My stepsister June had turned my life around. I had been a wreck, fired from two jobs for tardiness, embarrassing myself by leaking pee in public, unable to clean my house and unable to stay in a relationship.

First, June had visited me to bring pull-ups, diapers and the belted shields that have become my go-to. She knew I wouldn't wear them without prompting, I guess… she had made me try them all on for the first time, spanked me when I wouldn't try a diaper, then laid me down on my bed and diapered me up for the night.

From that time she's come over every single week to keep tabs on me and punish me when I need it, and gradually mother me back into shape. She's younger than me, only twenty-four, but so together, so dominant and firm, that I think I would do anything she said… especially if I knew one of her trademark punishments was coming.

Last night was an intense session with a new punishment. I had gone to the doctors' last week to renew my asthma prescription. It was my second day off in a row and I hadn't thought much of slipping on a pair of khakis with nothing underneath, cowboy boots and a t-shirt, before walking out the door.

In the waiting room, it had happened. I got that feeling in my dick and bladder. I'm used to ignoring it. When my incontinence has been bad, I wear pullups that can soak up a little leakage effortlessly, in case I'm out where can't change myself before it happens again. When it's been a while since it's happened, I wear an incontinence shield, thin and comfortable between my thighs with two elastic straps around my waist.

I can barely control it at the best of times. At the worst of times it just happens, and if I'm wearing something, no matter, just a brief warm feeling and I can excuse myself to change it.

But I was commando, so I left two very small dots next to the fly on my khakis. Surely no one noticed; for all they knew or cared it could have been droplets of coffee from earlier. The waiting room was almost empty, just an old man surely wearing more than a pull-up himself. No one knew.

But I had to confess to my life coach.

She was beginning to lean into the dominatrix aspect of her role in my life, in a subtle way, not altogether sexual. She wore a black top with a plunging neckline that exposed the very rims of black bra cups, maroon leggings and very high heels.

She sat on my couch in my relatively clean living room like she owned the place. She had a riding crop--it lived in the umbrella holder by my front door, but now it hung by her wrist on its rubber loop.

“You understand this is a serious relapse in your behavior.”

I felt like a dog being confronted with a spot on the carpet. “I understand.”

“I have to punish you much more severely than I would have had to six months ago, because you've broken a lot of progress. Have you ever had an enema?"

“Isn't that for constipation?”

"Medically, yes, but don't talk back. Today, you're going to get an old-fashioned punishment enema. Prepare the ottoman but put it directly outside your bathroom.

The ottoman lives in my house. It's what she sometimes ties me to for a spanking, and I find having it in my house is an effective reminder to stay on track. It's not actually for physical restraint, as I take my punishments like a good boy, but for the emotional ritual that puts me in the right headspace for a firm spanking. I think she enjoys it a great deal too.

I pulled the big cushioned footrest over to the corridor outside the bathroom and brought the straps and cuffs. I attached the leg cuffs to the feet of the ottoman on one end, and the hand cuffs to the feet on the other, then laid the waist strap under it on the floor.

She joined me. “Strip.”

I did. She was pleased to see that, in the privacy of my own home, I was wearing a diaper. As I took off my pants she ripped the tabs off the diaper and pulled it crudely from between my legs. It was barely wet.

She didn't have to tell me to assume the submissive position once I was naked. I knelt in front of the ottoman and stretched across it, putting my elbows on the floor on the other side. My back was bare and exposed, my ass sticking up.

Quickly, she cuffed me above the knee and above the elbow and pulled the waist strap up around me and buckled it, pulling it tight around me and the ottoman. I felt the odd euphoria: I was at her mercy.

“I knew I might have to punish you severely soon. I gave half a thought to a figging and caning, where I put a piece of ginger in your ass to keep you from clenching while I hit you with a rattan rod. But keeping fresh ginger is so expensive, and I'm not sure what you would do to deserve something that agonizing. So I settled on a punishment enema. I have the equipment in a sealed bag in my purse. You're about to get your guts filled up with hot sudsy water and hold it.”

“Yes, ma'am.” I was secretly horrified. This seemed like it would be excruciating. I wondered if I'd prefer the “figging."

“I'm going to put a diaper on you after the enema nozzle goes in, in case you fail to hold it for me before you get to the toilet. I won't punish you if something happens as you stand up; it will be hard not to squirt. But you will not be allowed to go properly until you've held it for five minutes. If you go before, it will be an ice cold enema next, and a severe spanking.”

“Yes, ma'am.”

She left me tied there and went to the kitchen for several minutes, then came back with something red that I didn't get a good look at.

Now, I'd been pegged once, by a bisexual girl that I went on to totally blow it with. It had been excruciating as she slid an oversized silicone dildo into what she had called my “mangina,” using only her hip muscles, no hands, and it made a mess when it came out coated in shit. I expected the nozzle to be agonizing as well. I hadn't seen it and had no idea of its shape.

I was surprised as it went in. It was thin and well-lubed and oddly soft. Then it wiggled inside me and I realized it was my stepsister's gloved finger gently probing into me. Then it was quickly withdrawn and replaced with something quite similar, but hard, something rod-like that tapered towards the base, so that when it was all the way in my anus was around the thinnest part with a small flange resting directly against the sphincter. There was no pain, as of a big rubber cock, and I didn't feel especially feminized by this penetration. It was designed to be in there, and it felt oddly right.

Then there was a tedious amount of time as she fitted a diaper to me in my odd position. I could feel a tube snaking down my leg out of the inner cuff of the diaper. When she was finished she put a firm hand square on my upper back and put some weight on it.

“You're going to want to expel almost as soon as the water starts to hit you. Fight it and I'll consider not spanking you later.”

