Both My Mother and My Sister...

Shortly after beginning to experiment with my sister's clothes, I was caught by both my mother and sister. A girl down the street had a dress for school that was made of some polyester fabric that caught the breeze and moved in ways that boys' clothes simply don't.  When my sister and I walked to school, I made it a point of trying to time it so that we walked just behind the group the other girl was in. I just loved how the dress moved on her.

My sister got the same dress in a different color. I so wanted to try it on and see how it felt but I didn't dare. The idea was enticing though, so I snuck out some of her older things and satisfied myself trying on her underwear, blouses and skirts. I did this any time I was home alone.

One afternoon I tried on this dress. It was as silky as I imagined and it slid so nicely against the nylon panties I had on underneath. I tested it several times by rubbing my hands up and down my front and back. My mother had come home in the meantime and came upstairs to find me. She came into my room and I was wearing the dress. I think she also saw me rubbing the material against my pantied bottom.

At first she said nothing, then sat me down on the bed and wanted to talk about why I was wearing the dress, asked how often I did this and lectured me on why i shouldn't take my sister's things. And of course while this was going on, my sister came home and saw the two of us in my room, sitting on the bed with me in her dress. She laughed and then asked what was going on.

Without hesitation, my mother explained that I was curious about her clothing and had tried on the dress but repeated what I had said about this being the first time. My sister didn't believe it and I don't think my mother really did. My sister asked if I was wearing her underwear too. My mother made me tell her I was but said I didn't have to show them. My sister asked if I got spanked or was getting a spanking and my mother said no. I promised I'd never do it again and my mother gave me a hug before getting up and the two of them left so I could change.

The next day my sister decided I deserved a spanking anyway, so after school and before my parents came home from work I had to model the dress for her again and ended up over her knee.

Joe438 Joe438
41-45, M
6 Responses Aug 23, 2009

Your sister liked something about that situation. Many women admit that they think it's sexy when a man tries on women's clothing. I was relieved to learn that my wife has always been turned on by a man in women's clothes. I did it up really well for Halloween. I was in a show dancer's constum with nice garter belts, stocking, gloves, and a great masquarade piece. Being a cashier at a grocery store, many female customers made it known that my appearance was a turn on to them. I was so decked out and sexy, that I wun the costume contest. Have fun dressing up if you chose to again and don't be shy, just go all out when you do it. I will try to attach my photo

That's an interesting question. My girlfriend wasn't too keen on my interests in women's clothes but she did come around eventually. I haven't been able to get her to 'make me' put on a dress for a spanking yet, but she has spanked me (pretty hard!) for lingering too long with the laundry when I help her fold clothes. It was something like "I don't touch your panties and I'd appreciate it if you'd not fondle mine", and then I got a long spanking over her lap after I spent too long looking at one of her skirts on a hanger. So I think she's getting more comfortable with spanking me. I don't know if she'd spank a stranger - I doubt it. Perhaps if we were good friends?<br />
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My sister on the other hand, could probably be convinced. She used to spank her ex-husband and I'm sure she enjoyed every second he was over her knee. She is a hairbrush spanker, so you'd have to be able to take that.

If we ever got together would your sister give me a spanking, or your girlfriend?

She knows I find women's clothes a turnon and that I love being spanked, so I can't see her thinking of that as a punishment. My sister made sure to tell my girlfriend that I had been wearing her clothes for quite some time before she caught me. While my sister was telling the tale, I had to take down my pants and show them I wasn't wearing anyone's panties. I didn't do it fast enough and my sister did pull me over her knee (in front of my girlfriend) and give me a couple of good smacks for not doing as I was told. My girlfriend later said it was pretty funny and a little hot watching my sister spank me.<br />
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My girlfriend has spanked me once after their chat for not telling my her about my interest in girl clothes and she warned me not to even think about trying on her clothes. I don't dare since I don't know if I'll get the spanking I want from her, a far worse spanking, or perhaps she'll dump me.<br />
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I'd love to find a way to have her spank me in panties and a dress. Maybe I'll manage somehow. Maybe I should ask my sister for help. I wonder if I could ask her to 'punish' me in one of her dresses while my girlfriend is around.

It didn't start as a very painful spanking but it certainly was painful by the time she was done. I had to undress and put on the dress and a a pair of panties while I stood in front of her. I was shaking and horribly embarrassed. I had put the panties on backwards and had to hold the dress up while she pulled them down, told me to step out of them and then had me step into them so she could pull them up. She patted me on the bottom and then sat on the bed and told me to lay across her lap.<br />
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While I was across her lap, waiting for the spanking, she asked me why I had tried on her dress. I said I didn't know and she gave me a couple of pretty hard smacks with her hand. After she threatened to get her hairbrush, I admitted that I liked the silky fabric and wanted to know how it would feel to wear something like that. I also admitted that I had done it before.<br />
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The spanking took about 15 minutes or so with the scolding (she was better at scolding than my mother was) and was pretty hard towards the end. My bottom was still sore a day or two later.<br />
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I don't have much opportunity to dress now. I've been dating a woman for a while who has spanked me a few times. She and my sister were chatting and the story came out. Once my girlfriend started speaking to me again, we talked about it and she's still deciding how she feels about this.

Do you remember what your sister was wearing when she spanked you? Would that have mattered? Thanks.

Wow, did she do it hard, just with her hand? Do you still dress and get spanked?