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Coming Of Age: Second Base

"Matt and Angie explore their budding relationship"

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Author's Notes

"I hope you enjoy my first attempt at erotic writing. <p> [ADVERT] </p>I’d love to hear your feedback and suggestions."

Growing up in an ultra-conservative home, I led a pretty sheltered life. My dad gave me the “birds and the bees” talk when I was a sophomore in high school. Let’s just say…it didn’t go very well. To say the talk was awkward would be an understatement. There was nowhere for me to hide. I just wanted it to be over. Even though I wasn’t super experienced yet with girls, I knew that his version of sex was out of touch, to say the least. Besides, I had already learned way more from hanging out with my high school buddies in the locker room and on sleepovers than from my dad’s feeble attempt at Sex Ed.

During my adolescence, baseball metaphors were commonly used to describe how far you went with your girlfriend. Thanks to several years on the diamond and my friend Sam Malone, this analogy was totally relatable. No, I didn’t have a real friend named Sam Malone…I’m talking about the fictional character of Thursday night Primetime Comedy fame. My favorite sitcom in the late eighties and early nineties was Cheers, starring Ted Danson as playboy Sam Malone, a former Boston Red Sox relief pitcher turned bar owner of the local watering hole “where everybody knows your name.”

Before using baseball references as terms for sexual exploration we absolutely must clarify the bases. It really is necessary, for the sake of humankind as we know it. This clarification is unfortunately a higher priority than most people realize as evidenced by successive generations seeming to increasingly screw up what these bases actually mean. Thanks only in part to characters like Howard Wolowitz from The Big Bang Theory declaring that he “got to eighth base,” which, according to him, was “seventh base with his shirt off.” Yikes! Thanks, but no thanks, Howard. 

Baseball Sex Ed. 101: First base has, and always will be: kissing. End of story. The kissing might get pretty heated and include lots of tongue. It may even involve necking and hickies but make no mistake, the use of the lips above the shoulders is first base. Once you round first for second base, things start getting less definitive but still maintain one basic boundary line: above the waist. Generally, second base means that the guy is touching the girl’s breasts in one of three likely scenarios: on top of the shirt, under the shirt on top of the bra, or the full safe slide into second base…under the bra with skin-on-skin contact. All three ways to touch the boobies are still essentially considered as achieving second base.

Major League home run legend Hank Aaron once said, “The triple is the most exciting play in baseball.” In sexual terms, this is also where things get much more exciting. The sexual reference to third base has slight variations that have minor-league and major-league implications that cross the aforementioned boundary line.

If you’re playing in the “minor leagues” then third base refers to below the waist touching on top of clothes, and maybe somewhat under the clothes…but overall it’s still just touching with the hands below the waist. Any of this touching can include ass, dick, balls, pussy, pubes, plus any of the adjacent erogenous zones. If you’re playing in the “major leagues” however, then third base is mainly referring to oral sex, plain and simple.

A home run, similar to the first base analogy, has one and only one reference: penetrative sex using sexual organs. Sure, we could break it down further to differentiate vaginal versus anal penetration, but it’s not that complicated really.

Now that we have literally covered the bases of Baseball Sex Ed. 101 our sexual analogy class is over for the day. So, let’s get back to my cumming-of-age story.

As a sixteen-year-old guy, I had been to first base several times with make-out sessions often getting pretty hot and heavy. Spin the Bottle was a popular party game in my day, which allowed for many private trips to another room or closet to spend a few minutes making out with a random girl. Fun times indeed.

I had a few trips to second base on top of the clothes with various girlfriends, which unfortunately left me “stranded on base” and having to keep my bat and balls in the equipment shed, so to speak. These “left-on-base” situations inevitably meant that I would be finishing batting practice later that night in my bedroom working on my one-handed batting stance…solo. Getting to second base those handfuls of times was fun nonetheless.

