I waited for Mistress to tighten my restraints. She had me tied to the bed with my arms and legs spread, my belly down and my ass and legs hanging over the edge. Mistress pulled the bindings tight, locking me in place.
The ropes felt so good on my new slender figure. The treatments Mistress had me taking the last few months, had taken quickly. I was never a large guy but now my arms were slim and nipples were sensitive and soft. I felt softer and more sensitive all over. I yearned for my mistress’ firm and rough touch.
Mistress helped me shave my legs and do my make up. She likes me looking pretty. When I saw myself in the mirror today I was surprised to see the feminine figure staring back. I felt so sexy.
Satisfied with the constraints, Mistress gave me a firm smack on my ass. I moaned at the sting, it felt so good. She had been penetrating me more roughly lately, using a larger strap-on each time. I liked the abuse. Her passion made me feel desired.
Mistress climbed onto the bed and sat on her knees in front of me. I looked up at her goddess body. Sculpted and powerful but also elegant and slender. She grabbed my hair with one hand and lifted my chin with the other, forcing me to look up into her eyes. Lust and passion filled those eyes, accompanied by a devilish smirk. My cock pushed up against its cage as a warmth filled my belly. Mistress has had me locked for a few months now, teaching me to cum another way.
“You look so sexy in that outfit.” Mistress complimented. She had chosen out for me a very revealing sailors outfit. The kind that always turned me on, back before Mistress helped me find my true self. I had no underwear on, white leggings and a skirt framed my feminine ass. A tight top that covered only the very top of my chest and the collar Mistress had given me.
Mistress herself wore all black. Tight black leggings that made her delicious thighs push out. A black g-string riding high over her hips. A corset accentuating her gorgeous figure and black tape in a cross pattern blocking sight from her perfect nipples.
Mistress traced my lips with her thumb, slipping it into my mouth. I dutifully licked and sucked. It turned me on so much to have my mouth played with.
“Your training has been going so well. Today we are going to do something different. Reward you for being such a good slut.” Mistress whispered.
“Thank you, Mistress.” I said between worshiping her thumb.
“Good girl. Now open wide.” Mistress pulled out a black ball gag as I eagerly followed instruction. She pushed it deep into my mouth while she tightened the straps behind my head. I pushed on it with my tongue and it barely moved from its place.
“How’s that?” Mistress asked.
“Gud misruss.” I mumbled. She smiled in response, leaning down and pulling my head up. She gave me a kiss on the gag and my heart fluttered. Her affection felt so good.
What happened next was something new. She put an earbud in each of my ears, muffling the sounds around me. Then she wrapped a dark fabric around my head and eyes, blocking the sound further and taking my sight.
I felt her get off the bed and move around checking my restraints. She made sure they were secure and comfortable. Each tug and touch felt so heightened as she moved around me. She smacked my ass again, causing me to raise my but in encouragement out of instinct. The sensation felt so much better with my other senses subdued.
She began kissing and groping me. Wet and sensual kisses and firm and possessive gropes. I was hers. My moans were uncontrollable and my cock pressed hard against its restraint. I kept my back arched and ass out, begging for what I knew was coming.
Mistress caressed, licked and kissed my ass. She was getting me ready. She started slapping me on each cheek, one after the other in a slow beat. Harder each slap, making my ass red and sore. My moans were constant and i started mumbling “please”, begging her to stick it in and fuck me silly. She ignored my pleas and continued to smack. The sting started to burn and my moans started mixing with cries.
She stopped her smacks, my ass burning with sensation, begging to be soothed. She went back to kissing me lightly all over. She kissed from my ass, up my back, taking her time. She then reached under and grabbed me by the throat and squeezed lightly. This is usually when she stuck it in, so I moved my hips encouragingly, grinding against her. I couldn’t feel any strap on, and she quickly let go and pulled back, giving me one final kiss on the right cheek and slapping my left, before retreating off the bed.
My body was alight with sensation. The ropes pulling on my skin, the burning sensation on my ass, the wet kisses left on my body. I moaned as I grinded on the bed, rubbing myself on the sheets. I was so horny. I waited for Mistress touch to return but it didn’t. She sometimes liked to watch me struggle in my restraints, tormented and begging.
