Chapter 1: How can Tim Miller’s blue balls get some relief?
By LiminallySpaced. Listen to the Podcast at Explicit Novels.
It was a Sunday morning, and my cock was hard in my hand. As an eighteen year old virgin, the strength of my erections was never in doubt, but their frequency was becoming distracting, to say the least. Hard when I went to sleep, hard when I woke up, hard at various impractical points throughout the day, my hormones were in a constant cascade down from my brain to my dick, swelling up my balls and begging to be released in an explosion of hot, white, euphoria.
As warm water showered down my body, I worked toward that release. Eyes closed tight as I stroked up and down, my mind tried to organize the overwhelming stimulus it took in on a daily basis as a horned-up high school senior. Lori's cleavage when she bent over to pick up her pen, the way Tara's tight gym shorts framed her perfect ass, Michele's lips and tongue running over the tip of her pen while deep in thought. my cock screamed at me, throbbing, egging me on like my own personal drug dealer, pushing me to imagine how these young women, my classmates, my friends, might act if they were with me right now, their bodies consumed by the same fire as mine, and what depraved things they might do to reach their own satisfaction.
But as I raced down the final straightaway toward ultimate pleasure, my mind’s fantasies landed in the same place it always did. Instead of my hand sliding up and down my cock I envisioned a mane of fiery red hair bobbing back and forth, lips, tongue and hands touching me, sucking me, desperate to pull my climax out of my body. Then, right as I was approaching the edge, the mental image became the emerald green eyes of my next door neighbor Sarah looked up at me, her large, firm breasts pressed together by her arms as both hands pumped my shaft and kneaded my balls. Her breath was as labored as mine, her eyes burned with the fire of wanton lust. We both knew what was coming, and she wanted it, needed it, as badly as I did. Sarah's hands, lips and tongue coaxed me closer and closer. My balls churned, coiling tight, my breath got ragged, and then time seemed to stop as Sarah placed the trembling purple head of my cock on her bottom lip, stared me right in the eye, and whispered.
Alexa Ruins My Moment
"Hey, I'm coming in!" My eyes burst open, hand off my cock and quickly closing the gap in the shower curtain as I angled my rapidly deflating dick away from the bathroom door. The abrupt entrance of my step-sister Alexa snapped me right back to reality, instantly sending me lightyears away from that glorious precipice of pleasure.
"You know it doesn't really work if you knock, after, you open the door."
"Eh, get over it, I wasn't looking, and besides, you've been in here for like half an hour. Other people need to use the bathroom in the morning too, you know!" Alexa was a bit older than me, and you'd think college would have taught her some new manners about sharing a communal space, but any tact she might have learned fell away as soon as she came home for a weekend, a holiday, or in this case spring break.
I always used to lock the bathroom, automatically, but when Alexa went off to college, I got out of the habit. That’s going to changed immediately. "Why are you even up this early? You guys were out until like 2 am last night," I challenged my intruding stepsister.
"Stephanie and I are going on a bit of a road trip today, so we wanted to get a jump on things," Alexa said as she sat pissing in the toilet. I was just an arm’s reach from her, only veiled by a cheap white vinyl shower curtain; But I stood there petrified by fear. Fear of Alexa’s complete disregard of my privacy.
Girls on the prowl
Alexa was out Saturday night with her friend, Stephanie. Stephanie & her parents lived in our upstairs rented-out apartment. Stephanie and Alexa had been inseparable for as long as I could remember. As a night owl myself, I had heard them stumble home late many nights, and last night was no different. Straining cock in my hand, the sound of the closing front door, along with hushed whispers and giggles as they walked by my room, triggered momentary mid-masturbation paranoia. I froze in silence, mid-stroke, to make sure I gave no indication of what I was doing, but the pressure in my cock never abated. In that moment my horned-up mind wandered to Stephanie, a tall volleyball player with long toned legs and more than enough tits. Last night, as I surfed porn at 2 in the morning, I heard her footsteps coming down the hall. I wondered where she'd been. Had she sucked someone's dick? Had she swallowed their cum? My cock throbbed.
Once I heard her bedroom door close, I thought the coast was clear & I started back up again. Thoughts of Stephanie lingered, and as I timed my orgasm to the cumshot clip I watched on my computer, in my mind's eye it was Stephanie’s face I saw, mouth open in a slight smile, happily splattered in white.
Just as the blast of cream abated, Alexa interrupted from the hallway; “What are You doing up so late?”
"Nothing, just watching a movie."
Her languid response of "Um Hmm" said she didn't believe me, but wasn't going to push it.
"Well just hurry up and finish, huh? You know mom hates it when you're late for church.” Her tone implied a double meaning.
Back to this morning’s shower.
I heard the toilet lid close, followed by a strong flush. “Damn it!” The sudden blast of scalding water led to my frantic overcompensation on the shower knobs, causing my cock getting a blast of ice cold ‘therapy.’ I finally got the mix adjusted, but as I looked down at my now totally flaccid penis and frustratingly full balls, I knew the only thing being finished right now was my shower. I rinsed, turned off the water, and stepped out.
