Story – Caught (pt.2)


By Ian Kovnats (Gaystoryman)

Copyright © 2008 ? All Rights Reserved

Part (2)

The question caught him off guard. He couldn’t help but notice that the man holding his camera was about his age, had a rather nice looking face, but the way he kept looking at Terry’s crotch seemed a bit unnerving. It was almost as if he couldn’t make up his mind about what he was staring at, which kept Terry feeling apprehensive.

Just someone I know

He must have said Damian’s name when he was jerking off, but he didn’t remember. It was all a blur really, other than he knew he had felt good, at the time, until now. Looking up, he couldn’t make out if the guy was disgusted or just unsure, as he stared down at Terry.

A quick glance did notice a bit of a bulge, which sort of relaxed him, but the solemn look on the guy’s face was disquieting, none the less. The way he had his lips closed so tightly, drawn even, wasn’t a good sign. Then too, he hadn’t made any threatening moves, yet.

You one of those porn actors?

Terry blinked, not sure what this guy’s game was. He was still holding onto the camera, rather tightly too which added to his nervousness, but his voice didn’t sound menacing, and honestly, his look wasn’t all that angry looking.

Uh, no, no I am not

Oh, so uh, what’s with this? You uh, auditioning or something?

There was something in his voice, when he asked, almost wistful, as if he sort of wished that was the case, plus when Terry had said he wasn’t a porn actor, the guy seemed to sag a bit, as if disappointed. This was becoming a bit weird, as he pulled his pants back up, careful to keep his eyes on the stranger.

Why? Uh, bit personal, don’t you think?

I suppose, that a problem?

Uh no, guess not, so uh, who are you?

Jesse, my folks own this property.

Oh, I didn’t, I mean I thought… I am Terry.

Cool, uh yeah guess the fence does need mending, and new signs put up.

At first he wanted to just sort of give him some smart ass reply, but the way he was standing, shifting his stance as if he had something on his mind, made him bite his tongue a bit. There was something different about the whole thing, not like he was yelling at him to get off private property, or threatening really.

Uh, I didn’t mean to uh trespass, uh didn’t see any signs, and the fence, well it is pretty well fallen down, uh, I’ll take my camera and leave.

It’s cool, I am the only one who comes out this far, uh, here, so uh, why the camera? You trying out for one of them internet porn sites or something? That would be trippy.

Terry reached forward, to take his camera, but the way Jesse looked, how he said it, made him hesitate a bit. Fuck, why not he thought, be better than saying he wanted to watch himself jerking off, added a bit of spice to it too.

Uh yeah, sort of, just sort of doing it on a lark.

Cool, be rather fun, all those chicks to dick, uh, if you get selected, still, it would be cool, plus it would make it easy to get chicks, not that you would need to, I am sort of, well, sounds cool man.

Uh huh, something to brag about I guess.

Yeah, it sure would make a guy’s friends jealous, I mean to be getting all that pussy, uh, you think I’d stand a chance? I mean I am not as well built as you, but it would be fun to see.

The way he looked, when he asked was rather arousing. Terry couldn’t quite put his finger on it, but he was definitely getting the impression that Jesse was a bit, well, more like a kid, than anything else. Like he was good looking, seemed to be close in age, but he acted like he was maybe 14 or so.

Well, uh, you have to be at least 18, and I don’t know, I uh guess you could uh try.

Turned 18 couple of months back, so that’s not a problem, uh, does it have to be a video? I uh, we don’t have one.

He felt relieved at that bit of news. For a moment he was worried, but hell if Jesse was 18, why did he act like he was just finding out about sex? Maybe it was living in the country, but the city wasn’t more than a good 15 minute drive, so was he one of those kids whose parents kept him at home? Christ just what he needed, to be caught whacking off on some cult property or something.

Oh, uh, well, yeah it uh does, I mean least I uh think so.

That sucks, uh, those cameras aren’t cheap, uh, can you rent them?

Actually, uh, this one is about $400, which isn’t bad, and I really don’t know, maybe you can borrow one from a friend?

I don’t have that kind of money, or friends with that kind of cash. Besides I don’t think any of my friends have one, then if they did though, I’d have to explain, but it would be kinda fun, I mean to uh, you know, see if they thought I was good enough, be a great way to get laid too.

He really did think Jesse was that naïve, the way he kept trying to bring up about girls, about sex. It was like he found someone who could tell him all he didn’t know, yet looking at him, he didn’t seem stupid, or ignorant. He had to know about sex, about this stuff, Christ he was 18, where did he go to school? Hick High? Still, it could be an act, but he just didn’t look like the type who could be anything, other than what he appeared to be.

