Curious Webcam Fantasy Pt. 03

We continue Gersh's adventure in curiosity in the middle of the two young jocks' cam show for an active audience....

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*beep* *beep* menu item again. Two fingers in hole. Tanner yells to Gersh, "time to flip over and show that pretty hole of yours again..."

Gersh is a bit apprehensive not being sure what to expect. He turns over and exposes his back side. Wearing a jockstrap for the first time, he realizes how exposed he is now that he has turned over. Then he feels two hands spreading his cheeks apart exposing his hole. And now, he feels some cool liquid dripping over the hole giving him a weird and wet feeling. He doesn't have much time to process this wet feeling before a finger is invading him and stretching him out. As soon as he relaxes with the one finger, he suddenly feels a second finger invade him and pokes around a few times. At first, it is painful and uncomfortable. As the fingers stretch him out, it begins to feel... well, not good... but definitely not bad. Tanner moves his fingers in and out for a bit before stopping. Gersh sighs.

"I think that may be enough of a tease for now" says Tanner. "That is definitely one tight hole. I hope he is going to be able to take this huge cock later tonight.... Maybe we need to plan some stretching fun... Gersh turn back around. I want to see how that cock of yours is filling in that jockstrap. Wow! Someone definitely got excited from a couple fingers in his ass. Wait until you feel something much bigger."

Tanner continued, "And while we all stare at Gersh's cock restrained in that jock, I am posting our next goal which is dual handjobs. Brandon and I are about to show Gersh how to jerk-off two guys at once. Only another 1000 tokens for that new experience for Gershie. And we will just work against our tip menu while we get ourselves to 1000 tokens."

*beep* *beep* "thank you for the tips" says Brandon.

*beep* *beep* menu item - 5 face squats

*beep* *beep* menu item - remove blindfold

*beep* *beep* menu item - 5 face squats

"Wow!" Brandon continues. "The tips keep rolling in. I can't remember the last time the tips flew in so fast. We have three menu items before I can even jump on the first one... this is going to be fun. And we are making our way so close to that next goal already. Gersh, time to lay down again on your back - face up."

Gersh lays down not entirely sure what to expect, but he is getting somewhat accustomed to being told what to do. He feels someone standing over him - thinking it is Brandon - so he is ready for whatever happens next. And then he feels it... pressure on his face and nose. It is there and then it is gone. Gersh guesses this is another squat. And within a few seconds, it happens again... and again... and again."

"Time to remove that blindfold, Gersh" says Brandon. "Then we can start again. This time you will get a great view of what is happening for the first time."

Gersh suddenly has light in his eyes. He can see. And before he has time to really get too comfortable, we sees Brandon's ass dropping onto his face. He nearly screams in horror. He sees Brandon's pink hole coming right towards him again. And again.

*beep* *beep* 5 face squats

"Wow! Our fans really like these face squats" says Tanner. "I think I need in on this action! Brandon, my turn."

Gersh suddenly sees a switch in asses in his view. And before he knows it, Tanner slams his ass right into his face. Tanner is a bit more aggressive and rubs himself on Gersh. Luckily, this goes quickly as he counts five face squats.

*beep* *beep* grind face

Before Gersh realizes what is happening, Tanner has turned around and laid down on top of him - in a sixty-nine position. He started to rub his jock covered cock all over his face. This definitely was pushing Gersh, and he wanted to touch himself but his hands remained tied. To his surprise, his jockstrap started to get some mouthing on it from Tanner while he was sitting there.

*beep* *beep* blindfold

*beep* *beep* finger ass

"Just a little tease... we don't want you cumming for a long time" says Tanner before laughing and removing his mouth and giving Gersh's cock a good rub. He grinds his face a bit more on Gersh before climbing off. "Hoping you liked feeling that dick on your face. There's gonna be a lot more of that real soon. I see how hard you are getting. Hope you don't explode."

Gersh sits back up awaiting what is next. And before too long, he is sitting in the dark again unsure what to expect.

"Wow! We are hitting these menu items so quickly tonight that we can't keep up. We are only a few tokens away from our next big goal. Keep those tokens coming" says Tanner. "Oh, and Gersh time to show your hole again. Turn over!"

*beep* *beep* finger ass

Gersh turns over and shows his ass. He thinks he is getting off easy this time. He sticks out his but as best he can. Then he is in a bit of a shock when he feels multiple hands groping his ass and rubbing that hole. He starts to anticipate more.

"What a nice tight hole you have, Gersh" said Brandon. "I can't wait to violate it with my huge dick. For now, I think you just get a couple of fingers. I'll be nice and add some lube too. We have a double for this, so we may have some fun here"

Gersh clenches in fear and then he feels fingers going into his hole. First, it is one finger. Then, it is a second one. He still isn't sure what to make of it.

Tanner starts to type on the chat. If I can get 250 tokens within the next sixty seconds, we can move from two fingers to this shiny butplug that I am holding in my hands. We can keep this a surprise from Gersh. Let's see if you can do it....

*beep* *beep*

*beep* *beep*

*beep* *beep*

*beep* *beep*

"Wow, guys! This is amazing. I can't believe you did that so fast. Gersh is in for a treat! And that also hits our goal. We'll share our treat with Gersh first, and then we will do some jerking. New tip goal in a few more minutes" said Tanner.

Hearing that Gersh was a bit worried. He knew Tanner had a sadistic side to him. Brandon continued to keep his fingers moving in and out of him. It definitely was hard to get both those fingers in, but Brandon did. And it did start to feel a little good. Just as Gersh was warming up to enjoy that feeling, Brandon's fingers disappeared. Then he felt that cold liquid again around his hole - this time he knew it was lube of some kind. Then, it was cold, metal rubbing against his hole. He had no idea what was going on, and then he felt the metal pushing into his hole. This hurt. It felt so big."

"Push out" said Tanner. "Relax! This is coming in one way or another..."

*beep* *beep* blindfold off

Gersh just did as he was told. And then he felt/heard a pop. It must have gone in. He definitely felt very full and overwhelmed with emotions.

"Why don't you take a look at your new accessory?" said Brandon.

With that comment, Brandon took off the blindfold. Gersh looked down. He couldn't easily see anything, but he definitely felt it.

"I think we should leave that in for a bit. Let's get you stretched out" said Tanner.

"And now, I want to get my cock rubbed," said Brandon. "Time for our jerk off session. And I think I saw a tip to remove the blindfold. I'm going to get this thing started with the blindfold on, and then we can take it off after Hersh has cocks in hand. Hope everyone is ok with that."

"Hersh, turn over and sit up," said Tanner. "It's time for some fun. Here is the drill. Gersh is going to jerk us off. He has two hands, and we have two cocks. So, perfect here. We sit on either side of him. And now for the fun part, he is going to jerk us off for 5 minutes. We have a special game going on while he is doing this."

"We have a special tip menu," continued Tanner. For every 10 token tip, Gersh gets a dick slap across his face at the end. For every 250 token tip, we extend the jerking off and token game for another minute. For every 25 dick slaps, Gersh gets a dick shoved into his mouth for a quick tease. And if anyone so desires to contribute 1500 tokens, Brandon or I will let Gersh jerk us off until we cum.