Sissy’s Mistake

I left too early, and I did a couple of extra laps with weights on my body. Sweat poured down my body as I stepped into the locker room. My bag hung heavy on my back as I huffed, trying to catch my breath. I noticed Jake as I came in, and I smirked as my lungs gasped for more air under the heavy exertion I just did.

Jake looked up as I entered with sweat still dripping off my brow. My steps came steady, and I stepped past him. "My girlfriend enjoyed your video last night," I told Jake with a smile. "I enjoyed the part where you begged to be raped harder by your own hand." I teased him as I began to unstrap my weights.

Jake froze, probably knowing someone else in the world now knew that I was sissifying him. I turned to see his blushing face as I finished packing my bag with the weights before turning to him. I turned to him and stepped back towards him. I towered over him and forced his head to look up at me. My smell must have been entering his nose as I stepped close as it scrunched. I knew I smelled terrible, but I forced him to look into my eyes.

"You're my sissy, Jake," I told him; my words sounded absolute. There was no question in my mind of this, "Your little sissy show last night proved that to me." I continued to attack him mentally as he grappled with my words. "Now, Sissy," I said with my hand landing on his shoulder. "Get on your sissy knees and suck my cock. You need to lube it up nicely for your insemination today." I finished my orders with a smirk.

Before Jake knew it and with my hand pressing on his shoulder, he fell onto his knees. My hands pushed down my pants, and my semi-hard cock appeared in front of him. The smell escaped into the room as my dirty cock resided in front of him. I took out my phone as Jake wasn't paying attention and took a picture too.

Jake's mouth opened to protest, but when it did so, I put my cock into his mouth. I chuckled at his predicament. The smell made Jake gag, but his tongue went to work regardless, pleasing me. My cock started to harden under his workings rapidly, and I began to tease him with words. "Ah, Such a good cocksucking sissy," I said, "Have you been practicing at home?" I asked him while keeping his head bobbing on my cock. The pleasure continued as I began to force his head deeper down on my cock.

I thought about something Crystal said the night before while he worked my cock, and I now wholly agreed with her. Jake was a natural sissy who used to think he was an alpha due to his sports position. My mouth moved without thought as I told Jake, "You're such a natural cocksucking sissy, Jake. You have the natural aptitude to be a cum dump. Luckily you met me so you could learn your natural place." I finished teasing him for the moment and pulling my cock out of his mouth, hearing the pop of the suction Jake was creating.

Jake looked up, his face blushing in embarrassment, and he finally spoke for the first time this morning, "That isn't true!" He retorted uselessly. This simple retort earned a snort as I slapped his face with my now hard cock.

"Did you bring lube?" I asked Jake. The question changing the subject startled Jake. I then noticed his blush deepened, and I knew he did. "Take out your bottle of lube; I want to feel the difference your ass feels like with it."

The shame that Jake must have felt as I told him to use the supplies he brought made him meeker. The verbal and mental assault I have been dishing on him seemed almost to have put him into a submissive trance. Still, I had an odd feeling as he brought out the lube.

It was a nagging feeling like something wasn't right. I was about to make Jake turn around and present his ass when I decided to follow my instinct. It was something about Jake's attitude. It was too submissive, as well as the video. It was like it was staged to make me feel like he was being trained quickly. This didn't sit right with me at all, and I decided to move. I pushed the sissy aside and grabbed his bag.

I then dumped all the contents onto the floor. Three items stood out to me as they fell. One was a phone recording this interaction, and another was a small unknown device, the last being a pen attached to a textbook conspicuously. I snapped open the pen seeing electronics fall out with a lens. I then realized Jake planned to get me to incriminate myself somehow.

No, I was going to give him a good fucking was what I was about to do. Jake would then act like he was being raped to the camera so that he would have something to defend himself. All of the meek acting he was doing and the restrained resentment were all for this. It would free him of me, and I passed Jake the phone, my tone frosty.

"Jake," I started, and he visibly flinched from me, mentioning his name. "Open your phone now," I ordered as my hand took the unknown device snapping it open. I didn't know what it was, but my hand strength then crushed it easily. I felt it poke my skin, but at this moment, I couldn't care less; I was livid.

Jake noticed my tone, and he opened his phone with his sissy instincts telling him to do so. Jake made a gamble to try and get leverage and failed. Now was time to deal with the aftermath. I looked through his videos and found nothing, and I checked his open e-mail. I only noticed the email from last night. I finished checking to find nothing, so I dropped the phone in my clothes.

"I am guessing you got these things while out getting lube," I said, my tone remaining frosty.

"Fuck you, Cunt, You are fucking raping me and forcing me to do these things," Jake said, his anger clouding his better judgment. I looked at him, seeing his resentment again, and I knew that Jake had planned this morning's meekness. I don't think he realized how much he enjoyed last night's video to me, though.

