Chapter 19

The image of himself from when he looked in a floor to ceiling size mirror burned itself into Gabe’s psyche. A beautiful girl, her wavy almost collar length hair all brushed out and shiny, her makeup perfect for some on screen starlet in a teen movie ready for the camera, not a blemish to be seen.

Her large chest pushing out the tight lycra long sleeve turtleneck and the front of her pinafore dress. The girl’s purple shaded hosed legs came out from the mid thigh length skirt of her dress, ending in cute black ballet flats. The semi dressed up girl looked shocked by her own appearance and all of it left him in a daze to the point he was not sure when or how he got in line to board the flight back to Nevada.

Blinking heavily, his heavily mascara covered lashes fluttered as he looked around and then down at the boarding pass in his hand. A small thing like changing his nails seemed to transform his normal hands into something feminine. Turning his hand over, letting the light in the room reflect off his pink lightly sparkle-covered nails, the sluggishness of his mind almost let his mind drift off again.

‘What is wrong with me?’ The coherent thought came through and suddenly reminded him that if he had been so lost in thought he might not have been doing a good job of keeping up the Gabriella act.

Unzipping his purse he found more cosmetics in the small white thing than had been there that morning, the presence of a lip plumping gloss told him where it all came from. Pulling out the compact mirror he gazed at his reflection once more, everything still looking to be in place.

Between doing this same action twice in the line for security and once more now it reinforced exactly what Gabe was trying to sell. People like Bryan who often looked over at who he thought was a pretty teen girl, only saw someone who was trying to make sure they looked their best or perhaps were infatuated with their own appearance. An impression that followed along with the act perfectly, but one that would haunt him when he thought about how others saw him as a vapid girl instead of a man of intellect.

Boarding the plane Gabriel made eye-contact with a thirty something year old flight attendant, her outfit far more modest and reasonable than the dream he had the previous night. Though she was still quite pretty and it hinted not just of a dream, but now a small private fantasy that seemed to build in his sluggish mind. As he moved down the aisle, trying to find his seat, he imagined himself as an attendant.

Looking at the number letter combination and comparing it to what he saw on his ticket, he imagined an older, more elegant version of himself collecting these tickets from everyone as he walked past them. Moving further and further into the depth of the aircraft he found himself at the very last row, with a stranger at the window seat already getting themselves comfortable. He wasn’t sure where the odd thoughts came from, nor did he have the mental bandwidth to explore it.

With a mental sigh he sat in the middle seat, placing his small white quilted purse under the seat in front of him. No one ever wanted the middle seat, but the one benefit of not being a large man was it made such places not nearly as bad. Things didn’t feel so bad, nothing felt like much to him at the moment and made him think that he just hadn’t gotten a true restful night of sleep. He wondered to himself if he could get his hands on a prescription for whatever medications Jenn had given him.

Unfortunately, no matter how many anti-anxiety pills he took, it could not stop the world itself from conspiring to make his life miserable, they only seemed to dull the pain, like the world was trying to kill him by degrees. In this case the blonde eighteen year-old that has been tormenting him this entire weekend, Bryan, practically dived into the seat next to him with a toothy smile on his face.

“Hey there Gabby.” Bryan said, feeling slightly giddy to be sitting next to the girl. One might think fate itself was conspiring to put these two together, but the truth was far from that. As Bryan had been standing in line, he had gotten a peek at Gabby’s boarding pass and was able to trade with one of the other students on the trip to sit next to her. They were more than happy to trade seats, no one wanted to really sit by the bathrooms in chairs that didn’t even recline.

“Bryan Wilcox.” Gabe said with a sigh in his voice, acknowledging the boy’s presence.

Hearing Gabby say his name in a breathy voice brought butterflies to Bryan’s stomach. Other students knew his last name was normal, they were in classes together and some teachers took attendance with full names. Her knowing his last name meant she had to have asked someone, or so he reckoned.

In reality, Gabe was one of those teachers that took attendance and had called the boy by his full name more than a few times, just as he had when he sent Bryan off to the office when he became a distraction. Right now the disguised man had done his best to keep the irritation and weariness out of his voice, but on this trip he didn't seem to have the power to send him away like he did in school

“I was thinking…” he started to say before the short five foot five girl got to her feet.

