** Author’s Note: I created this story based on a reddit Dirty Pen Pals prompt (probably 2+ years ago). It went from something small to a longer story. I combined the parts I’d written on reddit into this story. I might keep the series going or switch back to my Worst Roommate one. The main character, Mary, is in fact 18 for the story. Just a short, petite girl. Enjoy! **
HOOONK
Mary’s right hand slipped off the handlebar of her bike as she was torn away from her own thoughts by the car’s horn. Luckily she was just sitting at the intersection, thinking of last night’s embarrassment, instead of biking across the road.
Quickly looking up to her left, she noticed it was actually a U-Haul van with a guy behind the windshield waving her across the road. Blushing furiously, she put her hand back on the bike’s handle, purposefully avoided eye contact with the driver and began pushing herself across the road – standing up on the pedals with extra effort. Soon she was idly cruising on the sidewalk with her mind already thinking back to last night.
—-
All four years of high school, Mary had been the innocent girl that seemed to hover in the background of all the drama, cliques, sports games, and romances. The last one she regretted the most.
Sure, Mary had friends and people she talked with, but she’d always focused so hard on her grades and a couple extra-curriculars. So much so that she never put much effort into having a group of friends. Between honors classes, yearbook, the school newspaper, and volunteering around the neighborhood, Mary’s last four years didn’t include anything she’d secretly wanted. Best friends, sleepovers, late nights, parties, and even a little bit of romance… or sex.
At 5’1″, Mary was a short girl who was easy to not see in the crowded hallways of high school even at the age of 18. Everyone was so much taller than her that she literally flew under the radar. In her yearbook group, she’d noticed the surprised looks of other boys when they focused on her, but then they’d see one of the pretty cheerleaders or volleyball players and change focus. Barely over 100 pounds, Mary thought she was a pretty girl when she looked in the mirror: dirty blonde hair, firm and perky C-cup breasts that seemed large for her size, thin waist, and bright blue eyes framed in thin glasses. She’d been called pretty before. As well as cute, tiny, and ‘pixie’, but she didn’t feel… hot. Mary felt looked over.
Which was why she was pleasantly surprised to be invited to an end-of-the-year party for her high school class. Granted, they only had about 300 students in the graduating class, but to be invited at all was a pleasant surprise. Apparently one of the more well-off students’ parents said he could invite everyone and they’d have it at their house (more like mansion). Even if only 100 students went, it’d be the biggest get-together Mary had ever been to.
The night of the party, last night, Mary drove to the boy’s house and up the long driveway. Cars were parking in the front yard, so she found a spot, parked, and walked up to the house. Luckily there were a stream of kids filtering in through the front door, so she was able to join the group instead of arriving alone.
The first thing she noticed was the noise. It was so loud. Music she had never heard before was blasting with a beat and strong base that made her stomach bounce. Her fellow classmates were scattered around the house – sitting around a living room table, bunched up on couches in the family room, playing games at a large kitchen table, and an open door with stairs leading down to the basement which had a whole other song blaring. The entire house looked like a Hollywood movie where teenagers went crazy during a party. Luckily, it was either too early or there wasn’t actually any alcohol because no one seemed to be throwing a vase or breaking cabinets.
After dodging through crowded hallways, Mary made it to the kitchen and poured herself a soda while looking around for people she knew. Eventually she found a friend from the school newspaper, Casey, and started talking with her and her friends. Everyone was nice and friendly which helped put Mary at ease. After 15 minutes or so, she followed them downstairs for a ‘change of scenery’.
A similar atmosphere met Mary as she walked down the stairs. The railing up was open to everyone below and Mary self-consciously smoothed down her dress. On second thought, she realized it wasn’t necessary. Her knee-length dress was nearly double the length of the skirts and dresses other girls had on. Compared to them, Mary suddenly felt… old-school.
Mary followed the group she through the basement toward the back area where it seemed to be a little less crowded and quieter. They found a couple chairs, split off into couples and sat around talking about after-graduation plans. Most of the people seemed to be going to out-of-state schools, while Mary would be going downtown to a more arts-focused school in the city.
It dawned on her then that none of the people she was talking with were going to college with her. Her heart sunk even more after hearing the boys and girls around her talk about this party being the last hurrah for some of the couples. They’d stay together in the summer for a bit, but most people agreed that it was best to not have obligations when traveling away from each other for a whole year. Mary hadn’t had a boyfriend the past four years – no, her whole life. And yet the kids around her acted like they were moving onto new experiences.
Excusing herself to go to the bathroom, Mary started wandering away from the group and toward the nearest closed door in the basement. The first two she tried were locked (How many rooms does this house have? she thought to herself). Finally, the next door’s handle turned and she cracked it open. The room was dark inside so she fumbled for the light switch. Just as she flipped the switch, she heard someone say, “Hey wait!”
