Diary of a Horny Student Ch. 11

11

"HE WHAT?" I exclaimed.

Out here on the front steps of our house, my step sister Alex just told me that Brian, the guy dating her mom (my step mom), had also been the one to take her virginity. I was aghast with confusion.

"Who did what?" Came a voice from behind me. Turning, I saw Steph walking toward us while waving back toward an unknown man in a car. She smiled at him. She was in her work clothes, and the top buttons of her polo shirt were unbuttoned. That deep pang of jealousy shot dully into my stomach.

I wasn't sure what was happening, but I was definitely on edge for multiple reasons now, and I did not hold back. "You know that guy Brian? The friend of your parents' that my step mom Kelly is seeing?"

"Yeah, what about him?" Steph tossed back casually.

"Alex FUCKED HIM!" I said in a loud stage whisper.

"Excuse me?" Steph said in surprise, stopping in her tracks.

"Jesus, Tim, keep it down!" Alex implored, looking around for anyone who might have heard.

"YEAH," I continued, "not only did she fuck him, she lost her virginity to him!"

"What?" Steph said softly, clearly confused.

"Yeah! Our mom's boyfriend!" I said incredulously.

"I thought..." Steph started, "...you said you lost your virginity to Eddie Besser after prom!" Steph had a puzzled look on her face.

"I lied," Alex revealed, "Eddie couldn't get it up. I liked him, so I told him I'd tell everyone we did it." She ran a hand through her hair in stress. "I didn't want him to get made fun of, but also I didn't want it to look like I couldn't get a guy hard."

"But Brian..." Steph continued, still trying to make the pieces make sense.

"He was a fill-in bartender at a bar by my school. It was my birthday, and my roommate sort of set us up. He was a hot, older guy from out of town, I didn't know anything about him, and I sure as shit didn't think I'd ever see him again!"

She didn't know anything about him. She didn't know that before dating our mom, Brian had been in at least one videotaped threeway with Steph's parents Sandy and Don. She didn't know that he had shot his cum all over Sandy's face while Don taped it.

...but did Steph know?

"But it was just the one time?" Steph inquired again, even more interested in the details than I was.

"Yes!" Alex quickly responded, before backtracking a bit. "Well, no...I fucked him again in the shower the following morning. But that was it, I swear!"

I had seen what Brian had done with Sandy and Don--I knew how big his cock was--and the thought of my step sister taking that big fuckstick deep into her body under the hot water of a shower made my balls tingle.

"Are you gonna tell Kelly?" I asked (probably a stupid question).

"No, of course I'm not going to tell my mom that her boyfriend took her daughter's virginity!" Alex said, a scrunched "what the fuck?" look on her face.

"What are you going to do, then, try to break them up?" Steph offered.

"Yeah, I mean they can't keep seeing each other, right?" I joined. I didn't know if I really thought that, or if I was just jealous of the attention Kelly was paying Brian, attention that a part of me felt was still reserved for my dearly departed dad.

"I don't fucking know..." Alex said, head in her hands again, "I mean, it's definitely fucked up, but at the same time...she seems really happy." She rubbed the back of her neck slowly. "I just don't know."

We all sat there in momentary silence, until Alex got up off the steps.

"I need to take a walk," she said, passing between us.

"You want me to come with?" Steph offered, but Alex just kept walking.

"No, thanks, I just need to clear my head a bit."

Alex walked on down the road, leaving Steph and I standing alone in front of our building in silence. She had a forlorn look on her face, and her mind was clearly racing. I began to offer the chance to talk, but she stopped me before I could get two words out and curtly said "I gotta go," and headed inside.

Later that night, lying in bed, my mind was reeling from the events of the day. My friend Christine, the pastor's daughter, had ravenously sucked my cock after church, opening up an entirely new dimension of our relationship. Neither one of us knew what it meant, but I don't think I was the only one who wanted more.

Then I find out my step mom's new boyfriend fucked my step sister, taking her virginity, before he met my step mom. It was a very strange, sensitive situation, but maybe Alex was right--maybe the past was just the past and Kelly's happiness was the only important thing. Maybe it didn't matter what Brian had done with Alex. Or with Steph's parents.

And then there was Steph. There was a weird vibe tonight. Steph had seemed hurt by Alex's confession of lying about losing her virginity, and then even more so when Alex rejected her offer to talk. Did she feel like Alex was pulling away from her? How would that affect them when they were at the same school next year?

