David and Jess Ch. 04

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 Four:

I stared in disbelief for a moment, frozen in place as my mind reeled. Surely I must have misheard. Jess's hips pressed back against me insistently, driving me deeper inside. My doubts were quickly dispelled. "Please David," she pleaded with carnal desperation, "I-I want you to make me scream." Jess peaked over her shoulder, her head thrust to the covers with her ass pressed all the way to my pelvis. Her face was a bright red, and her gaze appeared distant, eyes swimming with lust. "I want you to use me."

Hearing her talk dirty caused me to swell within her. Her insides tensed in response. The girl facedown in my bed was so far from the now distant image of the boy I grew up with. Never in my life would I have imagined myself to be in this position.

I met Jessie in early middle school. He was a hefty kid, but as the years passed he quickly shed the weight. As he did I found myself marveling at his body.

He had pale delicate skin, his waist cinching in a slight hourglass figure. Though he tried his best to hide it, his chest was remarkable, even for a girl. In the brief moments where I had stolen glimpses I found it difficult to restrain myself. I did my best not to look, for both his sake and my own. His face never developed the usual masculine attributes of his peers, remaining largely hairless and soft featured. During our early years in highschool he started growing out his hair, as if accepting his feminine visage.

It wasn't long before I found myself crushing on him. I started accepting any girl who came my way, hoping to banish him from my mind. Nothing worked, however, as none of the girls I met could live up to his standard. I began questioning my sexuality, and exposed myself to other possibilities. Gay porn did little for me. On rare occasion I was able to find videos with a feminine bottom, reminiscent of Jessie. Pretty soon, such videos were the only way for me to get off.

Providence intervened that fateful day. As I entered his house that afternoon I could hear the echo of passionate cries. I cannot say why, but I felt compelled to flee to the basement, rather than leaving and coming back later. Nothing could have prepared me for what I found. I heard faint gasping as I began my descent, this time from downstairs. I cautiously peeked around the corner.

Jessie was on his back, hips pressed in the air as he masturbated. I found myself entranced, eyes glued to the events unfolding in front of me. He was wearing a pencil skirt pulled up above his hips, exposing sheer cotton panties beneath. I felt something stir within me. I knew I should leave but I couldn't. My hand unconsciously moved to massage my growing erection through my pants.

Jessie clutched his chest, massaging the sizeable mounds beneath his fuscia tanktop as his movements became more frantic. He ran his thumb and forefinger across the small length of his shaft. I had guessed that he would be small, but his manhood paled in comparison to my own. It looked so much more sleek and feminine. With a final gasp he erupted, painting his body with cum. He collapsed, panting heavily.

In a further act of uncharacteristic depravity, he began sucking his own cum from his hand. I leaned in closer for a better look, completely stricken by the image before me. The floor creaked beneath my feet, drawing his attention up. My fate was sealed the moment those steel grey eyes locked with my own. With no clue how to respond, I fled back up the stairs. I drove home, my head lost in a lustful fog. I spent just about every free moment during the remainder of that weekend pleasuring myself to that memory.

Though I do not know what possessed me to do so, I was grateful for whatever gave me the courage to make my move that following Monday. In my most outstanding moment of idiocy and bravery, I pulled him in for a kiss, and then on to my lap. In that moment I knew I had to make him mine. Nothing compared to the feeling of him. I made a mental note to break up with my current girlfriend as soon as possible.

Just as I was about to call her later that afternoon, Nick invited me to one of his house-parties. Usually I avoided them at all costs, knowing the types of things that went on there. I wasn't the type to engage in gratuitous anonymous sex. This time however, I saw it as an opportunity to move things forward with Jessie. I was elated to see him come down those stairs, though the night did not progress quite as I had imagined.

For once I was grateful for Vivienne's teasing nature when I saw his face light up at the effeminate nickname. In the past he often bristled at the mention of it. Over time he had come to accept it more, and now it almost seemed as if he enjoyed it. I did my best to refrain in the past, as I did not want to upset him. I also had more selfish motivations, as I thought if I began addressing him that way I would not be able to see him just another guy. He never quite explained if he wanted to be seen as a girl or not. I think he probably didn't know himself. I made another mental note, eager to see that expression again.

While I had mentally prepared myself to make a move on him, I did not expect the roles to be reversed. As the teenage orgy began to unfold around us I found him staring at me with a rather lewd expression, the alcohol splashing his cheeks in bright pink hues. Looking down at him now, it was very easy to see him as a girl. In fact, it was becoming difficult not to. Regardless of gender, Jess was the sole object of my lust and affection from that point on.

By that point I had begun subconsciously viewing and addressing Jess as a girl. she continued to catch me off guard, as she began massaging my cock in full view of the room. Even though the others were largely occupied themselves, it still sent my heart racing. I abandoned my restraint, toting her upstairs into a more private location. The atmosphere was heavy and prurient in the solitude of that room.

