The Cherry Poppers Ch. 21

"Jason ... you'll have to help me. I'm not sure what to do."

Jason helped her open his pants and pull them down. His cock was glad to be free of the tight confines and immediately tented his boxers. Once his pants were on the floor, Jillian pulled at the waistband of his underwear. Jason helped her again by lifting up so she could pull them down. His cock pulled down with Jillian's inexperience but bounced back up once his cock freed. It nearly hit Jillian in the chin as she pushed down his underwear.

"Oh, my!" Jillian exclaimed upon seeing Jason's cock for the first time.

He sat up and opened a few more buttons until her shirt was open. Jillian just stared at his cock as it quivered with desire. Her eyes were mesmerized by the sight and movement of it. She barely felt Jason removing her shirt despite helping him by moving her arms as he needed. Soon, she was naked on top except for her bra. Jason tried to reach around behind her to get at the clasps but she was pretty far down on the bed. Jillian realized what he wanted and removed the bra for him. Now it was Jason's turn to stare in awe.

"Fuck! Their incredible," Jason gasped, reaching for her breasts.

As his hands touched her firm, yet subtle skin, she finally looked up at him. He kneaded her tits and fingered the fantastic nipples. Stephanie's tits were a little bigger, Claire's more perfectly shaped, but these were two absolute beauties. The aureoles were magnificent, pink, and the size of huge marshmallows, and just as puffy. They looked like the most suckable nipples he had ever seen and they curved upwards. They were better even than Pam's brown Hersey's kisses. His fingers pinched the soft tips in an effort to further stiffen the half inch nipples already at attention.

"God, Jillian!" Jason declared as he continued to knead and pull on her wonderful nipples.

"Mmm ... that feels good," Jillian moaned as her hands managed to encircle Jason's cock.

Jason's hands pulled hard enough on her tits to force Jillian to lean up a little closer to him. As soon as she was close enough he fastened his mouth over one of the puffy marshmallows and sucked it into his mouth.

"Oh, god," it was Jillian's turn to say now.

She had played out this very scene in her mind the last week or two since meeting Jason. In her bed at night, when she was sure her roommate was asleep, she had touched herself pretending it was him. She had yearned for his touch, but her own hands couldn't equal the real feelings she had now.

"Ahh ... Mmm," Jillian sighed. "Keep doing that, Jason. That feels so good."

Jason switched back and forth between her breasts. They were handfuls even for his long fingers. 'What magnificent tits,' he thought.

Jillian's hands worked up and down Jason's cock. Her hungry eyes were back on the huge head of his cock and watched as a clear drop of fluid oozed from the tip and ran down one side to meet her moving hands. Jillian smeared the slick liquid on the shaft of his dick. Wanting more, her fingers teased around the little hole at the tip, soon to be rewarded with another glistening drop. This one she captured between her fingers to feel its smooth texture and slipperiness. She naughtily touched her finger to her lower lip and ran it across. It wet the surface and allowed her tongue to flick out for a taste.

Jillian lacked experience but she wasn't unaware either. She knew some of what she needed to do with his cock from talks she'd had with an older cousin years before. Her cousin had described to her the things she did with her first boyfriend's dick. She hadn't gone all the way but the other bases were covered many times. Jillian had been with two boys in high school but neither lasted long or got beyond a kiss and feel. Jason was her first bare cock to touch.

When Jason took a little break from sucking her tits, Jillian leaned back like before. She looked into his eyes as she settled over his towering organ. Another drop of pre-cum had already pooled in the little hole and threatened to run down one side of the large helmet like head. Jillian inspected the impressive dick in her hands, drinking in every aspect.

"Go ahead," Jason urged.

"What?"

"Kiss it," Jason said as if a mild command.

Jillian slowly lowered her head. She knew what he wanted. Her cousin had described every part of a guy's cock and how to give a proper blowjob. She'd learned from other girls at school too and an older friend. Now her moment was finally here. Everything she had tried to remember from her cousin came rushing back at once clouding her mind. She tried to separate the thoughts into what to do next. Jillian remembered one thing that her cousin had stressed. The area under the head was particularly sensitive. It was here she first decided to touch him with the tip of her tongue.

"Urgh," Jason moaned with the first tickle of her tongue tip.

