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Lisa’s Evolution Pt. 02: The Crossing Over

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Title: Lisa’s Evolution Part II: The Crossing Over

Author: Jack Riley


As I pulled into the driveway of Lisa’s large family house, I thought back to the previous year’s unexpected encounter at our favourite conservation park. Lisa, who had been my friend and ‘little sister’ for years, had unexpectedly decided I would be the first boy she would share her gorgeous 18-year old body with; well, at least some of it. And share she did right there in the small lake. Afterwards, we didn’t really talk about the fact that she had taken a significant sexual step forward, and had done so with me, her ‘big brother.’ Perhaps because of this, the drive back to our hometown had been surprisingly free of awkwardness. It seemed that what happened in the lake would stay in the lake. In fact, our friendship continued on as if nothing had occurred under the surface that summer. And now, as I reached Lisa’s front door in full reflection mode, I wasn’t prepared for what would come next.

I knocked and then walked into the family home that Lisa no longer officially lived at, but did use as a base of operations when she came back to our hometown to visit with everyone. Her life, now, as well as most of her stuff, was stationed back at her university apartment, which was in the big city where she knew she would stay to work after graduation from law school and admission to the bar. However, since her family had ‘abandoned her’ on this holiday, Lisa invited me over to spend some long overdue quality time together. We decided we would do a long bike ride to our favourite park and then chill over a nice dinner out and perhaps catch a movie.

Lisa and I exchanged a big hug and did a catch up over coffee in the kitchen before we started our day. She looked the same as the previous summer when I saw her last in person. However, as we talked and joked, it was clear that Lisa had continued her flowering into an ever worldlier young lady, which was a process I first noticed a year ago. She seemed even more confident and assertive now in terms of how she spoke, and stood, and looked at me.

“Law school suits you, little sister.” I confessed. She winked at me in response and then said, “Let’s see if you can keep up with me…on the bikes.”

As we did the 25-mile bike ride up to the park, the unannounced gathering of storm clouds altered our plan to take a dip in the lake there, which would have been interesting considering our last swim. Instead, we just headed back for home before the rain hit. Unfortunately, we got caught out in a rather heavy thunderstorm. As we peddled through a river of wind, I thought to myself that this wasn’t how I had envisaged the day with Lisa going.

Upon finally getting home, we parked our bikes in the shelter of her garage. We were both so soaked to the bone from the rain that Lisa suggested we take off our outerwear in the garage before entering the house through the adjoining laundry room door. I shrugged and striped down to my boxers. Lisa did the same, and this time I did sneak a peek. And as I did, Lisa turned to face me wearing a black sports bra and very sensible panties.

“Sorry big brother,” she said with a knowing smile, “No lingerie this time.”

I laughed it off. But, yes, I admit that I was disappointed. I did love, however, the fact that we were still close enough to casually strip down to our underwear together. And Lisa looked just as lovely as she did a year ago in the lake. Even in a sports bra and sensible panties, her tall 5’10, slim and athletic body was mesmerizing. And good lord, her tits were as big and firm and as provocatively shaped in an upward slop as I remembered that day.

As if Lisa read my mind or caught me checking her out or both, she said, “It’s ok Jackie, you can get a good look in case you need to use it later.” Then with a mischievous grin, she entered the laundry room to get us towels.

‘Wow,’ I thought to myself. ‘Did she just boldly imply or joke that I was going to jerk off later to that image of her in soaking wet underwear? Law school, indeed.’

As we toweled ourselves dry inside, Lisa then told me I might be able to find some track pants or something in her old room upstairs. She was going to grab a hot shower to warm up and get new clothes from her overnight duffle bag that she brought with her from university.

As I walked into her room with a towel around me, I saw just how empty and ‘out of date’ it was. Lisa’s parents kept it as a bedroom for her, but clearly Lisa hadn’t really inhabited this room since her high school days. There were still old teddy bears scattered around and figurines on the dresser; a dresser that seemed, just like her closet, to be empty of any substantial clothes. Empty, that is, except for what looked like an old sock and underwear drawer. Among the socks I found a pair of very girly-girl pink panties she probably hadn’t worn since she was in high school. I immediately felt pang of guilt and arousal as all guys do when they see girly underwear niğde escort they probably shouldn’t be looking at. I picked up the tiny panties, and thought about how tight these must be around my ‘little sister’s’ pussy when she wears them. There was no way I could fit into these, I realized, and reluctantly put them back. Also in the drawer were a pair of wine coloured pantyhose that I had seen Lisa wear a few times in the past when she wore that short gray skirt she liked to rock when feeling sassy. I remember thinking the combination was half preppy and half sexy. I held them up and thought, why not. I closed the door, dropped my boxers on the floor and then sat down on the bed to carefully slide the pantyhose up along my legs. Thank god I had naturally smooth legs, I thought to myself.

