Riddle Me This

Disclaimer: I do not own incredibly much at all.

Summary: AU. Slash. When James is expelled from school, he has no parents or home to go to. One night he meets a man in a bar, an older man who charms his way into the teenager's distressed life.

Warnings: More will be mentioned if needed for future chapters.

Pairings: Sirius/Remus/Regulus, Tom-Voldemort/James. Past Tom/Death Eaters.


Chapter 1: A Chance Meeting

"James, I have been fairly tolerant of your misbehaviour over the last six years," said Dumbledore gravely, surveying the young man in front of his desk. "But I am afraid, that after last week's vicious attack on a student, you have gone much too far. I am going to have to remove you from this school."

James Potter's brown eyes widened, "Y-you're expelling me?"

Dumbledore gave a small nod of his head; "I am afraid so-"

"But…I-I have no where to go!"

"I have already notified the Ministry of your expulsion, James, where you go upon leaving this school will no longer be any concern of my own."

Young James Potter, the seventeen-year-old ex-student of Hogwarts School of Witchcraft and Wizardry sat in a secluded little corner of the Hogshead in Hogsmeade, he was nursing a tankard of butterbeer that he had bought about three hours ago. He had been expelled from school a week ago, he had no where to go – no home to speak of; he hadn't spoken to his friends since he had left the school last week, they probably didn't even know why he had gone. He was also down to his last few sickles now; his parents had died last Christmas and had left him with very little, as they had disinherited him the summer before their deaths. He had only managed to survive the summer because he had had two very good friends who had allowed him to scrounge off of them the entire few weeks.

But what could he do now? He didn't have enough money left for another night of accommodation, he had been kicked out of the Three Broomsticks because he was very low on money, that had been yesterday; last night though, he had spent the night down an alley way with a stray dog. This morning, because he had been very dirty (a state which he could not stand), he had broken into the house of an old couple after they had gone out for the day (luckily he still had his Invisibility Cloak on him), and he had used their shower. He had left a few coins with a little note to them, in payment for the shampoo and soap that he had used.

The miserable teenager took a sip of his butterbeer and watched gazed around the musty old pub sadly. He was running out of things he could do for himself, with no money and no hope of finding anyone who would want to take an unfortunate little whelp such as himself in, especially in Hogsmeade, he was destined for many more nights in alleyways. He watched as a tall, dark haired man entered the pub; he had seen this man in here the last couple of nights, the same time as himself. In fact, he had caught the man watching him a few times.

As James had thought, the man, a very handsome one indeed, after ordering his drink from the Barman started to gaze around the pub. Eventually, the man's eyes rested on James, and instead of bashfully looking away as he had done the last few times, James stared determinedly back at the man, who's eyes he could tell, were a vivid green colour.

James continued watching as the man smirked and walked over to his table, which is in a far corner of the dark pub. Finally though, the young man looked away, he wasn't so sure if he wanted the attention or not.

"Can I?"

James nodded, glancing hesitantly up at the man, who really was very, very good looking at a closer distance.

"Now what would a good looking young man, like yourself, be doing in such a seedy little place like this?" questioned the man, his voice was quite innocently casual.

James glanced at the man's face again, he saw an intent look in those green eyes; he then glanced back down at the table and gave a small shrug, "I have no where else to go…"

"Oh? No school you attend?"

James took another sip of his drink, trying to savour as much of it as he could, "Was expelled last week."

The man fidgeted around for a few seconds, he then produced a small bottle from a pocket; James watched as the man unscrewed the lid and poured a bit of the clear liquid into each of their drinks. "You look like you could use a bit of alcohol in you."

James chewed his bottom lip before giving a nervous smile, "Thanks…" he took another sip of his butterbeer, there was no added taste so he thought that it must have been vodka the man had given him.

The man had some of his own drink before speaking again, "What is your name?"


"No surname?"

"…James Potter."

The man nodded slowly, "Potter… Yes, I remember your parents, I am sorry to hear of their deaths."

James snorted, "Don't be, I'm not. They deserved it."

"Did they, now?"

