Pop My Cherry
Jessica flopped down on the couch, exhausted from a typical day at work. She was a petite 23-year-old who was slogging through her first job after college - telemarketing. It was a dead end and she knew it, but this was the best she could find for now. To make the despair worse, her boss was also terrible to all the employees. Jessica had made it through another day though, and as she kicked her shoes off, she glanced up to acknowledge her housemates, Sarah and Leslie, as they passed through the living room.
“What’s up, Jess? Want to go out with us tonight?” Sarah asked.
“Oh man. I am trashed,” Jessica responded. “Maybe another night. Thanks though.”
The three of them shared an old Victorian house, and the rent, split between them, was about the cheapest deal you could find in the city. The house had “character.” That was about the nicest way Jessica could describe it. She appreciated the renovations the landlord did before they moved in, but it was still creaky, and a little drafty.
“I really need to relax,” she thought to herself. “Some alone time would hit the spot right now…” Once she had her feet propped up on the coffee table for a few minutes, her thoughts started to drift to other pleasures. Now she couldn’t wait for her roomies to leave - as soon as they were out the door she would take care of some sexual impulses. Jessica was still a virgin, and kind of sensitive about it, but she was a very active masturbator. A pro, really. Whenever she got the chance, she would set up elaborate sessions: Candles, soft music, a bath, soft blankets, and her trusty toy. These sessions could go on for a couple of hours usually. This practice made her very “in touch” with her sexuality, and she knew a lot about what felt good, but there was still something missing, and she thought about it every day: She still had never been with a man.
It wasn’t because of her looks - she was beautiful: Dirty blonde hair that she wore straight and shoulder length, dark brown eyes, and a small but well proportioned figure. Jessica just hadn’t ever been at the right place at the right time, she figured.
Sarah and Leslie finished getting ready and tumbled out the door. After slamming it a couple of times, and finally getting it to stay shut, they piled in the car and left. “Peace and quiet, finally!” Jessica thought. Her hand slid to her crotch and she rubbed it a couple of times through her jeans, just as a treat to herself. Then she went to her room and brought back all the items for a stellar session. She locked the front door, drew the curtains, lit the candles, and got naked. This time, this space, was just for Jessica.
Snuggled up on the couch in her blankets, dim candlelight all around her, the rest of the world faded into the background as she began to run her fingers softly across her own skin. Starting with her arms, legs, and neck, Jessica brought her whole body into the experience, teasing herself and saving the best for last.
While she was warming herself up this way, a thought popped into her head that she wasn’t ready for: Josh.
Jessica first met Josh when he had come to fix her computer several months ago. He was a high school friend of Sarah’s and she had recommended his mobile repair service to Jessica when the screen on her laptop died. Josh was very professional and did good work, and he was kind of cute too. He was 29, with short brown hair and seemed like he was in pretty good shape.
A week or two later, Sarah had invited Josh to a party at the house and Jessica learned a little more about him. He was 29, had been married and then divorced, no kids, and his business was doing fairly well. She was especially impressed by his easy, calm demeanor and the way he smiled at everyone he met. Besides thinking that he was cute, Jessica didn’t really think of him sexually, or as a potential partner. That’s why it surprised her that he came to mind when she was on the couch touching herself.
Jessica had just begun to move her fingers toward her vulva when the thought came, and then she stopped and opened her eyes. “Oh, I bet he would be fun to play with,” she thought. “Why did that never occur to me?”
Then her mind wandered to the day she first met him, and she glanced at her laptop on the coffee table. “The laptop... Work... Dammit, I’m trying to relax… Oh SHIT! The quarterly marketing report!” In her after-work haze when she came home, Jessica had forgotten a spreadsheet she’d meant to finish tonight. It was due tomorrow. This cum session would have to wait. She rubbed her vagina wistfully, just a few strokes, before she threw her bathrobe on. She was starting to get wet, and that made it more frustrating to pull her fingers away. Her own wetness had always turned her on even more, ever since high school, when she first began to masturbate.
