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The Skimpy Red Dress

"A transvestite's alluring dress leads to unexpected consequences."

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There is a very special sensuality in the image of a pretty blonde haired girl who is petite and shapely enough to be able to look great in a tight and skimpy dress. I confess to owning many of these types of sexy dresses. Because I am five foot five inches tall and slim, I am able to look rather alluring while dressed in one.

I have many styles and colors and usually favor black. Once in a while however, I wear a skimpy, bright red dress that speaks volumes. I have to admit that on one special night, it most definitely worked well for me!

When he asked me out I was ready to respond as I always had. No was always my response. Inexplicably for the first time ever, I found myself answering this man with a yes! During dinner a week later, he told me how much his first glimpse of me made him feel that we just had to meet. I liked listening to his insights and descriptions because his often flattering words so often had a way of making me feel special.

He first set eyes on me four weeks ago to the day, when he came into the club. I was standing by the bar while talking to a girlfriend, as he surveyed me from behind. He said that my alluring tight fitting bright red dress, narrow waist, shapely bottom and shoulder length blonde hair immediately caught his attention. He could tell I was young because my body was well proportioned and sleek.  My sensual body was on display in my revealing and shamelessly sexy dress.

He said he was even more wide eyed when he saw my fully exposed stockinged legs. My petite swimmers body and my sexy round derriere contributed to drawing him towards me. He jokingly calls my bum a truly special asset!

He said that the color of the bright red of my dress must have affected him like a stalking animal does when seeing blood! Upon seeing my five inch high red pumps he did hesitate for a moment. He thought I was perhaps too attractive wearing heels so extreme. He paused sharing with me that he feared that I could be a call girl!

I laughed so much when he told me that. I tend to minimize how overtly I dress. He also declared that when he saw my face and my smile everything changed. His words described his love for my bright red lips, elegant looks and what he called my piercing, sensual, very pretty brown eyes. “My long eye lashes and my perfectly made up face radiated.”

My shamelessly tight, bright red spandex dress, barely covered my shapely derriere. The dress was so short that my smooth legs and thighs were so exposed that my little red panties were barely covered. The thin, spaghetti strapped top, of my skin tight dress, plunged deeply, exposing the upper edges of my smallish breasts.

I felt great in my dress because I knew how it drew more than glances. A girl can literally feel the staring and gawking of men! I was a temptress and a teaser, but I was definitely not a pleaser.

Though I was perhaps overly alluring, he told me he saw an innocence and a subtle sensuality in my eyes. He claims he never saw a sexier young lady in his life. Some girls often love a flatterer. The thrill for a pretty and unique girl such as me to hear such inspiring compliments made my heart flutter! I was a bit of a sucker for flattery and male adulation.

He had succeeded in gaining my interest. Few if any guys had ever succeeded in the past. He was a very good looking. He was also a smooth talker who seemed to always know what to say. He was a quite likeable guy and his presence allowed me to feel a comfort that was very unusual for me with men. I was so often approached but put off by men. My developing attraction to him was novel and quite new.

That night he generously bought me drink after drink. We even danced several times together, something that I rarely did with a guy. I had only danced once before with a man and that was on a dare. This guy made me laugh and feel special. Very few guys seemed to be as nice and as down to earth as he was.

Though he was twice my size and more than twice my age, I was drawn to his warmth. There was something that I found to be very different about him. He was friendly, and was a very articulate talker. He was confident in himself, but I like that he joked about his imperfections. He was quite masculine and attractive. I also simply found him to be very kind, polite, and considerate.

He loved my perfume and yet it was I who was dizzied by the smell of his cologne. He was very well dressed and had such a surprisingly elegant manner about himself. I actually swooned a little when he daringly touched my smooth stockinged legs. Men in the past usually got a slap or a firm push when that occurred! He then came close, looked me in the eye and I melted like ice in summer.

I was mysteriously drawn to him and there was a doubtful pause. Suddenly I felt his lips meet mine. I was so moved and so breathless. A strange passion was suddenly unlocked inside me and my heart fluttered.

I was confused, yet smitten. My feelings and emotions had me stunned, yet I was infatuated. This was another first. I was baffled that I was being drawn to him. Prior to tonight I had never even dared dream that such a thing could happen to me.

