My name is Ricky and I love your site. I figured it was time to write you a letter about my story of diaper domination, since I think some people might enjoy reading about it. I am a 19 year old boy that never had a diaper fetish until I was an adult. From the time I hit puberty, I knew I had a very strong submissive streak and often fantasized about all sorts of naughty things. The bossy, overbearing girls at school were the ones I lusted after. Nothing turned me on more than the thought of a strong girl bossing me around and making me do embarrassing and humiliating things. I spent a lot of time online looking at the web sites of professional dominants and learned a lot about BDSM in general.
On my 18th birthday, I used all the money I got for gifts to make an appointment with one specific professional dominant in the city. I will call her Mistress M. She even had availability that day, so I got in my car and met her at the address she gave me. I arrived at her house right on time and she invited me in. We sat in the living room and she asked me what sort of things excited me. When I explained that I just wanted to be dominated, she pressured me for more details of my fantasies.
Nothing specific came to mind and she suggested an introduction to BDSM session, to which I agreed. She told me to leave the donation on the coffee table and to follow her into the basement.
Her basement was quite large and there were all sorts of bondage devices and furniture that I recognized from her web site. She showed me the bathroom and told me to undress and wait for her when I was naked. She came back into the bathroom as I was pulling my pants off and swatted me on the ass. Once I was naked, she told me to bend over and place my hands on the edge of the tub. Glancing back, I saw her pull a disposable enema bottle out of her pocket and lube the tip. She inserted the tip into my ass and squeezed the bottle until it was empty. I felt the immediate need to poop, but she held the bottle there for a moment as she told me to use the toilet and make sure I was empty and clean before coming out of the bathroom. I emptied my bowels and then cleaned myself with wet toilet paper to ensure cleanliness.
Exiting the bathroom, Mistress M was waiting for me. She was holding a riding crop and snapped my ass with it after telling me to follow her. She led me to a X frame on the other side of the room and put leather cuffs on my wrists and ankles. Facing the X frame, she attached the cuffs to the eye bolts on the frame so I was in a standing spread eagle position. A blindfold was placed over my eyes. I heard her walking around for a couple minutes and then felt her presence behind me right before she stuck a lubed up plug into my ass. It felt gigantic, but I think it was more surprising than anything. I grunted when the wide part of the plug passed my sphincter and I heard her giggle.
She spent a fair amount of time with sensation play after that. I felt the riding crop fall across my ass, legs, arms, shoulders several times. She would alternate that with some tickling from a feather as she tried to find my ticklish spots. At one point she ran a wet ice cube around my nipples, armpits and balls. She was trying to see what stimuli got me the hardest to narrow down my desires. As much as I disliked the crop, every stroke made my cock stand hard.
After the X frame, she put me on the spanking bench where I was fully bent over and my cuffs were again attached to eye bolts on the bench. This time she used a thin leather paddle to spank my ass and upper thighs. It hurt like hell, but I think the knowledge that the pain was being inflicted by a dominant woman was the real turn on. In any other situation that type of pain would have me running for the hills. When she finished with the spanking, she helped me up off the bench and told me to crawl behind her.
I followed her on hands and knees to the other corner of the basement, where she picked out a leather strap-on harness and a penis shaped dildo about the same size as my own. She kept smiling at me as she fastened the dildo to the harness and then pulled it up around her pelvis and fastened it tight. She stood in front of me with the dildo sticking straight out and told me to lube it up. I looked around for lube, but she told me to lube it with my mouth. I took the faux penis into my mouth and tried to get it as wet as I could, knowing full well what was coming. She kept calling me a dirty little slut and would press her hips forward a bit to press the dildo further into my mouth. I think she was trying to make me gag a little, but I have almost no gag reflex and took the entire dildo into my mouth and down my throat. This seemed to please her as she kept calling me things like a good little slut and a talented whore.
