Feminizing First Step Ch. 07

I was meeting my internet "daddy" for the first time today. His last text message to me had been very clear: tie myself to the motel bed and wait for him to arrive.

I stared at the antique bed with its black metal frame and headboard, wondering to myself if this was such a good idea. This rundown motel had been hard enough to find. I had never been to this rundown part of the city before. Now, having checked in and found my room, I glanced around the rest of the tired looking room. Not too much else worth noting. Heavy, stained curtains covered the windows, darkening the whole room despite it being only five o'clock in the afternoon. But there was enough natural light still coming through, so I left the room lights off.

I pulled out my phone and read his instructions over again one last time. Reassured, I got to work. I put my bag by the side table, reached in, and took out a pair of panties and some neckties.

My clothes came off next, and I got dressed per his instructions. No bra today. I took it off, put it on a chair, and looked down at my chest. My little breasts were growing, but they were still woefully too small. But I knew -or prayed rather- that I would one day grow into my D-cup bras. A few months of testosterone-blockers and oestrogen shots were simply not enough, I told myself, as I then moved on and removed my latex panties.

I put the latex undergarment (with the built-in mock vagina!) on the side table and instead grabbed the Victoria's Secret panties I had been commanded to wear today. The tiny thong was a perfect fit! Thankfully, I had always been blessed with large hips and a thick ass. As the pink thong slid up my rear, I tucked my shrunken boy parts in as best as I could. Satisfied that everything was in place, I took a second to admire them -I especially like the tiny, white bow in the front, right below my bellybutton piercing.

To save time, I had already done my makeup at home, but I still applied more mascara and touched up my lipstick in the bathroom. The last thing to go on was my heels. Balancing with one hand on the TV stand, I stepped into the 4-inch pumps. The stiletto heels dug deep into the faded carpet as I walked around the room making the final preparations.

Now fully dressed, my attention turned to the bed. The metal frame made a convenient tie down point for the arm and leg restraints. The best I could do on such short notice was some old neckties, but I knew they would work okay. I had tested all of it back in my bedroom the day before. After making sure the door to the room was locked, I walked over to the bed and hopped on top -leaving my shoes on. I positioned myself towards the headboard, but I remained resting on my stomach, facedown.

I carefully tied each of my ankles to the bottom corners of the bed using the silk neckties -silly boy things I had long ago stopped wearing. Slip knots made this an easy process. With each ankle secure and my legs spread wide, I shifted myself towards the center of the bed, so that I resting on my stomach atop a mound of pillows. Now with my ass angled slightly upwards, I moved on to the final task. This was going to be much harder.

Remembering my date's instructions, I fashioned another necktie into a gag and placed it in my mouth, fastening it behind my head. My short pixie cut did not get in the way -one of the reasons I had opted not to wear one of my wigs today. With my lips wrapped around the silk fabric, I instantly started to drool on the fabric -just like when I had tried it the night before. I next managed to get my left wrist secured to the metal headboard. Now with only one hand free, I put on the final item: a blindfold. With my vision completely obscured, it took me a while to find the necktie restraint for my right wrist. When I found it, I slipped my wrist into the loop and pulled on the loose end of the restraint with the same hand. This pulled my wrist and the rest of my right arm towards the final corner of the bed.

I was now completely tied to the bed. Spread-eagle with my ass in the air... as my date had requested.

Thankfully, I had had the foresight to put a pillow under my head, so I was mildly comfortable -if I ignored the fact that I could hardly move. I turned my head to the side as I rested against the pillow. The metal frame of the bed creaked as I tested my homemade restraints. A minute or so passed as I began to mentally process my situation. The room was freezing! In my excitement, I hadn't noticed. Nothing to do about it now, I thought. Did I make sure the door to the room was locked? What if the cleaning lady walked in and saw me? A young, helpless femboy in lingerie tied facedown to a bed would be quite a shock!

More time passed. The pillow started to become very damp from all my saliva. I was kind of glad that I couldn't see it. Everything was black to me. Mostly. I could see some ambient light coming through the edges of the blindfold. But not much. My feet began to ache in the confining shoes. The pain was too much. After much effort, I managed to kick them off and heard them fall to the floor. I hoped my date wouldn't be upset.

With all my senses dulled, my thoughts turned back to my internet sponsor. "Big John" as he called himself had befriended me months ago on an online dating site. I had set up my entire dating profile in response to seeing that my sissy friend Ella had new boyfriend. Jealous of Ella, I had posted a few cute photos online -just to get some attention. John had "liked" a few of my photos and private messaged me. And after some brief exchanges, he had offered to pay for some private photos of me in various stages of undress. It was good money and he was always so supportive and appreciative. One thing led to another, and packages started arriving at my house. Cute lingerie and makeup kits at first. But the deliveries soon became sex toys and other naughty stuff.

Back in the motel room, many hours must have passed. When I woke from my brief nap, I couldn't see any light through the edges of my blindfold. It must be nighttime now. Maybe nine or ten o'clock, I guessed. Maybe later. As I stirred from my brief slumber, I started to get hard in my panties. I humped the pillows under my body, desperate for some relief. But no success.