I have always been and will always be a “boob guy,” meaning that I love boobs as my first point of physical attraction. As much as I love boobs and always will, I wanted more than anything to get around the bases to home plate. After all, like most warm-blooded sixteen-year-old guys I had one thing and one thing only on my hormonal brain, albeit my lower brain, and that was: pussy. Sorry if that sounds crass, but as the home plate umpire often says, “I call ‘em like I see ‘em.”

Life in the eighties was pretty cut and dry. We didn’t have smartphones or smart cars. We didn’t have Alexa or Siri. It was a simpler time really. We didn’t have to worry about much back then, especially in our small town. As long as we made it home before mom put dinner on the table, we were golden…otherwise, we were probably going to bed hungry.

The eighties however was a tough decade for the average high school student. That decade is known for some of its classic coming-of-age movies, mostly thanks to the great John Hughes. Not everything was exactly like what you see in a John Hughes movie, but, now that I think about it, those movies weren’t too far from the truth either. The main difference between John Hughes’ movies and real life was that the nerdy guy never really got to have the hot girl at the end of the story. 

In that era, at least in my small town, there were really no teen subcultures of countless varieties like there are nowadays where you can be anything you want and “everyone is special” in their own way. As a side note, I think that these classic eighties movies did play a significant role in redefining those social boundaries in teen culture.

For the most part in the eighties, you were either cool or a nerd. By today’s standards, I was somewhere in the middle, not really fitting in with either crowd. Even though I was a two-sport athlete (always junior varsity and never varsity), by the standards of the day that put me in the nerd group by the simple fact that I wasn’t cool enough to be considered, well…cool. Also stymieing my social status was the fact that I had moved to town when I was in second grade and hadn’t been born there.

On the flip side though, I wasn’t dorky enough to fit in with the nerd crowd either. I had my share of dorky moments though which, again, destined me to be on the outside of the cool crowd. My main contributing dork factor was that I was also in the band. No, not a rock band but rather the marching band. In the eighties, being in the band was definitely considered to be not cool. More to come on that part of my life in a moment. 

Not being in the cool crowd didn’t really bother me too much most of the time. One thing I had learned from all of those awesome eighties John Hughes movies was that life wasn’t like the movies. Seeing his version of reality made me a realist in many ways…at least in my little world. I was fine with my place in that world. I wasn’t at the top of the food chain, but I wasn’t a bottom feeder either. And truthfully, I liked who I was and didn’t feel much pressure to be someone else just to fit in. I was for the most part comfortable in my own skin.

Being somewhat self-aware meant that I knew my realistic odds for landing a girlfriend of “Hollywood ending” status. Looking back now, it was by sheer fate that I ever met Angie.

Angie was way out of my league. Similar to me though, she wasn’t in the ultra-cool crowd and was definitely NOT in the nerd crowd. She was way too smokin’ hot to be a nerd. Angie’s parents were divorced, which was still kind of a cultural taboo back then. She lived with her mom, stepdad, and her brother in a trailer park on the outskirts of town. None of this bothered me in the slightest. But in our lame small town, if you weren’t raised in a wealthy neighborhood then you already had two strikes against you for your coolness factor. Angie’s coolness (and hotness) factor was attributed to her participation in the school dance/spirit squad. She had a perfect dancer's body: toned, petite, and with just the right curves that showed off all her best assets. She had barely an ounce of body fat on her. Her tits we a perfect B-cup that barely broke the curve of her flat chest. Most guys liked girls with bigger breasts, but I have always loved girls with smaller boobs. Angie was dynamite in a small package. 

While I considered myself to be self-aware, Angie was so much more than that. Angie oozed sexual confidence. She was sexy and she walked tall knowing it. Don’t get me wrong, she was not in the least bit stuck up. She merely flaunted the body she had because she was proud of it. I would sometimes get distracted during football practices because Angie and the rest of the dance team were on the other side of the practice fields working out while we were running after-school drills. The ease with which I was distracted was probably also why I was on JV and not the varsity squad. But those girls in their skimpy dance outfits made it, umm, hard to practice passing routes. 

