Alex and Penelope Ch. 13

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Author’s note: This chapter involves an anal plug. If this is something that bothers you, it is easily skipped and nonessential to the plot; only furthering Alex’s “training” of Penelope. Just as things should be with anal, I’ve been very delicate with the nature of my words.

If this is the first chapter you’ve read in the series, I highly suggest you check my profile and start from the beginning.

Thank you!


It had been a few months since Alex had really been able to dedicate any time to Penelope. While he’d hoped to keep training her, their time had been severely limited with his work, her classes, and Claire in the house.

And this week had been no different. Another day, another crisis. So their evenings were spent sweetly in bed, rinsing and repeating what had been done, but with new vigor. Alex was free, and so was Penelope.

But while Penelope was in school, Alex had a hard time concentrating on work, which is why his nights were going so late. He’d spent the entire weekend celebrating with Penelope, but now that they were free anytime they wanted, he could focus on his plans for her. Just thinking about what he wanted to do made him hard, and at six PM on Thursday, he dismissed Jessica, even though they had more to go over.

Jessica understood why he couldn’t concentrate very well. His wife was gone, and though she’d never liked Claire, and knew that Alex was unhappy with her, she kindly told him to take it easy tonight and tomorrow. That she’d work hard to make sure the bulk of his appointments were rescheduled for next week when he was feeling more up to it.

Alex and Penelope enjoyed another wonderful meal cooked by Beverly. When finished, he told her to head on upstairs to his room, then made his way to the kitchen.

“I’d still like the both of you here tomorrow morning through lunch, but I think you should take the weekend off,” he told her, barely maintaining composure. “I’d like to relax by myself until Monday while I sort things through.”

“And Penelope?” Beverly asked. “How is she with the news?”

“It’s been a surprise for the both of us,” Alex said.

“Of course,” she agreed. She’d seen how Claire had treated Penelope, and had almost said something a few times, even though it could have put her job in jeopardy. It would be nice for Alex and Penelope to spend some time together, maybe have some fun. Alex seemed like he needed it, and Penelope must be feeling relieved. “If you’re absolutely sure you won’t need us, I think we might leave and visit my sister in Massachusetts.”

“What a good idea,” Alex said jovially. This way he’d really have her all to himself, without any worry of anyone on his property. “Can I help you with that? I’d be happy to have my pilot take you.”

“Oh, I can’t,” Beverly said, overcome. “We can book a flight tonight and—”

“Unnecessary,” Alex cut her off with the wave of his hand. “First thing tomorrow, I’ll have him ready to go by . . . four?”

Four being exactly when Penelope got home, so they’d have cleared out by then.

“Oh, you’re so good to us!” Beverly cried. “Thank you so much!” She couldn’t help herself from hugging him, then blushed in embarrassment. Luckily, Alex smiled at her and lightly kissed her cheek, thanked her for how wonderful she and her husband were. Told her that she deserved it.

He waited until Beverly and Reuben had left out the back, then went up to his room.

Penelope was waiting on his bed, reading a book. Still dressed. That would have to change.

Penelope smiled up at him, then set her book down on the side table. It was amazing to be in Alex’s room now, though she hadn’t moved her things. She figured she’d wait until invited to do so. Because they’d had so little time together over the last few months, she wasn’t entirely sure where she stood with him now. Though last night had been amazing, so he must still want her, especially since he’d told her to go to his room after dinner.

Alex sat down at her hips and leaned down to kiss her. They’d celebrated for nearly a week, and he’d enjoyed it. But they’d need to talk tonight about where they’d go from here. He just hoped she remembered what she’d originally agreed to. Six months or so of learning from him to be sure they were sexually compatible. She’d been amazing so far, and he cared about her deeply. But sexual compatibility was extremely important in a romantic relationship, and there were things he wouldn’t be able to let go of.

“I know the last few months have been rough on you,” Alex said gently. “But it’s over now, and we can go back to the way we started.”

“I really missed you,” Penelope admitted. She was so ready to pick things up again after many lonely, sleepless nights. She’d fallen for him hard from day one, and couldn’t believe they’d finally made it through their biggest hurdle. It still didn’t seem real.