Jessica wrapped the bathrobe around herself, wiped her fingers off, and popped open the laptop. Then, to get down to business, she stood, gathered her blankets and dildo, flipped on the lights, blew out the candles, and returned her things to her room. Next, she headed to the kitchen, to fix a cup of black tea and clear her head. As she stood barefoot on the weathered wood floor, waiting for the water to boil, she leaned against the antique stove and absentmindedly rubbed her fingers together, feeling the dried residue of her own juices. Her vagina pulsed once at the thought of her own touch.
Jessica’s thoughts began to drift again, back to a familiar longing, something that she dreamed about more and more often: Losing her virginity. She was really good at having a quality cum session by herself, but she still didn’t know what a penis felt like, or the weight of a man on top of her. The kettle began to whistle, breaking into Jessica’s daydream. She made her tea, and wandered back into the living room where her laptop sat, like a monster, ready to devour her evening.
Jessica never did fully reconstruct what happened next. It might have been one of Leslie’s shoes that she tripped over, or she may have just stumbled on an uneven floorboard. Whatever the case, she tripped, and tumbled toward the coffee table, spilling her entire drink across the keyboard of her laptop. She pulled herself off the floor, shook the liquid out of her computer, quickly mopped up as much of the mess as she could with a few napkins that were nearby, and then rushed to the kitchen for paper towels.
“Oh no. I am so SCREWED!” she thought. “What if my computer is destroyed?” Before she went into full panic-mode though, she came up with a plan. She went back to the kitchen and dug around all the Chinese takeout menus and old grocery lists on the refrigerator and finally found it: Josh’s business card.
Josh arrived within minutes, and he was at the door before Jessica realized that she had never changed out of her robe. In her frantic state, she was too worried about her computer to care though, and let him in. She only had to slam the door twice this time to close it behind him.
“I doubt there is much I can do,” he said. “Usually a spill will really mess a laptop up. Did you try to turn it on after it got wet?”
“No,” she said. “I was too busy cleaning up the mess and calling you - I didn’t think to try it.”
“Oh, that’s actually a good thing,” he reassured her. “The power will fry the circuit board if it’s wet, so it’s better to wait until it’s completely dry. It’s a lot more likely that we can save this one!”
Jessica felt better already - she realized that she was in capable hands. “So can we get it running tonight?” she asked.
“Probably not, we need to be sure it is completely dry. I’ll need to take it back to the office, and I should be able to return it tomorrow sometime.” Josh noticed a wave of desperation cross Jessica’s face. “But I may have a spare in the truck that you can borrow if you have to get a project done tonight,” he said.
“Oh, yes, please! That would be wonderful,” she said.
Josh went to his truck and returned with another computer and all the peripherals. “Let me get this set up for you. How’s Sarah?” he asked. Jessica was glad for some small talk, and she felt like she could finally relax a little.
“She’s fine, she and Leslie went out tonight,” Jessica responded. Then she became acutely aware that she was only wearing a bathrobe. Josh was hunched over the dining room table, installing software or something, and Jessica was standing behind him, trying to pay attention. The next thing she noticed was that Josh’s jeans fit him really well. He shifted his weight, and her nerves sent tingles to her crotch as she watched the strong curves of his hips flex from one side to the other.
“This isn’t the latest version of word processing software, but it should work for your purposes,” Josh’s voice broke her reverie.
“Yes, I’m sure,” she responded. “I’m not doing anything too complicated.”
Jessica had tried quite frequently to figure out why she had never gone all the way with a boy. The closest she could come to an explanation was a few experiences in high school. She had her first real boyfriend in the ninth grade, and neither one of them knew what they were doing of course. That lasted a couple of months, and all they ever did was get together with their other friends and go to the mall.
Her second, and last boyfriend, David, came along in her junior year, and they dated until graduation. He seemed nice at the beginning, and they really enjoyed each other, but it was a year before he gave Jessica her first kiss. After that, they made out every chance they got, and it was enough for both of them. Until the week of graduation. David became very aggressive one night when they were out at a bonfire with their friends. They had wandered off from the group and in the darkness David started to get more physical than he ever had before.
Jessica really wanted to go all the way, and she thought she loved David, but he wasn’t listening to her, and he didn’t seem as sweet as he usually did. Just before things got really out of hand, one of their friends came looking for them, and David backed off, but the emotional damage was already done. Jessica broke up with him the next day, and she never had another boyfriend after that.