As I toweled off, my mind drifted to all the things I had coming up in the next few months. After tucking in my towel around my waist, I opened the bathroom door to abate the steam, so I could eventually check my hair in the mirror. I brushed my teeth while thinking about things like finding a prom date, making sure my summer job was set up, and getting ready for college in the fall.
As I went through the rest of my morning toiletry routine, several thoughts meandered through my head, but I was brought back to earth as my gaze fell on the bathroom window. The blinds were inexplicably drawn up so that this small window looked directly at Sarah's bedroom window, and as the fog cleared from the glass, it revealed the beautiful redhead whose lips I had just minutes ago been fantasizing were sliding up and down my cock. There she was, almost topless, with only a sheer black underwire bra shielding her perfect breasts from my eyes.
She moved around her room casually, looking for a top for the day, but I froze. I'd caught a glimpse of her puttering around in her room from time to time over the years, but usually it was as a silhouette through curtains, and always fully clothed. Her curtains must have been broken now, as this was a straight shot right into her bedroom, the morning sun illuminating her pale cleavage like a beacon.
I flicked off the bathroom light, shut the door, & clicked the lock. Standing there in the dark room, I could see Sarah, but all she saw was a screened dark bathroom window.
Sarah and I were friendly, but I don't know if I'd say we were friends. We had lived only feet from each other for many years, and had grown up going to school together, but we never really traveled in the same social circles. Regardless, as the years went by she developed into the most beautiful thing I'd ever seen. I was just too petrified by her beauty, and my own inexperience, to really do anything about it. Outgoing but private, I had no idea if she had a boyfriend, a girlfriend or what. My hormone-addled brain was dying to know her sexual history, and I had spent many nights imagining all its details for my own pleasure.
I felt the blood start to return to my cock, but another impatient knock on the door from Alexa snapped me out of it.
“Use the other bathroom,” I yelled in a defiant tone.
When I looked back, Sarah had gone, and instinctually my hand sprung to close the blinds, not wanting anyone to be privy to the magic portal I had just discovered.
The image of those busty, freckled tits stayed fresh in my mind as I got dressed. I wondered what her nipples tasted like. What her tits would feel like wrapped around my cock. How slowly my cum would slide down between them. Jesus I just wish I had cum in the shower. I really needed to snap out of this.
The smell of bacon brought me back to earth as I entered the kitchen. I looked toward the stove and saw another lovely sight; two long, athletic legs leading up to the shortest shorts humanly imaginable. Inside those shorts was an apple of an ass, and above that, a tight, spaghetti-strap tank top covered a long, tight back leading up to a messy bun of dirty blonde hair, with headphones on each ear.. The whole package gyrated slowly to a song only she could hear as she made herself breakfast. The blood once again started its pilgrimage to my cock.
"Hey, neighbor," I greeted Stephanie as I opened the fridge door in an attempt to hide my arousal.
"Oh, hey, Timmy!" she said as she whirled around to greet me. She knew I hated the name Timmy, but she never passed up a chance to tease me. It was clear when she turned around, that she had stayed the night, as her nipples were clearly visible through the tight fabric of the tank top. As the only man in the house, and not much of a threat at that, Stephanie was always very relaxed when she was here, which meant she had no problem hanging around in whatever she slept in. Alexa would usually follow suit, and their sleepovers generally meant a parade of unfettered tits and nipples covered only by the thinnest of garments. This was both heaven and hell for any boy my age. Even now my eyes couldn't help but lock in on her perfect tits, and she caught me staring before I could look away.
"Are you staring at my tits, Timmy?" she said with a wry smile. I scrambled and focused on something else to cover my ogling.
"Nah, I'm staring at that hickey on your uh, chest. You fall asleep on the vacuum again?"
"Very funny," she chuckled, "I bet you'd love to know where I got it, wouldn't you, perv?" It was true. I blew it off and tried to seem cool, but goddamn it was true. The little deep red mark peeked out from the hem of her tank top, on the inside of her right breast and it was driving me mad. Did she get it last night? Did she get it. from Alexa?
I'd never seen Stephanie with a boyfriend, and due to all the time the 2 girls spent together, I naturally wondered if Stephanie and Alexa were a little more than just friends. Stephanie’s upstairs unit was laid out fairly similar to ours, so her bedroom was right above mine, which meant I could hear loud music and girlish giggles pulse through the floor every time they hung out. Then one night, when it was extra quiet, the sounds of faint moaning snuck their way through the floorboards, in through my ears, and directly down to my dick. I was too shocked to do anything but sit there with an intense hard on; Alexa wasn't home; was she up there with Stephanie? Did she have those long legs wrapped around my step-sister's head? The fact that I was over hearing something so personal, made it taboo and voyeuristic, and hot as hell. I tried to keep the incident out of my mind, but when I heard those sexy little whimpers trickle down a second occasion, a third, I couldn't ignore it. Sometimes Alexa was home, sometimes she wasn't, and I'd listen closely, stroking along, wondering if Stephanie was touching herself, or if Alexa was touching her, or licking her tight cunt, or even if that tight cunt was wrapped around a hard cock. I'd match her intensity, getting faster and faster as she lost control, until the sexiest sound a woman can make freed itself from her mouth in a unique short-short-long pattern of ecstasy, and I would cum so hard I almost blacked out.
