Author’s Note: This story is completely fictional and did not happen. All names of characters are fictional and were made up. Please do not copy and plagiarize my work.

This story was requested by my dear friend John Connors. The celeb, themes and back story were all his choice. Enjoy!

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Miami Beach, Florida

Early sunrise was enough to disturb sleep with the curtains pulled back from across the room. Sunday had come and gone, along with what could only be described as a slight hangover from a fun weekend. Drinking was not something everyone could indulge themselves in on a Sunday evening. As James awoke slowly in his bed, he let out a loud yawn and stretched his arms out. He could never have spent the weekend partying like this last year, but the joys of life had to be celebrated now. Pulling back the blankets, the world slid into focus when his bare feet touched the white tiled floor below. A short trip to the bathroom was next in order after glancing at the digital clock on the night stand. 1:12 in the afternoon told James that he had overslept.

He brushed his fingers through his short dark hair. A slight five o’ clock shadow had darkened on his face after skipping two days of shaving. With a sigh, he closed the bathroom door and turned the faucet to run cold water. Life had changed a great deal for him in the past year now that he was out of the house and trying to make the best of his situation. Life had dealt him a difficult hand of cards. James considered himself to be lucky when remembering where he was two years ago. Living past the age of twenty-one was a miracle for him. Two months ago, James was still in the hospital recovering from a brain tumor. Upon first diagnosis, the chance of survival was slim. His case went viral on the internet due to a short career as a dedicated Overwatch player.

Two months later, donations soared. James had his online friends and connections to thank for fundraisers and raising awareness of his case. Still stuck in a hospital bed during that time, he underwent two surgeries. The hair was slowly growing back on his head, but James still covered his head with a black beanie hat. From all the money raised in donations, his medical procedure was a success. The news had come and gone by the time he returned to playing online. Internet trends had changed over time, and his story was likely forgotten at this point. James did not want to draw much attention to himself. To be able to travel from his home in North Carolina down to Florida for this event was already a treat in itself. Lucky for James, he only had a small Youtube following and another manageable community on Twitch, which he did not announce was the reason for his weekend hiatus.

The event ended after three days of cosplay events. James could at least hang his head on attending the full weekend, but yesterday made it all a blur of memories. On the final day, he encountered someone that he had only dreamed of meeting in person. Jessica Nigri had a booth, signing autographs over photo prints. James was surprised he had not found her at the convention the previous two days. He may have overlooked her after becoming distracted by the number of costumed Warcraft cosplayers. With a quick introduction, Jessica noted there was something familiar about James’ appearance. All he had to do was say his Twitch username, and Jessica remembered. She had shared his story and fundraiser via social media, but was curious why he did not have a booth for himself. James tried to shake off just how much his story had caught the attention of gaming communities online.

At the end of the day, he was not a masterful player. The following he gained online was due to his charisma and personality while streaming. Years prior, James had streamed other games as a prominent Starcraft player. Jessica had caught his gaze down to her heavy cleavage. She sat at the booth in a black tank top sporting the yellow Batman emblem. Her natural eye color was green, something James noticed right away. After seeing many of her cosplay shoots online, he assumed she had brown eyes. Her long platinum blonde hair was fixed up with that signature combover, revealing part of her right temple. After their brief conversation at the event, Jessica invited James for a night of partying. This was far from her first time in Miami, as she made it clear when the evening hours rolled through. South Beach became a fun place after the sun went out and stars lit up the sky.

Only once had James been drunk in his life prior to this weekend. He remembered throwing up and experiencing a hangover back then, but today was different. At least he had memory of Jessica and her friends encouraging him to take another shot from the bar. James could not recall the club they went to, but he could still hear those booming synth beats playing in the back of his head. Jessica had a small entourage. Two female companions and a tall man who was her bodyguard. Through the night, James learned that the girls were photographers, but he could not remember their names at all. Only one woman from the night was worth remembering by name. By the time James stepped into the Shower, he was grinning ear to ear as he wondered about Jessica. With his eyes closed, he envisioned her goofy grin and wearing that same black top. He knew she caught his wandering eyes glancing down at her cleavage more than once.

