My sister caught me crossdressing.

My sister caught me crossdressing.

I was twelve years old when my step sister caught me. I was in her room, returning her panties. She was older than me, a beautiful 19 and fully a woman. I stood in her room, guiltily holding her red silky panties.

Inside I could feel the tears welling up. I was confused, and had been taking her panties now and then, unsure why, but enjoying pulling them on and posing in front of the big mirror in my mother?s room, when the house was empty.

?I should tell your mommy, you know. It would break her heart, of course,? she said condescendingly. ?You wouldn?t care about that, though. Why would you care for other people?s feelings, if you think it?s ok to creep around taking their clothes.?

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Stephanie was calm, self assured and absolutely confident. She?d grown more confident in the last year or so, as she?d realised the power should held when it came to men.

There had been one or two boys at school, but she?d swiftly dropped them. Her interest lay in older men, who could hardly resist the firm young curves of her exquisite body. She knew how to parade herself to good effect, how to bend over to pick up something on the ground, sure to attract the attention of every male in sight. She knew how to manipulate with a smile, a mock gasp, and a giggle.

I had caught sight of her stepping out of the shower more than once. There had been an occasion when passing her door I?d heard the electric hum of what I knew to be a vibrator, and her heavy breath. Once I had even seen her pleasuring herself, through a partially open door. I?d watched, fascinated, and unseen.

When I think back, I wonder if maybe she?d left that door a little open intentionally. And then there was that horrible moment she walked in unexpectedly as I was returning her panties after taking them and playing with them in that confused, guilty way.

I?d sneaked silently from my mother?s room to hers, holding the offending garment. As I reached for the draw she stepped from her walk-in closet, where she?d been quietly doing something. I had thought her downstairs, watching something on television.

Well, I was wrong. I expected to be lashed out and berated. She?d done that plenty of times, after all. After she and her father had moved in with my mother, she left no one in any doubt about who ran the house. She controlled her father, as he answered her every whim ? and her father controlled everything else.

So, when the harsh slap didn?t come I was surprised. When the shouts and hair pulling failed to materialise, I felt even more confused.

?Do you look nice in them,? she asked.

?I didn?t do anything with them? I just had them, that?s all!?

?Oh, Michael,? she said softly. ?Don?t lie to me. Not unless you want me to tell your mommy.? She drew out the words, leaving no doubt about the menace behind them. Then more softly she continued.

?I think you wore them, and you did so because it feels nice.?

I said nothing, instead staring at my feet. She sat quietly on the bed, and motioned me to sit beside her. I did so, doubtful of her good intentions, but aware that this was surely better than the beating she could so easily have resorted to.

?Now, tell me the truth. Did you do it because it feels nice??

I continued to look at my feet, but nodded silently. I couldn?t face her.

?Well, at least we have the truth, now.?

She put her arm around my shoulders. Her body was warm and soft, and she said softly, ?Michael, you?re not the first young man to put on panties. It?s ok, you know.?

I relented and spoke, ?But it?s embarrassing. Boys aren?t supposed to??

?Oh, don?t be so silly,? she said in mock admonishment. ?I don?t like you taking my stuff, but I don?t really care if you want to wear girly panties.? Then she laughed and got to her feet.

She walked to her pantie draw and opened it. She then drew out a pair of very frilly panties that I could hardly believe anyone would have worn, they were so clearly meant to be looked at, rather than put on.

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?Why don?t you try these on?? she said. ?I like these ones. They feel wonderful.? She held them out to me, and was captivated by the silky fabric.

?I shouldn?t,? I said. ?It?s wrong/?

?Go on, Michael. Just for me.? She placed them in my hand and then pulled me firmly to my feet. With a touch of menace in her voice, she said. ?I want to see you put them on.?

I felt her hand on my belt, and quickly stepped away. Turning, I pulled down my trousers, eased off my underwear and swiftly pulled the panties on. As I turned around she was grinning at me.

