Auntie Rolanda Drives Richard Home... With A Detour free porn video

Auntie Rolanda Drives Richard Home....With a Detour! Installment Two by Jessica Aireson So, here I was, buck naked, kneeling before the gorgeous Phyllis who had just noisily ejaculated an enormous load of hot silky jizz into my eager mouth. I knelt between her legs, astounded at what had just happened. My mouth and throat savored the warm, milky, and slightly salty gelatinous mass. I was acutely attuned to the sensation of Phyllis's shapely and silky stocking-clad legs embracing my bare shoulders. She continued to breathe in short shallow gasps as her orgasm slowly subsided. I looked up into her heavily made up eyes, half hidden by her outrageously long false lashes, the lids glowing with colorful eye shadow and artfully shaped by thick black liner. She was still in another world as her spectacular orgasm took its toll on her consciousness. Her body continued to gently shudder spasmodically, and her sculptured red nails gently ran through my hair. Her long slender legs still softly caressed my naked shoulders as I gently stroked her stocking tops and kissed the naked skin between her garters. Finally she looked down into my adoring face and smiled affectionately. "Thank you, Darling," she whispered. "That was fantastic. You really are an incredible lover, Richard! Have you ever done that before?" With my mouth and throat awash in cum, I responded with the hint of a gurgle, "No, never," but quickly adding, "I loved it!" "Good, Sweetheart. There's a lot more cum where that load came from," she promised with a little wink of a deliciously made up eye. For the past few moments, I had forgotten the presence of Rolanda who still stood poised over us, slowly smoking her Virginia Slim and stroking her engorged clitty cock as she surveyed the waning passion of her spent tranny girlfriend and newfound convert below. From the sublime look on her beautiful face I could tell that she had thoroughly enjoyed her role as director of our erotic sexual encounter. "So Richard, did she give you a nice load?" I nodded appreciatively, my tongue lazily swishing the warm deposit of Phyllis's ejaculate around the inside of my oral cavity. "You know what to do with it, don't you Honey?" she purred provocatively. Unknowingly Influenced by post hypnotic suggestion, I nodded again, and then looking again into Phyllis's pretty eyes, I swallowed deeply, the still warm jizz spilling down my throat and tickling my waiting tummy. It was an amazingly satisfying sensation. "Would you like another cigarette, Baby?" She picked up the luscious green and white pack of Virginia Slims 120s and offered it first to Phyllis and then me. I was suddenly aware that my cock was still rock hard and protruding upwards at a nearly vertical angle as Rolanda lit our cigarettes with her lovely gold lighter. I instantly adored the taste of the minty smoke mingling with the remnants of Phyllis's milky cum, it was an unbelievably sexy combination, and I inhaled the creamy cummy smoke deeply. Phyllis pulled her beautiful legs up from where they had encircled my torso and reclined so that she was facing me on the glowing ivory satin sheets, smoking seductively like the true gay diva she was. Rolanda motioned to me to join her and then took a seat on the edge of the bed next to us as we smoked in the glow of Phyllis's post-coital relaxation. The feeling of the cool satin sheets against my naked body and the feminine style of my own smoking electrified me and suddenly I could feel my whole body language becoming very femme. My wrists were inexplicably limp as I caressed the silkiness of Phyllis' robe and stockings and smoked like a perfect womanly lady. My new "femme friends" smiled knowingly as they remembered the first time they had felt the same wave of gay femininity wash over them many years before. I felt as though I had unexpectedly yet willingly crossed a line in my young life, a line that separated the "normal" and conventional from a previously hidden and forbidden realm of delicious sexuality that I unknowingly had craved but never realized to exist. A dim comprehension crept into my mind that my abiding obsession with feminine, overly made up and turned out women might actually be a fascination with the accoutrements of femininity and not with the women themselves! From the serendipitous encounter with Ruthann's father and his best friend, both femmy gay men, I suddenly understood that the erotic allure of femininity was not necessarily linked to the underlying gender of the person portraying it! As a result, it was just beginning to occur to me that my erotic attraction to femininity was not exclusively the realm of genetic women. I had just discovered that my often