“Before we do anything tonight, I just wanted to discuss once more what we talked about a few months back,” Alex said. Penelope nodded, sitting up. He güvenilir canlı bahis siteleri stroked her cheek. “You are so lovely, and I want this to work. I care about you so much, Penelope.”

“I care about you too,” she said, feeling a relief through her body. He still cared about her and wanted her. She couldn’t have been happier.

“We’ve done a lot of things,” Alex continued. “And I think we’ve both enjoyed them all.”

“Oh, yes!” Penelope agreed, grinning.

“But we also have a long way to go,” Alex said. “We’ve barely scratched the surface, and I need to make sure again that you’re still willing to let me teach you everything.”

Penelope’s grin faltered, though only a little. She wanted to learn everything he had to teach. She wanted to be what he wanted, and would do anything to make him happy. But she felt like they’d done a lot. They’d had sex, she’d sucked him, he’d licked her . . . he’d even touched her ass that night in the hotel. She wasn’t sure what more there could be.

“I want to lay out a few things,” he said, rubbing her thigh. “We’ll be doing a lot in the future, and some of it might surprise you. But now that we have the house to ourselves, I need to be sure that you still mean it when you agreed to let me teach you, and that you’ll at least try everything once.”

Penelope nodded, looking him straight in the eye. “I still mean it.”

“Good,” Alex said with approval. “We’ll start here, then. I’ve given Beverly and Reuben the weekend off, and plan to now every weekend so you and I can share them alone. We will have to make the occasional appearance at parties and such, but otherwise I expect you here for me from Friday to Monday. Can you agree to that?”

Penelope thought about her friends, and the invitations she might have to turn down. “If a friend asks me out . . .”

“Then we can talk about that,” he said. “You’ll have to ask my permission, because on the weekends you are mine.”

That she could do. She wanted Alex more than she wanted her friends anyway, and they’d have time at school or weeknights to see them. She rarely went out on the weekends as it was, and usually only to escape Claire. Now that was no longer an issue. “I can do that,” she said with a nod.

“Good,” Alex said, rubbing his hand higher on her thigh. He felt her shiver and smiled. “So I have a rule now for the weekends. You’re to come immediately home from school on Friday’s now unless I give you permission to go out. From Friday to Monday morning, you are not allowed to wear clothes.”

Penelope gasped. It took a second to regain composure as her mind caught up. She didn’t know what to think. It meant they’d be playing through the weekend, which was all she wanted. She could spend every waking moment with him. But rules? She hadn’t exactly expected that. She was an adult.

But she was also his. And not only did she want to be, it also made her aroused that he was telling her what to do.

“When we’re not playing, I expect you in lingerie or less, depending on the weekend. For this weekend, lingerie will be fine.” Alex was getting hard as he laid out his rules for her. He was going to train her to bow to his every wish and command now. “That means that when we eat or watch tv, you’re not to be in anything other than the lingerie I give you. It’s only temporary; just until we’ve tried everything we can, but you might find you like it. Sound like a plan?”

Penelope nodded, her eyes wide. “Yes,” she said quietly.

“So when you come home tomorrow, you’re to immediately come up to my room and undress to your lingerie and wait for me. Can you do that?”

Penelope nodded.

“We have a word established, but it’s only to be used once we’ve started and not before to get out of it because you want to do something else,” Alex continued. “I expect you to at least try everything because I think you’ll like it. The word is only for the times when you feel something needs to stop. Are you still with me?”

“Yes,” Penelope said under her breath. She was surprised at herself; at how these demands were turning her on. She would never say no to anything he asked, and she’d drop anything for him if he wanted her.

“Good,” Alex said. “So tonight is your last night of freedom,” he said jokingly with a chuckle to punctuate that he wasn’t really serious. “We’ll do whatever you want to do tonight.”

Alex waited, hoping she’d want to play. He was hard now, knowing that he now owned her completely, without anyone getting in the way. And, oh, the plans he had for her. The things he would do to her.

“I want you,” Penelope said simply, a gentle smile on her lips.

“Then you have me,” Alex said.


Friday after school, Penelope immediately went upstairs to find Alex had laid out a set of lingerie on the bed. She’d worn some under her clothes today, but these were new. The bra was black satin, as were the panties. There were also thigh highs that connected to a belt with suspenders. She put them on, checked herself over in the güvenilir illegal bahis siteleri mirror, then sat down on her bed to read the required text in a book she’d been assigned today.

