A gay story: Becoming a Fan I put my car into park, sitting comfortably in the wide parking spaces of a parking lot I had never visited before. Staring up at the bar in front of me, the neon Rooster advertised to the world that this was the best chicken ever made. I highly doubted that, but what this place did have was a Trivia night, which I had signed up for online to meet some new friends. I had been a bit lonely recently; I drifted away from my old friend group a few months ago, as some of them had left the state, and the rest partnered up leaving me as the odd one out. I didn’t have too much money to dump on spare hobbies, so a free trivia night and beer sounded right up my alley, and worst case scenario I would just have an awkward night and try something else later.
I strolled into the bar and saw a few tables spaced out for the event, the one I was looking for had two men, which I spotted in the far corner. Strolling up I saw the pair a bit better having only had a blurry photo on the app to distinguish them. The larger man was Jack, who was impressively large, having a paunch to him with plenty of muscle to back it up, and a small amount of trimmed facial hair. Sitting next to him casually sipping a beer was Thomas. He was slender and looked roughly my age, which gave me hope that this would be a fun pair to hang out with. Extending my hand, I introduced myself.
“Hello, I’m William, you must be Jack and Thomas?”
The larger man grinned and took my hand in his, the size difference was enormous, with plenty of grip behind it.
“You would be correct, I can tell you’re going to be a valuable member of the team,” he said still grinning and put his hand down, after what felt like a bone breaking shake.
“And I am indeed Thomas,” the younger man said, with a much less firm hand shake.
“I hope you don’t mind but we already have a name picked out here, we’ve been going by the moniker ever since we started as a silly inside joke, it’s Beary Creamy.” Jack said with a bit of a sly grin.
“We’ll I’m not one to rock the boat, I’m just hoping for a good night of trivia,” I beamed, trying to put on a good impression.
The night went fairly well from there, I ordered the chicken, which did not live up to the hype, and a few beers. I learned through some conversation that Jack and Thomas were dating, and they had recently lost their third trivia partner, who was a powerhouse of sci-fi, movies, and comic book trivia. The men were both very friendly and easy to get along with, and if they didn’t disclose their relationship status I would never have guessed. We dominated the night, ending up second place, and losing by only 10 points to the cockily named team, First Place Team. They had apparently been dominating this particular bar at trivia for months.
“We’re going to beat their asses one day,” Jack cursed playfully, “but we did significantly better with our new addition, he said smiling in my direction.
“True, we would have been lost in the video round, and I still have zero clue what a Dalek is, but that won us so many points.” Thomas said cheerfully.
Before I could respond the announcer came by to take our picture, squeezing together at the table we grouped up before hearing a loud “CHEESE!” following by a flash and a gift certificate laid out with a congratulations.
Turning back towards Jack and Thomas I saw the certificate pushed towards me from Jack, “Consider this our welcoming present, we’d like to have you come back if you’re interested.”
“Of course, that was a blast, plus I need a reason to use the certificate. Can I get your guys’ numbers’?” I asked, just glad to make a new pair of friends, even if I was the third wheel.
I collected both of their numbers, and was added to the group chat, also named Beary Creamy. We chatted throughout the week exchanging memes, and just general silliness. Jack was incredibly skilled at photography I found out, creating most of the memes he sent from original content. I gathered that he was a small business owner and content creator for some app, and Thomas had an unrelated office job in marketing. Thomas was very reserved, and never really joined in the conversations that much, giving maybe a thumbs up, or a laugh when he really enjoyed something. For the most part though the weekly texting was just Jack and I.
The following weeks played out much the same, we met up every Thursday and proceeded to come in second or third, passing around the certificate amongst the group when we won. I felt like I had really found some friends, even coming over for a movie night or two during the week.
This Wednesday played out much differently though…
Opening my phone I opened the Beary Creamy group chat, to find an odd notification, Thomas has left the group, the words sat there staring me in the face.
“Hey are we still on for Trivia? What happened to Thomas” I wrote, cringing internally hoping I wasn’t right about the situation.
The response was quick, the three dots popping up at once.
“Hey I think I’m out this week, Thomas and I just split up, and I’m trying to figure some stuff out.”
Jack’s response confirmed exactly what I thought, brining my own turmoil of how to even handle this. I had never been great at this sort of thing.
“I’m sorry to hear that, let me know if there is anything I can do.”
