Do It or Lose It

"Well, they've known each other since childhood and for some reason have never hooked up," April started to explain. Gazing at Leah in silence, I nearly choked. Neither of us knew what to say, how to react.

"Oh wow! I never knew that," Samantha said, turning to study the expression on Leah's face and on mine. No doubt she wanted to observe that moment. The moment that we both processed the fact that we were about to see each other naked for the first time. To touch each other's naked bodies for the first time. To have sweaty, raw, passionate sex for the first time with a person we knew in every possible way... except that one. To see there written on our faces the knowledge of something that had been such a long time coming.

"Yeah they, like, know everything about each other and stuff. They've been best friends forever! But I also know everything about them," April continued, exhibiting a devilish amusement. "Including stuff they haven't said to each other, so..." She snickered.

Before I could ponder that comment, Nathan chimed in excitedly. "Have you ever even seen each other naked?" he asked, confusingly.

"Um... no..." I said, noticing that Leah wasn't about to reply on account to her having not appeared to take a single breath since I drew the card. Samantha squealed with delight.

Hell, I still didn't know if Leah would go through with it. I still hadn't convinced myself that she even wanted to. But there was April, running around like a madwoman, making preparations. "Let's give them the couch," she said. "I'll put a towel down, just in case it gets a little messy."

Matt snorted then turned to me. "Dude, if yooou jizz on my couch..." The crudeness of his comment suddenly made everything very real. I had barely thought about getting naked in front of Leah and here he was prompting me to imagine ejaculating on her, in front of everyone. My head was spinning.

April had left the room and returned in a flash with a towel to drape over the couch cushions. "You guys, I got this," she snapped. "Trust me, after all the listening to Leah, after all the bullshit being a good friend and keeping my mouth shut about her and Evan, I'm owed this. I'm the one giving instruction. Y'all gotta get outta my way." She started laughing.

Leah finally moved. She whipped her head around and cast April a cross between a glare and a pleading look. Leah seemed frightened, much as I imagined I looked myself. April ignored her and settled into a comfortable seat, as did the others.

Samantha gritted her teeth sympathetically and couldn't stop staring at us. She seemed like she wanted to ask us a million questions. I could imagine her saying, "Are you scared?" or "Can you believe you're about to fuck?!" or "I can't believe I'm about to watch you two have sex!" I could imagine telling her to please stop talking, stop saying anything at all.

Matt filled the silence. "Shit, we need some popcorn or something." The others laughed.

"Come," April said, finally taking on a sympathetic tone and pointing to the couch. "Come 'ere, baby. It'll be all right." She stared at Leah as if she really wanted to say, "Get your butt over here, you know you want this. I know you want this. Everyone wants to see you finally do this." I started to allow myself to believe that Leah really did want this.

Leah and I glanced at each other, wondering if the other would move. Somehow, we both kind of rose up at the same time. Slowly, we wandered over to the couch.

"So..." April said. "Evan... Ice breaker for you." I eyed her nervously. "Have you ever fantasized about being with Leah before?" Leah didn't quite turn to face me but I noticed her perk up.

"Um..." I mumbled, fumbling to find the right response. "I mean... I guess everyone fantasizes about their friends sooner or later." Everyone in the room seemed to groan at once and I realized that it was ridiculous of me to even assume that a response like that would get me off the hook.

April twisted her mouth to show her displeasure and let out a long, "Mmm-hmm..." Then she turned to Leah and said, "And what about you?" Her frown turned into a knowing smirk.

"Uh... I guess... what he said..." she answered, then let out a small laugh.

"Okay, I see how it is," April grumbled. "That's fine if that's all you want to say." Leah gave another nervous laugh. "In that case, there are other things your mouths can be doing besides spilling the beans." I gulped. "Evan... why don't you start by kissing her. And I don't mean a quick peck. I mean a real, passionate kiss."

"Fuck," I thought. We hadn't ever even kissed before. Or had we? Suddenly a remembered a playful kiss on the cheek, but that was years and years and years ago. Still, it swept in from the mists of time to remind me that it had once been so. I must have blocked the memory due to the sheer pain of longing that it had caused.

I turned to face Leah. Her eyes were like two deep, liquid pools. Something drove me forward. I wanted this.

