Alex and Penelope Ch. 11byrosess©
Author's note: If you enjoy this chapter, please consider going to my profile and starting from the beginning. I also personally respond to all messages, though do not comment on my own stories.
The party was wild, as was to be expected. The invitation had specifically invited single adults only, or couples without children. So it was no surprise when they showed up to see women around the pool already topless and tipsy.
They had arrived a little later than planned because Alex had "forgotten" to book time at the spa for Claire. She wasn't able to get in until noon, so they'd had to wait on her. Luckily it had given Alex and Penelope an hour or so alone.
Penelope immediately saw her friends in the pool and waved at them, joining them after a drink and a quick bite to eat. She was surprised to see women walking around without bikini tops, but Alex had warned her about Katie Spaulding's past, so it made sense.
She spent the entire afternoon with her friends while they shared all the gossip with her, pointing out certain people and telling her their darkest secrets. They had a lot of questions about Claire, but Penelope kept her mouth shut. She would never speak poorly of anyone, and certainly wasn't about to air the news that Alex was unhappy, though her friends seemed to know it.
Alex avoided Claire as much as possible, but it also meant avoiding Penelope. He was happy to see that her friends were here so she wouldn't feel too out of place, but knew she must be dying anyway in this crowd. He was extremely happy when Penelope asked if Ben could take her home because she was tired. He told her of course, knowing things would be getting wilder once the sun set. He wished he could join her.
Once dark, the hot tub filled with naked bodies toying with each other. The pool had couples making out in the corners, and Katie had given her permission to a few to stay over and head on up to their rooms.
Claire showed up at his side with Grace Pemberton and ran her fingers down his chest. "We were thinking maybe we should stay," she said seductively, eying Grace. "You know. The three of us."
Grace put her arm around Claire's neck and batted her eyes at Alex. She was lovely. Petite, black hair and dark eyes. But his answer was easy. "I'm up early to catch a flight," he said, his apology more to Grace than to Claire. "I should probably leave now, but stay if you wish."
Grace excused herself while Claire leaned in and hissed, "What the fuck is wrong with you?"
"I'm just not feeling it," he said with a shrug. He was, a little, and the thought of fucking Grace was intriguing. But he wasn't feeling it for her like he did for Penelope. And he certainly wasn't feeling it for Claire. "You staying or coming?"
"Fine, let's go," Claire said angrily.
They made their goodbyes, then left the party. Claire raged at him the entire ride home, but it was in one ear and out the other. He missed Penelope, even though it had only been a day, and was greatly looking forward to having her to himself again this week.
Alex, Penelope and Jessica caught a plane at six in the morning so Alex could make it to his eight AM appointment, the first of many. Once they arrived at the hotel, their bags were brought up to their rooms by bellhops. Alex paid the guy a twenty and sent him on his way, then turned to Penelope.
"Today's the worst of it," he said.
Penelope nodded once. "I know."
He let out a long sigh, then dashed over to her and swept her into his arms, planting kisses on her lips, cheeks, and neck. "I've missed you," he said honestly, something he didn't think he'd said in his life.
"Me too," Penelope said, grasping him tightly to her. She didn't want to let him go.
"Do whatever you want today," he said once he let go. "I'm sorry I can't stay, but relax here and order room service or a massage, or head out . . . just be careful if you're out alone."
After assuring him she would, he ran out the door to meet Jessica in the lobby.
Penelope spent the day in the room, fascinated by how luxurious it was. There was a large living space that could entertain at least fifty people, with a grand piano near the windows. A terrace stretched across the span, with two bedrooms on either side of the living space. There was even a bar and a kitchenette. She ordered lunch midafternoon, which was served to her under hot metal lids like she'd seen in movies.
After a shower, she dressed in a purple sheath gown and met Jessica for the musical.
She'd never been to a real theatre before. She'd been in a few of her high school's productions, but that was about as good as it got. This was too amazing. The lobby had crystal chandeliers hanging from the decadent ceilings, and the musical itself was an amazing production. She took it in with wide eyes, unable to think of much else outside of what was happening on the stage.
