stupid-plan
FIRST TIME SEX STORIES

Stupid Plan

Stupid Plan

by leader12
19 min read
4.76 (9300 views)
adultfiction

Nick was really enjoying his first year at college. He also was pleased with his decision to skip the huge state university where many of his classmates went and, instead, go to the smaller school in the next state. It was really his sister, Becky, who was now a junior at the same school, who convinced him. She loved the school and thought it would be good for Nick to expand his horizons and, maybe, break away from the "nerd" reputation he had in high school. Nick knew it cost more than the state school, but Becky convinced him their parents could afford it.

Of course, Nick didn't suddenly go from being a nerd in high school to being a sophisticated, partying, cool guy in one semester. But he tried to play fewer video games, talk about more than the latest scientific discovery, and engage in social events - even if he didn't feel comfortable. Becky helped by inviting him to some parties, and he was slowly feeling a little less awkward when talking to girls.

There was really only one thing that disappointed him at college: where was all the sex he heard about? He was two months into his second semester, and he was still a virgin. And it wasn't just the fact that he still had the virgin label that bothered him. The fact was that he REALLY wanted to have sex! It's all he thought about. Every time he saw a pretty girl, he'd wonder what she looked like naked and what it would feel like to have sex with her. Sometimes he hated himself for how much he thought about sex, but he couldn't help it. He REALLY wanted to do it.

One Sunday afternoon, he decided he needed a plan. After thinking about it, he decided it would be easy. He would simply ask a girl to be his first. And he knew exactly whom he was going to ask. The only girl he regularly talked to was Hailey. She would do it for him (or should I say, with him), wouldn't she?

He met Hailey last year when he visited his sister at school. She was Becky's roommate, and she was nice to him during his weekend visit. Since she was a freshman at the time, she was closer than Becky to some of the questions going through Nick's head. She joined Becky and him for most of the weekend events. She walked with them when Becky took him on a tour of the campus, and she joined them for a number of meals they ate over the weekend. In fact, she even hung out with Nick in their room when Becky had to attend some meeting for the sorority she had joined.

When Nick moved into the dorm, Hailey made a point of coming to say hi. She made sure Nick knew where her room was, and she told him to stop by anytime he wanted to talk. If she saw him in the cafeteria, often she'd sit down with him. She encouraged him to call her if he had any questions. And now he had a simple one: "Will you fuck me?"

For a minute, Nick thought this was a really stupid plan. But it was the best he could come up with, and he HAD to take some action. So, he checked his pocket to make sure he had the two condoms he had been carrying around with him since he bought some the first week of school, and he headed out toward Hailey's room.

He stood outside her door for a minute trying to decide if he was really going to do this. After weighing the pros and cons, there was a long list of cons: making a fool of himself, having Hailey get pissed at him, having his sister find out... And there was really only one pro: finally having sex. He decided the one pro outweighed all the cons, and he knocked on the door.

When Hailey opened the door, her big smile immediately made him feel better.

"Hi, Nick! What's going on?" she asked as she stepped aside, inviting him in.

"Uh, just taking a break from studying. How are you doing? Bad time?"

"No, not at all. I could use a break, too," Hailey said as she closed the door.

Nick sat on her bed, and Hailey sat on her desk chair. Her single room was pretty much the same as his double - just narrower. Instead of having a closet on each side of the door, there was only one closet. There was no "other side" of the door - it was at the edge of the room. There was a bed with a burgundy bedspread along the wall in front of the closet. On the opposite wall, there was a pink neon heart. Her desk, at the end of the bed, had a few pictures, with more pictures on the dark green dresser which was beneath the window.

Nick just looked at her for a few seconds. She had a very pretty face, and he loved the way her brown hair curled under her chin. Her ample breasts - they were a small C-cup, but Nick didn't know that - looked really good in the short-sleeve, pink V-neck top she was wearing. Her denim shorts displayed a lot of her long legs.

"How's the new semester going? Are your classes good?" Hailey asked.

"Yeah, not bad," he replied. Then he continued, "Hailey?"

The way he said her name and the look on his face alerted Hailey that there was a problem.

"What's wrong, Nick?" she asked with genuine concern.

Nick sat there quietly for a few seconds.

"I was wondering..." he started but then couldn't go on.

He stood up as he said, "Never mind. I gotta go." He started toward the door.