An intense pang erupted inside me the moment our lips touched. They were soft and warm. I detected a slight tang of red wine. Admittedly, I faltered upon contact as years of emotion became instantly stirred up. I recovered, restoring my efforts with vigor and taking her by surprise. I sensed her receiving my emotion and returning her own. I felt Leah crumbling right in front of me. I inhaled her scent, savored her lips, pressed longingly up against her body, involving my whole being.

As I finally pulled away, I saw us both rattled by the event, trying to regain composure but checking each other's eyes quietly as we both wondered what just happened, if what we felt was shared by the other. I saw her returning my gaze with her own; one that looked crazed, desperate, somehow even senseless.

"I know that look," mumbled April, suddenly shifting positions as if moved to action by the sheer gravity of the situation. We both looked back at her. "Guys," she said, her tone growing serious. "I can't believe, in all this time as best friends I'm the one who still has to tell you this... but... it's time for you two to fuck."

Her final word lodged in my brain and lingered there, burning in the recesses of my mind, conjuring up every fantasy or dream I'd ever had about Leah over the years until they consumed me entirely. Never in a million years had I imagined it would be under these circumstances but there it was, the moment of all moments, staring me in the face.

I slowly turned to face Leah, ready to look her in the eyes for the first time not as a friend but as a soon-to-be lover. With great anticipation, I steered my eyes to meet hers, desperate to receive that look of understanding about what we were about to finally do together.

However, they failed to meet their target.

Leah mumbled, "Excuse me for one sec," then rushed out of the room, staring at the floor in front of her. April became alert, as did I. I felt awkward standing there for the next few minutes, avoiding Samantha's disbelieving stares. Nathan shifted about nervously. I could tell the idea already had him uncomfortably aroused.

However, as the moments crept by, I began to worry about where Leah was. Hell, I wondered if she'd escaped out of a window. I thought: Did she even want to have sex with me? Maybe the idea turned her stomach. Maybe I was tragically alone with my secret desires.

When she finally returned, I felt like I was about to hear some damaging excuse for why she would not go through with it and have my heart broken.

Instead, she came and stood by my side, took a deep breath, and just said, "Sorry" aloud to the room. "Ready." And so, just like that, all my fears of rejection vanished and became instantly replaced with fears of having sex in the open, in front of my friends. Part of me, however, didn't care. If that was the price I had to pay for the thing I had waited for all this time, so be it.

"Okay. Leah, go ahead. Unbutton his shirt and take it off," April instructed her.

I stood ram-rod straight in front of Leah as she quietly stepped forward and reached for my shirt. I watched her fingers negotiating my buttons, albeit with a little extra effort on account of how much they were shaking. She had it unbuttoned and removed quickly before April instructed her to continue and remove my t-shirt. Soon, I stood there bare-chested and taking deep, heaving breaths. I caught a slight whiff of my own cologne evaporating off my chest, a seemingly sarcastic reminder of how routine it had become for me to do everything in my power to woo Leah any time we did anything together.

"Now his belt," April said. "Pants off."

Leah fumbled with my belt buckle and then unzipped my fly. With a series of shimmies, she managed to get my pants down to my feet where I stepped out of them, awkwardly aware of the way my cock flopped about inside my boxers. The movement seemed to catch her eye, drawing her attention momentarily before she quickly distracted herself with the task once again. It was there. She had seen it dangle about. There was no doubt. She removed my socks and stood back up, leaving me nearly naked, with only my boxers remaining.

"Okay..." April said slowly, rising up onto her knees excitedly. "Are you ready to see it, babe?" Leah shot her a look and took a hard swallow. "Why don't you take his boxers down now so you can finally have a look at Evan's penis."

I felt myself becoming rapidly aroused, swelling in my boxers until I hung thick and long down one of the leg holes. Then I felt it begin to rise and I started cursing myself under my breath. Leah directed her attention downward, eying the last piece of clothing on my body with hesitant curiosity. She slowly squatted back down in front of me, then raised her hands to grasp the elastic waistband.

Time seemed to slow down to a crawl.

I watched Leah's eyes as she began to slide the boxers down my thighs, observing with a sense of wonder as my body revealed itself. My underwear crept downward, one centimeter at a time. There were April's eyes. Samantha's. Even Nathan and Matt were glued to my groin.

