Pleasing My Conservative Girlfriend

[OnDRun]

Amazing story. I have dealt w/ girl just like Leah which makes it so much more realistic. Absolutely AMAZING!!!!

[BettyBoop]

Ha, she reminds me of myself, I'm very "conservative" how you put it in such situations. Go me.
Seriously though, I am in love with your story. Dudio, be proud.
Sorry I'm typing oddly, I haven't eaten so I'm weird.

[quidproquo]

Hey guys, sorry about the long wait. I should be back to updating regularly. As always, tell me what you think. If you have any ideas for upcoming chapters, I would love to hear them. Thanks so much for your support! It means a lot to me.

Chapter 3: Feeling out our Limits

I called Leah on Wednesday. It was on of the most awkward conversations I've had. Some of our friends were planning to hang out at the mall and then go see a movie. We decided to talk in person at my house and work out what had happened, and then meet our friends and walk to the mall.

She arrived at my house looking nervous but happy to see me. She came in quietly and hugged me. We walked upstairs to my room without saying much. I shut the door and we sat down on the bed.

She put her arms around me and her head on my chest without speaking. I held her. She was shaking slightly, but she clung to me very tightly.

We sat that way for a long time, on the edge of my bed, without saying anything.

I think Leah might have been crying, but her head was down and her long hair was covering her face, so I couldn't tell. I wanted to say or do something, but I had no idea what she was thinking. I thought she might be working up the nerve to break up with me. I held her and waited...

Leah said something very quietly, and I couldn't make out what she said.

“What?”

“I'm sorry.” I think she must have been crying because it caught in her throat.

I wanted to ask 'why?' but I was afraid she was going to say, 'because we can't be together,' or something. I was sure she was mad at me. Finally, I sucked in my breath and asked, “About what?”

“Monday night.”

“Sweetheart, I want to work this out but I'm pretty confused. You need to tell me what's going on.”

“I don't know... I, well, I feel really bad.”

“What do you feel bad about?”

“I just wish I had thought through things a little more.”

“Do you feel like we did something wrong?”

“No, I don't think so, maybe, I'm not sure...”

I had no idea what to say. She went on.

“I'm really sorry I made you leave and stuff. I probably like, really upset you.”

“It's okay, I'd just like to understand what's going on.”

“I just freaked out is all. Like, we were crossing these lines I hadn't thought about, and I was afraid we were going too far. Afterwards I felt like I had violated something, like I had broken a promise to myself. I'm sorry I haven't seen you, I just needed some time to think about what happened. But I know it hurt you, for me to send you away like that, and I'm really sorry.”

“It's okay.” I hesitated. “Did you come to any conclusions?”

“Yea, I did actually. I think I have it all sorted out, at least, right now.”

“Okay, umm, what did you decide.”

“I don't want to tell you.” I was afraid I didn't want to hear, either.

“Please.”

She took a deep breath, like she was steeling to do something painful. I thought I knew what it was, and I braced myself. She blurted it all out, very fast. “I've decided I want to be a virgin on my wedding night. I know it's weird and like nobody does it, but that's what I want. I only want to have sex with my husband, when he is my husband. I'm really really sorry, but I'm not going to give you my... virginity, and I know that's like, unheard of, so if you want to find--” her voice caught, “--someone else, who can, umm, make you happy... in that way... I understand. And I hope you'll still be my friend, because I really do... love you.”

I almost laughed in relief, but her face was so agonized that I caught myself. “Wait,” I had to check, “You're not breaking up with me?” I hugged her.

“No. I thought you would break up with me.”

“Why, because you wouldn't f-, I mean, have sex with me?” I tried to avoid swearing around Leah. She never said anything, but I thought it bothered her.

“I guess, yea. Isn't that kinda, like, really important to guys?”

I had to be honest. “Well, yea, but, I can control myself. I hope you know you're not just a sex toy to me, Leah. I would rather be a virgin with you than get laid with someone else.”

Leah looked shocked. She didn't speak for a full minute. “Really?”

