The Telemachus Story Archive

Educating Chrissie
By Hooder

Educating Chrissie

“You’re looking suspiciously happy this morning.”

Sam looked down, smiling self-consciously.

“Come on, tell us.” Martin lowered his head, trying to get into Sam’s field of vision.

“It’s nothing. Really.” The boy looked up, blushing slightly.

“It’s Chrissie, isn’t it! She said yes!” Martin elbowed Dave in the arm.

Sam nodded, embarrassed.

“When?” Asked Dave, fascinated. Chrissie was a babe. Long blonde hair, blue eyes, and hitherto unreachable, or so it had seemed. He and Martin were both as jealous as hell.

“Tonight. I’m meeting her at the boathouse at nine tonight.”

Both Martin and Dave let out hoots.

“What the fuck does she see in you?” Martin was smiling, but the smile didn’t go as far as his eyes.

“I dunno. I’m not bad-looking I suppose.”

Dave snorted. “Yeah, if you’re into the little-boy-lost look. I’d have thought she was more the hunky jock type. And talking of hunky jocks, isn’t she going with Brad at the moment?”

Sam sighed. “Brad may be a hunky jock but apparently he’s not so hot in the sack. Seems Chrissie’s looking for a bit more of a goer.”

“Bit more of a… And she’s chosen you?”

Sam frowned. “Yeah she did. I might not be a muscle stud like Brad but I’ve got a reputation. And the reputation says I’ve got stamina in bed.”

The bell went for the first lecture and they stood up. “Well you lucky fucker,” said Dave, gathering his textbooks, “have fun.”

Martin’s eyes narrowed as he watched the boy leave.

* * *

Sam was humming happily to himself as he walked down the narrow concrete path between the warehouses, thinking about what they were going to be doing tonight. He’d had a call from Chrissie’s friend Juliet: Chrissie had managed to get out of drama club tonight so they could make it eight o’clock instead of nine, if he liked. “Give you more time together,” Juliet had said with a giggle.

Sam had been only too pleased with the new arrangement.

He was passing the end of one of the warehouses when a figure in a black paintball mask stepped out of the shadows in front of him. He began to turn - but there was a second one behind him. They grabbed him, a hand went over his mouth, and between them they dragged him into the warehouse.

Sam tried to kick and struggle, but they were a lot stronger that he was and it was hopeless. Once he was inside the room he began to struggle more - in the centre of the space was a table, and it had straps on it. One of the masked guys held him still while the other stuck a long strip of duct tape over his mouth and pressed it down well, gagging him securely.

They forcibly stripped him and restrained him to the table. Naked and feeling very vulnerable, he stared up with terrified eyes at the two masked faces. One of the guys was big and muscular, the other more average.

The bigger guy turned and took something from the shelf behind him. He held it up so that Sam could see it. It was a long black plastic cylinder with a kind of ball on the end. The ball had an odd-looking, short sleeve attached to it, made of what appeared to be transparent, softer plastic. The sleeve had small bumps running over the inside of it.

Sam knew exactly what it was; he’d had one for ages, and he used it a lot when he was watching porn. It was a vibrator with a milking sleeve. For a moment he wondered what the hell was going on. Why the fuck were these guys intending to -

Suddenly he realised – and he went ballistic. He yelled into the gagging duct tape and tore at the straps holding him to the table. They didn’t move.

The two guys looked down at him and even though he couldn’t see their faces behind the black paintball masks, he knew they were smiling evilly. It all fell into place: the phone call from Juliet had been a put-up job, the big guy was almost certainly that bastard Brad, and they intended to empty his balls so that his date with Chrissie would be a fiasco.

Well that was not going to happen. He didn’t fancy guys – they did not turn him on in the slightest. Eventually they’d get pissed off and let him go. He narrowed his eyes. I don’t have any choice, he thought, so get on with it you fuckers. Do your worst. You’re wasting your time: there’s no fucking way I’m gonna cum for you.

His cock was completely soft. The smaller of the two guys reached down and took it in his hand. Sam was expecting him to pull it, maul it, squeeze it, and start stroking it firmly. But he didn’t. The fingers of one hand teased along the shaft and over the head while those of the other began to massage his balls very lightly. He was touching so gently that it almost tickled. Almost, but not quite. To his utter astonishment his cock began to harden slightly. The fingertips continued to stroke, working leisurely on him – and in spite of his determination not to respond, his cock continued to get stiffer under the skilful teasing.