I left that there, not expecting any response back, and contemplating the idea that this was the last I would hear from either of them. It wouldn’t be the first time someone retreated from the world after a breakup. Instead, I felt the familiar chiming and buzz of the phone in my hand; he was calling me.
“William, I don’t really know how to say this, but if you are serious about the favor, I need an absolutely massive one.”
Jack sounded, remarkably well considering the situation, his tone hinting at a bit more worry than anything.
“Sure, what’s up Jack? Are you doing ok with Thomas leaving?”
“Yea, so that’s what I need to talk to you about,” Jack intentionally leaving a pregnant pause at the end.
“Thomas was less of a boyfriend and more of a business partner,” he led, and after a deep breath resumed.
“So I run an OnlyFans account and Thomas was my friend and business partner… and he decided he wanted something different. I don’t know where he went or what he’s doing, but he blocked me everywhere so I’m in a bind right now.”
I let that sink in, that was not anything that I expected, ‘and where was this leading’ I thought.
“I had no clue, and I’m not sure how I can help,” I said, with a nervous laugh.
“So, I have a proposition for you,” Jack took a deep breath, “I need a model to make money, you won’t have to do anything you don’t want to, and you won’t have to show your face… Before you say no, all you would have to do would be stand on camera and get a blowjob. I just need a stand in until I find a replacement for Thomas.”
I was a bit speechless, I wasn’t exactly gay, and this was a big ask, there was a giant lump in my throat as I tried to find the appropriate response. There was no way I could accept this.
“I’ll pay you 60% of the proceeds from the cam sessions, which should be about a thousand dollars a week” He rushed in to add.
That gave me an immediate pause, I was by no means poor, but looking around the sparse 500 square foot room, there was a lot to be desired. That was a lot of money to say no to.
“All I would have to do is receive a blowjob, and no one will know it’s me?” I squeaked out, not sure I could handle what I was about to sign up for.
“Yes!” Jack beamed back through the phone, I could hear the wide smile on his face.
“Come over tonight around seven, just shower beforehand please, and I’ll pay you by the end of the week.”
“Ok I’ll see you in a bit,” I said meekly before hanging up the phone.
I felt my stomach flop, I can’t believe I agreed to this.
I drove up to Jack’s place, the small dark house illuminated by a few sparse interior lights. I took a deep breath and gathered my courage before walking up and ringing the bell. The door opened, and I was greeted by Jack in a black robe, with a wide smile.
“I’m so glad you came, I had zero options here, I needed someone fast. You are an absolute lifesaver, and I owe you huge.”
Jack was ecstatic, and I wish I had the same energy, I was insanely nervous about this whole thing.
“You’re welcome man, I try my best to help out friends,” I said running a hand through the hair on the back of my head. Flashing a flighty smile.
“Relax,” Jack reassured me, “this is not as intense as you’re thinking, and I know this isn’t exactly your thing. Just take a deep breath, this is just acting at the end of the day.”
He flashed me the warm smile and I did what I could, taking a deep breath and exhaling. He then held up a red jockstrap and nodded to me.
“This is clean, and it’s one of the main pieces of costume I use for my sets. It helps to set me apart from other creators. We always start our videos in these.”
This got me to finally crack up and laugh a bit, holding the red pair of underwear I felt like the tenseness was broken. I wasn’t in a completely serious alien world at this point.
“Ok, I can work with this, but isn’t this going to come off immediately,” I asked.
“Depends on the viewers,” he smiled, “Hopefully we get a good crowd, do our thing and log off early.”
“Alright sounds good.” I said, trying to sound cheery.
I stripped in front of him folding my clothes and placing them on the table, and sliding up the smooth fabric of the red jockstrap. My stomach was turning in knots, and Jack was gratefully looking in the other direction as I did, giving me some amount of modesty. Once I had everything all snug I stood up straight and awkwardly made eye contact with Jack.
“Ok so how do we do this?” I said, squeaking a bit with the last word.
“Follow me, and remember to take deep breaths, this is really the easiest thing in the world.”
He smiled back at me reassuring me and he led me into a separate room of the house I hadn’t been in before. There was a small foam couch in front of a large TV screen hooked up to a computer, with some soft blue lights glowing around the edges. The couch itself barely came up to waist level, and the soft foamy material made it seem light and very moveable. A camera blinked with a soft flashing light, pointed at the couch, obviously set up to capture the action. Behind the tiny couch looked like some exercise padding, placed over the hard wooden floors, leaving a large space in the middle of the room for what I assumed would be plenty of sex. Against the opposite wall of the TV was the last piece of furniture in the room, an open wooden workbench, filled with all manner of sex toys. Some I recognized as dildos, with progressively larger sizes going up, and some I didn’t recognize, like a series of small metal cages.