Once she got to college, Jessica stayed busy with her studies and didn’t get very close to any of the men, or women, for that matter. She was always hesitant, because David had seemed so nice for so long, and had just changed without any notice. How could she be sure that wouldn’t happen again? Even though he didn’t rape her, the emotional wound gave her a deep-seated distrust of intimacy. She was proud of herself for being able to fulfill her own needs though, and she got pretty good at it.
Jessica was always curious about what it would feel like to have a penis inside her, and one weekend during college she worked up the courage to shop online for a dildo. After browsing through what seemed like hundreds of pages of really shocking items, she found a small, plain toy, only about an inch wide. She didn’t think she could fit anything bigger, since she had only ever put her own fingers inside.
The day the small brown package arrived in her mailbox, Jessica’s heart was in her throat. She set up her usual, elaborate, cum session and prepared to play with her new toy.
Josh had been divorced for two years, and hadn’t had sex since his marriage began to fall apart a year before that. He and his wife, Sheila were one of those couples who just never should have been together. They hit it off just fine when they met in college, and at the time it seemed like getting married was the thing to do. The one part of their five-year marriage that he remembered fondly was their four years of intense sex.
After only a few times together, it was obvious to them that they were on the same page - their bodies and their primal urges were in sync. Any time Josh became curious about a kink, Sheila was excited to explore it. Whenever she asked to try a new position, Josh somehow had the energy and ability to give Sheila her fill, every time.
They just didn’t get along with each other outside the bedroom.
Josh’s breath had caught for a moment when he saw Jessica’s number come up on his phone’s caller ID. He had been interested in her as soon as Sarah introduced them.
He answered the call. “Calm down, what happened? ...Okay, I’ll be right over!” Josh did his best to focus on the job as he drove to Jessica’s house and set up the loaner laptop.
The software install was at 76 percent.
It might have been his growing attraction to Jessica, or a subconscious trigger. When she responded with “I’m not doing anything too complicated,” he had a small deja vu moment and a sudden memory of his first time with Sheila: The softness of her skin, the warm, inviting moisture of her pussy. That was always the sensation he remembered. They lost their virginity together, and the way her lips wrapped around his cock was like nothing he’d ever experienced before. Josh wondered what it would be like to take another woman’s virginity. Would it feel something like that night with Sheila? Maybe the magnitude of the moment for the woman would transfer to him as well?
Josh zoned-out for a minute, thinking about the pleasure of his first time, and came back around when the loading bar was at 98 percent.
“Alrighty, just about done,” he said, and turned around just in time to catch Jessica with a tell-tale expression on her face. She tried to look normal but it was too late. Josh knew what she had been thinking. The desire and hesitation were oozing out of her, and he knew that he needed to make a move or he would miss his chance.
“Jessica, there’s something I have been thinking about. I hope it’s not out of line. Can I ask you a personal question?”
Jessica suddenly felt very vulnerable standing in front of him, barely clothed, and under his direct and intense gaze. All of her lust for his body, and the latent thoughts about him during her masturbation rushed to the front of her mind, mixing her up, and causing her to lose her bearings. “Is he feeling the same thing I am?” she wondered. In this split second, all she could manage to do was blurt out a quick “Yes?”
Josh could tell that he needed to move slowly, but it was also clear that Jessica was interested. “I have been thinking about you - would you like to go to dinner with me sometime?” he asked.
“Um, I…” Jessica had been so mixed up in the surprising feelings of desire that something normal like going to dinner caught her off guard. “Sure, that would be fun.” She smiled, glad that he couldn’t read her mind. But right then, as though he could read her mind, he reached out, took her hand, and moved closer.
The electricity of this sudden closeness opened something in Jessica. She edged closer to him, and there was barely an inch between them. “This is crazy!” she thought. “What am I doing? I don’t know this guy!” The chemistry kept moving things forward though, as if the two of them were on a roller coaster that was already in motion. There was no stopping now. This is exactly the situation that Jessica had avoided for so long, and she was in territory that she did not have a script for.
