Social Media Star Ch. 05

[All characters are age 18+]

Lena's dildo definitely felt larger than Miley's. As her strap-on cock slowly slid into my ass, I moaned deeply and as I held my breath, gripped the duvet as hard as I could. The three girls had lubed-up their strap-ons generously, but I still felt every millimeter. When Lena's cock was fully inside me with its fake plastic scrotum pressed against my taint, I knew I was about to be fucked hard... for a second time. My first pegging session was not over yet.

My sister Miley had fucked me first. To be honest, I was so nervous I can hardly remember what it had felt like. But I do remember the girls first deflating and pulling out that wicked buttplug. When it popped out of my ass... and I felt that initial gaping sensation -it was unlike anything I had ever felt before! After its extraction, Miley had been gentle and had graciously warmed me up. I remembered wanting to hate it, but I had instead found myself loving it. Something about it just felt sooo good. But now my attention went back to the present. It was Lena's turn.

As I was trying to mentally process my situation, Lena abruptly slapped my bare ass cheek as she started thrusting. That sharp, stinging slap got my attention. Perched on all fours atop my bed, I looked back over my shoulder to see what my sister's friend wanted. She was directly behind me, fucking my ass doggy style. Her delicate hands were gripping my waist at the hips. I could see her abs flex and release as she moved rhythmically against me. Kylie and Miley were there too. They were atop the bed on either side of me. Both girls were getting a nice view of the show.

Lena made eye contact with me and said, "Timmy, focus! I shouldn't be doing all the work. Arch your back and thrust your boy pussy backwards!"

"Yes Lena," I dutifully replied. I initially had obeyed the girls out of fear, but like I said, I was starting to secretly enjoy my new predicament. As I arched my back and thrusted backwards, I felt a whole new sensation as the dildo began to rub against a new part of me. Maybe my prostate? Regardless, it was scratching an itch I never thought I had. I started grinning like an idiot as the pegging began to feel more and more pleasurable.

After a minute or so, I felt my sister Miley put a hand on my lower back as she said, "That's a good boy Timmy. Keeping arching your back. Doesn't Lena's cock feel nice?"

"It feels amazing, Miley," I replied. I couldn't help myself -it was the truth.

"He really is a little cock slut," Kylie remarked. My sister's other Amazonian friend was kneeling on the opposite side of me. I glanced over and noticed that she was rubbing her strap-on cock in eager anticipation. She would fuck me last.

"Thrust harder Timmy!" Lena shouted.

Without bothering to answer, I started rocking my whole body back harder -my ass now began to violently slam against Lena's strap-on harness every time she thrusted. The whole bed began to shake and loudly slam against the wall. Lena and I were operating in unison. I was taking the whole dildo up my ass, to its base every time our bodies met. The silicone cock must have been a good seven inches or so. Slightly larger than Miley's, but I could hardly care.

The pounding continued until both of us were exhausted. Sweat was now pouring down my face.

"Ok, break time!" shouted Miley just as Lena triumphantly shoved against me one final time, her hands gripping my shaking hips.

"That was fun!" replied Lena as she finally stopped her thrusting and carefully pulled away from me. I felt the dildo slowly leaving my ass inch by inch. It felt just as good leaving as it had felt going in. As its bulbous head plopped out of me, I could feel my ass gape again -this time just a tiny bit longer and wider. Deep in subspace, I let out one final moan as I rested my head on the bed, exhausted and empty.

As I tried to catch my breath, I could feel movement on the bed as the girls shifted positions. Lena moved to take Kylie's position by my side. Meanwhile, Kylie crawled her way behind my elevated ass and placed herself between my legs. It was now her turn. Still panting, I was startled when I felt hands touching and pulling on my limp, dangling cock.

"He's still soft as fuck!" Kylie remarked. I then had the indignity of more hands groping between my legs. I didn't bother looking beneath me to find out who was probing me.

"But you tell he's excited! Look at all that precum," Miley replied. More hands groped my limp cock and balls.

"I prefer him this way. Soft little sissy. His cock is useless anyways," added Lena.

