CATFISH BLACKMAIL
Disclaimer:
This story is a gay fantasy; no part of it is based in fact and none of the characters are intended to resemble real persons. This story contains sex between teenagers with some adults thrown into the mix. If you are underage or do not want to read about such matters, you should leave this webpage at once.
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This is my very first story; tips and suggestions are greatly appreciated. Thank you to the fans the encouraged me to continue writing, each and every email is greatly appreciated.
Titus V
SirTitusV@yahoo.com
Chapter Three:
Liam sighed as he watched his items slowly make their way down the checkout aisle's conveyer belt. Buying the cucumbers was easy enough since the clerk didn't know their intended purpose, but the smile that crept across the cashier's face as he attempted to discretely add condoms and lube left nothing to her imagination.
Liam had begged Jessica to let him use the lube and condoms he has at home, but hi his tormentor could not be deterred.
Adding insult to injury, the credit card machine was slow causing a small line to form behind the blushing swimmer. The couple next in line diverted their gaze when Liam glanced back at the growing line, catching the husband's unsuccessful attempt to suppress his laughter.
The special needs bag boy, who wouldn't hurt a fly, asked Liam if he would like his items bagged, picking up the cucumbers condom and lube for all of the customers in his line and the adjourning lines to gawk in either amusement or disgust. Snatching his purchases from the bag boy, the teen quickly rushed out of the store. In the parking lot, he took a picture of the items with the receipt as instructed. By the time Liam left the parking lot, he had to ignore three text messages from Meghan. She was wondering if he was still coming over after Liam rushed out of dinner (last chapter). Truth be told, fucking her would have made Liam feel less emasculated after this embarrassing day, but the other woman blowing up his phone with text messages gave him strict orders to get home immediately.
Once home, Liam ran past Susana, his family's housekeeper, up towards his room. Not giving her a chance to inquire about his day.
Standing nude in front of his mirror, with his computer recording the entire ordeal, the swimmer added some lube to his fingers to loosen himself up. He knew he was in for a very long night when he struggled to get the third finger into his tight hole.
Earlier that evening.
[Text]
Paul: Buddy, get your ass outside!
Jacob: Coming!
Slamming his front door, Jacob jogged over to Paul's truck.
"Hey man! What a day, huh?"
Jacob closed the door before turning to his friend. "I can't believe he's gotten caught by a fourth person. I thought he was going to die when Clayton took those pictures. Do you know him?"
"Yeah, I've seen him around school," said Paul, "he's rather gossipy, so there's a good chance that little encounter with Liam will be the talk of the school by the end of the week. At least at our non-fancy public school" chided Paul.
Jacob shook his head, "I don't think anyone would believe that Liam Mitchelle got naked in a dressing room and asked another guy to take a picture of his hole. Hell, I can hardly believe it and I have the recording!"
"That's true.," conceded Paul. "But he's certain to share that little bit of knowledge with the rest of the theater group or whatever lame shit Clayton's into."
"So, now what?" Ask Jacob.
"Depends. You've been in lust with the guy since you arrived at that fucking prep school. I just want Liam and Trent to feel even a smidgen of the pain they caused my family. By the end of the week, he may be begging us, I mean begging "Jessica", to let him suck our dicks just to keep quiet about the tapes and photos." Laugh Paul.
Jacob was momentarily speechless, he hadn't thought about an end goal of this catfishing. He never entertained the fantasy of Liam on his knees offering to blow him. The thought alone made Jacob feel light-headed as his distaste for the guy mixed with his general lust for the swimmer. Jacob had always been physically attracted to Liam but his arrogance and bullying was naturally a turn off for his victim. Jacob's better angels won the night.
"I don't know man. Blackmail is one thing, but forcing him to service us sounds a bit rapey."
Paul gave him a playfully smack in his crotch where Jacob's noticeable bulge was growing. "Well, little Jacob sure seems to like the idea! I mean a tight hole is a tight hole! Unless you prefer to get fucked...."
"Fuck off man. I just don't think we should take things that far."
Paul continued, "I think you're being too nice to this guy. He's been a menace to you since you arrived at that school. All I know is that if I had the hottest girl in school willing to be my slave for the week I'd be stoked!"
