Life of a Dominant Futanari Week 4 Chapter 153/39: Choices

Looking around the basement, my cock throbbed in anticipation. I was reaching my max slowly in needed to do something soon while looking at Crystal as she helped me set up for Kyle. I was about to attack her if I didn't start with Kyle soon. I heard the shower stop not long ago, and Crystal looked at me with a smile in reply when we believed he would be ready.

We both looked sexy as hell, and I couldn't help but wonder what was going to happen next. I placed a gift that I knew Kyle wouldn't know about. After cleaning it thoroughly, I placed it in the drawer, and Crystal turned to me as I put it in the drawer. "You going to force him to wear it or choose to?" Crystal asked.

"Choice," I said, turning and placing my ass against the counter as I looked at her. Toys lay on the counter, and Crystal stood by the chair I had once tortured Jake on. I knew it was used mainly for women in a gynecologist's office and would spread his legs. This was Crystal's chair, and it was modified to hold the person in place. I had used it before and was going to use it again. That wasn't the only one that was out right now, and the Pillory was out and secured to the floor.

Crystal looked great in her matching Fishnet outfit, and her breasts looked amazing to me. I stood up, walked over to her, and slapped her ass lightly. "I will change the speed of his training depending on his way of choosing. I cannot wait to see what he will choose in the end." I smiled and walked over to the bathroom door. I knocked lightly before opening the door and peeking just my head in, and I saw Kyle dressed back in that outfit.

His cute face was blushing, and the silver collar around his neck was attached to the crop top around his chest, with transparent bra straps poking over his shoulders. His stomach looked soft, and his stomach was visible before the black jeans that completed the outfit. His cute expression made my cock throb, and I smiled, looking at him. "Come out, Sissy," I said, "Today will be a day you will never forget. Come out within two minutes," I finished before closing the door.

I stepped back, walked over to Crystal, wrapped my arm around her, and kissed her. "Ready, Minx?" I asked.

"Oh," Crystal said, looking at me now in the eyes after we broke our kiss. "I am more than ready, and my pussy is dripping. I cannot wait to see what you do to him." She brought her fingers over my breast and toyed with my nipples a little and sent a slight pleasure through my nipples. "I cannot wait to see it all."

A second later, we both turned, and Crystal stopped teasing my nipples, and my cock throbbed. We both looked at Kyle in his cute goth looking outfit. He closed the door behind him and stopped when he looked at Crystal and me. His face blushed hard, and I could even see his ears turn red. His eyes moved slowly up and down, taking both of us in, and I saw a small bulge in his pants a half second later. The amount of blood flowing in his body must be enormous, and I couldn't help the smile on my face.

"Come here, Sissy," I ordered, beckoning with a single finger while my other hand stroked Crystal's fishnet-covered hip. My thumb stroked her hip softly, and Kyle looked in a horny daze as he stepped forward. I smiled as I pointed a the floor just a couple of feet away from me. He stopped exactly where I pointed, and I couldn't help saying, "Good Girl," With a soft smile. "You are working on that reward I promised," I continued a moment later, motioning a little around me, "Both my girlfriend and I got dressed up. What do you think?"

"YOU BOTH LOOK AMAZING, MISTRESS!" Kyle cried out in a second with that red blush, and I could see the confidence disappear with that statement. He started to stare at his feet and completed the image of a cute shy girl.

"Look at me," I said simply.

My words were like a command, and he looked up at me. His eyes looked into mine, and I reached forward and softly stroked his cheek. "Today, you will make a decision that could change your entire life, Kyle," I said, stepping forward and closing the distance while no longer holding Crystal's hip. "You are free to leave now with just the image of us as a reward. Or you can stay and potentially change your entire life forever. This will be your first choice," I said, looking down at him. I was over a head taller than him, and as he looked up into his eyes, I knew he was also looking at my breasts. They were in his face, and his blush was obvious to everyone.

A moment later, his eyes couldn't help it, and they landed on my breasts, and I watched him swallow. "I- I- I want to stay," He said, looking at my boobs, although my cock was standing strong very close by to my breasts as it throbbed in anticipation.

My hand reached down, and I leaned down a bit with it. My fingers pressed against his jeans over his bulge, and I felt his small cock in my hand and rubbed the fabric as my lips neared his way. "Sissy," I began slowly, my words soft and drawn out, "You are to remove these pants, but it must take you no less than thirty seconds to remove them. If you are too fast, then I will punish you." I felt his cock throb through the pants as I stood tall, and I stepped back, standing tall again.