Jack sat down on the couch his large bulky frame, comically fitting on the small couch, which had little to no internal framing, and squished out from him. I looked at him a bit closer now, this was the first time I’d seen him naked, well mostly naked. He was much bigger than I was, towering over me when we standing, and sitting down he was still impressive. The paunch I had seen at first was not as soft as I had imagined, he had a thick layer of muscle running around his body, with a moderate amount of fat protecting it. He was well groomed, most of his body hair having been trimmed to some degree, leaving him with moderate amount of hair that was seemingly everywhere across his lightly tanned skin. His facial hair was clean and closely shaved, having just a small beard which seemed to be the trend considering his head was bald. The irony of the one spot on his body he couldn’t grow hair. The only other noticeable feature, and it was very noticeable was the enormous package being held in his crisp white jockstrap. It was obvious he was built for porn.
I was keenly aware of the contrast here, I was similar to Thomas, which is probably why Jack reached out in the first place. I was much leaner, with almost no body hair on my torso. What I did have I kept neatly trimmed, preferring to be cleanly shaved everywhere for hygiene reasons. My own complexion was significantly lighter, as I was more of a homebody, leaving me with a very pale skin. Even the jockstrap was less filled out, which was a bit more embarrassing. My own manhood, looked to be less than half of what I assumed Jack was packing. The only thing I had on Jack was the hair on my head, which more than a few people were jealous of, styled into a neat short faux hawk.
“Come on over and stand here” Jack said, pointing next to him in front of the tiny couch and directly in front of the camera.
I buzzed back to life, and quickly stood in place, jolted out of my thoughts.
“Ok ready to roll director,” I smiled, trying to get through the nervousness. My stomach was still in knots, rolling over itself.
“Just breathe, you don’t have to do anything you don’t want to, if they ask you to do anything outside of what we asked, just nod if you are ok with it, and shake your head if you don’t want it. Either way is fine with me, lets practice now, are you ready to go.”
My heart was racing, and I felt like it was going to beat from my chest, but taking direction, I took the deep breath and nodded. Jack smiled, and turned to the computer, clicking the button, I saw the giant TV light up with what the camera was seeing. My bright red jockstrap framing the right side of the screen, with the left framing Jack’s brightly lit up face. The background was unfocused but you could see the blurry image of the toy table behind him. I then noticed the title of the cam show, Beary Creamy. The inside joke finally clicked, and I took a big breath in.
“Hey guys, we have a new performer today, Thomas is out for the foreseeable future so we have a new guy here today. He’s a bit shy and a first timer so please be kind to him.” Jack beamed into the camera.
A flood of people were in the chat room from the first moment, it seemed like he had a lot of regulars here. The messages were popping up with some condolences about Thomas not being there anymore, and more than a few of them were focused on me.
BiGuy85: The new guy has a nice ass, I’d love to see that thing put to work.
BigBear2: I need to find out where you get such cute guys.
TwinkleStar: This is going to be fun, I want to see you toss his cookies.
That last one made me immediately blush, but Jack was taking it in stride, laughing and responding to the comments.
“Well, you guys know the rules, but the only thing my new partner has agreed to is getting a blowjob, so as of right now, that is the only thing on the table.” Jack said with a playfully stern tone.
He knew how to keep them engaged, and a few of the commenters popped up asking him to take my cherry. Which caused my head to immediately shake no. Jack saw this from the corner of his eye and let out a chuckle.
“Don’t scare him off guys, if you want to see him get a blowjob leave a tip, and from how nervous he is it may need to be a big one.”
Jack was smiling, he was in full control of his audience, they were very obviously enthralled with his every word. Then a notification popped up on the screen.
POLARBEARx88 requested a rim job for 500 dollars.
I stood there stunned, someone was willing to spend 500 dollars alone to see me get licked in the butt. I looked down at Jack, who was already looking at me, waiting on my word. That was an insane amount of money for me to do basically nothing still. I nodded and turned around, as the screen went wild. Comments were pouring in, cheering on the donation. As soon as I turned around, I felt Jack’s large hands grab onto my round butt cheeks and spread them apart. I leaned forward a bit as I felt the scruff rub against my butt and one of the best feelings I’ve ever felt in my life, as his tongue darted on my asshole. Jack was more than skilled as he licked each way, the minutes felt like hours, and a few moans escaped me, which drove the comments even crazier. Once he backed off, the erection I was sporting comically strained the jockstrap.