Jake was a natural sissy, but someone in the room didn't know what they wanted, and now my anger was brought back, and the sissy was causing a rebellion. Still, there were holes in the lockers around me, and I decided to play it safe. I stepped over to the door, and Jake seemed confused about things. I clicked the lock shut and turned around.

"You, Have, Fucked, Up," I told Jake the truth. I was in front of him in seconds, and one hand grabbed the lube while the other grabbed his neck, and Jake was lifted by his neck into the air. I moved him into the showers. Here regardless, we were out of any hidden angles that a camera could hide. I shoved him into the stall before I took off my shirt.

Jake was coughing slightly as he regained his breath. It was a short encounter, but I moved away, turning on each stall. Soon the room started to fill with steam and the sound of showers raining water. Jake seemed to have smartened up in the time I came back, and I grabbed his neck again.

"Today, I thought about being nice to you," I told him an unprovable lie, "Through your bad actions though, I have changed my mind, sissy." I finished, and I started to use his lube on my cock. I was still curious about the difference it would feel like during sex. Jake started to try and fight me off by throwing a fist at me. I caught it and placed pressure on his knuckles as he gasped in new pain emanating from his hand. Soon He was on his knees as his other hand tried to take my hand off.

"Fuck you!" Jake almost shouted, drowned out under the onslaught of showers around us.

"No, Jake, I will fuck your sissy ass," I told him. I let go of his hand and grabbed his wrists. I then grabbed him, turning him pressing him against the wall. I then brought my lubed cock to his rosebud. "Jake," I began as I lined myself up, "You will learn that choices have consequences. Whether you like that or not doesn't matter to me. For now, though, your ass is MINE!" I announced to him, my cock slipping into his ass, realizing that the buttplug was on the shower floor at some point.

I could care less as I forced myself deeper inside him. His cry in the room is still covered under this sound of a dozen showerheads pouring down water. I pulled his long hair back and shoved myself deeper into him. His ass took my large cock deeper and deeper, the lube making it easier as a haze of steam started to thicken in the locker room.

Jake cried out at the forcefully undertaking of his ass, and my hand released his wrists as I pulled his ass off the wall and held his hips in place. Then Jake did the most sensible thing he had done all day; Jake found something to grip and prepared himself for the ride. I trusted in deep. I was at least fourteen inches deep, and I pulled out before I began to thrust in even deeper. I had memories of Crystal's womb on my mind and the pleasure of being balls deep. I cared about Crystal; I couldn't give a single fuck about the sissy under me. I trusted with my anger being vented with each thrust.

This fucking sissy thought that he could blackmail me back. That was his plan, and I started to fuck him even harder as I thought up a new plan while the pleasure invaded my mind. Jake needed a lesson about how life doesn't have him as the main character. I will fuck his ass into submission; I thought as I felt my full balls slap his ass. The slap woke me up from my thoughts as I heard the sissy under me cry out again.

With my mind awaking, I began to spank this disobedient sissy's ass. My hand came down repeatedly under the sound of water faster and faster. His cries became louder as my hand rained down while I raided his insides. I didn't care about how he felt as I rained blows down on his defenseless ass.

Jake cried out, and I felt myself reaching my peak as I felt his ass spasm. I knew the sissy orgasmed in my head, but frankly, I just got angrier. I wanted him to suffer, not enjoy himself. This sissy was having sissygasms while I fucked his ass. This was supposed to be a punishment, and here he was enjoying himself. I finally decided that I needed to make Jake too ashamed to even think of fighting back.

I trusted into his ass, hearing my balls slap his ass as I released inside his sissy pussy. I groaned as I started to ride out my orgasm deep inside him; The Sissy moaned as I did so too. Jake knew I just released deep inside of him.

As my ejaculation finished, I began a new, sowing more seeds into his ass. Jake yelped with my renewed thrusts as he thought I was finished after releasing my seeds the first time. "The Fuck!" He cried out to me in protest. My hand landed upon his ass was met with a moan as I made sure to poke his sweet spot as I drilled past it.

Soon Jake's cries grew louder, and his ass started to shudder more violently with my thrusts. Pleasure swarmed my head as I took sadistic glee in his plight. Soon, though, I was near the edge and released into Jake's sissy pussy as the pleasure-filled my head.

I slowly rode out my orgasm before I pulled out. Jake fell to his knees, his boy pussy gaping and winking at me. I grabbed the plug off the shower floor, making sure to quickly clean it before I squatted and filled his gaping asshole. Jake moaned at the sudden intrusion and turned to me in his shock. My hand reached out slowly and cupped his face. My hand lightly slapped him, making him flinch multiple times as the showers roared around us.

"Jake, You are the reason you're being sissified by me. You could have fucked off and never talked to me. You could have lived your life thinking you were the top dog. You are stupider and weaker than me. You will forever be a sissy slut from now on." I told him as his resentment shone through his eyes with tears inhabiting the corners of them too. "You have a girlfriend, don't you?" I asked him.