frustrating drive for sexual pleasure with women could perhaps be fulfilled much more easily and satisfyingly without all the drama I'd found so often to be associated with the opposite gender! It was quite a shocking revelation to my young mind! It had just been graphically revealed to me that in this formerly forbidden world, it was happily possible to become the object of sexual pursuit, not always the pursuer....and unlike most of the genetic women I had known, I was undeniably willing to be the enthusiastic target of effeminate gay conquest! Rolanda gracefully exhaled a creamy plume of menthol smoke toward the ceiling and then limp wristedly reached across my outstretched body to gently roll the cigarette to a neat point in the ashtray. I got a little sexual jolt from the sight of her heavy red lipstick stains on the contrasting white filter as her long slender gloved fingertips expertly manipulated the long cigarette. With the Virginia Slim perched femininely in her extended fingers, she gave me a devastatingly aloof look as she slowly reached her hand to my throbbing prick and gently stroked it with her non-smoking fingers. My body involuntarily spasmed as the sensation of her satin gloved hand caressed the taut skin of my hardness. It was indescribably erotic. I didn't know it yet, but I would later find that I would never get enough of this erotic forbidden pleasure....I had been enraptured by it! "Mmmmm, pre-cum, Darling! You really are a very naughty boy, aren't you? Does that feel nice?" she purred in her faggy gay voice, exchanging a knowing smile with Phyllis, who was again running her long dragon lady nails through my tousled hair. They couldn't have missed the ripple of goosebumps that quickly spread over my body. "Yes, Rolanda," I sighed, arching my back and thrusting gently into the encircling fingers of her smoking hand, "I really am a very naughty boy!" "From now on, you may call me 'Auntie Rolanda', Dear. I am the naughty, sexy Auntie that you always dreamed of coming home to after school, aren't I, Honey?" "Oh yes, Auntie Rolanda!" My heart leapt at Rolanda's prescient penetration of my frequent adolescent fantasies about rushing home to visit a darkly evil older sex goddess at the end of the school day. How did she know? Somehow she had read my mind, or perhaps she had conjured similar masturbatory visions in her own youth? I remembered that some of the sexy smoking mothers of my high school girlfriends had subtly come on to me on occasion after school, but unfortunately, nothing overtly sexual had ever come of those real or imagined opportunities. Now, "Auntie Rolanda" was hinting broadly at ready satisfaction of those puerile cravings. I couldn't believe my good fortune, even if the provocateur of fulfillment was a femmy gay man dressed and made up to be the incarnation of my fondest images of erotic desirability! Rolanda took her hand away from my throbbing, pre-cum streaked cock and took another long languorous drag from her cigarette, her half lowered and heavily made up eyelids still allowing her piercing gaze to invade my soul. "It's getting late, Honey, and I promised Ruthann that I would give you a ride home. Why don't you get dressed and we'll go?" In my disappointment, I missed the knowing looks and little smiles that passed between Rolanda and Phyllis. I obediently rose from the bed and put out the last of my Virginia Slim in the elegant crystal and gold ashtray, thrilling again at the sight of extinguished cigarettes with their bright stains of Phyllis' and Rolanda's creamy lipstick. I had always been fascinated by lipstick-stained cigarette remnants as far back as I could remember. I think it was related to my surreptitious observation of my mother's sexy girlfriends who all smoked, dressed sexy, and wore a lot of makeup. Reluctantly I dressed as Phyllis and Rolanda primped in front of the room's many mirrors. I enjoyed watching my new friends straighten their clothing, resmoothing their silky stockings and adjusting their garters. Rolanda went to the "wig closet" and ducked out of her large, professionally styled "big hair" wig. I was surprised to note that with no wig on at all and her close cropped short masculine hair fully revealed, I was just as sexually attracted to her as I had been when she was luxuriously coiffed only a few moments before, perhaps even more so. There was something very erotic about the stark androgyny of this femmy gay man, heavily made up and clad in very sexy women's clothing but with short cropped masculine hair! My cock, which had started to soften, suddenly sprang back to life. After looking through the large selection of glamorous wigs on the many shelves, she selected a shorter style, admired it for a moment and worked