“I’m…” Gabe pointed to the side where the plane’s bathrooms were, the word for what he wanted not coming to his mind. Normally his limited vocabulary was a falsehood used to sell the idea he didn’t have mastery of the English language or that the girl had more air between her ears than brains, but his mind was not reacting well to the meds, scrambling his ability to speak.

“Restroom? Ah, yeah.” Bryan stood to get out of her way before taking his seat.

The flight was almost done boarding so Gabe had a little time to release the pressure on his bladder and mostly not have to sit with the godawful boy and make conversation. Putting his hand on the bathroom’s door he stopped when something caught his eye.

On the small counter in the back was a small box with what he knew were individual size drinks. Grabbing a few bottles before getting behind the door of the bathroom, Gabe quickly opened the cap of the tiny bottle and drained its alcoholic contents down his throat. A sweet, cheap brand of whiskey, and unluckily, the first of them was a fireball which burned his throat. A karmic punishment for trying to escape back into the very habits that began his, at least recent, troubles.

The dress wearing man wasn’t feeling like he needed the drink, or at least he didn’t till he saw them, but the taste on his tongue, the burning down his throat hit him just right to quell a craving he didn’t even know he had. “Phew, so much better.” A genuine smile crossed his pink glossy lips as he looked at the bottle.

Cracking open the second one he drained its contents as well before having to deal with the struggles of relieving oneself wearing the feminine outfit he had on. Pulling up the skirts, pulling down the pantyhose and panties. ‘Nothing is allowed to be simple.’ he told himself, happy to have a few drinks in him now that he knew who would be his travel companions on the flight. A stranger that looked as if they would keep to themselves and a pain in the ass class clown.

As Gabe enjoyed the few moments of peace and quiet before the flight took off, Maria sat down just across from the man she was growing to admire. This particular plane sat eight seats per row with two aisles splitting the seats into groupings of three, two and three. Very efficient for seating the most number of passengers, but as she looked across the aisle to her supervisor, she giggled watching the much bigger man struggle to fit into the economy seat. Efficiency not always translating to comfort.

“Do you fly much?” she asked, trying to stifle the laughter escaping her lips.

“Yes'' Sam squirmed. “Laugh it up my dear.” He finally found the seat-belt and pulled it free to buckle himself in place. “I do, but you try flying when you’re six-foot five. You should have seen me back in college when I still worked out. Whenever we flew out for a game, I'd need to pay for two seats or else I'd be elbowing people left and right.”

“Yes, I recall you telling the students about playing football in college. You must have lived quite the thrilling life in college.” Maria leaned closer as she imagined the large man in full gear, holding his helmet under his arms as cheerleaders flocked to his side.

Reaching his hand up, Samuel knocked on the side of his head. “Oh, outside of the occasional head-trauma it was quite boring actually. I spent so much time either studying or working out that I sadly missed many of the parties.”

The dozen or so cheerleaders vanished from Maria’s mental image of Sam Banks’s fictional persona. She pursed her lips in curiosity as she decided to pass the time before take-off by digging into his past. “No cheerleader girlfriend?”

The question made the man laugh, a pleasant rumble that shook his chest. “No girlfriend at all. Not that I didn't have friends who were girls.” As an adult he could look back and see obvious signs of interest in some girls that he missed when younger. “We often trained with some of the female athletes at the college and they were lots…” Sam unconsciously drew out the word. “of fun. But again, by the time I was done with homework and exercise, I barely had the energy to eat dinner.”

Sam saw the pretty Hispanic woman open her mouth to ask another question, but he’d answered questions like this a couple times before, after people learned about his dating life. “And before you ask, no I didn’t date the cheer captain back in high school either. I went to an all-boys private school back then.”

“My dear, Samuel…” Maria smirked, showing just a hint of her white teeth with her smile as she said his proper given name. “You wouldn’t by chance be…?” A man like him being single and going to a boys school made Maria wonder if she had misread the signals she’d been picking up during the trip.

“Gay?” He shook his head slightly. “No, I’m your standard, red blooded straight male. Not that I have anything against gay folk. Sorry, I know that sounds defensive, I just get asked that more than I would like.” Rolling his shoulders, relaxed his body and began to slouch into his seat, thankful he at least had an aisle seat for his arm. “I know how hard it can be in school for folks like that and I don't want any of our students feeling like they need to be in the closet while I'm in charge.”