"Yeah, what of it bitch?" Jake said, coming back to himself.

My hand slapped him a little harder, but I stopped from leaving a mark. "You will go get a pair of panties from her tonight." I told him with a smile, "I will see you here tomorrow morning with a pair of panties on. If not, I will make you come over to my house for an intimate evening with my cock up your ass for a pounding you will never forget." My tone turned stern, "Do you understand me, you stupid sissy slut?" I said slowly.

Jake looked at me, filled with resentment, and nodded, not saying anything. "Good, now get them from that girlfriend of yours. If you can't, I want to see a video of you shopping for them in the mall. I want to see your selection of choices. I want to see you purchasing them. Then I will see at least a twenty-minute video of you fucking your sissy ass. Do you understand?" I finished.

Jake gritted his teeth and nodded. My hand slapped his face lightly, repeatedly increasing in strength until the following words came out, "Yes, Mistress," Jake said.

"Good," I said before standing up and turned on our shower. The water was feeling a little cool, but I left to grab my supplies and started to clean myself up for class. Jake began after me to clean himself up. I ignored him as he did so. I began to wash my hair when his question came out.

"Can you release me?" Jake asked meekly.

I looked down at him as I cleaned my hair. "No," I told him coldly, "Bad sissies don't get freed," I finished before going back to ignoring him. He started to protest, but I ignored him throughout the entire exchange. I finished and started to change. Jake came after me to continue talking about it as I buttoned up my shirt and placed my cock back into my clean panties. I then made sure every shower was off before unlocking the door.

I left an ignored sissy behind me as I traveled to classes getting some studying done before shooting a text of Jake about to suck my cock to Crystal. I smirked as I started to study and double-checked my work from the previous days.

An answering text didn't come till period. I smirked as I opened the text.

Crystal: Oh, My, God! <3<3<3 I can't believe I took your entire cock last night as well! My womb is trembling as I gaze at this picture. I can't even walk straight right now. Are you able to come over tonight? <3<3<3

Crystal knew I would be angry if she tried to turn me on while I was at school. I already had plans for tonight, though. I quickly typed up my answer as I made my way to the locker rooms.

Angela: Can't tonight, I have something planned to teach someone a lesson. Sorry, But Tomorrow should be good. I can't help but think of you're fantastic pussy!

I finished before sending it off. With that, I arrived at the locker rooms. Stepping inside, I saw Tracy with a bikini on. It was brown and nothing special. I walked past her and sat on the bench before looking at her.

"That's it?" I said, "A fucking brown bikini?"

"What, I look good!" She retorted, and I scoffed.

"You look fucking like a normal slut. You need to work to make me hard bitch. No, you failed to impress me even slightly with a fucking brown bikini. I decided on one of two options, though. Either you can go commando as punishment tomorrow throughout the school." I said, seeing her outrage at the thought with our school's uniform. "Or tonight, You will come over and be a slut for the night. If I am not satisfied, you cannot leave." I finished before I turned to start grabbing out my lunch.

As I did so, Tracy's mouth opened and closed like a fish gasping for air. "Fuck you!" Tracy cried out.

"Choose, Or I will, along with another punishment," I told her.

"Fine, I will be your fucking slut for the night," Tracy announced.

I smirked, and I pointed down. "Get on your knees and suck Slut. You will need some good lubricant." I told her, and she was on her knees. She crawled under my skirt as I started to eat my food while Tracy retrieved my cock from my panties.

I then started to eat while Tracy began to suck me off. She would earn moans from me here and there, but she really wasn't as good as Crystal. It was like going back a version as I ate. Still, I ate with a contented sigh and a moan here and there. I ate to the sound of slurping and groans as I watched some fingers pop out from between Tracy's legs while she sucked me off. I grinned but allowed it as I kept eating. Tracy was in for a night of trying to satisfy me, and it would be a marathon.

Soon I finished my meal, and I placed the container to the side as Tracy did something with her tongue on the tip of my head, earning another moan. I then pulled her head off and handed her a condom package, "Get my cock ready, Slut," I told her. Tracy was still much better behaved than her sissy boyfriend. She slipped it on after a couple of extra rolls down my cock. I then patted my lap.

"Slut get aboard for your ride," I told her with a smirk.

Tracy glared at me and pushed aside her brown bikini bottoms; I noticed the wet spot on them. I grinned as she lined herself up before dropping her hips without prompting. I smirked, and my hands grabbed her brown garbed breasts. I squeezed them harshly, making her groan as she moaned. I then moved my hand under her Bikini and noticed she wasn't moving. "Slut, Get moving!" I order her, and I noticed a shake in her legs as she moved up. Tracy only took about eight inches before she stopped, and I realized that she didn't want the same experience as last time.

