My Step Sister Caught Me

When I was 12 my father remarried and I gained a step sister.

After a year or 2 I had to try on her underwear I was very careful just to use dirty stuff from the wash basket at first. Eventually the desire to try on clean bras overcame me and I started to regularly raid her lingerie drawers.

She was 3 years older than me and had some lovely bras.

She started to suspect something was happening and dropped hints. One Day I bunked of school ill. Had a day alone at home just had to wear her bra pants suspenders and stockings. I think she guessed what I might do and came back from school early. She caught me and we had a big row she told my dad and step mum and I was in real trouble.

I started again after some months and she caught me again but this time she listened to my story and put up with me using her old stuff. 

She is the only person who knows of my continuing desire to be a girl and over the years has become quite supportive, but she really doesn't understand me.

I still wear her bras and pants when I stay at her house. Can't break old habits






sugerbear sugerbear
61-65, M
12 Responses Nov 14, 2008

Hey please read aunt Jane and the sleepover by great12345678910

sounds a lot like my youth

I didn't have a sister but when I was 8, about once a month my mummy would come to my room and give me a pillowcase full of her underwear and swimming costumes. It kept me occupied for hours and I don't think she ever saw me wearing any of the clothes. My favorite was a red shiny one piece bathing costume and I usually ended up rubbing myself to a dry ****** before giving the pillowcase back to mummy.

WOW, what a great Mom!!!

I was forced to dress as a girl one time and at the time i hated having to wear the the lacy tights but in a strange way i love to wear them now and i got caught by my parents a few times and they were not happy with me but it was them who made me this way:(

My sister caught me when I was 15 and she was 17. I was looking at one of her bras when she walked into the room. She asked me why I was looking at them, and just could not talk.She then asked me if I wanted to try them on. Surprise-surprise. What could I say. She had just come out of the shower, she was in her bathrobe, and said she would show me how to put one on. She took off her robe and there she was with out a stich of clothes on. She took a bra out of her draw and showed me how to hook it backwards, and then turn it around. I was still holding one of her bras, and she said now put it on. She put a pair of nylons, one in each side to fill it out. Next she said how about wearing a pair of my panties. She took out 2 clean ones and gave me one and she put om the other. I had to take off my pants, and when she saw my big hardon, she said that she had always wanted to see it. She was my sister so there was no way that she would touch it, but told me to jack off so it would be soft. I did and she said she did not think that there would be that much of it, and the color was not what she had thought. She asked me if I wanted to put on a skirt and a blouse for a couple of hours, knowing that Mon would not be home till late. This went on for at least a year, and each time I had to jack off for her. I finally told her that I would jack off only if she was bare naked. After about 6 months we would ********** in front of each other , and then get dressed. Now years later we still bring it up, and she knows that I wear panties and a bra all the time now. I have told her I was so glad that she broke me into wear fem clothing. She has always said that she wanted a sister, and I was at least a half sister to her.

It must have been an horrendous shock when your step sister came home from school early and caught you in her lingerie sugerbear. Her telling your dad and step mum must have understandably been unbelievably confronting and embarrassing. After playing with her bras and panties initially you were subsequently feeding the need within you which had been ignited. Once you have reached that stage it will continue to implode and demand to be fed. It is a natural part of your make up not understood by many. At least your step sister ultimately gave you a good hearing and has seemingly been very supportive largely. Similarly i started with my sisters pretty silky nylon panties, then her silky slips and bras, and inevitably in my case to her skirts and dresses. She has been wonderfully understanding and extremely supportive thankfully. Cheers, Fontana

When I started in my adolescence, around 4th grade, with mom's lingerie and nightgowns I doubt she knew. I think she may have discovered on the nights she'd come in and check how well I was sleeping. I'm sure she must've pulled my covers and discovered me all nice and comfy in one of her discarded satin nightgowns. Eventually I discovered new silky satin nightgowns, my size, in the drawer where I hid her old ones and ones I'd bought for myself (a benefit of working in Woolworth's 5 & 10 during high school). Nothing was ever said. When my wife caught me about 20 years into our 50+ years of marriage it was World War 3! She's still not happy about it but has become a little more tolerating of my full time panty wearing and sleeping in my satin long nightgowns!

I do believe you are correct, "casualwear". Sadly there seems to be no way to fix it with her either as I've already tried many times! Other than this one issue we are very happily married and will celebrate 51 years later this month! Thanks for your input. Berta

I was first caught by my Mom (I was six, it was the first time that I dressed myself). My wife caught me 1 month after we wed. The scariest was when my daughters caught me (They were 13 and 15 at the time). Read my latest blog, I will post it soon.

I have been caught, and have no problem with it. I once dressed all the way (lingerie, hose, dress,<br />
and pumps), and went to a beauty parlor, and had my hair and nails done!

WOW!!! How wonderful that must've been!

where I live that would cause a ROYAL fuss! small town just outside of Boston, but I would LOVE to cut and perm my hair...I was thinking about a pageboy!

I have had a manicure and pedicure 3 times recently at 2 different places! Was accepted by female technicians with no problems! Will go again!

Go to a different town! Go to Boston! Find a beauty palour, find there number and call and ask if you can get your nails done and ask if they would mind if you are enfemme! I gaurentee they will say no problem! If not find anothor place! They are a dime a dozen! average price ic $30! Enjoy!

"mslade", I'm north west of Boston on the NH border and share your fears. In spite of the new non-discrimination law that went into effect here in Mass. on July 1st, 2012 I fear that our complete public acceptance is still a long way off! If you are on the north side you might try calling Barbara at Florence's Fashions in Wakefield for some assistance. She helped me with a beautiful black feminine wig to wear over my light grey crew cut male do, I offer this as another option. I doubt you'd have any problem getting your hair and nails done at another beauty shop as "PJJA1000" suggested. Hope some of these options work out for you. I wish I had such an opportunity but know it cannot ever happen, sadly.

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I understand what you've been through. I have been caught many times wearing pantyhose by my mother and aunts, and even though they told me that I shouldn't wear pantyhose I keep on wearing them. Now I'm a happy 30 year old man that wears pantyhose everyday and over years of discussions with my mother I finally can have my pantyhose on my closet without been bothered.

Yes it was hard but I'm still crossdressing and love it more than ever

You are what you are!

I have never been caught OMG that must have been hard for a 12 year old boy. I caught sugarbear crossdressing on here, but here it's OK, We do it and love it too. We have our girlfriend here. XOXO Lisa