4 comments/ 50289 views/ 25 favorites Anal Training By: JerseyGirlBcom 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. Anal Training - Lesson #01 I hear your knock at the front door and open it to a vision of pure sex. Dressed in a short skirt, nylons and platform heels, you are the picture of classiness and sluttiness perfectly combined. Your skirt matches the color of your lipstick, and your dangly white earrings match your belt and platform heels. You're also wearing a very low cut top that exposes your luscious cleavage. As you step over the threshold your magnificent tit flesh jiggles invitingly. Then as you clomp across the tile floor in those platform heels, your generous ass gyrates underneath your skirt, while your shapely calves flex with each step. You are looking as hot as hot can get. I try not to drool. I invite you to have a seat in the living room. You choose the big easy chair and cross your legs, while I take a seat across from you on the couch. I can't help but notice how your skirt is hiked up just enough to expose the tops of your stockings. We exchange pleasantries, "How are you?", "What have you been up to?", etc. As we're talking, you uncross and recross your legs the other way. As you do, I catch a glimpse of the smooth inner part of your thighs above the stockings, and best of all, your bare crotch. I find this very arousing. First your cleavage and your ass, and now your slick pussy. Wow, am I getting a treat today. What's more, your skirt has moved still higher, so a tantalizing strip of your thigh is now in full view above the stocking top. I feel my cock quiver. I'm wearing some light and very tight cotton slacks, so you can easily see the outline of it down one thigh and my balls cramped along the other. I catch you looking and promptly reprimand you for it. I tell you you can only look when I tell you that you can look. You demurely nod, but then involuntarily peek again. You can't wait to have it in your mouth and in your cunt. I tell you that it's time you were SPANKED! I order you to come over to me this minute! You rise, looking like a school girl just caught with her hand in the cookie jar, and come over to me to lay across my lap. Your tits nearly spill out of your blouse as you bend down to lay across me. They bobble so nicely as you get into position, your ass pooched up, waiting for my hand. I pull up your skirt to reveal your plump cheeks framed in a white garter belt. Your nylon sheathed legs are waving gently in the air. Platform heels and all. I first put my hand between your thighs. You take the cue to spread them ever so slightly. I let my hand move onto your smooth pussy and my middle finger onto your clit. You are so warm and moist. I stimulate your clit briefly just to give you a start, then I quickly remove my hand and give you a good whack across your ass! "Ow!", you yelp. Then again, only harder. "Ow!" I take your two buttocks and push them together, then put my mouth on the crack and dart my tongue between them. Ooooh, you coo. Then I whack you again, then again! I whack you repeatedly, each one a little harder than the previous one. The spanked cheek is pinking up nicely now. I reach my hand between your thighs again to give you another clitoral tweak. It sends a shock wave through you. You wish I'd continue, but I don't. I pull my hand away again to whack your other cheek. Again! And again! The ass flesh ripples with each whack. Both cheeks are rosy now. You look so hot like that. With your ass readied for some real fun now, I'm thinking how much I'd like to ream it good with my big cock! How I'd like to pleasure you beyond anything you've experienced before. But I banish the thought; I know you're not ready for that. Instead, I decide that it's time for you to get your first anal training session. Training you'll need to prepare you for the day when I do in fact enter your warm hole. I tell you to get up, that I have something for you. I reach into my drawer of assorted butt plugs and pull out a small, beginners model. I show it to you briefly, then ask you to turn around and pull up your skirt. When you do, I put both of my hands on your lovely ass, grab as much flesh as I can, then gently bite the still pink bulges I have in each hand. Easy at first, then harder until it just starts to hurt. I then stop to let them fall back into place, and then to jiggle them to measure their mass in my hands. I then tell you to bend over, while I lick the butt plug and then put it up to your asshole. With the rounded tip up against you, I push until you open just enough to let it slip in. Its taper widens your hole as it enters. Then once the bulb is in, your sphincter closes onto the root end, which keeps your asshole stretched open about an inch. Nothing too severe. But at this early stage it feels huge to you. I tell you to try walking around with it in your ass. You tentatively take a few steps. Then I tell you to walk into the bedroom, and to hold up your