tagFirst TimeThe Shy Girl

The Shy Girl


Jessie Stephenson was a shy high school senior. All through high school she'd wished she was more like the outgoing cheerleaders or the captains of the debate teams or anyone other than herself. She spent the day trying to disappear into the shadows at school and was incredibly relieved when the final bell went so that she could get into her car and drive home. Some people remarked about her reticence, they couldn't figure out why she was so reserved. Some guys had asked her for dates and she'd blushed all over and mumbled an excuse. She didn't attend any school functions, despite being a very pretty girl.

Her shyness had started when she'd moved to this town, four years ago. She'd been tall and awkward, still going through puberty, and some kids had called her nasty names. Having already been a rather introverted girl she'd then pulled away completely and now she didn't know how to get out of this spiral. She was afraid people would laugh at her if she tried to participate. Inside herself she was sure that the boys who asked her out only did it so that they could make fun of her. She was much better off safe inside the house where she lived with her grandmother since the death of her parents.

Earlier this year her only friend at school, her mentor and the person who really believed in her and encouraged her to apply to go to college, had suddenly taken ill. Her English teacher, Mr Brown, had had a stroke and was now in a nursing home. He'd been replaced by Mr Andrews, and rather than being Jessie's mentor he set off a completely different set of emotions in Jessie. She was convinced that the whole school could see the way she looked at him and she'd gone from loving her English classes and seeing them as her refuge to feeling like every minute was torture.

Mr Andrews was in his early 30s, at least 6'2" tall with a fairly athletic build. His short hair was brown and his eyes were an unusual green colour. Jessie could not stop thinking about his eyes. They seemed to change colours when he looked at her and she tried to avoid his gaze. She loved him. In bed at night she fantasised about making love with him. She was as fascinated by sex as any teenage virgin and she'd spent hours on the Internet, looking at pictures of couples having sex and she wanted it all with Mr Andrews. She'd sometimes steal a glance at his crotch and get hot and bothered at the thought of his cock sliding into her wet pussy. While she pumped herself with three fingers and caressed her breast Mr Andrews' eyes were all she could see.

It was a Tuesday afternoon when Mr Andrews asked Jessie to stay behind after class. All other students ooh-ed and Jessie's face went crimson. She was sure he could see her shaking as it got closer to the end of the class, could it get any worse than this? She stayed in her seat while the rest of the class filed out of the room, some of them snickering and pointing at Jessie. She felt so humiliated. When the door closed behind the last of her classmates she walked up to Mr Andrews' desk.

"You wanted to talk with me Mr Andrews?" she said quietly.

"Yes, Jessie," he turned around and looked down at her from his raised pulpit and Jessie found herself staring right at his crotch. "I've been going through Mr Brown's paperwork and there's a letter here from Dartmouth, asking to confirm his recommendation."

Jessie's heart stopped. Oh no, it couldn't be, please don't let there be a problem with her application. "What's wrong?"

"There's nothing wrong as such. They say that your excellent academic records are impressive, but they're concerned about your lack of extra-curricular activities. For the last four years you've only listed community service at the retirement village activity centre and two years in the school choir. They're concerned that you might not fit in at college."

Jessie wanted the ground to open and swallow her. Her dreams of going to college and becoming a writer were rapidly disappearing before her eyes. "Oh," she said, quiet as a mouse.

"From what I've seen since I started here you're definitely Dartmouth material and I will let them know that," Mr Andrews continued. "But you're not going make it through your first semester at college if you continue being so quiet. At Dartmouth you'll be attending classes with students who have all been the stars of their English class and you'll disappear if you don't start speaking up in class and sharing your views vocally rather than just in excellent essays."

"I'm sorry," Jessie mumbled.

"Don't be sorry to me," Mr Andrews sounded frustrated with her. "It's your future that I care about. I want you to show everybody the talent that lies within you. Only those of us who've had the pleasure of reading your essays know how intelligent, interesting and wonderful with words you are."

Jessie looked up at him. He thought she was interesting?

"You're always looking at me with those intense blue eyes like you have a question for me." Mr Andrews sounded frustrated. "What is it Jessie? What do you want to ask me?"

"Make love to me, please?"

