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Crossdressers Talk About the First Time They were caught Crossdressing

caught crossdressing

Getting caught crossdressing is certainly not a fun experience. It can be a feeling of embarrassment or humiliation for most crossdressers. Since most crossdressers dress in private or secretly, there is a good chance of getting caught if they are not careful enough. Crossdressers can get caught red handed or from their feminine stuffs they forgot to hide properly.

In this article, we have compiled a list where Crossdressers talk about the first Time they were caught Crossdressing.


“In my early childhood, I began to develop quite a fascination in girl’s undergarments. I also became quite curious about stockings and pantyhose. My older sister wore pretty nylon panties and stockings which really had my keen interest.  I was having increasing thoughts about wearing her undergarments & outfits and even started experiencing restless nights trying to sleep.

I could feel the urge to get dressed as a girl increasing very rapidly and it was getting impossible to resist. So I decided during one day to sneak into my sister’s room and try whatever I could find to wear.

I picked the right time when no one was around in the house and went into my sister’s bedroom. I could feel my heart beating so faster and I was very excited. I opened her dressing cabinet and saw many panties and bra neatly folded in one corner of the cabinet. I gently touched them and I could feel how soft and silky they felt.

I picked one pink pantie and held it for a short time in my hands feeling it. I undressed my pants and the under wear that I was wearing and then stepped into the pantie and pulled it up my legs. It was amazing how great it felt. I posed infront of the mirror and couldn’t stop looking at myself.

Then, my attention went to her bra collection. I picked one of her padded bra and tried it on too. It took me quite a while to put in on since I had no experience wearing a bra before. After I finally got it on, I was so excited with the anticipation of wearing girl’s undergarments.

It felt really good and I couldn’t stop admiring myself in the mirror. Then after sometime, I took them off and put them back neatly to their former position in the drawer like it was before. It was my first experience of crossdressing. Since then, I would sneak into my sister’s room and try on her outfits whenever I had the chance.

Few months later, I was home alone one day and decided to dress up. Unknown to me , my sister was coming home earlier this particular day from university. I got myself dressed in her undergarments and also put on one of her floral dress. I was enjoying myself infront of the mirror when suddenly I heard the back door open and that gave me a big fright. I was completely taken by surprise and I didn’t know what to do. I was about to take the dress off when suddenly the door opened and my sister saw me and she was completely shocked.

I was incredibly embarrassed and I couldn’t look at my sister’s face. My sister after a while of trying to understand what was going on, came closer to me and asked me to explain myself. I was so shocked that I couldn’t really say a word. I could noticed that she was angry that I went through her stuffs. I was almost about to cry when my sister told me to sit down on the bed and talk to her.

Eventually I opened up and told her I was very sorry for going through her stuffs and I said I did it because I was really curious about wearing girl’s clothes. I apologized many times to her and she said it was okay. She then started to ask question about when the urges started and how long have I been dressing in her clothes.  I told her couple of times and finally told the truth to her.

She was very supportive and told me it was okay and she wouldn’t tell our parents. I was a bit relieved but still quite distressed after being caught by my sister. After some talking, I went to my room and took off all the clothes that I was wearing and got back into my own clothes. Then I went to my sister and handed her clothes back. She was quite surprised that I was wearing her bra and under wear too.

After that incident, my sister made me promise not to go through her stuffs again and if I really wanted to dress up, I should first ask for permission first.  She explained that it was not uncommon for boys to develop interest in girl’s undergarments and clothes. She told me that if I ever needed to talk about it she would be there to support me. After that, I got a bit relaxed and felt really grateful to have such an understanding sister.”

– Rachel Garner

8 Comments

  1. My parents divorced when I was 12. I started to dress up to and feel like the “woman” of the house, not the “man”. One night my mom was out on a date, so I dressed in my mom’s bra, panties, pantyhose, dress, heels, pearls and full makeup! It was so freeing. But, when she came home early, I was caught red handed. My mom was shocked and asked how long had I been doing this? I panicked and said this was my only time. A total lie. The next morning we had a very brief talk and she wrote the event off to the divorce as a one off. I’ve been dressing ever since!

