Truly Adventurous

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Jimmy finally has an adventure that he enjoys.
2.6k words
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Ah, finally the week was over. Jimmy had some idea of keeping this special. Friday evening, he thought he'd go round to his flat and spend the weekend there. What could go wrong?

He just didn't want to spend the weekend in his boarding school. He was an adventurous sort. A boy, eighteen. And truly adventurous.

He didn't like the way everyone thought of him as the "tough" guy in school. He considered himself a "softie", and you couldn't deny that his features matched that. It's not that he wasn't tough; he certainly was. But then, people just didn't see him as a little effeminate, a little delicate and soft. The way he wanted them to.

So he decided to give himself a treat, by going to the so-called "oxford bookstore".

He found the arts and comics sections most interesting. However, as he crossed the door, he thought-"what if I chatted up that nice girl looking up that big book?"

He could see it was some sort of big photography book, by some big photographer. She moved off to the counter, leaving the book on the table. Jimmy just stood there, looking at it.

It was the photograph of a boat, the one she'd been looking at. The sun was setting behind the hills on the other bank of this river the boat was on, next to the pier. The water shimmered under the dim, gentle light, gently ushering to him, as if it had many a tale to tell...

Jimmy's reverie was disturbed by a gentle tap on his shoulder. "So, you like photography?", a tall, bespectacled boy a little older than Jimmy stood next to him. Jimmy felt an exciting rush down his spine as the boy gently ran his hand along Jimmy's back, and back to himself.

"Uh, yeah, I kind of do. A little," Jimmy gave him "the stare". He'd practised this in front of the mirror to perfection. It was this delicate look, yet ever so piercing. The slightest blend of titillating cheekiness was mixed in it, but it was ever so slight. He added a slight smile to it.

The boy smiled back."I have a couple of friends coming along in a minute. Would you like to meet them?"

"Yeah, sure."

Jimmy sized up the boy from his straight side. Jimmy couldn't take him. The boy looked like he could pin him down and smash him.

Then Jimmy looked at him from his other side. The guy was attractive. Nice sense of colour, the brown jacket, blue jeans, white sports shoes. Those fine hands, the lean shape...

Jimmy as a rule, liked "ephebic" guys, the ones that didn't have much muscle, no facial hair, and preferably, long silky hair and hairless, slim bodies.

"Hey, I'm Adrian, by the way," the guy said. Adrian... Just right. Adrian. Hot.

"And I'm Jimmy, hi," Jimmy replied.

"That's Ben, and there's Alan," Adrian nodded towards his friends as they walked in, towards them. Jimmy was dazzled. So, effin hot!

jimmy was a little confused here. He didn't want these three guys to just sit there and discuss photography with him till it was time for tea. He wanted these guys to go with him to his apartment, or their place, and smash him. Crush him. Screw him. Or something. Thoughts of a spitroast were building up in his mind. That tension building up inside him made his breath nervous.

"So, you like photography, huh?," Ben asked.

"Yeah... And that," he said, smiling and nodding towards a book.

"The adventurous lover."

All three looked towards the book and grinned. It had a picture of a woman with her hands cuffed, all in orangish sepia, her apparent lover next to her.

Jimmy thought he'd be his usual, cheeky self. He stood up, as slowly as he could, and went over to the poetry section. Limericks. A paperback title. A cool lime green cover.

As he got back, he could literally feel their eyes prance ever so covertly to his ass.

'No touching,' he murmured, as he gently brushed his hand against Alan's chair and shoulder. He felt he was doing this really well.

No, he countered. He was doing this too fast. And should he really be doing this? What would his parents think? He was a schoolboy, and he had some duties-

He noticed Ben literally burning him with his eyes.Ben really wanted to get inside him, maybe more than the others. Jimmy placed himself gently into his seat, and laid himself on his chair. He pointed his feet towards Ben, as if singling him out.

'That's it,' he concluded. He was going to seduce the pulp out of these three, until they just grabbed him and gave him the proper seeing too he so craved.

He made sure not to say anything first, they would ask him about this or that, and then he'd reply, and only then, ask them about this or that.

Seven thirty. Whoops. His alarm went off. He was supposed to be in his flat by now, the landlady would be wondering. He told them this.

They just didn't reply. It was understood. He wasn't going back to the flat just yet. Jimmy let that go.

He stood up, his jeans clinging to his legs, accentuating every exquisite feature, the tight shirt showing exactly what he was made of.

