Pleasing My Conservative Girlfriend

quidproquo · 06-02-2009, 03:58 PM

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...

06-02-2009, 03:58 PM	#1
quidproquo Senior Member Join Date: Jun 2009 Location: The US of A Posts: 109	Pleasing My Conservative Girlfriend 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... Last edited by quidproquo; 06-02-2009 at 04:17 PM.