At age eighteen I had finally made it into one of the best universities in the country, yet my true life lessons and deepest learning would ironically take place for me during the weekends. I’ve had the complicated urge to dress up as a girl since my early teens. Eventually I consciously chose to act on my need to do so. Though I live a mostly normal existence and also do enjoy my male side, I was driven to find out more about the feminine side of my persona. A year ago at age seventeen my urges and need to be a girl in public were so great that it drove me to come out my room and closet.
When I got my driver’s license I was able to go into the city and explore. Soon I found the courage to dress in full feminine drag usually making myself up in my car and becoming my alternative self “Cari.” At night I began to daringly visit a night club in Boston that was transgender friendly. Being slim, short, petite and with purposefully long light hair, I had many of the prerequisites to be believable as a girl. I had already become quite expert at make-up and I soon found that with great care I could pass as a pretty young feminine girl in most public places.
Ironically even the prettiest girls in these transgender bars were most often guys and most of the so called girls were prettier than almost any woman around! With more practice and the benefit of youth I was lucky enough to become one of those considered by the bar patrons to be one of the prettiest. Unfortunately my sexy appearance and feminine ways did not always match what many often expected from me. The bar regulars too frequently assumed I was some kind of sexual professional or slut. Bars like this one had many professionals and usually they were the most enhanced and attractive. In going out to these clubs my education as a sexy looking transvestite was happening very fast. At times it was both dangerous and intense!
I am and have become a stickler for the details as a crossdresser. When I get dressed up I am literally all in. Every inch of my body is smooth shaven and pleasingly perfumed. From my red painted toe nails to my perfectly lined bright red lips it is hard to find anything about my appearance that would make the average guy think I am anything other than who I appear to be. I also have a swimmers build, a flat stomach and a naturally narrow waist. My deep feline desires cause me to be extreme in my dressing as my look is usually wearing only very high heels, stunning often overly revealing dresses, and the exposure of perhaps way too much of my smooth soft skin. The feline eroticism I feel from the clothing truly translates to how I actually look!
It is hard to explain but dressing up as a pretty woman is spiritually and emotionally meaningfully to me. I also find almost all feminine clothing to be incredibly erotic, sensual and even sexually stimulating. Going out in public as a girl simply began with the intention of being able to enjoy myself in my state of alter ego. As sexy as I felt and looked, I never took up with those relentlessly forward, shameless men who always seemed to assume that I was either a call girl or a hooker. I do confess that I loved the attention that men gave me, but my answer to their sexual inquiries was always a firm no. Things would begin to change gradually for me as I learned more about the under currents and realities of the mysterious LGBT world.
Being only five foot five inches tall and under a hundred and thirty pounds is a gift that I work hard at. I exercise regularly and watch my diet. Being believably slim and feminine enables me to wear almost any kind of dress. I have a true fondness for skin tight red or black dresses especially when they show almost the entirety of my thighs and reveal my skin just above my breasts. Being what my friends would call me – a city girl, can often be fraught with all kinds of inherent dangers. In my all too erotic and revealing manner of dress, just walking to a club from my car or to almost any place in the city usually attracted too many attentions. I enjoyed the danger of being bold at times but I would also often be just smart enough to have a cover up jacket or coat with me just in case the situation called for a lot more modesty.
I must have heard the words “Want to go out?” coming from car windows dozens of times in my walks around the city. It was actually often a call to hookers or prostitutes. Another irony is that it wasn’t until my eighteenth birthday and after I had been out almost every weekend for a year, that I was shyly and reluctantly talked into going out on a real date with a man. I expected a quiet dinner with my much older date but his kiss would literally change everything about how I looked at myself as a transvestite and as a pretty girl.
I slowly came to realize that all this dressing up and my urge to be so feminine and pretty had implications that I had long been in denial about. Being made love to by a man for the first time was not only shockingly unexpected but it rocked my world in ways I still struggle to describe. It was so powerful and so intense that it left me dazed in wonder and confusion. For whatever reasons being made love to by a man made me feel like the most attractive and sensual woman in the world. It almost seemed absurd to feel that way while having my own seven ample inches of maleness. I had apparently been both super naïve and in strong denial of my innermost feelings.
