For as long as my memory serves me, I’ve had a powerful desire to look and feel feminine. Despite being all boy, my challenge in exploring and fulfilling my desires would be quite a test in an often-intolerant world. My reality was that I had to choose to pursue these strong, mysterious desires in secret. I knew I had to balance familial and societal realities. I knew that friends and family would find my fetish like desires too different. It was my needs and natural want to experience my feminine side, that drove my exploration onward.
I was incredibly opportunistic and clever in acquiring a stash of make-up and feminine clothing by the time I was a freshman in high school. By my junior year, I had already courageously explored the world in public dressed like a girl. I believed - in my heart - that I passed as a female while taking a walk in a Boston neighborhood, when I had an opportunity to apartment sit.
By age seventeen, I was off to college and thrilled to have the opportunity to find a small one-bedroom apartment. For the first time I could be discreet. I could finally explore opportunities to become the girl of my feminine dreams. To accomplish this, I needed to be both ingenious and earn enough money to become the weekend female I so desired to be.
I took the perfect part time job. I had often visited a Boston wig, dress and accessories shop. I heard they had an opening, and I was hired because I had already learned about almost every item the store sold. I naturally knew about make-up and believably feminine hair.
The shop catered to women but almost equally to transvestites and crossdressers. I would make many a friend while working there. I could also try on wigs and high heels there - so my purchases were worthwhile and of the best quality for myself.
I had already acquired a significant collection of feminine things in the past two years while at home. Now in my apartment, for the first time I chose to shave every inch of my slim body completely smooth. After a full week of practicing make-up, dressing and walking around in heels I was buoyant. Before my college classes began, I felt that the mirror told me that I might be ready. My reflection had me thrilled beyond belief. I was excited and very willing to try some very daring exploration.
I so loved the intensely feminine feeling of my smooth-shaven, soft, perfumed, quite lithe body. My light brown, blonde streaked, auburn hair was shoulder length and feline. At only five foot five inches of height and merely a hundred and twenty-six pounds, I looked great in almost any dress. Being short made me even more believable while wearing high heels that were anywhere from four to six inches in height.
Using my recently bought blonde hair extensions and in my realistically feminine make-up and my girlish clothes, I believed that I could pass as a gal in public. Though I was scared and fearful, I was determined. The strong desire to be Cari in public kept me from staying back in my apartment. Now having some confidence, every Friday and Saturday Night, I would go out in public, dressed to the nines. I’d daringly go out to a transgender bar in downtown Boston.
Going out dressed as a girl to a bar was incredibly terrifying and intimidating at first. The sight of me - a uniquely pretty, young, sexy, believably feminine gurl in teensy dresses and alluring high heels, was a rather eye-catching spectacle to most. I don’t understand why I was never carded, but I must have looked older than seventeen to the door men. When I’d sit cross legged in a mini dress at the bar, I was literally like flypaper. Most of the men were unfortunately brutally forward and even often relentless, in my pursuit. Frankly, I was scared to death at times and the bartender who I would generously tip became my protector. As a result, I usually retreated to the company of the girls who were like me at the other end of the bar.
It wasn’t long before my sexy, sensual short dresses and elegantly feminine looks soon had me labeled as the ultimate tease in the club. Despite my no touch and tease only reputation, I was constantly chased, ogled, and pursued by dozens of sleazy, forwardly shameless, and seemingly thoughtless men.
The first few weeks out in public as Cari was a trial of tolerance. It was so difficult learning how to deal with every kind of human being. I didn’t know the real why behind my dressing as a girl, but I knew how much I loved how much being a girl made me feel. I felt sexy, and even aroused by my own appearance at times. I didn’t dress for anyone but for my own pleasure and my own personal delight.
As much as I did actually feel flattered by the attention that I got from men, I related better to the friendliness and understanding of the girls. Some of the gals even hit on me with seriousness and humor, but I found their ways far less threatening. The girls thought I looked incredible, and I was thrilled to get so much positive feedback about how convincing I looked like a gal!
Still, I loved being called pretty and even beautiful. I was often offered drinks by men. I was beginning to believe that I was very attractive. Being constantly told that I was sexually desirable, and alluring made me feel both deliciously feminine and delightfully sensual at the same time. If only those pestering guys would relent. I simply wanted to enjoy being the flirty, teasing girl that I so loved to be!
