Emptying Thomas

In the next few weeks Diane and Thomas fell into a steady routine. Diane would instruct Thomas that he was to be ready to receive her on certain days, she would stick her fingers in his butt, stretch his rectum, and thoroughly massage his prostate. At the end she would take his little cock in her mouth, suck his entire load down her throat and ride his face until she was too weak to sit up. For two people as anal as they were, the routine brought them a lot of comfort and mental peace. It was structured, orderly, and controlled. Diane finally had taken the full control over her husband’s ass that she desired, and Thomas was receiving orgasms that were approximately a thousand times more intense than any he had ever had with his dinky wiener. Neither had even come close to suggesting that they go back to vanilla vaginal sex; it was butt-sex or nothing.

Although what they had settled into was comfortable, Diane knew that she needed continue the training regimen. She was determined to become the sole and permanent penetrator in their relationship, the one with total sexual control over his BB&C (butt, balls, and cock). She knew that at this point Thomas would put up little resistance to her, but she knew his brain would become most addicted and amenable if she took things at an even pace.

The evolutions began slowly and their encounters gradually changed in a few ways. Firstly, since Thomas’ first milking he was regularly being drained and thus his balls were never able to swell to the abnormally humongous size that had started them on this journey. Diane actually believed that the persistent emptying was causing them to shrink further. She always inspected them before she went inside Thomas and most of the time they were just tiny little shriveled grapes that clung tightly to the underside of his cock. On one particularly cool afternoon she saw them disappear into his abdomen, leaving his underside looking smooth and flat. Before their anal play his little squirts had just never been enough to totally clear out all the cum in his prostate and testicles. Her play changed all of that: she extracted everything on every encounter. He was perpetually empty.

Second, since his balls didn’t require extensive massage, one of her hands was now free to play with herself. She bought herself a small vibrator and would press it against her clit in rhythm with her fingering. Between the post-milking pussy-eating and her vibe she was now orgasming nearly ten times every sexual encounter. She would be sated for a day or two, then the urge to get in his butt would return and she would instruct him to ready his hole.

Third, Diane was very pleased with how she had been able to train his sphincter. Thomas had never been tight per se but in their first few encounters she definitely felt him clenching and clinging with his rear muscles at just a finger or two. As time passed and he became more and more accustomed to being penetrated, his muscles were more accepting. During one session Diane realized that she could start him out with two fingers rather than one. That same day she added a third finger; they both came especially hard that day. After several weeks she now was able to start with three fingers and would occasionally work in her pinky as well. His butthole was just so eager to accommodate her and seemed to loosen every time they played. With every session, with every pleasurable movement of her fingers and orgasm, his brain was slowly coming to associate sexual pleasure solely with his ass. In the depths of his psyche, the recesses of his perverted brain was beginning to think that more, bigger, deeper penetration was what he needed to be happy.

In her mind, the only problem was that Thomas’ loads were absolutely pathetic. His tiny little testicles were only able to muster a few drops on each encounter. On the one hand, she relished the control she had over his cum, she chose to keep him empty and drained so he was perpetually empty and drained. In the future, though, she wanted him to make him squirt. She wanted to get in his butt and force massive loads of frothy cum out his tiny cock, to physically see how the power the power her anal intrusions were having on him. Thomas’ long-term training would need to include a regimen to help stimulate his production; there were a few more steps before she would set him along that path though.

Thomas had never been happier with his sex life. He had stopped masturbating entirely. This was part out of necessity, he was still totally unable to achieve erection without anal stimulation first. For the most part though it was because pulling his little nub had just never given him the same amount of pleasure as prostate massage did. He had always enjoyed orgasms, who didn’t? But for most of his life they were eminently forgettable; he would use two fingers to tug his little dicklet for a few minutes, shoot his tiny load into a tissue, clean himself and go about his day.

