Desperate Measures

After only a few dozen thrusts, Guin felt herself involuntarily clamp down. She'd felt something similar a few days ago, when Jack was rubbing her, but she felt it again now.

Last time, her feet had all been in the air, so she couldn't be sure if the same thing happened last time as this time, but her limbs locked in place as her fingers and toes curled and her claws stretched out, locking into the bedspread beneath them. Moments later, a spray of fluid gushed out of her, and she collapsed on a crumpled heap onto Jack's chest.

He wrapped his hooves around her. "Looks like you had a good time," he chuckled.

"Mhmm..." Guin couldn't handle words right now. She could barely handle thinking, much less speaking.

He began to stroke her back, but rather than being gentle, he was applying pressure. Every stroke moved her just a little bit, and that meant moving him inside of her. It was barely any movement, but she felt every millimetre as if it were a decimetre. Were her claws not latched firmly to the bed, her legs would be flailing wildly as the pleasure she felt was sending pulses through her body in rippling waves.

Soon, the pulses calmed in intensity, and she was left to her quiet, humming moans. "That was... great," she breathed, barely able to elaborate.

"Good," he smiled. "So now, there's something else I'd like to do, now that we know your maximum comfortable depth."

"Oh yeah? What's that?"

"I'd like to check your depth again. Can you go any deeper?"

Guin looked back. She could feel herself pressed against the medial ring, and any further than that was painful territory. "I don't know..."

"Just try," Jack urged. "If it hurts too much, you can always stop or come back. I'm not trying to hurt you, I just want to see how you feel."

Guin nodded and gulped, then closed her eyes and pushed back. To her amazement, she was able to swallow the medial ring, and even a few centimetres more before it became too much. As promised, Jack let her back up.

"You went a little deeper that time," he smiled. "See? You'll be able to fit the whole thing before you know it."

Guin smiled and placed her claws on his chest. He was a good teacher, and she was right to trust him.

He held her tight to his abdomen and rolled them both over, so that he was on top, then lowered her to the bed. "Are we going to do that "mission-style" the book was telling us about?"

"Missionary," corrected Jack. "And yes, that's what we're doing. I now know how deep I can go, so as not to hurt you. But if it does start to hurt, I need you to tell me to stop, okay?"

Guin nodded. That seemed simple enough. But as he began to push in to the medial ring, she stopped him.

"That one magazine talked about how we should have a safe word if things turn sour," she reminded him. "Shouldn't we have a safe word?"

Jack nodded. "The safe word is "stop.""

"But the magazine said to use a word that would seem out of place. What if I said "Don't stop?""

"Then I wouldn't stop." Jack leaned down to kiss her beak. "Safe words are for when regular words don't mean anything. If you tell me to stop, I'll stop. If you want me to go deeper, I'll go deeper. If you want me to go faster, just say so. All you have to do is tell me."

She nodded and let him go. He started off slow, just a few thrusts at a time. He would drive in with a fair amount of speed, then angle his hips and push against her insides as he slowly pulled out. He knew she could take it deeper than he was giving her, but the medial ridge was a good stopper. Also, he wanted to reserve a bit of length in case she wanted him to go deeper.

She didn't call out for anything for a bit. She didn't really feel that she needed to. He was making her feel spectacular, and she didn't even have to do anything this time. Her whole job was to lie back and let it happen.

As she didn't have to do anything, she didn't know what to do with her claws. If left alone, they would continue to swipe and swing. Her front claws were easy enough to manage, reaching back and grabbing the sheets, but her back paws were still flailing with every twitch.

That's when she had an idea. Jack could hold them down for her. She looked up, panting, and moaned out, "h-hard..."

She'd meant to say "hold," but everything in her mind was muddled. Immediately, she lost track of her claws as Jack began to drive deeper, faster, and push his dick harder against her vaginal walls. She was being reamed, and she lost the ability to care about where her feet were.

Jack, however, had not lost that ability. He was very aware of what was happening as her back claws dug into his chest. They didn't go deep, and from the look on her face, it wasn't out of any kind of malice. He knew she was in ecstasy, and to be fair, he'd never been with a gryphon before. He'd never even considered that her back paws would hold claws that would dig into him like this.

She came again before he did, and after he finished, he left himself inside of her, just up to the medial ring. She had passed out, and would be enjoying a nap, and he'd show her more when she woke up. But as she'd expressed an interest in stretching, he was going to stay inside of her for a bit. It would help her adjust to the size.

Granted, he knew it wouldn't be an overnight change. It would probably be a few more years before she could take all of him. She was made of flesh, after all, and it liked to return to form. But she was young and pliable, and that meant that she could stretch out now and be ready for a relationship with someone her own age when she came of age. It was unlikely she'd want to stay with a stallion thirty years her senior.