Diary of a Horny Student Ch. 15

Story Info
Tim and Steph go on a date and some hard truths are revealed.
5.3k words
4.78
16.5k
15

Part 15 of the 33 part series

Updated 12/29/2023
Created 04/01/2022
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15

It was a Wednesday night, and I was sweating.

The windows of my car were opaque with thick, wet fog from labored breaths, and my grunts mingled with high pitched squeals of pleasure as my hard cock drove in and out of Steph's tight, slick pussy.

Steph was the girl who lived upstairs, my step sister's best friend, the older girl who tortured me all through puberty. Now here she was in my back seat, bent over with her ass in the air, panties pulled to the side, moaning in delight as her tight body consumed my cock over and over.

Body always moving, slithering and gyrating, her moans and cries of pleasure made my dick even harder if it was possible. Tonight her moans were louder, throatier, as it was the first time I had ever fucked her from behind, and my thick cock was pressing into depths of her pussy neither of us had ever felt before.

Her pussy milked me. Her moans encouraged me. The vision of this statuesque beauty folded in half, writhing in front of me as I sunk my cock into her, her ass flared out to a perfect heart shape, put me over the edge.

As if she knew, her voice cut through the steam with a dusky, exhausted "Cum for me, Timmy, cum for me!" and that was all it took. My balls jerked and shuddered, my cock began to pulse wildly, and with one final, deep push my dams broke. I erupted in a guttural growl as geyser after geyser of hot cum shot up into Steph's body.

It had been a hell of a week so far.

Last saturday, after receiving the incredible strip tease and world-rocking blowjob Steph gifted me as a graduation present, I had asked Steph if she would go out on a date with me. We had been hooking up for weeks, and it was incredibly fun, but in that moment of post-nut clarity I realized there was something missing.

Earlier that day I had gone to lunch with my best friend Tara. I had learned the night before (in shockingly explicit detail) that Tara was in a relationship with Sarah, the girl who lived next door to me and also happened to be my longest teenage crush. But unexpectedly, at lunch Tara admitted to me that they weren't just hooking up with each other, they were actually dating.

Tara had hooked up with plenty of people, male and female, but I had never known her to be in an actual relationship. When I saw how happy she was in this new experience, how fulfilling she found it, I honestly got a little jealous.

I began to think about my relationship with Steph. It was messy, it was confusing, it was sexual, but was there anything more there? I felt like I might be falling for her--I had to know if it was more than just sex. I had to know if she possibly felt the same.

So I just blurted it out.

By the way her eyebrows arched I could tell I caught her off guard; kneeling on the floor with what seemed like a pint of my cum dripping down her naked chest, my question gave Steph pause. She looked at me for a moment, inspecting me, silently interrogating whether or not I was joking.

Without answering, Steph chuckled. Sighing, she got up, leaned forward, and kissed me.

"You're cute, Timmy," she said before padding off in search of a towel to clean up.

I sat there alone, my sticky dick cooling in the night air, trying to figure out what the fuck just happened.

The ride home was quiet. There was no tension, just a quiet calm. She rode with her back to the door, her feet propped up on my thigh. It used to feel like a move of dominance when she did this, but now it felt more loving. My hand rested on her leg, rubbing her bare ankles gently. It was nice.

"Where did you guys go last night?" I asked, trying not to betray the pang of jealousy I felt.

"Where did who go last night?" She answered flatly.

"Alex was in a pretty clear state of disrepair this morning, I just assumed you guys went out partying after I left."

There was a long silence.

I looked over at Steph, and she had a saddened expression on her face.

"Steph?" I asked, trying to bring her back to Earth.

"Nah, I was home all night," she said with sigh, "I don't know where she went."

Something was going on between them, but I had no idea what. Steph seemed surprised to learn Alex had gone out without her.

I parked in the shadows by our building and turned the car off.

"Thanks for tonight," I said as Steph sat up. She kissed me quick before exiting the car, giving my balls a soft squeeze. As she leaned toward the door I finally spoke up.

"Wait," I said, before she could disappear. She turned back toward me. "When can we do this again?" I asked, with a slight desperation to my tone.

"Like I said, Timmy," she smiled, "school's out."