"Have fun on your trip," I managed to choke out through a suddenly dry mouth. I grabbed a yogurt out of the fridge and went on my way. Today had been quite the test already, so heading off to church with my step-mom seemed like a great way to get my mind out of the gutter.
Or so I thought.
Despite working a dangerous job being a cop, my dad was never really one for religion. Neither was Kelly, my step mother, at least not until the night dad got injured in the line of duty. He passed away after two weeks in a coma, but Kelly's prayers never stopped. She found a great church shortly after we lost him, and the community of parishioners helped her, helped all of us, through a very difficult time. Alexa stopped going once she went off to college, but I continued to go with Kelly every week I could. I don't know if I believed any of it, but I knew me being there was soothing for Kelly, so I did it to make her feel good. I also did it because I missed my dad, and sometimes it really did help. One of the perks as well was a great youth ministry that introduced me to new kids from different nearby towns.
When I arrived, late as always; I was greeted by a warm smile and a discreet wave from the pastor's daughter, Christine. A cute brunette Italian girl, with a sexy, smokey voice, I had developed a crush on her almost immediately. She had a style that was conservative, but definitely not prudish, a tantalizing dichotomy that was on full display the first summer we met. Big, baggy t-shirts would hang loose, revealing little form, while also giving just the slightest suggestion of the small, perky tits underneath. Below were short shorts, revealing long, strong legs formed by years of running track, and skin that seemed to have a warm, perpetual tan regardless of the season.
A kind heart with a beautiful soul, Christine welcomed me into the church's youth social scene immediately and we became fast friends. I say emphasize friends, because I quickly learned Christine had a long time boyfriend named Eric. Eric was a good guy, but he wasn't a church goer, much to her father's dismay, and it was a source of much struggle for Christine as well. Having one foot in the godly world and one foot in the secular world can be very confusing, especially at our age. You see, despite being the pastor's daughter, Christine was still a red-blooded, 18 year old girl with wants and needs that boiled hot and furious just like everyone else. Christine trusted and confided in me, and while she never went into detail, I knew the pastor's daughter was doing SOMETHiNG sinful with her boyfriend; I just didn't know exactly what. This made my imagination run wild, but she was my friend, and doing her best to stay a good Christian girl, so I tried to ignore those thoughts as much as possible. I didn't always succeed.
After the service my eyes scanned the congregation as everyone milled about. They fell on a face I hadn't seen in quite a while; a face that sent a slight tingle straight to my painfully full balls; Rachel. Tall, with long, strawberry blonde hair, Rachel was definitely what would be called thicc. Cute and innocent-looking with big doe eyes, Rachel by far had the biggest tits I’d seen of any girl my age. Sturdy bras held up her two talents while a tasteful sundress gave a hint of deep cleavage, and hung off the crest of a plump ass and thick thighs. Another longtime friend of mine, Rachel and her family belonged to two churches, so It was a rare treat to see her in person. To the casual onlooker it wouldn't seem like she and I had much of a relationship, as we generally didn't do much more than a smile and wave or a quick hello, but she and I actually had a very lively online relationship that saw us talking digitally almost every day. We'd chat about everything and anything as two teenagers growing up in the world. I enjoyed talking to her, but things never got particularly saucy. I'd complain about girls and she'd humor my grumblings, but when it came to Rachel and boys, there didn't seem to be much there to talk about. She was very clear she was saving her virginity for marriage, and that's generally where things would end. Even so, there was many a night where after one of our long digital conversations I'd massage my cock to completion, while wondering what she did with those magnificent, innocent tits when she was all alone.
Making a bee line for me through the crowd now was Christine. After a big hug we chatted a bit, but I could tell something was off. It was a normal routine for Christine and I to take a drive and hang out after church, so we said our quick goodbyes, hopped in my car, and headed off to get milkshakes. Sitting in the parking lot, I decided to try and get to the bottom of what was bothering my friend.
"So what's up? You're being awfully quiet." I glanced over at her, taking note of her outfit. Today she was wearing a nice tasteful blouse, but her legs were on full display, reaching out from beneath a knee length skirt, which I noticed was currently bunched up tantalizingly at mid-thigh.
"It's nothing, it's just," she paused, shifting her legs together nervously,
"it's just, Eric. Well, actually, it's really me."
"Go on," I said, watching her pick the hem of her skirt.
"I'm just worried about what comes next. For us, Eric and me. College starts soon and we're going to be so far away from each other, and I'm. I'm worried there's not enough, you know, incentive to keep a long distance thing going."
I thought I had a feeling where this was going.
