Richard's First free porn video

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After one more lingering smoky kiss, I disengaged myself from Rolanda's arms and hopped out of the Cadillac's passenger seat. Always the gentleman, I strode quickly around the front of the car to open the driver's door for Rolanda to alight, completely forgetting that my stiff cock was still protruding from my open fly! As I opened her door, Rolanda slid off the rich leather seat and onto her 5 inch heeled red and gold pumps, her lovely gold clutch wedged delicately under the arm of her mink. She reached down with her satin glove and gently wrapped her fingers around my hardon...."Forget something, Honey?" she smiled wickedly. "Mmmm, it's still so hard!" she arched her eyebrows to show mock surprise, "I think you must like me!" I blushed. I always attempted to be suave (impossible for a 22-year old) and leaving my manhood pointing unerringly like a compass needle to sexual fulfillment seemed an embarrassing faux pax. "Sorry. Hope the house mother isn't waiting up for us!" I quipped, proud to think of an amusing response. "Yes she is, but you're looking at her and you've already been busted!" she laughed in that deightfully faggy gay voice of hers which I was beginning to adore. Recovering my mannners, as best I could, I offered the gorgeous creature my arm which she took appreciatively like a perfect lady. As we walked to the door leading to the interior of the impressive home, I discretely reached down and jammed my pecker back into my pants. Auntie Rolanda noticed, but refrained from whatever Mae West one liners may have popped into her head at that moment. A short flight of steps led up to the interior door, which I held open for her to pass into what turned out to be a spacious cloak and utility room. Rolanda flipped on the lights, then deftly darkened them with a dimmer. She took my hand in hers and led me into a spacious kitchen which sparkled in the reflection of its own dimmed lights. Glowing cherry floors and endless sparkling granite counters seemed to stretch on forever. I had been in a couple of these older mansions which fronted on Lake Washington before when invited to boring social events thrown by my parents' friends, but I was unprepared for the sheer elegance of the total renovation of this 1920s Tudor which had obviously been recently completed. I could see that she was an imaculate housekeeper, and I couldn't resist commenting on the fact, "My, Rolanda, you keep a beautiful home!" It's not me, Baby, I have a full time maid and housekeeper, Lisa, a young former trannie hooker slut that I rescued from the streets. She does do a nice job, doesn't she?" I let out a low whistle of appreciation as I nodded in agreement. I'd only seen the garage and the kitchen which was almost as large as my apartment, but if the rest of the place was half as beautiful, I had stumbled into virtual pleasure palace twice in one evening! "Does she live here with you?" "Yes, Sweety, she has her own little apartment over the boathouse. It's not huge, but she seems very comfortable there. She behaves herself, and I've given her my permission entertain an occasional trannie lover down there if they are quiet about it. I don't want to have problems with my neighbors, who are nosy enough as it is without thinking that I'm running a bordello for queens over my boathouse!" Accustomed to my crummy one bedroom apartment in the University District, I found Rolanda's home to be overwhelmingly opulent by my standards. Dimmed spotlamps recessed into the high cherry paneled ceiling glowed warmly, bathing the elegant kitchen in golden luminescence. She flipped another switch and a veritable wall of framed glass cabinets came to life, filled with exquisite china and crystal, all illuminated by strategically hidden mini-lamps. It was like looking at the latest edition of "Architectural Digest". Rolanda watched me soaking it up, obviously satisfied that I was suitably impressed. "Care for an apertif, Honey?" "Eh, yes, please, do you have any Cointreau, Auntie?" "Of course, I do, Darling. That sounds good to me too." She popped one of the china closet cabinet doors open and picked out two small but elegant snifters. Her heels softly click-clicked on the wood floor as she strutted to an immense panel of inlaid cherry and rotated it on a hidden center spindle to reveal a very well stocked vertical bar built into the back side of the door. She inventoried its contents for a moment, allowing me to admire her perfectly styled ash blonde wig and immense earrings from behind, my eyes irresistably tracing the outlines of her mink down to where it revealed just a tease of red satin gown above her red and gold pumps. It was a ravishing look of sexy elegance beyond anything my middle class girlfriends would ever have been able to muster. I couldn't help but note that she was probably wearing, in clothing, jewelry and accessories, the equivalent of my annual student stipend from my parents! Eventually she found the Cointreau amongst the scores of bottles and brought it back to where I was standing. She handed me the snifters and invited me to follow her deeper into the interior of the house. Progressively, as she switched on more lights, the grandeur of the place was revealed to my atonished eyes. We walked through a large dining room. The cherry-planked floor morphed seamlessly into red oak. A large Danish styled dining table with seating for twelve was firmly ensconced on a magnificent Turkish Hereke silk carpet, richly detailed in deepest wine reds and cobalt blues. The table was set as if dinner guests were expected at any moment. The effect was stunning. Rolanda paused to allow my eyes to appreciate the large paintings embellishing the walls. A large lighted china cabinet covered most of one side of the room, filled with even more sets of elegant crystal and crockery. "I have a fetish for Oriental carpets, Darling, one of my greatest weaknesses." Then she looked at me and said, "Except for wonderful young men like you, of course." I beamed at the obviously overt sexual compliment. She stepped closer to me and reached her gloved hand to my thigh, "Shoene Beine, Darling," she murmurred as we both remembered her first subtle act of gay flirtation at the outset of the evening. I blushed again, and my penis twitched for the hundredth time since I had met Rolanda and Phyllis. She leaned against me and again our lips met briefly in a sweet affectionate kiss. I was still amazed at how exciting it was to kiss a man wearing lipstick and full makeup! My fascination with Rolanda's elegant home had distracted me from my usual obsession with sex for a short while, but the kiss brought my attention back to the eroticism and pleasure that beckoned from somewhere in the dimmed recesses of Rolanda's elegant home. Rolanda again took my arm and walked me towards a spacious living room which lay a half flight of broad, oak edged slate stairs below the dining room. In the diminished lighting, through the recently enlarged windows of the living room, my eyes were drawn to the twinkling lights of Mercer Island in the distance, romantically reflecting off the calm waters of Lake Washington. Another impressive Middle Eastern carpet of mind boggling proportions, this one a Persian Isfahan, engulfed the expanse of gleaming oak floor, subtly flooding the room with its glowing hues. The living room was furnished with very comfortable looking overstuffed deep green leather sofas, chairs and love seats, all with golden accents and teak trim. The effect of wealth was mesmerizing for an impoverished college kid with his one and only car marooned in the repair shop! The room was deceptively polymorphic, with six walls of varying dimensions, the three largest backing to the view of the lake, and I supposed on nice clear days, the Cascade Range in the background. The smaller walls of oak paneling faced the windows and were tastefully hung with wonderful contemporary prints. A Greek marble column, sparkling dimly with subtle gold leaf accents, dominated one of the many corners, topped by clinging golden cherubs clutching bunches of grapes. Art filled the house, but not ostentatiously. It gave the home a delightfully androgynous feeling. No genetic woman would ever decorate like this, and neither would a swashbuckling executive-type man, but a gay transgendered head of a department store display department certainly would! She led me to a sumptuous loveseat with a nice view of the water. The landscaping outside was unobtrusively illuminated with soft hidden floodlights which showed off the carefully manicured hedges and foliage which served to screen the unshaded windows from the potentially prying eyes of neighbors. Standing in front of the little sofa, Rolanda turned her back to me and inviting my help, gracefully shrugged out of her mink, which I carefully draped over the back of a nearby chair. Her lovely shining red satin gown was now fully exposed to my appreciative eyes again. She sank gracefully into the soft leather of the intimate sofa, her sexy elegance competing for my attention with the commanding view of the darkened lake through the room's expansive windows. Eventually, she patted the cushion next to her, "Take a load off your loafers, Honey". I gladly accepted the invitation. An elegant glass cocktail table, richly trimmed in gold, sat in front of the two person couch. Femininely, Rolanda set the bottle of Cointreau on the table. "Pour, Richard," and then we both chuckled at the cleverly contrived verbal ambiguity between Ben Franklin's famous periodical, "Poor Richard's Almanac", my own impoverished financial condition, and the need to decant the apertifs! I was growing to appreciate Rolanda not only for her erotic attractiveness, but also for her quick wit and impressive intellect. After the supercharged sexuality of the events at Ruthann's parents' home, I was beginning to feel very comfortable with her, despite my nagging doubts about the outrageous homosexuality of the evening's events. I uncorked the Cointreau and poured a modest amount of the clear liquor into both snifters. "Mmmm, I love the aroma of the citrus," I mused as I swirled the snifters to enhance the release of the fragrance. I handed one to Auntie Rolanda and slid back onto the thick leather cushion of the loveseat. Rolanda opened her expensive purse and took out her golden cigarette pouch, clicked it open and offered me another Virginia Slim, which I eagerly accepted, instantly feeling surprisingly femme again. Something about smoking these femmy menthol cigarettes as if I had been doing it all my life caused my whole demeanor to change. She pretended not to notice the wave of femininity that swept across my entire body. I took the lighter and like a perfect gentleman, lit first Rolanda's and then mine. I inhaled the creamy smoke deeply, enjoying the tasty mixture of menthol and the orangey Cointreau. She did the same, smiled at me and touched my hand with her silky glove. The effect was deliciously pleasurable and I felt a species of relaxed contentment I had seldom if ever felt before in the presence of another person. I wanted to pinch myself to make sure I wasn't dreaming this, it was just too perfect. "Welcome to my humble abode, Darling. Do you like it?" (I was getting used to this swishy male in women's clothing calling me endearing terms, like "Darling" and "Honey" or "Baby". It just felt so unbelievably natural and warm.) "It's lovely, so elegant and yet comfortable too". I mildly surprised myself by choosing "lovely" instead of some other more masculine adjective. Something inside me was subtly changing, but naively, I couldn't.....or didn't want to....acknowledge it yet. The pleasure of immersion in the femme world on the other side of the gender line was incredibly seductive. Rolanda and Phyllis made it all seem so comfortable and normal. My previously unexamined macho and homophobic attitudes had suddenly and unexpectedly been put to the test, but the fears fell away like so many autumnal leaves in a soft breeze. The idea of being able to fulfill my sexual needs at will held great appeal. Phyllis had made a straightforward and persuasive argument for it, and I found my defenses melting away as I smoked my long white cigarette like a perfect sissified lady. Rolanda smiled, apparently pleased with my appraisal of her carefully crafted gay love nest. She already had elaborate plans for me and how I would fit into her libidinous yet elegant lifestyle. I had no idea how carefully planned this evening had been, and how cleverly and willingly I had been seduced into Rolanda's and Phyllis's transgendered gay lifestyle. Sitting