It was difficult for Alex, but he wanted to make her wait. So he pushed himself to work until six, then dismissed Jessica. Once she’d left, he called up the stairs to tell Penelope to come down to dinner. He wanted to be sure she’d followed his dress code; make her eat while half naked so he could stare at her.

He went to the kitchen and pulled out one of the dishes Beverly had cooked for this weekend for them to heat up, then while waiting on the food to warm, he uncorked a bottle of wine and grabbed two glasses.

When he entered the dining room, she was standing by a chair in the black set he’d laid out for her, and he smiled, pleased. “Very nice,” he said to her, then set up two glasses directly across from one another in the middle of the table. “Have a seat and drink some wine. Dinner will be ready soon.”

Penelope sat down, feeling a little strange to be in lingerie while Alex was still wearing his standard white collared dress shirt and black slacks. But sitting down covered the bulk of her body, and the wine would help her relax. She took a big sip and watched him head to the kitchen.

Alex returned with two plates and sat down, able to see Penelope’s perky breasts in the black satin bra. Maybe next weekend I’ll require that she’s naked, he thought to himself. Though that would probably take a little working up to. Maybe in a few more weeks. For now, this was amazing enough.

They talked through dinner and finished off the bottle of wine, which Alex thought was a good idea. Tonight he’d begin some training that she’d need to be relaxed for.

Once he’d cleared the plates, he helped her from her chair and walked her upstairs to his room. He’d have to start calling it their room, as he never planned to let her sleep anywhere else from here on out. But her things were still on the other side of the house, which was probably good. They were still a secret, and would continue to be for a little while longer. He didn’t want Beverly and Reuben to find her clothes in his room just yet.

Alex sat her down on the end of the bed, then leaned her back while crawling on top of her to kiss her lips. He worked his way down her neck, then across her chest. He still couldn’t believe this was real; that he had Claire gone and would soon be divorced. That he had Penelope all to himself whenever he wanted now.

He rose onto his knees between her legs and let his hand cup her pussy over the satin panties. He watched her smile up at him as his fingers rubbed; her arms lift over her head in pleasure with tiny moans. With his other hand, he located the buttons on the suspenders and released them so he’d be able to take her panties off. He’d keep the rest on for now. He liked how she looked in it.

Lacing his fingers into the tops at her hips, he climbed off the bed, taking the panties with him. While working them off her legs, he stared at her hairless pussy, ready to get to work on it. As he climbed back between her legs, he spread them a little wider, enjoying what they revealed.

Penelope felt his hands stroke her, his fingers light and soft. She moaned in ecstasy from his touch. When she felt his fingers slide down to her hole, she braced herself for entry. A second later, his finger was inside of her, tickling her inner walls.

Alex fingered her until she was wet. He was ready to fuck her, though that wasn’t his end game tonight. But his cock was hard and needed to feel her tight pussy around it. When he deemed her sufficiently ready, he unbuttoned his pants and freed his cock, leaving them on. He positioned, then slid inside.

Penelope loved how full she felt with Alex’s huge dick inside of her. He stretched her, and she always felt pain initially; pain that would eventually turn into pleasure as he worked her. She liked the pain now though. It made her fully alert and awake, serving as a reminder that his cock was inside of her, and that she never wanted to be without it.

Pumping at her, Alex hovered over her body and kissed her neck. His motions were cyclical, not thrusts yet. Just feeling her tight little pussy grip his cock and massage his shaft. “I own you now,” he said to her, looking into her eyes. He couldn’t help himself. Soon he’d have worked her up to calling her all sorts of names, but for now, he was reminding her. “I own your pussy.”

Penelope moaned as she heard him say it, turning her on even more. He did own it; she’d given it to him freely, and would continue to for as long as he wanted it.

Alex picked up the pace. Her legs wrapped around his back as he began to fuck her. With each hard thrust came a cry. He could listen to those cries for hours on end, and would, without a doubt.

It didn’t take too much longer; he’d been hard for her all day knowing that today was when it all really started for them. This was just the beginning. güvenilir bahis şirketleri After about five minutes of giving her some force, he brought his hand down to rub her so she’d come with him. Just before his release, he got his finger on her clit and pushed down as he came, feeling her muscles flutter against his shaft.