The room fell silent. Mr Andrews stopped pacing in front of her. Jessie finally realised that she'd said it out loud. Oh no! What had she done? She'd been wrong before. THIS was the worst it could get. With a yelp Jessie turned around and ran out of the classroom and out into the car park where she jumped into her car and drove home. She was happy her grandmother was out as she threw herself on the bed and cried like she hadn't cried since she'd lost her parents four years earlier. There were still six weeks to go before graduation. How was she going to get through them? Would they let her graduate if she cut school for 6 weeks? Would any other college admit her now that Mr Andrews surely wouldn't confirm Mr Brown's recommendation letter?

The next morning Jessie faked an upset stomach and her grandmother called her in sick. She did the same on the Thursday and Friday. Grandma was starting to suspect something, but she decided to give Jessie the benefit of the doubt and hoped she'd get over whatever it was on her own.

On the Friday afternoon Jessie was on her computer, writing a submission for a short story competition when someone knocked on the door. Grandma had gone on a daytrip with other senior citizens and wasn't due home for another five hours. Jessie got up and went to open the door. She nearly fainted when she saw Mr Andrews.

"We need to talk, Jessie," he stated and looked over her shoulder. "Is anybody else at home?"

"No, it's just me."

"Good. Please let me in."

Jessie stepped to the side and let Mr Andrews into the house. He walked into the living room and sat on a couch.

"Can I get you a cup of coffee, or a soda?" she asked him, desperately trying to avoid what he'd come here for.

"Nothing thanks," he said calmly. "Please sit down. You and I have to talk."

Jessie sat at the other end of the couch, her eyes facing the wall – she didn't want to look at him.

"Jessica," Mr Andrews' voice was soft as he pronounced her full name. "You haven't been to school since our chat the other day and I'm getting concerned. I've spoken with Dartmouth and they're going to offer you a place now that I've confirmed everything Mr Brown said about you."

"They are?" Jessie couldn't believe her ears.

"Yes, they are," Mr Andrews smiled back at her. "I told them what a passionate and intelligent young woman you are and that you'll be an asset to their school. But it still leaves us with one problem."


"What you said to me the other day."

Jessie blushed again. "I'm sorry, I didn't mean it, it just slipped out," she stuttered.

"I'm sure it just slipped out, but I think you meant it," Mr Andrews placed his hand on Jessie's shoulder. "Look at me, Jessie."

She turned her head and looked into his vibrant green eyes. He was so gorgeous. The image she saw of him when she fantasised never lived up to looking at the original.

"You asked me to make love to you," he said softly, his hand caressing her shoulder. "I haven't been able to stop thinking of the words you said. How old are you now?"

"I'm 18 and 2 months," she replied breathlessly.

"But I'm still your teacher, so it would still be wrong," he mused.

"I guess."

"And yet I've wanted to do this since the first time I laid eyes on you," he whispered and leaned forward to let his lips caress hers.

Jessie closed her eyes during the soft kiss and revelled in the feeling of his warm lips on hers. He ended the kiss far too soon.

"You're the prettiest girl in the school," Mr Andrews continued. "You're tall, but you still have a budding hourglass figure. Your long blond hair looks like liquid sunshine. Your breasts, what are they, C-cups? Your breasts strain against the material in your t-shirts, begging for someone to cup them. And you have such a luscious ass that I just want to touch when I see you walking away, swinging it in such a provocative and feminine manner."

"You think I'm s-s-s-sexy?" Jessie couldn't believe her ears.

"I've wanted you naked in my arms since the first week of teaching you. And then the other day, when you said those wonderful words to me... Do you feel the same way?"

"Yes," her voice was barely audible.

"Is that why you haven't been to school since Tuesday?"

"I was so embarrassed," Jessie piped.

"I know it's wrong, but I've been fantasising about you for months. And these last couple of nights... I can't get you out of my mind. And my hand is no longer doing the job."

"Neither is mine," Jessie didn't know where her courage to say those words came from.

"You ran away before I could give you my answer the other day. So I'll give it to you now," Mr Andrews moved up close to Jessie and placed his hands on her arms. "Yes, Jessie, I will make love to you, if you still want me to."