After several minutes of cocksucking, she stood me up and had me bend over a nearby chair. My midsection was draped over the back of the chair and my hands were on the seat. The cuffs on my wrists were attached to eyebolts on the front legs and my ankle cuffs were attached to the back legs. She removed the butt plug that was still in my ass, which caused me to wince a bit. It was quickly replaced by her dildo. She worked it in and out slowly at first, but pumped it in and out faster and faster over the course of a few minutes. She fucked me for about ten minutes until seminal fluid was draining from my cock. It was one hell of a prostrate massage.
My ass was sore and raw as she unfastened me from the chair and removed the leather cuffs. She said our time was up, so it was time to get my dressed. She had my clothes folded on a nearby table and led me by the hand to the table and motioned for me to get up. I figured she was going to dress me, so I hopped up on the table.
Then she told me to lay down as she pulled an adult diaper out of a nearby drawer. It was mostly white, but had the word ‘baby’ written across the front of it. I later learned it was a Bambino diaper. She told me to lift my ass as she placed the diaper under me and said that kind of ass fucking might cause some bowel issues and she was just taking precautions.
The diaper was taped up tight and then she pulled my underwear over the top of that. It was a bit more difficult getting my pants up, but we managed. She insisted that I look at myself in the mirror before I left and it was clear that I was wearing a diaper under my jeans. Mistress M then walked me to the door and told me to come back soon. I intended to…
I had to stop at a gas station to remove the diaper before I got home, because I still lived with my parents. Mistress was right about the diaper too. There was a little bit of leakage, but not much.
I saw Mistress M a couple more times over the next few months. I would have seen her every week, but I had to save money between visits. Then one day, she emailed me instead of the other way around. She told me that she was going to a kink convention and needed a submissive to assist her. It sounded exciting, but I told her I was too concerned with being recognized. When she promised she would hide my identity, I agreed.
The convention was in the same city as Mistress M, which was about 40 miles from where I lived. She said we would be staying at her place and I would be her assistant/slave for the entire weekend. The convention was from Noon to Midnight Friday through Sunday.
I arrived at her place at 10 am on the first day of the convention and Mistress took me to the basement to get rid. I was expecting a hood or something to hide my face, but she had other plans. We started much the same way as most of my visits started – with an enema. This time it wasn’t a small disposable bottle. She gave me a full two quart enema and then left me in the bathroom to clear myself out. Up on the table I went after that as she gathered a few items.
First she added a chastity device to my cock that was locked by a small padlock and the key was placed around her neck. Then she inserted one of her larger butt plugs. She commented that it was softer than the other, so I could wear it longer without issue. Next, she pulled out two of the familiar diapers and taped them on me tightly. The double thick diapers were covered by a pair of pink plastic panties that had a chain through the waist, which was also locked with a padlock and the key joined the key to my chastity.
Mistress helped me off the table and showed me a black latex maid outfit that she intended for me to wear. She pulled a set of petticoats up my legs and around my waist. Then a bra with built in breasts came next. This was followed by the maid outfit being pulled over my head and fitted over the petticoat and fake breasts. The petticoat made the dress flare out and after glancing in the mirror, I could see that it did very little to hide the diaper underneath. A pair of lacy ankle socks was added to my feet with a pair of mary jane shoes over that. Once I was dressed, Mistress spent about 45 minutes doing my makeup and fitting a wig to my head. When she was finished, she showed me the results in the mirror and even I didn’t recognize myself. A pacifier was stuck in my mouth and she told me to wait in the living room while she finished getting ready.
Being left to my own devices was a torture in itself. This humiliating attire was really getting my blood flowing and I began to get hard. It was then that I realized the true nature of the chastity device. Getting an erection was just painful. When Mistress M came to get me, I was standing with my legs spread trying to relieve some of the pain. She gave me a little lecture about how she used the chastity cage to make sure I was focusing on her and not my own pleasure.
It was time to go and Mistress helped me put on a long trenchcoat to cover myself. She said she didn’t think it was necessary, but the convention rules were no fetish wear outside of designated areas. As much as I enjoyed the embarrassment and humiliation, I was glad for that rule.