With her head inside the cracked door, Mary’s eyes took a second to adjust to the light before she noticed a boy sitting back on a chair with a girl kneeling on the ground next to him. His pants were gathered around his ankles, the girls shirt was pulled down below her breasts, and her hand was wrapped around his dick. His big dick, at least to Mary. For a split second it seemed like the girl was holding one of those large camping flashlights.
Then just as Mary was coming to grips with what was happening in front of her, the girl shouted, “Hey, get out of here you perv!”
With a slight squeak, Mary slapped the light down and quickly closed the door. She leaned against the door frame in shock as she got her breathing back to normal. Looking up, she noticed at least 10 people looking at her with confusion on their faces. Realizing that everyone was watching her, Mary’s face turned bright red and she quickly made her way through the basement toward the stairs – not even noticing her friends calling to her as she passed.
The rest of the trip through the house and all the way home seemed a blur to her. Mary’s face felt like a million degrees, her knees shook, and she had tears in her eyes. Her first time at a party, first time in a large group of peers, and she ruined it by peeping on a couple. How could she have ruined her first party so much? Mary was embarrassed and distraught the whole ride home.
It wasn’t until after she’d got home, ran upstairs, showered, and lay in bed that she began to calm down a bit. How could she have known what was happening in that room? It wasn’t her fault – she was just looking for the bathroom. Thinking on it even more, she realized she didn’t even recognize the girl and guy in the room. After a few deep breaths, Mary came to the conclusion she had blown everything out of proportion.
After finally becoming relaxed and beginning to fall asleep, the last thing Mary thought of before her dreams took over, was the girl’s hand wrapped around the boy’s large dick. The first dick she’d ever seen in person. She hoped it wasn’t her last.
—-
Upon waking up, Mary had breakfast, talked with her parents, then went on a bike ride around the neighborhood hoping she could get her mind off the party. It was a success, but only because she kept thinking back to what she saw in the room. Which was why she had sat idly at the corner of the street intersection and was startled by the U-Haul. Only to resume her same thoughts seconds later on the sidewalk.
Her face felt heated and it wasn’t by the warm morning sun. Even her knees seemed to be wobbly as she road. It was because of the dick she saw. Mary kept imagining it up close instead of across the room. She was sitting on the ground next to his chair. She had her hand wrapped around his dick. Would it even fit in her grip? Mary looked down at the handlebar gripped in her right hand and tried to compare it to the dick.
“Hey, careful now!” A man yelled.
Looking up quickly, Mary slammed backward on her pedals and came to a halt a few feet away from the same U-Haul van that pulled her from her fantasies earlier.
Turning to her left, Mary saw a young man balancing two boxes in his arms while facing her. He looked older than her, but still young – maybe in college? He had brown hair, looked pretty tall compared to her, and was… fit. His tight, white t-shirt looked a little smudged and his gym shorts appeared to cradle his ass. Get a hold of yourself Mary.
Blinking quickly, Mary met his eyes and said, “Uh thanks. My head was in the clouds.” She felt herself blushing as she thought of what her head was really thinking of.
The guy smiled at her – his eyes seemed to have an odd glint like he knew what she was thinking. Not like a predator, just… like he saw the way she looked at his gym shorts. Oh god, how long did I look?
“No problem. That’s twice you’ve spaced out. So, do you live in this neighborhood?” He asked while setting the boxes on the ground. His forearm muscles seemed to dance when he did it.
“Y-yes. I do. I’m just two houses down with my parents. Are you and your family moving in?”
“Yup. Well, me and my dad. Parents split up so we moved closer to his job.”
“Oh, sorry to hear about your parents.”
“Don’t worry about it. Long time coming really. Dad’s working and since I’m home for the summer he figured I’d love to do most of the unpacking myself.”
Looking from the guy to the U-Haul, Mary realized she had nothing going on. Especially when him and his muscles are doing all the work alone.
“Would you like some help? I probably can’t lift the heavy things, but I can unpack stuff with you.”
His eyebrows rose and a smile lit up his face. “Wow, that’d be great. Thank you. I’m David by the way.” David walked toward Mary.
Stepping off her bike and letting it slip to the grass, Mary took his hand in hers and said, “I’m Mary, nice to meet you.”
David picked up the boxes and showed Mary inside. He was on his last trip with the truck, so most of their things were already placed somewhere in the house. After stepping into the kitchen, he said Mary could help with unpacking the boxes here.
