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The Real First Time

The first time is not always super awesome.
The Real First Time

John was nervous all day long. It had been two years today since him and Jane began dating. They were sixteen when they decided to enter into a relationship with each other and he never expected it to last this long. Not that true love could not be found in high school, but he expected to have dated at least five or six other girls at this point. He was not going to deny he was attractive and five or six other women would not have been hard to obtain. Yet he remained with Jane, because she put up with his childlike behaviors and didn’t mind when he didn’t call her for days.

“So where are you taking her this evening,” his bro, friend not relative, asked him at lunch that afternoon in the cafeteria. He pondered the question over what appeared to be some sort of mystery meat. It was more than likely the same mystery meat they had the day before, only this time they had decided to cover it in gravy so that students were not as suspecting of it.

“I thought something along the lines of dinner and a movie,” John nodded. It seemed that was the best option out of things that they could do. They were eighteen, so it was not like they could go to a bar or party really. Plus he only worked a part time job on the weekends, so anything more fancy than that would be out of his budget. He had already asked his father to pay his car insurance this month, because he had not made enough money at work, so asking for money for a fancy date would be out of the question.

“Nice,” his bro nodded his head and dug into his plate of mystery meat, being the giant jock who would eat anything you put in front of him. “What movie you thinking?”

“I don’t know,” John answered, not really sure what was out these days. “Maybe some chick flick. That is sure to make her happy. She loves those sappy chick flicks that make us guys look like absolute jerks who cannot live up to such unrealistic qualities.”

“Dude,” his bro talked with his mouth full of food. “You should take her to a scary movie. That way she will get scared and be hanging all over your arms and shit. You are bound to get some pussy if you protect her from the scary movie.”

“Maybe,” John nodded in agreement. Not that John ever got pussy. Jane was on some bullshit kick of saving her virginity for marriage. If she was going to sleep with him, he had to pop that question and be tied down to her for the rest of his life. He figured that masturbating before-hand would be less stressful than saying ‘I do.’


“So what are we going to see?” Jane asked him at the burger joint they had just left. Sure it was not the most romantic dinner in the world but it was a special day and burgers were called for.

“I was going to let you decide,” he offered up to her. “Since I picked the dinner place and what not, figured we would see a movie you wanted to see.”

“What if I wanted to The Last Kiss, that new romantic comedy that just came out?” She asked him, obviously trying to push her limits, but he had already planned on having to see some lame chick flick for her this evening.

“I would be just fine with that,” he smiled at her. He had a decent imagination, he would just think of all the things he would be able to masturbate to later or what it would be like if some monster came into the movie and ripped all the heads off of the pretty people. “It is your choice babe.”

So they saw a chick flick and it was dreadful. She laughed, she cried, she asked him why he could not be more romantic and then it was over. He was happy that it was over. He was not sure how much more sap could be comfortably fit into this evening.

John drove her home after the movie and they stood awkwardly on the front porch before he leaned in and kissed her goodnight. The kiss lasted for quite a while: at least without sex, they had some pretty awesome make-out sessions. Though normally it was not so out in the open.

“I have a present for you,” Jane smiled at him. He was not happy about this. Besides the dinner and a movie, he did not buy her a gift. The night took all of his money as it was.

“I did not get you anything,” he frowned, worried that she was going to be disappointed and the evening was going to be ruined for the both of them.

“You gave me plenty this evening,” she smiled, trying to reassure him. “It is my turn to give you a gift.”

“Okay,” he nodded, suddenly excited. He hoped it was the video game that he had been talking about to her for weeks now. That would be the ultimate gift and reaffirm why he was still with her. She liked to get him things that he wanted, who would walk away from that?

“Come up,” she pushed open the front door slowly to a dark house. “Just be quiet, my parents are probably asleep and we can’t wake them up.”

“I could just wait down here and you could bring it to me,” he told her, not really a huge fan as it was of her dad. The last thing that he wanted to do was wake him up.

“You have to come up for it,” she placed her hands on her hips. “Or you don’t get it at all.”

“Fine,” he shook his head, walking slowly into the house. “But if your dad wakes up, I am out the window.”

“Deal,” she laughed. “If my dad wakes up, I will help you jump out.”

They both quietly made their way up to her bedroom and thankfully no sounds came from any other part of the house. Once in her room, he sat down on her bed, which he had done a million times before, except the door was never shut and the house was never asleep. They were generally watched so closely that he found it uncomfortable. That is why she came to his house more often than him to hers.

Jane disappeared into her closet and allowed him to wait anxiously. He was still wondering what it was that she could have gotten him, though he hoped completely that it was the game that he wanted. If so, he would probably be missing school tomorrow. New video games were always the best reason to fake being sick.

