Jessica Obeys

i know (apologetically)

i know (condescendingly)

its supposed to

you can take more

this is how you learn

good sluts take it

stop complaining

i don't care

i didn't ask

your pleasure is irrelevant

you shouldn't have done *insert mistake*

focus on pleasing me instead

you're not supposed to like it

don't talk back

you look so cute like this

you're mine and i decide what you do

its your punishment for *insert mistake*

shut up

good

you're supposed to be focused on my pleasure

get used to it

you can take it cant you?

you asked for it

beg for it to stop then

you look prettier overstimulated

you'll stop when i tell you to

*gagging them so they're quiet*

your only purpose is to be a fuck toy for me so don't complain

you know you like it

aww but you look so cute like this

stop lying

it cant be that bad if you're still talking

i know (apologetically)

i know (condescendingly)

its supposed to

you can take more

this is how you learn

good sluts take it

stop complaining

i don't care

i didn't ask

your pleasure is irrelevant

you shouldn't have done *insert mistake*

focus on pleasing me instead

you're not supposed to like it

don't talk back

you look so cute like this

you're mine and i decide what you do

its your punishment for *insert mistake*

shut up

good

you're supposed to be focused on my pleasure

get used to it

you can take it cant you?

you asked for it

beg for it to stop then

you look prettier overstimulated

you'll stop when i tell you to

*gagging them so they're quiet*

your only purpose is to be a fuck toy for me so don't complain

you know you like it

aww but you look so cute like this

stop lying

it cant be that bad if you're still talking

**The following is based on real events. As it has been sometime since it occurred, the events are most likely a blending of several sessions between my former anal trainer and myself. However they are as accurate a recounting of my experience and his skills as possible to the best of my memory. Please do not forget to rate the story once you have read it.**

Standing at the faucet, filling the water bottle with warm water, I wondered how long I had known Chace. Affixing the top to the water bottle, I climbed into the tub remembering corresponding with him on the dating website designed for single kinksters. Taking a deep breath, I squatted, inserted the opening of the water bottle into my rectum and began to squeeze.

All the thoughts about Chace immediately evaporated. The water swooshed inside my bowels and I couldn’t prevent the moan that escaped my lips. Every one of my muscles loosened as I squeezed once more. My bowels filled with the warm liquid and my sex began to tingle. I wasn’t sure if it was the pure sensation of giving myself a homemade enema that was turning me on or the fact that I was obeying him and preparing for our session.

Chace and I had been out one or two times before we agreed to play. We spent many conversations both online and in person discussing the rules for play. He was not my Master, he was my Trainer. I would address him as Sir. Our mutual goal was anal training.

Prior to meeting Chace, I was an anal virgin and over the last few years, our sporadic meetings have been dedicated to my anal training. His goal was for me to take his large, thick, masculine fist. Over the course of our meetings he had provided plugs of various sizes to help stretch my hole for him.

One this occasion, as I filled my bowels with water, I was instructed to clean myself with a homemade enema and insert a plug an hour before he arrived. It was a medium sized flesh colored plug. As I waddled to the toilet to empty the liquid sloshing inside me I wondered how long our session would last this time.

Expelling the liquid, I let out a large sigh. I immediately missed the feeling of the water flowing inside me. With a smile on my face, I decided I would do a couple more passes with the water bottle to ensure that I was clean. Purely for hygienic reasons, not for any sort of pleasure, I mused to myself as I filled the water bottle again.

After four more flushes with the enema I decided that it was time to get the plug ready. I wouldn’t want to disappoint him and not be plugged when he arrived. I had never been truly punished by him but I had a feeling I would want to avoid it.

I walked into my bedroom and collected the plug and lubricant. I crawled onto my bed, on all fours, naked, with my legs spread as I squirted the clear gel onto the cone shaped plug. Taking a deep breath, I brought the plug around my body and awkwardly probed for my own asshole.

The gel was cool and I shivered as I found my target. I took a deep breath and began to push. My anal ring protested; it had been about two months since I had last seen Chace, I may have been out of practice. Pressing harder against my opening I groaned as it gave, opening for the tip of the plug.