It was characteristic of small-town schools that many students participated in multiple extracurricular activities like sports, the arts, service clubs, and other organizations. Small-town life meant there were fewer students to spread around to all the available organizations. I had a wide variety of interests, which meant that I also was involved in many different groups…including the social outcasts of the marching band.

The marching band practiced in the mornings during first period. And on Friday gamedays, the spirit squad would practice their halftime routine with the band during first period. Fridays were my favorite days.

I loved Friday night football, even though I wasn’t on the field with the team but in the stands with the band cheering on the varsity guys. The main reason I loved Fridays, however, was because I played trumpet which meant that I was on the first row of the halftime routine…which meant that I had a perfect view of Angie’s tight, perky ass which was barely covered by her tight dance outfit. I won’t lie, there were many halftime shows that I marched off the field with a semi- or full boner because I spent too much time watching Angie dance instead of watching the drum major conduct. Damn. I still get hard thinking about her perky little body gyrating in front of me.

During the week of our first district football game, Angie busted me watching her dance during Friday's final run-through. The first time she caught me watching, I quickly averted my eyes and told myself that she didn’t notice. But several seconds later when I glanced back at her she winked at me and smiled.

Wait…what???

I sheepishly looked around to see if she might have been winking at someone else. But everyone around me was otherwise occupied with other things. Just to be sure, I gave her a quick head nod and grin…you know, the type that says, “Hey girl.” She grinned back and gave a tiny playful finger wave.

I couldn’t believe it. Was she flirting with me? A couple more times that morning during practice there was no doubt that she noticed I was checking her out. I was giddy with anticipation and felt a slight stir in my groin.

Right before the bell rang to go to second period, she was bending over to do some cool-down stretches as the spirit squad was finishing up the session. As she bent over, reaching for her outstretched toes, she glanced back straight at me. I was so entranced by her beauty that I didn’t even flinch. Fortunately, when she saw me looking goat her I was looking at her face and not her ass.

Whew. That was close. I just stared at her. Not in a creepy way, but in a way that pondered the beauty that was before my eyes. She was certainly the whole package. And deep down in hormone central, there was no doubt that my lust for her was in the zone. My trance was broken by her question, “Like what you see?”

As I shook myself back to reality, I replied with only a slight stutter, “Very much, I do, yes.” 

Angie was quick to fire right back with, “Well there’s enough of me to share. Soooo, I guess I could share some of me with you.”

I could hardly believe my ears. Was she offering herself to me? Surely, I was mistaken. As rehearsal finished up and we made our way back into the band hall, Angie came up beside me and asked if I would walk her to class. Of course, I quickly agreed. 

A few minutes later we were strolling the hallways side-by-side toward the science hall. As we walked, Angie let me know that she had also been watching me for several weeks. She thought I was cute and hoped I would ask her to the homecoming dance. I wasted no time and asked her right there on the spot. She kindly accepted her playfully manipulated prompt.

Before she stepped into the doorway of her biology classroom, I asked her if she had plans for after tonight’s game. She said she was hoping to hang out with this really cute trumpet player that was checking her out at band practice earlier. I smiled, only slightly embarrassed, and said that I could probably convince that cute trumpet player to ask her out if she was indeed interested. She giggled as she turned to go into her class. She squeezed my hand and winked as she walked away and out of sight.

Later that day at lunch, I grabbed my food from the vending machines and made my way through the maze of cafeteria tables. I soon noticed that Angie was sitting with several of her spirit squad friends. As I passed by her table, I realized that there was an open seat next to her. She motioned for me to come and sit. I gladly plopped down next to her.

As soon as my butt hit the plastic seat I was keenly aware that every eye at the table was focused on me. The circle of teen girls was breathless with excitement. To be honest, I was a little intimidated at that moment of group attention. But I quickly returned my gaze toward my sexy crush. She tried not to smile but was unable to control her undeniable attraction.

Only a few hours earlier I had been just an average guy with my closest dating prospect being my right hand. But now, I was sitting at a table full of girls where I was the center of attention. But I didn’t care about the circle of friends, I wanted to dive headfirst into the deep end of this beautiful brunette babe.