it onto her head, primping the bangs and curls expertly to give a natural and attractive appearance. The look was a little more severe and very hot. Suddenly pretending to notice that I had been watching her, Rolanda felt the need to explain, "Since we're going out in public, and not yet knowing your living situation, I thought I should present a little more 'conventional' appearance. I wouldn't want you to be embarrassed if your neighbors saw you driving up in my Cadillac with a flaming drag queen in the driver's seat!" she chuckled in her wonderfully androgynous lilt. Looking back on that moment, it was so revealing of my stunning naivete at the time. I confess that I had never heard the term "drag queen" before Rolanda had uttered it. It was a reflection of the sheltered "straight" life that I had led up until that starkly life-altering evening. Of course, I thought of myself as a hip young man of the world, someone incapable of being shocked or surprised by any aspect of human sexual behavior, so I pretended that I knew all about "drag queens", even though until then I didn't have a clue. Nonetheless, I now realized that I wanted to learn more about those newly discovered "drag queens", a whole lot more! "Well, Auntie Rolanda, I guess I do live in a pretty conventional neighborhood near some fraternity houses, so I appreciate your discretion", I said, trying my best to sound nonchalant about it. Although she had toned down her coiffure a bit to its short ash blonde style, I knew that her heavy makeup, satin gloves, immense diamond-studded pearl drop earrings, and five inch heels would at the very least make her look like a high class prostitute....a look, incidentally, that I liked very much! I decided that I would take my chances boldly disembarking from her Cadillac in front of my apartment house. If anyone I knew saw us, it might even contribute to my reputation as a man of the world! Phyllis had now managed to rearrange herself, appearing as though she had not just experienced her most explosive orgasm in many months. "Let's retire to the living room and have a nightcap, shall we?" Suddenly I remembered Ruthann's obese mother, "Tiny", whom we had left completely ignored upstairs in her "throne room", a prisoner of her morbid and non-ambulatory obesity. "What about Ruthann's mom?" I stammered. "I can't imagine she would approve of our....your, well you know what I mean." "Oh don't bother about her. She's probably fallen asleep watching TV as she normally does. But anyway, she knows about us and our little "hobby". She fully approves and even used to participate as "the evil mistress" when she was still able to get around the house. She loves our sexy persuasion!" Phyllis giggled, winking at me, as she reached over to gently squeeze my semi-hard cock through my dress trousers. I touched her in return, stroking her slender body through the silky material of her glowing satin brocaded robe. I could feel the outlines of her corset and garters as she leaned into me. My cock twitched and started to harden again. She pulled me to her face and kissed me softly, her tongue probing my teeth and lips expertly, her gorgeous eyes looking deeply into mine. Once again I experienced the intoxicating taste of menthol smoke and lipstick as I met her tongue with my own. I was partially enveloped in her satin robe and the swirling scent of her Giorgio. Impatiently, Rolanda cleared her throat and we reluctantly halted our passionate kiss, relaxing our embrace. "My turn, Honey," she purred to Phyllis. As Rolanda insinuated her femmy gay body between Rolanda and me, I became aware of the earthy scent of her full length Blackglama mink. She had lit another long 120 and held it femininely in her two outstretched fingertips as her other arm slipped around my waist and gently pulled me close to her. Gazing hungrily into my aroused eyes she took a slow deep drag from the cigarette and inhaled deeply. She then pressed her voluptious lips against mine while her tongue snaked into my willing mouth. As our tongues insistently darted against each other, she exhaled the creamy mentholated smoke deeply into my lungs. The intimacy of receiving her smoky essence into my eager chest was overwhelmingly erotic. I was totally captivated by her fragrant presence, writhing slowly against me. I moved to press my raging hardon against hers as she slowly arched the bulge of her gay effeminate genitals against mine. My hand caressed her hardness against my own and a little moan of pleasure escaped involuntarily from me into her warm wet lipstick- coated mouth. I felt light headed, nearly levitating as the sweet taste of smoke, Oscar de la Renta, and makeup invaded my being. Finally our lips parted. Phyllis stroked my neck and