After stepping out of the Shower and drying his skinny body, James felt his face. He considered shaving, but did not want to scratch his face up with cheap razors. At least, that’s what he assumed the hotel provided. Putting on a pair of underwear, he noticed his hard cock was fully erect. The result of thinking about Jessica in the Shower. It was a wonder he did not pleasure himself in the art of Masturbation while the water was sprinkling across his skin. Through his life, James only had a few experiences with girlfriends, but nothing beyond holding hands and kissing. Now at twenty-two years of age, he felt more nervous than ever regarding his virginity. Aside from the events of last night, one thing he could not shake was the odd feeling he had when Jessica flirted with him. They did not step onto the dance floor, but instead sat side by side at the bar. At one point, her busty chest brushed up against his left arm.

Some things were impossible for him to remember between drink after drink, but not that. James could not shake the feelings he had for Jessica. Partying with her was something of a dream come true, let alone meeting her in person. Stepping out of the bedroom, James walked into the living room of his hotel suite. The interior design was made up of white furniture to match the wall color. Over on the glass coffee table, his laptop sat next to a red backpack he had brought along with him. After checking in on Friday, James did not bother unpacking much, aside from some clothes and other necessities. He had not even gotten dressed yet. Still walking around in his white pair of underwear, cock bulging up as he searched for his phone. The last thing he remembered was Jessica and her bodyguard walking him up to his room.

Wandering out of the living room, James finally saw the phone sitting on the nightstand next to his black beanie hat. That was where he should have looked first. Before grabbing it, he glanced at the floor to see his pair of white shorts. James did not remember taking off his shorts or shirt last night, so someone must have offered a helping hand. Could Jessica have taken his shirt off? That wondered only maintained the erection in his underwear. Biting his lower lip, James giggled to himself and finally grabbed the phone. He tapped the screen with his left hand to see a few text message notifications. There was one from his mother, checking to see if he was safe during the trip. Another text was from his brother, also checking on him. Finally, the one that caught his attention was an unknown number.

‘Call me when you get up’

That could only be one person, James wondered to himself. Taking a deep breath, he could feel a hard adrenaline rush. His heartbeat began to rush. In a panic, James dropped the phone onto the bed. God help him, that had to be the Cosplay Queen demanding a phone call. Rushing back to the bathroom, there was a wooden chair sitting in the corner where room service had delivered his fresh clean clothes. Picking through three folded up shirts, James chose his black State of Decay 2 shirt and slipped it on. Now that he was properly dressed, the time had come to make that special phone call. Doubts were beginning to sneak into his mind. What if it was a prank from an old friend? The answer to his question would soon come. James exhaled a deep sigh, then pressed the dial button across the screen. The dialing tone greeted his right ear after lifting it.

“Hello? James, right?”

An unmistakable voice called out on the other end. His heartbeat was racing again upon replying.

“Yeah! Jessica, that you?”

“The one and only!”

He laughed at her response.

“How did you get my number?”

Jessica giggled at his question before answering.

“You gave it to me, silly! We talked about playing Overwatch last night, remember?”

“Oh… yeah… I forgot about that. I guess I had too many drinks last night.”

“You sounded pretty fine last night!”

At least she could not see him blushing, James wondered to himself. Unable to remember a conversation regarding games, he was worried that he may have embarrassed himself last night.

“If you’re up for it, mind if I come over and hang out? We didn’t get to spend much time alone yesterday.”

“No, I don’t mind at all. I’d Love to get together!”

“Great, I’ll be over in an hour.”

