Chapter 8

Theodore Hamilton, Theo to everyone but his family, was your friendly, though typical college jock. On the varsity basketball team at the local university, he was good enough to make the team, but not great enough for an athletic scholarship. He didn’t see this as a mark of shame, easygoing as he was, but his Aunt Bethany was insistent that he had to work doubly hard on his academic pursuits, regardless of how affluent his family was. The woman was not someone to give anybody a free ride, and didn’t make an exception for her nephew, so while she paid Theo’s tuition, this didn’t mean he could party through his college years for free. This was how he found himself working at a particular counter establishment in a particular mall food court.

“Do you guys have tacos?” The question came from a pretty blonde-haired, blue-eyed girl, startling the boy from his blank stare and boredom. Her infectious smile was enough to bring a little joy to an otherwise dreary day.

“Umm…no…” Theo checked his surroundings, just to make sure he didn’t accidentally clock in at the wrong restaurant. “This is a pizza place. It’s an easy mistake to make though.” The dozens of photos of pepperoni topped slices, said otherwise. “I can fold a pizza in half if that helps.” he joked, trying to soothe the disappointment that brought a pout to her kissable lips.

Evidently it worked, and as her face lit up, she asked, “Like a pizza taco? I’ve never had one of those before. Can you make me a pizza taco?”

“Sure!” he replied. A slice, folded or otherwise, wound run the same price so he told the girl, “That’ll be three dollars, and fifty cents.”

“Can it be a free pizza taco?” Clearly subtlety wasn’t her strong suit.

The giant of a boy chuckled, then rattle the tip jar to quickly guestimate its contents. The sound seemed sufficient, so he said, “It can be a free taco pizza if you eat it with me on the break I’m about to take.”

“Okay!” she answered excitedly.

“Why don’t you have a seat, and after I get my manager to come cover, I’ll bring it to you. How does that sound? My name is Theo, by the way.” The athlete seemed to have charm to spare.

“That sounds great, Theo!” It was easy for the boy to think she was excited to meet him, but really the girl was more excited for free food. Almost as an afterthought, she added, “Oh yeah, my name is Emery.”

Over the meal the two enjoyed pleasant conversation ranging from Theo’s burgeoning athletic career to Emery’s wild theories on the secret lives of house cats. The clock ticking down to the despicable time when his return to work was required, the boy decided to take his shot. “So Emery, are you doing anything Friday night?”

“Oh, I’ve got a date with my boyfriend.” It was like a knife to the heart. For a moment, Theo almost lost himself in a puddle of despair when he noticed the disappointed look on her gorgeous face.

“Do you not like your boyfriend, or something?” he asked bluntly, hoping she wasn’t a lost cause after all.

“I guess I like hanging out with him.” the girl answered honestly. “I just hate sucking his dick. I have to pretend to like it though.”

Theo was left speechless. Typically girls that looked like Emery were uptight, and kind of prudish. This one was unapologetically crass, and he found that absolutely charming. The guy sounded like a real asshole though. Finding his voice again, he asked “Do you think you’re going to break up soon, maybe?”

“Maybe…I want to…I just have to wait for the right time, or whatever.” From her expression she certainly didn’t seem like she was into the guy. At that moment a look of shock flashed in her eyes, and she laughed so hard, it startled her conversational partner. She explained “My tuck just came undone. I gotta go fix it before it falls out the bottom of my skirt.”

Theo was confused. “Your tuck? Like…?”

Collecting her purse, the girl went on, “My tuck. You know. Gotta keep my junk stuffed between my legs. Sometimes that thing is really annoying, you know? Like, it just gets in the way. Anyway, I really had fun, Theo. We should do this again sometime.” And with that she was off, leaving the flummoxed boy in her wake.

‘Her tuck...?’ he thought to himself, connecting the dots. ‘Oh shit.’ As the realization swooped over him, he was left with a lot to think about. He’d never been attracted to a trans girl before, that he knew of at least, and it was a lot to process, but not thinking himself a bigot, he tried in earnest. Beautiful, check. Winning smile, check. Charming personality, check. Friendly demeanor, check. Funny, check. Nice tits, double check. In the end, he decided a pretty girl was a pretty girl, and this pretty girl was sexy as hell.

For the next several weeks, Emery was there every Friday like clockwork. They’d share their meal, and each time he’d enjoyed himself as much as the last. When she texted him about a date, he got his hopes up, only to learn she was talking about her, as she described the girl, insecure friend. He agreed, not minding a pity date with one of Emery’s homely acquaintances, if it meant getting that much closer to the girl he was so smitten with. It should speak volumes then that after being introduced to the leggy supermodel called Emily, he could hardly remember the blonde’s name. It was love at first sight.

“Theo, this is Milly. Well Emily, but I call her Milly.” Emery said sweetly, nudging her friend towards the six foot five boy. “She’s a little insecure about her height, but I told her that would not be an issue with you. See girl, I told you. He’s like a backward or something on the basketball team.”

“I’m a forward.” Theo clarified, not taking his eyes off his date. She was stunning. Her plump lips looked perfectly kissable. Her made-up eyes glistened under the streetlights. She was curvy in all the right places. Incredibly stylish. Her hair alone was cooler than he’d ever be. It all had him worrying the goddess was suddenly going to realize she was way out of his league.