Kyle was left stunned for a moment before looking at me. He didn't know what to do, and we both watched him without saying a word. I wasn't about to tell him again, and it seemed a moment later that he understood what I meant. He shook his damp head and reached down, undoing the button on the black jeans. Again he paused, remembering the time limit, then turned around. I could see the understanding of what I was asking him to do now as I heard the unzipping of his jeans and him start to show his ass with those panties coming into sight slowly. They were not the sexiest panties, but I didn't care at this moment as they made my cock throb in excitement.

Kyle's asscheeks slowly came into view, and he turned to look at us, twisting his body inadvertently in this sexy way that seemed to make him have a slightly larger chest. He slowly removed those pants, and when he reached his thighs, he turned around again, and you could see the bulge off to the side where his cock was pressing against the panties. He looked ashamed but didn't stop as he slowly reached his knees before letting the pants drop and pool on the floor.

Both Crystal and I were grinning, and I followed up a couple of moments later. "Lose the shirt, now," I ordered, and Kyle undid the collar and tore off his shirt with much more haste listening to the words I said exactly.

"Oh, this Sissy has much more talent than the last one," I said, turning to Crystal. Crystal nodded in return but continued to watch Kyle as the shirt was placed on the floor. "Come here," I ordered, turning back to look at Kyle.

Kyle stepped forward and out of the clothes, and I looked down at his panties and realized that they would have to go too. I contemplated for a moment and decided against keeping them on. If they were a g string, a thong, or something less thick, I would keep them on, but at this moment, they would get in the way. "Take off your panties," I ordered in the silence I didn't realize had developed.

Kyle nodded with that blushing shy face, and his fingers hooked into the panties under my eyes, and he took them off. I could see his eyes drift down and take in the length of my dick. They didn't leave my cock as he knelt a little and got closer, and I saw his nostrils flair taking at the end of my cock, still a little dirty from Lexus hours before. Maybe I should have showered, but I thought that this was better.

He leaned into it, and I saw him take in the smell again, maybe thinking he was stealthy. Maybe he thought that I couldn't blame him for breathing in the scent of my cock. Air was a necessity, was it not? His brain pattern could be seen at this moment, and I felt my smile brighten as I saw him take everything in a while, taking off those panties.

What felt like a long moment was over when those panties hit the floor, joining the other clothing moments later. I reached down and cupped his cock that was pointing forward and bobbed up and down as it throbbed in excitement. I could see the anticipation and excitement as he looked up again, waiting for the next order.

My fingers stroked the soft skin on his cock, and I realized something in surprise. "No hair on you," I said with a grin, "Keep it this way," I told him and nodded to myself. I leaned down and closed my face to his. My hand reached out and stoked his cheek, and he looked at me surprised. A moment later, I took his lips with mine making his eyes widen, and I pulled back quickly with a smile standing straight.

Kyle again stood still, looking surprised, and his hand slowly rose to the lips that I had just kissed. His blush didn't recede the slightest as he realized it, and I pointed down. My cock throbbed, and it needed attention. "You may worship my cock for five minutes, Sissy," My eyes narrowed as excitement grew in him. "Make good use of it and pleasure your Mistress," I said with finality.

Kyle dropped to his knees a moment later and shimmied forward, where his head was just at the base of my cock and balls. He quickly leaned forward with that feminine face, and I felt his lips press against my balls. A moment later, he sucked a testicle into his mouth and massaged it slowly with his tongue. Pleasure tingled up my spine, and his fingers went for the shaft of my cock, softly stoking up and down the length.

Soft pleasure shivered up my spine, hitting my head, and my cock throbbed in his hand as I felt his second hand join the first. Both hands stroked up and down my shaft, and I felt his mouth open up, and I watched as his head backed away from my balls. His second hand, which had just joined the first, moved down to my balls and cupped them while he brought the head of my cock down to his face.

"I cannot believe I am doing this," Kyle said softly, barely hitting my ears, and I saw Crystal moving around behind him. My cock touched his cheek, and I felt his breath on the shaft of my cock as he rubbed it against his face a little while he took a closer look. His hand paused on my balls as he massaged them, and I moaned in pleasure while he stroked the shaft near the base of my cock.