She teased along the rim of the head and part way down the bulging part on the underside. Jason's continued groans told her what she was doing was pleasing him. Her tongue wet the surface of his cock as she tasted his male scent. Jillian concentrated on Jason's actions as she continued working his cock. When his hands kneaded her hair and pressed her mouth down harder, she complied. When his grip pulled her back to the tip and smeared a drop of pre-cum over her lips, she could feel the pressure he applied to get her to open. She did, taking the head of his big cock into her mouth for the first time.

"Oh, babe," Jason's growled. "That feels so good."

Jillian had heard that girls were supposed to take the guy as deep as they could. She bobbed on Jason's cock, going a little deeper each time. Jason's reactions spurred her on until she felt herself gag a little. Her throat didn't want to accept the huge intruder. She tried a few more times just to prove to herself that she couldn't go further.

"Mmm," Jason muttered.

Jillian's mouth was filling with saliva and her jaw began to hurt a little. She'd never had anything this big in her mouth for this long. She backed off to swallow and looked up at Jason. Her eyes were watering a little with tears.

"Nice," Jason complimented.

"Thanks."

"You went pretty deep," he observed.

"I couldn't go further," Jillian lamented.

"That's okay. Come here."

Jillian moved up Jason's body on all fours. His dick ran between her breasts and along her belly as she moved. He kissed her when she got above him. Jason's hands played with her nipples as they kissed making Jillian moan into them. Jason's cock nudged between her legs and the wet head tangled in her cute blonde muff. After a while Jillian's arms tired and she lean to one side, Jason follower her to suck on her nipples again.

"Oh, Jason. That feels wonderful," Jillian whispered.

He sucked her breasts and lightly bit her nipples for a while longer before moving over her on the bed. His cock persisted in probing around her pussy. Jillian thought he would move to take her next but instead he slipped further down the bed, kissing her tummy, licking her bellybutton, and nuzzling his face into her blonde bush. Normally, Jason preferred a woman shaved but something about Jillian's cute muff attracted him. He didn't know if it was the strong musky scent of her, the blonde hair, or the way her pubic hair tufted above her slit, but only a slight amount trailed down either side of her sex. It framed her sweet mound like a golden mane.

"Oh god, Jason. What are you ... Ahh," Jillian growled as Jason kissed her mound.

Having never been eaten, Jillian had no idea what to expect. Her older friend had told her about a lover that had eaten her and how fantastic it was but Jillian had little else for reference. It soon didn't matter.

"Oh, shit," Jillian growled as Jason moved from kissing to licking.

Jason used his fingers to part her moist tunnel. Jillian had been incredibly aroused since they started. Her cunt was a veritable full well as Jason lapped around the hole like a thirsty animal seeking her delicious nectar. When he dipped his tongue tip into her core, Jillian went rigid. Her body felt tight as a bowstring as Jason played her strings.

"Jason, please ... don't stop ... ahh ... more ... touch me ... ahh!" Jillian howled her need.

She had never felt anything this good. The pleasure he had given her nipples before was like a distant memory. This was tenfold better and growing. Her back arched off the bed and her hands played in his short hair. She pressed him to her sex and squeezed her legs around his head as if worried he would go away too soon. It wouldn't be long though.

"Fuck!" Jillian wailed.

Jason had purposely not touched her clit at all yet. His fingers pushed higher forcing the hood to open and expose the tiny little conjuncture of nerves. He chewed lightly on her lips and worked his way very slowly towards it. Jillian started cumming in a series of mini-bursts, like sparks going off in her brain. Her legs squeezed his head threatening to cut off his air.

"Urgh!" Jillian roared.

Jason had eaten his share of pussies but Jillian's was sweet and her reactions were incredible. He had driven women crazy before with his tongue but Jillian was like a rocket about to explode. She squirmed on the bed and bucked against his face as the bliss washed over her. Each new burst of pleasure was more intense than the last, yet she could feel them building towards something even more mind-blowing.

Flicking his tongue in numerous spots around her little clit was driving Jillian nuts. She had never felt anything close to this good. When Jason finally licked across her hyper-sensitive bud, Jillian roared.

"Ahh! Oh, god! Fuck!"

Jillian shook like her body was receiving massive electrical charges. Her legs clamped Jason's head so hard, he couldn't breathe and threatened to break his neck as she thrashed on the bed. Jillian's mind was numb with the pleasure. Jason didn't let up either. Despite fighting for air he managed to maintain the assault on her clit until she pushed him away. He didn't move far though and instead lapped up her sweet liquids leaking from her pussy like juice from a ripe fruit.

