Finance Bro to Diaper Brat
(Obviously, this is a work of fiction.)
It started with the rumors of a merger.
I worked at an investment brokerage. I was hired right out of U Penn. The firm paid to move me to Denver.
We traded derivatives. My division was doing great. Last year I got promoted. The promotion came with a significant increase in my base salary. The bonus was great, too. I was making more money than both of my parents. I bought a condo and a new car. Everything felt surreal. Almost too good to be true.
I met Owen the first weekend I was in Denver. That Saturday was my 23rd birthday. He messaged me first on Grindr. He knew exactly what he wanted. I was his type, too. I still lifted like when I was an athlete. I played lacrosse and football in high school. He was very forward about sex and kinks in our DMs. In person he was totally different. Very shy. Almost timid, actually.
Owen was hotter than he realized. He had no body hair at all. The tiny bit of facial hair he could grow was always clean shaven, too. His body was toned, but not overly muscular. His shaggy light brown hair flipped to the side of his face, every time he twitched his head to get it out of his hazel eyes. He was 19. Just a sophomore at UC Boulder. He had a swimming scholarship.
Our "situationship" was becoming more. We had been casual for a while. Very low key initially. Then we started spending weekends together.
Owen told me he still wet the bed. The evening routine was weird. His parents had rules about how Owen had to get ready for bed. He still followed them. I rolled with it. Just let my bedwetter boyfriend do his thing. The rules seemed super infantile, especially for someone in college who didn't even live at home anymore. Owen had to be diapered and in his pajamas at least two hours before bed. The diapers were thick. White and medical-looking at first.
Eventually, the rest of the story came out. It was a Friday afternoon. Owen had driven over from Boulder. He didn't have class. I took the afternoon off. I thought he was walking differently when he came in. He made some stupid joke. I used that as an excuse to playfully spank him. I expected it to sting a bit since he was just wearing gym shorts. Instead my hand landed with a soft "poof" sound. He wasn't wearing his regular boxer briefs. He was already taped into one of his diapers. It was about 2:30 PM.
The diapers didn't catch me off guard. I knew he was a bedwetter, after all. He already told me the story. Owen wore Goodnites Pull-Ups in elementary and middle school. But in 7th grade he outgrew them. His mom still bought them, for some reason. But his "night time problem" required more protection than Pull-Ups could provide. The transition to tape-on diapers coincided with puberty. That's when padding became more than practical.
I pulled his LuLu's down. He was wearing a diaper that was already wet.
"What, did you run out of underwear?" I teased, his shorts hanging around his ankles.
"Washing machine broke." He smiled, pretending like he wasn't lying.
"I doubt that, young man." I picked up his gym shorts off the floor and laid them on a chair in the kitchen. "You can have these back later."
"Nuh-uh!" Owen feigned indignation.
"It looks like somebody needs diapers anyway." I "checked" him, placing my hand on the front of his wet diaper.
I led him back to the bedroom. He took off his shirt and went down on me. Then I bent him over the bed and pulled down the back of his diaper. It was hotter than I thought it would be. That was our first "role play" session. Our initial foray into DDLB, I guess. It was also the first time we hooked up, when he was wearing a diaper, wet or otherwise.
Owen stayed in diapers that whole weekend. Something about it worked for me. And he was hugely into it, too. It seemed like something he wanted all along but was afraid to ask for.
We tried new things with diapers and role playing over the next six months. Chastity, spanking and light bondage with locking onesies. Owen usually was the sub. I was usually the dom. But we switched things around from time to time. The change of pace could be fun.
The brokerage announced "restructuring" in late spring. The layoffs started right after Owen's finals wrapped up for that semester. Owen was out of class and my "role" was "eliminated" in the first wave. My severance was enough to float me for six months. But it was a huge blow to my ego. I felt like I'd lost the core of my identity. I was laid off, along with more than with half the firm.
I didn't rush to apply anywhere else. It was the middle of May. This was the first time that Owen and I could spend that much time together. Owen's older brother helped me sort through the legal stuff. William was a lawyer, just like his father.
