Star Student Ch. 02

"Oh yeah... yes, sir..." she moaned in response as she vigorously worked her pussy, which was a frothy mess now, with my saliva mixing with her juices.

"I knew you'd like it," I said, stopping my rim job.

I gently traced a circle around her wet asshole with my middle finger, just before slowly slipping it inside. My fingertip penetrating Lydia's hole made her inhale sharply.

"You okay?" I asked, making sure I didn't hurt her.

"Yeah," she replied, "it just surprised me... it doesn't hurt."

I kept sliding my finger deeper, until I got to my second knuckle, about halfway in. I let my finger rest there as Lydia kept teasing her folds.

"Good girl," I whispered. "Keep playing. I'm just letting your ass get used to having something inside it for a bit."

Once Lydia's asshole released its clench around my finger, I began to slowly move it, both in and out and with light jiggles side-to-side.

My actions made Lydia squirm and moan. The stimulation from her ass mixed with her masturbation was rapidly pushing her towards a new type of orgasm.

Once my saliva was no longer lubrication enough, I pulled my finger out and grabbed the nearby lube that I had placed on the nightstand. I cracked open the flip-top lid, and squeezed a thick bead of the clear liquid in a long drip, landing on her asshole.

I smeared the greasy goo all around the edge of Lydia's anus, buttering her butthole as I lubed up my finger. Once she was slick and glistening with the lube, I slid my finger back inside, which slipped in easily now, forcing out a grunt of pleasure from Lydia.

I worked my finger in and out of her ass with more eagerness now, as Lydia ass was now more relaxed, and she was clearly enjoying it. My rhythm increased along with my depth, as I tried to match my dips with Lydia's rubbing.

My coordinated movements did the trick. Lydia began to gyrate and buck as her orgasmic tremors began.

"Ooooooooooh! Oooooooooooooooooh!" Lydia moaned. Her "Oohs" got longer the closer she got to cumming until she let out a long howl, followed by rapid grunts as she crescendoed and crashed into a mind-blowing orgasm.

I yanked my finger out of her clenched asshole just as she started to cum, making her squeal and jump, the anal sensations intensifying her orgasmic explosion.

When she had finished, Lydia collapsed onto her belly, face still in the sheets as she tried to catch her breath. She rolled over and looked up at me with a flushed face and astonished grin.

She sat up, winded and gasping, and laughed, "I REALLY did not think I'd enjoy this at all!"

Lydia rejoined me against the headboard, and slumped over onto my shoulder, resting as she tried to regain her composure.

She took a breath, then looked up at me, with a beaming smile. It was the same smile she had after I had taught her to suck my dick - the smile of a now not-so-innocent girl who thoroughly enjoyed a new sexual experience, and who was eager for more.

"I'm glad you're enjoying it, but this is the easy stuff. Just a little light butt play." I reminded her. "It wouldn't be punishment if there wasn't SOME sort of...discomfort."

Lydia's face switched back to concerned.

I grabbed the butt plug from the night stand, displaying it to Lydia as I said, "It's time."

Lydia started to get back on her hands and knees, when I stopped her.

"No, get on your back and spread your legs," I instructed.

Lydia leaned back against the headboard and slid down, keeping her head propped on a pillow as she laid her body flat and put her legs in a stirrup position.

"Good," I continued, "now hike your legs up to your chest."

Once again, Lydia obeyed. She raised her knees as I asked, cupping the backs of her knees with her hands and pointing her pelvis upward.

In this position, both her pussy and asshole were presented to me spread wide. Both were still slick with a mixture of Lydia's juices and the lube that I had already greased her butt with, but I added more lube, just to be safe.

Lydia stayed still while I squeezed more lube onto her crevice, letting it drip down the crack of her ass. I rubbed the slippery goo all over her wet pussy, lightly teasing it before I slipped my middle finger into her ass to replenish its lubrication.

Lydia bit her lip, enjoying my handiwork as I greased her asshole, slowly pulling my finger completely in and out in a steady rhythm. I ended by rubbing little circles outside her hole, making sure the opening was good and slippery.

"Play with your pussy for me, again," I commanded as I lubed up the butt plug, gripping the business end tightly with my lube-covered hand and twisting it in my fist.

Lydia brought her knees together, hugging the back of her legs with one arm, freeing up the other to carry out my command.

She reached around her thighs with her free arm, teasing her wet lips with the swirling fingertips motion that was obviously her preferred way to pleasure herself.

