The Crossdresser did not Realize who they Were messing with. (Futanari on Male Story) Chapter 3

Carly’s smile was dark and sinister, and I did not know what to do. The snap of the latex gloves made me tremble as I knew she was up to something, but I had no idea what. She moved forward, and not a minute later, my legs were bound up to my head with my ankles touching my ears and behind my shoulders a bit. She grinned, “I love how flexible you are, my good little girl,” She said and stroked her massive cock, and she finished binding my hands around my ankles. I did not even know why I allowed it. My head was forced forward, and I could see my cock and whatever she was about to do to my asshole. We both knew what she was about to start doing, and I trembled a little thinking about it. I had never done something like that to myself, and here she was about to make me take the fattest monster cock in the world. I trembled, but my tiny peen was hard and throbbing for her. I was embarrassed that it throbbed, but Carly did not notice. She was busy doing things and moving around her room. 

I had a chance earlier to look around the room, but now bound like this moving my head away from my tiny peen and ass was impossible with the bindings acting as blinders. Carly then appeared before me, and she towered above me. I could only see her ripped, muscular six-pack stomach because of how close she was. Her thick cock was visibly throbbing, and the blood moving through her massive cock was almost visible. I shivered, and she smiled as she picked up the lube and started to cover her hands in the clear liquid. She covered her hands, then put them down by my ass, and she reached forward and tickled my sphincter. I shivered, and there was a light-sensitive pleasure through me.  

She pushed against it, and my muscles tightened up; I whined a little, and her lube-covered hand found my nipple and started to tease it. “You are too tight, Angel,” She cooed, “You need to loosen up and relax for your Mistress.”

She pushed a little harder and teased my nipple, sending pleasure through my body. I moaned before I knew it, and my hips tingled, and she shoved her finger into me. The sudden penetration made my leg shake, and she pushed inside deeper, and she hooked it up into me, and my cock throbbed. I covered my face, and I felt an odd pleasure inside me as she pushed up and pressed against something deep in me. She thrust my finger into me and pulled back, pressing up against something deep inside me. I moaned, and Carly smiled, “You feel that?” She said, her voice teasing, “That is your prostate, Angel, and I am going to train it to make you cum again and again. You are going to be my little girl from this day onward.”  

The look in her eyes made me shiver, and her finger plunged into me hard. She pushed in and out of me, and her hand grabbed my tiny peen. I shivered and moaned as she made me try to thrust my hips up, and I did not understand the pleasure that was hitting my head. Her finger moved faster and faster inside me, and suddenly, Something in me spasmed, and my hips tried to thrust as my head blanked, and she giggled a little.

“Mmmm, you dry orgasmed, it seemed; let's see if I can get you to chain a little. You are so sensitive. It seems you have a larger prostate to play with,” She grinned, and I opened my mouth to say something. 

Nothing came out, and suddenly, she shoved a second finger into me, and my eyes widened, and I thrust up without thought. She pushed in and out, and she continued to thrust her fingers into me harder and harder. Her fingers rampaged inside of me with those fingers, and she started to rub my nipples and then pinched them. My brain blanked, and I moaned louder, my hips tired to move again as her hand moved faster. Then she pushed up against my prostate, she called it and thrust against it harder. 

My legs trembled, and my brain seemed to shake, and I felt something shudder in me, and my mind blanked. I could only watch as her fingers did not stop, as something in me seemed to rush through my cock. It was like a game, but nothing came out, and I watched as it did nothing, even though I felt like I had just pissed myself a little. She shoved her fingers in me, and her fingers pinched my nipples. She seemed to attack my brain with pleasure, and I moaned and moaned, not knowing what to say. 

My head was swimming in pleasure, and something hit me again, and just as I felt like I was about to cum again, she pulled out. My eyes widened, and she grinned as she pulled out a lubed covered out of my asshole. I looked at her, and she licked her lips, and her cock was throbbing deliciously. She turned around, her breasts swaying a little as she turned. She then showed me long, purple, one-inch-thick beads attached together with a white handle at the bottom, and she grinned. 

Then she covered it in lube, and I was looking down at my ass as she brought the purple tip to my twitching asshole, and she moaned as she shoved it inside me, and the balls teased the entrance of my asshole. She pushed it deep, and suddenly, it turned on and started to buzz. My mind exploded, and she leaned down, licked my nipple, and sucked on it. She thrust the beads into me, then pulled them out, and each made something inside me shudder. With each thrust, it sent me to the edges of reality, and suddenly, something exploded inside me, and it was like I was pissing, but nothing came out, and she grinned as my face turned red from the pressure inside me releasing. She grinned, “Such a good girl, cumming for mistress, you cum again, and we will move on to something even bigger so you can fit me after,” She said, and her tongue traced around my nipple, and she shoved it harder into me. 

My mind was a mess, and she picked up speed, and my body trembled, but I could do nothing. I tried to push against my restraints, and I was scared. I was scared of what was next, as something built inside me, and I did not understand it. This was not like the previous times. This was something deep inside me. The pressure around my balls and tiny peen was building, and I groaned as I tried to escape but could not move an inch. She continued to tease my nipple, and I felt something reach a point of no return. I was pissed, and she pulled back as a cloudy white liquid squirted out of my cock, and she went down and licked it all up.

