David and Jess Ch. 03

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 Three:

After a long period of silent contemplation, the two of us got up and decided to rejoin the others. My button-up was stained with strands of cum, so I wrapped it around my waist. I wore a navy blue crew neck t-shirt beneath, though I felt self-conscious because the impression of my chest was somewhat visible against the fabric.

The more in touch I became with my feminine side, the less my chest bothered me. Still, I worried about judgement from other. On the other hand, seeing David's approving glances helped quell those fears. Upon arriving downstairs it seemed as though the party crowd had dissipated significantly. Many had gone home, or found rooms to crash in. Viv and Nick sat on the couch watching adult swim on the big screen.

We took a seat on the couch, soon to be joined by Daniel sat at David's side. Nick and his girlfriend remained on the loveseat, puffing on the last bits of a roach while they browsed social media. They barely seemed to register our return, and it was likely they didn't even notice us leave. I hoped that was the case.

"You two have been gone a while," Daniel observed.

"Err, yeah, I guess," David replied, eyes glue to the screen as he avoided eye-contact. "Things were getting a bit much down here."

"That's an understatement. I came in here a while back to grab a steal a pack from Nick. Him and some dude we're spitroasting Val on the couch."

"Jesus Christ."

"Yeah, I don't think Jesus was anywhere near that mess."

David grinned, letting out a deep chuckle. "What've you been up to?"

"Fuck what I've been up to. What about you? I heard from Alison you've been busy."

"What're you taking about?" He replied, feigning ignorance.

"Ali was drunk as hell, but she said her and Devyn walked in on you getting head from some brunette-" His words cut off as if suddenly coming to a realization. He leaned forward, glancing past David towards me. I avoided meeting his eyes, hoping he would not see me blush.

"She's telling that to everyone, huh?" David asked, gritting his teeth in frustration.

Daniel certainly saw through the facade, though he did not out us. I trusted him to keep our secret. I was just glad Nick didn't find out or I was certain we would never hear the end of it. "Nevermind. You know how she likes to shoot her mouth off. I'll set things straight."

David gave him a grateful look. "I'd appreciate that."

Daniel headed back out of the room, pausing to ruffle my hair as he passed me. "Good on ya Jess," he murmured, loud enough that only I could hear it. His words brought a smile to my lips, and my expression brightened a little. David eyed him with suspicion. I could've sworn I saw hints of jealousy on his face.

Our conversation drew the attention of Nick, who meandered over to our couch. "I do believe I heard my name."

"Daniel was just discussing your exploits," David replied, shifting uncomfortably.

"What about yours? Word is you got caught in the act."

David groaned. "Drop it dude."

"Was she hot?"

It was apparent that he was not about to let this go quietly. David gave in, stealing a meaningful glance my way. "Yeah, she was." His words brought heat to my cheeks as my heart swelled with glee. I did my best to pretend I wasn't interested. It was fortunate Nick was not the observant type.

"I knew it!" Nick exclaimed, pumping his arm victoriously. "Knew we'd make a player out of you. I was a little worried you'd end up an incel like Jessie." He flashed an apologetic grin my way. "No offense dude."

"Don't you have some disgusting acts of depravity to engage in?" I waved him off with a roll of the eyes. Normally I would be more upset, but I was still floating from our romp.

"I believe I do," he replied with a smile, heading to the couch and scooping his girlfriend into his arms. "Drive safe," he shouted as he carried Viv up the stairs.

Finally we were alone again. The adrenaline from the night had finally worn off, leaving an awkward silence as we came to terms with what we had done. Just as I had begun having doubts, David spoke up.

"I don't regret it," he stated decisively, his hand reaching down to grasp mine. "Do you?"

I shook my head. "Not if you didn't."

"Then I'm really glad I came." He winced, once again regretting his unfortunate word choice. "You know what I mean. I'd have hated it if you ended up with another guy."

"That wasn't about to happen," I assured him. The two of us headed to the door, taking our time as we crept passed a slew of drunken seniors.

"Good. I nearly tackled Daniel back there."

"I noticed," I giggled. "You don't have to worry about him. I'm not going anywhere."