"Is this okay, sir?" Lydia panted, peering at me from behind her hugged up legs.

I nodded and smiled, then moved in close to continue. I teased Lydia's glistening asshole with the tip of the butt plug, in the same manner that I had been using my fingers. I gently circled her hole at first, occasionally nudging it barely inside.

Lydia let out a pleasured sigh at the touch of the toy against her ass, but she instinctively clenched up at the new, foreign object.

Eventually, her virgin ass relented, allowing me to dip the tip in and out of her hole in a gentle fucking motion. That was my cue that she was ready to try for more.

I grabbed the nearby vibrator and clicked it on, capturing Lydia's attention. She watched me curiously as I grabbed her hand, interrupting her masturbation, to hand her the humming toy.

"I'm going to put it in, now." I informed Lydia. I looked into her eyes and said, "I'm going to go slowly, but I need you to relax. The vibrator will help."

Lydia didn't seem to have any reservations about it now. I suppose she knew it was coming, and we were too far along the path to be concerned anymore. Either way, Lydia simply nodded at me in response, and touched the vibrator to her clit, prompting me to start.

Lydia let out a grunt of pleasure when the vibrations first hit her. She fought the urge to squirm in order to stay still for me. Her eyes were clamped shut, either in pleasure from the vibrations, or from bracing herself for whatever discomfort she expected from the butt plug. It was hard to tell which, so I let her enjoy herself a few moments before I moved forward.

I pressed the butt plug against Lydia's asshole with a steady, firm pressure. The tip slipped inside, sinking deeper, slowly. Once the plug had reached a point where it was too big to slip inside easily, I held it still while lightly pushing against it, never trying to force it.

As Lydia's asshole slowly relaxed, the plug would sink deeper inside. As the toy's girth got to its widest, Lydia winced as she felt it stretching her tight hole open. Her brow furrowed in both determination and discomfort, and she tooled her pussy with the vibrator more vigorously.

Finally, the bulbous, biggest part of the plug slipped inside. It disappeared into her butt quickly, almost as it had been sucked inside, making Lydia yelp in shock, and triggering a surprise orgasm.

The sensation of her ass accepting the large toy and clamping shut around the tapered handle end must have sent a jolt through her body that accented whatever pleasure the vibrator was giving her.

Lydia groaned and panted as she came unexpectedly. She involuntarily tossed the vibrator aside, still buzzing loudly, as she gripped her legs with both hands, trying to make sure she didn't roll or accidentally sit on the butt plug that was now firmly in her ass.

When Lydia was able to compose herself, I grinned and said, "See? I knew you'd like this!"

I turned off the vibrator and returned the now soaked toy to the nightstand as Lydia caught her breath, still holding her legs. She spread her legs open, trying to look down at her asshole to get a glimpse of the toy inside.

She saw the handle twitch as she clenched and released her ass, exploring how it felt inside. She laughed at the sight and said, "WOW. I honestly didn't think you'd ever fit that in my ass!"

"Yeah, but look at you now!" I laughed. "You're a regular butt slut, huh?"

Lydia frowned at me, stung by my joke insult.

"Oh, relax!" I groaned. "You know I was joking. I just meant that you're doing it. You can fit something big in your ass, like a champ."

Lydia forced a shy grin, but didn't reply. She still didn't like the idea of being viewed as a "slut" in any capacity.

"Lyds, it's fuckin' HOT." I explained. "Guys might be too shy to admit it, but every single one of them wants a girl who would want to do this - or at least be willing to give it a try."

She rolled her eyes and shot me a doubtful look, but at least Lydia didn't seem to be focused on the slut comment anymore.

"Soooo... what now?" Lydia asked, trying to shift the topic. She was still sitting there with her legs wide and a toy sitting in her butt. I could tell the vulnerability was starting to make her uneasy.

I got onto my hands and knees, leaning in to get my face close to her exposed crotch.

"You just relax, now." I instructed, breathing hot breaths against her pussy. "Let the plug do its job."

I greeted Lydia's glistening labia with a soft kiss, followed quickly with a playful licking and sucking, coaxing her back into a lustful frenzy as I ate her folds.

She inhaled sharply and let out a soft "Yes..." as she melted at my mouth's treatment. She let her feet rest on my back, giving her arms a break as she enjoyed my tongue's touch against her hard clit.

