Surprise Lessons (3)

Samantha and her little brother share an experience that’s new to them both.

It was Friday when Samantha and I were next able to get together. She had received a call asking her to come in Wednesday for day-long new-employee orientation at the hospital. They had set her shift schedule to start next Sunday, so she needed an early orientation.

Thursday evening, Sis offered me some more relationship coaching.

“We need to fix you up with at least one opening line for how you might walk up to a pretty girl and start talking to her. What would you say?”

“I don’t know. That’s always been an obstacle.”

“Okay. Well, how about something this: ‘Hi, I’m Tristan. We’ve never talked, but I’ve admired you from a distance, and I’ve wanted to talk to you for a long time.’”

“That seems good,” I replied.

“Okay, what would you say next? After she says, ‘Thanks, Tristan. I’m glad you did.’”

“Uhhh . . . I have no idea.”

“How about something like, ‘Thanks. It’s a little hard for me to work up the courage to introduce myself to a pretty girl.’ With the one sentence, you’ve admitted to your vulnerability, which most girls will find attractive, and you’ve paid her a nice compliment. Just don’t ever go into the childish crap like, ‘Hey, do you know this person?’ Or ‘Do you know that person?’ You need more game than that.

“Hopefully, she’ll reply something like, ‘Awww, you’re so sweet.’ Then, maybe the ice will be broken, and conversation will start getting easier. After that you can ask to walk her to her next class, or sit together at lunch, or meet up in the courtyard after school.”

“But don’t try to be clever. Just be sincere. And . . . so what if she doesn’t show any interest? She might tell one of her cute friends about you, and cute friend might signal you. But you have to put yourself out there. You’re not always going to score, but you definitely won’t score if you never try.”

“And don’t hold back just because she’s standing with a friend. If you wait to catch her alone, you might wait forever. She’ll probably be more open to talking to you if she isn’t alone. You know . . . protection in numbers.”

Friday morning, Sam was late getting up. It was almost 10:00 by the time she came into the kitchen. She looked as pretty as ever, wearing a flowery satin robe that dropped to the middle of her thighs. She walked right to me, then grabbed me in a hug. She smelled so nice, like scented powder.

“Good morning, little brother. I’ve missed you.”

I was relieved to have her initiate the contact. I‘d grown a little nervous about what might come next.

“I’ve missed you too, Sis. How was shopping yesterday?”

“Oh, it was fun. I didn’t buy anything, but it was fun helping Diane. She bought a lot of nice things. That’s what took us all day.”

Sam laughed, “It was fun, but more than once I thought of how much more fun it would be in bed with you.”

I laughed too.

“Wow, I’m glad you didn’t forget about me.”

That was my anxiety speaking.

“No. I surely didn’t. Is the coffee still warm?”

“Yep, when I heard you in the shower, I started a fresh pot.”

“Good boy. Very thoughtful.”

Sam poured herself coffee, then leaned against the counter.

“So, little brother, have you been good? Have you refrained from self-stimulated sex play while I’ve been otherwise occupied?”

I blushed. “Well, yeah. I resisted. It wasn’t easy a couple of times, because just thinking of you would get me so worked up. But I was trying to save my. . . how should I say it? I was hoping I was saving my ‘capacity’ for when we could be together again. I was hoping that might be today.”

“Good boy, again. That was my plan too.”

Sam took another drink of coffee, moved next to me, and learned against my chest. Her robe was loose against her breasts. I could see her left breast and nipple. Sam has gorgeous tits. I love the way her reddish-brown nipples are notably darker than her skin tone. Her nipples are like carefully sculptured accent pieces. The line of her nipples perfectly continue the line of her breasts.

“I want to feel your hands on me,” she whispered.

I reached into her robe and cupped her left breast in my hand. The warmth, softness, and sheer femininity of her was thrilling. I gently rolled her nipple between my forefinger and thumb. Sam whimpered in response.

I moved my hand down, under the belt of her robe, and gently stroked her flat stomach. When my hand reached her mound, and I as started to slip my middle finger down her slit, Sam pushed on my cock through my shorts. I dragged my finger up to circle her clit – as she urgently reached under my waistband and gripped my cock in a strong fist. I massaged her clit with my wet finger.

“Oh, baby. That feels so good. You’re making me so wet again. I want to do everything with you. Take me to bed now.”

After snuggling under the sheet, and kissing deliciously, Sam whispered.

“So, tell me again. What other fantasies have you had in mind over the years – when you were making yourself come? Don’t be shy. Whatever it is, I want to hear it.”