"Yes," James took another drink, he was feeling a bit more curious now. "What's your name, then?"

The man gave a smirk, "I have many names, but you can call me Tom."


Tom surveyed the boy in front of him, many thoughts travelling through his mind, "How old are you, James?"

James nodded, "Seventeen at the end of July," some of the initial wariness he had been feeling before was starting to ebb away, perhaps it had something to do with the bit of alcohol in his system now. Whether it was the alcohol or not, he was feeling a more comfortable with this man, Tom, now.

"Why were you expelled?"

James dropped his hands to his lap and starting fiddling with them in his lap, "Bad wrap sheet… I eh, 'viciously' attacked a student a couple of weeks ago… Dumbledore is a bastard."

Tom raised his eyebrows slightly, "Yes, he is," James looked back up at him again. "It looks like we have something in common then, a dislike of Albus Dumbledore."

"Guess so."

Tom was silent for a few moments, he then picked his drink up and finished it off before looking back to James, "Have you anywhere to go tonight, James?" A shake of the head from the boy answered his question. "How about you come with me? I have plenty of room at my house."

James hesitated, "I…I um…I don't know…"

"Come on," said Tom, his voice lowering a little. "What harm can it do? What have you really got to lose?"

James finished his own drink off, "…Nothing…I guess… Promise you won't hurt me?" He didn't care anymore, whether he was making the wisest choice or not, but like Tom said, what had he really got to lose? He had no where else to go, no family and very little money…

Tom smiled reassuringly, "Harming you is far from my mind, James, trust me."

"Come here," said Tom, as soon as the two of them were out of the Hogshead. James did as he was told, not wanting to annoy the nicest person he had met since he was kicked out of the school. "I'm going to double Apparate us to my house."

"I can Apparate," said James.

Tom smiled slightly, "I believe you can, but I like to keep the whereabouts of my home a secret, until of course, I know I can trust my secrets with someone," he pulled James to himself and held the teenager. "Hold on."

James did so; it felt quite good to him, being held like this by someone, despite the fact that that someone was a man and he had never thought of himself as gay, or at least bisexual. But right now, he was feeling a bit more than just gratitude towards Tom, perhaps even a little lust and…physical attraction.

Within seconds, James found himself outside a large, and rather stately house much like the one that he had grown up in. Except, this house was on the top of a low hill, and his childhood home had been on a plain.

"This is it," said Tom, letting go of the teenager in his arms. "Riddle House."

James chewed his bottom lip and nodded slowly. The house was rather imposing, he could feel a large amount of energy coming off of it, and it was like an extremely powerful wizard lived here. Perhaps Tom was extremely powerful, he wasn't really sure.

Tom looked to James, "Come, you must be getting cold."

"I am…a bit," replied James, he followed Tom into the house. He immediately felt so much warmer inside, in the not-so-small entrance hall. He fiddled with his shrunken trunk in a pocket, as he followed Tom into a dimly lit room, which appeared to be a rather impressive study.

Tom smirked at the look of wonderment on James's face, "Sit down, make yourself at home," he went over to his drinks cabinet and took out a bottle of Firewhiskey and two fair-sized glasses. "Have you ever had Firewhiskey, James?"

James had settled himself down on a leather couch in front of the fire, "Yes… I nicked a bottle from the Three Broomsticks after we won the Quidditch Cup last year."

Tom nodded and poured them both a generous glass each, "What position did you play?"

"Chaser," replied James sadly; he missed Quidditch now, as well. "I was the Captain of my House team, as well."

"You must have been very good at it then," Tom handed James a glass and then he sat down next to the young man. "I was never a Quidditch player myself, I lacked quite drastically in the hand-eye co-ordination department, I'm a fairly poor flyer as well."

James smiled, "I was flying before I could walk, my gran used to say I must've been born on a broom."

Tom took a sip of his Firewhiskey, "From the sounds of it, you are a natural," James grinned. "I preferred just watching the sport and concentrating on my studies."