next to me, Auntie Rolanda's pleasant noncommital smile revealed little of just how satisfied she was with her latest "conversion". But her plans for me, elaborate as they might be, could wait for the moment. She was simply enjoying being with me right now, pleasantly surprised at how much she was attracted to the innocent naivete' of her newest recruit. I had turned out to be much more facile than she had anticipated from her interviews with Ruthann about me for the past several weeks. On the basis of Ruthann's intuitions about me, Rolanda, the black satin Spider Lady, had spun her silken trap for me. The best of it for her was how willingly I had been entrapped without the slightest struggle. She did know from Ruthann that I was attracted to very feminine women and their adornments, but the evening so far had revealed to her that she had dramatically underestimated my "convertibility". This was becoming so much easier than she had thought it would be. So, for the moment, she was just going to flow with it and enjoy the sexual pleasure that she was quite sure would materialize shortly down the hallway in her opulent boudoir. Again, I was staring at her face, so attractively mature, and flawlessly made up to shame any genetic woman into irrelevance. I couldn't believe what had happened to me, but I was enjoying it. Whatever homophobic defenses I had once possessed lay in tatters, overwhelmed by the sexual attractiveness of my increasingly adored Auntie Rolanda, and the unexpected allure of the forbidden fruit on her side of the gender divide. I still was repulsed by the idea of sexual intimacy with a man, but my mind had successfully rationalized being very attracted sexually to a man within the context of buffering androgyny. As I briefly reflected on that, Rolanda picked up what looked like a remote control for a television and pressed a button. With an almost inaudible whirring sound, an enormous flat screen TV glided out of the ceiling, positioning itself between us and the windows. I was astonished. I'd never seen such a large screen before. "I like to watch porn videos sometimes, Darling, and this is my favorite place to watch it. I have a huge collection of gay and trannie films, we'll watch them sometime if you get bored with me." She smiled as she exhaled a plume of minty smoke and gently squeezed my hand. Another deft push of the button and the screen disappeared into the ceiling again, hardly making a sound. I loved to watch porn movies, but I couldn't imagine getting bored with Auntie Rolanda! It crossed my mind that it might be very exciting to watch porn while engaged in naughty transgendered sex on this wonderfully supple leather loveseat. "I'm glad you like my house," she purred, as she caressed my shoulder. Her smooth satin gown glowed seductively in the soft light of the room. I reached my hand to her thigh, gently stroking the soft silky material, feeling her garters and stocking tops. "It's perfect for entertaining, don't you think," she mused rhetorically as she exhaled another creamy plume of smoke towards me, electrifying my already semi-aroused body. "As an exucutive at the store, they expect me to throw my share of dinner parties. I think everyone at the store is suspicious of my sexual orientation, but they all just look the other way. None of them really want to know for sure. It's well known in the department store industry that most men in the display departments are gay. So they all come to the parties. The women seem to have a sixth sense about homosexuals and for some silly reason, they feel more comfortable with us than they do with straight men. I think the genetic gals assume we're gay until proven otherwise, and of course being married and having kids is not perfect litmus test either, look at Ruthann's father!" she laughed. We smoked and sipped our Cointreaus in silence for a bit, caressing and touching affectionately, a slowly developing feeling of sexual arousal was building again between us. Rolanda opened her purse again and fished around for her lipstick and compact. While I watched with admiration, she opened the mirror on the compact and pretending to ignore me, refreshed her gorgeous lips with more glowing red, and then expertly renewed her already flawless makeup with an elegant little brush. We finished our cigarettes, and Rolanda effeminately stubbed hers out, again exciting me with the sight of the creamy bright red lipstick stain on the filter. "Drink up, Darling," she purred, "the tour continues." She stood up and took my hand gently in hers, leading me to points fascinatingly unknown but eagerly anticipated. The house was a two story in the traditional Tudor style of the Roaring Twenties in America. Gesturing to an impressive curved stairway to the second floor, Rolanda explained, "Originally the house had all the bedrooms on the upper level, four rather small ones and only one bath, totally outdated. I had the contractor knock out the walls and create two guest suites with their own baths, a much more workable situation for overnight guests. I'll show you those in the morning." "Do you have family from out of town that visits you often?" I asked naively. "No, of course not, Honey, I'm talking about visiting queens, Silly." she laughed, trying to shock me a bit. "No, actually, I do have relatives back east who come out occasionally to enjoy Seattle. But I also have lots of swishy gay trannie friends who visit fairly often." She spoke to me openly about topics from her gay lifestyle as if she were discussing the weather. Obviously, she was completely comfortable with who and what she was. As I pondered the wonder of it, I thought to myself that she was in fact not just relaxed about it, but possessed with a sense of delightful self assurance regarding her gay transgendered lifestyle. To an ingenue like myself, still clinging to the remnants of my own homophobic denial, it was wonderfully refreshing! She led me into a hall off the living room. "This is an addition I had them put on for my 'Royal Suite'." Her hand squeezed mine. "Every queen has to have a royal suite, Darling," she chortled in her gay lilt that made me tingle with anticipation. The walls of the hallway were hung with signed Enrico Dalilamo prints. We paused to admire them. "'Enrica' was a queen too, Darling, did you know that?" She used the Italian feminine gender ending to "Enrica" to underscore the point. All I knew about Dalilamo was the fascinating style of his surrealistic work. I shook my head. "Even his kinky little mustache was penciled in, but without it in drag he was gorgeous!" she exclaimed proudly, "Very elegant slinky lady and always the belle of the ball." We continued down the hall to the master bedroom suite. Nothing I had seen so far had prepared me for what was revealed to my astonished eyes as elegant double doors swung wide to Rolanda's gentle push. It was enormous, a veritable home in its own right. The large windows were draped with gold satin brocades and shuttered with dazzling white plantation blinds. An immense four poster French provincial bed dominated one side of the room. As we approached it I caught a glimpse of the huge plate glass mirror suspended from the overhead framework, partially hidden by the brocaded satin draping that surrounded the top of the substantial four posted supports. Rolanda caught me looking at the mirror. "So I can see what I'm doing in the sheets, Honey" she hinted broadly. Elegant matching tables flanked the scrolled white and gold headboard. The bed was made up with glowing white satin sheets and pillows under a puffy brocaded satin comforter embroidered with golden threaded floral designs. Opposite the bed and in front of the windows was a stylish sitting area furnished with carefully coordinated period pieces....a love seat, two wing-backed chairs, all surrounding an elegant cocktail table. Everything in the room was immaculately clean and well kept like the rest of the house, the place was impressively spotless. I imagined Lisa, sexily clad in a maid's uniform, carefully dusting and shining everything while Rolanda was at work! Walls of tastefully coordinated dressers and armoirs were arranged against the walls on all sides of the room. I could see a spacious makeup table of the same style, its top covered with a vast array of the cosmetic necessities I assumed to comprise "drag queen" cosmetics. It was backed by a very large mirror which incorporated many tiny spotlights aimed strategically to where Auntie Rolanda would sit as she applied the contents of the glittering array of bottles and jars neatly arranged in an arc for convenient access. There were brushes ranging from big and fluffy to the tiniest fine bristled variety, all upended in elegant cylindrical holders. Row upon row of lipstick tubes were arranged in tiered cases, their beautiful enameled containers glowed in scores of elegant golds, silvers, and laquered finishes in countless hues. "This is the 'inner sanctum' of Auntie Rolanda's love nest, Sugar. I hope you approve," she smiled at me, batting her tantalizingly long false eyelashes at me in feigned innocence. She strutted in her heels to one of two large mirrored doors opposite the bed and swung the left door open to reveal the largest walk in closet I had ever seen. It was immense, nearly as large as my apartment, perhaps larger. It had a large granite-topped oak dressing island in the center that stretched perhaps twelve feet into the interior! Inside the door to my left were long racks of high heeled shoes, hundreds of them in every conceivable color and style. My eyes must have bugged out of my head as I scanned the overwhelming display of erotic high heels. Rolanda laughed as she watched the young lecher survey the contents of an entire shoe store. The fetish ran deep and I was temporarily speechless. "Honey, you come over to see Auntie Rolanda, and I'll model every pair of them for you. Some of them have soles that have never touched the pavement. They've only been worn to bed by a sexy little old lady!" she laughed her gay androgynous laugh that captivated and excited me. "They're all DLC-FMPs," she spelled it out in a tumble of initials. "DLCFMPs?" I managed, clueless. "Yes, Honey, 'Dorothy LaMour Come Fuck Me Pumps'!" I laughed out loud at the outrageously correct terminology. Rolanda rolled her eyes demurely, smiling innocently as if the word "fuck" would never cross her silky red lips! Peering farther back into the recesses of the immense closet, I could see scores of dresser drawers running down the wide center aisle, descending to the floor on both sides. Rolanda followed my gaze, "For lingerie and jewelry, Honey, can't ever have too much of that!" I nodded my head in abject astonishment, and my cock twitched as I imagined what wonders might be found in those layers upon layers of drawers....panties, nighties, stockings, girdles, corsets, bras....my curiosity was running wild at the hidden mysteries lying as yet unseen in those many tiers of drawers. Towards the walls there were four rows of sturdy upper and lower hanger support bars paralleling each other into the recesses of the closet, punctuated by vertical, built-in matching oak chests every few feet, each with lighted mirrors at upper torso height. Suspended by countless padded satin hangers were full length ball gowns of satin and sequins, smart tailored Chanel style suits in many chic colors and all with contrasting or white piping to underscore their businesslike designs, stunning short cocktail dresses, elegant pant suits, many brocaded satin cheongsams, both full length and intriguingly short styles, and at the end of one row, a huge selection of furs, perhaps fifteen or more in many different styles, long and short, big collared and bubble cuffed at sleeves and hems. It was a delicious secret garden filled with lusciously sexy and stylish women's clothing of every hue and description. I had heard the term "out of the closet" to describe gay guys that were no longer hiding their homosexuality from the straight world, but I had never imagined what some of those closets must have been like until I saw Rolanda's masterpiece! Auntie Rolanda let me look. She was obviously enjoying my astonishment at her overwhelming inventory of sexy clothes. Finally, she cleared her throat, "Baby, we can't stand here staring all night, or we'll never get well enough acquainted in the boudoir!" Rolanda led me to the first vertical set of drawers and rolled one open to reveal row upon row of dazzling earring pairs. "You like, Honey?" "Mmmm, you know I love those long dangly earrings that you wear, but I had no idea that you had this many to choose from!" "Yes, I'm afraid I'm a bit