skirt so I can see it as you walk. I watch your lovely ass jiggle as you walk, your cheeks grasp the butt plug tightly as you move. The sensation in your ass is a new one to you and you're finding that you're liking it more and more by the minute. You drop your skirt to the floor, then toss your blouse as you walk. I follow you into the bedroom, drinking in the view as I go. I come up behind you, not surprising you at all, as you have me in full view in the full-length mirror. I've taken off my pants and my cock is semi-hard, waving in the air as I walk. You gasp a little gasp. I come up behind you with you looking in the mirror and you feel my cock and balls pressing against the small of your back. I kiss the back of your neck below the ear, your dangling earring against my nose. You feel my hot and quickening breath. I tell you to spread your legs slightly, which you do with much anticipation in your eyes. I spread my legs too, but only to lower my now rock hard cock relative to your lovely ass, then slip it between your legs so that it sticks out in front of you. In the mirror you see a protruding dong against your wet pussy. You put your hand around it to give it a jerk. You reflexively slide your cunt lips back and forth over the shaft and quickly discover that that stimulates your clit as well. You begin to undulate your hips to produce the desired motion, all the while getting hotter and hotter. I reach around you to cup your fantastic tits in your bra, then quickly remove it to reveal your massive DD mammaries. Oh they're gorgeous to look at in the mirror! I fondle them shamelessly, cupping them up, banging them together to see the flesh wobble and ripple. The pink nipples hard as pebbles, longing for my tongue. You watch me in the mirror, then twist your head around to offer me your open mouth. We're all tongues! On fire! You're riding my shaft with your cunt, your ass is bumping up against me while the butt plug is pushing against my pelvic bone stimulating your anus in a way you've never felt before. The sensation is incredible! You are already galloping toward orgasm, out of control. You're having spasms, your hips are practically vibrating. You whisper, "Oh Jack...Oh Jack...Ooooooh!" I'm getting closer too, my cock is drenched in your juices, and the feel of your pillowy ass up against me is pure heaven. You're grunting now. The grunt of an animal in lust. You are a woman consumed by it. You are going to cum like an animal too. You scream, "Oh god, I'm cummmmmming!" As you twitch and jerk. Gasping for air! Undulating. Writhing. "Oooooo!" As you start to come down from this ecstasy, I slip out from between your legs and tell you that I'm going to tie your legs together at the knees and ankles. You're still in a bit of an orgasmic stupor, but you quickly comply. I have you stand next to and facing the bed, then I tie you. Tell you to get up on the bed on your knees. I get up behind you and push my throbbing cock into your pussy without delay. Since you can't spread your legs, you are extra tight, so I force it in hard. Also, with your legs together, part of your inner thighs can feel my slick shaft sliding in and out. I begin to pump you good. You can feel my cum-heavy balls banging the backs of your thighs, and my pelvic bone again pushing on the butt plug with each thrust. You feel so filled up you think you'll explode! My huge cock in your cunt and the butt plug in your ass is more than you can stand. You think you could cum again, but I've yet to take my pleasure, so you forego yours to focus on mine. I grab a handful of your hair and pull your head back like a rider restraining his mount. Your back arches. You yield completely to my lust. You want my thrusting cock deeper and deeper, then to have it explode. I'm nearly there. You are so tight in this configuration that I feel like you'll be squeezing the cum out of me any second. Only your asshole would be tighter. I'm taking shorter and shorter strokes as the passion builds. You're grunting again too, but it's a throatier, deeper grunt, as you're being fucked more deeply now. Your second orgasm will be more complete. More wrenching. You shudder. Your pussy is convulsing. You squeal and gasp for breath! "Aaaaah," I'm going to cum now too! I'm heaving. I shoot a massive wad into your cunt while simultaneously pulling out and spraying your thighs above the stockings. Huge globs are running down to the tops of your stockings, then onto the stockings themselves. White cum on black stockings! That is s-o-o-o hot! With you still on your knees I pull your head around to lick my dripping cock. Then I turn you around and force you to sit down, drawing your knees up closer to your face. You reach to the back of your legs to wipe some cum up to lick off your fingers. Cum still oozing from your pussy. You are covered in cum, and you love it. And the butt plug is still providing pleasurable pressure to your ass as you're sitting on it. I stick my cock in