Jacob stared in shock at his friend, seeing another side to him that he wasn't sure he liked. "I'm going to ignore how concerning that last statement was as I secretly dial the police," joked Jacob. "And it's nice to know that you also think Liam is hot"
"It's not like that, I just know he's an attractive guy, which means if he fucks us over we can sell his bait file for a pretty penny to the pervs online. Especially after he deflowers his ass with that cucumber tonight! Trust me, no one is going to feel bad if that privileged prick is brought down to Earth. He just get's me so angry, that's why I need your help man. I need you to keep my anger in check!"
"Paul, we are just having fun with him. Let's just agree that we don't do anything rash without the other's general consent. I don't want this shit blowing back in our faces. His family is no joke."
Paul sighed. "It's a deal. We do this together, but I am going to get that cash at the end of the week. I have some college visits lined up and two Tander dates setup with some freshman coeds in the area!"
"Dude, they are probably Catfishing you!" Both boys broke out into laughter.
"Speaking of getting into my pants, DeShawn invited me to Zach Roads' party after the game."
Jacob looked dumfounded, "I don't follow."
"DeShawn is bi."
"He's bi?"
""Jesus Jacob, I shouldn't know more about the guys at Brenton than you. Yeah, that's the word on the street. So maybe he's trying to get into my pants or something."
"Maybe we can't use Jessica on him."
"That's what I was thinking. But I just can't get a read on DeShawn. He's always been nice to me and we were cool back when we did camp basketball. I'll have to get a better read on him at the party. Have you had any luck with Trent?"
"Naw, since his little TokTik vids blew up it's been impossible to get him to answer Jessica's messages. I imagine he gets a ton of girls in his DMs."
"Alright, keep trying but we may move to Plan B." Paul started staring off into space before both boys received the photo from Liam with his grocery store purchases. "Excellent, our little bitch is ready! I'll let you know more tomorrow. Plan B requires a few more things from Liam. Starting with tonight's little show."
The boys said their goodbyes as Jacob headed inside of his apartment and Liam headed home. Both of them were excited for the evening's proceedings but for different reasons.
Liam tried a multitude of positions to fit the six-inch cucumber into his hole. Even with the condom and lube, the phallic-shaped fruit wouldn't get past his tight hole.
A finger was relatively easy, and despite their complaints his last two girlfriends let him try anal on them, so why did this hurt so much? For the first time in his young life, he actually sympathized with the discomfort his girlfriends and that slut from Spring Break must have felt. After repeated attempts at getting it into his burning hole, Liam decided to take a nice hot shower to relax. Despite the warm water he wasn't getting any further. At Jessica's suggestion, he went back to fingering himself to loosen up his hole. Finally he was able to get the tip of the cucumber past his sphincter but by 11 o'clock he hadn't made it very far in his attempt to take all six inches. Soon afterwards the exhausted athlete dozed off, falling asleep on his bed after shutting his eyes for just a moment.
Paul and Jacob had long since grown tired of waiting for the hunk to complete the task. Even a couple of warning texts couldn't move things along. Jacob convinced Paul to let Liam try again in the morning.
Around 5 AM Liam woke with a start. Dreading the trouble he'd be in for failing to get even half of the cucumber in his hole, he hesitantly checked his phone. On the bright side, sometime after he fell asleep Jessica gave him until his morning swim practice to finish the task. The bad news is that only gave him about half an hour to complete the impossible.
Liam winced as he got out of bed; his ass was tender from last night's activities. As he waited for his laptop to reboot, he bent over in front of his mirror to confirm that his asshole wasn't injured. Thankfully everything looked all right.
With the laptop once again recording, he watched his reflection in the mirror as added a thick glob of lube onto the cucumber before slowly squatted over the fruit.
On the opposite wing of the large home, Liam's mother was also glaring at her reflection. Watching intently as Susana, the housekeeper, assisted with the final touches to her hair. Her ever-obedient Chief of Staff, turned Campaign Manager, was going over the day's agenda from outside her dressing room. They were already behind schedule.
"Valery, I know you wanted to have dinner with Liam tonight, but we have a few donors upset about your statements regarding the President."