David quickly scanned the surroundings before slipping his arm around my waist, pulling me against him. "Good," he whispered, stealing a quick but passionate kiss that left me weak in the knees. I had never realized he could be so assertive, it was a side to him I had rarely seen before. I was the first to leave, but not before receiving a swat to my rear on the way out. I let out a muffled yelp, catching a glimpse of his mischevious grin as the door closed behind me.

My head was in the clouds my entire way home, it was a miracle I didn't miss a turn. I dropped the keys on the kitchen counter, and navigated to my bedroom. I discarded my button-up and jeans, and crawled into bed.

Morning arrived abruptly, welcoming me with a merciless hangover that plagued my whole body. I swung my arm out, slapping at my bedside table as my blaring alarm clock disrupted an otherwise idyllic slumber. I felt incredibly nauseous, and my head was wracked by painful pulsing. Memories from the night before began flooding in. I would have attributed them to a pleasant dream, had I not woken up in the same precum stained panties and crew neck shirt I fell asleep in.

I scrambled groggily out of bed grabbing clothing for school out of my dresser. I peeked into the hall and didn't see anyone. The bathroom was directly across from my own, so it was a short dash. I tossed my dirty clothes down the laundry shoot and hopped in the shower. I did not have long to revel in the hot water, however, as my sister began knocking insistently on the door.

I hopped out, toweling myself off and hurriedly dressing. I had picked a usual pair of skinny jeans, and a loose fit graphic t-shirt. I stepped out to find my sister waiting impatiently at the door.

"Dad figured you were out drinking and he's not happy." I winced, it was bound to happen. I had left my door open, so of course he realized I wasn't there. She leaned in, speaking more quietly this time, "and please stop stealing my clothes." I opened my mouth to object, but she stopped me before I could get a word in. "Don't try it, I know you did."

"I'm sorry," I responded dejectedly.

She sighed, taking pity on me. "I'll figure something out, a birthday present or something, if you really insist on continuing." I beamed happily and headed off to school, ducking past my dad on the way out. The last thing I needed to endure was a twenty minute lecture with a hangover right before school.

The day was mostly uneventful. My classes passed quickly, as my mind was elsewhere. The few times where I was called on to answer or read, I scarcely registered it. There was a passing rumor which caught my attention, about David hooking up at a party. Apparently his girlfriend was pissed, and he had broken up with her that morning.

I had not even realized he was dating someone. I felt a pang of jealousy, though I knew he never got anywhere past kissing with his exes. I was just grateful the rumor was about him and a girl, rather than myself. It wasn't that I wanted to hide things, but they were much simpler that way and I didn't want to cause David any problems.

Lunch hour came along and I found our usual table. Daniel and David were already there, though Nick was strangely missing. I peered around curiously, finally spying him in the back of the room.

"Viv snuck out to join him for lunch," Daniel explained. The dull roar of the cafeteria crowd exacerbated my headache, causing me to wince. "Hangover treating you well?"

"Wonderful. This is why I don't drink."

"I imagine that's not the only reason," Daniel responded in a sly tone. "How's your throat?" He teased. I nearly spit out my water as my face flushed with color. I wondered just how much he knew.

"It's fine, thanks."

"Leave Jess alone," David added, elbowing Daniel playfully.

"Just some light teasing, though I'm sure you've had your fill of that last night." Daniel winced as I kicked in him the shin beneath the table. "Alright, I'll ease up. I just couldn't let you off that easy. Seriously though, I'm happy for you."

As we finished lunch and headed back to the hall, David pulled me aside. "Are you free tonight?"

"I can be, if you drive me there. My dad's out for my ass after sneaking out last night." I paused, suddenly wishing I had worn more feminine clothing. "Can we just stop by mine real quick first? I gotta talk to my sister."

"Sure thing."

That afternoon David was already waiting at the entrance with my ride. His part-time work had afforded him an old beat up Hyundai he bought off his neighbor. It worked well enough for our purposes. I climbed in and we exchanged small talk on the drive over to my house. Fortunately my sister's car was in the driveway.

"I'm sorry about this, I'll try to make it quick."

