The wind in my hair as I ran down the empty streets this Monday morning was wonderful. Sweat started dripping on my brow but quickly cooled off in the autumn morning as September was coming to a close. My breathing was steady, and my smile was bright as I moved through the empty streets.
I heard a car pass as I reached closer and closer while the sun rose on the horizon. I was a little earlier than I thought, so I took a couple of laps around the entire school. I felt the sweat dripping from my body as I took the third lap and decided to head inside. The little sissy bitch Jake should be here by now as I saw someone running inside on one of my laps.
I entered the school halls and walked toward my destination with a single-minded purpose. I had an Idea for Jake that he wouldn't like, but I would enjoy immensely. I quickly reached the teacher's locker room and opened the door. Inside I saw him instantly. I could see the scowl on his slightly attractive face. His arm muscles were one of the few things I envied as my own never seemed to show. I looked over him, seeing him in the Male uniform for our school—the buttoned-up white shirt with black dress pants for men.
Jake's resentment and hate were painted on his face as he glared at me but held a healthy dose of fear. I came in dripping with sweat, and my smirk grew, "How was your weekend, Sissy?" I asked, knowing that it must have been hell.
"F-" Jake began, then visibly calmed himself. With a raised eyebrow, I watched and waited for a second, "I wish to be let out of my cage, Mistress," He finally said.
"Hmmm," I said, putting a finger to my mouth exaggeratedly, "No." Jake quickly opened his mouth, and I shook my head, "I will unlock it so we can clean your little pecker today. Oh!" I exclaimed as I had a sudden thought, "We can shave it tomorrow to make it look like the little baby dick it is!" I grinned, turning to him, "First though, You will be coming home with me after school today Sissy." I suddenly told him, surprising him.
"What? Why?" He suddenly asked.
I leaned forward, and I slapped him across the face with calculated force. "I am your mistress, Sissy; you will address me as such with respect I am owed." I was sick of having this discussion with him, and he held his face, startled at the sudden violence.
"Y- Yes Mistress," Jake stammered out.
"Good," I told him, leaning forward toward him, "Stop forgetting it, or else I will increase your punishment." I leaned back, "Now I have some things for you at my place, and you will take them home with you tomorrow morning. But we can have some fun after team practices. This isn't optional either, Sissy," I smirked, "Now time for inspection, Strip."
My order came out, and Jake was still taking it all in. The surprise on his face was completely evident, and he opened his mouth when I stepped toward him and placed a finger over his lips, "If you say anything other than 'Yes, Mistress,' or 'I look forward to it, Mistress," You will not like what happens to you." I told him, and he shut up. "Strip, It's inspection time, and I think my cock is a little hard; if your lucky, you could have my sperm in your ass all day long," I told him, and his expression wavered.
I stepped back, and I watched him as he finally stripped. His slight agility-based muscles came into view with a white bra came into view—the blush of shame on his face in full view as he unbuttoned his pants. Jake dropped his pants showing cute little white panties that I hadn't seen before on him. There was even a cute little white bow on those panties.
"Cute," I said, looking him over, "Show me the plug and chastity cage now," I continued.
Jake pulled down his panties, and the plastic cage was in full view. I grinned and twirled my finger around. Jake instantly understood what I meant and leaned forward, showing me the anal plug I left him last week. I grinned before reaching out and pulling the plug out of him. I didn't remember when I disengaged the plug for him, but I clearly did at some point over the weekend. It came out clean, and I smirked, "Cleaned your sissy ass for me. Not too long before this little hole should just be called a pussy," I mocked him.
I heard a moan as the anal plug was pulled out and a little pop as he came free. Jake didn't say anything, though, and I pulled out my phone, disengaging the chastity cage lock. I looked at my phone's settings and realized the battery was running low on the cage. I would have to charge it tonight or change him into the original that I got him. It made me smile thinking of his original and how I met my Girlfriend just a few weeks ago. Maybe I should do something with her to celebrate?
"Well, Sissy, You passed inspection; let's get you all cleaned up, so you don't get an infection or something. My cock could use a little Sissy slut on it, and since the plug came out clean, I think I will make sure it has something to plug after the shower. Go warm up the water, Bitch." I ordered, and the condescending tone it carried was prevalent. Jake blushed, and I could see the anger and humiliation that he saw. There was something else I saw too that I wasn't sure if I saw correctly. But maybe, Excitement?
I didn't know or care as I saw him take off his bra and start to head towards the showers. "I unlocked your cage Sissy," I said as he moved to make him pause, "Leave it by the sink so you can clean it up after," I finished, and I turned and glared at me.
"Yes, Mistress," He said, his tone not showing any resentment that his face was expressing. I saw him reach down and take off the cage for a moment while I took off my backpack finally and set it aside, grabbing my stuff to clean myself up. I grinned as I heard him moan in pleasure as his cock sprang free.
"Touch yourself, and I will punish you," I said as I heard that moan.