In the next few months I excitedly accepted and enjoyed the reality that I suddenly had a boy-friend! John was in his early forties, more than twice my age. He was generous and nice, fit and handsome and was happy to take my virginity from me. He also possessed a freakishly huge cock! It seems absurd that my first man was so ridiculously bigger than most. At nine thick inches my learning about pleasing him was more of a task than one would expect!
I soon had little objection because I came to love his magical cock. John was so very skillful as a lover that he could make me orgasm anally many times in a night. I also learned that learning to suck a nine inch cock takes lots of practice! I eventually figured out how to deep throat his entire monster cock all the way to please him. The day I felt his balls meet my lips was the day I knew that I was the kind of girl who truly knew how to fully please a man!
Long term relationships in the transvestite / transgender world are generally rare from what my friends always told me. It was nice and I felt lucky to have John’s attentions for almost a year. He even wanted to leave his wife for me. It was way beyond my thinking. I was in college and also enjoying my male life as well. I was in no way ready for such a commitment. It had to end. Being the other woman had been just right for my comfort level allowing me at the time to enjoy our unusual relationship without any real strings attached.
In nights back at the drag bar post boyfriend, I found myself in a place that I had never been before. I finally came to the realization that I enjoyed dressing as much to attract men as much as I did for my own personal enjoyment. This was finally a truthful, frank and honest admission about myself because I had denied the very bisexual feelings I had as well as the sexual feelings I had as a girl when I was all dressed up. My first boyfriend had obviously helped me change that! I finally understood how much I enjoyed the intimate company of a quality man. The only problem for me was that in this crazy transgender world there just did not seem to be many at all!
One night a couple of weeks later, I was introduced by my Transgender friend Sandy to a wonderful and again – older man who had an air about him that I found incredibly attractive. I of course just happened to be dressed alluringly in a teensy pink skin tight spaghetti strapped mini dress that left little to the imagination. My naturally soft smooth little male breasts were barely covered and my pink panties may have been visible in the back! The handsome man was apparently impressed and said I was absolutely the sexiest creature he had ever seen in the bar. He found my perfume dizzying and in my matching five inch pink sandal style high heels I felt sexy, even horny and in an almost lustful need for affection.
Roger was a very well dressed man and about a little over six feet tall and perhaps around forty years old. He reminded me a bit of my first boyfriend John but he seemed more polished and elegant. He had black and grey hair and he was both trim and handsome. I also loved his wit, his brown eyes and his quick smile. Being short and slender I seemed quite tiny next to him. Perhaps it was the usual free drinks or my friend Sandy’s introduction and winking endorsement that helped me find myself getting very comfortable with Roger. I instantly valued how Roger doted on me. Roger had both great awareness of what I seemed to like and a terrific sense of humor as well.
He generously bought me whatever drink or bar snack that I wanted. We soon talked in a pleasing manner that I would describe as surprisingly comfortable. We shared each other’s likes and dislikes. When our talking turned sensual, I found the flirting and energy between us to be quite delightful and even magical. This guy seemed like a true gentleman. He had me confessing my past sins and my naughty penchants better than a clergyman! When a pretty, somewhat inebriated girl tells a man the secrets about what she likes in bed she is either naïve, stupid or both! It would be a while before I would come to realize that this strikingly handsome, sexy guy was a “Dom” or dominant type. Sandy apparently knew about his inclinations but didn’t tell me. Little did I know that his style, persona and everything about him might have me melting like ice in the desert in a very short period of time.
Roger and I talked to near closing time when suddenly I became acutely aware of the enchanting nature of his gentle touches and his true charm. I had been sitting on the bar stool legs crossed and showing lots of leg while sitting close and next to him. I also realized just how overtly sexy and alluring that my teensy short tight hot pink spaghetti strapped mini dress and my sexy high five inch matching hot pink heels must have looked to him. I tuck my seven inches of manhood between my legs when I dress and it was in quite a state of hardness, making my panties feel way too tight! In spite of looking like a bit like a high class whore, (as Sandy had said to me!) I felt both pretty and very desirable around him.
Roger’s presence also made me feel very feline and quite sensual. It had been a few weeks since I had genuinely enjoyed a man’s company and Roger had me feeling that feminine high I so enjoyed when I was treated with caring and respect as a “female”. My appearance had such an obviousness to him that even I did not fully understand. My ease with him and my mildly drunken state had me feeling very erotic and sexual. I was melting in his company. Still my shyness, youth, fear of the unknown, inexperience and lack of confidence as a “woman” had me fearfully thinking of the future. I was perhaps not willing to risk anything beyond meeting him as soon as tonight. I wanted to find more ease with myself as the female with a man in a more sheltered and even controlled circumstance.