buttocks with her long red nails. I was in heaven! Phyllis hooked her arm through mine and Rolanda took my hand and we walked together into the living room where I was gently deposited on the sofa. Rolanda sank into the supple leather next to me, crossing her legs femininely as I admired her feet perched in her ultra high heeled red satin Springolator mules. I had been obsessed with high heels as long as I could remember and frequently took the opportunity to window shop in front of sexy ladies' shoe stores like The Wild Pair whenever I found myself in a mall. The first thing I noticed about any woman I met was her shoes, and the second was whether she smoked or not. High heeled pumps and sandals were so scandalously impractical. They were worn for one purpose only, to catch the eye of a man, and display inviting sexuality. My new lovers were obviously aware of the allure of their closet full of dazzlingly outrageous shoes in all the colors of the rainbow. They knew that five inch pumps were not only erotic attention-getters, they were an important element of a well baited gay transgender trap! "Scotch again, Richard?" The question snapped me out of my reverie about high heels and smoking divas with a "little extra" in their panties. "Yes, please, Auntie Rolanda, on the rocks if you don't mind." "Drambuie for me, Honey," Rolanda spoke to Phyllis, who was already sashaying towards the liquor cabinet in the kitchen, teetering femininely in her spectacular skyscraper-heeled pumps. Rolanda graciously moved a fresh gleaming crystal ashtray in front of us and femininely put out the remnant of her cigarette. Phyllis soon returned, balancing a little tray of drinks, a scotch for me and two Drambuies for herself and Rolanda. She placed the tray on the coffee table and seated herself next to me, opposite side to Rolanda, crossing her legs provocatively and allowing her long brocaded satin gown to fall open, again revelaing her gorgeous legs all the way up to her stocking tops. I adored the sight of her taut garters and the black welts of her silky stockings contrasting with the milky whiteness of her smoothly shaven thighs. The elegant "ladies" exchanged a wink as they watched me enjoy the erotic sight of previously forbidden fruits now so mouth wateringly available to me. We clinked glasses in an unspoken toast to future trysts (I hoped!) and sipped our drinks in silence, caressing each other's bodies lovingly. It was incredibly delicious to sit between these two glamorous femmy older men dressed as femme fatales as they touched and fondled me affectionately. "So, Richard, have you enjoyed yourself?" purred Rolanda. "I believe this evening may have been a revelation for you. I don't think you knew what wonders existed on the better side of the gender divide, did you, Darling?" I looked at her happily. "No, I had no idea what a lovely surprise had been awaiting me, Auntie. I don't know what to say, except 'thank you!' Thank you for inviting me behind the satin curtain." Phyllis smiled approvingly and gave my thigh a loving caress. "We hoped that our little hypnotic 'parlor game' might have the desired effect," she laughed. "I hope you won't regret it. The last time one of Ruthann's serious boyfriends was introduced to our 'hobby' he ran out of the place like it was on fire! None of us ever saw him again. Ruthann was really unhappy with us for awhile after that. The last time we successfully 'converted' one of her boyfriends, I thought she'd never forgive us." "'Converted' one of her boyfriends?" "Yes, he loved dressing up with us so much that he dumped her and became a flaming drag queen, Honey!" They both laughed as I lit two fresh cigarettes for them, and one more for myself (Unwittingly, I was now becoming a thorougly eroticized femme smoker too!). "Really? What has happened to him since you, ah, 'converted' him?" "Oh, he, or should we say 'she', still lives here in the city. Her femme stage name is 'Sugar Cane'. In gay male mode, he's a makeup artist and hair stylist with a huge clientele. He has a very tony shop where he tries his best to make ordinary genetic women look as good as we do! Of course, he can't!" They both inhaled thick mouthfuls of menthol smoke and laughed in their special gay way, enjoying the fact that no woman could ever look as good as they did. "Naturally, he does makeovers and gives makeup instruction for novice transvestites after normal hours too. And he makes housecalls for the 'closet queens'" Rolanda laughed androgynously again as she exhaled another creamy white jet of menthol smoke towards me. The swirling mixture of her seductive Oscar with the sweet smoke was intoxicating to me. "Occasionally he also does drag shows at a nice uptown supper club where straight people