Opening Up: Going Deeper

Aaron laid flat on the bed in nothing but his soaked pink diaper. A blue cotton towel rested under him, protecting the sheets from his dampness. Helen was digging in the closet again. The memories of his accident at work ran through his mind. He couldn't believe that had happened. It still felt like a dream. And what the hell was up with Addison?

Helen suddenly stood over him, looking down at him in equal parts disapproval and amusement. She set the baby wipes and a fresh pink diaper next to him. This time, she produced a bottle of baby oil and powder. She'd already explained the need to keep him clean and sanitary.

"If you're gonna keep pissing yourself silly," she told him, "you're going to have to keep wearing diapers. But, seeing as how you made the last one leak, I'm going to have to find a better way to fix this."

"Can I get out of the cock cage?" he asked hopefully.

"Only to be cleaned," she replied. "For now. I still plan to have fun with your little prick. It might not be gloriously huge, but I still need some good times every now and then. 'Sides, I kinda get a kick out of being the one in charge."

She smirked at him. He wasn't sure how he felt about her words. Silently, she removed his wet diaper and threw it in the the waste basket. A strong piss smell filled the room. Helen wrinkled her nose until it started to dissipate. Then, she leaned forward, lowering her lips to his. Her light, lingering kiss made his caged dick twitch. He whimpered in mild pain.

When she pulled away, he noticed her silver chain necklace. She pulled the necklace out of her cleavage and showed him the small black key on the end. She used the key to unlock his cage. He cock jumped to attention almost immediately, already dripping with precum.

"Looks like you really get a kick out of these diapers," she commented with a chuckle.

"Mhm," he muttered.

Using a few baby wipes, she carefully cleaning him up for the second time that day. Instead of being all professional, like she had been in the morning, this time she firmly gripped his full erection. With the wipe, she stroked the complete length of his shaft, from the balls to the head. He moaned and shivered lightly under her touch.

After a few strokes, she threw the used wipe away and continued stroking him with her bare hand. Her speed increased, her grip tightened. He bit his tongue. Without warning, she moved forward and took his entire dick in her mouth. He felt her tongue dance over his flesh while she cupped his balls with one hand. He jerked and arched. In moments, she was bobbing up and down on him. His moans grew louder and he became to tense.

"Unnn," he groaned.

Suddenly, she pulled away, leaving him high and dry. He protested loudly, but she slapped his dick in response. Precum mixed with her saliva gave his cock a glistening coat of wetness.

"Last time you came way too soon," she explained in a sultry tone. "I intend to let you cum, but only when and where I say. Understand?"

"Yes, ma'am."

With a smile, she stood up and slowly removed her blouse. Her large tits flopped out. He wondered why she hadn't put on a bra, but that thought slipped away the moment she started pulling down her jeans, revealing she had't worn panties, either. He licked his lips as his dick twitched. Her perfectly shaven cunt was just barely visible between her thighs.

Kicking the jeans away, Helen sauntered closer to him until she standing by his face. She leaned over the bed like she intended to kiss him again. But, she held her face a few inches from his, slowly breathing on his neck. Then, she leaned in more until her large breasts were in his face. With one hand, she rubbed her tits against his skin. His muffled moans made her grin. Using her other hand, she grabbed his throbbing cock and squeezed as hard as she could. His moans intensified.

Expertly, she swung her leg over his body and climbed on the bed atop him. Still holding him, she guided his tip to her pussy. Instead of pushing it inside right away, she rubbed him against her clit. It was her turn to moan. She started to slowly grind against his tip. He felt her getting wetter with every stroke. He wrapped his arms around her waist, placing his hands firmly on her perfect ass. She groaned when he squeezed her cheeks.

"Oh baby," she breathed. "Fuck me."

Further instructions were not necessary. She removed her hand from his cock and he instantly rammed all of it inside her eager pussy. She arched her back and let out an echoing moan. He was too aroused to start off gently, and began pumping his hips hard and fast into her. She bounced her ass in rhythm, shoving herself down on him as he came up. She sat up on him, her hands on his chest. As she kept pace, her tits flopped up and down, making him hotter and hungrier. He grunted with each thrust. She began to growl lowly. She dug her nails into his chest and ran her fingers downward, leaving red trails.

Her hands suddenly slid up his body to his neck. Pressing her thumbs against his throat and cupping her hands around his neck, Helen applied just enough pressure to minimize his air intake. They'd never tried choking before. The sensation was overwhelming and Aaron bit his lip in pleasure as he rammed his dick inside her even harder. He watched her tense, felt her hands tighten on his throat, and felt his own orgasm rising. He gripped her hips tightly for leverage and trust as hard and deep as he could. Her moans grew louder, more guttural. He felt her pussy tighten around him until she finally screamed and exploded. Hot, wet pussy juices poured over his dick. One more deep thrust and he popped. His toes curled as he shot several thick streams of cum deep inside her. They both twitched and spasmed for several seconds. She released his neck and collapsed on top of him. Her hot breath was on his neck.

"Fuck yeah," she breathed heavily.

She continued to lay on top of him as he stroked his fingers along her back. After a few minutes, she pushed herself up. Without a word, she lifted her ass until his prick plopped out of her pussy, coated in creamy white froth. She moved up until her freshly fucked pussy was over his face. As she lowered her cum-drenched cunt to his lips, his dick twitched again. This was new, too. Not the pussy eating, he did that often. But he'd never eaten her pussy right after fucking her.

