Their First Time
Eki 16, 2022 // By:analsex // No Comment
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After years of reading stories from others, I have finally decided to try one of my own. Feedback appreciated.
It was a fall evening, slightly cool, just after sunset. Cassie was with her boyfriend of 6 weeks, heading out to a dance club. They had just finished dinner and a couple of glasses of wine at their favourite restaurant.
Cassie and Jack were 19 year old university kids. One from the big city, one from a rural town. They had met at school, having happened to sit beside each other one day in class.
Jack was a bit of a shy kid, 5ft 10 and skinny. He had sparkly blue eyes and an impish grin. Cassie was 5ft 9 with brown eyes, long brown hair, and small perky breasts. She was even more shy than Jack. She noticed Jack beside her, thinking him kind of cute. And Jack noticed Cassie – he thought she was beautiful and he had a thing for long hair, but figured she would be way out of his league. He was just too afraid to talk to the girl in the seat beside him. The class continued on.
The next time they had that class, they again sat next to each other. During the class on a particularly challenging topic, Cassie asked Jack if maybe he’d like to study with her sometime. Jack understood the lesson pretty well, and said sure, he’d like that. Perhaps they could meet after classes in the student centre, since they could talk more than in the library. And maybe grab a bite to eat after. Cassie agreed.
Since that first meeting, things had progressed slowly but steadily. They went from studying together, to binge watching Stranger Things, to dinner, and a couple of movies. They held hands in class, and made out in his room, and sometimes in hers; kissing, holding, touching, petting. Always with their clothes on.
Tonight, after dinner, Cassie suggested going to a club. Jack agreed, even though he wasn’t much of a dancer. They got to the club, paid the admission, grabbed a booth and ordered a margarita and a daiquiri. Feeling good, they ventured out onto the dance floor. It didn’t matter that Jack was a bit awkward…. He was kind of cute, in a geeky sort of way.
After a couple of fast songs, the music slowed and he looked into her eyes. She nodded slightly, a smile spreading across her lips, and they embraced. Close and tight, her scent delightful, and her body pressed against him, he quickly became hard and somewhat embarrassed. Cassie could feel his erection and pressed herself into him, enjoying the feeling against her crotch. They bent their heads together, lips meeting, in a fiery kiss as they swayed to the music. Their lips parted, and as their tongues met, his hands slid down to her backside and he pulled her in tight. Cassie was in heaven, her pussy tingling, and she felt herself beginning to moisten. Want and desire welled up inside her. Conscious of her surroundings, she broke off the kiss and whispered in his ear, “Wanna come over to my place? My roommate went home for the weekend, so we’ll have the place to ourselves,” and then licked his ear lobe and ground into him, pressing herself into the bulge in his pants.
Jack had never done this before (neither had Cassie for that matter) and agreed, trying not to look nearly as eager as he felt. He took her by the hand, led her to the booth to pick up her purse and then out to grab a cab. Jack was on cloud 9 and tried unsuccessfully to think of something besides “is it going to be, could it be, am I going to finally do it?” Cassie was thinking the same thing, with thoughts of, “but will he still think I’m a nice girl, am I ready, is it baaad?” mixed in with, “ohhh, but I want to.”
The kocaeli escort cab pulled up at Cassie’s place. Jack tipped the driver nicely and ran around and opened the car door for his girlfriend. He liked that thought – “his girlfriend.” He helped her out of the car and caught a wink from the cabbie as he closed the door. Jack wrapped his arm around her, and they walked up to the door, staggering just slightly, in the glow of young love and alcohol. Cassie unlocked the door, pulled Jack inside and closed it behind him.
They headed to the living room and she turned on the stereo. As she turned, he took her in his arms and kissed her. Jack told her that he loved her, and that he had a confession. She had been the first girl he had ever kissed. She smiled at him, those brown eyes sparkling, and told him that although she had kissed a boy in high school, it had only lasted 2 dates and never got past that. She too was new to this.
They continued to hold each other and make out for a few minutes, when Cassie said “let’s get more comfortable, come up to my room.” Jack said, “Lead on,” and followed her like a little puppy. They sat down on the edge of the bed, and Jack leaned into Cassie, one arm around her waist, the other hand reaching up to her chest, and beginning to stroke her with the back of his hand. Cassie closed her eyes, tilted her head back and moaned softly, her nipples hardening and her pussy getting wetter.