I felt a sudden smack, hard on my ass. It made me cry out before the hand, larger and more rough than Mistress’ squeezed my cheek. Panic filled me suddenly, where was Mistress and who was this groping me.
I felt the weight of the figure as they put a hand on my back, pushing it into a hard arch. They then put the head of their hard cock into my asshole. I pulled against my arm and leg restraints but they held firm as the figure pushed slowly inside of me.
A long moan left my lips as I felt his cock filling me up. My body was begging for this. With one hand still pushing my back down, another now grabbed me by the back of the hair. He pulled, using the leverage to push his cock into the deepest parts of my ass. He held for a second before pulling back out and then back in. The hand on my back moved to grab my hips and the figure pulled harder on my hair. Each thrust started to build speed as my moans continued to escape.
Mistress had brought in a bull to fuck me. Another man with a big thick cock, and large rough hands. I was overwhelmed with pleasure as his cock thrust repeatedly into me. My g-spot was going crazy and I started to shake as I orgasmed from my ass. The bull stopped, with his cock fully in me. He watched as I shook and my mind went numb. God it felt good to cum from my ass.
I could hear a low muffled laughter as the hand let go of my hair and came down hard on my ass, making my brain tingle. It then moved to my other hip, mirroring the other hand and started pulling hard as he thrust into me. His motion was vigorous and his cock hit all the right places, all the right depths, it filled me perfectly.
A familiar weight climbed onto the bed in front of me. Mistress sensual soft hands held and caressed my face as I moaned repeatedly through my gag. She pulled her knees under me and let my chin rest on her thighs as she undid my gag. I drooled as the gag was pulled free and my moans became clear.
Mistress played with my mouth with her thumb and I sucked and licked it eagerly as I was being pounded from behind. My mind was mush, all I could think about was how good it felt. Each thrust gave a wave of pleasure, a warmth filling me up.
Mistress pulled off my blind fold, and removed my ear buds. She yanked on my hair to make me look up at her. I was moaning louder than I thought. She looked at me with satisfaction and lust.
“Do you like that cock filling your ass, my little slut?” She whispered.
“Yes Mistress,” I moaned. “Thank you Mistress.”
“Good girl.” She let go of my hair and let my face rest in her thighs as she undid the restraints on my arms.
As soon as my arms were free, two strong hands grabbed my wrists and pulled my arms back. He bent me back and continued to thrust, pulling me into him. My face was now at the height of Mistress’ breasts and she grabbed my face with her hands.
“Such a pathetic face. Does it feel that good?” She purred.
“Y-yeessss… mistres-s-s-sss,” I moaned with a blank mind. It felt so very good.
Mistress then leaned down and grabbed my nipples and gave them a loving twist as she kissed me hard on the lips. I melted into those lips and onto the cock filling me from behind. The orgasm radiated through me, making me quiver as I came from both my ass and my cock. Sperm spurted out in waves through my cage.
Mistress stepped back and giggled as she admired her work. I just quivered and leaked as I continued to be pulled onto the cock behind me, mind numb with pleasure. He pulled me up close to him, grabbing me around the neck and chest. He kissed me on the cheek and squeezed my nipple with one hand, my neck with the other. I grinded back onto his cock, reveling in the rough treatment. Mistress never had the strength to bend and manipulate me like this.
“You like being treated like this, don’t you?” He whispered in my ear. I nodded and moaned my confirmation. My vision began to fade from his tight grip on my neck. I grinded back on him harder in response as I started to see sparkles. Another anal orgasm radiated through me and I mumbled my appreciation.
I came back to my senses suddenly, laying belly down on the bed. I didn’t remember losing consciousness but it didn’t seem like more than a moment passed. Mistress was untying my legs and gave me a big smack on the ass to confirm I was awake. Hearing my cry, she pulled me back off the bed and onto the ground, pushing me onto my knees. She pulled my arms back and started trying them together.
The bull my mistress had invited sat down on the bed and watched, stroking his large cock. This was my first time really seeing him. He was large and muscular, no wonder he could manipulate me so easily. He had a hard stare that made me feel frightened and turned-on at the same time.
