Alex and Penelope Ch. 05


When he kissed her, she felt his weight, though he was obviously careful with it; not that he could have weighed all that much. His fingers ran through her hair, his kisses more passionate than ever before. It was hard to catch her breath, and she only could in the quick moments where he'd kiss down her neck before returning to her mouth. She kept her arms wrapped tightly around him, the skin of his back soft against her hands.

She was in heaven.

Alex kissed down her neck until his mouth was near her ear. "What do you want, Penelope?" he whispered. He hoped she'd say it herself, but if not, he had other ways of suggesting.

"I'm not . . ." Penelope said through ragged breathing. "I want this," she finally settled on.

"Yes," Alex agreed, taking her earlobe into her teeth. He listened to the moan, then released it. "But what to you want?"

It hit Penelope then what was happening. What was being offered . . . maybe. Was it? She couldn't figure it out. But no sooner than the thought crossed her mind than she'd made it up. She wanted him. She wanted him to make love to her. Her heart nearly choked her as it dawned on her that it could happen tonight. She felt hot, unable to even ask for it, especially if he didn't want to. Of course, he probably did want to, but how could she be sure?

"I . . ." she began. She couldn't say it. "I want you," she finally breathed, with special emphasis on you.

Alex smiled to himself. She wanted him, and the way she'd said it, she wanted him inside of her. She wanted her first to be him. He hadn't imagined she'd say no, but he'd played out every possible scenario. He'd considered what he'd say if she hesitated. He'd even considered what it would mean if she had given the firm no he dreaded; how it might make things awkward from here on out.

But she hadn't said no to anything else, and she wasn't saying no now. He wondered if she ever would. He'd work his hardest to find out.

He rolled off of her and worked his underwear off, then immediately rolled back on. He was too afraid she'd change her mind, though he also couldn't act too quickly. It was a delicate balance. He kissed her some more, only this time, he let his hard cock rub against her.

For her benefit, he looked down at her and quietly asked, "Are you sure?"

Penelope considered for a second, then bit her lip. She'd never felt so sure of anything. She nodded, never leaving his eyes.

Alex reached between them and positioned himself. Once in place, he brought his hands back up to either side of her head, staring into her eyes. He wouldn't leave those eyes again until they'd finished. He could see her fear now and smiled kindly. "Just relax," he said. "I wouldn't dare hurt you."

Penelope focused all her energy on relaxing, though the muscles in her legs ached, trying to close without her permission. She planted her lower lip between her teeth to brace herself; he was far too large to ever make it. It all seemed impossible.

Slower than he'd ever moved in his life, Alex pressed into her. Almost immediately her eyes slammed shut and she cried out in pain. He felt her fingers dig into his back and held deadly still as she rode it out. It took a few seconds, but the sound stopped and her eyes slowly eased open as she sucked in a deep breath. He pet her head gently, finding tiny beads of sweat had accumulated at her hairline.

"It hurts," she sobbed.

"Only for a minute," he said soothingly, then kissed her lips. "Just for a minute, then I promise you, it will feel good.

A single tear fell from her right eye and Alex's heart broke. But he knew that in a few minutes she'd be begging for more. This was to be expected. This was what made it so exciting, and thank god he was her first. Some shitty teenager would have rushed things. He wiped it away with his thumb, then eased a little deeper.

It was slow going; her muscles did not want to allow him entry. But once his head made it through her outer muscles, he'd be home free. He had to move a little faster now; Penelope was on the verge of telling him to stop, he could tell by the look on her face and the noises she was making.

So without further ado, he pushed with a little more force, ignoring her painful cry, until his head was in.

And holy fuck, what a feeling. It was probably because she wasn't relaxed, not by any stretch of the imagination. But she had the tightest pussy he'd ever entered. Her muscles gripped him like a vice and they'd spasm, trying to expel the foreign object.

"We're there," he breathed, his voice hoarse. "You're doing great."

"Mhmm," Penelope moaned bravely with the nod of her head. She hurt so badly, and didn't believe him when he said it would feel good. But people must like it or they wouldn't do it. She knew the first time would be painful, so she just had to get through this. Unfortunately, this was ruining everything that had happened up until now.

