Chapter 1

Lisa and her slightly older sister, Barbara, moved to my smallish town and high school when I was in grade 11. I soon became friends with both them and their very cool parents. In fact, in no time, I felt like a member of their extended family. Barb was in my grade, and her younger sister was two grades below, although I’m pretty sure she had skipped a grade back in her elementary days.

When I first met Lisa at my school, she was a tall, skinny, athletic, and introverted grade nine girl (a ‘niner’ as we called them) with a bit of that awkward ‘coyote ugly’ going on. She had a runner’s body and a Hillary Swank-type of face: pretty with a strong jaw line and cheek bones. In contrast, Barb had a softer, fuller, and more classic beauty about her. However, it was obvious even then that both sisters would likely inherit the impressive brains, boobs, and height of their mother. Yet, despite Lisa and her sister’s physical beauty, we developed a platonic relationship. I became like a brother to both of them. And while Barb and I were more alike in terms of being social extroverts, I spent a greater amount of time with Lisa due to our similar hobbies and sports. Barb, as it would later turn out, became engaged to one of my close buddies. One big family.

Lisa and I shared a passion for mountain biking, running, rock climbing, beach volleyball, and silly humour, among other things. But despite her adventurous lifestyle and level of comfort around me, she was a painfully shy girl when it came to romance. And as we became best friends, any possibility of us hooking up seemed to just naturally fade away. I dated a couple of her friends in high school (which didn’t help), and watched her with interest ‘from a distance’ as she slowly and awkwardly explored the world of dating with other guys in our school. But no matter what each of us had going on with our respective romantic interests, we always hung out a ton together and truly fell into a brother-and-sister-type of love. Still, I do admit to having had sexual thoughts about her every blue moon as I lay alone in bed at night scrolling through my mind’s menu of fantasies to (ahem) help me fall sleep. In my defence, this did help me reduce any sexual tension that was lurking between us. But at the end of the day, I loved Lisa like a younger sister.

The deep closeness of our friendship made our eventual and inevitable parting a sad day, when first I and then she graduated high school and went off to our respective universities. We did, however, keep in touch via social media and we met during holidays and summers if our schedules permitted when we came back to our hometown. In fact, I even stayed at her family home during one semester of university. And it was during one of these overlapping holiday breaks that I started to notice a significant change in my ‘little sister.’

The first clue that Lisa, now age 18, was no longer such a shy and awkward girl was when she caught me staring at one of her hot-looking cousins at the Christmas party her family was hosting. Their huge house was perfect for social events, and Lisa’s parents loved to throw ‘big parties on big holidays,’ as her cool dad would often say (hi, Mr. M).

As Lisa whispered in my ear, “I bet she is making you hard,” she simultaneously tapped the back of her hand against my crotch as if to check. She then burst out laughing. I laughed it off as well, but inside I was actually shocked, and could only blush. Clearly my ‘little sister’ was growing bolder. I wondered what might have happened at university to make her ‘flower’ in such a way.

The next clue happened during the following summer at a conservation park near our hometown, where we used to often visit during high school to run, mountain bike, and swim. However, due to our respective university and summer job schedules and other various reasons, we hadn’t gotten a chance to work up a sweat together for about 2 years.

After we hiked the trails, we headed back to my jeep, which I had left next to the park’s small but gorgeous manmade lake. It was surrounded by lush tree-lined hills and a narrow pristine beach that ran along one side of the lake. Here we talked about taking a dip in the water to wash off the sweat of the hike. However, Lisa revealed she had forgotten to bring a swimsuit. She suggested, to my surprise, that she just swim in her bra and panties, as long as I didn’t mind seeing her in girly-girl lingerie. She further explained that she hadn’t worn sensible underwear for the hike.

This caught me a bit off guard. Sure, underwear is pretty much the same as any two-piece swim suit, and I had seen Lisa in a bikini many times when she was younger; in fact, the image of her when she was a super skinny, but adorable, 13-year-old tomboy running around in a that little pink bikini still haunts me. However, at this moment, I found myself hesitant to call her ‘bluff’ about swimming in just a bra and panties. Maybe I was getting old, I thought.