Not another word was spoken. Mr Andrew's mouth devoured Jessie's. Their tongues played with each other, wrestled playfully, as Mr Andrews pulled Jessie up from the couch. Still kissing, she guided him to her bedroom that was dominated by a romantic, teenage girl's dream double bed. He placed her on the floor and slowly started undressing her. First he pulled off her shorts. She stepped out of her sneakers at the same time. Then he pulled her t-shirt off so that she was only wearing pretty white underwear. There was no sign of shyness anymore as she smiled at him. He kissed her again as he reached around to unhook her bra. He kissed each pink tip of her firm breasts as they were set free. Lastly he pulled down her panties, revealing a neatly trimmed blond bush. He laid her down on the bed and then started pulling his own clothes off. Jessie watched him as his tanned chest was revealed, showing a mat of curly brown hair, disappearing into his jeans that he unbuttoned next. She could see his cock straining against his briefs and she gasped as his full size was revealed to her. He climbed over her and lay next to her, his hands cupping her breasts and his lips descending on hers again.

"You're so beautiful," he whispered against her skin.

"So are you," she replied. "And you're so big."

Mr Andrews laughed as they both looked down at his hard 7 inches. It was the girth that worried Jessie more than anything. How was she going to fit that inside her? Mr Andrews had read her mind.

"Don't worry, my darling," he said calmly. "I'll take it slowly and your pussy will get used to the size and fit it all in."

"Can I ask you a question," Jessie gasped as he started sucking on her nipple.


"What's your first name, Mr Andrews?"

Mr Andrews laughed again. "It's Doug."

Jessie locked her fingers in Doug's hair as he continued sucking on her breasts. His tongue flicked across her erect nipple as his finger mimicked the action on the other breast. Jessie moaned out loud. She'd never realised how good it could get. She arched her body as Doug's experienced hands and mouth moved down, past her stomach and parted her legs to gain access to the private folds that nobody had touched before.

Just as she thought that he was going to take his big cock and slip it inside her he leaned forward and buried his face in her bush. His tongue licked along her moist slit, finally parting her pussy lips and gaining access to her dripping creases. She could hear him lapping up her wetness and she kneaded her tits as she revelled in the pleasure. He closed his lips around her clit and started sucking on it. She tossed her head back and forth as she didn't know how to deal with all this pleasure. Then he moved his tongue and penetrated her tight cunt with it. A steady stream of pussy juices flowed into his mouth as his tongue fucked her, slowly at first and then faster.

Doug's 5-o'clock-shadow created friction against her pussy that only increased the pleasure of his tongue fucking. With his tongue up her cunt his pussy juice covered finger started massaging her clit. Her moans got louder and louder. She raised her hips to feel his tongue deeper inside her. She was on fire for him and didn't know how much longer she could last with this intense pleasure.

"I'm gonna cum, Doug," she panted.

"Cum for me Jessie," he called out from her wet pussy.

She needed no further encouragement. Her body shook violently and her cunt gripped his tongue tightly as she cried out her joy. As soon as she was done cumming Doug climbed up next to her and kissed her deeply, letting her taste her own cum.

"You have a wonderful cunt," he smiled at her and caressed her tits. "I want to feel my cock inside it. Are you up for more?"

"Don't you want me to suck your cock first?" she asked with youthful naïveté.

"You're a virgin, aren't you?" he asked her softly.


"Then I'll teach you to suck my cock another time. Today is just for you. Today I'm fucking your tight little virgin cunt and showing you what a man and a woman are made for."

He started kissing her again and kneading her tits. As his hand made its way down to her pussy he could feel that she was getting turned on again. A dip of his finger in her cunt proved this. He positioned his knees between her parted legs and ran his pre-cum covered cock along her wet slit. She felt so good against him. Jessie moaned as she felt his swollen mushroom tip caressing her hungry cunt. It surely couldn't be long now before her long term fantasy would become reality. Mr Andrews was finally going to fuck her.

Jessie hungrily lifted her hips, opening her pussy like a rose. Doug swallowed deeply to stop himself from plunging straight in. She looked down and watched his cock against her hole. She kneaded her tits in anticipation. He grabbed her hips and slowly let his cock find the tight cave that was full of warm feminine wetness. She moaned as his big shaft started penetrating her. He was so big and she felt so tight. Once his whole head had popped inside he stopped and let her adjust to his size. She soon moved her hips to feel more of him and he started sliding slowly. He came to a stop and moved down to kiss her. As his tongue was in her mouth he forced the rest of his cock inside her, tearing through her barriers and causing her to cry with pain.