One Friday night, I was approached by an older, handsome and well-spoken man. He was funny and warm. He was - for a change - a guy who didn’t turn me off. He made me laugh with his sharp wit and quick, sarcastic sense of humor. My girl-friend Stephanie had previously shared that he was very fond of me, so I was careful to keep my distance.
He kindly bought me many drinks over the next few weeks. His doting nature and his generosity was gradually earning my trust. I began to feel a sense of friendship and confidence in him. He would meet me at the bar every Friday and Saturday night. When I would arrive, he’d always have a drink and a saved seat ready at the bar for me.
It was very new to me to be able to talk casually, and even speak jokingly with a man in this dangerous, wildly awkward environment. Jack was unique, patient and seemed very different from the other men I’d met. He would even thoughtfully walk me to my car each night after the bar closed.
Jack would hold my hand to make me feel safe when we were walking by people on the sidewalk or street. That made me feel feminine, safe, cared for and protected. I realized that his company made me feel so much more comfortable in the crazy Star Wars like bar I visited each weekend.
To me up until now, the simple feel of feminine things and being a gurl was more than enough of a reward for me. Now I had a male friend and my girlfriends at the bar were buzzing about it. I think they thought we were more than just friends because we seemed so compatible and cozy at times.
I had no sexual intentions, nor any willingness to seek more from Jack. He had asked me out to dinner several times, and my friends Robyn, Stephanie, and the Bartender Johnny, thought I was crazy to be so resistant. I resisted strongly, believing that I wasn’t gay or even bisexual. I was attracted to women, though.
The next Friday night, we had a great time talking together. We played pool and I lost to Jack a lot more than I won. Jack plied me with many a drink while we played as he usually did. I loved listening to his jokes and his observations of the very unique patrons at this alternative bar.
I innocently and naively enjoyed Jack’s company. I had accepted him as a friend and protector. That night, feeling brave and tipsy, I even said yes to dancing together a few times. Near closing time, he shocked and surprised me by taking me by the hand for a slow dance.
In all my times at the bar, I never even heard a slow love song playing, less been asked to dance during one. I soon found myself being held closely against him in my teensy mini skirt, silk stockings, and five-inch-high heel pumps. There was something surprisingly comforting but very different happening during our dance.
Jack was well over six feet tall. I felt very tiny and indescribably vulnerable in his arms. I was astonished by the pleasurable feelings from his closeness and touch. There seemed to be a unique warmth in being held against a man while dressed completely as a woman. Feeling his hands on me, separated only by thin silky material, made me shiver!
This had me swooning in confusion, yet I was gradually melting into his arms. As one strong hand grasped my waist tightly, the other hand gently found my bottom. I was breathlessly moved by the intimacy I felt from him. He gently drew me even closer, as I was stunned and shocked by the affection I was feeling.
I suddenly felt erotic flashes from his alluring touch and gentle caresses! I was honestly enjoying being a girl in a man’s arms on the dancefloor. As the music stopped, he kissed me deeply on the lips. I was reeling, stunned, and at the same time mesmerized. The dramatic delight of this intimacy and his tender embrace had me melting yet terrified.
For the first time as a gal, I felt stimulated by the presence and touch of another person. As his kiss became more intimate, I felt his tongue swirling gently into my mouth. I unconsciously reacted naturally by responding in kind. I was being French kissed by a man, and I did not push him away.
I was experiencing emotions and sensations that were astonishingly pleasurable. I must admit that I was staggered by my response. I could not fathom my unexpectedly willing reaction to him. Seconds later when I realized what I had just succumbed to, I scrambled away from him, just as the lights went on -signaling closing time.
Jack found me collecting my coat from the bartender. I was embarrassed and confused. I wanted to run or flee. More than anything, I was very aware that my own male-hood was hard as a rock. Our dance and a bit more had made me stimulated beyond belief! It is hard to walk in a dress and heels when one’s gurl cock is so hard and trying to escape a girl’s panties!
I had never reacted to a man in this way. I was dismayed and very much mystified. Jack could tell that something was not right by the horrified look on my face. He may not have known, but I was completely dumbfounded. I was more than embarrassed by my response and my extremely unexpected physical and emotional reaction to him!
