Ollies Lost Innocence

By Mason Hatfield

Published on Apr 1, 2023

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This is a work of fiction. Feel free to contact the author about the story.

This is a shorter, plot heavy chapter. I decided to split it off since the chapter was getting too long. Next one should be out pretty quick. Enjoy.


Eddie's heart sank when he saw Ollie's face on the phone screen. His roommate looked drained and disheveled, his hair messy and his eyes glassy. "Hey," Eddie said softly, trying to keep the anger out of his voice.

Ollie forced a smile. "Hey, Eddie."

"What happened?" Eddie asked bluntly.

Ollie hesitated for a moment, not wanting to tell Eddie about what happened between Tyler and Antoine. "It's nothing, really," he said with a shrug.

Eddie narrowed his eyes. "You texted me! You said you needed to talk. And then you ignored me for almost an hour! So talk, Ollie."

Ollie sighed. He knew he couldn't hide it from Eddie forever. "Fine," he muttered, looking down at his feet. "Tyler saw me talking to this guy Antoine after class and got jealous or something. He punched him."

Eddie's eyes widened in shock and anger. "What?! Is the guy okay?"

Ollie nodded quickly, not wanting to dwell on that part of the story right now. "Yeah, he just had a bloody nose."

"But still! That's not okay!" Eddie exclaimed.

"I know," Ollie agreed softly.

"And then what happened?" Eddie pressed on.

Ollie sighed heavily. "I talked to Tyler... confronted him about it, I mean. It was right before that when I texted you." He paused for a long moment.

"And?" Eddie asked, frustrated.

Ollie looked at Eddie for a second before angling the phone away from his face. "Erm--we went to an empty classroom to talk and... we had sex again."

"Ew," Eddie muttered under his breath before catching himself. He didn't want to shame Ollie for enjoying sex with someone who treated him poorly but it was hard not to feel disgusted by Tyler's behavior.

"I know I shouldn't have let it happen," Ollie continued, looking down at the ground as he walked. "But I just couldn't help myself."

"You need to stop letting him treat you like this," Eddie said firmly.

"Well...," Ollie said quietly.

"He choked you unconscious last time!" Eddie exclaimed, unable to contain his frustration any longer. "And now he's fucking you in classrooms? This is so messed up!"

"I can handle it," Ollie insisted weakly.

"No, you can't! Look at yourself right now!" Eddie cried out in exasperation. "You're all banged up and exhausted because of him!"

"It's not that bad..." Ollie trailed off uncertainly.

"Yes it is! You missed a class, didn't you?" Eddie prompted.

Ollie nodded sheepishly. "Yeah, I did... "Eddie--look, I'm sorry," Ollie said softly. "I know you're worried about me and I appreciate it. But I'm okay, I promise! Can we let this go until we're back at the dorms?"

Eddie sighed heavily, knowing that he wasn't going to get through to Ollie right now. "Fine," he said reluctantly. "But we're talking about this tonight."

"Okay," Ollie agreed with a small smile.

"Take care of yourself, okay?" Eddie said before ending the call.

Ollie was left alone with his thoughts as he continued to walk back to his dorm. He knew that there was something that wasn't right with what Tyler was doing, but he couldn't help feeling drawn to him anyway. It scared him how much power Tyler had over him and how little control he felt like he had in their relationship, but still... Tyler HAD agreed to calm down with the possessiveness a little bit, right? Granted he'd done so after fucking him stupid in a risky place and talking about how much Ollie was "his"... but Ollie liked being his. It felt dangerous, exciting, and forbidden. No one had ever valued Ollie as much as Tyler seemed to. Valued him so much that he punched a guy for him! That had been wrong but it felt good too in a twisted sort of way.

Ollie wanted to talk to someone about what was going on, but he wasn't sure who. He couldn't tell his parents--they would freak out and probably make him come home. And talking to a counselor or therapist felt too formal and scary. He thought about Antoine for a moment, wondering if maybe he could confide in him since it seemed like they'd had a connection, but that had already gotten his cute classmate in trouble... Other than Eddie he'd only really made some minor acquaintances here at school--so much of his time lately had been dominated by Tyler that he hadn't been putting in any effort to meet other people. Ollie sighed heavily. He really thought he'd made some headway with Tyler today. He didn't want to write him off just because Eddie thought he was bad news. Ollie wanted to handle this his own way, like he'd been doing.

He trudged into his dorm room and collapsed on the bed, still wearing the clothes he had on during his encounter with Tyler. He was exhausted from the emotional rollercoaster of the day and all he wanted to do was nap. He slept there as the afternoon faded away, not stirring until the sound of the room's door closing woke him up. Ollie blinked blearily at Eddie, who was standing by his desk looking disgruntled.

