Penelope's Punishment (6 page)

Rand smiled broadly. “I am indeed a lucky man in that regard. Lily is wonderfully responsive to anal stimulation.”

“Did you start with manual manipulation or go straight to plugs?” asked Richard.

“I plugged Lily with increasingly larger plugs each evening for about a week before she was ready for my cock.”

“Each evening you say?” asked Richard thoughtfully. “That sounds like a better plan then training Emmie on her rocking horse in the beginning.”

Alex listened to his friends discuss training methods for their little ones with a deep ache. He needed to find Penelope, and soon.

“I almost forgot,” said Richard, reaching into his coat pocket. “I secured the special marriage license you requested, similar to Rand’s.”

Alex reached for the piece of paper, smiling as he looked over the document that would secure him to Penelope.

“How the devil were you able to find out her last name?” asked Rand.

“You can thank Smitty and his underworld contacts for that feat,” said Alex, and he tucked the precious paper into his breast pocket, close to his heart.

Richard chuckled. “I have always thought it was a shame he was not born a lord.”

“I once said as much to him,” responded Rand. “He said he had no desire for the obligations and responsibilities that came with the trappings of aristocracy. He is perfectly content as a butler.”

“To Smitty,” cheered Alex as they all raised their glasses in a toast before heading into dinner.

Emmie and Lily

Richard and Rand made their way straight to the nursery after arriving home. They could hear giggling and laughter down the hall as they approached. When they opened the door they were greeted by the sight of both their little ones playing with dolls. They had just come from a bath and both were naked except for the pink ruffled drawers they wore. Their long beautiful hair curled as it dried by the fire.

As soon as the masculine presence was detected, there was a squeal of delight as both girls ran into their arms, shouting in unison. “Papa!”

Richard hugged his sweet bundle of delight to his chest. “How is my sweet little one?” he asked.

“I missed you. You weren’t here to give me my evening bottle,” Emmie said with a pout.

“I know, baby,” he said, gently stroking her cheek.

“I missed you too, Papa!” chimed in Lily to Rand.

“Did you, Poppet?” he asked as he ruffled Lily’s hair. “Are you having fun playing with Emmie?”

“Oh, yes, Papa!  She has the most beautiful dolls. Come see!”  Lily grabbed his hand and pulled him over to the fire. “I like the one with blond hair best,” she said as she showed him the pretty doll.

“Then I shall get you one just like it,” responded Rand as he sat in a plush chair and pulled Lily onto his lap. Lily rested her head against his shoulder and played with the buttons of his waistcoat.

Richard picked up Emmie and cradled her in his arms as he sat in the other chair in front of the fire. “And how about you?” he asked, brushing the tip of her nose. “Did you also have fun?”

“Yes, Papa,” responded Emmie, shyly burying her head against his chest.

“Emmie do you remember how Papa said that one day he would want to put his cock up your bottom like he does your cunny?”

“Yes,” whispered Emmie, sending an embarrassed look to Lily and her Papa.

“Did you know that Lily’s Papa often uses her bottom that way?”

“No.” She looked at Lily who was blushing furiously and averting her gaze.

“Yes. Lily’s Papa even plugs her bottom so that when he is not around she is always thinking of him. It also helps keep her bottom ready for his cock,” continued Richard in a soft, soothing tone.

“Would you like to see, Emmie?” asked Rand.

She watched in fascination as he instructed Lily to stand and then lean over his knees with her bottom in the air.

“Oh, please don’t, Papa,” pleaded Lily. “It’s too embarrassing.”

“Lily do as you’re told or you will get a spanking,” Rand sternly warned.

With tear-filled eyes, Lily stood and then rested her head and chest across his knees with her bottom facing Emmie and Richard. Rand pulled down her ruffled bottom drawers, exposing her pale bottom. There were still faint red welts from the punishment she received when she threw a tantrum over leaving her pony and coming to London earlier that day. Rand pushed his fingers in between her cheeks and pulled them open.

Emmie could see a pink circle, like a large button, in the center of her bottom.

“That pink circle is the handle of a plug, Emmie,” instructed Richard with a nod to Rand to proceed. Emmie stared in fascination as Rand grasped the handle and gave it a sharp tug. Lily groaned as her body resisted, clamping down on the plug. Rand pulled harder and Emmie gasped as she saw Lily’s poor bottom hole stretch wide as the plug slowly came out. Rand held it up for her inspection.