"STOP!" Hailey commanded. Not loud, not with anger, but forcefully.

Nick froze, obeying her directive.

Hailey got up and walked over to him.

"What's wrong, Nick? Talk to me."

Nick remained silent.

Hailey grabbed his hand, walked to the bed and sat down, pulling him to sit next to her.

"Nick, you can tell me anything. You know I'm here for you. What is wrong?"

As embarrassed and nervous as he was, Nick felt he had to talk to Hailey. She wasn't going to let him leave until she knew what was going on.

"So..., here's the thing," he started. Then he paused for a few long seconds. "I'm a virgin."

Hailey felt better knowing there wasn't something seriously wrong.

"Okay," she said. "That's nothing to be upset about."

"But it IS!" he said painfully.

Hailey put her hand on Nick's thigh in a sign of comfort, but, considering his "problem" and his planned "solution", it didn't really help. Finally, after a long pause, he decided to go for it.

"And I was wondering if you'd help change tha...", but he couldn't finish the sentence.

Hailey's eyes opened wide as she realized what he wanted. On the one hand, what he was asking was outrageous. On the other hand, she saw his pain. She felt good that he felt close enough to her to even ask this of her. And she knew he'd always remember her as his first. But then, the shocking nature of the request crept into her mind. She stood up and turned toward him.

"So, what was your plan? Were you going to tell me how much I'd enjoy your eight-inch dick?" she asked with just a touch of anger in voice.

Nick couldn't look at her. He was ashamed that he even thought this was a good idea. But, looking down, her softly replied, "Sorry. It was a stupid plan. And I don't have an eight-inch dick."

"Oh, that wasn't your big selling point? It's not eight inches? So, just how big IS your dick?" she questioned with annoyance, not even sure why she asked such a silly thing.

"I don't know," he answered softly.

"I asked you how big!" she repeated.

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Nick looked at her. "I don't know exactly how big it is. It's not like I've measured it," he said, embarrassed to admit he had actually measured his dick.

Hailey bent down in front of him, bringing her face right in front of his, and she stared directly at him.

"I do NOT like being lied to, understand? NEVER lie to me! I asked you a question. How big is your dick?"

Nick had never seen her this angry, and he was afraid she would actually hurt him if she thought he was lying.

"6.125 inches," he said, staring at her.

Hailey's head jerked back before she started laughing hysterically.

Nick was devastated.

"Too small?" he asked.

Hailey was still laughing as she put her hand back on Nick's thigh and shook her head, unable to talk.

Finally, she got her laughter under control.

"Sorry," she said, "I wasn't laughing at the size. It's not too small at all. It's kinda perfect. But that was kinda precise. Three decimal digits? Did you have a laser ruler?"

"No, of course not. But when I measured it, it was six and one eighth inches. I just converted it to decimal."

Hailey chuckled.

"Let me make a suggestion. I realize this won't come up in conversation very often, but JUST in case it does, I suggest you just say 6.1 inches, okay?"

Nick smiled painfully and nodded, realizing how stupid his answer sounded.

Hailey's entire attitude had changed after the laugh. Now, she simply felt bad for Nick and wanted to help him. She liked Nick. And he wasn't bad looking. And she knew it would give him a lot of confidence. And she chuckled to herself thinking, "and it sounds like he's got a nice dick."

Hailey stood up and walked toward the window, opposite the door, saying nothing. Then she turned and silently walked back toward the door, passing Nick, who was still sitting on the bed. When she got to the door she spun around.

"So, you planned this out, huh?"

"Kinda'"

"And did you bring condoms, or did you plan on trying to get me pregnant?" she asked, chuckling to herself at the absurdity of the suggestion.

"I brought condoms," he replied softly.

"So, did you think you were going to walk in and say, 'Hailey, please have sex with me,'..." and she started walking toward the window again. Once she got past Nick, she said, "and I'd just take off my clothes?"

And as she finished the sentence, with her back toward Nick, she pulled her top over her head.

She heard Nick gasp, and she smiled. She stood there for a few seconds and let Nick look at the back of her pink bra.

"Is that what you thought would happen?" she said as she unbuttoned and unzipped her shorts and pushed them to the floor, slipping out of her sandals and stepping out of her shorts.

She heard another gasp from Nick as he stared at her naked ass, seeing only the pink waistband of her thong and the thin strip that disappeared between her cheeks.