Theo was normally a confident guy, but standing in front of the girl that he expected to be unattractive, it all crumbled away like it was all bluster. It was only her timid demeanor, being unable to look him in the eye, that had him thinking she was probably one of those girls who went through an awkward phase in middle school before growing into her looks. This girl definitely didn’t realize how drop-dead gorgeous she was.

“Nice to umm…meet you. Do you go by Emily or Milly?” he asked, trying to center himself, feeling thrown completely off by the girl with a notch in her eyebrow. When the only response he got was a small shrug, Theo couldn’t help wondering if he had already stepped in it. “How about I call you Milly, if that is what your friends call you, and I uhh, would love to be friends with you.” The college-age boy was kicking himself for not saying something smooth, like her name is just as beautiful as her.

It felt like the guy was looming over him as Emmanuel averted his eyes down to the sidewalk, feeling both physically and emotionally out of place. ‘I would rather go by my actual name… or even Manny, rather than Emily or Milly… better yet I’d rather he not talk to me at all.’

The whole situation was kind of a mess when Theo tried for a hug, and got a hand held out waiting to be shaken in response. Embarrassed, he went to return the gesture, when she looked equally as embarrassed, and tried to hug him in return, his hand colliding with her breasts. “I’ll leave you lovebirds to it.” Emery said obliviously, as she turned and skipped away down the alley, completely forgetting this was all for ****, patting herself on the back for perfectly playing matchmaker.

Manny clung to himself tightly, unintentionally putting his ample bosom on full display, while he blushed furiously, and hoped he’d just go ahead and die on the spot. Theo nervously stroked the back of his own neck, letting the awkward silence hang for a second before saying, “I uhh, got us a booth already…if you still wanna…?”

“Oh, I do!” his date practically shouted, Song’s veiled threat of keeping the boy happy still fresh in Emmanuel’s mind. What he didn’t realize was that Song never met this guy before, and was merely implying being sweet to a boy was the best way to get what you wanted from him, in this case a ride home. Instead, the anxious teen took this as a command to pleasure this guy to the best of his ability, lest he suffer the same hell he’d unintentionally reigned down upon the girls for the past few months. Not that Song wouldn’t have preferred Emmanuel end the night with a dick in his face.

Inside, the two found that booth Theo mentioned, one of those big round monstrosities meant to seat half a dozen people. The nervous boy felt the need to explain, “My frat bros, and I are regulars here, so when I texted Roxanne, oh, uh she’s the bartender, she’s like real old, and not as pretty as you, anyway, when I texted Roxanne and asked her to save me a spot, I think she misunderstood, and gave me this, so sorry it’s like, so big.”

“No, it’s fine.” Emmanuel blushed from the embarrassment of being called pretty. The taller boy's words reminded him of Emery’s ability to cram so many thoughts into a single sentence, and it put him at ease, at least just a bit. He then remembered his dates with Song, and how they always said couples that squeezed into booths next to each other were tacky, so he took the seat across from the stammering young man.

“So umm…” Theo frantically searched his thoughts, trying to find any topic of conversation the chic girl wouldn’t find boring, “how old are you?” As soon as he finished his question he had to fight the urge not to literally kick himself.

“Oh, uhh…eighteen…you…?”

“I’m twenty-one.” Mental math wasn’t his forte, so after another extended pause, his brain finally came up with another question. “Are you gonna be a freshman?”

“I’ll be a senior in highschool.” Emmanuel answered, a little ashamed for being held back, and the sound of his own modulated voice. He felt compelled to explain, “I had some umm…family troubles…and I had to do eighth grade twice.”

“That’s rough…” Theo replied, the sentence hanging in the air. “I’m going into my junior year. Semester doesn’t start till next week, but a lot of us have already moved back in. It was easy for me since my family lives in town, and all...”

A solid thirty seconds went by without either saying a word when the bartender finally got over to the table. They had no way of knowing, but at the exact same time they both shared the exact same thought. ‘Oh thank god!’

“Hey Theo!” the thirty-something woman said excitedly with a well honed customer service voice. Clearly she was at the pinnacle of her profession. “What can I getcha?”

“Oh, umm, two waters, and…what do you recommend?” Normally the frequent party animal would have ordered a PBR and not thought twice about it, but he didn’t want to appear as unrefined as he actually was in front of the trendy cutie he felt blessed to actually get the time of day from.

Roxanne could actually see his eyes begging her for help, and with a wink she suggested, “We’ve got a nice red in the back. Let me bring the bottle with two glasses. Be right back.” This wasn’t the kind of place where someone would typically order wine, so the flagon was going to need a good dusting. The server disappeared for a minute, leaving the two to sit through another agonizing silence until she returned. “So what’s this pretty girl’s name?” she asked, setting the glassware on the table.

“Oh, this is Emily, but her friends call her Milly.” Theo answered, blushing just as brightly as Emmanuel was under the layer of foundation. Being introduced with the feminine name again felt like a physical blow to the feminized teen.

“Well, Milly,” she started as if it was a given that they were already friends, “let me tell you,” the woman wrapped her arm around Theo’s neck, halfway **** him, and pointed her finger at his scrunched up face, “this one's a keeper. Honest as he is tall, and kind as he is handsome.” She released the boy, and continued, “I’ll leave y’all to it. If you need anything just wave me down.”

