My Sister's Lingerie Ch. 01

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.

As illustrated above, my sexual fantasies and dirty daydreams as I stroked off with Brit's panty around my cock, staring at myself in the mirror, did not include those common to most males my age. While I may have been with a female in those panty sex sessions in my mind, I was not fucking her, not cumming as she sucked my cock, nor indulging in any of the full-fledged sex acts that I knew other teenaged boys my own age dreamed of. I was certainly curious about such things, but all of that seemed distant, far off, something I would probably someday enjoy with a woman. In the present, as there in my sister's room, wearing her lingerie, I was more than content to happily jerk off. At times, I did fantasize about being with a woman, but it was lingerie sex I dreamed of, sometimes both of us dressed in bras and panties. When we came to orgasm, we were still so dressed, the thin fabric stretched over our genitals.

As my excitement grew, jerking off there in Brit's room as had become my passion and habit, my masturbatory fantasies took a more forbidden, dirty turn: I was with another male around my own age, and his hands, determined, experienced, aggressive, were exploring my body, clad of course, only in feminine, skimpy undies. I relished it as he caressed and kneaded my panty clad butt, and groaned aloud as he slipped a hand around to my front and stroked my lace covered cock. In my fantasies I would not just wear panty and bra, but everything, the kinds of things the women in Penthouse and Playboy magazines wore: Garter belts and stockings, corsets and maybe even those girdles my mom had in her own underwear drawers. And towering high heels, of course, that would make my legs look more womanly. I would dream of prancing in front of my male lover in my sexy lingerie and modeling for him, as I did in front of the mirror, knowing how intensely hot I was making him. In my jerk off dreams, I was a sexy-dressed and horny and my partner would mount me, from behind, pressing his large, hot, firm erection between my pantied butt cheeks, humping me, as I bucked and pressed against the bed under me, until we both came, hard, loud, passionately, leaving my undies semen drenched. I was vaguely uncomfortable after such fantasies and felt guilt about them, but they gradually became more common and much more graphic.

My free hand held up the hem of my sister's slip and camisole and cupped my breast, or what passed for it, as I fantasized and jacked off before the mirror. My hands on my body, not those of a male or female lover. I gazed through a thick, sexual haze as I stroked and caressed, nearing the point of ejaculation. It would be a good cum, a great one, I knew, the first of several I would enjoy there in Brittany's room. Being all alone for the day, I was determined to spend it all in lingerie, even eating lunch in bra and panties. Sometime during my day alone I thought I'd put on one of the pairs of well-worn pantyhose that Brit had thrown away and I had saved. It was a real thrill for me to pull those things on, and how heavenly it was to caress and stroke my pantyhose-sheathed cock. As my sister would never wear those again, there was the added thrill of actually being able to cum while wearing them. What an exquisite, horny, happy day of dressing like a girl I had planned and the thought of that increased my arousal, bringing me right to the brink.

Of course when all was so perfect was when it all crashed down upon me. Thinking back, I do recall seeing the figures behind me reflected in the mirror as my hand pumped my panty wrapped cock. But I was more than half way lost in my sexual fantasies and it was the loud, angry voice of my sister that destroyed all my dreams of the moment and for the day ahead of me.

"WHAT THE FUCK!"

"What the FUCK are you doing?" Brit screamed, and my eyes focused on the two scantily clad female figures in mirror, just in back of me. I don't know why to this day, why instead of stopping and covering myself, I turned, still holding up the peach satin cami and slip up, and pumping my hot, hard dick.

"Asshole!" Brit yelled, her pretty face contorted in rage. She stood for a moment, there in her beach cover-up, which was open, revealing her shapely body, naked but for the very brief bikini I had worn more than once as I jacked off. Beside her, Kari burst out into near hysterical laughter. The hand gripping my erect cock froze, and I could feel it was too late to stop the inevitable, but I was unable to find the strength to move.

"Fucking asshole!" Brit said, her voice shrill, and she took the three quick steps to me. Helplessly, in near shock, I watched as she cocked her arm, and when her open hand painfully struck my face, she spat again, "Fucking asshole!"

Her words and the slap stung, but at the same time my body was racked with the indescribable pleasure of a very intense orgasm. And as strange as it is for me to write here, it was quite possibly the best ejaculation I had ever experienced up to that point. Just as Brit's palm connected with my cheek, a thick, liquid rope of semen spurted out of my cock, across the short distance between us, and splattered upon my sisters taut, naked belly.

"Oh, you fucking ASSHOLE!" Brit spat, feeling my wetness upon her body, looking down just in time to see another surge of hot ejaculate land upon her tummy. Her hand, slapping my face hard, for a second time, did nothing to stop a final and much weaker spurt of cum that wetly hit the brief triangle of fabric that made up the front of her bikini. I know I groaned, as much in pain as in the seemingly impossible pleasures of my long, hard orgasm.

"Stop it... stop it," my sister said to Kari, turning for a moment to her laughing friend. That loud laughter and the look upon Kari's face was almost as painful for me as my sister's firm slaps. But Brit's friend could hardly stifle, even with a hand to her mouth, a final few giggles as she looked at my lingerie clad body. Then Kari glanced at my sister, and saw my semen drooling down Brit's belly to dampen the top of her bikini and laughed loudly again, pointing at the results of my powerful ejaculation.

I let go of my cock, which finally seemed to deflate a bit, dropped both hands to my sides, not having a clue as to how to react, still more or less frozen before my outraged sister.

"You filthy fuck," Brit angrily said, looking down and then moving quickly, without the least amount of hesitation or shame, pushing down the cum-soaked bikini bottom, stepping out of it, revealing the lush, but so neatly trimmed blond hair that just covered her pussy. She wiped semen off of her body and then, hard, she thrust the wet thing, into my face, rubbing it in. I tasted my own semen, but could do nothing but stand and take it. Once more, I felt hot blood again bringing my cock to erection, despite my just finished orgasm, Kari's laughter and Brit's swearing and scolding. Part of my mind registered that I had never gotten hard again so quickly after getting off.

"I told Mom you were doing this, or something," Brit spat. "But no, she wouldn't do anything to stop it, just telling me it was a phase, whatever the fuck that is. You fucking pervert! Get out of here!"

Still clutching the panty in my hand, the one that had brought off my shameful, humiliating, but so intense orgasm, I hurried past the two young women, Kari standing and smirking, my sister moving towards her bathroom. I slammed my bedroom door behind me and threw myself down upon the bed, crying, still wearing my sister's underthings, still aware of my stiff cock and not being able to figure that part of things out. I heard the shower in Brit's room go on, then off, and soon, after I imagine she had changed into another swimming suit, she and Kari left the house once more. I was never to know what had brought the pair of them back to our home so quickly after leaving the first time, to witness my shameful act of crossdressed masturbation. Despite dwelling on the intense humiliation and pain of the unexpected encounter, I still had an unexplainable erection, and still wore my sister's peach underthings. Out of habit or not knowing what else to do, knowing nothing could improve my lot, I began to jerk off again. Fast and furious, I stroked my cock, using my bare hand, not knowing what I had done with the panty I had used prior. Feverish with lust, shame and need, I reached up and gripped the camisole, ripped it downward, tore it off my body, then grasped the panty down around my upper thighs and ripped that off as well, bringing it to my face, pressing it close, where Brittany's hand had punished me. Crying in distress and fear of what would happen later in the day, when my sister and parents returned home, I came, the semen that time not gushing in powerful spurts from my cock, but oozing slowly out to run down my shaft and onto my hand. Exhausted, my body still clad in my sister's sweaty and ruined lingerie, I dozed off for a fitful nap.