Now he was experiencing what true sex must feel like for people. His entire body was spasming in ecstasy to leave him out of breath and unable to think clear thoughts. He felt more connected to his wife than he ever had before. Something about being so passive, so open and accepting of her penetration had driven their connection even deeper. He wanted her to be inside of him constantly, to always feel her presence, a few fingers up his butt that seemed to be dictating the path of his life. He loved it.

Which is why when Diane told him that they would be doing things differently that day he was a bit hesitant, he had never been good with accepting change. He could have played with a few fingers up his butt every few days for his entire life and been content, why would he want to change anything? Those thoughts quickly dismissed themselves. Diane wanted to do something different, Diane was his pleasure source, he should listen. He trusted her to do what was best for him, he would follow her lead willingly and enthusiastically wherever it led.

It was early on Saturday morning and Diane had shuffled Thomas into their bathroom. Next to the sink was a black bulb with a 6-inch long nozzle protruding from the end. “This is an anal douche. It’s used to get your insides nice and clean so we don’t encounter anything too unpleasant during a more… invasive encounter.” She spoke clinically but on the inside she was incredibly turned on, her panties would assuredly need a heavy washing later. “I’ll help you this first time but, in the future, you will be responsible for maintaining a nice, clean bottom for me. I will fill the bulb with water, lube the nozzle, insert it past your sphincter, and empty the water into your rectum. Now net on our knees, bend over and spread our cheeks for me.”

Thomas obeyed immediately. He never had a single thought that told him to resist. His mind was willing and pliant, he would bend to her desires even if it meant pouring an ocean of water up his ass. Diane noticed how deftly he followed her instructions and smiled.

Thomas assumed the position and felt the tip of the nozzle at his hole. He pressed back, doing everything in his power to accept this new tool into his bottom. Immediately he felt himself filling up, he felt his rectum inflate as the water flowed into his ass. A minor cramp spasmed through his backside, he fought past it because he knew that he needed to please Diane.

“Once the bulb is empty, you will hold the water in your butt for a few minutes then empty it into the toilet. Douche yourself a few more times until the water comes out clean and then meet me in the bedroom. Since this is your first time I will be patient while you do this but in the future I will expect you to be ready whenever I want you to be.”

With those words she left Thomas bent over on the floor, the water roiling his insides while he clenched his lubed up asshole, trying to maintain control over himself. He emptied the water from his ass, repeated the process a few more times and at the end felt very clean in his back. It felt dirty to admit to himself but he enjoyed the process. The nozzle felt nice sliding past his sphincter and he would rock it slightly against his prostate as he squeezed the bulb. The water gently filled his ass, leaving his rectum packed and happy. While emptying himself he would scroll through porn on his phone, looking at images of other tiny-cocked men having their anuses opened by powerful women. By the end he was insanely aroused.

Once he was clean, Thomas bounded towards the bedroom to find Diane idly playing on her phone. Next to her on the bedside table was what looked like a little rubber tree. “Bend over the bed and spread your ass. I need to inspect your backside to see if you did the douching correctly.” He immediately complied and he soon felt her fingers at the sphincter. She had her index fingers lubed up and inserted them both. Ever so gently she hooked her fingers into his ass and started to pull his anus in different directions. His pliant hole allowed itself to be stretched and opened. It didn’t take long for Thomas’ perpetual moaning to begin and for his little cock to start seeing some life.

Diane looked inside her husband’s ass. She felt around with her fingers. She was pleased. Truthfully, she didn’t care if things got a little dirty but she loved the level of control she was able to force onto him. Thomas had agreed to shoot water up his own ass without a single word, he just did it because she instructed him to. She would need to continue to test the depths of her control over his butt.

After a minute or two she removed her fingers and left his ass to close. “Thomas, today I’m going to really stretch your sphincter out. I’m going to go deeper into your ass than I’ve ever gone. This will please me greatly and I believe you will gain a great degree of pleasure from it as well. To help facilitate my playing I am going to start you off by inserting a buttplug. You saw it on the table next to me. It’s a silicone sex-toy with a wide knob, tapered neck and wide base. It will go into your ass and remain there until I decide to remove it. This will help your anus totally relax for me.”