Josh was close enough that she could hear his breathing, and she noticed his shoulders, which seemed to tower above her, broad and strong. Her own breath quickened, and she took the next step: Reaching her other hand up, she placed it lightly on his shoulder. She looked him in the eyes and wondered where this was going. She saw a kind of tenderness that she hadn’t experienced in a long time.
Josh knew that Jessica had a lot of hesitation, but her receptiveness so far gave him all the signals he needed. He noticed her glancing from his eyes, to his lips, and back to his eyes. There was a subtle upturn of her head. “May I kiss you?” he asked.
“I… yes,” she barely whispered, and leaned in just a bit more. Josh closed the distance and still holding her hand, slid his other hand softly around her, resting it in the small of her back. He leaned down, and slowly pressed his lips to hers.
This first kiss was as warm and soft as a Saturday in May, when the only thing to do is lay in the sheets and breathe deeply. Jessica sighed, and relaxed into Josh’s arms, knowing, somehow, that he was a good man.
They moved toward the couch, and their kisses became longer and more intense. This was the moment when Jessica realized there was no turning back. Today was the day, and she was ready to finally lose her virginity.
“Take my shirt off,” he told her. Any other day, the suggestion would have shocked Jessica, but she was determined to go all the way. She slipped her fingers under the edges of his t-shirt and lifted it up over his head, revealing a chest with a perfect amount of hair, just enough for her to run her fingers through. Jessica placed her right hand on his large pectoral muscle, and she felt it flex as he raised his hand and put it on top of hers. “Now you,” he said. Jessica held her breath as she undid the belt of her bathrobe, allowing it to fall open a few inches. She reached up, pushed the robe off her shoulders, and it fell in a soft pile at her feet.
Josh’s face was awestruck as he took in the sight of her nude body. He had assumed she was wearing panties and a bra, and this was an unexpected treat. Her nipples, responding to the change of temperature, had contracted, and her areolas were only an inch across, but much to his delight, her nipples were still fairly large, about half an inch wide. He had developed a kind of fetish for thicker than average nipples ever since he saw some quite large ones in a video a few years ago, and Jessica’s were a treat and a welcome surprise. Her breasts were beautiful, perky C-cups. Her brown pubic hair was all trimmed short, but not shaved. She shifted her weight, obviously starting to get self-conscious.
Jessica was a excited, but a little scared, standing vulnerable and naked in front of Josh. “What if he doesn’t think I’m beautiful?” she wondered, almost panicking. “Well, it’s too late now!”
“I’m a virgin,” she blurted. She had no idea how he would react.
“I think you are beautiful!” he said, smiling. “I will take care of you. Don’t worry. I’ll be gentle.” He took her hand again and had her sit on the couch. Then he slowly stripped his pants and boxers and dropped them on the floor. Jessica’s eyes widened when she saw his penis. She had never seen a penis in real life, but it seemed huge. Standing fully erect, it was actually fairly average, two inches wide and seven inches long, but it was much bigger than anything she had ever put inside herself. He sat down next to her.
Josh placed Jessica’s hand on his penis, and felt her fingers respond, slowly wrapping around its girth. He then guided her hand down to his testicles, allowing her to explore the loose skin and warm roundness of them.
Jessica could hardly contain her excitement when she felt a penis for the first time. “It’s so smooth and warm,” she thought. “And BIG. I have no idea how this is going to fit inside me.” She could tell that her pussy was pretty wet by now. She felt the same giddy excitement as the day she hurried home from the post office with her first dildo. What would it feel like inside her?
Reciprocating, she took Josh’s hand and placed his fingers against her waiting vulva. His touch was gentle, and she smiled when he began to explore the edges of her labia, softly stroking the outside of her mound. Her legs involuntarily began to open wider, allowing Josh to use his whole hand to caress her. She felt her moisture spreading, as it covered his fingers and lubricated the rest of her crotch, and that turned her on even more. She could tell that it was turning him on too.
Josh noticed Jessica give an almost imperceptible quiver when he touched her labia for the first time. He was surprised at how wet she was already, and his cock began to throb when he felt her juices spreading. “Are you ready?” he whispered in her ear.
“Yes. Please be gentle though,” she said.