A moment later, he opened his mouth, and his nostrils flared as he took in the scent of my cock while his tongue lashed out, licking the bottom shaft of my cock. I felt his tongue drag along the bottom of my cock and pass over that sensitive spot at the bottom of the head of my cock. A large shiver of pleasure went through my body as I watched Crystal crouch behind Kyle and her hands found their way under his bra. Her fingers started to toy with his nipples as he finally started to suckle on the tip of my cock, sending more shivers of pleasure through me.

Moans erupted from my lips as I felt my cock slowly enter Kyle's mouth, as he made sure not a single tooth touched my cock. I moaned as his hands moved to massage my balls and stroke my shaft even faster, and I wasn't sure if I could last five minutes at this rate as the pleasure blasted my head in waves. His tongue and mouth moved to stroke my cock, and Crystal's fingers moved faster, and I felt Kyle moan on my cock as he sucked somehow harder. His dazed eyes looked straight down the length of my cock with a fervent look that was almost dazed. Pleasure assaulted me, and I moaned loudly, and I smirked, "You have received permission to swallow my semen, Sissy!" I announced as I reached the peak, "Receive your Reward!" I commanded just as I reached the peak a moment later, and I felt my balls dip up and off his hand before coming back down on them as they sent a steam of semen into my new Sissy's mouth.

His cheeks puffed up and decreased as rope after rope of semen flooded his mouth. Kyle was virtually drowning in my cum as more and more were released. I filled the room with a feminine moan as I continued to release more into his mouth. Moments passed before my ejaculation came to an end, and I looked down, not realizing I tilted my head back in pleasure.

In my white haze, I was still surprised by how much pleasure and how quickly Kyle got me off. Maybe it was because I had held myself back for so long, but I took a little longer than usual to come back to myself after releasing such a large load into his mouth. Looking down as the pleasure ended and he continued to suck on the head of my cock while swallowing, I noticed semen dripping down from his lips and noticed some on his hands. His eyes were dazed, and I could barely see his cock bouncing up and down without any semen coming out.

Kyle must be incredibly turned on, and I wondered if he truly knew which virginity I would be going for. Maybe he already anticipated it, and I was letting my ego interfere with things. I wasn't sure if I was wrong in some way on this. It didn't matter either as I took a step back, pulling my cock out of his warm mouth and feeling my cock slide in his hand. My cock popped free from him as I stepped back and realized I had no idea when kyle let go of my balls. I looked down at him and saw all the semen that spilled down his chin and onto his hands. A line of semen was down the length of my cock from his mouth.

Semen was on his lips leaking from his mouth, and some fell down onto his arms and knees. I noticed a little around his nose, and I couldn't help but wonder if it went up through his nose. That didn't matter as I looked down at him with a small smile, "Well, Sissy," I began with a smile slowly growing larger on my face, "Not bad work. You deserve a reward for that, and I will give you another choice later for a reward. For now," I pointed at the chair, "Get in the chair."

My words lashed out like orders, and I saw Crystal leaning against him with a large smile on her face. She knew what was coming, and her sadistic side was starting to show, and I couldn't be happier about it. Crystal might have a hidden Dominant side that her friends didn't know about, but as her girlfriend, I could bring it out, and I loved dominating her despite her dominant streak. Crystal seemed to whisper something in Kyle's ear, and he seemed to wake up and look at the chair, and I saw him gulp a little before finally getting up off his knees.

I watched him start to walk over, and I turned and grabbed the cart and put the toys I had planned for Kyle on the cart. I had a plan moving forward with this part, and as I heard Crystal strapping Kyle into the chair, making him unable to move, he finally said something, "W-W- Why d- do I n-need to be s-strapped d-down?" he stuttered out.

I turned to see Crystal smiling as she locked his feet in place, and I smiled as I finished putting on the last toy and bringing the cart over as Crystal finished restraining him. I had to hand it to Kyle. I could see his nervousness about being strapped down, but he still allowed it without resistance. He wanted to be good and rewarded and followed every instruction from Crystal and me. He was being such a good sissy that I couldn't help but want to present the choice to him earlier. Still, I controlled myself, leaving the choice in the drawer.