He stopped not long after Jillian went limp and dropped her hands and legs flat on the bed. Jason looked up at her and smiled. His face was coated in her wetness from nose to chin. He wiped his face with the back of his hand as he moved up on the bed. He looked at her cute pussy as he went. It was wet and ready for him. He noticed his aroused dick too, solid as steel and leaking pre-cum at the thought of fucking that wonderful virgin pussy and popping her cherry.

Once again, he had a brief moment of, 'I shouldn't do this to her before I make sure she definitely wants to.' However, his new, more callous psyche flushed that idea from his mind as soon as it appeared. He couldn't have stopped himself now if he wanted to. Short of Jillian pushing him off her, he was going to fuck that beautiful cunt.

In the past, he had asked most of the virgin women before fucking them, were they sure. With Jillian he just lined up his cockhead into the nook of her sex. He did look into her eyes though, and saw only worry, but no denial. He took that for her acceptance of her new fate, to be a woman soon.

As with everyone else, Jason attempted to take the woman's mind off the pending pain. He started passionately kissing Jillian, drawing mews of contentment and fervor from her. He kissed her and forced his tongue deep into her mouth. Jillian had never kissed like this with anyone and it drove her wild with obsession for him to keep on. Her tongue battled back with his and her hands held his head tight to her mouth as she ardently kissed him back. Mews of delight escaping her lips as they kissed.

Jason waited long enough to be sure her immediate attention was somewhat redirected from his throbbing cockhead poised at the entrance to her womb. He used one hand to make sure he was seated right, aligned to crash through her cherry, and bury his cock up her never used channel.

Jillian was truly caught up in his kisses and returning them, the stab of pain caught her by surprise. The stab was followed by a rush of pain that made her scream.

"Oww! Oh, shit!" Jillian cried.

He had broken through on the first thrust. The wetness of her pussy had aided his entrance. Jason held still, letting Jillian get used to the pain, and give it time to lessen. When he felt her death grip to his hips with her hands diminish, he pushed a little deeper causing a modest reaction from Jillian.

"Jason, it hurts."

"Just wait, babe. Give it a minute. It will go away and turn to only an ache."

"How can you be so sure?"

"It was the same for Kira and Tessa," Jason affirmed.

"Oh, god ... go slowly, please ... it's a little better now."

Jason lowered himself into Jillian a centimeter at a time it seemed. She was as tight as expected. His big cock forced the tight tube to open and accept its new role. No longer was it protected by its barrier. No longer was it inaccessible to a cock wanting in. Jillian was a girl no longer as Jason reached deep inside her.

"How does it feel now?"

"Better," Jillian replied. "Oh, god, I feel you deep inside me. You're fuckin' huge."

"I am big for your first but you'll like it more very soon."

"Still go slow please."

"I will," Jason said, moving a little to extract his cock from far inside Jillian's clenching vaginal muscles.

Jillian moaned a little when she felt Jason's cock withdraw and reenter her. It was hard to determine if it was a pained moan or a pleasure one but Jason kept going in measured time. He gave her moments to adjust to the steady pace of his cock stretching her open and then leaving her feeling empty and wanting more. The feelings started to change as Jason said they would.

"Oh, Jason. It feels incredible. Keep going."

He sped up a little but distracted her further from the dull ache in her sweet cavity by sucking on her magnificent tits. The nipples were distended and felt delightful in his mouth. He teased the little buds with his tongue and pushed the tip into the end of each one as he trapped it in his sucking lips. Jillian groaned her approval.

It seemed to both of them to have been hours until Jason was able to move inside her without a negative effect from her. Actually, it was only minutes before the results of his pumping hips now produced positive sighs from Jillian. His attentions to her sensitive nipples helped too.

"Nice ... so nice. Oh, keep going ... more ...more"

As Jason picked up speed, the nails of Jillian fingers once again poked the sides of his bare hips. He was sure she had drawn blood from the dull ache he now felt there too. This pressure to his hips was from pleasure now, not pain.

"Do me, baby. Fuck me good," Jillian implored.