obsessed with jewelry. Whenever you decide to call on Auntie Rolanda, you are welcome to pick as many pairs of these as you like for me to model for you. I love earrings, bracelets, and big gaudy rings. Would you like that, Baby?" "I was overwhelmed by the suggestion. I adored long earrings and flashy jewelry on ladies, and hated it that so many of my girlfriends seemed to prefer shorter earring styles or simple ear stud to the stunning "shoulder dusters" that fascinated me so. Now, I was by implication being invited to select from a dazzling selection of sexy ear adornments to my heart's content for the lovely Rolanda to wear for my pleasure. It was a delightful offer. I reached into the drawer and selected a pair of large pear shaped pearl drops, studded with diamonds and accented with gold. I held them up and enjoyed the sparkling of the rhinestone diamonds in contrast to the soft opulence of the large faux pearls. I handed them to Rolanda. "You want me to model them for you?" "Please. Yes I would like that very much," I whispered, once again becoming aroused by how much she seemed to enjoy pleasing me. Rolanda slipped the earrings she was wearing off of her smallish lobes and dropped them into a velvet lined wooden box on the top of the chest. The ones I had selected had spring-loaded clips covered with soft foam rubber caps to protect the wearer's earlobes. Concentrating on her image in the mirror, Rolanda expertly clipped the gorgeous objects to her lobes, then stopped to admire them and primp her wig a bit, before turning to me. "Do you like them, Sweety?" she purred, already knowing from the expression on my youthful face what the answer would be. I nodded affirmatively. She reached down and slid her gloved hand against the bulge in the crotch of my trousers. I was hard as a rock. "Nice, Baby, I'm looking forward to seeing all of that," she purred seductively, "up close and very, very personal." I felt my knees getting weak. The goose bumps were double-timing it up the back of my neck. She smiled at me as I admired her enormous earrings accentuating the platinum hue of her gorgeous wig. She knew exactly what she was doing to me and enjoying it immensely as she stroked my raging hard on, making time stand still for an electric moment. "Pick another pair," Baby Doll. "But I like those on you very much, Auntie Rolanda" I protested. "Just do as I say," Honey, this time more firmly. Obediently, I turned to the open earring drawer, again dazzled by the many pairs of sparkling shoulder dusters. "How about these," I pointed to a set with large rhinestones at the tops which suspended many graceful strands of twinkling diamonds hanging down seductively for a good three inches or more. "Yes, I like those, some of my favorites," she whispered. "Now, try them on." "You mean you want me to put them on your ears for you, Rolanda?" "No, Silly, I mean for you to try them on your own ears." I was stunned. She actually wanted me to model them for her. "Okay, whatever you say." I looked in the lighted mirror, seeing my strong masculine face staring back at me. She called me "Silly" and right now I felt very silly and embarrassed, but I complied with her instructions. I picked up one earring, admiring the design in spite of myself. I opened the clasp which made a distinct little metallic clink as my fingers easily overcame its light spring tension. Looking in the mirror, I carefully positioned the large faux diamond next to my earlobe and pinched the clasp closed on my skin. The protective rubber covering gripped the lobe in surprising comfort. The cascading stones winked back at me as I beheld myself with a long dangling earring on one of my ears for the first time. I picked up the matching piece of jewelry from its velvet lined compartment, and this time more quickly clamped it onto my other ear, I was unwittingly getting the hang of it. "What do you think, Sugar? Do you like them?" I gazed at my image in the mirror. Unexpectedly, I loved the weight on my earlobes. The beautiful feminine baubles gleamed back at me, looking somehow ridiculous and yet androgynously erotic at the same time. "I, I....think I like them very much," I managed to stammer. "They look great on you. Move your head around a little and make them sway a bit, catch the light." I complied, marveling at the feeling of adornment while watching the light show in the mirror. It was somehow exciting and naughty to see myself with elegant ladies' earrings streaming from my lobes and tickling the sides of my neck. Little electric thrills ran down my spine as I selfconsciously admired the jewelry in the mirror. "Good, I'm glad you like wearing them. Anytime you visit Auntie Rolanda, feel free to try on anything in this closet that fits you and makes you feel feel special and nice, or even a bit naughty." she gave me a conspiratorial wink. When you're here, you can do anything that feels nice or sexy and it will just be our little secret. Would you like that?" I blushed, but it was a generous invitation to explore newly discovered territory in an environment of safety and comfort. "You may take them off if it makes you uncomfortable, Darling," reassured Rolanda. "Wearing women's things can be a liberating experience if you find it pleasurable, but the first time can be a little unsettling. Just ask me, I've been doing it most of my adult life," she chortled. "Thank you, Auntie, that's very generous of you. I appreciate it. I think I'll leave them on for a bit longer. It's a completely new experience for me and it takes a little getting used to, but somehow it feels, well, exciting." Rolanda just smiled knowingly and proceeded to another set of drawers. She pulled the hidden lip under one of the drawers and it rolled silently open revealing row upon row of shiny silken panties. She selected a royal blue satin pair and unfolded them on the smooth granite top surface. "Here, these are for you to wear tonight." She held them up to show me the satin-piped round cutouts that could be for only one purpose, to expose a man's penis and scrotal sac. To make sure I saw the significance of that, she slid her gloved hand into the panties and allowed her long slender fingers to protrude through the holes, wiggling them seductively to make sure I got the point. "Now, let's get ready for the main event, Darling, shall we?" I felt my already hard cock stiffen as it became abundantly clear that we were headed for that enormous satin encased bed, just what I had been hoping for since Rolanda suggested that I spend the night at her place. She walked me out of the closet and to the second large mirrored door to the right of the first. The lights clicked on automatically as the door swung open. This closet was somewhat smaller than the first, but was lined with row upon row of men's suits, sportcoats, topcoats, ties, and racks of expensive men's shoes of every imaginable style. My quizzical look was instantly answered. "These are my boy's clothes. Ugh! At work, I have to look the part of an executive. I hate being in boi mode, but we do what we have to do in this world. The queens haven't taken over yet, so we all reluctantly play our little parts patiently until the revolution!" She laughed, enjoying the image of millions of drag queens running the world. "Here, take off your clothes. These vacant hangers are for you to place your clothing on," she indicated a vacant section among the amazing collection of lavish men's garments. Rolanda selected a long blue satin man's dressing robe that matched the panties she had left for me on one of the dressers. She handed it to me. "Here, Sugar, this should fit you." She swished out of the closet, and then before she vanished around the corner, she turned and said, "Excuse me for a minute, I'm going to prepare myself for beddie bye. Meet you in the boudoir, Darling, and don't keep Auntie waiting." She gave me a mockingly stern look one would expect from the perfect Auntie Dearest, and disappeared from view. I stood looking at the robe for a moment. Its silky material seemed less than masculine, but standing there wearing a pair of shoulder length diamond earrings made my hesitation about donning it seem exceedingly silly. I hung the robe on the vacant rod and proceeded to undress. My heart was racing with anticipation concerning what might transpire next. I carefully hung my trousers, shirt, jacket, and tie on the available hangers. I slipped my boxer shorts down, allowing my erection to pop out above the waistband. Now completely nude, I turned and picked up the satin panties that Auntie Rolanda had given me. They looked brand new, never worn. I loved the satiny feeling of the bikini styled garment. I pulled the panties up my legs, marveling at the soft cool silky feeling as they hugged my well muscled legs. I eased them over my buttocks and fitted my still very stiff cock through the satin- ringed hole. The satin ring was lined with elastic and it instantly conformed to the girth of my erection, surrounding it exquisitely in its silky grip. I reached down and fitted my balls through the larger lower hole, enjoying the firmness of the way it surrounded my sperm filled testicals. I removed the satin dressing robe from its hanger and slipped it over my shoulders, sliding my arms into the silky sleeves. The material was cool to the touch and incredibly sensual as it clung to my relatively hairless body. I loved the way it felt as I tied the belt around my aroused body. I walked back into the spacious bedroom, marveling at its size and tasteful decor. Rolanda had not yet re-emerged from her queenly closet, so I took the opportunity to explore the "royal suite". To my left there was an enormous bathroom. It was finished in large square black onyx and white travertine tile. Massive towell racks supported a large supply of oversized black and white Turkish towel sets, enough for a sizable beach party. A very large shower was enclosed in sparklingly clear half inch glass panels, and there were two shower heads on opposite sides. A gigantic jetted soaking tub of sculptured white marble lay next to a plantation shuttered floor to ceiling window that flanked its entire length. I lifted a section of shutters and took a peek. The window faced southeast with an expansive view of the lake and Seward Park in the distance. The tub was sculpted voluptuously to provide two comfortable adjoining seats so that two bathers could enjoy the therapeutic value provided by a myriad of strategically positioned submerged jets. I opened the door into the water closet which held a very expensive looking black ceramic toilet and matching bidet. A hook on the wall suspended a pearlized white douche bag. My heart skipped a beat. I was pondering what the significance of that might be when Rolanda joined me in the bathroom suite. She was wearing a shimmering full length brocaded gold satin dressing gown, the collar, cuffs, and hem trimmed with blonde mink. It was the most stunning piece of lingerie my young eyes had ver beheld. Her stockinged feet were tucked into a towering pair of gold kid ankle strap mules trimmed with ribbons of silver leather that wrapped seductively over the toes and carried back along the soles to outline the entire footprint and the highly arched heels and insteps and up to the ankle straps. She had changed out of her black satin into glowing opera length gold lame gloves. She had lit another sexy cigarette, its filter ringed with her bright Chinese red lipstick, and she was holding it in her outstretched fingers like the matinee idol that she portrayed so well, her wrist bent back limply as the perfect affectation of gay femininity. I could clearly see the dazzling row of pearl buttons that ran up the inside of her forearm and her long slender fingers were adorned with several large rings designed to compliment the pearl and diamond earrings I had selected for her earlier in the visit to her amazing closet. Rolanda spun herself around slowly, letting me take in the erotic way the shiny material draped loosely over the curves of her slender body. "Do you like, Baby?" she purred, stopping to take a long slow inhalation of creamy smoke, exhaling it gracefully through her voluptuously pursed lips. "God, Rolanda, I love it. You look absolutely smashing!" I was mesmerized by the ultimate fulfillment of a post-adolescent's most erotic fantasy. "I'm glad you're not disappointed, Honey," she beamed approvingly, with the self assurance of a practiced femme fatale. She was clearly enjoying my enraptured response to her efforts. "What do you think of my little bathing facility?" "It's simply stunning!" "I thought you might approve. Did you notice the double shower heads and the tub for