Do It or Lose It

The guys all shared mutual looks of bewilderment as we began to slowly take off articles of clothing, one by one, not realizing we'd be stripping down as a group and suffering the inevitable insecurity of covert body comparisons. It was further made awkward by the fact that Jenna stood there watching us, smiling happily any time our eyes met hers. Before long, the whole lot of us stood there butt naked, quietly breathing in deeply and trying not to think about the fact that our penises were out and exposed to the world, dangling down between our legs and trembling slightly as we anxiously awaited her next instruction.

We were soon led, one by one, to our individual rooms. Once we were planted inside one, a curtain was drawn across the entrance to secure our privacy. It was not terribly private, however. Sure, our neighbors would not see us, but certainly they would hear. The flimsy walls were far from soundproof and they didn't even quite reach the high ceiling.

So there I stood, alone and abandoned without a stitch of clothing, waiting nervously in a small, sparsely furnished den of sin. I had to laugh at first at how surreal it was. Was it going to be the weirdest thing I'd ever done? The best thing? Something I'd soon want to forget?

A few minutes later, I heard the girls being led in. There was not a peep from any of them, just the shuffling of feet and Jenna's distinct voice. I stood in the back of my room, ramrod straight, waiting for my "partner" to come through the curtain and greet me equally anxious and equally without any clothing on her body at all.

I listened to Jenna's instruction to the girls; for the most part, a repeat of the speech we received. She told them to undress and place their things on the same table. After some silent hesitancy, I heard zippers and buttons being unsnapped. The movement of feet and rustle of clothing. I couldn't help but imagine bras being pulled away from bodies en masse, a sea of panties being reluctantly slipped down to ankles, nervous, naked bodies standing about in a sea of breasts and pubes and anxiously awaiting the next step.

The realization that all the girls were standing nude on the other side of the curtain was a momentous knowledge to possess and it caused me to suffer a great curiosity. I thought about crossing the small room to peek out through the curtain and see them all standing there exposed and defenseless, Leah included, but somehow I couldn't make my feet move. For some reason, I thought for sure they would see me, shriek and holler. I don't know...

Anyway, it was too late and I was already kicking myself inside for not sneaking a careful peek. How could I have passed up the opportunity to have a look at the woman of my dreams standing there completely naked? Perhaps I just respected her too much. There wouldn't really have been time, anyway. Only seconds had elapsed since they finished undressing before Jenna began leading the girls to their partners. I heard them go one by one to the other rooms nearby. I heard curtains slip open a crack to let them slip through.

I found myself frustrated to neither see nor hear the exact moment that a naked young woman entered to find a naked young man standing there, their curious, cursory examination of breasts and genitals, the two of them suddenly aware of the stranger they were about to fuck on a soft red futon in the middle of the room.

Finally, my heart sank as I heard someone approaching my room. I remember tensing up, almost to the point of it being painful. My penis gave a twitch, already beginning to fill with blood in the sheer anticipation of what was going to happen. I obsessively wondered who it would be, going through each of the girls I'd just met like some kind of bizarre Rolodex.

Most of all, I wondered if it would be Leah herself; if this was the moment I had been waiting for my entire life. The moment that we'd finally see each other naked, bringing to an end an intense curiosity that I found myself hoping had haunted her for years, just as it had for me.

The curtain exhibited a sudden movement, slipped aside just a small amount, and let through an astonishing figure. An utterly naked figure. A shock washed over me as I was suddenly met with the sight of jiggly bits. Hairy bits. Bits normally kept well hidden from prying eyes.

Those bits did not belong to Leah.

Standing before me, legs bucking and teeth grinding tightly against each other, stood Carissa, the ruddy-cheeked young woman from Virginia with whom I had just exchanged brief pleasantries. She entered the room even more terrified than she had been before, appearing to gasp as she stopped on the other side of the curtain. The two of us stood there naked, ensnared in the sight of each other shocking nudity.

I couldn't help but analyze her body and mannerisms with feverish energy. She was particularly fascinating because of how awkward she was, swept up as we were into the situation that had brought us together so unexpectedly.