Suddenly I was so aware of my lithe, smooth shaven body and my feminine self. He drew my flat stomach against him and held my teensy waist. In my very high heels and feeling almost naked in my skimpy dress, I was feeling female and feline beyond any time in my life. His closeness and presence made me happy and my insides were electrified.

When this man hugged me, I felt beyond special. I felt his strength and I felt incredibly soft and lady like while in his arms. He told me that he thought that I was very hot and quite beautiful. I was finding myself dumbfounded and stirred by how both the combination of his touch and his words made me feel.

I was quite confused. I had been going out to clubs as an underage gal for a year. Having just turned eighteen, I had been pursued by perhaps hundreds of different guys over that time. None had ever really peaked any interest. My love for teensy tight fitting dresses and seductive clothes often drew men to me like flies but I was always known just as a tease.

Never once did I give in to their wants because I wasn’t even sure as to whether I even liked guys. So many of the men I met were rude and forward. It made any kind of trust and any kind of comfort in the company of most men quite difficult for me at times. Subliminally I enjoyed being hunted, but I obviously had never allowed myself to be caught!

What I did know was that up until now - I loved being chased and flattered by quality men. I was hung up on many things – especially when it came to even just the thought about having a physical relationship with a man. He also asked me the big question - though I am sure he knew – if I was a real girl. I was being sweet talked and yet he was obviously thrilled when I replied – “I’m really all guy under this dress.”

This man now knew my biggest secret. I was not your average girl with the seven and one half inches of male-hood that I possessed. I was a college boy who just loved the hobby of dressing as a girl. He told me there was no one sexier and prettier and more gifted, that he had ever met. I was falling for this guy like my brain had been re-wired!

Suddenly I had naively succumbed to the concept of having a not just an admirer, but more. Just the idea of having a boyfriend was so shocking and unexpected for me. Feelings and emotions welled inside me and my instincts allowed me to make just a little sense out of it. Girls were supposed to have boyfriends, I mused. I rationalized that it was normal for a pretty woman to be attracted to a handsome guy.

He would take me to dinner the very next week. I was suddenly quite smitten by the idea of our budding physical closeness and his presence made me feel vulnerable and even weak. I began for the first time to realize that I might give in to these new feelings. These new and powerful emotions were drawing me to him.

Feeling this attraction for a man had me reeling in feminine delight. Would I succumb and surrender? Was my being feminine my reason and perhaps excuse to do so? I was dealing with guilt and rationalizations, but everything about him just seemed to feel good. I would give in to finding out if I was right or wrong, to explore these powerful, yet confusing desires.

Four weeks later to the day, my life as a “girl” who had a beau had come a long way. We were suddenly more than just friends. The attractions and actions were fully playing out. My whole understanding of who I was had changed a full one hundred and eighty degrees!

Now I found myself in the privacy of his bedroom. My role as a woman has completely changed. Dressed in but a sheer little black bra, transparent black bikini briefs, black silk stockings and black high heels, I was in “uniform” for him.

We were now intimate and lovers. I was all in. My role was that of his mistress. I was seductively dressed for him. I had already surrendered to him. My behaviors were purely feminine and were guided by what he had wanted.

I was kneeling and in what he calls the position of wait. I had my hands behind my back as though they were tied. My head was down submissively until he would approach me. I had fully accepted this completely new role and purpose. I had become very talented in pleasing him in a very short time. This was about to be just a small part of our new dance ritual, so different from the dancing we did on the night we first met!

I had learned quickly about how men and women made love. I had very willingly engaged in very “intimate acts” with him. I was smitten by the joyous emotions and physical joy of coupling with a man. I had also engaged in some of these sensual, sexual acts enough times in the past month with him, so that I had become somewhat confident in my abilities.

As he approached my excitement surged. I now so loved the opportunity to please a man. He was close now and fully naked. I knew that he lusted in making me wait. I could see his already hard, huge, pre-cum dripping erection. He was excited to see me as the girls would say!