I already had a complete yet blind confidence in Roger which I almost never had encountered with the exception of John. He nicely asked if I’d like to go home with him and I wanted to say yes. I winked and honestly but fearfully said – “I’m tempted.” But I shyly but coyly told Roger – not tonight – but that I wouldn’t be opposed to a date with him in the future. Roger seemed pleased enough. He put my phone number into his phone while promising to call me early Wednesday evening to arrange a date for the weekend. I was very happy with his patience and sensed something very special about Roger. He made me quiver in his company and his strength, confidence and masculinity made me swoon.
Roger walked me to my car a block and a half away. I loved how he held my hand and how we walked arm in arm. He so skillfully held me gently and close to him. It was getting cool and at my car he hugged me while giving me the warmest most breathtaking kiss that I’d ever experienced as a woman. I arched my back and stood tall on my high heels feeling so small, so feminine and so vulnerable in his arms. His hands found my bottom and my weakening body almost dissolved into his hold. I was proud of myself because I was truly fighting the urges I had for more. I thanked him knowing in my heart that he would indeed call me on Wednesday evening.
Back at College as a regular guy Monday was a nice change. I was able to focus on my studies but by Wednesday my female mind kept thinking about Roger. I got home to my apartment early after working my part time job. I was enthused and hopeful about getting my promised phone call from Roger. I decided to partially dress femininely so I would truly feel like a girl for his call. Now comfortably at home, I was a hairless smooth skinned feminine boy enjoying the joy of simply being dressed in a sexy red silk negligee and string panties. I sat a bit anxiously in front of the TV waiting and hoping. When the phone rang right when he said he would call it pleased me greatly. Very few guys in a transgender bar are what I would call dependable. I had sensed that Roger might just be an exception.
I immediately felt comfortable while talking with Roger. We talked, joked and even flirted with each other for over an hour before Roger asked me about what I found sexy and sensual. He inquired if I liked the idea of bondage or discipline –and I did admit to sharing some positive fascination about it. Roger got me to admit that I had a submissive side. I confessed that I did like it when a guy takes “charge.” Roger was so persuasive yet so considerate that I was somehow spilling some of my deepest personal secrets that I had never admitted to anyone.
This quite private yet erotic phone discussion was causing me to get stimulated. He asked if I had ever experienced any B&D like I had admitted seeing at a couple of transgender parties. All I could offer up in my own experience was that I admitted to Roger that I had enjoyed it when I got a spanking (from John) in the past. I told him I never had thought too much about it but he was quite pleased with me and complimented my honesty. It was a few minutes more before we agreed that he would pick me up at 8:00 P.M. Friday night at my apartment. Roger’s earlier suggestion in our conversation that he might someday ask my permission to explore my submissive tendencies had me practically breathless in anticipation. My awareness into these propensities were ever expanding in spite of my denials to date.
On Friday I got out of my Chemistry class early and got home before 4:00 P.M. I spent the next two hours in my apartment preparing myself in what I call my “Feminine Delight Odyssey”! I take a warm bubble bath with bath oils and proceed to shave every inch and corner of my slim body all over from face to toe. In the mirror my lack of pubic hair and baby like face and my longish light brown sun bleached almost blonde hair makes me look like a feminine pre-teen boy except for my constantly hardening seven and a half inch erection. I wanted to be perfect tonight. It was very exciting knowing that I would be dressing not just for myself tonight. Getting all dressed up for a man for a date already has me in such a state of feline excitement that I think only a true transvestite or trans girl can understand.
I reveled in the preparation and joy of taking great care with my make-up. My tools included eye liner, false eyelashes, powders, blush, lipstick, and lip liners and more. I then painted my toe nails and glued long red nail extensions over my own longish nails making my male hands look suddenly so feminine. Next I added my first high quality blonde wig. It is designed to be taped to the scalp in the front and is so realistic that it can be convincingly be combed and brushed backwards off the face. I find my facial appearance breathtakingly feminine enough and incredulously (to me) pretty. With such normally long blonde hair I feel I have stunning appearance. In less than an hour I skillfully glued and painted myself into a very sexy young blonde “gal”. All I needed were my best choice of my wondrous female “clothes” of which I have an incredible two closet filled collection – perhaps a record for an eighteen year old!