Carissa had long, wavy brown hair. She was very tall, with an average build. She had a soft, sweet face that clashed with her voluptuous body, like a girl who had been caught by surprise as her body exploded into adulthood, leaving her bewildered as to what to do with it. Its features were disproportionately exaggerated. Carissa had perhaps the thickest and most visible pussy lips I'd ever seen, with a fluffy wisp of hair above them.

Even more dramatic were her breasts. They were huge compared to her overall frame; bulging, supple, unwieldy. She was visibly self-conscious about the size of her boobs and any attention they drew - but her solution for carrying them around only made them more striking to behold. She folded her arms across her chest, underneath, as if to make a tray for them to rest on, then let them plump up and protrude outward with her two wide, pink nipples leading the way. I found the whole thing impossibly adorable, the way she seemed to struggle with the pronounced appearance of her private parts.

The spectacle before me caused an instant erection. It was unavoidable and there was nothing I could do to fight it. There was no point, anyway. I wondered what she must be thinking as I endured the embarrassment that followed. Her eyes clearly dropped between my legs where they settled on my stiffening penis, sticking straight out from my body and pulsing softly.

I wondered what she was thinking as she gazed at it, stone-faced and frozen in front of the curtain. Did it make her excited? Did it make her feel more anxious? Was she coming to terms with the fact that this was the erect penis that perhaps she was about to have in her mouth and then inside her vagina, just as I gazed at her body and thought about the different ways I was about to experience it? The whole situation was confusingly, bizarrely erotic.

I couldn't help staring. Something about her was so thrilling. Perhaps it was because she seemed so awkward and insecure about her body. Due to her extremely defensive stance, I immediately assumed she was so shy in real life about finding a partner that she resorted to this. I felt bad about that, but it still seemed so obvious. Then I dismissed the thought, deciding I was being too superficially analytical. Who was I to know anything about this person from just a five-minute conversation?

Regardless, I reveled in the fact that she was a real woman; not some airbrushed, cookie-cutter girl from a Playboy magazine, no, she was not "perfectly proportioned." She was gangly, awkward, hastily groomed, and I loved it. I loved it because she had such an innocent, natural beauty. I loved it because I saw her insecurities and could relate to them myself. I wanted to make her feel better and for her to clear my own anxieties. I wanted to make an erotic connection with her, right then and there. Someone I'd only just met and barely knew. So there we stood, facing each other, at the point of maximum erotic potential.

"Hey Carissa," I said, eager to reveal that I had remembered her name.

"Hey Evan," she said, her mouth forming into a nervous smile.

"Um... I guess let's have a seat."

"Yeah, I could use a seat," she rushed to say, breathlessly. She rushed to join me at the edge of the futon, grasping at her heavy, jiggling breasts in order to contain them as she performed a light jog.

On the mattress, Carissa pulled her knees up to her chest and wrapped her arms around them. This was another wildly defensive stance on her part, meant to obscure her body. However, unbeknownst to her, it only served to cause her thick outer labia to squeeze through the gap between her thighs to form a bulging, fleshy sandwich that I found hard to look away from.

"So... this is interesting..." I chuckled.

"Yeah..." she said with a soft laugh. I could almost hear her heart thundering in her chest. So was mine.

"Let's see what we've got..." I continued, looking for something to say that would prevent the conversation from sinking into total silence. I scanned the table and described the various objects that sat there. However, announcing the presence of a shrink-wrapped dildo, a small riding whip, and other cheap novelties didn't exactly help to reduce any tension between us.

When I turned back to face her, all I saw were two big eyes on a face growing increasingly red.

"So... like... how do you want to do this? Is there anything you wanted to try?" I cringed listening to myself. I was getting way ahead of the situation. I just didn't know what to say.

"Um... I dunno," she said. Then she laughed suddenly and tried to hide her face. "Urrr," she exhaled through a quivering smile, rolling her head back and gritting her teeth, trying to flush the obvious tension from her body.

We laughed together and tried to shake off the nerves. I knew I'd have to do something or else we'd end up just sitting there at the end of the mattress the whole time and everything that had led up to that moment would be for naught.

