Who has been caught crossdressing?

Who has been caught crossdressing ,if so who caught you and what was their reaction

I have not, but the possibility of it is exciting! I wear panties or feminine underwear for men under my regular clothing. Being noticed while changing at the gym or peeking out of my pants when my shirt rides up has occasionally happened but I not had anyone remark on it. My wife knows about my panty wearing so being caught by her is not a thing.

My first wife , Mattea would buy me "questionable" underwear , and encouraged me to wear them openly around the house , She started with very tight rayon underwear with cute saying's and then stepped up to frilly , you can't mistake these for anything else , silk very tight very reveling underwear ,,,, that took up one corner of my dour . Once when they were the only choice as the wash hadn't been done , I picked the least offensive pair and went for a ride with the "bro's" . I quickly realized this was a mistake ,,,,,,, When I returned home ,,,,, all those underwear started disappearing .

I rode with a "club" ,,, I had responsibility's . I had a reputation that had to be maintained at all cost . If it became known that I liked ,,, or even unthinking wore such underwear would have brought it all down . It later became known that some of the ladies came up with this to show their influence and control over their men . Dirty Jack was the only one to pull it off and made it show his love for his "old lady" .He pulled up to Holtville air strip { a drag racing strip} peeled off his colors ,,, threw them under his bike to soak up the oil he was leaking ,,,, pulled up the hip huggers he was wearing until they were showing above his pants and called for his wife , hugging and tickling her until she started screaming ,,, It gave us all a good laugh and most of the ladies confessed what they had been doing .

So I don’t know if I been caught or not because I don’t have any choice of what I wear apart from work even then I only wear a work uniform.

My friends know that and except it I often wear clothes that are not worn by males. For example I don’t have any underwear and socks that say male.

I only have tops that say toddler thy have snaps on the shoulder or are totally female looking.

I only have joggers that are unisex or female. My night clothes are nighties or pjs that look toddler.

I often wear frilly over pants apart from work wear I wear panties with a pad over my diaper.

I wear frilly socks or knee socks both female and it’s depends on what I get out of the dresser

So the likelihood of getting caught is pretty high but then again my friends are more likely to have told them that I wear them because they don’t react like they didn’t know.

My family has recently been allowing me to choose more and calming things down due to the age of my father and my family saying I need to be more independent for my next move in life .

But I am always going to be a male sissy baby rather than trying to be a little girl.

Most of my clothes are that of a sissy rather then a lady apart from what I wear to work

I prefer the sissy baby look than the girl look so wearing frilly clothes and little dresses that don’t hide my over thick diapers.

I growing my hair out and then I going to put bows in apart from work.

When I was a teen my dad came home unexpectedly and caught me to a degree . . . I had been wearing my mom's panties and lingerie but when he opened the door they were all on the side of the bed out of view so he just saw me sitting on their bed naked . . . he quickly shut the door and was like "oh I picked up some donuts" and left. Nothing was ever said about it.

I work some navy blue silky and lace panties to a salon/spa once for a facial and haircut. Wasn't expecting her to ask me to undress for the facial. She left the room and asked me to undress to what I felt comfortable with so I went to panties and got under the blanket on the table (she left the room during this). At the end of the facial she wanted me to put on a robe for the next part and she held it out for me. I stayed on the table not wanting to get up but when she asked a second time I didn't really have a choice. She just kind of smiled and never said anything about the panties. But with the lace they were unmistakably panties.

Since then not really. I'll wear panties sometimes when I get massages but always something that could be "perceived" as men's underwear.

My wife saw some unusual accounts when she innocently ran our credit for a surprise auto purchase. It didn’t take her long to connect the dots and life has changed forever. In retrospect it was for the best.