I have a full closet filled with dresses and high heels! I have dozens of stockings, panty hose and a number of garter belts. I have over two dozen panties and a dozen or so bras. I always match my “colors” and tonight I decide will be simple basic black. My waist is a trim thirty inches but with my special waist cincher it will be three or four inches less. I put on a black garter belt over the cincher and add black silk stockings that attach with garter belt clips. I add a strapless bra and pull my breasts close to center resulting in totally realistic appearance of cleavage. In my full length mirror I cannot believe how sexy I look – even without my high heels!
I have four black dresses all of which are close to my heart. I know which one I’ll most likely choose but I try each one on adding my tall black platform sandaled high heels for final affect. I also tried on the light green skin tight spandex spaghetti strapped micro mini that I wore to the bar last week – which obviously now in the mirror’s reflection leaves nothing to the imagination. I understand why Roger found me so sexy and attractive. I also think the he saw me as a very naughty girl because few would dare to wear a dress like this out in public like I had! I knew what he might expect from me tonight and I was torn in spite of my apparent “need”. I was not sure at all that I was ready to be a man’s woman again in spite of a wondrous first experience with John.
I would go with a more conservative black dress with a tight flared waist, high back, but exposed but sheer chest and shoulders. The dress had a shaded lace black breast area which made my breasts look real. I changed into a longer wig that matched my hair and I thought I looked very pretty and even cute in it yet with a subtle sexiness. I wanted to look like an elegantly dressed woman and I was very pleased with the result. At eight the doorbell rang. I do love a man who is dependable and on time!
Roger met me at my front door. He smiled and complimented me telling me I looked breathtaking. This guy knew how to make a girl’s day. He was already drawing me in! Roger then took me by the hand and led me down the stairs to the street level. The forecast was for a warm fall evening so I felt good in this sexy black light dress and felt even better in the silky flesh colored stockings I had changed into. The contrast seemed better showing my smooth legs rather than mute them in black. I swayed my bottom just a bit while walking to his parked car about a half block up the street. I felt like a million and Roger so seemed to just know how to treat a girl right!
Roger had a very nice car and it felt quite enjoyable to ride along as his date in this bit of Lexus luxury. During the ride Roger asked me about school and my goals in life. He seemed to know a bit about a lot of things but he was surprised that I enjoyed being a guy as much as I did being a girl. He said that he assumed I was going to transition to female and would have surgeries. He assumed that I’d already had breast enhancement but I told him it was just clever bra and body contouring and even body color shadowing. I told him that I had no plans to alter my body and he said I was amazing to be able to look and be so feminine and to just be a transvestite. I guess that was quite a compliment that no one had ever mentioned to me.
Roger was taking me for drinks before dinner so we stopped at the club in Bay Village for a drink before a short walk to the restaurant. Roger was in a suit and white dress shirt and I must admit that I looked almost as well dressed in “black.” Johnny the bartender had to get a picture of us all dressed up and he took several of us from different angles and distances. He would even put one of our pictures up on the wall in the bar because he said we looked like a Hollywood couple! I was quite proud of how much we looked like a normal couple, though Johnny joked that I looked like Roger’s daughter rather than his date! I so loved Johnny and his sense of humor.
After two drinks we left to walk to the nearby restaurant for our dinner. It was only three blocks away but we were a little early so we took a little detour through park square to kill a little time and enjoy the night. We passed an adult lingerie shop which was still open. We both remarked at a sexy white spaghetti strapped bustier with matching white stockings and panties in the window that was incredibly sexy. Roger said he just had to buy it for me! In we went and he bought it for me. I was so excited and I promised him that I would model it for him!
Roger must have had incredible instincts or just plain great radar because my feminine emotions were suddenly locked on the stunning garment that sat at the bottom of the bag he was holding while walking with me.
“I can’t wait to try that on,” I blurted out honestly.
“My condo is only two blocks from here….,” Roger said.
“Let’s go!” I said thrilled that he lives so close. I had suddenly become a crazy, heated, sleazy gal who was fascinated and in lust with the feline bedroom outfit bought just for me.
Roger seemed delighted and almost amused. “I can’t wait to see you in that Cari. You look so hot now and in that I may lose my mind girl!”