I was moved by all of this, yet my responses had not make any sense in my heart or brain. I relented and allowed Jack - who I had accepted as my protector - to take my hand. He walked me to my car. All during our walk, he was tactfully trying to convince me to go to dinner with him the following week. I was still hard and walked awkwardly in my teensy dress and very high heels. I couldn’t wrap my head around such an idea.
I had never seriously considered going on a date with a man. I was obviously just a pretty, elaborately made up, boy in a sexy dress, makeup, and heels. Tonight had been crazy. I had been kissed by a man. I had felt something far greater than I could have ever imagined. Jack’s persistence in asking me out was overwhelming me.
Jack looked me in the eyes and asked if he could call me on Monday night. In the hope of saying good night with the opportunity to escape, I demurred by saying yes. We had never talked on the phone though I had given him my number if he promised not to call me during the week. I was not comfortable enough with my persona to take a call from a man while dressed as a guy.
Jack then boldly asked me if he could kiss me good night. I felt like I was being pushed but I submissively surrendered by saying yes. I felt so feminine when his tender kiss took me to a place I had never dared even consider. Suddenly I had become a very vulnerable, responsive girl. I was so mesmerized and so moved by the simplicity of his sensual lips on my own red lips, that I was breathless. I was unconsciously allowing him to stimulate and arouse me!
I did not push him away as our tongues once again met. Intense, feline lustful emotions filled my heart and soul. I had no understanding as to why I was reacting like this with a man. I felt passionate surges that were dizzying and intense as his hand drew my bottom against him. I instinctively drew myself closer to him.
Now closely against his pelvis, I felt something huge and hard between us. He was moved like I was and yet, at least momentarily, I was not afraid. The girls at the bar thought he was sexy. I did find him warm and doting, but his kiss was making me crazy. This did not make any sense to me.
My bottom was round and feminine and the feel of this man’s hands on my teensy body-hugging mini dress dizzied me beyond words. His hands and fingers gently caressed my body causing stirring new, erotic feelings that I could not comprehend. Each touch made me yearn for the why in what I was experiencing. His lips, tongue and hold had me helplessly absorbed in an almost forbidden passion. For the first time in my life, I truly felt completely like a woman. I was being held and excited in an intimate and yet captivating embrace, far beyond what I had ever comprehended!
I realized that I was standing on my toes against him in my high heels. I felt amazingly feminine and yet now dizzied beyond words. My soul was aroused and moved by this completely unexpected emotion. I felt simply like a real woman in the arms of a handsome and loving guy. Was this why I was a smooth shaven, perfumed pretty boy-girl?
Once again, I found myself flummoxed and thrown completely out of my element and experience. I pushed back from our locked lips gently. I was both stunned and confused. My flight instinct caused me to finally blurt out a response. “Call me Monday.” I said half breathlessly. I was still quite floored by my actions and willing reactions.
My confusion and need to regroup was in high gear! I needed to escape and to get back to my apartment safely. My mind was spinning from tonight’s events. As I drove home, I was both dazed yet amazed. I drove carefully having drank more alcohol than I should have. I need to regroup and think.
I got home stripped off my dress and heels. I put on a sexy black negligee. I went to bed feeling more like a woman and a female than I had ever felt in my young life. I couldn’t sleep. My mind raced recalling my feelings in his arms and embrace. I couldn’t keep my hands off my smooth, lithe body. His kisses had filled my mind with both wonder and fear. What was I? Was I gay? Was I bisexual? Was I just a girl when in a man’s arms? I was unnerved yet obsessed with tonight’s mind-blowing events.
My hand rubbed my ever-so-stimulated seven-inch cock. In my sheer black negligee, I was smitten about the wonder of being a girl and the eroticism of having being kissed by a man. Feeling haunted and yet sensual beyond my dreams, I shuddered into a powerful orgasm. The idea of being held AND kissed by a man, was perhaps something I had better come to understand sooner, rather than later!
Monday during my Psychology class, I was in a haze. I was still lost in the memory of Saturday night. Knowing that Jack would be calling tonight, was also weighing heavily on my mind. Had I been naïve about myself for all this time as a transvestite? Did I dress and look like an attractive gal for the purpose of attracting men?