"Take your time."

I rushed out of the car and inside. It didn't seem like my dad was home, but his work hours tended to be sporadic. If he came home now everything would be ruined. I frantically knocked on the door to my sister's room. She opened the door, peering through the crack curiously.

"What's got you so worked up?"

"You said you could figure something out, right?"

"Are you kidding me? I said for your birthday, that's months off."

"Please I really need this before dad gets back," I begged, with obvious desperation.

"You have a date to get to or something?"

"Yes," I admitted with a groan. My sister was fairly understanding, if prone to teasing. Her and Daniel were the only two souls I trusted with this information.

"Oh, shit. No way."

"I really need your help," I asserted once more.

"Is it a girl?"

I rolled my eyes exaggeratedly. "No."

She gaped openly. "I'll answer all your questions, and you can give me shit for it later, but for the love of God please help me," I pleaded.

We began by digging through a bin of her old clothes. My sister had a good eye for fashion, something I sorely lacked, so I trusted her judgment in selecting my date outfit. "Are you getting laid?" She asked, catching me off guard.

"Is this really necessary?"

"Kind of. It matters if he's gonna see underneath."

"M-maybe, I don't know." Given how our previous encounters had unfolded, it seemed likely. "Probably."

That was not the answer she had been expecting. The two of us regularly shared some of the more intimate details of our lives, so she knew I of my lack of partners and experience. "You move fast," she mumbled, digging through clothes.

She set aside a floral pattern sundress and a set of lacy satin undergarments. As much my sister hated to admit it, I had a similar cup size, so I had a wide variety of choices. She didn't have many shoes my size, but I managed to find a pair of strappy sandals that fit well enough. I stepped into the other room and nervously donned my new outfit. I emerged timidly, my sister gawking at me as I did so.

"Man, fuck you! You look prettier than I do," she exclaimed in her characteristically cass vernacular. "Do you want me to do some quick makeup?"

"Would you? It doesn't have to be anything elaborate."

"Anything for my little sister," she responded, her tone seeming simultaneously serious and humorous. I couldn't help but smile. She worked quickly, sending me over to the mirror when she finished.

I was shocked by my own reflection. The subtle eyeliner and shadow gave a surprising intensity to my steel grey eyes. The bit of contouring made my face more feminine and helped to round out some of my sharper features. It was like looking at an entirely different person.

"Don't start crying or you'll fuck up my hard work," my sister threatened jovially, "and don't forget to grab some spare clothes on your way out."

I embraced her gratefully before grabbing my bag and heading for the door. I did my best to remain composed as I climbed into the car. There was a hanging silence as David openly stared in disbelief. "Jess... Holy shit."

"You can thank my sister later," I replied, my cheeks burning as his hungry gaze ran up and down along the length of my body. "We gotta get going before my dad gets back or I'm in deep shit."

"Right." David snapped back to his senses and began driving us back to his mom's place. His mom was out of town for the week for work, so we had the small apartment complex to ourselves. As he drove, David stole numerous glances over at me, making me even more self-conscious than I already was. It was my first time wearing feminine clothing in public, even if it was only for brief moments to and from the car.

We arrived at the apartment, and David eagerly lead me inside. The door had barely closed behind us before he was all over me. He placed one hand on my breasts, kneading them incredulously. His other hand began at my thigh, sliding up beneath my dress to grab a hold of my ass. I stifled a small moan as he worked me over. The noise only seemed to encourage him as his groping became more fanatic.

"Y-you certainly don't waste any time."

"How could I? I mean, I kind of got a peak that one afternoon, but this is something else." I winced, recalling the awkward position I had been caught in. In one swift motion, David lifted me into his arms eliciting a surprised squeak from me. Despite my size the massive boy carried me effortlessly up the stairs and into his bedroom. He gently laid me down on the bed and positioned himself over me.

He started at my neck, biting and sucking on me until I was left with several sizeable hickies. I shivered at the sensation of him marking me, letting out a pleasant purr as his teeth dug into my flesh. He then began trailing small kisses all the way to my lips. As he worked his tongue into my mouth, his hands were busy below. He ran his fingers up the soft pale flesh of my thighs and up to my ass. He gave my backside a resounding slap, coaxing forth another yelp, which only encouraged him further.