His condo was large, beautiful and as elegant as he. There was a huge antique white and black marble fireplace in the center of the living room. His kitchen was huge and open with shiny, elegant black granite countertops. The dark furnishings looked like I was in an English Castle. I was more interested in finding the bathroom so I could try on this magic outfit! I went to the bathroom and stripped to my high heels. I put on the string bikini bottom and pulled up the sexy bustier. Then I put on the matching white silk stockings fastening them to the garters. In the mirror stood the sexiest girl I had ever seen. I was as excited as a little girl at her own birthday party.
I walked out of the bathroom and confidently posed on the shag rug for him. I could not believe the incredulously sexy “girl” was me! Roger had a camera nearby and coolly snapped a quick photo.
“You are stunning!” he said.
He took two more as I posed both thrilled and in lust! Roger was as excited as I was. I had unconsciously but quite willingly surrendered to him the moment he had bought this magical bedroom outfit. The kiss began almost the moment he finished taking the photo. Roger stripped in seconds and was nude and hard! I knew the outfit was just what I needed to feel “comfortable” in as a man’s woman and I was ready for much more!
I felt so filled with desire that I found myself on my knees. I was drawn to his naked body and his cock was magnificent. It was so large, long, yet so thick. He was circumcised and the head of his incredulous member was like an overgrown mushroom! A “girl-boy” usually learns quickly what pleasing is about. I was unafraid in spite of his size. I was just so needy and so ready to be me. My first boyfriend had taught me almost all that I needed to know. I loved pleasing a man this way and Roger was soon moaning and moaning. I looked up at him able to smile only with my eyes and feeling so proud of myself for being so pretty and yet yearning for much more. Getting him so hard immediately had me hard as a rock as well. What joy I was finding in man pleasing!
I was like a starving girl. I was so enthusiastic and worked up that I had Roger near orgasm in less than a minute. Fortuitously he lifted me instinctually knowing that his “girl” deserved more. I hugged him and found myself being picked up in his arms. I was melting, swooning and in complete comfort as I was carried into to the bedroom. Roger placed me down on the bed like a treasured child and gave me a wondrously deep kiss. Soon the magic of our coupling began to evolve into the most beautiful moments of my young life.
Roger was atop me and his lips and mine were locked in intense passion. Soon his tongue and mine were intertwined in the most mutually fervent kiss I could ever remember. I never felt more loved. I never felt more naturally female. My arms were around his back and his backside in ardent and willing surrender. In my “silk love outfit” I was his and in his arms I was where I belonged. There would be no stopping our expression of mutual infatuation and mutual need.
I was so happy that Roger didn’t hesitate to roll on a condom as I surged in the excitement of what was to come. He entered me gently as possible as I cried out in as much joy as there was pain. Beneath him and with my legs being spread and bent back I felt like I was ready to have all of him. The ridiculously huge cock head he possessed caused more than some discomfort but I wanted him so badly that he was soon thrusting into me almost fully. Roger’s strokes were thrilling and even exhilarating. To say I was inspired, electrified and in awe would be understating the height of my delight and joy.
Feeling Roger’s balls now pounding my girlishly round bottom was mind blowing and incredulous. In both my physical and my emotional realms this submissive realty had me so electrified and aroused that I somehow felt a desperate need not to become too submerged in all this wonder. I cared deeply about his pleasure. A good girl or a good “woman” looked out for her man first. Somehow I felt a desperate but conscious need not to become too overwhelmed in spite of this stunning loving.
As his powerful thrusts became rhythmic and driven I somehow I found myself biting my lip simply so I would not be vanquished by the throws of an early orgasm. My heart and soul were already there and my overwhelmed mind was above and beyond! His physicality and strength had me so helpless and his intense thrusts left me so thrilled that I was losing my mind!
The beauty of having an emotional connection with a man is intense. Even better was our mutual awareness. Roger already had me amazed, certainly overtly aroused, and in a state that was causing my body to shudder and quiver in the beginnings of orgasm. Roger must have sensed this from my desperate wails and my intense grip on his relentlessly grinding ass as I was also meeting his every thrust in pure instinct and lustful need.
Roger suddenly stopped his thrusting and this next deep kiss almost took me over the edge! Roger just knew how moved and frazzled I had become. He lifted me and put me over his lap! He spanked me hard as I winced and whimpered. I was shocked and surprised by this but in an odd way it seemed almost comforting. Ten hard spanks had me fully in his control. My hot behind had sobered me at least temporarily! His naughty smile and quick kiss to my hot red bottom made it all feel better!
