Pleasing My Conservative Girlfriend

[quidproquo]

Okay, my first story. Let me know what you think. (If you're just here for the "sexy" part, you should skip this chapter.)

The Background:


“Hold on, are you telling me you and Leah just started kissing three weeks ago?” Kyle was shocked. He had stopped walking along the path, and I looked back. He was staring at me.

I sighed. I knew this conversation was going to happen. “Yeah.”

“But, but, why? You've been dating her all year. I thought she was just shy about it in public.”

I took a deep breath. “Listen, Leah is like, really conservative and stuff, okay?”

“What does that mean?”

“Like, she's into like, modesty and going slow in a relationship, and like, waiting til marriage, and stuff...”

“Waiting til marriage to fuck?”

“Yea.”

“Holy fuck, man! That's like, I mean, I know she's kinda cute but like, that's so not worth it man. Why do you want to date a little prude girl? What's the point of having some pussy if you don't get any pussy?” Kyle was not the most eloquent guy I knew, but he was my friend.

“Dude, it's not like that. Like, it's not about sex or like her being hot or whatever. I just really like her. She's really nice.”

“But like, you guys are always hanging out together in her basement. What are you guys doing?”

“We watch movies and talk. Usually when her parents go to bed we cuddle a little. Sometimes we kiss.”

“Dude, that sounds so boring.”

I thought about it. “Not usually. I just love being with her.”

“How do you know she's not bored?”

I hadn't thought of this. “I dunno. Maybe she is. I should ask her.”

“You're un-fucking-believable. I can't believe you Leah's such a prude. She seems so outgoing and fun and shit.”

“She is, she just has like, standards, and stuff.”

“So, you waited a year to kiss her just because you thought she'd freak out about it?”

“Umm, yea, pretty much.”

“Did she?”

“You know, I was really scared, cause I thought she was going to flip out, but and she was kinda uncomfortable at first, but she's really getting into it. I'm actually pretty surprised.”

“Yea, man! You're gonna get in her pants!”

“Dude, it's not like that. Like, we'll do it when we're ready if it goes there and stuff, but I just want her to know I love her.”

“All right, I can't listen to any more of your mushy crap. You're a lost cause.”

I sighed and Kyle and I kept walking. Pretty soon, we got to his house, and several intense games of Halo replaced conversation about my girlfriend.

2 days later....

School had ended a few weeks ago, and I was enjoying the summer weather. Leah was on vacation with her family, and she was due back today. We had planned to hang out when she got home, and I was hanging around waiting for her. The sun was starting to set when she texted me saying I could come over.

Leah lived about 3 blocks away, so I started walking over. We had started dating last September, and since we did, we had been hanging out almost everyday. We were both 16, and we had just finished our sophomore year of high school. When I turned the corner onto her block, I saw her sitting on her front steps. When she saw me, she jumped off and started running towards me.

She was wearing a cute little t-shirt that stretched across her chest and short shorts. She was usually pretty modest, I had never even seen her cleavage, but she always looked hot no matter what. She was short and skinny, about 5'1 and 95 pounds. I honestly had no idea what size her boobs were, they really weren't that big overall, but they were pretty nice in proportion to her tiny body. I was happy with them anyway. She had a slender waist and toned abs. She was something of a late bloomer, and she was just beginning to get hips, and her ass was pretty small, but it was tight and well toned.

I caught her in my arms as she ran to me. She looked up at me and smiled. She had a beautiful face. She had light brown hair down her back with clear blue eyes. Her family vacation had recently tanned her skin and caused freckles to blossom all over her face. I could feel her boobs squeeze against me, and my cock started to swell. I let go of her, afraid she would feel it.

We said hello, and she started chatting happily about her vacation as she led me into her house.

To be continued...

[Coyote]

well i think that this is incredibly well written. Keep it up and this could be a hit

[LittleRayRay]

I love it :-)

He he.

Nice story :-)

[Officelover]

I like this.

It seems to be unique.

I't well written.

Good job.

[BLOEM51]

Nice story. I really like the story so far . Keep writing

[fire]

This is a really good story and it is really well written. Well done, keep going and I really think this could be an amazing story

[Lil C]

keep going dude it sounds cool

[quidproquo]

Okay, first real chapter. Nothing too sexual here either, so if you're one of those people, once again, skip ahead. Please give me feedback, as this is my first story.

Chapter One: Leah's Idea

Leah and I were sitting on the couch in her basement, watching the end of another movie. Leah's parents and siblings had gone to bed, and she had cuddled up close to me and laid her head on my chest. I noticed her fiddling with a lose thread in the couch, and what Kyle said came back to me, and I wondered if she was bored.

We had already seen this movie, so I didn't mind talking to her during it. I kissed her on the top of her head to get her attention.

“Are you bored?”

“Yea, a little bit.”

“Do you want to talk?”

“Okay.”

“Tell me more about your vacation.”

“I already told you most of it.”

“You didn't tell me about your family. How was seeing your cousins and stuff?”

“It was pretty good. We mostly just hung out by the lake and played games. All the girls went shopping and sunbathing. That was a lot of fun.”

I was mildly surprised. Leah was a pretty active, sporty girl, and I couldn't picture her having fun just lying around by the water.

