Jennifer's Morning Challenge
Cut to: Jennifer and Preston standing in the fitness room. Jennifer keeps trying to adjust the leotard to not fit so snuggly on her flabby middle-aged body.
Jennifer: "Are you guys freekin' serious with this? You want me to do the same gymnastics routine I did when I was a hot 23-years-old again now that you've turned me into a frumpy cougar?"
A voice off camera says yes.
Preston: "If it's any consolation the other girls... er women have to do the same things with their older bodies as well..."
Jennifer: "Yeah but I bet the other girls challenges didn't involve them contorting their bodies and doing cartwheels..."
She takes a couple deep breaths and attempts a cartwheel. She puts her hands on the mat and lifts her flabby bare leg off the ground but puts it back down. She attempts two more false starts before managing to get her legs both off the ground together but her form is bad and she tumbles into a crouched position. She winces as she stands back up and rubs the back of her pale thighs.
Preston: "You uh... you still look like you're in pretty good shape for uh.."
Jennifer: *Smirking* "For a what? For a middle-aged soccer mom?"
Preston: "Uh Yes?"
Jennifer: *Rolling her eyes and smiling* "You're too cute Preston! So what are you getting out of this? Because if I was in your shoes and had to stick around while all the hotties my age were getting older and older all around me i'd be running for the hills! Hell, if they weren't promising to give me my youth back at the end of the season i'd be out of here! What do you have a thing for older women or something?"
Preston: *Blushing* "No! No of course not!"
Jennifer: *Grinning, surprised* "Oh my gawd! You do! Don't you!? Haha!!"
Preston: "I um..."
Jennifer: "Hey don't be embarrassed! That's kind of awesome for me! We can hang out together and get through all of this now I know you're not gonna be grossed out by my newly gained crows feet and saggy ass!"
Preston: "Um do you still want me to take pictures of this for your social media or...?"
Jennifer: "Fuuuuuck no! I don't want my like mom to look um my insta and see that i'm almost as old as she is! Besides... I'm going to need an extra set of hands to get through these positions..."
Preston: "Okay! So uh first is folding your body in half..."
Jennifer: *She pinches her flabby mid section* "Yeah that's not gonna happen... Let's just shoot for 'touching my toes'."
She takes a deep breath and holds her arms out in front of her and then slowly lowers her upper body down to the floor. Her back rounds and her belly pooches up into rolls as she bends downward keeping her legs straight. Her faded red hair cascades downward as she reaches with her fingers and just barely touches her toenails.
Jennifer: *Grunting* "Oh come over here and help guide my back..."
Preston comes over and puts his hands on the bare freckled back of the older redhead as she breaths in and then exhales and stretches her body lower.
Jennifer: "Thats good... your hands are kind of clammy though..."
Preston: "Oh sorry!"
He takes his hands and wipes them dry on his pants and then places them on her back once more as she hangs down.
Jennifer: "Ugh this is rough... Now I understand why I can never get my mom to workout with me... Okay you know what will help me get through this? If you distract me by spilling some tea..."
Preston: *Chuckling*
Jennifer manages to get her hands to grasp the veiny tops of her feet.
Jennifer: "What's so funny?"
Preston: "It's just... with your older voice... I've never heard a woman your age talk about 'spilling tea'."
Jennifer smirks at him as she slowly rises back up to a standing position.
Jennifer: "Ha ha. Very funny."
She begins to arch her back and reach down, she starts to lose her balance.
Jennifer: "Ooo okay hunny you're definitely gonna have to brace me for this one... just put both of your hands firmly on my back like you're about to lift a table..."
He braces her and with his support she stretches all the way back. Her saggier breasts tumble up to the top of her chest as she leans heavily on his hands and arms to keep her upright.
Preston: "Uh how long do you need me to hold you?"
Jennifer: "Don't you dare say i'm heavy!... Now back to the tea. So, if you're secretly into hot MILFs I bet you were losing your shit at 40-year-old Haley giving you a lap dance today..."
Preston: "Yeah it was um... Yeah I really enjoyed it."
Jennifer: "She looks like the hip owner of a record store or a comic shop she opened back in the 90s... or like the 'cool mom' at a PTA meeting, the one that drives to the school in a Vespa!... Okay so I need to do a handstand, which means you've got to slide on down to my baggy ass and give me a boost so I can get my stupid flabby legs upright!"
He follows her direction, moving down to hold her buttocks as she kicks off the ground and groans using the momentum to get herself into a leg stand. Preston holds the older woman by her ankles as she wobbles on her hands trying to balance her weight, her tits pulling her chest toward her chin.
Preston: "Yeah she uh has an imaginary daughter that's starting college this year..."
Jennifer: "Holy shit seriously? That's fucking wild! She's still supposed to be in college! And now she thinks she has a daughter that age? Oo! Oo! Preston, put me down! The bloods starting to rush to my head..."
He lets her go and she tucks her legs in and flops down onto the mat, rolling over and sitting up red-faced. She shakes it off and holds out her hand for him to help her up. He tugs her back to her feet and she rubs her lower back panting for breath.