Nick was breathing heavily. He had seen girls in bikinis, and some of Becky's friends wore some fairly revealing ones, but none of them had ever worn a thong. Seeing Hailey's full ass on display already had Nick getting hard. When Hailey reached back, unhooked her bra, and tossed it on the floor, Nick couldn't restrain himself.

"Oh, Jesus!"

This brought the biggest smile so far to Hailey, but she still didn't let Nick see it.

Hailey crossed her arms, covering her breasts with her hands, and she turned around to face Nick.

"Is this what you were hoping for, Nick?"

Nick slowly nodded as his eyes went up and down Hailey's body, wishing he had x-ray vision to see behind Hailey's hands covering her breasts and to see behind her thong. She gave him a minute to enjoy the almost-naked but not-really-so-revealing sight.

Then, in a soft, loving voice, she said, "take off your clothes. I want to see that 6.125-inch dick of yours."

Nick pulled off his shoes and socks, then stood and ripped off his shirt and pants in record time. He was standing in his boxer-briefs, with his hard dick straining to get out.

Hailey was surprised Nick was in such good shape. And she noticed there wasn't a single hair on his chest, which she liked. She was getting excited at the prospects.

"I can't see your dick."

"I've never been naked in front of a girl," he quietly said, embarrassed.

"You know, it's hard to have sex without taking those off," she said smiling.

Nick nodded, realizing the stupidity of his comment. He pulled his underwear down and kicked them to the side. His hard dick was pointing straight at Hailey.

As Hailey took a step toward him, with her hands still covering her breasts, she said, "Wow, that's a nice dick." Then, with a chuckle, she asked, "how big is it?"

Nick smiled.

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"6.1 inches."

"Mmmm. Perfect," she said, complimenting his dick AND his answer.

As she got closer and closer to Nick, he was both incredibly nervous and incredibly excited. When Hailey was a couple of feet away, she spread her arms and said, "Hug?"

"Oh, FUCK!" Nick said, as he looked at Hailey's breasts - the first breasts he had ever seen in real life. "You're so beautiful."

Her large breasts were perfectly round with quarter-size dark red areolas. Her nipples were hard, and Nick's head kept jerking left and right as he kept moving his eyes from one breast to the other. Hailey smiled at Nick's expression, but then she started her own staring - at Nick's cock. It was a little thicker than average and circumcised. His pubic hair was trimmed short, and it was totally shaved directly around his dick and further south.

"Touch them," Hailey whispered.

Nick took a deep breath and raised both hands, cupping both breasts. They both groaned. Nick gave a few gentle squeezes, and Hailey was surprised at how good she was feeling.

"Gently pinch my nipples," she whispered.

As Nick simultaneously pinched both nipples, Hailey moaned. But it was Nick who let out the loudest groan when Hailey wrapped her hand around Nick's dick.

"OH GOD!"

As Nick closed his eyes, Hailey smiled. She slowly stroked his dick for a few seconds before kneeling. When she licked the underside of his cock, from his balls to the tip, Nick gasped and grabbed Hailey's shoulders. Hailey wrapped her hand around him again and remained motionless, looking up at Nick. After a few seconds he opened his eyes. He looked down at Hailey and found her smiling at him. She loved having complete control over a guy, knowing she could do anything she wanted.

In this case, what she wanted was to make Nick come. And she didn't think it was going to take too long.

She placed the tip of his dick in her mouth and swirled her tongue around. Nick subconsciously gripped her shoulders even more tightly. Hailey liked his total submission. She tasted his precum and was now sure he wasn't going to last long, which was fine with her. The whole point of this was to make sure he DID last longer the second time.

Nick didn't intend to fuck her mouth, and he didn't even realize he was thrusting his pelvis into her face. With his eyes closed, he was unaware of anything except the incredible feeling encompassing his entire body. Eager to finish him off, Hailey started softly strumming Nick's balls. He let out a loud groan.

It was only a few seconds later when he barked, "Hailey! Hailey! I'm gonna cum!"

Hailey continued exactly what she was doing, and she was ready when she sensed his cock twitch and felt the squirt of warm cum hit the back of her throat.

Nick grunted with each shot, and Hailey smiled to herself as she continued swallowing each spurt. When he seemed done, Hailey ran her tongue around one last time. She kept her lips pressed tightly around his softening member as she pulled it out to completely clean him. His hands released their tight grip on her shoulders, and Hailey stood.

