Male 24. I was home alone last spring so I did what I usually do when home alone - I dressed up in my mothers clothes. Bra, pantyhose, high heels, jewelry, lipstick and wig. This time, after putting the garbage in the chute on our floor [we live in a apartment building], I realized I locked myself out of the apartment. Panic struck me hard, because my mother doesnt know I crossdress. And she would be home in less than an hour. Then to my horror, my next door neighbor came into the hallway. Reacting in a loud voice she managed to get 2 other neighbors to open their doors. I wanted to die as they mocked me. Then my mom got home, and she freaked when she saw me. She ordered me inside, and the interrogation began. Turns out she suspected all along I was raiding her closet. She was very vocal about her disappointment, and grounded me for a month, and forbidden from crossdressing. Later on she said she'd give me a choice The one month grounding, or 3 month grounding but I could continue crossdressing, and had to do all the chores and housework. 3 months was brutal, but the thought of not dressing up for a month was worse, so I took the 3 months. She handed me a few dresses and a pair of spike heels she didnt wear and said they were mine. Then she made me shave my legs, chest and underarms. It was totally weird dressing up in front of my mom, but I was glad she was letting me. One catch - I had to do the housework dressed in her clothes and in those spike heels, tight pointy toe pumps with almost 5 inch heels. Anytime I showed discomfort, she would say Thats what I wanted. Oh BTW its 7 months and tho I'm not grounded, I'm dressing up more than ever, still doing housework, wearing makeup, and everyday I have to massage my mothers feet. And she insists I'm a sissy-fairy and a poor excuse for a male.

Comments

Anonymous

by Anonymous on Dec 2, 2012 at 11:21 PM

You got grounded at age 23!?

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Anonymous

by Anonymous on Feb 4, 2013 at 5:47 PM

This would have been more believable if you had said you were in your teens.

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Anonymous

by Anonymous on Feb 14, 2013 at 6:08 AM

It's true. I still live at home cos I cant afford to move out yet. But I'm glad that I got caught cos I dont have to dress up on the sneak anymore. I'm buying my own age appropriate female clothes and have hooked up with 2 other crossdressers who are now friends. Since I have moms approval, I dont mind massaging her feet.

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Anonymous

by Anonymous on Dec 1, 2015 at 9:07 AM

I started crossdressing wearing my mother's and sisters clothes too. I have been caught by my sister in her cheerleader uniform and underwear. Divorced now but caught by my ex in her lingerie too.
I have been caught at work having anal sex toys and had to explain to my coworker before.
Now I tell the girls I date I am crossdressing sissy boy up front. This makes breaking the ice a lot easier when looking for a strapon dominatrix.

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Anonymous

by Anonymous on Jul 14, 2016 at 6:46 PM

M, 24. I was caught dressed in my moms lingerie and spike heels while doing self bondage. I was 20 at the time. I would tie myself to a chair - ankles, legs, waist, and chest. I would have shemale porn on the dvr. I gagged myself with my dirty socks. The last step was cuffing my hands behind me, The key to the cuffs was in the middle of an ice cube next to me. I had to wait for the ice to melt to get free. I figured I had plenty of time, until my mother arrived home way early. I was trapped. I don't know what freaked her out more. That I was wearing her clothes, tied up, or the shemale porn. The pre-cum on her panties really set her off. Needless to say I was punished.....

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