Preston: "Yeah so she wants to set me and her daughter up together."
Jennifer: *Giving him a sympathetic look, emphasizing all her newly gained frown lines.* "Awww Preston! You're thinking she's not even considering a hook up like we all did last night? We did have a three-some last night right? I was pretty hammered so I barely remember... Hold still..."
She moved behind him and does a running jump onto his back. He stumbles forward with a gasp as the sudden weight of this middle-aged woman hanging off of him.
Preston: "Yeah uh two nights ago... well last night too but I don't know about tonight. I think she sees me as a 'kid' now even though i'm technically older than her..."
Jennifer: "Yeah what's up with the other women all thinking they're like Gen Xers now? Like it's not enough that they frump us all up but they have to like mind fuck up into thinking we're a bunch of boring old Karens?"
She attempts to climb on his back. Preston holds his hands out at his hips and Jennifer uses them as foot holds to get up onto his shoulders. She slips her older legs down across either shoulder and presses her cottage cheese thighs against his cheeks as Preston reaches up to brace her soft waist.
Jennifer: "You know they had framed pictures of these two redheaded teenagers in my room when I woke up? Like are those supposed to me
my kids!?"
Preston: "Oh yeah yesterday you were talking about having a bunch of annoying school-aged children so I guess now that you're in your 40s they are probably in high school."
She begins to climb around him, slipping her legs around his head until she was sitting on his shoulders with her crotch in his face.
Jennifer: "But they're not real right? Like its a photoshop job to like play into the whole 'aging through our lives thing?"
Preston: "Yeah as far as I can tell - like no one has shown any signs of giving birth and like half of you claim to be moms now..."
Jennifer: *Smirking* "And you've been checking i'm sure..."
Preston: "Uh..."
She tumbles into his arms and cups his face giving him a kiss with her pruned lips.
Jennifer: "I'm just teasin' ya!"
She backs up and begins doing some stretches with her legs.
Jennifer: "Okay now the wicked hahd stuff! Come on over here and hold my leg."
Preston does so as she raises the plumper leg up as high as she can get it.
Jennifer: "Okay now push it up as high as you can - slowly! And if you hear a pop - stahp!"
Preston: "Okay..."
He lifts her leg as high up as her can while she clings to his shoulder for support. He manages to actually get it to where her toes are pointing to the ceiling, his fingers pressing into the soft fatty tissue of her thighs.
Jennifer: "Ow ow ow okay that's good! Better than I thought I would do at this age."
She quickly brings her leg back down.
Jennifer: "I'm going to have to ice my hamstrings when we're done... or you can always ice them if you're not too busy..."
She winks at him as she gets down on her stomach and stretches her legs up toward the back of her head lifting her upper body as much as she can.
Preston: "That's pretty good too!"
Jennifer: "Yeah nowhere near touching my nose with my toe like I could do 2 days ago... or 20-fuckin'-years ago I guess!"
Preston helps her back up and she brushes herself off.
Jennifer: "So i'm gonna keep doing this routine even when i'm like little old granny Jennifer?"
Preston: *gulps* "Uh yeah..."
Jennifer: "What if i'm like so old and frail that I can't even walk on my own?"
Preston: "I'd have to move your wrinkly old body around myself then I guess?
Jennifer: "Ooo you're looking forward to that aren't you? For my own sake i'm hoping i'm senile as fuck by then!"
She waddles over to the door way and looks at it warily as she grips both sides with her hands and spreads her feet apart so that they are on either corner of the door frame.
Preston: "I don't know... I kind of like having a friend to talk to who doesn't like think she's so much older than me and who I don't have to pretend like we aren't on a reality show that magically aging everyone..."
Jennifer: "Well when you put it that way... Okay I need a lot of help for this one. I know you're scrawny but I need you to lift my old ass up as much as you can so I can climb this doorframe."
Preston: "Okay..."
Preston reaches down under her and hoists her thighs up, straining to lift her. Jennifer pulls herself up and begins walking her feet higher and higher up the frame. They manage to get her halfway up with Preston holding her by her right thigh and crotch and Jennifer wedging her left leg against the frame.
Jennifer: "All right I think that's the best we're gonna do."
Preston: "And uh don't worry... you're gonna be hot at any age you get up to."
Jennifer gushes at his compliment. She hops down and flops on top of him toppling him over back onto the mat as the 43-year-old in a super tight fitting leotard lays on top of him.
Jennifer: "Awww Preston, you're just like the sweetest guy! I'm totally going to get Haley to come fuck you tonight! Don't you worry! I'm your MILFy wing-woman!"
Preston: *Smiling excitedly* "Thanks!"
WHAT SHOULD WE DO WITH TRUTH OR DARE ON DAY 3?
- Skip It!
- Do a whole new round of it!
- Do the truths and dares from Day 1!
- Do the truths and dares from Day 2!
- Pick the best truths and dares from Days 1 and 2 and do a combo!