I was anxious, aroused and intensely stimulated while somehow trying to be patient. He took my chin. I looked up at him with a still somewhat innocent smile and he told me what to do. His words were direct and rather naughty. I did my best to tease him with my tongue, but I also selfishly wanted to taste him right away.

My senses had so expanded in my new role as his girl. I now adored even the smell of his pre-cum and his organ. I treasured the taste. I so enjoyed the sensation of taking his huge spectacular manhood into my lips and then further into my mouth and throat.

I cherished looking up at him and winking seductively with his hard cock in my mouth. There was such joy in seeing his pleasured face. Even better was hearing the lusty moans and groans elicited by my efforts! I was smiling, but you could only see it in my eyes!

I adored sucking and even worshipping his huge, ridiculously large, mushroom headed eight inch cock. He had led me to become his girl and his lover. He was teaching me his dominant ways and I had surrendered to him with a willingness that was mesmerizing. Being submissive for me now in my mind, was just what a good girl should do. Pleasing a man, was what I so enjoyed and so wanted to do.

As I worked is cock into my mouth the proof of my own pleasure and delight could be seen in my wet, stretching, sheer black silk panties. Bulging inside of them was my own erection. It was so hard and spewing so much pre-cum that the crotch area was already soaked. The deeper I took him into my mouth and throat the more his moans made me more eager and more enthused. I couldn’t get enough.

I had learned to take every inch of his thick eight inches a week before. Now I was thrilled to know I was a quite capable lover. My improved technique and my zealous enthusiasm brought him even greater joy. I worked him relentlessly until I felt the base of his hard penis at my lips. Then I thrilled feeling his enormous balls at my chin. This accomplishment excited me so much that it almost brought me to orgasm.

There is a certain amount of duress in performing this act. I have learned out of necessity to deal with the challenge. A girl who wants to please a man has much to learn. Oral sex with a man so marvelously gifted, is not an easy task at first. His huge cockhead hurts my throat at times and my need to control my gag reflex is sometimes a constant struggle.

I labor greatly to breathe through my nose. My capitulation to having both of powerful his hands controlling my head is against all instincts, especially while keeping my hands dutifully behind my back. Each hard thrust challenges my every breath. Keeping myself steady on my knees while being deep throated, takes almost a gymnast’s skill, balance and perseverance.

The task of deep throating my man is a test that keeps me at complete attention. I’d switched to Revlon Colorstay Lipstick for obvious reasons, but I still could see a muted red tinge from it all along his beautiful shaft. I lust in tasting and feeling his cock in my mouth and throat. At times I worry about how perverse I might be! Red lipstick on my lover’s balls clearly displayed that I was a very, very good girl!

The additional struggles of sucking the huge cock of such a well-endowed man certainly includes the important orgasmic part. As much as I thrill to the feel of his ejaculation in my mouth and throat, it is the point at which I need most to be aware and on my toes – though I’m on my knees! It is my intent to swallow all of his seed so there is nothing wasted. I’m naughty, a good girl, I’m his slut and I so enjoy the taste!

The overwhelming task of gulping stream after stream of his wildly spurting cum is enough to drown a person if they are not careful. I’m still learning, but I can modestly boast that I recently accomplished the feat of every drop swallowed.

I do love the lusty feel of his invading cock into the depths of my throat and gullet. It’s naughty, nasty and so overwhelming to be so thoroughly used for his pleasure. Ironically, I so covet the fact and the reality, that I am his and for him to use for his personal pleasure.

Accomplishing these deeds just makes me proud to be such a capable and willing and in his words - “slut for him!” He has told me what a fast learner I am and his words fuel my successes. This time I won’t need to swallow his swimmers because he has much more in mind for his girl. I am usually treated to the joy of having him staving off his ejaculation so that we can more formally mate.

Being made love to as his woman has a power that is difficult to describe. It has become what I need and want as the person who is his and his lover. Now I find that just the idea of having his cock in my bottom makes me crazy. The act has quickly become my idealized function. To me, having him inside me there is what I feel is my perfect role with him.

I am all girl in my brain when I am in his strong arms.

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When I feel the wonder of being bred and being filled with shot after shot of his genetic fluids deep inside my bottom, I feel like a true and genuine woman. Breeding, is a word that makes me yearn and thirst for him. Being bred, fully transforms me from being just a pretty transvestite, into an actual woman in both my heart and in my soul!