As soon as I did, I felt my cock stiffen just a little and I wasn’t sure why. Was it the lingering effect of having just seen Lisa in her underwear downstairs or seeing and touching her little panties in the drawer? I know all guys get turned on by panties and stockings and pantyhose, but that was because of how naughty they looked on the girl. But here I was getting a bit of a stiffy by actually sliding hosiery up my legs. I nevertheless stood and continued to pull Lisa’s wine-coloured pantyhose up over my hips, my butt, and finally my cock. And as the material of the pantyhose made contact with my cock, it actually twitched further to life and grew a bit more off to the left side of my groin where it was held firmly in place and pretty much parallel to the ground by the tightness of the pantyhose.

“Wow, Jack” I heard Lisa exclaim in surprise from the bedroom door that she had silently opened. “I see you found something you like,” she laughed as she walked into her room toward me. Despite her laughter, her dark brown eyes were wide with shock.

My head jerked toward Lisa, who was still in her sports bra but now with a towel around her hips. Time froze, but I did reflexively place my hands over my bulge, and then managed to say in a very guilty way, “Ah Lisa…I couldn’t find much else.”

“Surrrrre,” Lisa acknowledge in a still amazed tone. “But that doesn’t explain this,” she said accusingly as she moved my hands away from their covering positions near my crotch and then nodded toward it like a lawyer pointing out evidence.

With my hands now at my sides, I felt the heat of her stare, which focused right at my semi-erection, which was not standing up directly, thank god. Rather it was pinned off to the left side of my hips by the pantyhose. However, it was still clearly bulging outward and fully visible under the thin sheer red material.

“Now that needs explaining,” Lisa said no longer laughing but still clearly both amused and surprised as hell. She shifted her wide eyes back to mine in search of an answer. And when I just stood there silent like a kid with my hand caught in the cookie jar, she looked back down to my bulge again.

“And Jesus, Jack, I knew you weren’t small, but didn’t know you were packing such heat. I must have been preoccupied in the lake with my own…revelations,” she said with a small blush. This was a clear reference to when she hand straddled me last summer in the lake in order to share her body with her favourite ‘big brother.’ I remembered that while she had pressed her panty covered pussy along my shaft under the surface of the water, she never actually saw it. But Lisa could certainly see her big brother’s cock now, exposed as it was with just the sheer wine-coloured pantyhose covering it.

I felt humiliated at being caught like this but also getting further aroused as I stood there before my ‘little sister’ wearing such an intimate and feminine part of her clothing that let her –indeed invited her to- look right between my legs at a cock that was clearly enjoying being inside of her hosiery. And while I have always been proud of my size (too proud, some girlfriends had said), I was honestly embarrassed to be showing it to Lisa like this. But I have to admit, I did like that she implied it was big. There was something naughty about having a little sister know and acknowledge that her big brother was well hung. Lisa’s voice snapped me back from the slow motion awkwardness of the moment.

“So tell me,” Lisa began as she once again shifted her eyes back to mine in search of answers, “what has given you such a hard-on?” There was a serious curiosity in her voice.

“I don’t have a hard-on” I protested almost automatically, and then added more truthfully, “well, not fully.”

“Oh, not fully? Lisa, mimicked my words and looked back down between my legs as if to check out my story. “Well, that sounds like a challenge, big brother. Should I leave you alone with my pantyhose so you can get fully aroused?” She giggled at the suggestion.

“No,” I said way too quickly, and meaning I didn’t want to pleasure myself with her pantyhose. This might have been a lie, I thought. But Lisa ‘the lawyer’ jumped all over my testimony.

