The Big Idea

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Her best friend offers her boyfriend to take her virginity.
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DanDraper
DanDraper
1,141 Followers

***All characters are over 18 and are fictional. Any resemblance to any real-life persons or situations is purely coincidental.

.....

KATIE'S STORY

Katie woke up feeling like shit. She laid in bed wondering what the hell she was thinking of drinking as hard as she did last night. It took her a few minutes to realize she was fully naked under her blanket and suddenly remembered the incredibly handsome man she was hanging out with at the bar. She looked over at the other side of her bed. He was not there, nor were there any signs that he was around.

She remembered him taking her home and her having to drag him into the bedroom. She thought long and hard, trying to remember if they had sex or not.

"Oh, I remember now," she said to herself.

It took a moment, but she suddenly remembered feeling very sick. The guy recognized that she was going to throw up and quickly took her to the bathroom, got her head in the toilet, and she vomited like she had the Spanish flu.

After that, everything was very hazy. She had no idea how she got naked and into her bedroom, or if she had had sex with the man she met. She doesn't feel like she had sex, but then again, she wouldn't know how it would feel afterwards. Katie was a virgin, or at least she thinks she still is, depending on what happened to her last night. She was setting out to finally have sex, but was hoping to remember the experience as she hadn't planned on drinking so heavily.

She heard a noise outside of her bedroom, she could tell there was someone in her kitchen. If it was the man she took home last night, he could shed some light on the subject. She found some clothes to quickly put on and left the bedroom. She was incredibly nervous about seeing that man. She hoped she hadn't fully embarrassed herself in front of him.

As she reached the kitchen, her nervousness went away and was replaced with disappointment. It was not the sexy man she hoped she had sex with, but her best friend Jennifer, making coffee.

"Good morning, sunshine," said Jennifer.

"Good morning," Katie replied. "This is going to sound awkward, but did you see someone else around her before?"

"Oh, you mean that super sexy Marine you took home last night?" Jennifer asked. "I have to say, you've got good taste."

Katie sat at the kitchen table, trying to ignore the massive hangover headache she was getting.

"I don't remember much after I vomited last night. I'm trying to piece together what happened."

"Let me fill in the gaps for you," said Jennifer, as she got two cups of coffee ready for the both of them. She handed one to Katie and took the seat next to her. "He took you home because he saw how drunk you were from the way you were all over him despite how much he resisted your advances."

"He resisted me?" Katie asked. "I thought it was mutual."

"You were drunk, you thought what you wanted to think," Jennifer reminded her. "So, after he took you home and you repeatedly tried to get him to fuck you, but he didn't, he saw you were going to throw up and took you to the bathroom. After you vomited and began crying on the floor—"

"I cried, oh no," Katie said, looking very embarrassed.

"He then looked through your phone and called me. When I came, he helped me get you washed up and undressed and took you to bed before he left, and I slept next to you all night."

"Oh God, I feel so stupid," said Katie as she took a sip of her coffee. "Did the marine leave his number by any chance?"

"Katie, that guy was gay," Jennifer revealed. "I know because when I arrived, I first accused him of trying to take advantage of you. That's when he told me he was gay and showed me proof by showing me photos on his phone of him and his boyfriend, some of which had them making out with each other."

Katie felt like the biggest idiot in the world. She couldn't believe she spent the whole night hitting on a gay guy.

"That means, it was all for nothing," Katie began to say. "That means I'm still a—"

Katie stopped herself before she revealed anything she didn't want Jennifer to know.

"Yes, you're still a virgin," said Jennifer. "The gay marine told me that's what you were crying about after you vomited."

"Oh, shit."

Katie felt incredibly embarrassed. It was a secret she was trying to keep from everyone.

"I can't believe you never told me you're still a virgin," Jennifer snapped at her. "I'm your best friend; these are things you should be telling me."

"It was embarrassing to be a woman my age and still a virgin. I couldn't tell you or anybody, let alone you."