The phone clicked, hanging up. Left standing there in his thoughts, James slowly smiled to himself. How could he turn down a day of hanging out with Jessica Nigri? Though he had nervous feelings inside, James was at least confident about this afternoon. With an hour’s time, he decided to grab the hotel service phone from the night stand. It was time to call room service and let someone else tidy up the suite. James paced out of the bedroom, hurrying back into the living room and grabbing his laptop. Lucky for him, the erection was no longer poking up in his shorts, but he knew it would return. The way Jessica talked to him on the phone, he was left wondering for a moment if she was toying with him. The last thing he could do for now was admit his virgin status to her. He went to fetch his beanie hat, slipping it over his head to hide the surgical scars behind his right ear.

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3 HOURS LATER

Heat came through the evening hours, burning hotter than the waking moments of the afternoon. This Florida weather was something else to James, regardless if it was summer time or not. Before Jessica arrived, he took a short trip on the balcony from the sliding glass door. Even with shade above, the heat was still too much for him. He slid the door closed and turned on the air conditioner before her arrival. When her knuckles knocked on the door, James tried to fight off the sudden nervous tension that built up inside him. Jessica greeted him with a friendly smile. She came over in a black jacket covering her body, but James noticed a light blue pair of high heels. In her hands, she carried a black bag in her hands. After asking her about the contents, Jessica explained that she brought over a camera and tripod.

There was another reason she wanted to stop by besides him. Jessica explained to James that she wanted to use his hotel suite as a backdrop for a glamour modelling photo shoot. The pictures were for her FansOnly page online. She joked that she needed a new shoot ‘for the members of Titty City’. Those words made James excited, but nothing could beat the moment when Jessica unbuttoned her black jacket. She pulled it off, dropping the attire to the floor and standing firm in her latest outfit. James’ lower lip fell upon witnessing her stand there in a skimpy outfit. Light blue socks extended up to her thighs. A lacy blue thong covered her snatch with slight see-through garments at the front. James’ eyes had already enlarged at that sight alone. A silk blue ribbon was attached to the front of the thong, and the side ribbons extended over her hips.

His eyes noticed the pink folds of her womanhood, visible from the sheer see-through fabric of her thong. Jessica turned around, revealing her buttocks and showing him the lacy blue ribbon tied at the top. Her lingerie outfit was complete with a sheer push-up bra shoving her busty breasts up. The bra was also in that light blue color, complete with matching shoulder straps like her thong. Jessica’s perky nipples were visible through the see-through fabric. Standing there in amazement at her outfit, James only told her how gorgeous she looked. He had leaned over, trying to contain the instant erection that poked up in the front of his shorts. All Jessica did was giggle at his reaction. Little could James have guessed that he would be behind a camera working on a glamour shoot today.

He had no experience with handling such cameras, but Jessica must have chosen him for a reason. At least that was what he wondered to himself when they prepared the tripod. She claimed that his hotel suite had the perfect scenery to use in the background. Jessica quickly made use of the furniture for numerous poses. She instructed James to set up the tripod across from the couch first. The camera itself was a large black metal video recorder, but set for snapping photos and still shots. James explained to Jessica that he had no experience with such a device. All she did was shake her head and tell him what buttons he would need to press. With the tripod, there was little concern of shaky shots. With slight practice, James learned how to zoom in with the camera, and then the living room began to light up with flashes.

An hour passed between the first photo shoot. After enough poses and teasing expressions on her face, Jessica got up off the couch. James remembered seeing her photo shoots a few years ago. He held off on confessing to her that he had masturbated to them in the past. Those memories helped, as he knew what sort of shots Jessica wanted. All while she teased him with the words ‘Titty City’. That came when she sat up on the couch and moved her hands over the straps of her bra, teasing him with a slight bounce. Jessica took a moment to fix her hair up before they set up the next photo session. She arrived with her signature combover to the side, revealing the right side of her head. A few locks dangled from both sides, but the rest of her platinum blonde hair was curled up in a ponytail.