?There,? she said. ?Now you look pretty.? She stepped closer and ran her hands over the waistline, and I instantly became hard. She giggled again, noticing but not commenting on my obvious excitement.

She stood in front of me, and then with her hands on my waist slowly pulled the panties higher.

?It feels good,? she said. ?Doesn?t it??

I stared at my feet once more and nodded.

?Good. Would you like to try a slip, just to see how it looks??

She stepped into her walk-in closet and came back with a silky burgundy slip. She handed it to me, and uncertainly I stepped into the light skirt like garment.

?Michael, you look lovely. Perhaps just a little lipstick. Let me??

?No,? I protested.

She had already reached over to her dressing table and pulled a crimson lipstick out. She pressed it to my lips. Slowly she applied it, looking into my eyes as much as my lips. She watched me melting before her.

Once the lipstick was applied, she stepped back, and in a very circumspect way said, ?Now, some heels to finish off.?

She put my feet gently into the heels she wore, which were a perfect fit at the time. Then taking my hand led me into my mother?s room. We stood side by side and looked in the mirror.

What happened next took me completely by surprise. She leaned over and kissed me fully on my mouth, and reached down to touch soft frilly panties.

?Mmmmmm?.? She said. ?Now, you will always want this, wont you?? Her voice was soft and gentle. It eased over my confused mind, and seemed to sweep me along.

I stood torn between erotic excitement and complete subjugation. My lipstick slightly smeered, I looked quite feminine, but for the sharp bulge in the panties.

?You will always want to wear these little panties and be a little bitch boy.? She kissed me again, my head spinning. Then in a harder tone she added, ?And you will never, ever get over it.?

I looked at her more confused than ever.

?You see,? she went on in matter of fact tone, ?You can?t ever help yourself. You think of me, and you wish you could be like me, and you wish you had a soft warm pussy to offer men, and you will always want to be that which you can never achieve.?

?I don?t need to punish you, Michael, for taking my things,? she continued, her voice hardening. ?You will punish yourself enough. I?m not even going to try to stop you,? she said, her voice now as cold as steel.

?No, I want you to take a pair of panties whenever you need them. And each time you do, you are planting the seed deeper and deeper, and making it harder and harder to stop yourself. You see, it?s you that will be the instrument of your punishment.?

She stepped back, her face sneering now.

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?In fact,? she said cruelly, ?I want you to dress for me. I?ll tell you when. But if I say so, you?re going to wear the things I tell you. And if you don?t your mommy is going to hear about it. Oh, and don?t think I won?t tell my friends who have younger brothers at school with you, I?m sure they?d all like to hear about your recent adventures. And then when you have a girlfriend, if you don?t do exactly as I tell you, they?ll hear about it too.?

With that she swept from the room.

Over the next few years Stephanie made me dress for her entertainment three or four times. Sometimes she would reward me with a kiss, or a glimpse of breast, and once a touch of her soft down like pussy. She guided my hand there, teasing me against her. I don?t think she got off on it at all, it was all about temptation and control. She just wanted to know that she could make me do this ? or anything she wanted.

Often she would lie provocatively on the couch as though unaware of me, her skirt riding up, exposing some pantie, and then she?d slowly turn and fix me with a stare, knowing I couldn?t pull my eyes away. Then she?d smile, secure in the knowledge that she was completely in control. For a young teen it was agonising. Many times it was made worse by my mother not noticing her tormenting me, even when she seemed to do it quite blatantly when people were around.

Most of the time I was too frightened to dress, for fear of being caught, yet the frustration and desire was always there. And as Stephanie had said, it was growing.

And then came the day when my mother and step father separated. It was several years later, and I lost touch with Stephanie, until today.

In the intervening years, once or twice at college, then when I was married, and went on the occasional business trips, I would find myself looking for panties, and taken back to that moment, as though against my will. And her words always came back to me, ?You will always want to wear panties, like a little bitch boy.?

And she was right. It would never stop.

And here we are, forty years later. And Stephanie has contacted me, to talk about ?old times?. I am looking at her email right now, wondering whether I should respond.

The End.


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