  2. All sounds o so familiar….

  3. I was 5 years old and my teenage aunt was babysitting me for my mother. I got into a mud puddle and made a mess of all my clothes. My aunt, fearing my mother’s wrath upon her return, so auntie took my clothes to launder them. Having nothing else for me to wear she adorned me in a pair of her white nylon panties. To this day I remember the cool, smooth, soft fabric as it touched my most sensitive areas. I had to have more! I got home later and found a pair of my mother’s pantyhose in the laundry bin. I had to try them on. It was like heaven! I had to have more! This went on as I aged. Taking the time to secret away something soft and silky, wear it for awhile and then put it back. One day, when I was 10, I was wearing Mother’s pantyhose under my jeans. No socks. While playing outside, my sister noticed my “tan” ankle right away! She immediately ran into the house to “tell”! My parents brought me in the living room, yelled at me, made my drop my pants and stand there in front of the entire family in just pantyhose. My mother laughed and my father yelled! I was horrified. I didn’t dress in anything like that for several years. Then one day at the age of 13 I decided it was time to try pantyhose again. I was experiencing the “rush” of puberty and couldn’t stop thinking about how it would feel to wear pantyhose again. I snuck some of mom’s hose to my room, put them on and even did my exercises in them. Later I found a bra that was in a pile of “yard sale” clothes we were going to sell. I took it! It fit very nicely. I also found a one piece bathing suit that used to be mom’s in that same pile of “yard sale” clothes. I now had an “exercise” outfit. I couldn’t stop wearing that outfit. Black bathing suit, white bra, tan pantyhose. I thought I was “gorgeous”. While laying on my side and doing leg kicks, I noticed there was a strong swelling in my “private area”. The more I kicked my leg in the air, the more I felt that “rush”. Then all of a sudden, I exploded in a way that I had never ever experienced before. It was MAGIC!! It was also, messy. I was scared and hid my clothes thinking something was wrong. BUT I couldn’t forget the experience. So I washed the clothing, put ’em back on and exercised again! As you could imagine, exercise became a high point of my existence! Then I tried “self massage” while wearing panties and hose and bra and a nightgown. All purloined items from my mother and sisters. That nylon nightgown over the panties and hose was another episode of pure magic. Fast forward to a few years later and my first real love. A very attractive young lady who had a hankering for her boyfriend to let her “dress him up”. I acted like I didn’t want to, but inside I was about to scream! I made love to her while dressed like her. I can not even begin to explain how high I was from that! It took days to come back down!! The next time, she put make-up on me. I found lipstick to be especially sensuous!! Sharing lipstick was even more luxurious! One day we were playing dress up at my apartment when some friends unexpectedly dropped by. They knocked. We wouldn’t answer. I heard them say “His car’s parked outside, why isn’t he here?” My heart was racing. There was no way I could be caught by them and still be able to face them later. Finally they left. But one of the girls said she could smell perfume! A couple years later that girl and I broke up. I found out later that she revealed to one of my best friends that she and I played “dress up” and did it a lot. He wouldn’t let me live it down! He bought me pantyhose and lingerie as birthday and Christmas gag-gifts. I kept them and enjoyed them, unbeknownst to him! At least that’s what I thought….I was asked to be in a womanless beauty pageant, along with some other guys in my office. I agreed to. Oh, I acted reluctant about it, but I was thrilled on the inside. So I used the pantyhose from my friend and a dress that another friend gave me as a gag-gift when all my friends were alerted to my ex-girlfriends stories. (she turned out to be a vindictive little thing, and SHE left ME!) My friend, who came to the pageant, asked me if I was wearing the stuff they had given me. I said “Sure, did you think I’d go pay good money for this stuff?” Trying to act like a “guy” about it. I had a female friend from the office loan me a wig and do my makeup. I was very proud of how I looked. Apparently so was my friend. After the pageant he said he wanted to talk to me. I told him I’d get changed first and he said “it really can’t wait”. We went to his car, a 1972 Monte Carlo. Significant detail because that car didn’t have bucket seats up front. Long story short, my friend put “the moves” on me. Told me how he found me attractive, and always wanted to have girl “like me”. I was overwhelmed. I told him that I didn’t really think of him like that and that I was into girls. He put his hand on my knee and while making his case, he slid that hand up my thigh. It was sooo warm. My heart was about to burst! I was sooo scared, confused and weirded out all at the same time. I could feel my eyes welling up and I didn’t realize how close his face was to mine until it was too close! He softly kissed my lips and then pushed in for a deeper kiss. All the while his hand was caressing my thigh, then he moved to my groin. He said “oh, somebody is a little wet!”. I couldn’t deny it, I was very hard and very wet. I’d never had a man touch me there and I have to admit it was a thrill and a half! Just then, from outside the car, some girl yelled for my friend. Called him by name. She came to passenger side of the car. The way I was turned I had my back to her. She asked if we were coming to town and my friend said he didn’t know, but maybe! She said she’s see us later and then went to her car and left. My friend looked at me and said “Well, that got hot and heavy pretty quickly, didn’t it?”. I answered that it did and that I had better go. I opened the door and slipped out onto the parking lot. He told me to “think about it”. Adding that we could “have a real good time together!”. I told him I would and I even thanked him for making me feel special! He smiled and said “anytime!” I left and we never talked about that night again. I’ve been tempted to bring it up a time or two, but never did. I wish now that I had let him take me down that path…I really do.