The conversation continued, Maria following the lead of her boss as she relaxed, getting comfortable in her seat. The questions about relationships flipping on its head as he started to ask probing questions. The two laughed as they exchanged various embarrassing stories about life back in the nineties.

Emerging from the bathroom, only after an attendant knocked on the door, telling Gabe he needed to get seated before the plane took off, the petite crossdresser stumbled through the aisles.

Gabe attempted to slide past the blonde boy as best as he could, trying to keep his skirt back in place. Small as he was, the confines of the seats were smaller and he couldn’t help it when his leg pressed against and rubbed on Bryan’s jeans. The experience of pantyhose was a new one still to him, other than loving when he could rub his fingers over a girl’s leg that was wearing them. So the touch sent a small shiver down his spine before he could take his seat.

Soon as the pretty latina sat back down next to him, Bryan turned his full attention back to her. “Hey, so what I was trying to say…” the teen started to say before being interrupted once again.

“Shhhh.” Gabriel knew exactly what he was going to tell him, but some of his own actions surprised him as he touched his index finger to the boy’s lips as he shushed him. “For the flight I’m going to…” His mind blanked once more, the word he was fishing for coming to him first in his mother’s native tongue. “Dormir.”

Feeling her touch, and seeing the slow flutter of her lashes as she paused before saying something in Spanish had Bryan’s brain feel like it had been hijacked. What happened the night before with Sarah had been amazing and gave him real confidence instead of just something he faked most of the time.

He internalized it along with how he had acted like a coward when Gabby had tried to suck his cock and was going to shoot his shot with the girl. But that casual touch to his lips had him pause long enough that he saw her get comfortable and close her eyes like she was going to sleep. The word dormir, clicking to place, knowing she meant sleep. “Umm, okay, sweet dreams.” He touched the girl's shoulder, giving it a squeeze, the uncertainty in him settling when she didn’t pull away from his touch.

He was a bit saddened as he had sat for a few minutes now patiently waiting to try and talk to the pretty girl he’d been flirting with the past few days. They’d barely met, but already he felt like a connection was being made between them.

It brought a smile to his face though when Gabby seemed to drift off to sleep almost instantly, the preflight safety announcement didn’t make her stir a bit and much to his delight her head drifted off to the side to rest on his shoulder. Bryan held his breath as he tried to keep the girl in place as he raised the arm rest between them and slipped his arm around her shoulder. A soft, almost gentle snore coming from her as the simple lean into him turned into something more akin to cuddling when her hand moved to rest almost lovely on his chest.

The pair stayed that way for a good while anyone walking by getting a glimpse at what appeared to be a couple enjoying one another's company. Bryan mostly keeping himself occupied by listening to his ipod touch, content to just keep himself still. That was until the pretty thing attached to him shifted slightly mumbling, her hand sliding down his chest to fall lightly on the crotch of his jeans. Looking down, his heart beating heavily in his chest he gazed on her little fingers laying right across where his member was. Bryan’s hormones and instincts he couldn’t control took the sight as a hint and blood redirected its way to his groin.

Still he didn’t dare move, afraid if he did Gabby would realize that he was getting a hard on just from the slight contact. Bryan had worked up the moment he could be with the girl in his head so much after that moment at the museum that he just couldn't help himself. So he just sat there, one arm around her as her hand rested atop of his growing dick.

A pair of girls in the same group a row ahead of them had taken notice of the new girl being so comfortable with the boy. By now rumors of Gabriella’s antics on the trip had gotten to all the students. It seemed to them the girl hardly had any standards, just a slut. Now she was draped over Bryan Wilcox, a boy that had a reputation for himself for being the biggest horn-dog at the school. No self-respecting girl would dare give him that kind of attention if they cared at all for their reputation. One of them talked about how they would warn Gabby about him, so they didn’t end up like Millissa Carter.

Back when he was a sophomore, Bryan had chatted up the girl and before Millissa knew it, everyone knew she was the easiest girl at school. The thing was, with how the new girl acted, they didn’t see a reason to step in. Bryan’s reputation mixed with hers made it seem like the perfect couple, at least till one of them inevitably cheated and moved on.