As Mary got to work unpacking the utensils and cooking ware, she’d glance up and watched David walk in and out of the house. He must have been an athlete or maybe still is because he looked amazing. Easily 6 foot or more, his arms weren’t huge, but they had some defined muscles. His calves looked like he ran or biked. And… well, she couldn’t see his stomach but she figured it was just as defined as his arms and probably covered in a sheen of sweat –
Mary shook her head and tried to focus back on putting things in drawers. But even thinking of his sweating body reminded her that her forehead had a bit of a sheen to it as well. Apparently they didn’t have their A/C on and it was starting to get to her.
Luckily, David came inside at that moment and put down a box with finality. “Whew, last box. I’ll close the door and put the A/C on. I didn’t want to let it run with the front door constantly open.”
A few minutes later and Mary felt the occasional breeze of artificially cold air. David had walked over to the kitchen counter and they began talking about their lives. School, friends, summer plans, and things to do in the area. Pretty soon Mary had everything put away in drawers and cabinets and had cooled down enough that she didn’t feel like beads of sweat were gathering along her hairline.
David stood up and began tugging his shirt away from his body, “Well, I feel pretty gross and sweaty. I’m going to take a shower real quick. We don’t have the TV setup, but there’s at least some water and beers in the fridge. If you’ve still got time, you can grab whatever you’d like and I’ll be back down in a couple minutes.”
“Yeah, sure. I’ve got nothing planned today and a drink sounds good.”
“Great. We can go grab some food after as well,” David said with a hopeful smile.
Mary matched him and said, “I’d like that.”
As Mary walked to the fridge, David bounded up the stairs to take a shower. Although tempted to grab a beer, Mary took out a bottle of water and unscrewed the top as she walked to the kitchen windows facing the backyard.
“Uh, hey, Mary!” David shouted from upstairs.
“Yeah, are you okay?”
“Yeah, yeah. Could you grab a towel for me? I’m pretty sure they’re in the family room – I completely forgot to grab one.”
Mary saw the box immediately – it was conveniently labeled ‘Towels’. She grabbed the top one and walked upstairs. When she reached the top she noticed a door to her left was cracked with David’s head poking out.
“Thank you! Didn’t even realize until I was in here,” David said with a laugh.
“No problem. I’ve done that before as well.”
Mary reached the door and handed the towel to him. As the door began to shut, she saw through the crack was a mirror and in the mirror was David’s gloriously rounded butt. Her eyes shot open, but the reaction went unnoticed as David closed the door and she heard the curtain being moved.
Wow, if that was his back, I wonder what his front is like?
Mary stood there for a moment before she regained composure and began wandering around upstairs. The house was a good-sized place with what looked like three bedrooms. One was the master and had a built-in bathroom. The other two were regular rooms – one with a bed and various clothes that were most likely David’s. The last room had some weights and exercise equipment and a TV sitting on the floor. As she was looking around in the weight room she heard the bathroom door open and footsteps as David went to his room.
A second later two loud thumps echoed down from the hall. Walking quickly down the hall, Mary saw his bedroom door cracked and called out to him as she reached out.
“Oh, I just dropped -” his voice cut off as Mary pushed his door open and they both stared at each other.
David was holding a worn, white football helmet in his hands and stood facing the doorway. His brown hair was in a partially dry mess and his clothes were nowhere to be seen. He definitely played sports and his six pack abs were exactly what she’d imagined. Mary’s gaze drifted down and she drew in a sharp breath.
His dick was big. Even bigger than the one she saw in the room and it was just lazily pointing at the ground. His soft dick was bigger than the hard one Mary had seen in the downstairs room. Could she even fit her hand around it? “Wow.”
David watched her expression as she zoned in on his dick. Her eyes widened even more than when he called to her outside and she looked at his butt. Mary’s mouth was open and even as he watched her tongue snaked out and licked her lips. With a smile creeping across his face, he moved the helmet to one hand and let it hang by his side.
“Oh sorry, the helmet fell off my bed. I didn’t mean to scare you.”
Her eyes still focused on his dick, Mary only stammered a bit, not really making sense even though she meant to say, “It’s ok.”
David’s smile got even bigger as he watched her stand there in shock. He usually had girls gasp when seeing his dick, but never stand there mutely. This girl was something else. It’s like she’d never seen a dick before. Maybe she hadn’t? His dick twitched as he thought of what else she hadn’t experienced.
“Oh.” Mary exclaimed as she watched his dick bob up and down in front of her. She looked up to David, saw his big smile, and immediately blushed. He could simply see how flustered she was – he probably knew how inexperienced she was as well. Mary wanted to run out of the house, but she couldn’t will herself away from him and his – oh my god – slowly growing dick.
