Alice's Adventures in Subland, Chapter 2

Alice lay on the floor panting, a sheen of sweat on her forehead after the forced orgasm she had just experienced. Half an hour into our first training session she didn’t look like she would be able to make it through the rest of the hour. I had allowed her a very brief respite to gather some strength, but I was keen to press on.

“That’s enough time for you to recover, Alice,” I said, “so far you have learned how to present your mouth and your pussy for my use. You need to learn now how to present your anus. Turn yourself over and get onto all fours.”

Alice moved slowly, following the command, her legs still now twitching a little with a few aftershocks from her orgasm. Once she was on hands and knees I moved round behind her to inspect her backside, noticing how her soft round buttocks still bore the marks from her earlier discipline with the riding crop.

“Now spread your knees apart, as far as you can. Good, now lower your head to the floor and put your hands behind your back.”

With this movement Alice’s buttocks parted, exposing her anus and pussy, the lips still engorged and wet.

“Now push your chest down towards the floor, arch your low back so that your anus is as far up in the air as you can manage. This will be uncomfortable for you, but if you practice holding this position every day you will find it easier in time.”

I knelt between Alice’s parted legs and rested a hand on each of her buttocks, smoothing the skin in large circles, feeling the slight give of the skin. I took my time to take in how completely exposed she was in this position, examining her neatly puckered anus, the surrounding skin shaved as smooth as her pussy. Reaching down between her legs I allowed my fingers to slip just a little way into her vagina, slick with her secretions, and she shuddered at the touch in this still so sensitive area.

“Tell me Alice, have you had your anus penetrated before?”

“Yes, sir,” she replied, remembering the way I had instructed her to address me.

“Did you enjoy it, Alice?”

“No, sir, it was painful.”

“I hope that you will learn in the coming weeks that there is often little to distinguish between things that we find painful and those we find pleasurable. I intend to use your anus regularly for my amusement, and you will find that with repeated use you will experience less pain and greater pleasure.”

I squeezed a little lubricant onto Alice’s anus, the sphincter tightening to withdraw against the sudden cold. With my index finger I gently massaged the slippery jelly around her arsehole, feeling the little folds in the skin around her entrance. Alice did not make a sound as I applied a little pressure, but she reflexively pulled her bottom away at this new sensation.

“You must remain in position, Alice. It will be uncomfortable, but you must keep your anus held as far up in the air as you can, and not resist. Show me that you can endure this and you will be rewarded.”

Alice once more arched her back, pushing her backside up from the floor and I again applied a little pressure with my finger, the tip slipping inside a little past the first tight ring of muscle before meeting a little more resistance.

“Take slow deep breaths in and out Alice, and bear down a little and you will find your anus opens more easily.”

I continued to press with my finger, applying no extra pressure but as Alice followed my instructions her anus relaxed and my whole finger slipped inside her as she let out a small gasp of discomfort.

“Very good Alice, but you really are very tight back here and if I am to use your arsehole for my pleasure you need to be able to open yourself to me much more easily. For the remainder of today’s lesson I will teach you how to train yourself to accept objects in your anus easily, and improve the strength of your muscles to allow me greater pleasure in the future.”

Sliding my finger from Alice’s anus I returned to the drawer which held various tools I had purchased for her training. I had a set of six black rubber butt plugs in various sizes, starting from a very narrow plug only as wide as my finger with the largest of such a width that I suspected it can’t have been intended for actual insertion, being around 6cm at its widest point. I applied lubricant to the smallest and knelt again by Alice who had managed to remain perfectly in position, her cheek pressed to the carpet, hands behind her back and arse in the air.

“Deep breaths again Alice, you should find this easy.”

Placing the tip against Alice’s tight sphincter it only required a very gentle push for the whole length to be buried within her, her anus closing around the narrowing just before the wide base and somewhat disappointingly not causing her the slightest moan.

“Now Alice I would like you to stand for me in the initial position.”

Alice stood and returned to the first pose I had taught her, hands clasped behind her head, feet a little more than shoulder width apart, shoulders well back to push out her chest.

“Along with a little gentle stretching of your anus, I am going to teach you about stress positions and predicaments. The position you are holding at the moment probably feels quite comfortable, but as the minutes pass you will feel an increasing strain on your shoulders, the muscles will begin to ache and burn. Eventually the muscles will start to fail, at first just shaking a little, but as the pain builds you will finally be unable to keep your arms where they are. You are now in a predicament. If you are unable to stay in position, or if you ask me politely whether you can change position, I will replace the plug in your anus with the next largest. Once the next plug is securely inside you I will place you in another position that you will have to maintain. There are only five plugs left, and I fear that the largest might cause you some permanent damage, so I would suggest you endure the discomfort of the stress position for as long as you can. We have a little more than 25 minutes remaining. I have some work to do, but I will be watching, and remember you can always ask to come out of position should you feel able to accept a larger plug. Good luck.”