Then, finally, it happened. My naked penis flopped out and wobbled in front of Leah's face. Half erect, there was no turning back now. I watched as it quickly lengthened the rest of the way, stiffening dramatically in front of everyone's eyes, pulsing at the rate of my heartbeat and gently twitching higher and higher into the air as my shaft became rigid and firm. Leah paused suddenly, her eyes bulging for a moment as she examined my exposed genitals. They focused briefly on the thick, ridged head of my cock, then traveled along my lengthening shaft until it met with my testicles dangling between my legs, and then she looked up to observe my neatly groomed pubic hair.

The room was silent. Everyone watched breathlessly as she projected a sense of quiet wonder and a twinkling of desire. She quickly tugged my boxers down the rest of the way, avoiding the wild swing of my stiffened member, then stood up, her eyes never leaving my cock. Finally, she raised her eyes to mine to offer a soft expression of longing.

"It's okay," laughed April, sensing Leah's hesitation. "You can touch it. Go ahead and caress him." April was all-in on the instructor thing. She wanted it all to herself. Clearly, she'd been waiting for that moment, much as I had. She sought satisfaction and she was going to get it in all the ways of her choosing.

I watched Samantha raise her hand to her mouth, gawking at the two of us, her cheeks and neck flush with deep color. I felt that much more aroused seeing Samantha so aroused by the two of us. Leah reached out and softly grasped my cock where it began to throb in her hand. Together we looked down, watching as it strained painfully, sliding along the inside of her open palm. I could hear Leah breathing deeply. Then I felt her give me a gentle squeeze as if to see how hard I'd become.

I looked up at her face and she quickly responded in kind. As I felt her hand begin sliding back and forth along my shaft, we gazed into each other's eyes. Her bright blue pupils were unsteady, distracted, driven left and right as if by the waves of emotions and scattered thoughts erupting in her mind like dynamite. Yet somehow we still connected there, sharing the same wild realization that at that moment she was actually stroking my fully erect penis.

"Dude, he has a big cock. Look what you've been missing out on all this time!" laughed Matt. Leah turned red and briefly looked away from me.

Samantha gasped. "Oh my god! Matt! You're so-" she didn't finish her sentence. She just resumed her stare that had been fixated on us, full of equal parts shock and wicked amusement. I felt my head spinning. I was lightheaded.

"Okay, that's great. Now, Evan, it's your turn," April continued.

Leah whipped her hand away, leaving my stiffened cock to bounce excitedly in the air. She instantly clammed up, realizing that I was about to undress her. Slowly, I reached out toward her body, carefully watching her eyes. I saw her inhale sharply when I made contact. I struggled a little bit getting her shirt off due to my own nervousness. It bothered me that all my emotions were plainly on display.

Leah had on a simple white bra. I was instantly mesmerized with the deep well between her breasts but I was too afraid to take a proper look. I moved on, slipping down her pants to reveal an equally simple pair of white panties. At the first sign of even the slightest evidence of the faint impression of her labia, I quickly rose back up, my heart racing wildly.

April laughed softly, seemingly giddy at my intense stare at the woman in front of me. "Excited?" she asked me, her sinister grin broadcasting her quiet delight.

"Y-yeah..." I said, unable to offer much more than that basic fragment of honesty.

"I'll bet you are..." she said with a smirk. "When you're ready, I'd like you to begin removing Leah's bra and panties so that the two of you can stand before each other, naked."

As if on cue, triggered by the next step in the slow unfolding of April's wicked plan, Leah began shaking. I took a step forward and slid my hands around her back. She flinched. "Are you okay?" I asked, ready to back away. I suddenly felt terrified at any sign of discomfort. "We don't have to do this if you don't want to. It's just a game."

Leah just stared into my eyes. I remember struggling to understand exactly what she was thinking. It seemed like an eternity of not knowing. However, this strange sort of disappointment seemed to be forming on her face in response to my question. A moment later, everything came full circle. All that we'd been through together, everything we had ever meant to one another, suddenly became crystal clear.

It was as if our friendly little games were always meant to prepare us for their real purpose, in the midst of establishing itself, right there, on that evening.