two?" I nodded appreciatively. "Bathing is so much more enjoyable when you can do it with a good friend," she winked at me lasciviously. "Let's retire to the boudoir, Darling, don't you think we should? It's getting late, and we don't want to fall asleep before our feet hit the pillows," she laughed at her bawdy innuendo to oral sex. She strutted to the lavatorio where more cosmetic items shared a wide space on the countertop between two stylish sinks. Peering into the wall to wall mirror, she uncapped a slim applicator and carefully coated her lips with a transparent gloss. "This is a sealer so my lipstick won't smear. I am looking forward to a lot of hot kissing tonight, Baby, and I don't want to leave all this cocksucking red in the wrong places!" I felt a little shock at her explicit reference to "cocksucking" while enjoying her directness. The juxtaposition of the classy and well mannered lady with her use of a very naughty word struck me as humorous with an undercurrent of compelling eroticism. She used a nearby hairbrush to primp at her beautiful head of ash blonde hair, alternately teasing and brushing the delectible little swirls of whiteness, as she held the cigarette femininely in her other hand. She put down the brush and picked up a gold enameled perfume spritzer and sprayed a generous amount on her neck and the sleeves of her gloves. "I hope you love White Diamonds as much as I do, Honey." I was speechless as I watched the show, all staged for my impending seduction. But this time, uniquely, rather than being the seducer, I definitely had the electric impression that I would be the seduced! Suddenly, she seemed to notice me in the blue robe, my borrowed long earrings still dangling to my shoulders. "Darling, you look wonderful in that robe. Do you feel nice in it?" "Yes, Auntie, it feels so silky against my skin," I rhapsodized. She strutted over to me and used her long gloved hand to stroke my back through the satiny material, descending to my buttocks encased in the satin bikinis where she carressed my bottom and gave it a little squeeze. Finally, she slipped her arm around my waist and guided me back into the bedroom. "Let's have one more nice cigarette, and then explore things under the covers." She led me to the white brocaded French provincial love seat and we sat down together. A sparkling clean crystal ashtray sat in the center of the matching cocktail table in front of the little two person sofa. Rolanda femininely stubbed out her cigarette and picked up a gold cigarette box and slid back the top revealing a fully stocked layer of Virginia Slims 120s and handed it to me. I offered her one, and then took one for myself, again holding the hypnotically long white cigarette in the same femmy way that Rolanda did. I picked up the elegant table lighter and flicked it to life, lighting Rolanda's and my own Virginia Slims. Again, I felt the satisfaction of the rich menthol smoke filling my lungs in an almost sexual way. I loved the way it tasted, felt, and smelled. We sat close together on the love seat, caressing each other's thighs through the silkiness of our sensuous garments. I looked dreamily at Rolanda as she gracefully exhaled another jet of creamy smoke. She was the picture of femme perfection, everything I had ever dreamed about, and she was a man! Amazingly, that fact made me want her even more urgently. Phyllis's words about gay transvestites understanding what other men wanted better than women did was proving to be so convincingly true. I wondered what having sex with Rolanda would be like, and couldn't wait to find out. My prick and balls were enjoying the constrained feeling of the special panties that Auntie had insisted on my wearing, and I could feel the silky softness of my dressing robe rubbing against the helmet head of my engorged cock. It was downright blissful. As we smoked our sexy cigarettes, Rolanda gently pulled me to her. Staring deeply into my eyes she placed the cigarette to her lips and hollowed her blusher-accented cheeks slightly, drawing the sweet smoke into her pretty mouth. Then without taking her eyes from mine, she inhaled deeply and kissed me with her open mouth. Our tongues darted against each other as she slowly exhaled the smoke deeply into my eager lungs. I devoured the smoke as I inhaled her naughty smoky essence, tasting the menthol combined with the minty remnants of her mouthwash and the perfume of her lipstick. It was almost overwhelmingly passionate and pleasurable. We kissed hungrily for a long while, our tongues exploring the sweet wetness of our mouths, caressing each other's bodies gently, and exchanging little sounds of pleasure. Finally, we pulled apart, looking lovingly at each other as our arousal built. I reached down and felt her crotch, gently caressing the bulge of her sweet ladycock inside her panties. I could feel the outlines of her garters and a supple corset which supported them. The skirt of her stunning gown fell open, revealing her taut filmy black stockings with the alluring black welts and the tiny seams that defined the posterior curves of her perfect legs. Her gloved hand found my stiffened prick through the silky material of my robe and began to stroke it slowly. It felt indescribably wonderful. I moaned involuntarily as the waves of sensation permeated my entire body. We finished our cigarettes, kissing and sharing the smoke intimately until it was all gone. Rolanda stood, pulling me up with her. She wordlessly urged me towards the beckoning bed. She pulled the comforter back to expose the sea of glowing satin sheets that stretched invitingly across the expanse of bedding. Rolanda knelt on the bed and gracefully maneuvered herself onto her back, her head delicately supported on a sumptuous pile of satin encased pillows. She opened her arms and invited me onto the bed. The feeling of my robe's material sliding over the satin sheets electrified my already sexually overcharged body as I crawled to join Rolanda's reclining presence. Lying together, we began kissing again, ever more passionately and insistently. Rolanda untied my robe and pulled it from me. She softly grasped my cock which protruded from the satin-ringed hole in my satin bikinis. "My God you have a gorgeous cock, Sweety!" she hissed passionately. "I want some of that big juicy horsecock in every one of my orifices that I can fit it into, Honey," she moaned in her velvety almost lisping gay whisper. "Ive wanted a piece of that action ever since I first laid eyes on you at Phyllis's tonight." She was talking dirtier and dirtier to me as her libido unleashed itself. "Baby, I want to suck it and fuck it and spray your jizz all over. I want it on the outside and the inside of my fucking body!" I was getting increasingly aroused as her bawdy talk and the silken embrace of her legs and arms cocooned me in a grip of intense pleasure. I was panting with anticipation, kissing her neck, her arms, her legs, her buttocks like a mad man. "Grab my prick, Honey!" she implored me with a moan, "Here's a pair of gloves for you to use on it. She pulled a pair of short satin stretch gloves from beneath a pilloow and handed them to me. I swiftly pulled them onto my hands, enjoying one more time the feeling of silky material on another electrified part of my body. I pulled her robe open to reveal a beautiful gold lame' corset with wide black garters trimmed with an overlay of gold lace. "Kiss my tits, Honey, and bite my sweet little nipples, please," she begged. The constriction of the tightly laced foundation garment forced what could almost pass for cute little titties out of the bra top of the bustier. I could see that her nipples were erect and quite well developed, especially for a man. I leaned forward from my kneeling position and began licking and suckling on her tiny breasts. They reeked of Oscar mixed with White Diamonds and I was loving it. I gently bit her nipples and her body spasmed with pleasure. "Yes, Darling, bite my baby nipples, that feels so fucking good" she panted. I was caressing the bulge in her panties with my satin gloves while I gently nibbled on her elongated nipples. She was writhing on the satin sheets now, filled with the pleasure she so desperately desired from me. The low lighting in the room illuminated a pair of gold satin panties which matched her robe. I could clearly see the entire outline of her erect cock through the glowing material. Rolanda reached down and pulled her panties to the side, exposing her stiff girlcock to my ministrations. She started jacking her hips, driving her beautiful shecock up and down through the encircling grip of my gloved hand. All the while that I had been pleasuring her, Rolanda had been stroking my cock expertly, as no genetic woman would ever know how to do. The pleasure was excruciatingly delicious and I had to start being careful not to blow my load while we were just getting started. Rolanda was simultaneously coming to the same conclusion. Breathing hard, she pushed my hand away from her shecock. "Slow down, Baby, or I'm going to go over the fucking edge if we aren't careful." I reluctantly slowed the pace as she released her perfect grip on my raging cock. We were breathing like a couple of dogs in heat, panting wildly. I collapsed onto the sheets, facing her. Our eyes were wild with the urgency of desire as we kissed unblinkingly, slowly regaining our normal breathing as we caressed each other's backs and shoulders gently, letting the passion subside a bit as we willed this incredible experience to last longer. The intimacy was delicious as we lay next to each other, our legs, arms and torsos touching, the mutual pulsations of our cocks slowing gradually as we gathered ourselves for the next round of pleasure giving. My bared toes explored the delicious outlines of her high heeled shoes thrilled that at last I had found someone who wanted to make love with her sexiest shoes on! I looked up into the overarching mirror for the first time and enjoyed the vision of her filmy stockinged legs intertwined with mine as I played footsie with her high heels! Rolanda reached over to the bedside table and picked up a cigarette, handing me the lighter. "Let's take a little break, I want this to last all night long." I flicked the gold Dunhill and lit her cigarette. She inhaled deeply and then offered it to me with a soft wet French kiss as she exhaled her hypnotic essence into me again. Suddenly the inspiration of a forgotten promise hit her consciousness, "Honey, you liked my fur, go fetch my mink, please, I want to make love to you in my mink!" No further urging required, I slid to the edge of the bed and stood, my erect pecker protruding proudly from my blue satin bikinis. I strode into the living room and retrieved the sumptuous fur coat from where I had draped it over the green leather chair. Rolanda was waiting for me. She had gone to the closet and exchanged her gold lame' gloves, for a shoulder-length black kid pair. She was smoothing the paper thin leather onto her slim arms when I reappeared with the fur. "Do you like them?" she purred. The supple kidskin rippled slightly as she used her fingertips to fit the material perfectly to her long thin hands. I nodded appreciatively as I helped her shrug out of her gorgeous dressing gown and into the softly glowing fur of the mink. The effect of the fur coat, the stockings, the heels, and the gloves was mesmerizing. She reached for my still throbbing cock and I felt the soft sensation of the leather grip my manhood. The feeling was sensational. Using my prick as a handle, she pulled me to her and kissed me deeply again, her wet tongue scraping my teeth seductively. The mink folded around me. I could feel the heavy satin lining caress my thighs and legs as we embraced tenderly. Locked in the embrace, she danced me slowly over to the bed and together, as if one person, we collapsed onto the satin covered mattress again. She sat me up on the edge of the bed and slowly, gracefully, her eyes never leaving mine, she sank to her knees. Her coat spread out silkily against the rich silk of the glowing Hereke. Her gloved hand had never left my hardness the entire time. She gently forced my legs apart. She looked up at me from her heavily madeup face, her eyes half closed beneath her outrageous eyelashes. Provocatively she licked her lips. My body was rigid with anticipation as she slowly lowered her head and allowed her lips to slip over the engorged head of my cock. The feeling of her voluptuously painted red lips sliding down the shaft of my erection was indescribable. I heard myself inhale sharply as her mouth touched the skin over my pubic bone. She had taken it all! Ever so slowly, her eyes