Regardless, I played it cool and told her with a shrug that it was her call. She smiled and immediately removed her light fleece jacket before starting on her t-shirt and hiking shorts. I opened the jeep’s door adjacent her to give my ‘little sister’ some privacy; or at least perception of privacy. “Ever the gentleman,” she noted.

As we both undressed, I could feel her eyes searching out mine. Perhaps this was to see if I was checking her out; or was she daring me to look? Regardless, she seemed amused by the fact I was either looking down at my now bare feet or glancing up directly at her eyes. I actually thought it was chivalrous of me to not sneak a direct peak at my ‘little sis’ while I striped down to my swim trunks, which I had thoughtfully worn as underwear under my hiking pants in anticipation of a possible swim (smart boy).

Perhaps wanting to be playful, or maybe just semi-disappointed that I had become too much of a prude to sneak a look, Lisa asked me a question that I still remember to this day. Standing there now in only her underwear with her hands at her sides, she focused my full visual attention on her by asking, “Jack, can you see my nipples through his bra?”

Yes, she asked that!

And without thinking (slow male brain) I automatically looked directly at her chest and became actually speechless for a second (and I’m never speechless). My flustered reaction made her laugh out loud in what sounded to me like a victory celebration of sorts; has the younger sister turned the awkwardness tables on the ‘cooler’ older brother?

I had already known in the back of my mind that Lisa’s adolescent body had developed what were likely sizeable breasts back when she was around 16, but she always wore self-consciously baggy clothes to conceal or downplay them. However, what I saw now truly surprised me.

My ‘little sister’ had grown up.

Lisa was now standing right next to me in nothing but a lingerie-style lace bra and matching panties. And the flimsy dark blue bra she had on did almost nothing to hide her surprisingly very large and obviously firm tits, which defied gravity by actually slopping upward as they jutted out from her slender teen body. And to make matters worse, or better, the thin sheer material of the bra cups was obviously designed to teasingly display her nipples, not really hide them. Lisa must have known this.

In what felt like slow motion, my brain continued to register more details about the new (at least to me) naughty features of my ‘little sister.’ Her large nipples (which I had wondered about once or twice) were a light brown colour and sat proudly atop the firm peaks of her provocatively-shaped upward-sloping breasts. And as if to demand even more attention, Lisa’s nipples appeared to be somewhat hard as they seemingly pointed right at me.

Were they hard, I wondered like all men do about nipples, because of the cool late summer breeze or because of how naughty she must have felt about exposing herself to me and the public park area? Her panties looked to be a bikini style (at least she got the name right), which hugged her narrow hips closely. And while the delicate lace panties looked thin, they were not sheer like her bra (thank god), and thus provided adequate concealment for whatever lay between Lisa’s long and well-toned legs.

As surreal as the moment was, there was one thing for certain; Lisa looked beautiful half naked.

Her skin, which seasonally turned from a near lily white in the winter to a light brown under the summer’s sun, was gleaming from the sweat of our hike. And the blue colour and delicately feminine design of her bra and panties provided a stunning contrast to her golden sun-baked skin and to the tall athletic frame of her 18-year-old body. My god, Lisa. Just look at you now.

I was speechless until I could no longer be.

“Well, Lisa,” I finally responded in as much of a matter-of-fact tone as I could muster, “Uh ... you have clearly grown.”

She laughed, and I realized I hadn’t really answered her question. “And... ?” She promoted me again as if practising for her future law career. “Can you see my nipples in this bra?”

I found it simultaneous unsettling and a tad kinky to have my best female friend, who had clearly developed from a 13-year-old adolescent tomboy into a strikingly hot young girl, literally command me to look at her overtly sexual lingerie-framed tits and then submit to a cross examination about her nipples. I was going to jail.

“Yes,” I began as I finally pulled my eyes off her exposed body and back up to the dark brown eyes that were smiling at me. “If it please the court, I declare the nipples in question are poking out demonstrably,” I finished, hoping the attempt at humour would make me look less flustered.

Lisa giggled, and without missing a beat replied, “Then we better hurry into the water, Officer Jack.”

She pulled me by the hand after her and we started a short nervous dash to the lake as if we were skinny dippers looking to limit our exposure on the way to the waves.

