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I'm a Jersey Girl in my thirties. I enjoy reading and writing erotica that have BDSM themes. I am submissive. Having always played behind doors, I am just getting out into the real world scene: attending munches and classes. I have a fondness for rope....








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**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.
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.
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?”
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.
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.
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.
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.
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.
“O
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