This was not fair. Guys did not handle cocks like this, they worked on them hard. This one seemed to have techniques that guys shouldn’t know. Sam started to struggle again, trying to get his cock away from those fingers, but the straps limited his options a great deal and any movement he could make was followed easily by the gently stroking fingers.

With horror he realised that he was almost fully hard now.

The smaller guy stopped his teasing, held Sam’s cock by just the base, and nodded to his accomplice. The muscular lad pushed the sleeve of the vibrator carefully over the top of the erect cock. He looked Sam in the eyes – no doubt smiling again – and switched the device on.

Sam yelled into the gag – he had never felt anything like that before. There was a huge difference, he realised, between doing it yourself and having someone else do it when you had no control over it. The soft sleeve gripped his cock and the small bumps took his foreskin with them as the guy slid it slowly up and down over the boy’s cock head. It felt more horny than anything he’d ever experienced and he felt himself quickly approaching orgasm. For a moment he gave himself up to the amazing feelings – and then the reason these guys were doing this to him came back to him with a slam. He struggled in the restraints and swore into the gag, but the vibrating sleeve continued to milk him slowly as if he were simply lying there and letting it happen.

No! He was going to cum! He screwed up his eyes in concentration but it made not the slightest difference: his body arched and his spunk shot out in long arcs that landed on the bottom of the table. The devilish device extracted every drop from him before the guy switched it off and removed it.

He lay on the table panting. The fucking bastards. His cock was beginning to soften. Well, he’d still be able to function with Chrissie. Fuck them. He waited for them to release him.

They did not release him. They left him strapped to the table while they sat down on wooden chairs and smoked a cigarette.

The smaller guy looked at his watch and nodded to the other one. They got up and came back to the table. What followed was a repeat of the first milking. For the second time the vibrator made Sam shoot his load.

That must be it, he thought.

But no. Another cigarette, and then they returned. This time the smaller guy stood at the side of the table. He produced a black rubber glove and snapped it on, then took a small bottle of lube out of his pocket and applied it to the middle finger. Bending down, he pushed his hand under the boy’s perineum and felt around for his hole.

Sam had never had anything up his arse and he fought to stop it going in, clenching his muscles as hard as he could. But it did no good - the finger slipped inside gently, and continued in until it was fully inserted. It felt very strange, and he thought to himself with grim satisfaction: that is not going to work. It’s not making me feel horny in the slightest.

The finger began to fuck him slowly, and the guy began to stroke his cock again, but this time just on the head. His fingers slid over the shiny glans, teasing all around it.

Sam felt stirrings of interest start again. No. This must not happen. He’d already cum twice and another one would probably finish him. The muscular guy was just standing there, watching what was going on.

The fingers on Sam’s cock were beginning to have an effect, and – to the boy’s horror – the one inside his arse was starting to feel worryingly horny now. He couldn’t stop himself imagining what it would be like to cum with that finger fucking him. It was a very seductive thought.

His cock was hard again and he waited for the vibrator to be be put back into position – but instead the small guy just carried on stroking around the cock head and pushing the finger in and out slowly.

It was impossible to fight these feelings. They crept up on him no matter how hard he tried to stop them, or to think of other things. It wasn’t like he was being milked hard; it was like he was being gently encouraged to cum. Nothing more than that.

And it was working. The boy felt orgasm approaching again. He knew it was pointless to struggle but he couldn’t help himself. Then his struggling turned into hip thrusting. The finger was fucking his arse, and he was fucking the ones on his cock. There was nothing he could do about it: he came for the third time. He closed his eyes in pleasure: that finger up his arse made it feel more intense than ever. His body shook as he came helplessly into the milking fingers. He collapsed back onto the table.

This time they did release him. They tied his hands behind his back and pulled a black bag over his head, then rushed to make their escape. He got free quickly, but even so, they’d gone, and when he looked outside there was no sign of them.

Swearing, he pulled his clothes back on, then looked at his watch. It was 8:55. The bastards’ timing had been perfect. He hurried down the path towards the boathouse.

* * *

“So,” said Martin, with an innocent smile, “how did last night go?”

A corner of Sam’s mouth lifted. “Oh, it went very well. Very well.”

Martin frowned and the smile evaporated.

Dave grinned. “Yeah? Tell us!”

“Well I don’t think Chrissie’s going to be interested in Brad any more.” The nascent smile on Sam’s face grew into a full grin.

That vibrator the two guys had omitted to take with them in their rush to get away had proved a big hit. Chrissie had never seen one before – and Sam knew exactly how to use it.

He’d had to take the milking sleeve off, of course – you didn’t need that with girls...