He didn't move. He kept kissing her as she panted and felt the pain of his cock in her virgin cunt. Soon the pain ebbed away. Soon all she felt was a hunger for more. She started returning his kisses and moving her hips. He responded by grabbing her legs and parting them wider and pulling them up. He now had full access to her hungry cunt. He slid out almost completely and then he slammed back in. He gyrated his hips, letting his cock take full possession of her cunt. She moved her hips with his, eager to get him deeper. Each thrust of his slammed his balls onto her wet ass and his pubic bone hit her clit. She moaned louder and louder. Doug's cock in her cunt was heaven. She loved fucking more than she'd ever imagined.

Jessie tugged her nipples and pulled her tits that bounced with each of Doug's slams into her tight cunt. She panted with pleasure and kept looking down to see the wonderful sight of his thick cock being sucked into her hungry cunt. He had an intense look of concentration on his face as he pumped her faster, harder, and deeper. They were still teacher and student, but now he was teaching her new things, new skills. He leaned forward to bite her nipple and she squealed with joy.

"I have to cum, Doug," she finally whispered, unable to speak louder.

"Me too, baby, cum for me. Cum around my thick cock."

With a scream of pleasure she let herself go. Only the weight of Doug's body on top of hers stopped her from falling off the bed as her body convulsed uncontrollably and her cunt gripped his cock hard. The increased pressure on his pumping cock was all Doug needed to send himself over the edge. He groaned loudly as he finally let her cumming cunt milk him dry. Load after load of hot, thick spunk was sent up her womb as his body bucked in orgasmic pleasure. He soon collapsed on top of her.

With Jessie in his arms Dough rolled to his side, his cock still lodged inside her wonderful, warm cunt.

"That was incredible," he kissed her.

"It was better than anything I ever imagined," she admitted.

As Doug's shrinking cock finally slipped out of Jessie's cunt she felt a mixture of his and her cum flooding out of her. She looked down at his sticky member.

"Can I lick it off?" she asked and he nodded in reply.

With their cum flowing down the insides of her thighs she moved down and took his limp cock in her mouth and circled it with her tongue. He groaned as it started growing harder in her mouth and pulled her up again.

"My darling," he said with a smile. "If you do that we'll have to do all this again and it's already 5.30. I don't think we have time for it."

"Oh no," she gasped. "Grandma will be home shortly. We have to get dressed."

They quickly stepped into their clothes and as Jessie arranged the sheets to hide the blood of her lost virginity and the wet stain of cum Doug wrote something on a piece of paper. They opened the windows to let some fresh air in and he took her in his arms and kissed her again.

"I've written my address down for you. I'm home all weekend. Please come and see me. I want to make love again."

"What if anyone sees me?"

"Nobody will see you if you drive around to the back of the house."

"I'll be there tomorrow."

"I was hoping you'd say that. Then I might teach you how to suck my cock."

"I can't wait." She couldn't.

Jessie and Doug were drinking a cup of coffee in the kitchen when grandma stepped in.

"Grandma," Jessie smiled. "This is Mr Andrews, my English teacher. He's got some great news."

"Mrs Stephenson," he greeted grandma with his winning smile. "I received word today that Dartmouth will offer Jessie a place in September."

There were cheers and hugs all around and grandma tried to convince Doug to stay for dinner. He declined and soon walked out into the evening, satisfied and hungry for his wonderful young lover. Jessie did stop by the next day, and the next, and as often as she could during the six weeks leading up to graduation. She learnt to suck his cock. She learnt to ride him. She learnt to take him from behind. She even learnt to take him up her ass. Everybody was amazed by the change in the shy girl. She opened up completely. She started talking to people. She was no longer afraid to speak up in class. Everybody attributed it to her being accepted to Dartmouth. Jessie and Doug exchanged secret glances that they knew different. After her graduation speech Jessie sat down next to Doug and whispered to him "I'm pregnant."

In September Mrs Jessica Andrews enrolled at Dartmouth. She was 5 months pregnant and she lived with her English teacher husband just outside the college.

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