Emmie thought it would be long and straight like the dildo on her rocking horse but it was much scarier. It was shaped like a triangle, with a small tapered end that got much wider before getting small again and ending in the handle.  

“No, Papa! No!” she started to cry and struggle on his lap. “I don’t want a plug up my bottom!”

“Looks like someone needs to be reminded who is in charge,” said Richard as he stood and carried a crying Emmie out of the room.

Rand stroked Lily’s still exposed bottom. “You did very good, little one.”

“Oh, Papa,” she cried into his lap. “It was so humiliating.”

“I know sweetheart, but it will help your new friend Emmie to understand what is expected of her.” He raised Lily up to stand before him. She watched as he unbuttoned his trousers and took out his cock. He fisted the length and watched as Lily’s eyes grew wide.

“Please don’t. I’m still very sore from last night.”

“Now, Lily, you know the paddling you received this morning was only part of your punishment. What was the other part?”

Lily didn’t want to respond, so he gave her exposed nipple a small tweak.

“That I would have to take your cock up my bottom,” she said, biting her lower lip.

“Good girl. Now turn around.” Lily reluctantly obeyed.

“I want you to spread your cheeks. You are going to slowly sit down on my cock.”

He watched as she opened her cheeks and bent her knees, her rosebud was already opened up from the plug. He lined up the head of his cock to her back passage and grabbed Lily’s hip to help guide her down. The moment his head breached her tight band of muscle, Lily resisted and tried to stand back up. He kept a firm grip on her.

“Papa, it hurts too much!”

“It is supposed to hurt. It’s a punishment.” He pushed down on her hips, watching as her little bottom hole slowly swallowed his length.

When her bottom rested against his lap and his full length rested deep inside of her, Lily paused trying to get used to the bite of pain and the awful feeling of fullness.

“Now raise your hips up and push down on my cock again, faster this time.”

Lily sobbed as she did what she was told. She could feel the ridge from the head of his cock scrape against the tight wall of her back passage.

“Faster, Lily.” She moved her hips up and down on his cock, each time it getting easier as her body adjusted to the assault.

“How does it feel to fuck your own bottom with my cock, Lily?” Rand reached between her legs to stroke her wet cunny.

“It hurts, Papa,” she whimpered.

“I know, baby, but I also know you like a little pain to heighten your pleasure. Your sweet little cunny is dripping with cream. Should Papa let you cum, despite your punishment, because you were such a good girl earlier?” Rand swirled his finger around her clit.

“Oh, yes, please Papa.”

“Push down on my cock, harder…faster…make me cum first.” Lily moved at a furious pace till she felt his fingers push into her hips stilling her as his own hips thrust up. She could feel his cock swell as he came with a growl deep inside her bottom.

“Your turn, little one. I want you to cum while Papa’s cock is still up your bottom.” He rubbed his thumb against her clit as he pushed two fingers deep into her cunny.

The pleasure from his fingers mixed with the still throbbing pain in her bottom was too much for Lily. She came with a shout, grinding her cunny down on his fingers. She leaned back against his chest with a sigh.     

Rand pulled his fingers from her still clenching pussy as he pulled his cock from her bottom. He rubbed his fingers through her cream and his cum.

“Remember Lily. We don’t waste Papa’s cum.”

She opened her mouth.

##

Richard forced a crying Emmie over his lap.

“You were a very bad girl,” he admonished. “Pull down your drawers and ask for your spanking.”

“I’m sorry, Papa. I’m sorry. Please don’t spank me,” she wailed.

“Emmie, right now you are getting twenty smacks. Do you want to make it forty?”

“No, Papa,” she sniffed as she slowly pulled her drawers only half way down, exposing just the tops of her bottom cheeks.

“All the way, Emmie,” admonished Richard. She quickly complied not wanting to anger him further.

“Now what do you say?”

“Can I please have my spanking for being a bad girl, Papa?” she said through her tears.

His flat hand came down on her vulnerable bottom with a loud smack. Emmie howled at the first impact and clutched at his pant leg. He continued to pepper her bottom with swats till it glowed a bright red. Her little feet kicked out uselessly. Emmie would never get used to the hot sting of a spanking. Her whole bottom throbbed with pain.