Yeah, uh…

Maybe you could… uh nah, never mind

No, go ahead, what?

Well, I mean, you are here and done yours, maybe uh, maybe you could take one of me? I mean, I can maybe pay you for the film, and you could uh, maybe send it with yours?

You serious?

He had blurted it out, and saw how Jesse seemed to take a step backwards, surprised by Terry’s words. It was like he knew he was doing something wrong, or thought he was. Besides, looking at him, he wouldn’t mind seeing him jack off. There was no mistaking that Jesse had a decent body on him, and might be one of those that looked even better without clothes.

Well, yeah, why not? You think I’d stand a chance?

Uh, sure, I guess, but uh, you sure about this? I mean if they uh, I mean you’d have to uh, oh hell, sure, if you want, I could uh record you, I have some spare disks.


Uh yeah, it takes little discs, like the music one’s, they uh, don’t use film, it’s uh all digital.

Cool, bet they are expensive?

Nah, about $4, so sure, I mean if you really are serious.

Yeah I am, uh, what do I have to do?

You really are 18, I mean you gotta send ID and all, so uh, you are, right?

Yeah, I got my ID here, see.

He took the plastic license from Jesse’s hand, feeling how warm the hand was to his touch. Terry looked at it, and did the math in his head, and Jesse was right, he was 18, not feeding him a line.

Well, uh, seeing as how I can move around, uh, you just sort of strip, then well, you know, you play with yourself, sort of make it sexy, not just uh, jack off, but uh, build up to it.

Like what you were doing?

Uh yeah.

Cool, yeah I can do that, uh, you think I have a shot?

I don’t know, I suppose.

So, uh, do I take all my clothes off? I mean you didn’t, so do I…

Well, I didn’t have anyone to hold the camera, so I tried to just, you know, do what I could in front of the camera.

Oh, maybe you want to redo yours? I could hold the camera for you, course you’d have to show me how to work it, but, I mean I could do that if you want, I mean seeing as how…

Damn, the idea of jerking off, of shoving his toy up his ass, while having Jesse watching, recording it, was adding to the ache in his crotch. The whole idea was almost too good to be true, but maybe he was lucking out. Like, how long could he go without something decent happening?

Maybe after, I uh, I mean kind of hard to do it again, so soon.

Yeah, I hear ya man, so, do I lay down after I strip? Or should I do it all standing up?

Well, uh, maybe start off standing, and uh, well, then yeah maybe lay down on the blanket, to uh, finish.

Okay, what about, I mean, you had that uh, do I uh need to, I mean that looks a bit…

Jesse had turned his head, to look down at the blanket, where Terry had left his dildo. It lay there, next to the lube. Looking at him, Terry could see he was sort of puzzled, unsure of himself, as if he didn’t really know what it was.

The idea of filming him, of having him shove a dildo in his ass, while he watched was making him feel rather warm, sweaty even. He wiped his forehead, and realized that Jesse was waiting for an answer.

Oh no, well, I do have a smaller one, so uh, yeah, if you want, it uh, it might help. They uh, they don’t require it, but uh, do say it would uh, be better if you used one.

Weird, uh okay, I suppose if it helps, I can try, does it hurt much?

Nah, not if you do it right. Takes a bit to get used to at first, but its cool.

How do you, I mean I never used one of them, how do you know you are doing it right?

It’s not hard, uh, you could practice first, see if you uh, want to use it.

I don’t know, that one looks awfully big to go in such a small place, it has to hurt.

Here, this one is a lot smaller, and if you use enough lube, well, it just sort of slides in real easy.

Oh, I can use this one instead of the bigger one? Won’t they sort of, you know not count as good?

Watching Jesse holding the smaller dildo he had pulled out of his bag, he couldn’t help but feel his dick jerk a bit inside his pants. Christ he was getting hard already, even after shooting a huge load minutes earlier.

Shouldn’t matter, for a first time, it’ll be just as good.

So, how do I? I mean try it out, do I…

Just uh, well, drop your pants, and well, you bend over and then you sort of get it between, and find the uh, the spot, then slowly work it in, uh you push in, only uh when you are comfortable, stop if it hurts, till you uh, get used to it, then, uh, well…

I don’t know, uh, what if I uh, what if it gets uh, well…

I got stuff to clean it with, just make sure uh, make sure you put enough of the lube on it, first. Uh, maybe put some in your uh, in there first.

Huh? How do I? Man there is a lot to this.

He could see the concern in Jesse’s face, the way his nose was a bit wrinkled up, the corners of his mouth turned up as well. His eyes were narrowed, and you could tell he was thinking about it, wondering how to do all that Terry had explained to him. He really was that much of a rookie, which made him a bit nervous.

