Social Media Star Ch. 03

[All characters are age 18+]

A lot has happened since my last update. My sister's Hollywood career continued to take off. She got small speaking roles on a few TV shows and booked several commercials. All the while, her Facebook and Instagram accounts garnered over a million followers each. She and my step-mom were ecstatic.

Meanwhile, I became more and more involved with my own sponsor:FemBoy Inc.With each passing month, I received new products to use and review on my own social media platforms. Most were various types of lingerie and shoes. Recently, I started taking a special diet and vitamin pill they offered. Off camera, I continued to wear their boy-friendly panties, makeup, and other feminine garments around the house. But I still hadn't worked up the courage to dress in public while wearing their attire.

Today began with me waking up still wearing my special vibrating panties -and nothing else. After my embarrassing introduction to them months ago, I had initially sworn to never wear them again. But that vow had not lasted long. I now found myself secretly wearing them every night. I had settled into a routine: the tiny underwear's built-in vibrator brought me to orgasm when I first went to bed and once again in the morning. Despite my best efforts, I had developed an almost Pavlovian reaction to wearing them. I had begun recently to worry about my addiction to them. I hadn't stroked my cock in months and couldn't remember the last time I got morning wood. Was I losing interest? Or was it the special vitamins FemBoy had me taking every day?

But today, I had a more pressing problem on my hands.

Right now, I was staring at that very problem. It was sitting on my bed. Weeks ago, I had received yet another package and letter from FemBoy Inc. They wanted me to try out and model a new product. The box and letter were now sitting on my bed.

I nervously rubbed my neck. I had put off this problem for too long. I was now out of time. Today was the final day. The final day to post pictures and a video of myself using their new product. I was at risk of breaking my sponsorship contract if I didn't post a demo video by midnight tonight.

I looked anxiously at the black silicone sex toy resting on my bed. I shuddered at its size and purpose. Why!? Why had they sent me a buttplug? And an inflatable buttplug at that! When I had first received the bizarre sex toy, I had quickly thrown it back in its shipping box and had forgotten about it. At the time, I thought that there was no way I was going to model that. No way! Panties were one thing, but this? This was crossing the line.

But now, glancing at the time on my phone, I knew I was out of time. Last night, while I laid awake with my underwear vibrating away, I had made up my mind: I couldn't lose my modeling contract with my one and only employer. It was my only source of income. I needed the weekly paycheck from them. I also found myself thinking about my online followers. For some strange reason, I didn't want to let my loyal fans down.

Earlier this morning, in a desperate attempt to end this ordeal, I had lubed the black silicone plug and had tried to get it in my ass. But I had failed. It was too big, and the rubber tube and squeeze bulb at its base had made it awkward to grip. It didn't help that I had never tried anything like this before. Attempt after attempt had failed. Afterwards, I had broken down and done the unthinkable: I asked for help. With sweaty palms, I had texted my mom and filled her in on my "little" situation so to speak. Unsurprisingly, she had instantly agreed to help me. I also learned that today, thankfully, Miley was at lunch with her friends, so she wouldn't be here to see what was about to happen.

As I stared at the cardboard box, I could hear my mom downstairs getting things ready and rearranging furniture. Knowing it was past time to start, I grabbed the buttplug from its box and walked slowly downstairs. I wore just a small pair of running shorts. No make-up or heels today. I wanted to keep my face off camera as much as possible for this demo video. Or at least try. Underneath my black shorts, I wore a FemBoy Inc. branded G-string. It was a bit too small for me -I barely fit in its little, pink pouch- but I knew I had to wear their merchandise whenever I was on camera. It wedged itself up my backside with every step I took. Hopefully, the tiny underwear might be able to stay on while we filmed the buttplug demo. I was soon to be disappointed.

I found my mom in the living room setting up the lighting gear. I noticed that the large, leather recliner was out of place. It was now in the center of the room. The large, overstuffed seat was surrounded by lights.