So fortunately/unfortunately I'm still not sure, I got caught with my girlfriend's panties, stockings and a sexy mid-length(?) skirt on. I hadn't had time to try on her bra and sweater before getting caught. I was sniffing the sweater's armpits, sometimes my girlfriend seemed to, for one reason or another not worn anti-perspirant/deodorant. Unfortunately she had worn a very feminine smelling deodorant, but there was a faint armpit odor. I was trying to figure out which side had more armpit scent when I got caught. Just to set the tone a little, my girlfriend was a little taller than me in medium heels, and maybe tall as me (6 feet) without shoes, at the time I weighed about 155lbs, she weighed about 120lbs. When she was in her teens and early 20's she was a model for Harley Davidson. So when her sister caught me, it was incredibly akward embarrassing and arousing. She just started laughing. She didn't get the same genes my girlfriend did. She was about 5'4 and 135lbs and dressed like a farm wife. (Because she was?) She sort of laughed and inhaled, staring at me, and being she couldn't exactly leave, her ex-husband dropped her off, I guess she felt we should just be adults about it and talk. She asked if they were her sister's clothes, I said "the t-shirt is mine"... She kind of snorted. "Well I'm surprised you don't have her heels on, her feet are big enough!" She tried to joke. I laughed and said "she has big feet but her shoes don't fit me" I said. Then came the real questions. "Why are you wearing her leather skirt and stockings? "And panties! She added after lifting the skirt high enough to check. I yelled "well it's a good thing, what if I hadnt been?" "I guess I would have seen your bare ass." At this point she was too calm and I was too wound up. "Well?" "Well what? Well why am I wearing xxxxx's panties and skirt? I don't know, I saw the panties, smelled them and put them on and just kept going I guess". "Do you like it?" "I don't know what to say, can I get changed?" I asked. "Go ahead, I'll wait." Came the reply I knew was coming. She always had a crush on me and I knew she was enjoying this. "Can you wait in the living room like a person?" She shook her head and held out her hand. "What?" I thought she wanted to hold hands or something weird. "Panties, give me xxxxx's panties." She said with sass in her voice. I had enough and wanted to get to the bottom of what we were doing. "Why would I give them to you, I got them out of the laundry basket and the skirt was on the bed I capable of putting them back where I got them" I told her. "I'll tell xxxxx you were stretching her leather skirt out, by wearing it!" She won't care, she wears my, never mind.. What do you want Denise?" "Put the sweater on and let me see how you look". "And then we're done, you'll let me change?" "Yep" I grabbed it and put it on, it had stretched out boob spots in the front and was a little snug everywhere else. I turned around and showed her. "Okay, now we're done, let me change, why are you here so early anyway?" "I am without a car so I got dropped off when I could get a ride. Go ahead and change." "Fine." I was not, and am not, the shy type, so I decided I would start stripping and she would get embarrassed and leave. I took off the sweater and my t-shirt rolled up with it. I was pulling my t-shirt back down and I felt her grabbing my cock and grinding against my butt! "Denise what the fuck?" "What? You guys are broke up anyway." I gave in, she was a little cutie in her own way and Ms. Snot wasn't the have sex while you are broken up type anyway. I leaned over and kissed her, she seemed surprised but kissed back. She moved behind me again and pulled up the skirt, and pulled down the panties! She knelt on the floor and started sniffing my ass! "Denise what has gotten in to you?" Xxxxx said your ass always smelled good, well for an ass.." 'You guys talked about our sex life?" "She is my sister" She reached around and grabbed my cock, buried her nose in my cheeks. She started pulling the panties down, and I turned to face her. She grabbed my cheeks and pulled me toward her face, my balls were apparently face height because she started licking them. My cock was stiff against her forehead, she stuck some fingers in my asshole and I nearly spewed semen across the top of her head. I pulled her up but she didn't take her fingers out. "Lay on my lap" she told me. I was confused and horny, asked if she meant the bed or where? She let go of me and sat on the padded chair. "Right here". When I stepped over to her the panties fell around my ankles. She chuckled, and guided me across her lap. I was fully expecting a spanking, instead she went back to anal penetration with probably 3 fingers this time. She asked if I liked it, I said "obviously" which apparently came out snarky because this was to be the first time I got my asshole fisted. No lube, No undue pain, just bliss. I rubbed against her thighs and she just kept fucking my ass with her fist and wrist, in and out, in and out until I spewed hot sticky semen on my legs, her jeans, the leather skirt and the plushy chair. She got up almost as quickly as I did. "We have got to clean this up before Xxxxx gets home!" I agreed and apologized for not reciprocating the orgasm. She said "I got what I wanted". With a smile she took the skirt to the laundry room to clean it. I put my clothes on, tried to clean the semen off the chair, not very successfully, and that was the end of the whole deal. I moved out, Denise never talked to me about the afternoon of embarrassment and semen, and Xxxxx married the guy she had been screwing behind my back... (I think it was a height problem, her new boy toy was 6'7'.). I will never forget it as it was a very weird, very embarrassing, very good afternoon.

