I've wondered for a long time if my mom knew I dressed. I'm gonna try to keep it short in a list format since it covers several years
1. When I was in middle school just hitting puberty I noticed my mom had stored some of her extra clothes in my closet which at the time had a whole half that wasn't used. I didn't really touch them because they were mostly tops and outerwear. She took them out after a while and put them in the guest room which housed most of her extra clothes. One day when I was searching the upper shelves of my closet I found a pair of white bikini panties I figured my mom had forgotten them there from when she cleaned out the closet. But now I realize she not only had a dresser and a closet to store them in the master bedroom as well as a fairly empty guest room closet and dresser to store them in. Anyways I wore these/washed them for a while. They looked a lot like my tightey whiteys which made me feel at ease trying them on.
2. As time went on I wanted another pair as these were worn out so when my parents went for walks or to dinner I would sneak into their room and try on panties. Eventually I saw a bra so I got into wearing those while they were out. I would wear multiple bras(probably stretching them out) her used panties so as not to avoid suspicion the spandex and often a pair of her boots. Eventually I wanted to wear a women's top to complete the outfit but I knew if I moved them around in her room she would know so I would sneak those out of the guest room where she stored the clothes she didn't usually wear. Eventually I got into her skirts and dresses that were stored nearby. My mom was a pretty forgetful person and would often leave her clothes thrown about the room so I would take pictures of where I found everything so I could put it back just as is. My mom never really asked me about this and I figure she never knew because of how careless she was about putting stuff away
3. One weekend in high school my parents went on vacation leaving me to myself of course I dressed but unfortunately after they returned I had left my moms purse on a table. I made up some excuse that I had needed a towel after spilling a bunch of water and I had grabbed a towel from their bedroom (where they store most of the towels) and the bag was inside it (they store bags in the same cabinet). I figured they wouldn't buy it but they would think I had a girl over since I was a teenage boy with the house to myself
4. When I was a freshman in college my mom used to do my laundry. I didn't own any women's clothes at this point. She would often mix my load with whatever was in the house and she'd separate them all while packing my stuff. One week I got back to my dorm and there were 7 pairs of my moms panties all stacked together on top of my boxers. I went home that week on Friday and my mom never mentioned them so on Sunday when I was gonna ask her to do my laundry I told her she had given me her underwear she laughed and said oh I was looking for those I was going to ask you. my brother made some snide remark and then we went on with our day. I do think 7 is a lot to not notice that you are missing but we come from a pretty conservative culture so I reasoned that even if my mom had thought that I had she would feel embarrassed to ask for her panties back.
5. Sophomore year in college I went to costco to buy supplies for school and I picked up a pack of boxers when i showed them to my mom she asked me if I was sure those were the ones I wanted which struck me as odd because they are boxers there isn't a big selection and also my parents don't usually ask me if I'm sure I want something because I usually don't ask them if I'm not already sure
6. Also sophomore year in college. My aunt stopped by she was moving to different country and she dropped off a box of stuff from her old house that she though we could use. It was all glassware and kitchen stuff wrapped in my cousin's clothes. I asked my aunt why she wasn't just sending the clothes to her daughter a 5 hours drive away. My aunt said they were from her goth phase and she would likely just throw them away. anyways my mom didn't want the stuff so she tole me to take a look some of the glassware to my new apt. Later when I visited my parents house the box was in the garage I sorted through the clothes but most of them were shockingly too small for me especially around the hips. So I took a couple skirts a few pairs of pants and the lone pair of panties which upon closer inspection was yellowed with urine and caked with discharge. In the weeks I would visit my mom she told me on a few occasions that she doesn't know what to do with the box and my cousin is never coming back for her clothes
7.In my last year of college i had my own room so I was free to underdress I just had to hide everything from my roommates who would frequently enter unannounced. I never took my laundry home during this time because I had a laundry machine in the house I was renting. however it might have been suspicious that I left almost all of my pairs of boxers at my parents house so that I would have no choice but to wear panties to class everyday
8.One day when i returned for the weekend I found a pair of deep blue bali high cut panties, and one of my dads socks on a table. I knew my mom had said she sometimes used my room to fold laundry but this struck me as odd. she usually would fold all the laundry downstairs on the couch while watching tv (which is next to the laundry room). The guest room right next to mine had the iron and steamer steamer so it would make more sense to either do it there or while watching tv as my room was barren without my stuff in it. As forgetful as my mom was particularly with clothes I thought this had to be on purpose. Even if she had done laundry she would have stacked all the clothes together not a pair of panties with my dad's sock both of which there would be a substantial amount of by laundry day. I mulled over it until sunday night when I figured **** it if she's testing me I might as well do it I ditched my boxers pulled up my big girl panties and headed out.
