David and Jess Ch. 01

This story is entirely fictitious. All names and likenesses are fabricated, and all characters depicted are over the age of 18.

This story is multiple pages / chapters, and involves elements of romance and erotica.

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Chapter One:

"Have you ever thought about guys?" David inquired, sparking a tattered green bic lighter.

"Have I ever thought about guys?" I echoed, eyeing him sideways as he exhaled a billowing cloud of smoke. He passed the pipe my way, his massive hands dwarfing my own as well as the small glass fixture.

I was not a small guy by any means, measuring just under six foot. David, on the other hand, towered above me at nearly 6'8". He had bright blue eyes that seemed as if they could pierce right down to your soul, and lean but rugged features. The guy certainly stood out in a crowd. During highschool he kept his bright brown hair buzzed short, and had just begun sprouting whiskers. I was somewhat jealous, as I could not grow facial hair for the life of me. "You know..." He trailed off, scratching his chin uncomfortably.

"I haven't got a fucking clue," I admitted, taking a long draw on the pipe. Since entering highschool smoking weed had become a regular vice, and our favorite pastime.

David's face flushed slightly, somewhat uncharacteristic for the stoic giant. "Are you into guys?" He asked more blatantly.

I sputtered a cough, brushing a brunette lock from my face. This was by far the last thing I expected out of the other boy. "I... Uhm... No," I lied through my teeth. I stole a glance back at him, his expression seemed to conceal a hint of disappointment. Probably just my imagination.

Sexuality wasn't a common topic between the two of us, save for the rare exchange of gossip regarding sexual conquests, and from what I had heard the larger boy was strictly straight. "Why?" I asked, wondering if some new rumor about me that had surfaced.

I had never dated a girl, so there were a number of salacious rumors floating through school about my preference in partners. Most of them were baseless, as I had never had a boyfriend either. It wasn't that I had no interest in either side, my tastes were just a bit complicated. I did my damnest to keep those tastes hidden.

"Eh, forget I mentioned it," he replied dismissively, and that was the end of that conversation. We quickly changed the subject, discussing new releases of video games and griping over recent homework assignment. The rest of the week passed in the blink of an eye, and it was the weekend before I knew it.

I finished my daily three mile jog and headed to the shower, taking a moment to look myself over in the mirror before hopping in. I had always been the fat kid growing up. Whether it was because I liked food too much, or because I had an unfortunate metabolism, it's hard to say. Once I hit highschool I began exercising religiously and sharply cut my caloric intake. In the first year I lost nearly a hundred pounds. Now in my senior year, I had developed a modest amount of lean muscle.

Despite all this hard work I could not help but grimace at the sight of my own body. The fat that has collected on my chest stubbornly refused to leave despite my best efforts. I was often teased about it, leading to a developing complex and the nickname "c-cup" by some of the jocks. Swimming was a dreaded event in school, as I often received remarks about my feminine shape and lack of body hair.

Finishing with my shower, I headed to the basement to play 'Mortal Kombat: Deadly Alliance' on the shitty little CRT set up next to the couch. My family rarely came down, making it a small sanctuary where I rarely had to worry about disturbances. A half hour into my session I heard a clamouring upstairs, which was strange, as no one was supposed to be home that day.

My sister must have had a similar thought, as I heard her and her boyfriend heading to her room. Only a few moments passed before I started to hear the creak of the bed. Her room was right above where most of the consoles were located, and the floorboards did little to muffle sound.

I found myself getting flustered from the noises above me. They probably did not think I was going to be home today, a fair assessment as I often disappeared to my friends houses on the weekend. I turned off the television, sitting in silence as I listened to the gasps and moans above. The coarse fabric of my sweatpants began to tent.

Deciding to indulge myself, I headed to the laundry bin across the room. I dug through dryer filled with a myriad of clothes from myself, my sister, and my father. I selected a skirt, tanktop, and ribboned cotton panties from the bin before heading back to the couch beneath my sister's rooms. I quickly donned the garments.

I took a moment to admire myself. Somehow I felt less self-conscious about my chest and feminine aspects. As I grew older, stealing my sister's clothing became a regular indulgence. The fitted tanktop did well to accentuate my hourglass waistline, and the sizeable fat deposits on my chest seemed less out of place. I did not have particularly wide hips, but regular exercise had lead to a well toned rear and legs. I lifted the hem of the skirt, revealing my modest erection peeping from the top of the panties.

Occasionally the subject of comparing size would crop up within my group of friends, and it was always one I avoided. "I'm just average," I would tell them vaguely, refusing to divulge any further information. I was only three or so inches at my peak, and when flaccid I could scarecly call it a manhood at all, as it looked more like a clit. The one instance where my friends decided to compare visually, I quickly dismissed myself from the room.

When I was dressed in my sister clothes, however, I did not have the same envy. In such feminine clothing my small cock did not seem so shameful. If anything I felt it added to my more feminine appeal. I laid on the couch, running my hands along the soft pale skin of my thighs and up to my pelvis. I began to stroke my already throbbing member in time to the passionate noises emanating from upstairs. My other hand slipped beneath the fabric of my tanktop, slowly working across my toned abdominal, and up to my chest.