“Oh, there are a bunch. One big one is that I’m really curious about how girls masturbate. I read a story once about two guys and two girls that shared an apartment at college. They were just friends, but the good part of the story was when they all decided to sit in a circle, and all masturbate in front of each other – at the same time. That image made me come so hard, so many times.”

“Hmmmm . . . That does sound sexy. So, do you want to see me make myself come?”

“Oh, yes. I would love that.”

“That’s a good one,” she said. “Because I’d like to watch you jerk off too. I like to see your come shoot out of that big cock of yours. Why don’t you get down between my legs now, and lick my pussy some . . . because you are VERY good at that. Then, you can kneel between my legs. I’ll finger myself while I you watch, and while you stroke yourself. Maybe we can come at the same time again. We seem to be good at that. Does that sound like it might work for your fantasy?”

“Oh, God, Sis. That sounds like my dream come true.”

Her pussy tasted wonderful, as always. After licking her slit, I put my hands on the bottom of her thighs and urged her legs high to her chest, and wide apart. For some reason, I was almost crazy with desire to lick my sister’s puckered butthole again. I started at it very gently. Sam just moaned in response,

I’ve read that some girls with dark skin now actually try to bleach their buttholes. Apparently they think a pink butthole looks cleaner, sexier, or something. I don’t understand that. It’s very erotic to me to see the ring of Sam’s asshole being darker that her skin tone. Just like with her dark pussy lips attract my eye in such an exciting way.

I stiffened my tongue. With a tongue full of saliva, I worked it into her tight hole, at least as much as I could, which was not much.

“Oh, fuck,” she said. “That’s hot. I’ve never had a tongue in my ass before. It’s nasty, which makes it even better . . . but come up here now, babe. I want to come soon.”

I got back on my knees between Sam’s legs. I leaned forward and kissed her again. She kissed me back, urgently.

“Do you want to watch me finger myself now?”

“Oh, yes.”

“Do you want to watch me finger fuck my pussy?”

“Oh, God, yes.”

As I knelt upright between her legs, Sam put the soles of her feet on my upper thighs. I stroked my cock slowly. She surprised me when she reached under her thighs and spread her pussy lips wide apart. The contrast of seeing her pink hole framed by her dark pussy lips nearly made me come. I had to stop stroking myself.

“I know you are highly visual. Does it excite you to see me spread my pussy open for you?”

“Oh, so much. It’s so exciting that had to stop touching myself in order not to come in that moment. Your pussy is so beautiful. You are a vision, and not just between your legs. All of you.”

Sam laughed. “Well, thank you for the compliment. A lady does like to be admired.”

Sam kept one arm under her thigh. She inserted the middle finger of that hand into her pussy hole as she rubbed her clit with the other hand.

“This is how I make myself come sometimes,” she told me. “And you have me so hot now, that it won’t take me long to come.”

She added her index finger, fucking herself with two. She plunged her pussy hole faster, at the same time her rubbed her clit more furiously. I still didn’t dare touch myself. The scene was so hot that I thought I might come in about two strokes.

I moved my left hand down to caress Sam’s beautiful butt. I slipped my finger along the bottom of her slit, getting it wet with her slick juice. I pushed that finger between her butt cheeks to feel her butthole. I moved my finger lightly over her hole. I put a little pressure on her tight ring. I was intending that just to flutter those nerves when my finger slipped right through her tight ring – with surprising ease. My finger was in her asshole up to my first knuckle.

“Oh, God, baby. This is nice. I’m very close to coming. I want you to come with me. I want you to shoot your come on me. I want you to come on my pussy. I want to feel your cum splash my belly. I want your cum on my tits.”

“I can come at any time, Sis. Just tell me when.”

I started slow stroking my cock. She took her fingers out of her cunt and pinched her left nipple. She was now frigging her clit with urgent speed. I removed my finger from her butthole, and reached up to roll and tug her other nipple.

“Oh, fuck. I’m there now. Come on me now, baby. Oh, fuck. Fuck.”

As Sam grimaced, and jerked her torso slightly up off the bed, I pounded my cock with my fist. In only about six desperate strokes, my cum was spurting hard, and I was lost in the bliss of those firing nerves that clenched my pelvic muscles. The first lash of my cum landed on her chest, streaking over her right breast. The second two landed on her stomach. The rest spurted weakly onto the back of her hand.

When Sam’s contractions stopped, she asked me to move a bit so she could relax her legs together. I lay down next to her.

“Oh, Tris, that was really good . . . again.”

Sam scooped up finger of my cum from her chest. She put it to her tongue and swallowed.

“I like your taste.”

She scooped another blob onto her finger, and raised it to my mouth.