She wasn't lying. There was a click which I found out later was her taking a stiff clip off the rubber hose. About half a second later there was a strange feeling immediately inside my ass, and a moment later a rush of heat and odd sensation into my guts, like the sudden flow of diarrhea in reverse. But I felt like I was about to sent it rocketing back out my ass.

Somehow I muscled it back and the feeling was clear. My guts were filling up with hot water, and there was a scouring ache. I felt like my entire being was being invaded and punished. My dick was hard and irritated by pressing against the diaper.

The feelings were all new and all uncomfortable and all felt like a punishment. I became bloated and felt the waist strap more than I had before--she'd left it a little looser than normal. I also noticed at length that her hand was still hot on my upper back.

“I need to go,” I said, blood rushing to my face as I strained to hold it in.

“Do not.” She wasn't asking.

More and more came. I felt my guts move as my intestines inflated.

“I have to…”

“If you do, the punishment will increase.”

I strained, clenching my ass around the nozzle, which became uncomfortable as the flange pressed into my cheeks on either side.

And, suddenly, there was no flow. I was quite full and I felt like I was about to explode, but it suddenly wasn't getting any worse.

She removed her hand.

“The five minutes began when the water ran out. You have about 4:45 left.”

“Yes, ma'am."

“I think I'm going to have to start spanking you over my lap sometimes again. You and I have clearly grown apart if you're disobeying me like this.”

“Yes, ma'am.”

“But don't think I'm going to go easy on you when I don't spank you on the ottoman.”

I could barely speak. I grunted then choked out “yes, ma'am.”

“I'm always spanking you with a hairbrush after this. You're a big boy and hand spankings are too gentle for you, apparently.”

“Yes, ma'am.” I felt like I was about to uncontrollably shit.

“Are you embarrassed when you get a little stiffy when I spank you over my lap?”

I decided to be honest. Maybe she would punish me harder, but maybe not.

“Yes, ma'am, I hate it when that happens.”

“Well, you'll just have to avoid getting spanked, then.”

Suddenly, I just went. A geyser of frothy, soapy water must have sprayed into the diaper all around the nozzle. I was still full, but less distressed.

“I just… squirted, ma'am.”

“For shame!” She smacked me hard on the middle of my back. “You had two minutes left on the clock. I'm going to extend your punishment another minute. If you don't mess your diaper up any more, I won't do the cold water enema, but you're getting a hard spanking over my lap after this.”

I groaned and said “yes, ma'am.”

It was less than a minute later that the same thing happened again.

“You've been very bad for this punishment. We're going to end this enema now and add the rest of the time to your second enema. Seven-twenty five for the second one, Kullen. You're getting what you deserve one way or another.”

“Yes, ma'am,” I said.

She untied me and had me stand up. I saw that the bag that had been draining into my ass looked just like a red rubber hot water bottle. Next, she dramatically ripped my diaper off. It was stained brown and slightly sudsy. She held it near my face. It smelled more soapy than anything. “Disgusting. What are you, a baby?”

Then she yanked the nozzle out and let me sit on the toilet. It was an agonizing five minutes, dealing with the stomach cramps and shitting out little pellets and soapy water. Finally, a big shit came out and the floodgates were opened. Before long I felt mostly empty.

She had me wipe and flush. "I'm not taking the time to tie you up again. I'm just going to handcuff you to the shower curtain-rod and let you take it standing. This way, if you decide to shit yourself again I'll know.

A minute later I was standing there in the tub with my hands over my head, and June crudely shoved the nozzle back into me and unclicked the bag, which she had refilled in the kitchen.

This time the aching was different in character, and I could clearly feel icy cold water squirting into me and… oddly stimulating my prostate.

This time the retention too, was difficult for a different reason. My guts still ached from the soap, but gravity was more of a problem this time. I wanted to just open my ass and let all the frigid water drain out. It felt like it was all sitting directly on the sphincter, which was tightly clenched around the white plastic nozzle, and I shivered and felt my insides and anus go slightly numb.

Time passed. June regarded me from the closed lid of the toilet, her legs tightly crossed. She did not spare looking at any inch of my naked body, from my armpits, exposed by the position my arms were chained in, to my cock, which she had seen a few times before, but never seemed to linger on until now.

“Alright, your time is up.”

She let me expell on the toilet, then ushered me into the shower where she stood outside and sprayed me down with the hand sprayer, then toweled me off roughly herself.

Then she led me by the hand to the couch, and without so much as the courtesy of the towel on her lap that she had given me when she spanked me in this position before, she drew me across her lap. My dick was already hard, and she shifted around with an innocent expression until it was between her thighs, which she gripped it tightly with. I blushed hard, my heart pounding in my ears.

“I want you to count," she said, getting the hairbrush from behind the couch cushion where she knew I would have left it. Then she hit me hard with it.

“One, ma'am, thank you.”

“You can call me by name for this.”

“Yes, June. Thank you.”

She hit me rapidly three more times.

“Two, three, four, June. Thank you.”

After ten she seemed satisfied. My ass had the tender burning and sensitivity it hadn't had since the last time I was spanked as a child. A tear ran down my cheek as she gently kneaded the area she had just tanned.

Then something happened I did not expect. She still had a glove on the hand she'd been spanking me with, and she spread my cheeks with the other hand and started working a finger into me again, this time with only the natural lube of the rectum. Almost immediately she found the prostate and began to massage it. There was a gentle movement of her thighs around my dick as she rubbed the sensitive part inside me with her fingertip, until… oh, this was wrong, this was wrong…

I came between her legs.

“There, there. It's okay, Kullen. I wanted to let you know I forgave you. Now let's diaper you back up.”