go to see 'a queer in gear' and get their little sexual kicks. You know, there are a lot of men out there who have fantasies about being with girls like us, but don't have the guts to cross over the line of convention. The poor bastards live their pathetic little repressed lives, fantasizing about having sex with a transvestite lover, or being one themselves, but they never have enough courage to explore the 'dark side' where they would be so much happier!" Rolanda chuckled, secure in her own gay superiority to ordinary heterosexual men like the one I had always thought I was, at least until a couple of hours earlier, and now despite my woozy gender confusion, still thought maybe I should be. "So, are you going to abandon Ruthann and join us on the dark side, or are we simply going to give you another hypnotic session to erase our tryst from you memory, and forget that giving your first transgendered blow job never happened?" I was suddenly impaled upon a dilemma I hadn't expected so soon. Despite my conscious aversion to what had recently happened, I couldn't bear the thought of not experiencing the joy of transgendered sex with my newfound lovers again. Furthermore, the "girls" had cleverly left me with a still raging hardon pleading for sexual release. My prick started thinking for me and I said, "Well, Auntie Rolanda and dear Phyllis, I guess I really haven't had any time to consider it. I'm still overwhelmed with what I've just experienced." With an incredibly innocent look on her face, Phyllis vacantly raked her fangy fingernails over the bulge in my trousers, pretending not to be the slightest bit interested in my ambivalent answer. My prick surged against her touch and I could feel another little trickle of precum leak into my boxers. "I really care about Ruthann," I tried gamely again, "and I know she cares a lot about me." Neither of my companions were deceived by my words while my cock was so obviously twitching in my pants! "Honey, I love Ruthie as only a parent can, but don't you think you should give this a lot more thought? She's got three little kids and she's living mostly on child support from her dirtball ex-husband. You're a sophomore in college with your whole life ahead of you. Think about it. You are preparing yourself for life and you haven't experienced much more than a taste of it. Do you really want to quit school and take on the responsibility of raising three children right now? On the other hand, you are probably constantly distracted by the need for sex and pursuing girls to get it. You take them to dinner on your limited student budget and do your best to get into their panties. Then there's all that drama when they want you to marry them for taking their virginity. It's a never ending viscious circle when you're constantly in the hunt for pussy." Rolanda paused and we all took deep inhalation of menthol smoke, exhaling as the images of my frustrating life as an unfulfilled sex addict played in my mind's eye. Rolanda reached her shimmering satin-gloved arms around my shoulders and pulled me to her, giving me a sweet little sympathetic kiss. "Ill bet you jack off three or four times a day out of pure frustration, don't you, Dear?" Jolted by her use of the term "jack off", I lowered my eyes and nodded honestly, feeling as though I were a little boy who had been caught with his pants down. Her mature awareness of my private sessions of self gratification served to shame me for my inability to get laid as often as my testosterone filled body craved. "Yes, Auntie, I'm afraid I do." I murmurred in embarrassment, but somehow relieved that someone else knew of my masturbatory crimes and actually sympathized with me. "On the other hand, Honey, you can have Phyllis and me for your happy sexual gratificatication anytime you wish. We'll always be waiting for you, wearing our sexy gowns and furs, our makeup and glamorous wigs, our exotic jewelry, our yummy satin undies and stockings, and smoking our long white cigarettes...." I could feel myself being swept up in the image of all those femmy temptations that I longed for my occasional girlfriends to exhibit for me, mostly unsuccessfully. Frustratingly, I found that even if my girlfriends reluctantly yielded to my hints at how I wanted them to dress and make up for me, they inevitably used it as a form of entrapment. A few smoked like proper ladies, or took it up to please me, but it was always a trap. I was already becoming aware that they were all nesters, using sex to get the security and intimacy that drove them. Although some pretended convincingly, they didn't really enjoy sex the way men did. To them it was a tool, a lever, the tender cage of male domestication. Rolanda interrupted my silent introspective musings