My 36C breasts were pressed between myself and the bed as I lowered my chest, pushing my ass in the air. My body tingled all over. The feeling of my ass being filled always sent me soaring into a fuzzy world of subspace.

I stopped pushing, and the plug slipped back. I ensured that it did not fully leave my ass and exhaled slowly. One thing that Chace taught me was to always breathe, slowly, deliberately when engaging in anal play. It helped relax my body. The short rapid breaths were what tensed me. I needed to be completely relaxed if I was going to take his fist today. He had gotten so close last time.

With another deep breath I pushed the plug again. I groaned louder as it went in farther. My pussy twitched my wetness increasing as I worked my asshole wider and wider with the plug. When I looked at the plug, it didn’t seem that long or thick. However, when I work it into my ass, it feels a mile long and impossibly girthy.

Again, I let the plug slide back. I am convinced I took the majority of it that time. In my head, I hear Chace’s voice coaxing me, instructing me to breathe. My entire body warms despite being completely nude in December. The tone of his voice, how deep it was, it always caused my sex to tingle.

This time, I tell myself, I am going to take the whole plug. I am going to, for Chace, to prove to him how good of anal slut I am. To live up the nickname he gave me: “butt slut.” It sounded silly when anyone else said it. However, from him, the term of endearment, caused instant arousal.

Pressing the plug firmly, it began to slide further and deeper into my ass. My anal ring stretched wider and wider to take the girtiest portion of the plug. I let out a loud moan as the plug pops past my ring, and slips into place. The last portion, the widest portion, is always the part that causes my body to shake.

Immediately, once the plug has settled into its position in my bowels, my entire body tingles and I feel myself trembling. My head is swimming, and I do not feel like I can move. My pussy is pulsing and my ass is full. It sort of feels like I have to use the restroom but I know this will pass.

It took a few minutes, remaining in position, for my arousal to subside slightly and my brain to defog. Every inch of my skin is infinitely more sensitive than it was prior to wearing the plug. My nipples stand at attention and my clit twitches. I slowly slide a soft, plush, robe over my body and realize my breathing is heavy.

Chace knocks on my door a half an hour later. My heart flutters as I walked to the door to answer it. We exchange a quick hug and a kiss on the cheek. He is dressed in black, Nike, polyester, draw-string, track pants and a plain T-shirt. He had told me he was going to stop by on his way to the gym.

He is about five or six inches taller than me, with tanned skin, thick, firm, hard, defined muscles in his arms and legs. He has a broad chest that is shaved bare. His eyes are brown and his hair is so dark, I am sure it is black. He has it gelled neatly in place.

After our greeting, Chace took a seat on my couch. I am glad that I did not bother getting dressed. He has no need for me to be in clothes. It would only delay the inevitable.

Tapping his thighs, Chace indicated that I am to lie across them. Quickly, I pulled the bottle of lube from my robe before discarding it. I had it to him before I position myself across his thighs.

Chace always used gloves when he worked my ass. I was thankful for this. The gloves always helped his fingers slide easier into my body. I felt the latex hand begin to caress my buttocks lightly.

“Breathe.” He instructed me simply.

I close my eyes and inhale deeply. His wide fingers gripped the neck of the plug and he slowly began to pull it from me. I parted my legs, and allowed my head to dangle. The familiar sensation of submission began to wash over me. It started in my toes worked its way up my legs, pausing at my sex and ass as Chace slides the plug back and forth and then rises through my chest.

My head began to fog almost instantly as he worked the plug in and out of my ass. I felt my anal ring stretching to accommodate the girth of the plug. I moaned low while biting my lip as the tingles radiated throughout my body. Chace tugged the plug out of me completely.

“Did you follow instructions?”

“Yes Sir.”

“You are all clean?”

“Yes Sir.”

He playfully slaps one then the other ass cheek and I squeak. I heard the cap of the lube snap and the squirt of the gel. I try to mentally prepare myself for his training.

“Breathe.”

I sucked in a deep breath slowly and I felt that Chace was going to start with two fingers. The tips of what I assume to be his index and middle finger begin to press against my anal ring. I shiver as he pushes them in, forcing my body to open for him.

As I moan, I can feel Chace’s erection begin to grow under my chest. It is pinned between my body and his thigh. His fingers open a bit in my hole and I whimper. I am immediately met with a sharp slap to my ass cheek with his free hand.