The gleam of the scarce street lights outside, the darts of light of cars racing past, the romantic, slow, music from speakers hidden somewhere, it all just created such a beautiful picture. He was the jewel that added to it, the centre-piece...

The four of them stood up, every eye on him, trying to catch a last glimpse of his graceful yet muscular figure, the buttons down just toshow a little glimpse of the smooth chest...

He quickly moved to the table and picked up an encyclopedia he'd noticed. It was on tanks or something. He grinned at them as the counter guy billed the book.

Perfect. Great. Finally he had that book! He'd wanted it for months, and now got it... That book. Yes.

'My little reminder of today's events', he thought to himself.

The car was a large one. Jimmy, off course, sat in the middle of the back seat, so Alan and Adrian sat on either side of him. Ben was driving. Perfect for Jimmy to tease him, get him to want to rip his ass apart and crush him and spank him till his knees felt wobbly and weak.

He let Adrian hold his hand. His spectacles suited him so preciously, the nice, black tortoise-shell frame, that teary glint in his eyes, such a piercing glare.

Jimmy suddenly realized what an error he might be making. What if they really were some kidnappers, or sadists or something? What if they raped him and killed him? What if they- oh no, it was too disturbing. But it was too late, he knew he couldn't run away now. He was totally vulnerable.

Alan was awkwardly fiddling with his phone.

'Hey, Alan', Jimmy said. The two boys thighs were brushing against each other, and he knew Alan just didn't want to shift, even though he must be extremely ticklish.

'Hey', he replied, his breath almost audible now. He wanted it. Any moment now he could start toying with Jimmy's hair, or kiss him, or push his head down for a blowjob.

It was a little sudden, which caught Jimmy off guard. Alan had run his hand along Jimmy's back, and now he had it across his waist, gently caressing and squeezing him.

"Hey... no touching,' Jimmy grinned as he protested.

Ben got out, after parking the car. He was a little bit jealous, Jimmy felt. He opened the door of the house next to the car, and Alan gently helped Jimmy out, even though he obviously didn't need it. They were treating him just the way he wanted them to, like some vulnerable, delicate thing. Wow.

Jimmy stood with his back to the door, as Ben slowly began to unbutton his shirt. Ben was near Jimmy's neck now, brushing his lips on that smooth bare skin.

Jimmy was afraid. Afraid of the fact that he was going to lose his virginity so unceremoniously. He was terrified of injury, what if they bungled it up and choked him? Or if he fell somewhere. He was terrified of what they might expect. Words such as "Deep throat" kept flashing around in his mind. He felt horribly guilty, he wasn't even supposed to be doing this...

The door flew open behind him, and soon enough he was bundled up inside, and onto a rug. He thought of the girl with the photography book, and found he didn't really relish being inside her anymore.

He was kneeling down now, the three others over him, as he hesitantly pulled down their jeans to expose the hard penises he now so guiltily wanted inside him...

He had no idea what was happening now. He just looked up at the faces above him, with the hands that gently stroked his hair as he slowly masturbated the closest penis, his mouth over its top, his hands oscillating to and fro in accompaniment.

He didn't want this to end here. He wanted more, all of his fantasies of so many nights came rushing back to him, what he wanted.

Ben lifted him up, and took him towards the bedroom. Now was the real fun, all set to begin. Alan and Adrian held hid hands down onto the table, as he bent over it.

"Wham!'

'Ýou dirty little slut,' Ben hissed.

Give it to me!'

Ben's hand gently groped the round perfection of Jimmy's ass, somewhat distracted by something. Perhaps, it was the musky smell of the room freshener, or the gentle, greenish light that spread from the little lamp. He squeezed.

"WHAM!'

He let fly again. Jimmy moaned, unable to resist under the weight of Adrian's and Alan's grip, totally helpless.

'WHAM!'

'WHAM!'

Ben let off two more spanks in quick succession. He felt powerful now, his prey helpless and completely helpless and at his mercy.

Jimmy was high with excitement. He felt a little awkward, too. He was beginning to feel himself getting hard.

Ben slipped his hand along the side, and slowly unbuttoned the jeans that Jimmy was wearing. He slid down the fly, and groped about at the boxers he found underneath. He touched the semi hard penis, and played with it, masturbating it.

'Do you guys have condoms?', Jimmy asked, in a terrified, subdued tone, against every single one of his urges. He knew he shouldn't risk.

Ben did not reply as he slipped one over his cock and peeled off Jimmy's jeans, and boxers, bringing them just above his knees.

No, he thought, changing his mind. He took the jeans and boxers right off, tossing them in a bundle onto the floor.