I had just begun to relax against my makeshift restraints in frustration when I heard footsteps just outside the door. I could hear a keycard being swiped! The electronic door mechanism made a mechanical clicking sound, and then the door opened. Warm, humid summer air entered the room. I could feel it on my exposed ass cheeks. I tried talking but my gag garbled all my words. I was incomprehensible. Then the door closed shut with a loud slam. I again tried mumbling and craning my head back, trying to get a glimpse. But no luck. I was completely blind.

I sensed someone in the room. The light switches were being turned on. Trying to get my date's attention, I awkwardly fought against my restraints, making myself bounce against the bed. The bed only squeaked in response. I heard no reply!

Next, the door opened again. Now I began to hear people whispering. MORE people!? What was going on? This wasn't part of the arrangement! As I began to freak out, I could hear more and more people shuffling into the room. I could hear their footsteps and soft voices. I smelled cigarettes and weed. As I was processing what was happening, I then heard loud bangs and thuds against the floor. The whole room shook in response. They were bringing stuff in with them!

In full panic mode, I fought against the neckties holding me to the bed. But the ancient metal frame of the bed held true and my knots only got tighter. What had I gotten myself into!? I could sense people busy milling about the room. I then heard what turned out to be bright studio lights being turned on. Seconds later, I sensed the warm heat from these lights on my nearly naked body. They were using photography lights...was this becoming a film set?

My heart was racing. However, my initial fear was gone -replaced with something else. There was no denying it -I could feel myself getting more and more excited. And I did not know why. When I began to feel hands caressing my ass and pulling at my thong, I knew I was in for a long night...

I then heard more heavy footsteps. Another person had just entered the room.

"Ok good. The sissy bitch followed my directions," said a deep male voice.

"She's ready... just like you said, John. We have everything set up now. Are you good to go?" replied a loud female voice.

"Fuck yeah!" the same male voice yelled. This must be Big John, I thought.

"Well, the cameras are all setup and recording. If you don't mind John... we need to get started. We have a long night ahead of us," replied the woman.

"Don't need to tell me twice, Michelle."

The room filled with laughter. There were definitely many more people in the room. Starting to worry again, I could no longer keep quiet. Desperate, I grunted into my mouth gag, making an "ahhhhggg!" sound. This noise got their attention.

"Quiet Kitten!" shouted Michelle. I felt a heavy hand slap my left ass cheek and I involuntarily grunted again through my gag -in a mixture of pain and pleasure.

Michelle added, "Don't try to speak again... unless you want more of that!"

Still reeling, I kept quiet and heard more shuffling in the room. A belt buckle was being undone. Clothes were being taken off. Next, I felt something heavy get on the end of the bed between my outstretched legs.

The heavy weight shifted closer and closer to me. Large, rough hands grabbed my waist. My thong snapped loudly against my skin as it was pulled to the side, out of the way. I then heard the man between my legs spit and felt a warm wetness against my sissy asshole. I was about to lose my real anal virginity! I impulsively wiggled my ass in anticipation.

A heavy hand pushed down on my lower back as I felt his cock begin to press against me. I opened up slowly to him. As he entered me, I felt a sharp pain that seemingly lasted for an eternity. But the pain eventually went away -in its place came a wonderful sensation. A sensation that I had never felt before. His cock must have huge! Larger than any strap-on I had ever taken.

Once inside me, he began to fuck me. Mercilessly. The whole bed moved as he thrusted into me. I pulled against my restraints with each of these thrusts. My wrists and ankles started to be rubbed raw from all the friction and wild motion. Not that I noticed. My whole attention was focused on my daddy. I was in heaven. Girls were right... nothing could compare to real cock. I knew I could never go back to dildos or my mom's strap-on.

Occasionally, I heard Michelle shout commands like "grab her hair" or "slap her ass"... but I could hardly hear her voice over the sound of the bed slamming against the wall and John's grunts. I moaned and moaned through my gag as the waves of pleasure poured over me. I don't know how much time passed, but I know I had multiple analgasms... at least by the time John finally climaxed. He pace began to quicken and he pulled me harder and harder against him. I felt his cock swell inside me as he ejaculated in my boy pussy with a loud grunt. What a new and delicious feeling! After a few seconds, he pulled out, and I felt his warm cum drip out of me and down my taint.

"That was a good piece of ass. You were right, Michelle!" he stated, as he got off the bed. The bed shifted causing me to rock against my restraints. I felt more of his seed ooze out of me.

"That was a perfect performance, John. Tyrese... you're up!" shouted Michelle.

Tyrese? Before I had time to think, I felt another guy get on the bed. They were running a train on me!

"Here's a towel, Tyrese. Clean her off. The cameras are still rolling, but I can edit this all out," said Michelle.

"Thanks Michelle," replied a new male voice.

Someone wiped me down, and before long, I felt something being inserted into my ass... I tensed up before realizing it was just a bottle of lube.