I decided that talking about it wasn't going to get anywhere. Instead, I just gave her a wordless gaze, as comfortable as I could make it, full of soft, serious affection. She immediately quieted down and locked eyes with me, realizing that something was indeed about to happen. I reached out and gently stroked her hair, figuring it was an easy way to make contact without much pressure. She just looked at me like a deer in headlights.

Still unsure what I was doing, I felt myself leaning in for a kiss, merely because I was used to doing that with women I was actually romantic with. I did it slowly, making absolutely clear what my ambitions were to give her more than enough time to back out. Before I could even reach her lips, I felt her nipples graze against my chest. Her body tensed up immediately. Then our lips connected. Hers were soft and warm. I felt her strained breath on my face as she breathed through her nose.

We began kissing softly for a few minutes. She came to the table with a sincere interest which made me feel less anxious about the situation. It was a comfortable way station to remain at as we collected ourselves and discovered each other's cautious willingness. Eventually, I decided to be brave and I reached out for her body again, this time to cup her breasts. I felt her react again as my hand connected with her soft, spongy flesh. Her large boobs acquiesced to my curious fingers. Carissa's whole body was surging as her lungs filled to capacity and then deflated.

Up to that point, I honestly couldn't tell if she was truly excited for what we were about to do or if, deep down, she was thinking about fleeing through the curtain. However, just a few moments after I began to caress her breasts, I had my answer. As if just needing me to take the first step, I suddenly felt her hand grasp eagerly for my erection. Her entire body jerked suddenly with emotion as she wrapped her fingers around it and gave it a soft squeeze. It pulsed hungrily at the core of her fist.

I felt a sudden excitement as I discovered her exceeding my bravery under tremendously awkward circumstances. As I began to play with her nipples, I felt her begin to stroke me. Her trembling hand traveled up and down the full length of my shaft as it sprouted eagerly from my lap. I was no longer convinced that her tremors were the product of nervousness alone. There was clearly also a growing excitement.

The wall had been broken. It was officially on between us.

The kissing became more passionate as we realized the degree to which we could touch and explore each other's unfamiliar bodies. We groped each other, blindly but tenderly. Despite all the times I'd been with a girl, I felt something entirely new at that moment. A potent, explosive sexual energy that I'd never felt before. It burned inside me like a fire.

After cautiously seeking each other's tongues for a while, we pulled away from one another. Carissa seemed to feel embarrassed about the way she was touching me and avoided looking into my eyes. Instead, she looked thoughtfully down at my penis as she gave it curious strokes, lifting it up and down as she went, having a look at the underside, and at my firming testicles. I was so turned on by her innocent exploration of my body that I could already smell my own musky odor blooming between us. A smile broke out across my face. Carissa looked up at me suddenly, meeting my grin with her own. I felt things starting to relax between us.

However, her anxiety partly returned as my hand traveled down the inside of her thigh. It was obviously apparent what part of her body I wanted to explore next... and which she felt the most insecure about. I felt giddy like it was my first time with a girl all over again. Somehow the strangeness of the situation made everything feel uncomfortably, thrillingly new again. She leaned back nervously, resting onto her forearms and eyeing me cautiously. Carissa allowed me to move her legs aside and part her hips. She seemed incredibly nervous as I sat there gazing at her beautiful, lightly hairy pussy beginning to gape slightly as she opened up to me. I knew that if we'd just make it through this area of insecurity, who knows what we might be able to do together.

I reached out and gently touched her labia, splitting it open slightly to reveal the pink inner flesh of her vagina. She was already becoming wet. I wanted to sink my fingers inside her body but I reeled in my impatient curiosity. Gently, I began to stroke her labia and the inside of her thigh. She began cooing quietly and slipped into a kind of trance. Her folds parted easily, permitting me to stroke along the velvety flesh inside. Soon, her hardening nub began to peek out. I circled it with my fingers and she moaned loudly.

Carissa's eyes flashed at me. Just minutes earlier she had avoided looking at me at all. Now she seemed to be directing me questions that she did not want to vocalize.

"Do you... want me to eat your pussy?" I whispered. As nervous as I was, it thrilled me to just ask such a question out of the blue to a woman I'd only just met.