"You mean you think because you're not having sex with him he'll find greener grass somewhere else?"
"Well, sort of, I mean. Can I; can I tell you something?" She started to blush.
"Of course," I said. My cock twitched.
"Well, Eric and I. we've always tried to keep each other. satisfied. but a couple of times it's just. the heat just got too much to bear, and we. had sex."
"Oh no way!" I said, trying to play it cool while secretly my mind started racing. I shifted to hide my growing erection as any previous attempt to keep my thoughts of Christine chaste were instantly gone. I imagined her on her hands and knees, that tasteful skirt bunched up around her waist with her hot ass in the air, moaning in ecstasy as her tight, proper cunt got stuffed with a hot, throbbing cock. My fantasy was short-lived however.
"Yeah, only a couple times, because honestly. I just really couldn't enjoy it. He was a total gentleman and all, but the whole time I couldn't stop thinking that I was doing something wrong; something bad. And not in a hot way." My dick was deflating as I listened to my friend's legit crisis. "I was so uncomfortable every time, we could never really get going, and he wouldn't even. you know. cum."
My cock twitched with life again slightly. Even though this wasn't a sexy situation, I couldn't help but note the hotness of hearing the pastor's daughter talk about cum.
"And so you're worried that he's going to get to college and find a girl who's not uncomfortable about it and forgets about you?"
"Actually no, I'm worried about me. I'm worried that this is my body telling me I'm not with the right person, and that I need to be with someone more; godly."
Now don't get ahead of yourself, she wasn't talking about me; she knows I'm not much more than a weekend warrior for Christ, and this was something that was clearly weighing on her quite heavily. The sins of the flesh were bringing her to a serious cross road, and she had some hard decisions ahead of her.
"You know, one thing I know for sure is that I trust you. You've always had a great mind for my shit, and that's why I know that if you trust yourself, trust your gut, you're going to make the right decision." I assured her.
She smiled that warm smile, and I thought I saw her tan thighs ever so slightly squeeze together.
We finished our milkshakes, and I drove her home. Every so often I'd catch her eye and she'd smile again, as the late afternoon wind whipped her chocolate hair around in a frenzy. Before she got out, she leaned over, kissed me on the cheek, and said "thanks Tim. You're a good friend." I watched her sashay towards her front door, making sure to pull her skirt back down before she went in.
Instant Messages
As I drove home my mind raced again, and the tightness in my pants returned. I wasn't so much thinking of the awkward, uncomfortable sex Christine had had, but the thing she had said before that. Satisfied. They tried to keep each other satisfied? What did that mean? Was she jerking him off? Was he moaning in her ear as he spurt cum all over her hands? Had she tasted it? Had he tasted her? Was she regularly gripping the sheets and writhing around as he tongued her clit? Surely the pastor's daughter was keeping it respectable, but what was it like that first time? Maybe over-the-clothes dry humping just got so intense that they lost control. Maybe that sexy, smokey voice breathlessly cried out those two magic words. "fuck me."
The stimuli of the day clouded my mind for the rest of the evening. Dinner and tv with Kelly was a blur; -all I could think about was getting upstairs and setting my blue balls free. I said goodnight to a returned Alexa, packing for her journey back to school tomorrow, headed to my room and fired up my computer. Waiting for me there was a message from Rachel. We chatted about nothing in particular for a while, and then, as the night grew later, quieter, she started to get a bit nosey.
"So where'd you and Christine run off to after church?" she inquired.
"Just went for a drive to get milkshakes; we do it almost every week."
"Um Hmm; milkshakes. " Was this a little bit of sauce from Rachel?
"Why, you jealous?"
"A little bit," she responded, "I love milkshakes. "
I let it hang there, not sure how to respond. Not sure if this was innocent teasing, or if it were a double entendre from this proper, Christian girl whose family belonged to Two churches. I didn't have to wait long though as a new message popped up, changing the subject.
"What do you think of this new top?" it read, accompanied by a picture. It was a tight grey button down blouse. Two buttons were undone, but that didn't relieve the pressure her massive tits put on the other buttons. Her hips were cocked in such a way as to accent all her curves. Blood started to flow to my cock.
"Looks great! I replied as I absentmindedly stroked the tightening crotch of my jeans.
"What about this one?" popped up, another photo attached. It was a red, form fitting V-neck with a plunging neckline. Pictures weren't entirely uncommon from Rachel, but these. these were different. Her tits looked amazing, pressed up and out, a long chasm of cleavage between them. Beautiful, massive tits. Tits that as far as I knew, no man had ever touched or seen. My cock was hard. I pulled it out.
"The perfect top for church," I joked, staring at her magnificent tits as I slowly stroked. She posted "lol" and quickly followed up with a third picture, a picture that sent a hard throb right through the length of my cock as I picked up pace. A tight, green spaghetti strap tank top hugged her body, wrapped lovingly around her epic tits like the other two tops, but unlike the other two tops, there was something missing here. Her bra.