The job market had proven tougher than I thought. Most of the entry and mid-level investment banking jobs were being automated away. AI was changing the field I'd only broken into two years prior. Owen's older sister helped me sell my condo. Julia was a high-end realtor. An associate William worked with handled everything.
I actually made money on the condo, somehow. Like a lot more than I expected. It seemed like there would be serious tax implications if I didn't buy another one soon. But Owen asked his older brother to help me out. I was glad, too. At the time I was in a bad place. My psychiatrist in Denver diagnosed me with clinical depression and anxiety. The only reason I saw him before was to refill the ADHD meds that I'd taken since middle school.
William drew up paperwork of some kind. I just signed it. I didn't read it beforehand. It was Memorial Day weekend. Owen, William and the rest of their family were at their lake house in Telluride. I signed a power of attorney earlier that week. William created a trust and moved my assets around. He explained everything. This was a special kind of trust. I was the sole beneficiary with exclusive rights to the income that the assets generated. But I could not access the principal. The only person who could do that was Owen. I was fine with it.
There was one more piece of paperwork as well. William said that conservatorships weren't usually appropriate in these kinds of situations, but it might be an option with my medical history. It had fringe benefits, too. My insurance would be covered with some other expenses. That was a huge relief. It wasn't like I could go back on my parent's insurance.
My mom had retired and my dad died when I was in the 8th grade. I was absent for about half of the fall semester. There were problems when I went back to school. My grades were dropping. I was being "disruptive" in class. My childhood bedwetting even came back too. It was all humiliating. My mom said I was lashing out at home. There were other things too, but I don't remember them all.
Way back then a family friend arranged for me to be evaluated by a psychiatrist. I was diagnosed with mild autism (level 1), ADHD, anxiety and depression. There were a few other things, but they didn't seem important then. The point was to get extra time on tests and to have my absences excused. I got an IEP and a 504, plus all the medical excuses I needed for absences. I took the meds and went to therapy. I didn't like the SSRIs or the benzos. I felt like an empty shell on the mood stabilizers. But the stimulants really helped.
I didn't tell Owen about any of that until his brother asked about my medical history. I didn't understand why that was relevant to anything Owen's brother was doing. But William asked and I'd gotten over the humiliation by then.
William was going to file some kind of a petition. I had to talk to a psychiatrist that consulted with William on legal stuff. The shrink was old. Really old. She and I met about four times over the following week, for an "independent evaluation" and report for whatever William was doing. The shrink had my medical history and all the records going all the way back to when I was 13, when my dad died.
That shrink was exhaustive. She went through everything in my history. She asked me about everything. I thought I was going to die of embarrassment when she asked me if my bedwetting came back, after I was laid off. Truth be told it had. I didn't share that I was already wearing diapers at the time, because of the kinky shit Owen was into. She wrote new prescriptions for anxiety and depression. I didn't even ask for them. She scheduled follow up appointments for the next six months. I didn't want to read the report she prepared. William gave me a copy and said the odds were in our favor.
The petition was granted about a week later. William tried to tell me what it meant but I didn't really listen, because Owen was planning to move off campus the following semester. His parents bought a condo in Boulder. We both moved in. I was still unemployed. His parents gave us a few thousand dollars per month for expenses. After all, the principal in my "trust" was barely large enough to generate income.
The first check came in July, right after we moved in. It was for a few thousand dollars and I was going to cash it, but when I opened the envelope I noticed that Owen's name was on the account. I thought it was super weird, but whatever. I still asked him about it.
"Don't you remember?" Owen asked. "William filed the guardianship petition last month. I was appointed, so I had to be added to everything."
"What do you mean . . . . appointed. Appointed to what? To manage the trust your brother set up" I was confused.
"No that was already in place, silly." He kissed my forehead. "I was appointed your legal guardian."
"My what?" I knew what a legal guardian was. But I could not imagine how my younger boyfriend who was still in college could be the legal guardian of anyone. Much less myself.
"Yeah. It's like I'm your parent. Or your babysitter. William explained all of this. Remember? Memorial day weekend. We were both there." Owen acted like this was no big deal. "You're going to love what I ordered, too."
"Um . . . . what did you apply for?" I was blindsided.