Between my legs the fabric of the dress began to tent. In my current position I had no way of concealing it, much to my chagrin. David noticed it as well, flashing me a mischevious smile. "I know you spent a while on these clothes, but all I want to do is rip them off of you."

"As long as you don't ruin them," I consented nervously. Not needing any further encouragement, David pulled the dress up over my head and tossed it to the side. He looked down at me lustfully, his eyes settling on my panties. My small cock pressed against the delicate satin fabric, begging to be released. David reached down to pull them off, though I stopped him halfway through. He gave me a disappointed look.

"You first, you've got way too much clothing."

David chuckled, stripping off his shirt and tossing it aside. His body was lean and muscular. A small trail of hair lead from his abs and down to the waistband of his pants. Following my gaze, he removed those as well, leaving only his boxers. "Is that good?" I nodded, very pleased with what I saw.

David's hands returned to my panties, tugging them down with avid desire. My small member slipped from beneath the fabric, the tip leaking precum onto my stomach. He grinned widely at the sight, as I hid my face in embarrassment. He pressed himself up between my legs, causing me to straddle him. I could feel his cock pressing against my own through the fabric of his underwear.

Pulling my arms away from my face, David began exploring my mouth once more. He deftly unclasped the front fastening of my bra, and I internally thanked my sister for her foresight in easily removable clothing. He played with my breasts, pinching my nipples between his fingers and eliciting a feminine squeal that surprised even me.

I could not constrain my voice as his hand unexpectedly gripped my cock. "You make such lewd noises," he observed teasingly.

"I-It's no fair, I can't help m-"

My train of thought was soon interrupted as his thumb light massaged the tip lightly. I squirmed beneath him. David worked his way down across my chest, leaving it covered in his marks. He sucked on my nipples, my cock still throbbing in his hand as I writhed in pleasure. "D-David stop, I-I'm going to-"

"Cum for me sweetheart," he commanded in a deep tone, silencing my stammering. His words sent me over my limit and my body obeyed, as if submitting to his will. I convulsed with a mewling cry, my cock spraying cum across my stomach, and chest. I lay beneath him, drenched in my own cum as I gasped breathlessly.

"David that was..."

"We're not done yet."

With a gentle but commanding strength, he took me by the waist and flipped me over. I squeaked in shock as David pulled me up towards him by the hips, bending me to his will. He began spreading my ass, teasing my hole with his finger. Using my own cum as lubricant, he started to press inside. I squealed at the strange sensation as he worked his finger deeper into my ass. I had never explored that part of myself, though I was admittedly curious in the past.

David pulled out briefly, only to stick a second finger in. I whimpered with need as he thrust in and out, loosening my hole in preparation for his eagerly throbbing member. Before long he discarded his boxers and positioned himself behind me. He leaned down, whispering into my ear. "Can I put it in?" I nodded, nervous but resolute in my decision. "Brace yourself baby, this might hurt a bit."

A white hot pain shot through my insides as he inserted the tip. I had no idea how I had managed to take him into my throat, as his thick phallus pressed slowly into my tight ass. I cried out in pain, causing David to hesitate. "Do you need me to stop?" I shook my head furiously, and began pressing my hips back into him to show my determination. Slowly but surely I took him further, my body forming to the shape of his member as it became more accustomed.

"Almost there hun," he coached me, slipping the full length of his manhood into me. As he pressed all the way in I could feel him rubbing against my prostate. I moaned lasciviously. The feeling was surreal, a mix of pain and pleasure beyond measure. Cum leaked from my flaccid cock onto the bed below. "I'm gonna start moving," he warned me before pulling back out. The second thrust was easier, as my body welcomed him with enthusiasm.

David's thrusts were slow and steady, as he was clearly concerned about my well-being. I wanted more, I wanted him to ravish me. I whimpered slightly below him as I felt overcome with selfish desire. "Do you need me to stop?" He asked worriedly.

"H-harder," I begged with a primal desperation, my mind lost in a haze. "Fuck me harder."