“Looks like my new co-star likes that,” Jack said with a wink to the camera, “And thank you Polar Bear for the donation. Does anyone want to see the climax here?”
The donations started pouring in, I saw the counter climb higher and higher, we were already at a couple thousand dollars before I knew it. Jack looked at me, and I knew what was next as I nodded. He pulled the fabric of the jockstrap down, freeing my erection, it wasn’t huge by any means but compared to him it was completely dwarfed. He took it into his whole mouth and expertly sucked and maneuvered his tongue in ways I have never felt before. His hands wandered over my backside, rubbing my butthole, still slick from his saliva as he continued to bob faster and faster, which only egged on the chat room. I exploded quickly filling his mouth with cum, which he swallowed immediately. I nearly collapsed from the experience, my knees shaking as I came. Jack turned back to the camera smiling.
“I think he may be spent now, but if you guys are nice he may just come back.” Jack said with a smile.
The comments continued to come in, with more than a few people exclaiming that it was the hottest show they’ve seen in a long time. I seriously doubted that considering how tame it was, but I did feel flattered having so many people compliment my body and cock.
Jack took the comments in stride and continued to talk to his fans before ending the session at the normal time, with no other sex acts. We did have quite a few offers on the table, but I was spent, and declined all the offers that came after.
Jack thanked me for helping him out, and by the end I had more than a thousand dollars after taxes, from just one show. He sent me the money on my phone through cash app and I departed, getting home, and falling asleep immediately.
I woke up the next day, fully refreshed, the night before having completely exhausting me, and ready to start the day and go to work. As I sat up, I saw a message from the Beary Creamy chat group, swiping into the phone to read the familiar blue bubbles from Jack.
‘That was a great show last night, thank you again for filling in, the crowd loved you.’
‘Also we got a proposition on my Fans account to make a video, call me if you’re interested so I can explain, but it’s a bit more involved than last night.’
I wasn’t sure what to say, so I quickly responded back.
‘You’re welcome, it wasn’t as bad as I was expecting, and I guess I’m a star now LOL. But I’ll call after work.’
I left the chat there and got on with my day, heading to work and going through the motions. My mind couldn’t stop replaying what happened last night, and how that made me feel. I had never done anything like that before, and I could see the appeal now. My stomach was in knots again, and by the end of the day I was rushing home to call Jack. Picking up the phone I navigated to past calls and hit Jack’s name when I found it. The ringing on my phone caused my heartbeat to accelerate to what I assumed were probably dangerous levels.
“Hey Jack, so what’s up?” I said, trying to keep an even tone through my nerves.
“Hey buddy, so one of our viewers has a very specific fetish, and this is going to take a bit more time to complete, but it pays two thousand dollars for the final product, plus whatever we make camming it and you still won’t have to show your face.”
My jaw dropped hearing those numbers, that was an insane amount back-to-back. I understood now how he afforded that house, and his lifestyle. Jack was incredibly skilled at this.
“Ok so what does it involve?” I queried, having a million possible ideas floating into my head.
“So I was able to negotiate a bit, and what this person wants to see is you locked up in chastity having your butt played with over the course of the week, and then have you cum all at once. We wouldn’t have to have sex, but I would just be using some smaller toys and fingers. I guess the instant erection from the rimming got some ideas flowing.”
He paused as he finished saying it, leaving the ball square in my court, my mind was a bit of a blur taking all that in.
“Will this hurt at all?” was the first and only thing that came to mind.
“No, it may be a bit uncomfortable at first, but I’ll make sure to keep the toys small and go very slow for you. It’s better for viewership too, you need them to be hooked on something,” he said, with a very professional business tone to it.
“Ok, I’ll do it, as long as were still hiding my face.”
I could hear Jack’s smile through the phone, “Of course, just remember to breathe and have fun, I’ll see you tonight.”
After we said goodbye and my stomach finally stopped turning over itself I gathered myself together and got a quick shower before heading over to Jacks house again. This time I pulled up in a bit more light, giving the house a far less intimidating vibe than the last night. I stepped up to the door not even bothering to knock. Jack was on the couch, still fully clothed, typing away on his laptop. Seeing the light filtering in he looked up, smiling as always.
