Another Video

Story Info
Sissy blackmailed into dildo video...
2.6k words
4.59
13.1k
17
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

My first story! Based on a true story. Would love feedback!

"Another video, by tonight", the text message read.

Shit.

It had been months since my black mailer had requested me to send a video of myself to him. I knew it was my old roommate that was doing this, but I couldn't do a thing about it...

About two months into living together, he walked into my bedroom without knocking. We were both living in an off campus apartment together when the incident occurred. Upon opening my door, my roommate Darren witnessed something that he has held over my head since that day. There I was on the carpeted floor in a black shoulder strapped floral fishnet bodystocking and lacy black g-string. I was squatting, holding onto the edge of my bed for balance while lowering myself almost entirely onto a 12-inch black dildo. The black veiny dildo was as thick as a soda can and as long as my forearm, suctioned to the ground by one of my large class books.

Before I knew what was happening, I turned my head around to see Darren standing in the door frame, phone out, videoing what was taking place in front of him. As quickly as I could, I raised myself bending at the hips from the ground, the dildo remained suctioned to the book as it made a wet plop noise slowly leaving my ass. I stood in front of Darren with simulated cum lube running down my stockinged legs as it escaped my gaping hole, pleading for him to stop recording. From this point forward, I knew I was fucked....

With all of the anxiety filled thoughts running through my head, all I could reply was "OK". I waited, but no response. I thought he had forgotten or at least given up on his little game. I wanted to escape the moment. I wanted to be as far away from reality as I could, but this was real. I picked my head up from my phone, looking around at the other people on the metro city bus. It had been almost a year since I had lived with Darren. I was now on my own in a small studio apartment in the city. "Approaching 5th & Cook Street", the bus driver announced over the intercom. This was my stop. I didn't want to get off the bus. I didn't want to go home.

I slowly made my way up the steps to the 4th floor, dreading the moment I would reach my apartment. I opened and closed the door, slung my backpack down, and sat on the ground with my back against the door. I sat with my knees up to my chest and arms around them, staring into nothing. I continued sitting in my coma state for at least 30 minutes. I looked at my phone again. It was all still there. As the sunset and darkness grew throughout my apartment, I couldn't handle this lingering over my head any longer.

I turned the lamp in the corner of the room on, as well as my desk lamp giving as much light to my little apartment as I could. I sat on the edge of my bed untying then removing my sneakers, then my socks, and then my jeans. I stood up in just my blue t-shirt and boxer briefs, bending over as I slowly removed my underwear. My legs and ass wear shaved, but there wasn't much hair on my body to begin with. Standing at 5'8, I wasn't the poster boy for masculinity. My 22 year old lower body filled out more than the rest as I had run track throughout high school and kept a decent figure through out college. The two girlfriends I had always jokingly admired my thick ass, but not until I got into my secret hobby did I begin to imagine what it really meant.

With the curtains closed, in just my blue t-shirt I walked over to the other side of the bed towards my dresser. Pulling open the bottom drawer, I retrieved my necessary belongings from under my pile sweatpants and shorts. I grabbed the large bottle of cum simulated lube and tossed it on the bed behind me. With both hands I grabbed my black dildo, holding it in front of my face for a moment, always mesmerized by its pure power over me. My anxiety began to mix with excitement, but also fear. At this point I had a task to complete, as slutty as it made me feel. Lastly I sifted through my lingerie, deciding what to wear. I finally decided on high-waisted dark black crotchless pantyhose with a matching black g-string.

I put all my belongings on the bed and sat down. The anxiety was overcoming me once again. What was I doing? It was one thing to have this hobby in private and maybe recording myself once in a while, but every time this happened it shook me to my core. I convinced myself to just get it and pretend as if this wasn't to blackmail me.

