Diary of a Horny Student Ch. 02

2

The events of the previous night played back in my head as I showered the next morning. The godly Christine's confession of sinful activity with her earthly boyfriend Eric; the swelling cleavage and hard nipples of Rachel pushing the boundaries of a girl who as far as I knew had never even kissed a boy; the soft orgasmic cries of Steph, my step sister Alex's best friend and our upstairs neighbor; and then there was Rachel's "promposal" that I of course said yes to as I floated back to earth from a mind-shattering masturbatory climax. I had a prom date! It wasn't for MY prom (I'd deal with that when I dealt with it), but it was a prom date nonetheless. I toweled off and peeked out through the blinds of the bathroom window, hoping to catch a glimpse of Sarah, my gorgeous redheaded neighbor with the perfect tits, but alas she must have already left for school.

I descended the stairs and found Alex and Steph in a tight hug, the two lamenting the fact that they'd be separated for the next few months as Alex was headed back to college, her spring break now over. I wondered about them. They were close. Very close. And even now, their hands touched each other in a way that was innocent enough to the rest of the world, but to an eighteen year old, horned-up virgin like me it seemed very...intimate. When I snapped out of my ogling, I was slightly mortified to see Steph's eyes cracked open in her embrace and looking right at me.

I said my goodbyes to Alex and was on my way out when I heard a voice call from behind me.

"Hey, Timmy, wait up!" It was Steph. Ugh, and she called me Timmy. "Could you give me a ride to work? I'm late."

She was dressed in an unflattering two-tone combination of polo shirt and slacks, golden blonde hair up in a messy bun; it was the ever-bland uniform of the coffee shop barista. Steph was taking a year off, after a disappointing freshman outing at the local state college. While she was thinking over her future as a higher education student, she grabbed whatever job she could find to help make ends meet while still living with her parents.

"Yeah, sure, hop in," I said. She slid in through the driver's side of the old boat of a sedan that I drove, lifting up the arm rest to shimmy across the bench seat to the passenger side. She turned toward me as I got in.

"So," she started as she laid out her long legs, placing her feet onto my thigh, mere inches from my cock, "you've finally got me all to yourself in this big roomy car...what're you gonna do to me?" A slight grin and a cocked eyebrow followed.

There were lots of things I wanted to say. This girl, this older woman, had teased me as long as I could remember, and as she grew older and her tits got fuller and her ass got rounder, I was the first one to get the test run of all her newfound sexual confidence. In the summers, when she and Alex traipsed around in bikinis, I knew Steph was bending over extra far for me when she'd get drinks out of the fridge, making sure to arch her back when she knew I was looking. I was the guinea pig for her feminine wiles, and she knew she had me by the balls.

"I'm going to drive you to work, Steph," I flatly intoned. I WANTED to say I was going to spread those toned, volleyball player legs and lick her pussy until I heard those heavenly moans of hers up close and personal--that sexy short-short-long release of pleasure I knew so well at this point; that erotic sound of release that drifted down through the floorboards when she would finally cum. But I didn't, because my only defense against her teasing was to play it as cool as possible.

"I wanted to talk to you about something, Timmy." My mouth went slightly dry. For a moment I panicked, wondering if she knew what I had heard last night. Had SHE heard ME? Had I unknowingly let out an audible moan as I shot my load, thinking about her hot, spasming pussy mere feet above my head?

"I don't know if Alex mentioned it at all to you, but I really want to be able to transfer to Alex's school next year. In order to do that, I really need to nail this final credit class I've been taking, and so far I am...not. So...I was wondering if you could help me out with some school stuff. Like a tutor."

Well this was unexpected. I was headed to college for writing in the fall, so that'll tell you right there that I wasn't an academic whizz, but I guess you could say I knew my way around a textbook. I was happy to help a family friend, but as I thought about it, I realized this put me in a very interesting position. For the first time in my life, I had the upper hand on Steph. Now, I wasn't going to be a TOTAL creep about it, but I did think of a way to use it to my advantage, a way to make up for years of teasing.

"Yeah no problem at all," I replied, "but I want something from you in return."

"I can't pay you much, but sure"

"Not money," I said, looking her in the eye as I rolled to a stop in front of her coffee shop.