I sighed, and I groped her breasts hard before I left them. My hands landed on her hips as she shakily lifted them. "Slut, This is how you move your hips!" I announced, and I lifted her ass up to the tip before harshly thrusting her ass upon my cock. My cock barged through the door of her womb, making her holler out loudly. I then began to pull her off before forcing myself deeper into her. Tracy wrapped her arms around my neck as I started to force her ass to get fucked faster and faster upon my cock.

Tracy wrapped her breasts around my face as she clung on for dear life as I rocked her world with my cock plunging deeper into her womb. The Second penetration brought even more pleasure for me, and soon I felt Tracy's ass on my lap. With it, I felt my cock pressing harshly against the inside of her womb, forcing it up. This caused Tracy to grip me harder, and her mouth sank into my shoulder as she screamed.

I felt her body shudder, and her pussy ejaculated. I was merciless on this slut, and I started to fuck her even harder without care as I raided her womb. Tracy kept her head in my shoulder blade and screamed with each thrust. Her pussy spasmed as her world was rocked from orgasm to orgasm until I moaned and released my load deep inside her womb, filling the condom.

I pulled out slowly as I finished releasing, feeling still annoyed as I exited. I pushed Tracy to the side, whose legs twitched from her last release. I checked my phone to see Crystal messaged me. First, I checked the time, and I found I was low on it. I looked down, and I walked to the bathroom part to clean off the skank juices on me that Tracy left. It wasn't perfect, so I sprayed my skirt with some water to cover it up to make it look like water fell on it. With that, I turned to Tracy. "Park, one hour after school. I don't want my parents knowing I have a skank over." Tracy looked at me with resentment, and I smirked as I left after picking up my stuff.

I made it to class a little early, and I immediately opened my books. I started to think about what I could do in the future as I opened the books. Sports at this point were off the table. I would definitely keep up my workout routine; these muscles need constant love. I then thought about the offer Crystal talked about. I thought about dominating random men, and I had no problem doing that for money. I wasn't sure about it being as much as Crystal said, but I would talk to her about that tomorrow when I would make my way to see her. It would be a Friday too, I believe, and I would have the weekend off.

This was a realization that the first week of school was about to come to an end. I started to contemplate how much my life has changed in the last three days since that fucking sissy tried to rape me. This brought back all the pent-up anger all over again. I soothed myself, knowing that I would cuck him tonight with his girlfriend. He would try to have her save him, and she would disappoint him so that she would go see his tormentor. Then have her skank of a pussy shaped never to be able to feel pleasure from him even if I released him.

I smirked with my last thought as the Teacher came in and started to teach physics. It was a class that I didn't find hard as long as I kept on top of studying. Soon the teacher began to teach her lesson as I remembered the text from Crystal. I snuck a peek at it.

Crystal: :O I can't believe it! Jk, I understand your busy tonight, but it sounds like something ominous. Still, I think I need a night to go finish some paperwork at the store as long as I can make it there. My legs are still trembling hours afterward! Are you busy tomorrow?

It wasn't until after class, and I sent a text back to her while on my way to Gym.

Angela: Yeah, I need to put someone in their place tonight. Tomorrow I will be free to come over. With the weekend, I can probably stay around longer too. Although I think my mother is angry at the moment. I will have to do something to appease her anger; otherwise, I will feel it at a random moment. My mother can hold a grudge.  P.S. Never win a game against my mother and leave after winning. It will be a moment you will regret later.

I got a text not too long later.

Crystal: Noted; I look forward to meeting your mother, to be honest. I have to ask due to curiosity. Did your sissy Misbehave? I can feel the anger about putting someone in their place.

I arrived at the locker room and entered as I typed my response.

Angela: Yes, Let's say he tried something that pissed me off badly. I decided the best response is to make sure his girlfriend will never feel pleasure from him permanently. I also added a couple of twists for him. I will say though you will enjoy the videos later though.

I felt a sense of putting myself out there with that text. The reply came pretty quickly afterwards, and I had a hopeful feeling.

Crystal: I won't be mad as long as you record it and send me some of it. That fucking sounds HOT! <3<3 What did I do to deserve such a fucking hot Girlfriend? You will totally fit in with the swingers part of the community!

I felt a sense of relief. Our relationship was really new, and I have no idea what Crystal's bottom line was. All I Knew was that It was farther down than I thought. I had no problem showing the Skank being forced to submit tonight to Crystal if she wanted it. As I opened more up to Crystal, the more she accepted me. I felt warm about this as I started to have more feelings for her.  I sent a quick reply.

Angela: Okay, I will send you a video of a skank being fucked to submission.

I heard a second bell and knew I was running late and got into my Gym clothes. I rushed out to join the others as they lined up for the Gym teacher. Today was volleyball and I smiled as the class was split into four teams to play.