I moved over and smiled as I placed the cart just out of view, stepped past the chair, and entered his vision. My cock throbbed seeing him so helpless in the chair, looking so girly with that bra across his chest, although it was a little out of place at this moment. I turned to Crystal and smiled that she returned a moment later. We both turned to Kyle, and I stood before Kyle and grinned. "It is for your safety." I told him, "The Safe word is Red light, Sissy," I continued more seriously, "If in the next bit of time you use this safe word in any context whatsoever, I will stop. Crystal will stop whatever we are doing and release you. Do you understand this?" I asked.

"Y- Yes, M-Mistress," Kyle stammered out nervously.

"I am not done with just this," I continued a moment later, "If you say Yellow light, I will tread carefully and slow down any play we do, Sissy. This means that you do not mind me continuing but proceed with caution as you are not sure if you like it. If you use this word, we will talk about it at a later time and why you felt that way at the time. Most of all, though, I will not be mad if you use these words in any context. I am not here to rape you or hurt you in the end. I am your Mistress, and I want you to enjoy what I do to you, not hate it. Is that understood?" I asked.

Kyle smiled, and I could see a new expression on his face that I couldn't quite place the emotion. "Yes, Mistress!" He replied a moment later.

"Almost done," I said, and Crystal nodded, "Last ground rule as we play, Sissy. As you noticed, we are using the Traffic light safe words system. That means there is one more light, and that would be the green light. This is a simple way for you to communicate enthusiastic consent with something that I just introduced. Obviously, there are other ways to communicate that, but it is another way to communicate that. Is that understood, and have you understood the safe words?" I asked.

"Mistress, I understand the safe words you put forward," Kyle said. I could see the excitement on his face, and I nodded.

My smile grew large, and I stepped over to the cart just out of his vision. I grabbed latex gloves and smiled as I put them on my hands. I started to put them on just out of his vision as Crystal came over and grabbed two suction vibrators with a grin. I could see the excitement on her face as she joined me today. She walked back into his vision and said, "I am Mistress's assistant tonight, Sissy," Crystal said, "I do everything Mistress orders even if you don't hear her ask." She told him as she reached forward, opened up his bra, and found his nipple. I saw Kyle looking into her eyes before looking down as she put the suction cup to his nipple and a light moan escaped his lips as the clear suction cup pulled on his nipple. A moment later, the first buzz sounded in the room, and I grabbed my lube.

I walked around as Crystal replaced me where I was standing a moment earlier, both of us walking around the chair clockwise. I stood between his legs, and Kyle's eyes widened as he saw the bottle of lube in my hands and my gloved hands. "W-" He started to stutter before I shook my head.

"We cannot leave this hole unlubed, Sissy," I told him as I crouched and grinned as his asshole was tight looking. I didn't know if he was expecting this, but it didn't matter as I lubed up my right hand and started to pour the lube down on his twitching cock just as my cock also throbbed in excitement for the show that was about to start in a moment.

Lube poured down his cock, and I heard Kyle suck in a breath as the lube slid down his cock. My hand reached out, stroking his cock lightly, and I felt his cock throb in my hand. I let go quickly, and my hand trailed down his small cock and balls, which I lightly gripped for a moment before I reached his now twitching asshole and poured more lube down onto my hand and teased the little hole with my index finger. Instantly I heard a moan and his ass tightened up instinctively.

"M-Mistress?" His voice sounded nervous, and I smiled, looking up at his face as he saw me squatted before him.

"Shh," I shushed him, "Relax and enjoy, Sissy. Let Mistress Guide you to a new you," I told him, and he looked unsure.

A moment later, I felt his sphincter relax a little, and I took the opportunity. My finger glided in, and I heard a moan escape his lips. It was a tight asshole, and I pushed in with the lube. My finger glided in, and I started to fuck his little twitching asshole with my finger, slowly taking my time before I started to hook it up a little.

"Ah!" Kyle let out a loud moan and looked down in surprise, and I heard his hands press against the restraints. A moment later, I hooked my finger brushing against the same part of his ass I did a moment earlier. "EEE!" he squealed a little, and I noticed his cock push up off his chest, and I smiled.

My finger inside of him started to hook up with each thrust now, and Kyle started to bite his lip in reply as his face was blushing a bright red, and I realized that I must have hit his prostate or G spot. I grinned, knowing that, and I began to assault the spot I found and put the bottle of lube to the side and reached up, and wrapped my fingers around his throbbing cock. My hand covered his entire cock, and it was no longer in my sight, with my hand covering it completely. I started to stroke it slowly, and Kyle began to moan loudly, and my finger hit that spot inside of him.

