by Jane Matisse
Jack looked at her. “Masturbation is a normal part of human life,” he responded slowly, his gaze so intense she thought she was in danger of bursting into flames. “If you’d rather not do this, I could take you home.” He sounded a little hesitant.
“You’re too drunk to drive,” Penelope slurred.
“A taxi. Whatever.”
Penelope looked at Jack for what felt like forever and quickly gulped down the drink that was in her hand, letting it give her the boost of courage she needed. “Let’s go to bed, Jack.”
* * *
Jack’s heartbeat went into overdrive, and his cock pulsed. He was surprised he’d even had the chivalry to suggest he would take her home if she wasn’t ready. He was as hard as he could be inside his jeans. He’d gotten a fucking hard-on the moment Penelope had suggested he sleep with her. He was still coming to terms with it himself. Maybe it had to do with the curve of her ass, or the look of unadulterated lust in her eyes. There was something about Penelope he found intriguing. Her innocence, maybe? That hidden confidence that took a bit of digging to release from the deepest part of her personality. God, he wanted her against his better judgment; he wanted her in his bed. She stood before him, looking as skittish as a deer. Without another word, he leaned in and kissed her. He immediately felt her respond and heard her glass fall onto the carpet.
Their breathing came in sharp bursts. Jack led Penelope through the small hallway leading to his bedroom. He walked her toward his bed until the backs of her legs hit the edge of the mattress, and they fell ungracefully onto the sheets. After getting themselves comfortable, Jack began to unbutton his shirt. He could see the desire in her eyes, the unconscious licking of her own lips in anticipation of his next move. He couldn’t remember the last time a woman had looked at him with such unguarded emotions. His women were usually experienced, which was great for him, but they used coyness as a fetish rather than it being a personality trait.
His large hand slowly slid up the hem of her black dress until it rested extremely close to her wet sex.
Easy, Jack. You don’t want to scare her away, do you?
He waited a little for Penelope to become more comfortable with the lack of personal space, despite his desperate need to be inside her. The slight changes in her expression were like turning the pages of a book. He pressed his lips against hers in an effort to distract her before sliding his hands around her lacy black underwear and slipping them down her thighs. She shuddered underneath him, and he enjoyed her response. He drank it all in.
It was her first time. He was going to be her first. This was going to be the moment she would remember for the rest of her life, so he had to be sure to make it the most memorable night. The thought stroked his male ego and it was about to make his head explode.
Both of them, actually.
He immediately jumped out of bed and heard her whimper in protest.
“Hold up, let me turn the light on,” he responded before lighting a small lamp beside the bed. He turned back to climb on the bed, and stopped. Penelope was trying to cover herself against the dim light. He chuckled. “Too late for modesty now, don’t you think?”
* * *
Despite the dimness of the lamplight, she was feeling a little uncomfortable. Darkness seemed to create an invisible cloak of confidence around her. Light made her vulnerable. Even a little light. Jack walked back to the bed and kissed Penelope, no doubt trying to settle what little nerves she had left. His hand finally reached for her sex and his finger slowly filled her wetness. She gasped against his lips, her breath caught in her throat. It was overwhelming, but she was too overcome with desire to worry about the embarrassing way she was huffing and puffing. No one had ever touched her this way before, let alone undressed her. She could feel his hard-on pushing against her leg.
It must be uncomfortable to be trapped in denim, she thought, trying her best not to lose complete control, which was apparently a difficult task when there was someone massaging her clit and stroking her. Penelope hadn’t been too keen on Jack looking down there. It wasn’t exactly pretty to look at, but he certainly didn’t seem to mind it in the least.
“God, you’re so wet,” he whispered in her ear.
How many nights had she daydreamed about a moment like this? A man holding her in his arms and showing her how much she was desired, whispering sweet, dirty nothings in her ear. Jack fit the bill perfectly, and he was skillfully moving his fingers with confident strokes.
In, out. In, out.
