Best Laid Plans – Part 1 – Chapter 6

They continued to lounge in the bed for another twenty minutes, laughing and talking.

The stress Pam had felt all week was gone as Ted had agreed to continue their relationship. He had brought her to his bed, where he had brought her to orgasm repeatedly and ruthlessly.  It had taken her all of the twenty minutes to get her heart rate back down to normal. She was glowing inside now that she understood what a phenomenal lover she had. As Pam would admit, she was anything but a virgin. She had shared her bed with at least a dozen men since giving up her virginity in high school. But not one of those men could begin to compare with Ted. His ability to bring her to orgasm was simply beyond comparison.

Ted reached to touch her cheek. “I think it’s time we had something to eat. The odds are we’ll get wild and crazy again before the night ends.”

“I certainly hope so,” Pam replied, taking one of his fingers in her hand and moving it to her mouth. “You can’t give me half a dozen orgasms and expect me to sit quietly the rest of the night.”

“Then, perhaps I should give you one of your presents before we eat,” he said as he rolled off the bed and walked into his closet. Ted sat on the bed and handed Pam a box. “I didn’t have time to wrap it,” Ted apologized.

Pam grinned from ear to ear. “I love presents. They are always so wonderful, especially this one, as it’s the first present you give me since I’ve become your mistress.” Pam sat up and opened the box. She found a small piece of tissue paper and quickly pulled it out. “Oh my,” she gasped as she reached inside the box and removed a glass butt plug, holding it up to admire it.

“You know what that is, don’t you?”

“Sure,” she replied in a whisper. “It’s a butt plug.”

“Have you ever had one?” Ted inquired.

“No,” she whispered, still examining the glass object. “I’ve never had one or used one.”

Using his serious voice, Ted said, “You’ve told me that you will never tell me no. You’ve said that you are mine to command.” Ted put his hand on her bare leg and looked into her eyes. “Baby girl, you have the finest ass I’ve ever seen, and I must have it. This little tool will prepare you for anal sex.”

He studied her facial expression before saying, “Look in the box. There’s something else in it.”

Pam put her hand in the box and removed a tube of lube.

Ted thought she might have blushed.

“How does it…” Pam’s voice faded away.

“Well,” Ted said, taking the toy from her hand. “I suggest you cover the thing with a large glob of lube and then insert it into your ass.”

“Show me how,” Pam insisted as she rolled over on her tummy and spread her legs.

Ted had felt this would happen, so he wasn’t surprised or upset.

“First,” he said, while opening the tube of lube, “We apply some of this slippery stuff directly to your rosebud.” He covered his thumb with the colorless product and touched it to her puckered opening. Ted pressed his thumb directly against the hole before moving his digit around in a circle.

Pam was still exhausted from their earlier activities and couldn’t attempt to stop him even if she wanted to.

After slowly stroking her anus, Ted added more lube to his thumb and pressed it into her pucker. He could feel that her relaxed state allowed him to penetrate her lovely ass easily. Ted pushed his thumb in up to his first knuckle and stopped. “How does that feel?”

“It feels naughty and dirty,” she answered, her mouth in a pillow. “But it feels good,” she added before giggling.

Ted took his thumb out and added more gel. He then reinserted his thumb, this time, all the way. Ted smiled when Pam growled. “Still good?” he asked.

“Fuck yes,” was her answer, with her face deeper in the pillow.

Ted left his thumb inside her ass for several minutes while his fingers played with her wet pussy. Finally, he slipped one of his fingers inside her vagina before gently gliding both finger and thumb in and out of both her holes.

Pam’s growl got lower and louder.

After another minute, Ted took his hand away and picked up the butt plug. He gave the plug a liberal coating of gel before bringing it to Pam’s asshole. “Just relax,” Ted whispered as he began pushing the glass toy into her.

When the toy popped into place, Pam made an audible gasp. “Fuck!” she said.

“Now we’re going to leave it where it is for a while,” Ted explained. “I assume you can feel it.”

“Indeed, I can,” she replied. “But when do I get your cock in there?”

“Let’s just say that we’re in anal training right now,” he said and patted her bottom. “Let’s get something to eat and discuss it.”

Pam looked back at Ted. “Are you going to take it out now?”

“Nope,” he said as he stood. “The whole point is to prepare you for something else and your mind centered on the right things.”