He stood up, and placing one of his hands above her on the back of the couch, used the other to guide the head of his cock to her dripping, waiting pussy. The first touch made them both wild, and as he slowly pushed the head inside, he watched her mouth open and her eyes widen in shock and ecstasy. She inhaled sharply as his hardness penetrated her. He paused. “Are you okay?” he asked.
Jessica was barely able to respond. “Yes. Please, more!”
Josh’s ass flexed as he inched his penis carefully, a little further into Jessica’s ripe, yearning pussy. He stopped again. “How are you?” he asked.
“Mmmm. So good,” she said. “I have wanted this for so long.”
“Me too,” Josh said.
Jessica felt blood rushing to her vagina, swelling her vulva, and tightening around his cock. She was worried that she wasn’t doing the right things, that she wouldn’t measure up to the way Josh’s previous, more experienced partners had performed. As though he had just read her mind, Josh whispered in her ear: “Take a deep breath, I know this is your first time. You don’t have to do anything special. You are amazing, and beautiful just the way you are!”
She looked into his eyes and saw reassurance there. She followed his instruction and took a long, deep breath. Just as she did, he pushed his solid cock all the way in and held it there. The feeling was like nothing she had ever felt before, and her jaw fell open. She was paralyzed with the pleasure of it. She thought nothing could be better than this, but just as the thought came, it was gone because something better did come. Josh’s eyes had closed with the ecstasy of feeling his penis completely engulfed in Jessica’ warmth, and after pausing a moment, he slowly pulled out until only the very tip was still toying around the inside of her pussy. This vacancy, after such fullness, was more than Jessica could handle.
“MORE!” she arched her back, trying to get his cock back inside. “Give it to me!”
This reaction switched him on, as though he were a machine. He rammed back inside, giving her the full length again, and surprising her with his force. After this stroke, he made a rhythm, beginning to pound her over and over.
Each time he buried his dick deep inside her yearning snatch, the energy of his thrust shook her, bouncing her tits and pulling her legs and toes in. After a few moments of this treatment, Jessica became aware of the distinct (and somehow pleasurable) sound and feeling of his balls slapping against her. Her toes began to tingle.
Josh was an animal. His thrusting kept going, unabated, for ten more minutes. Just as Jessica thought he must be getting tired, he got a new wind, and pounded her flesh even harder. She wasn’t sure how much more she could take - she felt like she was going to explode. Then she felt wave after wave, something like the sensations she got during her masturbation sessions, but more intense.
Her involuntary moans, soft at first, but growing louder and stronger, sent a message to Josh that she was close. She opened her eyes as his body began to pulse harder, coming closer to her. Sweat was beginning to glisten on his skin. She noticed the muscles in his shoulders, felt his breath, and his fingers intertwined with hers.
Then it came. Like a tidal wave, and stronger than any orgasm she had ever given herself. her entire body convulsed in complete mind-numbing pleasure. Her legs wrapped around his back, pulling him in. Her hands tried to break free of his grasp, and, being unable to move them, his strength gave her another pulsing wave of pleasure.
After a few moments, sensing that her orgasm was ending, Josh focused on her perfect, thick nipples and kicked his own pleasure into gear. He felt the beauty of her untouched body, like a hunter who finds a forest valley that has never been explored; the creases of her soft, young skin, waiting for his touch. The passion and glowing expectation on her face sent him over the edge. His body tensed. His cock pressed into the bottom of her pussy and began to throb. His cum filled every crevice of her tight snatch.
As he collapsed, tenderly stroking Jessica’s cheek with his fingertips, he placed another kiss on her lips and took a deep breath.
Jessica was enthralled by the feeling of his cum inside her. Her pussy was throbbing, and the tingling was still coming across her body. She felt some of Josh’s load start to move down her vagina, and placed her hand at her opening. Her heart leaped when the cum, mixed with her juices, touched her fingers. She looked at Josh, and realized he had been watching the cum roll out of her. She caught the sticky mess, and slowly rubbed it around, coating her swollen labia. Josh’s eye’s widened.
“Are you sure you’re a virgin?” he asked.
“I’m not anymore!” she smiled.