Merrill and Jake had dinner, alone. She asked, "Jacob, do you remember when you reviewed your seven virgins for me? I said that I would need more detail on numbers three and four. I'd like to hear it, now. Please keep in mind, dear, that I do not hold the teenage Jacob Taggert to a mature standard of behavior. You will not be tried as an adult."
Jake sighed, and said, "Not my finest hour. Okay, I'll tell you all the gory details. Number three was Kelly."
Kelly was a pretty girl. She had light brown hair, in a short, dutch-boy haircut. Slim, small-breasted, with a perfect ass. Her face and smile were enchanting. What set Kelly apart, for Jake, was her intellect. Kelly was probably the smartest girl Jake ever had sex with. She was in every honors class. Jake knew her only because they took Spanish together, and there was no honors class in Spanish.
She made it clear that she was attracted to him. She patiently disregarded the fact that he was not on her level, mentally. She was into his looks. He was the strong, silent type. They were both seniors. She had already been admitted to UCLA. She did not want to show up, there, a virgin. Subconsciously, she decided to sleep with Jake, shortly after they began dating. Kelly pursued Jake for his looks, fully as much as he ever pursued a girl for her looks.
They made a pretense of getting together to study Spanish, but both were interested only in sex. Kelly was from a very good family. They were caring, educated, and conservative about sex. Kelly needed to make Jake jump through some hoops, just to preserve her self-image as a "good girl." She was forbidden to visit Jake at his house, or be alone with him at her house.
Jake gave Kelly her first kiss, at school. Their study sessions, at the dinner table in her parents' home, devolved into makeout sessions, whenever her mom was not present for any reason. Kelly's sister, Christy, at sixteen, was two years younger. The sisters strongly resembled one another. Kelly and Christy were very close.
Christy, too, was attracted to Jake, on more of a little girl infatuation level. Kelly rolled her eyes at Christy's flirtations with Jake. Outwardly, Jake did not react to Christy. He was certain both sisters had incredibly tight pussies. He felt certain he would soon find out about Kelly. As to Christy, he intended, eventually, to imagine her, while he fucked Kelly.
Kelly was ready. One Saturday afternoon, there would be no one home until the evening, leaving Kelly and Jake several hours alone. She greeted him at the door. He immediately mauled her, kissing her deeply in the mouth. "Let's drink!" she suggested. They broke into her parents' liquor cabinet. She clumsily prepared an awful cocktail, which she drank nervously. Her hands shook. He knew that she was trying to settle her nerves. He therefore expected to be taking her virginity, momentarily, so he only sipped his drink.
When she downed her drink, she slammed the glass down, threw her arms around Jake's neck, and kissed him passionately. He said, "Let's go to your room."
"Okay." He led her upstairs. Kelly's room was outrageously girlish. She had a ruffled canopy bed. The room had the overall pink theme, complete with stuffed animals, that she had since she was a little girl. Once inside, Jake began peeling off her clothes. She helped.
Experience had taught him to save the final reveal to the end. He knew that a reluctant girl could easily change her mind, if either of them were fully nude for more than a few moments. When she was down to bra and panties, he stripped to his shorts, which strained against his erection. She turned down the covers. He removed her bra and panties, and she slipped into bed. By the time she turned around, he was nude. His cock raged.
He climbed into bed, next to her, and started to rub her clitoris with one finger. He had done this before, when she was partially clothed. He got up on his knees, produced a condom, from nowhere, and put it on. She lay back on her elbows, and obviously very nervous. He had experience with reluctant girls. He knew that, if she panicked, and tried to back out, the whole thing would turn ugly. He would likely have to spend a lot of time and effort to get return to this point.
His solution was to take her consent, and run with it. He separated her legs, and kneeled between them. He leaned forward, over her, gently moved her upper arms along her sides, grasped them firmly in his hands, and leaned on them with outstretched arms. In his mind, it was now a done deal. She had tacitly consented, and he would not allow her to change her mind.
He looked down, nestled his cock at her slit, and probed for her entrance. Kelly felt the head of his cock parting her lips, and panicked. "Wait! Wait! No, Jake, please wait!" He ignored her. She had willingly journeyed with him to this point, after weeks of buildup. She had consented. She was just nervous. He thought it unreasonable for her to expect him to stop while entering her because of a momentary case of jitters.
He pushed inward, parting her vaginal tissues with his big cock. She squealed, and said, "No! No! I said, no! Stop!" Her hymen partially tore, as he passed it. She ceased trying to stop him, and began to complain about the pain. "Ow! Ow! It hurts! Ow!" Hers was the tightest vagina he had yet entered. He applied considerable force to continue his entry. He moaned with the sensation of her warm flesh gripping his cock.
When he was halfway in, she began to cry. He put more of his weight behind his drive, and buried himself in as far as he could go. Still ignoring her, and focusing on the sensations on his cock, he pumped his hips. He drove his cock into her, against the mysterious, spongy tissues that lay beyond her vagina. He came quickly. He grimaced, grunted and groaned for a short while, thrusting his hips, and shuddering.
When finished, he opened his eyes, and looked at her face, for the first time. She cried audibly. Her eyes were red. Her face was streaked with tears. Her vagina held his cock in a warm embrace. He pulled out only because the condom was full.
Jake rose up on his knees, at her feet. While he squeezed the overflowing condom off his cock, Kelly brought her legs together, and rolled onto her side, crying more loudly. He tied a knot in the condom, crawled out of bed, and dropped it in the trash can. He stood, looking down at her. He congratulated himself on his conquest. He thought it had gone fairly well. He thought about how tight she had been. He wanted to enjoy that pussy of hers. He wondered how much tighter the younger, smaller, Christy might be.
He put his hands on the bed and leaned over, saying, "Kelly, it's okay. It's okay. You did fine, Kelly."
"I told you to stop! I said no! I said no!"
"Kelly, it was too late to stop. I couldn't stop. I couldn't. You let me, Kelly. I didn't force you. I can't just stop in the middle, like that. It will be okay, Kelly."
"Please get out. Please just go away!"
"I will wait for you, downstairs. I won't leave until you talk to me."
When Kelly came downstairs, wearing different clothes, she would not look him in the eye. She let him embrace her. "Kelly, it won't be as bad, next time. I promise. Maybe you can drink some more, and it would relax you, and it won't hurt." He kissed her, tenderly. He groped her, against her resistance. "I love you, Kelly. I love you." He worked hard to regain her trust.