your mouth again for a finishing suck. You run the tip of your tongue into the hole in my tip. Oh, that's wonderful! I untie your legs and with you back up on your knees and your ass up, I gently pull out the ass plug. Your sphincter is stretched again as the bulb slips out, but now gapes momentarily before closing. Mmmmm, that's lovely. We'll be working on more gape in future lessons. I take you in my arms. That was so deliciously nasty we are still coming down. We need to cool off. Catch our breath. We kiss. Soon you're telling me how satisfying that was for you, and that you're excited about the prospects of more anal stimulation in future meetings. You had no idea how it would move mountains for you like it did. I nod, as I long for the day when I can enter you in that way... Anal Training - Lesson #02 We decide to meet at a hotel, as both of our houses are busy lately with the kids being at home and our spouses off. It's been a while and both of us are anxious to get together. You've been using your butt plug trainer for a few weeks and now think you're ready for the next phase. I know I'm ready to take you there. We meet in the downstairs lounge for some adult refreshment before going up to our room. You look as lovely as ever and are dressed to kill. It's a warm summer night so you are sans nylons, but you're wearing a very cool pair of strap-on heels that are open all around. Your nail-polished toes show, and your heels are exposed except for a thin black leather strap. Your ankles are bare, as are your luscious calves and knees. Your short skirt shows off your beautiful legs. Also, because it's so warm, you're wearing the skimpiest little top that barely conceals your obviously large and overflowing bosom. When you walk the flesh is moving in so many directions it's impossible to concentrate! What a pleasant distraction you are. We sit at a small table to chat. You tell me that you've been using the smallest butt plug to stretch yourself, but explain that it's now too small to be effective. You need to go to a bigger model. I nod approvingly, pleased at your progress. I want to make tonight's lesson as new and exciting for you as I can. I'm not sure though who's going to enjoy this more, you or me. It's not long before we decide it's time to go upstairs. As we walk arm-in-arm across the lobby to the elevators, heads are turning to watch the vision of sex beside me. Your gorgeous legs, that fabulous ass, and your jiggling mammaries are any man's dream. When the elevator door closes us in, you turn to me with those bedroom eyes of yours and stand up on your toes to kiss me. Your moist mouth and active tongue soon have me in a whirl. With your tits against me, you reach down to feel my cock, checking it's status, running your hand along its length through my pants. It responds to your touch. You can feel it growing in your hand as we kiss. I bend down to put my mouth on your exposed tit flesh above the neckline of your blouse as we hear a ding. We've arrived at our floor. Inside our room we quickly resume our embrace. I turn you around and bend you over with your ass against me. My burgeoning cock is riding right in your crack through my pants and your skimpy skirt. You push your plump cheeks against me, imagining how it would feel if I were to enter your ass like this. We gyrate together for a minute, then I tell you to take off your panties and sit on the bed. I drop to my knees and crawl over to you as you spread your legs to greet me. Your pussy is glistening, just begging to be eaten. I work my tongue along your inner thighs, then on to your luscious cunt. I can't get enough of your juices, your fragrance envelopes me. I want all of your pussy in my mouth. You lift your legs up in the air as I tongue your clit. Then I move down across the lips until my tongue finds your other little hole. You love to have me there. My hot tongue darting. My breath on your most private parts. This is where your essence resides. Here, between your legs. And I am ministering to it. Paying homage to it. With your legs already up in the air, I push your knees back further toward your chest, which exposes more of your asshole to me. I plunge my mouth onto it, then penetrate it with my wet tongue. Flicking in and out. You moan. You are breathing harder. I've reached your inner being. You feel like you are going to cum. It's a strange feeling because your cunt is not being stimulated at all right now. Just your ass. But it would feel so good, and so right, if you could cum like this. I pull butt plug #2 out of my pocket. It's a half inch larger in diameter than the first one I used the last time we met. I put it up to your mouth to lick, to lubricate. You do it eagerly. You can't wait for it to enter you. I press it up against your hole. You relax into it nicely. I can tell you've been practicing. It slips in smoothly when I apply enough pressure. Then disappears as you close around it. Your asshole is now stretched more