At first, Carissa seemed positively aghast that I asked her this, yet she lay fully back onto the mattress and quickly nodded. I crawled forward, examining her pubic area adoringly, lost in every sensual detail. She seemed to hold her breath as I lowered toward her crotch. Then, contact. She gasped softly as my lips graced her labia. It was as if she'd been touched there for the first time ever. Her body jerked to life, desperately opening to me and to the thrill of having succeeded in doing something that was both terrifying and miraculous at the same time.

I planted kisses along her long, deep slit, then loosened her flesh with the tip of my tongue, stroking her delicately as I had done earlier with my fingers. As she quivered, I found myself suddenly awash in her body's natural odors, along with the faint traces of some other flowery scent. I imagined her lightly dabbing her body down there with her favorite perfume before leaving home as an extra means of seduction, or else as an act of insecurity.

I gave into my curiosity, sucking at those moist lips and dragging my tongue through her depths as she became feverish and creamy. Her sudden jerks and squeaks only drove me wilder as I continued to work her pussy with my tongue, fascinated by the generous secretions of her body and their earthy savor. I lashed excitedly at her body, building her into a frenzy of emotion, teasing her bulging clit until it left her unhinged.

When I finally rose from her pelvis with the need to rest my jaw, she sprung to life. I became excited at her apparent enthusiasm for taking a turn. I quickly sat back and allowed my cock to spring upward, fully distended and awaiting her lips. She quickly lay down between my legs and curled her fingers around me as before, then guided my penis through her lips and over her soft tongue.

There was no doubt about it at that point. As nervous as she'd been on the outside, her inner state raged with the same fire that mine did. I knew in an instant that she wanted my cock. She wanted to lick it, to taste it, to feel its angry pulse against her tongue as she devoured it whole. Still, there was an enchanting awkwardness laced through her enthusiasm, placing fully on display her absolute, lingering disbelief at the very act she was performing. Carissa continued her intrepid sucking as I squirmed in pleasure, watching her nostrils flex and bulge as she breathed in deeply and investigated my musky scent all the while.

As Carissa finally pulled away, my cock sprung from her mouth and stiffly bobbed in the air, still glistening with her saliva. She licked her lips softly then bit them nervously. We both knew what would come next, although now we were unquestionably better prepared for it. Carissa swept her hair aside as she scooted further back, onto the center of the futon, then threw herself down onto her back again, sending her heavy breasts into a playful wobble. No longer did she display any horror at the thought of letting me see them bounce and swing about freely.

I slid forward, holding my cock between her legs. We exchanged brief glances, quietly assessing each other's state. I eased into it, taking the swollen head of my penis and rubbing it back and forth along the dewy, pink flesh between her legs. When I saw her begin to shiver, I pressed forward and began forcing myself inside. I felt her inner muscles stretching wider for me, welcoming me into the depths of her body. As I did this, she grasped for my arms, gripping them tightly and letting slip a small gasp.

I slid smoothly into her tight pussy. Her eyes widened and we smiled at each other, both of us rapidly increasing the frequency of our breaths. As I began to slowly thrust forward and back, I could feel myself beaming. She gazed up at me with sparkling eyes, her mouth slightly ajar, as if amazed that this was happening.

And just like that, we were fucking. Two complete strangers, grinding together like frantic lovers.

I observed her delight; delight at her own pleasure, delight even upon seeing my own. Carissa grasped my body firmly as if afraid I might escape. She began to occasionally close her eyes with a brief withdrawal into herself to savor the pleasure. Meanwhile, my eyes toured her body, absorbed in the animation of her weighty breasts, the dark wisp of hair between her legs, in contrast to the paleness of her body, her thick, pronounced labia which had begun turning rosy with friction, and the sticky, audible suction of her body as it continued to further lubricate itself in response to my efforts. Then we began to stare fiercely into each other's eyes with a wild determination as we both jerked our hips together in unison, feverish and horny.

If I had to describe the expression that began to subsequently develop on her face, it would simply be the perfect distillation of joy. Her eyes were filled with silent laughter. Her mouth curled at the sides, struggling to maintain composure before it flourished into a fully realized grin that reached ear to ear. We fucked hungrily, facing each other with open hearts and obvious amusement. I grasped at her boobs as they shifted up and down her chest, excited by the movement of her body and the felicity with which she eagerly pumped her hips against mine.