"Hey," Ollie yawned.

Eddie crossed his arms over his chest. "Hey yourself. Looks like you slept for a while."

Ollie sat up, rubbing his eyes. "Yeah, I guess I was more tired than I thought." He paused for a moment before asking tentatively, "Are you still mad at me?"

Eddie sighed heavily and walked over to sit on the edge of Ollie's bed. "I'm not mad at you," he said softly. "I'm worried about you."

"I know," Ollie replied quietly.

"Erm--can we talk?" Eddie asked.

"About what?" Ollie said dumbly.

Eddie rolled his eyes. "About Tyler, dummy."

Ollie hesitated but then nodded slowly. There was a pause. "What do you want me to say?" Ollie asked eventually when no words seemed forthcoming.

"I don't know!" Eddie exclaimed frustratedly before taking a deep breath and trying again: "Well--for starters, I want to know how you're actually feeling about everything that's been going on."

Ollie shrugged, not meeting Eddie's eyes. "I don't know," he muttered. "Confused, I guess? And a little scared... but also excited?"

"Excited." Eddie repeated flatly.

"Yeah," Ollie admitted with a sigh. "I mean... Tyler makes me feel things that no one else has ever made me feel before. It's like this rush of adrenaline and desire all mixed together..."

"But at what cost?" Eddie pressed on gently.

Ollie didn't answer for a moment, instead staring off into space as he thought about everything that had happened between him and Tyler over the past month and a half--the theft of his virginity in an alley way; rough sex; the cross-dressing; the spanking and choking; the fucking on campus in an empty classroom; the possessiveness; the way he'd punched Antoine just for talking to him...

"I don't know," Ollie repeated softly. "I know some fucked up stuff has happened... but some amazing things have happened too! And I really think we made some progress today. He said he won't do anything like punching Antoine again."

"That's not progress, Ollie," Eddie said firmly. "That's just him saying what he thinks you want to hear so that he can keep controlling you."

Ollie looked at Eddie, his eyes wide with shock and hurt. "You don't know that!" he exclaimed.

"I do know it! Think about it--has Tyler ever actually done anything to show that he cares about your well-being? Has he ever listened when you asked him to stop doing something?"

"He...he says that I'm special to him. That I'm everything to him..." Ollie trailed off uncertainly.

Eddie rolled his eyes again. "Words are meaningless without actions behind them," he stated bluntly.

"But I like being with him!" Ollie protested.

"I get it, okay?" Eddie replied, throwing up his hands. "I understand why you're drawn to someone who makes you feel desired and loved in a way no one else has before... but Ollie, I don't think this is love--or even healthy desire!"

Ollie was silent for a moment before speaking up hesitantly: "But what if there is nothing wrong with the way we're getting along?"

Eddie sighed heavily as though steeling himself for another round of discussion on this topic: "There is so much wrong with it," He emphasized each word slowly and carefully as though they were made out of glass that could be easily broken by an overly forceful tug into reality. "I know you're new to this... but, this isn't how relationships should work."

"My parents got together after my dad punched a guy who'd been talking smack about my mom at a bar," Ollie pointed out defensively. "They've been married for twenty-five years."

"That's... not the same thing, babe," Eddie said gently.

"But it shows that sometimes people do crazy things for people they care about!" Ollie countered.

Eddie hesitated before speaking again, feeling like he was walking on eggshells around his best friend. "Yes--but it doesn't make those actions right or healthy and you deserve better than that!" Eddie exclaimed. "You deserve to be with someone who respects your boundaries and treats you like an equal partner--not a possession!"

Ollie looked at Eddie for a long moment, his expression conflicted. "I know you're just trying to look out for me," he said finally.

Eddie nodded, relieved that Ollie wasn't pushing back as hard anymore.

"But I don't want to lose Tyler," Ollie continued firmly.

"I'm not saying you should break up with him right this second," Eddie replied quickly before adding more forcefully: "But I think we need to figure out a way forward where you feel safe and respected by him."

"But Eddie, I feel like I've done that. That I'm doing that. That's what you're not hearing," Ollie said. "You weren't there today, you're only hearing about the crisis, not the resolution."

Eddie sighed heavily again, knowing that he wasn't going to convince Ollie right now. "Okay," he said finally. "But promise me that if there isn't the progress that you hope there is, you'll rethink this?"

"I will," Ollie promised.

"And if anything feels off or wrong, promise me you'll call me?" Eddie pressed on gently.