"Oh Timmy, I'm so glad you asked for my help with this. Wish you would have asked sooner. You know I'm always here to help," she said, as she adjusted the last lighting tripod. Her hair was in a tight bun and she was wearing her clear framed glasses. She was dressed casually like she was going to run some errands. She had on an untucked collared shirt with its sleeves rolled up, yoga pants, and running shoes.

"I don't think this should take too long mom. They just want a short video of the toy and how it works," I replied. I couldn't bring myself to say "buttplug" in front of her.

"Alright, alright... but your face isn't done up Timmy. Want me to help with that?" she coyly asked.

"No, no... I don't need to show my face for this," I explained, secretly hoping she bought it.

"If you say so, sweetie. Now...are you all set?" she asked as she playfully patted the back cushion of the chair, inviting me to approach.

"Yes mom."

I walked over to the large chair and gently placed the buttplug and its attached rubber tube and pump on a nearby side table. The room's large Persian rug felt soft beneath my bare feet. When I was in front of the chair, my mom raised an eyebrow at me. I knew what she was getting at. My shorts had to come off. I quickly slid them down my legs and stepped out of them, kicking them to the side.

"Pink panties Timmy? Cute!" she said as she playfully pulled at one of my G-string's sidebands.

"Do you want me on the chair mom?" I said, trying to distract her.

"Yes! I thought it would look best if you were elevated, rather than on the floor. Right? Anyways, take off your panties and hop on."

"What? Oh... I want to keep them on. I'll just pull them to the side when we film," I explained.

"If you insist... now get on the chair. I recommend kneeling on the seat cushion with your stomach pressed against the backrest. That way you can grip the back of the chair for support... if you need it."

I nodded in agreement and got on the chair. The leather cushion felt soft but cold under my knees. I gripped the back of the chair -almost giving it a bear hug- as I repositioned myself. Once I got in a comfortable position, I looked over my shoulder. She was right behind me.

"Timmy arch your back...that's a good boy. Keep arching it. Okay, I think we're all set."

As I kept my back arched, I heard her walk away and grab the buttplug off the table. I then heard the snap of latex gloves and then a loud squirt of something. Craning my neck, I saw her rubbing clear lubricant all over the large toy with her now gloved hands. The black silicone glistened under the lights. The toy must have been over 6 inches in length. I turned away and involuntarily shivered. I then heard her walk back over to the chair.

"Now keep arching your back Timmy and spread your legs a bit. Good boy. That's it," she said in a soothing tone. I felt her gloved hand on my lower back. She began to press down hard.

"Ready Timmy?"

"Yes mommy." I swallowed nervously as I said this.

"Pull your G-string to the side."

"Yes mommy." I reached back and pulled it out of my ass crack and moved it to the side. It snapped loudly against my bare ass cheek as I released it.

"Good boy. Now try and relax Timmy. This might feel a bit... awkward."

"Please go slow," I begged. The anticipation was killing me.

A second after the words left my mouth, I felt something hard and wet begin to be pressed against me. I instinctively flinched. But I quickly recomposed myself and gripped the back of the seat as the pressure began to build. She said nothing. With one hand on my lower back and the other pressing on the buttplug, she was slowly working the silicone toy into me. My tight asshole was barely budging. Just like earlier this morning! I began to worry that nothing was ever going to happen. But after a few more seconds, I could feel myself just barely opening up. I felt an initial sharp pain as this happened. But it slowly passed as the lubed silicone toy was slowly pushed into my ass. I could feel sweat dripping down my forehead.

"Keep still, honey. It's almost in," she said, keeping her tone soft and reassuring. She repositioned her hand and started to lean more heavily against me.

I could feel the pressure building and building. Then something shifted. My virgin sphincter gave up its fight. I began to really open up to the silicone intruder. The buttplug felt cold and wet as it slid slowly into me. I closed my eyes as the sharp pain quickly passed. The plug was in much farther than I had achieved during my morning attempt.