“I’ve tasted my pussy. I want to see you swallow your own cum.”

I sucked my semen off her finger. Actually, I had tasted myself before, so was not totally new. But it was something else to have my sister feed me my own cum.

“Sexy,” she said. “I love you.”

“Oh, I love you, too, Sis.”

After resting for a couple of minutes, Sam announced that she needed a little something to eat.

“But, I’m not finished with you yet, bucko. I‘ve got something new in mind for our afternoon.”

After lunch, we had almost more than three hours before mom would get home. On her bed again, I lay on my back, while Sis deliciously scraped her fingernails gently over my stomach and down over my cock. She moved her head down stomach, kissing and licking me gently. She took my half-hard cock in her mouth and sucked me while fondling my balls.

“Oh, Sis, that’s wonderful. Your mouth is so warm and soft.”

She sucked and stroked me until I was full hard again. Then she came back up to whisper in my ear.

“Tris . . . something I want to tell you . . . I’ve never had butt sex. But Annette tells me that she quite likes it. She’s not a slut, and she doesn’t do casual sex, but she is quite liberated. She says that she can sometimes come harder from a cock in her ass than from one in her pussy. I can’t understand that, but I’d like to try it.”

She went on, “I’d have a hard time trusting any other guy for butt sex my first time, but I’m comfortable with you. And from the last few days, it seems like you might be interested.”

My heart was pounding. The idea of fucking my sweet sister’s ass was another super erotic fantasy.

“Annette suggested that if I ever want to try it, I should work on stretching myself open first, so that it wouldn’t be painful. In fact, that’s part of the reason I got up late this morning. Because I decided that I want you to fuck me in my ass, I’ve been working on getting a fat sex toy comfortable in my butt. This morning it was finally pretty easy. I’m sure noticed how your easy finger slipped in my backside this morning, because I noticed it.”

“So, what do you think brother? Would you like to fuck me in the ass? This would be a first that we can share.”

“Of course I’d like that. But I don’t want to cause you any pain. I couldn’t enjoy anything that was hurting you.”

“There’s no need to worry. We’ll just go slow at first. I think it’ll be fine. And if it does hurt, I promise I’ll tell you . . . How would you like to do it? Would you like me on my knees, and fuck my ass from behind, or me on my back?”

“Oh, God, Sis, either way is fine with me. How about both? How about if I work it in slowly while you’re on your knees? Then, once it’s comfortable, I’d like to do it with you on your back. I want to look at your pretty face, and your gorgeous tits, and your sweet pussy. But I’d also rather do whichever feels better for you.”

Sam got on her knees, with her head on a pillow, and her back deeply arched – so her ass was high the air. That view was again stunning. Her pouting pussy was dripping. I gave it a deep lick again – to lap up all of her sweet cream.

She handed me a tube of lube.

“Work this in my rear hole with your fingers. Then grease your cock good.”

It was a work of joy to stick my fingers in her ass, having her full agreement. I worked one finger, then two. With the index fingers of each hand, I worked to spread her hole wide. I stuck the fingers of each hand in her tight ring, and slowly stretched her open in all directions. None of it seemed to cause her any discomfort.

I pushed the head of my cock against her brown, puckered hole. It seems that we had prepared well, because I slipped in pretty easily. Sam just gave a small “uh” sound as my head pushed through her tight ring. I held still for a moment, eased the pressure back to let things adjust, then pushed in another half inch.

“Is this okay?” I asked.

“Yeah. It feels fine. Just a little weird, especially when you pull outward. I don’t really want to say what that feels like. How is it for you?”

“It’s wonderful. Even though went in easy, you still feel so tight around my cock.”

It was supremely erotic to see the ring of her butthole stretched tight around my shaft.

“Go ahead and work it deeper,” she said. “Let’s try to get you all the way in, and see how that feels.”

I eased deeper, about half an inch with each stroke. When my cock was half way in, Sam suggested I pull all the way out, put more lube on everything. That made things even easier. It wasn’t long until I my public bone was again pressed hard against her butt.

“Mmmm. Take it half way out now, okay? . . . Yeah, that’s much better. All the way in is a little uncomfortable. Try slowly out and in from there, but not all the way in.”

After five or six short strokes, she volunteered how things felt.

“Oh, my God. That is so good. I never felt anything like this before. My thighs are quivering – vibrating.”

“Oh, Sis. I’m getting too close. This has me so aroused. Can we try it on your back now? I need a little break – I don’t want to come yet.”

