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

[quidproquo]

Hey guys, sorry to take so long. This chapter was really hard to write. I tried to make it 'sexy' without being unfaithful to Leah's character, which was really hard. I always appreciate feedback. This is the first chapter with any 'action' so please let me know what you think. I'm new to this, so I'm not sure how this is. Ideas for the future of the story are also appreciated in PM. Thanks guys!

Chapter Two: Breaking New Ground and Walking on Thin Ice

Leah looked worried again and thought for a moment. “Umm... truth.”

I hesitated. I didn't want to freak her out by asking something too personal. If I did we might never play again. On the other hand, I didn't want her to be bored. I decided to start slow.

“What is your favorite feature?”

“What do you mean?”

“Like, what part of your body do you like the best?”

“Umm, I'm really glad I'm thin, even if I'm not as curvy as other girls, because fat girl get made fun of all the time, and I'd probably be really insecure if I were a little bit heavy.”

“Okay, but that's not a part.”

“Oh, come on, that's close enough.”

“Nope.”

“Alright, umm... Man, this is really hard. I don't like much about me.”

“If you can't think of anything I'm going to be worried about you.”

“Umm, okay, I like my hair.”

“Why?”

“You don't like it?”

“No, I just asked why.”

“Umm, I dunno, I like having long hair, and I like that it's pretty light but not blonde. It's kinda unique I guess.”

“Okay.”

“Okay, my turn, truth or dare?”

I hesitated. Some of Leah's shyness must have worn off on me, because suddenly I wasn't sure I wanted to do a dare. “Umm, truth,” I said.

Leah thought for a minute. “What's your favorite feature on me?”

“I really like it when you smile, but I guess that's like a mixture of your cheeks and your freckles and your teeth and lips and your dimples. Is that cheating?”

“No, that's okay.” Leah smiled extra wide, and I held her for a moment.”

“Truth or dare?”

“Truth.”

I decided to push us just a little. “What color is your underwear?”

Leah paused for a moment, and I tried to read the expression her face, but it was no good. She could have just been trying to remember what color her panties were, or she could have been having a deep internal conflict about answering the question. Her face was blank, I couldn't tell.

I was so tense I think I held my breath, because I started to pass out. Suddenly, Leah laughed.

“You know, I can't remember!” She lifted up the bottom of her shirt and reach into her shorts. She pulled out the top of her underwear, showing light green cotton panties. She laughed again, “Green!” She pushed her panties back into her shorts and put her shirt back down. I sighed, I was safe. She was having fun. I gave her a kiss.

She looked up at me. “Truth or dare?”

“Hmm, dare.”

Leah spoke right away. It was obvious she had already thought through this.

“Show me your underwear.”

I hesitated. I wasn't very comfortable around this new, more open Leah. I didn't know where her limits were.

“You mean you want me to take my pants off?”

Leah blushed. “Oh, no. Umm, sorry. I just wanted you to pull your up like I did.” She looked worried, like I would be mad or something.

I tried to put her at ease. I smiled, “Oh, sure.” I pulled up a few inches of my blue boxer-briefs. Leah blushed again, but she smiled too.

“Do you wear briefs?”

“No. These are boxer-briefs.”

“Oh. What are those?”

“They're like boxers— ” I paused. “Do you know what those are?”

“I think so. They're like baggy shorts, right?”

“Yea, except they have a fly in front so you can pee without pulling them down.”

“Oh, okay.”

“So, they're like boxers except they are usually a little tighter and have have a pouch to support your balls, and it helps keep you from hurting them when you run or sit down wrong or something.”

Leah looked embarrassed. “Okay.”

“So, anyway, truth or dare?”

“Umm, truth.”

“Hey, are you ever going to choose dare?”

“Umm, maybe.”

“How about we make a rule?”

“What?”

“No more than two truths in a row”

“Okay. But I already chose truth. I'll pick dare next time.”

“Alright. What's your bra size?” Five minutes ago I never would have asked Leah this, but since she'd just asked to see my underwear, I figured I was safe.

“Umm, 28 A.”

“Really?”

“Yea. I'm sorry.”

“Sorry?”

“Well, don't guys like girls with bigger boobs?”

“Leah, I think you're really hot how you are. Don't worry about it, okay? I was just surprised because I think you have pretty nice boobs, and I thought you'd wear a B or something.”

“I tried for awhile, I have a couple bras that have B cups, but they're really loose. I thought I would grow into them, but that was a few years ago, and I'm still an A. Oh well.”

“Well, I'm happy with them.” I held her for a long time without either of us saying anything. I knew she most be feeling very vulnerable, and I wanted to reassure her. I felt very uncomfortable. I was sure that, sooner or later, we were going to get somewhere that Leah was uncomfortable with, and she was going to freak out. On the other hand, I had been waiting for her to open up a little for almost a year, and this was fun. It was obvious that she was finally feeling comfortable with me, I just didn't think it would happen all at once.