I looked at her. “I hope you think more highly of me than that.”

She looked ashamed.

I continued, “We don't have to do anything you don't want to do. Hands off, I promise! This isn't just about having fun, I want you to feel respected and stuff and not guilty because, umm, I love you too.”

She wrapped her arms around me in a hug that seemed much tighter than she should have had the strength for. Not content with this, she wrapped her legs around me too and pressed her face against my chest. I ran my fingers through her hair.

I was happy that she seemed happy, and happy that I had finally told her how I felt, and happy that we were still together and she seemed to have forgiven me for the other night. I let her stay like that a long time, and she didn't move, and I was worried she might be crying again. I tried to lighten the mood.

“So, I'm guessing hands off isn't exactly you plan though...”

She shook her head and looked up at me. “I thought about that a lot.”

“What did you decide?”

Once again, she blurted out everything very fast. It was obvious she had been meaning to explain all this as soon as she found out if I was going to leave her. The 'I love you' must have set her off track, but she was back now. “I decided that I had four categories. First, there are things I'm morally opposed to, outside of marriage. Sex, obviously. And like, anal sex,” she looked embarrassed, but pressed on, “and stuff. I'm never going to do that stuff with you unless we get married.” I nodded to indicate I was okay with this. I was surprised how okay I was with never getting inside my girlfriend, but somehow, that wasn't what I cared about most.

Leah continued, “Category two is stuff that I'm morally opposed to doing right now, mostly because I think I'm not ready to do it at my maturity level and stuff, but I'm okay with doing it eventually, before marriage, but I can't promise a time line, and it might be we never get to do stuff in this category either. Category three is the stuff that I'm morally okay with doing right now, but I'm just not emotionally comfortable with right now. That's stuff I am okay with and actually want to do, and will do with you in the near future as I get more comfortable. Category four is stuff that I'm okay with, right now.”

I was shocked that she had thought this all through so analytically. I knew that she hadn't been very open to me the past year, so there was a lot about her that I didn't know, but as I found out more about her under the surface, it was not what I would have expected. I shook my head in surprise.

“I can tell you've given this a lot of thought. You're feeling pretty analytical lately, huh?”

“I thought you deserved some clarity.”

“Thanks, I actually appreciate that a lot. I think some clear boundaries would help us a lot. My parents always say 'communication is key to any relationship.'”

“Okay, I'm glad I didn't freak you out.”

“Not at all. So, tell me, what is in what category?” I was a little apprehensive about this question.

“Umm, category two has getting naked, touching under our clothes, like bare skin, and, umm, masturbation and stuff,” she blushed bright red when she said this. She looked at me like I might break up with her again, but I was trying to hide my excitement. My girlfriend, the incredibly hot, beautiful girl sitting in my lap has just told me that, eventually, she would let me see her naked. I was very happy.

It must have showed, because she continued. “Category three has touching my boobs and my crotch, putting your hands in my shirt or pants, seeing me in just my underwear, and stuff like that.”

“Okay, so tell me the stuff you are okay with right now.”

“Okay, category four. Umm, making out, seeing me in swimsuits, feeling my butt through my clothes, spankings, and umm, hopefully me touching your crotch, if it's okay with you.”

I smiled, “Yea, it's okay with me.”

She seemed to relax. She straightened up, and began to take off an oversized navy sweatshirt. For the first time, I was relaxed enough to appreciate her appearance. She was wearing jewelry, which was rare. She had a long silver necklace on with matching earrings and bracelet. She was wearing lightweight khaki colored capris, and she had just removed her sweatshirt to reveal one of her nicer tops. It was also navy colored, and she always wore it with a laced white spaghetti strap underneath, both because she liked the color combination and because it was much too low cut for her to wear alone.

And that was what she had done. The undershirt was missing, and I was staring at her cleavage for the second time in my life. She was wearing a lacy black bra, and her shirt was curt low enough that I could guess it was a push up bra. I knew she was an A cup, but I couldn't imagine it now. The soft, lightly tan, perky breasts that pushed out from her chest seemed huge on her slender frame.