Katie and Jennifer both grew up with religious families and went to the same strict Catholic school where they met and became best friends. Katie was always the more religious of the two, while Jennifer was the more fun one who was more obsessed with boys. Jennifer was the first of their entire group of friends to have sex in their senior year, while the others lost their virginities throughout their senior year.

Katie lied to her friends in order to impress them by saying she had sex with her then-boyfriend after their senior prom at a hotel they got. She had planned to lose her virginity to him, but right before she was going to get undressed for him, her Catholic guilt got the better of her and she began crying, telling him how she couldn't do it. Her boyfriend did not want to put any pressure on her and told her she didn't have to do anything she didn't want.

After that, she told him he could tell his friends they slept together because she knew he was also looking forward to it. She felt embarrassed about still being a virgin herself, so she lied to her friends about sleeping with him and how great it was.

Over the years, she made up excuses not to sleep with the men she dated, often because of her religious beliefs. To avoid embarrassment, she lied about the men she had slept with to her friends; never too much to make herself look like a slut, but not too little to make herself look like a prude either. When pressed for details, she kept it vague and said what she thought was right.

She had hoped that she would eventually find the right man, get married, and it would all be over. But she was on the verge of turning 30, and it was getting too frustrating for her. At that point in her life, she didn't care what her religious beliefs told her about waiting for marriage; she just wanted to get laid.

In the last year, Katie had tried to have sex with the few men she dated, but she was having incredibly bad luck with them; one guy turned out to be married, another also had religious hang-ups about sex, and two others were just straight-up jerks to her. She was close to two other guys, one who had a bad case of premature ejaculation and always shot his cum right before they got to business, and another who couldn't get it up at all and refused to get Viagra.

She tried to do an online hookup using Tinder and other similar apps, but found that some of them were straight up creepy. She didn't know how some of her other friends were able to find online hookups without getting stalked by some of those weirdos. One guy she found online seemed like an ordinary guy until she found out he wanted them both to have sex while dressed in fluffy animal costumes; she couldn't get away from him fast enough.

After getting a little desperate because she was less than a week away from turning 30, she decided to just meet a guy at a bar for a random hookup. She went to a bar that was frequented by military types, hoping to be fucked by a handsome war vet who had just come back from overseas. She heard from her friends how good in bed most of them were and hoped it was true. She only drank to calm her nerves about being there for a hookup, only to find herself drinking too much and not realizing she was hitting on a gay guy the whole time.

Katie confessed everything to Jennifer, who still looked dumbfounded from hearing how her best friend was still a virgin.

"This is unbelievable," said Jennifer. "Those nuns at Catholic school really did a number on you."

"I'm surprised I didn't become one of them," Katie replied.

Jennifer was surprised that Katie had no luck getting a man to sleep with her. She would've figured she could've had any man she wanted. Katie was a very attractive woman, with long red hair and a decent figure. Her breasts weren't huge, but she had seen her naked and could tell she had a good pair on her that most men would love to get their hands on.

"So, you had no sexual experience whatsoever?" Jennifer asked. "Like, other things besides intercourse?"

"What do you mean by that?" Katie asked.

Jennifer motioned with her hand to mimic giving a handjob.

"Oh, yeah, I have given plenty of handjobs," Katie revealed. "I had to eventually do something to keep some of the men I dated happy. And in the last few years, I learned to give oral sex as well, and let guys finger me."

"At least you've done something. So, I understand why you went to that bar last night, so let me help you with your problem."

"Help me how?" Katie asked.

"I'm going to help you get laid, of course," Jennifer replied. "You have three days before you turn 30, and I'm going to hook you up."

"How are you supposed to do that?"

Jennifer assured her, "Just leave it to me. You were ready to find yourself a random hookup. I can find you that hookup myself."

"So, you're just going to get me a guy to help me get laid as if it's that easy?"

"Do you want to be a virgin in your 30's?" Jennifer asked.

"No, of course not."

"Then just leave it to me."

JENNIFER AND JOSH

Later that day, Jennifer's boyfriend, Josh, came over to her apartment for dinner and a movie, and, of course, to spend the night with her. The dinner was alright. Jennifer had become a better cook than she was when they first met, especially since he gave her advice on how to improve her cooking skills.