It was around then that Gabe started to actually stir, his mostly **** mind feeling something warm pressing into his hand, causing him to reflexively close his hand around it, gripping it as his unconsciousness started to change to consciousness. Raising his head off Bryan’s shoulder he smacked his lips together twice attempting to come to his senses.

To Bryan though, Gabby had lightly taken hold of his now hard cock and once again had started to flutter her long lashes at him while making kissy faces at him, or so he interrupted it. Accepting she had been more awake than he thought, Bryan used his arm that he had around the girl to pull her closer and press his lips to hers. The moment it happened it felt like fireworks sparked in his mind, her grip on his dick grew tighter. While her body was stiff her mouth slid open allowing him to slide his tongue first across her perfectly kissable pink lips and into her mouth.

It was the first time Gabe had ever been kissed. The short man had enough game to have kissed a handful of women, but he was always the one to initiate. The one that started a kiss, never the one on the receiving side. The small distinction from being the kisser, and being kissed meant a lot when he was the one being kissed as he awoke like some princess from a fairy tale. He felt at the mercy of the male that was holding him tight.

He could feel his tongue invading his mouth. The feminized man’s mind foggy from just waking up and a cocktail of things running through his system with the **** and medication he couldn’t find in him to put up an ounce of resistance in his surprised state.

The kiss only lasted a few moments, Bryan instantly wanting to press his lips to hers once more. Things had happened instantly and now he found himself out of breath just like the girl he held, each gazing upon one another like, locked in that moment, giving anyone looking upon them the impression of a pair of lovebirds. Moving his other hand to the girl’s hip the boy desperately wanted to pull her into his lap to continue their makeout session. While his mind wished they were back at the hotel or in his own bedroom.

Gabe’s body pressed into the other male’s body, his arms holding him close, a seatbelt assisting to keep him in place the feminine man froze, clenching all of his muscles as another pair of lips were pressed into his own. The mixture of both **** and the medication in his system had made it easy to fall asleep, but it really only made his critical thinking skills that much worse. “I aww, bathroom.” he said in a small, almost pleading voice. Gabe’s surprise the hands around him let go.

Unbuckling himself, Gabe got to his feet and almost instantly plopped back down, his slumber on the plane causing one of his legs to fall asleep as well. Not willing to stay here he stumbled to his feet to try and return to the aisle, the smallest bit of turbulence swept him off his feet and he had soon fallen backwards onto Bryan’s lap. Attempting to grab the seat for balance only left the dress wearing man grasping onto Bryan. “Oh!” The startled cry came out as he felt the teens hands once more upon his body as the two collided.

‘Plump, pink, kissable… fuckable lips.’ Bryan thought as he leaned forward as he pulled the girl down into him, initiating another kiss. His eyes had focused on those lips as she pretended to fall into him. One arm wrapped around her waist to help press their bodies together, the other reaching up to run through her hair, fingertips gently rubbing her scalp as he turned his head and slightly opened his mouth as they kissed.

He was positive he could hear her groan in pleasure into his mouth as she shivered in delight. Unable to help himself he pushed his hips up, feeling his enlarged member press into his jeans and against her silky purple nylon covered leg. The hand on her lower back shifted down to her supply thigh feeling her leg and pressing it into his lap and swollen cock. Once he thought the trip was going to be boring, but right now he was thrilled to have come on the trip as he slid his tongue up against Gabby’s. Her pushing up against his tongue almost like the beautiful latina was trying to use her own to push his out of her mouth.

The person sharing their row glanced over to the teenagers doing their best to share a seat and make out like they were in a movie theater. They could see passion there between the two, the girl squirming against her man and him making sure their bodies had as much contact as they could. They were sure a flight attendant would put an end to that kind of behavior, but it was none of their business, so they turned away to look out the window.In fact,

“Mhmm!” Gabriel gasped for air as he pulled back from Bryan, a trail of saliva pulling out between them before falling away. Being kissed, feeling what he felt in the boy’s pants made his stomach roll, but he still found himself feeling flush. “No.” Gabe whispered aloud when the boy tried to pull him back in for round three. “B-bathroom.” he ended up whispering to Bryan’s ear as he tried to assert himself, but unable to bring more than a small voice forward.