And, as I trailed behind her for the first few steps, I just happened to notice (ahem) the back of her panties for the first time. They were similar to a thong style but a bit wider so as to cover her butt crack rather than disappear into it. However, most of her pretty ass cheeks were left exposed to the afternoon breeze, and to her big brother’s guilty gaze. I couldn’t help but notice her bottom had the same hardness and gymnast-type shape as it did when she was in high school: her buns were impossibly narrow across the width, like that of much younger girls, but they protruded out invitingly with a perfect roundness that demanded attention. Oh, little sister. I quickened my pace.

After we dove for cover under the water and then came up for air a considerable distance out from the shoreline, I glanced around to see if anyone had noticed anything, such as a half-naked girl. The scattered families near the beach and adjacent picnic area seemed oblivious. Or were they just being polite?

Meanwhile, Lisa, seemingly nonchalant, had already started off on her swim to the other side of the relatively narrow lake. I followed in her wake determined to catch up. One of the many things I loved about Lisa was her energy and level of compete. Whether it be biking or running or academics, she always pushed herself -and me- to go a bit further, a bit faster, and a bit harder. This is why I was certain she would reach her goal for next year of getting into a top law.

I did catch up, and we swam the width of the lake together, roughly 400 yards at our crossing, and then back again to about the spot where we had started. Lisa was right in front of me as she stood up in the slightly higher than waist-deep water to plant her feet on the sandy lake bottom and catch her breath from the twenty-minute or so swim. As she pulled back her chestnut brown hair from her face, two men sitting fairly close by on the shoreline gave a restrained but clear cat whistle from their lawn chairs tucked under a huge beach umbrella. Even at 20 yards distance, I could clearly see that they had already had a few beers, and, judging by their big friendly smiles, were harmlessly enjoying the late afternoon sights and sounds of the beach. Good on them, I thought.

I assumed that when Lisa first stood up and faced the beach, she had forgotten that she was wearing what basically amounted to a see-through bra, especially now that it was wet. Regardless, she quickly spun around to put her back to the two admirers, and then pushed into me to hide her chest against my body. I couldn’t’ help but chuckle and then reflexively hug her. She was the shy girl once more, it seemed.

Lisa looked up at me (she was tall for a girl at about 5’10, but I had at least 3 inches on her) and smiled with an embarrassed ‘oops’ expression before saying, “Well, I guess I just gave them a show.” She then pulled herself into my chest even more tightly than my initial hug had offered. It was as if she wanted to burrow deeper into the modesty and safety of our embrace.

And as we huddled together in the warm water recovering from the fairly demanding swim in a shared silence that we were both always at-ease with, I expected to feel like I often felt when we shared an embrace: like I was truly the big brother; the best friend; the protector. Lisa had often echoed this by telling me from time-to-time how comfortable and safe she felt with me. I loved this about us.

But something was different just now.

Yes, the warmth and familiar love were there, as were the feelings of trust and safety, but something new seemed to be creeping into the mix. Was it the sexy boldness of Lisa’s surprise ‘lingerie show’ earlier? Or was it how her lingerie graphically revealed the adult-like sexual development of her ripe teen body? Was the unspoken and subtle sexual tension that had sometimes existed between us starting to rise to the surface from its previously well-buried place? Did Lisa feel it, too?

While my mind searched, I could feel my body become acutely aware of ever little detail during this still moment in time. I was aware of how my ‘little sister’s’ surprisingly large and oh-so-firm breasts were pressing against me as we hugged. And I was painfully aware that her warm sleek skin was touching mine in so many other places: her arms around my back; her flat stomach rising and falling against mine as our breathing slowly recovered from the swim; her chin resting on my broad shoulder; her breath blowing gently on my neck.

Something new was happening, and it was involuntary, at least for me.

And, now, that most infamous involuntary muscle of all males was starting to react between my legs in a way it hadn’t ever done before while I was with Lisa, not even when we spooned while watching movies or hugged-it-out for minutes at a time like we were doing now. I couldn’t help it; my cock twitched into a semi-stiff state.

Did she feel it?

Without breaking our embrace, I moved my hips away from hers to hide my arousal. Lisa gave no hint of noticing, but she did suddenly announce with a playful tone, “You are just going to have to hide me until those two big muscle-bound men leave.”