I looked at Angie and asked if she minded if we went someplace a little more private. She never broke her lock with my eyes and said, “I’m all yours.” She coyly agreed with a clever innuendo.

We grabbed our food and books and made our way toward the courtyard. I opened the cafeteria door as a gentleman should do and I let her walk in front of me. And of course, I also wanted another opportunity to check out her sweet, perky ass. There was one open picnic table near the alumni fountain, so we rushed over to grab it before anyone else.

I can’t remember what I ate that day. I can’t remember everything we talked about during lunch. But I can remember feeling like I had met my dream girl. I can remember thinking to myself, “Wow, this girl is too good to be true.” She was definitely too good for me…yet somehow she was just right for me.

Maybe it was a tinge of insecurity, or maybe it was curiosity that prompted me to ask. “Angie, can I ask you a question?” I said.

“You just did,” she quipped. “But, yes. You may.”

“You’re gorgeous,” I blurted enthusiastically, “Like way prettier than the other girls at our school.” 

She grinned and lightly bit her lower lip. Then she said, “But that’s not a question.”

“Sorry,” I stammered, “I mean…why me? Why…you…why are you, you know…interested in…in me?”

Angie didn’t hesitate for even a second. She replied, “I know what I like when I see it. And if you must know, I think you have sexy legs.”

“Huh?” I wondered out loud. “What do you mean?”

“Well,” she blushed, “I’ve been watching you at football practice, and I’ve even come to some of your JV football games to watch you play. I couldn’t help but notice that your legs are, well, really sexy.”

I had never really thought about it before but I guess it made sense. As an athlete, I was a wide receiver and an outfielder. I loved hiking and camping and other outdoor activities. I was also a lifeguard at the city pool during the summer. All of these activities led to my legs being well-toned and tanned.

While I had never considered myself or any part of my body to be “sexy” as she put it, I had trained very hard in my workouts and hobbies to keep my legs in good shape. My calves were chiseled because I needed to be on top of my game. I was in better than average shape and she had noticed…more than noticed, actually…she was interested.

“Thanks,” I said to her, “I think you’re pretty sexy too.” 

With a coy little smirk, she came back at me asking, “So what do you think is my best feature?” Her question had a tone of curiosity and confidence. She wasn’t being overtly daring, but I’m sure she wanted to test my response.

In my mind, I knew that I lusted and fantasized about her perky, tiny tits. But I knew in that moment of early introductions it wouldn’t be polite to say that to her…yet. So I went with the more obvious answer, given what had happened at band rehearsal that morning. Her cute little ass was an easy number two in my mind, so that’s what I said to her, “I really like your cute little butt.”

With another flirty smirk she said, “Mmhmm, I thought you were looking at my ass today in practice."

She paused slightly to watch for my reaction. I may have blushed a little bit. I know I felt my face get warmer instantly.

So that I wouldn't suffer too much, she chimed in by saying, "My mom says I have a doodlebug butt.” 

“Huh?” I almost spit out a sip of Dr. Pepper as she mentioned her mom’s thoughts about her ass.

“Yeah, mom says that my butt is wound up tight and round like one of those little doodlebugs…you know the roly-poly ones.”

We laughed out loud together at the silly comparison.

“What?” I said in playful disbelief, “No way, lemme see.”

Angie stuck her round tush out to the side and I was offered a free peek at her cute little butt cheek in her Jordache jeans. All I could think at that moment was, “Damn what I wouldn’t give to get in those jeans.”

Over the next few weeks we started officially dating, making out, and cruising together up and down the strip in my dad’s Toyota Camry…not the coolest car for a guy my age, but it got me around town. On several occasions, while cruising through town, Angie and I get bored and decided to go find a secluded spot to make out.

Everyone in high school knew a handful of locations that were ideal for these types of private activities for couples. When we would go parking on Saturday nights, we would usually start by looking at the stars through the windshield and talking about our families and life in our small town. After some time the conversation would turn more sexual and we would share the latest gossip of who was having sex and who was cheating behind their lover’s back…typical high school drama.