"Listen, Tim, don't get any ideas, I'm not paying you with blowjobs or something, so forget it." She called me Tim, not Timmy. She was holding her breath, but her feet didn't move from my thigh.

"Come on, don't be crazy, I don't want that," I chuckled, "I want you to go to the prom with me." I felt her exhale in relief.

"The prom? That's it?" She laughed, relieved, "sure, Timmy, I'll go to the prom with you." She gathered her things as she started to leave.

"But I want you to wear something slutty," I called after her. She paused, giving me a look that told me she understood what I was up to.

"Something slutty, huh? So you can look like a big man in front of your buddies?"

"Something like that," I smiled.

She paused a moment, considering, and then leaned close in. She ran a finger down my cheek. Her polo shirt hung off her body, the top buttons undone. I could see the swell of her supple breasts, hugged by her black bra. "Tell you what: you help me get an A and I'll wear something so hot there won't be a soft cock in the whole class.

My mouth was like the Sahara. I snapped out of it as she playfully slapped me in my stupid slack-jawed face. The power was hers once again.

"So why don't you pick me up after work and we can get started tonight!"

"Y-yeah...sounds good..." my cock was iron. She popped her head back in right before she left and gave me a knowing smile.

"Thanks, Timmy." And then she was gone. I watched her perfect ass swish away before I drove off, balls blue once again, and late for class.

School was dull, but my sexual frustration was ever present as I was caught in the seemingly unending parade of perky teenage tits, tight teenage asses, and pouty glossy lips. All so close, but also so, so, far away. The only highlight was creative writing class. The teacher, Ms. Dorman, was a recently engaged 28 year old with thick-rimmed glasses and a beaming smile. Always dressed fashionably but not provocatively, she was the epitome of cute. She had a way of making friends with the more dedicated students, so I, along with my good friend Tara, had become more than students at this point, almost like peers. This meant that as graduating seniors, Tara and I could spend our time in class taking it easy and catching up with each other.

"So you went from having zero prom dates to having TWO prom dates in less than twelve hours? Miller, you dog, that's amazing!" She cackled, clapping in celebration. A raven-haired, pale-skinned, classic "art school" type, I had lusted after her for a long time, but I could never tell if it was the lust of true attraction, or simply a result of the fact that I was a horny teenager, and she was the closest female who talked to me regularly. Either way I chose to push that aside and focus on the fact that she was one of my closest friends. That didn't mean the lust ever fully went away, though.

Casually goth but full of sexual confidence, Tara never shied away from accessorizing to accent her considerable assets. Today, slim, black jeans with strategic tears in them framed her tight curves. Long necklaces wrapped around her neck and plunged into the deep cleavage of her perfect D-cup tits, tits cradled by a tight, bustier top. And they WERE perfect tits. I knew this because Tara was also the closest thing I had ever had to a sexual partner.

Close friends that we were, we talked about anything and everything, and being two horned up teens, our conversations would always inevitably skew dirty. Tara was the sexy scenester girl that seemingly everyone wanted to fuck, jock or nerd, male or female, and she loved the buffet of options before her. A theater nerd here, a football player there, she always seemed to have some new perversion or experience she wanted to share. We were still awkward kids, however, so as a way to diffuse the awkwardness we developed a method of discussion to match our maturity: truth or dare.

We learned a lot about each others' sexual lives through truth or dare, and it allowed us an element of comfort that brought out total honesty. Through truth or dare Tara told me the most personal of things, things like the fact that she loves to suck cock, and that one time our class valedictorian Suzie Travino almost went down on her. It also coaxed her into showing me her vibrator, the one with the one-two-three, one-two-three buzzing pattern she liked. Not to be undone, but with much less direct experience to relay, I in kind told her about what kind of porn I watched, the time I came in my pants at a church youth camping trip, and how I jerked off to the sounds of Steph orgasming a floor above me, among other things. Nothing was off limits.

The night of her eighteenth birthday party, she and I were the only ones left, and we were lounging in the dim light of her finished basement, recounting the events of the evening while delightfully buzzed on over-boozed punch. We laughed about the chaste game of strip poker that broke out but ended before any nudity happened, and how high school jock Ben Pepper hung around way past his welcome, clearly expecting something to happen with Tara. Her eyes sort of drifted far away at the thought, so I took the opportunity.