Huh? Her choice of words in describing the ‘beach whistlers’ struck me as odd. And just as I was about to look to see if indeed they were body-builder types, Lisa lifted up her legs and wrapped them around my waist like I was a safety buoy in the middle of the ocean that she was both clinging to and climbing up on to prevent a watery death. This unexpected straddle move elevated her body upward relative to mine; up far enough to so that her chest was at roughly the same level as my chin and just a few inches away from my face. I’m not sure if this was her intention, but Lisa certainly wasn’t shying away from holding this rather intimate position.

It was a position that really made it hard for me to avoid looking at my ‘little sisters’ tits (again); tits that were both beautifully and wickedly framed by her sexy blue bra; and tits that were teasingly exposed behind the thin, sheer, and now wet material of Victoria Secret. A material that allowed Lisa’s large nipples to poke through, and -my lord- they looked like they were starting to get hard (again) right in front of my eyes.

Déjà vu, Jacques.

The same question as earlier sprang to mind: was it the slightly cool breeze that was making my best friend’s nipples harden or the fact I was looking right at them as they protruded out just inches from my face like a siren song? Or was it the fact that Lisa’s crotch -similarly covered in lace lingerie- was now pressing on my hard lower abs as she squeezed her legs slightly to maintain her position. Or was it the fact that my hands had instinctively moved to the sides of ‘my little sister’s’ tight bottom to help support her bold underwater gymnastics move.

Whatever the answer, I couldn’t find it on Lisa’s face. She did, however, have a semi-mischievous grin going, but that could mean anything; for all I knew she was about to start a play fight with me, something we had done many times, but never with her half naked like this.

Regardless, I turned us a bit in the water so that my head and wide shoulders were now between my new passenger and the beach. This gave Lisa’s tits, which had become even more visible when she mounted me, something to hide behind.

“Such a gentlemen,” she chuckled with approval.

I also broadened my underwater stance a bit to steady our balance, which had the added benefit of lowering our bodies a tad further into the warmth of the lake and away from the somewhat cool breeze above. As I did so, I realized I didn’t really need to support Lisa with my hands, as the water was doing most, if not all, of the work required to keep her buoyant and in place on my hips; her strong legs around my waist could do the rest if needed. Nevertheless, I kept my hands on the sides of Lisa’s bottom, somewhere they had never been before. She didn’t seem to notice my hands, but my reflective mind was starting to go down some naughty paths.

Why was my ‘little sister’ wearing a sexy bra and thong-type panties on our hike? Was it an attempt to provoke me? Why was I seeing this new bolder side of Lisa for the first time in the middle of a park lake? Had she developed some kind of exhibitionist kink ... and I was just along as a bodyguard? Or was this watery semi-public place a perfect spot for her to naughtily tease her ‘older brother,’ but also ensure that things couldn’t go too far? And why wasn’t I moving my hands away from her innocent but deliciously round ass? Was it because the naked flesh of her exposed butt cheeks felt both so nice and so wrong in the gentle grip of my large hands?

Just then I realized I had a problem. Her straddling of me had positioned her hips right against my lower abs, which was fine; it felt more than fine, actually. The problem was that while my semi-awake cock was currently hanging off to one side and not bothering anyone, it might just decide at some point to get hard and grow up, especially considering my current situation. And this meant that if things continued to escalate, Max (its nickname from a previous high school girlfriend) would soon be trying to stand straight up and expand to the middle of my abs as it always does when fully erect (yes, I’m bragging about my size). And the problem standing, or rather sitting, in its way would be my little sister’s bottom. She would know for sure that Max was hard.

I tried thinking about football, and despite how good Lisa’s body felt and looked wrapped around me in the lake, this body control strategy actually seemed to be working. Working, at least, until Lisa started playfully interrogating me.

“So Jackie,” she began using the version of my name she seemed to reserve for when she was up to mischief or in need of a favour, “Why haven’t you asked me why I’m wearing lingerie today.”

Oh shit, I thought. The fact that girls could easily and always read the minds of men was diabolical. God is clearly a woman.

