Chapter 96

Jacob wakes up in their room in the Ranch Motel with his head buried in Izzy’s hair. He pulls his head back as he regains consciousness, removing the hair from his mouth. His arms are tightly wrapped around her, and she is holding his arms tight to her chest. Jacob remembers falling asleep snuggled close

The next instant he remembers having sex with Izzy last night.

Then he remembers the harness and the strapon. There is a sense of loss and betrayal. He moves slightly, and Izzy whimpers in her sleep. He experimentally shifts his hips, and Izzy moans. ‘Oh god, did I fall asleep inside her last night? Is it still inside her?’ he asks himself as he feels his cock swell in the diaper. ‘Oh right, I was wearing a diaper last night.’

He mentally feels his diaper, and it’s dry. He breathes in more of the smell of her hair.

“I love you.” He whispers and snuggles tighter, but he soon realizes he needs to pee. He pictures getting up, going to the bathroom, and leaving Izzy here alone. Not to mention the toy still inside her, or at least still touching her vagina. He couldn’t tell. “I can just use the diaper, right? That’s what it’s made for, right?” he says quietly, asking himself for permission to do it. 

He shrugs mentally and pushes gently. It’s all the permission his bladder needs to let go and start to flood the diaper. He panics and tries to slow the flow, but the bladder has other ideas. 

He fills it until it swells.

Izzy, mostly still asleep, feels the warmth of the diaper and wiggles her butt tighter to him, nuzzling against him. The tip of the toy rubs against her opening, and she murmurs and pushes back. The tip slipped inside her. She moans and starts to wake up. She pushes back harder, and the tip goes deeper inside. “Mmmh, Jacob, you’re so hard,” she whispers, pushing back more, taking ⅓ of its length. She squeezes down on the toy rhythmically.

They very slowly work into a rhythm of Jacob thrusting and her pushing back in synchronous motion. The tip of the toy pushing on her G-spot. Her bladder full, she fights with the urge to get up and go pee. Instead, she blindly grabs the vibrator.

She makes a soft moan as she parts her lips and puts the tip directly on her clit. “Oh God,” she whispers.

The vibrations are enough to go from playing around to aroused. Jacob’s penis is bumping on her G-spot from behind as he kisses her neck. “Don’t come in me, Jacob; it’s too risky,” she whispers as she feels Jacob’s hands on her breasts. She feels him teasing her nipples and pulling on them gently.

“Oh god, just fuck me, who cares?” She says, pushing back harder, getting ¾ of the toy inside her. She rhythmically squeezes and pulls on the toy with her vagina.

He obliges; meanwhile, his erection is rock hard inside the diaper. He thrusts like she likes it, long and hard in and slow and gentle out. “Are you sure I should cum in you?” he whispers into her ear.

“No, I am not sure. But I want it.” She reaches back to grab his butt and pull him closer, but her fingers land on the diaper instead, and the illusion is broken for her.

“Oh, it’s your other penis. Then yes, you can fill me.“ She slides the vibrator down until it hits the fake cock, the vibrations being transmitted into his diaper, and the material gently hugging Jacob’s cock. She can hear him moan in her ear. 

Jacob, feeling empowered, goes faster, the whole situation hot enough and with enough movement to make him feel like he could cum. He imagines what it would be like to fill Izzy again with his or the toys cum, and it pushes him close to the edge.

Izzy can feel his hot breath on her neck. She can feel his thrusts getting erratic. “Are you going to cum in your diaper… again?” she says with a little chastisement in her voice. 

She turns the vibrator up and moves it to her clit. She thrusts against him as he thrusts forward. “I think I want you to cum in it,” she whimpers as he feverishly fucks her.

His rhythm starts to falter. “Are you going to do it? Going to cum in your diaper instead of your girlfriend?” She teases, ‘This is so hot. When did I become like this?’.

Jacob is trying not to cum as hard as he can. He is biting his lip to the point he is afraid it will bleed. ‘I just have to hold out long enough for her to cum first,’ he begs the universe, ‘please let me have that much.’

She shifts the toy, and the edge of it hits her clit just right. She feels the built-up pressure let go, and she starts to orgasm. She feels a warmth spread out from her vagina and a warm, fuzzy feeling spreading across her body. Jacob is still pounding her roughly, and for a moment she considers telling him to stop, but instead She reaches back and holds his hand, pulling him into her deeper.

“That’s right, fill your girlfriend, fill me with your other cock while your other one finishes in your diaper.” She feels him make short, sharp thrusts, filling his diaper full of cum.

They lay there in a heap smelling of sex. 

Jacob wraps his arms around Izzy and holds her tight, the toy buried in her. She reaches back to touch him inside the diaper; it’s warm and wet.

“How did that happen?” Izzy asks, concerned.

He buries his head in her neck, ashamed. “I didn’t want to get up,” he admits. 

“So you just wet instead?” She asks incredulously, but she stops and thinks about it. He didn’t want to get up and stop cuddling. Instead of disgust, she feels the warmth of love and connection. And not just because Jacob’s other penis is still inside her.

Jacob sits silent. “There isn’t much of my dignity left, is there?” He whispers after a long silence. He pulls the covers over his head.

Izzy laughs and pulls the toy out of herself. She feels the empty sensation and turns around and kisses him long and slow. “Let’s wash up.”

They walk to the bathroom, and Izzy unhooks the harness, tossing it in the shower. Then she untapes the diaper, putting it into the trash. She watched him hide behind a blank expression. “I really thought helping you out of a diaper would be unpleasant.”

“Then why did you do it? Jacob asks his childhood trauma poking its head out from under the bed.

Izzy doesn’t answer his question; instead, she pushes him toward the shower. “Let’s go wash up, pee boy,” she says. Jacob stands looking ashamed, trying to figure out what to say.

Izzy waits a few seconds, then gives his bare ass a playful spank. Jacob winces at the sting, then bites his lip. ‘Why did I like that?’ he wonders to himself as they climb into the shower.

They take their time washing each other up. With Izzy paying special attention to Jacob’s privates. They get dressed, Jacob in normal underwear for the first time in what feels like forever and Izzy not filled with cum, with similar feelings.

Jacob starts to feel good about himself. Their strange sex is comforting and fulfilling.

Izzy’s watch buzzes first, then Jacob’s. “Report to the bar to see Jack Harrington,” the watches say.

“Good timing? Or are they watching us?” Izzy asks her clean boyfriend.

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