"Truth or dare?" I lobbed at her. She looked at me from her seat on the floor, arms draped in such a way that the tops of her heavy tits casually pushed out through the opening of her tight button down, creating some excellent cleavage.

"Truth," She smiled.

"What exactly was Ben expecting that made him stick around so long?" I inquired. She playfully bit her thumbnail in slight embarrassment.

"Another blow job probably."

"Another?"

"Yeah...he'd been after me for a while, and since Friday was my actual birthday, and I was a little drunk, I told him after the game I wanted to blow out his candle."

"You did NOT say that," I said in disbelief.

"I did!" She cackled, embarrassed, "so we drove out to The Spot, and started making out. It was all getting me going, so I took out his cock and started sucking..." she trailed off.

"But?"

"But...it was less of a candle and more of a damp noodle. I must have sucked his dick for 15 minutes but nothing happened! He told me to stop and tried to get it going himself, but no dice--I had my tits out and I was rubbing them and being all sexy, but nothing worked! Finally we just gave up and he drove me home." She looked wistful for a moment. "Funny thing is, I had always wanted to see a guy jerk himself off. What a disappointment.

"Ha! Yeah, you're not missing much," I replied, my hardening cock insisting I picture Tara lustfully rubbing her firm tits in my mind's eye. A short silence hung in the air, until Tara broke it with a question.

"Truth or dare?" She said, sipping her punch.

"Truth!" I proclaimed. Tara made a disappointed face.

"Boooo, Miller!" She jeered. I found it extremely sexy when she'd call me by my last name. "It's my birthday, come on!"

Still buzzed from the evening's festivities, I gave in. "Fine, fine, dare!"

She smiled, and climbed up onto the couch next to me.

"I dare you," she started, "and remember it IS my BIRTHDAY..."

"Uh oh..."

"...I dare you...to jerk off for me."

Time froze as I processed the request.

"...WHAT?" Responding to my hesitation, she shifted herself closer to me, her spilling cleavage inches from me now. I did my best not to look.

"Yeah, I mean...like I said, I've never seen it before, and Ben was a dud, so...why not?

It was a great question. I had jerked off thinking about her plenty of times on my own after our truth or dare sessions. I'd stroke furiously while I thought about my good friend Tara, the goth girl with the fantastic tits, on her knees slurping away on a big dick, or legs spread with Suzie Travino's face in her pussy, or getting fucked in any which way her wet pussy wanted to take it. But this was different...right? I mean, she was actually here!

"Why don't you ask one of your actual fuckboys to do it?" I said, trying to play it cool, while also unconsciously shifting myself to try and diffuse the tingle in my balls.

"Because...asking a guy just to let me watch him jerk off is kinda weird, isn't it? I mean they already think I'm a freak, but...I don't know. It's a kind of intimacy I don't think they'd be ready for. I trust you, and I know you won't try to jump me or anything.

"Tara, I don't know, I've never...in front of anyone..."

"It's a lot, I know, I promise I won't touch you or anything," she added, sliding away to the corner of the couch, out of arms' reach. Yeah, god forbid she actually TOUCH me..."this isn't foreplay, I just...want to see what it's like."

I stared her in the eye in silence. She was serious. I went over the implications in my mind. Would this ruin things between us? Would it make things better? Was I overthinking it?

She looked back at me. Perched on her knees at attention, I watched her nervously fidget with the fishnet stockings she wore under her black denim short shorts. I could see the faint outline of hardening nipples through the fabric of her button down.

Slowly, under the low mood lighting of Tara's basement, I reached down, unbuttoned my pants, unzipped, and pulled out my cock. I looked at Tara, but her eyes were fixed elsewhere. Her tongue slowly ran back and forth across her bottom lip as I began to stroke.

Now, after all this talk, you'd think I'd be rock hard, but I was...not. I don't know if it was the booze, or the stress, or the awkwardness of the situation, but my team was not immediately ready to play.

"I'm sorry, Tara, this is just a little too uncomfortable, I don't know if I can..."

"I know, I sprung it on you," she mused. Pausing in thought, suddenly a wry smirk flashed on her face. "I know this is awkward, and you know what? Fair is fair."