He took her lips in his mouth, sucking gently but fervently. His tongue darted over her folds. He worked up to her clit, then flicked it with his tongue. She groaned with pleasure and started to grind on his face. She wove her fingers into his hair and pulled his head closer. He shoved his tongue inside her, tasting her strong, slightly acerbic flavor. He could even taste his own bitter cum. He recognized it from the last time she'd made him eat his own spunk. This was even better.

It didn't take long for Helen to tightened her thighs on his head. He kept licking and sucking her pussy until she let out a loud, lengthy moan and came in his face again. Her second spurt sent hot streams of her cum down his throat. He lapped up every drop eagerly and tried to keep going. But she pulled away.

"Mmm," she said, sliding off the bed. "You're the best pussy eater I know. Even better than that lesbian lover I had in college."

He licked his lips and smiled at her. Before he could reply, however, she leaned in and kissed him. As he kissed back, she slid her tongue into his mouth and over his tongue. For a few moments, they let their tongues dance. Then, she ended the kiss.

"You get good things for being a good boy," she told him. His cock jumped at the phrase. "But, you still did piss yourself silly at work and made a huge fucking mess. Good boys don't do that. And since you were already being punished with a diaper for last night's incident, it looks like I'll have to up the anty."

He swallowed hard. In a way, her newfound love of punishing him really got him hot. But, she seemed to favor public humiliation. And while that idea thrilled him, he was still getting used to actually doing it. He watched as she put the cock cage on him again, effectively ending the idea of another bout of fucking. She slid the pink diaper under him and opened the baby oil bottle. Slowly, maintaining eye contact the entire time, she rubbed the oil over his inner thighs, his balls, and his ass. He shuddered in ecstasy. Then, she applied the baby powder. The powder stuck to the liberal coating of oil. Lastly, she closed the diaper around him and taped it shut.

"There," she said. "All ready for your next accident."

He moved to sit up, but she pushed him back down. He looked at her and she wagged a finger at him. He watched as she opened her dresser drawer and pulled out a pair of panties and a bra. A tiny spurt of piss squirted out of him into the diaper. He immediately knew where she was going with this.

"Helen-"

"Uh, uh, uh," she said. "You're a little baby bitch, pissing yourself and wearing diapers. You don't get to use my name unless I say so."

"But-"

"Do you want me to make you wear this for a month?"

He clamped his mouth shut. In the back of his mind, he knew he could put an end to this. But then, he wouldn't get to have any fun. Besides, he'd always wondered what it would be like to wear women's undergarments. He'd been a crossdressing little boy growing up, until his father found out.

He lifted his legs when she commanded and watched as she slid a pair of pink polka dotted panties over his thick baby diaper. The panties fit surprisingly well, despite the fact that he was not the same size as Helen. She sat him up and helped him into the white padded bra, and it also fit perfectly. It was as if she had bought these just for him.

"Now, if you're gonna wear a bra," she said, "you have to look like you have boobs. Otherwise, what's the point? Did you know it's pretty easy these days to buy breast forms?"

He shook his head. She opened the dresser again, this time withdrawing two C-cup breast forms. His cock jerked in the cage and he moaned gently against the pain. If she noticed, she didn't show it. Instead, she fitted the forms into pockets in the bra he didn't know where there. When she was finished adjusting the fake boobs, she observed her handiwork.

"Perfect," she smiled. "Now, for the rest of the wardrobe."

The rest? Another spurt of pee leaked out into the diaper. He watched as she reached into the closet and came back with a short blue plaid skirt and a white v-neck blouse. If it were even remotely possibly, he would have been full erect at the time. But the cock cage worked so well that he didn't even have a bulge. Which, considering he was about to be dressed up like a woman, would help complete the illusion.

She gestured for him to get off the bed and he obeyed. She helped him get dressed, and then adjusted the boobs again to make they were sitting perfectly. His legs were naturally hairless. As was his entire body, in fact. He had never thought he would need to be hairless. She produced a small black handbag and a black leather purse.

"You're going to take me to a nice dinner tonight," she told him. "But you're gonna look your best."

His face flushed. It was one thing to do this in private, but to walk around outside - and even worse, go to a public restaurant - all dressed up in women's clothes, that was something else. Something he'd always wanted to do, and something he'd told Helen about when they started discussing their deepest fetishes. Only, he had never expected her to go through with the idea.

Now, she led him to the bathroom and sat him on the toilet seat. "You're going to learn to do this yourself," she said, opening the small bag. "But tonight, I'll do it for you. We'll work on the lessons later."

So she planned on more of this. His dick twitched at the thought. He sat perfectly still as she withdrew makeup and lipstick from the bag. With the kind of expertise only a woman had, she applied a bit of mascara, eye shadow, lipstick, and makeup. Lucky for him, he shaved daily.

When she was done, she nodded. "Good. Now, one more thing and then you can see the handiwork. Sit right here. I'll be back."

She left him in the bathroom for a minute or two. When she returned, she carried a long, dark wig. It matched his eyebrow color almost perfectly. She really had thought this out. But, they'd only discussed his kinks a few days ago. Had she bought all this in that short time? He didn't have time to consider the thought before she situated the wig on his head. After a couple of careful brushes, she seemed content.

"Alright," Helen said. "You can look in the mirror, now."

He did so, and was beyond surprised at what he saw. He barely recognized himself. He really looked like a mildly attractive woman. He considered how soft and light his natural voice was. Unless he did a lot of talking, no one would suspect he was really a man.

"Your name is Alice," she told him. "At least, while you're all dolled up like this."

Alice. He liked that name. He smiled. In the mirror, a red-lipped, dark haired Alice smiled back.