"Oh, Mistress, Please," He moaned out, "Mistress, Mistress, please, too much!" He cried out, and I heard him pressing against the restraints as I quickly hit him internally and externally. A moment later, a second finger pressed against his ass, and Kyle moaned as I pulled my index finger out and stopped stroking his cock just before my middle and index finger pressed in and penetrated him, making him loudly cry out. My fingers started to thrust in and out of him faster, and my hand moved a moment later.

"Oh, God!" Kyle suddenly cried out, and I felt his cock throbbing in my hand as I assaulted that spot inside of him and he was a moaning mess as his cock spewed out semen rope after rope into my hand as my hand continued to stroke his cock. He moaned, and my fingers hooked inside of him till his ejaculation finished.

When his ejaculation stopped, I smiled and stopped stroking his cock, but my fingers inside of him only slowed down. "How was your first orgasm, Sissy?" I asked as I straightened my fingers, stopped assaulting his prostate, and focused on stretching.

"Amazing." he sighed, barely audible to both Crystal and me.

"Crystal, Stage two, please," I told her. Kyle looked confused, and Crystal picked up something from the cart and brought it over even as my fingers moved slowly inside of him. They glided on lube easily stretching out inside and giving him a soft tease that made him moan softly.

Crystal brought over a tissue and cleaned up the head of his small cock of semen which was tossed to the side like trash. Then two egg vibrators showed up in her hand, and she grinned, and his eyes widened as she began taping the eggs to the head of his cock. "W-What?" He began to sound nervous as his cock was still only a little hard after cumming.

"Shh, Sissy," I said and pulled my fingers out and took a toy that Crystal handed me just as she finished strapping on the toys; now I had a good inch half anal bead string, and I picked up the lube and started to apply it liberally as he looked down. A moment later, his attention was completely on Crystal as she put the remotes in his hands.

"Better not knock them off, Sissy," Crystal said, "I have been ordered not to change the settings if they fall off your hands," She warned, then turned them to the max.

The effect was immediate, and his head hit the back of the chair. He loudly moaned out into the room as his sensitive cock was assaulted with two strong vibrators, and his cock was no longer going flaccid. "M-M-M-Mistress!" He cried out, "It, It, Feels Weird!" he yelled out, and I saw him biting his lip. This was only the start, and I loved this sissies reaction. We hadn't even finished the start of phase two as I took the beads and placed them against his ass.

"Enjoy your reward, Sissy!" I ordered loudly over his screams and pushed the beads deep into him. I watched as his eyes widened as more and more beads pushed into his ass quickly, each hitting that sensitive little prostate as nine and a half beads pushed into him. A moment later, after pushing them all in, I started to pull them out, and his eyes somehow widened even more.

Finally, as I pulled them all out except one bead, I began to push them back in and hit the switch on the end, turning on the beads. Powerful vibrations assaulted him, and I watched his hips attempt to push up off the chair with the restraints stopping the movement. His hips tried to thrust up against the restraints, and he tried again and again as I shoved the beads in and out of him.

"MISTRESS! I- I-!" Kyle cried out, and I watched as Crystal moved her lips to his ear.

"Cum, Sissy, Empty your watery sperm," Crystal said. Kyle froze with his ass slightly off the chair before his cock sent rope after rope of semen on his chest with wide-open eyes.

"That's right, Sissy," I commented as I shoved those beads in and out of his ass at an increased pace. His sphincter was struggling to grip onto the beads as they moved in and out of him, and I applied more lube, "Let out all your manly juices," I commented, "Release it all!" I demanded, and Kyle released more and more semen, but it came to a stop, and he collapsed onto the chair. I shoved the beads deep into him and stopped fucking his ass, just letting the vibrations assault him for now.

I stood tall, no longer squatting, and took off my gloves, and reached for new gloves as I moved around the chair. Crystal grinned as I replaced her with his head and whispered, "Tell me who you belong to, Sissy," I ordered softly, directly into his ear.

"I belong to you, Mistress," Kyle softly replied, his voice sounding indistinct as his body trembled in the massive post-orgasm.