"That's it. Remember to take deep breathes, kitten," said my mom.

Her encouraging tone helped distract me as more of the toy slid into me. I felt a growing fullness feeling. A strangely familiar sensation. I was now taking the whole buttplug with little resistance.

"How much more mommy?" I asked, eager to end this increasingly humiliating experience.

"Almost there, Timmy. Just one more sec-"

Before she could finish her sentence, I felt myself abruptly clench around the narrow base of the plug, involuntarily pulling the whole thing into my hungry ass. My ass let out a slurping sound as it swallowed the plug -I could feel the excess lube squirt out and run down my taint.

"Oh my god Timmy! You took it like a champ! I am so proud of you!" she stated, repeatedly slapping my ass in excitement.

Without bothering to reply, I shifted myself on the leather recliner. The buttplug moved inside me as I repositioned my body. Every time I moved, I could feel it press against something deep within me. I felt waves of pleasure every time this happened. Not wanting to reveal this strange sensation, I tried to keep a straight face as I gawkily moved around on the chair. I needed to get this over and quickly!

"Mom, I think we can start the demo now? Right here should work, right?" I said, trying to act natural.

"Yes kitten. This should work perfect. Let me get the camera."

Without turning around to look, I heard her take off her latex gloves and leave the room. I remained kneeling on the seat of the recliner, facing the headrest. She quickly returned, this time carrying a video camera on a tripod. I turned around again and watched her as she deftly set it up and turned it on. Before I could change my mind, I could see the red record light blinking at me.

"You'll... you'll edit this video later? Right? The company just wants a few photo stills and video clips for their website. Nothing fancy," I explained, trying almost to convince myself more than her.

"Absolutely dear. But to be honest, Miley will probably have to do it when she gets back. I don't know how all that stuff works," she replied.

"That's ok I guess," I answered. As I shifted on the recliner with my plugged ass towards the camera, I felt my G-string slide back into place between my cheeks.

"Timmy, your panties..."

"I know. I know." I quickly reached back and grabbed the black strap between my ass cheeks and pulled it aside, releasing it against my left butt cheek with a loud snap. We both knew that FemBoy Inc. would want clear, unobstructed photos of the buttplug in my ass.

"Timmy, this is ridiculous. Just take them off. They'll keep getting in the way."

"This will work fine. See! They're staying out of the way," I said, shaking my ass to demonstrate.

As I did this, I could feel the black G-string strap slide right back between my cheeks again. Damn! I should have known that this ridiculous G-string was too small for me.

"Timmy... we are wasting time. I have a hair appointment at three. Just take them off and we can get this done and over with."

"I just don't want to be completely naked on camera. I don't want people... or you... to see my boy parts."

"Ha! Give me a break Timmy. It's nothing I haven't seen before. Now come on... don't be shy." She snapped her fingers and pointed to the floor.

"I guess we're only shooting my backside anyway," I reasoned, trying again to bolster myself.

"Exactly dear. Just your backside. They probably won't see your 'boy parts' anyway..."

Satisfied and without getting off the chair, I slowly peeled off my G- string. I felt myself pop out of the front pouch as the tiny garment slid down my thighs and to my feet. I carefully kept my backside towards my mom and the camera the whole time. Despite my attempts to keep my modesty, I began to blush as I kicked off my pink panties onto the floor.

I had never felt so exposed: I was now completely naked, perched upon the leather chair with only a buttplug inside me.

"See? That wasn't so hard. And now... let's pump you up!" shouted my mom.

Before I could reply, she walked towards the chair and grabbed the dangling rubber bulb. I could feel the connecting rubber tube tug against me as she moved around. Thankfully, this did not pull the whole buttplug out. It remained firmly in position.

"Don't worry, Timmy. I know what you are thinking! I have the camera focused just on your cute little butt... I'll just stand here to the side and pump up your buttplug. I'll remain off camera!"

"Do you think that's necessary, mom? I don't think we need to show that..." I pleaded. I was starting to have second thoughts. I knew what was coming.