“Happy anniversary.” Jane reappeared out of the closet in panties and a bra. His heart stopped. Never in a million years would he had expected to see her out of her clothes. She did not even like it when he ran his hand under her shirt when they made out.

“What is this?” he asked excitedly, putting his hands in his lap to cover his instant hard on that he had received. He knew it was a rookie thing, but he was a virgin and there was a half-naked girl in front of him. What else would you expect?

“I want us to be together,” she told him. “I know that I always say that we should wait for marriage, but who really does that anymore?”

“I have no idea,” he smiled up at her. “Are you sure you want to do this?”

“Yes,” she smiled, walking over and standing in front of him. “I am sure.”

John pulled Jane down onto his lap and she kissed him. Their lips danced together and she ground against his hard cock, which just continued to get harder. He eventually had to move her hips back because he could not take the rubbing any longer. He was not ready for this to be over.

“I don’t want to do the oral thing,” she threw out of nowhere, which ruined his hopes for the next few minutes. “Sorry, I thought about it but it just seemed kind of gross.”

“That is okay.” He smiled, kissing her again and running his hands up her sides until he reached her breasts. He took the change and grabbed them between his hands and for the first time ever she did not pull away. Her head moved back and she moaned. This was really happening, she really wanted to have sex with him.

“I have wanted this for so long,” he smiled at her, reaching behind and fumbling with her bra, trying to figure out how to pull it apart. Finally she reached back and helped him snap it off of her. It fell down her arms and revealed her perfect breasts. “Can I suck on them?”

“Yes,” she nodded and he could tell that she was nervous.

John leaned in and took her left nipple into her mouth and sucked on it lightly. She moaned slightly, her head leaning back again. He began to suck a little harder, running his teeth over the surface.

“Ow,” she called out. “Watch it.”

“Sorry,” he apologized, taking note to never do that again.

“It is okay,” she laughed. “Just be careful.”

He continued to suck at her breasts until she pushed him back, obviously having enough. She seemed to be wanting to get on with what they were doing and he was fine with that.

Jane crawled off of his lap and took off the rest of her clothes, asking him to do the same. He jumped up quickly, almost losing his balance but caught himself. He was out of his clothes just as quickly as she had asked him to be, his hard cock standing straight up.

Jane looked down at his cock which was a good six inches and smiled nervously. He did not think it was anything special but he hoped that she at least liked it. She then moved over to the bed, pulled back the covers and crawled in, he soon followed.

They laid there under the covers for a few more minutes, kissing and touching each other’s bodies. He then climbed on top of her and leaned down to kiss her some more. She slowly spread her legs beneath him and he slid in between them, his cock resting against her smooth pussy. The excitement almost too much to handle.

“Are you sure you want to do this?” he asked her again. He did not want to make her do something that she was not ready to do, though this had been all her idea to begin with. He just went along with all of it because he was a guy and he wanted to have sex with her.

“I want this,” she nodded. “Just be gentle.”

John nodded his head and reached down between their legs. He took his cock into his hands and worked to put it in the right place. It took him a minute or so, but soon he found her semi wet opening and slowly pushed the head of his cock into her.

“Oh,” she cried out.

“What?” he asked pushing forward. “Do you want me to stop?”

“No,” she tried to smile. “Keep going.”

John pushed slowly into her. It took a while, but soon he was all the way inside of her. He held himself there for a moment, enjoying how warm and wet her pussy was. His cock was in pussy heaven and he was basking in it.

“Okay,” she smiled. “I am ready, keep moving.”

John pulled his cock out, not all the way but back to the tip and then slowly pushed it back into her. He did it slowly a few times but then began to push harder into her. He pumped hard into her a few times and it soon became too much. He could not hold it anymore and he exploded inside of her, his entire body tensing up as he came harder than he ever had. He then collapsed on top of her.

“Oh my god,” she cried out. “Did you just come inside of me?”

“I am sorry,” he apologized, crawling off of her. “It was an accident.”

“I can’t believe you did that,” she yelled at him, loud enough to surely wake her parents.

“Look. I said I was sorry,” he argued back at her.

“Get out,” she yelled at him. “You are such a jerk.”

John got up and quickly threw his clothes on. He could not believe that she was being such a bitch about a mistake. It was not like he meant to come inside her.

“Oh my god,” she repeated to herself, looking up at the ceiling.

“Look,” he walked over to the side of the bed. “I am sorry.”

“Just get out,” she cried.

“Yep.” He nodded, leaving her house and rushing home.


“Hey bro,” John’s bro ran up to him before first period. “How did it go last night?”

“Nailed it,” John laughed, smiling from ear to ear, reaching up to fist bump his buddy. “Totally nailed it.”

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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