Jason was a little surprised by Jillian's words. He had expected her to be the quiet type, responsive, but silent in her enjoyment. He was a little shocked to hear profanity now and nasty talk coming from her lips as he fucked her deep.

He sped up and could feel heat building between their tightly clenching bodies as Jillian held him to her on each inward thrust. Her hips had started intuitively responding, pushing up into his downward thrusts, causing him to go even deeper. Her pussy was like wet silk on his cock. It gripped tight but with a velvety touch that made his balls contract with the wonderful sensations.

"Fuck me, Jason," Jillian howled so loud someone right outside Jason's frat room would have heard.

"Shh," Jason gasped with a laugh. "The cook will hear down the hall."

"Oh, it's so good ... so good though ... keep fucking me, please."

Jason started really pounding into her. He rose up on his arms to watch her beautiful tits sway and shake as he pumped hard into her newly open womb. He could feel the head of his cock burrowing deep inside Jillian. Her pussy was fantastic and he could drive all eight plus inches of his fat cock deep inside her. Not many women he knew could take so much of him without some pain. Ariel had let him pound her tiny pussy but if he went to deep she grimaced in pain. Jillian took him and wanted more.

"Damn, what a great pussy you have," Jason roared.

"Gimme that big cock, baby," Jillian shot back.

'Shit, she's almost as dirty talking as Tessa,' Jason mused to himself.

Jason hammered Jillian as if she were a seasoned whore. Gone was any semblance of pain it seemed. Jillian encouraged him for more no matter how hard he fucked her. She could take it and wanted more. Sweat began to form on their bodies and drip off Jason's forehead. Their bodies slapped together like wet rags. The room was full of the sounds of their fucking. The bed creaked loudly and the scent of sex filled the air.

"Oh, Jason ... I'm going to ... I'm going to cum."

Jason knew it wasn't long for him either. This surprising sex machine was driving his cock delirious with pleasure. His balls were tight as a fist against his cock as he buried himself completely in her velvety snatch again.

"Me too," Jason gasped, remembering they hadn't discussed him cumming in her.

Fortunately, Jason lasted longer than Jillian. He fucked her until she shrieked and sunk her nails deeper into his sides than before. Her world seemed to melt into her pussy as it seemed to draw pleasure from every pore of her body.

"Fuck Me!" Jillian screamed, once again too loud.

Her cunt clamped down on his cock like a vise. He could barely move she held him so tight. Waves of bliss coursed over her body like ripples through the water after a stone strike. Jason watched the intense pleasure grip her pretty face in a tight clench. She even looked like she wasn't breathing, as he felt his own climax simmering.

When Jillian went limp, Jason quickly extracted his cock from buried deep inside her. It was coated with Jillian's fluids as he grabbed it furiously and started pumping himself off. Jillian opened her eyes to see him on one knee, with his other leg spread over her and across the bed, aiming his cock at her tits and belly.

"What should I do?" Jillian asked hurriedly.

"Rub my balls, babe."

Jillian's hands had barely touched his tight testicles when Jason growled and his cockhead expanded. Jillian watched mesmerized for the first time as she saw a cock ejaculate. The first shot surprised them both and ricocheted off the inside of her left breast and smacked her in the neck below her chin. She shrieked and pulled back a little but couldn't take her eyes from the discharging cock. The next two volleys of cum were huge and completely saturated her right breast in hot milky sperm. It looked like icing on a cherry covered cupcake as it ran down into the valley of her tits.

"Oh, my," Jillian gasped.

"Argh," Jason roared, as several more smaller shots left a white trail down her chest and into her bellybutton.

The last drops further saturated her already wet pussy hair. The blonde muff was darker now and painted with streaks of white. Jillian kept watching transfixed to the head of Jason's cock as one last drop hung suspended from the tip. She thought she had never seen anything so wild before as the sight of Jason's cock firing bolts of white male seed.

"God," Jillian panted, still recovering from her own mind-blowing orgasm.

"I'm afraid I've made a mess of you," Jason apologized. "Let me get you a towel."

"Wait," Jillian said before he could move.

"What?"

Her hands had never left his balls. She had felt them spasming as they coated her with their pent up cum. She now saw a streak of white across her left forearm and some on her hand. Her fingers grabbed his still rigid cock and pulled him towards her. Her eyes implored him and he gather what she wanted, if only a bit surprised again by her aggression. He moved up so she could.