When she returned to the room, Alex was waiting for her on their bed, no longer in a suit, but still in black slacks and a white shirt. She ran to him and jumped up, ignoring the fact that she was in an evening gown, and threw herself on top of him, kissing him deeply.
It was eleven, and Alex was wiped, but once he had Penelope in his arms, he could think of nothing else he wanted other than to take her, despite having a six AM wakeup call. It felt like it had been months rather than days since he'd had her.
"Okay," he chuckled, grabbing her and helping her off. "How was the show?"
"Oh, it was perfect!" she cried happily, climbing off the bed. "Everything about it. I cried at the end."
Alex rose and turned her in his arms, letting his fingers mold around her breasts. "I never want to hear of you crying."
"But it was only because I was so happy," she said, leaning back against him. "Thank you for the tickets. Jessica cried too!"
"Jessica cries?" he laughed, unable to think of his assistant like that.
"How was your day?" Penelope asked.
"Long and hard," he said, then kissed her neck. "Very much like my cock right now."
"Mmmm," Penelope moaned, pressing back further. Sure enough, she could feel him against her lower back.
Alex located her zipper and pulled it down her back, then shrugged her straps off until the dress had met the floor. He was happy to find she was in those sheers he'd bought her, minus the waspie. Kissing her neck, he unclasped the back and pulled the bra from her, then reached around her and clutched her tits, using them as handles to pull her back against him.
Penelope moaned, letting her head fall back against his shoulder, sinking into the feeling of his body against hers. She felt his hands slide down her stomach and meet her hips, then his fingers dip into her panties. He slid them down slowly, then reached between her legs and massaged her. She felt as though she'd collapse, as though her knees would give out and it would only be that hand holding her up. She wanted to balance on that hand for the rest of the night.
Alex spun with her until she faced the bed, then lifted her until she was able to climb onto it. He'd expected to be too tired to mess around these first few nights, expecting it would be Wednesday before they found the time. He was tired, but now that she was here, there would be no sleeping until he'd fucked her.
"Stay like that," he whispered. Her knees were bent and her elbows had her propped up, perfect for him to fuck from behind. He unbuttoned his pants and pulled the zipper down. They fell down his legs to his feet. He pulled his cock from his boxer briefs, leaving them on, and rubbed himself with one hand while toying with her pussy.
Penelope felt a finger dip inside of her and she let out a moan, then looked back at him over her shoulder. She could see him rubbing himself, his eyes on her ass, and she smiled. She was ready. She didn't care how he did it; hard, soft, slow, fast . . . just as long as he did. She needed him just as badly as he needed her.
Alex positioned himself and fed her his cock. "Uuuhgh," he moaned as he felt her muscles grip him, still so tight it was unimaginable until felt. They definitely needed to get some sleep tonight, so he'd have to be quick with it, not that it would be a problem. He'd been ready to cum the second she'd walked in the door after just thinking about her. He got his hands on her hips and pumped himself inside of her, focusing on what she felt like hugging his dick. No man alive would ever want for anything after being inside of her, and he knew how lucky he was.
Penelope rode each thrust feeling like a pro now. There was nothing she couldn't handle at this point. She'd sorta hoped he'd give her another chance to prove herself on top, as she knew fully that she could do it now. She had hit a point where she didn't feel normal without it inside of her, though it still stretched her to the limit. She liked the pain of his girth; liked that every muscle and nerve fired rapidly when he was inside. Mostly she just liked the feeling of being filled by him, as she never felt she could be close enough, even with him inside of her.
Alex groped her ass, pinching it and enjoying how it would leave red marks when his fingers left it. Oh, how he wanted to make that ass of hers red, covered in handprints and welts by the time he was finished with it. He mentally promised himself that after they got back home, that was exactly what he'd start to do. He'd require that her ass was red and swollen for at least a week, maybe longer. He'd find a way to make her give him cause to do it, though he'd do it none the less.
His thrusting was harder now as he thought about her ass and all the things he'd like to do to it. He was so close now, and they'd only been at it for no more than ten minutes. God, he'd really needed this.