Nick opened his eyes and smiled, looking into Hailey's eyes. Then he remembered Hailey's tits were right in front of him, and his eyes studied them for a second before he looked back at her.

"Oh my God, Hailey. Thank you." Returning to his shy self despite the just-completed intimate act, he asked, "Can I kiss you?"

Without answering, Hailey leaned in, tilted her head, and placed her lips on his. Nick wrapped his arms around Hailey's waist, and she put hers around his neck. It was a few seconds before Hailey opened her mouth, and Nick responded in kind. Their tongues quickly found each other, and the kiss became more passionate. Nick slid one hand onto Hailey's breast, gently caressing it. He remembered Hailey's earlier instructions, so he started gently pinching her nipple. She replied with a soft moan. This continued for a few minutes until Nick broke the kiss. He looked at Hailey for just a second before lowering his head and taking her other nipple into his mouth. He flicked his tongue over it, and Hailey whimpered as she grabbed the back of his head to hold it in place.

When Hailey made her decision to "help" Nick, she was mainly thinking about doing this for his benefit. But now, things had changed. Without any single event triggering it, Hailey was now very turned on. Nick's tongue and hand were stimulating her nipple as well as anyone. Her entire body was tingling, and her pussy was wet.

As excited as Hailey was, Nick's exhilaration was off the charts. Even ignoring his first blowjob - which he certainly did NOT ignore - he couldn't believe he saw Hailey's tits - let alone was actually touching them and sucking on them. As much as he wanted to fuck Hailey, he would have been happy to continue kissing her and her breasts for the next three or four hours.

After five or ten minutes, Nick moved his mouth back to Hailey's, eager to slide his tongue back into her mouth. He continued massaging her breast and nipple, which made Hailey very happy. She was a little surprised at how good a kisser Nick was, and she felt remarkably good as he tended to her breasts. But she yelped in surprise when Nick slipped his hand into her panties and slid his middle finger down into her wet slit. Without pausing, he slid that finger into her soaking pussy. He was shocked at how wet she was. Since this was a first for him, he didn't know whether or not this was normal, but he didn't really care.

"FUCK!" she cried out, as she thrust her pelvis into his finger.

Nick slid his finger in and out a few times before pulling it out and quickly moving his lubricated digit to her clit. He started flicking his finger back and forth as she pulled her mouth away from him and cried out between gasps of breath.

"Yeah! Yeah! Yeah!"

Nick moved his mouth back to her nipple, flicking his tongue across it at the same pace that his finger was stroking her clit. Add in the way Nick was pinching her other nipple with his fingers, and Hailey's body was fully charged. It was less than a minute before she exploded.

She whimpered with each contraction as she rhythmically thrust her pelvis hard into Nick's hand. Her head jerked back with each spasm as her eyes and face scrunched up, almost looking like she was in pain. Nick was so happy he could give this pleasure to Hailey, and he continued to stroke her clit and flick his tongue across her nipple throughout her orgasm.

After twenty or thirty seconds, Hailey went limp and molded her body against Nick. He pulled his hand out of her panties and wrapped his arms around her, hugging her tightly as she laid her head on his shoulder. Once again, Nick could not believe his current situation. He smiled as he felt Hailey's breasts push against his chest. And once again, he thought he'd be happy to hold her just like this for a few hours.

After a minute or two, Hailey let out a satisfied, "Mmmmmmmm".

After another few seconds, she pulled her head away from Nick's chest and smiled at him.

"That was really nice. Thank you."

Then she gave him a short, simple kiss on his lips.

"But we still have some work to do here, don't we?"

She reached down and wrapped her hand around his dick, surprised it was semi-hard.

"My my... someone's already getting excited."

"Jesus, Hailey. I've never STOPPED being excited since you pulled your shirt off. This is not exactly a normal day for me."

Hailey started laughing.

"Well, maybe it will be more normal in the future," Hailey said.

It took a second for Nick to register what she said. Was she referring to this being more normal with HER, or was she just suggesting he'll have sex with others in the future? He didn't want to get into a conversation about her meaning right now since she had her hand around his dick, and he didn't want to distract her. But the thought that this could happen again with her caused his dick to twitch and quickly reach full hardness. Hailey noticed.

"Anxious, are we?" she asked with a smile.

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