"As my belonging, I demand more cum, Sissy," I told him, and I reached around him, and I kiss his cheek, and turned his head to his eyes could barely see my face as I leaned over the chair and over his shoulder and reached down scooping semen off his chest and onto two fingers. I brought it up to his lips, and his mouth opened. He took his cock juice into his mouth, and I felt his tongue on my fingers as he sucked his semen off my fingers with a moan.

"You're not done," I told him, pulling out gloved, wet fingers and scooping more of his semen onto my fingers as Crystal started to move the anal beads much slower slowly and Kyle moaned in reply as I fed him more and more of his semen. I watched his cock harden again under the vibrations and the much slower penetration of the anal beads.

"Mistress," He moaned out, "Please, Mistress," He begged without saying what he wanted.

"What do you want?" I asked softly, leaning over him.

"You, I want you, Mistress," He moaned, and I smiled.

"Then cum for me more, Sissy, and you can have me tonight. I want to see you cum more," I replied, and I stood straight again and reached for the cart. This time it wasn't beads. It was a small crop that was only half a meter long, and I looked down at him. "Cum more for me, Sissy," I said, my voice turning harsh. "Minx now," I ordered.

Kyle moaned, and his eyes widened a second later as the crop landed on his balls, with a carefully controlled hit waking him up from his post-orgasm bliss. A moment later, Crystal began to pull out the beads before pushing them in, and his cock jumped, and I turned down the vibrators on his cock as he cried out. "Why!"

"Mistress Demands more Cum. You will be punished for each minute you fail to cum, Sissy!" I announced as Crystal pushed the beads in and out of him. He moaned and groaned, and time passed without him cumming as he had just done twice in a row, and my crop landed on his scrotum, making him jump in the chair in an attempt to flee and cry out. His scream and crying sounded in the room, making my cock throb hard. I wanted to take him and fulfill his wish, but now wasn't the time. He was too tight, and a moment later, the crop landed on him again, and he cried out again.

"PLEASE, MERCY MISTRESS!" Kyle begged, "I AM TRYING TO CUM!" He cried out, begging for that sweet mercy.

"Then don't try," I said with the crop moving up in the air and coming down on him as Crystal fucked his ass pussy with anal beads, now sliding in and out of him without much resistance. He cried out again as the crop landed, and his eyes widened, and instead of cum his cock leaked a large amount of precum.

"O-O-Ooooh!" Kyle cried out, and tears poured down his cheeks. "PLEASE!" He cried out, and I grinned, my cock throbbing hard.

"Sure," I said, and instead of hitting him, I pushed the leather of the crop to the base of his balls and swiped up and down once, twice, and three times and his cock throbbed visibly and got larger and smaller before sending a rope of semen out.

"AHHHHH!" Kyle cried out in a ruined orgasm that sent his senses reeling, and I turned to Crystal.

"Stage three, Minx," I ordered. Crystal nodded and pulled the beads out, and I passed her gloves. She took the gloves and covered her hands before lubing her hand up completely and starting to lube up his ass. She took her time, and I reached down and made Kyle look at me.

"Sissy, Are you ready?" I asked him. I reached over and smiled as Crystal prepared him.

"Ready for what, Mistress?" Kyle asked as I moved over to Crystal.

He looked down at me, and I took the bottle of lube and covered my cock completely in lube, stoking it up and down. Crystal moved to the side and smiled as she prepared to watch, and her finger slipped off the gloves and pushed into her honeypot.

I smiled, "Are you prepared for your reward?" I asked, "To lose your virginity?"

Kyle's eyes widened, and he looked up at my face and down at my cock. His facial expression changed rapidly multiple times, and I didn't know what he was thinking. I looked down at him, and his cock was hard yet again. He wasn't turned off, and I grinned, "Now is your last chance, Kyle," I told him. "Now is your moment to back out and stay a virgin, or will you become my little sissy bitch?" I asked.

"I- I-" Kyle looked down, and I could see indecision, and I knew at this moment he was thinking of being in my pussy. He wasn't going to get that privilege.

"Five seconds, Sissy," I told him.

Indecision remained, and he looked up and down rapidly, "Four," I continued.

"Three!"

"Two!"

"One!"

"TAKE ME, MISTRESS!" He screamed with a blushing face.

"Take it, you sissy Slut!" I snarled, and I pushed forward.