Her hand reached up and stroked his nipples, sending ripples of pleasure to his rock hard cock. He leaned back, and lifted his shirt over his head and tossed it into the corner. She smiled and did the same, watching him stare at her perky white breasts, almost drooling at her. She giggled and when he asked why, she told him that he looked like a kid in a candy store… And that it was cool because she wanted to be the candy. Her nipples were hard, and they so much wanted to be licked and sucked, and appreciated.
Youporn and movies aside, Jack hadn’t actually seen real live tits before. They were amazing. Lovely, white, firm to the touch, and hard nipples surrounded by small areolae. He squeezed her left breast, stroked the nipple, and watched as she squirmed in delight. He brought his face close, blew softly, and gave it a little peck. Cassie melted, laying back on the bed. He snuggled up and moved in close. This time he touched his tongue to the nipple, licking it ever so lightly at first, and then more firmly. He could hear Cassie mewl. After a couple of minutes, Cassie nudged his head to the other, neglected breast and whispered, “It’s jealous and I think it wants to be sucked.”
Jack took the cue, and wrapped his lips around her right tit, sucking deeply, lapping the nipple in his mouth. She had never felt anything like it. Cassie’s chest was on fire. Her cunt was now drenched, and sending signals of its wants to her brain. Earlier in the night, she had thought she wanted to continue to move things along slowly, but now all she could think of was how awesome this felt. And she knew that Jack was the one she wanted to share this with.
Cassie’s hand reached down between them and found Jack’s member almost bursting out of his pants. She rubbed from base to tip and back, stoking the flames of Jack’s desire. She reached for his zipper, pulling it down and fumbling with the button, to open his pants. He reached under her skirt and stroked her through her panties, noting how wet they were. His index finger settled on her slit, and he stroked up and down like he would rub behind a cat’s ear. Cassie had never felt so good.
Jack paused to help darıca escort Cassie remove his pants and underwear, and tossed them over by the shirt in the corner. Cassie also took the opportunity to pull off her skirt and panties and send them off the bed. They stared at each other, naked for the first time. His penis, no, it was a cock, stood erect; the head a bright purple and veins sticking out. She wondered how that would fit inside her – it was certainly much bigger than her fingers, and she wondered how it was going to feel.
Jack looked at Cassie. She had light brown fur on top, and swollen lips, the folds covering her entrance. The lips were a lovely shade of pink, glistening with her dew. He reached to touch her, as she wrapped her hand around him, each sending new and wonderful ripples of delight to the other. He gently explored her, stroking her delicate folds, his finger sliding easily through her juices. He paused at her top, touching the nub he found there. She drew a sharp breath and whispered, “gently Jack. She’s very sensitive.” He moved back to her lips, ran his finger along her slit to slicken it, and then lightly rubbed the clit. It was like a bolt of lightning went through Cassie. She arched her back and cooed out loud. Her cunt was on fire with pleasure. It never felt like this when she did this herself. Jack moved back to her slit and unfolded the labia, then slid a finger slowly inside her. She was wet. She was warm. She was soft. And she made the most delightful sound as he pressed inside her.
He curled his finger within her, making that “come here motion.” Cassie spread her legs wide and pressed herself to him. “That feels soooo good”, she moaned. “Don’t stop.” He pulled his finger almost all the way out, then slid it back in deep. In, out, in, almost like playing a violin. Cassie writhed on the bed. Wave after wave of pleasure was building up inside her. As he stroked, he took her breast in his mouth, sucking deep, and lapping her nipple. First one and then the other. Cassie tingled all over. He slipped a second finger inside her, and continued to pump, and then began to move his thumb around her outside, finding her clit. Cassie cried out in delight. “Mmmmmm…… That…… Feels….. So….. Good.” Then as he continued to rub and stroke, she felt a big wave come on. Jack saw her body tense, a glow come over her face, her nipples became even more taut. Her breathing shallowed. Cassie felt the wave build, every part of her on fire. The wave carried her up and up, and she breathed, “uh uh I’m uh uh mmmm cumming.” The orgasm hit her and she squeezed her legs tight around him. Her pussy started to spasm, and she exploded from deep within. Jack felt her pussy clench and clench, like it was trying to pull his fingers in. He watched her as she came. She was beautiful. She asked him to stop for a minute, as her pussy was now hypersensitive. A warm glow came over her face and she smiled at him and Cassie said, “Wow.”