about the frustration of girls, "Unlike genetic women, we share the same sex drive and gratification that you do. With us there's no 'quid pro quo', Darling. We both want the same thing as you. With us, we love strong handsome men, or femmy lesbian trannie sisters, but for mutually satisfying sex with no hidden agendas. We just love the sex act like you do, and better yet, we're always 'in the mood' without being promised the moon in exchange! Doesn't that sound a lot better than what you've been going through since you first discovered that your prick is for more than pissing through?!" That last line was too explicit even for the gay Queen Phyllis, "Rolanda! Let's remember that we're ladies here! Rolanda bitchily ignored the reproach and inhaled another sweet mouthful of minty smoke, exhaling it demurely toward the bulge in my pants. "Well, my darling boy, you don't need to make up your mind about it tonight. Just enjoy the sweet knowledge of your "new discovery" and you'll come to the right decision, just as we did. Remember, we think you are the hottest and most interesting young man we've met in ages," she looked at Phyllis who nodded agreement as she stroked my thigh lovingly with a freshly lit VS menthol perched in her first two fingers as only a glamorous diva queen can. It drew the precisely intended instant attention from me to her long red nails and the large rings on her three gracefully curled back fingers. "We almost feel guilty about stealing you from Ruthann....but only almost!" she smiled provocatively as if the theft were already a confirmed reality. We finished our drinks and smoked a last cigarette together. "I really should be getting you home, Richard," Rolanda said wistfully as she arose from the leather sofa. I reluctantly agreed, my prick still craving relief. Phyllis walked me to the door as Rolanda excused herself and ducked into the magical guest bedroom to change her shoes to ones more appropriate for driving. She soon caught up with us in the entry foyer wearing incredibly hot gold lame' five inch heeled pumps trimmed with red patent piping. She carried a medium sized matching gold envelope purse tucked under the arm of her fur. Rolanda looked fantastic in her shorter wig, red satin gown, and full length mink with its elegant shawl collar. Rolanda and Phyllis paused at the front door and pecked each other affectionately on each cheek. Phyllis gave me a deep wet tongue-probing kiss and slipped me her cell phone number on a slip of paper. "Call me anytime you want to see me, or just chat about things. I'm always 'available', Honey," she whispered into my ear during one last hug. She kissed me quickly one last time as she gently dug her long fingernails into my palm, letting me know that she couldn't wait until what she hoped would be our next erotic encounter. Rolanda and I said goodnight to Phyllis, thanking her for her hospitality and a wonderful evening and turned to walk towards Rolanda's Cadillac parked directly in front of the townhouse's entryway. It was a recent model four door Brougham, gleaming pearlized white, a perfect car for an elegant lady like Rolanda. She slid gracefully behind the driver's seat and I shut the door, walking around to the passenger's side and letting myself in. Rolanda started the Caddy and expertly backed out of the carport. It was difficult for me to take my eyes off of her softly glowing new gold heels. They were devastatingly eye catching. She looked so glamorous in her fur, pretending to ignore me as she drove through the nearly deserted streets. Her slender hands limpwristedly manipulated the wheel as her feet, wedged into the shiny pumps, worked the pedals as if she had been born wearing five inchers. It was a thing of beauty to watch, which I did with abject fascination. We drove in silence until we had joined a major arterial. She seemed to know where she was going without asking me where I lived. Finally, Rolanda handed me her gold lame' purse. "I need another ciggie, Honey. Would you be a doll baby and light one for me, please?" I opened her purse and found the cigarette case, a matching gold leather pouch, and opened the clasp with a soft little "click". The cigarette pouch had a slender holster on the front which contained an elegant gold Dunhill lighter. I took out a long 120, held it like a lady in my outstretched fingertips, touched the lighter to the tip and inhaled the rich smoke deeply. It was deliciously satisfying and the mintiness seemed so feminine to me for some reason. Rolanda noticed my feminine smoking style, and smiled as I placed the freshly lit cigarette into your outstretched gloved fingers. I loved watching her hold the cigarette as she drove. I had always admired women who could smoke elegantly