Mistress finished trying my arms and connected a leash to my collar. She walked over to her bull, pulling me along by the leash, then handed it to him.
“I’m going to let you two get further acquainted,” She said after turning to address me. “You will show him how much you appreciated his cock by using your mouth. You will call him Master and you will be done when he is satisfied.”
“Yes, Mistress,” I said. “Thank you, Mistress.”
She smirked, leaned down and gave me a loving kiss on the mouth. Then she stood back up and left the room. Leaving me alone with my new Master.
He yanked hard on my leash, pulling me into him. His cock inches from my face, my mouth started to water. Mistress had me practice often on her plastic cock, along with several toys. She disciplined my technique harshly and rewarded my efforts appropriately. I loved having my mouth played with but this was new to me. A real cock. It radiated a scent and warmth, twitching as my master waited.
I stuck my tongue out and licked the tip before giving it a kiss. I looked up at Master and he eyed me lustfully and expectantly. Mistress always said to look her in the eye and to show my enthusiasm. I started licking him up and down his shaft, kissing him all over his cock while looking back up into his eyes.
With my arms bound I had to use my mouth to position him. I wrapped my lips around the end of his cock and sucked as I slid him slowly into my mouth. I let him see my eyes as I started to work my mouth up and down his cock. The enjoyment on his face made my cock swell in its cage. I let his cock slip out of my mouth with a satisfying pop sound and started to again lick him up and down, kissing him, worshiping him.
“Enough of that,” He said “I want to feel the back of your throat. Show me how deep you can go.”
I was eager to impress him but his cock was bigger than anything I’d tried before. I used my tongue to guide the tip into my mouth and sucked with my lips as I slid it into my throat. I went slow but quickly met resistance, making me gag and pull back off his cock. As it slipped out of my mouth he grabbed the hair on top of my head, yanking it up and slapping me across the face. I whimpered at the sting and began to tear up.
He held me by the hair and stuck his cock back in my mouth. I could feel my makeup running down my face, something Mistress always enjoyed.
“One more try, little slut, before I make you.” He said as he let go of my hair.
I looked up at him frightened. Will he slap me again if I fail, or will he do something more? I turned my attention to my task and took his cock down my throat. I met resistance again but I pushed through, making my eyes water. I tried to swallow to bring it in all the way but there was a barrier I couldn’t pass. I looked up at him worried as I started to gag. I pulled back off his cock and he grabbed me again by the hair. He gave me a slap across the face and then a backhand across the other cheek.
“I’m sorry, Master,” I whimpered. “You’re too big.” He used a delicate finger to wipe my tears from my cheek, then put his cock back into my mouth.
“Try again. I will help you.” He said in a firm voice, releasing his grip on my hair.
I whimpered with his cock in my mouth. My cheeks blazed with a warm sting. I couldn’t do this, he was going to slap me again. I took his cock deep into my throat, pushing up to the barrier I found last time. There I stopped and began to gag but as I attempted to pull back, he grabbed me by the back of the head with both hands and pushed me down, hard. I broke through the barrier and my lips touched the base of his cock.
My eyes watered and my throat resisted but he held me firm. I looked up at him pleading with my eyes. He smiled wide as he held me there struggling on his cock.
“Good girl,” He whispered. “See what you can do with a little encouragement.”
He finally let his grip go and I pulled back off his cock, sending a spray of saliva. I coughed and spat, gasping in between.
“Please, Master, no more.” I begged.
“No more? We are just getting started, my little pet.” He said with a devious smile. He grabbed me under the chin with his hand, holding my eyes on his. “I’m going to fuck your throat now and when I cum you are going to swallow every bit. Now, what do you say?”
“Y-yes, Master.” I wined. “Thank you.”
“Thank you, for what?” He asked me.
“T-thank you… for… ,” I paused, thinking. “Thank you for making me your little slut.”
“Good girl, now open wide.” He said as he put his cock in my waiting, obedient mouth. I felt so used and pathetic. So why was I so turned-on? My cock was leaking and my asshole flexed hungrily. God, I wish he would fuck me again. That was the selfish thinking of a little slut, I had to earn it.