“Mmm, Sissygasm,” She moaned and licked up more of the cloudy white liquid I pissed out, and she grinned and licked her lips and pulled back the beads, and she said, “You like that, my good little crossdressing girl?” She asked, her voice confident that I did, and my mind blank with pleasure, and she grinned, “I am going to make you sissygasm again like a little bitch, look forward to it.” 

My mind heard the words but could not listen as the world was clouded white. I could only see her perfect ass moving around before me in the distance. She was moving around the room, and I could not even register what it was that it was doing. I was mesmerized by the tiny pool of cloudy white liquid on my stomach that I felt like I was pissed out, and I had no idea what it was. It wasn't cum, but it was not piss, and Carly called it a Sissygasm, and I had no idea what it was. I shivered, and she brought something up, and my eyes widened. 

“What?” I asked, my voice strangely even more feminine as she brought a large machine up to my asshole. The thing now pointed at my ass was something that I did recognize. It was a long black dildo with a mean-looking head that was at least half as thick as Carly’s massive cock. Her smile brightened, and she poured lube all over the black appendage, and she lined it up to my asshole, which was when I noticed the steel behind it. There was a machine behind it, and it looked sinister. I had no idea what that machine was about to do, but something told me I was supposed to be scared, and her smile confirmed it.  

“This is a sex machine, my little cute Sissy. I need to train your ass, and you need to have it loosen up and get used to having sissygasms. For that, you need to get fucked, and I can't do that because I am too thick, so this will help us. Your asshole is still a little too tight for this, but after it rampages you with three thrusts a second on its max settings, you will cum a bunch, and I am going to make sure that you are ready for me,” She explained, but I barely understood a thing. 

My mouth opened and closed, and there was only one thing that escaped my mouth, “Mercy,” I begged, and her cock throbbed as I said that word, and her smile somehow brightened even more.

“That's right, Angel,” She moaned, grabbing her breast with one hand and her cock in the other. “Beg, Beg for me to stop, and I won't, I want to fuck you tonight, and you are going to let me. So beg for mercy, but I am merciless,” She promised me.

Then she pushed the tip of the massive black cock into me, and I shivered as it pushed into me and went deeper into me till it stopped halfway with at least five inches into me. I felt so full, and she grinned and then held up a remote. She pressed a button, and it seemed to turn on, and there were two dials. She twisted one, and it started to move. The lubed fake cock pushed into me, and my mind was blank. I could only watch as she watched it move deep into me. Then, pull out slowly. It was fucking me slowly, and the slurping sound of it pulling out my ass resounded in the room. Then it pushed in, and she moved beside me and showed me the remote and pressed her breasts against my leg, and her cock rested on my stomach. I could feel it throb in me as she looked into my eyes.  

The look in her eyes chilled me to the bone. The delight in her face spoke volumes. She put the remote on my chest so I could see her two fingers move and twist it a little. The machine picked up speed, and that thing inside me quivered. Pressure started to build, and she grinned. She watched inches from me as I watched the machine plunge in and out of me slowly.

It made me feel so full, and my cock throbbed hard. I did not know what was happening, and I was scared as she moved the dial more. My mouth opened and closed, but nothing came out. I desperately wanted to say something, and she looked into my eyes with Violet and Amber's eyes and said, “Beg for me, please, Angel. I love begging, begging me to stop, begging me to cum, begging me for anything; I love hearing your voice. Let me hear it as I make you cum again and again.

I shuddered, but as she brought her fingers toward the dial and twisted it, the machine started moving faster and faster. It was now moving in and out of me constantly, at least in or out once a second, and I cried out, “Please, too much,” She suddenly slapped me, to my surprise. 

“Mistress, I am Mistress when we are having sex, Angel,” She ordered, and I shuddered as the pressure built. I had no idea what was happening, but the disapproving look in her eyes was something I did not want to see. 

“Please,” I cried out, “Mistress,” I added quickly, “I- I don't understand, W- What is happening, it- it- It~!” The pressure seemed to reach a max, and she giggled and brought her fingers to the dial, and my eyes widened, “NO-~!” I was cut off as the pleasure exploded in my head as she moved the second dial, and this time, it was not thrusting faster. This one made it suddenly start to vibrate, and my head disappeared. 

Stars in the sky started to shine through, and that pressure exploded. I felt my mouth open and the air leaving me, but I heard nothing. I saw the delight on Carly’s face as I felt like I was pissing all over myself. 

What I saw, though, was the cloudy white liquid shoot out of my cock hard and fast and squirt all over me, and The machine never stopped. I shuddered, and the pressure started to build again. Her fingers moved again to the first dial, and she twisted it, making it move faster. 

The fake cock plunged in and out of me faster, and no human could match the speed as it plunged in and out of me every second, hitting something deep inside of me and pulling out before thrusting in a half second later. It was relentless, and the pressure built up quickly, and I finally heard myself scream, “NOOOOO~!” 