He continued stroking her as his thumb focused on Penelope’s clit, making deliberate circles around it, teasing her senses with featherlike touches while his other hand squeezed her breast. It was driving her mad, and she couldn’t catch her breath long enough to tell him to touch her the way she wanted. Then, as if he’d read her thoughts, his fingers began to add the right amount of pressure. She couldn’t seem to stop the movement of her body, grinding against Jack’s hand as she cried out.
“That’s it. Let it go, Penelope.” She could no longer contain her panting and couldn’t stop from writhing. His dick was hard against her leg. Almost immediately she felt her release, squeezing around his fingers and letting out a sultry moan.
God.
Before Penelope had a chance to catch her breath, Jack quickly got to work on her dress, pulling it up and over her head. Her first instinct was to cover herself, but Jack was two steps ahead of her and pinned her arms above her head before she could move them. He leaned over and nipped her neck.
“This is very daring lingerie,” he murmured into her ear.
“I was planning to be a little daring tonight. It was supposed to give me a boost of confidence,” Penelope breathed.
“And did you get that confidence?”
It took Penelope a moment to answer. “I’d like to think so,” she replied, her hands reaching around Jack’s neck as she leaned up to softly kiss his lips. He responded with vigor and quickly set to work on her see-through bra. He slowly slid the straps down her arms until her breasts were free for his eyes to feast on. Her milk-chocolate-colored nipples were tightly peaked against her light skin.
She had been nervous to be completely naked in front of Jack, but he seemed to enjoy being pressed against her full form. The sprinkle of hair on his chest tickled her nipples. A moan escaped her lips.
“Like that?” Jack asked. She could only nod.
“Uhh, Penelope. You’re killing me here.” Jack’s denim-covered groin began to rub up against her wet sex.
“Jack, I think I want you inside me now.”
“You sure?”
“Just do it!” Penelope was getting annoyed and the need that was rebuilding inside her was making her restless. Playtime was over. She needed the real thing now. She helped Jack pull his jeans down, which was no easy task with their choppy, desperate movements.
“Wait a minute. Gotta do something first,” he said with a heavy breath. Penelope looked down to see his fingers tearing at a foil packet.
A condom. At least one of their heads was screwed on right. She watched in fascination as he slid the rubber down his long length. Jack finally kicked the jeans off his legs and flung them off the bed. He leaned over Penelope and touched his forehead with hers as she felt his breath on her lips.
Their breaths mingled with one another’s and both of their bodies were beginning to turn slick with sweat. Penelope let her hands wander over Jack’s back, feeling the muscles that adorned his body. She slowly slid her hands down his spine, over his hips, around his sides, and reached the sprinkling of hair on his lower abdomen, just below his navel.
* * *
“Penelope, what are you up to?” he asked breathlessly.
“I’m going all the way,” she whispered, gently touching his hard cock.
“Oh fuck,” Jack grunted. “As much as I’d like for you to keep touching me that way, we’ll leave that for another time.” He moaned, placing Penelope’s hand to his chest instead. He slid his hand down to he
r wetness again, his fingers penetrating her entrance.
“Oh my. Oh, God. Jack!” Penelope couldn’t stop herself from moaning his name.
His strokes came faster and his thumb added pressure to her nub, which threw her over the edge with a cry, only this time, without letting her catch her breath, he entered her quickly, letting the largeness of his cock sink into her tight center. She stiffened beneath his weight.
“You okay?” Jack asked, trying very hard not to give in and fuck her brains out.
Penelope only nodded. He knew his cock must feel intrusive inside her tight body, but it would nearly kill him if she told him to stop.
“I promise it’ll get better.” He rubbed her clit to ease the feeling of his cock. He could feel her growing wet again, making it easier for him to thrust at a steady pace.
“Oh, God.”
“Close, but not quite,” Jack joked good-naturedly, a bit breathless and tense. Penelope chuckled and lightly slapped his shoulder.
“Jack, shut up. Just move.”
He was a little confused at the command until Penelope began to wiggle her hips from side to side.