I was a young teen, an only son with four sisters, I was the oldest. My sister had just started wearing training bras and the dirty laundry was in the basement and I would sneak down there at night and grab some of my sisters clothing, panties, nylons, bra and even a blouse or skirt and I would take them back to my room and put them on. I had many late nights like this and would rub myself through the clothing, it was such a turn on.

One night I guess I fell asleep and I woke upon to my mother screaming at me and pulling at the clothing. I was so surprised. She left crying and then I striped off as quickly as I could and hid on the covers. My father came into to ask why my mother was so upset and I said I didn't know. She never spoke to me about it and I still like to wear today.

I’m an accountant in private practice. I enjoyed wearing lingerie under my business suit or sport coat. I liked thigh high stockings and garter belts, panties. Often a shapewear garment. I often wore a bra. I always checked myself in the mirror to be sure nothing showed. Or so I thought. I also kept 2 ‘confidential’ file cabinets. Two of the drawers had lingerie, heels and dresses I would wear at lunch when the two women were away at lunch. One had been with me 6 years and the other, Garnette, 2 years. One day after a lunch time dress up, I was sloppy hiding my bra. Maybe the tie wasn’t right or coat not buttoned. Garnette came in to announce my next appointment. She looked at my chest, then at me, and in a low voice said, “Your bra is showing! Mrs. Cornwall will see it. I’ll stall her 5 minutes so you can take it off.” She quickly left ? room. I was horrified, embarrassed, frightened, all at the same time. It took the 5 minutes to take off the bra get dressed and calm down.

I was scared after the appointment. What was I going to say to Garnette? How could I face her? Was she going to be at her desk? Or had she left the office shocked to discover the boss cross-dressed? Would she tell Ruth, the bookkeeper? I just sat there. Garnette knocked a couple minutes later and slipped in. I tried to say something but nothing coherent came out. She said, ‘Take it easy. I’ve known you cross dressed a long time. When you interviewed me for the job, Ruth told me you were a great boss, ran an honest caring practice, did well by your clients. However you cross dressed, and wore lingerie to work. She said if that were a problem I should turn down the job. It wasn’t an issue so I’ve been here two years. I asked if this was the first time she’d seen my bra. She said this was the first time it was so obvious, but as she was on the look out, often it was easy to see bra straps on the back of the jacket, top of the lace under the shirt, and bumps of the garters on the pants. Several times I’d been lax closing the drawer and leaving a garment out. She said she and Ruth always made a lot of noise coming in the office and waited a while before disturbing you. Before Garnette came, Ruth had seen me twice with my clothing in disarray appearing that I had rapidly dressed. Moreover they’d discovered my selfie files on my computer.

Now I knew that they knew I was a cross-dresser. A bit later they asked if I’d dress up for them. After all they’d seen the photos. After hours I did; first time I dared wear a dress and have someone actually see me. Garnette became my enabler; after a lot of transitioning work I became a full time cross dresser. In San Francisco people come out as trans with less problem that 20 years ago. In some clubs women told me not to use the women's room; some guys who like transwomen hit on me. Six former friends severed relations. I lost four clients who told Ruth they didn't like a trans. The rest just accepted my appearance.