"Brad, you know that's all bullshit. I haven't spent time with my child in over a week. All I said is that he could spend a little less time on social media"
"I know ma'am. But, we are already behind of the past two fundraising quotas. We can't afford to upset donors in the final stretch."
Losing her temper, Valery flung the double doors open, almost causing Bradley to fall into the room. "Goddamn it Bradley! You do know I have a son right?"
"Yes, ma'am, but..."
"No, you listen. You, not me, not the donors, but you, have made it impossible for me to do my job as a candidate and mother." Valery gave one of her tight smiles that indicated yet another tirade. " If I remember things correctly, it was that shit of a PR team you built me that suggested I make the statement. So if I am going to bail you out of this mess, then you can be the one to tell Liam why his mother is once again, skipping a family dinner."
Bradley stole a quick glance at Susana who was slowly shaking her head at the irony of the situation.
"Now, Bradley! Aren't we running late?"
Bradley stormed down the hall as Valery strolled down the staircase to her waiting SUV. At least her tirade can be added to the hundreds of hours of audio and video he compiled on Valerie. He suspected that once she won, she won't be keeping him around for long. Especially with her aspirations for the Senate.
Forgetting that Liam would be up for swim practice, Valery didn't see the point in personally disturbing a cranky teenager early in the morning.
Bradley was pleased to see the light shining under Liam's doorway, the boy may already be awake. As he approached the door, he heard a faint sound of moaning. Was this kid jerking off? Bradley could almost hear his heartbeat as he placed an ear to the door.
"Oh, god it hurts." Said the teen as he impaled himself on the disappearing fruit. He was amazed at his ability to take such a, relatively, large object up his ass. Two more inches and he'd be able to keep his reputation and life.
Outside of the door, Bradley wasn't sure if Liam's sounds were from working out or jerking off. But the boy sounded like he was in pain and pleasure. After the rough start of his morning, thanks to the brat's vial mother, embarrassing at least one member of this wretched family might turn things around. Throwing caution to the wind, Bradley gave a brief knock then swung open the door.
"You're mother wanted me...." Bradly froze in shock. The intrusion caused Liam to lose his balance fully impaling himself on the last two inches of the cucumber with a howl.
"Oh, oh shit, ouch!" yelled the teen as he rolled onto his stomach. His asshole felt like it was on fire!
"I'm so so sorry. I thought you were just getting ready and we are already late so I..."
"What the hell are you doing walking into my room without knocking?" asked the grimacing teen. Liam realized that Bradley was eyeing the tip of the cucumber sticking out of his ass along with the lube and discarded condoms on the floor.
"Get out, just get the fuck out!"
"Ok. But, are, are you ok? You look like you're in pain." Bradley took a step into the room before closing the door behind him. "Should I call for a doctor? Come on man, we have the same parts and your mother would kill me if she found out you were injured and I didn't do anything"
"I said, get out!" Liam was still in pain, but back on all fours as Bradley slowly exited the room.
A few steps down the hall, Bradley heard Liam call out for him.
"What's up, man?"
In barely a whisper Liam stated that he couldn't get the cucumber out.
"Oh shit! It's stuck?"
"I can't get it out and it fucking burns. My ass is killing me! I need to get this out!
"Um, that's way outside of my job description," chuckled Bradley.
Liam couldn't believe he was making jokes while he suffered through the pain of a 6-inch cucumber up his ass. "Can you cut the jokes? I need your help; if anyone found out about this I'd be dead. Seriously, my mother can never know."
Bradley crouched down near the teen. Never in his wildest dreams did he imagine seeing Valery's son presented to him in the doggy style position with a cucumber shoved up his ass begging for his help.
"Ok, I'll need you to breathe and this will have to be quick. Your mom is waiting."
"Just do it." Liam was so used to having Bradley around that he was confident in his discretion. He would have preferred to avoid using his mother's staff, but if it really is stuck then this beats a trip to the ER. Bradley has already kept a number of the family's secrets. He even used his connections and law degree to get Liam out of the mess with Officer Kresgie, Paul's father.
