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Try Anything Once

A young college virgin loses her virginity to her best friend of many years, in her dorm room.
It was about ten thirty at night and Ivy was busy working on her chemistry homework. She was sitting at the desk in her small dorm room while Kyle, her best friend of about three years, was sprawled on her bed, typing away at an essay assignment. Ivy was a petite girl, no taller than five feet three inches with shoulder length straight blonde hair, which she compulsively would run her fingers through. When she was in deep concentration she tended to bite her rosebud lips.

“What do you think of this statement?” Kyle asked, “It’s for my economics paper… While analyzing my results I came to the conclusion that I was a bit of an outlier…” He looked up at her expecting feedback

“Let me read it in the context of the rest of the paper.” Ivy said as she crossed the room and sat next to Kyle’s extended form.

He rolled over onto his back lacing his fingers behind his head and shutting his eyes while Ivy quickly scanned his essay. Kyle was tall, about six feet and he was thin. Despite a slightly gangly look he was very muscular, especially his well sculpted abs.

“I think you could probably do better than this, Kyle.” Ivy said as she turned the screen of the computer back to facing Kyle.

“Or… you could just fix it for me.” He said expectantly, opening his eyes and flashing Ivy one of his famously charming grins.

“Guess again big boy.” Ivy retorted jokingly and she swung her legs off the bed to return to her work at the desk. Once her legs hit the floor however she felt his strong arms grab around her waist and pull her back onto his lap. They had been best friends for long enough now that physical contact was a welcome form of expression between the two of them. They would often walk down the street with linked arms.

As Ivy sat on Kyle’s lap he tucked her hair behind her right ear and whispered, “Pretty please write my essay for me? I promise I’ll return the favor.”

“Not a chance!” Ivy said, “Besides, I have work of my own to do.”

“Fine” Kyle said dejectedly, and with that he released her from his grasp in his arms and leaned in to give her cheek a big smooch, as was his flirtatious custom. Just as he was puckering up though, Ivy turned her head to tell him that she would be happy to proofread his essay as long as she didn’t write it for him. What happened next surprised them both. Instead of him kissing her cheek, and instead of her telling him this fact, their lips met, just for the briefest of moments.

Ivy quickly pulled her head away and moved off of his lap. She looked into Kyle’s eyes, and to her surprise, he kept her gaze. She had been feeling like more than friends for a while now, but she never knew how he felt about her.

“So,” Kyle said without moving his eyes from hers, “I’m not sure if I felt a spark there, it was a bit too short.” He inched towards where Ivy was sitting on the bed, and said, “Maybe we should try that again.”

Ivy’s heart leaped and she felt a blush creeping up her neck and onto her already rosy cheeks. She nervously ran her fingers through her hair. Ivy was a virgin and had essentially no experience sexually, aside from her solo explorations. She moved herself towards where Kyle was now sitting on the bed and crossed her legs in front of her.

She was looking down at her lap when she felt Kyle’s hand grasp her chin and move her face to meet his. Again, their lips met, this time sending a surge of sensation through her stomach and deep into her sex. She felt as though her heart had migrated from her chest and was now beating in between her legs.

Slowly and sensually Kyle’s tongue danced around Ivy’s, as if testing her reaction. She saw his hands move from their spot on the bed and then she felt them run through her hair at the nape of her neck. Ivy’s breathing was increasing and she audibly moaned into Kyle’s mouth.

As if emboldened by her moan Kyle’s hands continued their migration from her neck and down her back to the bottom edge of her dress. Ivy stretched up onto her knees and put her hands on Kyle’s shoulders, giving him the go ahead. In one quick move he had it up and over her head, leaving her in just a bra and her wool tights. He paused for a moment, and when she didn’t protest he moved his hands to her bra clasp. He continued kissing her, more passionately than before, while his expert fingers deftly unhinged her bra. He slipped the straps from her shoulders and had the garment on the floor before it could even register in Ivy’s mind what she was getting herself into.

Kyle had had a reasonable number of sexual partners, due to his talents in charming the ladies. If only he knew just how many girls had crushes on him, he would be the most laid boy on campus. This was better for Ivy however, because he knew what he was doing and could ease her into her first time with the skill of a veteran.

She felt his hands cupping her small breasts, his thumbs on her perky nipples and a feeling raced through her body down into her lower abdomen. She moaned again tilting her head back in pleasure.

He then pushed her shoulders down so that she lay on the bed with her head on the pillows. He kissed her gently on the mouth and then ran his hands down her naked upper body before stopping his hands at the waistband of her tights. He looked up at her expectantly. Ivy simply arched her hips up slightly. She was agreeing to devote herself to him fully and give him her virginity.