After dinner, Jennifer brought out a cake for dessert. She bought it from a bakery as she had failed in her last few attempts at making one on her own.

"How's Katie doing after last night?" he asked.

Josh was there when Jennifer got the call. They were about to go to sleep after fooling around when her phone kept going off, and she answered it, thinking it was Katie, when it was some other guy who took her home. As Jennifer explained to him what had happened to Katie, he tried his best not to laugh at her situation, especially the part where she found out the marine that she was hitting on turned out to be gay.

Afterwards, Jennifer told Josh about Katie's big secret and was floored when he heard it. He knew she was very religious, but never thought she might be a virgin. He knew a lot of religious people growing up, and they never stayed virgins for that long. Even the few religious girls he dated before Jennifer liked to fool around.

"I can now understand why she wanted a bar hookup," said Josh.

"So, that brings me to what I need to ask you. I want to help her get laid before she turns 30 in a few days, and I thought maybe you know someone among your group of guys who could help her out."

"You want to set her up with one of my friends for a random hookup?" asked Josh. "How about I hook her up with someone to date? I know a few who are good boyfriend material for her."

"No, she needs to get laid fast. Dating could take time before sex. I know some people move fast these days when dating, but not always."

"Ok, I guess I can think of one or two people who could help," Josh told her.

Josh thought long and hard, thinking about every one of his friends and even considering his brothers and a couple of cousins. For everyone he thought of, he could find a reason why they wouldn't be a good idea, even for just a hookup. A lot more of his friends are either married or in some other kind of relationship these days. A few others now live too far away and probably won't travel a few hours just for a hookup, no matter how horny they may be, especially at such short notice. There were one or two guys he knew of who were definitely into random hookups, but they were such jerks, he couldn't do that to Katie. There were a few others, but they were more of the relationship type of guys, not the random hookup types.

"So, can you think of anybody?" She asked because Josh was taking a long time coming up with a name.

He told her, "No, I can't think of anybody. Everyone I know has a reason why I can't suggest them."

Jennifer felt very disappointed. She was really hoping Josh could come through for her. But after he explained to her all the reasons, he couldn't suggest any one of them. She had no choice but to agree with them. He apologized for not being able to help, but Jennifer said he didn't have to because it wasn't his fault. She told him to forget the subject and they cleaned up the table to be ready for the movie they were going to watch.

They were on an 80's movie binge over the last month, watching some of the best films of the decade. They didn't go in any particular order, just randomly choosing whatever film from that era they wanted to watch. Tonight's film was "The Big Chill" from 1983, about a group of former college friends who spend the weekend together after the funeral of one of their friends. They loved the movie; it was a funny yet heavy-hearted film.

One of the things Jennifer found most interesting about the film was how the character Sarah wanted to help her friend Meg, who wanted to have a baby by getting her husband Harold to sleep with her. It was an incredibly awkward situation for someone to ask their husband to knock up one of their closest friends, but she convinced him to do it and they still remained friends afterwards.

Jennifer was surprised that the character of Sarah came to that kind of decision, but definitely understood; when your friend is in need of something, you would do anything to help them out. She found this relatable to her own situation with her best friend Katie and came to the decision that she should offer up her boyfriend just for one night to help her lose her virginity.

She wasn't going to ask Josh about this right away after the movie ended, so she decided to wait until the morning to bring it up. When the film was finished, they discussed the film for a while, telling each other what they liked most about it. Afterwards, they went to bed to make love, and he spent the night.

In the morning, Jennifer woke up earlier than Josh to make his favorite breakfast, blueberry pancakes. She knew she wasn't that good of a cook, but she was a queen at making pancakes. She had gotten a good stack ready for him just as he came into the kitchen.

"Oh, nice," he said as soon as he saw the pancakes. "What's the occasion?"

"Just because I like you so much," she told him.

They gave each other a big kiss and sat down to eat breakfast. Jennifer wanted Josh to be extra happy to make him ready to ask him her big favor.