As Roxanne walked away, Emmanuel finally took the time to get a good look at the boy he found himself on a date with. What Emery said was right, handsome if you were into that sort of thing. Chiseled good looks, and cleancut hair, not dissimilar from what the feminized boy had woken up with that morning, but trimmed closer on the sides. His plain white t-shirt, and jeans said he wasn’t the type to worry so much about style, and his letterman jacket painted a picture of a person very proud of their athletic accomplishments. The pressure was on, and fearful of a worse punishment from the girls, Emmanuel did his best to strike up a conversation. “So you play basketball, right?”

That was all the prompting Theo needed. In an instant not an ounce of shyness remained, and he went on for twenty uninterrupted minutes about the previous year, how much he scored, his many assists, and his hopes for the upcoming season. Never one for sports, most of it went over the skirted boy’s head but he smiled and nodded just the same, afraid to cut the athlete off with any questions, though he really wanted to ask what the hell division three was.

The befuddled look on his date’s face told Theo he might be boring the poor girl to ****, only then realizing he hadn’t yet offered her a glass of the wine which was still sitting full on the table? He poured for them both and slid one across the table. “Drink for milady.” As soon as the utterance escaped his lips, he cringed, thinking he sounded like one of those fedora wearing incels.

Emmanuel looked at the beverage fearfully and said, “I don’t think I can drink here. Like, I don’t have my wallet, let alone a fake ID.”

“Don’t worry about that, pretty girl.” Theo snickered. “I’ve been drinking here since freshman year, and they’ve never once asked. Pretty sure they’d go out of business if they did.

“Don…” Emmanuel closed his lips feeling his cheeks warm from being called pretty once more. He had really only started to feel confident in himself recently, but all of that went out the window the second he woke up with tits the size of melons. “Don’t they ever get fined?” the boy turned girl asked, unsure whether or not to trust his date’s confidence. Apprehensively, he picked up the glass, and took a little sip, then waited for the S.W.A.T. team to come bursting through the wall like the Kool-aid man.

The conversation between the two stuttered, making both not only feel awkward, but both also believing themselves the cause. A topic would be brought up by one of them, the other would make an innocuous comment about it, and then there’d be silence after. This process repeated itself for an extremely excruciating half hour. Theo didn’t know whether to be embarrassed, or relieved when from across the bar came a voice shouting, “Theodore fucking Hamilton! You suave mother fucker!” Turning his head and feeling the shift of the long unfamiliar hair and the swaying of his earrings, Emanual saw four college students making their way across the floor to the booth. Two guys, and two girls, each proudly wearing their greek letters stood at the table, when the one who’d been abusing his vocal chords looked Emmanuel straight in the face, and said, “Scooch, sugar tits. Move next to your boo, so we can all sit down.”

“Jesus fucking Christ, Porkchop!” Theo yelled, covering his eyes, mortified that this obvious douchebag was actually his best friend.

“Yeah, Steven! God you’re such an ass!” the redheaded girl in the short denim skirt agreed, swatting who Emmanuel could only assume was her boyfriend on the back of the head. “I’m so sorry about that. I swear one day I’ll house train him.” Clearly she was used to apologizing for the meathead.

“It’s not a problem, really.” Emmanuel said, feeling like it was somehow his fault. He stood up and found a seat on the outside of the booth next to Theo. Out of the corner of his eye, he caught the obnoxious boy getting a good look at his exposed leg peeking out from the very short skirt.

“It really is.” the girl assured him. “Don’t worry, he’ll pay for it later. She then stuck her tongue out at the guy, and said, “I’m not sitting next to you now. You can make out with Jason instead.” The four slid into the table, the two boys first, followed by the two girls. The one on the end, as far from her partner as she could manage, asked, “Aren’t you going to introduce us, Theo?”

“Oh right.” Starting from the outside, he pointed to each person, saying their name. “This is Britney, Stacy, Jason, and this Asshole is Steven, but everyone calls him Porkchop. Guys this is…”

When the basketballer motioned towards Emmanuel to introduce him he jumped at the chance to curb the Milly nickname. “I’m Emily Brooks.” Saying it outloud in the feminine voice hadn’t lowered the impact on his masculinity. In fact it actually felt worse to say it himself. He wasn’t even sure why he added his last name.

“Hi, Emily!” the girls said in unison, while the boys gave a half hearted wave.

“I love your outfit!” It sounded like a scripted line a person would say to break the ice, but the jealousy in the black haired girl’s eyes said she truly wished she could steal it off the younger girl’s body. “Where did you get it?”

“Oh, umm…” The petrified boy shyly kept his eyes on the table. “The Hanger…in the mall…I work there, I guess.” As soon as he said it, he wondered why he felt the need to elaborate. He’d have a lot of explaining to do if they ever came in when he was working, and found a boy named Emmanuel instead. In reality they’d never have known they were one and the same. ‘Why did I say that!? Why did I give them my last name!?’

“Girl!” Stacy shouted, startling the feminized boy. “Are you a freshman at Central this year? Have you pledged yet? You have got to pledge Zeta!”

“Zeta?” Emmanuel was completely lost.

“Yeah, your boyfriend’s an Epsilon, right? We’re their sister sorority. Like, we do events together, and charity stuff…and parties!” the last part said with particular jubilance. It was clear where Stacy’s priorities were.