"The benefits cover medical supplies. So, I got a few that I thought we'd enjoy." Owen laughed. "It will be like I'm babysitting you! "
"I am literally 23 years old. I do not need a babysitter." I argued, emphasizing the "not."
"Yes you do, diaper boy." He grabbed the front of my diaper and squeezed. It was so hot.
I could feel my dick straining in the chastity cage.
Owen bought the chastity cage before I sold my condo. I kept him in it at first and held his key on my key-ring. But he made me give the key back after I agreed to move in with him.
Right after I gave the key back, he pushed the front of his gym shorts to reveal an already-wet diaper. Then, after pushing the front of it down he unlocked the chastity cage I'd kept him in and laid it on the foot of our bed.
Owen walked back into his bedroom leading me by the hand.
"Lay back, kiddo." He instructed, positioning me at the side of our bed. I didn't comply. I was almost stupefied.
"I said lay back, brat!" He pushed me back onto the bed. This was a side of him I hadn't seen before.
Owen pulled my jeans and underwear off.
"Are you going to be a good boy and cooperate?" He took one of his diapers out and held it up. "Or are you going to get a spanking?"
I raised my legs up and rested them back down on top of Owen's shoulders. He slid the diaper under me and positioned the diaper under my butt.
He eased my legs down beside him and I tried to close them.
"Not so fast!" He stopped me. I saw him pick up the chastity cage and grab the key.
"Hey! Wait a second. What . . . . What are you doing?" I tried to protest as Owen put the first part of the chastity cage on me.
"You can still earn yourself a spanking, young man!" He reiterated, laughing.
He locked the chastity cage on me without further resistance. Then, he powdered me and put a glove on his right hand. After he lifted my legs, I felt him slip a Vaseline-covered finger inside my butt. He put one of our butt-plugs inside me. I was looking straight up at the ceiling when I heard the glove come off, and felt the front of the diaper brought up over my lower abdomen. The tapes came next.
I tried to sit up, so I could look down to inspect Owen's damage. All four tapes were expertly secured in place. But Owen wouldn't let me off the bed yet. He just took my shirt off.
Instead of taking his clothes off too, he walked to the dresser and opened the top drawer. That was "my" side of the dresser. I hadn't unpacked any of my clothing yet.
Owen took out a onesie. It was big enough for either of us. But it didn't look like the baby themed onesies he liked. This one was solid gray. It had sleeves and a zipper in the back.
"One foot in each leg." He instructed. Owen used a magnetic key to unlock the button that concealed the zipper running all the way down the back. He unzipped the zipper and held it in front of me.
"Owen . . . come on now." I had never been locked in a onesie before.
I stepped into the onesie and he pulled it up. The legs came halfway down my thighs, close to where the boxer-briefs I was wearing before did.
He put his hands on my shoulders and made me turn around.
I felt him zip the onesie up, from my lower back up to my neck. Then I heard the magnetic button covering the zipper lock in place, with the key he'd just used.
"We'll try these for a while, kiddo. You look so cute!" He kissed my forehead and "checked" my diaper. "Still dry!"
"Duh." I replied, sarcastically. "You just put me in all of this."
"Don't make me spank you." Owen cautioned.
Owen made me drink three bottles of water over the rest of that afternoon. He changed me once. But only to remove the butt plug before he drove us to Chipotle for dinner that night. The chastity cage stayed on. But I was wet when we left. I was still wearing the onesie. Thankfully it was covered by my jeans and a t-shirt.
The sex we had that night was the best since I met him. He liked everything better this way too.
That following morning he re-diapered me. I had really wet through the night. But it wasn't humiliating. He praised me for it.
I was his "kiddo" after that night.
Owen kept me diapered 24/7.
The chastity cage almost never came off.
There were more onesies, too.
Owen treated me like a 23-year old toddler.
Some of his friends even started to "babysit" me.
I got spanked whenever I didn't cooperate. Which was . . . often. I liked it when Owen did it. Not so much when it was one of the babysitters, though.
We started to get deliveries of medical diapers through insurance. An "incontinence, unspecified" diagnosis was added to my medical records in the weeks to come.
At least Owen didn't make me call him "daddy," although some of his friends who knew about our arrangement teased me about it.