Her hands drifted up to the buttons on her shirt, and began to undo one after the other at a tantalizingly slow pace. When she reached the last one, she ran her hands up the exposed skin of her stomach, over the glorious, protruding cleavage presented by her black push up bra, convening them at the clasp that lay between her breasts.

She paused there a moment, then undid the clasp, pulling the cups away like Moses parting the red sea, revealing to me the most perfect set of full, milky white tits I had ever seen--the first set I had actually seen in person. Full, but still firm, and topped with two hard, pink nipples, they had the most wonderful jiggle to them as she took her shirt and bra all the way off. They were works of art. Settling back into her corner of the couch, tits fully on display, she looked at me. Our eyes met in a silent confirmation of "this is really happening," then hers drifted downward toward my cock.

"There. That's more like it," she said through a wry smile. I was now rock hard. I began to slowly stroke as I took in the vision before me. Tara was entranced.

"You know, and I'm not just saying this Tim...but you have a fantastic cock," she said in a manner almost clinical, but the way she subtly shifted her body closer implied her interest was more than academic. Either way I felt it throb hard and proud in my hand.

I continued to stroke as my good friend watched, my head darting back and forth from her exposed chest to anywhere else in the room, in a vain attempt to avoid staring at her exquisite eighteen year old tits.

"It's ok to stare, Tim," she said, her breasts giving an erotic shimmy as she shifted a bit closer, "it's why I took them out." I gave in and looked directly at them, cock throbbing in approval; but it wasn't just her tits--it was the whole package. Her short, dark hair framing her face, accenting her thick, back eyeliner; the sheen of her wet lips as her tongue periodically slid across them; the choker she wore tight around her neck; the ridge of her collar bone catching the low light, its cast shadow creating a frame for the works of art on her chest; the position she sat in, legs tucked under almost like a pinup model, her curves a winding highway that ran over her petite waist, around the flare of her hips, and down her coiled legs.

I heard a sudden intake of breath as the first pearl of precum crested the head of my cock and dripped down the shaft. She was as turned on as I was, she was just trying to play it cool.

I decided to give her her money's worth, and pulled out every masturbatory trick in my book. Trading off hands, pausing periodically to rub my balls, massaging that magic space just behind them; Tara was eating it up. Hypnotized by my self pleasure, she drifted one hand down to her right breast, and began a soft, instinctual stroking of her nipple that she didn't even realize she was doing. More precum ran down my shaft as my cock throbbed.

Suddenly breaking her own trance, and realizing what she was doing, I think she decided this needed to wrap up before things got too out of hand, because what she did next was an expert-level execution of almost instant orgasm.

"You know, if you're still not fully comfortable, I can set the stage for you even better if you'd like," she cooed as she shifted closer to me still, now just inches away as I stroked my cock just for her. "Just close your eyes and picture yourself at home in your bedroom,."

Not wanting to take my eyes off those amazing tits, but also too far down the pleasure path to argue, I shut my eyes.

"There you are, just stroking away at your fantastic cock...when suddenly you hear something coming from upstairs." She leaned in close to my ear.

My eyes snapped open as soft moans of pleasure spilt from Tara's mouth to my ears. She was mimicking Steph's forbidden sex sounds, the sounds that had driven my dick to explode harder than anything else ever had up to that point.

"That's not fair!" I pleaded but she didn't stop, and neither did I. She continued her performance, orgasmically cooing into my ear, matching my speed as I stroked faster and faster, my cock vibrating as the precum flowed. My breath grew ragged, Tara's moans grew louder, and as I reached the edge, the point of no return, Tara mimicked perfectly the unique cry of Steph's orgasm--the short, short, long moan of ecstasy that accompanied her spasming pussy.

"Jesus Christ, Tara!" I cried as I clenched my eyes, and my balls erupted. I audibly moaned, and jerked as a torrent of hot cum launched its way up the shaft of my cock and into the open air right in front of Tara's face, four, five, six, times.

"Oh wow!" I heard Tara say through my orgasmic haze, followed by another "wow" and "There's so much!" as my cum kept pumping.

Hand and cock slick with jizz, I stroked to completion, slowly coming back to earth as the pulses in my cock got further and further apart. Spent, I let out a deep breath. My hand, crotch and stomach were absolutely drenched. I looked over at Tara, who hadn't moved an inch. She was taking it all in.