Just as he felt himself crest, he reached around and rubbed her hard with his fingers. She moaned, her hips bucking back to meet him now. Just as he located the hard little nub with his fingers, he unloaded. With his orgasm, his fingers pulled up against her hard and he felt her muscles spasm around his cock, sending another load shooting into her depths.
Still inside, he couldn't get her ass out of his head. And then he decided it was time. He'd planned on waiting much longer before training it. He'd still wait until they were home to make it red, but he wanted her to have plenty of time getting used to the sensation.
So as he slid out of her, he kept her hips where they were so she wouldn't collapse.
Penelope wasn't able to fall onto the bed like her muscles wanted, so she sort of fell back, her butt meeting the balls of her feet. Her breathing was slowing as she rubbed her face against the soft comforter, still riding out a few aftershocks.
But it had been incredible. Not nearly as much pain as she'd had, more a pleasurable kind from being stretched and prodded. She missed his cock immediately and wanted it back. She turned her head to look over her shoulder at him, finding him still staring at her ass. She grinned, his hands still on her hips.
"More?" she asked playfully.
Alex laughed. She never ceased to amaze him. He rubbed her ass. In the fetal position she was in, he could see that little hole he wanted to train perfectly; just a tiny dark pucker. "Maybe," he said, letting his hands slide inward until his thumbs were an inch away. "If you're a good girl, maybe I'll reward you. But I want to try something."
"I'll be good," Penelope said.
God, she sounded just like the perfect little wanton slut. He smiled to himself. She'd be doing things she never imagined when he was done with her. Though he'd never be done with her. Just done training her.
He slid his thumbs a centimeter closer. "I'm going to try something," he said. "And if at any point you're uncomfortable, you tell me and we'll stop."
Penelope stiffened. Something new was going to happen and she wasn't sure she was totally ready. She moved to sit up, but his hand met her back.
"Stay like this," he said.
Penelope relaxed back down, though she was far from really relaxing. "What are we doing?" she asked timidly.
"Just something new," he said, sliding his hand back into place. "And unlike everything else, you really need to be honest with me about this. You don't even have to use our word. Just say you're done, and we're done."
"But then I won't be rewarded," Penelope said, her brows furrowed. This was something big, and she knew it.
Alex chuckled. "I'll reward you just for trying," he said. "Just relax."
"But if I say no," Penelope began, feeling the worry. She couldn't even finish her thought.
For a second, Alex was confused, but then he remembered their talk and he relaxed his shoulders. "I don't want you to say no to this," he said. "This is something that will take time. I'm only saying that you hold out as long as you can, and when you're done, we stop and we'll try again later."
Penelope bit her lip and nodded.
Using his left hand, Alex lowered it to her still wet pussy and dipped his thumb inside. He heard Penelope's moan of pleasure as he rubbed it around in slow circles while he massaged her right cheek. Once satisfied that it was sufficiently wet with the combination of their juices, he brought his right hand around to her side and held her hip, then slid his left back up onto her cheek.
Very slowly, he moved his hand until his thumb was poised over her tiny little pucker. He lowered it down and let it rest as Penelope let out a yelp, her body jumping.
And that was just from a touch . . .
Penelope was completely lost. He'd just touched her . . . she couldn't even make her mind form the word, and when it did, it felt like she'd whispered it to herself. My asshole, she thought. After the initial shock, she took a deep breath and tried to keep perfectly still, as she'd promised she'd try anything.
Alex waited another few seconds, keeping an eye on her, but her head fell down, held up by her arms crossed at her forehead. Her breathing was quick, but as it evened, he gently began to massage her with his thumb, making small circles. He wasn't exactly a patient guy, but with this he absolutely would be. This was the first step in the longest of his journeys with her, and he knew it would take a long time before she'd accept his cock. Right now he just had to get her used to the idea of something there.
The noises she made were thrilling, as always. Tiny little high-pitched whimpers, that sounded more like eh's than anything else, each coming with a quick burst of breath. He applied a little more pressure, though kept the circles insanely slow.
"How are you doing?" he asked. It was necessary. There would be times he didn't care how she was doing. Well, he'd care, but he'd act like he didn't. This was not one of them. It was extremely important that this was enjoyable or he'd be denied access forever.
