Posted on Thu, 18 April 2019
Aside from one regular, I haven’t had many sessions with diaper fetishists. Maybe a dozen in total over the last few years. The first of those sessions holds a special place in my heart though.
I was 19 and working with a pro-domme in the city. She almost didn’t accept me, because I was still in high school. Before you start making assumptions about why I was in high school at 19, my father was in the military and I attended the 8th grade in Japan. When we moved back to the US, they wouldn’t accept that year abroad and I had to repeat the 8th grade. Trust me when I say it sucked.
Anyway, I was working with this pro-domme as a switch for sessions. She would never allow clients to top me, but would often top me in conjunction with her clients or simply use me as a prop to entice them. Sometimes that meant just being tied up naked in the corner for aesthetic reasons, but usually it meant being spanked while the client watched in anticipation of what was about to happen to them. Mostly, however, we would play off each other as we teased and humiliated our clients.
One day, we had a client coming on a Saturday morning. He wanted a scenario of being sent to detention, where the headmistress would strap him down, then spank him until he was bawling, plug and diaper him. We had a scene planned out where I would be another student in detention, already sitting there when he arrived. She would tell him to sit in one of the desks in the area set up like a schoolroom, then take me to the front of the class and spank me over the teacher’s desk. Then she would put me in the corner and follow through with his scenario.
When the doorbell rang, I rushed into position and she went to answer the door. He had given the name of Tommy, but when I heard him speak from the other room I recognized the voice. It was the voice of a boy named Tony that went to my school. I freaked out and rushed into a different room before he saw me. When she brought him into the space, she noticed I was gone and told him to sit quietly while she rounded up a lost wayward student.
As soon as she saw me, she knew something was up from the look on my face. Quickly and quietly, I told her he was a student at my school. Her first worry was that he might be too young, but I knew he had just turned 18 a few weeks earlier. However, he had a reputation as a bully at our school and had repeatedly made homophobic remarks to a friend of mine and often commented about the weight of many of the girls. She asked if I would be willing to switch it up a bit and perhaps put an end to the bullying. Under normal circumstances, such a thing would never be appropriate, but we knew we would never follow through with any threats. We just had to count on him not knowing that.
She returned to the classroom with a folder and began to read off the script she had prepared. Essentially admonishing him for his behavior in school and how his teachers had repeatedly referenced his infantile behavior and common use of fart humor. He was then lead across the room to the large desk and she told him to bend over and grab the edge on the other side. Once in position, she attached the cuffs dangling from an eye hook to his wrists, effectively trapping him in this position.
His pants and underwear were unbuttoned and pulled down to his ankles, exposing his ass. He was clean, but she pretended to see skidmarks in his underwear and admonished him.
“Infantile behavior is the least of it. Who leaves skidmarks in their underwear?! You’re like a big baby.”
Then she pulled a good sized butt plug and lube from a drawer and held it in a way that he could clearly see it.
“We’re going to have to take steps to make sure you don’t mess yourself during your spanking.”
He looked worried, but his erection was also pressing hard againt the desk.
Applying just a little bit of lube, she pressed the tip against his asshole and pushed it in slow and steady. He winced at first, but it quickly turned into panting and groaning. When it slid into place, he started humming loudly to prevent himself from squealing.
To take his mind off it, she began spanking him with her hand. Slowly at first, as she sternly talked down to him for his poor behavior, but picked up the pace until his ass was a bright pink. He didn’t give much reaction to the spanking though, so she paused to retrieve a short leather strap from the desk drawer. His correspondence said he wanted to be spanked until he was bawling – and he didn’t want a safeword, because he would definitely use it too fast. Normally, we wouldn’t do sessions without safewords, but this was a fairly mild session overall and nothing dangerous would be occurring.
With the first stroke of the strap, he bucked on the desk and tried to twist out of the way. It didn’t work, as her aim was too good, and she started raining down blows on his plugged ass. By the fifth stroke, he was begging her to stop, but he wasn’t bawling yet. He started crying by stroke fifteen and was finally bawling by the time she reached thirty. She went to fifty for good measure, partially due to the knowledge that he was an actual bully.
After a few minutes, the bawling subsided and she released the cuffs from the desk. His hands were still cuffed together though to prevent him from rubbing his ass or removing the plug. With his pants and underwear still bunched up around his ankles, she guided him to the end of the desk and had him use a footstool to climb up onto the desk. He took a violently deep breath as he sat down on the hardwood, a result of the welts on his ass and the plug still inserted in his rectum. He lay on his back and watched as she gathered a colorful ABDL diaper, baby oil and baby powder.