“Hey man, perfect timing, the show starts in about thirty minutes, I put some stuff in the bathroom, since this is going to be a bit more involved, we need to be clean inside and out. Just use the douche I left in there, and if you need help there are instructions next to it,” he said nonchalantly, as this entire thing was perfectly normal for him.
I was again in a bit of a state of culture shock.
“Ok, I’ll go figure that out,” I said, still nervous about every step I was taking in this whole new path.
Returning a few minutes later, a bit humbled but feeling as clean as I had ever felt in my life, I had on the characteristic red jockstrap left in the bathroom for me with the cleaning supplies. Jack was sitting on the couch, changed into his own outfit, the crisp white jock the only thing on his body as he typed away on the laptop.
“Ok I think I’m ready,” I said smiling, and shaking a bit internally.
Jack smiled up at my pulling away from his laptop again, “Alright let’s get setup.”
He stood and walked me back to the studio, past the small couch sitting directly in front of the camera, and back towards the toy chest grabbing a metal cage which looked far too small for me.
“Pull down your jock please, were going to attach this, and surprise the viewers when they see it.” He smiled.
I pulled down the underwear, as he kneeled in front of me and placed my soft cock in the steel contraption, locking the base around my balls. I hear a click as he locked it in place and gave it a small jiggle to make sure everything fit correctly.
“Ok were all set, the plan is to sit on the couch, you will be across my lap with a selection of toys, they get to bid on which ones to use, but nothing here is going to be very large,” he said gesturing to a small selection of toys, which seemed very tame in comparison to some that were behind it.
“Are you ready to start this? I can still see your head nod and shake if you want out at any time, but don’t expect anything outside of the bounds tonight.” He said staring into my eyes.
I nodded, just like last time, the lump in my throat not dissipating, as I walked over to the couch. Jack sat down and I took my position across his lap, with the upper part of my torso outside of the camera. I turned to watch the screen, and Jack sat clearly in frame, his bulky presence taking up the larger part of it, with my butt perfectly framed over his lap. The large bulge in his white jockstrap sitting underneath me lying in wait. He clicked a button on the screen, and I saw the chat start to pop to life as we went live.
“Hey guys, we’re back, and we have a special event for you,” he smiled, as I flexed, hearing the session start.
“Our friend is back and he’s agreed to some additional fun for one of our very generous viewers,” he grabbed my package nested in the jockstrap,” he’s been locked away and agreed to have some fun with our toys for a week.”
Jack pulled me onto my side displaying my package front and center for the camera before pulling the jock to the side and revealing the gleaming cage.
“If you guys want to see some toys, you know the drill, we’ll go easy on him today though,” he said with a wink as the chats started to roll in.
BigBear2: I want to see that pink one stretch him out.
POLARBEARx88: I can’t wait to see him after a few days of this.
Twinkerbell601: Find the big ones!!!!!
FloridaGirl01: Can’t wait to see that juicy bottom explored, this boy is cuter than the last.
I blushed at the last one, I didn’t realize women loved gay porn, and really didn’t expect one to be so forward about wanting to see me used. Just then I felt a wet and slippery digit start to explore my butt, as Jack slowly started working one of his large fingers inside. He worked it in very gently just as he has agreed to but, his finger was still certainly incredibly large. I felt the first knuckle make its way in, and I took a sharp intake of air, holding my breath. The world seemed to hold still as the chat went silent for a moment.
“He’s doing great folks,” Jack said, and looked over at me smiling.
“Just a bit more, and then we’re in the clear,” he said softly looking at me, as his middle finger continued to inch inside of me.
The chat was nearly silent, as everyone watched in rapt attention, before Jack finally sunk in the final knuckle. I took a deep breath and looked at the chat that suddenly came to life with cheering.
TightTom: He took that like a champ, I can’t wait to see him with a cock in him.
TinyTina: God he is so sexy, I want to see more.
BIGBEAR2 donated 50 dollars for the white one on the left.
I saw the words pop up on the screen as Jack turned to me, looking for approval. I nodded, before feeling the entire length of his finger leave me, and the head of a small realistic white dildo start pressing against my ass. Jack squirted a bit of lube on it, before starting to inch down again, slowly and methodically. He paid close attention to my breathing, and when I stopped or held my breath, he waiting for me to acclimate, eventually putting the length inside me, as I felt the small silicon balls rest against my butt cheeks.
