Surprise Lessons (1)

Sexy sister is home for the summer and decides to help brother with self-confidence.

I woke to the sound of mom heading out for work, and to the smell of coffee.

“I’m leaving, kids. You two have a good day.”

I heard Samantha answer. “Bye, mom. I love you.”

Sam was home for the summer, between her first and second year of college. I was sad when she left home last fall. It was nice to have her back. I just turned sixteen, and she’s almost four years older than me.

Our single mom works full time as a legal secretary, and Sam had pretty much looked after me for years. I love her like crazy. I rarely saw any girl that I thought was prettier than her. If I had try to describe her to somebody, I would say that she is slim, with a great figure, and long, straight, medium-brown hair that she most often wears in a cute pony tail. I would also say that she looks a lot like Zoey Deschanel. They both have that sweet, innocent, endearing, loveliness.

I rousted myself from bed, slipping into a pair of cargo shorts and a polo shirt. Barefoot, and needing to pee, I headed to the hallway bathroom. The bathroom door was ajar. I pushed it open and walked in thoughtlessly. I looked up just in time to see my sister lowering herself to sit on the toilet, with her shorts and panties down around her ankles. She looked at me in surprise, as she sat the rest of the way down.

“Oh, my gosh, Sis. I’m sorry.”

“It’s okay. No worry. I should have closed the door, but I thought you were sleeping.”

“Again, sorry” I said, turning back towards the hallway.

“No need to leave,” she said. “I won’t be long.”

I heard her stream of pee start. The sound rapidly increased in volume.

I was stunned. I’d never seen my sister in anything even close to such a intimate way. My dick was already half morning-hard. Hearing her pee, it suddenly sprung tight against my shorts.

“Uh, you mean, you’re okay with me being in here?”

“Yeah, it’s okay.”

I could see her eyes move to the growing bulge in my shorts.

She smiled slightly as she reached to gather a wad of tissue. Her next question surprised me again.

“Does it turn you on to be here with me while I pee?”

Her splashing stream continued.

I stammered and looked at my feet. “I’m sorry,” I said.

“What do you mean to be sorry for? It’s probably a natural reaction. I find it rather flattering.”

As her flow stopped, I watched as Sam raised slightly off the toilet seat, reached behind her butt, wiped herself, and dropped the tissue into the toilet. She stood up, turning towards me as she reached down to push the flush handle. She was apparently not embarrassed because her movement let me see the shaved top of her slit. This was my first ever glimpse of a girl. She squatted slightly to reach her shorts that were still at her ankles. My cock got even harder as this revealed more of a hint of her pussy.

With her clothes back in place, Sam took a step towards me. She leaned forward and kissed me on my cheek. She whispered, “Why don’t you do your morning
things, then meet me in the kitchen. I want some coffee.”

As I quickly showered and brushed my teeth, my mind was racing. For years it had been my fantasy to see my sister naked. For years I had watched for any chance to glimpse her bare tits, or more. She had just let me watch her pee, and briefly see her smoothly shaved slit.

A few minutes later, I joined Sam in the kitchen. She was propped against the counter, drinking coffee and looking at her cell phone screen. I’m not a big coffee drinking, but I poured myself a cup, and leaned against the opposite counter. Sam put her phone down.

Sam laughed a bit, “So, was that the first time you ever saw a girl pee?”

“Yeah. Well, really, I’ve never seen a girl, uh, do anything before.”

“Tell me how it is going for you with the girls. Did you have a steady girlfriend last year?”

“No. No girlfriend. Oh, there were a couple of girls at school that I liked, but they both had boyfriends. I never even talked to them.”

“That’s surprising – that you don’t have a girlfriend.”

She was silent for a moment, apparently thinking about that.

She went on, “It’s probably mostly just your lack of confidence. In the last year you’ve grown into quite a handsome young man. Do you remember when Annette came to spend a few days with us last Christmas?”

I nodded. Annette was Sam’s roommate, and new best friends from college. She came a few days early to drive the both of them back to school. She stayed with us for two nights. Annette is a pretty, petite blond; though not as attractive Sam.

“Annette told me, more than once, how good looking she thought you are. She said that if you were a little older, she might try to hook up with you.”

I didn’t know what to say. I felt flattered, but also felt my cheeks getting red and hot.

“If you’re interested, little brother, I think I might be able to help boost your confidence with girls. I would like to see you have a sweet girl in your life. I’ve always thought that you were cute as a bug, but since Annette’s comments at Christmas, I’ve come to realize that you’re also quite sexy.”