Leaving my t-shirt on I stood up and quickly snugged the g-string in my ass crack, snugging my small cock into its pocket. I grabbed my tights and carefully pulled them up, aligning the foot seams and pulling the slack up each leg. Finally, I wiggled them over my ass and into place, with them hem just below my belly button. I moved to the bathroom and watched myself align the crotch cut out perfectly from my navel to just above my ass crack. I faced the closet as I looked over my shoulder to the mirror as I admired my full ass squeezed into the tights, slightly bent over with the bare middle revealing my black g string poking out at the top of my ass. I always enjoyed how I looked in tights, and my body was reacting to the slut I saw in the mirror.

Regardless of the reason this was happening, I was getting excited. I peered around the room for where I should suction my monster dildo and impale myself. My flushed faced gaze fell upon the toilet. I picked up my lube and dildo with each hand and walked over to the toilet, closed the lid, and set them down on top. I went back and grabbed my phone to set it up for my video. I placed it on the bathroom counter in such a way that from floor to ceiling I was within the whole shot, standing in front of the toilet.

The time had come. I hit record.

I walked back over to the toilet and grabbed my black dildo. On my knees next to the toilet, I stood him upright and securely suctioning it to the top of the toilet seat. Within inches of my face, I grabbed it with two hands and stared in awe. It held such power over me, I completely forgot about the video. I raised myself to sit my ass on my heels, just straight up enough to have my face slightly above the massive tip of the cock. I licked it from the balls to the head, over and over until it was soaked with my slobber. I began stroking it with both hands while sucking the head of my master as it stretched my mouth. I bent it slightly so I could take as much of it in my mouth as I could. Stroking it I began to fill my mouth with as much black cock as I could. Slowly up and down I could only get about 4 inches of the monster before my jaw began to fight back. Subconsciously my eyes rolled up and I began to force as much of the wet cock into my mouth as I could, forcing it against the back of my throat, expanding my jaw to its limit.

I unsheathed the cock from my mouth with a suctioned pop, strands of slobber hanging from the massive cock to my mouth and my chin, with the neck of my shirt soaked. I slumped my ass back onto the floor, still holding onto the monster staring up at it. I looked back at the phone, only imagining what the sight it was capturing looked like. Getting on my hands and elbows in front of the toilet, I aimed my arched ass at the phone. I squirted handful of cum lube into one hand while bracing myself on the ground with the other. I maneuvered my chest and face on the ground in front of the toilet with my hands ready to get to work behind me.

With one hand I reached in my crotchless tights between my ass checks, pulling the thong to the side. The other smeared the cum all over my fingers and began to lather it between my thick ass cheeks. Instinctively I positioned my knees wider, allowing my ass to spread more. I began to take my index and middle fingers and rub the lube all over my eager hole. Without a fight my ass let my fingers in, regripping them as they pushed more and more cum into my ass, preparing me to be bred. I lay there with my ass up and spread fingering my ass, allowing it to get used to the penetration. Wet slopping noises filled my apartment and my brain. I wasn't event thinking at this point. I couldn't wait any longer.

I got up onto my hands and knees and stood myself up. I moved myself over to my phone, close to my full length mirror inspecting the mess between my ass cheeks. I put my hands on my knees wide apart and bent over looking over my shoulder, ensuring that I was ready to be bred. My small cock was standing hard, pulling my g string tight, disappearing between my cheeks in my crotchless tights again. I walked over to the toilet standing in front of my master, staring down as it bent it self over slightly from its girth. Again I grabbed my cum lube and poured enough in my small hand that it started spilling over the sides. I knelt down once more to finally prepare my black cock. I smeared the cum all over my hands and slathered the monster from balls to tip in a thick translucent cum, mesmerizing myself again. There was so much it began to pool at the base, as if it had already spurted a huge load all over itself.

Aware of the phone behind me, I straightened my legs and bent back up. I sized up the black cock in front of me, determining the best position to allow it to reach deep in my stomach. I decided I would straddle the toilet with my ass facing the phone. I slowly walked forward realizing I wouldn't be able to just squat my thick ass over it. My master was so big that I had to put my legs on each side of the toilet while balancing myself over him on my toes. Even raising myself on my toes it was still mere inches from my ass. While on my tippy toes, I grabbed the base of the toilet in front of me for balance, while I reached for my dildo between my legs with my other hand. It was so wet and slippery I could barely hold on. With my hand not even grasping the entire width of the monster, I slowly began to lower myself until it was beginning to part my cheeks.

