When it comes to feminization, I am fairly conflicted. Sure, I have lots of fantasies about it, and I have a fairly good wardrobe from which to chose. However I frequently have to convince myself that being dressed is OK.
As a child I remember trying on my mother's or sister's clothes when I was so young it wasn't even sexual. As I went through puberty I would occasionally masturbate wearing a pair of panytyose or something similar. Often times tying myself up while doing so. As soon as I would cum, I would be so ashamed and humiliated. I would swear to never touch another piece of women's clothing.
When I was a teen I would steal panties from the dresser of a friend's sister, or a local store. I would wear the panties occasionally and keep them hidden away. Back then, my go to method of masturbating was me lying on my stomach and rubbing my cock into the mattress or a pillow. When I got in the mood to use the panties I owned I would put them on. I would tie my ankles together with rope, a belt or a tie. I would then tie my knees together. I would gag and blindfold myself and then roll onto my belly. I would take another piece of clothing like a shirt. I would put my wrists in the arm holes behind my back and I would twist my wrists spinning the shirt until it had my hands restrained. I would hump the mattress and edge myself until I couldn't take it any more and would then have an orgasm. I would be lying in my cum until I could free my arms. Eventually I would go through the same shame and humiliation and throw everything away.
As a young adult, I started having partners that I could share my fetish with a bit. This allowed me to re-acquire some feminine items without having to hide them too much. It was still very mild compared to today. But when a breakup would occur I would discard the items in shame yet again. This was in the days before the internet, so I had no clue how widespread crossdressing was.
This cycle would repeat itself over and over. As I got older my dressing in women's clothes got a bit more advanced. I acquired makeup and would very occasionally dress and put on makeup. The biggest humiliation I would experience would be if I dressed, put on makeup, tied myself up and came. I would have major post orgasm drop, and would start to clean up. I would see myself in the mirror with makeup that takes forever to clean up. I would feel like such a freak of nature. I would have clothes that would need to be hidden. A few days later I would be ok, but it would be months before I would do this to myself again.
When I was married, my wife somewhat encouraged my dressing. Even though she encouraged it, I hid a lot from her. I traveled at the time. I would frequently go on a trip and as soon as I got to my destination, I would hit a Walmart or Target and buy some pantyhose or stockings. I would wear them out to dinner and when I was back in my room. Those days I masturbated 2-3 times a day. I would throw the clothes away before I got home. Several times in my marriage, she would have me dress more often, but it would ebb and flow. I never got the feeling she really liked it. After we split, I took every bit of kink related items to a storage unit. If there was one thing I learned over the years, it was that this need would come back into my life.
That takes me to my current relationship. Not long after I met Mistress I was in the storage unit getting some kinky items to show her, including clothes. Once Mistress found out about the clothes she made me put on every single item of women's clothes I owned. She put the clothes into 2 piles, one I could keep, the other I had to get rid of. She said that she wanted me to be her classy and sexy girlfriend, not a tramp (although I do believe slutty occasionally has a place). For the next few months, Mistress had me dress frequently. When we would go out to the movies, I had to be wearing panties, garters and stockings. When I would come over to her house she told me what to wear under my clothes. She bought me nighties to wear at her house. At my house we would have elaborate nights with me in full dress, makeup. We would have dinner and drinks. Mistress would make me pose while she took pictures of me. Then we would have sex, frequently with her taking me with her strapon. I felt like her girlfriend when we did that. She allowed me to start accepting being dressed in women's clothes for the first time in my life.
Yesterday Mistress had me wear something feminine "top and bottom" under my male clothes. I chose a pink camisole, and pink panties. At our friend's house for brunch Mistress kept pinching my sore nipples, hitting me in the balls and reaching into my shirt to remind me of my camisole. When we got home I started to strip so I could get back into my dress and heels. Mistress stopped me when I was just in my panties and camisole. She told me if I stayed that way I could skip putting the dress and heels back on. Since I was buzzed from brunch I went with it. Looking back, I am embarrassed that I paraded around for hours that way.
Today, I am sitting at my desk in a black and white dress with black boots. My head's spinning after reminiscing about my past. I am still conflicted, but I think that is a good thing. I will never be one that wants to "show off" my dressing. I will always be a bit reluctant to be dressed. I am glad I don't fully enjoy being dressed. I live for the mind-fuck. The shame and humiliation is what does it for me. The threat of being dressed in public. Mistress treating me like a woman. Seeing my feminine self in a mirror when I feel masculine puts butterflies in my stomach.
All of that being said, Mistress has assured me that she truly does enjoy seeing me dressed feminine. That's important to me as if she didn't then this wouldn't be fun. Having her tell me that she now expects me to be dressed 24/7 at home is a great mind-fuck. Adding shoes to my outfit made it that much more real. If she decides to add anything else I am sure it will have the same effect. The more she pushes the more I am in awe.
Since I am conflicted, having to decide what to wear causes me sensual stress. I feel very controlled and erotically humiliated. At the end of the day, I think I have the perfect balance of acceptance and reluctance and that make it work.