David nearly laughed as he watched Mary almost lean forward while his dick began to rise. His cock is around 5 inches soft and 8 inches when hard. While he knew he wasn’t the biggest ever, David definitely never had complaints from the girls he’d been with. Now that he was in a different neighborhood with his dad, he didn’t have anyone nearby to hang out with or continue last-summer flings. Mary, this seemingly innocent girl who was enthralled by his dick, seemed to be the best bet he had for something interesting this summer.
Placing the helmet on his bed, David began to slowly walk toward Mary. After two steps toward her, David saw her eyes look up to his along with a quick intake of breath, before focusing back on his now 6 inch cock. When he was three feet away from her, he watched her hands open then close at her side. With one foot between them and his cock at nearly full length, David called her name to get her attention.
With wide eyes, Mary looked up at him. Apprehension, fear, excitement, and lust seemed to blend across her face.
Still smiling down at her, David whispered, “You can touch it. If you’d like to.”
Mary’s head lowered until her eyes focused on his bobbing dick. It seemed to be pointing at her chest. The head of his dick was large, red, and perfectly formed. Like all the drawings she’d seen in books and movies and the videos she occasionally looked at online. He was circumcised which seemed to make it look even larger. Smooth skin lead down his long shaft to his hanging balls – bigger than the largest grapes she’d ever… put in her mouth. The hair around his crotch was trimmed very short and he looked… he looked so clean. Mary’s hand was halfway to him before she hesitated.
“Go ahead,” he whispered to her.
Mary’s hand closed the gap and her index finger made contact first. She trailed it around the top of his head and around the underside. When her finger touched the bottom, David’s dick twitched away from her finger before settling back down against it. Mary moved her finger to the top again and slid it toward the base, closing her hand around his shaft as she did so.
“It’s… so warm. And soft. And hard. And big.” Her voice dripped in wonder and lust.
David chuckled at her response. This girl was definitely new to this. If his wasn’t the first cock she’d held, he would give up sex for life. Actually, that’d be ridiculous, but he knew he was right.
Trying to hide his eagerness, he softly said to her, “You can see it better on your knees.”
As if in a trance, Mary slowly dropped to her knees and easily switched her grip so her thumb was wrapped around the bottom of his dick. Wrapped around would be an exaggeration, her hand couldn’t close all the way around it. There was a two inch gap between the tip of her fingers and thumb.
When she was on her knees, Mary felt his dick strain again in her hands. It felt powerful, yet delicate at the same time. The tip of his dick seemed to wink at her and she saw a drop of fluid slowly form inside the hole. As the bead of liquid grew in size, Mary slid her hand toward the tip and used her thumb to spread the fluid around the head – rubbing in circles just inches from her face.
David breathed in deep as she rubbed his head. Looking up at him, Mary saw his reaction and a shy smile wiped away the awed expression she’d had on her face since she walked into his room. She focused back on his dick and continued to rub the head with her right thumb while her left hand wrapped around his shaft and slowly moved up and down.
Mary had read stories online and watched videos of girls doing this, so she knew what was supposed to happen. But she never realized this is what it felt like before. As if she had control of him, but only just a little. She couldn’t even wrap her hand around the shaft and it seemed to almost pull out of her grip each time it throbbed. While she was the one with the grip, his dick felt big enough to be a weapon if he wanted it to be.
Her slow hand movements kept up until David spoke to her again. “It’s a little easier and feels better with lubrication.”
Mary looked up a little confused. Lube? Does he have that sitting around? “Um, you want me to use lube?”
David chuckled and she felt it trembled through his shaft and into her hands. “No, um, not actual lube. But… spit work as well.”
“Oh. Oh right.” Spit, her mouth, a blowjob. At first she felt so dumb – of course that’s what he wanted. This was fast for her, but it was also the first dick she’d ever touched and she just graduated high school. Everyone else was leagues ahead of her. Mary transferred her lack of knowledge into determination. I can do this. I don’t want him to think I’m some prude who doesn’t know anything. How hard can it be?
Moving her thumb, Mary leaned forward and breathed in. He smells like fresh soap. Her tongue quickly snaked out and settled under his head. She pulled her tongue in and traced it along the bottom to the tip and flicked upward. Pulling her tongue back into her mouth, she realized the liquid tasted a little salty, but not bad at all. Mary licked the head again and also trailed her flattened tongue to both sides of his head before wrapping her lips around the tip. Her mouth felt a little full and she didn’t even get whole head in!
Tongue swirling, she moved her head a little forward and felt her lips drag up and over the crown before settling behind the ridge. A few swirls more and she felt saliva building up in her mouth. Mary slid the dick from her mouth and ended by suctioning her lips at the tip and swallowing the spit in her mouth. She breathed in slowly and looked up at David’s face.