"I agree. But let's not get distracted. Timmy has one more cock to service!" Miley replied. I felt Kylie place her large hand on my lower back for support.

"Timmy, you know what's coming. Be polite and ask Kylie to peg you," Lena instructed.

I meekly nodded to Lena and looked over my shoulder and softly said, "Please Kylie..."

"Please what...?" Kylie retorted, gripping my hips harder.

"Please fuck me..."

"Beg her Timmy!" shouted Miley impatiently.

"Fuck my boy pussy! Please!"

"With pleasure, Timmy!" Kylie replied. As soon as she said the last syllable, she shoved the massive dildo into my gaping asshole. No teasing, no coaxing. Within a second or two, the whole thing was in me. It was the longest object I had ever taken in my ass and almost as thick as the buttplug at its max setting.

"Ahhhhhh!" I managed to scream as her strap-on rammed home. When my well-stretched asshole clenched around the base, I felt Kylie's massive weight slam against me, shoving me forward. But her strong hands on my hips pulled me right back. Back in position, I felt her slam the strap-on into me once more. And again, she pulled me back. She was fully in control. I was just along for the ride.

"Go Kylie!" cheered Miley in approval. I could feel my sister bouncing up and down on the bed in excitement.

I started to grip the bed cover with my hands, desperate for support against Kylie's massive thrusts. Gripping my pink duvet in my shaking hands, I remembered to arch my back in response to my pegging. With my ass up and stomach curved down, I instantly felt my prostate repeatedly stroked by the silicone intruder. As my world shrunk, I closed my eyes and focused on the building pleasure sensations.

With my mind drifting away, I could just feel Lena and Miley get off the bed. But Kylie kept pounding away at my ass. Desperate for more and without being told, I thrusted my ass back to meet her savage thrusts. We quickly got a nice rhythm going, causing the bed to slam repeatedly against the wall. My ass was getting sore, but I didn't care. I could feel something building within me.

Hearing a door squeak open, I opened my eyes to see Lena and Miley pulling something out of my walk-in closet. Out wheeled a large black tripod with a video camera on top! I tensed up as I watched them wheel the ungainly tripod nearer to the bed. They deposited it just a few feet from the side of the bed and began playing with its many buttons and viewfinder. With a few quick adjustments, the video camera and its enormous lens was pointing directly at me.

Shifting my weight nervously on the bed with Kylie still fucking me, I slowly worked up the courage to ask, "Miley what... what are you doing?"

"Just setting up the camera, silly. You know your sponsor, Femboy Inc, requires you to do videos of each of their products... videos they post of their online store..." she replied, as Lena delicately took the lens cap off.

"Do we have to do this now?" I replied through gritted teeth. Kylie was picking up her pace and I was really starting to feel it.

"Yes! How else do you film a strap-on demo? Timmy... you really ask stupid questions sometimes. And I almost forgot, your corporate sponsor actually wants you to film something different this time."

"What!? Different how?"

"Your sponsor wants you to film a sales advertisement for their product! A short clip they can post anywhere online to drum up sales!" Miley revealed.

"What... an ad? What kind of ad?"

"Just a short video. Should be simple to shoot. They even provided you a script... Lena, get the cue cards from under the bed," Miley replied, pointing to something under the bed.

"Sure Miley," Lena answered. I watched as Miley's friend got on the floor, reached under the bed, and pulled out a large poster board with text handwritten on it in black ink. Her strap-on bobbed up and down as she stood back up with the large placard in her hands. From my position on the bed, I tried to read the handwritten text, but Lena noticed and turned it away from me. She then went and stood by the video camera beside Miley.

"Like I was saying, the Femboy company wants you to read this little message into the camera as you are pegged," Miley continued.

I tried to focus on what she was saying, but Kylie was relentless. Trying to compose myself as I felt Kylie's hands grip my hips harder and harder, I managed to ask, "What message? Can I read it first?"

"Absolutely Timmy. First, let us get the camera set up. And by the way, Kylie... do you mind being on camera?" Miley replied.

In between deep breaths, Kylie answered, "Not really. But can you just crop my face out? I don't mind if the rest of me is captured..."