Ted took her hand and helped her slide off the bed. Once she stood, he got one of his shirts for her. Ted helped her put it on and buttoned it enough to still show what he wanted to see. He took her by hand and led Pam to the kitchen.

“Can you feel it when you walk?” he asked.

“You bet,” she answered in a soft voice. “How could I not feel it?”

“That’s the point,” he told her with a grin. “Now then, let’s start with a nice bottle of wine. I’ve already made sure that we have enough for the weekend.”

They spent the next twenty minutes sitting at the kitchen island, eating, drinking, and talking. Ted noticed Pam fidgeting and seemed to be losing track of their conversation.

“Is something wrong, Pam?” he asked.

She looked at Ted with wide eyes. “Do you suppose we could go back to the bedroom? This butt plug is driving me crazy, and you might say I’m so horny I’m about to scream.”

“If that’s the case,” Ted replied with a grin, “let’s go.”

By the time she was inside the bedroom, her shirt was on the floor. She was naked again and moved onto the bed. Pam was on her hands and knees, with her butt facing Ted. “Take care of me, Ted!” she demanded. “Fuck!” she shouted. “I want it right now!”

Ted dropped his shorts before walking up behind her. He saw that she was dripping wet and decided to warm her up a bit before taking out the butt plug. This time, Ted was not concerned with pleasing Pam for the first time in quite a while. His cock was so hard that it hurt, and he knew the only thing that would make that pain go away was slipping into Pam’s hot pussy and fucking her hard and fast. His gentleness was gone, and he just wanted to mount her and ride.

He moved over her and felt the cool softness of her ass cheeks against his belly. He might have wanted to linger over that feeling for a while, but the tip of his cock came in contact with Pam’s pucker. Half of the head was inside her when he felt her heat. He hesitated another second before pushing it inside her cunt, listening to her loud groan. She was so wet and hot that he didn’t hesitate a second before thrusting his cock in and out of her. By his third stroke, she was making noises, and by the sixth, she was encouraging him to go deeper, harder and faster.

He assumed that the excitement of the moment and the uninhibited sex made her talk this way, but he was totally aroused. With every stroke he pushed into her, she met him with a push in the opposite direction. But when she reached between her legs, grabbed his balls, and squeezed them, he knew it was time to move on to the next stage. 

Ted pulled his cock out of her pussy and began to stroke it up and down the crack of her ass. He was so well lubricated from all the flowing juices inside her pussy that he decided he wouldn’t need more lube to enter her ass. Ted took the end of the plug in hand and began to twist it. “Can you feel that?”

“Yes!” she said loudly. “Take it out. I want your cock in me now!”

Ted twisted and pulled on the plug until it popped free. Putting the head of his cock against her gaped opening, Ted slowly pushed about halfway into her. To his surprise, when half of his cock head was in her, Pam pushed back hard enough to make it sink all the way in.

For several seconds he held still, just feeling how wonderful it was to be in her ass. He was feeling the coolness of the skin of her butt pressing against his belly. The tight skin of her bottom pressed against his pelvis, and the softness of her beautifully rounded ass overwhelmed him.

Finally, Ted leaned forward, saying, “Does that hurt, love?”

He was a little surprised when she answered. “No, it doesn’t. In fact, it feels quite wonderful.”

Her response wasn’t what he was expecting. “Really?” he asked.

Her voice was soft when she said, “Honestly. It feels wonderful. Don’t move for a few seconds, and let me adjust. You’ve stretched me to my limit, but I think you could easily make me cum this way.” She paused for a few seconds before saying, “Could you move just a little? I want you in my ass, but I want you to be gentle for now.”

Ted moved slowly, pushing in and out an inch at a time, hoping not to create pain. This wasn’t how he had imagined he would take her beautiful ass, but here it was, by her request, and he thrilled at the sight of his cock disappearing inside her ass hole.

“Deeper, baby,” she said in a loud whisper. “Give it to me a little harder.”

Ted was happy to grant her request but quickly realized that getting what he had wanted for such a long time had pushed him toward a climax. He was hoping not to spoil the moment by getting off prematurely when he heard Pam say, “Cum in my ass, Baby. I want to feel you cum inside my ass!”