When she went silent, I mumbled, “Well, thanks. That would be great. I’d like to have a girlfriend, but how do you think you could help?”

“I think I can coach you on what girls like, and how to treat them. And maybe I can convince you that you are attractive enough to girls that you have no reason to be so shy. Come here.”

I took the three steps to where Sam was standing. She’s is 5’8” to my 5’10”. She was wearing sandals, white tennis shorts and a loose, flowery tank top that reached down to her hips. She pulled me into a tight hug. I was instantly aware of her firm breasts pressing against my chest, and aware of how good she smelled, like powder and perfume. It was heavenly to be in such an embrace with my beautiful sister. It was the stuff of my dreams.

“Now, kiss me,” she said. “That’ll be our first lesion. And in every way you touch a girl, be gentle until she gives you a sign that she wants it to be more firm.”

“I’m so nervous,” I said, “I’m shaking inside.”

“That’s okay. We’ll get past that. I love you brother. I want you to kiss me.”

I lowered my head a bit and put my lips to her soft lips. Her mouth was so sweet. My head was spinning. Sam moaned slightly. I felt her tongue part my lips and press against my teeth. Tasking her queue, I opened my mouth a bit and felt the tip of her tongue dance against mine. Until that moment, I had no idea how wonderful, and sexy, such a thing might be. I became aware of my rock hard cock now pressing against her thigh. She kissed me more deeply, at the same time pressing herself hard against my crotch. Sam moaned again, pulled slightly back and kissed my face and my neck. She pulled further away and spoke.

“Oh, my. That was lovely. One would never know that you’re a beginner at that. Remember, always keep your focus on doing what you think would feel good for her. I liked that a lot.”

“Now, put your hands behind my back and slide them up under my top . . . Now, gently stroke my back with your fingers . . . Yes, like that. That feels nice.”

My fingers confirmed what I thought I had felt with my chest; that she was not wearing a bra.

“So,” she said. “You’ve never felt up a girl’s tits?”

I couldn’t help but laugh a little.

“No, definitely never. Well, only in my dreams.”

“Okay, let’s fix that now. Move your hands to my front, and lightly stroke my stomach . . . Yes, that is nice too . . . now gently work your way up my front. I can’t speak for all girls for sure, but the girls that I know all do appreciate a gentle touch. You can caress my breasts. I would like that.”

To hear her give me that invitation stirred a swarm of butterflies in my stomach. Shakily, I worked my way up under her shirt to touch the undersides of her breasts. I traced around her soft and warm globes with the backs of my hands. As my finger’s brushed over her nipples, Sam gasped slightly.

“Oh, little brother, that feels nice.”

To my shock, Sam reached down and squeezed my cock through the fabric of my shorts. With sudden urgency, she worked open the buttons of my fly and pushed my shorts down over my hips so they dropped to the floor. I was suddenly very glad that I’d decided not to put on any underwear beneath my shorts. Sam encircled my cock with her cool fingers and stroked me slowly.

“Your cock feels so nice in my hand. Now, kiss me again.”

We kissed with even more passion. Her tits are too big to fit entirely in my hand, but I cupped them both as nearly as I could, and gently rolled her erect nipples between my thumbs and forefingers.

Sam whimpered more deeply as she released my cock and gently cupped my balls.

“Oh, my God,” she said. “You’ve gotten me so aroused. When girls get aroused, their pussy will get wet and slippery. And my pussy is very wet right now.”

It was a shock to hear her even speak the words “cock” and “pussy”.

She reached up, took my right wrist in her hand, and guided it under the waistband of her shorts. She spread her legs slightly and moved my hand down to touch her mound.

“I want you to touch me between my legs,” she whispered. “With your middle finger, feel down the length of my slit. You’ll feel how wet I am.”

Sam rested her head on my shoulder as I fingered her gently. For the first time my life I was not only feeling a girls tits, but I was now exploring her pussy with my fingers. Several times, I stroked my finger slowly up and down her slit, spreading her lips a bit wider, and probing a bit deeper each time. I was amazed at how wet and slippery she really did feel.

“This is very nice,” she said, “But enough of this standing. It’ll be lot more comfortable if we go to my bedroom.”

Sam kissed quickly kissed my lips, pulled back and said, “Give me a few minutes to get ready, then come to my room.”

As I watched her walk to the hallway, I was in a state of bliss. I had to check myself to be sure that I wasn’t dreaming.

More times that I could count, I had masturbated to fantasies of doing sexy things with my pretty sister. The hallway bathroom was between our bedrooms. Many times I had masturbated to the sound of her peeing loudly in the toilet, or the sound of her showering, imaging seeing her naked in those moments.