Without effort my thong was moved to the side and my hole met the head. My brain was spinning, eyes rolling, I couldn't process a thought. I guided my dildo as it began to slowly meet my eager hole, and then I knew I had to have encourage him in. I began with small bounces, as the noise of the wet cock touching my hole began to fill my brain. I finally had the head in after some work, but I was still on my toes. With wet slops it had slipped out a couple times, but I held onto it as I forced more of my ass down onto him. I no longer needed to hold onto it, so I braced both my hands on the base of the toilet in front of me. I arched my back, sticking my ass out for leverage, and began to work my ass slowly up and down. I wasn't even a quarter of the way down. The wet sounds of my ass meeting my black dildo filled the room. With more force I encouraged more of him into my widening hole, and I could finally stand on my feet. The camera watched it all.

The view of me hunched of the toilet in my crotchless tights and blue t-shirt filled the frame of the phone. I began to thrust down harder slowly, and work my way up until just the head of the cock was still in me, and then force back down. It was inching deeper, at least half way, and I could feel it begin to shift my guts. With my head lulled back and my mouth open drooling, I continued to work my fat black dildo into my ass. I needed to be fucked. I sped up the pace with what I already had inside me, inching myself lower as I did. My legs burned, and my guts were on fire, but I didn't care. With each upward thrust now the monster wasn't even reaching half way out my hole. I widened my stance, put my hands on my knees, stuck my ass out further. I could tell I was close to the bottom, it was reaching a familiar spot in my gut that I knew.

I slid myself as high as I could from this position and pistoned down deep on my master. I held it deep after each thrust, the sloshing sound of my ass eating my dildo was unbearable. With one final determined thrust, I raised my ass slowly back up and pushed down hard. I had bottomed out. I could feel his balls resting on the skin of my exposed ass in my tights. I could feel the huge cock deep in my stomach, it was a feeling unlike anything else. I held it there as my eyes rolled back into my head. I raised back up slightly, and forcefully rammed my black dildo deep into my stomach. With one hand I raised my shirt and held it under my chin. I could see my master poking out the skin of my stomach.

Once more I place my hands on the base of the toilet and slid the cock as far up as I could onto my toes, and rammed it back deep inside of me. Instantaneously with the last deep thrusts I could feel my orgasm building until my small cock spewed cum up to my stomach and onto the toilet base in front of me. I lowered myself back down once allowing my black master to rest inside of me as I rest my head on my arms in front of me. I had been bred. I needed the real thing.

I regained enough energy to stand myself upright again, with my dildos head still inside of my weak hole. I arched my feet to my toes, reached between my legs and held onto the cock. I lifted one leg and with a final heave my master slumped out of my ass with a loud wet slop. I stood straddling the toilet still, my ass wide open and cum leaking out and down my tights. I walked over to get my phone to send the video before I passed out.

The phone had stopped recording over an hour ago.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
AnonymousAnonymousabout 1 year ago

I love this story! I related to the power the big black dildo has over you. Anxiety mixing with excitement is at the core of my sissy experience. The relinquishment of power. The need to be dominated. I love it all.

Share this Story

Similar Stories

Trapped and Trained Ch. 01 Man is drugged, then dressed up and trained to be a slut.in Transgender & Crossdressers
Lesser of Two Evils A man's choices will transform him into a cum slut.in Transgender & Crossdressers
Sissy Sammi Surrenders Blackmailed Sub sissy.in Transgender & Crossdressers
Willing to do anything A debt costs a man his dignity.in Transgender & Crossdressers
Making of Tina Ch. 01: Caught A story about forced feminization.in Transgender & Crossdressers
More Stories