“You went sunbathing?”

“Yea, do you like it?” Leah looked up at me.

“Yea, you look good.”

She smiled. “My cousins took me to buy a bikini so I would have bad tan lines.”

Now, if you don't know Leah, this doesn't sound strange at all, but if I hadn't been sitting down, I might have passed out. Leah was always very concerned about being 'modest' and 'appropriate.' I tried to encourage her to loosen up a little more, but I'd been taking it very slow, because I liked her a lot and I didn't want to scare her off. She was pretty skittish about her body and sex and things like that...

“Wait. You wore a bikini? In public?” I was trying not sound too shocked.

Leah laughed. “Yea, I know, right? They talked me into it, and I thought I was going to really hate it, but it was kinda fun once I got used to it.”

“That's cool.”

“Is that okay with you? I thought about calling you and asking if it was okay with you.”

“Of course it's okay. Why would you need to ask me?”

“Well, I'm your girlfriend, and I don't want make you look bad or whatever.”

“Why would you make me look bad?”

“Well, like, I just don't want to seem like a slut or anything.”

“Leah, sweetheart, I promise you: You have never, ever seemed like a slut. Every girl in the world wears a bikini. You're pretty tense about this kinda thing. You really need to loosen up.”

Leah looked thoughtful. “My cousin Veronica said the same thing. I just want to really respect my body and maintain a good reputation, you know?”

“Yea, I know sweetheart, and I appreciate that, but I think sometimes you're a little more serious about it that you need to be.”

“I'm sorry. Does that bother you about me?”

“No, no. Leah, I like you a lot the way you are. I just think you might enjoy life more if you could chill out about this stuff a little bit.”

Leah seemed to brighten up. She kissed me, and said, “Thanks! You're probably right. I don't mean to be a prude... Maybe if I'm like, being really anal about something you could let me know, like, quietly, you know?”

I gave her a hug. “Yea, sure.”

Leah lifted up her shirt to show her tanned stomach. I was shocked. I had never even seen her stomach before. She looked scared but excited.

“So, was the bikini a good investment?” She put her shirt down quickly, looking nervous.

“Yea, you look gorgeous.” I pulled her back towards me and held her.

We sat in silence for awhile. This time though, Leah didn't look bored, she looked conflicted, like she was deep in thought. After we sat there for awhile, I thought she might be upset about something. I started to worry that she was regretting showing off her newly tan stomach. I was worried that if she felt bad about tonight, that she would be even more tense and uncomfortable with her body than before. I didn't know what to say.

“Are you upset with me?”

“No, why?”

“You just look like something is wrong.”

“Nothing is wrong, I'm just a little tired.”

“Do you want me to go so you can go to sleep?”

Leah help unto me. “No, I want you to stay. Can you stay?”

I laughed. “Sure, I can stay. What do you want to do?” Honestly, I was getting kinda bored of just sitting there.

Leah looked at me. I could tell she was trying to decide if she should say something or not.

“Hey, just spit it out.”

“Have you ever played Truth or Dare?”

“Umm, when I was younger. Where did you get that idea?”

“From some of my cousins.”

“Oh yea? Did they play?”

“Can't tell, it's a girls only secret.”

I smiled. “Okay. So, did you ask me because you want to play?”

“Umm, maybe...”

“What do you mean, maybe?”

“I just don't want it to get to sexual or go to far, like, with the dares, you know?”

“Yea, I understand. If there was something you were uncomfortable with, I would give you a different dare or whatever. I wouldn't want you to do anything you're not comfortable with, you know?” I said as I held her close, “I want you to always feel safe with me, okay?”

“Yea, thanks. Sorry, just, one more thing.”

“Anything.”

“Promise me you'll never tell anyone, not anyone, if we play, okay? Like, don't even tell people we've talk about this, or anything. Please?”

I laughed a little. “I wouldn't do that.”

“Promise me.”

“Okay, I promise.”

“Thanks.”

“So, do you want to play tonight?”

“Ummm... yea!” Leah looked less nervous and more excited.

“Okay, who should go first?”

“Umm, you ask me first.”

“Okay,” I said, “Truth or Dare?”

To Be Continued...






Okay, please let me know what you think. I already have some ideas for the game, but any suggestions for how the game should go or ideas for truths or dares that would fit the characters would be greatly appreciated. Ideas for the story in PRIVATE MESSAGE only please. Please don't post on the thread, because if I use your idea it would have given away the story. If you haven't noticed, I'm trying to really work on suspense in this story. (Let me know if that is actually working or not.)

Please let me know what you think about the character development. Are the characters 3 dimensional enough? I hope you like it, next update soon.

[mrjd3000]

Brilliant story so far! Definitly looking forward to the next installment.

[Dare_Me_Anything]

i think this could amount into an interesting story - keep it up

[Desril]

Great story, excellent writing and grammar, keep it up!

[Person]

Very good story- one of the best stories I've read! Keep it up!

[Coyote]

As I said before , this I'd very well written. It is also very realistic. I can picture this happening In real life. Hope you keep it up

[BLOEM51]

As I said before.it`s a very good story. Really like it

[New and Shy]

This is great so far. Can't wait for more.