Popping Cherries

Friday at lunchtime in Chad David's classroom, he was looking over his lesson plan for the last three periods of the day.

"Mr. David?" a shy voice in his doorway made him look up, standing there looking very nervous and hesitant was Clarissa, one of his favorite former students. The 40 year old teacher smiled welcomingly at her.

"Hello Clarissa, what can I do for you?" Even though he was forty years old, he was in great shape and with his long black hair and bright green eyes, the handsome man caught the eye of a lot of the high school girls, he was the most fantasized about teacher at McKinley High.

"Well um..." her voice trailed off softly for a moment, and he admired the pretty hazel eyes which were filled with shyness with their long trailing lashes, and her heart-shaped face which was framed with brown curls, "I was talking to Claudia you see... and I was wondering..." ah, now he knew what was coming, and he had to admit to himself that this pretty student was one that he'd hoped would come to him, "I was wondering if you'd do for me what you did for them."

Leaning back her considered, since he was a high school teacher, he did have to be careful what students he took home for his special "lessons". Mostly it was girls who were still virgins and wanted to lose their virginity with as little pain as possible, and as much enjoyment as they could get out of it. Apparently word got around. Clarissa was a senior now, not his student (he taught Junior English), and he'd been attracted to her when she'd first come into his class the previous year. With her short sun-burnished brown curls, petite 5'4" curvy figure, he'd have been hard pressed not to fantasize about her a little. Firm young round breasts under the blue v-neck shirt with a tight firm ass covered by her knee-length black skirt... and she wanted to give him her virginities... he only took girls who had no sexual experience at all.

"Close the door Clarissa, and come sit down. I need to ask you a few questions before I can answer you." He watched as she did so, and could feel his dick already getting hard under his desk as she moved. She really was one of the most attractive young ladies to ever have come to him. And he did like them young, although he refused to touch one under 18. One day he might be found out and fired for his activities, but he wouldn't be arrested.

Sitting down at the chair beside his desk, the nervous girl could barely look at him as he watched her face intently.

Finally he asked, "Are you 18?"

"Yes, my birthday was last week... I know you don't take girls before that so that's why I waited."

"Have you ever given or received oral sex?

She shook her head, her cheeks turning a delicate shade of pink.

"Vaginal? Anal?"

Still shaking her head no, the color in her cheeks was becoming darker.

"You do understand that when I take you on, I do all three of those?"

Nodding, she looked at her hands gripped tightly on her skirt in her lap.

"What's the farthest you've ever gone with a boy?"

Her voice was soft, shy, "Last year at junior prom, my date and I kissed when he took me home and he felt my... my breasts, but only over my dress."

"Are you on birth control?"

"My mom put me on it last year for my period."

"Why did you come to me?"

"Because Claudia told me that it was the best experience she'd ever had... and she's had other guy's since, and she said that it barely hurt at all and that now she wishes she could come back and do it again, she also said that all the guy's think she's incredible because of everything you taught her." He saw that her knuckles were turning white she was clasping her hands so hard.

"Are you afraid of it hurting?"

"Yes."

Sitting back, he nodded slowly, "Clarissa, I would be glad to." As she lifted her head, he could see relief on her face and he smiled, for a girl as painfully shy as she was it must've been hard to gather the courage up to come see him. "Can you come home with me after school?" Nodding, he could see some excitement spark in her eyes.

Smiling at her, he pushed his chair back and unzipped his pants; her eyes were huge as they fell on his 9" prick, it was very long but rather slender, which was why virgins appreciated him so much. That and he knew how to use it.

"Come here, we'll start with your mouth and take care of everything else this afternoon." Smiling encouragingly, he could feel his dick pulse as she knelt in front of him, hesitant, "Hold it in your hands," he used his own to guide her placement, "Now lick the head." Tentatively, her pink tongue came out and gave it a soft, exploratory lick, with that first touch she became a little more confident and licked the pink crown again. Moving her tongue around his peehole, she gained even more confidence as he leaned back in the chair and moaned.

