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.