Her plea wasn’t soft and gentle. It was a demand, and Ted lost all control. Within seconds, an explosion erupted in his head and cock. Hot cum shot out and up her ass. Pam pushed back against him driving his cock even deeper into her. Another explosion of hot cum, and again she thrust back against him as she cried out. A third explosion, and she pushed back hard against him once again until his cock was completely buried inside her sexy ass. She pushed back one more time, his cock exploded, and one more volley of cum flooded into her.


Despite his just having a massive orgasm, his cock was still as hard as he could ever remember. He slowly moved his cock out and back into her, feeling that she was totally lubricated by the spunk he had just deposited in her. He moved a little faster. It felt as if he was driving his cock through a silky glove that gripped him tightly. She was soft, tight, and hot. He heard her soft moan and then felt, more than saw, her hand move between her legs to rub her clit as he fucked her ass.

At this point, his cock was so sensitive that each thrust into her sent shivers through his body. Ted was just moving out of instinct, hoping to please her. He was happy that his member had remained extremely hard, allowing him to continue to excite and satisfy her. He thrust progressively harder and deeper when he heard her start making pleasure sounds.

“Give it to me hard,” she almost yelled at him. “I’m cumming. Oh god, I’m coming.”

Ted pounded into her ass hard and fast until he felt her go limp under him. After waiting a while for her orgasm to subside, he removed his cock from her tight, slippery tunnel.

“Not yet,” she whispered to him. “Please, just leave it there a little longer.”

He waited another minute before he slowly pulled out of her. Standing behind her, he looked down to see her hand between her legs.

He watched as his cum began to seep out of her ass, slide down between her legs, over her pink pussy, and finally drop in her hand. After the second drop hit her open palm, Ted heard her chuckle before she said, “I wonder what that could be?”

“Some people will just do anything to keep from getting a wet spot on the sheets,” Ted said with a chuckle before tenderly kissing her ass cheek. He moved away from the bed, heading for the bathroom. Coming back just a few minutes later, he found that Pam had not moved. Her hand was in the same spot but was now covered with his cum. He placed a hot washcloth over her exposed rosebud and was rewarded with a loud moan. As he gently cleaned her butt and hand, she purred with satisfaction.

“I never thought I would enjoy someone washing my behind,” she told him, “But that feels almost as good as your cock inside me.” When he stopped, Pam turned over and gave him a big smile. “You really know how to show a girl a good time, big fella.”

Giving her an equally big smile, Ted said, “I always try to make my guests comfortable, but I don’t recall having gone to this extreme before.” He turned to go back to the bathroom, stopped, and said, “But I certainly hope that I get the chance to do it for you again.”

“Based on my recent experience,” she responded, “I think the chances of that happening again are extremely good.”

Ted came back and lay down beside Pam. “So, what do you think of your first experience with anal sex?”

“I think the jury is still out on that,” she said. “I think we’ll have to try it again to arrive at a final assessment. I should think another twenty times will lead us to a final decision.”



Pam opened her eyes on Saturday morning to see she was alone in bed. The clock beside her showed 10:23 AM. “Good lord,” she sighed as she threw back the sheets covering her. Pam grabbed a shirt and pulled it on without using the buttons. As expected, she found Ted drinking coffee and reading the newspaper in the kitchen.

“Were you going to let me sleep all day?” she asked with a tone of seriousness.

He smiled and replied, “I was going to wake you at 10:30. You woke up early and spoiled my surprise.”

Pam pulled his face between her breasts and ruffled his hair. As his mouth worked its way to one of her nipples, Pam noticed that Ted had set two places on the island with silverware, napkins, and coffee cups. “Were you planning on feeding me?”

Ted let go of the nipple and looked up. “If I’m going to continue using your body as a personal sex toy, I’ll be required to keep you nourished. It’s nothing fancy. I have a coffee cake in the oven to keep it warm. Just take a seat, and I’ll feed you.”

Pam started to take her seat and saw a box in the middle of her plate. “What’s this?” she asked, picking it up.

“That’s another gift,” he replied while removing the coffee cake from the oven. “You seemed to enjoy the gift from last night, so I thought you deserved another.”

“I can’t imagine anything better than last night’s gift,” she said while shaking the box gently.

“Go ahead. Open it,” Ted said while pouring a cup of coffee for her.

