Desperate Measures

Jack returned to a silent house. He checked his bedroom first, and finding that Guin was not there, checked her bedroom next. She was lying on her bed, two magazines and a book in front of her, looking them over intently. From the pictures, he could tell what they were.

He cleared his throat and Guin looked up. "Oh. I didn't hear you come in."

"Care to explain what you have, there?"

She looked it all over rather swiftly. "I wanted to learn how sex worked."

Jack sighed, then nodded. "And since I was being a stubborn ass about it, you opted to try to learn it yourself through means such as this..."

Guin lowered her head. "I wouldn't use those exact words, but yeah..."

"What words would you use?"

"I would have tried to avoid calling you a stubborn ass..."

Jack chuckled. "You're a good kid, Guin. But I have been stubborn, and I am an ass. My name is literally Jack Ass. That's who I am, and that's what I've been."

Guin was silent. She didn't want to agree with him, but he was right.

He walked over and sat down. "Is there anything else in this collection?"

She pulled out the rubber dick, still in the box. Now that the comparison was fresh in her mind, it was smaller than he was, by a wide margin.

"Still in box, huh?" asked Jack, inspecting it.

"Well, I did open it... I'm just using the box for storage."

"You cleaned it, right?"

She nodded.

He took a deep breath, draping it over his shoulder. He then picked up the magazines and book, as well as Guin, and carried everything back to his bedroom, where he laid it all out. "I want you to tell me the truth, Guin. Does Jenny know anything about this?"

"She knows about the box I kept everything in, but not what was inside it. She hasn't seen any of this stuff. Neither has Kurt."

"Good. It stays that way, understand?"

Guin nodded.

"These things are staying in her from now on, too. They'll be safe, and you can still use them, but just with my supervision. Do I make myself clear?"

She nodded again, vehemently.

"Good." He sat down. "They'll learn eventually. I was going to teach Kurt before too long, and with him having a marefriend, I should do it soon, but Jenny... I think you should be the one to talk to Jenny about it. I'll coach you through it, don't worry, but it's going to happen. You have a few years to prepare."

"But I don't know how to teach her how to do it. I don't even know."

"That's what we're going to start on today." He picked up the rubber cock. "Do you know what this is?"

"A penis."

"Almost. It's a dildo; a facsimile of a penis. And a small one, at that. Do you know how to use one?"

Guin shook her head. "I've only used it once, and I think I did it wrong."

"In truth, it can be used to replace a dick in most scenarios," explained Jack. "If I'm asleep, for example. Don't ever do that again; you nearly gave me a heart attack with that scream."

Guin nodded. She was already never going to try that again, because of how much it hurt, but if Jack was in agreement, then it was mutual.

"Good. Now, let me show you the most important things you'll need."

Next to the bed was a shopping bag, and he pulled from it a bottle of clear liquid and a cardboard box. He opened the cardboard box and pulled out a small sleeve, then lay down next to her on the bed.

"This is a condom. It's also called a rubber. It's one of the most important parts of sex. It's a protective film that goes over the penis to prevent unwanted pregnancy."

"But what if I want to become pregnant?"

"Then you don't put one on. But always ask, first. If you don't want to discuss it, always wear a condom. It's the safest choice." He picked up the dildo. "Now, if I knew you had this, I would have bought condoms in this size, and I could let you practice on that. But since I didn't know, I guess we're going to go back to plan A." He opened the sleeve. "These are in my size. But first, I will need to have an erection."

Guin nodded. "How does one... make that happen?" she asked. "Every one I've ever seen has already been out or was tucked away. I've never seen the change."

Jack nodded, then picked up the book. "There should be a section here at the back... Ah, yes." He turned it around and showed her what he was talking about. "Now, I don't want to seem a selfish lover, but it's important that you learn how to do this. Use your claws on me like he uses his hoof on himself, but make sure not to use your talons. Breaking the skin is a bad thing. And if you have any questions, just ask for help."

Guin followed the instructions in the book, and it wasn't long at all before Jack's cock began to slither out of its sheath. It was even floppier than the rubber one, despite how hard it had been last night. "Am I doing this right?"

"Yep. Keep going, though."

"But it's all floppy."

"Think of it like a balloon," answered Jack. "when it's only halfway inflated, it's all floppy, too. But when fully inflated, it's firm and likes to hold its shape."

As he tried to think of arousing things to help her along, he suddenly felt a wetness on his tip, and had to look as Guin's cheeks began to puff out.

"What are you doing?"

"You said it was like a balloon. I'm trying to blow it up."

"Just rub it with your claws." He intentionally twitched, using his abdomen to yank it upward a small amount. "See? Working just fine. We'll do mouth stuff later, just focus on your claws for now."

It wasn't long at all before he was nice and firm again, standing straight up. Jack ripped open the sleeve and pulled out what looked to be some kind of gasket. "I want you to pinch this part, hold it at the tip, then roll this down the sides."

She did as he said, and seconds later, he was covered in a thin green film. "Did I do it right?"

Jack nodded. "You did it exactly right. Make sure you do this every time, unless both you and your partner want kids. Now, let's talk about lube..."