"Did you go to Hogwarts?" asked James curiously; he was feeling very comfortable now. It must be due to the alcohol, he though. The alcohol and the arm around his shoulders…

"Yes, I did," replied Tom, rubbing James's shoulder lightly. "When Dippet was Headmaster."

"I think he left the year before I started… What House were you in?"

"I was a Slytherin, Prefect and Head Boy."

James gazed at him, his eyebrows drawn together in worry. "Slytherin?"

Tom nodded, "Yes, is that a problem?"

James hesitated a little, "Well…no… It's just… I've always been wary of Slytherins, 'cause up until you, every single one that I've met have been absolute bastards," Tom snorted. "…I guess not all Slytherins are bad, then?"

"No, I guess not," replied Tom; he moved his arm from around James's shoulders and rested his hand on one of the teenager's thighs. "A vast majority of us are, though."

"But you're not so bad."

"Thank you."

James drank more of his Firewhiskey, not caring anymore that it was burning its way down his throat; he then frowned slightly. "Why are you being so nice to me? You barely know me."

Tom traced little patterns on James's thigh, noticing the boy was becoming very relaxed from the heat and the alcohol. "I may not know you well right now, James, but we can soon change that."

James turned his head so he could see the older man's handsome face, "I'd like that very much," his eyelids started to droop a little.

Tom took the glass out of James's hand and placed it on the coffee table, he then brushed a hand through James's messy black hair, "Are you tired?"

James stifled a yawn and nodded, "A bit, yeah," he was enjoying the feel of the hand in his hand the one stroking his thigh. Tom was looking even more attractive to him now, and James felt the need to do something quite daring right now. "Tom?"


"Can I kiss you?"

Tom raised his eyebrows in amusement, "If you want too."

James leaned forward and tentatively brushed his lips against Tom's; they were soft and moist and moved nicely against his own. The seventeen-year-old had certainly done his fair share of kissing while he had been at Hogwarts, but he had never gone beyond a snog and grope in a dark corner, unlike Sirius and Remus. He opened his mouth as he felt a persistent tongue flicking at his lips; he let the tongue into his mouth, allowing it to glide along his own.

Though his experience was limited James knew for certain that this was the best kiss he had ever had. Not that this surprised him, Tom was obviously far more experienced than himself.

Finally though, Tom broke the kiss, his hands cupping James's young face; "Would you like to continue this upstairs?"

James hesitated for a moment before nodding, "I'd like that."

James soon found himself spread eagled on Tom's huge bed, his top discarded on the floor and the older man laying half on top of him.

"I need to confess something," said James before he went any further, his lips already swollen from the kissing. Tom raised his eyebrows curiously. "I-I've…I've never had sex before."

Tom smiled and brushed James's flopping fringe out of the boy's eyes. "I had guessed, your timidity isn't something I would expect off an experienced young man," he pressed a gentle kiss to James's jaw. "Saying that, if you do not wish too, I will not make you."

James lifted his head and kissed Tom on the lips, "I do want too, I just… I don't know what to do…"

Tom trailed his right hand down James's pale neck and chest, down over the teenager's flat stomach, and he rested the hand on the growing bulge in James's trousers; James gasped at the contact. "You'll soon learn," he massaged James through his trousers, delighting in he wanton moaning it caused. "There is a lot that I can teach you, James."

James whimpered and pressed himself into Tom's hand, "…I'm…a willing student…"

"Good," Tom slowly undid James's trousers, as he started kissing the young man again.


James lay contented, and only a little sore in Tom's bed, his head on the older man's chest. He now had something else in common with Sirius, he could now identify with what his best friend said about sex; Sirius had been right, sex was fantastic. Though his first time had been a bit painful, it was much better the second time around; he was rather hoping now that he could hand around and learn more off Tom, like the man had said.

"Still awake?"

James smiled slightly, "Yeah…just thinking," he nuzzled his head against Tom's chest when he felt the man's fingers thread through his messy hair.

"What about?" Tom was gently massaging James's head.

"Just something my best friend used to say when I was at school…about sex being the best thing ever."

Tom smirked, "And what do you think about it?"