"I will," Ollie repeated softly, leaning in to give his roommate a hug. Eddie easily returned his smaller roommate's embrace. Ollie gave great hugs.

"I love you, you stupid slut," Eddie said, kissing Ollie's hair. "I just don't want anything bad to happen to you."

Ollie smiled into Eddie's shirt. "I love you too, you nosey bitch," he said affectionately before adding more forcefully; "But I don't want to spend all of our time talking about Tyler."

Eddie smiled weakly at his friend's attempt to change the subject. "Fair enough," he said with a chuckle before pulling away from the hug and launching into a story about his latest theater class assignment--a one-act play where they had been tasked with creating three dimensional characters and believable conflicts within just 30 pages. Ollie listened intently, grateful for the chance to talk about something other than his complicated relationship woes--hoping deep down that somehow everything would work out in the end between him and Tyler despite Eddie's warnings...


Ollie waited anxiously for Tyler's text or call, but it never came. It had been three days since their last encounter in the classroom, and Ollie couldn't shake off the feeling that something was wrong. He was used to Tyler going MIA for a few days at a time, but this felt different. The silence between them seemed almost like a punishment for Ollie confronting him about his possessive behavior. Eddie noticed how anxious and on edge Ollie was becoming as each day passed without any word from Tyler. He didn't want to rub salt into the wound by bringing up Tyler's absence or stirring up more drama.

Instead, he tried to distract Ollie with fun activities around campus - going to book talks and poetry readings together, hanging out with Eddie's theater friends, playing Mario Party... But even though those moments brought some temporary relief to Ollie's anxiety, he always found himself checking his phone for messages from Tyler when they were alone once again.

Ollie sat in his dorm room, staring at his phone for what felt like hours. He had finally mustered up the courage to text Tyler after four days of silence. He found a funny gym meme online that he thought Tyler would appreciate and sent it along with a message: "Hey, saw this and immediately thought of you haha." But there was no response. Ollie's heart sank as he waited for a reply that never came. He couldn't help but feel like Tyler was purposely ignoring him.

There was only one more week before midterms and after that it would be winter break until late-January. Ollie would be going home for the holidays. He realized he had no idea what Tyler's plans were; if he was going home or staying in his apartment. What if Tyler didn't reach out before then?

The next afternoon, Eddie noticed Ollie's mood had taken a serious dip again. He sat down next to him and placed a gentle hand on his shoulder.

"Hey, you okay? You seem really down," Eddie asked.

"I don't know... I haven't heard from Tyler in five days," Ollie replied, looking at the ground with tears welling up in his eyes.

Eddie took a deep breath and decided it was time for him to speak up about his concerns. "Ollie, listen... I'm worried about you. Tyler's been treating you really poorly; he's possessive and violent towards other people who get too close to you--and now he's neglecting you."

Ollie looked at Eddie defensively as tears welled up in his eyes; "I can handle myself."

"No, that's not true," Eddie interjected firmly but kindly; "You've been visibly upset since last week."

"I just wish he would talk to me..." Ollie trailed off as the tears began streaming down his face.

"Babe," Eddie sighed before continuing gently; "Maybe if he doesn't want anything more to do with you then that's for the best..."

"But... but I can't just let go of something like this..." Ollie's voice wavered helplessly between sobs now

Eddie wrapped an arm around him tightly and pulled him into a hug. As Ollie was crying into Eddie's shoulder, his phone suddenly buzzed and lit up with a new message. He hesitated for a moment before pulling away from Eddie's embrace to check the notification.

It was Tyler.


Tyler lay back on his couch, relaxed and comfortable as his old gym buddy eagerly sucked on his massive cock. It felt good, no doubt about it. Peter was a skilled cocksucker--despite being straight--and Tyler had trained him well to take his cock back in their freshman year. But even as he moaned with satisfaction at the sensation of Peter's mouth working up and down his shaft, Tyler felt like something was missing--a sense of boredom creeping in. He craved something else--something fresh and exciting. He wanted Ollie.

Tyler took another drag from the joint in his hand and leaned his head back on the couch while Peter continued to slobber on his cock. It felt good as always, but Tyler's attention wasn't on the cocksucker between his legs. He was thinking about Ollie. The kid was still so innocent in many ways, even after everything they had done together. He'd come a long way from the wide-eyed twink whose innocence Tyler had snatched away in an alley. He missed the way Ollie would look up at him through thick lashes while kneeling before him; how obediently he obeyed every command given to him by Tyler without hesitation.