"What do you think about Katie?" she asked.

He replied, "She's a great person."

"Do you think she's pretty?" she asked.

Josh had to think about that for a moment because it sounded like a trick question; most women don't ask if their boyfriends think their friends are pretty.

"And before you have to think about it, this is not a trick question. I generally want to know," she assured him, because she could see he was worried about answering the question honestly.

"Ok, yeah, she's a pretty girl," he responded. "It makes me more surprised she's still a virgin; I would've figured a lot more guys would be all over her."

"Yeah, it's too bad she couldn't find the right one to show her how wonderful sex could be."

"If you want, I could still set her up with the guys I said would be good boyfriend material," he told her. "She may still have to be a virgin after she turns 30, but she could wait a little longer."

"I think I know one guy in particular who could help her with her situation," said Jennifer. "A wonderful man who I know personally is amazing in bed."

She said that last part as she grabbed his hand and looked deeply into his eyes.

"Where are you going with this?" he asked. He had his suspicions but wanted to hear it from her.

"I think you should be the one to take Katie's virginity," she finally revealed.

Josh burst out laughing, assuming Jennifer was making a crazy joke. After he finished laughing, he saw in her face how serious she was.

"Oh shit, you're serious?" he asked.

"Yes, I'm serious. She knows you, she's comfortable around you, and I personally know you can show her a good time in bed."

"What made you think this would be a great idea?"

Jennifer reminded Josh about the move they saw last night and explained the reasons why it would work.

"That was just a movie," he told her. "No woman in real life would offer up her husband like that, let alone her boyfriend."

This was not going as smoothly as she hoped it would. She thought Sarah convinced Harold and Meg too easily to sleep with each other, and it did look like the movie never fully showed the conversations she had with them to convince them either. She still had to try nonetheless.

Jennifer continued to say, "I still think it should be you. If not, she may not have that chance for a good long time. Even if you do set her up with one of your friends, who knows what could happen in the long run? She needs this before she turns 30."

"Is having to do this before she's 30 really that important?"

"Would you have been OK with being a virgin after 30?" she asked in response.

Josh thought about it for a moment. He lost his virginity just after he turned 18, almost 15 years ago. He was no Casanova, but he did alright over the years with women until he met Jennifer, the best relationship he ever had. He would do anything for her, but he never expected her to ever ask him something like that.

He thought about Katie's situation as well. Being a virgin at 30 was kind of bad, although not unheard of in these modern times. He thought it was a bad idea, but at the same time, he couldn't help thinking how Katie nearly got into a bad situation the night before.

"I can't help thinking how lucky she was to have run into a gay guy who helped her out the other night instead of some creepy dude who would have taken advantage of her and possibly hurt her. She is very naïve when it comes to this stuff, isn't she?"

"Yes, she is," Jennifer replied.

"And you're sure you would be OK with this?" he asked.

"It's just one night, you would be helping someone out greatly, and our love is strong enough to overcome any kind of awkwardness about it."

He thought about it some more, needing to be absolutely sure it was definitely a good idea. It may be an easy decision for some men. Some of his friends would've said yes right away, not caring about any consequences. But he was a different kind of man. He felt there were lines you shouldn't cross, and he never cheated on anyone. Technically, he would not be cheating since it was done with Jennifer's encouragement, but it was still very similar.

"So, is that a yes or not?" she asked demandingly.

"Hey, give me a break. You just sprung this on me like five minutes ago, and it's still early in the morning."

She backed off to let him think about it some more, but she was getting anxious for an answer. She watched him eating his pancakes as he continued to figure out all the pros and cons of the situation. She couldn't blame him. As much as she hoped for a quick yes answer, she knew it was a highly unusual request.

"Ok, I'll do it," he finally answered. "Only because I don't want her in another situation like she was in the other night and at least I can prepare her for what she may experience."

Jennifer was so excited that she grabbed Josh by the shirt collar and pulled him in for a big, passionate kiss. She let him go, and he had a big smile on his face.

DanDraper
DanDraper
1,141 Followers