Ironically, Psychology class was about the concept of denial, which suddenly had great meaning. Had I been repressing and purposefully rejecting my emotions and feelings? Was I just a whore in waiting as my friend Stephanie would joke? Did all girls like me eventually succumb to a man sexually? Deep down inside, I doubted it—denial—but I knew that I really wasn’t sure at all.
I went home early from class, unable to stay focused. I bathed, shaving my body elegantly smooth, in a luxuriously soapy bubble bath. Just thinking about what it must have looked like to see me standing on my tippy toes with Jack's hands on my waist and bum embracing me in a deep kiss. That must have been an incredulous sight! I was finding my maleness to be responding and expanding as I recalled the scene.
I envisioned myself in my teensy little minidress and stockings, made up to the nines and in a man’s arms. I unexpectedly had outlandish thoughts running wildly through my mind. Did I want more from Jack? Was my behavior simply girlish? Was I ready to dare to find out?
Suddenly I realized how naïve I had really been. Jack most certainly wanted more from me. I had clearly felt his hardness against me when we embraced. I realized that Jack had been pursuing me not just from day one – but for months.
Now it was becoming clearer that my answer tonight to Jack about dinner would be perhaps the most important decision of my young life as Cari! Half asleep in the joy of the warm bath I closed my eyes. My friend Stephany’s words kept coming back to haunt me. She used to joke that I was wasting time just going out to the bars.
“You are the most fuckable girl in the bar, girl,” she would often say! “You need a man to make you a woman - she would joke! Her words now seemed wise and even perceptive. But was I that kind of girl? Denial, according to my Psychology professor, was a very powerful force! My mind kept thinking about the crazy feelings that I felt while in Jack’s arms Saturday night. His warmth and attentions made me feel very feminine indeed. It just felt so good. I was struck by the moment. At the time it had felt even wondrously natural.
I felt I was watching the late-night scene where I was standing on my toes in my high heels while he held my narrow waist and curvy bottom in our embrace. I felt feminine and female beyond words. My soul was touched by feeling like a real woman in the arms of a handsome and loving guy. Was this why I was a smooth shaven, perfumed pretty boy-girl?
I kept convincing myself that I was not some kind of slut or whore like Steph always called the Trans gals in the bar! Part of me was convinced I would say no to Jack when he called about our date tonight. The other part of me was not so sure.
I got out of the tub and toweled off. I was in a sexual state of frenzy just thinking about whether I could have sex with a man. Was I that kind of gurl? Suddenly, Saturday Night, and every night I had gone out as a woman, was making more sense than ever! Jack had made me truly feel like a woman. I liked this man, and I would indeed dare to go out on a date with him! It was just for dinner.
When Jack called, I was sitting purposefully on my couch in my little sheer little pink teddy and high heels. I felt like a naughty minx. I felt comfortable and spoke softly and seductively in my most feminine voice. He asked me if I was alright, apologizing in case he was being too forward Saturday night. I foolishly blurted out that he really knew how to kiss! Jack was thrilled and pleased. “So, you will go to dinner with me?” He asked. I paused, breathlessly afraid, yet knowing down in my heart that I was more than willing to see this man as his date.
“Will you kiss me good night?” I joked. “I would like that very much if it is okay with you, Cari.” He said soothingly. We then talked for almost an hour. I honestly talked about my fears about sex and whether I was that kind of girl! At least I was honest. He assured me that there would be no pressure. The only plan would be dinner and drinks at the club after. Jack was so smooth.
He then spilled a secret to me. The slow dance song that never happened at the club, was the result of a twenty dollar bill he gave to the DJ! My first slow dance with a man was cleverly orchestrated! I laughed, flattered, feeling so stupid and very naive! Jack was a very clever man!
He would pick me up at seven Friday Night. I was excited yet I was a wreck. I knew that I had decided down deep in my soul to find out what I was really made of. Most importantly, I wanted to find the perfect dress. I hoped to be the perfect female date for him on Friday night.
Now I realized that THIS Friday Night, I would be dressing for him! I found this not just new, but incredibly exciting and tantalizing! I went shopping the next day after class downtown. I found a beautiful gold, size three, sequined, body-hugging short dress, that was dreamy. I already had gold five-inch-high heeled pumps to match. This outfit was perfect for an elegant gurl going out on a date. Friday couldn’t come soon enough!