I left Alice as she was and sat at my desk, switched on my laptop and started browsing through my emails. I could see Alice out of the corner of my eye, but did not want her to have the satisfaction of my attention, so pointedly ignored her. I hoped that this would give her a sense of worthlessness, a plaything of which I was quickly bored and had no real need for. As the minutes ticked by I could see that Alice was struggling to keep her hands behind her head, her elbows were coming forward and she was bowing her head a little.

“Alice,” I snapped, “that is not the position that you were taught, now head up, and keep those elbows wide apart with your shoulders back.”

She tried her best to stand erect, but the burning in her shoulders must have been terrible, her face was screwed up in concentration and her arms were shaking with the effort.

“Please sir,” she managed to say through gritted teeth, “may I change position.”

“Of course Alice, as we agreed, but first you must present me your anus once more.”

The relief she felt when her arms fell to her sides was plain on her face, and she rolled her shoulders as she knelt, trying to ease the burning. Back on the floor, face on the carpet and arse held high I gently tugged at the base of her butt plug which slipped free easily. Applying lube to the second smallest plug, only a little larger and longer than the first, and pressed this into her anus. I was not surprised that at this size she once again accepted the plug easily, but of course there were four still remaining.

“Stand facing the wall. Now spread your fingers and place the tips high up on the wall as far up and as wide as you can reach. Now spread your legs as wide as you can, up on the tips of your toes, and edge back from the wall so that your weight is supported by your finger tips.”

Alice followed each instruction, until she was spread eagled, up on her toes and leaning forward at such an angle that she already was struggling to support herself. The black base of the butt plug stuck out from between her buttocks and I couldn’t resist grabbing it and giving is a little shake, just to remind her it was there.

“This plug is still much smaller than my cock, so I expect you to be able to take it easily and without any fuss. I don’t want to hear a murmur from you now.”

Gripping the base of the plug I pulled it out roughly, Alice’s body jerking with the pain of the unexpected extraction but managing not to cry out, just inhaling sharply through her nose. With equal force I pushed the plug straight back in again, and even though it was fairly narrow the sudden tension in her buttocks and back told me that it hurt. Goodness only knew how she would cope with the larger plugs. Putting my hand between her legs, I once more slipped my fingers between her pussy lips and was surprised to find that she was once more dripping wet.

“Don’t tell me you’re enjoying this Alice. All this discomfort, the humiliation of it all. Can it really be turning you on? I’m not sure I like the idea of you finding your training pleasurable, this really won’t do you know.”

A couple of strides across the room and I picked up the riding crop where I had left it earlier and gave it a couple of swishes through the air, the sound letting Alice know what was coming. Without any further warning I gave her a good hard whack across her buttocks, Alice momentarily failing to keep position as she jumped away from the sharp pain. Fearing worse however, she swiftly returned to her pose, legs wide and leaning far forward supported by her fingertips on the wall above her head. Her shoulders and legs were shaking again as the muscles struggled to hold her position, so I gave her another crack with the whip, harder than before.

“You are having too easy a time of it today Alice. Your training is for my pleasure, not yours.”

Another whip across the buttocks, a sharp crack as the leather met her exposed flesh, followed by an uncontrolled yelp of pain.

“I don’t want to find you sexually aroused again unless I have expressly allowed it.”

I whipped her again, her cry louder this time as she fell forward to the floor, unable to take the combined strain of the position and the unexpected sting of the riding crop across her backside.

“Oh dear, Alice. It appears you have failed to maintain the required position. Present me your anus please.”

Alice hesitated a little before lowering her head to the floor and clasping her hands behind her back; a reassuring sign that she wasn’t finding this easy.

The next butt plug was about 10cm from tip to base, and nearly 4cm at its widest point, I expected Alice to start having a bit of difficulty from here on. As before, I eased out the previous plug and lubed the next. The black rubber slipped in quite easily to about halfway, Alice’s anus having become a little more relaxed by the previous two plugs, but then there was more resistance and Alice drew her bottom away, obviously uncomfortable with this step up in size.

“Alice, I know you can take this. If you can manage this size then you’ll be able to take my cock inside you with ease. I want you to think of how happy I’ll be when you can please me in this way, how I will reward you if you take me in your arse without resistance or complaint. I believe you will find great satisfaction in being able to submit to me in this way.”