than before though. The base is a half inch wider. It feels large to you. Like really intrusive. You feel completely plugged up, clear up into your abdomen. You aren't, of course, but that's the feeling. I hold the base and pull it very slightly out. Just enough to stretch your hole a little, then to relieve it as the bulb moves back in. You moan, it's uncomfortable, so I let it be for now. I want to kiss you for being such a good girl. You are still aroused, of course, and want me to fuck you. I decide that that would be a good thing to do now to help you through this phase. I stand up and pull down my pants. My cock is fully hard. I get on top of you, missionary style, and put the head of my cock between your wet pussy lips. While we do some deep french kissing I slip into your hungry cunt. I'm fully into you and my balls are against the base of the butt plug. You feel their weight against it pressing it into your ass. I begin to stroke in and out. As I thrust in you feel my balls banging on your ass and the ass plug. It's very pleasurable to you, particularly after enduring the insertion of the butt plug. In fact the combination of my cock and the butt plug gives you the fullest feeling you've ever had! You love my cock plunging into you while the ass plug vibrates with each impact of my swinging balls. You are getting banged big time. And it's wonderful. I continue to pound you. I'm going deeper with each thrust. Our tongues are going at each other the same way our genitalia are. We are in a full fuck now. Humping like beasts. Grinding and thrusting against each other. The passion rising with each stroke. You feel yourself welling up, you are going to come apart. It feels like I'll split you in two. You want release now! You have to cum. You heave and pant. You're going mad! Involuntarily, your mouth opens wider, we lose our lock as you gasp for air! Nearly choking as you convulse. Shuddering at the hips. Cumming huge! "Oh!" "Oh!" "Oh!" "Oh!" Then your mouth is back on mine. More tongues as you writhe to the last of your orgasm. I'm hotter than a pistol but don't cum. I have other plans for us that will take care of that in due time. I just wanted you to get off as a little reward for being such a good girl with your anal training. You've made very good progress in a very short time. After you've calmed down I tell you to stand up. I tell you to walk around the room with the butt plug in place like you did in lesson #1. I watch you as your cheeks surround it as they bump along with each step. That is a lovely sight. My pecker, having calmed down some after pulling out of you, perks right up again. I tell you to lay on the bed while I cuff your ankles, then your hands behind you. I tie your legs together just above the knees. The skin on your legs is silky smooth and I want it to stay that way so I don't bind you too tightly, just snug enough so that you can't separate your knees. I then put a ball-gag in you pretty little mouth and fasten the straps on your head. You're new to ball-gags so the sensation of being gagged is unfamiliar. I love seeing you like that. Helpless, really. At my beck and call. And so-o-o hot!!! I would love to fuck you in the ass right now, but I must let you complete your training first. I grab your hair to pull your head back. Saliva is beginning to appear around the edges of the ball-gag. You'll be drooling soon. With you on your side, I put my cock between your magnificent tits, pushing them together. They are heavy and oh so fleshy. Your nipples are fiery red. And hard. You love my cock there. You wish I'd put it in your mouth, but of course the ball-gag makes that impossible. I put my mouth on one of your nipples. Suck it hard. Nibble it with my teethe, flick my tongue over it. You moan in the ball-gag. I put the head of my cock on your nipple, put the tip of your nipple in the tip hole of my cock. "O-o-oh." You love my precum lubricating your nipple. Now the other one. Then I wave my cock over your face to tease you. Let my balls drag over your face. Oh how you'd love to lick them. I grab your hair to pull your head back so I can rub my cock over your lovely neck. My balls dangle onto your throat. You are getting the full sense of my manhood, but you can't do what it is you want to do the most, and that is put your mouth on it. I roll you over onto your stomach for a birdseye view of your luscious rump. So full, so fleshy. M-m-m-m. I grab some of your ass flesh. Bite it. Knead it with my fingers. Jiggle it to see it ripple. Play with your ass like it was my own private play toy. You love your ass being fondled like this. I spread your cheeks to get a good look at the butt plug in your little hole. So delectable! I lay my now fully hard cock between your cheeks, right across the butt plug. You feel it's size and mass as I slide it up and down your crack, my balls trailing over the back of your legs. I grab your hair again, pull you back hard and stick my tongue in your ear. Saliva