The pose she struck had her tits pressed hard against the tight fabric, and protruding from the center of her succulent breasts were the cast shadows of two nipples. What exactly was going on here? Did Rachel really want my innocent opinion, or was this choir girl aiming at something more erotic? Regardless of intent my cock strained hard in my hand as I stroked faster.
"That one is. very nice" I timidly wrote, belying the state of total, heated arousal I was currently in.
"Which one is your favorite?" popped up as I struggled to maintain composure. As I began to hack out a one-handed response, suddenly trickling down from above me were faint grunts and moans.
Oh my God. it was Steph!
I picked up my pace. With Stephanie’s orgasmic edging above me and Rachel's glorious, fat tits in front of me, my dick could have cut a diamond.
"Three" I typed, testing the parameters of Rachel's innocently sexual game as the sounds of Stephanie’s hot pleasure rained down upon me. My hand was a blur on my cock now, the three bubbles of Rachel's impending reply teasing me as Stephanie’s impending orgasm egged me on. Her moans were getting quicker, more ragged, my imagination running wild as we both careened toward the edge, and then it came; that final sound of her release. Two short, quick grunts and one long, elated moan that melted from her throat, down through the floor.
At that exact moment, Rachel's reply arrived. Two words, "mine too," so sexy to me in that moment, accompanied by another picture of her green top, this time her immaculate tits pressed together by her arms as though presenting them just to me, her nipples visibly hard through the tight fabric.
I came.
After a long day of frustration and erotic stimuli for my hormone-addled brain, my tight balls rocketed a torrent of hot sperm out of my cock in three, four, five, pulses, drenching my hand and stomach in fresh jizz. My mind seemed to float out of my body in a euphoric blast, eyes squeezed tight, the vision of Rachel's hard nipples and Stephanie’s wet cunt projected on my eyelids as I pulsed through my orgasm.
Finally, after what seemed like hours, I started my descent. My cock flagging, sticky with cum, my breath returning to normal. I sat there, in my post-nut haze, trying to come back to earth.
Three dots appeared on my screen. Then a new message.
"Hey. do you maybe want to go to my prom with me?"
My spent cock twitched.
Chapter 2: Tim gets a prom date, and story time with Tara.
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 Stephanie, my step sister Alexa'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 Alexa and Stephanie in a tight hug, the two lamenting the fact that they'd be separated for the next few months as Alexa 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 Stephanie’s eyes cracked open in her embrace and looking right at me.
I said my goodbyes to Alexa and was on my way out when I heard a voice call from behind me.
"Hey, Timmy, wait up!" It was Stephanie. 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. Stephanie 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 Alexa traipsed around in bikinis, I knew Stephanie 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, Stephanie," I flatly intoned. I WANTED to say I was going to spread those toned, volleyball player legs and lick her cunt 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 cunt mere feet above my head?
"I don't know if Alexa mentioned it at all to you, but I really want to be able to transfer to Alexa'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 Stephanie. 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 sinister 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 other’s 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 Stephanie 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.
"Boo, Miller!" She jeered. I found it extremely sexy when she'd call me by my last name. "It's my birthday, come on!" She argued.
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 fantasized 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 cunt, or getting fucked in any which way her wet cunt 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, black 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 Stephanie’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 Stephanie’s orgasm; the short, short, long moan of ecstasy that accompanied her spasming cunt.
"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.
"That was. AWESOME, Miller; you got a real talent there!" she finally said, smiling. I laughed a relieved laugh and relaxed. "Here, clean yourself up," she said, reaching down and handing me her discarded blouse. I began to wipe her shirt all over my cock, but stopped as my eyes drifted over and landed once again on her beautiful breasts. A glint of light reflected off something wet. In my orgasmic explosion, a stray dollop of cum had landed on the inside of Tara's left breast, and had left a small, shimmering trail as it dripped down into the valley between them. My cock throbbed one last time.
She caught my gaze, looking down to see what I saw. She smiled that wry smile, and leaned in, kissing me on the side of the head, her hard nipples ever so slightly brushing my arm.
"Thanks for a great birthday," she whispered, and got up, gathering her clothes, and headed toward her bedroom to change. "Feel free to clean up in the bathroom, I'll be out in a minute."
I did my best to make myself look presentable, all the time thinking about what had just occurred. My friend, the object of lust of many classmates of mine, just asked me to jerk off for her, and I did it. She showed me her tits. I thought of the stray drop of my cum that hugged their curves.
I shook it off and left the bathroom, but Tara was still nowhere to be seen. I wandered over to her bedroom door and was about to knock, but halted as I heard the faint sound of buzzing coming from inside. A distinct one, two, three, one, two, three, pulsing buzzing pattern, at that. I went back to the couch and waited for Tara to return. Or maybe finish. It was quite an evening, and somehow managed to bring us even closer as friends.
After school, Tara and I went to the mall to hang out. Chatting in the food court over a soda and some fries, we continued our dissection of my new prom-related situation.
"I mean it's a fun place to be in I guess, but it's not like it's going to lead anywhere; I've pretty much guaranteed my virginity stays intact on prom night," I bemoaned.