She possessed a salacious drive that night, as she devoured my cock with shocking fervor. The sight of her on her knees was remnant of so many of my fantasies, I almost thought I had to be imaging it. As her eyes locked with mine, I could no longer hold back. I took a handful of her hair, gripping it lightly as I thrust deep into her throat. She moaned with delight as I did so, appearing to revel in her submission.

This afternoon was no different. I could tell she enjoyed me taking a more dominant role, as she stared up at me with wide and hopeful eyes. How could I not oblige her? My grip on her tightened and I plunged the full length of my member into her. She screamed out passionately, gripping the sheets in tight handfuls. I did not afford her a moments respite as I continued to thrust. She moaned and squealed in rhythm with my pounding. At that moment I was glad I didn't know my neighbors.

I reached beneath, taking her cock from behind. I could feel it stiffen at my touch. Her body shook with pleasure as I stroked her in time with my prodding. Her voice became more intense as I did so. I pulled out, much to her dismay. She looked back at me with an adorable but frustrated pout, panting heavily in the brief pause in action. I flipped her over on her back in one swift motion. She squeaked in surprise, a delighted smile pulling at the corner of her lips upon being so easily manhandled. I could feel myself getting close, and wanted to prolong our embrace just a little longer.

The new arrangement also provided a much improved view of her face and body. I resumed my position inside of her, coaxing a delightful moan from those delicate pink lips. I leaned forward, grabbing her wrists and pinning them to the headboard. She seemed so small beneath me, her wrists easily fitting within the grip of a single hand. I teased inside of her with slow, deliberate thrusts. Her breasts and cock jiggled with each motion.

In such a position she could not hide her embarrassment, her body and expression were both fully exposed for my pleasure. I reached forward with my spare hand, taking hold of her member. It was so slight and delicate that I only needed my thumb and two fingers to stroke the length of her. I maintained my grip while I fucked her ass, pinning her with one hand and pleasuring her with the other. She struggled to retain her composure as I ravished her without mercy.

I knew I couldn't last much longer, and it seemed like neither could she. "Now be a good girl and cum for me," I leaned in and whispered. Her body responded dutifully to my command. I closed my hand around her, engulfing her petite cock in my sizeable fist. I could feel hot liquid burst into my palm, leaking between my fingers. I continued to grip her, stimulating her softening cock with her own ejaculate. Her body quaked in response.

Her flush and flustered expression, her taught but soft body, her unrestrained and feminine voice. I knew I could no longer hold back. I released her wrists, slipping my arm to her waist as I pulled her body against me with one final heave. I came deep inside, clutching her body against my own. Cum leaked down the length of my phallus, dripping from her ass as I filled her to the brim. I held inside her for a moment, maintaining the position as we shared a fiery kiss.

After a quick shower, the remainder of the afternoon was spent spooning and lounging on the sofa. Evening turned to night and I urged Jess to gather her dress and other belongings. She pouted the whole time, reluctant to leave as she begged me to let her stay. It was definitely tempting. I yearned for more time with her above all else. I knew that once she went home it was unlikely we would get another chance for privacy for a while.

Unfortunately, her father was already upset over the night she snuck out to Nick's party. I was willing to bet he was pretty pissed about her doing it again this afternoon. Her father was a good guy, but I didn't want to get on his bad side, especially if I wanted to go anywhere near Jess in the future. It took every last bit of willpower I had to tell her she couldn't stay. The drive home was filled with a bitter sweet silence.

I pulled up to her house, her father already waiting impatiently in the doorframe. I gave her hand a tight squeeze, not daring to sneak a kiss or hug despite my overwhelming urge. She had enough to deal with without her father raising further questions about the nature of our relationship.

"Thank you," she said, hesitating at the car door, "for everything. Really." I felt like shit leaving her like that.

"Anything for you," I responded, a lump rising in my throat.

As she was leaving she whispered one final farewell. "I'll see you soon... I love you."

My eyes went wide and I found myself speechless. I stammered helplessly, entirely caught off guard. Before I had a chance to respond the door closed behind her. She turned briefly as she headed to the door, her face flush red in the glow of the headlights, and a nervous smile on her lips. My heart hammered harder than it had any time in the past week, which was saying something given all we had been through.

Of course I saw Jess at school the next few days, but we rarely had much time together. Her hickies were still obvious against her pale complexion, and she turned meek whenever the subject was approached. Despite Nick's insistent digging, she didn't divulge any information besides that her dad had noticed the mark and was incredibly pissed. I felt a little bad, but strangely proud of my handiwork.

Her dad had her on full lockdown, enforcing a strict curfew at all times out of school. I enjoyed the brief periods we spent together, though we were never truly alone. Unfortunately her father had also confiscated her phone, which severed the last line of private communication we had together. I carried the weight of the words I could not say for weeks.