"Now put it in your mouth, make sure you keep your lips tight around it, but don't let your teeth touch it." Clarissa's pink lips parted and she opened her mouth to engulf the head of his dick, he hissed as his head was surrounded in the wet warmth, "Good, now move your hands down to the base and put as much of my dick in your mouth as you can." Surprisingly, she apparently had no gag reflex at all and she actually moved her hands away from the base of his dick as her mouth slid all the way to the base of his penis, her throat pulsing around him.

Pulling her head up by her curls, he looked at her suspiciously, he didn't think she'd lied before, but he'd never had anyone be able to swallow his entire length on their first try, "Are you sure you've never given head before?"

Clarissa blushed and shook her head, "No, I just don't have much of a gag reflex anyway, and Claudia showed me how to practice on a banana," her voice dropped to a low embarrassed whisper, "And I wanted to impress you so I've been practicing every night."

"Well, I am impressed," he smiled at her, and she smiled back in pure pleasure at the compliment as he pulled her head back towards his extremely hard dick, opening her mouth immediately to take his length back down her throat, "Since you don't need your hands at the moment," he kept his hold on her hair as he breathlessly instructed while her mouth slid up and down over his dick, "Use them to cup my balls, squeeze very gently and tug very gently, roll them around..." his hips thrust up as she tugged slightly on the sack, "oooooh.... that's it, good girl."

She had incredible instinctive technique, her tongue fluttering over his shaft as her mouth sucked and her throat pulsed... it was one of the best blow jobs he'd ever had, and he couldn't wait to see how she was in bed. He began to push harder as his balls were gently squeezed and rolled in her small hands, finally using his own hands to move her to his rhythm.

Holding her head, he pushed her down so that her mouth was tight against the base of his dick and held her there. His balls boiled up and he groaned as her throat convulsed around his head while spurt after spurt of cum shot out of his dick and straight down her throat. Her mouth continued suckling even after his dick started shrinking, she was so eager that she'd swallowed every drop of cum.

Looking down at the pixiesh brunette in front of him, he stroked her curls and smiled tenderly, "Clarissa, you are going to be one of my best students yet." Pleased and proud, she let his dick fall from her mouth as he leaned down and kissed her lips gently, "Lunch is almost over, get to your next class and meet me back here at the end of the day."

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At Chad David's house, Clarissa stood meekly in his bedroom, completely naked while he looked over her small body. At 5'4", with 34C breasts and a bubble butt with a narrow waist in between, she was deliciously curvy, a perfect hourglass figure; her mound was completely shaved and hairless, pink pussy lips peeking out from between her legs. Chad groaned as he pulled her into his arms and kissed her, so far she'd already proved to be a natural at cocksucking, and one of the most attractive girls he'd ever taught.

"Mr. David..." her voice was breathy as she moaned his name while his lips traveled down her neck. Since he was 5'9" it was getting too hard to lean down to her body, so he lifted her up by her narrow waist, and her legs wrapped around his body as he cupped her buttocks with his hands, kissing down the curve of her breast to the strawberry nipple. He began walking over towards the bed as he sucked her nipple into his mouth, a pleasant shudder coursing through him as she whimpered. Next to the bed he set her so that she stood in front of him.

"Undress me," his voice was harsh with desire and lust as she slowly began unbuttoning his shirt and pulling it off him, then his pants. Looking up at him, she waited patiently for his next command. Dear God but he loved her attitude, "Lie on the bed on your back."

It almost made him want to cum immediately, seeing her curvy figure spread out on his bed sheets, innocent gaze waiting patiently. Getting onto the bed next to her, he lowered his mouth for another kiss, letting his left hand trail down her body to her breasts. Gently he stroked the swell of her flesh, slowly working his way in to the nipple, when his fingers gently closed over the nipple her mouth opened under his in a gasp and her back arched.

Clarissa was on fire with sensation as her former teacher's hands caressed her body, heat was spreading all over her breasts and heading straight to her pussy. Laying his body on top of hers, she could feel the heat of him, and she moaned and moved her hips, yearning for something... she just didn't know what. His hands moved up her arms as his mouth devoured her nipple pushing them above her head so that her breasts were totally open and exposed. Even after his hands came back down to her breasts, kneading the soft flesh, she kept her arms above her head, hands tangled in her curls. She wanted to feel everything.