"Jesus Christ, Miller, how blind are you?" My face scrunched at the accusation "This girl Rachel basically showed you her tits to convince you to go, and Stephanie seemed to accept the terms of your partnership very quickly. I'd say your chances are much less than zero."
"I don't know. Rachel is just such a straight-laced church girl. as much as I'd love to see those tits of hers in the flesh, I don't see it happening. And Stephanie. Stephanie gets off on teasing me. She always has. I expect her to do just enough to get me hot and bothered, then leave me high and dry."
"Maybe. maybe not, is all I'm saying."
Truth was, I would have loved it if Tara was my date for the prom. She and I never had a bad time together, and for an event like the senior prom, I really wanted to be there with someone who wanted to be there with me. I would never go so far as to assume anything other than a platonic date would take place, but I'd be lying if I said I didn't hope the romance of the evening unearthed some feelings between us that were. Less than platonic. Unfortunately, she got snatched up almost immediately by this guy Chris, one of a few potential suitors she had been "talking to" lately, and I was left to figure out an alternative.
We sat in a comfortable silence for a moment. I watched her gaze travel across the room as she languidly tongued a French fry. Bud Pepper was with some of his fellow teammates, and he was trying to be sly as he cast eyes back at Tara.
"Hey, you gotta pick Stephanie up soon, right? We should probably go," she said suddenly. I agreed, taking note of the incident.
When I got home I practically sprinted up to my room, locked the door, and pulled my achingly hard cock out of my pants. I breathed a sigh of relief, and as I started stroking, I thought back to the car ride with Tara, to the moments before we picked up Stephanie. As we drove, Tara was unusually quiet, so I gave her the opportunity to vent.
"Bud is still after you, huh?" I chuckled in disbelief, "can't that guy take a hint?"
"Well." her voice trailed off, that trademark smirk forming on her lips.
"Tara," I droned, in semi-disbelief.
"It's nothing!"
"Truth or dare, Tara!"
"Dare!" She said defiantly, trying to swerve my question.
"Fine; I Dare you to tell me what's going on with you and Bud!"
"Ok, ok!" she said, giving an exasperated sigh, "He texted me on Saturday night."
“And. "
“and I met up with him after my parents went to sleep." My cock twitched.
"and. "
"And I might have. sucked his dick again." There it was!
"Wow! I'm surprised; it didn't sound like you were too interested after last time"
"I honestly wasn't, but I was really, really horny, so I figured what the hell."
"Well what happened? Was it better this time?"
"It was better, definitely. It was almost great, but then he ruined it."
"What happened?"
"Well we drove out to The Spot and started making out, and he was all over me. Rubbing my tits, grabbing my ass, rubbing my cunt through my shorts, the whole nine, so I backed him off for a second and laid down some ground rules."
"Because last time was a dud?"
"Exactly. I told him that I wasn't touching his dick until he got me off first. What happened last time was no big deal, but I wasn't gonna keep doing this if I wasn't getting anything out of it. I wasn't that invested." My pants grew tighter as she talked.
"How'd that go over?"
"About thirty seconds later he had two fingers in my cunt and his mouth on my nipple." I shifted slightly in my seat. Out of the corner of my eye I saw that smirk. She caught me.
"Problem was, he wasn't very good at it. No technique, just sorta rubbing all over the place, so I put my hands on his face to stop him, looked him in the eye, then gently pushed his head down toward my crotch. He got the hint. I said 'good boy.'"
I was trying to focus on the road as my mind took me on a divergent path thinking about my sexy friend taking a bit of a dominant role with this alpha male jock, lying there like a queen while her fuckboy lapped at her wet cunt. I imagined him sliding his fingers in and out, covered in her sweet juices, and the little moans she might make when he hit just the right spot. I thought of her squeezing her own fantastic tits, gently rubbing her nipples the way she did while watching me jerk off.
"So you got what you wanted then?"
"Yes and no. Honestly he just. he just had no idea what he was doing. I mean, you give me a tongue and I'll get off every time, but I had to do most of the work myself. I might have scared him a bit though."
"Oh?"
"Yeah. I made him get on his back so I could straddle his face. I grabbed a handful of his hair and just ground my cunt all over his tongue. I just. straight up fucked his face."
"Oh wow." Oh wow was right. I had an iron bar in my pants.
"It was working though," she said wistfully, "I fucked his face, making sure his tongue hit the right spots, and let my mind drift to more arousing imagery."
"Such as?" It was a reach to ask, but I was in too deep now.
"Just other things. past experiences. past. visual stimuli. " I thought I saw her eyes flick down momentarily to my crotch. "Between that and the fingers inside me, it didn't take me long to cum. It was. nice."
My balls were boiling at this point. The image of my friend Tara, the goth sex kitten, straddling Bud Pepper, her perfect tits spilling out while she fucked his face for her own pleasure caused sweat to form in the middle of my back.
