Author’s Note: This is an erotic novel in many chapters. If you enjoy this chapter, I highly suggest checking my profile and starting from the beginning. This is my first time submitting to Literotica.com, and I appreciate you taking the time to read what I so enjoyed writing. Thank you.
Alex lifted his watch from the patio floor to check the time. It was almost four, and they’d relaxed in the sun alone together for the last time.
“I made dinner reservations,” he said, reaching over to her chair to take her hand. “Feel like letting me take you out?”
“Sure,” she replied, though she felt mixed emotions. It was their last day together before he’d be busy with work again, and she’d hoped they’d spend the whole day playing naked. Instead they’d barely touched; only a few brushes here and there, or an application of sunscreen. She was a little disappointed that they’d be going out instead of staying in to play, but mostly she was disappointed that this week had come to an end. Everything would change now, and she wasn’t ready for it.
“Why don’t you go shower and get ready,” Alex suggested. “We’ll leave here at five thirty.”
Penelope agreed and left the patio. Alex followed so he could clean up and dress. He wasn’t too thrilled about a few hours of her in real clothing, but he figured he’d been a real jerk not taking her out somewhere nice this entire week. And he had an evening planned. And the evening started the moment she’d enter her room.
He’d ordered something for her the day after their shopping trip, and when mixing a drink, he’d taken the box up to her room and laid it on her bed.
When Penelope entered her room, a lilac box sat on the foot of her bed, wrapped in a white bow. She smiled in confusion as she walked over it and saw it had a folded white card. Lifting the top, there was a note.
Saw you look at this when we were out. It was wasted on a mannequin, so it had to be yours. Hope you like it.
Penelope untied the bow and lifted the lid. White tissue was held together with a gold embossed sticker, a name she didn’t recognize scrawled in black. The tissue ripped as she pulled the sides away.
Inside was the pink and black polka-dot lingerie she’d seen in the shop downtown. Her jaw dropped as her fingers trailed across the satin, the softest fabric she’d ever felt. The cups had an underwire, and she pulled the tag from the back to look at the size. 32B. Exactly what she wore.
She left it there to take a shower, and couldn’t stop thinking about it while she cleaned. She’d never owned anything that could be considered sexy, and the word didn’t scratch the surface of how she felt about the lingerie. Once dried off, she walked naked into her bedroom and pulled out the panties.
They fit perfectly, so soft and smooth against her skin. She turned in the mirror to admire how the thin fabric enhanced the curve of her ass. The panties alone made her feel luxurious. She was hastier with the bra, and once she had the back clasped, she found it fit her like a glove. The tops were more squared than curved, and the wire pushed her breasts up high on her chest, making them look the size of baseballs.
She walked back over to the box and found more pieces, then remembered the mannequin. Black sheer thigh highs with lace at the tops, along with the suspenders. She undid the eyehooks and wrapped the suspenders around her hips, then worked the sheers up her legs. They attached to buttons on the elastic that hung down.
Penelope returned to the mirror. She looked like a pinup model straight out of a Vargas watercolor, only even sexier. She turned this way and that, looking over all angles. Finally she went to the closet, feeling it was a shame to cover up the luxurious lingerie.
Once in a black cocktail dress she’d bought from the first store they’d entered, she slipped into black pumps, knowing they must look wrong. They hadn’t been shoe shopping, and these were from her graduation and the nicest shoes she owned, but she still hoped no one would be looking at her feet.
She met Alex downstairs in the foyer. He wore a black jacket and white shirt, black slacks; no tie. He looked like he’d stepped off the cover of a GQ magazine, and when he met her eyes, he grinned.
Penelope looked stunning. The dress hugged her, then flared slightly at the hips, sashaying with each step. Her hair was half up in a twist with curls cascading down over her shoulders. She put the Real Housewives of the neighborhood to shame, even though she seemed unsure of herself. In his eyes, that made her better than the whole lot of them.
Ben was waiting by the town car and held his breath when he saw Penelope step out of the house. Tonight had been the first time he’d been called all week, as Reuben had told him Alex was on vacation and wouldn’t need his services. He watched Alex escort her to the car with jealousy. She was the same beauty, only more magnificent now.