drips from the ball-gag. My hot breath in your ear sends you. You're overwhelmed with my closeness. Your pussy and your ass are now longing for my cock. You'd love to have me enter you right now! I slap your ass. You recoil. I slap it again. It wiggles with each blow. You mumble through the ball-gag to do it again. I slap it again. And again! Your muffled squeals tell me you're loving it. You're under my complete control. But you trust me completely so you're not afraid. You love me doing this to you. I tug on the butt plug again. I don't pull it all the way out, but just enough so the bulb is stretching you again. "O-o-oh," you groan. You feel like you're going to split. I let it slip back in. Then I tug on it again. "O-o-oh," again. Then a few more times. You are doing wonderfully with this. Beginning to enjoy it now. Finally, on the last tug I pull the butt plug all the way out. Your lovely asshole gapes open momentarily before closing. God that's gorgeous! I remove the ball-gag; your lips and chin are covered in saliva. You are so hot, I can't resist. Our mouths gobble each other! I place the head of my cock right on your hole. Your fabulous ass cheeks grip a couple of inches of my shaft. Then I slide the tip of the head in just enough to stretch you back to the point that the butt plug achieved. You like the warmth of it so much better than the coolness of the butt plug. If it wouldn't hurt, you'd love to have me ram it all the way in. I let it sit for a minute, then pull back a fraction of an inch so that you close some, then push in to expand you again. Then repeat many times. It feels like you're being fucked in the ass, but without full insertion. You love it! It's incredible! You feel so hot. Your gasping again. You moan, telling me how fantastic it feels. I tell you that you can cum this way if you wish. You can have your first ass orgasm with a cock stimulating you. And you can be in control. "Oh god, thank you," you say. You push against me, stretching yourself then relaxing back, then pushing again. It's having the same effect as when I was pushing on you. You are gulping now, panting and gulping. You can't believe the sensation in your ass! You are going to cum again, and cum oh so good! Your ass cheeks shudder, the flesh shaking like jello. God what a sight! I think I'll explode with you. You groan a deep groan, "ooooooh!" Finally, quick spasms take you to the final height! You cuuuum...oh sooo good! Your beautiful green eyes roll back in your head as you are in pure ecstasy! Now I'm having spasms of my own. The sight of you in such bliss with your ass cheeks gripping my shaft as you convulse is just too much. Cum shoots out of me before I can even think about controlling it. The hot stream injects your ass! It's flow warming and lubricating your hole. Which opens slightly more with the pressure from my head. "Oh gawwd!" you gasp! "Oh gawwd!" Now it's all in your crack too. And down your leg. I rub my cock in it, then offer it to you to lick. You clean me with your talented tongue, curling it around the head and lapping along the shaft. "Mmmmmm," you coo. But I don't hear you, as it is now I who is in ecstasy. Finally sated, I uncuff your hands and your ankles, and untie your knees, giving you a soothing massage of the bound areas. I lie down next to you with my arms around you. We kiss. We snuggle for awhile. You are so beautiful like this. You look so content and so satisfied. I never want to let you go. Anal Training - Lesson #03 I can't wait to see you. I've already rented a room for us and I'm sitting here waiting for you to arrive. I have some wine, and some ice water, but that's all in the way of refreshments. For equipment, I've brought along the third butt plug, the largest, along with some rope. I'm wearing very thin cotton dockers and no encumbering underwear. My shirt is open in the front exposing my modest amount of chest hair. I'm in loafers with no socks, very casual. I've instructed you to wear whatever you want as long as you have on nylons, garter belt and heels. Panties are optional. After what seems like an eternity, I hear a knock at the door. I bound to it with anticipation. You are stunning! Dressed to kill. Low cut dress that you're spilling out of, wide latex belt with matching purse and high heels. My eye immediately gravitates to your spectacular cleavage, then quickly up your smooth throat to your full lips. You're wearing bright red lipstick. Oh my. My eyes must widen as you wink and smile. Then as you walk by me into the room, your tits bobbling with each step, I swallow hard. You are blowing me away! Once in the room, we put our arms around each other for a hello kiss. Oh, those lips. We have a seat together on the couch. You cross your legs and look at me like you're my adoring student. Which, in a way, I guess you are. But I always feel like I'm the one enriched whenever we meet. You're the one to be adored. The one holding all the cards. I'm just so much