One afternoon, I received a text. I nearly tumbled from my bed in shock as I saw her name at the top of my screen. Her contact was a little outdated however, as it still read 'Jessie'. I would have to change that later, the name seemed so ill fitting now.

'Hey you!' Her text read.

'Hey yourself. Been too fucking long.'

'Tell me about it. My dad is starting to ease up a bit... still won't let me out after school.'

'At least we can text now. Felt like I was going crazy.'

'Kind your fault you know. Dad was super pissed bout the hickies. Least he didn't check my bag.'

'I had to mark what's mine.' I paused, panic setting in momentarily. 'He didn't know it was me right?'

'Thank fuck no.'

We spent that whole night, and just about every night from that point on texting back and forth without fail. The year was dragging on painfully slow without her company, but Thanksgiving break was nearly here. After what felt like an eternity, Jess's father finally relented and lifted the ban on her after school activities, albeit with some restrictions.

'When do I get to see you next?' I texted, feeling hopeful.

'School bonfire?'

'Not exactly the quiet venue I had in mind.'

'We'll make due.'

Our highschool had a number of unusual traditions and events. One of those was the yearly bonfire, which took place a few days before break. A massive pile of kindling was assembled in the courtyard behind the school and everyone attended to observe the towering inferno. All things considered, it seemed like a dull event. Students found ways to add their own fun, sneaking in alcohol or drugs past the handful of monitors who enforced school rules.

The day of the bonfire arrived and I found myself with an excited but nervous energy. I could not hold still all through classes. The few times I saw Jess that day she seemed similarly excited as well. After school I met her outside the side doors, managing to catch her alone for the first time in a while. I escorted her on the short walk to her house, exchanging small talk along the way. Neither of us had spoken much about our sexual exchange, nor the bombshell 'I love you' she had dropped as she left.

Despite this, our relationship had obviously changed. I had dumped my now ex-girlfriend the day after Nick's party, and had seen no one since. Though we had not discussed it, in my mind we were exclusive. I was fairly certain she felt the same. As we drifted farther from school I slipped my hand down, taking a hold of hers. She jumped a little at the sudden contact, but didn't pull away. I ran my thumb across her hand. It was so slender, smooth, and delicate.

Jess's face was bright red as I did so, which was humorous given how bold and shameless she had been that night when she begged for me. I felt myself getting excited and quickly banished the thought. This was not the time to be thinking about that. We reached the door, but before she could open it I lightly grabbed her and pressed her to the wall.

She let out a small surprised yelp. I brushed a lock of hair from her face, my hand lingering on her neck. Jess leaned in eagerly, expecting my advance. Of course I obliged her. Our kiss started slow, but began increasing in intensity as our passions flared. It had been our first kiss in weeks. She gasped softly as I pressed my tongue into her mouth.

The sound of knocking on glass caused us both to jump. Jess gave a mortified squeak as she saw her sister in the window adjacent to the door.

"Fuck," I stated. I had rushed things, too excited to wait until we had a more private moment. "Did she know about us?"

Jess grimaced. "She knows now."

"Fuck," I repeated. "I'm so sorry Jess."

"Don't worry about it," she consoled sheepishly. "She knew I had a date with a guy, but I was a little ambiguous about the details."

With a few calming breaths we headed inside. Jess's sister was waiting eagerly in the hall, smiling impishly at the two of us.

"Brother in law!" She greeted me, exacerbating my embarrassment. "I have to say, I wasn't expecting it to be David. You two are cute together though."

"Sara, please," Jess begged.

"Please nothing, you promised details and welched on our deal. Did you at least enjoy my efforts David?"

My face turned bright red as I recalled how stunning Jess had been after her small makeover. Both the sight and feeling of her in that dress was still firmly burned into my mind. "Yeah," I admitted begrudgingly.

She beamed proudly. "I hope you're not planning on sweeping her off for the night. Dad will keep her locked in the house till she's thirty if you do."

"Nothing like that, there's an event after school so we were just stopping here first.'

"Oh! The bonfire?" Jess's sister Sara was just a little older than us, and had gone to our school before graduating. I nodded. A mischievous grin began to spread on her lips. "You two are seniors now." I knew where this was going, rolling my shoulders uncomfortably. There was a strange tradition among the seniors. Though the school had discouraged it, they did little to enforce any restrictions.

"I don't think-"

"Can I borrow some more clothes?" Jess interjected, her face filled with chagrin.

Her sister was just as surprised as I was. An awkward silence persisted as we both stared at her in shock. A while back a group of seniors started this long running joke of crossdressing at the bonfire. It was a strange tradition, and while many had gone through this right of passage, I had doubted that Jess would take part. Even though she had begun to embraced her feminine side recently, she had spent her whole school career insistently asserting to her peers that she was in fact male.

"You're going to crossdress at the bonfire?" I asked incredulously.