The crowd went wild again at this toy, and Jack spent a few minutes gently pushing it in an out of me taking his time. He would occasionally answer the crowd keeping them engaged, while continuing to stroke in and out of me, applying a bit more lube every minute or so. I was very astutely aware of the cage now, my erection was trying to burst out as I was being just casually toyed with. I had never wanted to ejaculate so hard in my life, and every time the balls rested against my butt cheeks, I felt a tingle down my spine sending pulsing waves into my caged cock. The strain was unbearable, and this was the most exhilarating sexual experience of my life. I even forgot I was on camera for a second just focused on the pleasure happening in my backside.
TinyTina donated 100 dollars for the new boy to jerk off his daddy.
I flushed at the new order coming in, that wasn’t as much as the first night for just standing passively, but at this point I was incredibly sexually charged. Jack looked over and I gave him the nod, as he smiled and clicked accept.
I stayed on his lap, with the toy still slowly penetrating in and out of me as I fished the cock from inside Jack’s jockstrap. The monster was semi hard already, with thick veins running the length. I shuddered a bit when I remembered all the comments suggesting he put this giant thing in me. I tentatively gripped it around the shaft and began to slowly stroke it, I was in an incredibly awkward position here, reaching under his legs as he sat down stroking as best as I could. The comment section when wild again as people loved watching this go on. I got plenty of cheers and some requests for me to blow him, which was not likely anytime soon. I continued to jerk his cock picking up speed as he did, the toy going in and out of my butt was matching my own pumps, we had a rhythm going at one point, both of us breathing heavier and heavier until I felt the familiar spasm in my hand. His cock erupted semen, shooting on my jock and down onto the floor with thick white ropes. Once he felt is orgasm he pushed the toy in as deep as he could reflexively, and my toes curled feeling it tingle that spot, as I let out a soft moan. I was so close to orgasm, the cage was painful as my cock wanted to break free, this was encroaching on agony.
The chat section loved that performance, with a ton of tips going out, saying they couldn’t wait for next time. I was spent and breathing hard, I needed to cum, but that wasn’t in the cards yet.
“Goodnight folks,” Jack said, “We will see you tomorrow as we keep working on this special video.”
I felt the tug of the toy as Jack removed the full length from me, fairly quickly, now discretely aware of the cold air, and how stretched out I was from that session.
“Great job,” Jack said smiling, “We netted another couple hundred dollars from that, not nearly as impressive as our first gig, but you can never predict these things.”
He gave my butt a playful slap, as he moved me over to sit on the couch.
“So come by tomorrow and lets keep this up, next Thursday we will take that cage off, and both be a lot richer… I also wanted to say I appreciate you doing this, I know it’s fun for me, and it seems pretty fun for you, but this was a huge ask, I just wanted to say thank you.”
Jack smiled at me, and I did my text book nod.
“You’re welcome, I will admit I’m having a lot more fun than I expected, and it’s not too much of a pain in my ass,” I laughed a bit, evoking a bigger smile from Jack.
“That’s the spirit, let’s get cleaned up and I’ll send you on your way.”
Jack let me climb off him, as he grabbed a rag and cleaned up his studio, I removed the red jockstrap, tossing it in the dirty clothing pile in the corner. I said my goodbyes, and headed out, the cage still tightly gripping my cock, it was all I could think about on the drive back and heading to sleep.
The next day was incredibly hard to concentrate, every time I moved, I was acutely aware of the cage restricting my movement. I got lost in conversations occasionally, needing to be snapped back to reality. Finally, once I got to the end of the day, I was rushing to get over to Jack, my trepidation was completely gone by this point. I was counting the time down, waiting for our session tonight, taking an extra-long shower, and cleaning myself everywhere.
This night went nearly the same as the last, except the toys had a few bigger ones in the mix, which Jack priced higher. Still nothing terribly large, and it all felt amazing as he was working it into me.
We had a rhythm going doing the same show every night, the toys getting slightly bigger, and the crowd steadily watching my descent into the world of professional sex work. By the last night the toys were nearly as big as jack himself, and all of them were driving me crazy, I couldn’t believe how much I ended up loving this feeling.
After the show Wednesday night, I was pins and needles, I needed to cum insanely hard, all I could concentrate on was the light at the end of the tunnel. Thursday we were done with this, and I would be quite a bit richer. Jack stopped me before leaving though.