Yes, he’d definitely have to try and get her in the sack. He couldn’t wait until he’d be driving her to school every day in a few weeks. He’d be alone with her, free to hit on her without his boss—her godfather—giving him the evil eye for it.
They pulled up at the restaurant and walked up an honest to god red carpet to the door. The valets in uniform smiled at Penelope and bowed their heads, and for the first time, Penelope felt like she fit in here. She wasn’t just the little naïve girl from her tiny town anymore. She was a part of this life.
Dinner was like a dance. There were no prices, the menu straight forward. The restaurant offered three different five-course meals with wine pairings for each dish. Four people waited on them alone. One carrying wine, another carrying the dish. The second Penelope would put her fork down, a waiter would silently appear and sweep her plate away while another wiped the tablecloth free of crumbs or spills with a metal slate, while another had the next dish at the ready.
Rinse and repeat.
“I’ve never seen anything like this,” Penelope commented over the coordination. It was amazing; she didn’t feel like she was even being watched, but someone had to be orchestrating the dance. She sipped her wine, then took a bite of her filet mignon. Just as with the salad, the soup, the pasta with chanterelles, the wine complimented and enhanced the taste.
Alex couldn’t have been happier. It was nice to be with someone who appreciated this, rather than bitched and moaned over stupid little things like a waiter taking a split second too long with the next dish, or commenting on a couple nearby who didn’t have any class. He watched with delight as Penelope delicately cut tiny bites and brought them to her mouth, how she sipped her wine, her motions elegant and still unsure.
And he couldn’t stop thinking about later.
She deserved this. She’d been magnificent. When he’d bought her a car for her sixteenth, he’d done so out of guilt like an absent parent making up for the time he’d been unable to spend with her as she grew up. When he’d offered to pay for her college, he’d done so because he knew her parents couldn’t and he owed it to them, and her, as her godfather. When he’d offered to let her come live with him, he’d been looking forward to the rare minutes he’d get to spend knowing the little girl he’d adored before his busy life and second wife took him away. When he’d first caught sight of her outside of his estate, he’d felt dumbstruck, as this wasn’t the little girl he’d remembered, this was a young woman. When he’d seen her in her yellow bikini, he’d admonished himself for thinking of her as a woman instead of his goddaughter.
Then he’d touched her body, and she’d enjoyed his touch. Now he thought of her as a woman he wanted to bed for as long as she’d let him, and he hadn’t even had sex with her. He thought about what they’d done thus far and contrasted it to the woman sitting across the private table from him. She was blossoming into exactly what he wanted from her.
A lady on his arm and a whore in the bedroom.
It would take a while, but he still looked forward to training her, and again, he couldn’t believe his luck. Not only had this pure, virgin beauty come to live with him, but she wanted him in return. He’d been wanted, and he’d wanted, but nothing could touch what he had on the horizon with Penelope.
It was eight thirty when they returned to the car and Ben drove them home. Alex was careful to sit far away from Penelope so no one would suspect anything. His staff had seen him behave as a playboy; seen him cheat on his first wife, seen the plethora of women between his marriages. The naked women during his pool parties. Ben had been witness to Alex having sex in the back of the car more times than he could count on both hands.
But Penelope was sacred. He wasn’t hiding her, or maybe he was, for now. He looked forward to the day he wouldn’t have to hide it, but even then, he couldn’t imagine mauling her in the back of the car like he’d done with others.
At least not for a while.
After dropping them off, Ben returned to his own car and left for home, thinking about Penelope the entire way.
Alex shrugged out of his jacket and hung it on a hanger in the coat closet off the foyer, then turned to Penelope. “Why don’t you head up to your room and change,” he said, adding the perfect amount of implication into his voice of what he expected. “I’ll be up in a few minutes.”
So, no movie tonight, Penelope thought happily, and hurried up the stairs knowing that they’d be playing tonight in her room. She had no idea what to expect, but she couldn’t wait to feel him. His hands on her skin, maybe his penis in her mouth again. Maybe they’d fall asleep together in her bed.