Taking a deep breath Bryan nodded excitedly with a joyous grin on his face, not paying any mind to anyone else around him at that moment. The combination of what Gabby had offered to do, tried to do to him before and how she practically started to give him a hand job over his pants right there in the seat, he was more than ready for the next step. After all, he had done something similar to this just the other night, making this the best trip of his life. Standing up he took the hispanic girl’s hand and started to lead her to the bathroom.

They had gone a few feet, standing in front of the cramped area, it only occurred to Gabe at that moment to pull his hand away. “Where are you going?”

Hearing the teasing question, Bryan leaned in close, putting his hand on the dark haired girl’s shoulder. “Joining the mile high club with you, beautiful.”

Confusion and fear went through Gabriel, shaking his head he looked into the taller boy’s eyes. “No.” Taking half a step back he put his hand on the door handle. “No.” he repeated himself.

A look of bewilderment went across Bryan’s face. “No?” he asked, his expression changing into something harder. “What do you mean no? You just… fuck.” He shifted from trying to clarify to cursing to himself. “Fucking cocktease.” Turning abruptly to his side he took the few steps he needed to sit down in his seat, doing so hard enough that the other row's occupant took notice.

‘She acts like she is going to rub one out on me, tells me to go to the bathroom with her and then tells me no?’ He clenched his jaw, grinding his teeth against one another. ‘What a bit… no, fuck. She is still mad about before… Gabby is showing me that not only could have had fun with her yesterday, but also had a sure thing today and I… fuck.’

While Bryan tried to make sense of the situation, Gabe slid into the bathroom feeling his stomach churn and a sense of wrongness about him. He didn’t actually need to use the restroom, so he just sat there on the toilet seat, his mind giving him information in drips and drabs.’What am I going to do? He kissed me and I grabbed his… I felt his… no, no. It was more than likely his phone, I was grabbing his phone.’

Gabriel was still more than a bit out of it, making it difficult to hold onto his thoughts even as traumatic as they could be, but thankfully with the medication in his system he had an extra layer of defense. “What would Gabby do?” he found himself asking, no answers coming to him.

His mind dreamily slipped back into the moment. “It must have been a big phone though… no! Snap out of it! You’re not that kind of woman… I’m not any kind of woman, I’m a man!” But his own words sounded hollow when he could see the large chested teen model in the bathroom mirror. Not a single ounce of masculinity there to confirm what he had said. “No, I… I’m Gabby. I’m a seventeen year old girl going home with her mother.” He repeated his mantra several times. What had just happened had been… a thing, but he couldn’t let it ruin everything. ‘I’m Gabriella Grace DeLeon.’ He was inches from the finish line and was not going to fall short.

“Gabriella Grace DeLeon is a girl. I am a girl. I like fashion and make-up and music and… and boys… like Bryan? No, not like Bryan. But if Gabby likes boys… which boys does she like?” Gabe did not enjoy the possible answers he seemed to be given. ‘Bryan is a disgusting pervert. Jake… seemed to have his own baggage with Sarah. Evans? I barely know him… and yet I gave him a lap dance… Banks? Ugh no, he’s like, way too old for her… me. Why am I even thinking about this?’

With no answers to his questions and finding himself once more lost in his own reflection as if he was a bird, he realized he ultimately had to return to his seat. Gabriel stood before the blonde teen, holding the seat to steady themselves as the plane hit a small patch of turbulence. “We aren’t… going to talk about what happened.” Gabe said, meaning any of his interactions with that problematic boy.

Pressing his lips together in a line, Bryan nodded, looking up to the girl standing next to his seat. “If you answer a question first.” When Bryan saw her nod he pressed on, already knowing the answer to his question after looking it up. “How do you say beautiful in Spanish?”

“Hermosa, why?” Gabe asked with a slight shake of his head.

Standing up and stepping into the aisle to let the girl take her seat, Bryan smiled. “I will do whatever you say hermosa.”

The teenager was more than a little taller than him, and standing this close to Bryan after the two had kissed and being called beautiful made Gabriel feel a spike of shame. There were so many people around that he wanted to run and hide. On the plane though there was nowhere to go, so he looked at the floor, his cheeks burning as he got back into his seat. When Bryan sat down Gabe glanced at him, when their eyes met he turned away quickly. ‘This flight can’t be over soon enough.’