on mine, she slid her mouth back up until her lips were suckling on the glans. With an imperceptible increase in rhythm, she began to repeat the movement of her lovely head, up and down my hardened shaft. I moaned with the extremity of my pleasure and began to move my hips, slowly thrusting my cock against her descending and ascending movements on my manhood. It was incredibly delicious. "Oh yes, Auntie," I breathed, "Suck your little boy's cock, take it all, Auntie." Rolanda moaned as I surprised myself with my dirty talk. She obviously enjoyed it. I could see her other gloved hand stroking her beautiful she cock as she continued to give me the best blow job by far that I had ever experienced. I could feel the sperm welling up in my prostate. With her mouth filled with my throbbing prick, she released her alternating grip on the shaft and began to gently stroke the skin of my ball sac. The combination of her sexy fingers on my balls and her warm wet mouth devouring my pole, the feeling was nearly overwhelming. I wasn't sure how long I could last without losing control and spraying me built up load of cum all over the inside her mouth. I resisted the strong temptation to let go, and regained control, just enjoying the sensations of the silky blow job. Finally, I couldn't chance the premature ending of this beautiful experience. I reached down and lifted Rolanda's chin, pulling her mouth from my hard on. "Rolanda, you must stop that. I want this to last. I'm getting very close." She looked up at me lovingly and complied with my request. We eased ourselves back onto the satin heaven of the bed, allowing our intense breathing subside once again. We sat with our backs against the headboard, cushioned by the many soft pillows. Rolanda lit our cigarettes this time and we sat quietly, smoking like ladies as our gloved hands stroked each others penises gently, keeping them hard, but holding our orgasms at bay. "Richard, I love your beautiful cock" she intoned sincerely in the gay lisping voice with which I was becoming incredibly enamoured. "I can't believe what a wonderful lover you are for such a young man. I'm very impressed with your gentleness and affection." "Thank you, Auntie." "I'm a lonely gay bitch, and I've been looking for someone like you a long time. You are a very special kind of person. I never expected that you would be so eager to cross the gender line. You've surprised me very pleasantly. Do you like your Auntie Rolanda, Honey?" "Yes, Auntie, more than you could possibly know" I murmured as I exhaled another creamy plume of menthol smoke toward the mirror above us. "I feel so lucky that I met you tonight." "Richard," she paused to take another femmy inhalation of smoke, "I want you to know that you are always welcome here. If you enjoy this, I want you to come to see me anytime you feel like it. I want you to have a warm welcoming safe place to come and explore your sexuality. It would break my heart to think of you in your student apartment, jacking off all by yourself, when you could be here with me discovering the joys of gay transgendered sex without guilt, without regrets." The sincerity of her invitation to have sex with her anytime I felt horny was very moving. I had entered a new chapter in my life. Previously I had thought that sex with another man would be disgusting, suddenly I was enraptured by it. I was quickly losing my interest in the false hopes of relationships with girls which always seemed to lead to unwanted complications and frustration. In contrast, this seemed so easy and natural, so free and liberating. I was loving it despite my lingering reservations about the propriety of it. I felt as though I had fallen through the worm hole just like Alice in Wonderland, but unlike Alice, I adored this previously unseen and unknown world I had suddenly fallen into without warning, and I wasn't sure I wanted to find my way back to whence I'd come! Auntie Rolanda inhaled another lungful of smoke and kissed me sweetly, again injecting her smoky love potion into my inner being. "Baby, I want you to do something for me that will make me very happy." "Anything you want, Rolanda," I compliantly replied. She spread her lovely legs seductively as the mink fell open to expose her gold corset, all the lovely garters, and the silky stockings. She had strategically put her satin panties on over the top of her garters. "Pull down my panties, Sweety." I gently tugged the glowing satin garment from her smallish hips and slid her panties down her legs and over her erotic high heels. "Now, Darling, suck my peepee for me, please," she instructed. I knelt on the silky sheets and slid my lips over the purplish head of her engorged penis which was oozing little rivulets of pre-cum. Her crotch had been bathed in multiple spritzes of Oscar. She smelled sensational as my mouth descended to the base of her shecock. I could taste the milky saltiness of her precum, it was a new experience for me but delicious. I could hear the click of the butane lighter as Rolanda lit another cigarette. "How sexy is that?" I thought to myself, "she's smoking like a diva while I lovingly suck her cock." I could also hear her little moans of pleasure as my lips and tongue found the most erogenous areas of her shaft. She started to slowly thrust her hips as I devoured her "peepee". Her buttocks squeezing rhythmically against the sheets made a soft zinging sound as the satin slinked against itself. I could also hear a similar sound behind me as her thrusting legs moved the sharp tips of her high heels against the satin. "Oh fuck, Baby, that is soooo good! You are sucking Auntie so well. Don't stop, Honey, slurp my balls too!" she implored breathily as she smoked. I released her shecock and with my gloved fingertips, I lifted her ball sac so I could engulf one of her nuts in my wet mouth. The skin was completely smooth and velvety, not a trace of hair or even shaving stubble. I would learn later that she had gone to a laser hair removal clinic to remove all her body hair permanently. My mouth was watering as I continued to stroke her peepee with my satin glove and slowly but hungrily devoured first one and then the other of her large testicles with my mouth. She groaned appreciatively. I could tell her balls were very sensitive and that I was giving her exactly what she wanted. "Oh yes , Darling, she whimpered, that feels so fucking good!" Her hips were bucking more urgently now, forcing her engorged cock up and down through the encircling fingers of my hand. I could feel my long earrings gently caressing the sensitive skin of my neck as she moved against my torso and head. She exhaled a delicious plume of smoke into my face as I suckled on her gorgeous balls and jacked her peepee. Her moaning became more pronounced, transforming into a louder and more insistent groaning with each stroke of her cock. I could tell from my experience with her in the car that she was getting close again, ready to shoot her girly cum all over the place, something I wanted desperately to experience for some unknown reason. Again, she pulled away from me, panting like an animal in coitus. "Stop, Honey, you're going to make Auntie cum." Reluctantly, I released her velvety scrotal skin from my salivating mouth and let go of her pulsating shecock. I pushed myself up to my hands and knees, certain that I must look ridiculous with my long earrings framing my masculine features, and my hard cock still sticking straight out of my femmy panties. It made an incongruously androgynous picture for Auntie to remember, I'm sure., Rolanda lit a cigarette and handed it to me. Her eyes had a wild dreamy look as she slowly batted her sexy eyelashes in my direction. "That was unbelievably wonderful, Sweety. You are a dream lover, Baby Doll. You make Auntie feel so special, she sighed, still out of breath from the sexual exertion. "Thank you, Auntie, I was loving it. I wanted you to cum for me." "Not yet, Baby, Rolanda has a special finale' planned for us. I know you'll love it," she smiled as she blew a thick cloud of menthol smoke at my chest and crotch. "I want us to cum at exactly the same time, Honey. I think you might like that." She said it almost as if she were talking about making a deposit at the bank. Her sexiness made my whole body react with little waves of sensation up and down my legs and arms. I leaned towards her and gave her a sweet little wet kiss and exhaled my smoke into her mouth. "Yummy, Honey" she whispered, playfully touching my half erect cock with the delicious kidskin of her glove. I could smell the soft leather combined with the earthy aroma of her sumptuous mink wrap. The fragrance compellingly mingled with her swirling cocktail of perfumes and of course the intoxicating aroma of menthol smoke. I felt dreamily entranced by all the sensory stimuli invading my tingling mind and body. "Take a look at my pussy, Baby Doll." Her request stunned me for a moment. She slid her upper body down off the pillows, and lifted her hips so she could thrust one of the pillows under her bottom. I worked my way back down to her lower torso again, giving her still stiff peepee a little peck on its still swollen head. She laughed and thrust it towards me wickedly, poking me in the cheek. I gave her my most lecherous look as my earrings swayed against my cheeks. More serious now, she lifted her gorgeous legs up over her torso exposing her buttocks, spreading them with her gloved hands. I was surprised to see something gold in her rectum, glowing dimly in the subdued light. I leaned closer to examine it. What I found was the convex shape of a gold plated object, with sparkling rhinestones imbedded in its surface. "What do you think, Honey?" she asked innocently. I lifted my head so that I could clearly see her face, obviously expressing amusement at my naivete'. "It's my golden bolt. If you pull it out, my ass falls off!" she laughed hlariously. I was shocked by the sight of a foreign object inserted in a place I associated with unmentionable biological necessities, and I was equally shocked at the very unfeminine expression of humor, so out of character for the elegant Rolanda. She stopped laughing and resumed a more classy expression. "Sorry, Darling," she apologized, recognizing the look of mild distaste on my face. "I couldn't resist. I'll try to behave myself, but sometimes my ugly masculine tendencies resurface at inopportune times." She paused to take another sexy inhalation from her cigarette. "It's my buttplug, Darling. Be a sweety and pull it out for me." I knelt below her erect thighs and grasped the diamond-studded head of her "device" and started pulling it towards me, not knowing at all what to expect. I knew about dildoes, of course, something I'd read about that naughty girls used to masturbate with, but a buttplug was a whole new experience for me. The plug yielded to my efforts revealing a short slim golden shaft penetrating Rolanda's anus. Before much outward movement, I encountered significant resistence. "Keep pulling, Honey, it will come out if you try," she smiled. I pulled much harder and to my amazement, a largish spherical portion began to emerge from the confines of her encircling musculature. Suddenly the spheroid popped free and with less constriction from Auntie's pussy hole, a conical portion of the plug finally emerged, tapering gracefully to a smaller globular tip as I slowly pulled the rest of the device from her rectum. I held it up in wonderment. Its surface was dripping with little rivulets of a clear oily substance. "That's scented lubricant, Honey. It keeps Auntie's asspussy nice and soft for a special lover like you, and it makes it much easier to insert and extract my butt stretcher." I placed the plug on the bedside table. Still speechless and a little wide eyed at yet another discovery of the gay transgendered world that I had so recently been ushered into. Bemused, Rolanda watched the wheels turning in my naive brain. She was enjoying the fact that she had a malleable student in her clutches, ready and willing to take her instruction. She had plenty to teach me, we were both sure of that. "Have you ever eaten a girl's pussy?" Remembering that I had very recently eaten Ruthann's baby-enlarged pussy with great abandon, but not wanting her "Uncle Raleigh" to know about that, I allowed that I had eaten a few pussies in my day, man of the world that I was. "Good, then you know what to do for Auntie, Darling." She batted her huge eyelashes at me with feigned nonchalance. "Now show me what you can do, Honey." I again knelt below Rolanda's buttocks and began hesitantly to lick the remnants of the lubricating lotion from around her rosebud, still gaping