You just uh, well put some on your fingers, and uh, well you slide them uh in, and uh, well coat the inside, then put some on the uh, dildo, and well, get it there and just, work it in, as you uh, as uh when it feels okay.

How much, how much of that do I use?

Well, uh, I guess till you feel like uh, hell, you uh, want me to do it for you? I mean, if you uh…

I guess, I mean if uh, man this is weird, but I don’t know how much to use, or how to tell, so, uh, this is weird man.

Yeah, I had to have someone help at first too, uh, it was no big deal, so if you want…

Okay, yeah, that uh, that would be cool then. I kind want to do it right, it be so cool to land a gig like that, make all my friends jealous.

He couldn’t help but laugh, which made Jesse smile a little. Seeing that grin, made Terry’s heart skip a beat, as it really lit up his face. He looked so innocent then, and his eyes were sparkling too, as if he was proud of himself. It was like a peacock, strutting its feathers for the first time.

Jesse moved over to stand on the blanket, and he turned his body so that his back was facing Terry. He stood there for a moment, then glanced back and gave Terry that grin again, as he unbuckled his belt.

What if it uh, what if it hurts too much?

Just tell me, I’ll stop, but don’t worry, you’ll do fine.

Really? You think so?

Yeah, I do.

With that, Jesse turned his face away and looked down as he unzipped the pants, then pushed them down his legs. Terry watched at how quickly the young man dropped his pants, and at how white his flesh looked. Least most of it, as there were some red welts across his buttocks, but he didn’t want to ask, afraid of maybe Jesse changing his mind.

Yet, as he stepped up closer, he could see several of the red welts, not old, criss crossed over the entire buttocks. He let his hand reach out, to touch the outline of one, felt the cheeks tremble to his touch.


That’s okay, it doesn’t hurt anymore.

Your uh, your dad do that?

Jesse turned his face around, and looked up at Terry. There was a darkness in his eyes, a sort of sadness he hadn’t seen before. It gave him a bit of a chill, as he looked at Jesse, then at the red welts.

No, that was from the Pastor, my uh, penance for uh, well, just penance for somethin’ I did. Is it uh, is it gonna make my chances worse?

He sucked in his breath, as he thought about it. It wasn’t that he was religious himself, but from what little he did know, and had been involved in as a kid, the preacher didn’t go around tanning someone’s bottom, certainly not an eighteen year olds. It obviously wasn’t something Jesse wanted to talk about either, as he swallowed, and tried to put it out of his mind.

Huh? Uh, no, no it won’t.

Okay, I guess I am ready, if you are.

Terry could see how tense he was, how his legs were stiff, and yet as he reached down for the bottle of lubricant, he felt the excitement growing. It wasn’t everyday he got to lube up a straight farm boy, which Jesse obviously was. Plus, he’d get the double reward of having it all on Video, including him jerking off.

He poured some of the lube onto the tips of two fingers, and then with one hand, he gently pushed the two cheeks apart. Jesse spread his legs a bit wider, adjusting to the touch. Terry put the lubed fingers near the small of his back, then slowly let them slide down the opened cheeks, along the tender flesh of the valley between.

The two cheeks seemed to quiver a bit, as his fingers moved down, and between them. He could hear Jesse holding his breath, as the fingers finally came to Jesse’s rectum. The muscle was tight, and the whole body suddenly seemed to tense up even more.

Take a deep breathe, hold it, and let it out as you feel my fingers push in, okay?

Jesse just nodded, as Terry heard him taking a huge breath in. He waited a second, before he began to push forward with one finger, feeling the muscle resist him at first, then gradually ease up, so that his tip began to move inwards.

Terry felt the body shake, felt the young man release his breath, then suck it in again as the tip of the finger worked a bit more in, a bit more past the tight muscle. He could feel how tight he was, how the muscle clung to the edges of his finger tip, despite the lubricant.

His other hand held Jesse by the hips, as he let his finger stop, the very tip just inside. The body was shaking a bit, but soon calmed down, as he then pushed in a bit more, keeping the pressure steady and slow. Terry heard Jesse grunt as the finger pushed inwards. It felt so warm, so tight that he closed his eyes, pushing the finger in a bit more, until he felt his knuckles pushing up. He had his whole finger in, and so far, Jesse hadn’t asked him to stop.

He twisted it a bit, which made Jesse moan, a sort of soft whimper really. There was no doubt he was enjoying the finger in his hole, as Terry began to slowly pull it out, but before it could pop free, he stopped. He let it stay there, letting Jesse get used to it, then after a slow count of three, he pushed back in, feeling the muscles grip his finger, as it slid past them.

