Bill was a Schmuck, the ungainly lanky fellow who carried his schoolwork in an old leather satchel his dad had carried to school. Bill never cut classes, he did his homework every night before he brushed his teeth and then went straight to bed. He was clumsy and no good at sports except golf, and who played golf in high school back in the sixties and seventies?

Bill never had a date to go to the school dances with but he was always there. He stood in one corner all night and watched the couples dance close; the guys placing their hands on the girl’s asses when they danced close to Bill’s corner away from the eyes of the teacher chaperones. Bill walked home from those school dances and he would lay in his bed masturbating as he had watched so many of the other kids pantomime sex on the dance floor.

Many of those lonely nights, after whacking off, Bill cried himself to sleep.

‘I will never have a girlfriend; a girl who cares about me; who loves me,’ he thought, sometimes out loud, in his lonely room.

Bill was a lonely schmuck, doomed to graduate high school a virgin.

Dorothy was a sweet, cute girl with freckles, crystal blue eyes and a lovely smile. Dorothy had a lovely average size figure, not slim, not chubby. Dorothy had lovely large breasts. She was a living, breathing dream.

Dorothy walked with her schoolbooks held close to her soft melon-sized breasts. She was a member of the in-crowd, but unlike her friends, she was kind to everyone else in school, even Bill the schmuck.

On the rare occasions that Dorthy walked alone from one class to the next, Bill would fall in step with her and offer to carry her books. Dorthy always smiled and handed over her books to Bill who grinned broadly and carried the books like highly prized objects. Arriving at her classroom, Dorthy always thanked Bill very sweetly and said, ‘Bye Bill.’

Bill would float to his own class often late because his class was in the opposite direction from Dorthy’s class. Bill was hopelessly a schmuck.

Dorthy’s steady fella was Johnny B, one of the athletic jocks and a member also of the elite in-crowd. Everybody knew that Johnny B was cool. He lettered in football, track and baseball. He was tall and well muscled and had always had a girlfriend; Dorothy being the latest.

Bill secretly longed (impossibly) for a date with Dorothy, although he had no idea how one went about getting a date. He was equally clueless about how to behave on one. Then, of course, Bill knew he could never compete with Johnny B.

Being Johnny’s steady best girl, Dorothy knew full well her duties as a girlfriend. On Friday night dates, the post-dance ritual was to go to Lover’s Point which overlooked their town. This is where the couple indulged in sweaty teenage sex in the backseat of Johnny’s Chevy convertible. It was the behavior expected of all popular girls in the high school and Dorthy paid her dues in full each Friday because this is what steady couples do, right?!’ There was a standard to be upheld after all.

One evening, Dorothy had had enough of Johnny’s selfishness and one-way kind of love. They fought in his car, broke up and then Johnny drove Dorothy home.

The next morning, the high school was abuzz with the news of the break up. Dorothy walked from class to class oddly cold and quiet and to herself.

Bill saw his chance, probably his only chance. He walked up to Dorothy during the afternoon break and did his best to chat with her.

Dorothy looked up at Bill the schmuck with new eyes. His puppy-like devotion struck her as genuine and sweet.

Bill stammered and generally made a mess at his attempt to ask her out. She placed a soft hand on his arm and said, “I’m free on Friday. Why don’t you come by at 7?” Bill had been rescued.

Dorothy stepped into her afternoon class smiling back at Bill. Bill walked like a zombie; in a near-dream state to his last class of the day. It is not clear how Bill got home that afternoon, so thick was the fog of his daze.

The week passed agonizingly slow for Bill. Throughout the week, he sought advice from his older brother and his most date-experienced friends. Bill took copious notes and reviewed them constantly. Hey! Bill is a schmuck; remember? But he formulated his plan for spending time with Dorothy. He spent as much time walking her to her classes as possible.

Dorothy was smitten by Bill’s attention and thoughtful words. Maybe Bill wasn’t such a schmuck!

By Friday, Bill was prepared for his test and his only chance to win Dorothy.

He arrived at Dorothy’s house promptly at 6:55 pm (Bill was a schmuck and schmucks are never late). He drove the family car; a ‘65 sea foam green Pontiac Catalina station wagon.

As he walked Dorothy to the car, Bill did his best to look and act calm. Inside, Bill was a nervous wreck. Dorothy smiled at Bill’s attempts to be the perfect gentleman. ‘God!,’ she thought, ‘why is this boy so hot?!’ Wasn’t this Bill the schmuck!?

As Bill meticulously worked his plan to show her a good time, Dorothy was formulating her own plan. Bill was about to become a very lucky young man!

They did a drive-in movie followed by a soft drink at the local drive-in hang out.

Bill was having the time of his life being out with this living doll. As they left the drive-in, Dorothy slid across the bench seat to sit closer to Bill. Her thigh touched his and she placed a gentle hand on Bill's knee, which made Bill’s leg tremble.

They’d talked about everything they could think of from the movie to events at school. Bill felt like he was about to run out of anything to say. Dorothy was soon to bail him out again!

As the evening got later, Dorothy said, “Bill, we should go to Lover’s Point. It’s a nice cool night and we can continue our talk there away from the noise of traffic and other people.”

Bill steered the station wagon toward the Point, becoming visibly more nervous. He thought to himself, “I’m in deep shit now! She’ll find out I have no idea how to even kiss her.” He drove in silence pondering his impending failure on this date.