Alex stood in the study watching the clock. He’d been wondering if he should grab a condom from his room, but knew she was on the pill. He’d seen the case in her bathroom a few days back, and teasingly asked her why a virgin was on birth control. She’d blushed and told him her mom had got her on it when she was sixteen just to be safe, and she’d stayed on it because she liked how it regulated her body. He’d laughed as she explained how nice it was to “only go through . . . that” every three months.
So, no condom. Unless she asked for one, and he’d absolutely comply. Her first time would need to be special. He only hoped that if she had reservations that he could keep them at bay and talk her into it. He’d been able to think about little else for a week, and once he’d made up his mind that it would be tonight, there was no going back.
Only a firm no would keep this from happening.
Exactly five minutes later, Alex walked up the stairs. Her door was open and he stepped into the frame.
Penelope stood at the foot of the bed in the lingerie, as he’d hoped, looking more beautiful than he’d even imagined. Bikinis were one thing. Expensive lingerie was quite another. If he could ever figure out a way to make it happen, she’d never wear anything else again. But for now—right now, she was a vision. Her hands were at her sides, and he could see that she was nervous standing there in full view by the way her fingers wiggled at her thighs. Her head was ducked low as she stared at him through her eyebrows, but her face was the last thing he was looking at.
The pink bra with black polka dots kept her breasts firm and round, not that they weren’t firm already with how young she was. The cups pushed them high. Below, her tiny stomach was just as firm and now with a stunning tan. Where her hips slightly flared, the fabric of the suspenders began, drawing lines down the front of her thighs until they clasped the black lace. There was a sliver of skin between the belt and her matching panties. Though her legs were pressed together, there was a tiny triangle between her legs of air where her thighs never met.
Penelope watched Alex stare, saw how his eyes slowly travelled her body. She felt as good as naked, but didn’t dare move. She’d spent the last five minutes trying to figure out where to be, and had decided to stand here. She wouldn’t move until he did.
Alex unclasped his cufflinks and set them on the dresser near the door. Slowly, he unbuttoned his shirt, taking his time so he could continue to stare at her as long as he could like this. He’d always found it amusing that lingerie’s sole purpose was to be removed, so he wanted this image imprinted in his memory.
Once his shirt was off, he carefully laid it across the top of the dresser, then made his approach. When he reached her, he placed his hands on her cool shoulders and felt her shiver with his touch. Letting his hands trail down to take hers, he kissed her cheek softly. “I can’t honestly recall the last time I was stunned by such beauty,” he said, and he meant it.
Penelope blushed, she knew, her cheeks filling with heat. Her eyes met the floor in hopes he wouldn’t notice and think of her as ridiculous. She felt one hand slide around to her back, her chest meeting his. He used the other to brush her hair behind her head, then kissed her neck tenderly. It was amazing how her hair never tickled her unless he was the one moving it.
Alex bent his knees as his hands rubbed their way down to her ass. He lifted her up into his arms, her arms and legs wrapping around him, and carried her to the bed. He gently laid her down on top of the blankets. His movements slow, he walked from post to post, untying the drapes around the bed. They were alone in the house, but he wanted the bed to be the only world that existed. As he walked back around, he pulled them shut, catching glimpses of her sprawled on the bed in her lingerie as he did so. Once back to the original side, he climbed onto the bed and shut the curtains behind him.
Closed off, Penelope felt like a princess. A bed with curtains like this was regal. They were a crème color and thin enough that the well lit room kept the bed glowing, though it softened the harsh lights. It felt private and intimate, as though they were the only ones that existed in the world.
Still sitting up, Alex brushed the back of his hand across her cheeks. So innocent. So beautiful. He let his hand trail down her neck, then turned it so his fingers could trace the upper curve of her left breast. The bra did wonders in really accentuating them; something the mannequin just couldn’t convey. He let his fingers trail a line between them and down her sternum. He continued the line down to the suspender belt, flattened his hand, then rubbed it firmly back up.
He’d never really taken this much time before, but with Penelope, he wanted to savor every moment. Her skin was silky smooth. His fingers met the wire of the bra and he left his hand there, then bent in to kiss her.