Pulling my phone out, I opened up a new text message to Tara. I desperately wanted to talk to her about all this, but I couldn't bring myself to write.

I was caught in an indecisive daydream, when suddenly I was snapped out of it by the buzz of an incoming text message. It was from Steph.

"Wow, that was pretty fucked up tonight, huh?" it read. I hesitated before answering. We hadn't talked casually in quite a while, and given our recent past I wasn't sure what the bounds of our relationship even were anymore. But still, I needed someone to talk to, and seemingly so did she.

"Yeah. I don't even know where to start," I replied.

"I can't believe Alex had sex with my parents' friend..." she wrote back. Her statement was general to the whole situation, but it was clear which part of it bothered her the most.

"Did finding that out make you sad?" I inquired. I was taking a risk--Steph and I had never talked about her and Alex, but it seemed to me she left me that door open for a reason.

There was a long pause between messages, and then three dots preceding "I'm not sad she slept with him...I guess I'm a little sad she lied to me about losing her virginity though. We always told each other everything when it came to that stuff."

Three dots, then "I told her everything about when I lost mine."

This message caused a stir in my balls. I thought back to our conversation the night I put my whole foot in my mouth by admitting I could hear the sounds of her orgasms through the floorboards above me. My day had left me confused, but never more sexually confident, so I decided to push it.

"Yeah well, you never finished telling ME about it, you know..."

A long pause.

Three dots

The dots disappeared momentarily, then appeared again. She was writing SOMETHING.

"Perv" was all that came through.

Damn. I blew it.

Then an emoji: ":P"

My cock twitched.

I paused. I didn't know how to respond. I wanted to keep pushing, but there was something I needed to know first, so after a long pause, I typed "So who was that guy who dropped you off?"

Three dots appeared, then disappeared, then appeared again followed by "A friend from work."

"Just a friend?" I sent back, probably too quickly.

"Maybe..." she replied, followed shortly by "...maybe not."

There she was--Steph the tease. But something felt different about this. It wasn't just teasing, it was...flirty.

"Why, you jealous?" popped up on my phone. The truth was, I had no right to be jealous--it's not like she and I were in some sort of exclusive relationship, or really ANY relationship for that matter. And besides, what sort of hypocrite would I be to say yes when I, myself, had had my dick in another girl's mouth just hours earlier?

A teenage boy sort, that's what.

The question hung unanswered, as I fretted over how to respond. She was always playing some kind of game, so I responded with the one thing she'd never expect: honesty.

"Yes." I typed back.

There was silence now. No bubbles, just silence. Maybe this wasn't the right move after all. Then again, maybe it was the truth she needed to hear.

Three bubbles.

"Go wait for me on the back porch," she replied, "I want you to show me how jealous you really are."

My cock went from six to midnight almost immediately. The back porch was an enclosed porch off the back of our building that was a shared space, but had no windows facing it, and was covered in shadow from the overhanging trees. It was dark, it was quiet, it was secluded. Being as late as it was, there was sure to be no one around to bother us.

"Give me five minutes" I texted back. I still had Christine's dried saliva on my cock from earlier in the day, and I needed to rinse off just to be prepared.

I thought about Christine, and Rachel's reaction at church, and Steph's awkwardness the night before. I was feeling cocky and confident, and ready to push my luck, so I followed up my text with an addendum: "And wear something slutty."

"Excuse me?" she quickly responded.

I smiled, and kept pushing. "You heard me."

Another long pause. Maybe I found the line and crossed it. Maybe she didn't like me displaying power, and decided it wasn't worth her time. Maybe--

Three dots.

"I'll see you in five minutes."

My cock throbbed, and my stomach sank. I just played a pretty heavy power move...what if I wasn't ready for what came next?

After a rinse, the careful walk down the back stairs to the porch felt long. The cocky confidence I displayed started to ebb away, and nerves began to set in.

The porch was empty when I arrived. Moonlight made enough of my surroundings visible, so I made my way to the big bench seat along the back wall. And waited.

Ten minutes passed. Then fifteen. This was it, I knew it. Steph set me up just to blue ball me when I showed some backbone.

I was about to leave, fed up with another chain jerking by Steph, when I heard the soft squeak of the porch door as it pushed open.