Dorothy smiled at him in the dark of the car feeling a little pity at Bills nervousness and a lot of excitement at thoughts of what she planned to do to this delicious innocent sweet boy. She was smitten with Bill and knew just how to ease his fears.

Arriving at Lover’s Point, Bill parked in a secluded area and turned off the motor. “I’m about to go down in flames!” he thought in panic. He had a boner the size of Texas and prayed that Dorothy could not see the bulge in his pants in the dark.

Dorothy looked Bill in the eyes smiling and moved closer to kiss him. Her hand slid stealthily up his thigh and came to rest on Bill's crotch. She kissed Bill's lips sweetly, using just a tiny bit of her tongue to coat his lips with lovely wetness.

Dorothy touched Bill’s erection and spoke in a soft sexy voice, “Oh Bill, what do you have for me here? You’re so big and hard!”

Strangely the kiss had put Bill at ease and being felt up by Dorothy was closer to heaven than he’d ever been… He suddenly knew just what to do.

The couple snogged and grew more and more agitated and horny. He rolled down all the windows including the rear window on the tailgate.

It was a perfect night and a gentle cool breeze further excited their senses.

Dorothy unbuttoned Bill's shirt as he fumbled with the buttons on Dorothy’s dress. She lowered her dress to the floorboard. Dorothy then unbuttoned Bill’s jeans and pushed them down. Now wearing only her bra and panties, Dorothy kissed Bill again and again.

His head spinning, Bill quickly picked up on how to kiss from Dorothy’s patient example and ran his hands over her smooth pale skin. She shivered but not because of the cool night air. ‘This boy has some untapped lovemaking skills,’ she thought to herself. She was falling in love with Bill, there was no schmuck here in the car with her, only a quietly sexy lover who knew instinctively how to give and not just take.

Dropping her panties and bra to the floorboard, Dorothy straddled Bill's legs, holding his rigid cock between her thighs and playing over the shaft with her soft hands.

Bill prayed he would not blow his load and feverishly thought-recited golfing tactics and techniques to distract himself from getting over-excited. He was losing the battle.

Dorothy sensed his anxiety and whispered in his ear, “It’s okay, Bill, we will take it slow and easy. You are going to be really proud of yourself.” She breathed into his mouth and tongued his lips while saying dirty things to him like “Bill, you’re making my pussy tingle and touch my tits like this.”

Dorothy laid back on the car seat and said, “Lick and bite my nipples gently.” Bill followed every instruction to the letter.

“Now, kiss slowly down my body to my puss with lots of kisses along the way! That feels so nice Bill.” Dorothy shivered again under Bill's considerate and gentle attentions.

Dorothy thought to herself, “Johnny could learn a thing or two from this guy.” She trembled under Bill's loving caresses and kisses. The teacher was becoming the student… Bill had skills…

No longer shy and unsure of himself. Bill, emboldened by Dorothy’s coaxing, took on the role of alpha lover and began to explore her body with new confidence.

Dorothy’s breathing was uneven as she said to Bill, “Can you eat my pussy, Bill? Johnny never would do that.” She drew her breath in sharply as Bill’s tongue softly searched her labia, pierced her velvet hole and finally found her clit. Dorothy was in heaven.

Following human instinct now rather than knowledge, Bill became the gentle aggressor and lovingly dominated Dorothy’s body… He took time to lavish attention on her and pleasures her alone. His own desires raged on in his brain. Somehow Bill knew what to do for this amazing girl.

Dorothy finally spoke out, “Bill I want your cock in me. Please fuck me!!” She drew his dick to her opening and maneuvered the tip around the outside of her cunt, gathering her wetness onto the tip of Bill's hot cock. She thrust her pelvis skillfully upward as she pulled him down into her hot wet pussy.

For his part, Bill instinctually seemed to realize gentleness was essential here and slowly inserted his cock into Dorothy’s wet cunt.

Both young people were laboring for breath but were anxious to please each other. She never had known a boy to be so gentle and loving. He never knew a beautiful young woman could do such lovely, naughty things to his body…

They quickly found a rhythm and became more aggressive as the inevitable orgasm stole upon them both. He was lost in her and she was equally lost in him.

Dorothy screamed, “I’m coming, Bill! Fuck me harder!! Own my pussy!!" She clawed his back and kissed his neck over and over.

Bill began to thrust harder and faster into Dorothy’s hole. He marveled at how her pussy could grasp him so tightly. He felt powerful and confident for the first time in his young life as his body dominated this soft yielding, completely wonderful girl.

As pleasure overtook her, Dorothy’s shouting turned into a sob as tears filled her eyes. She had been loved not just fucked and she was undone. She clung to Bill’s sweaty chest and pressed her breasts into him. She held him tightly.

Bill embraced Dorothy and pulled her as close as he could. He was no longer Bill the schmuck. He was Bill, Dorothy’s lover.

He pushed his class ring into her hand and said with newfound confidence, “Be my girl, Dorothy! I love you.”

Dorothy said, “I was just about to tell you, Bill, don’t even think about trying to get away. You’re mine now and I love you!”

They lay naked in Bill’s station wagon talking and laughing quietly. Things were different now.

Bill wasn’t a schmuck anymore, and Dorothy would gladly abandon the popular crowd to stay with her boy. They spooned and fell asleep.