He stayed inside of her for a few more minutes, feeling her aftershocks, then slowly slid from her. He climbed off the edge of the bed and opened a drawer containing all the items he’d ordered specifically for her that used to live in a guest room.

“Lay on your stomach for me,” Alex said.

Penelope rolled over, still feeling her body quake from her orgasm. She couldn’t believe what she’d missed out on all these years, but was glad her first had been Alex. She watched him squeeze a bottle over his hand, a clear liquid falling to his palm. He rubbed them together, then sat down beside her and began massaging her shoulders.

It was important that Penelope was totally relaxed, so Alex massaged her with oil for a good fifteen minutes, working her muscles. He felt them ease under his fingers until she was completely relaxed and limp. He then reached back into the drawer for the bottle of lubrication, and squeezed a quarter size dollop into his palm. He left it there and massaged her ass cheeks with his oiled hand, now dry enough to move them around.

“Why don’t you get your knees up,” he suggested.

Penelope lifted herself and brought her knees under her, then relaxed back down, using her crossed arms to steady her head. She felt Alex massage her ass and was already feeling aroused once more. She could never get enough of him touching her anywhere, but there were certain areas that really got her going, and her ass was one of them.

Alex was able to see between her cheeks now, so he ran his fingers in the lube. He placed two against her tiny rosebud and heard her gasp. He didn’t move. Once he saw her shoulders relax, he rubbed softly in little circles, massaging her hole.

After a few minutes of this, he poised his middle finger and gently pushed.

“Oh my god!” Penelope cried, unable to stop herself. He’d touched her here before, but this felt different. He’d definitely gone inside a little, more than he had the previous time. Last time it had just felt like a little pressure. This time she felt . . . wrong.

“Relax, Pen,” Alex urged, able to feel how she clenched. He made little circles against the muscles to ease them open. “You need to relax and let me do this. If you tense up, it’ll only make you hurt.”

Penelope tried to focus on relaxing, but the task seemed impossible. How does one relax when something like this is happening?!

After another minute, Alex pushed further, to his first knuckle. She cried out, but once he paused, the cry died out and there was only quick breathing left over. He again repeated the action of making small circles with his finger.

Then he pushed once more, to his second knuckle.

“Oh, no!” Penelope cried. “I can’t!”

“You can,” Alex said soothingly. “And you will. Just relax. You’ll like it, I promise you.”

This was absolutely happening. It was time to start training her ass so eventually he could work up to her taking his cock, which would be no small feat. She was tiny and he was large, and her muscles did not want him in here. They clenched with such force that he felt like the blood had been cut off to his finger.

He curled the tip slightly, listening to her cry with his movements. Her cries only made his cock hard; made him want to give her more. He spun his finger and curved again. Keeping it curved, he twisted his finger around in semicircles, getting faster with each one.

It was time.

He eased out of her and returned to the drawer. He located the smallest of the plug’s he’d ordered, a pink one that was the size of a pinky at the tip, the size of a thumb at its widest before it’s thin base. There was a larger circle at the end to keep it in place once inside.

Careful she couldn’t see, he lubed it up near her ass so she wouldn’t know what it was until after it was inside. Placing it against the tiny hole, he urged it inside.

“Oooh!” Penelope cried. Whatever he was doing was cold and hard. It was unlike his finger, which meant it was something else; something he’d grabbed from the drawer. A vibrator maybe? She didn’t think she could take that if it was turned on.

Alex slowly fed the plug inside. It was easy with how slick it was, though he was still very careful so he didn’t cause too much discomfort. When it hit its widest part, Penelope wriggled. “You have to relax!” Alex cried. “Shhh. I’m not going to hurt you. You’re only hurting yourself. Just breathe.”

Penelope’s breaths were short gasps, and she knew she probably sounded like a woman in labor, but she had no control over it. She felt so stretched in such a bad place!

Then, suddenly, it was like the thing had been sucked inside. She felt a force, then her muscles eased a little.

Alex watched as the plug sunk in, sucked without him having to push. It was now embedded inside, her muscles wrapped tightly around the thin base. He brought his head back and admired her ass. Where a hole should be was covered with a flat pink circle, holding a plug inside of her.

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