9. After graduating I lived at home for a year 6 months of which I studied for grad school entrance exams. I underdressed for most of this. I tried not to wear anything with too much lace or girly colors and I hid my bras and panties pretty discreetly in my room. my mom worked almost everyday so I would do laundry while everyone was gone.
10. One day I laundered a bunch of towels after going to a couple pool parties I laundered a few towels and I forgot to take them out of the dryer. When i woke up one day my mom asked me who had laundered the towels and I said I forgot and she said I folded them but I found a pair of girls underwear in the dryer with the towels. She held out a pair of my vanity fair bikini panties with lace. I told her i didn't know how they got there and she said she would ask my brother (who is gay) about them. I knew if it went to my brother I would never hear the end of it so I eventually told my mom that I had just taken everything out of my pool bag and thrown it straight into the wash. And maybe some girl had accidentally placed her underwear in my bag. My mom said well you can't return them and they are in good condition so we should donate them. So I put them in the large donation bag in the hallway near my room. Not sure she bought it but I think it was more likely that she thought I had slept with some girl at the pool party and she had left her panties with me. I started laying low trying not underdressing for a few months. I worried that even my granny panties were thick around the edges and were giving me pantylines
11. However after I finished my exam I wanted to get back into underdressing before moving out for grad school so i started underdressing everyday wearing my girliest of panties hot pinks baby blues tangas thongs g strings. I spent most of these months partying heavily often I'd return drunk and leave my pants on the floor. I entered my room on a few occasions and found my jeans carelessly thrown on the floor with maidenforn pink polka dot panties in them or pajamas with a sky blue vs pair in them. my parents and brother never entered my room so I wasn't too concerned but it still seemed very risky.
12.Eventually the donation bag had reappeared outside my room outside my room. Now it was filled with my moms various clothes It was very close to my room and bursting out of it was a double pack of Kotex light days pantyliners some kotex regular pads and and overnight maxi pad. I wondered why my mom was donating these now as she had gone through menopause years ago. I fished through the bag found a nice pencil skirt a tank top 3 of her really worn out barely there bikini panties and finally my pair of vanity fair panties. I knew my mom would likely not go through the bag again as it was full so I fished these out as I was heading off to grad school soon. A couple weeks went by and now I was leaving for grad school by the end of the week. I noticed my mom had removed her pantyliners and maxi pads from the bag but I figured the panties were so far down that she hadn't gone through the bag. But I wondered if she was testing me by putting the bag outside my door for so long. One day she asked me to take this bag to goodwill and donate it. It was weird the week before leaving for school my mom was handing me a bunch of her clothes. I fished out what I wanted and donated the rest.
13. We went shopping before I moved out bought almost everything except underwear. which wasn't surprising because my mom hasn't bought me underwear since high school. the first time I visited home however she asked me if I needed any clothes especially underwear she said I could just shop online and use her credit card to kohls. Which is quite bizarre for her as she insists all clothes shopping should be done in person. Although I had a few pairs of boxers that she had bought me from kohls in high school, she often told me how good kohls was for underwear. I knew she had bought almost all of her bras panties and hosiery exclusively from Kohls. I declined because it seemed suspicious that she wanted me to buy online and that whatever I bought would show up on her statement.
14. Since then the past couple of times I've come back she's told stories about 1. some time there was a man dressed like a woman in a movie theater that she went to with her sister and how it freaked her out. and 2. most recently she told a story when it was just the two of us about her new coworker who dresses like a woman and wants to be called a woman and how he has done a lot of great work for disabled people so in spite of "his private" life he's a great person.
I'm sorry for how long this is I guess it's kind of like a life story. So i guess my question is what are your thoughts on all of this. My parents especially my mom is a pretty hard republican. Aside from their political views my family belongs to a culture where being feminine for a man is a really bad thing and she definitely believes in that. When my brother came out my mom was devastated and my dad as well to a lesser extent. My mom has always wanted a daughter but my brother has never been into fashion or anything he's pretty disgusted with panties and bras and skirts etc. I really do think she would be averse to a crossdresser child but at the same time the original tighten whiteys the blue panties left in my room and the bag of donations all seem too convenient.