Richard made her stand up and face him.

“How does your punished bottom feel, little one?”

“It feels all prickly and swollen,” she sobbed as she rubbed each cheek.

“Are you sorry for talking back?”

“Yes, Papa.”

“Good, now go get your cushion and pacifier.” 

Emmie started whimpering. She knew what her cushion and pacifier meant. Papa was going to stick his cock in her mouth. Out of all of her training, she hated that the most. It was so intimate, so invasive. She got her cushion and laid it on the carpet in front of the fire. She knelt down on it and tilted her head back with her mouth open, just like she had been taught. Papa stood over her and pulled out his cock.

Emmie stared at the large, bulbous head as he took a step closer. He traced her lips with his head, his pre-cum leaving a glistening sheen on her cute, pink mouth.

“Open wider, baby.” He pushed his cock past her lips, feeling her tongue swipe around trying to force him out. Richard slowly thrust and then withdrew, each time nudging in further.

Emmie choked as his cock hit the back of her throat. She raised her hands to push against his thighs.

“Put your hands down,” Richard ordered. “Remember to breathe through your nose. Papa’s going to push against the back of your throat again. Try to relax and keep your jaw down.”  Richard closed his eyes as he felt her tight throat squeeze his cock, her tongue stroking the underside.  

Emmie tried very hard to do as Papa asked. It was scary, having his big cock force its way into her mouth.

“Good girl. You took much more of Papa’s cock this time. I am very proud.” Richard gripped his staff and vigorously pumped up and down. “It’s almost over, baby. Just keep your mouth open so I can give you my cream.”

Emmie watched as he tightly fisted his cock, grateful he didn’t thrust it that fast into her mouth. Richard groaned, his cream coated her tongue.

Emmie could feel the silky texture as she took in the salty flavor. She knew better than to swallow. She waited as Papa picked up her pacifier. It had a large round tip to match the head of Papa’s cock. He pushed the pacifier into her waiting mouth and tied the pink ribbons in a bow behind her head.

“Go and lay down on your back in the middle of the bed and suck on your pacifier while I get a few things ready for your training session.”

Emmie did as she was told as Richard gathered up the ointment jar and various sized plugs. He placed them beside Emmie before reaching over to remove her pacifier. Emmie’s wide eyes took in all the scary plugs and started to tear up. Richard stroked her hair.

“Don’t worry, little one. Papa always wants what is best for you. Haven’t you enjoyed it when Papa has made you come with his tongue in your tiny rosebud?”

Emmie nodded.

“And haven’t you always liked it when I pushed my finger up your bottom as I take your cunny?”

Again, Emmie nodded yes.

“I promise, you are going to like my cock up your bottom even more. It will just take some training.”

“Will it hurt?”

“Yes, it will. Very much at first, but we will take it slow. I’m going to stretch your bottom hole each night with one of these plugs.”

Emmie started to sob at the prospect of having a scary plug up her bottom each night.

“Hush. You have such a tiny, tight bottom hole that Papa doesn’t want to harm you when I push my big cock up inside.”

“Why? Why do you have to take my bottom?” Emmie asked as she started to cry in earnest.

“Because it will please Papa and I know it will eventually please you. Now you must do as you are told,” he said sternly, “with no more nonsense.”

Emmie nodded okay, too upset to speak.

“I want you to lift up your legs and hold them there behind your knees. Keep your legs open. Don’t close your knees.”

Emmie hated this position. It always made her feel so open and vulnerable. Shuddering when she heard the dreaded sound of the ointment jar being opened, Emmie took a deep breath to prepare herself. The ointment jar always meant something unpleasant like an enema or her temperature being taken up her bottom.

Richard worked up a nice amount on two fingers. Emmie hissed when he took hold of her punished cheek to hold her steady. Swirling the tips around her rosebud, he could feel it constrict and clasp.

“You need to relax, little one.”

“I’m trying.”

He began to apply pressure to her sensitive ring. Feeling a sense of satisfaction when he felt the tight muscle give way and his fingertips pushed in past the first knuckle.

“Ow…ow…ow…,” whimpered Emmie, gripping her knees harder.

Ignoring her pain, Richard pushed in further till both fingers were in to the hilt. He rocked his fingers back and forth, coating her tight passage with the thick ointment.