I found myself cutting out of class again early Friday as I was focused only on our date. I so love the preparation before I go out but today was very different. Shaving my body, putting on beautiful fingernails and coloring my toenails were just a few of the details that took a lot of time. I very much luxuriated in the titillating process I so enjoyed.
By six PM, I was more than ready. I reveled in my beautiful gold sequined dress and matching five-inch heels. In the mirror I looked stunning. My long, eyelashes, makeup, earrings and bright red lipstick framed the very sexy face of a stunning young lady. I believed that the young woman reflected was an exotic young girl worthy of having herself on a magazine cover! Jack was who I was dressed up for and I was confident that he would be proud of how I looked. I just knew it.
Ready with an hour to go, I decided to pass the time by trying on some of my favorite lingerie. I removed my dress and set it on the nightstand. I have a half-dozen baby doll nighties, a few long sheer nightgowns and all kinds of combinations of bra, garter belt and stockings. I had purchased corsets, bustiers and more.
I have almost every feminine color in my night things. My sexy evening bedroom wear was always just that. I’d considered them more of a fetish thing because I felt so incredibly and exotically sexy in them. I loved to go to bed in them. I would dream of being the girl that I was every weekend.
Call it irony or naïveté, but my rationale for wearing these wonderful sensual outfits was purely for the joy of the silky, feel on my sleek, feminine body. There is certainly much historical relevance of these sexy silks. Their purposefulness almost always for sexual seduction and pleasures beyond. I wore them because I looked and felt very sexy in them. I did not consciously understand at the time how useful these outfits might be!
I tried on several of my nighties and lingerie outfits. I looked most stunning in my red corset with matching red silk stockings. My bedroom has full length mirrors next to the bed and I was in love with the erotic young red lipped teaser reflected. She looked like a European model. She was truly beautiful with long exotic lashes, stunning lightly shadowed eyes and a wispy, narrow waist.
I switched to an even more suggestive and ultra-feminine nighty. It was a silky, black lace, sheer two-piece bedroom special. The upper lace bralette was transparent and lacy. The bottom was a flimsy, flirtatious, lightly ruffled mini dress like bottom. Beneath it came with only a teensy string bikini bottom. I pulled it on carefully because it was so delicate in the hope it might cover my quite excited maleness!
Suddenly the doorbell rang. I had become so enthralled with the Euro model in the mirror modeling in front of me - that an entire hour had passed without my being aware! Strangely, my panic was muted because I knew Jack would understand. He always did. Using the intercom, I warned him that I wasn’t ready, yet I invited him up and buzzed him up into my apartment.
I opened the door and there he stood all dressed up with a dozen roses in his hand for me! I was moved beyond belief. Still in my most recently modeled sheer black lingerie and heels, I let him in. He looked me up and down wide eyed and smiled. “Oh my God! You are the sexiest thing I have ever seen!”
I wasn’t planning to be seen so undressed! I was so dumbfounded at the obvious nature of my skimpy, skin revealing appearance that I couldn’t speak! I was naive and his seeing me like this was never in the plan. I closed the door behind him as he approached me. No words escaped my mouth as his lips immediately found mine. I instinctively kissed him back. I swooned as I felt his hands warmth on my naked derriere. Things were happening fast. This was not dinner!
I don’t know why, but in some kind of instinctive manner I felt the urge to act like a woman. I slid to my knees, even though this was something that I had never done before. I never even consciously considered taking a man in my mouth and lips - yet I was unzipping his pants! My first girlfriend had pleased me so, a few times, and somehow it seemed right! He was trying to put down my roses while I pulled out his cock and gave it a kiss!
It was huge and already erect. The term huge, however, was an understatement. I licked the head and gently placed my lips around the widest part of his enormous mushroom shaped cock head. Jack just kept repeating his surprise. “Oh my! Oh God,” he kept saying, as I explored the feel and taste of a man’s cock for the very first time in my very young life.
I am honest when I say that before last Saturday Night, I would have never dreamed of doing the things I was doing! The head of his massive and thick nine-inch cock was huge. I too was very stimulated. I went to work on it with both curiosity and enthusiasm. I was learning on the job!
I liked the taste. Even more, I loved to hear Jack’s moans. His cock head and cock were massive, yet I was eager and willing to please! I slurped and slurped and looked up at his pleasure filled face. The huge head of his thick, massive cock barely fit into my mouth. I took as much as I could looking up at him for a reaction like my naughty girlfriend had.