Chace slides his fingers back and forth within me as I squirmed in his lap. I feel my ring tested as he works a third finger inside me. I groan loudly and I am slapped on the ass one more time. The sting sends shocks through my system.

“You haven’t been practicing have you?”

“No Sir.” I admitted.

His hand slaps three more times down on my ass as he pumps his three fingers in and out of my anal canal. I whine loudly. He had told me so many times that I need to practice in between our sessions. I have tried to explain that I don’t because it’s not the same. He doesn’t seem to care.

“If you practiced you would be able to take the big plug by now.”

Chace had brought over the largest plug I had ever seen in my life two visits ago. It doubled, almost tripled, the girth of the plug I had just used on myself to prepare for him. It had made its way inside my body at one time. However, it caused a small rip. I bled and begged him to take it out.

 Chace applied ice and soothed me once the plug was removed. He checked up with me several times after that session to ensure that I was healing properly. Our play time was less often since that session. He had been asking me to practice at home to ensure that it wouldn’t happen again.

I wasn’t sure if I was just being defiant by not doing as he asked. However, it was so much more enjoyable when he was the one working my asshole. There was something about being in his lap with his fingers opening me more and more that stroked my submissive side.

I felt his fingers spreading inside me again and I wiggled in his lap. He began to massage my shoulders with his free hand as he opened my ass.

“Breathe butt slut. You can take more. I know you can. Just breathe and relax.”

I tingled all over. I loved when he called me “butt slut.” It rocketed me deeper into subspace as he worked his pinkie into my anal canal. I groaned both in slight discomfort and in pleasure as his fingers stretched me more and more.

I had the majority of his fingers, minus his thumb, buried within me to the last knuckle. I could feel the knuckles of his palm against my ass. He held them there and pressed his thumb into the muscles into my back. I could feel my body relaxing and the tension leaving me.

“Clench around me. Work those muscles.”

I had no idea how to do this, so I tried to do as he said. His fingers were still trying to open within me but I squeezed as much as I could. He continued to work my shoulder muscles as I did this.

“Good butt slut.”

He praised me and I swooned inside. My pussy was on fire, my ass was full, and my heart was pounding. My breathing, I tried to control, long deep breaths. I inhaled deeply and slowly and exhaled just as slowly trying to calm myself.

Keeping his hand in my ass he tapped my head. “Okay slide down. We can work on your deep throating and your ass at the same time.”

I shift myself down the couch. His hand stretched, with his free hand, he begins to slide his pants down under me. His cock, at full attention almost nine inches and about as thick as my wrist, springs free.

I positioned myself on all fours and lower my face to his cock. There is a pearl of pre-cum already seeping from his slit to greet me. I swipe my tongue over the head of his cock and sample what he has to offer me.

With a groan, he forces his thumb against my anal ring and my head down. My lips pressed tightly together, I suck his cock down into my mouth. The mushroomed tip pressed against my throat and I whine trying to focus on his cock and not the pain I am beginning to feel as his thumb presses into my ass.

I bob my head up and down on his cock taking more into my throat each downward thrust. He rests his free hand on my head and I can hear his breathing increasing as his fingers twist inside my ass. His knuckles feel sharp against my ass cheeks as he pushes them deeper and harder into my ass.

“Down.” He said as soon as I brought my head up.

I slide my head down but not as fast as he would like. Using his free hand, he holds my head down farther than I had intended to go. His cock fills my throat, blocks my airway, and he begins to count. I can feel the pressure in my face as my throat tries to reject his erection pulsing around him.

Once he reaches fifteen, he releases my head and I pull up. Drool connected my bottom lip to the spongy head of his cock. I gasp for breath and he works my ass. I let out a loud moan before he pushes my head down again.

This time, I take his full length without question.

“Stick out your tongue.” He instructed me.

I try to oblige. His cock slips further into my throat with increased room in my mouth. My jaw is stretched to take his girth. My asshole opens more as I feel him try to move his fingers inside my tight hole. He is pressing his knuckles into me, and if I could I would whine.