“She’s not my girlfriend yet, guys,” Theo clarified, clearly very embarrassed by his friends, but the implication that they were on their way there didn’t go unnoticed by Emmanuel.

Stacy gave her friend the side eye, before focusing on his date. “Well, you should scoop him up sooner rather than later, sweetie. He’s the hottest prospect still on the market after all.”

“Hey!” Jason, the giant boy with shoulders as wide as he was tall yelled. He was feigning anger, but the amused gleam in his eye told a different story.

“I said on the market, baby.” his girlfriend explained, lifting herself up the foot required to plant a tender kiss on his lips of who Emmanuel could infer was her boyfriend.

Britney nudged her bestie playfully, chastising her. “Bitch, you just want to take advantage of her discount.”

“No, I don’t!” Stacy replied in mock astonishment. A fit of giggles later, she clarified, “Okay, maybe a little, but just look at her. She’s clearly Zeta material.” She brought her attention back to the new girl, and looked her straight in the face. “Seriously, Emily. You should pledge. Rush isn’t nearly the nightmare it used to be.”

“I…uhhh…” Emmanuel searched his brain for any excuse, terrified of disappointing the two women he’d only just met, before realizing he could just tell the truth. “I’m a senior in high school. Not even sure if I’ll be able to get into college now.”

“Bitch, hush.” Stacy scoffed. “Central is totally a party school. If you have a pulse, you’re getting in. Next year is better anyway. Me and Stacy will be juniors, so we can sponsor you. You’re a shoe-in.”

“She’s not wrong.” Britney affirmed, though with a far more measured enthusiasm than her exuberant sorority sister. While this conversation was taking place, the guys were mostly grunting to each other about scores, and beer, but the whole time, Theo could hardly take his eyes off his date. This didn’t go unnoticed by the redhead, who after a short while interjected, “Guys, I think we interrupted. They’re trying to get to know each other, and we barged in head first. Let’s go play pool.” Not waiting for an answer, the girl stood up, and glared at the rest of her party till they followed.

“Okay, Britney. You’re right.” Stacy sighed, collecting her purse, and fighting her way out of the round booth. The boys followed, and soon the four were standing at the edge of the table while the girls said a long goodbye.

While this was going on, it occurred to Emmanuel that he'd just met these people and the girls were already much nicer to him than his friends ever were, at least when they weren’t being **** to love him. The instant sense of inclusion felt good, though tempered by mention of trying to make him into a coed.

“Alright, y’all.” Stacy said, mistakenly thinking the new girl’s anxious expression was because she was too polite to ask them to leave. “I want shots! Let’s get the fuck out of here!” With a knowing wink, and a playful smile she said, “Have fun, you two!” before grabbing her bestie by the arm, and heading to the bar.

“Later, bro.” the boys grunted. Suddenly, again, the two were alone, only now Emmanuel was cuddled up close to his date with no idea how to get away smoothly. A look at the clock on the wall told him his mom was but an hour or two away from arriving home, and that was something he absolutely did not want.

“So, tell me about yourself.” Emmanuel asked, trying to keep the conversation going. The last thing he needed was this boy losing interest, and stranding him on the opposite side of town. “What’s your family like?”

“Oh, well…” Theo was hesitant. Dumping his complicated home life on this girl might scare her away before she had the chance to get to know him. A brief moment of pause gave him time to weigh the pros and cons. After realizing she’d been nothing but kind since the moment they met, he decided to take the plunge. ‘Better to rip off the daddy issues band-aid sooner rather than later.’ “Um, I was basically raised by my Aunt.”

Emmanuel’s ears perked up. If there was one thing he could relate to, it was an absentee parent. He asked, “Mom and Dad not around?”

“Not exactly.” The boy’s face fell for just a moment, the twinge of pain in his heart evident. “I never knew my mom. She died in childbirth.”

“Oh my god! I’m so sorry!” Emmanuel’s sympathy was genuine. Regardless of whether or not this guy was expecting something, that was a situation the trapped boy thought no one should have to deal with. “What about your Dad?”

“He’s a doctor. Actually, he was pretty overbearing when I was born. Since I was a preemie he was relentless making sure I stayed alive. Kept worrying that I was gonna be underdeveloped.”

Emmanuel peered into the giant boy’s eyes, his heartbreak for the youth evident. “Clearly he didn’t have to worry there.”

“Haha, yeah.” The pain softened a bit from the girl’s kind words. He ended up taller than he ever could have expected, and liked the fact the pretty girl was also an above average height, at least for her gender. Theo continued, “Anyway, aside from his obsession with my treatment, he was a mess. Not that I remember, but apparently that’s why we had to move in with my mom’s sister, Aunt Bethany. The woman is a taskmaster, but she’s great. I don’t know what my life would be like without her, and I don’t want to think about it. Once I got a little older, I started looking more and more like my mom, and my dad pulled away hard. When my Aunt said something about it he just told her my face broke his heart all over again.”

Emmanuel was at a loss for words. “That’s just…heavy…Where is he now?”

“Well,” Theo rubbed the back of his neck as he thought about his father, “he met my Mom doing Doctors Without Borders, so after a few years, he decided to go back to that. Closed his practice, and that was it. I stayed with my aunt, and he took off for Timbuktu or wherever. He still shows up sometimes, but it’s few and far between.”