When his lips left her mouth, he kept his forehead against hers. Penelope felt his hand travel across the top of her left breast, then his fingers cupped inward. They traced the top of the bra from center on out, then hooked into the strap. He pulled it from her shoulder, then rose to look down at her again. She loved the way he looked at her. She never wanted his eyes to leave her body.
The strap gone on one side looked so good, Alex did the same with the other. His fingers traced small circles over her skin until he finally had to see. He pulled the cup down from her left breast. Her nipple was hard, her tiny areola still holding the same magic as the first time he’d seen them exposed. He brought his lips down and kissed her nipple, then cupped her breast and began to suck.
Penelope moaned, her legs writhing in pleasure as Alex’s hot mouth worked her breast. The first time had been wonderful, but this felt special. It was the atmosphere, she decided. The dinner. The sexy lingerie.
After giving her other nipple some special attention, Alex decided the bra needed to come off. He took her arms and wrapped them around his neck, holding them in place to help pull her up. He only let go when he was sure she’d hang on, then deftly unclasped the back. He kissed her as he lowered her back down on the mattress, then left her mouth to watch her body. Slowly he pulled the bra from her and flung it to the far corner of the bed.
He played with her for a long time; much longer than he’d thought he would, but he couldn’t help himself. Her tits were too mouthwatering to stop, let alone the noises he’d get when he’d do something like pinch or bite. It amazed him that he was entertained by this alone when he had far more entertaining things coming.
Finally he kissed a trail down her stomach, sliding along the bed as he did so until he was sitting by her knees. He unbuttoned the elastic suspenders. One by one, he pulled the sheers from her legs, feeling her smooth hairless skin as he did so. The actual belt posed a problem. “Roll over,” he said softly, urging her with his hand. Penelope rolled onto her stomach. He was taking so much care with everything; anyone else and he’d be ripping the items from their body. Each hook was done as an individual until he’d released all six of them. He pulled the sides down and spent time rubbing her back, letting his hands glide over her ass and grasp her cheeks.
When he helped her roll back over, he toyed with the top of her panties. Without him saying a word, she lifted her ass from the bed and he quickly pulled them down to her knees. With the drop of her back, her feet went up and he worked them off, sending them to join the rest of the items.
Now she was completely naked, and he spent a minute or so just staring at her. The next few minutes he ran his hands over her skin; her breasts, her waist, her sides, her hips, her thighs. Finally he urged her legs apart and cupped her pussy in his hand.
“Ahhh,” Penelope moaned, her back arching. She closed her eyes to just feel the warmth of him there. Then his fingers moved, his hand gently rubbing. She couldn’t stop her head from moving in gentle circles with each motion he made, his touch still shocking and sublime. She didn’t foresee a time when she’d ever get over his hand there.
Alex let his hand slide all the way down and under the mattress until his thumb was poised at her entrance. He slowly dipped it inside, finding she was already slick with her juices. He didn’t know if it was there, but he wanted to find out. Leading with the pad of his thumb, he quickly met a thin, flexible membrane. In the center was the hole that would allow it to tear once he’d entered her, so he didn’t push any further. He knew hymens could be broken by anything, even falling wrong on the seat of a bicycle. But hers intact not only confirmed her virginity, it confirmed that not even her own fingers had explored herself.
That would be another thing he’d have to teach her. He wanted to watch her masturbate, and would, eventually.
He played with her folds, using her own juices as lubrication. She’d moan and writhe and wriggle and cry, hold her breath, then gasp. He took his time with this, as well, enjoying the reactions he was getting. It was important to take his time here so she’d be ready for him.
When Penelope felt his hand leave, her eyes opened and she caught him removing his pants. She sat up on her elbows. “Oh,” she said, ready for the next part. The part where she played with him. He was out of them now and let them fall off the side of the bed. She could see his erection through his black boxer-briefs, and reached out. “Let me—”
“No,” Alex said, shaking his head. “Tonight is about you. Lay back.”
Penelope was surprised, but not displeased, not by a long shot. He was still going to play with her, and she was so wet and aroused, she wanted to feel an orgasm at his hands or mouth once more. She lay back and watched him climb over, positioning his knees between hers.
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.