My fetish for wearing women's underthings had started many months prior, but it was during the end of summer break from high school in my eighteenth year, back in 1973, that it all took a dramatic, humiliating turn. I don't recall how my interest for dressing in feminine underthings began or what prompted me to first put on one of my older sister's panties for the first time. But still, after all these years, I recall so clearly the intense, erotic thrill of stepping into and pulling up one of Brittany's brief, sexy panties.
There were many aspects to that exciting act of clothing my body in the opposite gender's most intimate of clothing: The sneaking around to get at my sister's underthings was one part of it. Waiting for her to leave the house so I could slip across the hallway between our bedrooms in the upstairs of our home, was so nerve-wracking, but thrilling. Just opening the dresser drawer where Brit kept her lingerie kicked up the excitement a couple of notches, turning the tightness and warmth I felt in my crotch into a stiff erection. My hands trembled so, as I reached into the drawer, lightly touching the silky, lacy items of lingerie, things usually so close to my sister's naked body, things that felt so good against my own skin. Frequently, I would drop to my knees before the open drawer, as if in worship, inhaling deeply, powerless to stop from doing what I was sure I could not live without and brought me such indescribable pleasure.
In a heady, horny state, I would select one of Brit's panties and put it on, the excitement increasing with a surge, as my balls and stiff cock were embraced and pressed to my body by the tight, sensuous fabric. Always, I would turn to the full length mirror there in my sister's room, to admire in the reflection my slender body wearing the sexy little panty. I was always so highly sexually aroused when I was so clad, and the sexual excitement would increase once I added a bra and pulled on one of her half slips. Mind clouded, body trembling, feeling the heat in my groin, the warm stiffness of my cock straining against the panty, I would stare into the mirror, running my hands up and down my lingerie clad body, from upper thighs to the brassiere stretched across my chest, back down over my pantied ass, up in front over the bulge, again and again. I wished so desperately I could fit into my sister's pumps, particularly high heeled ones she had gotten to wear with her senior high prom dress, but sadly, they were too small for me. I dreamed too of having a wig to wear, to enhance the womanly look of the feminine dressed body I admired in the mirror. I don't think I realized it at the time, but my passion was not just for the lingerie, but in creating the illusion that I was a girl myself. Not that in any way did I wish to be a female, I simply wanted to present a better feminine look. I had quickly learned that my arousal and satisfaction could be increased by selecting a couple more panties from the drawer, wadding them up and stuffing the cups of the bra, to give myself a more girlish look, but still, so much was missing.
Once dressed, I naturally had the overwhelming desire to relieve the intense arousal I was feeling by jacking off. I'd masturbated before I started wearing Brit's undies, of course, but after that first couple of times of getting off when playing with her lingerie, I only felt completely satisfied and sated unless clad at least in one of her panties. I had learned early in my dressing experiences that my dick would leak as the need to ejaculate increased, leaving a tell-tale spot on the front of whatever panty I was wearing. I so lusted for the feeling of slick nylon or sexy lace against my cock while getting off that I solved the problem by going to the clothes hamper in a corner of Brit's room, reaching in to find a panty she had already worn, one I could wrap around my hard dick and stroke off with. It made my experience so complete, so wonderfully fulfilling... At least until the next time the urge came over me, which seemed to happen more and more often. When given the chance at that age, I could go through the process every day, easily.
And so it all began the morning of the day I refer to at the beginning of this memoir, during August of the summer break. I was eighteen and ready to be a senior in high school, and Brittany was a year older, going to be off to her first year of college in the fall. Our parents were working that day, and my sister was off to the beach with her best friend Kari that morning. I had stayed in bed late, listening to our folks leaving the house, then, after what seemed to be so long a time, the sounds of Brit busy in her bedroom stopped and I heard Kari open the door downstairs and call in. Brit answered, and soon the front door of the house closed behind them and I got up to watch the pair walk to Kari's car. Two very attractive young women wearing short and flirty beach cover-ups over bikinis, off for a day at the beach while I carried out my plan to spend the time dressing in lingerie and masturbating.
Naked, in her bedroom, my cock already hard, I stared down into her lingerie drawer as I had done so many times before, aware in detail of all the silky, lacy, intimate secrets within. I had already decided on what to slip on for my first masturbatory experience: That sexy little four piece set in a pale peach that Brit had gotten as a birthday gift just months prior. I remember blushing hotly, trembling a bit as she unwrapped her present, hoping so one noticed the effect the satin undies had on me. I was so jealous that she was to be the one lucky enough to be able to wear the lovely, sexy things. But it was finally my turn that August morning, and with shaking hands I pulled on panty, half slip and hooked the bra before filling each cup with two wadded up panties. Brit had a shapely, womanly body, and I was well aware, based partly on comments by my male friends, that she was particularly attractive to the opposite sex. I pulled the camisole over my head, neatly put it all in place. Her panty was just a little bit large on me, Brit having a more generous butt and hips, but still, the fabric did stretch a bit as my balls and stiff cock filled it. In a trembling, intensely sexual state, I admired my body in the mirror, caressing myself, reveling in the sensation of wearing the seductive, womanly lingerie. It was hard to keep from concentrating my hands too much over the bulge of my cock in the front of the panty, but I was so aware that as horny as I was, I'd leak my fluids generously. Careful as always to not leave the wet evidence of my use of Brittany's undies, I searched through the soiled clothing hamper and found a nylon brief to use to completely pleasure myself. So eager to enjoy my day in lingerie, I was already thinking of the next set I would dress and admire and please myself in: The particularly sexy black lace bra and matching panty.
Lifting the slip and holding it up with one hand, I pushed the panty down so that it merely supported my balls, leaving my stiff prick nakedly exposed. Wrapping the panty around my cock, I slowly stroked it as I admired the figure in the mirror, playing out sexual scenarios in my mind. I was not very sexually active with young women at the time. I had a somewhat steady girlfriend, Loren, but she never let me get much further than heavy kissing and feeling her up through blouse and brassiere. I was not overly aggressive about it, and in fact I was very much a late bloomer when it came to the opposite sex. And strangely, even when pawing at her clothed breasts, my lips locked to hers, I thought not so much about her boobs, but the bra that was supporting them. I wondered about her panty, as well. Was it a lacy bikini? Maybe a satin brief? How I wished I could get her to strip down for me, not so I could take things too far, but only to admire the sight of her lingerie clad body and tenderly caress her body through those intimate garments. Sometimes in my thoughts, Loren graciously offered to take off her undies and let me wear them. That really aroused me, the thought of a woman seeing me so dressed. On those dates when Loren wore a skirt, and she allowed my hands to stroke her pantyhose sheathed legs (from a few inches above her knees, and down), I dreamed of wearing them myself. That dream came true when I found a couple of pairs of Brit's old pantyhose in the trash. I relished wearing them and caressing my own legs and the nice bulge I put in the front of them.