His eyes seemed to be on fire with lust and his smile was filled with surprise and happiness. I did this, Mary realized. No, I’m doing this now. And he likes it.
As if to affirm her thoughts, David said, “Wow. That feels amazing.”
Mary smiled shyly and said, “Thanks. You have the biggest dick I’ve ever… had.” Mary blushed as she realized she almost said ‘seen’. But he probably already knew.
“You’re doing great. Keep sucking my cock like that – you’re a natural.” Inwardly, David smiled. He watched her shoulders perk up and her neck straighten as he called her a natural. This tiny little girl just felt like she accomplished something by simply sucking on his cock. Maybe she truly is a natural at this.
As if to affirm his thoughts, Mary slid his dick back into her mouth with two more inches traveling past her pursed lips and being coated in her warm saliva. Her tongue swirled, her left hand continued stroking up and down, and she felt the spit gather in her mouth. Instead of swallowing she started trying to take more of his dick into her mouth so the saliva spread down his shaft. About five inches in and she felt his head hit her throat and her muscles clenched up. Mary quickly pulled back and took a deep breath. I can do better.
David watched her put another five inches back in her mouth then open her lips a little bit letting spit drool down to her left hand. That hand used the spit to coat the rest of his shaft all the way down to the base. Good lord, he thought, this girl truly is a fucking natural cock sucker.
A few more repeats of this process and his entire shaft was soak in her spit. Mary’s lips moved up and down, now with six inches of his cock, but that seemed to be her stopping point. She would alternate her suction from hard to soft and occasionally run her tongue from the base to the tip and back down.
Mary heard his breathing getting faster and watched his hands clench a little. Looking up at him, she made eye contact and raised her eyebrows.
“I’m almost there Mary.”
Oh god, do I swallow? It didn’t taste bad before and guys seem to like that. Hopefully he tells me when.
Mary moved only a few inches in and out of her mouth, but her right hand switched to stroking while her left cupped his balls. She picked up speed with her right hand and felt his breath quicken with the stroking.
“I’m going to cum,” David breathed out.
Mary watched his eyes close shut and felt his hands hold onto her head. She now held his shaft with both hands and tried to milk him into her mouth with just the crown of his head inside of her lips. His breath exploded out and with it a shot of cum hit the top of her mouth and landed on her tongue.
Mary looked back down at the dick between both of her hands and partially filling her mouth. Her head felt light and her body seemed to be buzzing all over. Her head, neck, chest, and pussy seemed to be on fire. A trembling in her toes seemed to shoot up her legs and explode inside of her in an area she didn’t even know existed – this was nothing like when she’d try touching herself. Mary was orgasming from sucking his dick – her body shook and she simply held on.
Another two blasts had shot out of his head before she felt like her mouth was getting too full and she swallowed. It was definitely heavier than earlier, but not any worse. She actually didn’t mind the taste and let him finish before she swallowed again. The head and shaft twitched as she held still and simply watched him slowly gather his breath. Mary took him out of her mouth and rested her cheek against his shaft as her breath came back to her as well. Lowering her body slightly, her butt rested on her heels as she felt her leg muscles get back under control.
David’s legs felt shaky, but he stayed standing and opened his eyes to look down at Mary. He watched her go from resting his cock against her cheek to kissing up and down the shaft. Soon she was planting kisses on his head before simply holding his cock and staring. Good lord, this girl is hooked.
Mary took a deep breath and looked up at David. She smiled in anticipation and put her current thoughts to words. “Can you put this big dick inside of me?”
Upon hearing her question, David’s cock and stomach both leapt. He could probably be this girl’s first and end up having her around all summer. If she was so receptive of giving him a blowjob and now asking him to fuck her…
David knelt down on the ground to get a little closer to her level. While he lowered himself, Mary’s hands kept a soft grip along his shaft even after he was finally kneeling. “I’d be honored to do that for you. But it might help if I wasn’t the only one not wearing clothes.”
“Oh, right,” Mary said with a laugh. Her hands pumped twice more before she begrudgingly let go of him and stood up.
Mary wore a light blue tank top and running shorts that ended slightly above mid-thigh. Not super tight shorts, but still showing a good amount of leg. Within seconds her shirt and shorts were on the floor next to her discarded sandals. Mary watched David’s eyes, which were glued to her bra-covered breasts, as she reached back and grabbed hold of the clasp. Even after what she’d just done, Mary felt a little self-conscious. While she may have willingly sucked his dick, she’d never been naked in front of another guy before today. With a deep breath, she unlatched the bra and pulled it away from her arms and stood there apprehensively with her arms at her side.
