Getting caught crossdressed?

[CurtGiles46]

Have you ever been caught crossdressed?

I’ve been interested in this idea since a male student was caught crossdressed in my college Theater class. Several students found him behind the backstage curtain trying on a dress from the costume rack. I had been behind that curtain just a few days earlier and I saw the female costumes.

But the most that I did was picking up a pair of pantyhose and rubbing it against my face.

After the male student was caught, I had fantasies that it was me who got caught.

 

[AlexBailey]

Sure, many times.

I used to wear my older sister’s clothes she had grown out of, especially her sports uniforms. Sometimes I would fall asleep in them and my mom would find me in the morning.

Another time my high school girlfriend’s mom walked in on us while we were cuddling and I was wearing my gf’s cheerleading uniform.

I’ve CD’d in public fairly regularly at times so being ‘caught’ isn’t really a big deal anymore.

 

[Tayloroc]

That’s an excellent attitude!

 

[AlexBailey]

Actually, the most ‘caught’ I ever felt was by my parents when they found out I’d been cross dressing all day my senior year of high school.

My Christian stepfather had been upset about my cross dressing from an early age, but having a sister who was a few years older gave me easy access. My mom knew about my interests and though she was nosy enough to find my stash of clothes she mostly kept it secret from her husband.

Their biggest fear was that I was gay, so when I hooked up with the captain of the cheerleading squad they were very happy, they thought I’d ‘grown out’ of my kinky deviancy.

We had a school event were girls dressed in American football gear and played a game at the stadium on a Friday night — my girlfriend recruited me and a few other guys to be cheerleaders for the game.

I’d gone to my gf’s house early in the morning so she could make me up in her uniform for the day at school, so I spent the whole day in classes as a cheerleader, then in town and at the stadium that night.

I had avoided going home all day because my parents were the only people in town I didn’t want to see me that way, but someone told them about it. They were upset and gave me the silent treatment until the Saturday newpaper came out with the story of the Powder Puff football game with a corner picture of us cheerleaders.

They said I had humiliated them.

 

[muycurioso]

Actually, the most ‘caught’ I ever felt was by my parents when they found out I’d been cross dressing all day my senior year of high school.

My Christian stepfather had been upset about my cross dressing from an early age, but having a sister who was a few years older gave me easy access. My mom knew about my interests and though she was nosy enough to find my stash of clothes she mostly kept it secret from her husband.

Their biggest fear was that I was gay, so when I hooked up with the captain of the cheerleading squad they were very happy, they thought I’d ‘grown out’ of my kinky deviancy.

We had a school event were girls dressed in American football gear and played a game at the stadium on a Friday night — my girlfriend recruited me and a few other guys to be cheerleaders for the game.

I’d gone to my gf’s house early in the morning so she could make me up in her uniform for the day at school, so I spent the whole day in classes as a cheerleader, then in town and at the stadium that night.

I had avoided going home all day because my parents were the only people in town I didn’t want to see me that way, but someone told them about it. They were upset and gave me the silent treatment until the Saturday newpaper came out with the story of the Powder Puff football game with a corner picture of us cheerleaders.

They said I had humiliated them.

sorry someone had to F it up for u

 

[AlexBailey]

sorry someone had to F it up for u

No worries, I had recently turned 18, it was my first time really out without being shut down by an authority. It was very empowering.

 

[tristantrotsky]

That’s an excellent attitude!

Being caught wearing only very brief frilly panties, by two older boys who teased and tormented me and threatened to tell everyone about my secret, unless I sucked their cocks. Scared and nervous, but I had no choice, and sucked them both off, pretending to be reluctant and not enjoying it. But they lied, they told everyone else anyway...

 

[Tayloroc]

Sounds delightful!!

 

[BizTrav]

Have you ever been caught crossdressed?

I’ve been interested in this idea since a male student was caught crossdressed in my college Theater class. Several students found him behind the backstage curtain trying on a dress from the costume rack. I had been behind that curtain just a few days earlier and I saw the female costumes.

But the most that I did was picking up a pair of pantyhose and rubbing it against my face.

After the male student was caught, I had fantasies that it was me who got caught.

Most of my dressing was in the safe confines of the hotel room. Getting "caught" was a result of open curtains and doors. One frisky morning, feeling brave, I decided to show out for the folks

 

[klippert]

I caught a neighbor of mine when I was home from college.

