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Grandfather finds me crossdressed

May 6th, 2006 9:37 pm MDT

  It is 1946 or 1947, to the best I can estimate. I am 12 or 13 years old, and I have this special attraction to women's shoes and stockings, and underthings. Of course I am attracted by girls, but these other parts are overriding issues. I am living with my grandparents and my grandmother, Nona, was an excellent dresser, has always worn very nice shoes and had a good looking figure. She was naturally slim and athletic and has that knack for always looking good. In those days, that meant wearing girdles and padded bras. And your guess was right, I couldn't stay out of her underwear drawers! That, and the fact that my best friend had two sisters, who were among the best looking females in our school, kept me right on a sexual edge all of the time that I was awake. It was wrong of me to have stolen a pair of one of the sister's "Bass Weejun" penny loafers, but fears of humiliation or punishment were not the highest things on my "list". I just had to be close to those beautiful shoes! There was a really powerful underlying need to cause me to steal them. I didn't have a clue as to what was going on inside of me, but I had to do it. Well, in the moments when I could be alone in our house, which usually was every afternoon from  about 3:30 to 5:00PM, I got to play with my toys! It wasn't long before I began to wonder what  the heck was that dribble stuff coming out of my penis, as I was wearing my grandmother's panty girdle and Pam's penny loafers, and walking around pretending to be like a girl... the best I could, anyway. It wasn't long before I could make that "fluid" happen, and it felt oh so good when it came out. I could make it feel especially good by lying on the floor and moving my hips to grind my pelvic area on the rug. Later I figured how to tie ropes around my crotch and legs to increase the tension and so that there would be a constant rubbing on my penis as I sat, or walked or ...nearly any activity. So I was able to "get off" nearly every afternoon, except on weekends when my grandparents stayed home. I was really glad when Monday came around! So here I am, just an uninformed kid, not having any understanding or knowledge even of the notion of masturbation, or erections... or that such a thing as intercourse existed. I had seen the word "fuck" written under bridges... but I had no idea of what it meant. I actually believed in the "virgin birth" but didn't know what that meant, either. And here I am having an orgasm nearly every day. What do they say about ignorance being bliss? Well it wasn't exactly bliss, as I felt secretly ashamed of what I was doing. In my heart I knew it wasn't right. I had been brought up as a Catholic... which compounded the problem. Little by little, I was able to enhance what I was doing, with more elaborate use of ropes... bondage was definitely a turn-on, and also collecting other bits of female clothing. It seemed easy to "pick things up" here and there. And you know that was also part of the thrill. There is an additional rush from fondling and playing with things you have gotten from stealing ... the rethinking of the original happenstance is still stimulating. So there I was, dressed as a female, but not wanting anyone to see me like that; wearing women's underwear, wearing "girl's" shoes, and all(self)tied up. And all of this was done without any outside knowledge of what the hell was going on! I believed it was all wrong, but the rush was so good that I was going to find a way to do it no matter what, and just as often as I could. A Crisis: As I implied, this process continued to elaborate and I was now moving my activity from a dim corner of the basement to the upstairs living area of our house. That added to the thrill and guilt, and provided an even higher rush. One day as I was wearing Nona's nylons -seamed, of course, as that was the only kind in those days, and her panty girdle with garters, together with my friend's sister's penny loafers and bobby socks carefully and neatly folded down around my ankles, and I had tied myself to the toilet ( I told you this was getting more complex...) and was in the midst of getting erect and excited, I heard the front door open. Oh, oh! This was not supposed to happen! There were loud deliberate footsteps heading right for where I was... and my Grandfather burst through he bathroom door! There I was, tied tightly, in a sitting position on the toilet, and dressed like that!             He was shocked, and temporarily stalled.... I was mortified and ashamed to the core, and could not have imagined anything worse ever happening.... But I could not do anything about it for my ankles were tied together and to the base of the toilet, my knees were tied together, I had shoelaces tied around my penis and balls, I was wearing Nona's best leather belt, and one of her bras, and I had self tied my wrists as best I could. Oh, what a humiliation. All I could do was to stare at the floor and wait for whatever was going to happen. I could not even look into my Grandfather's face. After what seemed like an eternity of waiting, and Grandfather regained "some" composure, and he briefly uttered "Get this all cleaned up and put away. I don't want your Grandmother to see you like this." And he walked out and closed the door.    Nothing more was ever, ever, said about the incident. Epilog: Driven by my hormones which were excitedly crowding out nearly everything else in my bloodstream, I simply got better at hiding what I was doing and continued to cross dress, to let bondage turn up my thermostat, and never looked back. The incident did not deter my pleasures nor has not inhibited my excitement and satisfactions in any way. It is now fifty-five years later, and I still find the same thrill that I had originally discovered ... except that  it is now 5inch patent high heels, leather clothing, handcuffs, whips, and bondage ... and I don't much care who is wearing the attractive female clothing, my female partner or myself. And I have found wonderfully great pleasures as a male dominant to females, except that my thrill is multiplied, as I play that scene crossdressed as a domme.

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  • Luscious Lisa Lips
    Re: Grandfather finds me crossdressed Luscious Lisa Lips May 16th, 2006 3:58 am MDT my dear, you should become an authoress and do some writing professionally. the story above is so incredibly visual and perceptual that anyone could relate to your words. throughout the years, and there are many, many of them, many similar scenarios have happened to myself and i am sure---to many others. i can remember some 60 years ago---the look and feel and the texture of my mothers burgandy floor length velour dress----like i almost have it on right now. and i used to tie myself in a very similar manner to the way you did, and i would grind on the floor while bound---later using a pillow as it was more comfortable....you have struck home with your candid and honest experiences.................................lusciouslisalips               kisses from me my dear for bringing all of this to light once again.... 
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