His free hand has moved from the top of my head to my nose. He pinched my nose closed and begins to count again. My head cannot move, because he has it held in place. This time he goes to twenty and I am dizzy by the time he lets me up. I am gagging, trying not to throw up in my living room.

“Good girl. This time I want you to lick my balls when your head is down.”

I whimper feeling his fingers pumping in and out of my ass. It is both painful and pleasurable. My clit is begging for attention. Chace does not pay attention to my pussy when he is working on anal training. He has told me that is my responsibility.

Chace has me deep throat his cock, pushing my boundaries and my gag reflex almost to the limit for nearly a half an hour. While his cock slides in and out of my throat his fingers disappear inside my asshole and stretch it more and more. Ultimately, I am not able to take his fist.

He tapped my shoulder as I struggle to breathe deep breaths. My chin covered in salvia, my nose dripping, and my cheeks tear stained. Chace always used my mouth hard and my face dripped in proof.

“Come I need to take that ass. You are gaping nicely.” He compliments me as he slid the plug back in.

With all the work that he had done to my ass the plug feels small. However, both he and I know that the large plug is still not an option. I half fear that the plug will fall out from the amount of stretching he has done to my ass.

I crawl to my bedroom behind him. He stops short of my bed and turns facing me. An evil smile crosses his lips. When they spread I am offered a glimpse of his perfectly straight sparkling white teeth. I am in awe of his beauty. He is truly a beautiful man.

“Open your mouth.”

Kneeling back on my heels I do as he commanded. I do enjoy listening to him, obeying him. However, I can’t seem to bring myself to do what he says when he is not around.

I am completely stunned when he spits. The first glob of spit lands on my cheeks just below my eye. I want to wipe it off. I want to scream at him. I want to tell him it’s disgusting. However, I don’t. I don’t because I am so deep into subspace, I am so in that moment, I would do whatever he asked.

The second blob of spit lands in my mouth. I want to retch. I close my mouth immediately. I want to spit it out. It feels so wrong, so dirty, and I am so horny and humiliated by the act of him spitting on me I can’t believe I am not telling him to leave.

“Swallow.”

I whimper slightly as I do what he told me to. My whimper is met with a fast, quick, and hard slap to the face. My head turns sharply and the sting radiates through my chest down to my clit. God I want to be fucked hard by him.

Chace grabbed a fist full of my hair and brings my head to his erection. He rubs the salvia coated rod against my face. My own spit is rubbed into my cheek. It is so humiliating, so humbling, and so erotic.

“Open.”

I open my mouth and he begins to pump his cock in and out of my throat. The retching noises coming from deep within my throat do not deter him. He thrusts harder and deeper while pulling my head to meet his shaved crotch. My nose bounces off his pelvis as drool pools on his balls.

When he lets go of my head he pushes me back with his cock. I fall backward and he smiles down at me. I am gasping for breath, panting, trying not to throat up. I can barely focus on the world.

“On the bed. Hold your ass open for me.”

I scramble to do as he says. I am lost in my submission. I am so turned on; I know I would do anything he would ask. I get on all fours first and then lower my chest down. This is the same position I was in when I plugged myself earlier and hold my ass cheeks open.

His now glove free hands effortlessly pull the plug out of my body. I shiver feeling my anal ring open to allow it to be expelled from me. I let out a loud squeal and I immediately miss the feeling. I miss the fullness; I miss the submissive feeling of being plugged.

Chace wastes no time, and he doesn’t go gentle. I feel the bulbous end of his cock press against my opening and I begin to moan. He forced it inside me and I trembled feeling the pop of the widest portion of his cock slip inside me. He pushes himself deep into me, full bore, to the hilt, I take his cock.

The force with which he enters me causes my legs to give out, and I fall flat onto the bed. His hands rest on my wrists using them for leverage, he begins to thrust back and forth. His cock opens my asshole more and more as he slides in and out of my well-greased hole. He has always been generous with the lube when he is anally training me.

“You’re so fucking loose now butt slut.” He growls as he pummels my ass.

All I can muster is a groan and a gurgle. My brain has completely shut down. I feel his entire weight on my back. One of his hands snakes around and grabs my throat. The other covers my mouth, using his thumb he pinches my nose. I can’t breathe.