 

[BizTrav]

I caught a neighbor of mine when I was home from college.

And???

 

[ChrissyCD64]

Caught? I've never tried to hide it, I never wear male clothing.

 

[storypost603]

I caught a neighbor of mine when I was home from college.

did anything more happen? I wish you would catch me....

 

[MarksExperiences]

My wife knows now. She caught me 2 years ago at our home being pegged by her best friend Dianna. Dianna was calling me Shania. She was screaming "IM GOING TO FUCK YOU HARD SHANIA. YOU GOD DAMN WHORE." LOL My wife walked in on that.

 

[Phillyguy28]

Omg! What happened after that? Your story sounds awesome.

 

[Tayloroc]

Wow!!

 

[ChrissyCD64]

My wife knows now. She caught me 2 years ago at our home being pegged by her best friend Dianna. Dianna was calling me Shania. She was screaming "IM GOING TO FUCK YOU HARD SHANIA. YOU GOD DAMN WHORE." LOL My wife walked in on that.

My wife loves to watch me get fucked, by real cocks though. She likes to watch me fuck other sissy CD's too.

 

[bimori]

My wife loves to watch me get fucked, by real cocks though. She likes to watch me fuck other sissy CD's too.

When I was married to my first wife I love to dress up in her panties and teddies. I was lucky enough to be able to self suck so one time she was working late I dressed up and had my legs over my head sucking my cock. I was so horny and closed to Cumming in my mouth that I didn’t hear her come in. She came in the room and I could here her gasp at the site. I jumped up and started to undress. She said oh no if you want to be a girl I’ll make you a girl. She made me get back on the bed and to get my legs over my head and lick my cock. She took her vibrator out on her drawer and started to rub it on my balls. Mmm it felt so good she told me to get the head in my mouth as she started to fuck my ass with her toy. It hurt so bad but felt so good. My cock was so hard in my mouth the toy rubbing against my prostrate. She said that’s it slut suck that cock make it cum in your mouth bitch. In about 2 minutes I started to cum harder than I ever had before she was fucking my ass so hard. Her toy buried deep in my ass I couldn’t hold it any longer my cock exploded in my mouth. I thought I would choke on my cum. She would stop fucking my ass. My body was shaking she finally let me roll down. I reached for a tissue to spit into and she started to laugh and took the tissues away. She said no you want to be a girl then you need to swallow every drop slut. I did as I was told and swallowed the biggest load of my life. Mmm it was so go get caught.

 

[rockynook]

I never had the experience of being caught. My sister began feminizing from an early age.
I loved it,and we continued for years.
Being feminized and controlled by a women seems natural.

 

[Tayloroc]

I was caught by my daughter. But she was ok with it

 

[Tayloroc]

I never had the experience of being caught. My sister began feminizing from an early age.
I loved it,and we continued for years.
Being feminized and controlled by a women seems natural.

Love your avatar!

 

[richgo50]

never been caught dressing but a co-worker caught me buying pantys and a bra. he looked puzzeld , I said they were for a girl i knew. he said oh yea , well bring her by the house for a dinner date one night..... hes still waiting to have that dinner date.
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I would love to prepare dinner for you.

 

[Tayloroc]

never been caught dressing but a co-worker caught me buying pantys and a bra. he looked puzzeld , I said they were for a girl i knew. he said oh yea , well bring her by the house for a dinner date one night..... hes still waiting to have that dinner date.
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Just when I think you couldn’t get prettier..

 

[ChrissyCD64]

never been caught dressing but a co-worker caught me buying pantys and a bra. he looked puzzeld , I said they were for a girl i knew. he said oh yea , well bring her by the house for a dinner date one night..... hes still waiting to have that dinner date.
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My wife and I wear the same size, so I would have picked out two sets and we would have dressed up and gone to his party as slutty sisters.

 

[luvslingerie200]

I was caught by my daughter. But she was ok with it

I almost got caught by my stepdaughter. I was dressed in lingerie, chatting and jerking off in the infancy of aol chatrooms. She came home unexpectedly. Thankfully I had locked the door and she had to fumble with her keys, I heard her and spotted her thru the front door glass and was able to spring to my bedroom and put sweats on over the top of the lingerie.....whcih was hers BTW. I did not however close the computer down.