His eyes were closed, and he was moaning. “Oh God, Cari!” he cried repeatedly.
I was thrilled that I was bringing him so much pleasure! Soon Jack needed to beg me to stop so he wouldn’t explode into my no longer virginal lips and throat!
Jack pulled me up. He kissed me deeply and I was a goner. I had already found a natural submissive nature, essentially believing I was female. He carried me to my bed like I was a precious little girl. He skillfully removed my little black lace, string panties and placed me on my back. His kiss was phenomenal! Soon his tongue swirled in my mouth and throat.
He lowered his mouth lifting my lace bralette top easily exposing my soft, flattish breasts. The feel of his tongue and mouth suckling my nipples had me awash in the most feline feelings of my young lifetime. I suddenly realized that this crazy encounter was amazingly erotic and most of all I felt so thoroughly like a girl!
Jack’s girl was moaning in pleasure. She was crazed with passion and lust. Next, he moved lower. On the bottom edge of my bed, he bent back my legs exposing my bottom. Soon I felt something so delightful and stimulating that I thought I would lose my mind. His tongue was swirling at the entrance to my anal opening! I thought I was going to explode in orgasm!
Feeling his tongue in my most personal place was more than just a mind blowing. There is nothing I’ve ever felt that was more erotic and sensual. His tongue probed me, and I sensed that he was readying me for the inconceivable! I was so turned on and electrified that I didn’t care anymore that this man possessed the biggest cock that I had ever seen. If I was a little more confident, I may have even begged for it.
After at least five minutes of incredulous oral attention, Jack came up for air. “May I fuck your beautiful ass, sweet Cari?” he said smoothly. I knew my answer, but I was half scared to death. “Please be gentle!” I whined in need. His work on my bottom and opening had me more than half-convinced.
His entry was very painful. His cock head was almost the size of a fist. I recalled that I had played with cucumbers and all kinds of things in my anus when I was younger. It didn’t correlate with my dressing in my mind. Nothing like Jack’s cock had ever seen my insides, though. It was very fortunate that Jack knew that this was all new to me. He was and would be my cherished first.
Jack was as gentle as a man with a nine-inch cock could be breaking in a virgin! He talked with me, soothing my fears, as each fraction of an inch of his monster moved forward. My appreciation for him soared as his brutally huge cock slowly rocked deeper and deeper into my insides. I felt like I was being skewered by a telephone pole, yet I still wanted him.
I was struggling. I was unaware that I was nervously breathing hard and close to hyperventilating. He wisely stopped, checking in with me to see if I was okay. His sensitive way had a delight that kept me from rejecting the forwardness. Jack’s gentle kisses and assurances soothed the pain that was overwhelming me. Jack skillfully kept me from feelings of panic.
He had me take deep breaths. I was slowly relaxing but there was so much more of him to come. After a few minutes of slow rocking and gentle, but overwhelming fuck strokes, he kissed me deeply. Even though our lovemaking was just beginning, his kiss renewed my enthusiastic want. I felt his huge cock head ram into a place in my depths that suddenly felt like I was being stabbed by a knife. The pain was unbelievable. I cried, shrieking out, tensed, as tears ran down my cheek.
Jack apologized and backed off slightly. Then using some kind of strange twist, his huge cock found its way beyond and even further into my depths. My eyes must have been crossed and my disbelief was at a peak. Gradually though, the pain ebbed, and I found myself responding in a subtle kind of way - to his forward, firm, thrusts.
Now with my lover’s huge cock past what I would learn was my prostate, I was being fucked more firmly. Despite the pain, I was irrationally aroused. During this overtly unnatural skewering of my bum, I found myself tensely holding his ass with both hands encouraging him, rather than holding him back. Jack slowed momentarily, stopping to kiss me deeply once again.
That kiss put me in feline heaven. I was suddenly transformed into a place and existence in which I felt so loved. I was being made love to like a real girl. I could not describe the ecstasy and mind-blowing joy that filled my body and heart. Now that Jack had made me into naughty gal, I loved every thrust, kiss and moment.
The intimacy of the deep kiss and his swirling, searching tongue - coupled with the feel of his monster-like cock searching my depths, was beyond overwhelming. I was smitten and love struck with the intensity. The deep emotions that I felt were blowing my mind. In the deepest places in both my body and soul, I was a girl being intensely loved!