"I'm fiiine," Penelope whined, though she wasn't sure that she was. She'd had a lot happen to her, some of it quite painful. This wasn't painful at all, though it was really strange, unlike anything she'd felt in her life. She couldn't imagine why he'd even want to touch her there, but he seemed to want to, so she let him continue. "Yeah," she said, sounding more sure. "I'm fine."
Alex sucked in a deep breath and nodded. She was doing great. This had to be a shock to her. Sex was pretty straight forward; something people expected and knew how to do instinctually. This was another thing entirely. He applied a little more pressure right on her hole until he felt the pad of his thumb sink ever so slightly.
"Ahh!" Penelope cried, mostly out of shock. Was he actually pushing in? That couldn't be right. But it felt that way.
Alex turned his thumb so it was aimed down now and gently pushed until just the middle of his nail. He wasn't to the real muscle yet; in fact, that was what had stopped him. He needed to get to that muscle to relax it, and it was not relaxed. It was absolutely closed for business. So he spent a couple minutes massaging it with slow circles, knowing this was about as far as he'd get to go.
And he was right.
"Okay," Penelope said. "Okay. I think—"
Alex immediately removed his thumb before she could finish, and he heard her relieved sigh. He'd taken virgin asses before with only about a half hour work up, but those women hadn't been virgins only weeks earlier. They'd been experienced, usually enough that they'd had something in there before. A finger, a plug, a dildo, beads . . . .
He had all four ready for her in the coming weeks.
Alex released the hold on her hip and gently urged her to fall to her side. She was clearly happy to do so, but wouldn't look at him. He stripped his boxers off, then removed his shirt and climbed onto the bed beside her, pushing her over as he did so. Her back was to him, so he held her in his arms and kissed her cheek. "That was very good," he said soothingly.
Penelope shook her head. "Was that it?" she asked.
"No," he said gently. "We're going to try that a lot. I'm just working you up to it."
"Up to what?" Penelope asked, aghast that they were working up to anything involving that area.
Alex chuckled, petting her head. He decided to be honest. She should know why. "There are so many parts of your body that I love. Your face, your breasts, your hips, your legs, your arms, your pussy . . ." He paused to kiss her. "And there are places my cock loves," he said with a laugh, trying to keep it light. "That sweet little mouth of yours, for one. I miss that, it's been a little while. Obviously it loves being inside of you, or I wouldn't be fucking you every chance I got. It's all I think about when I'm not with you."
Penelope dreaded where this was going. "But, uhm . . ."
Alex ran his hand down her side until it rested on her hip. "You also have the cutest ass I've ever seen," he said. "Tonight was just a first step. We'll take our time, but eventually, I want you to let me inside of it."
"But," Penelope said, her lips trembling. She couldn't fathom it. "That's impossible."
"Oh, I promise you it's not," he said. He kissed her shoulder. "It will happen, Penelope. And by the time it does, you'll not only be ready for it, you'll want it."
Penelope slammed her eyes shut, unable to imagine a day when she'd want that. His cock was already too big for her to take where he had! "I don't think—"
"Just tell me you'll try," he urged. "Tonight. That wasn't so bad, was it?"
She considered, easing her muscles. "No," she finally conceded.
"And each time we'll just do a tiny bit more," he said. "There will be times that you hurt, you know that by now. But this is something we work up to. We'll work through this together."
Penelope bit her lip, still unable to cope with this new information. But he'd been gentle and it hadn't been so bad. Just a shock, no pain whatsoever.
"Okay," she finally said.
"Good girl," Alex breathed. "I think I promised you a reward. What can I do for you?"
Penelope thought for a second. She'd wanted him again, but now she didn't know if she could do anything. Even if he was slow, her thoughts would be on what he planned to do to her ass, and she wouldn't be able to enjoy it.
But this, she enjoyed. "Just . . . hold me until I fall asleep?" she asked tentatively.
Alex laughed. He sat up and managed to work the comforter and sheets out from under her to cover the both of them, then wrapped his arms back around her tiny body. "That I can do," he said, holding her tightly.