Transferring his mouth from one nipple to the other, he nibbled delicately at the tender flesh, enjoying the moans and whimpers as well as the movement of her hips beneath his body. She was marvelously responsive, and he kept his hands on her breasts as his mouth moved lower, leaving a burning path of kisses across her stomach. Reluctantly taking his hands from her breasts, he spread her thighs before him, opening the pink wetness of her pussy to his eager mouth. Hooking her legs over his shoulders, he eagerly ran his hands back up her sides to her breasts and nipples as his mouth nibbled on her inner thighs. The musky sweet smell of her pussy filled his nose as he worked his mouth closer and closer to her bucking hips, when he finally began licking delicately around the outer lips of her pussy she let out a high-pitched whine, pushing her hips high in the air.

Slipping his tongue into the inner folds of her pussy, he explored every crevice of her soft wetness, the sweet taste of her juices filling his mouth. Clarissa was arching her back and clutching the pillow above her head, gasping for breath as the most intense sensations gripped her young body. She could feel his tongue pushing into her tight virgin hole as his fingers pinched her nipples in a firm grip. Something inside her exploded as his tongue wriggled in her hole, and she let out a wordless cry as intense pleasure swept over her, the mouth on her pussy pushing her higher and higher on an endless climax of heat and ecstacy. Her head thrashed as his mouth moved higher on her pussy, sucking on the delicate pink clit, her voice rose in a wail of pleasure as her whole being vibrated and pulsed madly.

She barely noticed, in the intoxicating heat of orgasm, when he broke through her maidenhead, having got into position during the waves of her intense climax when the pain of first entry would be completely lost in the throes of ecstacy. It was only when she noticed his face above her own flushed one that she felt the slight throb of pain in her pussy, but it didn't matter; her body was glowing in the aftermath of orgasm, and the astonished pleasure on his face as his dick moved in the exquisite tightness of her wet sheath completely did away with any real notice of the hurt. Moving slowly, letting her body adjust to his long dick, he carefully pulled and pushed his dick in and out of her extremely wet and wonderfully tight pussy. Grunting, he tried to concentrate on going slowly so that he didn't hurt her.

Wrapping her slender arms about his shoulders, Clarissa's lips moved delightfully against his ear as she whispered, "Please.... more.... harder..."

Groaning, her teacher lost all control and began thrusting quick and hard in and out of her deflowered pussy, and she cried out as slight pain intermingled with a lot of pleasure coursed through her. Strong arms pressed her close into his hard body as he ravished her body, her nipples rubbing against his hairy chest and her little clit sliding against his hard groin as his dick stretched her wonderfully. Clarissa arched her back and let out a high moan as the wonderful feeling started building between her legs again, with every thrust the moan became louder and higher-pitched, until it was almost a scream as the heady waves of her orgasm crashed over her again. Chad groaned her name as her tight pussy gripped him even tighter in the throes of her orgasm, her body quivering against his own. He began to lose jet after jet of hot cum into the molten heat of her body, continuing to pump so that her orgasm continued until he was finally spent, and rubbed gently against her until the long wailing moan subsided into a soft whimper as the sensitive flesh of her pussy quivered.

Kissing her lips, their tongues danced slowly as his dick softened and reluctantly slid out of her warmth. Smiling down at her tenderly, he told her, "That was incredible." And it had been, she really was going to be his best student ever. It almost made him wish that he took repeat students.

Sighing, he rolled off of her soft body as she smiled shyly and happily at him, "Now what?" she asked, eager for more new and amazing experiences and feelings.

He laughed at her newfound confidence and curiosity, "Now, you use that talented mouth of yours to clean me off, but leave the bottom half of you up here so I can start getting you ready to lose your last cherry."

Eagerly, the sweet girl got on all fours, her head down at his penis and small pink tongue already licking their combined juices from his groin. Chad again wished that this wouldn't be his last time with her, she was eager and willing to try anything he said, and her responses were amazing... some girls would put up a bit of a fight before cleaning him off afterwards, or would suddenly want to stop even though they knew part of the deal was their virgin ass, and then he'd have to go through the whole rigamarole of convincing them. Not Clarissa, she had the body and experience of an angel, but the heart of someone who was born to please men. Positioning her so that she had one leg on either side of his head, he rubbed her soft thighs and ass cheeks before dipping his finger into her pussy, covering it with a mixture of their cum. Rubbing the messy wetness on her asshole, he pushed just the tip of his finger into the tight crinkled light brown hole.