My scream sent a shudder through me, and I pissed out that clear liquid, and it kept cumming out of my tiny peen, and she reacted by twisting the knob to make it go even faster, and I shuddered, and more cloudly liquid came out of me. The smell of her roses invaded my mind along with the pleasure, and it was like a sensory overload. I screamed harder as my body spasmed and trembled. My hands pushed against the restraints, and my feet tried to kick out, but the bindings were tight. I could not move, and I heard her wonderful delighted laughter as I pissed out more and more of that cloudy white liquid that was not semen, and she did the unimaginable to me at this moment. 

Her hand came down on my cock hard and slapped it, and then the world exploded in a new way, and she turned off the machine as semen shot out of my tiny peen. My brain melted, and the pressure disappeared as cum shot out of me with force and hit myself and her. I could see the tiny white droplets shooting all over the place, and she giggled, and I felt her throbbing cock on my stomach leave. She moved away, but I did not care. 

I could not care about anything at this moment. My whole body was focused on the stars clouding my vision, and suddenly, I was empty again. I could not even pay attention to that either. I barely breathed, and it was like breathing was my entire world. Air in, air out, I needed it as my cock throbbed and I shuddered. 

My eyes were unfocused, but suddenly, something snapped in front of me. Carly was snapping her fingers, then she slapped me, and she grinned as I focused on her. “What was that?” I groaned out in question, and she grinned. 

“That was a massive hands-free sissygasm. I needed to slap your balls to take you over the edge, but I think you needed it,” She said, her charming sex demoness voice filling my ears. It was a pleasure to hear that voice, and she waved something in front of me. I looked at it, and it was another black phallic object, and it was dripping a lot of lube down the entire length. She grinned as my eyes focused on it. 

“What is that?” I asked, even though something in my head told me I knew exactly what it was. 

“This is an extra long buttplug that gradually gets thicker so you can take my cock. This is the final step before taking me, Angel,” She promised, and I shuddered as I looked at it and I felt myself pale, a little unsure, and she rubbed my twitching asshole. “I am looking forward to us joining together, love; you have no idea how much your reactions have made me fall for you even more, Angel,” She said, the look in her eyes making me shudder, and she pressed the tip against my asshole without another word. 

“W—We can—" I tried to begin to say something, but the moment she pushed it in, I forgot everything. She pushed it in more and more, and it dove into the depths of my body. I felt it get bigger and bigger inside me as she pushed it deeper. The deeper it went, the more full I felt, and then she stopped suddenly.

“Look at that,” she said with a smile and dangerous-looking eyes. You took it all,” she said like it was a compliment. Now, I am going to let you adapt a little before I take you, Angel. Prepare yourself,” she said and walked away.

My eyes widened as she went away out of my sight. I had no idea how to react, and I looked at the pool of cum and cloudy white liquid on my stomach and around my cock. I was locked in this position, unable to do anything more than beg and watch. I did not even know how to feel about things right now, and I shuddered as I sat here lost.

My asshole twitched, and I tried to move, and it moved the thing deep inside me, and I moaned. Something deep inside of me tickled, and it felt good, but I did not like it either. No, I liked it and hated it. I had no idea what Carly was doing to me other than training my ass to take her, and now that she was gone, the fog was clearing, and I found my asshole twitching on the toy inside me. 

Would my ass ever be able to go back? Would I be able to go to the bathroom properly after today? Why did it feel so good when she did that ‘prostate’ thing? My mind was in chaos, and I had no idea what to do till I heard Carly come back. 

Her cock was throbbing, and she grinned and looked down at me. There was a happiness in there that I had not seen till now, and she stroked her cock, and I noticed the gloves were gone. Her white cock was whiter than even my own, and she stroked it slowly.  I could see the skin moving up and down slowly, and I had no idea what to say or do as she looked at me with lust-filled eyes. “Angel,” She said, her voice husky, “I have been with friends doing this before,” She said, “But I have never done what comes next either with someone. I have fantasized so many times, but no one ever wanted to take the final plunge. I want you to remember, this is not just your first time; this is mine too.” She said, and her excitement grew. 

I looked at her, shocked. 

This sex demoness was a virgin? That had not to be true! She felt so experienced!  

She reached down and grabbed the base of what was inside me and pulled. I shivered, and it slid out of me slowly on lube; she grabbed a bottle of lube in one hand as she finished pulling it out, and I watched as ten inches of whatever that toy was left me. She tossed it away like it was nothing, then she squatted down and put some type of attachment on the bottle, and she pushed it against my ass, and suddenly something lukewarm shot into me. The contents slipped deeper into me, and I realized that my lust clouded mine. She was filling me up with lune, then stood and poured even more lube on her cock, and it was dripping down to her thick balls with how much she put on. 

“Now, we can never be too careful with lube; I want to be able to use this even more in the future.” She commented, and she grinned, and I shuddered. 

This was it, wasn't it, and I watched as she moved to line her cock up with my spasming little hole, ready for us to join together for the first time tonight, and my heart beat quickly in my chest. My nose brought in more of her rose-scented body with the smell of my useless semen, and I shuddered as it pressed home. 

I took a deep breath, anticipating yet scared of what was to come.