Getting caught crossdressed?
- Thread starter CurtGiles46
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luvslingerie200
Experienced
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- Aug 25, 2013
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it was
What was your wife's reaction?
I'm wondering the same thing. I hope it was good luck!
jakie69
Slutty gurl
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- Oct 7, 2022
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I’ve been caught by a few people I’ve the years but the one that changed my life was being caught by my wife. She knew I crossdressed and encouraged it for sex, but she didn’t know I was serious about being crossdressed full time and eventually transitioning. When she caught me I was dressed in lingerie, wearing breast forms, full make up, nails painted and riding one of her dildos while watching shemale porn. My dress is been wearing and heels were on the floor and if she’d arrived home sooner she’d have caught my fuck buddy balls deep inside me. Instead I carried on once he’d gone, being rather drunk and high I was just lost in the moment. That’s when she came home early
At the time it was a shock and it caused a lot of heartache and arguing. In the end it was the best thing to happen to me. She accepted me for who I am and supported my transition. It helps that we have an FLR relationship and she’s dominant while I’m submissive.
At the time it was a shock and it caused a lot of heartache and arguing. In the end it was the best thing to happen to me. She accepted me for who I am and supported my transition. It helps that we have an FLR relationship and she’s dominant while I’m submissive.
TrailerHitch
Adventure Seeker
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- Oct 2, 2022
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My wife fully embraces and supports my bi-curious desires and has said go for it if that is what I want. But she also made it very clear that if she ever catches me in panties we are done. That's not a big deal to me because honestly I have never explored that aspect of my sex life. I would be lying if I said I was not curious about it, but not enough to risk losing my wife.
hbcacouple
Literotica Guru
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- May 9, 2002
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We deliberately run the low risk of encounters. Going places where we might run into someone that we know. Wearing a filled bra usually under a sports jacket. Usually very slightly filled. Where the risk was very low, we have gone out with actual breast forms and light makeup.
I am bisexual myself. My friends and me long suspected a younger cousin to harbor bisexual/ gay feelings. His walk, talk, pony tail, hairless, thin frame and his boots made me almost sure. But when ever I asked him, he would deny it. The following year, when he joined college in another city, he was teased by some guys and told us about it. So some of my friends had some friends near his college and they found a guy in the college who was willing to keep an eye on him. A few weeks later, that guy sent us a pic...
https://thumb-nss.xhcdn.com/a/X1mUxdGWII3Yb486itfpZg/024/486/399/v2/2560x1440.207.webp
It was the cousin - dressed as a girl!
The guy had somehow found my cousin's secret online cross dresser identity and befriended him and even had a sex date with him. Then he shared his online profile and pics with us
https://cdn03.imaglr.com/storage/uploads/135582/2026/07/z9cXJRsdDAmQryK5KdWUbemJnAW7MBXmwJHEUeyF.jpg
then a video like this https://ip254333384.ahcdn.com/key=u...origin=283656267/108000/108801/108801_gif.mp4
My friends then invited them to a house party and we revealed our true selves to each other.
https://thumb-nss.xhcdn.com/a/X1mUxdGWII3Yb486itfpZg/024/486/399/v2/2560x1440.207.webp
It was the cousin - dressed as a girl!
The guy had somehow found my cousin's secret online cross dresser identity and befriended him and even had a sex date with him. Then he shared his online profile and pics with us
https://cdn03.imaglr.com/storage/uploads/135582/2026/07/z9cXJRsdDAmQryK5KdWUbemJnAW7MBXmwJHEUeyF.jpg
then a video like this https://ip254333384.ahcdn.com/key=u...origin=283656267/108000/108801/108801_gif.mp4
My friends then invited them to a house party and we revealed our true selves to each other.
JakesFriend
Virgin (No)
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- Aug 2, 2026
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So much fun in so many ways with these girls.
JakesFriend
Virgin (No)
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- Aug 2, 2026
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Same here. I wanted to be caught. I think she liked it as much as I did.
LindsayGurl
Really Experienced
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- Aug 3, 2016
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- 411
I got caught once. My roommate was still in college and would normally leave at around 7am for classes. Heard him go out the front door at around 7. So I dressed up. Fucking completely. Heels, stockings, skirt, belly tank top, wig, make up. Since he was "gone for the day" I went downstairs to get a soda. . . Wrapped around the corner and he was on the couch. Just a "WHAT THE FUCK! ! ! " came out of his mouth. I just ran upstairs. Was just flipping out with anxiety the rest of the day/weeks thinking how to explain it when I saw him. But he ended up never saying a word. He has still never mentioned it to this day and it's been like 5 years. Some things really show when you have good friends. I was sort of hoping he would mention and want to play sometime. But he didn't so I left it alone as he did for me.
wish that had turned out for you, but better than it might have I guess
LindsayGurl
Really Experienced
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- Aug 3, 2016
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- 411
Yeah and I don't know if acting on it would turn out quiet as I would imagine. He has been a long time friend since middle school. But you never know, might have gotten really crazy since we do know each other so well.
yeah, that's a beautiful dream!!!
Happyandgay
Gay Slut
- Joined
- May 11, 2026
- Posts
- 126
Multiple times.. I have been wearing women’s jeans, shorts, shirts and panties since my senior year of high school. After coming out as gay to my mom and sisters, I would swap various things with my twin sister, who was rather chesty, and had bigger hips than I, she’d buy thing wear them and hate how big it made her top look, or didn’t like how the bottoms made her look, and come trade with me, usually they fit perfectly on me, and she liked the roomy men’s clothes. We never swapped out undergarments, that would be gross, but I did have her buy me a pack of flowery women’s bikini briefs, and few items from Vickie’s from time to time. She’s a lesbian so she didn’t care. My mother who did the lion’s share of the laundry, was just like, “whatever”, so she didn’t care. Hell she’d put underwear “from Santa” out for us at Christmas, nothing fancy, but like a 3-6 pack of panties for each of us. The only feminine thing I really ever wore was underwear, and this awesome pink sweater, otherwise one would really have to stare at my crotch to realize that the fly was going the opposite direction. Didn’t have P.E. My senior year either so no worries.
The first time I ever got caught, but it really wasn’t a big deal at all was when I was home from college over spring break, and it was my third year, I was in a somewhat serious relationship with a guy back at school, he was an older local man, so he stayed there due to work. I had gone shopping and was in the bathroom at home trying on my purchases in front of the bigger mirror. I had a keep pile and return pile. I had bought a few fun items from Frederick’s to spice up for the man back at school, and I was in the process of seeing what my butt looked like in this purple lingerie set and it looked good, he’s going to take me to pound town in this keeper! .
I then heard “that’s a good color for you” from my mother at the sink. I was mortified. She looked at a pile and told me red was definitely not a good color, got a cough drop out of the cabinet and left.
The first time I ever got caught, but it really wasn’t a big deal at all was when I was home from college over spring break, and it was my third year, I was in a somewhat serious relationship with a guy back at school, he was an older local man, so he stayed there due to work. I had gone shopping and was in the bathroom at home trying on my purchases in front of the bigger mirror. I had a keep pile and return pile. I had bought a few fun items from Frederick’s to spice up for the man back at school, and I was in the process of seeing what my butt looked like in this purple lingerie set and it looked good, he’s going to take me to pound town in this keeper! .
I then heard “that’s a good color for you” from my mother at the sink. I was mortified. She looked at a pile and told me red was definitely not a good color, got a cough drop out of the cabinet and left.
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