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I couldn’t stop thinking about her sexy body and wondering what she looked like naked…especially her tits. I would often masturbate in the shower thinking about Angie's tits as thick ropes of cum would splash across the tile shower floor. My hormones were raging inside me, but I knew that I would have to pace myself and be patient, waiting for the right moment to push the boundaries of our sexual exploration.

As our relationship began to grow, we quickly became more open about our sexual past and how far we had been with other girlfriends and boyfriends. We learned that each of us was still a virgin and had we had limited experience with petting and making out. That knowledge added to our excitement, knowing that we would be starting our sexual journey from relatively the same place.

The more we talked about sexual things the more we would get turned on and start making out. It only took a couple of weeks of making out for my hands to find my way to her perky boobs. As I tested her comfort with my hands on her chest, we of course started with my hands on top of her shirt and when I knew she was comfortable with that, I moved my hands under her shirt. This was the first time I had ever felt a girl’s underwear. It was exhilarating.

At this point my cock was so hard I could barely stand it. I could easily tell that she enjoyed the feeling but she was not wanting to go much further. So for a few more weeks, my hands were deterred by a thin piece of silky fabric. I was falling head-over-heels in love with Angie quickly, so I didn’t want to pressure her into going too far if she wasn’t ready. I knew the time would come if I would only be patient with her.

After a few weeks of learning every silky millimeter of her collection of bras (most were pretty simple back then), I finally was able to fully make my way to second base.

After the football season was over and the holidays were quickly approaching, we sat in the car late one weekend night making out. Living in the Gulf South, the late Fall rarely got very cold but would fluctuate between miserably warm for that time of year and cold-ish. When the weather outside was getting cool, I would like to refer to it as “nippy,” for obvious reasons. On this particular night, I would truly discover the ecstasy of that nippy air.

We had found a very secluded dead-end road where some new houses were being built on the edge of town. This new development meant that there were no street lights and no people around for as far as we could see. It was truly a perfect place to make out with my sexy girlfriend. Since the weather was cool we decided to sit on the trunk of the car as we talked. As usual, our conversation was mostly fun and playful. We laughed as we recalled the immature drama of high school life. We complained about our stupid classes and made fun of the teachers that were ridiculously annoying. As we talked under the glow of the full moon, we threw small rocks at the construction sign that marked the end of the new street. Throwing rocks gave me an idea that would help me test the boundaries of our sexual experimenting.

“How about we play a game,” I suggested. 

“What do you mean?” Angie smiled and cocked her head, playfully suspicious.

“Okay. We pick a target and the one who hits closest to the target gets a kiss from the other.”

“But if we are both kissing then aren’t we both considered winners?” She pondered out loud.

“Well of course, isn’t it better when everyone wins?” I came back. She smiled and agreed to play along.

First we picked the large sign at the end of the street. We both threw a rock and both landed our projectiles. We kissed sweetly for a few seconds. She smiled big as she pulled away and gave me a little wink.

We acknowledged that our target was too big so next, we narrowed in on a utility pole on the side of the street. She fired her rock and missed. I threw mine and it glanced off the edge of the pole, not a direct hit but it still counted. Angie leaned in and planted a big kiss and drove her tongue deep into my mouth. We passionately wrestled our tongues for a few moments and broke apart with a slight gasp for air.

“You know,” she observed, “this game isn’t exactly fair since you play baseball and football…both games that require skill at throwing. I’m just a dancer. I don’t work my arms as much as you do.” With that question, she gave me her sad puppy eyes and a playful pout as she noted my advantage. 

“Alright,” I lightheartedly caved. “I’ll tell you what. You can pick a tougher target for me and I’ll pick one closer up for you. That way it balances out.”

“Deal,” she answered enthusiastically, poking me in the ribs. 

After we picked our next targets we each took our turns throwing and each of us narrowly missed our marks. We agreed to try again and this time she landed squarely but my rock drifted just a bit outside.