“Oh, shit,” he breathed, and slid deeper inside her, then withdrew only to enter her wetness again.
“Oh my! Yes, faster,” Penelope called out, her head thrashing from side to side, a clear indication of her submission to pleasure. “Wh... uhh... oh God, Jack!”
“There you go. Come on,” he replied, moving at a faster pace. He wanted to brand her, make her skin smell like him, and permanently mark her so she’d never be able to forget he was her first. It could have been the masculine boost he needed, or something different altogether. He decided not to dwell so much on it and focused on sliding his tongue along hers.
“I-I’m almost... there... Jack!” And just when she reached the peak of her orgasm, her wetness closing in around his hard cock, he thrust deep. His balls tightened and his cum released. He grunted and groaned, slowly rotating his hips inside her, post-orgasm. His arms gave way and he fell onto his side, his head bent at the crook of her neck.
After they had caught their breath, Jack stood to dispose of the condom in his bathroom trash can.
“Sorry. I should’ve gone slower,” he said softly as he returned to the bed. A small snore answered him, and he looked down to see Penelope had fallen fast asleep. He chuckled a bit to himself and lay back down, pulling the covers above them both, his eyes closing. The last thought that popped into his mind was the hope Penelope wouldn’t cling to him in the morning.
CHAPTER THREE
Speaking from experience, being a twenty-six-year-old virgin is a bit of a burden. I don’t have any virgin friends, and the friends I do have just happen to be gorgeous women with wonderful personalities. It’s obvious they have a lot of guys lined up, just waiting for a chance to breathe the same air as them. But my question to you, reader, is this: Is it any better losing your virginity for the sake of it?
DIARY OF A WALLFLOWER: Entry 103
Penelope woke up to a throbbing head. Her eyes burned with the reflection of the sun in the room. She slowly opened her eyes, letting herself focus on her surroundings. Her eyes fell on a pair of boxer shorts on the floor.
“What the fuck?” she murmured, her voice groggy. She sat up, and the covers fell to her lap, exposing her naked breasts. “What the hell?” she said, a little louder this time.
There was a slight grunt and some movement to her side. Her breath caught in her throat, and she practically flew off the bed, grabbing a throw blanket off the floor and covering herself with it. The large body turned toward her and let out another sleepy sigh.
“My God, he’s beautiful,” she murmured, trying to keep quiet.
In that moment, everything that had happened the night before came to her in a flash. “Oh, my God.” The sex. The wonderful, pleasurable, mind-blowing sex. The moment Jack had first thrust inside her, she’d felt both a slight burning sensation and a completeness. She was no stranger to penetration. She had used slim vibrators before. The only difference was that this time, it had been a real cock inside her and it was larger—much larger.
A loud ringing tone jolted her from her memories, and she headed out of the room toward the sound. She found her clutch carelessly thrown on the sofa in the living room, and opened it to grab her phone inside. She looked through the text messages and the missed calls, all from Stephanie and Jasmine. She sent Stephanie a quick message, letting her know she was alive.
Penelope walked back and looked around the bedroom, spotting a dresser. She quickly opened the first drawer and looked through the neatly folded clothes until she found a large hoodie and sweatpants with a drawstring and threw them on.
“I’m stealing your clothes,” she whispered to a sleeping Jack. “There is no way I’m walking out in the dress from last night.” Penelope activated the location settings on her phone, trying to figure out where the hell she was.
“Venice Beach, not bad.” After looking through the numbers for a cab, she found one and called.
“Yes, could I have a cab here on Sixth and Longfellow, please. Thank you,” she whispered. After grabbing what little she had brought, pulling on a pair of his socks, lifting her hair back into a ponytail, washing off the gunk on her face, and brushing her teeth—with his toothbrush, wasn’t like they didn’t have their tongues down each other’s throats the night before—she spotted his wallet on the floor.