I had seen plenty of boobs in movies and stuff, but I knew her body would always be uniquely mesmerizing to me. She noticed me noticing. The old Leah, the Leah I had known only a week ago, would have been upset that I was staring, but something seemed to have changed in her, something had relaxed.

“Do you like them?” She emphasized the last word, and I could tell that she didn't care what I thought of her top. She wanted to know what I thought about her. She wanted me to look at her breasts and tell me how they were. I couldn't get over it...

“They're perfect, Leah.” I said softly.

“Thanks. It's kinda my way of apologizing.”

“For what?”

“Hurting you, on Monday.”

I wanted to tell her that she hadn't hurt me, but it was a lie, and she would know it.

“This makes up for it.”

She looked troubled. “No, I don't think it does.”

“What?”

“Well, honestly, I thought this would be pretty embarrassing, and it would please you, so I thought ti would be a good apology, but I enjoy letting you see me, it's not hard at all, I would do it for enjoyment, anytime. So you see, I'm still being selfish.”

“So?”

“So, if I'm going to do something to make up for Monday, I shouldn't enjoy it. You'll have to tell me something else I can do, to make it up to you.” I thought about arguing with her, but Leah had a strong guilt reflex, and I knew I wouldn't win. Also, I was excited about the idea of her doing something else I would enjoy. I thought for a moment.

“Okay.”

“So, a spanking?” Leah's voice was nonchalant, but her face looked hopeful.

“No, you like it when I do that, that wouldn't work.”

Leah pouted, looking embarrassed that I had figured that out.

“Okay, what.”

I thought for a moment. “Give me your panties.”

Leah looked uncomfortable for a moment, and then she nodded. Quietly, she kissed me and got off my lap. I stood up next to her. She pulled back the comforter on my bed and then climbed under the sheets. She unzipped her khakis and slid them off under the sheets, and then paused, looking truly embarrassed.

“You're too good at punishing me, you know that?”

“You quite literally asked for it, dear.”

“I know.” She seemed to resign herself, and pulled her panties off. She handed then to me from under the covers. I took them, and she blushed. They were lacy and black, and looked like they matched the bra. She looked up at me intently, and I realized she was waiting to find out what I thought of her underwear.

I smiled. “Very hot.”

She smiled back, and didn't move.

“So, does a sheet count as 'through your clothes.'”

She only thought for a second. “It does, if, and only if, you tell me when I'm getting my panties back.”

“Well, you'll get them back tonight, after the movie, if you finish your punishment.”

“Which is?” She smiled, intrigued, but tried to look annoyed.

“You have to buy a thong tonight at the mall, and wear it home.” Leah looked mortified.

“In front of our friends!?”

“Yea, I had an idea about that. Kyle is bringing his girlfriend, and Alice and Brad are the only others coming. I know Alice has a thing for Brad, which makes it more or less a triple date. You girls could stop at the Victoria's Secret and all buy underwear together, and you know, get the guys opinion. I'm sure pretty much everyone would go for it, and it would probably make it less embarrassing for you, and all you have to do is suggesting going into the store, and everything else should happen naturally.”

Leah looked comforted by this idea, but not what you would call happy. “Okay, well, I guess it is supposed to be a punishment. I'll do it.”

“Good girl.”

“So, I do this, and I get my panties when we get back to your house?”

“Umm, only if you wear the thong home.”

Leah tried to look angry, but it only worked halfway. “Alright, I deserve it, you have been successful in giving me appropriate penance for my sin.”

“I'm glad you're happy.”

“I'm not happy, you're still too far away.”

“Oh, right.” I laid down next to her. I pulled the sheet down as far as I could without exposing her nude bottom half. I wrapped one arm around her back and turned her so she was lying on her side. I kissed her gently, playing with her lips. She seemed very happy with our new, more liberal boundaries. I reached to touch her ass through the sheet and hesitated, unsure if she would freak out again.