Due to the pain, this was not going to be an easy extraction. Bradley told Liam to lean against the bed on his knees with his ass out. This gave the swimmer the added benefit of biting down on his sheets as his novice ass slowly gave up the cucumber.
The boy's moans were reasons enough to go slow, but Bradley was aware that his mother was waiting outside in the car. To soothe the experience, he started rubbing Liam's lower back and telling him to relax.
Despite the pain, Bradley was able to slowly removed the six-inch cucumber from the teen's puffy hole. A sight Bradley would never forget, especially because halfway through he took out his cell phone to record the extraction while the swimmer's head was buried in his sheets. He made sure to scan around the boy's room, catching the teen's sports posters of himself to ensure that there would be no mistaking the fact that this was Liam Mitchell's ass on display before putting his phone away.
"Well, this will go down in the history books as the oddest thing I've had to do for my job. As usual, this stays between us. If you'd like, we can talk about this later."
"Yeah, maybe," said Liam as he grabbed a pair of boxers to regain his modesty. "Um, can you please leave?"
Bradley had to place his bag over his crotch to hide his erection as he exited the room. Not that Liam would have noticed since he could hardly stand to look in Bradley's direction. The excitement of the moment quickly evaporated as Bradley was greeted by the displeased look of
Valerie at the bottom of the staircase.
"Don't ever tell me we are running late, then spend nearly 10 minutes delivering a simple message. What were you doing?"
"Liam wanted to chat. I'm sorry ma'am." Bradley had to suppress a smile as he walked past her towards the waiting SUV. He'll have to keep an eye on that boy. What self-respective straight teenager would get themselves into that type of situation?
Liam was just speeding out of the garage when he received another text message from Jessica.
[Text]
Jessica (Paul): Wow, you took it all! Good job, but I told you to fuck yourself with it. Not just sit on it. Where are you?
Liam: I'm sorry. That's the best I could do. Just leaving my house for practice. I'm running late.
Jessica (Paul): Be a dear and grab your new speedo.
Liam groaned in frustration. Before rushing back up into his house.
"Liam!", bellowed Coach Stephens, "I want to see you after practice. Now, hurry up and get changed, we are almost done with warm-ups."
Save for the burning sensation in his asshole, the swimmer felt back in his element. But the ache in his asshole was nothing to the pit in his stomach that he felt after getting a small lecture from his coach for his tardiness. If he was going to be a co-captain, he had to set a proper example.
Leaving coach's office, Liam was relieved to see that he didn't have any text messages from Jessica. Chucking his speedo and heading towards the shower, Liam was walking towards an open shower before he received a stern look from Mac, Sean, and Henry. The lower-classmen were waiting patiently at the end of the line for their turn at the showers.
Remembering their deal, Liam awkwardly found his place at the end of the line, much to the amazement of the rest of his waiting teammates.
Seconds later Cliff came out of the shower area. Flipping his towel over his shoulder to show off his rather hefty package.
"Mitchell! What are you doing standing around with the kids?"
"Just trying to lead by example. Last in, last out. Am I right?"
"You really are kissing a lot of ass for that co-captain spot," ribbed Cliff; another contender for the title.
"I think it's good that he's leading by example", bellowed Coach Stephens as he departed to his private changing area. "This is still a team sport after all."
Liam couldn't help flashing one of his arrogant smiles as Cliff walked away. Causing Mac to roll his eyes.
"Hey Captain", mocked Henry in a whispered tone, "what's going to be your excuse for the rest of the week?"
"Yeah, is beating off in the locker room also a prerequisite for co-captain, because if so, Sean should have been made Captain in 6th grade!" ribbed Mac as he pushed Sean into an open shower spot.
"Just drop it so we can get out of here." Liam was already tired of the good boy act. Having three freshmen holding that jerk off incident over his head (Ch. 2) was going to make a long week, even longer.
Back at his locker, his phone was vibrating like crazy from a string of text messages.
[Text]
Jessica (Paul): Morning lover. How'd did your teammates like your new speedo?
Jessica (Paul): I'd love to see you in them! Take a quick snap of yourself before you head to class.
Liam: I'm sorry. I already changed.
Lied the swimmer.