Now Kyle didn’t want her naked quite yet, oh no. He wanted her to beg and he knew just how to do it. Kyle positioned Ivy’ss legs so that her feet were against the bedspread and his head was in between her legs. He could do anything and everything with her in this position, and he intended to do so. Slowly Kyle ran his hands over her thighs and calves, knees, and letting them rest underneath her ass, effectively pushing her hips up towards him.

He then bit the inside of her thigh gently, evoking yet another moan from Ivy. He could smell her through her tights, but he didn’t want to take them off quite yet. With his hands under her butt he licked and kissed and nibbled at her tights clad thighs, moistening the stretchy fabric. He worked in a quickly diminishing radius that was zeroing in on her hot, presumably moist pussy. He was teasing her and he knew it was working. Every time he got close to her slit he could feel her tensing up and trying to coerce him to put his mouth on her…so he finally did.

Still wearing her tights Ivy audibly gasped when she finally felt the pressure of his skilled tongue on her highly sensitive clit. She wanted him so badly and pushed her hips into his face. He sucked her little clit through her tights, feeling his saliva mix with her own moistness dampening his face and his chin. After what felt like an eternity to her Kyle moved his hands out from underneath her and to the edge of her tights. He grabbed the pulled them down, past their now very dampened crotch and off. Kyle then snaked back up to her now panty clad sex and licked her slit firmly, making Ivy squirm, before grabbing her lace panties with his teeth and pulling those off too.

Kyle then looked at Ivy very slyly and pulled her hips towards him so that he could latch onto her pulsating, hot pussy. Ivy threw her head back against the bed and her hands reached down to grab the comforter as Kyle’s tongue made first contact to her naked and overly excited flesh.

“Uuunngghhh!” She moaned turning her head to the side so as to cover the noise. She felt Kyle’s tongue circling her clit while his hands held her hips securely to the bed. He didn’t want to risk her falling off.

Kyle fastened his mouth onto her clit and was moving his hands from her hips to have better access to her still wet poon when he felt a vibration coming from the back pocket of his jeans. His cell phone was ringing .

“Don’t you dare answer that.” Ivy gasped, as she watched him fish his phone out of his pocket. Kyle stood up off the bed and looked at the caller ID on his phone before flashing Ivy yet another award-winning grin.

“Yello” Kyle said into the phone, winking at Ivy. She was too busy covering her face with her hands to see this though. “Naw, I’m not doing anything, just studying with Ivy in her room.”

At the mention of her name Ivy peeked through her fingers and up at Kyle. God he is so sexy, Ivy thought. The way he was standing with his phone to his ear was tugging his shirt up ever so slightly, giving her a slight view of his wonderfully athletic body. She could just make out the tops of his hipbones and the definition of the muscles there. She closed her eyes and began to picture what he was packing underneath his jeans and boxers. She could feel herself coming down a bit from her excitement, and was debating finishing the job herself, with her own hands.

“No problem man I’ll get it to you tomorrow” Ivy heard Kyle say into the phone, distracting her from her steamy thought session. “Now really isn’t a good time for me, I’m kinda busy.”

Kyle looked at Ivy knowingly.

More like getting busy, thought Ivy

“Yeah I’ll see you tomorrow man. Take care man.” Kyle said and hung up.

Kyle walked back over to the bed and placed himself on top of Ivy’s clothed body.

“Now, “ he said, kissing her fully on the mouth. “Where were we?”

Kyle pushed himself up onto his hands and watched as Ivy snaked her own hands down her body, stroking her pert breasts and stopping to stroke her clit.

“Ah, yes.” Kyle said and repositioned himself between her legs. Ivy kept her fingers on her clit and she could feel Kyle reopening her pussy lips with his fingers. He began to trace around her vaginal opening with his middle finger. He then flipped his hand so that his palm faced the ceiling and slowly put his middle finger halfway into Ivy’s slit.

Ivy was a regular masturbator and was used to putting items, such as her fingers into her pussy, so she knew that one finger was just not going to cut it. As Kyle began to stroke her pussy walls with his finger Ivy continued massaging her clit.

“Kyle, you’re gonna need more fingers that that” Ivy told him, still working her clit.

Abruptly Kyle removed his hands from her sex and positioned his mouth over Ivy’s active fingers. Ivy let her head fall back against the bed once more and her hands found her aroused nipples. She felt Kyle slip two of his fingers back into her pussy and he continued licking her clit. She could heard her juices squelching in her pussy with every ‘come hither’ mover that Kyle made and she felt an orgasm building, the sensation starting in her stomach.

Kyle created a vacuum around her clit with his mouth, and swirled his tongue expertly over it. He kept his fingers moving inside her although he could already feel her vagina reacting to his touch. The walls of her pussy were closing in on his fingers and he could tell her clit was getting more and more sensitive as he could see her squirming from his tongue. He could see an orgasmic blush spreading over her smooth milky skin.

Ivy’s breathing began to increase as her hips moved more wildly. Kyle knew it wouldn’t be long now.