putty when I'm with you. But I try to keep up appearances nonetheless, hoping you won't notice how vulnerable I am to your overwhelming charms. I tell you that tonight will be your last lesson. Tonight will be your final exam. You tell me you've been practicing with plug #2. You've used it until it feels small and now you want to move up to plug #3. You are a prize student, a very quick learner. I tell you to lay across my lap, which you do eagerly. Your soft body, while still clothed, begins to arouse me already as you seem to be in perpetual motion. Your legs wave slowly in the air as your voluptuous ass cheeks bobble beneath your dress, just like your beautiful tits that are literally spilling out of your dress. A shock goes through me at the sight of you. I put my hand on your leg at the knee, then move it up along the nylon to the stocking top and onto the flesh of your thigh. I push the hem of your dress up to expose your plump ass. God you're gorgeous! You look at me as if to say, "It's yours, Jack, all yours to do with as you please." I spread your luscious cheeks to inspect your opening. You have a classically round asshole. One that looks like it was designed for what we will soon be doing. I show you butt plug #3, the two-incher. I let you lick it before placing it up against your hole. You let out a barely audible gasp, as I push on it. It slips in smoothly until the widest part of the bulb encounters resistance. I push harder, you wince, but then relax nicely, letting it slip all the way in as you close around it. You've gotten by the hardest part. This little sequence is a major turn on for me. Seeing your ass swallow that bulb and your sexy moaning have caused me to swell considerably. You can feel me pushing up through my pants. A hardening knob is now poking you from below. It's aligned with your pussy so it's not like it's uncomfortable or anything. You wiggle a little to rub against it. You're starting to get a sense of what is going to take place tonite. I pull out on the butt plug as I did in lesson #2, then let it slip back in. Then repeat. You're loving it. You're really into the anal pleasure thing now. You've learned so much. As before, I have you get up, drop your dress to the floor, and walk around with it in your ass. You look absolutely fantastic in your bra and the nylons, garter belt and heels. And with the butt plug between your cheeks you are practically sex on wheels. I'm nearly breathless. You parade around for me, well aware of the effect your having on me. You can see my bulging cock in my pants and sense that I'm aroused more than at any time you've seen me in the past. You offer to unzip me to set me free. I say, "Yes, please do." You bend down, your mammaries hanging down with you, and you remove my cock AND my balls from my pants. I still have the pants on, but my fully erect cock, with my hanging balls are outside my pants like an appendage completely separate from the rest of my body. I tell you to go sit on the bed. You clomp over to it in a most appealing way. Your flesh jiggling seemingly everywhere on your voluptuous body. Oh god! I tell you to sit down, which you love doing because it puts pressure on the butt plug, a sensation you've learned to appreciate very much over the last few weeks. You look back at me, with my cock and balls hanging out, and the blood rushes to your head. You'd love to get your hands and mouth all over them. I tie your ankles, then your thighs just above the knees. I tell you to get up on the bed on your knees with your back to me. I tie another piece of rope to each rope around a thigh and let them lay beside you for the moment. Then I tie each of your wrists to those ropes. Your hands are at your sides and your wrists are tied to each thigh above the knee. I tell you to sit down on your heels and lean forward so your tits are against your upper legs. Your ass is sticking out behind you to very delicious affect. I see the butt plug bulb straining to escape your ass, but it can't. I cinch up all ropes tying your wrists to your thighs. Then put one last rope around your legs so you can't straighten them out. You are a bundle now. Your wrists are immobile and your legs are crunched up under you. Your head, neck and mouth are completely unencumbered, but you are otherwise immobile. Needless to say, you are looking as hot as hot can get. It's time for your final exam. I reach for the butt plug again, pull out on it to stretch you to the max again. In this position you feel like some of your insides might be coming out with it. But you hang in there. Your learning to love having your asshole stretched. After a few tugs like this on the butt plug, I go ahead and take off my pants, then proceed to rub my cock on your ass. Then down the back of your thighs. "O-o-o-oh," you say, "That feels good." I get up on the bed to straddle you, letting my cock and balls trail over your back. I then get off you to get in front of you. I grab your hair and