I imagined her gripping his hair, running her clit back and forth over his tongue, eyes shut tight in ecstasy, climbing toward climax, until she cried out in orgasm, her tight cunt pulsating on the fat fingers pistoning inside her.
"Well that's good," I said, trying desperately not to reveal my heightened state of stimulation, "so I assume you kept your part of the deal too?"
"Of course! I was looking forward to it; you know how I love a challenge almost as much as I love sucking cock, and I had some unfinished business."
"And I assume he had no trouble this time?" My mouth was dry.
"Actually he did." She grew a little pensive. "I could tell he was trying too hard, so I told him just to close his eyes and relax."
"And?"
"And that definitely got the ball rolling. I love feeling a dick get hard in my mouth, so when I felt that boy getting bigger, God, my cunt was just DRENCHED. Even more so because he kept getting bigger. and bigger. and bigger. "
"Seriously?" The erotic fog in my brain parted momentarily as now I was just legitimately interested in the spectacle.
"Yeah, Miller, his dick was Huge."
"Well now I'm just jealous!"
"I said his dick was huge, not fantastic," she said, that wry smile coming back to her lips.
"Could you, you know. "
"No, I think I got maybe half of it in? It was a little frustrating but, God, I was just drooling all over this thing, I was so fucking horny for it. It was like I needed it in my mouth. At that moment my sole job on this planet was to get this cock to cum." Her thighs squeezed together as the memory rolled through her mind.
Rolling through My mind was the thought of Tara on her knees in a car not too different from mine, her wet, dripping cunt bouncing in the air, while she slid this huge cock in and out of her mouth, salivating like it was her last meal. I thought about her tongue running over the head as her hands pumped his throbbing veiny rod. I thought about her desperately trying to fit it all in her mouth, about her feeling its heft on her face as she sucked his balls.
"I was doing my best, trust me, my best, but something still wasn't right. He just wasn't all the way hard. So I pulled out the secret weapon." I couldn't wait to hear what it was. Did she rub him between her tits? Did she fuck him?
"I had the head in my mouth, one hand pumping his shaft, and then I slowly and gently ran my other hand down, over and past his balls, and gently pressed his asshole with my finger."
"And. he liked it?" I could literally feel my cock leaking precum in my pants now. If I shifted too hard in the wrong direction, It would be the camping trip all over again.
"His cock got so hard, so fast, that he almost impaled me. So, I just start pressing on it over and over, like Morse code or something, and he's moaning, and twitching, and I can feel his cock getting stiffer in my mouth, and his balls are tightening, so at just the right moment, I push my finger in his ass up to the first knuckle, and he explodes. There was so much cum, I think I only managed to swallow half of it before I got overwhelmed and just jerked the rest out with my hands. It was All Over me. I felt Good though. I Did it."
In my room, remembering this story as I frantically stroke my cock, this is the moment that puts me over the edge. I think about Tara, her dark lipstick smeared with juices, hanging on for dear life as this huge cock erupts hot, white semen into her salivating mouth. I think about her stroking and sucking, and the feeling of satisfaction she felt as his dick spasmed and pulsed, spasmed and pulsed, over and over, feeding her the milky reward she wanted so badly. Then I think about her having to pull off, overwhelmed by the volume this behemoth honored her with, and I picture her wry, satisfied smile, lips and chin streaked in spurting cum. White lava flowing down his thick trunk, over the black nail polish on her skillful fingers. His cum cresting through the air and spattering her perfect tits, just like mine had, slowly caressing their contours as it drips down into the space between them, just like mine had.
I groan. I tense. I cum.
In my post-orgasmic haze, I think back to the rest of the conversation, and for a moment I feel guilty in my pleasure. She had said earlier that it was ALMOST great, but that Bud had ruined it. After a silence that you could cut with a knife, where I think we both needed a moment to adjust to the arousal this story was creating, she explained why.
"So there I am, drenched in his jizz, loving it, feeling like a million bucks, and he just says. " She paused, a sudden influx of emotion catching her off guard, “he says ' wow. You're just as good as they said you'd be.'"
My dick started to deflate
"I was on the top of the world and in a split second he made me feel like a cheap whore." She didn't cry, but her emotions definitely bubbled to the surface. She gazed out the window blankly for a moment. I'd say I was at a loss for words, but really I just knew that at that moment anything I said would do much less than help.
"But hey, you live and you learn, right? At least I got to cum!" Just like that she was back. I just chuckled, trying to process everything, trying to separate my horniness from the fact that this asshole treated one of my best friends like dog shit. We pulled up to Stephanie’s coffee shop, and parked.
"Listen, Tara, I. "
"Forget about it, Miller," she smiled, "I already have."
I knew she was lying, but I didn't press the issue.
"Is that her?" Tara pointed as Stephanie stepped out of the shop, looking around for my car.
"Yep." I flashed my lights at her, and she smiled as she came bounding over. Her smile quickly turned to a confused frown as she opened the passenger side door, revealing an unexpected Tara.
"Hey there Stephanie, I'm Tara," she beamed, "Tim's fuck buddy!" Stephanie’s face scrunched.
