Fine...

You decide to pay Sid his salary of $400 a month.

Sid: "I knew this wouldn't be an issue! You're a standup guy, Matt." He says, still naked with his hand on your shoulder.

Alyssa: "omg thank you baby, you won't regret it!" She kisses you deeply, clearly very happy. "Maybe we can take a shower together, so I can thank you properly..."

Sid: "That's not a good idea, Matt is in a delicate place right now in his training. He needs to get his dick more sensitive...so he can't be cumming just willy nilly anymore. But we can hit the showers no problem. Matt can clean up here in the meantime, right?"

You: "Uhm...sure....I get it"

Sid: "Thanks, bud. You know how much I like getting cleaned up by your girlfriend. Gives me fond memories of our first night together..."

As Sid and Alyssa get up to shower. Sid turns back.

Sid: "Oh, one more thing, you should move your stuff Into the guest room, and just sleep there for a few months. If I'm gonna continue the lessons, it's best for Alyssa to sleep in the same bed as me. Plus it's bigger so...you get it, right?"

You: "Oh...uhm, actually I want to sleep next to Alyssa..."

Sid: "Nah, this is for the best, Matt. But you should check in on us regularly, to see if we're fucking, then you have the opportunity to learn something. Ok, bud? Alright." He says before leaving you with the mess on the sheets, the floor, and your pathetic dick.

You finally pull off the condom and put on some pants. You can't really feel your dick anymore, but you assume it's from all the rubbing earlier. As you clean up the mess, and start moving your stuff over to the guest room, you can hear Sid and Alyssa fooling around in the shower. Laughing, smacking, kissing, acting like lovers in there....but Alyssa assures you it's nothing to worry about.

For the next few weeks, your life sets into a routine. Every day, you fuck your pathetic little plastic pussy on the floor, with a desensitized dick, and a condom on. While Sid is on his bed, fucking your girlfriend in all the possible positions you can imagine, then some you can't imagine. And everytime, he goads you into watching him cum inside your girlfriend. You've seen it so many times now, it should be no big deal anymore, but it still hurts. Meanwhile, you keep paying Sid $400 a month, except he raised it to $500 a month, to cover expenses.

Turns out, those expenses were various cock rings for him, sexy, revealing clothes for Alyssa, and a little surprise for you.

Sid: "I've got a gift for you, bud! Come here!"

You raise your eyebrow in suspicion..."what is it?"

Sid: "Well, since you have so much trouble with your desensitized dick. I've bought this for you!" He says and whips out what you know to be a chastity cage. "I promise, wear this for a couple of weeks, your dick will be super sensitive!"

You: "I don't know...."

Alyssa: "Oh, please babe. I can't wait for you to finish the training so we can finally have sex!"

You: "Really? We can have sex???"

Sid: "After this, bud" and hands you the chastity cage.