guide your mouth to my cock. You go to work on the head with your tongue. You love me in your mouth. My cock was made for your mouth. Your luscious red lips grip it while I slip it down your throat. Your in the perfect position for deep throat. Your chin is up and your mouth and throat aligned for maximum penetration. Oh you're good! Your saliva is dripping from your chin as you suck me completely into you. My pelvis against your nose; my balls against your chin. You're a dream. Those bright red lips, your slithering tongue, and that sucking action is divine. A woman for the ages! Abruptly, I pull out to take care of more important matters. You didn't quite get your fill of my cock, but you long for me to attend to your ass. I get back behind you again to exercise the butt plug. I give it a couple of tugs, stretching you more each time, but then pull on it until it slips out. Your gorgeous asshole stays gaped open. Oh that's beautiful! I now tell you that I have a surprise for you. I put my throbbing cock up to your gaping hole and slip the head in. It slips in smoothly. You moan, "Oh please, all the way. Give it all to me, Jack." I push in slowly, inch by inch, to be sure you can take me. You're doing wonderfully. I push more, my thick shaft disappearing into your dark hole. Oh it's so warm and smooth. I pull back momentarily, then push all the way in. You groan, "God that feels good!" Your sphincter grips me tightly as I start to move in and out. My balls press against your wet pussy with each slow thrust. I'm penetrating your ass to your core. You've never known this sensation before. It is new, and it's wonderful! It feels like I'm taking up residence in your body. All of me, splitting you in two. I pick up the pace. You groan. My balls, now slapping against your pussy, are driving you wild. You are overwhelmed by the whole sensation of being totally fucked in the ass! You are getting hotter and hotter with each of my thrusts. Your restraints make it hard for you to push against me, but my man meat up your ass is all you need to push you over the top. Your grunting. Deeply. From way down in your being. You are experiencing the beginnings of your first full-cock ass orgasm. It feels like your insides are going to fly out. Like you'll truly explode! It's not localized to your pussy like you're used to; it's your whole body that's going to explode. We are both building now. My cock is reveling in every thrust I make into you. Your ass flesh rippling with each impact of my pelvis. What a sight! Pumping your glorious ass! Your squeals! Your hungry groaning! It's all so delicious! My teacher's work is nearly done. You have passed every test. And it's so gratifying to see you enjoying it as much as you are. I'm coming up fast. I'm giving you all the cock you've ever had. You are all the ass I ever want. Pounding you deep. I grab a handful of your hair and pull your head back like a rider yanking on the reins. You arch your back just right. Incredibly, I'm now able to penetrate you even more deeply. You give out a low grunt. Then another. Then with each thrust. You are in a kind of trance now. Pure ecstasy. You shudder. Spasms come over you. You are cumming from all the way down in your darkest recesses. Shaking. Jerking beneath me. Your ass cheeks squeezing my cock spasmodically. My balls banging against your soaked pussy. Oh god! I'm going to cum too! I pull hard on your hair, twisting your head slightly. You cry, "Oh yes-s-s! Give it to me! Oh yes, fuck me! O-o-o-oh!" I ejaculate a massive load into your magnificent ass! Heaving and convulsing as I do. I can barely breathe! I'm gulping for air! "Oh your ass! Your beautiful ass! You've taken all of me! And loved every inch! Oh the sweetness of it! I'm in heaven!" I roll us over on our sides to take a few finishing thrusts. You are still gasping as I pump you some more. Ball draining pumps. The cum in your ass, so warm and wet, coats my cock as it slithers in and out of your new love hole. That is so nice. I kiss the back of your neck, nibble your ear. Settling down, finally. I fondle your tits from behind you. I love my hands on them. They are so soft and fleshy. What comfort they offer, and what fun post-orgasmic play they provide. Time to slip out of you and untie the ropes. Time to set you free. We kiss. You thank me for opening your life to new pleasures. I thank you for giving so much pleasure to me. More kisses, then time to dress and depart. As we do, I'm already longing to be with you again. Anal Training "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. The two of us are gasping for breath, his heavy, muscular, and powerful; glistening in sweat body is on top of my soft, pale, dripping in sweat body. I feel the spurts of his cum shooting deep within my bowels. His arms are on either side of my head and his face is nestled into the crook of my neck. I have no idea how long our training session lasted but I know I am looking forward to the next one.