Cassie ran a finger along Jack’s shaft from the base at his balls to the swollen head, never having touched a penis before. He shuddered, never before feeling this level of pleasure. It was sooo much better than when he touched himself. She moved to touch his balls, cupping the shrivelled skin in her hands, and feeling the balls roll slowly in her hands. She squeezed gently, but not quite gently enough, and Jack said “easy there”. He told her that he loved her and planted a deep and passionate kiss as they fondled each other’s private parts. Cassie whispered, “I want you,” in his ear. He asked if she was sure, and she smiled gölcük escort and nodded.
Jack rolled slightly and said, “Let me grab the condom, it’s in my pocket.” Cassie squeezed him and said, “No. Let’s just do it naturally. I’m on the pill, and it is the first time for both of us.” Jack almost came on the spot. He positioned himself between her legs and couldn’t believe this was happening. He fumbled for a bit, trying to find her spot, his cock anything but patient. “A bit lower,” she said. “Almost.” And then he was lined up and he felt her on his tip. Heaven. She was warm. He asked if she was sure once more. She looked at him and nodded. Jack pressed slowly, and felt her lips part around him, an unbelievable feeling as her warmth wrapped smoothly around his head. He paused and withdrew, coating himself in her juices and pushed in again slowly, this time a bit deeper and then almost withdrew.
Cassie tried not to tense up. She had heard that it could be painful when he took her for the first time. As he entered her, she was amazed at how her body opened up, and how he was beginning to fit inside her. It felt great. And then he withdrew and started to press in again. “Here we go,” she thought.
“Here we go,” he thought as he continued to press slowly inside her. He had read that he needed to be gentle, and he wanted her first time to be good. He also knew that for many, the hymen has broken long before the first time and so he didn’t know what to expect. He pressed into her. Slowly, 1/4 of his cock covered in her slickness, then 1/2, and then all the way in. It felt divine. She moaned as he filled her up, waiting to feel him get blocked at her maidenhood, and then feeling him continue deeper and deeper, unimpeded. She had never felt so full as when he hit bottom. Electric pulses ran within her as he made his way in. Jack stopped fully inside her and whispered “I love you, Cassie.” She whispered back, “I love you too, Jack.” He started to withdraw, feeling the air on his shaft and her friction on his head. His entire being seemed to be concentrated on his cock and the pleasure, oh the pleasure that he was feeling. He pressed in again, a bit more quickly and smoothly, then continued to pump at that calm pace, knowing he wasn’t going to last long.
Cassie felt herself fill and empty, fill and empty and felt a second orgasm start to build within. Jack tried to hang on as best he could, but it felt so fantastic, he knew he wouldn’t last long. He pumped in and then out a few times, and he started to feel his balls contract. He pressed in again slowly, and could feel the pressure building; the nerves in his cock electric. Nothing had ever felt anywhere close to this good. Then out slowly, and then back in. This was going to be it. He pressed in and felt the cum getting ready, his entire dick was on fire. Cassie moaned as her orgasm built and said, “cum with me Jack.” He reached deep within her, felt his cock expand and then explode, jetting his seed deep within her.
Feeling him pulse inside her, Cassie climaxed at almost the same time, her pussy clenching him tightly, holding him in, and sucking in his seed. Jack felt her cunt twitch around him as he throbbed, jetting ribbon after ribbon of his cum deep within her. Then as quickly as it came on, his orgasm ebbed, replaced by a wave of deep contentment. The only word he could think of was “mmmmmm,mmm.”
Cassie smiled up at him, post orgasmic bliss washing over her. “Thank you,” he said to her. “Mmm, thank you!” she replied before he kissed her gently. She felt him shrink inside her, and felt his warm cum begin to drip within. Not bad for a first time she thought. Not bad at all.
Jack smiled down at her as she looked up at him. He gave her a tender kiss and felt himself shrink inside her. Not bad for a first time, he thought. Not bad at all.
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