Tracy takes it in her ass

The massive dildo is now slick with the juices from Tracy's pussy, but you decide to help further lubricate it before she sticks it in her much tighter asshole. You grab a large bottle of lube which you placed near the squat rack earlier in the day and generously coat the dildo. Tracy looks on with a worried look on her face in anticipation of what's to come.

"Alright slut, seeing as it's your first time, you only have to do 5 reps in your ass."

"Thank you sir." Tracy doesn't seem to have a lot of words to say as she stares at the dildo contemplating just how much the thing will stretch out her asshole.

She takes a deep breath before preparing herself above the dildo. Just as she did with her pussy, she positions her rear hole just above the dildo and lifts one leg up before using one hand to guide the thing towards her asshole. Her asshole has now recovered from its previous gaping state as a result of the bike workout and is sitting firm and tight. It takes some brute ****, but Tracy finally gets the dildo to enter her tight hole and lets out a frustrated moan as she works the tip into her ass.

"Fucking hell, this thing might be too big sir." Tracy turns her head over her shoulders and looks at the serious look on your face.

"Are you disobeying an order, slut?" She lets out an audible gulp at the idea of what punishment awaits her if she fails and looks back down at the dildo with a look of determination on her face.

With a bit of squealing and a large amount of swearing, Tracy finally manages to lower herself onto the dildo so she's in a standing position above it. Perhaps the rest would be easier, people always say the tip's the hardest part. With a few deep breaths Tracy grabs onto the bar and lifts it off the rack, now mentally psyching herself up for what's to come. Finally feeling ready, she slowly starts lowering herself down onto the thick dildo, taking lots of short sharp breaths and letting out the occasional "OH FUCK!" as she struggles to take the monstrous cock up her ass. From your rear view you can see how taut the skin around her asshole is being stretched as she descends lower and lower and her asshole stretches around the gradually increasing girth of the dildo. Tracy finally reaches the bottom of her squat and as soon as she does so she rapidly pushes back up to a standing position, barely being able to handle the thickness of the dildo.

"Oh fuck, my ass was stretched so tight! Please sir, don't make me do that again."

You slap her ass cheek hard and grab onto it. "I said five reps and I meant five reps slut. Now show me how obedient you are and do another squat."

Tracy has a look of fear on her face, maybe she's afraid of the punishment she might meet if she fails you now or maybe she's afraid of taking this massive dildo up her ass another time. But nonetheless, Tracy regains her look of determination and starts lowering herself down into another squat.

"Ohhhhh fuuuuck! My asshole's gonna be ruined after this!" She screams out in response to the pain in her stretching hole.

As she descends lower and lower onto the dildo you imagine how far up the thing is inside of her and picture on her back where it would be up to. That thing is rearranging her guts for sure. You can see in the mirror Tracy's eyes are starting to water from the pain and her mascara is running down her face. However, Tracy manages to get through the next four reps, with great difficulty mind you. Finally reaching the top of her final rep Tracy moves as quickly as she can manage to put the bar back on the rack before popping the dildo out of her ass. Her asshole makes an audible pop sound as she pulls the tip of the dildo out of her hole. Her legs are trembling from the workout and she looks like she's struggling just to stay standing.

"Look at your gaping asshole slut."

Tracy turns around to point her ass at the mirror and grabs her cheeks with her hands, spreading them to show off the visible gape of her ass. You can see straight into her cavernous rectum and some leftover lube along with her ass juice is leaking out around the edges and dripping down onto her yoga pants around her thighs.

"Oh fuck!" She cries out, looking at how completely destroyed her asshole is. "Will it go back to normal." She says to you with a worried look on her face.

"Don't worry, it should. Or at least I hope so for your sake." Tracy bites her lip in fear at the thought of her asshole never fully recovering.