She was inches away from me, looking at me with her beautiful pale blue eyes. “It's okay, really,” she breathed, very softly, and stuck her tongue in my mouth, flicking it lightly over my front teeth, teasing back and forth.

I lost it. I held her close to me and we turned so she was on top of me, the sheet twisting to keep her naked ass covered. I reach down and ran my had over it. It stuck out obviously, strong and muscled from her athletics but strangely soft and wonderful to the touch. The sheet was thin, and I ran my ran over her ass while she plunged her tongue further in my mouth.

I didn't mind if we stayed at this level forever. I didn't need to sleep with her, this was wonderful enough, more than I deserved. She certainly seemed to be enjoying herself. Her breathing was coming faster, and she was making little moaning sounds. It seemed like she was trying to get her tongue as far into my mouth as she possibly could. We began to grind against me, and her movements were stimulating my already erect dick.

Suddenly, I recognized my mom's voice just outside my room. “Sure Kyle,” she was saying, “They should be in here. I'm sorry they kept you waiting.”

“No problem,” I heard Kyle say. I looked up in horror, and Leah moved to kiss my neck, apparently too much in her own world to realize we were about to be discovered.

The door nob was turning.

To Be Continued...

[BettyBoop]

Woah, talk about cliff hanger, your story just gets better and better. It was definitely worth the wait, do carry on .

[quidproquo]

Thanks Betty, it's good to be back. Next chapter is almost done!

[MasFresco]

Wow man, this is really awesome. I'd like put it on Interesting's story writing level.

[nitsuga]

Wow this is a really good story! I love it.

[Do Anything Girl]

This is the best story i've read on this site. Your doing an awesome job with it. There is still so mush more potential left in this story.

[cameem]

wow! this is such an awesome story i cant wait to see more!

[Nohbdy123]

I like it a lot.
Although I'm pretty sure it's fiction, if you said it was nonfiction, I would believe it.

[Orbital Shark]

Wow, this story is amazing.......keep posting, thx

[HeadHunter_t]

this is a grate story keep going it just gets better and better as it goes.

[urlilslave080]

Great read really great, it so different and unique, you explain everything with the detail needed and you give Leah the feelings, emotions and actions of a normal person put in that situation keep up the great writing.

[quidproquo]

Chapter Four: Focus

Leah noticed what was happening, and we reacted simultaneously, jumping of the bed. For a second I caught a glimpse of her bare ass, but I turned and moved quickly towards the door, hoping to spare Leah the humiliation of giving Kyle the same glimpse.

Kyle was opening the door as I arrived, and I acted quickly to slow them down without arousing suspicion.

“Hey Kyle!” I said loudly, and stepped directly in from of the door. It opened about 8 inches before it hit me in the nose. I groaned much louder than necessary and pushed the door closed.

“Oh, hey, sorry man. You out of the way?”

Kyle opened the door again, more slowly and walked in. I stood as close to him as possible, trying to obstruct his view of Leah, talking loudly, trying to draw his attention. It seemed to work.

“Hey man, are you okay?” Kyle looked concerned. I was holding my nose.

“Yea, I'm fine, you just surprised me, that's all.”

Kyle was about to respond when he was distracted by the sound of Leah zipping up her capris. He looked from her, to her black panties, lying on the floor, and back to me, smiling. I gave him a stern, meaningful look, and he looked genuinely sorry for disturbing us. He nodded once and pressed his lips together, and I knew he was promising not to mention what he had seen. Well, at least until we were alone. Now one was more supportive of me getting in Leah's pants than Kyle, who couldn't seem to understand why I would stay with someone who I didn't seem to be making progress with, as he put it.

“Hey, I just came up to let you guys know that we're all here, and Laurie is kinda impatient to get going, she wants to make the matinée, so she wanted me to see if you guys had lost track of the time or anything.”

“No, we were just heading out when you almost broke my nose.”

“Sorry about that.”

“No problem, are you ready sweetheart?”

Leah appeared at my side and kissed my cheek. “Yea, I'm ready,” then she looked at Kyle. “Could you give us just a moment?”