Jake froze and nodded before heading to the shower. A second later, I heard the shower turn on, and I took off my outfit and weights, setting them aside for later. I didn't waste time, and I wrapped up the sweaty clothes and put them in my bag. I wouldn't like wearing them later, but I was used to them; for school. I turned and locked the door, ensuring no one would enter before I headed over to the showers taking some soap and shampoo with me. I stopped outside the stall that Jake chose today and saw him looking at me with the water falling on his back.
His expression was unreadable, his cock hard and his hand inches from it. "What a good sissy," I commented, looking at him. "You are learning finally," I told him with a grin stepping toward him. He didn't retreat from me, and I grinned inches from his face, "On your knees," I said as I pointed toward my half-hard cock. "Get it all wet with your spit," I ordered him.
Jake looked at me for a moment, and I decided I would mess with him. While he looked at me, I grabbed him, pulled him close, and took his lips. I mashed mine against his and conquered his mouth quickly, my tongue invading and pinning his tongue down. Jake's eyes widened, and instinctively he fought, and I let him go. I pushed him back, and he stepped back into the divider. I stepped forward, and I grinned. I spat as he opened his mouth, and my spit slipped into his mouth.
Jake coughed as the surprise spit entered his mouth, but my hands were on his shoulders, and I pressed him down while he was still off-balance. "Look, Jake," I said, my hardening cock in front of his face, "Your rightful place," I told him.
I reached down, slapped him with my half-hard cock, and the wet sound was loud even with the shower. Jake winced, and I pinched his nose, forcing him to open his mouth again. He cried out a little before I stuffed my half-hard cock into his mouth. "Show me all your progress this weekend, Sissy," I ordered, and it took a second before the suction in his mouth began.
Jake started, and I knew, at this point, it was the familiarity of the task that he only began learning this week that made him do this. The mentality that it would be over faster if I released a load into his mouth. I grinned as I felt him moving his head back and forth. I took a half step back, allowing the sissy more space to suck my dick. He instantly used it, and I felt his hands touch my thighs as he began bobbing his head up and down.
The water of the shower fell on my head as I looked down at the sissy seeing him move and eventually pop my cock out of his mouth. Jake's tongue licked up the side as I heard him take deep breaths. This sissy was learning, and I couldn't help but smile as I felt the pleasure start as I reached full mast. Jake didn't stop, and I began to wonder if he had started to enjoy doing this. I moaned to let him know my pleasure as he took my cock into his mouth again.
Much to my surprise, as I looked down seeing his hard sissy cock; he never moved his hands from my thighs. I don't think Jake even realized that disobeying my order came to his mind. I grinned, and I brought my foot under his cock. He froze as my bare foot pressed against his balls and cock.
"Continue, Sissy," I ordered, "Don't cum unless I order you to." I finished.
Jake popped my cock out of his mouth and licked the head of my urethra, sending a shiver of pleasure through me as he replied, "Yes, Mistress."
I pressed my foot, balancing on the other while stroking his cock from underneath and using my toes to play with his balls. A moan of pleasure left his mouth, and I continued stroking him as he moved his head along the length of my cock. I felt a low surge of pleasure, and I continued to toy with the sissy while he moaned in response to my stroking. Jake began to fuck his throat and began to be more enthusiastic about sucking my cock as I continued to stroke his cock with my foot.
A couple of seconds later, I let go of his balls with my foot, reached up, put his cock between my big and little toe, and began to stroke his cock. "Cum, Sissy," I ordered as he moaned, "Cum like a sissy slut to my foot, knowing you will never be able to touch my pussy with anything other than your mouth," I told him.
Jake took my cock deep, and I heard him moan loudly, rumbling my cock as he took eight inches of my dick in his throat. I felt a burst of warm liquid on my leg and foot as I felt his cock throb on my foot. His moan was loud and long in the shower, and I grinned, looking down at him. "No rest for the sissy," I told him, and I quickly pulled his head back by his hair. "STAND SLUT!" I ordered suddenly.
Jake was in some post-orgasm bliss and needed to breathe. I didn't give him a chance as I started to pull him up by his hair. He stood under my direction before I turned him around and pinned him to the wall making the knob of the shower press into his stomach. I didn't care about him as he cried out in pain. I was busy lining up my hard throbbing cock to his puckering little asshole, and I dove in deep. Jake moaned as I drove deep into him before thrusting the rest of the distance, making him a sheath for my sixteen-inch cock.
"Mistress!" He cried out, his voice a mixture of pain and pleasure. I still didn't care as I began to thrust in and out of the sissy bitch. "Ah, AH, AH!" He moaned as I took a pace and slowly increased it with each thrust. His cries sounded in the locker room, and I was reaching my peak.
I had one hand on his shoulder while the other went around to his cock, which was still hard as a rock. I grabbed his balls and tightened my grip on them as I thrust in and out of his little sissy boy pussy. "Who owns you, Sissy?" I asked without thought.
"You, Mistress, You own me!" Jake cried out in the heat of the moment.
"Better fucking believe it, Sissy," I replied and found tightened the grip on his balls, feeling them throb.
I pulled his balls, and he cried out and came as I felt his cock throb above his balls just as I reached my peak and sent the first rope of semen deep into his ass. I didn't pause and thrust into him more, making him moan as I rode my orgasm, sending rope after rope of semen deep into his boy pussy. Moaning, I rode his ass, slapping my hips against his ass, sending shivers of pleasure through my body, and Jake moaning, he experienced a pleasure of his own.