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"You do have a choice Richard. You don't have to do it, but life will be so much easier for you if you do. If you do it nothing changes except that you will never sleep in my bed again. Although I'm going to be taking on the role of CEO you will still be president of the company, you will still have your country club membership and you can even keep your bimbo. If you don't do it you are out of a job, homeless, probably not able to buy your little blond slut a cup of coffee and the only way...

2 years ago
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Richard the StockmanChapter 7

Richard invited his parents to the graduation ceremony and they drove to Gatton on Thursday, 1 December. The ceremony ran from about 10 to 11, before it became really hot. Andy and Sybil then helped Richard load his accumulated detritus into their (new) Ford Falcon and a few things into the (rusting) Jeep. “It’s done well over these three years,” Andy remarked. “Yes. I’ve had no major problems: plugs, belts, shocks, tyres, wiper blades, but nothing large.” “Well, it’s little over two hours...

3 years ago
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Richard the StockmanChapter 2

Lamorbey Station seemed to comprise a sprawling house, a second, smaller house, a pair of barracks-like buildings, and a number of barns and sheds. At first it seemed more extensive than College, but fewer people. Richard had been introduced to the Millers and several other people at dinner, but he recalled none of them. He’d slept in his swag on the floor of Ferd’s room. They were up at six, washed, and outside to join a group of about forty, half of whom were aborigines, to hear the day’s...

1 year ago
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Richard the StockmanChapter 3

Lamorbey Station seemed far away when Richard pulled onto campus early on Monday. He’d spent Friday night in his Jeep, near Tambo, an hour past Blackall. He’d lunched and dined out of the esky. The next night he’d spent in a motel in Roma, where he’d enjoyed a shower. Last night he stayed at the Royal, an older hotel in Gatton, and so was well-rested. He was also in a good mood. He’d opened the “pay envelope” and discovered ten five pound notes – far more than he’d expected for just under...

3 years ago
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Richard the StockmanChapter 5

The year ended. Richard drove west and north, arriving at Lamorbey on schedule. He was welcomed by Janey with an exuberant night of sex. In the morning he was welcomed back by the foreman and many of the crew. Ferd was in Emerald on a “shopping trip.” Ferd turned up in mid-afternoon. He’d been purchasing ammunition: .30- .30 and .30-06 cartridges and a box of slugs for the 12-gauge shotgun, which Richard had never seen. The “hunting party” was to be made up of Ferd, Richard, Janey, Al, and...

3 years ago
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Richard the StockmanChapter 6

Richard asked for the Christmas to New Year’s Day week off and drove to Southport in two harrowing days, with extremely high temperatures. He was welcomed by his parents with the news that “Cat’s on a cruise to Auckland.” After unloading the Jeep he showered and re-dressed. It was a luxury to have real hot water on tap. “How are things?” Andy asked him. “Well, I’ve worked hard for two months and I think I’ve learned a lot. I’ve been talking to one of our Aboriginal drovers and learned from...

2 years ago
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Richard the StockmanChapter 4

“It’s actually just under 30,000 acres,” Richard was told about two weeks later. “Can you explain?” “Of course. First of all, it’s unclear to me whether the property is within the bounds of Womalilla or of Mungallala. Most likely Mungallala’s too far west. I don’t think Brisbane’ll have to adjudicate. But the land itself extends south of where that two creeks you crossed join to an unnamed east-west road. The land is lightly wooded in the east and shrubby in the west. Because of the...

4 years ago
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Richard the StockmanChapter 8

Richard drove to Mitchell on the 28th, taking a room in the nearly-empty Richard’s Hotel. He ate dinner, washed up and slept. It had taken nearly nine hours to cover the 400 miles from Southport to Mitchell. But he felt invigorated in the morning. After a hearty breakfast, he drove to the store, and bought a 600’ coil of 1/4” manila, a small sledge, a bright orange grease marker and a 40’ measuring tape; he also bought ten pounds of sugar, two bricks of chewing tobacco and a tin of pipe...