"No problem," Lena replied as she began adjusting the camera and looking through its viewfinder. She lowered the angle of the camera just a fraction of an inch.

"Perfect! Now all we see is Timmy and his cute little face! In the background, I can still see you Kylie pegging him! But nothing from the neck up," Lena remarked.

"That's fine with me, but let's hurry up, I'm getting tired," Kylie said.

Miley and Lena smiled and nodded in agreement. Within the next minute, they finished setting up the camera.

"Ready Timmy? The camera is already recording, so start whenever you want!" Miley shouted.

"Yes Miley," I replied through clenched teeth.

"Remember to smile, Timmy! We all know you're enjoying this!" Lena added.

I put on a nervous smile as I watched Lena turn the large placard around. She held it at chest level, just to the side of the camera so I could just barely read the handwritten script. Squinting my eyes, I had a hard time focusing on the text.

Miley instructed, "Keep smiling Timmy and read this out loud and to the camera!"

My eyes finally focused and at last, I found out what I had to say:

Hi girls! My name is Timmy and I loved to be pegged! And like a good sissy femboy, I only get fucked by Femboy Inc. brand strap-ons! They feel so good in my boy pussy! Order today and get free shipping! Be a good sissy bitch like me and find out what it's like to get really fucked! (blow kiss to camera)

I read the text over and over, trying to make sense of it all. It became more embarrassing and humiliating with each read. I bit my lower lip as I tried to think of a way out of this. But I knew I had no choice but to say it -I kept remembering the awful contract I had signed. During this interval, I had completely forgotten about Kylie pounding away at my ass. I could see both Lena and Miley eyeing me, waiting for me to start. I suspected one or both of them had a part in writing this humiliating speech.

With growing impatience, Lena crossed her arms and said, "Come on Timmy. Let's go..."

I nodded briefly and stopped biting my lower lip. Taking a deep breath, I raised my neck so I was looking directly at the camera. I tried to stay still, but I couldn't help but bob up and down a little bit every time Kylie humped me.

"Smile!" instructed Miley as she irritably threw up her arms.

I smiled at the camera and began talking.

"Hi girls! My name is... Timmy and I loved to be pegged!" As I read this first line aloud, Kylie began to quicken her pace.

"And like a good sissy femboy, I only get fucked by Femboy Inc. brand strap-ons!" Kylie started to pound me harder and harder as I made my way through the script. I felt her hands move from hips to my shoulders. She was trying to find more leverage.

"They feel so good in my... in my boy... in my boy pussy!" It was just too humiliating... I had a hard time saying that part out loud. Lena and Miley giggled as I stumbled over the "boy pussy" phrase. Miley again motioned for me to keep smiling. I recomposed myself, grinned stupidly at the camera and continued.

"Order today and get free shipping! Be a good sissy bitch like me and find out what it's like to get fucked!" Kylie shifted her dildo as I said this last sentence. I immediately felt something change in me. I had felt something similar earlier in the day with the buttplug. My prostate began throbbing and pulsating out of control. I knew I was going to cum.

But I wasn't finished with the script. Remembering the last part, I looked up, puckered my lips, and blew a kiss to the camera. Right after I blew that kiss, I felt myself start to have convolutions in my ass. I was having another ass-gasm! Before I could stop it, my boy pussy started pulsating and greedily pulling on the strap-on. As I climaxed, my eyes rolled back into my head and I involuntarily moaned and gasped... all as the camera was recording. I even started to feel something slowly drip out of my cock. Deep down, I knew it wasn't precum anymore, but I was too embarrassed to look.

Kylie finally stopped as my asshole convulsed for the last time. I didn't even feel her pull out. By this time, my whole upper body had collapsed onto the bed, and I was resting on the side of my face. I just laid there, ass up, face down as I tried to collect myself. I was still panting and gasping for air.

I knew I would never be the same. This was how I wanted to cum from now on. It was just... better. After what seemed like hours, but was probably just a few seconds, I looked up and saw the three girls, still wearing their strap-ons, by the camera tripod whispering to each other. What else did they have planned for me? I licked my lips as a final bit of lube dribbled out of my boy pussy.

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