as they drove, it was just another connection with sexy femme smoking that I had always harbored as long as I could remember. She had discretely spread open the hem of her fur and hiked up the long satin skirt so that I could see her creamy white thighs above the tops of the welts of her smoky black sheer stocking tops. I lit another cigarette for myself as I admired the garters straining to tighten the silky material firmly against her shapely legs. She drove on as we enjoyed our cigarettes, filling the inside of the Cadillac with the aroma of menthol smoke and Rolanda's freshly applied aura of Oscar. I scooted over towards her a bit on the rich leather upholstered bench seat so that our legs were touching. The sensation was delicious. Rolanda reached down and caressed my thigh with the gloved hand that daintily held her cigarette. Her touch was electrifying and my erection hardened again. It had been alternately rock hard and semi erect for three hours at that point, and was getting uncomfortably firm again. My boxers were still damp with all the pre-cum that had leaked out of my prick during those hours of nonstop arousal. Rolanda broke the relaxed silence. "Honey, please unzip those pants and take out your cock for Auntie to play with." I quickly complied. My raging hardon protruded straight up from my fly now. Rolanda put out her cigarette in the Caddy's cavernous ashtray and soon her feminiized satin touch was thrilling the overstretched foreskin of my engorged penis as she drove onto the freeway towards downtown Seattle. "Feels nice, doesn't it, Darling?" A softly moaned "Mmmm huh" was all I could manage in response as my buttocks arched against the leather seat, guiding my prick up and down through her encircling fingers. She smiled at me in the mirror, obviously enjoying the look of silky pleasure in my half closed eyes. "Auntie loves the feel of a hard cock in her hand while she's driving," she said as she slowly worked the satin of her glove against my tingling penis. "Pull my panties down, Sweetie, and see if you like the feeling of one too," she insisted gently. Without further urging, I quickly complied with her request. I pulled the red satin of her long center split skirt the rest of the way open to reveal matching red satin panties barely containing a delicious bulge of hardness glowing through the silky material. I gently eased the encapsulating satin aside and Auntie Rolanda's clitty pole sprang upwards to full extention. Although I had never thought of a cock as being pretty or attractive before, I suddenly realized that hers was incredibly beautiful. It was smooth and pink, with a bullging symetrical purplish helmet head. The sight of it in the soft glow of the maplight made my mouth water with the irresistable desire to swallow it. Below Rolanda's hard prick lay a pair of velvety depillitated balls. Her cock was average sized in my estimation, but her semen-engorged balls were much larger than mine. I couldn't resist the urge to softly explore them with my fingertips. The scrotal skin was incredibly smooth and moist with the texture of velvet softness to my gentle touch. Rolanda obviously liked the feeling as she moaned a soft insistent "Oh yesssss, Baby Doll" through her bright red lips. She continued to stroke my cock as I began to return the favor. Suddenly, Rolanda had a burst of femmy inspiration, "Richard, in my purse I have a silk scarf. Please take it out and use it to fondle my clitty and my balls!" she moaned. I opened her gold purse again and among the makeup, cigarettes, compact, wallet, and perfume spritzers, I found a carefully folded long black silk jersey scarf. I wrapped my left hand in the silky material, thrilling to its slipperiness as I encircled Rolanda's throbbing cock and began to slowly run it up and down the length of her shaft and over the bulging helmet of her glans penis. With my right hand, I cupped her pretty testicles gently with my fingers through the silky scarf. It was incredibly naughty and erotic to me, which excited my already stiff cock to a new level of arousal. She uttered a deep moan and squirmed subtly on the soft leather seat as she tried to concentrate on the nearly deserted road slipping by at 70. She was breathing very hard now in short spasmodic bursts. It was clear that she was adoring the erotic sensation as she breathily urged me not to stop. I surmised that she was nearly ready to cum, but strangely, I didn't want it to be over so quickly, at least without me being able to accept her ejaculation in my salivating mouth! Finally, she gently tried to push my hands away from her perfumed crotch and managed "Stop, Honey, I want to make this last. I adore you and the sensations you're giving me, but I want more than just