"Oh come on! That's the whole point. Prospective buyers will want to see how it works!"

Not wanting to respond, I watched as she gripped the rubber squeeze bulb in her left hand. She then gave me a devilish grin and squeezed the bulb. The effect was immediate. Something began to instantly expand inside me.

Shocked, I let out a spontaneous "Oh!"

"You liked that Timmy? Let me give it a few more squeezes."

With each squeeze, the buttplug grew inside me. I could feel a pressure building against my bladder -I felt like I almost had to pee. She did not stop pumping.

"Mom please slow down..." I pleaded as the plug grew and grew. The pressure was unrelenting.

"We need to do a full demonstration. Just stay still, kitten. Mommy will take care of you."

I closed my eyes and gripped the back of the chair. I could feel myself being stretched with each pump. I lost count of how many. Meanwhile, the awkward pressure sensation in my ass was changing into something else. All of the sudden, my ass began to rhythmically pulsate, pulling the buttplug in and out. Now I was practically feeling a deep pleasure sensation every time she squeezed the rubber bulb. I started to get tingling sensations spreading throughout my body. Too nervous to look down, I knew I was leaking precum from my dangling cock. I prayed that that was not going on camera. Worried by where this was all heading, I felt like I had to stop her.

"I think that's enough mom. I can't take much more..."

"Just a few more," she curtly replied, cutting off my protests.

She continued to pump away. But after a few more seconds, when my ass had been stretched to its limit, I felt the plug stop growing. I was right on the edge with the novel sex toy maxed out. Despite reaching the limit, I could hear her continuing to squeeze the bulb again and again to no avail. Quietly relieved, I turned my head around and looked at her. Our eyes met. She wasn't done with me yet. With a mischievous smirk, she gripped the connecting rubber tube and gave it a firm tug. This violent motion caused the plug to abruptly shift inside me. It pressed hard against my prostate. I went over the edge.

I let out a loud moan as I had my first anal-induced orgasm. All on camera. It was unlike anything I had ever felt before. My body tingled all over. As the waves of euphoria hit me, I could feel warm cum drip out of me. My ass began to throb over and over on its large intruder. With each pulsation, more cum dribbled out of me and onto the leather chair. This seemingly went on for an eternity. I did not want it to stop. As the ecstasy ebbed, I glanced down to see a large puddle of cum beneath me.

"Now THAT is what I call a thorough demonstration! Timmy, you made quite a mess!" she said proudly.

"I'm sorry. I... I couldn't help it! You shouldn't have pulled on it like that. I-" I stammered at loss for words.

"What's done is done, Timmy. Now put your little underwear back on. We need to get this place cleaned up. I'll put the camera away."

"Why?" I asked, as I clumsily shifted on the chair. The squeeze bulb and tube were now free and brushing against my legs.

"Your sister and her girlfriends are coming over to celebrate her latest gig. She should be here in ten minutes or so."

"What?! She's having friends over? Why didn't you tell me before?" I asked as I quickly got off the chair and stood up. I remembered to cup myself with my hands as I did this. The buttplug felt uncomfortable as I stood on the rug.

"Well I'm telling you now. Come on Timmy, put your panties on and let's clean up."

"What about my buttplug?" I asked, trying to mask my concern. The phrase instantly filled me with shame.My buttplug. What had I been thinking asking her for help? Why had I put myself in this ridiculous position? My mind was racing.

"Oh... I think we can leave it in for now..." she replied with a coy smile.

My mom kept standing there with her arms folded. She was clearly enjoying my predicament. I was beginning to panic. I felt so exposed as I desperately looked around the floor for my dainty underwear. I felt the squeeze bulb and tube swinging behind me -almost like a rubber tail. I knew I would need help taking it out. Sweat was beading down my face.

"What! No! Help me take it out! It's too big for me to-"

Before I could finish my sentence, I heard the front door open. Miley and her friends were here. I clenched hard on my buttplug.

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