He lay perfectly still as she lifted his legs and slid the diaper under his butt. She told him to hold his legs up while she applied the baby oil, which he did by grabbing his pants. As she rubbed the oil into his welted bottom, he started to get an erection, but she ignored it as she finished the oiling and added powder. When she pulled the diaper up between his thighs, she lowered his legs and had to force his penis down to tape the diaper closed. Now diapered and complacent, she pulled him to his feet, eliciting another gasp as his weight pressed against the plug and welts once again.
She removed his cuffs and directed him to the large 10′ long white board on the wall, where she gave him a dry erase marker and told him to write “I am a diaper baby that belongs in nursery school” one hundred times, alternating between five different colors with each line. He got right to work.
While he was writing, she came to find me and we discussed me coming back in. Rather than playing a school girl in detention, I would be the teacher’s assistant and tease him about the diapers. He would obviously recognize me from school, so I could “insinuate” that if he doesn’t stop bullying my friend, his secret diaper fetish would be exposed to the school. We both had ethical reservations about it, but we also knew we would never follow through with it. As long as we didn’t specifically threaten to out him, we could just rely on his own fear to guide him down that path.
When we walked back into the room, he didn’t even turn his head. It was obvious he wanted to, but was worried it would have consequences. As he continued writing lines, we started having a conversation behind him.
Me: “Oh no. Another diaper baby in detention?”
Mistress: “Yup. You should have seen the nasty skidmarks in his underwear. Actually, no. You don’t want to see them. Disgusting.”
Me: “His handwriting even looks like it was done by a preschooler.”
Mistress: “Pathetic.”
At this point, he was starting to recognize my voice and we could see the apprehension in his body language. He was clearly worried it was me, but hoping it wasn’t and was actively trying to avoid turning his head in any way that I might be able to see his face. For all he knew, I just arrived and had no clue who he was yet. His fears came to light fast when I spoke again.
Me: “I heard he’s quite the bully. Likes to make disparaging remarks about gay students and anyone that might be a little overweight.”
Mistress: “Well, we might need to have him in detention more often. That type of behavior is unacceptable.”
By now, he was clearly shaking as he struggled to focus on writing lines. He knew it was me and he knew that I was aware of who he was. It was time to end have that talk.
Mistress: “Tony, please turn around.”
She intentionally called him by his real name, rather than the fake name he had given. He turned slowly to face us – tears welling up in his eyes.
Mistress: “Is it true that you bully other students?”
He nodded.
Mistress: “Is that an appropriate behavior?”
He shook his head.
She chose her next words very carefully, avoiding any actual threats and leaving any insinuations to his imagination.
Mistress: “Nobody needs to know about your visit here today, and my assistant is surely not going to tell anyone, but I also don’t want to hear about any more bullying. Do you understand me?”
He nodded again.
Mistress: “Alright, good. I want you to come back here in two weeks. I’ll message you with the details. No charge, but you’re going to be punished again. I would like to hear glowing reports about your behavior between now and then. Understood?”
Again he nodded.
Mistress: “Good. Now turn your diapered butt around and finish your lines.”
He turned around and got back to work. The shaking stopped, which meant he felt better about the situation. I’m sure he thought he could avoid any problems by doing the simple task of not bullying anyone.
At the end of the appointed 90 minute session, he had only finished about sixty lines. She told him he would be punished for the missed lines when he returned. Finally, she told him to pull his pants up and head home. He was still plugged and diapered with instructions to keep them on until he got home. We never reused anal toys, so the cost was always factored into sessions.
The following Monday, my friend that he bullied sat with me at lunch and told me how Tony had apologized for bullying him and promised not to do it anymore. He theorized that Tony was still in the closet and only bullied people to deflect from his sexuality. I kept the real reason to myself. Over the next two weeks, Tony went out of his way to compliment people and apologized to those he had bullied in the past. He genuinely seemed like a happier person after doing so, despite the reasons that triggered it.
At his follow-up session, he stood quietly as I reported on his progress. She told him she was proud of his progress, but that he still had punishment due. Once again, he was bent over the desk and cuffed. A longer plug with a prostate stimulating nub was inserted into his ass, then she used the same leather strap to blister his ass until he was wailing. This time, however, before applying the baby oil which would surely elicit an erection, she locked up his penis in a plastic chastity device. Finally, she put him into two diapers to increase the thickness.
Once again he was sent to the white board with instructions to finish his sentences and add another hundred for the delay. He spent over two hours writing out his lines 135 times. The entire time, the prostate stimulating plug kept his cock pressing hard against the chastity cage, which caused some rather comical discomfort. When our afternoon session canceled, she decided to keep him around another two hours cleaning the space. Afterwards, she removed the chastity and one of the diapers, before pulling up his pants and sending him home.
We both graduated about a month later. He returned for one more paid session a week after graduation, using his graduation money to pay for it. I don’t know if he continued to session with her, because I moved halfway across the country for college and started working with another pro-domme.
I have a few other stories about diaper fetishists I’ve seen over the years. I’ll try to share more when time allows.