“Well, I gave you my virginity. The least you can do is pay for my cab,” she softly told a sleeping Jack. Penelope grabbed a twenty-dollar bill from his wallet on the floor. There was a pen and a notebook on the corner desk. She ripped out a page and scribbled a small note, leaving it on the bedside table along with his wallet. With one last look at the beautiful, sleeping man, she quietly slipped out of the room, leaving her first lover and all the memories of the night they’d shared together.
* * *
“You scared the shit out of me, stupid! I was calling you all morning thinking the worst that could have happened to you!” Stephanie scolded Penelope, walking through her apartment door. “Where did you go? Huh? Don’t you know how to use a phone and call back or send a stupid text mess—”
“Hey! Hey! Okay, I get it,” Penelope responded, feeling a little guilty. “Look, I’m fine, I’m alive, and I’m here.”
Stephanie only grunted and threw herself on the couch. Penelope sighed good-naturedly and went to sit next to her friend. “Did you have a good night?”
Stephanie lifted her arm from her face and gave her the stink eye for a moment, before smirking. “Yeah, I did. Went home with what’s-his-face and we shared phone—” Her eyes widened. “Wait a minute! I should be asking you this!”
“What?” Penelope asked innocently.
“Oh stop playing with me, Penny! You went home with a sexy stud. I was drunk but I wasn’t shitfaced.”
Penelope’s face turned tomato-red. She didn’t want to explain her sex life to her friend. “Uhh well... I—”
A sudden knock at the door made her jump.
Who could that be?
“Is it him?” Stephanie asked suggestively.
“No, it’s not! I don’t think so.” Penelope was unsure, walking toward the door to unlock it. She barely had any time to turn the doorknob before Jasmine barged in.
The first thing she did was stare pointedly at Penelope. “Penny! I was so worried! Where did you go? Who were you with? You know it’s not safe to go out alone with a guy you barely know.”
“Hey, wait up! Both of you had flings last night, and I’m the one who can’t go home with a guy? Seriously? That is very unfair.”
“You’re new meat, Penny! If you’ve never done it before, it’s a risk you’re taking. We just want to watch out for you,” Stephanie replied.
“Well, you guys won’t have to worry about it again because last night was the first and last time I’m ever doing that.”
There was silence from her friends. Penelope looked from on
e to the other. “What?”
“What’s the story?” Stephanie asked.
“What story?” Penelope said innocently.
“Stop fooling around, Penny. We can both tell you were fucked very thoroughly last night,” she retorted.
“Yeah, you smell like it, too.” Jasmine wrinkled her nose.
Penelope looked at them both, incredulous. “Well, maybe because I haven’t had time to take a shower this morning. I had just been here for five minutes before Steph decided to pay me a visit!”
“So you did do it!” they both exclaimed.
“Details, details!” Stephanie squealed.
Penelope was speechless, the warmth of her blush creeping up her neck. “I went home with the guy and spent the night at his place. End of story.”
“Wait, what do you mean, end of story?” Jasmine exclaimed.
“I mean that I am not going into any details.”
“Well, was he any good?” Stephanie inquired.
Penelope hesitated. “If last night was any indication of how sex really is, I would definitely want to do it again,” she confessed, a small smile on her face.
There was more squealing. Penelope cringed at the sound.
Jasmine responded first. “So, did you get his number or what?”
“Yeah, are you meeting him again?”
Penelope shook her head. “It was a one-time thing with a great guy who took pity on the virgin—”
“Oh, fuck off, Penny! If he sexed you up, that meant he wanted you big-time!” Stephanie angrily explained.
“Either way, we won’t ever meet again. It was a great experience and I enjoyed it.” Penelope explained how she’d woken up and left without disturbing a sleeping Jack.
“That’s our girl. No walk of shame,” Jasmine replied. “And hey, you got a memento to remember that night forever,” she continued, pulling on the hoodie Penelope was wearing.
“I guess so.” Penelope took a deep breath, taking in the aroma of Jack’s clean clothes.
“So, are we going or what?” Stephanie asked, waiting impatiently to leave for their lunch.