“Uh ... not sure. Did some new boyfriend buy it for you?”

“Oh, please,” she mocked. “I’m still single. The guys at my uni are all such pervs. They are always trying look down my top at my tits or get me drunk so they can get into my panties. They certainly aren’t trying to buy me any of Victoria’s Secrets.” Lisa laughed at her clever turn of phrase.

Keeping thinking about football, came my mental mantra reminder. But damn, I was a curious boy and asked, “So ... you haven’t let them do either?”

“Not yet,” came an immediate and proud reply. “But, it’s kind of sad, I know,” she confessed upon further reflection. “Especially sad, to be honest, since I’ve been so damn horny lately. Not sure what’s going on with me.” She laughed at her own bluntness, but I was shocked for the second or third time today (I lost count). We had previously talked in general about our respective romantic relationships, but never the intimate details. And did she just tell me she was still a virgin? I was fairly sure she was when she graduated high school based on comments she had made back then about waiting for marriage or the right guy (bla-bla-bla). But I had just assumed a lovely girl like Lisa, even a romantically awkward one, would have lost their cherry after two years of university.

“But...” she continued, as she looked down her chin at her lacy bra-covered tits that protruded outward in a heavily sexual manner, which contrasted so naughtily with an otherwise innocent-looking teen body, “I have been saving these ‘gifts’ for the just right boy, Jack,” she told me as she moved her dark brown eyes back to mine.

Jesus H Buddha. Was I the ‘right boy’?

I’m sure I had a full-on-nerd grin stretched across my face as I felt like a chivalrous but very horny knight looking for something interesting in the distance to reinforce my resolve. Lisa, ever the observant ‘lawyer,’ noticed I was avoiding looking at the subject of our conversation: her gift.

“It’s ok Jack, you can look at them,” she said in a tone one might use when talking to a frightened child or when dangling a string in front of a kitten. “I know you’re a gentleman,” she continued. “And I’ve been asking myself recently, why should I feel pressure to let some pervs at university be the first to enjoy them? Why not share them with someone I have respected and cherished and loved for so long? Even if he is my big brother. Unless, of course, you don’t like them.”

Oh, sweet Jesus ... football.

“No-no, Lisa,” I hurriedly said to remove any doubt about my thoughts on her beauty, all the while trying to process the implications of her loaded words. I quickly accepted her voyeuristic offer and looked directly at my little sister’s chest. Lisa, still enjoying her mounted position on me, smiled knowingly as she saw my eyes shift and focus.

God, I just loved how her big tits were sloping upward so firmly from her body right toward my face, with nothing but sheer blue lace separating them from my eyes and from my mouth. I also noticed how this deliciously transparent bra was the only barrier (or was it an invitation) separating our longstanding friendship from a descent into something more wicked.

I couldn’t help but feel both guilty and enticed by how Lisa’s now wet and semi-exposed tits looked far too big for both her slender young body and far too big for any ‘little sister.’ Half of my brain still registered Lisa as that innocent 13-year old girl I first met and became friends with. But the other half was now seeing this little girl with big sexy tits that looked like they were demanding attention.

And she must have known this all along, I thought. She must know how much guys get turned on by big firm tits, especially on the skinny body of a teen girl like her. And she knew, regardless of the fact that we were best friends, I couldn’t help but want to see her tits when teasingly exposed in such a naughty way. I am a man. She knew she would turn me on with her sheer lingerie-wrapped tits, and that I couldn’t possible resist her offer to enjoy them. And this made her ‘gift’ of sharing them with me all the more naughty. And with this confidence, she clearly wasn’t waiting for me to ask, she was just giving me my present, ready or not.

“I do like them, Lisa. They are very pretty,” came my weak reply.

“Them? Pretty?!” Lisa shot back, in a somewhat disapproving but playful tone. Not the answer she was looking for, I guessed. “You can call them tits. I’m not 13 anymore, big brother” she playfully scolded.

“Um, yes, your tits are pretty, but also sexy. Actually, ok, your tits are amazing. Just like you,” I quickly added at the end in an attempt to soften my initial confession that may have come off sounding a bit pervy; I suddenly wanted to keep being the ‘right boy’ in her eyes. But her next question made me realize she was giving me the green light to be fully honest, and maybe even a bit naughty.