“I love your naughtiness Cari. You know I am in charge of you and that I am your Daddy!” His words had me smiling and a bit dumbfounded as well.
Now Roger was on his back and was lifting me and centering me over his huge hard missile. He had already torn off my already stretched new and now used panties. He must have sensed that I so loved being on top and it was like he just knew it. In my sexy white bustier top he felt my nipples while firmly squeezing and cupping my breasts as I rode him. This just added to my madness. I soon became lost as a female pleaser grinding down on his cock and balls loving every down thrust and just so needing every stroke after stroke. Roger met my down thrusts with powerful up thrusts and the ride was sending me to heaven. Having my breasts held firmly while riding and feeling every huge thick inch of him deep inside me was just way too much!
I became conscious of the huge wall mirror on the entry side of the bedroom and our reflection was as clear as day. A truly sexy and beautiful woman was riding a man with a huge hard cock. It was perfect love scene or even perfect pornography. Then I saw the large bouncing erection on the stunning girl beneath her white nighty and it was only then that I realized that the scene was even more incredulous than it looked. “She” was a he, and she was me. I was so moved by the reflection that it happened right then. I was truly over-come by the stunningly beautiful scene of the expression of such real and mutual sexual passion and need! In my mind when making love to a man I was purely female. Being filled by a man’s huge cock was completely convincing of my female persona and role!
My cock and even my brain now exploded in lightning like flashes. As I began to flow and explode into the throws of the most intense orgasm of my life I shouted and cried out in high pitched wails. “Oh Roger” I kept screeching. “Oh Roger!” My anus and sphincter contracted intensely magnifying the wondrous effect of the deepness and thickness of his cock in my body. I spurted load after load of hot cum onto my lover’s belly and into my hot sexy love outfit. I was stunned and moved beyond any experience in my young life.
My physical and emotional contractions brought Rogers orgasm on almost as quickly. His guttural grunts and groans filled the room with the music I most wanted to feel and hear! Roger’s cries and his trembling body beneath me just kept me in the throes of the longest and most satiating orgasmic experience of my young lifetime. When it finally subsided I was dizzied and flabbergasted as I bent down needing so badly to kiss him. The depth of our kiss and the genuineness of our emotions did not require any words.
Roger and I both seemed stunned by the passion and the physical and emotional wonder of it all. We kissed for many minutes with his huge but still hard cock deep inside me. I was a wreck yet still lit up being so astounded and stunned by all of these feelings of incredulous wonder. It wasn’t until many hours into the morning that our hunger subsided. We never needed or wanted any food!
Sunday morning came and to my great delight I found that Roger was in no hurry to let me leave. He told me how pretty I was and beautiful and sexy my bottom was! He said that he always felt that I had the sexiest ass in the bar as well! He kept telling me how naughty I was and I joked that maybe I needed another good spanking. Roger didn’t hesitate! I sensed Roger was a quite dominant man and his expert tanning of my backside by his powerful hand lit me up in ways I had never comprehended or experienced. My cock was painfully hard as he told me to thank him for each spank. “Daddy” needed to teach his “girl” to be good, even though I had been!
Now more than just the thought of being a man’s “little girl” seemed to cause me a bit of a rush and an amazing outpouring of new emotions. I felt almost helplessly small, incredibly feminine and a bit dazed and confused by how I seemed to enjoy being controlled by him. In contrast though I never felt safer and more protected in the company of a man. I loved submitting to the spanking and I felt a readiness to learn more about a man who I knew had dominant tendencies from our sexy conversation on Wednesday night. I had so much of a sense of trust for this man and the role of being “his” was making my heart tremble with nervous excitement.
“I have some toys and a room you might like Cari.”
Intrigued, I admit I swooned a bit as Roger walked me down the stairs to a room that he had to unlock in the basement. I knew people had special rooms and even some extremists had dungeons and stuff. When we entered the room I was actually a little disappointed at first. I was expecting at least something that could be at least naughty. Roger put the lights on and there was simply an exercise room with benches and machines.
It was well lit and one wall was curtained in black. Roger walked me over to the curtain area and pressed a button as the curtain moved automatically revealing some things that I found most intriguing. Hidden behind the curtain was an area that doubled the purpose and size of the room. I was wide eyed as I saw an entire area and wall exposed. There were a menagerie of rather unique devices. I had been a spectator at some of my friend’s parties where bondage and discipline was themed. I knew what people used at least some of these “things” for!