Ollie had fully succumbed to Tyler's preferred brand of domineering, rough sex with a sweet side, but he still had that annoying little Jiminy Cricket conscience in his ear, worried about the dynamic between them. Tyler had noticed that the little voice inside Ollie was being amplified by his roommate--and now this guy in his writing class. Tyler grunted, half from frustration and half from Peter throating his huge cock like a porn star. He ran his hands through Peter's hair, encouraging him, and his thoughts drifted further.

He'd been neglecting Ollie for nearly a week--a punishment of sorts for confronting him in public about punching that bitch from Ollie's class who'd gotten too close to him. Of course that had been an overreaction. Hell, he was even proud of Ollie for standing up to him, and he'd made perfectly clear that he was still in charge by fucking him silly in a vacant classroom right after. But still... Even though Tyler loved how devoted Ollie was to him, he also enjoyed making him squirm with neglect. It was a power play and Tyler thrived on the control it gave him, but now he was starting to miss the twink's soft skin, his desperate moans, and the way he would cling to him after they were done. He was down bad for this kid in a way that he hadn't been for anyone in ages.

"Stop," he said abruptly, pushing Peter off of his cock.

"What's wrong?" Peter asked nervously, wiping strings of drool from his chin with the back of his hand.

"This isn't what I need right now," Tyler replied coolly. "Get out, Pete. Go see your girlfriend."

Peter nodded wide-eyed and quickly moved to the door, sensing that Tyler was in a mood. Tyler stared off into space for a few moments after he left, his cock slowly softening against his thigh. He picked up his phone and opened up his messages with Ollie. It was still near the top of his texts since the twink had sent him that stupid meme, probably in a desperate attempt for contact. It was cute.

"Come over now, baby girl," Tyler texted.

He knew that it would take Ollie might be upset that he had ignored him for the last few days. He might take a little while to arrive. But he would come. Tyler needed him here as soon as possible. As he waited for Ollie's response, he took another hit from the joint and went to wash himself up.


Ollie's heart skipped a beat as he saw a notification from Tyler on his phone. He pulled away from Ollie and wiped his tears, eager to see what he had said after days of silence.

His mind raced as he read the message from Tyler. "Come over, baby girl." That was all it said. It wasn't an apology, or a reply to his text from before, or any sort of acknowledgement of him as someone special. He should be upset, he thought, but suddenly none of that seemed to matter to him anymore.

Tyler had asked for him. He wanted him! He read the text again--baby girl--Ollie knew what that meant... Tyler wanted him to dress up in the schoolgirl uniform again. He felt a mix of excitement and nervousness at the thought of dressing up for Tyler again. It had been a while since he'd last done it, but he remembered how much pleasure it gave them both. But then Ollie looked at Eddie, who was still sitting close to him on the bed with concern etched onto his face. Ollie felt embarrassed by the situation; Eddie had helped him do his makeup perfectly last time, and now here they were once again...

"Eddie... I know this is weird," Ollie began hesitantly.

"What?" Eddie drawled out skeptically, not knowing what the text had been.

"Tyler..." he said, gesturing at his phone. "He-he wants me to come over..." he smiled slightly; "...and to dress up for him again." Ollie blushed as he said it, embarrassed for so many reasons.

Eddie's expression was stony, and he placed a hand on Ollie's shoulder. "Ollie, what were we just talking about? He treats you like shit. Why are all goo-goo eyed again?"

Ollie's eyes widened as he showed Eddie the text from Tyler. "But he doesn't treat me like shit, Eddie. He wants to be with me," Ollie said defensively.

Eddie sighed and shook his head, annoyed to be saying the same things over and over again. "Ollie, I know you have feelings for him but that doesn't excuse how he treats you."

"But what if I was just being stupid and he wasn't ignoring me? What if it was just Tyler being Tyler?" Ollie asked. "

Eddie rolled his eyes and shrugged, looking at Ollie with pity. He knew that no matter what he said, his roommate would still go over to Tyler's place.

"I don't know, Ollie. It's your call. But don't forget that you deserve someone who treats you with respect and kindness."

"I know, I know," Ollie said sheepishly as he looked at Eddie. There was a long silence. "Um... last time... you helped me with my makeup to make me look like a girl..." His voice trailed off, hesitant to bring it up but knowing that he needed Eddie's help once again.

His roommate sighed and ran a hand through his hair. "Yeah, I remember," Eddie replied wearily, rubbing his temples. "Babe, I can't keep doing this for you. You know how I feel about him."

"I know, I know," Ollie said quickly, feeling guilty for putting Eddie in an awkward position. "But please... I can do cute boy drag makeup but I can't do what you can do! I just need your help, Eddie. Please?"