  4. I’ve been there Susan. I was dating a woman whom I told that I crossdressed. She was ok with it and didn’t place any restrictions on my dressing. I used to go out from time to time but mostly for my personal pleasure and occasionally we’d make love while I was wearing a bra, panties and thigh high stockings.

    After we married she let me continue for a while but after about 3 months told me that it disgusted her and I had to stop. She also thought that she was worried I was gay and that my constant crossdressing was a manifestation of that. I quickly purged my feminine wardrobe and fit a few months I got by but soon afterwards I went back to dressing with a vengeance. I obviously kept this hidden from my wife but after a number of years she caught me through my internet browser history. I agreed to stop once more but a few weeks later I was going crazy not dressing so I placed a Craigslist ad for a spare bedroom with a closet to keep my things and dress up and maybe venture out.

    I got a few positive as responses but the best situation was one that made me uncomfortable because it was from a man and I felt uncomfortable being in a man’s house while I dressed up. I just felt ‘weird’ but I really needed to dress up and his place was close and clean, and he only asked $100/month and he was a non-smoker.

    We met and agreed and I paid two months, one month security and a month in advance. I started going to his place a couple times a week and the first few times he was away but on the second week he was there. He was good though and I dressed up and stayed in my room for a while while I admired my female appearance and frankly I was considering pleasuring myself.

    After maybe 20-30 minutes he spoke up through the door and said I was more than welcome to come out and we could sit and chat or I could go out and come back or if I didn’t want to I could just stay in my room but that I was welcome to be social.

    A few minutes later I decided that since he knew what I was doing and he seemed like an ok guy plus he wasn’t too old, young, weird or anything that I would take him up on that and I went out and we talked. He was super cool and complemented me on my appearance which was nice. I went out for a while but came back soon afterwards. We talked for what I thought was a few minutes then I realized another hour had passed and I had to scoot!

    The next times I went there we spent more and more time together and at some point within the first month I let him hug me. I found myself confused and also I noticed he was aroused. I also noticed that both of our hearts were beating very fast! This went on for a few minutes and then almost at the same time we kissed! All of a sudden both of us were aroused and we were all over each other, I had never done this before! We went to his bedroom and started becoming passionate.