“No? Oh, you want to me to stay nişantaşı escort here. You like me seeing you like this… stretching out my poor pantyhose with your big………brother?” She ended here question with a self-satisfied smile from her play on words.

I didn’t answer, but the answer was yes, I realized. Standing here so exposed, so humiliated, and being interrogated by my best female friend was…exciting. And I wondered if Lisa was picking up on the sexual energy I must have clearly been radiating.

“Well if you are going to wear them, at least wear them right.” And with that she bent over a bit at the waist to reach down and rather forcefully shift the pantyhose around my hips to straighten them or the seams or some such. What did I know? But this motion caused the pantyhose material to rub so deliciously on my cock that it twitched in response and grew further. The angle also shifted a bit so it was less off to the side of my hips and now a tad closer the centerline of my abs. I was worried, strangely enough, that if it kept growing toward the center of my abs -where it always goes when fully erect- it would pop out of the top of the pantyhose. Thank god her hosiery was so tight on me that it acted like a restraining harness on my cock.

“Jesus, Jack, you weren’t kidding, it is getting bigger,” Lisa declared and then bit her lip as if in thought, but maybe it was just shock, I wasn’t sure. Maybe it was a facial reaction from a sudden pang she felt in her mind and body that betrayed her naughty interest in -or arousal from- what was growing between her big brother’s legs.

She finally asked without taking her eyes from my cock, “How big does it get?”

“About 9 inches or so,” I replied.

Lisa stood back up fully looked at me hard in the eyes. “Liar,” she declared but with not much conviction.

Then something change. I could see wheels spinning in her mind as she held me in her lawyer’s stare. There was that same mischievous and determined look in her wickedly smart eyes I remember so well from the lake last summer when she started her teasing and the “sharing” of her body with me. And when she next spoke to me here in her bedroom, her voice was void of the amusement and shock it had a minute ago. Now it was lower, even a tad flirty, but still with a lawyer’s edge to it.

“So Jackie, you didn’t answer my question. What is it with the pantyhose fetish you’ve got going? I mean I know you love my panties.”

I quickly thought back to how she teased me with them in the lake.

Lisa continued the interrogation as if she were inside my head. “I know this because of how you reacted when I rubbed my panties on you in the lake. Which, by the way, I felt bad about after. Not the sharing of things with you, which I loved and cherished, but the fact you must have been so blue-balled afterward. It didn’t occur to me then, my bad. “But now, naughty boy, I think it’s my pantyhose you really want. And maybe we should see if we can make a right out of these two wrongs.”

I stood in silence not sure what she meant by ‘two wrongs’ and not daring to ask or move.

“So, explain big brother. Help me help you. How is it that my pantyhose have caused this?” she nodded toward the bulge between my legs that had actually started to throb listening to her talk about our time in the lake and her panties.

I didn’t really know the answer, but I started my ramble anyway. “No sure, Lisa. I was just looking for clothes and I saw that your panties were too small, and there really wasn’t much else. So I tried on…these…” I testified in what I though sounded convincing innocent until I looked down to see how guilty my semi-erect cock looked bulging out and extending far off to the upper left side of my hips. I then hurried to add, “And maybe I just wanted to feel how you must feel when you wear them.”

My beautiful lawyer jumped on and through this courtroom opening that I gave.

“Oh, so you wanted to feel girly? Because that is the only time I would wear these coloured stockings…to feel feminine and girly and sexy. That is what hosiery is for, Jack; for females to feel like girly girls for boys to notice. Boys aren’t supposed to wear these, Jack.”

Lisa then thought for a moment before quickly adding, “You know, I took a psychology of sex class at university and learned that some alpha males like to wear girl’s underwear and such to explore their submissive girly side. Is that you Jackie? Do you want to be a sissy girl sometimes and submit to someone more powerful, Jack?”

Lisa’s expository examination of the causes of my erection standing there for both of us to see, with its taboo question and implied conclusion made my cock twitch again and straighten further under the pantyhose. It was not threatening to poke out of the top left side of the pantyhose’s waistband.

“Oh my, ” Lisa commented, her voice breaking from her lawyer’s tone back to her small-town girl for just a second, but making no secret of ankara olgun escort the fact she saw my cock lurch up more. The interrogation then continued.