“Wow…just…wow…” Emmanuel blinked a few times, his eyelids feeling heavy as he tried to wrap his head around what his date was having to go through.

The corners of Theo’s mouth turned up in a slight smile seeing the girl flutter her eyelashes at him, like she was trying to use her charms to help cheer him up. “Eh, he’s a great dude, but a shitty Dad. What are you gonna do?” Theo took a swig of his drink, and then **** a smile back onto his face. He turned to his date, and asked, “What about you? What’s your story?”

Emmanuel didn’t want to get into specifics, he had already given away too much, so he kept it brief. “Dad is gone, and even if he could come home again, there’s no way my Mom would let him. Teenage parents made stupid teenage mistakes, but she makes it work. Bust her ass to take care of us.”

“What does she do? Is she also a fashion expert?” Theo asked, unconsciously leaning in a little closer to his date.

Further probing caught the feminized boy off guard. No one had ever taken that much of an interest in him. When asked how he was doing, he always just shrugged or just said fine, knowing no one really wanted to know more, but on this rare occasion, this person actually did.

Emmanuel had no clue Theo’d already made up his mind to marry this girl. Every tidbit was another piece that made up the beautiful picture he was blessed to have met. “Oh, uh…no. She works at Target during the day as a stocker, and at night she’s a receptionist at a hotel. She also does Uber and stuff. Gotta make ends meet I guess. It hasn’t been as bad since I started working though.” The skirt-wearing teen shrugged a little. He was happy to help his mom, even if she insisted he shouldn’t have to work.

Theo perked up with an inquisitive look in his eye. “Wait, which hotel does she work at?”

“Ahuva Bahyeet. Why?”

“No shit!” the boy said excitedly. “That’s where Aunt Bethany works. She’s the operations manager.”

“Wait.” the teen coughed, clearing his throat after the feminine voice slipped. “Your aunt is Bethany Long?” Emmanuel had never met the woman before, but he’d heard that name from his mother plenty of times.

“Holy shit, yeah!” Theo replied. “It’s a small world. I feel bad for your mom though. I hear Aunt Bethany is ruthless at work.”

“Yeah, small world,” the boy turned girl agreed, trying to hide that panic washing over him. His only experience with anyone with any type of clout was Song’s mother, and he knew firsthand that if anybody hurt her little Star, she’d hang them by their testes. He thought, ‘Holy shit, I’m gonna get Mom fired.’ It was another layer of terror added to his already mountainous list of anxieties. Emmanuel had to do everything he could to keep this boy happy, especially now. For the rest of the night, a smile wouldn’t leave his face. He was going to be the happiest date this boy ever had. If Theo asked him to jump, he’d have asked, “Off what?” His mother worked hard, and he wasn’t about to screw up her job over his own selfish behavior. Suddenly remembering his mom’s imminent arrival, he checked the clock again, that smile plastered on, just like Song’s used to be. What he didn’t realize was that most people, not even Grace Rim, would fire someone just because their kid’s relationship didn’t work out.

“Everything okay?” Theo asked, noticing the girl’s glances. He didn’t want her to feel pressured to stick around, but she hadn’t yet moved to the other side of the booth when he dumped all his family drama, so that was a good sign.

He felt a little relief when she explained, “Yeah, umm…I just left my phone…my umm purse…yeah my purse…all of it at home, and…”

“Oh, screen anxiety.” He finished her sentence for her, completely understanding, or rather not, but he didn’t know that. “I feel like that all the time. I got so wasted at a party last year, and lost my phone for like two days. I thought I was gonna die.” Seeing a golden opportunity, Theo decided it was time to go out on that limb. It was strange to the boy that it was even taking this long. With Emery, and pretty much every other girl he’d been interested in, he had no problem diving in head first, but with this one, he didn’t want to ruin his chances before it even got off the ground. Nervously, he draped his arm over Emily’s shoulder, and prayed he didn’t get slapped in the face for his troubles. When it didn’t come he pushed his luck a little further. Moving his other arm, he rested a hand on the beauty’s supple thigh, and found a firm muscle underneath that baby soft flesh. Leaning in and practically whispering in her ear, he asked, “Do you jog, or something? Like track and field?”

“Something like that.” he heard the bashful girl reply, her own voice a breathy whisper. In reality Emmanuel ran a lot, just in everyday life, like getting to the bus stop. Though it started with trying to avoid his many scuffles with the neighborhood toughs he frequently found himself in conflict with. If his date could have seen his face from where he was sitting, he’d have seen a person terrified, on the verge of tears, but **** to not piss off the boy, and incur the wrath of his furious ex. His thoughts on Song, Emmanuel did his best to emulate the tiny Asian-American girl. He took a deep breath, and tried to create a cute, but seductive guise. Turning to face Theo, practically able to taste the jock’s breath, with a giggle, he asked, “Theo, you wouldn’t want to take me home, would you?”

In an instant, any fear the frat boy had of the beautiful thing’s rejection went right out of the window. He was ready to be patient, and end the night with a handshake and a hope that she’d call, but instead, she was basically throwing herself at them. She didn’t seem like the type to hook up on the first date, but here she was, asking to come to his house. Trying to contain his glee, and hoping he still looked cool enough to keep her attention, he cleared his throat, dropping his voice a bit, and said, “Yeah, babe. Of course. Just let me finish this bottle of wine, and we can go.”