"Well, now that I've actually done it," James lifted his head, a mischievous glint in his brown eyes. "It's certainly up there with Quidditch and chocolate."

Tom raised his eyebrows in amusement, "It seems I have a bit of work to do to push it to the top of your list."

"It seems so."

"Little brat."

The teenager snorted with laughter, "Thanks."

"You are very welcome, James."

James put his head back down on Tom's chest and gave a deep sigh.

"You're a bit young to be sounding so forlorn," commented Tom quietly; he was starting to get quite sleepy. "What's wrong?"

James chewed his bottom lip, a nervous habit of his; "I may as well leave now, you're not going to want me to stay for long… Ow!" Tom had just clipped him around the head, much like his mother used too.

"Don't make such stupid assumptions, James; I wouldn't have invited you here if I had no intention of you staying."

James frowned slightly; he could feel a bit of a change in Tom's charmingly nice demeanour… Perhaps that had only been a ploy to get him into bed. "I still don't understand why you would want me, though…"

When Tom spoke this time, there was an air of impatience to him; "I like you, James, and I rather fancy the idea of getting to know you better."

James still wasn't entirely convinced, "I think you've gotten to know me quite intimately, wouldn't you say?"

"James, I may like you, but that does not mean that I will tolerate such attitude from you."

James was absolutely certain now that Tom's charming exterior up until now had been an act; he could tell that he was only on the edge of discovering the true Tom Riddle. "…Sorry…"

Tom ruffled James's hair, "Apology accepted… Let's get some sleep and discuss this further in the morning, all right?" all traces of impatience and annoyance gone from his voice now.



By late the next morning, James found himself on his back; his mouth fully occupied, his legs around Tom's waist as the older man thrust into him. He groaned into Tom's mouth and clawed at the man's back; he could certainly get used to this in the mornings.

"Oh god… Tom!"

James came hard and loudly, a new sheen of sweat breaking out over his body; he whimpered as Tom continued to pound into him until he too, reached his completion. The teenager let his legs fall back to the bed, and tried to catch his breath, when Tom rested on top of him and him deeply.

"If I didn't know any better…" panted Tom. "I'd say you've had many lovers before myself."

"I'm a fast learner," James shifted a little, or at least, he tried too. "Can I…have some breathing room?"

"Oh…sorry," Tom carefully pulled himself out of James, and settled down next to him. "I look forward to teaching you much more…"

James grinned a little, "I thought you said we were going to do some talking this morning?"

Tom had finally caught his breath, "I did, didn't I?" he turned onto his side and propped his head on a hand so that he could gaze down at the flushed James. "As I am perfectly fine with you staying here, there are no rules, really. You can go wherever you please within my house and the grounds, and do as you please, within reason, of course… However, saying that, there is just one rule," James raised his eyebrows. "The drawing room is out of bounds, you are not to go into that room at all. It is the room to the right of the staircase; you won't be able to mistake it, as it is the only room downstairs that is always sealed."

James still had his eyebrows raised slightly, but he nodded; he could tell from Tom's seriousness that is he were to attempt getting into this drawing room then he would most definitely pay for it. "All right… Can I ask why the drawing room is out of bounds?"

"I'd rather not say… At the moment, anyway."

James yawned and stretched, arching his back in the process before slumping back down into the comfortable bed; he was fully intent on having another nap.

Tom pressed a kiss to James's sweat dampened hair, "At your young age, you shouldn't be exhausted so quickly."

James smiled sleepily, "Talking of age, I don't know how old you are."

"I am thirty-eight this December," replied Tom honestly. "And apparently I have far more energy than you do."

"Maybe you can whip me into shape…" mumbled James, as he started to drift off to sleep; it didn't bother him that the man next to him was the same age as his parents would be if they were still alive. In fact, he didn't feel that he had a care in the world right now.

Tom pressed a kiss to James's slightly parted lips, "You have another sleep, love, we can talk again later."



A/N: How was that for the first chapter to yet another new story?

Next Chapter: A month later. James is cornered by Lucius Malfoy and learns a few things about Tom. James is still oblivious to Tom's real identity and he pens a letter to Sirius.