“Hey William, there is something I wanted to discuss with you.”
Jack was looking at me, still naked from the show.
“I wanted to say a couple things, I’ve really enjoyed connecting with you like this, I feel way better about having you here than Thomas. It’s been really fun working with you, and if you wanted to stay on, I’d love it if you stayed here permanently.”
Jack said this looking directly into my eyes, the first time he wasn’t all business in our conversations about this entire event.
“If you agree, I want to make tomorrow really special. I want to have sex on camera and capture that for the audience, I think they would like it, and I would really like it. There is absolutely no pressure if you don’t want to, but I think this has been an amazing week.” Jack smiled at me.
I had a lump caught in my throat again, back to the first night of doing this whole thing, and just nodded.
“Sure, I think I’m ready for that. This was much more fun that I would have ever dreamed, the cash is just a fun after effect.”
Jack laughed at that, “Does that mean I can pay you less?” He jabbed.
“Never, in fact, I think I need a raise,” I said, smiling at him.
We parted ways that night, and all I could think about was how the next day would play out, dreaming about the event. The cage still reminding me of the initial contract that started the whole thing.
My Thursday flew by, I barely remember anything at all happening that day, just completely focused on my night. The only homework I had was to take an STD test, as did Jack, which came back clean for both of us. Once everything was in order I got ready with a long hot shower for tonight’s performance. When I drove up to Jack’s house today I parked and jumped out of the car, heading in for what was surely my last day in captivity.
Jack was waiting on the couch, he was already dressed for the show, his laptop out answering fans and creating the content videos. He jumped up and smiled when he saw me.
“Alright, are you ready? Today should be a blast.” He said, as happy as I’d ever heard him.
“As much as I can be,” I said nodding.
We sprinted together down to the studio and moved the couch out of the way. My stomach was turning in knots, but this possibly the most exciting thing I had done in my entire life. Jack zoomed the camera in to the center of the room and had me get on my hands and knees facing the screen. I had to adjust a few times, first left, the right, then left again until I was perfectly in frame. He grabbed the wireless keyboard and mouse and brought them over. Putting them on the floor next to us.
“Are you ready” he asked.
Looking at my face, front and center on the screen I nodded, before Jack started the session. Comments poured in instantly, with everyone noticing not only the difference in setup, but also the perfectly framed face in view.
“Welcome to out stream everyone,” Jack boomed out, “We have a very special event planned today, it’s my friends first time and we are sharing it with you.”
The chat exploded with tons of applause.
BigBear2: Finally I’ve been waiting for this show for a week.
TinyTina: He’s even cuter than I imagined, now let’s see him get to work.
I blushed at all the comments, and all the compliments on me, before seeing the tips flood in. Everyone was throwing money at the show, to a point that I was a bit shocked by the display. I didn’t have much time to process as I felt Jack squirt some lube onto me and slowly start rubbing it in, starting with his finger. I watched my own face on camera reacting to every movement, as did the thousands of viewers we had amassed. He gently removed his finger, while lining up his giant cock he stared forward into the giant TV screen and stared into my eyes.
In a very slow and soft stroke he began burying his giant cock in my ass, the friction was driving me crazy as my own cock pulsed to get out of its prison. The onlookers were going crazy at this, my facial reactions spurring on their comments.
Cockavore: He’s really loving that cock, he was born for this.
POLARBEARx88: This stream gets better every day, I wish I had my own boy like that.
Once I felt Jack stop I realized he was fully buried inside me, the length resting for a moment, before he gripped my hips much harder.
“Get ready Will,” he said gently with a smile, before pulling out and plunging back in.
The force of his hips drove me forward a bit, as I felt his throbbing cock resonate inside of my, hitting that spot that felt so good. Jack pulled back once more and found his rhythm, plunging in and out of me harder and harder, my ass cheeks bouncing off his hips as he pistoned into me. My face was flushed, as I watched my first time being fucked on camera, with the large man behind me driving in and out with his giant cock. I felt every inch moving inside of me, my own hips bucking back into him meeting the thrusts. The small cage holding my cock hostage dangled in the jock strap, pulsing with me. I was completely lost in the moment, until I felt it. Jacks cock pulsed inside of me, filling me with cum, driving me over the edge as well. My own cock exploded in its cage, leaking cum through the cage and dribbling out. Jack pumped a few more times inside of me, depositing his cum as deep as he could before we both collapsed on the ground. Tips were pouring in, as we tried to catch our breath, we exerted everything into that act, and I felt like I ran a marathon. Jack rolled over onto his side and got up on his knees facing the camera, his softening cock dangling now.