4 years ago
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Richard the StockmanChapter 9

Time flies, they say. Richard knew from school that Ovid wrote “omnia mutantur, nihil interit” (everything changes, nothing perishes Metamorphoses XV), where he later refers to “tempus edax rerum” (time the consumer of things). But what eats up the days, the weeks, the months? One of the Greeks wrote that everything flows. 1962 certainly flowed away. Like water or sand through your hands. Jenna was pregnant again. Joyce would have a sibling before she was three. Ferd was married, but was...

3 years ago
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A Confession A Night of Firsts

I hope you enjoy it. Please PM me or comment below and let me know what you thought. Of course I also encourage voting. If you go into the Forum section of the site you will see the Sex Stories Section. The CAW10 entries are there... I strongly suggest reading them as they are wonderful and written by very talented people. Enjoy! A Confession – A Night of Firsts I am a bit worried as I write this. Mostly because of what I have done and what I know, with absolute certainty, I...

4 years ago
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A Confession A Night of Firsts

Introduction: A teen girl meets the guy she wants to make her a woman. Hello! Thank you to everyone who has been encouraging me to keep writing. This story is not intended to be part of a series, but I hope it is well received. I hope you enjoy it. Please PM me or comment below and let me know what you thought. Of course I also encourage voting. If you go into the Forum section of the site you will see the Sex Stories Section. The CAW10 entries are there… I strongly suggest reading them as...

2 years ago
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Firsts

Dedicated to a lovely young lady that would have graduated in 1960 with a first initial of "J" First and most important, this is a totally true story. Because it is true, there is little sex and what there is, has not been embellished to the best of my knowledge. One almost always remembers their "Firsts." Their first kiss, first date, first love, first sex and first crush. This is a story of all the above and more. I have always been a shy person. All through my freshman and sophomore...

3 years ago
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A Night of Firsts

Anita lay naked on the bed, her body trembling with anticipation. Her small breasts heaved against her chest as she looked at him. Her eyes focused on his finger tips as they reached into the waistband of his black boxer briefs. A fairly significant bulge stuck out. She knew it was going to hurt. But she didn't care. She wanted to feel a cock inside her for the very first time. It was Alicia who suggested Bobby.Bobby and Anita had known each other for about a year, they met through Alicia. She...

3 years ago
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A Long List of Firsts

It’s funny how simple things trigger memories in a person. Sights, sounds, smells and even feelings of pain or pleasure can spark a flashback. That pain I was now feeling as my cock strained against denim made me recall how all this began. 15 Months Earlier It was Friday night, not long after leaving work, where I found myself in my favorite place. My home away from home, at least from the time just prior to my divorce until now, where I could relax before heading home or in this case to...

2 years ago
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My night of many firsts

I was never a big hit with the girls in High School and I was a virgin by the time I graduated. Now with living at home and just working I didn't have a real chance to date. It was the 80's and I didn't have a computer yet and when I hit at the age of 18 I was able to go to the Adult bookstores and I was a k** in the candy store. Well I would gather up some masturbating supplies and race home to jerk off, some of the items I would get were the local swingers magazine. I figured that I wanted to...

2 years ago
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A night of many firsts

I was a horny but shy guy in school and I never had the guts to ask girls out. After getting out of high school I finally had to shed my virginity. I was a regular at the local adult bookstore and I decided to get a swingers magazine. I still lived at home so I had to try to find someone to host After sending several letters out I got a reply back from Joe and Patty, they were in their mid 40’s. Patty was a tiny blond with a nice body. Joe was a taller guy 6’3” about 250 with a slight beer gut....

3 years ago
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A night of firsts

I was a horny but shy guy in school and I never had the guts to ask girls out. After getting out of high school I finally had to shed my virginity. I was a regular at the local adult bookstore and I decided to get a swingers magazine. I still lived at home so I had to try to find someone to host After sending several letters out I got a reply back from Joe and Patty, they were in their mid 40’s. Patty was a tiny blond with a nice body. Joe was a taller guy 6’3” about 250 with a slight beer gut....

2 years ago
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A night of many firsts

I was never a big hit with the girls in High School and I was a virgin by the time I graduated. Now with living at home and just working I didn't have a real chance to date. It was the 80's and I didn't have a computer yet and when I hit at the age of 18 I was able to go to the Adult bookstores and I was a k** in the candy store. Well I would gather up some masturbating supplies and race home to jerk off, some of the items I would get were the local swingers magazine. I figured that I wanted to...

2 years ago
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A Night of Firsts

A Night of Firsts By Sexy Laura This story is property of me, and may not be resubmitted without my consent. [email protected] ************************* "Tommy.. Can you give me a hand for a second?? Please???" I hated when my sister Shelley asked me for a favor when she had clients over. I always feel uncomfortable. Especially since my sister has a clientele that is slightly different then most people would imagine. She is a professional dominatrix. Complete with the...

2 years ago
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Night of Many Firsts

Night of Many firsts (Part One)Don Abdul ©She was engaged to be married, but a couple of weeks to the wedding, her whole world came crashing down around her, when she received an anonymous tip that took her to a motel on the edge of town. At the motel, she caught her man, and her would-be maid of honor, stepping out from a raunchy fuck fest…..The trauma of that incident and the heartbreak it caused her would have put some other person in a sanatorium. Dawn however is a sister with attitude, so,...

2 years ago
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Night of Many Firsts

Night of Many firsts (Part One)Don Abdul ©She was engaged to be married, but a couple of weeks to the wedding, her whole world came crashing down around her, when she received an anonymous tip that took her to a motel on the edge of town. At the motel, she caught her man, and her would-be maid of honor, stepping out from a raunchy fuck fest.....The trauma of that incident and the heartbreak it caused her would have put some other person in a sanatorium. Dawn however is a sister with attitude,...

Bisexual
3 years ago
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Richards Time

Richard had little use for his wife anymore. He couldn?t even remember why he had married her, aside from it being a naïve college sweetheart thing. He had been a bright young ROTC cadet, on his way to a commission in the Army, while she had been an ambitious marketing major, seeking a career in advertising. Well, Uncle Sam had dragged him around the world in 19 years of service. He had no choice in where he was stationed. This was something that Lacey had never grasped. She had constantly...

4 years ago
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richard goes to fat camp part 1

hello richard my name is wendy but you can call me maam welcome to boys fat camp are you ready to do whatever it takes to loose weight ?yes maam my method works but you have to do everything i tell you no argueing no questioning me if you can't do that then leave now i have to loose weight maam i'm fed up being the fat boy , now i'm 19 it really can't be passed off as puppy fat anymoreok strip and get on the scales lets see what we are dealing with um everything ?of course naked come on don't...

1 year ago
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Richard and Nikkis Humiliation Part 1

It was only when her husband Richard promised to ensure her anonymity that Nikki agreed to go out with him and dance in wild fashion and wear the party dress he picked out for her. The club in Tribeca was a long ways from where they lived, but it was one of the hotter clubs and everyone there was in their late twenties or early thirties and looked hot. And going there for the third time now, Richard had got them a hotel so they would not be in their own community to satisfy Nikki’s fears of...

Group Sex
2 years ago
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RICHARD AND HIS STEPSON

My stepson Richard was a very nice quiet boy. Very shy. He was 18 years old but looked much younger. His mother was a bit of a slut and I loved her for that. However, she never really liked Richard and he came to me for love and attention.She told me that he was a fucking looser, never be a real man and was in summer school so he could finally graduate from high school. He would come home from summer school and give me a big hug and kiss. I loved his kisses. I guess I should mention that I...

1 year ago
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Richard the lll

Richard the III Janet L. Stickney [email protected] Richard left on the Crusades, leaving his maiden alone, longing for his return. She cried out went he left, telling of her love for him, hoping, pleading, that he would not go. Richard, with but a single glance back at her, rode off on his quest. The maiden, her eyes filled with tears sank to the floor in despair, her gown draped around her as her impending loneliness descended on her. The curtain fell to the resounding...

1 year ago
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Richard

Bound at the wrists, Richard was draped over a sawhorse in Dietrich's basement, much to the delight of several of his wide-eyed friends. The sexy, bearded German, whom the victim had met over the internet, was giving a small demostration of his leather skills to the appreciative gathering, who sat in abject silence as Dietrich began probing the prostrate man with an irrigation bulb. Richard winced as the hot liquid was injected into his anus, instantly clenching his sphincter closed, more by...

Gay
1 year ago
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Richard the Sissy gets Caught by Sis

Richard the Sissy gets Caught by Sis by Joney Cunningham Gina is making keep a diary of my sissy training. She says all girly sluts keep a diary of their training. It was the ending of a long day, so Gina told me to wash up and put on a pink baby-doll nightie. I was really sore from my ass to my mouth. My jaw really ached because of all the pussy eating, asshole licking, and cock sucking I had done that day. Gina made sure there was skin softening liquid in the bath water with...

4 years ago
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Richard Rachel their play date MDomFSub

-Richard and Rachel have been dating for a couple of months. Yet to get intimate ,they’re both extremely kinky and both are well aware of their sexuality. Richard is dominant ,a sensualist at his core ,chicks with high pony tails and an innocent physicality are enough to give him a raging hard on. Rachel is a 5’6 goddess ,bubbly ,confident ,outspoken and ambitious on the outside ,though once the doors are closed ,Richards gaze is enough to make her cunt wet. A sensualist sub slut of the first...