“Oh my god! Ok.” Ivy said breathlessly as an orgasmic wave went over her, shooting spasms through her entire body. “Don’t stop”

Kyle didn’t stop, instead he quickened his fingers even more and continued ot suck her clit with intentional fervor, sending Ivy over the edge. Kyle could feel her vaginal walls spasming around his fingers as those same spasms sent quivers throughout her body. Her legs flew straight out in front of her and threatened to squeeze his head in its place. She arched her back and let out small moans when she could get enough air to her lungs.

Kyle let up on Ivy’s sex, letting her recover, and placed him next to her on the bed. She rolled onto her side to look at him.

“You’re blushing” He said, making her blush even more, “How was that?”

“You’re kidding right? How do you think it was?” Ivy asked jokingly.

“Do you think you want to continue? We could stop here if you’d like.”

“No” Ivy said seriously. “Let’s do it. I’m ready.” And she scooted her warm body over to him and planted a kiss on his mouth. “As long as you have a condom.” She said seriously.

“Of course I do” Kyle said, hastily jumping off the bed and beginning to strip. He pulled his shirt up over his head showing off his solid abs and then began to unzip his pants.

“Let me” said Ivy, now sitting at the edge of the bed. She linked her finger through his belt loop and pulled him close to her so that she was level with his fly. She continued to unbutton and unzip it. She then pushed down his jeans leaving him standing there in front of her with his boxers on, but with a very apparent boner.

Ivy looked up at him nervously before linking her thumbs into his waistband and tugging the flimsy fabric over his engorged penis. Kyle kicked his boxers into the large pile of clothes on the floor and continued to stand there, only now fully naked.

Ivy took his cock in her hands and unsurely began to rub her hands up and down it. She could feel it pulsating throughout his six and a half inch length and she looked up at him again, only to see his eyes closed. She took the lubricated condom from his fingers, opened it and slipped it onto his shaft, taking the utmost care to roll it all the way down to the base. All of those health classes finally paid off for something at least.

Once Kyle was fully protected Ivy leaned back onto the bed and lay down again with her head on the pillow.

“Be gentle.” She said, a nervous tremor in her voice.

Kyle knelt in between Ivy’s legs, pushing her knees up against her chest. He licked his fingers and rubbed her slit once more, taking care to get it as wet as possible. He slipped his fingers inside her once more before putting the head of his penis against her pussy. He rubbed his dick up and down her slit, getting as much lubricant from the condom around it and then positioned his penis at her opening.

“Relax” he said knowingly, the confident nature in his voice relaxing Ivy instantly, and with that he began to move his penis inside Ivy’s virginal pussy.

Ivy’s breathing began to increase again as she felt her nerves getting the best of her, but then she felt Kyle’s familiar fingers against her clit again. Boy was he talented at keeping her wet. Ivy’s pussy began to adjust to this invasion of man meat and she could feel the ridges of his dick hitting her pussy walls. She began to relax as Kyle started thrusting ever so gently in and out of her, with each thrust increasing the amount he inserted into her, until she was taking him fully.

“How is this for you? “Kyle asked concernedly, the physical exertion apparent in his voice.

“Mmmmmm” Ivy simply moaned, beginning to push her hips back into his thrusts.

Kyle, encouraged by this took Ivy’s feet and placed the soles of them against his warm, glistening chest. This angle had his penis stroking her g-spot with every thrust and Ivy’s breathing was getting heavier and heavier because of it.

Kyle felt himself increasing in excitement as he could feel the swells of excitement starting in his belly. He locked eyes with Ivy and she seemed to be giving the go ahead, as he had already made her cum.

Kyle couldn’t hold it any more. With every thrust he could feel it building, but he didn’t want to go any harder, at risk of hurting Ivy’s virginal pussy. He continued to thrust into her gently, but effectively putting himself over the edge. His ass tensed up and he pushed his full length into Ivy’s pussy, making her gasp, as he felt the tip of the condom fill up with his seed.

Ivy could see him orgasming inside her and she tightened her kegel muscles around his hard rod. When his spasming stopped he pulled out of her ad pulled off the condom. He threw it into the garbage and pulled his boxers back on, to prevent any flow of bodily fluids to Ivy. He then laid himself next to her and looked her in the eyes. Neither of them needed to speak, but they could both feel the peace that had come over the room. Neither of them knew what was to become of their friendship, but neither of them cared. For the moment they were still abuzz by what had just happened, and they were riding their hormones back down.

Ivy felt herself dozing off, only to be brought back to consciousness when she heard the vibrating of Kyle’s cell phone against her hard floor.

“I’ll call them back, whoever it is” Kyle said, smiling to himself.

Ivy began to laugh, “Of course you don’t pick it up now!” She said as she rolled her eyes, and she pulled the comforter around the two of them and snuggled close to Kyle’s still warm body. She quickly fell into a deep sleep.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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