Having pulled my shorts back up, I hesitantly walked through the open door to Sam’s room. It was not unusual for me to be there. Many times we had sat on her bed together and played games, or just talked.

Her room was still decorated as it had been during her high school years. It was all very feminine and frilly. There were no posters on the walls, no high school pennants, or junk like that. It was just tasteful girly décor; and it always smelled nice.

Sam had pulled back the duvet cover, and was laying between the sky blue sheets with her head propped on her elbow, facing the door. I hesitated.

“Come here little brother.”

As I walked towards the bed, she suddenly said, “Stop.”

I froze in place, wondering what her order meant.

“Now,” she said, “Your price of admission is to let me watch you take off those clothes. I want to see what you look like. I mostly want to see your naked tight butt. There’s no need to be embarrassed. I will take care of you. I really just want to admire you.”

I lifted my shirt over my head, and chucked it into the corner.

“Very nice,” she said. “Now, the shorts.”

Still shy about it, I sheepishly lowered my shorts to the floor, and stepped out of them. It added to my embarrassment that my cock was standing at full attention. I resisted a desperate urge to hide myself. For several seconds, Sam just stared at me, her eyes moving up and down my body.

“Oh, my. That is beautiful. I guess I need to stop calling you ‘little’ brother. THAT is not so little. Turn around and let me see your butt . . . Mmmmm . . . quite lovely, really lovely. I don’t know why seeing a boy’s tight butt is so erotic to me, but it really is. I guess maybe because it makes me think of laying on my back, with those hips driving between my legs, my ankles locked around that ass, and my hands feeling those tight buns. I’m sure most any girl would like this view. Now, come here and get under the cover with me.”

As I slid under the covers, Sam pulled me to tight to her chest.

“Kiss me some more, little brother. It’s almost impossible for a girl to be kissed too much.”

We kissed deeply. I felt the thrill of her whole naked body in close contact with mine. It was an indescribably delicious feeling. She put her left leg over my right hip. I felt her warm, wet pussy pressing my thigh.

“Now, little brother, kiss my breasts. I want you to suck on my nipples.”

Sam raised the sheet to reveal my first look at her beautiful tits. They were stunning, very erect, and bigger than I imagined. Not knowing about such things, she told me later that they are size 34C.

We both have slightly dark complexions, and her body is the color of cream with a dash of coffee added. Her nipples are silver-dollar-sized, with puffy, reddish-brown nipples. I tenderly cupped under her breasts.

“Oh, my God, Sis. Your breasts are the most beautiful things I have ever seen. They’re so soft, and warm.”

“I’m glad you like them,” she whispered hoarsely. “Kiss them a bit, then lick my nipples, and suck them gently into your mouth.”

Reverently, I did just as she asked. As I suckled her nipples, Sam whimpered in a most endearing manner. I was so aroused by this time and I felt that the barest touch of my cock would make me come.

Sam seemed to read my mind. “We have all day for this, so there’s no hurry, but I imagine that you are quite ready to come by now. Am I correct?”

“Yes, but I don’t want this to end.”

“Oh, it won’t end any time soon. For now, I don’t want you to be uncomfortable, because I have many more lessons in mind for you. And I think you won’t be able to properly concentrate if your balls are so full of your cum, aching for release.”

Sam threw the cover all the way back. She reached down and brushed her fingernails over my rigid member, and my balls. It was thrilling to be touched.

“How about if I stroke your cock a little, while you finger my pussy again? Does that sound like it might work for you?”

“That sounds heavenly, Sis.”

For the first time in my life, I felt another hand stroking my cock. My hips and butt muscles tensed with each stroke. I fingered her wet slit. In combination this was the most erotic thing I’d ever experienced. Without really trying, my middle finger found her wet hole. At the same time, Sam reached down to her pussy. She dragged her own finger through her slit, alongside mine, then brought that wet finger to my mouth and put it to my lips.

“Here, I want you to taste my pussy.”

I sucked her finger into my mouth. Not only did I taste her, but I smelled her, and the combination was delicious. It was such a girl taste and smell that it excited me beyond description.

“Oh, my God, Sis. I love the way you taste. But I’m going to come so soon.”

“That’s fine, little brother. I want to watch you shoot your cum.”

Sam gripped a little harder and stroked a bit faster. It wasn’t more than five more strokes of her hand when I reached the point of no return. Every muscle in my bottom seemed to contract in the same instant. Involuntarily, my hips raised off the bed.

“Oh, God, I’m coming now.”