Finally I spoke up. “So, it's your turn to ask me.”

“Oh, right. Truth or dare?”

“Truth.”

“Have you ever measure your, umm, penis?”

“Yea, I think most guys have.”

Leah blushed. “How long is it?”

“Ah, that's two questions.”

“Oh, come on.”

“Nope, you'll have to wait for next time.”

“Alright, fine.” She seemed to be having fun again.”

“Truth or dare?”

“Well, I guess I have to pick dare.”

“It's about time.”

Leah made a face at me.

“I dare you to put an ice cube in each bra cup and leave them there til they melt.”

Obediently, Leah got up from the couch and walked across her basement to the spare refrigerator. She walked back to me with a tray of ice cubes, and took out two. She stuck her hand down the v in her shirt and put one in. She grimaced at me.

“Oww, it's really cold.”

“That's the point sweetheart.”

She glared at me and put the other one in, and sat back down. I could see the ice cups making two large lumps near where I imagined her nipples were.

“Your turn, truth or dare?”

“Dare.”

“Take your shirt off, and put ice on your nipples until next turn, but you have to keep your shirt off until I say.” Leah and I had never gone swimming together, so I don't think she'd ever seen me with my shirt off. I was decently muscular with a little definition in my abs, but not a stud or anything.

I took my shirt off, and Leah stared at my chest. I took a sharp little breath as I put the ice on my nipples.

“Now you know how I feel,” Leah said and grinned.

“Okay, let's hurry this up. Truth or dare?”

“Truth”

“Have you ever worn a thong?”

“No. I think it's be uncomfortable. I thought about about buying one to find out, but I am afraid my mom will find it or something.”

“If you are ever afraid of your parents finding something, you can keep it at my house. My parents never come in my room or anything.”

“Okay, I'll keep that in mind. Truth or dare?” I took the ice off my nipples.

“Truth.”

“How long is your penis?” Leah tried to act casual about it, but I could tell she was really excited to hear the answer to her question.

“Umm, it's a little under 7 inches, the last time I checked.” I was sure Leah had never seen a penis in her life, and had no idea if that was a good or bad size. Nevertheless, she looked really impressed.

She hugged me, and I got wet spot on my shirt from the melting ice in her bra. “That's cool,” she said. I could tell she wanted me to know she approved.

“Truth or dare?” I asked.

“Hmm, dare.”

“I dare you to show me all your tan lines from your vacation.” Leah hesitated. “It's not like I'm going to see much more of you than the guys at the beach did.”

“Yea, I guess that's a good point.” Leah pulled on her v-neck so it stretched down and exposed part of her bra. I had never seen her cleavage or even her bra straps. I got hard instantly. The bikini her cousins got her was apparently pretty skimpy, because the exposed part of her boob was still tan. She pulled her bra down until most of her boobs were showing, and finally I saw about half an inch of pale skin.

“You're really hot.”

Leah smiled. “Thanks.” She stood up and hooked her thumbs in her shorts. She pulled them down slowly along with her panties until I could see her tan line. I also noticed a few dirty-blonde pubes sticking out, but she didn't seem to notice, so I didn't say anything. She turned around so I could see her butt, and started to pull her shorts down again.

“Can you see it yet?”

“No.”

“Okay.”

She pulled them down some more, and I could see the top of her buttcrack.

“Now?”

“No.”

“Really?”

“Yes.”

“Alright. Tell me when you do.”

“I will.”

She pulled them down again, and I could clearly see the top of her buttcheeks, and then I saw her tanline. I thought about taking advantage of the situation and not tell her, but I decided to be honest.

“I can see it.”

“Okay, can I pull them up now?”

“Yea.”

Leah pulled up her shorts and sat back down. “Hold on,” I said. “You're missing two tan lines.”

“What?” I pointed to where her tan legs bet her short shorts, and then to the bottom of her boobs.

“Oh, no, please, I can't show you that, that's SO much skin!”

“Well, if you don't want to do the dare you agreed to, you could always take a forfeit.”

“What's that?”

“It's a punishment for not finishing a dare?”

“Like what?”

“I dunno, depends on who's playing and what works.”

“Well, what do you think a good forfeit would be?”

“I think a spanking is a good punishment.”

Leah thought for a moment. “Okay. How many?”

“Hmm... I think 50.”

“Fifty! That's a lot.”

“Well, you know...”

“Can I take half if I show you one more tan line?”

“Okay.”

Leah stood up again and lifted up her shirt to her bra. Then she pulled her bra up to show the bottom part of her boobs. I told her when I could see her tan line, and she put her shirt down. It was obvious that Leah had been spanked by her parents, because she was not awkward about it at all.

I was sitting on the edge of the couch, and she laid across them with her lower stomach on my knees. This left her with her elbows and feet on the floor and her ass prominently displayed.

“You ready?”

“Yea, just stop staring at my ass and get it over with.” She had a hint of excitement in her voice. I sighed; she was still enjoying herself.

