Dear Auntie Helga,
I was 19 when I was first introduced to chastity. It came when my girlfriend and I were talking about moving in together. She had been on my computer and had found a large stash of porn sites in the history and was appalled. So her stipulations were that I would have to be chastised and that we would have to sleep in separate rooms. I reluctantly agreed. The day we moved into our first apartment she had me strip down and then pulled out a black chastity device. After I calmed down and my penis softened she fitted the device on me and then put the lock on. She told me that she would be keeping the key.
Of course I did nothing but complain for the first two weeks and that was when she had finally had enough of my whining to be let out and allowed to at least play with myself. She grabbed me and pulled me over her knees. I was shocked at how strong she was. She began spanking me. I laughed at first but after twenty or thirty smacks with her hand I started to feel a slight sting. Then she grabbed her hair brush and began spanking me with that. I struggled to get away but she held on strong. I could really feel her hair brush even through my jeans. She stopped at one point and told me to stand up. She started unbuttoning my pants. I tried protesting but she was persistent. After she had my pants down she pulled me back over her knees and started scolding me. After she scolded me she started with the spanking again. At one point I just about fainted from the pain. I kept begging her to stop, but even after I was crying she continued. When my body eventually became limp she slowed up on the spanking and continued a little while longer. When she finished spanking me she made me stand up and I went to pull my pants up which was answered with another smack of the hair brush.
She grabbed me by the ear and made me waddle over to the corner. She made me stand there for an hour. When the hour was up she made me kneel in front of her as she sat in a chair. She told me that if I whined about the chastity any more she would spank me each and every time. She scolded me for being a perv in the first place and that it was because of me that she didn't trust me without the chastity. After the scolding she did give me a big hug and told me that I needed to go to my room and think about things for a while. I stood up and pulled my pants up with a wince as I pulled them over my butt. I went to my room and came to the realization that my butt was to sore to be able to sit so I laid face down on my bed. Some time passed and my girlfriend came and got me for supper. She knew I was sore so she was nice enough to put a pillow on my chair. We sat in silence for the better part of the meal, when she asked me if I was going to whine about the chastity any more. I told her no. She asked me if I understood that if I did I would be spanked again. I said yes I understood. She told me that she would decide when I would get out of the chastity and that I needed to earn her trust on it. She also told me that she liked knowing that my body was being saved for when we were to get married.
Every week afterwords I was tied to my bed and the chastity was taken off and my groin was shaved bare. Then it was right back into the chastity device. One day after shaving me I noticed her pull out a different chastity device this one was clear. She told me that it was also smaller, and when I started to complain about that fact she lifted my legs and began spanking me. This was the second spanking that she was giving me and I couldn't even resist as I was still tied to the bed! She spanked me with her hand at first and this time I felt the sting immediately. She stopped at one point and walked out of the room only to return with her hair brush again. I screamed and cried for her to stop but it did no good. She kept spanking me until I went limp. She put the new chastity device on me and scolded me. She then left me tied to the bed and walked out of the room closing the door behind her. She left me there for almost three hours.
When she untied me she made me stand in front of her for another scolding. She laughed at one point telling me that I was such a sissy boy since she was able to spank me to tears. She then told me to stay where I was until she came back. When she did come back she had a pink thong in her hands. She told me to put it on. When I started to stammer a bit she gave me another few quick swats with the brush. She told me that since I was a sissy boy I should be wearing panties but for the rest of the night I would be wearing this bright pink thong and no pants that way she could see the beating she gave me. After supper that night she told me to do the dishes and when I was done I could stand in the corner until bed time. I went to bed wearing nothing but the pink thong.
The next day when I came home from work she told me to strip naked. I did as I was told. She then told me to throw my boxers away. I asked her why, all she did was pick up the hair brush and I knew better. I immediately threw them away. She pulled out a bag from the side of the chair that she was sitting in. She told me that because I was being such a sissy I was going to start dressing as a sissy. She pulled out a bunch of panties and nighties. All pastel colored of course. Some had bows on them others had lace. She picked out a pink nighty and matching panty. The panty had a small bow on the front of it along with some lacy frills across the butt. She handed them to me and told me to put them on. I did so very slowly. It was humiliating. After I had them on she began to laugh at me which caused me to burst into tears and go running for my room. She followed of course. She sat next to me as I laid on my bed and cried. She stroked my hair and told me that I shouldn't be embarrassed about being a sissy but that I obviously was since I was laying there crying just from wearing girls clothes. She told me that from then on every morning she would pick out my panties for me and every day when I got home from work I was to strip down to the panties and face the corner by the door, she would come and get me and that she would have my night time outfit picked out.