As she leaned against the car’s trunk I leaned in and cupped her face in my hands. I looked deep into her eyes and moved in to her luscious lips. The kiss was not as passionate as the others from that night but when I pulled my head back and opened my eyes she was in a trance with her eyes still closed.

“Woof,” she said with a low sultry tone in her voice. “You better not kiss me again like that I’m likely to jump your bones.”

I knew she wasn’t ready yet to go all the way, but her response told me that she was melting under my romantic spell.

“So what’s next?” She prodded, “What target do you have your eye on next?”

I couldn’t pass up that double entendre, so I offered my next twist in the game.

“I have my eye on you, Doodle Bug,” I replied, “So let’s make it a little more interesting.”

With a hint of caution in her voice she proceeded, “Okay.”

Realizing that I was throwing her guard off, I further explained my idea. “This time the one of us who is closest to their target gets to remove one piece of clothing from the other person,” I suggested, bumping up the sexual thermostat by a significant degree.

This potentially would be the biggest step in our sexual progression if it turned out how I hoped. We had done plenty of petting above the waist with our clothes on. And our hands had occasionally wandered to each other’s butts during steamy make-out sessions. But we hadn’t yet taken anything off.

In a flash, I wondered if I had pushed her too far. Was she ready for that? Was I ready for that? You bet I was…but was she? For sure I didn’t want to pressure her or be in any way disrespectful, but my hormones were also raging for this beautiful girl as we had gotten to know each other better.

“Matthew Blake, I am NOT playing strip rock throwing whatever with you out here in the open. What if someone drives by?”

I knew she was serious because she used both my first and middle names. Her response was firm but still coy and playful. She was beaming with pleasure as I could see on her face, but she obviously wanted to be careful and pace herself. I retreated ever so slightly with a compromise. 

“Okay, okay,” I smiled back at her, “How about we make this our last round of target practice for the night and have one prize, each chosen by the other before we throw, so we know the stakes at hand.”

She thought about it for a quick moment, and with a huge grin on her face she agreed. “If I win,” she said, “you have to kiss me like you did earlier…like when you took my breath away.” I happily agreed.

“And if I win,” I responded, “then we get back in the car and I take your bra off.”

She smiled instantly, but with a clever upward turn in the corner of her mouth. “Fine,” she quipped. “But I get to pick the targets…both of them.”

I knew she was playing hard to get, but I could also tell from the red flush around her neck that she was ready to make out. After all, the romantic and sexual tension had been building through our playful evening in the cul de sac. She grabbed my jacket pocket and pulled me in toward her. Her eyes were starry with sensual anticipation. Her fiery gaze froze me where I stood. Her scent filled my nostrils and combined with the glow of the full moon to heighten my desire.

We were falling in love more quickly with each passing week, and I knew that Angie was my first true love. Without shifting my eyes from hers, I could see puffs of steam coming from her mouth and disappearing into the breeze.

I knew she wouldn’t likely make things easy for me in this final round of our made-up game, but I agreed to her terms. How could I say no to her, glowing in the moonlight and literally steaming with hotness?

She picked my target to be a small “No Trespassing” sign that was about 150 feet away and marked the boundary of a neighboring hay field. I looked at her quizzically, knowing that she had picked the farthest target yet.

Then for her own target, Angie picked the same sign we started with…the one at the end of the street…that was our easiest target. It was only about 30 feet away and was much bigger than my sign. I cocked my head to the side in disbelief and smiled at her, knowing that she had skewed the odds to be in her favor. I could tell she was toying with me. But I was up for a challenge and I wasn’t about to let her see me back down.

I looked around for the perfect rock. There in the dirt just off to the side of the road was a rock just smaller than a baseball that had a fairly round shape to it. It wasn’t perfect, but the weight and shape were as close as I would likely find in this construction zone. She picked up her rock, one that was much smaller than mine, and returned to her spot at the back of the car. 