For a moment, her body tensed and she paused in her licking, but after her ass clenched and then released around his fingertip a few times she adjusted and started licking him again, now moving her mouth down to the wetness on his balls. As she sucked on of his balls into her mouth he started sliding his finger into her ass up to the first knuckle, when she didn't even pause in her suckling he slid it all the way in. Moving it in and out a few times, he sighed happily as she sucked the other ball into her mouth and he could feel his arousal starting to stir again. He pulled the finger out as her mouth closed around his dick, gently sucking and caressing it with her tongue; he could feel his dick starting to harden with her encouragement as he slid two fingers into her back door. The tightness was incredible, but she didn't resist at all as he worked the two fingers in and out of that stretched hole.

With his dick standing at full mast as she slid it down her eager throat, he added a third finger to the crinkled hole, and she moaned a little, her body wincing as the fingers burned a little in their journey. Still, nothing was actually feeling overly painful, he was being very careful in how he stretched her, and she could actually feel herself starting to get a little turned on as he slid his slick fingers in and out of her ass. This was the part she had been the most worried about, she'd always heard that it hurt terribly to have anal sex, and even Claudia had said that it had hurt her some, but she wanted it too. She wanted it badly, and the slight amount of pain was even turning her on a little. Her ass felt full, maybe a little uncomfortably so, but she felt dirty and naughty with her former teacher's fingers in her ass and his dick sliding in and out of her throat; the whole situation made her extremely turned on and horny.

Pulling her mouth from his dick, she pulled her ass off his fingers and got on all fours next to him, looking back entreatingly, "Please, do it, please fuck my ass now...I think I need it."

Those dirty words coming out of that sweet and rather innocent -if admittedly less so after the past hour - mouth, made Chad's eyes practically glaze over with lust. Faster than he could have imagined, he was kneeling behind her, positioning his dick at her slightly stretched hole. Slowly, her ass stretched around the head of his cock and she moaned as the pain shuddered through her body... oh he was hurting her wonderfully. As he slid another inch into her slick back door she lowered her head onto her forearms, leaving her ass high in the air for him to plunder, as she panted and tried to adjust to the exquisitely painful invasion. He began to work his dick back and forth in her ass, slowly working inch by inch into the stretched orifice, letting her adjust as his dick traveled deeper into her brown hole. Whimpering, Clarissa pushed her ass back onto him, shoving the last inch of his dick into her so that the pleasant sensation of being painfully full swept over her completely as his dick was completely buried in her hot little hole.

Chad groaned and laid his body over hers, reaching his hands around to grasp her breasts as he moved his dick in and out of the slick hole; it was the tightest back door he'd ever been able to sink into... a lot of the girls wanted to be totally stretched out as he entered them. Clarissa seemed to revel in the discomfort and slight pain. As he pinched her nipples, she struggled to push herself back up onto her hands, wanting to be able to push back against him as he plundered her no longer virginal hole. She gritted her teeth and began ramming her soft firm ass against his body every time he slammed home, a new kind of pleasure sweeping over her as her ass was filled and refilled with his hard dick.

Using his arms, Chad leveraged her up so that she was at a 45 degree angle, holding her up with one hand flat against her stomach and the other buried in her pussy, rubbing her clit and stroking the wet folds with his fingers. Clarissa cried out as the position allowed him to burrow deeper into her ass, finding new areas to explore and stretch, her head fell back as she started squeezing her own breasts, pinching and twisting the tender nipples.

As yet another orgasm crashed over her, she started crying out obscenities, completely lost in the moment, "OH GOD... FUCK MY ASS MR. DAVID.... FUCK ME.... OH FUCK ME HARD!!!! CUM IN MY ASS!!!! OH GOD I'M CUMMING MR. DAVID!!!! FILL ME UP WITH YOUR CUM!!!!!!!!!!!!!!!"