One of the kinkiest enema that I did to myself when I was a teenager was to not poop for a day, then give myself an enema the next morning. Upon waking up, I would not pee or poop.
I would use my mother's enema kit and wear her panties. I would slip her panties on while I prepared the enema. My penis was engorged and sticking out the top her panties while I assembled the kit and ran the water to make it warm. The running water made me want to pee so badly.
I slid the long tip into my full rectum and released the clip to start the flow. The pressure of the warm water in my full rectum made me start to pee. I peed all over my mother's panties before I came or released the enema.
The next time that I gave myself a kinky enema, I decided to make it a punishment enema. I withheld my poop for a day and no pee when I woke up. I put a suppository deep into my rectum, pulled on my mother's panties and assembled the enema kit. I was struggling to get everything ready. I was so full already and my hands were shaking because I was so nervous.
I pulled the panties to the side and slid the tip into my full rectum. I could barely move without the enema tip sliding out or needing to pee. I hadn't even started the enema. I had to do something. I grabbed a large cup from the top of the vanity and filled the cup with my warm pee. The enema tip slid out again while I was peeing.
Now my punishment was to hold the cup of my pee in one hand palm up while I gave myself the enema with the other hand. If I spilled the pee out of the cup, my punishment was to drink the pee. I allowed myself to insert the nozzle into my rectum before holding the cup, but it was going to cost me an additional 5 minutes of hold time.
The long nozzle was buried in me and was being held in by the panties. But. between the warm water and the suppository, I was cramping badly. I could not reach the clip to turn the water off and not spill my pee from the cup. One big cramp hit. I put my free hand on the shower bar to hold myself and I spilled some of the pee!!!
I submissively, and according to my punishment, took a few sips of my pee. I could not believe my predicament - my belly was swollen, I was wearing my mother's panties, I was hard as a rock and I was drinking my own pee.
The enema nozzle started to slide out of me again. I quickly slipped my mother's panties off of me. I could not wait any longer. I started to masturbate hard. It only took a few strokes before I started to cum. As I was cumming, I began to release my enema into the shower, As I did, I poured the rest my pee all over my body.
I took a shower and fell asleep! I was exhausted.