David’s eyebrows rose and his eyes widened, but for a few seconds he didn’t say anything. Then he blew out, looked at her face and said, “Wow, you’re gorgeous.”
With her cheeks suddenly flushing with blood, Mary looked to the side then the ground. “Really? You think so?”
“There’s no doubt in my mind.”
Her confidence renewed, Mary’s smile curved into something a little devious and she quickly slid her white pantie down her legs and stepped forward out of them. She placed her hands on his shoulder from less than a foot away and said, “There. Now we’re even.”
David’s eyes snapped down to her thin patch of nearly see-through blonde hair sitting above her visibly wet lips. He leaned forward and kissed her belly button causing her stomach to flutter. “Well, not quite even yet.” Sliding his hands from the back of her thighs to her ass, he lifted her up and stood at the same time.
A squeak escaped her lips as Mary was lifted up in the air. Her hands gripped his shoulders tightly and kept her arms locked while legs wrapped around the middle of his back. As she felt both of them turning, the movement putting her back to the bed. Mary looked down between the gap of his stomach and her thighs to see the shaft of his swollen dick disappearing below and behind her. Jesus, would that even fit? She thought to herself. Her hands were one thing, but putting it somewhere only her fingers and (one time) a marker had been seemed nearly impossible.
Watching the trepidation build on her face, then seeing her eyes focusing on his dick, David said, “Don’t worry, I’ll make sure you’re ready first.” He lightly placed her on the bed – letting Mary’s back settle down and her blonde hair fan out around her head. Kneeling in front of the bed, David used his hands to spread her legs out to either side as his mouth kissed down from her bellybutton, past her short blonde fuzz, and then stopping as his lips rested at the top of hers.
Looking up, David met Mary’s eyes as she eagerly watched him positioning where no man had ever been. He narrowed his tongue and slipped it between her lips and slowly slid downward. As his tongue tasted her from top to bottom, Mary’s head fell back to the bed and her eyes closed. Reaching the bottom, he poked his tongue further inside of her before flattening it and running back to the top.
David felt her tremble through both legs as he repeated the process a few more times. Each pass seemed to gather more and more of her wetness on his tongue as her excitement reached levels she’d never known existed. Despite wanting to get her off for the amazing blowjob she gave him, he had to loosen her up a bit as well. Removing his right hand from her thigh, his lips and tongue went to work on her clit as his right middle finger began sliding up and down between her lips.
It feels sooooo much better than when I use my fingers, Mary thought as his tongue slid up and down her pussy.
Then his lips trapped her clit and she felt his tongue sliding in circles and lines and shapes and… she didn’t care it just felt amazing. Her fingers gripped the bed sheets and she tried to steady her breathing but seemed to forget to keep breathing out. Each breath ended with a shaky exhale and her eyes stayed firmly shut. Mary felt her head tingle like she had just spun around and around in circles.
Soon enough she felt something solid but warm begin pushing inside of her. For a moment she thought she was finally experiencing sex for the first time, but realized his tongue was still sending shocks from her clit to her fingertips (and her shoulders, ears, eyes… she felt it everywhere). David’s finger slid in slowly and gently just a little bit before retreating and pushing further.
I knew I was missing out, but oh my god I was really missing out, Mary thought as another person was pushing a finger deeper and deeper inside of her.
It felt like his finger was three times deeper than hers could ever go. New areas opened up inside of her and she felt all of it, loved all of it. Mary moved one hand to her breasts and began rubbing and toying with her nipple as her other hand ran up and down his arm.
Bending his finger a bit, David began rubbing the top of her pussy on each pull. He was already deep enough to have the back of his other fingers resting against her on each push inside. Mary’s breathing seemed to echo with a moan and groan – matching with his in and out movements. David then switched his middle finger with his ring finger for a few plunges. Once it was sufficiently wet, his fingers pressed together and he eased them both inside of her. Her hand sliding up and down his left arm gripped tight and he watched her squeezing tightly to her own breast. It took at least ten in and out movements before he felt her pussy accepting his two fingers.
Damn, she’s tight and I’ve only got two in.
After a minute of his two fingers pushing and stretching her pussy, Mary realized she’d been holding way too tight to her left breast. Letting go, she slid her hand down her stomach and combed her fingers into his hair. David’s tongue still kept up slow but steady movement on her clit while his fingers slid and curved and stroked inside of her. Something seemed to be building up within her. A warmth that was spreading from the inside of her stomach and up her chest. Her arms and chest felt warm but had goosebumps at the same time. Every time she felt his fingers slide deep and his knuckles rest against her outer lips, it was like 50 butterflies jumped in her stomach at the same time.