Jack slowly increased the pace of his powerful, deep thrusts. Holding the heels of my high pumps, I think he was as surprised as I that his balls were now slapping against my anal opening and ass cheeks. I think he was as shocked as I that I had taken every inch of his ungodly, over-sized cock.
Now I realized that I was no longer afraid. His fuck strokes were so welcome and so intense. I could never have dreamed of the combination of the pleasure, the pain and the staggering intensity of truly being a woman in a man’s arms. This was far more than a physical act for me!
Gradually, Jack’s pumping and fuck strokes increased in speed and intensity. As we both melted together, his deep, powerful fuck strokes became blur like. All I could do was hold on to his ass with my fingernails dug in. I whined in shrill shrieks and squealed loudly each time his cock found home in my depths.
This sexual coupling was outrageously wondrous. This pain, pleasure, and my overwhelming surrender had literally turned me into a woman. This new consciousness and my reality truly shook my core. My soul was truly female.
Jack was an enormously skilled man. I was so near to orgasm from simply being fucked. His lips again met mine and our tongues intertwined. The intensity of his sudden, rapid, purposefully firm fuck thrusts had me spinning into near madness. Jack’s moans were getting louder and deeper.
The potent vigor of Jack’s physical passion and his deep French kisses were bringing me over the edge. Nothing ever felt more overwhelming or more powerful. I began to see stars and lose myself as I felt heat deep inside me. As his growls and groans became frenetic, I suddenly realized that he was releasing his mating seed into my depths!
I cried out in convulsive wails. I was very aware that I was being bred. Moved beyond any sanity, I found myself orgasming literally from the inside out. Deep inside me the pleasure exploded from the very place his genetic fluids were spewing wildly. My whole body convulsed and shook. We were both orgasming with such intensity that our cries must have sounded like a wildfire.
My shrill shrieks filled the room as his deep grunts and groans mixed with mine. Perhaps it was the emotion of being bred like a man’s wife. Perhaps it was simply the joy of the astonishingly powerful anal orgasm that had me in a state of delight and happiness that I never could conceive of. His mouth again met my lips, and I would never, ever be the same gurl ever again!
My whole body was shaking and quivering from the convulsions and wild delight of my orgasm. I may have even passed out briefly. When I woke, I was being held firmly and kissed on the neck and ear. “Oh Cari, you are so special!” Jack whispered in my ear. Still overwhelmed, all I could do was hold him tight.
Exhausted and confused, he helped me under my bedcovers. He joined me, hugging me from behind, spooning me. His huge cock still felt quite hard against my bottom, and I rubbed my derrière against it. I knew that I wanted to feel it back inside me again. I was now no longer confused about myself. The upcoming events of the evening would clarify just how much I thoroughly enjoyed being a woman in the arms of a man. We never left the bed until morning.
For nine months, I was his girlfriend and his exclusive mistress. Friday and Saturday nights were spent most often in my bedroom rather than out on dates. I joked with him after a month that his promise of a dinner date was fraudulent! He did take me to dinner, finally!
I’d dress up for him in lingerie in the bedroom, only to have him strip me in seconds! Our physical and sexual relationship was stunningly intense and rewarding. I learned quickly what it took to please a man. The first and to me the most important part was learning to please Jack orally. I simply kept working at figuring out how to take every inch of his nine-inch cock into my mouth and throat and three months later I proudly succeeded!
Jack was a married man who eventually claimed to love me more than his wife. I can’t help but think his love for me had mostly to do with my developing cock sucking talents. Too many women are reluctant suckers of cock. My first girl friend told me her mom always told her to keep her husband close – and that meant in her bed! I apparently was succeeding at that better than Jack’s wife. The girls at the bar say no one sucks cock better than a trans gurl!
When a man is married, things can get very complicated. Nine months later, we mutually agreed that we had to sever our intense sexual and emotional relationship. It had to be - yet I wondered if I would ever find a man so physically talented - and who would be able to bring such pleasure to a girl like me. We both knew that breaking up was the right thing for us to do. I will always remember Jack fondly. Jack was my first and he liberated my feminine heart and soul. I was forever changed. Pretty girls so often get what they deserve. Perhaps it was always my fate.