“Ladies first,” I said to her as I gestured with a slight bow. With barely a step she fired her rock with a direct hit square in the center of the large orange sign. The rock pinged off of the aluminum and landed with a crack against the asphalt. I congratulated her for her perfect toss and playfully patted her on her butt, much like baseball players do to say "good game, dude." She appreciated my enthusiasm.

Next, I prepared for my own turn. Being an outfielder, I had made throws like this before from right field to catch a speeding base runner diving for home plate. In fact, this throw was a little shorter than most of the outfield throws I was used to making. My target was about the same size as home plate it appeared. However, I would not have the freedom of a moving target like the catcher’s glove, should I be slightly off my mark. I had to be zeroed in. With the mounting pressure, I knew I had to make this throw count. I wanted more than anything to see Angie’s perky, tiny titties.

I took a couple of steps backward and twisted the ball of my back foot to steady my stance. With a few quick strides forward and the full extension of my arm, I hurled my stone through the air. The rock sailed forward as the moonlight highlighted its arch through the night sky. We both held our breaths as we awaited its result.

It only took a couple of seconds for the loud clank as the rock collided with the upper right corner of the metal sign. I pumped my fist in the air and spun around to face Angie. She was grinning as big as I'd ever seen her beautiful, dimpled face.

She leaped into my arms. Her lips locked onto mine instantly. My hands grabbed her torso to keep her from falling, drawing her tightly into my chest. We were both breathing heavily. I could feel her breasts pushing against my chest. I could once again see the steam from our mouths bellowing into the night air. We kissed deeply and fought over each other’s tongues.

Still loosely locked in our embrace, we scrambled for the back door handle. As I slid into the back seat our hands were roaming freely. She braced her hand on my chest and threw her left leg over my lap and plopped down only my pulsing cock, restrained by only layers of denim and our underwear. The moment was hot and heavy but I resisted the urge to dry hump her since I knew she wasn’t ready for that. We hadn’t even touched each other down there yet.

She leaned firmly into my torso and shifted her weight slightly which only served to rub agonizingly on my stiff cock. I followed by grabbing onto her tight doodlebug butt and squeezing tightly. Her ass was firm and incredible to the touch. I had never grabbed her with this much intensity before. We weren’t frantic but we knew we were on a mission.

I took a pause and gazed into her eyes, which were again on fire. At that moment, she caught her breath and steadied her focus. She awaited my next move.

“Time for you to receive your prize,” I said, unable to take my eyes off of hers. She was virtually motionless. Faintly I noticed a slight movement of her head up and down to acknowledge my offering. I caressed her hair away from her face and ran my fingers down her cheek and to the nape of her neck, tickling her skin with the backs of my fingernails. She shuddered with pleasure. I took my other hand and repeated the tantalizing gesture across the other side of her face and neck. Again she shivered in the cool evening air.

I slowly cupped her face and lightly brushed her cheeks with my thumbs. I leaned into her as she slowly moved in to meet me. Our lips met with a spark of excitement. My tongue tenderly searched for hers. They danced inside our mouths. There was something almost magical about that kiss…like one of those kisses you see at the end of a movie. Like one of those kisses I never thought I’d experience…with a girl that I thought would never be into a guy like me. Maybe John Hughes wasn’t that far off with his scripts after all. Maybe the nerdy guy did wind up with the hot girl.

Our kiss must have lasted for several minutes, but I wasn't sure because I lost track of time. It was incredible. In fact, it was perfect.

As we eventually pulled away from our kiss, we opened our eyes and leaned our foreheads into each other. “Wow,” was all she could say. 

“Ange,” I started to speak, but she pulled her finger up to my lips interrupting my reply.

From her hovering position in my lap, she drew me into her chest for a firm hug…the kind of hug that says ‘you are my safe place.’ She held me like this for at least a minute.

Because of her position in my lap, this embrace conveniently had my face tucked into her chest. I could feel the slight swell of her right breast on my cheek…and she was nipping out. I could feel the stiffness of her nipple against my face as she held me in place. I opened my eyes and could see her left breast mere inches away. Its nipple was pointing boldly through the fabric of her bra and shirt, begging to be released.