James had commented that her hair was flawless. Jessica moved to the white lounge chair, bending over for some proper booty shots. That was the cue for James to unmount the camera from the tripod and use it in his own hands. He was confident that he would not mess up and shake the camera. When Jessica turned around, she grinned and jiggled her breasts. He did not need to be told where to guide the lens of the camera, capturing several shots of her perfect enhanced tits. “What do you plan on calling this shoot? Blue Monday?”, his question caused Jessica to laugh. She teased James again after stepping out of her high heels. Jumping up and down, her tits jiggled and shook. The photo session continued out of the living room and to the large kitchen bar. All James could do was follow her through the lens of the camera as she climbed up and dangled her lovely legs from the white marble counter.

A break was needed after the third series of photos. James called room service, ordering what was essentially dinner at this time of day. He did not realize that he had skipped breakfast and had not eaten all day. Jessica did not bother putting her jacket back on. Together, she shared a pizza with him. It was funny to watch her sit there at the dinner table, hovering piece after piece above her big tits between bites. They shared cans of Pepsi supplied by room service, all while sharing a conversation about live streaming video games. Jessica was willing to hear about his experiences on Twitch. For a moment, James missed playing Starcraft competitively online. Jessica teased him about the possibility of a Kerrigan cosplay outfit, assuming a new Starcraft game may come out in the future. After eating, James was willing to pick the camera back up and resume their photo session. Hours had passed throughout the day, but so far he was having fun with Jessica.

“I think you’ve snapped enough photos to make up an entire set. All that is left is to do a bit of filming. Think you can handle that?”

Standing face to face with James, she grinned. Their eyes met, but only for a brief few seconds. He glanced down at her cleavage for what felt like the hundredth time today.

“Someone is a little distracted right now!”

That opinion only made James blush. His cheeks turned red as he bit his lower lip, flashing the front row of his teeth. Jessica took the camera from him, rolling her eyes. Tensing up, James curled his toes. He could feel cold sweat beginning to form across his forehead. He watched her take a few steps back, placing the camera down on the kitchen counter. Jessica knew the effect she had on him. She moved her hands over her breasts, jiggling them in the lacy blue bra.

“I guess I should go on and tell you this. Jessica, I’m not the kind of guy you think I am.”

She stopped and slid her hands onto her hips. James took a deep breath, then he finally blurted out the truth.

“I’m a virgin.”

With a gasp, Jessica gave an exaggerated look. He recognized that silly face, knowing it from watching her videos in the past. She then burst out laughing loudly.

“Oh god, I knew it! I knew there was something funny about you! And here I was, thinking you were about to tell me you had a girlfriend.”

Quirking her eyebrows up, Jessica giggled.

“As if there is anything else that was going to stop you from constantly looking at these.”

Her hands moved back to her bra, shoving those tits together for a slight jiggle. She did not appear bothered about his confession at all, so James let out a sigh of relief. He was almost mesmerized by her shaking boobs alone. Jessica stepped a bit closer to him.

“James, just relax. I didn’t come here just to take pictures.”

Giggling, she placed her left hand on his shoulder and then reached out with her right. He felt her snag the beanie hat from his head, and now his short hair was revealed to her. Since she took an interest in his head, James spoke about it.

“I don’t have enough hair to hide my scars from surgery. Now you know what the hat was for.”

She noticed the scar through his short hair. James could feel Jessica’s fingertips brushing across his head and then her big green eyes leered at him. She breathed into his face, parting her lips as she shoved her busty chest up against him. He threw his arms around her and pushed his lips against hers. James had some experience with kissing, but this was something else entirely. To be able to kiss Jessica Nigri tenderly, she had helped ignite feelings inside him he had never felt before. They continued to kiss as Jessica slid her right hand down and grabbed the bulge in his shorts. James abruptly stepped back, breaking their lips aside as she began to giggle.

“You’re really nervous about this huh?”

Nodding at her, he swallowed his breath.

“Yeah, I’ve never done anything like this before, and it’s not just that. With you, that makes it pretty-“

Cutting him off, Jessica spoke over his words.

“Special?”

There was nothing else for James to add in words. He watched her grin, then shake her fists up and down in excitement.

“You should be excited, I know I am! I get to be your first. I always dreamed about doing this with one of my fans.”