Eddie's face was a mix of frustration and concern. His mind swirled with his options. He knew he should shut Ollie down and let his friend figure this out on his own--hopefully coming to the conclusion that it wasn't worth the effort, danger, and heartache. But Ollie wouldn't make that choice, of that Eddie was sure. So what? Eddie dolls him up to look like a sultry, sexy coed and sends his roommate off for a night of... what exactly? Hot sex? Degrading and dangerous, hot sex? Another night of Tyler digging his claws into Ollie's mind, body, and soul? Shit. Ollie was going to go to Tyler no matter what; there wasn't anything Eddie could do about that. So... would making him look perfect help keep the dominant, possessive man in a good mood? He looked back at Ollie.

"Fine," he snapped, harsher than he'd intended. "But only because I don't want you looking like some sad clown when you're trying to seduce someone." He dramatically rolled his eyes as he spoke.

Ollie couldn't hold back the grateful smile that spread across his face as Eddie begrudgingly agreed to help him get made up as a trap crossdresser once again.

The conversation lulled into an uncomfortable silence as they worked together to transform Ollie into the perfect schoolgirl fantasy--pink panties, pleated skirt, white blouse knee-high socks and shiny low heels; curly brown wig styled in pigtails held by two pink bows; cheeks rosy from blush. Eddie expertly did Ollie's eyes and lips before finally speaking up again.

"Sweetie... You're my best friend... More than anything else," he sighed heavily before continuing hesitantly; "And if someone hurts my friends... I get angry."

"I know, Eddie," Ollie replied softly as Eddie put finishing touches on his face. "But I really like him... he makes me feel good... I know you think that's crazy..."

Eddie looked away from the makeup and into his eyes with a sad expression on his face. "Babe, you can't keep making excuses for him."

"But he's just... complicated," Ollie said defensively.

"Complicated? Honey, that's just an excuse for bad behavior," Eddie replied firmly, focusing intently on Ollie's eyes with his brush. "You deserve better than this."

Ollie sighed, feeling Eddie's frustration, but he didn't know how to respond... so he didn't.

Eddie seemed finished with the makeup and stepped back to take a look. "Am I good?" Ollie asked quietly.

His roommate took a deep breath and let it out slowly, as if releasing anxiety. "See for yourself sweetie," he replied softly, gesturing towards the mirror.

Ollie turned to face himself in the mirror and gasped at how beautiful he looked--like an innocent schoolgirl caught up in something forbidden. His cheeks were rosy from blush, lips plump and glossy from pale pink lipstick; eyes framed by thick black lashes accented by eyeshadow that made his blues stand out even more; hair styled perfectly into two cute pigtails held with pink ribbons.

"You're... amazing, luv. Thank you so much." Ollie whispered as tears prickled in the wells of his eyes.

Eddie smiled sadly at him, seeing how much pleasure it gave Ollie to dress up like this for Tyler--even if it meant putting himself through emotional turmoil time and again. He studied him carefully before speaking up once more hesitantly--futilely. "You know... you don't have to do this if you don't want to..."

Ollie's painted eyes met Eddie's in the mirror and he played with his pigtails as he replied softly; "I want to."


Tyler sat on his couch, checking his phone every few minutes for a response from Ollie. He had sent the text almost an hour ago now and still no reply. Tyler was starting to get impatient; he wanted him here now. He knew that it was his own fault for ignoring Ollie for days, but he couldn't help himself--he'd needed some time alone after their last encounter; needed to make the twink suffer a little bit. But now that he had finally reached out to Ollie again, all he could do was wait anxiously. He wasn't supposed to be the one suffering... Tyler took a drag from his vape as he waited, scrolling through Instagram and trying not to get too impatient. His feed was a curated mix of body builders, twinks, and science memes, but he was just mindlessly scrolling past everything. Just then, his phone buzzed with a new message notification. His heart picked up speed as he saw that it was from "Little Ollie."

"I'm on my way," the text read simply, with a little white heart emoji.

A sort of relief washed over Tyler at the sight of those words; suddenly everything felt right again--the power dynamic restored just by knowing that the little twink was coming over in response to his summons. Why was his heart beating so hard? He didn't ever have this sort of emotional reaction to a twink and certainly not to an overeager repeat. But now Tyler felt like he himself was the overeager repeat. Jesus. He tossed the phone onto the coffee table without replying and took another hit from his vape, leaning back into his comfortable couch to wait for his baby girl's arrival.

Next: Chapter 7


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