David watched her legs, her arms, her head and hands move more and more. She was building up and he wanted to push her over the edge. Repeating his previous switch-a-roo, he swapped his ring and middle finger for his middle finger and index for multiple pumps inside of her. Once both fingers were nearly dripping, he put all three at her entrance and began pushing forward.
Immediately her lower back heaved off the bed and he felt her muscles clench on his fingers. “Oh fuck!” she nearly shouted as she experienced an even further stretch.
Three fingers? That’s so much! Is this what his dick will feel like when he pushes it in?
After a few strong clenches on his fingers, David began small movements in and out. Repeated motions, slightly deeper each time, and three fingered curls we causing the blonde beauty in front him to build into a trembling mess. A minute later and he was pushing in and out with full strokes as her pussy repeatedly clenched and unclenched on each push. Her breathing was ragged and moans were almost a constant stream of sound punctuated by strong breaths in.
Feeling it was time, he increased the speed of his fingers and began rapidly flicking side to side with his tongue. The change in Mary was nearly instantaneous. Her legs clamped shut around his head and hands rushed up to hold her face then tightly grip the bed sheets above her. Something unintelligible rushed out from her lips – David couldn’t tell if it was her thighs blocking sound or she just wasn’t making sense anymore.
Moments later her pelvis pushed up toward his mouth and he let her push him upwards as the rest of her body clenched up. Her legs squeezed tighter, her knuckles were white and her head was leaning back nearly looking at the other side of the bed. Large quakes rocked her body and a loud groan vibrated into his ears from her legs.
David slowed down his fingers until they were simply held inside of her. He gave her one last lick before removing his lips and breathing in deeply. Slowly, he guided her body back to the bed as her breathing returned to normal. Once she was settled down on the mattress, he slipped his fingers from her warmth and watched her legs weakly fall to either side. With a smile, his right hand gripped his cock and he stepped forward.
There wasn’t any part of her body that didn’t feel like it had fallen asleep but now was waking back up. Little tingles of electricity seemed to dance across her skin and it felt like her vision would never go back to normal. Black spots and squiggly lines dance across the ceiling above her. Mary ran her fingers through her hair and breathed deep. After a long exhale, she raised her body with her elbows and looked to David. “That was absolutely amaz—”
Nearly laughing out loud, David watched her face go from relaxed contentment to absolute surprise as the head of his cock slipped inside of her. Mary’s eyes traveled from where his cock was slowly pushing inside of her no-longer-virgin pussy to his face. Then she looked back down to where their bodies were locked and switched her balance to her left elbow. Her right hand slid down her stomach and her fingers spread out on either side of her pussy – cradling both her lips and his shaft.
“Oh my god. It’s… so warm and… and big… and full,” Mary stuttered out the words as David pushed a little more inside of her.
Three fingers might not have been enough, David thought as the vise around his cock seemed to stop him from moving at all.
All he could manage was barely moving his head in and out with a little bit of his shaft sinking into her. But even so, the expression on her face was an absolute delight. Pain, excitement, lust, surprise, and… anticipation? They all met together as she simply watched him slowly moving inside of her.
What seemed like minutes later, David felt her relaxing around his shaft and he pushed another inch inside. Muscles clenched tight and he seemed to go no further again. Multiple small movements and the process repeated. It seemed to take forever before he was even five inches inside of her. At that point, Mary’s arms seemed to give out and she just laid back on the bed. Grunts and moans accented each thrust inside of her. Both of her hands just rested on her breasts while her eyes stayed shut and her head was turned to the side.
David wrapped his arms under her thighs and gripped his hands around her hips. Using the new leverage, he began increasing the pace of their process and soon had a little more than six inches sliding in and out of her. Her inner lips seemed to stretch on each pull and caved in on each push. At seven inches her hands gripped tight onto his forearms and he looked up to see her watching him.
“Is that all of it?” Mary asked which a soft voice.
Holding eye contact, David pushed with finality and sunk all the way into her until their bodies met. Her eyes popped and her mouth opened in shock as he said, “That’s all of it.”
“Oh my god. It’s deep. I think it’s in my stomach,” she said with incredulity.
“Does it hurt? Are you ok?” David asked with a bit of concern.
Mary breathed in a few times and he felt her pussy flexing around his cock. “I’m… full. It’s not painful like it hurts. I feel like I’m stretching for the first time. It… it feels good.” The last words were punctuated with a smile on her face.
“Just wait,” he responded as he slowly began pulling out.
Both of them moaned at the sensation and grunted has he pushed all the way in for the second time. The third time was a bit faster and by the sixth time her ass met his thighs, they had a steady rhythm going.
