Teaching Her to Open Up

I had been dating Caroline for a short time, maybe a month, when I decided to break it off. She is a beautiful woman, about 5' 3", a small build with an incredible ass and a nice, firm pair of breasts. She is very intelligent, a great all-around package, but she was too reserved for my tastes.

Caroline was raised in a very wealthy, conservative, Bible-thumping household. Even though she is in her late 40's, and raised two good kids by herself, her parents still have a hold on her life.

We had slept together three times during our time together, and it was nothing spectacular. As I said, Caroline is a beautiful woman, and has an incredible body, but even looking at her nude couldn't make up for the lack of fire in the bedroom.

We had plans to go out shopping together Friday evening to find a dress for Caroline to wear to her cousin's Christmas party, which we were supposed to go to in a month. We were going to meet for a drink before we went, and I decided that would be the perfect time to end things with her.

The break-up actually went smoother than I expected. Caroline had told me that she had a problem getting past the first couple of months in a relationship, and I didn't know how she would take it. She took the news quite well though, and we parted ways.

Late that night, as I was sitting on my patio having a cigar and a bourbon, my phone rang. The caller ID told me that it was Caroline, and I briefly debated whether to answer it. I really didn't want to deal with it right now, so I let it go to voicemail.

When I listened to the message the next day, I heard Caroline asking me about getting a couple of things that she had left at my house. I called her back, and told her that I was free that afternoon, and could run them by her place, or we could meet somewhere.

Caroline had some errands to run, so we decided where to meet. When we both got there, I brought Caroline her things, and as I was saying goodbye, Caroline asked if we could talk for a minute.

I was really hoping to avoid any rehashing of what happened last night, and why, but I knew that wasn't going to happen, so I decided to get it over with.

"Sure, I have a few minutes," I told her.

"What is it about me that makes men run after only a month?" she asked, getting right to the point.

"Caroline, you don't want to do this," I told her. "It was just a lack of chemistry, that's all."

"I felt chemistry, though," she responded. "If you didn't feel any chemistry, why did you sleep with me?"

"Caroline ..." I started.

"I want to know," she cut me off. "If you didn't feel any chemistry with me , why did you sleep with me? Am I just a notch on your bedpost?" she demanded.

Knowing that there was going to be no avoiding this, I decided to be blunt with her.

"No," I told her. "I felt there was some chemistry, that's why I wanted to sleep with you. I don't have notches in my bedpost, as you know, having been in my bed."

I wasn't sure how much further to go, so I paused a second to see if that would satisfy her. Of course, I had no such luck.

"So what happened?" she asked. "Am I that bad in bed? I know that I don't have a lot of experience, but I didn't think that I was THAT bad."

I knew that there was no way around it now, so I decided to put it all out there. "You're not bad," I told her. "You are just too ... uptight, and conservative. Sex with you is just too vanilla."

"Well, I just don't have much experience," she told me. "I don't know what to do."

"Experience has nothing to do with it," I told her. "It is all about enthusiasm, about opening up. You have to loosen up in bed. Sex is all about having fun. You seem to approach it as a burden, or a chore."

"I enjoy it," she responded, "especially with you. You are the biggest, and the best that I've ever had."

"Look," I finally told her, "I told you in the beginning that I was not looking for a serious, committed relationship right now, and you just aren't FWB or sex-buddy material. Your body sure as hell is, but your mind isn't. I'm sorry."

"Help me then," Caroline responded, almost sounding desperate. "I want to be like that. I want to be the type of woman who men think of when they think of sex. I'm tired of being a revolving door for men. Please."

"You can't," I responded. "You just aren't like that. You aren't open-minded enough to be that person that you want to be."

"I can be," she answered. "I want to be."

I knew that there was only one way to satisfy her, but I had to do this on my terms. I knew that if she agreed, I could have a little fun turning her into a high-class slut.

"OK," I told her, "I will help you, but there is one rule that you have to follow. If you ever refuse to do something that I tell you to, it's over. No questions."

Caroline looked at me for a second, and said "OK."

"OK, what?" I asked.

"OK, I will do whatever you tell me to," she responded softly, looking at the ground.

"Look me in the eye and tell me," I said firmly.

Caroline looked me in the eye, and said to me, "I will do whatever you tell me to."

"And what happens if you refuse?" I asked.

"If I tell you no, then the lessons are over," she answered, keeping eye contact.

Still not believing that she would go through with it, I smiled, looked at Caroline, and said, "OK. Wait here a minute."

We were in the parking lot of a mall this whole time, and I went into the mall. I knew that Victoria's Secret was close to the entrance that we were nearest, and I headed straight there. I remember Caroline telling me one time that as far as she was concerned, thongs were for sluts. I also knew what size she was.

I bought a dozen pair in her size, and headed back to the lot. She was still standing where I left her when I got back.

I looked at her dress, a light, flowery summer dress, and looked into the bag that I was carrying. I pulled out a pair of lavender thong panties and handed them to her.

"Put these on," I told her.

Her eyes widened as she realized what I was holding, and she took them in her hand.

"OK," she responded, and turned towards her car.

"No," I told her. "Right here."

"Right here?" she asked, shocked. "Out in the open?"

"Yes," I told her. "Right here, out in the open. Just reach up under your skirt, pull down what you have on, and put these on."

Caroline looked around, reached up under her skirt, and pulled off her panties. I put my hand out, and she handed them to me. I could feel the warmth from her crotch, and they felt a little damp. I knew then that I had her. She was excited by all of this!

Looking around a second time, Caroline pulled the thong panties that I gave her on. I could tell by the look on her face that she was a little shocked, and a bit pleased, by how they felt on her.

I put the panties that she handed me into my pocket, and handed her the bag with the rest of the thongs. "I want you to wear these from now on, unless I tell you differently. Do you understand?" I asked her.

Caroline looked up at me and said softly, "Yes."

"Good, I'll call you later," I told her as I walked back to my truck.

Later that afternoon, I called her. "How does that thong feel, walking around all day?" I asked, as soon as she answered the phone.

"It feels nice," she answered softly.

"Do you like the way it feels, rubbing against your pussy while you walk around, with all of these people around you?" I asked her teasingly.

She gasped when I said that, but she answered. "Yes," was all she said.

"Good," I told her. "Call me when you get home." I hung up, and prepared for the evening. I decided that I would try to push her as far as I could tonight, to give her a taste of what she was in for.

That night, we were sitting in Caroline's home, having a bottle of wine. I knew that would help her relax, and I brought some additional assistance also.

As we finished the bottle of wine, I put some jazz on the stereo and pulled out a joint. I had a kid at work find me some high-grade smoke, and I knew it would help her relax and open up even more.

Caroline smoked the joint with me after a brief protest, and when we were done, I knew that she was ready for the evening's festivities to begin.

We went up to Caroline's bedroom suite, and I took her straight to the bathroom. She has a Jacuzzi tub, and I led her there. While we stood there, with Coltrane softly wailing in the background, I got behind her, and while gently breathing and blowing on her neck, I started to slowly remove Caroline's clothing.

When she was nude, I had her step into the tub and sit at the edge. I had brought along my beard trimmer, so I grabbed it and her razor and cream and stepped into the tub with her.

"What are you doing?" she asked as I turned on the water.

"I'm going to shave you," I told her. "Just sit back and relax."

"But, I ..." she started.

"But you aren't going to argue with me, are you?" I cut her off.

"No," she said meekly.

I turned the water on to warm it up, and got down between Caroline's legs, opening them up. I could see moisture starting to dew up on her pussy, and I knew that she was enjoying this more than she wanted to let on.

When I had her legs spread, I took my trimmer and turned it on. When I touched it to Caroline's body, she let out a gasp. I had never even thought about the vibrations from the trimmer affecting her.

I started to trim the hairs from around her crotch, and she started to squirm as I got closer to her pussy, leaning back to give me better access. The pot and the wine had clearly taken a good hold of her mind, and she was enjoying what was happening to her body.

When I had all of the hairs trimmed down, I turned the trimmer off, and I heard a small moan come from Caroline's lips. I smiled as she gasped and moaned as I poured warm water over her almost bare, moistening pussy.

When I started to rub the shaving gel over her pussy, she groaned louder, and moved her hips slightly.

Caroline was wiggling and moving her hips in small motions as I shaved her. As I got to the area around her clit, I intentionally slid my thumb over her swollen bud as I moved it out of the way. When I did that to both sides, Caroline let out a loud moan and sighed.

When I had her entire crotch bare as the day that she was born, I poured more warm water over her, and patted her dry.

When she was mostly dried off, I helped her step out of the tub, and I sat her down on the outside edge. I rubbed a lotion over her newly shorn mound, intentionally avoiding her clit. By now, Caroline was almost ready to explode, but I wanted her to wait.

I led her back to the bedroom, and had her stand in the middle of the room. I went to a bag that I had brought with, and pulled out some more of my purchases from the mall.

I pulled out a silk camisole and matching silk thong. "Put this on," I told her, and I opened a second bottle of wine that I had brought up.

When she had the lingerie on, I handed her a glass of wine, and looked her up and down. She did look incredible, and I was tempted to just throw her down on her bed and fuck her silly, but I knew that I had to keep up with my plan.

While she was drinking the wine, I went around her room and lit some candles. Soon, the room was filled with fragrances, and Caroline had finished the glass.

After I put the glasses down, I went to my bag and pulled out a silk scarf. I walked up behind Caroline, and started to softly glide the scarf over her body, and eventually tied the scarf around her eyes, blindfolding her.

She gasped softly as I tied the scarf around her head, and I led her to her bed. I laid her down, bent down to her ear, and whispered to her, "I want you to touch yourself." She gasped when I said that, and started to say something, but I cut her off.

"Listen to the music, let the music and the buzz take you away. I am not here. That is why I blindfolded you. You are alone in your bed, you are horny, you want to touch yourself. Enjoy yourself," I told her softly.

"But I can't do that in front of you," she protested.

"I'm not here. Nobody's here but you, in a dark, candle lit room," I whispered. "Explore your body. Please yourself. In order to tell someone else what you like, you have to know what you like."

I placed her hands on her belly, and walked away from the bed. I turned the music up slightly, and quietly pulled a camcorder from my bag. As I was finding the perfect spot to set it up, Caroline started to move her hands. Soon, she was rubbing her breasts through the silk, and her breathing started getting heavier.

After playing with her breasts and nipples for a few minutes, she started to slide one hand down to her pussy. From where I was sitting, when Caroline spread her legs and slid her hand down, I could see a large wet spot on the silk.

As she slid her hand over her silk-covered clit, Caroline let out a loud gasp and moan, and started to pull on her nipple with her other hand. I knew that the feel of the silk was just adding to the sensations that she was feeling, and I sat back and enjoyed the show, getting it all on video.

It didn't take long before Caroline was starting to cum. She was rubbing her pussy faster and harder while humping the air, and she was pulling harder on her nipple. Soon, she started to moan and groan loudly, and started to shake.

Finally, Caroline was hit with her orgasm, and she moaned loudly. "Ohhh!!!" she wailed, as her body shook and she cupped her pussy and squeezed her breast.

I knew that she had to have had a good orgasm, but she still seemed to hold back some. When she came down from her orgasm high, she was still lightly rubbing herself. I quietly went to the side of the bed, and while she was rubbing the silk, I gently pulled the covering aside, so that she was rubbing her bare pussy. Her pussy was soaked, and her fingers slid over her bare skin easier that they did on the silk.

When she felt her bare, wet skin, Caroline let out another gasp. She started to flick her clit, and was humping her hips again. After a couple of minutes, she had a couple of mini- orgasms, and seemed to be slowing down. I went back to my bag, and pulled out the last of my purchases, a 6" long, silent, waterproof vibrator.

I walked to the side of the bed again, turned the vibe on, and gently placed it in her hand. She let out a long, loud moan when she felt the vibrations on her pussy, and immediately started to slide it over her clit.

"Oh my god," she moaned as the vibrations shook through her body. She had her feet planted on the bed, and was humping the air. Soon, on her own, she slid the hand that was pulling on her nipples and brought it down to her seeping pussy.

By now, I had taken the camcorder in my hands, and was getting even better views and close-ups. I had a hard-on that was threatening to burst through my pants, but I was trying to concentrate on Caroline.

The hand that was on her nipples went to her clit, and she started to slide the vibe down lower. Her breathing was getting heavier, and she was moaning more and more, with her hips moving in every direction.

Caroline rubbed the tip of the vibe all around her pussy, coating it in her juices. After a short time of this, she slid the vibe down to her soaking pussy, and started to slide it in.

"Oh my god!" she yelled, as she slid the vibe as deep into her wet hole as she could. She rubbed her clit faster, and she kept moaning, "Oh my god, oh my goddd!! Ohh!" as she brought herself to another major orgasm.

I was alternating the camera between her face and her pussy as Caroline brought herself to her orgasm. Finally, she tensed up, shoved the vibe all the way in, holding it at an angle that would get the top of her pussy, and stroked her clit at a rapid pace.

"Oh my god! Oh god yes!" she yelled, as her orgasm overtook her. Her body shook and quivered and I saw an incredible amount of fluid ooze out of her pussy around the buried vibe.

As her body came down from what seemed to be an incredible climax, I gently reached between her legs and turned the vibe down, and then off. As the orgasmic high wore off, Caroline started to drift off to sleep. I went around the room, blowing out candles and turning off the stereo, until I knew she was asleep.

When I knew that she was out, I untied the blindfold and opened it up along her pillow. I slowly slid the vibe out of her still tight pussy, and I heard a faint moan and got a little shake when I withdrew it. I then placed it on her bed table, next to her clock, right where she would see it.

I pulled a sheet over her to cover her, gathered my things, and went home, letting her sleep. Before I left, however, I left her a note, under the vibrator, that said, "Wear these tomorrow," and placed another silk thong alongside it.

The next day was Sunday, and I knew that Caroline went to the 10:30 services at her church. I also knew that for at least an hour after the services, her entire family stuck around for a gathering of the clans, as it were, in the social center, next to the church. I decided to drop in and make an appearance.

As soon as I walked up to the building, I was glad that I wore my best suit that day. This was obviously a very conservative congregation, every male in a suit, and every woman in a dress. It kind of made me think that this was probably what an Osmond family reunion must look like.

I was able to pick out Caroline and her family immediately. All of the women, Caroline, her mother, and her three sisters, all looked alike. They all had the same beauty body type. They also, especially the mother, looked like ice princesses.

I chuckled to myself when I got a good look at Caroline. She looked like she had woke up late, and rushed to get to church on time. Walking past her family, I even heard her say to her mother, "I just overslept. Big deal."

I made my way around the room, nodding and saying hello to people, who obviously had no idea who I was, but were far too polite and "well-heeled" to ask me any questions.

Eventually, I saw Caroline head towards the coffee, and got in line right behind her. When I knew that no one was around to hear, I leaned into her, and whispered in her ear, "Are you wearing your silk thong today?"

Gasping, Caroline spun around to see my smiling face. She was surprised to see me, and her face had a million emotions all at once, from a brief smile to shock.

"Good morning. How are feeling today?" I asked, teasing her.

"I, uh, I'm fine, thank you," she was finally able to get out.

"You haven't answered my first question," I reminded her, smiling.

"What? Oh," she said. "Um, yes, I am," she whispered.

"You are what?" I asked, enjoying this tease.

"I am wearing my silk thong," she answered in a hushed voice. "What are you doing here?" she asked.

"Why, I came to see you, of course," I answered. "You know, of course, that I am going to want proof of that."

"Proof? What kind of proof?" she asked as we walked away from the table carrying our coffee.

"Well, obviously, visual proof would be best," I smiled at her.

Before she could respond, an older woman approached us, and said in a loud voice, "Hello Caroline. Who is your friend? I don't believe that we've seen him around before."

Not at all upset or insulted that this woman was speaking about me as if I wasn't standing right next to her, I just smiled at the old cow.

"Aunt Honore, this is Kurt. He's a friend of mine," Caroline told this woman.

"Oh," her Aunt responded. "Is he your boyfriend? I mean, you two were just talking awfully closely."

Before Caroline could respond, I cut in and told the nosy cow, "We just started dating recently. You might say that we are still testing out the chemistry."

When the old woman finally finished with the interrogation, she waddled back to the family to report what she had learned, and I led Caroline away.