Tyrese was gentler than John. Thankfully, my boy pussy was already nicely loosened up. His thrusts were slower but deeper, with his huge balls slapping hard against me. After a few minutes of him fucking my ass, I felt him pull out and then felt the jets of cum on my back. Another new but lovely sensation!

I could hardly savor this delicious feeling before another guy took Tyrese's place. Mike was his name... I think? After Mike was Darnell, followed by at least two others. I lost track. At some point, I must have passed out. When I awoke, it was still night time. But my restraints were gone! My mouth was free of its gag too, but I could taste something weird in it.

Still resting on my stomach, I slowly turned over in the bed and propped myself up on the cum-soaked pillows. My panties were long gone and a strange, lacy bra had been tied around my neck.

The room was dimly lit with only a table lamp. Large metal tripods with video cameras were still in place around the bed, but the portable studio lights had been turned off. The rest of the room was a complete mess. Liquor bottles, random cups, beer cans, condoms, dildos, and trash littered the room and covered the bedside tables.

Blinking my eyes and trying to adjust to my surroundings, I saw that I was not alone. A stern but beautiful looking black woman was sitting in one of the side chairs. She was dressed in a white tracksuit and smoking a cigarette. In her other hand was a dog leash. My eyes followed the leash to the other person in the room. Ella! My sissy friend was kneeling on the floor beside the woman! And she was completely naked... apart from a pink dog collar around her neck. She looked beautiful with her hair in pigtails and large golden hoops in her ears. Her little, castrated nub stuck out between her legs. Ella smiled back at me before looking back down at the floor. What was she doing here?

The woman took another drag on the cigarette before putting it out on the ashtray. She had clearly been waiting for me to wake up. Smiling, she turned in her chair to face me.

"My boys are busy taking a break right now, Kitten. But don't worry they'll be back," she firmly stated.

"You're Michelle?" I asked, although from her voice, I was sure she was her.

"Yeah."

"What... what is this? What's going on?" I asked timidly.

"The start of your new career, sweetie!"

"Career?! What the hell are you talking about?"

"Your mother wants you to be a porn star! A sissy porn star! She contacted me and I was glad to help. Ella here has been working for me for a long time now. Your 'Big John' is a longtime collaborator of mine too."

Michelle tugged on the leash as she mentioned Ella. The kneeling sissy smiled and quietly nodded as Michelle talked.

"I have had a lot of success with your friend Ella. But since she has been neutered -so to speak- I have been looking for someone more... well more like you, to be frank," Michelle continued.

As she continued to talk about her porn production company, my attention drifted back towards the bed I was sitting on. I first noticed that a large double-sided dildo was resting on the end of the bed by my feet. I also realized that something was still in me! I discretely reached down and felt the hard plastic base of a butt plug. They must have plugged me after they had "finished" with me!

Noticing me fingering my new buttplug, Michelle then said, "I would leave that in if I were you..."

She then tugged on the leash and said, "Ella get up and on the bed. The break is almost over. We have another scene to shoot."

"Yes Mistress Michelle," said Ella. She dutifully got up, stood on her bare feet, and then hopped on the bed beside me. As she sat next to me, she leaned over and gave me a kiss on the cheek. Part of me was glad she was here.

"The next scene involves the both of you. I need you to get on your hands and knees facing each other," commanded Michelle. She got up from the chair, walked over to the bed, and grabbed the two-sided black dildo.

Ella and I repositioned ourselves on the bed so that we were facing each other. Our sissy asses practically hung over either side of the bed. With us in position, Michelle reached between our heads and placed one end of the dildo in Ella's waiting mouth and the other end in my outstretched mouth.

"Perfect! You two girls look adorable!"

With our mouths full, neither one of us could respond to Michelle's comment. But I saw Ella's eyes light up in delight. She was enjoying this. Michelle then untied one of my neckties from the bed and carefully wrapped it around our heads. She deliberately pulled it tight before fastening it into a knot -forcing Ella's and my head together. Our outstretched lips met in the middle as we were forced together. We were now kissing each other around the massive dildo. I could even taste Ella's strawberry lip gloss.

From the corner of my eye, I could see Michelle grinning -she was pleased. She quickly moved on to the studio lights. After the bright lights had been switched back on, she then did the same to the three video cameras. I could see their red 'record' lights blinking. While this was happening, every time Ella or I shifted ourselves on the bed, the massive dildo in our mouths shifted too -often pressing at the back of my throat.

"Our next scene is about to start. I want you girls to stay right where you are! And remember to have fun!" teased Michelle as she gave each of our bottoms a little pinch.

Right as she finished talking, I heard footsteps outside and the door open. In streamed almost a dozen guys. Huge, beefy looking men. Michelle walked over to them and starting talking in low tones with them. Shortly later, two black studs walked back with her, took their robes off, and positioned themselves on either side of the bed, directly behind Ella and me. I couldn't move my head to look at the guy behind me, but the guy behind Ella was massive -his arms covered with tattoos. If only she could see him! Before I could warn her, someone pulled out my butt plug. Then huge manly hands were on my hips. With the cameras rolling, Ella looked hungrily into my eyes as our lips began to be pressed harder and harder together...

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