The first spurt of my semen arced high in the air, landing on my chest, just below my chin. Three more spurts landed on my breast bone and my stomach. The last of it flowed down over Sam’s fist. It was the most intense orgasm I’d ever had.

“Oh, my,” she said. “I can see that you really did need to come. That was quite sexy, and quite impressive.”

Once I stopped panting and relaxed a bit, Sam reached to her night stand for a damp towel that she had obviously already prepared. She tenderly wiped up my cum.

“Thank you, Sis. That was so good.”

“You’re welcome, brother. I’m glad you liked it. But once you are up to it, it’s now your turn to make me come. Normally, it will get you further with a girl if you tend to her needs first. But, this was a special situation.”

“How do I make you come?”

“Well, there are several possibilities, but my preference at this point would be to have you lick my pussy until I come. Does that sound agreeable to you? Do you have any hesitation about kissing a girl down there?”

“Not at all. I would do anything for you. I want to see you down there. I really want to kiss and lick you down there. I want to taste your pussy some more.”

It was warm enough in the house that we didn’t need any covers. Sam threw off the sheet, and gently urged my head down.

“Kiss my stomach. Kiss me all the way down to my pussy.”

I moved so that I was on top of her, with my hips between her legs. As I scooted down towards the foot of the bed, I gently kissed her tits, moving slowly down as I kissed her soft and downy stomach. As I worked my way to her mound, she spread her legs wider apart, and entwined her fingers in my hair.

“Oh, yes, baby. Now, lick my pussy.”

I inhaled her slight musky scent as my tongue contacted her outer pussy lips. Her pussy lips were about the same shade of reddish brown as her nipples. I’d watched enough porn to have seen some variety of pussy shapes and sizes. Sam’s inner lips stuck out nicely, but delicately. It is easy to say that no pussy ever looked nicer than hers. I ran my tongue over both sides of her every crevasse and fold. I tasted her slippery liquid, which really had almost no taste, gathering and swallowing all that I could scoop up with my tongue.

“Oh, yes, little brother. That is so nice. Stick your tongue in my pussy hole now . . . Oh, yes. Fuck my pussy with your tongue.”

Even though I had no real world experience, I had seen enough porn, and read enough stories, to know about the sensitivity of a girl’s clitoris. After licking all around and inside of her wet hole, I moved up to where I understood her clit to be. With my tongue at the top of her slit, I felt her hard, pea-like nub. As I licked that nub, my beautiful sister squealed in delight.

“Oh, yes, baby. That’s the good spot. That is so hot. You’ve got my pussy so hot. Now, gently suck on that. Take it gently between your lips and put and little suction . . . Oh, yes, that is wonderful. That’s perfect. Now, with the index finger of your right hand, slip your finger into me.”

For the first time in my life, I felt the inside a of girl’s pussy. I felt the slippery and velvet smooth walls of her cavity.

“Yes, that’s perfect. That feels so good. Baby, one more thing, just inside the entrance of my pussy, on the top side of my vagina, you can feel a bit of a rough place with your finger tip. That is also a very sensitive spot. It feels good to have you gently massage that spot while you suck on my clit. Yes, just like that. That is so good. You are doing perfect, baby.”

As I alternately licked and sucked on her clit, and I slipped another finger into her hole. I alternated between finger fucking and massaging what I understood to be her G-spot.

“Oh, yes, baby. I’m getting really close. You’re going to make me come. Suck just a little harder, baby. Yes, finger my pussy a little faster.”

I looked up to Sam’s face, and saw that she was caressing both of her tits. She rolled end of her nipples between her fingers and pinched them lightly.

“Oh, fuck, baby. I’m going to come now . . . I’m cummmming.”

Sam’s face took on a grimace. Her hands flew to her sides and she balled the sheet into tight fists. Her hips bucked and she pushed her pussy hard into my mouth. She jerked hard 6 or 8 times. With the same timing, I felt her pussy squeezing my fingers, and her breath huffed out huskily. Very slowly, her body relaxed as her orgasm subsided. She stayed dead still for a moment before speaking.

“Mmmmm. Oh, baby, you did that so well. I came so hard. Now, come up here and kiss me.”

As moved up between her legs, and put my face close to hers. My face was wet with her pussy juice.

“Mmmm,” she said, licking my face. “Your face smells and tastes like my pussy. I like it.”

Sam reached down between us and gripped her hand around my once-again-rigid cock.

“Oh my, it seems like you might be ready to go again. Lift u p a little.”

I raised up on my elbows. Sam guided the head of my cock to her slit, moving it up and down her wetness. She then stopped moving it, right at the entrance to her vagina. She just held me there for a moment, looking into my eyes. I tried to speak, but could only get out a single word.