Kyle tried not to look surprised. “Yea, sure, we're all downstairs. Take your time.” He shot me a wink before her disappeared, and I shut the door again.

I turned to Leah. “I'm sorry.”

“Don't be, I'm not. I wanted to thank you for covering up so well. That was brilliant.” She pulled my head down to meet her lips and resumed kissing me like nothing had happened. I smiled and opened my lips for her. After a minute, I began to worry about our friends waiting downstairs.

“Hey, do you think we should, you know, head down?”

Leah sighed, making a show of being disappointed, “Yea, I suppose so. I asked for a minute because I was hoping you would store my panties somewhere less conspicuous while we're gone.” She smiled up at me, intentionally being extra cute.

“What's in it for me?”

Leah thought for a moment. “You get it pick which thong I buy.”

“Deal.” I walked over and picked up her panties. They were still warm, and my cock hardened, visualizing her in them, and then without them. Out of curiosity, I looked at the label as I slid them inside my locking desk drawer. I rummaged around and found the key, locking them in, and placed the key in my pocket.

I turned around. “Size four, huh?”

Leah looked uncomfortable. “Yea.”

“You are incredibly hot.”

“Sure, whatever.”

I looked at her, concerned. “What?”

“Nothing.”

“Tell me.”

“I just wish I had, like, a big butt, you know, and like, hips and stuff.”

I grabbed her butt and picked her up with both hands. She smiled and wrapped her legs around me. I went out on a limb, hoping she wouldn't think I was shallow. “Your ass--” I swore intentionally, for emphasis, “--is one of my favorite features.”

“Really?”

“Yours is better than any girl's I know.” And I meant it. I liked everything about her the best. She smiled and kissed me again. “We should get going.”

“I know, but I haven't seen you in so long.” She didn't stop. I let go of her slowly, trying to let her down, but she hung on to me and continued the kiss. I was flattered by how into me she was, but I was worried she would be upset if our friends inferred what we were doing--her reputation and all that.

“It's time to stop.”

“Not yet.”

She had her arms wrapped around my neck and her legs wrapped around my waist, with her crotch grinding against mine, and her butt sitting out, exposed. I gave it a hard, swift slap that made a satisfying cracking sound, and she pulled back. I looked at her sternly.

“What did I tell you?”

Leah looked rebellious. “Are you going to spank me for kissing you?”

“I'm going to spank you for making our friends wait, if you don't get a move on.”

Leah's face looked conflicted. I knew she wanted to keep up the pretense that she didn't enjoy getting spanked, but I could tell she anted to intentionally disobey me so I would do it.

“Oh, fine.” She scowled and got down. She turned and walked towards the door. I slapped her ass again, more as a sign of affection than to keep her moving, and she giggled like she was getting away with something.

As we walked towards the stairs to go down and meet my friends, she seemed to remember something and stopped, looking at me.

“Do you want me to wear my sweatshirt.” She indicated her slightly excessive cleavage. I could tell her shirt was not meant to be worn without an undershirt.

“No, you look fantastic,” I kissed her and went on, “I trust you, I'm not worried about you getting with someone else who likes you, and I kinda like it when guys are jealous of you.”

Leah looked surprised. “Like that would happen.”

“Happens all the time.”

“Really?”

“Scouts honor.”

Leah seemed mildly disconcerted. “Well, they're wasting their time. I only want you.”

“I know, but say that again.”

“What.”

“That you want me.” I inflected my voice to mean something different.

She wasn't put off. “I want you.” She moved closer and came to kiss me again. I leaned back.

“Focus, we need to go.”

“Fine.” We walked down the stairs, and saw our friends waiting at the bottom.

To Be Continued...








Thanks for all the support! I had hoped to go a little further in this chapter, but honestly I'm a little stuck with what to do next, especially with the new characters I just introduced, and this felt like a natural stopping point. Next chapter in a day or two. Sorry this one isn't as exciting, if that's your thing. Next chapter has some more action on the drawing board!

[Orbital Shark]

Wow, I'm really starting to like this...........