“Right.” Emmanuel agreed, his eyes turning back to the clock, the countdown to his doom not stopping for anything. He looked at his own empty glass, saying, “Let me help you with that.” He poured two glasses, and started guzzling down his own. It was gone in a flash, and he was pouring yet another. That one went down just as quick, when he noticed Theo was still sipping the first. Compelled to hurry, he placed his well manicured hand on the bottom of the boy’s glass, and tipped it up into his lips, nearly **** the youth.

Theo, for his part, was only too happy to chug the dry beverage, glad this girl seemed to be in quite the hurry to get him into the bedroom. Another glass for the both of them, and then one more, and suddenly the two were in a very different state of mind. Any inhibitions he had left were utterly destroyed.That was when Theo decided to swing for the fences.

Emmanuel had drank before, even been tipsy, but in what seemed like an instant, he was suddenly very drunk. Between the speed of consumption, and his empty stomach, the wine hit him hard. The room began to spin, and it almost got away from him, but instead he was given a new center to focus on when his date’s lips collided with his own. For just a moment, he began to panic, but knowing he couldn’t disappoint the boy, his mind threw up the best defense mechanism it could muster in his **** state. His thoughts drifted back to Emery, making out with her on that picnic blanket, and how his heart swelled. At the time, she was the greatest thing to ever happen to him, and compared to his present reality, it was a much better place to be. As the two parted, the taste of wine on his lips, he was brought back to reality when his eyes met Theo’s, and he managed to slur out the question, “Are you ready to leave?” Blinking heavily, a sense of worry shot through him. ‘Was that rude? Should I kiss him again? Do I have to kiss him again!?’

Theo, his heart exploding with joy, tried to play it cool, but failing completely, answered, “For you, babe, anythink.” Luckily Emily was just as intoxicated as him, far too drunk to notice his gaff.

As they stumbled out of the establishment, Emmanuel began to make the long walk to the parking lot, only to be stopped by the wobbly boy, turning his date around, and pulling them in the other direction. “Car not this way?” he asked in broken English, tripping slightly in the block heels.

“It’s at the house.” Theo explained. “Like right across the street from campus. It’s only a couple blocks. Do you want me to carry you?”

“I’ll be okay.” His date giggled, and it was almost too cute for him to bear. Wine hit him harder than beer and it seemed the girl was similar, or at least a cheap date. The way she moved and behaved was adorable. The smashed girl asked, “You live across the street from a Christmas monster?” while sitting down on the pavement, and taking off her footwear, apparently having decided to carry them for the rest of the journey. The long nails made unlacing them a virtual impossibility, so the drunken teen grabbed the shoe by the heel, and yanked it off. This repeated on the next, and both times Theo got a good look at those silky panties Emmanuel himself had yet to see.

“I live across the street from school.” he answered, oblivious to the joke. It didn’t matter to the lovestruck boy though. The sound of her laughter after such a rough start was a welcome change. “I also live across the street from a liquor store on the opposite corner. Do you mind if we stop by there on the way?”

At this point the teen was white girl wasted. His brain had decided to stop making new memories before they even left the shopping center. Struggling to focus, Emmanuel kept one thought in mind, and that was that he needed to keep this boy happy, no matter what. He was Emily, and Emily was supposed to be sweet after all. “Of course I don’t mind.” Still tasting the boy and the booze in his mouth, he asked, “Can you get me some gum though?” Trying to stand and failing, he noticed the matching polish on his toenails, and surprisingly the first thought that crossed his mind was, ‘Pretty.’ Emmanuel had to crack up at the absurdity of it all. Doing his best baby voice, he held up both arms and said, “Help please.”

Theo pulled the girl up effortlessly, her feet lifting off the ground for a moment, before catching her between his chest and arms, giving her a quick kiss. While stunned, she blinked and kept her lips puckered. “Of course, babe.” If Theo had had the money, he would have bought her the whole store.

While Theo was inside the liquor store, Emmanuel was left standing to the side of the building, just out of view of the cashier. Wobbling on unsteady legs, he nearly fell asleep upright, but then a car pulled up with a guy hanging out of the passenger side window. “Hey there, honey. You looking to party?”

At this point, the skirted boy had completely forgotten how he was dressed, and thinking back to the typically hostile interactions he’d had in parking lots such as this one, he dropped his shoes, and raised both fists, stumbling, ready to fight. In a voice drifting somewhere between Emmanuel’s and Emily’s, he asked, “You wanna go, assssshooole?”

The guy turned back to his buddy incredulously, and said, “This bitch wants to fight.” then explained, “No, sweetheart. I want to fuck.”

Drunkenly, the lanky teen snickered, and after dropping his hands, said, “Well then go fuck” Emmanuel paused for a split section to hiccup before continuing, “yourself!”

Ego bruised, the guy shouted back. “Whatever bitch! You’re ugly anyway!”

That was when Theo came through the door, quickly believing he understood the situation, being slightly more aware of his surroundings than his date. “Is there a problem, fellas?”

“You need to get your girl, bro.” the guy said. “We were just trying to be friendly.” Brave enough to harass a teenager in a parking lot, but no more than that, the two men drove off without another word.