What I really have is the greatest Mistress aguy girl like me could have.
As a child I remember trying on my mother's or sister's clothes when I was so young it wasn't even sexual. As I went through puberty I would occasionally masturbate wearing a pair of panytyose or something similar. Often times tying myself up while doing so. As soon as I would cum, I would be so ashamed and humiliated. I would swear to never touch another piece of women's clothing.
When I was a teen I would steal panties from the dresser of a friend's sister, or a local store. I would wear the panties occasionally and keep them hidden away. Back then, my go to method of masturbating was me lying on my stomach and rubbing my cock into the mattress or a pillow. When I got in the mood to use the panties I owned I would put them on. I would tie my ankles together with rope, a belt or a tie. I would then tie my knees together. I would gag and blindfold myself and then roll onto my belly. I would take another piece of clothing like a shirt. I would put my wrists in the arm holes behind my back and I would twist my wrists spinning the shirt until it had my hands restrained. I would hump the mattress and edge myself until I couldn't take it any more and would then have an orgasm. I would be lying in my cum until I could free my arms. Eventually I would go through the same shame and humiliation and throw everything away.
As a young adult, I started having partners that I could share my fetish with a bit. This allowed me to re-acquire some feminine items without having to hide them too much. It was still very mild compared to today. But when a breakup would occur I would discard the items in shame yet again. This was in the days before the internet, so I had no clue how widespread crossdressing was.
This cycle would repeat itself over and over. As I got older my dressing in women's clothes got a bit more advanced. I acquired makeup and would very occasionally dress and put on makeup. The biggest humiliation I would experience would be if I dressed, put on makeup, tied myself up and came. I would have major post orgasm drop, and would start to clean up. I would see myself in the mirror with makeup that takes forever to clean up. I would feel like such a freak of nature. I would have clothes that would need to be hidden. A few days later I would be ok, but it would be months before I would do this to myself again.
When I was married, my wife somewhat encouraged my dressing. Even though she encouraged it, I hid a lot from her. I traveled at the time. I would frequently go on a trip and as soon as I got to my destination, I would hit a Walmart or Target and buy some pantyhose or stockings. I would wear them out to dinner and when I was back in my room. Those days I masturbated 2-3 times a day. I would throw the clothes away before I got home. Several times in my marriage, she would have me dress more often, but it would ebb and flow. I never got the feeling she really liked it. After we split, I took every bit of kink related items to a storage unit. If there was one thing I learned over the years, it was that this need would come back into my life.
That takes me to my current relationship. Not long after I met Mistress I was in the storage unit getting some kinky items to show her, including clothes. Once Mistress found out about the clothes she made me put on every single item of women's clothes I owned. She put the clothes into 2 piles, one I could keep, the other I had to get rid of. She said that she wanted me to be her classy and sexy girlfriend, not a tramp (although I do believe slutty occasionally has a place). For the next few months, Mistress had me dress frequently. When we would go out to the movies, I had to be wearing panties, garters and stockings. When I would come over to her house she told me what to wear under my clothes. She bought me nighties to wear at her house. At my house we would have elaborate nights with me in full dress, makeup. We would have dinner and drinks. Mistress would make me pose while she took pictures of me. Then we would have sex, frequently with her taking me with her strapon. I felt like her girlfriend when we did that. She allowed me to start accepting being dressed in women's clothes for the first time in my life.
Yesterday Mistress had me wear something feminine "top and bottom" under my male clothes. I chose a pink camisole, and pink panties. At our friend's house for brunch Mistress kept pinching my sore nipples, hitting me in the balls and reaching into my shirt to remind me of my camisole. When we got home I started to strip so I could get back into my dress and heels. Mistress stopped me when I was just in my panties and camisole. She told me if I stayed that way I could skip putting the dress and heels back on. Since I was buzzed from brunch I went with it. Looking back, I am embarrassed that I paraded around for hours that way.
Today, I am sitting at my desk in a black and white dress with black boots. My head's spinning after reminiscing about my past. I am still conflicted, but I think that is a good thing. I will never be one that wants to "show off" my dressing. I will always be a bit reluctant to be dressed. I am glad I don't fully enjoy being dressed. I live for the mind-fuck. The shame and humiliation is what does it for me. The threat of being dressed in public. Mistress treating me like a woman. Seeing my feminine self in a mirror when I feel masculine puts butterflies in my stomach.
All of that being said, Mistress has assured me that she truly does enjoy seeing me dressed feminine. That's important to me as if she didn't then this wouldn't be fun. Having her tell me that she now expects me to be dressed 24/7 at home is a great mind-fuck. Adding shoes to my outfit made it that much more real. If she decides to add anything else I am sure it will have the same effect. The more she pushes the more I am in awe.
Since I am conflicted, having to decide what to wear causes me sensual stress. I feel very controlled and erotically humiliated. At the end of the day, I think I have the perfect balance of acceptance and reluctance and that make it work.
What I really have is the greatest Mistress a
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