I can feel his hot breath in my ear as he begins to whisper to me.

“That’s it, take my cock, open your ass for me.”

I close my eyes, swimming in submission, my brain so fogged. I can only concentrate on the fullness, the feeling of his cock pistoning in and out of my ass, and his voice. God his voice, his throaty, husky, deep, masculine, commanding, dominant voice. Any and all semblance of control I once had has evaporated. I am his.

“You’re such a fucking slut.”

The feeling of being owned, of being taken, of being dirty has taken ahold of me. I hope it never lets go. He however, has removed his hand from my mouth and I am now panting wildly. I had gotten dizzy from lack of oxygen yet; I would not have stopped him. I was so his in that moment, if he wanted me to lose consciousness I would have.

His other hand is now squeezing. I can feel the pressure against my throat, the arteries on the sides of neck, and the pressure in my head. I can’t breathe again. I choke and gurgle and he continues to drive his cock harder and deeper into me.

My mouth opens, but nothing comes in or out. I cannot inhale and I cannot exhale. I can just be fucked. He can do what he wants to me. There is nothing I can or want to do to stop him. He feels heavy and powerful. I can feel his muscles against my body. I am drunk on his dominance.

He lets go of my neck and I breathe again. I suck in air desperately. He rears his body up, pulling my hips with him. I am back up on my knees a bit, my legs parted obscenely wide. His cock was pounding hard and deep within me. I can feel his fingers digging into my hips as he pulls me back. I groan in pain but he does nothing but continue to fuck harder.

I have lost all sense of time. I can only feel what he is doing and hear what he is saying. He continues his assault of slurs and insults regarding my sluttiness. His cock barrels in and out of me, and all I can do is moan, groan, grunt, and push back against him.

“Squeeze my cock. Clench.”

I do my best obey him. He praises me: “Good butt slut.”

My chest, my sex, my clit, my entire being flutters and blushes when he praised me. He pushes himself in harder bouncing off my ass as he does. And then I hear him. I hear his deep guttural groan and he collapses on me again.

So, we all know Ushijima would be one of those: “Move your hand or I’ll make you” types in bed, right?

"So sweet," your boyfriend mumbled as his tongue ran from your entrance to your clit. "It's a good thing I'm not diabetic because I can eat you out indefinitely."

"Tae!" you whined. Squirming under his touch because you had just come down from your orgasm and were too sensitive for his mouth. "I want you inside me."

"All in good time, sweetheart." He stuck his middle finger out and started thrusting it in and out of you lazily. "It's been so long since I've tasted you. Won't you let me enjoy this first?" And before you could even answer, his lips were wrapped around your clit again. Sucking it between his teeth to nibble on you playfully. And just when you closed your eyes to relax, Taehyung switched up his technique, pounding his finger roughly and flicking your clit as if he was trying to reach a high score.

"Taehyung! Please!" you gasped. And your hands found his hair, trying to pull him off you.

He just groaned in reply, sending vibrations down your cunt. And he grabbed your wrists and pinned them on the mattress right next to your ass. Now just his mouth all over you. He was eating you out like a starved man and you couldn't help but cry out as his abusing tongue made you cum again. However, this time he didn't leave you any chance to breathe. Kept slurping up your juices as they flowed out of you, nose all up in your clit and making you yelp. Your thighs closed tightly around his head as a reaction to his attack, and you tried to move away.

Taehyung pulled away for a second, glared at you, and then slapped your pussy with one hand. Making you scream loudly.

"Behave, sweetheart," he spoke in a warning tone. "Now sit still and give me another one, like a good girl, 'cause I know you can do better than that." One arm wrapped around your thigh, the other coming down to push two fingers inside you this time. He didn't thrust them in and out, instead keeping them buried all the way in and curling them to find your swollen g-spot. And when you pulled his hair this time, he was unbothered. Lost in your pussy physically and metaphorically. Almost more moans coming from him than you.

"Baby, you're killing me," you whined with difficulty, mouth wide open as you struggled to breathe well, chest heaving and head spinning. All you knew was how you were clenching around his digits, how he was tinkling you in just the right spot that had your toes curling. And when you came again, it was harder than ever before, wetness spilling out of you intensely and coating your boyfriend's nose and all of his bottom face. His fingers were burning you, his mouth only stopping for a moment.