2 years ago
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Richards dick

I hadn't spoken to Cait for I think almost three weeks and I picked up the phone every day to call her but I didn't do it, and then one day her dad came over to fix something on mom's car but she wasn't home from work yet so he sat down in the living room to wait for her. And I made coffee for the both of us and we talked and it was really nice but then he said “So what happened between you and Caitlin?” and I just looked down and said “I don't know” because of course I couldn't tell him.So he...

2 years ago
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Richard the Sissy

Richard the Sissy by Joney Cunningham Hi, my name is Richard, or should I say Regina now. I am a sissy. It all started when I was 15 and my parents had taken my 13-year-old sister out of town for the weekend. I had a part-time job, so I couldn't go. My parents told me that the paid Gina, the high school senior across the street to decorate my mom's sewing room. Gina was into interior decorating and had gained a reputation of doing great work. They told me she would have a...

4 years ago
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Mayhem in a PillChapter 12 A Day of Firsts

First day of school for both Murphy kids saw a return of a family tradition: Mom fixed a full breakfast for everyone. Pancakes, bacon, sausage, eggs, fruits and all kinds of baked goods. She generally cooks for the family, then the mothers from the neighborhood carpool come and enjoy a wonderful meal at their own pace. There were usually a few empty bottles of wine in the trash when the kids returned home from the first day of school. Rumor has it the same carpoolers also got together toward...

1 year ago
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A Real Challenge A Night of Firsts

Reassured of my dominance, I licked his cum off my hands and went back to his friend. I patted his hard cock on my tongue, moaning playfully. I was having the time of my life, people were stopping in the street to watch, and I was loving it. I took the second man’s cock back into my mouth again and again, slowing going deeper each time. Then I kept my tongue out, flicking along the underside of his shaft as I took him down my throat. As the tip of my tongue touched his balls, he came, sending a...

First Time
2 years ago
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A Night Of Firsts

The date did not get off to a good start. I arrived early as always, ordered a drink and found a nice seat outside to enjoy the amazing summer sun that for once was beating down on London. As the minutes ticked by I began to think that I’d been stood up. Suddenly, fifteen minutes late, my phone buzzed with a message apologising but assuring me she was on her way.She finally arrived thirty minutes late and I was taken aback - she had looked very cute online but her picture really didn’t do her...

True
2 years ago
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Living Next Door to Heaven 163 Firsts

"Mr. Clinton, this is Brian Frost." "Hello, Brian." Did he sound exceptionally cool? "Sir, I have been given the privilege of accompanying your daughter, Cassandra, on her first official date this Saturday." "I'm aware. She told me months ago. I suppose there isn't much I can say about it, now. What is it you wanted?" "I wanted to make sure my choice of activities would meet with your approval before I purchased the tickets. The Notre Dame Ballet Company is performing...

1 year ago
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A Few Firsts

OK this time in my life was turbulent, as far as sexual relations developed, with here I am at the beginning of the Sexual Revolution, Vietnam Protests, Protests in general, Peace Love Dope, Flower Power, Flower c***dren, Acid Rock, Jimi Hendrix, Janis Joplin, Timothy Leary, even the dawn of Gay Rights. That plus I had a head start in knowledge. I was torn between what I was taught was proper and paths others led me down. My girlfriend, which I was taught was the normal thing, I thought, where...

4 years ago
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Firsts

"I need to find someone to take me camping," she said while standing in my cubicle. We'd just been talking about how much we enjoyed camping and the outdoors and I'd been showing her some of my nature photos. I can't even remember what brought it all up, but it was fun to open up with a coworker like that. I like to feel the intimacy that comes from opening up to others and having them accept me. It's even better when we have similar interests and I can feel that rapport growing almost...

3 years ago
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A Night of Firsts

We had been building up to this for many months. She was the gorgeous account manager, I was the admiring customer. She had captivated me from the first moment we met, and countless texts, emails and phone calls later, I knew she was someone very special. Innocent on the outside, something much more intriguing on the inside. After a fabulous dinner, followed by a few drinks in one of those hidden bars that only the locals know in my town, she boldly told me it was high time I delivered one of...

2 years ago
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A Fist Full of Firsts

David Miller and his wife Mandy were an attractive looking couple in their late thirties. Mandy stood just under five and a half feet, with David nearly six. Though David had always admired his wife's full rounded breasts as being one of her major attributes, her tight muscular ass was certainly another which he couldn't help but reach out and fondle whenever she walked by. Mandy of course thought her eyes to be her best feature, an almost cobalt blue that was accentuated greatly by her near...

3 years ago
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A Lot of Firsts

My encounter at the Seattle ABS frightened me so much that is was three or four months before I would go into another one and I had transferred to San Diego in the meantime.I had been thinking about that blowjob and decided that since I had enjoyed it so much I was curious to try some more and what better place to try to find more than another ABS. There were a few of them some distance from the base so it seemed safe. This was back before Don’t Ask Don’t Tell so the services were still...

4 years ago
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A Vacation Of Firsts

We find Eric St Clare naked and under the sheets of king size hotel bed, oblivious to the rain and thunder outside. His arms are wrapped around a stunning dark haired beauty clad only in nylons and garter belt. They are sharing gentle kisses on each other's necks and lips as Eric allows his hands to run across her naked breasts as well as her nylon covered legs.A soft moan escapes the brunette's red parted lips as Eric slowly draws his fingertips up the back of her leg and he marvels at the...

Trans
1 year ago
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Billys Firsts

Some time ago my older sister caught me out in the Rumpus room with a girlie magazine. I was having a quiet wank over a full page layout of a gorgeous blonde bird who was sprawled out on a bed working on her fat juicy pussy with a huge dildo. I was only 14 at the time and my sister was a well developed 15 year old and aggressive with it. She grabbed my mag. and with a wicked grin she flounced off out of the room calling over her shoulder "I've got you now you little bastard, one peep out of...

3 years ago
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Stupid BoyChapter 2 Many Firsts

Labor Day was the busiest day of the season for Dad and his Parks and Recreation staff. The parks would be full and it was the last day they had the public pools open. Greg and I always had to help in some way. For some reason Greg had gotten out of helping this time. He got up early and left for the day. Dad made me help the lifeguards at the main pool. You had to be 16 to do it for money so I was an unpaid volunteer, or that was what Dad told me. By 11:00 am the pool was packed. It was a...

3 years ago
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So Many Firsts

I was out of town on a business trip. Work ran late at the client's office and I was a little tired, but really wanted a drink. Not knowing the area, I just drove around until I found a decent-looking bar. As I made my way in, I only noticed that the lights were dim and the bar was set up like a relaxed club. The theme was very post-modern and there was electronic music playing in the background, but nothing too loud. I streamlined my way to the bar and asked for a drink. As soon...

4 years ago
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Chosen Frozen IIChapter 16 Day of Firsts

The General sat behind his desk, grumbling to Chaz, who was ensconced in one of Michael's Shanghai Art Deco guest chairs. Chaz carefully hid his growing amusement. Bâtisse himself was now quartered in a pen out in the main dome near the base fire hall, with a replicator that pumped out carefully measured quantities of weed and shrubbery clippings every few hours. He was a source of endless fascination for everyone on base, young and old, and did not lack for visitors. "Only fucking goat...

1 year ago
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Ajs night of many firsts

My name is Josh I am 21 and I live with my girlfriend Ashley and her best friend Pamela. Ashley and I have been dating for 5 years. She is the most beautiful girl ever. She is 34-24-32, 5’5” and her hair was straight and black. Pamela was 5’3” had black hair measured 36-26-36. Ashley and I were very sexually active and she was very much bisexual so it was no surprise that the 3 of us had had a lot of threesomes and group sex. Ashley was very comfortable with me being sexually active with her...

Group Sex
4 years ago
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A Day of Firsts

"Ken?" my wife, Danielle, said to me one night while we were lying in bed. "Yea?" Here it comes, one of those "what are you thinking about" questions. Not quite. "When was your first time?" she asked. "Huh?" I said suprised. "You know, sex,"she said. "Mine?, you wouldn't want to here about it,"I said. "No, c'mon, I do." She snuggled up close to me. I put my hand up and ran my hand through her soft dark blonde hair. "Hmmmm, well,... My first time was back in ninth grade. "No...

1 year ago
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A Night of Firsts

Olivia here with yet another true story. My hubby and I had met and befriended a black couple at a Lifestyle party. There was a mutual attraction, but nothing came of it at that time. Olivia here with yet another true story. My hubby and I had met and befriended a black couple at a Lifestyle party. There was a mutual attraction, but nothing came of it at that time. It was getting close to several months before the holidays and Rich, Shana’s husband, was getting deployed. The next ladies...

Group
2 years ago
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A True Night of Firsts

For the better part of a year, my wife and I carried on an MFM threesome with a younger man we had met online. He lived a little over six hundred miles from us, so meeting him took planning and travel. Jason was a great lover for my wife, and with his bisexual side, he and I were able to work together to satisfy my wife every time we met. Other than incidental contact in satisfying my wife, Jason, and I had not ever had any contact one-on-one. My wife had always remained our full center of...

4 years ago
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A holiday of firsts

Not long after the events mentioned in the previous story, my sweety and I found ourselves heading into Germany for a well-deserved, and more importantly, nice and private vacation near the beach. The idea of having that small brown canvas love nest to ourselves for slightly over three weeks was almost unfathomable. Next to already being a couple of permanently horny adolescents, the prospect of having the other to ourselves for almost a month had kicked things into high gear to say the least....

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