She didn’t wait for him to respond, she just took the toy and put it on butthole and started to push. She found his anus just as pliant as usual. At first she was disappointed, she had read that most people are tight at first. But her euphoria over quickly seeing the toy disappear into his willing asshole quickly won out. Diane didn’t want a prissy tight asshole to play with. She wanted something she could abuse and she had found it. The plug slid in deeper and deeper until it she saw his anus become taut over the very widest part. She paused her, marveling at the sight of his stretched butthole willingly accepting her toy.

With one final push she got it seated in his butt. The base settled between his cheeks. She saw the plug shift a few times and knew that he was clenching and unclenching his sphincter around the toy. She suspected that part of that was subconscious, but she suspected that her husband was doing some exploration as well. Diane reached between Thomas’ legs to take his cock and balls into her hand. She was pleased to find his balls tiny and his cock hard. “The plug is 6-inches long and about twice as thick as this little guy. You should thank me for putting more into your butt than you could ever get into my pussy.” She didn’t need to tell him this, she just wanted to reinforce that she had the power in their relationship.

The feeling in Thomas’ ass was blissful. He felt full, he felt stretched, he felt extremely comfortable even though he now had a fairly large hunk of silicone lodged himself of his ass. The buttplug didn’t move much, it didn’t try to stroke his prostate or massage his rectum. But it did stimulate his ass. He felt his butthole clenching and unclenching around the neck of the toy causing the base to wiggle between his butt cheeks. The slight movement of the plug gently pushed his prostate. He looked down to see a tiny strand of cum dripping from his little cock.

“Okay Thomas. I’m going to run a few errands. You will keep the plug in until I return. I don’t care if you remain naked or put clothes on but I expect you to be back in his exact position — nude, bent over the bed, plugged, ass ready to go — when I return at exactly 1:00.” With those words she left him in that position. In the distance he heard their car kick to life and drive off.

Thomas lay there for a few minutes. He was very quickly used to the sensation of the plug in his ass. Although the widest part was a little larger than his wife’s three fingers, the neck that his sphincter was currently grasping was fairly narrow. His anus didn’t hurt, it didn’t ache or burn, it just buzzed with sexual energy. He glanced at the clock and saw that it was just before 10:00, he had three hours of plugged up time to kill. He glanced around the hallway and saw that his wife had closed their blinds and window-shades. Thomas mentally thanked his wife for providing him the privacy and opted to remain naked. Without anything specific to do, he decided to get a few chores done and bounded off to the kitchen with a mental plan to clean dishes, dust, and do his wife’s laundry; since they started their new play he had noticed that Diane was going through underwear very quickly.

Walking with the plug was a new sensation. The rocking motion of his butt cheeks caused the plug to move to and fro inside him, lightly stimulating his prostate and rectum. He found himself walking with almost exaggerated motions, swinging his hips and swaying his ass to get maximum stimulation on the plug. Every once and a while he would see a tiny drop of precum ooze from his cock. At first he looked around for a tissue or a towel. After a few times he opted for a new approach. He swirled the drop a bit on the head of his cock, gathering the fluid on his finger, and then brought it to his mouth and sucked it off. It tasted a little salty, he liked it.

For the first half hour or so he stayed rock hard. His tiny little man was doing its best to stand proud and attentive. An outsider would have just seen a pathetic little cocklet that could only get hard when a bigger, longer, wider plug was shoved in his butt. But as time when by and as the tasks in front of him and the plug behind him occupied his thoughts his cock shrank back into its tiny nub form. He paid it no attention; his attention was all on his butt. Thomas went about his tasks quickly and efficiently, his energy weirdly focused by the reminder that Diane was, in a way, inside him. Two people as anal-retentive as Thomas and Diane never kept a messy house, but it was near immaculate by the time he was done.