"That's right, sweetheart," Taehyung panted, licking his lips but not bothering to wipe himself from your squirt otherwise. His hands were holding you down with force because you were almost shaking away from him. And then he dared to bring his mouth back down on you. "Give me another one of these."

Taehyung was nearly choking himself on your pussy, quite literally drowning as he didn't stop to even breathe and you were squeezing his head so tightly. But he stayed put, arms wrapped around both of your thighs so that you couldn't go anywhere and shaking his whole head more instead of just flicking his tongue. He made you cum again, and again, eating you out until you were so sensitive it only just hurt. And you were crying, tears falling down your cheeks as you were begging him to stop. And he still wouldn't listen.

"Taehyung, baby, ple–ease!" you moaned after you gushed on his face once more. "Please! That's enough, baby, please."

The man stopped his movements, and you sighed in relief. He got up to look at you, pouting at the mess you were. Hair dishevelled even more than his, tear stains all over your cheeks, lip trembling, eyes red. He groaned at the sight, dick twitching because something about you looking wrecked made him so horny, and he crawled over you until his face was hovering over yours. A sweet hand stroking the tears away.

"Okay, sweetheart," he whispered. "Don't cry. It's okay."

You closed your eyes to enjoy the intimate moment, trusting him in caressing your pain away. But then you felt his dick pressing upon you and you yelped, too sensitive to handle even the lightest touch. "Tae!" you gasped. "I– I can't!" Your boyfriend connected his lips with yours, kissing you deeply and moaning into your mouth as he rubbed his dick over your slick folds to wet himself before he started pushing inside you. And you broke the kiss to cry again. "A–ah! Baby, it's too much!"

"Shh..." he purred. Dick slipping in and out only halfway and yet still hitting you too deep for your comfort. "I know you can take me, sweetheart." His voice was so much softer than before. Yet his thrusts started picking up the pace and pounding your sore pussy right open. "There you go! There you go, sweetheart. See? You're taking me so well."

Your nails were scratching his back so hard you were certain you were drawing blood. But it only made him fuck you harder until he bottomed out and you were full and all stretched out. "Oh my God," you moaned. Even in the pathetic state you were in, tears streaming down your face from the sensitivity, you loved the way your boyfriend was fucking you.

"That's right," Taehyung gasped, switching his attack to sharp and deep thrusts. "So good for me. What a good girl. Look at you, sweetheart. Your pussy is taking my dick so well even after all the times I made you cum." His head was buried in the crook of your neck and he bit you, hard, until you were shouting from pain. Rutting against you faster as he was chasing his own high. "Gonna make me cum, sweetheart. That sweet, little pussy of yours feels so good around me, gonna make me bust right away."

You hissed, thighs squeezing around him. "Baby," you moaned. "Give me your cum, baby. Fill me up." You were begging because you wanted him to stop, still crying from the abuse of your cunt, but your words turned both of you on so much, Taehyung grunting in your ear and pounding you harder.

"My good, little girl," he whined. "Take it." And he spilt all of him deep inside you, making you cum one last time.

your gf riding your thigh, her hands on your chest grabbing at you so desperately. trying to get herself off, and your hands just gently on her hips. feeling them rock back and forth, getting faster and harder when she gets close. then you can feel her getting a little tired, and frustrated because she wants to cum but needs your help. she'll whine for you to help her and not just watch. so you grab onto her perfect love handles and help her get off. faster and harder than she was going to get her off. but once she's cum you don't stop. you switch nice and low and slow - but you keep her sliding on your thigh. she's trying to keep herself up but it's getting harder to do the longer you keep going. overstimulating her. her head's fallen back from just how good it feels, grabbing harder onto your arms because it feels so good. she cums again from the overstimulation and can't hold herself up anymore and lays down onto your chest. skin to skin and you tell her how good she's done for you, brushing her hair and rubbing her back. you grab her some water and lay her down next to you on her side of the bed and you wrap her up in the blanket, cuddling with her till she falls asleep.

Technically, they do stop, but only to push the vibrator down from your clit and shoving it into your hole to watch you convulse before whispering in your ear: