Teaching My Virgin Sister

While asking her, I had my fingers crossed. Please let it be yes.

"Did you get it?"

She was smiling, and that was a good sign, but then I noticed that she was tense, and that there was sadness in her eyes. My heart sank. She was putting on a brave face.

Then as her eyes lit up, she suddenly shrieked, "I got it!"

Before I could speak, she gave me a hug, so tight, that I was struggling to breathe.

"Congratulations, that's the best news I've heard for a long time. Now I think you should release me, before I pass out."

That made her giggle. Then, after letting me suffer for a few more seconds, she let me go. How could my Sister, who was so small, squeeze so hard?

"Did I fool you?"

"Yes. Hook, line and sinker. You were very convincing. I thought that you'd failed the audition."

"Good, that's what I wanted you to think."

"One day you're going to be a famous actress. A star of stage and screen."

"Do you really think so?"

"Absolutely!"

She might be, but there was still a long way to go. However, what she needed now, was for me to believe in her.

Courtney is nineteen, and I, Ethan, am twenty seven. For as long as I can remember, I have been worried about my little Sister. She has always been shy, lacking in self-confidence. That was until nine months ago, when something happened. She started acting.

We were walking past a local theatre, when a poster caught her eye.

'Have you ever thought of acting? We are Theatre For All. Don't be shy, call us today. You never know, you might like it.'

To my surprise, it interested her. After some encouragement from me, she rang them. The next day, with me by her side, she met with Matt. He was brilliant, putting her at her ease. He even made her laugh. Then, to everybody's surprise, including hers, she took to it like a duck to water. Three months later, she had a lead role in, 'An Inspector Calls'. I might be biased, but in my opinion, she stole the show.

Fast forward to now, and she was to star in an Off-Broadway show. It's a new play by a young Writer. It's called, 'A Woman Scorned'. And the woman that is being scorned, is my wonderfully talented Sister!

When I called Emma, to tell her the good news, she was as excited about it as I was.

"We should celebrate. See if you can get a table at Luigi's. Try for seven o'clock."

By some miracle, I managed to do that, but it could only be at eight. I didn't mind, it was a very popular restaurant, and most times, you have to book well in advance if you want to eat there.

At seven thirty, we picked Courtney up from her place.

As soon as she was in the car, Emma asked, "What's it like being a big star?"

"I'll tell you in six weeks, after the opening night."

That made us all laugh.

The evening was, as I hoped it would be, a fitting celebration. Good food and excellent wine, and even better conversation. We laughed a lot.

On the way home, while Emma was driving, I thought about my Sister, and our relationship.

Our Father left us when Courtney was only two, never to be seen again. My Sister has no memory of him, but I do. From what I remember, we are better off without him. I think Mother realized that, but it was hard for her bringing up two children on her own. It made her bitter and resentful, and at times, she took it out on both of us. Consequently, neither of us have a close relationship with her, but we do with each other. When, surprisingly, a year ago, she met somebody, and they moved away together, it didn't upset us. We were just happy for her. As long as we have each other, we are OK.

But what does Emma think about my Sister? Fortunately, for all concerned, the same as me. We met three years ago, and have been married for two. She regards Courtney as the Sister that she never had, rather than as just her Sister-in-law. And, to make it all nice and cosy, Courtney adores Emma. If she didn't, then I probably wouldn't have married her.

Four days later, rehearsals started, and now, while we were eating our evening meal, we were waiting to hear from Courtney. She had promised me that she would call.

"If it's a success, do you think it'll end up on Broadway?"

I was hoping so, but it was best not to look too far ahead.

"It might, apparently, both the Writer and Director, despite only being in their early twenties, have a lot of experience. This could be their breakthrough show, taking them into the big time, and Courtney with them."

We had just finished our meal, when my Sister called. I put it on speaker.

I asked, "How was it? Did you dazzle them with your amazing talent?"

"It was OK."

It had been said, without any real enthusiasm. It sounded as if it hadn't gone well. She then told us all about it, but there was no mention of any problems, or difficulty. I got the impression that she was keeping something from us. It was best not to ask. She would tell us, but in her own time.

When the call ended, I looked at Emma. I could tell that she was as concerned as I was. But hopefully, the next rehearsal would be better.

It wasn't, and you didn't need to be Hercule Poirot to know that, because, unexpectedly, my Sister came to our apartment, and she was crying. The tears were rolling down her face, and her eyes were puffy.

Between sobs, she said, "I can't do it."

I asked, "Do you want to talk about it?"

"Yes, but only with Emma."

That stunned me. She was my little Sister, and I was always there for her, and now she was pushing me away. It was as if she'd thrust a dagger into my heart. I looked at Emma, and she shook her head. The meaning was obvious. Don't say anything, just let me deal with it.

I left the room so that they could talk. But what was the problem? I had no idea, and trying to guess what it was, would only make me more agitated. I would just have to wait until they had finished, and then hopefully, when Courtney had gone, Emma would tell me all about it.

Half an hour later, they joined me in the kitchen. Courtney's face was red and blotchy, from all the crying, but now she was smiling, and it was obvious that it was genuine. I was relieved. Whatever the problem was, it looked as if it had been resolved. I had the good sense not to ask any questions, and shortly after, my Sister left.

"So what was all that about?"

"I'll tell you, but I'm not sure you're going to believe me."

I was now intrigued, eager to know. However, frustratingly, I had to wait until she had made herself a coffee, before she started.

"In act two, there is a sex scene. She makes love to Romeo, the other main character."

"So all that crying was because of that?"

"Yes."

That surprised me. There was now nothing unusual about having sex scenes in a play or film. In fact, it's almost compulsory. She was going to have to get used to it, if she wanted to become a successful actress.

"I don't understand why that upset her so much. It's not as if she's going to have to do it for real. It's only acting. It's no big deal."

"It is when you're a virgin."

That made my jaw drop, though I don't know why. Thinking about it, it shouldn't really have been a surprise, because I couldn't remember her ever having a boyfriend. But my Sister's sex life, was something that I had never considered before. And having to think about it now, was making me feel very uncomfortable.

"But it's even worse than that."

"What do you mean?"

Being a man, I couldn't think of anything worse than being a virgin. When, aged eighteen, I'd managed to bed my first woman, I'd been ecstatic. And, because she'd been ten years older than me, and experienced, it had been extra special.

"She has virtually no sexual experience at all. Some kissing, and a brief feel of her tits, on the outside, is it."

Then, to make it clear, how limited my Sister's experience was, she spoke again

"Nobody has ever got their hand inside her bra, or inside her panties."

I was finding it hard to believe. She was nineteen years old, and she had never experienced the pleasure, of having her nipples sucked, or her pussy fingered. Thinking about that, was making me feel uncomfortable, but alarmingly, it was also exciting me.

"And do you want to hear the best bit?"

I thought that she was joking, but when I saw her face, I could tell that she was being serious. She really had more to tell me, and I had no idea what it was.

"She has never even played with herself."

Was that her idea of a joke? When she nodded, I knew that it wasn't. So what she had said was true, but I still wanted her to confirm it.

"You mean that she has never..."

She finished it for me.

"Yes, she's never had a climax."

I shook my head in disbelief. Then, without any warning, she dropped a bombshell.

"And, so that she can be convincing, when she acts out the sex scenes, you are going to have to teach her."

I was speechless for several seconds, and then I blurted it out.

"You want me to fuck my Sister?"

That made her laugh, almost uncontrollably, but I didn't know why. What she had suggested, was no laughing matter. I was always happy to help my Sister, but that was something that I couldn't do.

"Don't be silly. You don't do it for real, you just act it out."

"Isn't that going to be awkward, even embarrassing, for both of us?"

"Yes, but as I told Courtney, you have to get over it. This is her big break, and if it doesn't work out, she might never get another one."

She was right. And if doing this for my Sister, helped her to achieve her goal of being a famous actress, it would be worth it. But I was definitely not looking forward to it!

The next day, while I was at work, Emma called me. It was a short conversation.

"Go round to Courtney's apartment tonight. She is expecting you at six."

It was sooner than I had expected, but I didn't complain. It was probably best to get it out of the way. Until it was done, it would be a worry for Courtney. And the longer she waited, the worse it would be for her.

I was delayed at work, so I didn't get to my Sister's place until seven.

"I thought you weren't coming."

She was smiling, so I knew that she wasn't annoyed, but I still felt the need to apologize.

"Sorry Sis, I had to finish off something at work."

"It's OK."

Then her face changed. Gone was the smile, replaced by a worried look. I could understand that, because I was worried as well. I knew what I was here for, but I had no idea how I was going to do it.

To put her at ease, I said, "Don't worry, I'll be gentle with you."

It worked, sort of, because her smile was back, but it wasn't as radiant as before. She was still anxious.

We started with her telling me what was in the script. Most of what was to take place, was in the living room. The couple would make love on the floor, in front of an open fire. They would be covered by a blanket. But the first part was in the kitchen, where they kissed for the first time.

"We can skip the kissing. Let's go straight to the..."

I'd stopped, because I could tell from the look on her face, that wasn't what she wanted to do. But why not? Then I suddenly realized that she wanted to start at the beginning. She wanted me to teach her how to kiss!

We were now in a close embrace. I could feel her breasts against my chest, and our heads were only a few inches apart. When she hugs me, as she often does, we are even closer together than this. But this was different. It felt more intimate, because of what we were about to do. To pretend to kiss.

"Do I close my eyes?"

"You can if you want to. It's up to you."

"What does Emma do?"

At first, I wasn't going to tell her, but then I realized that would be silly. It wasn't as if I was betraying Emma, by revealing some big secret.

"She keeps them open."

"Then that's what I'll do."

"OK, let's start. We need to put our mouths close together, but not actually touching. Then you pretend to kiss me."

At first, I thought she was being silly. The jerky movements and contorted face, were to make me laugh. But she wasn't. It was how she thought she should react. I had to stop it.

Eagerly, she asked, "How did I do?"

In a word, 'awful', but I had to let her down gently.

"It needs more passion. Try to imagine that I'm somebody that you have always wanted. Just let yourself go."

We tried again. It was slightly better, but still a long way off what it should be. When I told her, she was on the verge of crying.

"It will be better in rehearsals, because you will really be kissing."

"We should do that now, to make it realistic."

I shook my head, and then, to make it clear that it was out of the question, I said, "No, you're my Sister. It wouldn't be right."

This time, she couldn't hold back. When the tears came, I almost cried as well. It was breaking my heart. Should I change my mind?

After all, it was only kissing, and we would be doing it for an innocent reason. When I told her that we would do it, the sobbing stopped.

After wiping away the tears with my hand, I put my mouth on hers. For a few seconds, she didn't react, and then she started moving her mouth. We were kissing, but without any real emotion. Then she parted her lips. It was what Emma did, when she wanted my tongue in her mouth. And, without thinking, I reacted as I would with her. It should have freaked Courtney out, perhaps even made her cry again, but it hadn't. Her response was both surprising, and alarming, because she was now eagerly sucking on my tongue.

It was as if a switch had been flicked. Changing her from a shy virgin, who didn't know how to kiss, into an experienced lover.

It hadn't taken her long to demonstrate, that actually, she could really kiss. And if she performed like this in rehearsals, the Director, and her fellow actor, would be impressed. But I didn't stop it, I let it continue. I could fool myself, by saying that it was just to make sure that she had got it right, but that wasn't true. I was now doing it for one reason, and for one reason only, because I was enjoying it. And the proof of that, was my cock, because it was now fully erect.

We had now kissed for at least ten minutes. And it had been as passionate, as if I was with Emma. We had taken so many turns exploring each other's mouth, that I had lost count. We needed to stop.

When we parted, we were both breathless. This hadn't been acting, it had been for real. When I saw her face, I could tell that she was thinking the same thing.

"I think that we can say, without any fear of being contradicted, that you nailed it."

That made her giggle. When she had finished, she said, "So far so good, but what do we do now?"

I didn't know. I hadn't given it much thought. Was there any detail in the script? When I asked her, she told me that there was, and she then quoted from it.

"After kissing passionately..."

I interrupted with, "We can tick that box."

