[Time Jump] Matt visits Pippa

We jump forward in time, Matt and Miss Pippa's first meeting when spectacularly, resulting in a quick and strong kinky friendship. While they initially only flirted a little following their initial encounter, their correspondence quickly expanded to include regular exchanging for photos and roleplays, even video game strip bets and forfeits. Over time, Pippa and Matt fell into a regular routine. Whenever Pippa reached a maximum level of horniness and needed it dealt with, she would text Matt who would rush over to her house to attend to whatever Pippa needed.

At first this was as simple as sex, Matt happy to provide access to both his penis and ass for Pippa's pleasure. But soon Pippa's needs became more complex, centered around her need to humiliate Matt. As she explained it, "Sometimes I need to feel some very specific emotions to release sexual tension". Unfortunately for Matt, this often required him to be in either very demeaning or very exposed positions (often both). Luckily, he had quickly found great pleasure in humiliating himself for Miss Pippa, as she conditioned him with orgasms whenever he adequate degraded himself for her.

It had started with just the occasional comment about his penis size. A little jab about his "little guy" or how he was "lucky he was good at foreplay". Matt would protest but would quickly be admonished. But soon she was escalating things. One day when Matt argued about his penis size, Pippa pulled him over her knee and spanked him. And Pippa was dressing Matt up in smaller and smaller outfits when he came over and even when they went out! She made made him clean her house in neon pink briefs, and even had Matt wear strappy, leather sub-undies to work.

Then the chastity cage arrived and Matt found himself reaching a new level of submission. Pippa took great joy in controlling his ability to cum, using it to highlight their dynamic whenever possible. Worse, when Pippa put the cage on Matt, it amplified any and all sexual thoughts he had. He would see Pippa in a sexy outfit, and he would be greeted with his head pressing against the small cage, leading to an aching in his balls. The cage made Matt extremely easy for Pippa to control. After a week without an orgasm, Matt was often eager to do any and everything to earn some release. As she pushed that time longer and longer, Pippa found she really could get Matt to do anything.

And it was with this knowledge that she had planned this evening. She had made Matt wait the longest he had ever waited, an entire month, just to make sure he was as compliant as possible for the night of events in store. If he followed her orders, Pippa would let Matt's little guy out of the cage at the end of the night, for him to finally enjoy himself like he never has before.

So this is where we find Matt, sitting in his cage, wringing his hands and fidgeting as he sits on Pippa's couch, terrified but dying to get through to the end of the night. He is waiting for Pippa to come downstairs and reveal her outfit for the night, as well as his. She had instructed him to shower and groom, but Pippa had informed Matt he would be changing into a special outfit once he arrived.

Suddenly music turned on upstairs, sultry tones introducing the dominant beauty at the top of the stairs.