Standing there Emmanuel touched his tongue to his puffy lips. “They didn't wanna fight…my lips…” The sentence was left incomplete, his kisser feeling out of place and swollen.

“They didn’t want to fight your lips?”

“What?” Emmanuel said, tucking some of the long hair to one side of his face behind his ear. “Fight my lips, that's funny, you're funny.”

“Come here.” Theo said, not exactly the image of sobriety himself. When his date came closer he used his free hand to cup her chin. “I will fight your lips.” He spoke the words before leaning in, seizing the opportunity to kiss the pretty girl, feeling his heartbeat quicken as he did. “You ready to get out of here?” When she nodded he was about to hold her hand with his, but noticed she had walked away from her shoes.

After the encounter, and the kiss, Emmanuel had almost forgotten them, but Theo had enough sense to collect the pair before heading to the crosswalk. Only when at the mouth of the gravel driveway leading to the three story house occupied by a dozen young and horny idiots, did the shorter of the two realize going barefoot was a bad idea. He looked at the shoes in Theo’s hand like putting them on would have been equivalent to passing the bar exam.

Theo chuckled, and placed them in his dates arms, then scooped Emily up, his hand under her butt, then carried her in one arm, and a six pack with the other, all the way to the front door. He didn’t stop there though. In the house, he effortlessly made his way up the stairs, and for the first time since middle school, Emmanuel felt absolutely tiny.

The frat boy was grateful his junior year allowed him his own room, and he was excited to christen it. Plopping the girl down on his dingy loveseat by the bed, he opened two beers with a lighter, handing one to Emily, before taking a seat next to her. The room spun for a moment, but his stomach settled, and after that, the only thing he could see was the beautiful thing staring back at him expectantly. “Sorry it’s messy.” His desire for her grew every moment she held his gaze.

“My room is always messy.” Emmanuel said, looking around enviously at the giant space. It was then he noticed a little brown stuffed bear. He jumped up from the couch to pick it up, and make sure he wasn’t hallucinating the out of place plush. “This is a little cuter than anything I was expecting to find here.”

Seeing the pretty girl holding the stuffed animal caused his heart to sing. “Yeah, my Aunt gave it to me when I was little, so I wouldn’t get lonely when she’d have to go to work. You know? Like Teddy Roosevelt. Because we have the same name.”

It took a minute when suddenly the understanding dawned on the tipsy flirt. “Oh, your name is Theodore. Theo is your nickname. I’m so drunk, lol!” Emmanuel didn’t even realize Emery had rubbed off on him a little, and he’d just spoken out loud in text slang. “So, Teddy Bear,” the new pet name coming naturally, it was clear Emery had even more of an effect, and Emmanuel was pretty proud, as obvious as the comparison was. “What should we do?” he asked, holding the bear to his enhanced chest. ‘Boys like it when a girl gives them a nickname.’

Theo patted his leg, and waved the cutie over. “I love how you call me Teddy Bear. God you’re so cute. Why don’t you come sit in my lap, and I’ll show you.”

Emmanuel’s inner monologue was for once, kind of prideful. For once, he felt like he was nailing something, even if that something was playing the part of the flirtatious love interest to a college jock. He strode across the room, and plopped down on the athlete’s lap, wrapping both arms around his neck. “You're tall.” the drunken teen said like someone might say the sky was blue.

In an instant the two were sloppy kissing, and Emmanuel’s thoughts drifted back to Emery. Those kissing lessons were apparently paying off, because Theo was clearly enjoying himself. Closing his eyes, Emmanuel was with the blonde girl again, as his tongue explored her mouth. The girl’s grip was a lot stronger than before, but that was fine with the teen, and if anything was actually kind of a turn on. Someone wanting to tear off his clothes was sexy as hell.

Theo felt the hot babe’s soft skin under her shirt, and as his hands found their way to the front, and reached second base, the girl shuddered, but didn’t stop him. Her breasts were a masterpiece, and he had to fight the urge to squeeze them as hard as he could. The gum she’d been chewing since they left the store wound up in his mouth. Most people would find that gross, but Emily could have spit it on his floor, and he’d have thanked her for it. The kissing, just touching her even, had already started the process, but hearing her moan made his pants feel too tight and restrictive.

Still necking with Emery, Emmanuel melted into a puddle of lust. The girl had never been so rough with him, and even though his swollen chest hurt a little, it also felt so very very good. His lips moved down to her neck, and were met with a little stubble, something he was positive the lovely lady had never had to deal with before. If the feminized boy had thought about it, he’d have been incredibly grateful for the whiskey-dick saving him from a very unpleasant erection trapped in that cage, though the more turned on he felt, the more uncomfortable the feeling grew. Cracking open his eyelids, he remembered what was actually going on, and like a defense mechanism, his brain said, “Nope” and he closed his eyes again, trying to wow his girlfriend with the new level of skill his lips had reached.

Thoroughly turned on, Emmanuel knew what his girl liked, and that meant it was time for a little oral pleasure. After getting up, and finding his way to his knees he felt the throbbing erection pressed against the jeans with his well manicured fingers. Emery didn’t usually wear jeans, so it was a struggle to get the restrictive garments down around his partner’s ankles. “Oh, someone’s big.” Taking the cock into his mouth, only one thought crossed his mind and part of it had already slipped free from his mouth. ‘When did her dick get so huge?’