We spent the first few hours of the convention walking around looking at the stuff people were selling. Mistress bought a few items and I had to carry them. We ate lunch at the buffet inside the convention center and then Mistress said we had an appointment. It turns out she was one of the first day presenters and was doing a presentation on “Age and Gender Roleplay” and I was her prop. She had me standing on stage as she discussed all the aspects of gender roleplay and would point out to the crowd that I was a male, but made a very pretty sissy girl. When she got to the subject of ageplay, she made sure to point out that I was thickly diapered. At one point she had me hold up my dress as she unfastened the lock on the plastic pants and pulled them down to my knees with the diapers right behind them. She noted the use of the chastity device and how it kept my focus on her and not my own pleasure. When someone from the crowd asked about stinky diapers, she turned me around and had me bend over to show everyone the plug in my ass. At this point, a woman from the crowd said I had a very spankable butt, so Mistress invited her up to give me a few swats. She swatted me with her hand a couple times and then Mistress handed her a leather paddle and told her to turn my ass pink. She gave me about ten swats and then returned to the crowd as people clapped. Mistress pulled my diapers and plastic pants back up and had me turn to face the crowd again. The humiliation was making me hard again and I was almost in tears from the pain of my engorged cock pressing against the device.
The rest of the convention was mostly uneventful. Mistress spoke to her friends at great lengths while I stood by waiting for orders. The last few hours of each day was a large play party and Mistress made great use of me. She would lock me in the stocks and let her friends spank me or fuck me with her strap-on. Some of them would test out new items they purchased with me as their guinea pig.
During the play party on the second night, Mistress told me that she would remove the chastity device for the rest of the weekend if I gave her friend a blowjob. Although I consider myself straight, I had often fantasized about being dominated by a man. Coupled with the fact that the chastity device was driving me insane, I agreed. She took me over to her friend who seemed delighted and we went to a semi-private area off the corner. He was already semi-hard when he pulled his cock out and I got down on my knees and took him into my mouth. It only took me about two minutes to make him cum and Mistress insisted that I swallow every bit. It tasted nasty, but it made me feel good to see her pleased by it.
Good to her word, she pulled down the diaper and removed the chastity cage. The rubbing on my cock as she removed it got me hard instantly, which made it difficult to pull the diaper back up. She told me to make it go away or I would be punished, but I couldn’t stop it. She kept flicking it with her fingernails, which just made it worse and in less than a minute I had an involuntary orgasm which squirted semen onto Mistress’ outfit. After wiping it off, she pulled me over to a nearby set of stocks and locked me in. She spanked me harder than she had ever spanked me before and my ass was on fire. Tears were streaming down my face before she was done. She told me that letting me out of the chastity cage was a mistake and proceeded to reattach it before pulling my diapers back up and locking my plastic pants. I was told I would be staying in the stock until the party was over in three hours.
After 30 minutes, my back was aching. I didn’t think I could possibly stay this way another 2.5 hours, so I asked Mistress if she would let me out. She said I wouldn’t learn a lesson if it was that easy. She did give me an option though. She said she would take 30 minutes off my time for every blowjob I gave while in the stocks. I agreed and a minute later she hung a piece of paper near by head that said “Free Blowjobs”. Almost immediately the first taker walked up and asked if it was for real. Mistress told him it was, but that he would need to wear a condom. She handed him a condom as he pulled out his cock and rolled it down his shaft. He placed the head of dick at my lips and I sucked the best I could with limited movement. It only took him about two minutes to cum. It was another five minutes before another taker walked up and we repeated the same steps as before. One hour off, a little over an hour to go. The third guy was already in line waiting for his turn and again he was a fast cummer.
I only had 35 minutes left when the final guy walked up. He had a monstrous cock that barely fit in my mouth. I had no control as he basically just fucked my mouth for fifteen minutes before finally cumming. He took a lot longer than expected, so it really only took 20 minutes off my punishment. Mistress let me out of the stocks as he walked away and thanked me for the entertainment. I promised to do better if I could.
After that convention, I no longer had to pay for Mistress’ services. I spent nearly every weekend with her as her personal assistant. I am kept in chastity when with her and diapered full time. She often uses me when her clients are looking to session with another submissive. I graduate from college in three years and Mistress has already expressed interest in me becoming her full time slave boy. I can’t wait.