I would watch the butt plug wiggle as her body would tense and relax at the pleasure Lydia was feeling. Her breathing was getting steadily heavier, which (by now) I had learned was a precursor to an orgasm.

Just as she was getting close, I stopped my oral efforts to ask, "You enjoying this?"

Lydia's eyes parted into an intoxicated gaze as she dreamily smiled and gave me a nod.

"Good." I said as I backed away and stood. I turned to grab the lube.

"Your pleasure is the most important part of all of this." I continued as I re-opened the bottle, squeezing some of the liquid into my hand. "No matter what, when it comes to sex especially, if you're not enjoying it, you shouldn't do it."

I began to rub the slick goo up and down the length of my shaft, greasing it up for what was coming. I looked into Lydia's eyes as I took long, slow strokes, enjoying myself as I prepped my cock for her ass. She was enjoying the show, lightly touching her pussy as she watched.

When I had worked my cock into a stiff rod that was slippery with lube, I stopped and asked, "You ready?"

Lydia stopped touching herself and her face turned serious at my advance. She had thoroughly enjoyed herself so far, but everything we had done so far was basically advanced masturbation.

Now, she was about to enter new waters, and her face showed it. Not only had she never had a man inside her, but she certainly had never had one in her ass.

Additionally, my cock and the butt plug were two entirely different instruments. While the plug had a bit more girth, my shaft was considerably longer. Lydia eyed my hard-on timidly, not even trying to hide her concern.

"Look," I sighed, "if you truly don't want to do this, you don't have to. I mean it."

I scanned her face to see if my assurance had any effect. She still looked hesitant, so I tried to make her laugh instead.

"I'll have to come up with some other kind of punishment, of course," I laughed, "but I seriously won't ever make you do something you truly don't want to do."

Lydia smiled and let out a short chuckle, and looked into my eyes.

"I trust you." She said, still reserved. "It's been fun so far, and you haven't given me any reason to think this (gesturing at my erect penis) would be any different."

She averted her eyes as she thought, then added, "Just please be gentle!" In a fearful tone, returning her eyes to mine with an unsure gaze.

I sighed and assured her, "I'll be giving instructions, but you will be completely in control. Until you want me to be instead."

She held her stare for a moment, and then nodded.

"Good. Now, back on to your hands and knees." I commanded.

Lydia silently complied, crawling forward until her ass was in the air, pointed at me once more. The butt plug's handle stuck out like a stumpy tail.

"I'm going to take this out now," I said, gripping the handle that was now slippery with lube and Lydia's leaked juices from repeated orgasms. Her entire crotch and butt crack were wet with the slick mixture.

I lightly pulled at the toy as the bulbous part slowly appeared, easing out of her butthole. Once the widest part slipped past her anus, the rest came out with ease. I slowly removed it until the tip emerged, stretching a string of lube with it as it pulled away.

I put it next to the dampened vibrator Lydia had used earlier. One toy had filled her ass to stretch and relax it. The other had been used to mask initial pain with pleasure. Both left small puddles of nectar as they drip dried on my nightstand. I was going to have to clean that later.

I grabbed the nearby lube one last time to make sure Lydia's ass was good and ready. Nothing can ruin anal quicker than drying out.

I squeezed a small drip onto her hole, then used the head of my cock to rub it in. The touch of my tip against her asshole made Lydia tense, readying herself.

"Relax," I pleaded. "I'm just going to stay still right here," I added, gently pressing my cock against her ass. "You work me in at your own pace."

Lydia's asshole was relaxed enough from the plug and teasing that it swallowed the tip of my cock easily with barely any pressing, but stopped there.

Lydia leaned back against me, with just enough force to allow my cock to inch deeper. She exhaled as she felt my cock slip deeper into her asshole, trying to relax.

"Mmm it's nice and warm," Lydia moaned as she pressed deeper. "Feels nice."

She kept pushing back slowly, gently easing back off when she'd hit a point where my dick stopped sinking deeper, only to push back down to work it in further.

At about halfway in, it looked like we had hit a wall. Although Lydia's ass was lubed and relaxed, it wasn't accepting any more of my length.

"Play with your pussy," I sighed, enjoying the warmth and tightness of her ass gripping my meat. "It will help."

Lydia obeyed and reached underneath to tease her pussy, letting the pleasure distract her attention away from her asshole's endeavor.

As Lydia played, I pressed with a little more force, pushing my cock deeper into her asshole. My methodical diving was working. I was able to slowly sink my shaft deeper into her ass, finally feeling my balls touch her working fingers as they diddled her clit.