“I’m having sex. Oh god. You’re fucking me. I know… I finally…” Mary trailed off as she held on and gave in to the sensations.
A chuckle shook out from David as he listened to her coming to grips with what she’d always been jealous of others experiencing. His gaze traveled from his plunging shaft, up to her bouncing breasts that seemed too large for her form, and up to her face. A wide smile appeared on her lips after every breath in as she basked in the feeling of being full. The feeling of a warm cock sliding in and out of her – stretching her in a whole new way. The feeling of being fucked.
Changing positions slightly, David moved her legs toward the ceiling and placed them on his shoulders. She was short enough that her calves rested on top of him – her knees just weren’t the right length. Leaning forward, David placed his hands on either side of her body just below are armpits. Closing the gap between them, he moved his head forward and kissed her deeply. The first kiss they shared and her legs were pointing at the ceiling while his cock was balls deep inside of her.
The new angle had him pumping nearly straight down into Mary. She felt even fuller now, as if this angle allowed him to completely fill her like the other one couldn’t. Or maybe it was the closeness of their bodies. Or the way their tongues wrestled and breaths mixed. Whatever it was, Mary moaned into his mouth as his thrusts sped up and the intensity increased.
David hadn’t been fucking her more than ten minutes and he already felt the familiar tingle deep inside of him. Mary’s tightness was getting the best of him. He couldn’t even think of the last time a girl he fucked was this tight. Hands grabbed him on either side of his face and pulled him from the kiss. He recognized the heavy lust-filled look in Mary’s eyes as she looked up to him. “Fuck me, oh god please fuck me.”
The thrusting speed increased and on each downward thrust he pushed his cock up just a little bit more. Mary’s face pressed into the crook of his neck and he felt her breath each time she encouraged him to fuck her. Each time she said it, Mary’s voice seemed to increase in pitch. Desperation crept in and her breathing struggled to remain constant.
“Fuck me. Oh, god, again. I’m going to… going… I’m… cumming!” Mary shouted as her calves pressed into his shoulder and her fingers dug into the back of his neck.
Her body was wrapped up so tight against him that the trembling wasn’t as wild as her first orgasm, but it was no less strong. Muscles deep inside of her pussy fluttered tightly around his cock and David began to feel the edge coming up to him as well.
“I’m going to cum,” he struggled to say between thrusts.
“Yes!” Mary encouraged him as she pulled back to watch his eyes squeeze shut. A small flash of thought swept across her mind about him finishing inside of her, but was slapped away by a quick reminder of being on the pill. “Do it,” she whispered with a smile on her face.
David’s stomach, legs, arms, and ass clenched as he thrust deep inside of her and let go. His eyes saw stars beneath their lids and a trembling exhale traveled past his lips. Four or five spurts of cum streamed into her before he felt his body losing the strength to stay upright.
Mary watched him move his arms around her legs to free them from his shoulders then lower down to his elbows above her. His warm and shuddering stomach rested against her breasts. She wrapped her legs around his back and held him close. “That was amazing. Thank you,” Mary said as he began opening his eyes to hers.
“Me? Haha, thank you. Damn, you’re something else Mary,” David laughed with her.
“Really? I am? It felt, it felt wonderful. I’d thought of it, but oh my gosh this was so much better than I imagined.” Words seemed to stream from her mouth after hearing his praise. Mary felt excited, proud, and eager.
“I’m glad,” David responded. “You are a natural at it. Definitely blew my mind.”
Feeling his dick begin to soften, David slowly withdrew his cock until it popped out. Looking down, he watched a dribble of cum appear at the bottom of her lips, then lazily slide further down to her ass. With a grin, he turned over onto his back and laid next to her. A soft, wet slap accompanied his softening dick as it fell backwards onto his stomach.
Turning his head to Mary, he watched as her hands softly rubbed her pussy lips and smeared his cum around them, then up further onto her stomach. Mary’s head turned as well, but looked down at his cock and the fluids mixed into a sheen around it. Her body straightened up then moved closer to the bottom of the bed until she turned onto her knees and straddled his legs. A look of wonder and awe covered her face as she wrapped both hands around his slick shaft and softly moved her hands in circles.
Mary looked up at David and saw him curiously watching her movements. Gazing back down at the soaked dick in her hands, she lowered her head and began to lick up their combined juices. First her tongue swirled and swept up whatever she could into her mouth. But soon she was bobbing up and down on all of his slightly hard shaft. Not being at full length, the base of his dick repeatedly felt the warm suction of her lips. Within a minute, Mary had cleaned him completely and let out a deep breath.
Still holding him in both hands, Mary raised her head and asked, “Can I try being on top?”