    Long story short I put my hand down his pants and he unbuckled them and he was hard as steel. I found myself going down on him and after a few minutes of me giving him oral he stopped me and asked if I’d be willing to let him try to penetrate me. I told him I was willing to try but if I couldn’t do it or I changed my mind that he would stop. In any event it was amazing. It took a few tries but he was able to enter me and make love to me.

    After a year I finally decided I couldn’t keep going like this and asked my wife for a divorce. When we separated she confronted me with ‘have you been having an affair?’ ‘do you have a girlfriend/boyfriend?’ I paused for about a minute and began to think she already knew so I told her I had a boyfriend. She told me she was shocked that I told the truth but that she already knew everything which she did. Apparently I left my Yahoo account logged on on her laptop and she read and saw everything I had been doing for the past year and a half.

    The good news is that I am now living with the man I was renting from and that we are now in the same bed.

  5. I’ve been crossdressing for a long time,,but it wasn’t until a few years ago that I got made by a coworker..I was at a sex club in Las Vegas on New Years Eve,and a friend that I worked with walked in without me seeing him..He looked at me and smiled..I kinda got nervous,and walked out of the club to my car..His car was parked right along side mine..I have some bumper stickers on my car that I know he recognized,since he’s been in my car before. All of a sudden I really didn’t give a crap about being caught..I knew someday,someone I know would see me..We eventually talked inside,and actually told me I looked really sweet..Kinda made me feel weird,but hey I like compliments,and I do look rather nice all dressed up..I later found out from one of the other CD’s there that he frequents the place regularly,and has a thing for girls like me..I don’t think he ever said anything to any of the guys I work with,maybe because he’s an admirer,and wants to keep that hushed

  6. I had a similar experience when I rented a room in a house.
    In a matter of months, I was dressing as Alison more and more with the active encouragement of Steve. We were both turned on by my increasing femininity – no body hair, more make-up, a professional wig and extremely sexy, erotic clothing and silicone 38C breast forms.
    We would have a cuddle then a kiss. Much later he would caress me and touch me up – both of us getting very turned on. I bought an enema kit for the night he wined and dined me Knowing / Hoping that IT would happen.
    Huge turn on but we took our time. He was very gentle and considerate. After a few minutes of a bit of pain I had the best orgasm EVER.
    That was me hooked forever.
    Sorry to say he moved abroad after 14 months so it all ended.

    Love Ali xx

  7. The time I was caught, but not confronted:

    I was in the house alone in the evening, dressing in my mother’s bedroom. It was located just as you entered the front door. All of a sudden, the front door opened and my mother moved swiftly past. I immediately started undressing. She yelled out for me, and I remember telling her I was naked. “Why are you naked?” she asked. Of course, I had no answer. I came out of her room as soon as I was decent. The conversation moved on, and the incident was never discussed.

    There is no way she didn’t know what I was doing. For whatever reason, she never addressed it.

    Sometimes I wish I’d come out to her then about my dressing, but all things considered that would probably have been selfish. She allowed me to continue. There was no call to put something on her.

  8. I started to dress when I lived in Germany. One night, while sat back on my couch in a cute outfit playing video games, someone walked into my room. I immediately channeled the deepest guy voice I could and told them to get out.
    The next few days were awkward, because I had no idea who walked in on me. I had no idea how much they saw, or how many people they had told. Did they see anything at all, or did they just open the wrong door and hear yelling? Did they hear my heels as I went to get up and confront them? I should have just locked my door. And I was always careful about locking my door, but that was the one night I forgot.
    In hindsight, my downstairs neighbor HAD to know that I was dressing. The click-clack of heels would have been a dead giveaway.

    The only other time I think I have been caught, was today. Walking on my porch (which is surrounded by tall hedges), I came into a high visibility area just as a neighbor was driving by. I wasn’t paying attention like I should have been.
    Now, this neighbor probably didn’t see me. But it’s still worrisome to think that they know, and might tell others.

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