“But I like staring at your ass. It's a nice ass,” I teased, “So, how hard should I do this?”

Leah looked up at me, very sincerely, “I didn't finish the dare, do it as hard as you want.”

I spanked her, and I expect her to squeal, or something, but she was completely silent through the whole thing. Her butt was more toned than I expected, and by the end my end was probably as sore as her ass.

When I finished she looked up meekly and asked, “Is that it?”

“Yea,” I answered gently.

“Okay,” she said and got back up.

“Okay, so, do you want to keep going?”

Leah smiled again, “Yea, truth or dare?”

“Truth.”

“Did spanking me turn you on?”

I froze, embarrassed, but I realized my silence had already given me away, so I might as well be honest.

“Yea, it did, sorry.”

Leah leaned into me, “Don't be sorry, I take it as a compliment.”

“Oh, okay. Umm, truth or dare?”

“Dare.”

“I dare you to bring your bikini down here and change into it, in front of me. You can turn your back to me so I don't see your boobs, and you can use a skirt to change your bottoms so I don't see your ass, but you have to be here when you change.” I said this very quickly, in one breath.

“Umm, okay.”

Leah disappeared upstairs for a few minutes and returned with a skirt and her bikini. She stood in front of me with her back to me and pulled off her shirt. I gazed at her smooth, tan skin. She unclasped her bra and dropped it on the floor next to her shirt. I could see the sides of her breasts from behind her. They jiggled slightly as she pulled on her bikini, adjusted the cups, and then tied the the straps around the back of her neck.

Next she pulled on the skirt and reached her hands down the front. A moment later and her shorts lid to her feet. She kicked them off. After some difficulty her green panties slid to her feet also. She kicked them off and stepped into her bikini bottoms.

She pulled them up to her thighs, but as she pulled them up her skirt rode up with them, and she stopped. Then she let the skirt fall back, covering her bikini bottoms. She reach down inside the skirt and pulled the bottoms up the rest of the way without letting me see anything. Finally, she pulled the skirt off and stepped out of it, leaving her standing in front of me in her bikini.

The bikini was a light metallic blue. It shone in the incandescent light as she walked towards me. I'd seen plenty of girls in bikinis, and I'd seen them in nothing at all on the internet, but seeing Leah like this was so different. I didn't just think she was hot and want to do her, I also thought she was beautiful, and I wanted to hold her.

She sat in my lap and kissed me. I put my arms around her and was surprised by the feeling of so much skin and so little clothing. She wrapped her arms around me, clearly enjoying the feel of my skin as well. Her face was an inch or two from mine.

“So, truth or dare,” she whispered.

“Dare.”

“I dare you to let me feel your dick through your pants.” Leah looked more excited than ever, but also really nervous. I could have imagined it, but I thought the crotch of her bikini looked wet. I guided her hand down to my crotch.

She hand felt my shaft through my pants, and she rubbed it for a second, and suddenly, she froze. She looked really scared. I put my arms around her, but she was stiff. She wouldn't look me in the eye. She stared off into space.

“Leah, what's wrong?”

She didn't answer me.

“Leah!” I gave her a light shake. She snapped out of it.

She looked at me. Her eyes looked watery.

“I... I dunno...”

“Don't know what?”

“I, umm, I'm just not sure if this is right.”

“What do you mean?”

“Like, I dunno, I just should have thought about this more, and I didn't at all. Maybe this is too fast.”

“Okay, we can slow down.”

“I'm sorry, I shouldn't be doing this.”

“I though you were having fun.”

“I was, I am, I just, I think... I think you should go.”

“What?”

“I'm sorry, I know this must be really confusing for you.”

“Yea, it is.”

“I just, I just need to think about us and stuff and I just need some space. I'm really sorry.”

“You mean you don't want to be with me.”

“No! No!” Leah cried out and held on to me. “I want to be with you, I just need to think some. Okay? Please? Please don't be angry with me. I just, I don't know what I'm doing, and I need to think and know this is okay, okay?”

I was silent for a long time.

“Yea, I understand. I'm sorry I rushed you.”

“No, it's okay. I enjoyed it. Just, let me think awhile, okay? I'm sorry.”

“Okay. Let me know when you want to talk. I'll be around.”

She held me again. “No, not like that. Not that much space.”

“What then?”

“Could you just call me, like, the day after tomorrow?”

“Yea, okay.”

“I'm really sorry.”

“It's okay.”

“Okay, umm, could you go now?”

“Yea, I'll talk to you later. Bye.”

I put my shirt on, kissed her, and walked out the front door, feeling like I was going to vomit. I had had a great time, but it wasn't worth it if I had lost Leah over it. I hoped she was just freaked out, and things would be normal when she calmed down. But honestly, I had no idea what was going on...

To Be Continued...

[BettyBoop]

Wow, I really like this story, it's original and brilliantly written, I think I shall subscribe to this thread. I hope you continue.