When I was a teen , I was caught by my sister when she came home early from track team practice. I came home from school, and pulled a pair of Mom's panties ( Bikinis) , Mom's bra, and pantyhose from the laundry room. I put them on and was walking around in the living room , when Marie walked in the door. She saw me . I ran to my room and locked the door. Marie banged on the door, then she went away. Mom came home from her job an hour later. Marie told her what she saw. Marie was 2 years older then me. Mom came to my room, and told me to open the door. I did. Mom sat down and said let me see what you were wearing. I handed her the panties, bra, and panty hose. Mom said you are not in trouble for wearing women's clothes . If you feel you have to wear them the urge is to strong for you to deni . But you are in trouble for taking my clothes. These are mine, they are personal , you invaded my privacy. Mom asked me how long I was doing this. I told her since the summer, it was now November. Mom told me to take off my pants and underwear and lay face down on the bed. I was going to be punished for violating her privacy. She spanked me with a strap till I was crying. Mom then said this is the first part of your punishment. Tomorrow will be the seconded part.

Well tomorrow was Saturday. Mom called me down for breakfast, Marie was already eating. She saw me and started to giggle. Mom warned her to stop. Mom said to me Tony sit down and eat , then we are going to the mall shopping. Oh I said, ok . I was thinking maybe she changed her mind about the second part of the punishment. Although as soon as I sat down I felt the first part, it still hurt.

. Mom drove to the mall, we parked and walked to one of the 3 big department stores there. Marie was smiling, then she giggled again. Mom shot her a look and she stopped. I followed Mom and Marie . I noticed we were heading for the lingerie department. I started to lose my breath, and die of embarrassment. Mom turned to me. Tony If you fit in my panties you are a size 6. You go there and pick out 4 pairs of panties, any color , any style . They will be yours. You can wear them or not wear them . But you will never touch mine again . Do you understand. Yes Mon I said. Go . I went as soon as I started to look through the rack a sales girl asked if I needed help. I was so embarrassed, so humiliated I couldn't talk. I heard Mom who was standing with Marie, tellbthe sales girl that he was buying 4 pairs of panties for himself, because he likes to wear them. The sales girl giggled and asked me do you want briefs, or bikinis, or a thong. I couldn't speak. I mumbled I don't know. Mom said get a couple of bikinis, a brief, and a thong . The sales girl smiled. Come let me show you. There are different colors, some have lace. By now the store was getting crowded. Women and girls were looking at me going through the racks , and giggling. I picked out 4 pairs of panties with the help of this 19 or 20 year old sales girl. With Mom's prompting of the sales girl they were nylon , lacey, and sexy .

That was the easy part , Mom new the size. But them Mom told the sales girl that he will need 2 bras. We didn't know the size. The sales girl saw how uncomfortable I was. I was almost crying. She brought me by the department office where there were less people to see. She took a tape measure and measured me. She asked Mom what size cups and they along with Marie all giggled. Mom said let's go with a A cup. The sales girl lead me to where the bras were. She asked Mom sexy or everyday. Mom laughed, sexy. They had ne pick out 2 . A black one and a white one with lace and bows. I thought we were done, when Mom said oh yes a pair of pantyhose. With that doe we left. Mom said you wear these things in your room. I don't want to see them. When they are dirty, you hand wash them and hang them in the laundry room. They don't go in the dryer or you will ruin them.

That's how it started for me.

My wife found my makeup i kept in a size 13 shoe box. She quickly knew it was mine and stoped having sex with me after I confessed everything. I have not had sex fir over six years and probably never will. We still love each other but are now sexually incompatable, unless i can get her to wear the strap.

She has made me a cuckold and has boyfriends to take care of her sexual needs.

My mother caught me in her clothes when I was 12 she wasn’t best pleased but she kept me in her clothes until until my aunty and cousin came over which they did nearly everyday they both feel about laughing but mum put me over my knee in front of them it was so embarrassing, but it still didn’t stop me dressing