“What about my nipples, Jack?”

As she asked, she squeezed her athletic thighs and legs on my hips and back just enough to cause her vulnerable panty-covered pussy to push forward an inch or two and press against my hard abdomen. In response to the naughty words and the feeling of my ‘little sister’s’ thinly veiled pussy now deliberately pressing up on my stomach, my cock twitched and grew harder despite my best efforts at self-control. It was about to make contact with her bottom, I realized. It was then that I surrender to it and to the moment.

I looked directly at Lisa’s jutting tits just inches from my face and confessed in a rather husky voice, “Your nipples are perfect, Lisa. So big and so long. They look like they are aching to be sucked.” As my words fell out of my mouth my cock took it upon itself to press against the side of Lisa’s bottom and along the upper part of her leg.

“Oh my,” was her reply. I wasn’t sure if it was in response to my words or my underwater probe. “It looks like you have gotten bigger as well,” she continued in obvious reference to my earlier comment about her. Her teasing continued. “Are you trying to poke my bottom, sir,” she said in mock formal language.

I’m sure I looked bewildered, guilty, and semi helpless. And as if to tease me more, to push me more, she leaned in close to my ear as if to tell me a secret, and in doing so the side of one of her lovely breasts briefly rubbed on my face. Oh god, I wanted to squeeze and suck them, sister or not.

“You know Jackie,” she whispered in the exact same innocent 13-year old girl voice she had before, I had one football player at university tell me he wanted to put his big cock all the way up into my little bottom.”

My mind reeled and my cock jumped at these shocking and deliciously naughty words that clearly were meant to arouse me or torment me or both. My twitching cock expanded and now pressed urgently against Lisa’s bottom as if trying to find more space to grow. Lisa, with a knowing grin, obliged it. She pulled her hips away from my lower stomach so that my erection could range free and rise up along the middle of my abs. I was grateful for this release until I felt the head and part of my shaft actually push past the tops of my shorts to escape fully naked into the water (I should of tied the trunks), which -thank god- was high enough to easily cover our lower bodies and then some.

Lisa, after a moment, and while looking directly into my eyes, slowly and gently attempted to return her hips back to where they had been previously stationed on my lower abs. But with that movement, her little panty-covered pussy now pressed ever so lightly - but unmistakably - against the exposed part of my now almost fully erect cock. While I stopped breathing for a moment, I saw Lisa inhale sharply and her eyes flash wide with recognition as her innocent pussy gingerly made contact with my cock through her panties. I could actually feel the lace and the softness her tiny pussy beneath it right on the skin of my engorged shaft.

My god it felt so good and so wrong all at once.

My cock twitched from this taboo lacy contact, and as it expanded to its fully hard state, I felt Lisa’s body tense as a slight vibration ran through it. All the while she kept the crotch of her thin panties and the treasure behind it exactly right where they were causing me so much delicious desire: ever so lightly making contact with my now rock hard shaft.

We both remained perfectly still. Neither one of us spoke nor acknowledge what had just happened. She looked into my eyes with a satisfied smile on her face, but there was also a flicker of lust, and I could see her breathing was just a tad bit more noticeable now as her breasts rose and fell slightly. As for me, I was still holding my breath in fear I might shatter this surprising and naughtily surreal moment.

We both remained perfectly still.

“Am I hurting you,” she asked after a long, long, long pause, and with a voice that was less steady than before but still in control. I knew it wasn’t a real question as Lisa wasn’t placing any of her weight on my vulnerable bits: my cock and balls. Rather, her weight was carried partly by my hips, which her legs wrapped around, but mostly from the buoyant force of the water. Her question was really a discreet acknowledgment to me that she knew exactly where her pussy was positioned. It was an indirect calling out of the elephant in the room: a little sister’s pussy -with nothing but thin lace to protect it - was ever so delicately touching against a big brother’s rock hard cock. And Lisa wanted to signal to me, without actually acknowledging it, that this wasn’t an accident; she was going to keep her vulnerable little pussy right where it was on purpose, ever so gently touching and teasing her big brother’s cock through the thin material of her girly panties as she straddled him in the water.