She noticed that the top of the box had the word ‘Lelo’ printed in gold letters. As she began to open the box, she thought it looked expensive. With the top removed, Pam looked inside. “What is it?” There were two things inside the box, but their use wasn’t evident.

Ted set the cup down by Pam’s plate and took the box from her. He took out the smaller item and put it in her hand. “This little egg-shaped thing goes into your sweet pussy. The little tail on it remains outside.” He put the gadget in her hand before taking out the other item. “This is the remote control that gives directions to the egg.” He pushed a button on the controller, and the egg in her hand began to vibrate.

“Oh my,” she gasped, looking at the egg in disbelief.

“Go ahead,” he suggested. “Put it in, and let’s see how it fits.”

Pam spread her legs and slowly pushed the egg inside her pussy. Once it was in, she asked him, “Is that right?”

“It looks right to me. Let’s just test it.” He pushed a button, and Pam gasped.

Pam stood in front of him with her eyes wide and wearing a crooked smile. “Oh my!” she said again.

“It has five levels of vibration speed,” Ted explained as he changed the vibration from one level to the next. “It also moves.” He pressed another button as Pam sat down with her legs spread apart. Ted continued to push the controller’s various buttons, and Pam continued to be amazed.

Ted leaned over to kiss Pam before setting the controller down. “I saw it at the adult toy store and thought it might be a fun thing for us to have. I can just imagine that we can have a lot of fun with it at the office.”

“You plan on using this… thing on me in the office?” Pam asked in disbelief. “I’ll never get any work done if you tease me all day.”

“You’ll be the most relaxed woman in the office.” Ted picked up the controller and turned on the motion.

“Oh, fuck!” Pam shrieked.

“Wait until you see the one that goes in your ass,” he said while changing the setting with the remote.

“You got something besides the butt plug?” she whispered while enjoying the feeling inside her pussy.

“I’ll show it to you later,” he said with a grin. “It looks like a finger and vibrates. I think you’ll enjoy it when I take you from behind.”

“Turn this one off,” Pam demanded. Her eyes were shut, and her hands gripped the countertop.


Their first weekend as confirmed lovers was long and delightful. Pam came to Ted’s house on Friday night, and they didn’t leave it again until Monday morning. All the new toys had been tried out and found to give exceptional rewards. From the time that Pam arrived on Friday until Monday morning, she was never fully dressed. On Saturday afternoon, Ted had turned on the television to check out which sports were being televised. However, it didn’t take Pam long to convince him that her bedroom sports were much more fun as well as being participatory.

Before Pam left Ted’s house on Monday morning, he handed her the new remote-control toy. “Remember, I want you to have this in when I get to the office,” he told her.

She grinned at him, saying, “I feel that office life will be drastically different from now on.”

Ted handed her the glass butt plug. “I’ll expect you to wear this to work on Tuesday.”

“Are you going to be prepared to work late on Tuesday and lock me in your office after the others go home? If I wear that thing all day, I’ll be climbing the walls by 5:00.”

“That sounds delicious,” Ted laughed. “Now, you go on. I’ll be in around 10:00, and you can ask me about my weekend so the others can hear.”

“Not until 10:00,” Pam asked. “You have another girlfriend coming by for a quickie?”

“I have some research to do first. No one will miss me.”

“I will,” Pam huffed.

“You’ve spent nearly three full days with me. I would think you would enjoy a couple hours without me in your face.”

Pam gave him a mischievous grin. “We could always call in sick and go back to bed.”

He turned her toward the door and patted her butt. “Get going, missy. You don’t want to get into trouble with your boss.”

Pam opened the door and quickly turned back. “That reminds me. Now that we’ve introduced my ‘perfect ass’ into the game, I think that we’ll also need to explore spanking.”

Ted had a quick twitch in his crotch. The idea of spanking her fantastic ass was off-the-charts exciting. “We’ll discuss that later.”

Ted watched her drive off before going into his home office and turning on his computer. He went to the Adam & Eve website, found the search engine, and typed in ‘restraining devices.’ Ted smiled when the screen filled with a new variety of sex toys. “Yes, here we go.”

Thirty minutes later, he had placed an order and was assured his purchases would arrive by Thursday. Turning off his computer, Ted smiled, “Next weekend should be very interesting.”