Slowly he let his finger go in and out, not wanting to rush it, or make him feel uncomfortable. At the same time, he wished he could reach down, and grab his own cock, because it was turning him on like nothing else had before. Hell, he’d love to reach out and grab Jesse’s dick, but he knew that would be a deal breaker.

Getting control over himself, he pulled his finger out, and heard the sigh from Jesse. He quickly lubed the smaller dildo, and placed it, as he had his finger. Just as then, Jesse tightened up, his cheeks quivered a bit, as Terry began to slide the head of the dildo down between the cheeks.

As before, Jesse shuffled his feet, spreading his legs further apart, or at least as far as he could given how his pants were at his ankles, restricting his movement. Terry could hear Jesse’s rapid breathing getting more ragged, as the dildo came to the hole, and he gently pushed it forward, so that the head was just lightly pushing the tiny muscles apart.

Jesse grunted again, as his body shook, and he looked back over his shoulder at Terry. His eyes were wide open, as he looked hard into Terry’s face.

It hurts a bit

I know, just take a few deep breathes, then take another, hold it, and slowly let it out, the pain changes, and it goes away, don’t worry, you can do this.

I am trying.

You are doing fine, go on take a few more deep breathes

Terry waited until Jesse had taken several breathes, then leaning over, to whisper softly into Jesse’s ear, he told him to take one more, to hold it, and to slowly let it go.

As he heard him begin to exhale, he pushed firmly on the back of the dildo, feeling the resistance from Jesse’s muscle, then suddenly he was in, the muscle had given in. He heard Jesse cry out, but he didn’t tell him to stop, as he continued to gently push forward.

He could feel the body all tense up, feel the muscle inside trying to prevent the thinner dildo from going further, but his was the stronger force. His hand pushed on the end, while the other reached around, to hold Jesse, at his waist, pulling him back towards him and the dildo sliding into him.

The touch of his hand over Jesse’s bare belly made him tremble a bit, and he could feel the stomach ripple too, as he held him firmly, pulling back. There was no resistance from Jesse, as his body sank backwards, as he managed to slide the dildo in past the tiny pink hole. He could hear him groan, feel his body shudder, as his insides were gradually spread apart.

Feeling Jesse’s whole body shaking was making Terry sweat, as he held him close. His hand pushing the dildo in, his other hand feeling the muscles rippling under the skin of his stomach. The sound of Jesse’s panting made him moan himself, which he quickly cut off, fearing it would tip Jesse off.

Uh you can reach back, and move it in and out, just take it slow, okay?

Uh, it hurts, I don’t know man, uh maybe…

It’ll be easier later on, you’ll be able to uh spread your legs more, that’ll help.

You sure? It isn’t all that bad, but I don’t know. It’s weird feeling something in there.

Yeah well, you’ll get used to it, go on, you reach back and uh, you move it in and out, just don’t take it out, until you are ready.

Terry stepped back as Jesse’s hand came back, and brushed past his. It was like touching something electrical, the energy or spark just seemed to make his whole body flinch. His eyes were glued to the way the hand moved, as he grunted a bit, as he tried to work the smaller dildo in and out.

He couldn’t help but stare at the butt cheeks, at how they glistened from his sweat, and how they moved as he tried to get comfortable with the dildo inside. Terry felt his own cock stirring, and he adjusted his own package, as finally Jesse seemed to have had enough.

Taking it out, he held it in his hand as he stood up, grunting a bit, and turned his head to stare at Terry. His eyes were rather sparkling, sort of like saying he was proud of himself, at being able to do it.

The pain wasn’t as bad as I thought.

Yeah it goes away quickly, as long as you take it easy, uh, well, you ready? I mean to make your video?

Jesse nodded as he bend down, to let the dildo rest on the blanket, and pull up his pants. As he zipped up, and turned around, there was no mistaking the thick bulge in the front. The dildo had certainly gotten him excited, as Terry bent down, and taking his rag and the plastic bottle of bleach, began to clean the dildo.

He reached inside his bag, pulling out some bottled water, that he ran over the dildo, then he pulled out a fresh bottle of lubricant. Looking up, he could see how attentively Jesse was looking at him, watching his every move.

Standing up, he picked up the camera, taking the disc out and putting it away in his bag. He grabbed a fresh one, inserted into the compartment, shutting it and looking up at Jesse.

Okay, so, uh just sort of try to ignore me being here, okay, don’t look at the camera if I move out of view, it’ll seem more natural then, okay? Ready?

Jesse looked at him, and nodded.

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