It was dark, and I couldn't make out who it was at first. My stomach dropped a bit as I considered the possibility that it was anyone but Steph, but then as the figure strode toward me, the moonlight revealed her features like a rising curtain. Ankle socks on slender feet; long, athletic legs, bare in the moonlight, stretching up until her hips disappeared under the drape of a long buttoned down shirt.

A button down shirt that was not buttoned.

Instead, the two halves hung loose, revealing a runway of smooth, skin running from the nape of her neck, over her collarbone, between the braless cleavage of two perfect breasts, and down her tight, flat stomach, punctuated by a pair of dark panties drawn tight over the lips of her pussy.

My mouth started to water, and my erection immediately returned.

Steph stood in front of me quietly, hair done up in a messy bun, and looked at me as I stared, dumbfounded, at the goddess before me. "Is this what you wanted?" I nodded. She closed the distance between us slowly.

I felt one thigh surround me, and then the other, as she straddled me on the cushioned bench. She gently grasped on to the window sill behind my head, locking me in place. My hard cock strained up through my shorts, desperate to touch her as she hovered her pussy above it.

"So you're jealous, huh?" she said, gyrating slowly above me, tantalizingly close to my cock.

Any power I thought I had was for the moment gone. All I could do was nod.

"Say it." She said.

"Yes." I choked out.

Then finally she lowered herself down, and ground her pussy against my hard cock. "Would you be jealous if I did this to another man, Timmy?" There was only the thinest of fabrics separating us now, and I could feel her heat on me.

"Yessss" I groaned out in answer to her question.

"Why?" She inquired, as her slow gyrations continued to put exquisite pressure against my hard cock.

"Because..." I began. I could barely think, but I managed to eek out a response. "...I want...this...I want...YOU...all to myself." I swear this was more effective than a lie detector test, or truth serum.

"I see," she said with a smirk. Then she leaned backward, sitting up straight. slowly dropping her shirt off her shoulders, she revealed her full breasts to the cool moonlight. Hard nipples accented perfect slopes that arched off the flat of her chest. I had seen them that night in the limo, but I had never touched them. My hands floated from my sides onto her muscled thighs in nervous anticipation.

"Why shouldn't I do this to other men, Timmy?" She breathed, grinding into my cock again. My eyes were locked on her tits, squeezed together and pushed up as she crossed her arms in front of her. "Why don't you convince me?"

I licked my lips like a hungry dog.

My hands slid up her glass-smooth thighs and gripped her ass--that fantastic, athlete's ass that I had seen flaunted in front of me for years and years--pulled her tight to my body, and with with a deep growl dropped my head into her breasts, latching my lips around one of her hard, perfect nipples. I sucked hard. Steph gasped.

My lips and tongue were a whirlwind of suction and pressure. "That's it...that's a good boy," Steph whispered between shortened breaths. My hands squeezed the globes of her ass tightly, and I felt her muscles flex between my fingers as she slowly humped forward and backward. She was rubbing her drenched pussy along my painfully hard cock, practically fucking me.

Her gasps and squeals were coming more frequently now, clearly overwhelmed by sensation. I sucked harder, and with a groan she lurched forward, catching herself on the edge of the window behind me. My hands left Steph's ass, and snaked their way up over her hips, across her stomach, then up and under the two heaving breasts that now hung free in front of my face.

These were breasts that had teased me. Breasts that had dared me to look as hard nipples pushed through thin sleepwear, or cleavage thrust up and out at me in swim suits and push up bras. Breasts that taunted me with what I would never have. Breasts that now sat gently in the palms of my hands.

I squeezed and kneaded, and Steph and I both let out pleasurable moans in unison. I felt her shift and grind her pussy against my titanium-hard cock as her breathing became more ragged. Pushing her tits up toward my face, I took another nipple into my mouth, and Steph slapped one hand over her own as a loud cry involuntarily lept from her throat.

Her hips rode me harder, triggering her pleasure center on the clothed shaft of my cock over and over again. My lips and tongue bounced back and forth from nipple to glorious nipple, sucking, licking, pulling--I could feel her starting to shake with mounting pleasure.

