.  If you fall off me then you lose.  She reached down and set him astride her ankle.  

Her legs were horizontal but the gap between the coffee table and the sofa was pretty far for him at this size and he wasn't sure if he'd survive the fall.   He stayed low on his belly with his legs and arms spread out and inches his way along until he reaches the top of her leg.  Anna comments "Wimp, you could have just walked across but you crawl across."  

Jack looks up at the next part of his journey.  Although Cali is reclined a bit it is still a very steep climb up her stomach and chest.  He climbed up stood on the top edge of her belt.  He grabs some material of her t-shirt and pulls himself up using both his hands and feet to make slow progress to the top.  This worked until he got to her breasts.  The material stuck out over her amble breast and Jack had a dilemma that he can't get over so he has to go around working his way to her side to continue his journey.  It takes a while and his muscles are starting to hurt but he up to her collar,  

Her lips are so close but this would be the hardest part of the trip to them.  He would need to climb over her face to get to her lips.  Cali meanwhile has the camera on her phone in selfie mode she she could watch you nearing her face,  Jack reaches out to work his way to her face but just as he shifts his weight her head moves ever so slightly.  He tries to grab on but air.  She starts tumbling and he can seem to stop himself as he careens down between her breasts bouncing off the t-shirt and landing on her stomach.  He continued to roll and passed over her flat stomach.  He just needs to grab something to stop falling and he reaches for her belt as he rolls past it.  He has a loose grip for a second but loses it and falls toward the space between her legs.  With perfect timing, Cali spreads her legs a bit and Jack falls down between her thighs to the couch below.  "You're back to zero, Squeaker." she said as she closed her legs back together trapping Jack beneath them pinned to the couch.

"Good challenge" Anna tells her friend, "You knew he would get that close and ten fail, so demoralizing.  It's awesome."  Cali laughed "Actually I just wanted a kiss.  Didn't think about all that other stuff.  Now it's your turn." as she spread her legs and took Jack out holding him in her fist.