“Well, that was intense. Thank you everyone for being with us, the video will be uploaded to our fans page this weekend. But I think we need to take a break for the night.” Jack smiled into the camera before ending the session.
I felt Jack kneel next to me and pick me up, swooping me high in the air as he walked me down the hall and into the bedroom. He laid me down on the bed and spooned in behind me, gently cradling me as I regained my breathing.
“That was the most intense thing I’ve ever felt,” Jack said, “I really think there may be something here.”
He left pause at the end as I searched my thoughts, turning around I looked at him in the eyes and nodded. Before leaning in and kissing him. This was the start of a new chapter in my life.
Epilogue
2 Years Later
We just finished our trivia outing for the week, and tonight was my first anniversary with Jack. We had tied the knot at one year, in a very public event on our page. I found that Jack really had an interest in permanent jewelry. On the car ride back, I touched the eternity collar around my neck, it was a plain silver piece of jewelry designed to never be removed. The silver band was hard metal fashioned in a loop, with a small inscription reading “Beary Creamy Forever”.
My cock strained against the cage, picturing the show we had planned. Every anniversary of our first time we did a special show. The show where I accepted Jack’s marriage proposal and had the collar attached forever, was the last anniversary and this year we had a special guest coming.
As we parked the car, I stepped out seeing a familiar face, Thomas was there smiling with his new boyfriend, Mark. He certainly had a type, Mark was also an impressively built man, rivaling Jack. He had Dark ebony skin, and a thick midsection covering hard muscle with a wide smile always plastering his face. They were the other pair we did trivia with now once Thomas came back into the picture. He had left when his family found out about his sex life and work in porn, sending him into a bit of a spiral for a couple months. After a bit of therapy and lot of introspection he reached back out to explain and apologize. We welcomed him with open arms and with our roles reversed a bit, continuing the friendship we had started.
We all sprinted inside to start the show, we had given Thomas a free subscription to our show as a friendly gift and today was the first time we were going to invite them in to be part of it.
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“This is going to be a blast,” Mark was giddy, at the thought. He was a huge fan of ours, often watching it as he and Thomas had sex.
“You have no idea how much more fun it is filming,” I smiled back before donning the Red Jock, as was customary.
Thomas got back into his old uniform too, as both him and Mark couldn’t keep their hands off each other. The excitement in the air was electric.
We rushed into the filming room with me and Thomas sitting in the center of the room, with Mark and Jack on either side of us. I heard the click and a tingle immediately went up my spine.
“Welcome back, we’ve got a few special guests tonight and a very special show planned, tips are welcome, but we aren’t going to tease you guys too much today,” Jack said with a wink.
Walking over to the toy chest he picked up a massive double ended dildo and tossed a bit of lube on it. My cock immediately pulsed in the cage seeing this, Thomas and I took our positions like we agreed beforehand, taking every inch of the massive dildo between us until we were cheek to cheek. I was facing Mark now, as he sat back with his hard cock facing me, I took the head in my mouth as I began bouncing between the cock in my mouth and the cock I shared with Thomas. We fought to fuck the double ended dildo hard, as I sucked his boyfriend with reckless abandon. Ever since the first click of the cage, I had been more sexually charged than I thought was possible. I loved every second of this, sucking the giant black cock in front of me, taking a second to look back I saw Thomas and Jack back to their glory days. Thomas was sucking his cock with as much intensity as I was sucking his boyfriend. I wanted to race, and I was sure I was going to win. I pumped the cock and worked the dildo as fast as I could before hearing Jack moan. Seconds later so did Mark as thick ropes coated my face.
Thomas and I took a second to breathe before I felt him move away and the dildo come free. I turned around to see Thomas right next to me, as I felt him pull my hips down and lay me on my back, he stripped off his jock, and pressed his cock into my ass, and began slowly fucking me.
“I’m glad you and Jack found each other,” he breathed in my ear, slowly drilling his cock in and out.
“But I won the little game, so your ass is mine,” He smiled as he picked up his pace and continued to drive into me.
Grabbing my cage for leverage, he used it to pull my hips back and forth before ejaculating inside me and collapsing on top of me. We were drenching in cum and panting.
Jack sat back watching with a smile and a wink, “Happy anniversary.”