Leah leaned forward a little, bringing her mouth close to my ear, and spoke softly, grasping for whatever last, flimsy bit of privacy we still had.

She simply said, "Do it or lose it."

I felt my whole insides collapse in a burst of emotion as she pulled away from my ear with a wide, nervous grin. Our eyes connected, communicating the understanding that she'd just, in our own special, private way, told me how much she wanted to proceed. I felt a certain crisis overtake me at that moment. So many years had passed that I'd lived in anguish with the desire for Leah. I'd grown up with her at the center of my adolescent curiosity about the female body, the target of the full blossoming of sexual desire as I grew up and became an adult, the fantasy model by which I had compared all partners I'd come to have ever since, including the very stranger I'd been with recently while Leah lay nearby with someone else that should have been me. However, it had all led to this very moment; the moment when all curiosity would vanish, fantasy and reality would become one. Leah's beautiful, naked body was about to exit my dreams and enrobe itself in living flesh.

I could almost hear her heart thumping in the core of her chest as I moved slowly for the band of her bra, following it all the way to the back. As I gazed at the soft inward slope between her breasts, I could see her trembling with intense emotion. My fingers found the closure and began the brief task of unhooking it. I felt Leah's eyes on me as if desperate to catch my expression upon having my first glimpse of her private places.

My hands were shaking as I pulled the bra forward, letting the cups fall away from her body. My breath stopped as I looked down and watched her breasts gently bounce free and wobble ever so slightly as they settled into place, extending proudly from her chest. They seemed to me to exemplify everything that was sweet and feminine, from their delicate roundedness, to the pale impression of a nearly-extinct tan line, to the vigilant nipples swelling from their tips like two rosy coins. I wanted to bury myself in their warmth, immerse myself in their soft cushioning, then feel the hardness of her excited nipples on my tongue.

Leah gazed at me with a serious, longing expression, reading the suffering on my face and reflecting it back with her own desire. It followed me as I slid down along her body toward the final unknown territory of her body. I craved the opportunity to explore the limits of her private femininity with tenderness and adoration and there it was, obscured by just one small piece of fabric.

I grasped her panties, eye-to-eye with the apex between her thighs. I began to slide them down, slowly, savoring the moment. A sharp line of hair emerged, then more after, until a soft, thin bush blossomed forth. Neatly groomed, it was not too thick, having the appearance of light brown, silky fur. I continued downward until I saw the delicate pink flesh of her labia emerge, much sparser with its finespun, gossamer hair and already quite swollen with erotic excitement. I found myself so entranced with the exquisite lips of her naked pussy that I lost myself for a moment, drowning in its feminine charms.

Suddenly aware of my own fascination and feeling mildly ashamed, I stood up sharply, now eye-to-eye with Leah who seemed like she'd just witnessed the bright skies open up after a long and dreary rainstorm.

"Damn..." I heard Matt say with an authentic sincerity. I couldn't help but laugh softly to myself for having the same reaction.

I'd long since forgotten that April merely asked us to stand there before each other, naked. No, we already wanted to touch one another, to explore our desires, to bring physical expression to our secret urges. I began to slide my hands across her arms, exploring her safe zones at first. Her skin was covered in tiny goosebumps. I felt her hands on my body as mine traveled down the sides of her torso. Little by little, we mapped each other's terrain with an obvious fascination, enthralled in the vast expanses of naked flesh and bashful at each visual encounter with an especially private bit which we still lacked sufficient bravery to examine with especially close attention.

It was April, again, who had to prompt that leap. "Evan, you can touch her elsewhere, too," she said somewhat impatiently. "Don't be afraid to caress Leah's breasts and pussy." As she said this, she hoisted herself up higher on her knees, running her hands over her own body as if instinctively mimicking the contact she wanted so badly to witness.

A magical, sparkling sensation showered through me as I heard her say those words, inviting me to bring my fantasies to life. Leah's hands dropped to her side as if preparing to suffer the pleasure of my curious touches. Growing bolder and more eager, I moved my hands up her stomach toward the undersides of her breasts. I felt her soft, pliable flesh collecting in my hands as they rose up over them, then slid over the tips, feeling her hardened nipples dragging across my palms. There I cupped them gently, assessing their weighty bulk, and then felt them quake briefly as Leah suppressed a sudden laugh.