I started to gently massage my breasts, pinching my nipple between two fingers and eliciting a gasp. I usually remained adamantly silent during masturbation sessions, but something about crossdressing coaxed forth my voice. My voice had never truly broken as I advanced through puberty, leaving me sounding more like a husky voiced girl than a young man.

I could tell that things were reaching a climax above me as the intensity of their exchange increased. My own gasps and moans echoed my sister's as I closed my eyes, imagining myself in her place. I pressed my hips up, assuming a submissive position as I came closer to orgasm. Thick white ropes of liquid sprayed across my chest, covering me from stomach to chin in my own cum and staining my pilfered outfit.

I lowered my hips with gasping breaths. Running my finger along my face, I wiped off a string of cum that had fallen just below my lips. I plunged the finger deep into my mouth, savoring the bitter, salty flavor. It was at that moment that I leaned up from the couch and found my gaze locked with David, who stood in shock at the bottom of the stairs.

I had no idea when he got there. For the giant lanky kid that he was, he was strangely light-footed. An awkward silence hung in the air as we stared at one another in utter disbelief. Coming to my senses, I yanked the blanket off the back of the couch and covered myself. I opened my mouth, hoping to explain myself, but no words came out. He practically lept up the stairs, but not before I got a peak at the bulge in his jeans.

We did not talk for the rest of the weekend. I spent the entire time panicking about what happened. I assumed he let himself in, though I had not heard the door open. My sister had a tendency to leave the door unlocked, and David and I had a level of familiarity where surprise visits were not uncommon.

How long had he been standing there? How much had he seen? No matter the answer it was too much. The image of his wide eyes staring at my cum soaked visage was forever burned into my memory. I was sure it was the same for him. I also could not forget the protruding fabric of his pants, and our previous conversation sprang to mind. I briefly entertained the idea that he liked what he saw, though it seemed outlandish. In reality, I was dreading our next encounter.

Monday arrived, and I was grateful that we shared few classes that day. Unfortunately we still had lunch at the same time, so there was no way to avoid him altogether. At the very least there would be others at the table, and it seemed unlikely that soft-spoken David would bring up a subject like that in company.

David was already at our usual table next to Nick and Daniel. Nick and Daniel nodded in my direction and resumed their conversation about a rather busty girl Nick had his eye on. Even though Nick had a girlfriend, he had a nack for sleeping around. For a brief moment my eyes met with David's before he quickly looked away, his pale complexion becoming highlighted with hues of crimson. I took my seat at the opposite end of the table, my eyes glued to my tray as I ate.

"Yo David are you alright?" Nick asked, placing a hand to his forehead. "You're burning up man. You sick or something?"

David flinched at the contact, his gaze darting over to me for a moment as I peaked up from my meal. "Y-yeah, just didn't sleep too well last night or something." He brushed away Nick's hand. "I'm fine, don't worry about it."

"Nick's right, you look awful dude," Daniel added.

"I'm fine," David snapped in return, wincing slightly at his tone. "I'm just tired. I'm gonna go lay down in the nurse's office," he mumbled, leaving his tray behind.

"Jessie you go check on him, we'll take care of the trays," Daniel noted. He must have noticed my wistful stare as David left the cafeteria. Daniel had a keen eye, and tended to see right through me.

With a measure of reluctance I headed into the hall after him. The guy must've booked it to the nurse's office because the hallway was already empty by the time I got out. I took my time heading after him, anxiety building with each step I took. I placed my hand on the doorknob, taking several deep breaths to prepare myself.

"Are you going in?" A voice behind my asked curiously. I whipped around to face nurse Westheimer, my heart leaping in to my throat. "David is laying down for a moment, seems like he had a mild panic attack."

"Is it alright if I go in?" I asked uncertainly.

"Did you two have a fight or something?"

"N-nothing like that." I could feel myself getting flustered and turned away towards to the door.

"Ah. I was just going to get some coffee. You head on in," she offered, though I doubted that was her original intention. It seemed as if she was giving us space, having sensed the nature of our conflict.

I mumbled a thank you under my breath and headed inside, closing the door behind me. David lay on the farthest bed on the room, a damp cloth covering his eyes and forehead. I could not tell if he was conscious, as he did not react to the door, nor my footsteps as I approached.

I stood at the side of the bed, watching the rhythmic rise and fall of his broad chest. He wore a nondescript white t-shirt that displayed the thick muscular build of his biceps and forearms. I found myself tempted to reach forth and touch them, though I managed to restrain myself. Unsure of how to begin, I lightly cleared my throat. David flinched, reaching up to pull the cold compress from his forehead. He recoiled as he realized it was not the nurse at the side of his bed.

"H-hey," I began uncertainly, taking a seat at the chair next to the bed. "Are you alright?" He sat up and gave an affirming nod, though he continued to do his best avoiding eye contact. "A-are we alright?" I added.

"We're alright," he assented softly.

"Listen... about what happened. Can we just forget about it?" I pleaded hopefully.