I skipped church the following day. With all that was going on with Steph I was definitely not ready to see Christine again yet. The pastor's daughter had hungrily sucked my life out through my cock not too long ago, with an implication that it wasn't just a one-time thing. I was not ready to deal with that yet.

Truth was I DID want it to happen again, but between her desire to resist temptation, and my budding relationship with Steph, it didn't seem like a good idea for either of us. As far as I was concerned my cock belonged to Steph right now, and I didn't want to hurt her.

Besides, I don't even know if I would have had anything left for Christine after what Steph had been doing to me. We had two weeks left before Steph left for college, and we were determined to make them count. School was out, alright, but boy was I learning a lot.

Steph didn't have work on Sunday, but her parents had errands to run, so on the pretense of going out for a run I slipped up the back stairs to Steph's unit, and managed to give her two loads of cum before they got home.

Monday I picked her up from work, and minutes after I arrived I was on my knees. I ate her pussy till I heard that short-short-long reverie of her orgasm, and then she rode me hard and milked out another white explosion with her freshly-pleasured pussy.

Tuesday she wasn't closing up the store, so when I picked her up she asked that we "take the long way home," which translated into a slow, languid session of road head that ended with Steph getting a mouthful of my hot jizz that she gleefully swallowed down.

Wednesday was a bit trickier. Neither of us had anything on the books, so she told her parents she was going to the mall, and I told my step mom Kelly I was going to Tara's. I picked her up at a predetermined spot, and we went out to The Spot for the hot, sweaty fuckfest described above where I took her from behind for the first time.

It had so far been a week of intense carnal pleasures, but as I pulled my softening cock out of her well-fucked pussy, I just couldn't get one thing out of my mind.

"So, have you given any thought about what I said the other night?" I said between sweaty, ragged breaths.

She unfolded from her coital position and slumped back against the back door, her tits heaving as she huffed and puffed herself.

"About what?" She said, clearly pretending she didn't remember.

"About going out on a date."

After a moment of contemplation she crawled over to me, her tits swinging seductively. "Why, you wanna take me to the movies so I can suck you off in the back row of the theater?" She purred, dipping her head down and taking my slick, softening cock back into her mouth to suckle on.

"No, no," I laughed, pulling her off my sore, swollen manhood, "I just...I wanna spend time with you."

She laughed.

"It's not like we just met, Timmy," she laughed, "Plus, do you know how much of your cum I've had inside me this week? I'd say we know each other pretty well!"

"I know, and don't get me wrong, I LOVE this," I chuckled, the laughter quickly dissipating to something more sincere, "but...do you remember when you asked me what I wanted? Well nothing has changed. In fact I mean it even more now. I want...more."

"You just want to fuck me in the ass, don't you?" She said seductively, deflecting my statement

"No!" I said with an exasperated laugh, "I want YOU. I want to take you out on a date. A REAL date."

Steph's demeanor changed.

"I'm gonna be gone in less than two weeks, Tim," she said, finally matching my own sincerity, "I'm going to college, you're going to college...it doesn't make sense for this to be anything more than it already is."

"I'm not asking for next week, or next month, or next year, Steph," I said honestly, "I'm just asking for right now. And right now what I want is to take you on a date."

She smiled meekly.

"And if ass stuff is on the table still after that, sure, I'd love to fuck you in the ass!" I joked. She laughed heartily and slapped me on the leg

She looked at me for a moment, then looked away, almost embarrassed.

"Oh boy, this is a bad idea," she said under her breath before looking back at me and saying "sure, Tim, you can take me on a date."

My face broke into a huge grin. She tried to stifle a smile of her own but did a terrible job of it.

I leaned in, and she pulled me close for a long kiss. My cock hardened as our bodies mingled. I gently slipped back inside her perfect pussy, and we gripped each other tight as we made slow, passionate love. Soon her orgasm washed over her, and as that wonderful chorus of hers began, so did my own orgasm; as those two short moans escaped her lips my balls pulled up towards my body, and with her final, long moan the spring inside me snapped, and I once again filled her body with my seed.

We decided on dinner Friday night, and agreed it was a good idea to take Thursday off to recharge ourselves. I was excited. Nervous. Most importantly I needed someone to talk to about all this. So I picked up a pizza and went over to Tara's.