I relaxed my throat as he grabbed the back of my head and pushed me down hard. All in one, I took his massive cock. He held me in place and started grinding against my face. I did my best not to resist him, but every now and then I’d gag and pull back instinctively. He would just push me down harder and tighten his grip.
He would pull me down deep to the base of his cock and hold me there for a moment before pulling me off him to gasp for air. Occasionally he would slap me before shoving me back down on his cock.
He started to build in intensity and speed, forgetting to let me breathe, as he lost himself to his lust. In his moment of ecstasy he held me down hard on his cock. I felt it pulse and explode deep in my throat, each pulse sending another spray. I sucked on his cock and drank down every drop. Feeling warm from the cum and for giving my master what he desired.
He let his grip drop and I focused hard not to lose any of Masters reward. I pulled back slowly, sucking hard as my lips ran back along his cock. As my lips popped off the tip, I swallowed the cum that didn’t make it down my throat. I then opened my mouth wide, tongue out, in presentation while gasping for air.
Master grabbed my tongue and inspected my mouth, breathing heavily from his climax. I held my pose but couldn’t stop myself from smiling in satisfaction.
“Very, good girl.” He said “You were worth every dollar. I’ll have to make sure to give your Mistress a tip.” I barely registered what he just said. I felt too good, satisfied completely by his praise. My Mistress will be so happy.
I returned to worshiping his cock, making sure it was clean. He leaned over me and gave me a slap on each ass cheek. After, he pushed me off him, got up and knocked on the door.
“We’re done,” he said after knocking. Then he started putting his clothes back on. I sat there on my knees obediently, but I wished he would fuck me again. I felt so good and so horny, I just wanted more.
A moment later, Mistress stepped in. She and Master briefly talked about my satisfactory performance before giving Mistress a roll of notes. He then left and it was just me and my Mistress. She leaned down and inspected me.
“Well you’re one messy looking slut aren’t you?”
“Yes, Mistress.”
“You did so well. You followed your training perfectly, so much faster than the others,” she said to me. “Tomorrow we are going to do this again, maybe even a few times. I have a feeling you’re going to be very popular. For now though, I think you deserve a reward.”
“Please, Mistress,” I said eagerly. “Thank you, Mistress.”
She left my arms tied as they were and added rope to my legs, locking my heels against my thighs, keeping me on my knees. She tied a bar between my ankles, keeping my legs spread. To my surprise she unlocked my chastity cage and let my cock swell to its full size. It had been so long since I had it free, it looked so big. She then got up and returned with some toys.
She pulled a tight band over my cock, down to the base, keeping me from cumming too easily. She then sucked on a large butt plug, staring at me while she did so. I bit my lip in anticipation. She stepped over me and pulled on my tied arms to force my face to the floor and my ass up. A smack on each cheek, then she slipped it in. After that she pulled me back up by the hair.
She continued to work, sucking on my nipples briefly to get them erect, then putting on special clamps. The sting felt good. She used body tape to attach little vibrators all over my cock. She used a rope from the ceiling to attach to my collar, pulling it tight to keep me from wandering, my back straight. She put my blind fold back on, taking away my sight.
“Now, I have some friends coming over tonight and I don’t want them to hear my little slut making a fuss in the next room,” She gave me a hard passionate kiss on the lips.
“No, Mistress. I’ll be quiet.” I moaned.
“Oh,” She said in a cheery tone. “I know you will be. Now open wide.” She slipped a small dildo down my throat, then locked it in place with straps around my head. It reached to the back of my throat, only just allowing me to breath. I mumbled a pathetic protest but Mistress just laughed.
“Now, I’ll be back in the morning, to clean you up for tomorrow. You enjoy your reward.” She kissed me on the cheek and activated the toys.
The plug in my ass, the vibrators on my cock, the clamps on my nipples, they all vibrated. I moaned in surprise at the sudden onset of the overwhelming stimulus. I thrashed around in my constraints as waves of pleasure washed over me. My cock was already beginning to leak and my ass pulsed with warmth. My moans made me gag on the dildo in my throat as I struggled to breathe. I whimpered and moaned as I heard the door to the room close and lock. It was going to be a long night.
Source: reddit.com/r/eroticliterature/comments/rzks2c/graduation_day_for_a_sissy_bdsm_feminization