His tight sphincter resisted at first. I pushed slightly harder, and I felt it give way a second later. "oooooOOOOOOOOHHHH!" Kyle moaned out as I pushed inside of him and his voice got louder as the head of my cock pushed deep inside of him. His rectum accepted me, although it was tight as it stretched slowly as I pushed inch after inch into him. His ass spasmed on me, making me stop as I didn't want to hurt him. Crystal reached down and slowly pulled off the vibrators. His cock jumped and fell back onto his stomach just as the fifth inch of my cock pushed inside of him.

"OH GOD!~" he cried out in a little feminine voice that hit the spot in my ears, and I pushed an extra inch faster than I meant to. I felt his body moving to accommodate more and more of my cock, and Crystal's hands found his cock and started to stroke his cock. His hips moved without his conscious thought moving up and down my cock, sending another inch of my cock deeper inside of him. I stopped at seven inches as the resistance made me think I would hurt him if I went deeper inside his tight ass.

I pulled out faster than I pushed in, and his mouth opened up wordlessly. I only pulled out two inches, and I felt his ass spasm a little on me. To retaliate, I pushed back in, and he moaned in reply. Crystal stroked his cock, and his hips tried to escape even as I pushed back seven inches into him before pulling back out all the way to the head of my cock. His ass gripped me like a vice, and I slowly pushed in with the lube allowing me to slide in deeper and deeper, back up to seven inches. "Ready?" I asked. "Ready to get made into my Sissy Slut?" I asked again.

"M- Mistress!" He cried out in reply, no longer able to articulate anything meaningful, and I felt my control slipping. I pushed in and pulled out quicker without going deeper, even as I watched his cock throb in Crystal's hand harder and harder. I was reaching a peak and his ass spasmed on my cock as I sheathed seven inches deep into him, feeling his ass and muscles tighten and loosen just as he cried out.

"FUCK I AM CUMMING, MISTRESS! SAVE ME, SAVE ME, MISTRESS, I AM CUMMING!" He screamed as a large rope of semen erupted from his cock into the air, landing on his face, closely followed up by another and another landing on different parts of his body all while his ass gripped my ass hard just before each release into the air.

My cock throbbed, and I wanted to pound him into submission. A second later, without thought, I started to pull out and push in. "Now, I will breed you, Sissy," I said as I took in this moment. I felt fuelled, and I pushed into him again and again, taking my pleasure from him. As his moans sounded animalistic as I took his asspussy for the slut that I was going to make him but reaching no deeper than seven inches, and I moaned as Crystal stroked his cock that had attempted to turn flaccid in her hand.

Kyle groaned and moaned as I took his ass, and Crystal stroked his cock, not letting it go flaccid, and he cried as his ass tightened on my cock. Pleasure and the feeling of dominance slowly took me, and I did quick, shallow thrusts, never going deeper and moaning as I was reaching my peak. I lost myself to the pleasure as I took the Sissy's virginity for my own and moaned out louder, and reached forward as I reached the peak and felt my hand tighten around his balls.

We cried out in feminine moans that echoed in the basement, and I released my semen straight into his ass pussy without thought. I felt his balls in my hand, thrusting lightly as he came once again. I watched as his cock lacked semen into Crystal's hands while my cock sent a rope of semen again and again into him. Kyle's moans hit me in a spot that made me gyrate my hips even as I only had just under half my cock inside of him. Kyle moaned, and I pulled out, sending another couple of ropes of semen onto his chest and cock and balls, more than doubling the amount of semen he left there.

I took large breaths as my ejaculation stopped, and I turned to Crystal as Kyle lay there, his eyes almost vacant. His expression showed nothing but pleasure as he looked down at himself. Crystal walked over to the drawer, took off the gloves, and opened the drawer. She took out the silver cage with a key, walked over, and handed it to me.

I snapped my fingers as I moved closer to Kyle and grinned. "Kyle," I said in the almost silent room. He turned to me, and I smiled. "Now you get to choose if you want to accept my last reward," I said. My smile couldn't hide my sadistic intent. "Do you want to belong to me and be caged?" I asked, holding the chastity cage before him. "Would you like to be my Sissy bitch?"

Silence reigned, and Kyle was blushing as he looked at me and my cock. His eyes lost that vacant look, and time seemed to stand still, waiting for his answer. I had no idea how long it took before Kyle replied, "Yes, Mistress, I want to be your Sissy Bitch."