We laughed, we caught up--it felt good. Of course our conversation veered toward the sexual, as it always did, and all of a sudden I felt the room get very hot, and my pants start to tighten, as Tara regaled me with the details of how she fucked Sarah with a strap on for the first time the other night. I had witnessed the two of them lick each other to orgasm with my own eyes, but even so, the thought of my best friend fucking my biggest crush with a thick strap on dildo brought my soldier to attention.

Not to be outdone, I saw her tale of sapphic penetration and raised her the story of my graduation present. Now it was Tara's turn to squirm, her legs rubbing together, her finger getting lost in the hem of her shirt, her breath getting ever so shallow. As I told her the details of my messy finish on Steph's chest, I saw Tara's demeanor change. The pale, flat of her chest that was visible under the cut-wide neck of her heavy metal t-shirt began to flush, and she started to fidget, as though she was trying to shoo away some unwanted feeling.

"Well, what about your dare?" She said finally, after a long, thick silence.

At lunch with Tara last weekend, during a game of truth or dare, she had dared me to take a video of me and Steph fucking and send it to her. In her mind it was evening the playing field since I had seen her and Sarah fucking the night before. My horny, hormone-adled brain seemed to agree to that logic, and amazingly I said I'd do it.

I had all but forgotten about it until Tara mentioned it.

"I don't know, Tara," I said, trying to navigate the thick tension in the room, "I don't think it's right."

"I didn't know you were such a chicken, Miller" she chuckled, a devilish smile on her face.

"I know what you're trying to do, Satan," I said, playfully making the sign of the cross with my index fingers, "but things are going really well with Steph, and I don't want to ruin it.

"Fair's fair, you know," she said with a mock sadness.

"I know," I responded, then dropped my tone into sincerity, "I just can't have any more deception between us."

"Fine, fine, I understand," she said with a long sigh. "It's too bad," she continued as I took a sip of my own drink, "I bet you look great when you fuck."

I choked, I sputtered, and ended up with most of my mouthful of drink on the front of my shirt.

Tara burst out laughing, and after a minute to catch my breath I joined her.

This girl was something else.

Friday rolled around and I was nervous. Nervous and excited. Sure, Steph and I had spent plenty of time exploring each others' bodies at this point, but we hadn't just sat and talked like two normal people for a very long time.

I was looking forward to it.

I tried to make myself look presentable and adult, doing my best to hide the fact that I was just a dumb, horny 18 year old. I chose slacks and a nice shirt with a blazer, but stopped short of going full tie. I thought I looked pretty good, all things considered.

While putting the finishing touches on in the bathroom, I glanced out the window toward Sarah's. The room was dark. I wondered where she was. I wondered where Tara was, and if they were there together.

Suddenly her light popped on. Caught in the middle of a giggle fit, Sarah tumbled into view. Following close behind her, equally overcome with giggles, was Tara.

I was transfixed as the two beauties drew close to each other, embraced, and began softly kissing between fits of laughter.

I felt my balls begin to tingle, and blood rush toward my cock.

The two fell onto the bed, and then Sarah pushed herself up and pulled off her loose-fitting sweater. Her hand reached back and popped the clasp on her bra.

My hand drifted toward my zipper...

NO!

Snapping myself out of it, I shook it off, left the bathroom, and turned off the light. Tonight was about me and Steph.

My phone buzzed. It was a text from Steph. My stomach sank, thinking that she might possibly be backing out.

"Pick me up at the bus stop up the street." it read. I was confused--we had agreed to meet outside and leave the house together, but clearly there was a change of plans. At least she was still coming, so I texted back an affirmative and headed downstairs.

"Wow, looking sharp, Timmy," Alex said as I gathered my things, "where are you off to tonight?" She leaned against the kitchen counter drinking a glass of water.

"I could ask you the same thing," I replied. Dressed in a dress that went down about mid-thigh, split in the middle with a big, brown belt, there was a nice cascade of bare leg that poured down into mid-length cowboy boots; Alex was looking pretty good herself tonight. "Big date or something?"

"No, just hitting country night at El Tornado with some friends." She said, finishing her water. El Tornado was a bar a town or two over, and it was an open secret you only had to LOOK 21 to get in.

"Well, I DO have a date tonight," I said proudly.

"Timmy, you don't need to get dressed up to go to the adult bookstore," She laughed.