Feeling his heat fill my depths sets me off like a crazy person. I almost always have to monitor myself from losing all sense of control! That is why I so enjoy the next and idealized part of our dance of pleasure.

He lifts me from my knees and kisses me deeply making me breathless and thrilled. He literally lifts his little flat chested girl from the floor and gently placing me onto my back on the bed. The anticipation and excitement of what I know might be next, already has me lathered and crazed in lust. I know he is going to fuck me but first he has a little treat and some careful preparations for his young, pretty, little girl.

I’m always well prepared for him as well. I have shaven every inch of my body smoothly for him. I am silky and sleek, and as hairless as a “girl” can be. I bathe and use numerous skin softeners leaving me gloriously feminine to the touch. My perfume is exotic and French. My body is something I am proud of and it pleases my lover greatly. My smooth, lithe, perfumed body, and my softened heart, belong entirely to him.

He purposefully lifts my ankles and spreads my legs. Bent helplessly backwards, back my anus is fully exposed and available to him. To my great delight he ignores my hard dripping cock. I’ll orgasm if he does that to me. Immediately his mouth and lips find my anal opening. His purpose is to wet me and to lubricate me. He does this so that his huge, long, thick male member can invade me with much less struggle.

In the process I am moved and enjoying the sensations beyond belief. I can’t explain just how personal, how exciting and how pleasurable it is to feel his tongue swirling at my anus. The exquisite feel and nature of his probing licks devour my woman’s place. I’m already frazzled. This is so stimulating to me that I am already hyperventilating!

The first time he ever did this to me I was so moved that I lost it and orgasmed! He was totally amused when my pulsing, stimulated cock unexpectedly went off in spurt after spurt. I squealed in disbelief as I exploded with his tongue probing the insides of my sphincter! I must admit I was embarrassed by my total lack of physical and mental control.

I have been since been taught to have much more patience and discipline! My goal is to be the perfect lover for him and it is because of my true respect and genuine appreciation for him. He has both physical gifts and lovemaking skills that any woman would truly lust for. I feel lucky, fortunate and thrilled to be the object of this man’s affections!

As Jack works my anus with his skillful mouth and tongue I struggle mightily. The delight is so overly stimulating that I have to breathe deeply, while carefully biting on my lip. The frazzling pleasure I’m experiencing is immense.

Knowing this, he will often choose to stop and pause to spank my exposed bottom. The stings remind me of my role and place. To orgasm now would be selfish and I’m not that kind of girl! I am a naughty girl after all and a good spanking is almost always well deserved.

His talented tongue makes me frantic and I fight the urge to explode. I learned on our first night in our relationship, that I am one of those somewhat unique girls who can have true anal orgasms. Both his oral attentions to my anus and deep anal penetration can set me off like a rocket ship. I suppose I am lucky but it also makes me behave like a true slut and whore because of how stimulated I get from his skilled love making. I think I am enamored with more than just Jack’s cock!

Suddenly he spins me and I find myself ass up and bent over his knee on the bed. It is time for me to get a spanking. Jack is a dominant guy and I have learned how wonderful it is to be the true submissive to him. He loves to redden my bottom and my like for feeling his powerful hand sting me there often astounds me. It also has an even greater effect on me.

I guess I am a natural sub and he is a natural and true dominant. This all makes sense to him but now it does to me as well. I find that my frequent disciplinary spankings feed many of each of our needs. Jack loves to teach me and guide me into greater self-control. The spanking reminds me of my place and my role. How could I ever forget?

I so greatly appreciate the guidance and the emotional joy that submission and surrender brings to me. Sometimes Jack will have me watch myself be spanked in the mirror and I find it incredibly stimulating to witness the reddening of my sexy bottom! There is a blissful rapture for me in the stings, resulting in a warmth that I feel both on my bum and for him!

I count every individual spank and thank him for each with genuine sincerity. In spite of what is sometimes shockingly painful and stinging pain to my ass cheeks, I remain disciplined in my counting. I am grateful for my lessons and for unexplained and mysterious reasons, each whack kindles arousals in me that most definitely fuel my enthusiasm.