Liam: Can I take one tonight?
Jessica (Paul): I'll let this one slide, but you owe me a picture during your lunch period. No excuses.
Liam finished changing. As he put on his blazer and grabbed his bag, Mac and Henry dropped a pile of dirty towels at his feet.
"Um, have you forgotten our little deal or should we start talking about your little locker room activities?"
Liam didn't even bother responding as he dropped his bag to pick up the discarded laundry. As Mac and Henry departed, Sean came around the corner with the dirty towel cart.
"Here, you can place them in here."
"Thanks", said Liam. Not too pleased being on the cleanup crew, even with the extra set of hands.
Sean stuck around to help gather the remaining towels. Liam, being none too patient, even snatched two from the freshmen still drying off; leaving them naked and damp. Not wanting to challenge a known bully, the Freshman focused on getting dressed and away from the short-tempered Junior.
As Liam and Sean made their way back to the laundry room, Sean pointed out that Liam forgot to wash yesterday's laundry.
"I know you had...other things on your mind but we have to do it daily or we might run out of towels," beamed Sean.
Liam stared dumfounded at the machine. "Can you show me how to turn this thing on so I can get out of here? I have homework to finish and I've had a long night."
"Didn't you do this when you were a freshman?"
"When I was a freshman I was already on the varsity relay squad and qualified for State. So no, I was not a laundry bitch. Can we get to this already?"
Ignoring the insult, Sean taught the junior athlete how to operate the machine.
The boys made it back to their lockers to grab their bags and head to class.
"Simple right? I think laundry is sort of fun when you don't have to fold it or put it away! I don't mind helping you this week, man."
Liam eyed the blushing sophomore suspiciously. Was this kid hitting on him or something?
"I appreciate your help, but I don't need you perving around me all week. I can handle the laundry, just leave me the fuck alone."
"I wasn't perving...I", the kid was flummoxed, "I just wanted to be a good teammate."
"Sure, I saw you checking out my co..."
Just then Coach Stephens emerged from his office, "Boys! I appreciate your help in here but you should be getting over to the cafeteria if you want to grab a quick bite before class."
Liam and Sean quickly grabbed their belongings. Without a word, Liam stormed off as Sean looked on cursing himself for being so lame.
Liam was surprised that he didn't hear from Jessica until the last period just as he was gaining hope that she had forgotten about him. He put on a brave face, joking with his friends as he made his way to the pool for the afternoon swim practice. This time taking up a spot in the locker room's handicap stall to change into the new speedo. He felt more exposed as he heard his teammates were coming in and out of the restroom area with the general banter of high schools after a long school day.
With the camera in place and set to record, Liam removed the hot-pink speedo from his bag. Somehow, it looked even gayer than it had that morning. Stripping off the remainder of his clothes he gave the camera another 360-degree view of his ripped tan body before bending over to put on the colorful swimwear.
Liam started to panic as he remembered how small this pair was. In his rush to get out of Sports and Stuff, he failed to get the proper size. By the time he forced the speedo over his ass and dick he was at a loss for words. The garment looked like it was made for a child, leaving a part of his ass crack and pubs exposed.
There was no way he could go to practice like this! Coach would bounce him off the team!
Outside of the swimming and diving complex, Jacob snuck into one of the back entrances leading to a small hallway outside of the swimming arena. Through the small glass window on the door, he had a clear view of the pool. Paul suggested scaring Liam since he was almost certain that he would never go through with the assignment.
An hour and a half later, Jacob was trying to soak up the pizza oil that fell onto his textbook as Paul sat down in his booth.
"How was practice?"
"I should ask you the same thing," grinned Paul.
"He chickened out and didn't go through with the pink speedo."
"Did you have the video?"
"Yeah, send it to me."
"Ha, I told you he'd pussy out. This will work in our favor. We can up the payout for the end of the week and scare the life out of him." Paul started fiddling with his phone.
Jacob looked down at the notification he received from Jessica and Liam's chats.
Text:
Jessica (Paul): You're dead. [Video sent] The deals off.
"So you're really getting into this." Jacob had some probing questions for this friend since he was turning out to be the mastermind of this little game.