On her back, with her knees high and a pillow under her butt, Sam’s feet were again on my thighs. This was all so that her butthole was well above the bed. Again, I pushed the head of my cock against her brown hole. Again, it slipped in easily. In three slow strokes, half of my length was again in her ass.

I liked it better with only half my cock up her butt, and while she was on her back. This way I could still the ring of her asshole gripping my cock, which was hot to watch, and I could also see her pink, open pussy. At the same time I could look at her beautiful face, and her stunning tits. The whole thing was so exciting that it was quickly getting very difficult for me to hold back from coming. Because I was concentrating on not coming, I could only do the slowest strokes.

“Is this okay, Sis?”

“Oh, yes. It feels really good. I had no idea. But I’m ready for you to really fuck my ass now. Anytime you’re ready.”

In just a few more strokes, my orgasm was boiling up again. I was so close. But I wanted to let her feel me really fuck her ass, at least for a bit. For distraction, in my head, I started counting backwards from 100 by sevens.

“Oh, yes, baby. Keep doing this. This is so hot. My pussy is so hot.”

I asked her, “Will you play with your tits again, while I fuck you? I really like watching you do that.”

I was also hoping she might come sooner with that extra stimulation.

Finally, after half a minute of my mental math, with my eyes closed most of that time, my loins had settled down.

“Is this still good, Sis?”

“Yes, it’s great. I feel something like a hunger in my thighs that will only be satisfied when I come. I’m getting close now. Can you go a little faster?”

I thrust faster. Her pussy lips opened a bit as I withdrew each stroke. Seeing her pink hole open and close this way got me even more excited.

“Oh, God, yes. That’s perfect. Please don’t stop. I’m so close to coming. Keep going, baby. Fuck my asshole.”

I thrust even faster. I was about to the point of no return.

“Sis, please come soon. I can’t hold back any more.”

“Oh, fuck, yes. Are you ready to come in my ass now? I’m about to come. Come in my asshole, baby. Come in my asshole. Now!”

On her command, my cock control muscles clenched, and my cum raced up my cock and into her bowels. Spurt after spurt of my come splashed where no semen had ever touched before. My release was bliss.

Again, Sam’s hands flew to her sides, and she balled the sheet into her tight fists. Sam pretty face tightened. Her knees clamped together as her legs muscles contracted jerkily. At the same time, I felt her butthole ring clamp my cock in spasms.

“Oh, shit . . . Oh, fuck.” She groaned.

Gradually, Sam relaxed, her knees still together, my cock still inside. I gently nudged her knees apart again, and slowly pulled out. Sam’s butthole gaped open. She moved her hand under her butt and felt her asshole with two fingertips.

She laughed, “Well, you sure got me loosened up. This is a new experience. I can’t seem to close my asshole. That ring of muscle is just tired, I guess.”

Her open asshole was smoking hot to see. I reached my hand down and stuck my middle finger all the way up her butt. She didn’t seem to mind. As I massaged the rim of her still-slippery hole, it slowly closed up.

Sam raised her butt a bit to slip a towel under her. My legs were a bit cramped too. It was relief to lay down next to her again.

“Oh, my God,” she said. “I’ve never come so hard before. Until now I thought the whole thing of an ‘anal orgasm’ was some kind of fairy tale made up by guys who just wanted to fuck girls in the ass . . . But you did it all so good, Tris. How was it for you?”

“Oh, fuck.” I said, “It was so hot. It was wonderful. You are so sexy.”

“Mmmm. You too.”

“I love you, Sis.”

“I love you too, sweetheart. I haven’t been with a whole lot of guys, but you are the best lover I’ve ever had.”

We lay quiet for a couple of minutes until Sam suggested that we go take a shower together.

As the warm water soothed us, I lovingly soaped Sam’s tits, her pussy, and the crack of her ass. To just feel the soft roundness of her body was delicious – the soft roundness of her tits; the soft roundness of her globes of her ass. And to run my soapy middle finger down the crack of her ass, and between the lips of her pussy was still the stuff of my dreams.

“Mmmm. That is so nice,” she said.

In returned, she lathered my cock and my balls, and fingered the crack of my butt.

I don’t think I could ever choose whether it was better to do that to her, or have her do that to me.

To my great surprise, Sam then slipped her soapy finger part way into my butthole.

“Oh, Jesus.” I said.

“Turnabout is fair play, little brother. Next time, I’m going to finger fuck your asshole while I suck your cock. So be ready.”

My beautiful sister kissed me again. It was my turn to whimper as she probed my mouth with her warm tongue.

“But don’t worry. I’ll be gentle, too.” She whispered in my ear.

She whispered again, “Do you need to pee? You still owe me one.”