She ignored me.

"Romeo reaches for her breasts. Janet gives them to him willingly."

I had to smile. Romeo and Janet. Apparently, the names had been chosen to mock conventional stereotypes. My Sister had explained it to me, but I wasn't convinced. The Writer probably thought that he was being clever, but he wasn't. He was just being a twat!

"OK, we can do that. I pretend to touch your breasts, and you act as if you are enjoying it. I then tell you how you've performed."

She was now thinking about it, but I didn't know why, because it wasn't complicated.

"Wouldn't it be better if you put your hands onto them? It will help me. My reaction would be more natural."

She had surprised me with that. I knew that I should say no straight away, but I decided to consider it. I was here to help her, even if that meant doing things, that others might think were inappropriate.

She was wearing a baggy T-shirt, but it couldn't hide her prominent breasts. Emma's were impressive, but hers were at least a cup size bigger. Yes, it would be more realistic, if I was to touch them. But if I did, we would be crossing a line. I was about to say no, when she spoke again.

"It would only be on the outside. It's not as if you are putting your hand inside my bra."

So that's OK then? I could tell all my friends at work that I've played with my Sister's tits, but they shouldn't be shocked, because she kept her clothes on!

"And it's not as if I'm going to tell anybody."

That shouldn't have made me change my mind, but for some reason, that I couldn't figure out, it did.

Casually, I said, "OK, let's do it."

We kissed for a short while, before I moved my hand towards her breast. When it got there, she tensed. I waited until she had relaxed, before fondling it. I loved its firmness. From what Emma had told me about her, her tits had been played with before, but not very often. So I started gently. Then shortly after, I got bolder, more ambitious.

I now had both hands on her, one on each of her firm breasts. Fondling had become groping. What had once been gentle, was now rough. But she wasn't complaining, she was moaning. This now wasn't to teach her, it was to give both of us pleasure.

When I started pulling on her nipples, her moaning became louder. Despite them being covered by a bra and T-shirt, I could tell that they were big, much bigger than Emma's. I desperately wanted them in my mouth. To be the first to do that.

My hands were only supposed to be on the outside, but they were now going under her T-shirt, and she didn't try to stop me. When I got to her bra, I thought that she might now say no, but instead she leant forward, and I instantly knew why, it was so that I could reach behind her, and unhook her bra.

It was now on the floor, and her top was pushed up. My mouth was eagerly sucking on her nipple, and my fingers were on the other. This was good. Tits don't get any better than this, and I was making the most of them. It was special, and I could tell that it was for her as well. Every time I sucked hard, greedily taking in not just the nipple, but as much of her breast as I could manage, she gasped. She was definitely making all the right noises, and at the right times. Regarding her tits being played with, there was nothing I could teach her.

If this was Emma, it would now be time to finger her. And she would be eager for me to do it. Should I do that to my Sister? No, feasting on her magnificent tits, was bad enough, but putting my fingers into her most sacred place, was out of the question. That was a convincing argument, but my cock wasn't listening. It was rock-hard, and throbbing. And it was in control. It might end with some harsh words from her, or even a slap across my face, for trying to go too far. But I was going to go for it.

I managed to unzip her jeans, and to unbutton them, before she stopped me from pulling them down, by holding onto them. I tugged on them again, but she held firm. I was frustrated, but there was nothing that I could do about it. It was obvious that she wasn't going to change her mind.

After taking my hands off her, I muttered, "I need the bathroom."

I waited until my cock was down, and I had composed myself, before returning. As expected, she was fully clothed. But what would her reaction be? I had no idea. She might be regretting what had happened, she might even be angry with me. I was her big Brother, somebody who should take care of her, but instead, what I had done, is take advantage of her.

"Thanks, I've learnt a lot. It will really help me when I rehearse it."

And then, to confirm that everything was OK between us, she gave me a big smile. To say that I was relieved, was an understatement.

I stayed for another half an hour, while we talked about lots of things. But there was no mention of what had happened. It was the elephant in the room.

As I was leaving, she gave me a kiss, but just a peck on the cheek. Then, with my hand on the door handle, about to leave, she surprised me.