A full thirty minutes before the appointed time he returned to the bedroom and resumed the position; he couldn’t risk being late and losing out on whatever his wife had planned for his butt. He sat quietly, gently squeezing his sphincter around the plug and obediently waiting for her return.

Diane was proud of herself for having such control. She was proud of the control she had over her husband, he took the plug easily and without question or hesitation. And she was proud at her own self control for walking away and not viciously taking his ass there and then. Her goal was to get him used to being anally stretched for longer and longer periods of time. Eventually she would maintain a constant presence in his butt, he would never be able to escape the physical reminder of her anal control.

To that end she opted for a patient approach and found an excuse to leave the house to go shopping. At the very first store though she found her mind overwhelmed with thoughts of anal. She quickly found the ladies restroom and thanked her past self for deciding to bring her vibrator in her purse. She barricaded herself in the first stall and had the vibe on and glued to her clit before she even had her pants fully down. As she got closer, she turned it vibe up, not caring if anyone else could here the noise. Her climax was swift and sloppy. Her mind began to return to her, it’s utter fixation on the fact that she had left her husband plugged and naked for a few hours receding to the back of her brain. She packed up the vibe and composed herself. This orgasm was just about clearing a few cobwebs, she would achieve her ultimate sexual pleasure later that day.

Her errands proceeded in much the same way, she walked, she looked, but mostly she was thinking about what she was going to do to her husband’s butt. She relieved herself again an hour later. This time when she was done an older lady threw her a judgmental stare when she emerged from the stall. Diane slyly thought a nice butt-fucking would probably do the judgmental prude a lot of good; some people just needed to be anally dominated for their own good.

At around 12:15 Diane decided it was time to return. She hadn’t actually bought or accomplished anything while out running these errands but she had heightened her own sexual tension. By the time she was home she had leaked through her panties, if she wasn’t wearing black jeans someone would have seen a small wet spot of pussy juices forming on the crotch of her pants.

When she arrived home she found the house in excellent condition. She had vaguely hoped that her husband would put himself to use and give things a nice cleaning but she didn’t think that Thomas was yet ready to have that particular level of control foisted upon him. Seeing this, she mentally noted that she would have to move some of his programming up in time. If her anal probing was already causing him to serve her needs without being explicitly instructed then his mind must be very willing to accept her control.

Diane ducked into a spare bedroom where she had had her new secret toy hidden. She opened the box and saw the dildo inside. 7 inches long, a wide mushroom head and ultra-smooth shaft. The material was hard enough to stay up on it’s own while still being pliant enough to bend and give; it was perfect for going in an ass. It was wider than anything Thomas had ever had in his sphincter. He would be very well-stretched at the end of the session.

Underneath the dildo was her harness. She quickly shed all of her clothes, put the cock through the o-ring and slid the straps up. It was a jock-style harness with straps that went on either side of her. She secured them in place, tightening them low around her of her ass cheeks. She had done this ritual every day for the last week, donning the strapon cock and marveling at herself. She stroked it, humped the air with it, swung it around. At least once a day she also would close her eyes, jack off the cock and touch her clit. Slow jacking at first that turned into her furiously handling the dong by the time she was ready to climax. She always got off so easily while doing that.

The reason she chose this particular room for her secret wardrobe shows was the floor to ceiling mirrors it had all along one wall. She looked at herself, marveling at the massive tool she was wearing. Diane had only had a cock for a week and was already obsessed with how big it was. Every time she looked in the mirror she felt herself swell with confidence on seeing her beautiful pecker sticking straight out from her body. It was so powerful looking and was somehow simultaneously both so masculine and feminine. It didn’t have fake veins or balls, it wasn’t trying to be realistic. It was just a big-ole girl-cock, perfect for spelunking up her husband’s boy-pussy. She had no idea how Thomas had been happy all those years trying to pretend that his dinky little weenie was a real cock. In her mind, her big, fake strapon dildo was more of a real cock than his shriveled dinklet would ever be. She was glad that she was training his ass to be a sex organ instead so he wouldn’t ever have to worry about his pathetic penis ever again.