"Tara! Goddamn it!" Tara just giggled and climbed over the front seat into the back. "Come on in, Stephanie, that's Tara, my asshole friend."
"Um Hmm. am I interrupting something?" She said as she slid into the car, flipping up the arm rest and replacing it with her bag.
"Absolutely not. I was just about to drop this jerk back home." I said. Tara chuckled.
The ride to Tara's was uneventful, and we chatted casually. When Tara left to get out, she said her "nice to meet you" to Stephanie and asked me to help her get her stuff out of the trunk. Tara didn't have any stuff in the trunk. Going around the back of the car, I opened up the trunk, blocking the view from inside the car.
"What's going on, Tara?"
"I just wanted to tell you to be careful with her. I think she likes you more than she lets on."
"No way, she just likes teasing me." I said, shaking it off. Tara cocked an eyebrow.
"Oh yeah? Did you see that smile drop off her face when she saw me in the car? Or when I said we were fuck buddies?" I just shook my head and laughed.
"I don't know anyone who would react normally to a surprise like that!"
"Well how about when she flipped up the arm rest between you? That's some body language right there, boy." I paused, but still wasn't convinced.
"Nah, I don't think so. it's fine, Tara, really." Giving up, she put her hand on my arm, and slid it down to grab my hand gently.
"Ok, ok, just. keep your antennae up, huh?" She was a good friend.
"Sure."
"Good!" She punched me in the shoulder and chuckled before jogging off. She was an asshole friend.
I sat in my room, cleaning up the spent cum from my now flaccid dick, thinking about everything Tara said tonight. I thought about Stephanie, and the possibility that maybe she was actually into me. I had to put it out of my head though, as I was about to head up to her unit for our first tutoring session.
My computer dinged as a message from Rachel popped up on the screen. My cock twitched. I ignored it. I was late.
I never in a million years thought I'd be helping Stephanie, my step sister's best friend, the hot older girl who took pleasure in teasing me all through puberty, study for college classes, but here we were.
Stephanie’s mom Sandy greeted me at the door with a warm smile, their cat Foofy casually strutting by behind her. I'd never spent that much time in Stephanie’s family's unit, but as a flighty highschooler I did have a tendency to forget my house keys, so Sandy gave me an open invitation to hang there until someone else came home any time I did. She and her husband Don were both great people, very welcoming. They kept a key under their mat, and encouraged me to use it if need be whether or not they were home. I tried not to make a habit of it, but I did take advantage of their generosity a few times over the years.
A gorgeous mid-40's housewife, Sandy's long, toned legs and mane of glowing blonde hair made it fairly obvious where Stephanie got her looks, but Sandy had one advantage Stephanie had yet to develop: two beautiful, extra large, mature breasts that still sat rather high and firm on her chest, despite their size and age. Now don't get me wrong, Stephanie was no slouch in the tits department, near as I could tell, but her mom was on a whole different level. Stephanie had tits; her mom had BREASTS.
Sandy was never shy about showing them off either, which got me excited any time our families would get together, especially in the summer. Wrapped in deep V shirts, or bikini tops that held her glorious melons like weighty bowling balls, our backyard cookouts became exercises in hiding erections. One particularly embarrassing summer I found myself standing across the BBQ buffet table from Sandy as she reached over to grab some extra napkins. I looked up from my plate right as her deep cleavage lowered itself to my eye level, and my gaze got lost in the plump, meaty chasm presented before me. My eyes followed, hypnotized as she straightened up, but quickly snapped out of it, as her exit revealed Stephanie standing there. Her face was scrunched in displeasure as she stared at me.
"Were you just looking at my mom's tits?" she accused. I had no chance of a coherent answer, so she called me a perv and ran off to tell Alexa about what a perv her pervy step brother was. Mortified, things got worse as the next person to sidle up to the table was Don. Expecting to get chewed out by a protective husband, Don surprised me. He just gave a hearty chuckle and said "Don't worry about it, Tim; happens to me all the time!"
He gave me a wink and chuckled again as he continued on. Despite the affirmation, it was the most embarrassed I had been in a while. That didn't stop the vision of Sandy's succulent, bursting cleavage from playing a starring role in that night's masurbatory exploits, of course.
Juicy tits aside, however, Sandy was just a regular, unassuming mom and housewife, mild mannered and friendly to all. She worked at the public library, and was a member of the P T A when Stephanie was still in school. She coached girls' soccer and made great salads, and would stop herself after one glass of wine before things got "too crazy." She and Don were even known to go to a church service with us here and there on the odd Sunday. They were both really great to us after my dad died, and Sandy had long been one of my step mom Kelly's best friends. That's why Kelly would always just shake her head and give a friendly chuckle when Sandy's twin assets were on display, knowing that showing some deep cleavage was probably the closest Sandy ever got to being naughty.
Oh, if Kelly only knew what Sandy really did when she wanted to be naughty.
To be continued in Part 2
By LiminallySpaced for Literotica.