The heat on my bottom is wondrous. I glow in the excitement, electricity and lust the stings cause. Each affects my willingness to surrender in full. It shapes both my softening state of mind and my own hard, straining, dripping and overly stimulated cock.

As a dominant and controlling man Jack never seems to give away his next want or desire. He enjoys keeping me on my toes and I listen and react as quickly as I am able. When his command comes, “On your hands and knees!” I quickly turn myself and in seconds I am in position, raising my nude bottom in wait in the manner that I have been taught.

I am obedient, responsive and very willing to please him in every manner that I can! This man is a wonderful teacher. Daddy’s lessons have always been well received by his very well-behaved little girl! Now with both a red hot bottom, and a very wet well licked and well probed anus, I’m in a frothing state of need and readiness. I feel so inflamed and in want.

He teases me by using his probing finger to tease and torment me.  I am needy and frustrated and he knows it. This is just another lesson in discipline and personal self-control. I can’t beg him. I must show both control and my understanding of my place.

Finally I am asked about what I need from my lover. My words are humiliatingly frank and honest and I am too embarrassed to repeat them! I state my wants and needs to him and blush at my honesty and shameful words. They will be our secret!

My Daddy is more than ready to assert his dominance over me. He knows exactly what his submissive needs and he will make absolutely sure that his willing pretty willing – sub, with a dripping, pulsing, erection, will get everything that she deserves!

With my ass raised while in the doggy position I quiver in anticipation. I am in both fear and a state of wishful anticipation. He is just so huge. I don’t know if my anus will ever stretch out fully for him. I try to think that each time it gets easier. That is how he wants me to think. I do believe him.

His entry hurts and I let out a yelp. In spite of my well lubricated opening, this is a very difficult task. He is just so big that the initial thrusts really cause me some serious duress. I breathe out as an athlete does hoping to relax myself so that he can fill me more fully. I tell myself repeatedly that the pain will lead to pleasure. I know that it will but it doesn’t help these first knife like jabs that my body, anus and sphincter are struggling with.

The beginning of our coupling is always somewhat difficult due to his enormous size. His huge mushroom shaped cockhead is like that of a Greek god. He does not have to be patient because he is the one in charge. I will accept the initial pain and the duress. I need him at least as much as he needs me.

It is his need and his pleasure that is important to me. I am a natural submissive. I know how much pleasing him it will please me in the end. (No pun intended!) I want him so badly that in spite of the pain, I help by attempting to meet each thrust with my needy, up raised bottom.

I wail in genuine pain during those first, sharp, thrusts. I am tense and my anus is unyielding. After more hard strokes the agonizing throbbing aches begin to become more tolerable and a little more diffuse. Taking a cock that is so thick and huge, capped by a truly oversized mushroom shaped head - is a true challenge. Daddy is telling me what a sexy ass I have and how much it deserves his cock. “Yes,” I wail out desperately. “Yes! Oh yes Daddy”

He tells me via a litany of naughty words just how naughty I am and how much I deserve a good fucking. He is so right and in the throes of love making, I love being told these things in his sometimes quite profane words - what a real slut that I have become. A girl should never have a problem with the truth and in my state of need I most surely don’t!

Soon my Daddy is firing his massive hard cock deeply into my ass and bowels. I relax just a little, when his balls and pelvis reach my ass. The spanking like sounds of each thrust finding my backside are filling the room echoing from the walls. He is so far inside me that I feel fully skewered and completely overwhelmed yet now I am feeling better and my spirits are surging.

Daddy is reaming my ass so thoroughly that the hurting thrusts are now beginning gratify me. I’ve learned that pleasure mixed with pain can be intoxicating.  His desire and skill causes a thrilling and joyous sensation that rivals anything I have known.

I am happy, elated and delighted while cooperating with each thrust. I manage to meet each of his furious fuck strokes as I unconsciously yet instinctively raise my ass, to meet each, powerful, colliding, lunge and stroke. My hard cock is bouncing like an out of control spring. It almost hurts as it is so hard.