The butt plug still halfway inside her arse, Alice started to push back onto the rubber cone and millimetre by millimetre it began to sink further inside. I allowed Alice the luxury of dictating the pace, pleased that she was making such an effort to please me, letting her take little breaks as her anus opened little by little to accept the plug. Finally she passed the widest point and her anus closed around the narrowing above the base as she emitted a soft sigh.

“Good girl. Tell me how that feels.”

“Uncomfortable, sir. I don’t think I can keep this in,” Alice replied, cheek still pressed to the carpet.

“Does it hurt?”

“It hurt a little going in, sir, now it just feels uncomfortable, like I desperately need to take it out.”

“How do you feel, knowing that your efforts have made me pleased with you?”

“I’m very happy, sir.”

“Alice, you have done very well. I hoped that we might work up to the next size, but time is not on our side, the hour is almost up. As a reward for your good behaviour and for being such a good student I am going to fuck your arse. Would you like that as a reward?”

“Yes sir. I would love to have your cock inside my arsehole. Thank you for being good to me.” I was very pleased at how well Alice was adopting the submissive role when she addressed me.

As Alice said this, I took my once more hard cock from my trousers and applied a good sized blob of lube to the tip. As I smoothed the lube down my shaft I could feel that I would come very soon, so made no delay in pulling gently at the base of the plug which protruded from between Alice’s buttocks. Her sphincter was tight around the narrow neck of the rubber cone, not allowing it to escape easily this time. Pulling harder I instructed Alice to push out a little, and she wriggled a little to try and help me extract the plug. With a little groan she managed to open her anus over the widest part and the remaining length followed easily. Quickly tossing the slippery rubber toy aside I knelt between Alice’s legs and applied the tip of my cock to her anus. The slow loosening with the plugs had had a great effect and I barely had to push at all to sink my well lubed length inside her all the way to the base.

Alice still had her hands behind her back and I grabbed her wrists in each of my hands, using them to pull her body onto my cock, penetrating her as deeply as I could, feeling the strength of the muscles of her anus squeezing at my base. I withdrew slowly until only the tip of my cock was held in her anus and then once more pulled her back onto me, plunging deep inside her as let out a soft groan of discomfort.

“I need to fuck you harder in order to make myself come. I want you to tell me if it hurts you at all. I won’t stop, but I just want to know.”

And with this I started to fuck her arse with increasing force, each thrust faster and harder than the last, my cock almost completely leaving her body before thumping all the way back into her, all the while gripping her wrists tightly behind her back. Alice groaned with each stroke, the noises initially of suppressed pain, but as the rhythm quickened they became the moans of deep pleasure.

The sight of my cock plunging in and out of Alice’s anus, the slapping of my hips against her red-streaked buttocks as I thrust deep into her and the sound of her ecstatic groans were too much for me to last long. I felt my cock begin to pulse and with three more deep thrusts I was coming deep into her arse, releasing her wrists and smacking her quivering cheeks as my sperm shot into her. Grabbing Alice by the hips I pulled her hard against me as my cock rhythmically emptied the last drops of semen into her. As I withdrew, she once more rolled onto her side on the floor, breathing deeply, her skin shining with sweat.

“Alice, I am sorry but we have run out of time today. You may dress.”

Alice climbed to her feet and began to replace her clothes, slowly and with some effort following the exertions of the last hour.

“We need to discuss payment, Alice. As advertised, the fee for my services is £100 for a one hour lesson. I hope that you feel you have learned some valuable lessons today, but it is my practice not to demand payment if you believe that your time has been wasted or that you have learned nothing. I should add however that if you choose not to pay, you may never resume your training with me.”

Alice reached into the pocket of her jeans and produced five neatly folded £20 notes which she offered to me, averting her gaze as she had been taught.

Taking the money from her I said, “You may look directly at me now, Alice.”

Alice made eye contact with me for the first time in more than half an hour. Her expression was difficult to read – a faint smile perhaps, a suggestion of fear, obedience, a desire to please.

“Alice, you have shown great promise today and I am pleased with your performance, and the effort you have made. There have been some fairly elementary errors, but we will iron these out with time.”

I kissed her lightly on the forehead, a wide, grateful smile springing to her face.

“Thank you, sir,” she breathed.

“Now be on your way Alice. I expect you at the same time next week, do remember to dress appropriately.”

We met again one week later.

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  1. loveanal says:

    omg i wish that was me my master started me out at a medium sized butt plug on the frist session

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  2. 21yrsoldvirgin says:

    Omg this story is so great!

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