“Can . . ?”

“Yes. You can fuck me,” she whispered. “I want to be your first.”

She pulled on my cock just enough that I barely slipped past her entrance.

“Go slow at first. It’s been a while for me, too.”

Sam moved her hands to my hips. By just flexing her fingers, she gently urged my hips to her. I felt her pussy walls open up a bit, and let my cock begin to slide in. With about two inches in, she reversed her pressure on my hips, and urged me to withdraw a little.

“Yes. That’s it. Just work your cock into my pussy a little at a time. Give me time to adjust to your size.”

Very slowly, I stroked in an out, moving slightly deeper with small stroke. What I was feeling must be about as it feels in heaven. She was so warm, and snug, and inviting. It was like liquid silk around my cock. She was so wet that I slipped in her with almost no resistance.

“Oh, yes, baby. That’s perfect. You feel so good inside of me.”

After about eight or ten slow strokes, my pubic bone was tight against her mound. There was no deeper to go. Sam hooked her legs around my back, and held me inside of her. I moved my mouth to hers and kissed her deeply.

“Oh, Sis, I love you. I love you so much. I have dreamed of this, but I never thought it could really happen. I think you are the most beautiful girl in the world.”

“I love you too, baby.”

I moved my head down to suck on her tits while my cock was deep in her pussy.

“Oh, Sis, your tits and your pussy are so beautiful. Your entire body is so sexy.”

“And I like yours too, my young stud brother. Now, fuck me.”

I began slowly stroking nearly the entire length of my cock in and out of her pussy. I raised up to support my weight on my hands. I look down at my waist. I wanted to see my cock sliding in and out of her. It was stunningly erotic to see the lips of her pussy encircling my shaft as I withdrew it on each stroke.

“Oh, yes, baby. That’s so good. You can go faster now.”

I began thrusting harder, with more urgency.

“Oh, yes, baby. That’s it. Fuck my pussy. Fuck my pussy with your big cock. Fuck my cunt. Do it hard and fast now.”

I was trying to hold back my orgasm, but I was losing the fight. Sam was gasping and moaning.

“Oh, fuck, I’m going to come again soon . . . yes, baby. Harder, baby. Fuck me hard.”

Her hips began thrusting upward to meet each of my strokes as I pushed into her as hard and fast as possible. My own orgasm was boiling up. To hear such nasty talk for my sweet, beautiful sister was sending me over the edge.

“Oh, baby. I’m so close,” she said. “Don’t you dare stop. I want to come around your cock. I want to feel you come inside of me.”

“Oh, Sis. I’m close too. I’m going to come again.”

“Yes, come in my pussy. Now, baby! Come now!” she shouted. “Oh, fuck. Oh, fuck. Oh, God. I’m coming.”

My body responded faithfully to her command. My loins contract fiercely again. As Sis was bucking from her own orgasm, and as my cum rose, I pushed in deep, then held still. With a eight or ten strong contractions, my cum spilled into my sister’s most intimate cavity.

We lay there for a minute, silent, with me supporting most of my weight with my hands on the mattress on each side of her.

“Oh, little brother. That was so good. You were perfect.”

Together, we rolled to our sides, face to face, her leg under my hip, with my half-hard cock still inside of her. I reached up and caressed her nipples.

“Mmmmm. That’s nice. You seem to be understanding the gentle part of the lessons quite well. I’m liking that very much about you.”

Sam reached over me to a small, dry towel that was on her night stand. As she moved it towards her sex, I slipped out of her. I moved my hips out of the way so she could put the towel between her legs.

Sam laughed. “I just don’t want to mess up my good sheets too much.”

“Can I kiss you again?” I asked her.

“Anytime, my dear.”

As we kissed, I felt strong emotions rising. I was surprised when my tears starting flowing silently. Sam noticed.

“Oh, sweetheart. What’s wrong?”

“I don’t know if I can explain it. I just feel so emotional. My heart is so full of love for you. And I started feeling afraid that I’m going to lose you.”

“Oh, my love. Don’t be sad. You’re never going to lose me. We won’t always be able to do sexy things with each other, but I can promise that I’ll never stop loving you. Someday, probably fairly soon, you’ll find a girl that you will love with just as much intensity as you are feeling now. And she will rock your world, too. But I’ll never forget, and I will never regret, what we just did. I’m honored that I was your first. Plus, I’m not at all finished with your lessons. If it’s okay with you, I’d like to continue this tomorrow – after we’re rested.”

Sam laughed, and added with a whisper to my ear, “And when your balls are full of cum again.”

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