I reveled in this moment of blissful desire. I didn’t want this to end, but I also was staring at the target of my desire pointing up at me. I waited for her to make the next move.

Slowly she leaned back and looked me straight in the eye. Her face was so beautiful in the dim light of the moon. Her motion was tantalizing as she reached down to the hem of her shirt and steadily pulled it over her head. Her wavy brown hair cascaded over her bare shoulders and bounced in slow motion. I stared in disbelief at her sexy black lace bra. This was a new one that I hadn’t felt before. It was classy and sexy in a perfect B-cup package. Angie’s skin instantly had goosebumps from the cool air. I pulled her close to my chest and held her tightly, rubbing the bare skin of her back to warm her up. 

My fingers bounced over the strap that held her bra in place. Still holding her close I whispered in her ear, “Are you sure?” Her reply wasn’t exactly what my horny adolescent body wanted to hear, but I was still happy with her response.

She said, “I love you, Matt. I’m still not ready to go all the way, but I hope to do it soon. Just not here in the back seat of your dad’s car. I want it to be special and everything about it to be perfect.”

I didn't know it at the time, but she was working on a plan that would lead to home plate for us. And in her mind, the right time was coming soon. I knew she was worth the wait. In truth, I was honored that she was giving so much thought and consideration to such a big moment: losing our virginity together.

I pulled back from our embrace and looked into her eyes and said, “Ange, I’ll wait if you’re not ready yet. I love you so much. I just want to be close to you right now.”

With that, she reached behind her back and undid the clasp on her lacy bra. My eyes were transfixed on her immaculate chest as the fabric slowly slid away from her skin. The top of her bra caught for just a moment on her rigid nipples before it fell between us. In an instant, my eyes were presented with the most beautiful sight. I was mesmerized by her delicate breasts.

I had seen pictures of boobs in magazines before, but this was the first time that I had seen the real flesh of a living, breathing sexy female before my very own eyes. It was incredible. She was incredible.

I couldn’t believe how perfect her skin was. There wasn’t much rise to her mounds, maybe a little more than an inch off her flat chest. Her nipples were pointy, small, and dark brown…a stark contrast to her lightly-toned skin. Her nipples poked out another half inch from the peaks of her tiny mounds.

The sight of her topless was absolutely stunning. My mind was taking hundreds of mental images to file away for later masturbation sessions…images that I would revisit hundreds of times throughout my dating life and even into my adult years. 

On theme with the evening’s playful game of rock throwing, my new target was now in clear view. Two bullseyes in the center of perfectly round signs of innocence and beauty.

My hands had drifted down to her waist as Angie had removed her shirt but I knew they would have a mind of their own now. I lightly caressed her side as I moved toward her breast. Goosebumps trailed closely behind my fingers as they moved up her torso. Every inch of her exposed skin tingled with anticipation.

I placed the palm of my right hand over her breast…exhilarating. Jolts of pleasure raced from my hand to my brain and down to my lower brain between my legs. My senses were on overload but I knew that I had to maintain self-control.

I leaned in to kiss her left breast as I cupped and explored the right twin. I gently sucked on her sensitive nipple. It stood even higher than before as if it was magnetically drawn to my wet lips. I flicked my tongue around its peak and felt the contrasting textures between the nipple and the areola.

She shivered at my touch and drew in a slow, deep breath. She softly moaned, “Ohhhhh, Matt, that feels sooo goooood.”

Instantly I realized that the Bryan Adams song “Heaven” was playing on the car radio. Could this moment get any better? Could this girl be any more amazing? Could this be heaven?

Reaching second base was a moment that is engraved in my memory for all eternity. I had dreamed of this moment for so long, and it was even more spectacular than I ever could have imagined. I had finally sampled the most perfect, tender flesh. I never wanted this night or this moment to end. But it was only just beginning. 

More to come…

Published 
Written by Swillie1990
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