I pulled out of his ass and smiled as he fell to his knees. "Turn around," I told him, and Jake froze again for a moment before doing so. "Clean my cock up, Sissy," I ordered again and sighed in pleasure as I felt him suck out the semen leftover.
I let him clean my cock for a couple of moments before I stopped him. "Stand," I said, "We need to clean up, and you, Sissy, need to be plugged again to get all the nutrients from my semen." I finished with a smirk.
"Yes, Mistress," Jake said, his face flushed from the humiliation and the heat of the shower. I moved, grabbed the discarded soap and shampoo, and washed Jake's now flaccid cock.
On the other hand, my cock was still at full mast as I could go for a couple more rounds of sissy ass. I didn't, though, as I didn't know how much time was left. I stopped cleaning Jake's cock, stopping when it began to harden again.
I washed instead while Jake seemed to be watching me. His expression was one of loathing and thought while he looked at me, and I turned while washing my breasts. "Did I say you can look at my body, Sissy?" I asked, my tone carrying a dark undertone.
I didn't need to say more, and he turned away. Then I realized a mistake I had made; I forgot to record!
I felt a little annoyed at this and began to wonder if I should just purchase some things for this room to record. I instantly shook that thought out of my head, though, and I looked at Jake's back. "Go clean your cage and butt plug before coming to show it off to me, Sissy," I ordered while I moved down to wash my legs. "If you are a good sissy, I might even reward you tonight, Sissy," I finished.
Jake was looking away and nodded, walking out of the shower stall. "I watched, and I wondered what the dumb sissy thought. I didn't know, but I thought it was funny that he thought he could do anything. Still, I reminded myself I should give him a look over before I was done with him today.
Jake didn't want to be in his current circumstances, so he might try getting a recording of his own to use against me. Mutually assured destruction was a smart decision, but it wasn't one that I wanted either. I had a lot of revenge on Jake, and I would not be able to complete it if he got his hands on something like that. I would prefer not to let that happen, so I needed to pay attention.
I sighed and washed my hair before rinsing it off. I heard the sink in the bathroom stop, and Jake came in wearing the chastity cage. I twirled my finger as I stopped shampoo from entering my eyes, and Jake turned around and spread his ass cheeks, showing them to me. "Good," I said as I saw the plug inside of him. "I will be out in a second," I told him as I finished rinsing my hair, "You can stay like that for a second while I dry off. I stepped out and grabbed the towel I had prepared, and dried myself off. I slapped his ass as I passed and moved to his bag while I said, "Continue standing there," I said as I unzipped his bag.
"Mistress?" I heard, and I looked through his bag, finding his phone, and I looked around the room, finding nothing amiss.
"You are free to dress and leave, Sissy," I told him, "I want to see you on the sidewalk when I finish Volleyball, Sissy; ready to go."
"Mistress, I can, Mr. Trimmers!" Jake began, and I shook my head.
"I don't care," I cut him off, "You follow my orders over Mr. Trimmers. Now go!" I told him and pointed at his clothes. "I don't want to hear you until after school." I finished and grabbed my phone, snapping a picture as he moved to put on the panties. I waited a moment, pulled up the app as his leg was in the air, and locked the anal plug.
He moaned and almost fell face first before righting himself. A further blush of shame painted his face. He moved to put on the bra, and I watched for a moment while locking his chastity cage. I then ignored him as I reached into my bag and pulled out my clothes. Looking at the time on my phone moments before, I still had some time, but I needed to study; otherwise, I might start falling behind. That was the worst as it takes longer to catch up than to keep on top of it.
I saw Jake leave the locker room smiling as he took his backpack. Jake's sissy ass was full of my semen, and I wonder how long till the semen enema took to work through him. I shook my head and turned my attention to putting on my black bra and panties today. Usually, not a good choice with our school uniform, but I didn't care. I had a woman's body with large F cups. Before I got my new bras, I was running low on bras that fit. The black ones were today's option.
I finished getting ready and packing my stuff. I finished packing up and took a last look around the room just in case. I found nothing and left the room wearing the weighted vest while putting the weights on my limbs into my backpack. With everything cleaned up, I left the room with a smile on my face.
I couldn't wait to play with Jake tonight.
Jake was going to hate it.
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Hey Everyone,
So, a short announcement, first of all, next month I will be gone for half the month on a much-needed vacation. I will be posting a chapter at the start of the month, then I will be off for much of it. This is something to help me avoid burning out as I work a full-time job and write.
So for September, I will post one chapter when I go and one when I come back, and I will start going back to my one a week for most of my stories in October. Just wanted to give you all a heads up, so you know why I am not posting in September.
If you want to check out the Discord, here is the link.
https://discord.gg/7gckg3VxyY
Also, I have two new stories on Amazon.
I Sissfied my step Bro book 3
The Demon Queens Handler
You can also support me at my Patreon if you want to read ahead for as little as 1.50$ CND
www.Patreon.com/madjic