"That's easier said that done," he murmured in return.

"How much did you see?"

"I saw enough..."

I could feel tears forming at the corner of my eyes. "I'm sorry, I didn't mean to. I don't want this to-"

"You didn't do anything wrong," He interjected, cutting me off. He glanced over, sensing the distress in my voice. "I said we're okay, right?"

"It doesn't feel that way," I grumbled, feeling embarrassed. I had come to comfort him, but somehow the roles had been reversed.

"I don't get it," he began with a sigh, "but I won't hold it against you."

"Why not?" I asked, my head buried in my hands.

David frowned, pursing his lips. "Jessie, it really wasn't that bad, I mean it kind of makes sense. It's not like I hated it."

I peaked up at him curiously. "What do you mean?"

"You've always had a girlish figure, and you wear kinda androgynous clothing," he explained, wringing his hands together nervously. "You don't act like most guys either, except for maybe the excessive video games."

I grimaced, but he wasn't wrong. I had never felt like other guys, and I did my best to maintain a gender neutral appearance because it seemed to suit me better. After I had begun losing weight I grew my hair out to shoulder length to match my new image. Around the same time I had begun wearing skinny jeans, though I opted to wear looser tops to conceal my chest. I had several piercings in either ear, as well as one on my eyebrow and lip, though I couldn't wear those at school. From an objective standpoint I probably looked more like an edgy tomboy than an actual boy.

"I meant the other thing."

"Nevermind," he dismissed, turning to study the wall awkwardly.

"You said you didn't hate it."

"I know what I said," he groaned.

My curiosity got the best of me, and I stood up, leaning over the bed and into his field of view. "Why didn't you hate it?"

Clearly flustered by the close proximity, David scooted back a little. "Aren't you the one who said to forget it ever happened."

"Now I am asking you to tell me."

"It was kinda hot, alright?" He blurted out, "It looked good on you."

"The clothes or the cum?" The question came tumbling out. I was mortified at my own words.

David gawked at me in pure shock. "Jesus Jessie," he responded, managing a chuckle despite everything.

"Heh, sorry," I laughed weakly.

An awkward silence persisted excruciatingly before David broke the tension. "Is that... something you do often?"

I returned to the seat at the side of the bed, my legs feeling unsteady beneath me. "Yeah, sometimes." I ran my hand through my hair, a nervous habit of mine. "It's not something I'm proud of, no one else knows."

"I won't tell anyone," he assured me. The tension began to ease as we discussed the elephant in the room.

"Thank you," I mumbled timidly.

"Is it sexual? Are you trans or something? I don't really know anything about this kind of stuff." My discomfort must've been apparent, as he quickly added, "we don't gotta talk about this if you don't want to though."

"It's alright... I just feel more like myself in those clothes," I admitted. "I'd be lying if I said there wasn't a sexual component though. I don't know why I do it." I felt a tear cascade down my cheek. "I've tried to stop, I-I don't want to be like this."

David swung his legs over to the side of the bed, turning to face me. He reached out, brushing away the tear with a surprising tenderness. "It's alright."

Those simple words broke the walls I had carefully constructed over so many years. A riptide of emotions burst forth within me. I collapsed into his lap, bawling my eyes out while he silently stroked my hair. After a few minutes of crying I managed to calm down and catch my breath. I apologized copiously as I dried my tears.

"Don't worry about it," he consoled me. A small smile tugged at the corner of his lips. "Somehow you're even cute when you cry."

I peered up at the towering boy in a mix of confusion and embarrassment. As I opened my mouth to object he leaned down, taking my chin in his hand and placing his lips against my own. I pressed back into him eagerly without a second thought, lost in the heat of the moment. I stood up from my seat, as the difference in height made the positioning awkward. David had no objects as he pulled me against his body with a surprising passion.

David's tongue began to work its way into my mouth with a gentle insistence. I accepted him with enthusiasm, our tongues writhing against one another. It was my first real kiss save for a few instances in my early years, though I hardly counted those. David seemed experienced enough, as he deftly explored the inside of mouth with his tongue. Suddenly David gripped me from behind, pulling me onto his lap. I let out an involuntary yelp as he did so, the ease of which he handled me was both shocking and arousing. I enjoyed how small and helpless I felt compared to his massive stature.

Clearly I wasn't the only one excited, as I could feel the impression of his growing excitement against my stomach. I pulled back from the kiss, a string of saliva falling from between our mouths as I breathlessly panted. David snapped back to his senses and pulled his hands away from my ass, which he realized he had been groping hungrily. It was at that time that the door swung inwards without warning. Nurse Westheimer's eyes widened, bewildered at the compromising position she found us in.

"I said you could use the room, though this isn't quite what I meant."

I scrambled off of David and back into the chair, the both of us laying out hands across our laps to hide the evidence of our carnal shame. "I'll give you two a minute and then you have to get to class."

"T-thank you," I squeaked awkwardly, my cheeks burning intensely. Once I managed to calm down, I mumbled a hasty goodbye to both David and the nurse, and proceeded to dart into the hallway. My heart hammered relentlessly against my chest the whole way to class.