“Yeah, I really do need to pee.”

“Well,” she said, “I know that last time I said I wanted to hold your cock while you pee, but I’ve changed my mind. I wanted to feel your hard stream on my pussy.”

Sam leaned against the end wall opposite me. She reached down and spread the top of her slit wide apart, exposing the nub of her clit. That was so damn sexy to see.

“I want you to feel you pee on my clit.”

I was rock hard again. To see her exposing herself like that was thrilling.

The puffy, reddish-brown nipples that capped Sam’s stunning tits pointed right at me. With her chin down, Sam coquettishly looked up at me with her big brown eyes. She half smiled.

“How’s this?” she asked.

“You’re a gorgeous vision.”

I relaxed enough to get my stream flowing. I clenched whatever deep muscles it is that control it, to force a hard stream. I pointed it to her clit, and to her fingers.

“Mmmm. That’s nice, baby. That’s hot.”

As my stream started to weaken, she said, “My turn.”

Spreading her pussy lips wider, my pretty sister released a fat stream of pee. Shifting her hips forward, and wiggling her hips side to side, she directed her stream at hit my feet and lower legs.

After a few seconds of watching her pee, I quickly stepped forward. I extended my arm and reached between her legs, cupping the mound of her pussy with my hand. I may be weird, but it was very sexy to feel the warm stream of her piss hitting fingers. I put my other hand to her left breast, and kissed Sam’s soft lips. This time it was I that excitedly explored her mouth with my tongue.

Sam moaned softly.

When the flow of her pee stopped, I gathered her to me, and turned her around to warm up under the shower.

I nudged her to lean against the wall, and got on my knees. The water was streaming down her belly. I took a breath, put my face in the flow of water and licked all of her slit that I could reach. Even though there was a lot of water, and even though I just soaped her slit, I could still taste and feel her slippery self-lubrication. I turned my head, took another breath and resumed sucking gently on her clit.

“Oh, baby. That is still so good.”

I stood up and guided her waist so she was leaning against the back wall of the shower, facing me. The water warmed us both from our chests down. I pulled her hips away from the wall and put my again-rigid cock between her thighs. By lowering my butt, and angling my hips upward I was able to find the entrance to her pussy with the head of cock. It slipped in easily. At this angle, I couldn’t reach inside very far, but it was enough. I slowly stroked in and out of my sister’s wet pussy.

Sam whimpered.

I reached up and fondled her tits. I rolling each nipple between thumb and forefinger.

“Oh, God, Tris. I think you’ll make me come again if you keep this up.”

I stroked my hips faster, at the same time I lowered my mouth to suck one of her tits into my mouth, as I tweaked the other with my fingers. It wasn’t the most comfortable position, but I hung on, wanting Sis to come again.

“Oh, harder, baby . . . I’m coming soon.”

I thrust faster, and sucked harder.

“Oh, I’m coming again. Oh, shit.”

Sam put her mouth to my shoulder, squealed, and bit me gently as she jerked her hips into mine.

“Oh, fuck,” she said. “You made me come again.”

“Turn around,” I whispered. “I want to come now – while I fuck you hard from behind.”

Sam’s head was turned to rest her cheek against the wall, with her hands flat on the wall. I held her hips, using them to pull us together at the same time I thrust into her pussy. It took a while of hard thrusting for my cum to rise. My thighs were slapping hard against her ass.

“Oh, fuck, Tris, I’m going to come again . . . Yes, keep fucking me hard. Do you like having your cock in your sister’s cunt? I like it, baby. I want to feel you come in my pussy again.”

“Oh, Sis, yes. I love it. I’m going to come now . . . I’m coming.”

Sam squealed again as my cock pulsed, and the first spurt of my cum splashed inside her warm pussy.

“Yes. Oh, fuck,” she groaned. “I’m coming too. Oh, God, yes.”

As my orgasm finished, Sam nearly slumped against the wall. I turned my lovely sister aound, and enfolded her into my arms. We leaned on each other, in tired support.

“Oh my God, little brother. I think you’ve ruined me – at least for today. You’ve done fucked me well and good. I’ve never come four times in one day before, much less four times in one hour. My little pussy and asshole need some rest now. I’m glad I have tomorrow to rest up before I start work on Sunday.”

Sam was scheduled to work four 10-hour days – Sunday through Wednesday. She got a daytime shift because the hospital paid a big bonus for off shifts, which meant they had enough willing workers to cover nights.

I had told Sam that I planned to go at my job hard those same days, so that we maybe we could sometimes be together on Thursdays and Fridays.

“I think I would like that,” she told me.

More to come . . .

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