"Fuck yeah," I groaned as I felt my lap meet her ass cheeks, pressing against them. "I'm all the way in, Lyds. You're doing so good."

I stood still for a moment, letting her new hole get used to my cock's length and girth.

"I'm gonna let you take control," I said. "You move against me until you're comfortable."

Lydia started rocking gently, working my pole in and out of her tight ass. She started with tiny motions at first, slowly building to longer, more fluid lunges.

I could hear her sighing and gasping as she took more of my cock at once with each rocking motion. Her hand was a blur beneath her, vigorously massaging her soaked pussy. Since I couldn't see her face, it was hard to tell if her noises were from pain or pleasure.

"You ok?" I forced out through a groan, caused by the incredible feeling of having my sister's ass clamped around my cock as she rode me.

Before she could answer, Lydia's asshole gripped my member tightly as she clenched up and let out a loud moan. She was cumming.

She planted her playing hand back into the bed to steady herself as her body bucked against me, tossing her hair back and wailing as her pussy dripped.

I put my hands on her hips to steady myself, so I wouldn't fall over as she convulsed in pleasure, but Lydia must have thought I was taking over.

"Yeah, fuck my ASS!" Lydia hissed when she felt my hands grip her waist.

Her command ignited my lust, which I had let out in a controlled stream until now. I thrust my pelvis forward as I pulled her to me, quickly stuffing my cock all the way inside her ass.

Lydia yelped, shocked at my thrust. I ignored her cry in my fervor, pulling her by her hips into me until her ass cheeks pressed against my pelvis, and my balls pressed against her wet mound.

I pulled out slowly, but thrust back inside with a quick shove, making Lydia whimper through clenched teeth. After that, I fucked her with slow, steady, deep strokes, pulling all the way out until the head of my cock had to press back into her asshole, and sinking back down all the way to my base.

Lydia concentrated and exhaled, like a woman in a Lamaze class, trying to relax and manage the pain as I had my way with her asshole.

She gripped the bedding beneath her with clenched fists at first, but as her ass got used to being fucked, she remembered my lesson, and let her hand tease her pussy again.

Before long, Lydia's little cries of pain turned into moans. The pain had subsided and given way to pleasure as I kept up my steady rhythm and she tended to her clit.

It felt divine being balls deep in my sister's asshole. It looked even more exquisite. I peered down at her glistening ass, her cheeks shining with excess lube from her crotch and my hands, as I watched my cock disappear into her tight tunnel.

"Please fuck me faster, sir," Lydia whispered. "You're gonna make me cum again!"

I had been fucking her at a steady pace so far, to help her get used to the thrust, depth, and other sensations that one would need to acquire tases for in order to enjoy anal. Clearly it had worked.

I sped up until my controlled strokes became harder thrusts, ending with our bodies slapping together. With each delightful slap, my balls would bump into Lydia's working hand.

She stopped rubbing her pussy to caress my balls, making me pause my rhythm to enjoy the dual stimulation of her touch while her ass kept a warm, tight grip around my shaft.

"They're so tight and full of cum!" Lydia panted in a husky voice.

I knew that tone. Whenever Lydia's voice turned breathy and full of lust like that, she had turned a corner. She was now so aroused that she had completely abandoned her cuteness, demureness, and even dignity. For the moment, my sweet little sister was my whore.

"Yeah, you fuckin perv!" Lydia growled. She looked over her shoulder at me and added, "You like fucking your sister's ass? Huh? HUH?" My sister's fuck-crazed expletives made me rock hard as I nodded in response.

Her "huh"s morphed into prolonged moans as she grew closer to cumming. Her eyes tightened into a squint of pleasured pain. She closed her eyes, turned her head away, and gripped the bedding with both hands once more as I reamed her to another orgasm.

Lydia's hole clenched and relaxed around my cock as she moaned with each orgasmic wave, massaging it as I kept fucking her. She bucked against me, pushing all the way to my base, as she wailed in bliss.

My own orgasm was imminent. Lydia looked so hot in the throes of her climax, and fucking her ass was everything I dreamed it would be.

I stopped moving momentarily, trying to stave off cumming for just a little while longer, so that I could savor the visuals and sensations, but it was no good. My loins tensed and I let out a quick grunt as I felt my load rising.

"Yeah! Give me that cum, coach!" Lydia gasped, excited that it was my turn.