“Or Jack, do you just want an excuse today to show your ‘little sister’ how big your cock really is when it gets hard? And that is certainly something my thin pantyhose are doing for you; making you hard and showing off your big cock.” Lisa was in full lawyer role now. There was no trace of my little sister whom I had met years ago in high school.

And Lisa’s naughty choice of words and interrogation style — which perhaps were designed to simultaneously illuminate, humiliate, and further incite me for my taboo enjoyment of her pantyhose- was making my hard cock start to throb and ache for touch. And as if reading my thoughts, Lisa then placed a hand on my lower abs, so agonizing close to -but not touching- my cock. She then let her long fingers ever so slightly stroke the red material of the hosiery as she continued her teasing words.

“And this thin hosiery, Jack, is certainly not hiding anything, is it? I can see your cock straining right against it. Do you like how my pantyhose feel on your shaft, Jack?”

“Yes,” I confessed, helpless to stop my answer and helpless to stop my cock from twitching again and now flexing to its full length and thickness as it pointed toward the top of my left hip.

Lisa’s hand was a mere inch from it, but her eyes were right on it as she commented in a voice I remembered from the lake when she got turned on by our touching, “That is big cock, Jack.”

And whether it be from her feeding off my excited state, or from her hand so naughtily close to my raging hard on, or from seeing the size of my cock that she and her hosiery had made so big and hard, I could sense Lisa was also becoming aroused. I had certainly not forgotten how she has been so sensual and excited with me in the lake. And I was now remembering how she could, even back then, talk a very naughty talk for such a good girl. I was now witnessing firsthand how her skills had improved.

Lisa continued on with her lawyer’s voice but with less success or attempt at covering the sexual tension that was now clearly mixed in. In fact, let the towel drop from her hips as she moved her mouth closer to my ear as if someone outside the interrogation room might hear. I could feel her breath and body so close now. Like an experienced interrogator moving in for the kill, she made sure there was not an inch of space between us; not an inch between her large sports bra-covered tits or her panty-covered narrow hips.

“Or it is about me, Jack? Is it about knowing that you are wearing the same pantyhose I’ve worn before? Which would be naughty, wouldn’t it? These pantyhose that are rubbing on your legs have rubbed on mine,” she teasingly declared as her hand that had been on my lower abs now moved to rub my right thigh through the thin wine-coloured material. “And the hosiery covering your ass has cupped my bottom as well.” She put her reaming free hand on the side of my hard butt cheeks and rubbed ever so gently before continuing. “And Jack, the material stretching so tightly on your cock right now… is the same that held my little pussy so close.” With that, her hand on my right thigh moved up to the left side of my groin and hips and ever so gently pushed one fingertip onto the shaft of my cock as if to challenge the big bear to come out and play.

“Oh Jesus, Lisa, ” I whispered as I watched my little sister move her hand directly toward my cock and then saw and felt it visibly push on my shaft, which twitched with both a satisfied need and urgent desire for more.

I stood there throbbing and processing such a rush of mixed emotions as my best female friend whom I loved like a sister, respected fully, would defend with my life, and whom perhaps I not so secretly desired, had caught me in her pantyhose; in fact, had caught me getting a hard-on in her pantyhose. And rather than throw me out of her house, she had responded by indulging my taboo reaction.

No, she was more than indulging my perverted reaction, she was inflaming it in a most naughty and teasing way. Her gorgeous brown eyes were fully looking right at my 9 inches of rock hard guilt that was throbbing insider her pantyhose. Now one of her slender long finger was pressing on my shaft through its pantyhose harness; her pantyhose harness.

And she wasn’t done with me yet. I could not have expected what happened next, nor could I have known how much I would enjoy it.

“So tell me big brother,” Lisa continued, “what is the answer? Why are my red girly-girl pantyhose making you so hard?”

I stood in pathetic silence with a brain that stunned my ability to speak yet was hyper sensitive in reaction to her finger pressing on the shaft of my cock. As if reading my thoughts, again, Lisa took that finger away as she moved to stand directly in front of me. My man radar immediately noticed her nipples were making points through the sports bra and I reflexively glanced down to her tits. This is why I didn’t see her right arm moving until after I felt the smack. In fact, it was a quick motion of the wrist and hand -and not so much of the arm- that produced the slap. The realization of what just happened registered in my brain just a split second after the sharp but low level pain did.

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