Her breath was short and sharp, one hand gripping my shoulder, head hung with closed eyes. She was in that glorious, final straight away now, racing toward the edge, so I focused in on one nipple, giving it all I had while my other hand squeezed and kneaded her other breast. Her hips thrust and shook, sliding her clit long and hard against my cock, tiny cries of "that's it...good boy.." sneaking out as she fed me her breast. It felt almost like magic, like some sort of ritual, as my lips and tongue began to summon her quaking orgasm.

I suddenly felt her arm wrap around my head, pulling my tight to her bosom, her hot breath directly in my ear, and at the crest of a deep, long gasp of air, I felt her body tense, followed by that sweet, heavenly triplet of moans--short, short, long--as Steph spasmed in exquisite, rapturous orgasm atop me.

She held me tight as the pleasure coursed through her. The only motion between us was her hips thrusting forward against my cock, slowly but deliberately, almost involuntarily, as she rode out the length of her climax.

Her thrusts became slower, and then stopped. I felt her body relax, heavy breaths still hot against my ear. She released my head, and pulled away from me, popping her nipple out of my mouth. I wasn't about to let those breasts go that easily though, and while she was still coming down from the high of her orgasm, I leaned back in and covered the space between her tits with soft kisses, gently squeezing and caressing her breasts as I did so.

Finally she pushed me back, and looked down at me. She was gorgeous, her supple breasts exposed to the night air, rising and falling with deep breaths, nipples swollen from my ministrations, skin flushed with the heat of orgasm. There was still lust in her eyes, and for a moment I thought she might lean in and kiss me, but the moment passed, and she slowly, but steadily, dismounted, leaving my still-hard cock pressing to the sky.

We sat quietly on the bench for a moment, just breathing, a far away look in Steph's eye.

Finally I broke the silence. "Was that convincing enough for you?"

Steph looked me in the eye and chuckled a bit at my brashness. She let out a long sigh, and then looked down at my straining erection tenting my shorts.

"That looks uncomfortable," She said. All I could do was nod.

Sidling up next to me, pushing her naked tits into my arm, she reached down and began pushing down my shorts. I lifted my butt to help her, and soon my straining cock was stretching high and stiff into the moonlight.

"You know," Steph said as she danced her fingertips up and down my naked thigh, "you're right--I never did tell you how I lost my virginity."

I let out a long sigh as I felt her fingers delicately run up and down the length of my dick.

"I could tell you now..." she continued, as her fingers traipsed down to my balls, then back to the head of my cock "...but I'm going to be very disappointed if you don't make it to the end of the story..."

I closed my eyes and groaned as she dragged her nails up and down my length.

"Do you think you can make it?" she said, a cheshire grin on her face now. This was Steph in full tease mode...but at that exact moment I wanted nothing in the world than for her to tease me more.

"Yes," I choked out, "tell me."

"Well," she began, "we were at a volleyball tournament." Immediately my mind jumped to the girls volleyball team--short shorts, long legs, competitive juices flowing, each team member a passionate young woman.

"We didn't win, but it didn't matter, we were really all just looking forward to the afterparty." Their parties were legendary. The thought made my cock bounce as she trailed her nails over it.

"All the teams got together and had a rager at the hotel. The coaches were all out at their own conference, discussing next year's tournament, which meant that all us girls were left to our own devices. After a hard-fought tournament like that, you can bet we all needed some...release."

She said that last word with a sigh behind her breath, and her hand squeezed my swollen balls gently.

"I can't tell you how many times I've wanted to kill the other team on the court, only to end up licking their middle blocker's pussy later that night." My cock surged as I imagined Steph with her face between the legs of another hot, athletic volleyball vixen. She smiled and let out a soft giggle as it bounced.

"But this tournament was different," she continued, lightly painting her fingers up and down my length, "because it was the first one with our new assistant coach...Mr. Ridley." My eyes went wide, and I snapped my head towards her.

"RIDLEY?" I said in disbelief. She just smiled that sultry smile at me again, and continued to tease my cock with her fingers.

"He was young, he was hot, and I had put his reputation to the test LONG before that night, Timmy," she breathed, as she circled a finger around my tip, spreading the beginning drop of precum all over the head. I groaned.

"You...you..." was all I could get out as I focused on the sensations coursing through me.

"Oh, I had his cock in my mouth many times before that night, Timmy," Steph said as she continued encircling the head of my cock, "we had a routine - after practice I'd stay behind and help put the equipment away, and then I'd get on my knees and suck his cock till he came in my mouth."