Of course the next day when I got home I walked right into the apartment and without hesitation was pulled over my girlfriends lap for yet another harsh spanking.
Within two years a lot changed for me. Most of my male clothes were thrown out and replaced with girls clothes. My socks became anklets. On the weekends I wore dresses styled like a little girls dress. During the winters I was dressed in footed jammies instead of nighties for bed, all of course had very girly prints on them. My bedroom slowly changed and became that of a little girls. With pinks and whites being the dominant colors. Even my chastity was changed out for an even smaller pink one. My girlfriend had taken complete control of me. I was now very sissified, doing all the house hold chores, and doing anything she told me to even running her bath and turning down her bed for her every night.
On her 21st birthday I was allowed to wear boy clothes but only because I was to chauffeur her and her friends around all night. Every time my girlfriend got out of the car she made sure to remind me that I was wearing panties and a bra and that if I didn't want her friends to know I had better behave.
When my 21st birthday came around I was allowed to wear boys clothes out and go and party. I was completely drunk by the time we got home and had a hard struggle putting on the nighty she had picked out for me. The next morning when I woke up my life changed again. I woke up in a wet bed and to a very mad girlfriend. I received a very excruciating spanking and plenty of corner time. When she scolded me she informed me that since I peed all over the bed and the cute nighty and panties that she had so lovingly bought for me, that I would need to be diapered at night.
I tried to argue against her telling her that it was just from drinking to much, but she had none of it. I was spanked again and spent more time in the corner. She told me to go and take a bath and that she would be out for a little bit and when she got back I had better be in the corner holding my peed in panties and nighty. When she got home, and told me to turn around I seen her holding a bag of adult diapers in one hand and another bag in the other which contained powder and cream and wipes. She told me to put the nighty and panty down and lay down on the floor. I refused and got spanked again for the third time that day.
As I laid on the floor afterwards I was told that I would wear whatever she told me to and that since I peed the bed like a baby I obviously needed to wear diapers to bed. I was told that I was not allowed to use the bathroom while being diapered and that I was not allowed to touch the diapers. Every morning she would remove my diaper only if it was wet and that if it wasn't I would be wearing it till it was. The first night I couldn't bring myself to pee in the diaper and come morning had to stand in front of my girlfriend as she scolded me and then made me stand in the corner until I wet the diaper.
Once it was wet she made me stand there for another hour before removing my diaper and telling me to shower. It was back to panties for the day until I got home from work. I did as always and stripped to my panties and stood in the corner until my girlfriend came and got me. She led me into my room only to find instead of another pair of panties, a diaper was in its place. I could do nothing but cry. My girlfriend had a fix for that and immediately put a pacifier in my mouth. She then took me by the hand and laid me down on my bed and powdered and diapered me.
I have not had an orgasm since I was 19 years old and have been in diapers since I was 21. When I turned 25 my girlfriend decided to put a catheter in me so I was fully diaper dependent. The catheter is still in 7 years later so I'm sure I am incontinent at this point. I have not used a toilet for anything in 7 years. Of course my girlfriend mocks me and teases me all the time. When I am out of the house She likes to remind me that no one knows about me, but she might just be willing to expose me to everyone if I don't behave. When in the house I am a full on sissy. I have an anal plug inserted every morning that I wear while I am at work. My paychecks go directly into her account.
I have never been very happy about my situation but my girlfriend is very pleased with it. She gets anything and everything that she wants whenever she wants it. I don't ever see my life changing back. I will forever be her diapered sissy slave.
Thank you for your letter Trevor. I suppose you could try seeing her control as a good thing, she obviously cares for you, she has stayed with you all these years and has been trying to help you by controlling your body. Sure there were some rough times to start with but now you have come to the realization that you are her sissy, that you belong.