There is a dull pain developing in my depths as I realize that my prostate is now being pounded. My good fortune finds my lover re-positioning me so his cock goes deeper, and even further. In what seems impossible he thrusts around and beyond it. His skill is marvelous and my own desperate cries and words make my appreciation for his skill absolutely clear to him.

I am reminded again of my maleness as I feel my ragingly hard boner is bouncing against my pelvis as I absorb each of Daddy’s commandingly potent thrusts. I still feel so female in spite. When Daddy entered me and took my virginity a month ago I was forever changed. For me being fucked is almost spiritual. Each stroke and thrust I feel in my depths is satiating and soothing, in spite of my being so overcome.

Daddy’s rapid fire fuck strokes are incessant and even angry. I am overjoyed because only a true submissive can be so fully appreciative of such fervent talent and ability. I am holding on for dear life in fear of my own early orgasm, biting my lip and hoping my lover is near. My desperate cries extolling my Daddy make it clear where I am.

I am nearing both physical and emotional madness! My Daddy has me so in need! Suddenly Daddy’s thrusts become frantic. He grabs my waist and begins to drive his member incessantly into my depths. In what is a constant blur of rapid fuck strokes I cannot believe the power, speed and competence of his talents. He cries out “Oh yes baby!” and suddenly my world has hope in finding a semblance of control.

I will now be allowed to orgasm. I’m beyond joy as now Daddy is filling me with spurt after spurt of his

streams of cum. He gushes hot jet after jet into my deepest place as I lust in the unmistakable feel of each hot spasm. I am being bred and nothing I know moves me more!

I cannot help what happens. I see stars as the swelling explosion begins. I go off into a wild, quaking, body shaking orgasm that begins in my depths near his swimmers. The joyous heat sends shock waves from my head to my toe. Anal orgasm is incredulous and this man makes my vulnerable body and mind explode into helpless pleasure waves that have me breathless, reeling and satiated beyond what I can even believe!

As each and every spurt of his genetic fluids shoots into me, I seem to react even more greatly. I continue to experience orgasming quakes and tremors. The quivering spasms are like intense electric shocks of pleasure. The lightning like waves leave me in awe and disbelief. My Daddy has taken me from physical joy to a land of emotional and spiritual wonder!

We collapse together on the bed as he kisses me on the neck. He turns me as we then kiss face to face. His tongue searches my willing mouth and we hug intensely. I know that I have never felt more wanted, needed and satiated and he smiles and asks if I’m ready to give him more joy. The wide smile on my face will give my answer away!

The night is young and my response is more than predicable. “Of course I am ready Daddy! I wouldn’t miss it for the world!” I say smiling, and looking right into his handsome, warm, brown eyes. I am hooked and in his web and grasp.

I am like the prey of a spider being so helpless. There is such fate in the joy that I experience with this man. Later I’ll be in his handcuffs and I don’t and won’t care about the location of the keys!

Forty eight hours later I’ll be showered, freshened, made up nicely and ready to go home. I’ll wear red high heels, black stockings and the sheer black bra in which I began my Friday night with Daddy. Daddy’s a bit of a romantic. When I get my final kiss and final spank on my bottom, I’ll walk seductively back to my car for him while wearing only that same wonderful skimpy red dress that he says he will always remember me for.

I drive back to my apartment. I need to get some sleep and be ready for my morning classes. Still enamored with my felinity, I decide not to shower or go back to being a guy until the morning. I sleep in a sheer baby doll nighty without the panties.

As I dream I feel my lovers breeding fluids leaking from my bottom, I can’t keep my hand of my male hood. One last orgasm ends another weekend in which I have lost count. I dream about the weekend all night long.

Next Friday night won’t come soon enough. I’ll be even more thrilled and excited when I knock on his door. I’ll be wearing something sexy and skimpy for him. I will wear whatever he should request. I’ll be prompt and on time and when I enter his door, I’ll tell him that I am once again ready to be his.

Daddy’s kiss and the intensely wondrous feeling of his hands on my bottom, will send waves of delight right through me. My surrender will be complete and I will please him again and again. Girls know that there is nothing more alluring than the perfect dress. I hope my skimpy red dress will last me a very long time. I'm fine with the fact that I don't get to wear it much anymore!

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Written by carichristi
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