Alex was losing her, and he knew it, so he gave up offering encouragement and began to slowly push in deeper. It was thrilling, no matter how much he ached for Penelope, who was doing so well. She'd gone from first base to home in less than a week, so it must be a shock.

He pulled gently back, then pushed in. His motions were slow, but he was fucking her. It felt too fucking incredible to stop. As noted before, it would only take that firm no to make him stop, and he hadn't received it yet. He still watched her face, the creases, her eyes held firmly shut. She still looked beautiful, especially because this is what she looked like losing her virginity. Losing it to him. This is what she looked like the first time they had sex, with him inside of her.

After another minute or so, her face softened. The fingers that he'd barely noticed digging into his back eased up, and he could feel her muscles relax as he slowly pushed in and out. It was getting easier.

And then she uttered a moan that sounded like pleasure.

Relief washed through Alex. She was through the initial shock of it; the first pain. She was very small, so it would probably take a long time for her to get accustomed to his girth, but she was doing much better. Her eyes finally opened and met his, and a tiny smile appeared on her lips. He immediately brought his mouth down to kiss her, never losing his gentle rhythm.

Alex had been right. It still hurt like hell, but it was getting easier. She couldn't believe she'd ever doubted him, and swore she'd always trust him from here on out. He was so kind and gentle. He'd been careful with her. Encouraging. She felt embarrassed that she'd made such a fuss, but it had been pretty horrible at first. But now, even through the pain, there was pleasure to be had. Mostly it was emotional, not physical. Alex was inside of her. He was her first. And though she felt stretched to the limit, she still didn't want him to ever leave. She'd feel empty with him gone.

"Better?" Alex asked a few minutes later. He could do this for hours, though he'd have to make himself cum quick, just so this would remain pleasant and she'd want it again. "How you doing?"

"Fine," she breathed. "Yes, better."

"Good," he said, then kissed her again. He needed to focus. He wasn't sure how long they'd been going, but it was at least ten minutes by now. She'd need him out soon so she could recover. So he focused on the body beneath him. Thought about what he'd just done. He'd taken her virginity, and was having sex her now. He thought about the many ways he would fuck her in the future. He thought about making a rule that when she was in his house, she'd wear only the lingerie he'd buy for her. He thought about the things he could show her; what he could teach her. He imagined showing her off at his parties. Fucking her any way he wanted, everywhere. Spanking her if she disobeyed.

All these things combined had his pace picking up without consciously realizing he was doing it. Penelope was moaning quickly and in rhythm to his thrusts, which were getting deeper and harder. With one final thrust, his seed emptied inside of her and he cried out with the release.

Penelope knew he'd cum by how rigid his back was, his chin up high. He was in so deep, and he'd frozen there. She was moaning through her teeth, bearing the pain, and couldn't decide if she was disappointed or relieved that it was over.

Alex slid out of her and fell to her side. He looked down, seeing his cock glisten with her juices and the faint trace of blood as it softened, then immediately grabbed her and held her to him. He knew he had to comfort her now, show her his gratitude. It needed to remain special for her first time. For their first time.

After a long time, he finally broke the silence. "Tell me what you're thinking."

His jaw nearly dropped; he couldn't believe he'd actually uttered the words. When was the last time he'd cared what anyone was thinking?

"Mmm. I guess I'm thinking I'm lucky," Penelope said, nuzzling her cheek against his chest.

Alex chuckled quietly. "And why's that?"

"Well," she said, considering. "It hurt."

"And that makes you feel lucky?" Alex said teasingly.

She lightly slapped his chest. "No," she said through a laugh. "It would have hurt no matter what. I'm lucky that it was with you."

She thought she was lucky? He was the one who'd just had sex with this eighteen year old virgin goddess. Her in his arms was a constant reminder of how lucky he was, not the other way around.

"I'm sorry it hurt," he said, and meant it. He enjoyed inflicting pain sexually, but only to someone with experience who wanted it. She'd wanted it, but hadn't known what kind of pain to expect. She'd been amazing. "Next time it will feel good. Even better the time after that."

Penelope smiled. She knew it would get better. It was that there would actually be a next time with him that left her grinning from ear to ear.

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