I got heated, and was just about to tell her who exactly my date was with when her phone rang, she answered it, and quickly walked out of the room.

I cooled down. Nothing was going to ruin this.

Getting in the car I headed out, taking the first turn off my street, and saw the bus stop ahead of me. Waiting beneath the low light of the street lamp was an absolute vision.

Hair done to perfection, each strand placed for maximum effect, Steph wore a light leather jacket over a tight, sleeveless top. A maroon skirt hugged her hips and covered her legs down to just above her knee, but her calves were bare and glimmered in the light as they swooped down into ankle high boots.

I pulled up next to her.

"Let's go before people start to think I'm some hooker or something," she chuckled, dropping in to the passenger side.

We chatted a little as we drove to dinner, but I couldn't focus on too much conversation. My attention was split between safe driving, and getting every slight peek I could muster at those gorgeous legs. My cock was hard already. This date was all my idea, I had wanted a night where we could just spend time together, but I was desperately close to abandoning it all and diving head first between those thighs.

Somehow I held it together and we made it to the restaurant in one piece.

Dinner was nice. A mid-level Italian restaurant was as nice as either of us could afford, but the food was good and so was the company, so neither of us complained. We talked and reminisced. We gave each other a hard time about the old days, and I got her laugh, which is confidence-boosting rocket fuel to any man. I learned she loved to kayak on the river with her dad, she learned I took gymnastics till I broke my ankle when I was twelve.

It was truly a real date, the first real date I had actually ever been on, but still, something was gnawing at me.

"So how come I picked you up at the bus stop tonight?" I asked with trepidation during a lull in the conversation, "I thought we were going to meet out in front of the house?"

Steph smiled meekly and pawed at her tiramisu with a fork. I knew the answer, but I wanted to hear it from her. I decided just to go for it.

"How come you're so afraid for her to know about us?"

Her fork stood still.

"Are you embarrassed to be with me?" I said.

"Honestly?" She said, finally looking up at me, "Yes." My stomach dropped. "Or at least I was...at first."

I felt a smile tug at my lips but I fought back as I listened.

"I know our...history...and when I asked you to help me with that exam I honestly did just need help, and you were the closest person I knew who could help me. Something changed when we started spending time together, though, and I found myself...attracted to you."

I felt a stir in my pants as her tongue quickly snaked out across her lips.

"I think that's why I reacted so harshly when you told me about your little audio voyeurism. I didn't know how to handle anything I was feeling. Even at the prom, what happened in the limo...at first I didn't think it would go that far, and then I told myself it would be just once, but..."

She took a sip of her drink. The pause felt like an eternity

"I don't let people in easily, Tim," she continued, "but you...you got in."

"Then why are you so afraid of Alex finding out?" I pressed.

"Tim, how do you think she would feel if she found out I was fucking her younger brother?" She said with a long sigh. "There's enough weirdness going on there as it is, I didn't want to make things worse."

"What IS going on with you two? I asked. Steph's eyes went somewhere far away

"I don't know. Ever since I told her I was going to be going to the same school as her, she's been pulling away." Her fingers began fidgeting with her napkin. "I don't think she wants me to go."

She was clearly upset. My fingers snaked out across the table and touched hers. She didn't pull them away.

"Hey," I said, her eyes clicking back up to mine, "let's get out of here."

We walked hand in hand back to the car. She grabbed me by the lapel of my coat and pulled me in for a hard kiss.

"Tim, when we get home...I don't care who sees us." We smiled. I pushed her back against the car. Our tongues collided as my hand slid down her body. I rocked my thigh in between her legs, pressing tight against her pussy. She gasped, then pushed me off. "But first, I have a surprise for you."

She smiled that sly, devilish smile of hers and slipped into the car. I adjusted the iron rod in my pants and walked around to the driver's side.

I could barely keep my eyes on the road as I drove toward Steph's "surprise." She sat in her usual, seductive pose, back against the door, legs stretched across the bench seat, feet resting on my thigh. I could feel the heel of her boot ever so slightly grazing against my cock as we drove.

When we got to the surprise, a big grin broke on my face, and I felt a surge in my pants. Steph had gotten us a hotel room. It wasn't anything fancy, but it was a place that was just for us, a place with a bed and some privacy.

12