Like a good host Roger walked me by each and explained them “in the second person”. He would say “The Cross is for people who might like to be spread for varying purposes….The slings are almost always used as fucking devices…. The bench’s here have use for discipline and also sexual purposes.”
I was aghast but breathless. I knew down deep in my heart that things were changing. To my surprise I was more than curious. There was an unusual black leather pad on the floor. Roger explained that a submissive would kneel down on it and she would usually have her hands tied behind her. It was for the purpose of servicing of her dominant. It had cuffs attached for ankles as well. I found it stunning!
Like the proverbial moth drawn to a flame I let my emotions and my erotic flashes speak. I asked if I could see what the leather pad felt like. Roger grinned and told me that I most certainly could. I knelt down on it as Roger showed me where to place my knees so the ankle shackles could be attached. I felt so vulnerable and yet that is perhaps just what caused me to ask to have my legs shackled. Roger had an efficiency with this gear that was demonstrative of lots of experience. With two quick clicks my ankles were locked while Roger asked if I also wanted to try the handcuffs.
I didn’t really know why but I wanted to be vulnerable and helplessly in his control! Yes – I said trembling in a combination of fear, excitement and anticipation! Roger quickly went to a drawer in the wall and soon my hands were cuffed firmly behind my back.
“Are you OK?” he asked kindly.
Like an excitable school girl my answer was another yes.
“Yes, Daddy,” he said looking me in the eyes.
I gladly and obediently repeated and enthusiastically replied with a very feminine “Yes Daddy.” and looked up with a smile!
Roger had me look at myself in the mirrors to my right. I was helplessly poised to be a man’s pleaser and I knew it both consciously and unconsciously. I was so pretty, so helpless and I was stimulated and aroused beyond belief! Roger knew I wanted to go further but he was a gentleman of “the code” and asked first. Now for the first time in my young life I was helplessly about to serve a man. When he shoved his huge cock into my mouth and throat I knew I would at least give my all to be the very best girl that I could be for him!
I loved Roger’s huge cock and as he grabbed my head and began to use my mouth and throat I found my soul in a place I never would have dreamed of. I loved bringing him pleasure. I had no control at all as Roger overwhelmed me with his eight thick inches until I could feel his balls slapping at my chin. I focused on breathing through my nose while I struggled with my gag reflex. Roger would sometimes pause and allow me a bit of time to recover but he was pretty relentless. Amazingly I still felt like I so belonged right where I was!
A girl in my situation has no choice but to remain focused on her job and purpose and though I struggled I was enthused and even thrilled by my predicament. The crazy even very confusing thing was that my servitude and helplessness seemed so very, very right. I had surrendered to him like no other person on earth and if a girl-boy could have a revelation while performing fellatio on a man with her hands and feet tied behind her back I sure did. I so wanted to please him and I worked and sucked his cock better and harder than I ever sucked a cock in my life!
Roger was moaning thrilling me and bringing joy to my enthusiastic struggles. My throat was his and I spread my lips and mouth so wide that I was completely his. I was neither slave nor prisoner yet it was so much better. I was now being owned by a man who apparently – I was more than willing to be owned by. I was his for his pleasure and hearing his moans had me near to what I might call my own emotional orgasm. I was never more turned on and never more willing to please anyone at any time or place.
Roger’s moaning filled the room. I was succeeding in every way possible. There was such freedom in the joy of being helplessly his! One of my friends at the bar used to tell me how “B&D” set her free. Now I didn’t think she was crazy at all. In spite of being his property and his pleasure giver my own cock was so hard and so erect that it was almost painful. There was little doubt how this role I had been placed in had moved and awakened me. I loved being his personal pleasure girl.
Suddenly Roger pulled out leaving me breathless and empty. I opened my eyes ready and hoping to see his man cum gush from the huge head of his man tool. I was more surprised though when he bent down and I got a long kiss on the lips. I found myself lusting for more and his searching tongue was more than rewarding enough.
Roger looked me in the eye and said, “You know how to please your Daddy and it looks like Daddy has found a perfect little slut to please him. You’re a very good girl. I’ll spare you the spanking. I’m going to get you out of this and into the sling.”
End Part One