Paul looked at Liam quizzically as both boys ignored the string of cell phone notifications. No doubt from Liam's meltdown.
"I'm straight Jacob. But, I've never had this type of hold over someone. It's like Ramsey in GoT. It's just hot to take an asshole down."
Jacob had to smile, "You're not planning on castrating Liam are you?"
"Not physically, but maybe a bit mentally. I don't know, the money sounds nice and his humiliation sounds even better. We still have to get Trent and DeShawn. Those two basically follow Liam's orders."
To cement his masculinity, Paul gave a little smile and wink to a table of girls across the restaurant. They quickly turned away blushing. Jacob was never attracted to Paul but the guy was cute with his dark hair and brown eyes. He was lean and just simply cute. His mother was Japanese and his father is Irish, Scandinavian, German, hell who even knows. Together they created a cute 6'3 boy-next-door.
With the fun time over, Paul had to get a pizza delivery order out the door. He instructed Jacob to ignore all thirty-plus text messages and future messages they received from Liam. He will handle this when he gets home.
For maybe the hundredth time this week, Liam's mouth dropped as he saw the video of himself strutting into the pool with his normal back speedo on. He rushed out of the locker room in the hopes of finding Jessica but ended up crossing paths with a Meg. She was all too ready to lay into him for not texting her back after rushing out of dinner.
Liam brushed her aside as he jogged out of the area towards the back exit where the video was shot only to find a dark hallway with no signs of Jessica.
"What's with him?" Asked Courtney as she climbed down from the high dive.
"Nothing, he's just being a typical jerk", moaned Meg as she stomped off to the girl's locker room.
Liam tried desperately to get Jessica to respond to his pleas but was left with silence. He was just finishing his dinner which felt more like a death row inmate's final meal. Liam nearly threw up when he started getting Twitter messages from classmates and friends about his little shirtless selfie outside of Sports and Stuff (Ch. 2). Jessica wasn't lying; the pictures were being released by some dummy account that tagged his name. Of course, most of the notifications were Likes from female classmates. This release was enough to make the swimmer almost throw up his dinner as he sent 10 more desperate messages begging Jessica not to release his nudes and jerk off videos.
Text:
Jessica (Paul): I said the deal is over. This was just the appetizer to ensure we have people's attention.
Liam: Please, please, don't do that! I couldn't go out there in the speedo, those are team rules. I'll do anything but please don't do this
Jessica (Paul): If you are going to beg, have the decency to show your face. Facetime me. Now!
Liam darted from the dining room up to his bedroom before slamming the door shut, this time remembering to lock the door.
Paul and Jacob were ready for the evening's entertainment. Both were greeted by an ashen-faced hunk on the verge of what appeared to be real life tears! The silent treatment and Twitter posts really did the trick on this once arrogant jock.
Pushing back some of his golden blond hair, he begged them not to destroy his life.
"What have I ever done to you?" cried the jock, "I thought we were having fun. Why are you trying to ruin my life?" A couple of tears had started to run down Liam's face. For the first time in his life, he felt overwhelmed and powerless.
Text:
Jessica (Paul): Save the tears. You chose this.
"Please, I can make it up to you, I promise. If we meet in person I can prove to you that I'm a good guy and will stick to my word. Just give me a location for us to talk it out. I promise."
Text:
Jessica (Paul): I'm getting turned on seeing you beg. You have one more shot, but defy me again and your life is over. The price for your videos and photos just increased to $5000 in cash on Saturday.
Liam didn't hesitate to the terms.
Jessica (Paul): Since you fucked me over today, I think it is only fair for you to return the favor...
As instructed Liam retrieved the cucumbers he hid under some items in a desk drawer. He laid both of them at his feet before grabbing the lube and pulling off his clothes.
Despite a night of practice he still wasn't comfortable sticking things up his tight ass.
Text:
Jessica (Paul): I don't have all night. Make sure you finger yourself and use lots of lube.
Liam began finger fucking his sensitive asshole. Even a single finger seemed to burn after the morning's assault.
Text:
Jessica (Paul): Work another in there. I want you to get up to three, you slut!