He applied lube onto his penis, and onto Jimmy's hole, then placed his hand's onto the boys waist, holding him firmly. He slipped his penis into Jimmy, gently in and out. Slowly.

Down below, jimmy felt the most awkward pleasure he'd ever felt. Am I really doing this? Is this me?

He somehow couldn't stop himself from thinking of himself doing pushups on the polished wooden floor of the hall, it served to distract him from the pain of being fucked up the ass for the first time ever.

He now felt Adrian slip his cock slowly into him, and Ben and Adrian together pounded him as he knelt over Ben, his prostate throbbing, the amazing pleasure of his screwing engulfing him.

"Thank you!', he screamed, as the two of them increased their speed. Alan stood wanking by the side, until he stepped right up to Jimmy's face, thrusting his cock towards him.

Alan grabbed Jimmy's head and held it still, mouth fucking the boy, his hips moving back and forth, his cock dipping in and out of Jimmy's throat.

Jimmy, in the middle, was excited. Triple penetration! He'd never expected he'd ever be fucked, both by men or women. He'd thought he'd been destined to go a virgin, but no, here he was, triple teamed by probably the hottest guys in town.

Adrian just wanted to subdue and bully this cheeky, cocky, little bottom bitch. He smashed his hand onto Jimmy's ass, over and over again. So, fucking, cocky...

The rain tip-tapped on the roof, it was the rainy season. Jimmy groaned and moaned, as he was spitroasted by Alan and Adrian. He looked up submissively at Adrian, as he sucked the hard penis that stood proudly in front of him.

Jimmy knew that the strawberry flavor condom covered cock could do a lot more just yet.

"Come on, fuck me missionary,' he pleaded.

Adrian lifted Jimmy's head, and let him lie on his back, picking up his feet and placing them over his own shoulders.

Ben entered the boy's mouth and throat as slowly as he could, as carefully and gently. This was a risky move. Alan brought out a long, thin cane, and brought it swishing down onto Jimmy's underfoot, as Adrian pushed himself inside.

Jimmy felt desperate, he brought his hand down to play with his own penis, pushing Ben away with the other if he was choking.

Jimmy was in a sticky mess. Lube spread all over his ass, and some saliva was around his lips, marring his doll-like beauty, yet making him all the more attractive in this crazy, sexual way.

His own dick was throbbing now. He left it. He wanted to wait a bit. Adrian was coming now, Jimmy could feel the condom fill up with semen, huge quantities of it. His anus throbbed, he felt hot.

Adrian pulled himself out of Jimmy, holding his legs in his arms. He let go, and held him in his lap while the other two fucked him, one in the ass and the other at the mouth.

Now the two of them brought up close to Jimmy's face, expecting blowjobs. Jimmy complied, Adrian holding him at the waist from behind.

Ben and Alan couldn't tolerate it anymore- they shed their condoms, and made Jimmy suck them off. Jimmy, deep within, felt happier- finally he would get jizz on his face!

He opened his mouth, smiling appreciatively as the two of them came, jizz splashing onto his face and lips, on the eyes, onto the cheekbones. His face glistened under the semen, as he rolled went into his mouth around to fully appreciate the salty, tangy taste.

Now all of them knelt down around Jimmy, who sat up on the edge of the bed, supporting himself onto his arms. They moved to satisfy him, sucking his cock, groping all around. They listened to his every demand, then rolled him onto his fours. Ben and Alan inserted their fingers into Jimmy's ass, tickling his prostate as best as they could, spreading the lube all around, while Adrian sucked him off.

The most heavenly feeling in the world; Jimmy was lost in an amazing high of ecstasy, until his own watery cum came dribbling out and oozed onto the sheets of the bed.

Jimmy collapsed lightly onto the mattress, tired, wondering what would happen next. His three fuckers held him down under the blanket, not letting him move.

Jimmy was amazed, he loved being held down like that; he didn't want to move, he just wanted to lie around with these three guys, in all their own filth, all the sheets crumpled and crushed, jizz all over his face like some slut-mask, his ass still slippery with lube. Jimmy felt like he was made of jelly, he couldn't move his legs. He wondered what he'd do if someone tried something now, he would be so screwed, so totally vulnerable, he wouldn't even be able to run. He turned to these three for comfort and protection in his weakness.

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63lsmith63lsmithover 8 years ago
NICE

Hope you have more chapters on Jimmy.

aclassyladyaclassyladyover 8 years ago

This story definitely lives up to the title. He was truly adventurous. Good story and waiting to see if there will be more to this.

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