a lovely handjob in the car," she breathed, "I want a lot more, Baby, and I think you do too. You can tell how fucking horny I am, but I want our first time together to be even more special." I reluctantly agreed with the sentiment, enraptured by the thrill of this new sexual universe into which I had so recently and unexpectedly been propelled. Somewhat hesitently, I allowed her hands to stop me from the rythmic stroking of her erect clitty pole and relaxed my silky grip around her throbbing hardness. "Let's have another cigarette and relax for a bit" she gasped as we sped along the interstate toward the city. "Darling, how would you like it if instead of driving you home, I took you to my place and you could spend the rest of the night with me?" If you had asked me the day before if I would agree to spend the night having sex with a femmy gay man, I would have found the suggestion absurdly disgusting, but now, after my unexpected introduction to the world of transgendered pleasure, I immediately responded with an affirmative reply to what promised to be the most delicious invitation I had ever received in my young erotic life. "Good, I think you'll be glad you went home with me tonight instead of with Ruthann to her ratty little house filled with three screaming kids!" Rolanda's statement awakened me to the reality of how my evening had begun....being taken to meet the family of my latest girlfriend, only to be unexpectedly introduced to the fetching world of gay femininity. It was the first thought I had given to Ruthie since discussing the frustrations of college boy heterosexuality on the couch with her father as Phyllis and her "Uncle" Raleigh as the glamorous Auntie of my dreams, Rolanda! The same sexy Rolanda who had just invited me to her house for the night! I lit us two more cigarettes and we smoked in sexy silence as Rolanda took an exit that guided us to a neighborhood of posh homes south of the freeway near Seward Park. Soon we were slipping down a long driveway which led to the front of a stately Tudor home overlooking Lake Washington. The street side of the property was shielded in privacy by an encircling thicket of large Madrona and Douglas Fir trees surrounded by high, well groomed English Laurel hedges. Admittedly I was in awe of Rolanda's affluent neighborhood and especially the understated opulence of her elegant home. "My, I had no idea that window dressing was such a lucrative occupation!" Rolanda pressed the remote for the rightmost garage door in the trio of three, and guided the Caddy into what had once been a cavernous carriage house. "Honey, window dressing, even when you're the veepee of the display department doesn't pay this well, but fortunately I inherited a modest amount of wealth from a distant relative, so I do live comfortably as you can see. Working at the store does have its advantages though. My status as a corporatee executive allows me to buy much of Rolanda's clothing, shoes, jewelry and furs at substantial discounts. You do seem to like furs, Richard" she slyly observed as I stroked the soft sleeve of her mink wrap. "Yes, Rolanda, I love furs on ladies. They are so elegant and glamorous. I've always dreamed of making love to a classy lady wearing a long full length fur for me. I often fantasize about it when I masturbate." I was suddenly embarrassed by my second easy admission of the evening to another person that I "jacked off". Despite the shame that the confession to Rolanda evoked in me, it was somehow refreshingly liberating at the same time. She smiled understandingly at this repeated frank confession of youthful indiscretion. "You'll find that the reality is so much more satisfying than the fantasy, Darling. I think that you'll be pleasantly surprised by my large collection of lovely furs." My heart skipped a beat at the imminent possibility of sex while encapsulated in the heavy satin lining of a full length mink or fox worn by my transgendered lover! The garage door slid soundlessly closed behind us as the Caddy glided to a stop in the spotless garage. Auntie Rolanda turned to me and with her slender effeminate arms gently pulled me to her by the lapels of my sport jacket. Her heavily made up eyes glowed in the soft light of the garage's interior as she looked intently through my eyes into my soul. "Give up all hope, ye who enter here" she whispered, and then she slowly leaned towards me and pressed her fragrant and slightly sticky lips to mine, exploring my mouth with her sensitive tongue, and once again, her gloved hand stroking my still exposed cock with its warm electrifying silkiness. I knew then that I had started down a divergent path of pleasure which I had never expected and from which I might never return! To be continued....