A groan escaped from the swimmer's mouth as he added the second finger. Slowly loosening up his hole. He started to grimace when a third was added. He was only up to his knuckle before Jessica commanded a deeper probe.
Text:
Jessica (Paul): Keep doing that till I tell you to stop. Start sucking on your green little toy.
There was hesitation after the last command. Sucking on a cucumber felt way too similar to sucking on a dick. He could never live this down. Knowing he had no choice in the matter, the blond hunk brought the six-inch cucumber to his mouth. Slowly kissing and licking it as he fingered himself for the camera. He never felt more queer and vulnerable than in this moment.
Text:
Jessica (Paul): You know I want to hear you talk dirty.
Liam began sucking the tip before taking it out of his mouth to give the camera one of the sexy looks he uses on girls.
"Mmmhm, master. I love sucking on this big cucumber."
Text:
Jessica (Paul): Say you wish it was a dick!
"Please don't make me....I'm not gay!" One last glance of himself in the video feed of him on his back with three fingers in her ass made the comment almost comical. the swimmer sighed then to the inevitable.
"Mmmhmmm, master. I wish this was your fat dick. I love sucking on this big dick."
Text:
Jessica (Paul): Good boy. Now tell me how much you want to fuck yourself.
Paul wasn't particularly hard watching this unfold, but he was getting a bit aroused at the sight of Liam turning degrading himself before his very eyes. Jacob on the other hand was mesmerized by the entire scene. Cumming for the first of many times that evening as he watched Liam squat over the cucumber again.
Thanks to the fingers and lube, he was able to sink down an inch with relative ease. Liam found that rotating in a circular formation was the easiest way for him to slowly sink further onto the cucumber. Of course, this motion only helped to show off his amazing and now sweaty abs to the camera.
15 minutes later and his face was a mixture of pain and determination as his beautiful ass accepted more than half of cucumber. Liam began slowly bouncing up and down on the fruit as his lube slick hands attempted to hold it in place.
Text:
Jessica (Paul): Get on your back and fuck yourself with it. Start jerking off.
The subservient jock got on his back with his ass towards the camera as he continued fucking himself. Try as he might he just couldn't get his dick hard.
"I can't get hard while doing this."
Paul smiled to himself.
Text:
Jessica (Paul): That's fine baby. You can take the cucumber out and put on some porn to finish up. But tell me before you cum!
Relieved, Liam pulled the cucumber out with a fart sound from the lube before tossing it onto his discarded boxer briefs. He was embarrassed as he saw his pink asshole slowly close. Loading up his phone it did not take long for the teenager to get a hard-on. Sounds of lesbian porn could be heard off-screen as he focused on the two women going at it.
Liam's impending "O" face was a clear sign that he was about to cum. Just then, he heard the chime from Jessica's chat.
Text:
Jessica (Paul): Cum all over the cucumber! You better not miss!
The swimmer had just enough time to grab the green phallic before he unloaded his warm spunk. Most of it coated the fruit with the rest on his hands. He sat back as he caught his breath from the post cum high.
Text:
Jessica (Paul): Lick it off!
Eating his cum was the least of Liam's worries at this time. He's already licked his off of a bathroom wall, "But it's been in my ass!"
Text:
Jessica (Paul): That wasn't a question. Suck it off like you made other girls suck you off over the years!
Liam wanted to throw up. Not that it inherently looked dirty from the novice anal action but just the thought of doing "ass to mouth". Not seeing much of a choice he brought his tongue up to a part of the load before licking it off. Before taking cum covered tip into his mouth. There would be no way to live this down. First, he fucked himself with this thing and now he's sucking his load off of it. Not even his favorite porn star would be this nasty.
His reflection in the camera feed cemented his shame. Liam once again felt a tear from rage and humiliation as he pretended to love the taste of his cum and his ass for the camera.
Paul's final order forced Liam to scoop up the cum on his hand and place it at the tip of the cucumber before one more plunge into his ass.
"Oh yeah, I love having that hot cum inside of me. I need it at both ends." He read his script that would convince anyone watching that he was nothing more than a closeted gay slut.
Inside, Liam was burning with rage. This week couldn't end fast enough.
To be continued...