“God damn!” Theo shouted, happy most of his frat brothers hadn’t moved back in yet. Heaven forbid someone interrupt this gorgeous lady demonstrating her mastery of the craft. Never in his life had a blowjob felt so good, which was especially surprising given the amount of **** coursing through his veins. His hand found its way to the back of Emily’s head, and gripped her hair tightly as she pumped up and down. Just when he was about to explode, he stopped, and pulled her off.

The meaty member being pulled free from Emannuel’s mouth caused his brain to give the drunken version of the blue screen of **** before rebooting. “Did I do something wrong?” Emily looked like she was about to cry, and Theo’s heart broke for her. Never in his life had he seen a person so dedicated to pleasuring another.

“Of course not, babe. I just want to save that for you.” He picked the girl up, and tossed her on his bed, and after struggling to get his pants the rest of the way off, joined her. As quickly as she dropped to her knees and with how rejected she looked when he took his cock from her mouth, he promised himself that he was going to let her finish the next time. Feeling happy that short skirts existed, he threw up the fabric and grabbed the girl’s panties, nearly tearing them as he slid them down her long smooth legs. The jock was expecting to practice cunnilingus for the first time in a while when he was surprised to find a penis not dissimilar from his own locked up for safe keeping. ‘Oh shit.’ He took a moment to process, hoping his confusion didn’t show, hurting the poor girl’s feelings. It hadn’t occurred to him that she could be transgender like Emery, and it came as a shock. A little self-talk helped him work through it quickly though, realizing that he didn’t have a problem with Emery, so why would he have a problem now. Sooner or later, he was planning on crossing that bridge anyway.

From there, he decided to try something else, and after fumbling through his nightstand for a rubber, and some astroglide, he was prepped and ready to go, pressing his phallus slowly into the girl’s puckering butthole.

‘What the fuck is happening?’ Emmanuel wondered. There was nowhere for his thoughts to flee. He and Emery had never done anything like this before, and his mind could no longer protect him from reality. He nearly screamed, but then the thought of his mother standing on the side of the road with a cardboard sign entered his thoughts. He shoved that to the back of his head, and meeting eyes with Theo, gave himself a pep talk. ‘Okay, this isn’t weird. You’re not Emmanuel. You’re Emily. Emily really likes Theo…like a lot. Of course Milly would want to have sex with him. You’re Emily. You’re Milly. You want to have sex with him. He is incredibly hot after all, and what a cock. Be a good girl Emily, and make this boy happy.’

Emily, a newly acquired shield, took over, and she started to relax her sphincter enough to let the rest of the engorged penis work its way in. It hurt at first, but less and less with each thrust. She cringed, clutching the bedsheets. ‘Milly would want to be fucked…Mom needs Emily to make her date happy…she would be happy.’ Feeling the weight of Theo pressing down on her - in her, she welcomed the girth with joy. As the pain subsided, the pleasure began to swell, and the new girl was actually starting to enjoy herself. “Err, errrr, er.” The grunts started to subside as genuine pleasure washed over the feminized boy, their imprisoned member straining against the metal holding it. “Eh, eh, ehhhh, eh.”

For a few seconds at a time, Emmanuel would poke his head back in to freak out about liking something he absolutely wasn’t supposed to like, but Emily would stuff him back away, and moan, letting Teddy Bear know what a good job he was doing. “Fuck… fuck… fuck me, Tedddyy, Teddyyy! Oh fuck, oh fuck.” After that, it was easy. If she let the boy have his way, he definitely got what he wanted, and she could just let herself bask in the pleasure that washed over her body.

Pressing his condom-covered dick to the trans girl’s hole, Theodore thrust gently but firmly with his hips, it taking all of his control to not just ram his cock all the way in. The fact that she had one of her own, locked away in a little cage thing or not, was a shocker, and if he wasn’t so drunk and horny he might have paused to have a conversation first. How much he liked the girl, how connected he felt, would have him accept her, but his mind was thinking more about carnal desires in the heat of the moment like how tight her body felt. He could feel her squeezing her ass around his cock as though she wanted it to stay inside of her forever. The way Emily’s groaning evolved, growing in pitch till she started to call our his name, begging him to fuck her. It was music to Theo’s ears and it was all he could do while thrusting to not explode right there and then. “Mmmm Emily, fuck yes…Emily!” It felt good to say her name as he felt her warm body writhe underneath him. She wanted him and he wanted her.

The only thing preventing them both from finishing immediately was their blood **** content. It couldn’t hold off for long though, and as they crescendoed together, Theo spilled his seed into the condom while her’s gushed out onto his sheets. It was Emmanuel’s most troubling, uncomfortable, and painful orgasm of his life, thanks to the cage around his own dick and the new experience of his rear end being stretched.

Both their clothes covered in sweat, the boy kissed her on the lips, and then the forehead, before rolling over and laying on his back beside her, as the two breathed heaving breaths. If he’d have just been a little more sober, he might have stopped himself, but compelled, the words escaped his lips. “I think I’m in love.”

Emily bathed in the afterglow, having just had the time of her very short life, but right behind her, Emmanuel was ready to scream. As a mental construct, a shield, it was her job to protect the mind from what it considered trauma. Between it, and being blackout drunk the teen boy wasn’t about to remember cumming from being fucked in the ass.