Happy Endings

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Desiree learns the tricks of the trade.
4.9k words
4.56
67.5k
17

Part 1 of the 2 part series

Updated 09/22/2022
Created 10/17/2012
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As I sat in Julie's bedroom, my high school's self appointed sleazy easy slut, whom I'd so long held discreetly in my deviant mind as an idol and often dreamed of having the same reputation; she appeared dumbfounded as if her brain were stuffed with cock. Innocence was always in her mind while with me. Her thoughts of me were nothing more than a boy who likes hanging with the girls. To her, I had no cock. I was just another girlfriend.

She knew little of my hidden desires and anticipations of my 18th birthday that would offer freedom from the closet that captivated my true feminine self.

So close to my coming out and with her being completely oblivious to my desire to her wardrobe, I could not resist the temptation of the thievery rapidly running through my feeble sissy thoughts, as I eyed the class slut's pretty flower print mini-dress that draped her chair. The same dress she'd teased all the boys with, the very one I longed to slip into and become her. I could not help but to see myself draped in her feminine wares.

As was often the case, her phone was busy with horny suitors. She'd left the room, as I hoped, for a phone call and just before she came back, I succumbed to my weakness and managed to securely hide her skimpy flowery mini-dress under my jeans and bid her farewell soon thereafter.

As I made my escape, I could not help to ponder that although male and even with the desire I had for her, I did not want to feel her soft skin, her blonde hair, her vagina upon my penis. I only wanted her dress. I needed to be her. Female, seductive, wanted, desired and deep in my mind, somewhere hidden, fucked with a big long cock.

All week I fondled that soft feminine dress. I could not wait until Saturday, my birthday into adulthood; my long awaited destiny to debut to the world the pretty girl I'd secretly perfected in the closeted dream world of my childhood home.

I would finally be given the freedom to cruise the interstates as my alter ego Desiree, via my very own car. I had accumulated everything a girl could need. Beautiful blonde wig styled just like Farah Fawcett's, the queen of the decade. Heels, hosiery, bra, water balloons for breasts, a min-girdle from Mother's lingerie drawer and now this beautiful cute mini dress once worn by our school's known slut. It was her I secretly hoped to emulate, the easy lay, the girl who went down, the girl who effortlessly teased all the boys. I could not wait for darkness to fall upon my night of coming out.

No sooner than I'd been given the keys, once darkness fell, I was bound for a predestined rest stop nestled way down a lonesome highway, known to be often absent of travelers.

Slipping into the girl's room, I quickly transformed myself from slim petite boy to vivacious woman and strutted back to the car with the confidence of a young beautiful girl of the south.

The anticipated click of my heels on the pavement deafened my ears to all sounds around. The feeling of it all overwhelmed me to the point I had no notice of the world around me. I was lost in femininity. I could feel the flesh of my cock between the cheeks of my bottom as I walked, as it was secured trapped by the girdle's spandex. The smoothness of my shaven legs encased in silk pantyhose, the breeze upon my bum rushing up my short mini dress, my water balloon tits bouncing with each step, all this filled my mind with nothing more than complete womanly thoughts and desires. I felt like Julie.

As I made my way to my car, a man in the shadows suddenly appeared and startled me beyond belief as he came directly to me with an angry look on his face.

I froze in fear, trembling as obvious as a leaf blown by the wind, understandably frightened of being discovered as a mere boy dressed as a girl.

I looked at him and found his eyes transfixed upon mine and as if I were bound in leathers, seemingly unable to budge a muscle, I merely stood there in the darkness, trembling like a spanked schoolgirl.

"Just what do you think you are using the Ladies room, boy." he asked forcefully.

Shaking with fear, I replied. "What?"

"Don't what me, you want me to snip off that prick of yours and stuff it in your mouth? You certainly don't look like you need a dick, at least not your own." he said, never cracking so much as slight grin.

"Please sir, I'm just an innocent transvestite, please, please don't tell on me." I begged, with the thought he might be a security guard for the rest stop.

"Tell on you? Ha, you wish I'd do just that, I bet. Then you'd go to jail and be fucked up that queer ass of yours by all those horny prisoners. I bet you'd really enjoy the big dick brothers in there. They would fuck your sissy ass but well, you fucking fag." he declared.

By this time, I was almost crying. My legs felt like candle sticks melting, about to crumble. I fell to the pavement upon my knees and begged him to let me go.

"Well sissy boy, long as you are down there, why don't you suck on this and I'll me show you what your life in jail will be like." he said, unzipping his trousers and flicking out his long limp hooded cock directly in my face.

I froze just as any virgin girl would. Tears flowed from my eyes upon my lips.

"Go ahead, faggot, use those tear drop lips to suck my cock. I know you want to, you fucking queen. If you don't do it voluntarily, then you will no doubt learn the meaning of being man-fucked, you prissy cock sucker. Might as well learn now sissy boy, because soon as the cops get here, they will be toting you to a place where you will become nothing more than a cum bucket." he threatened.

Trembling, I moved my head closer, as I heard him laugh deviously and continue his verbal threats. I realized I had little choice. I tried to channel Julie. His limp cock arched directly in front of me, he shook it teasingly as he slapped it against my tear marked cheeks. Part of me wanted it badly, the other part wanted to flee as if a scared schoolgirl. I closed my eyes and opened my painted lips.

I could smell the stench of his dick being tucked in his trousers without the benefit of a shower for quite some time. The fear within me was so prominent; it was as if I was without free will when my virgin lips met his flesh capped cock. Even though mindfully reluctant, my painted mouth opened easily as it glided onto his soft cock.

His uncircumcised flesh moved as my pink lips kissed his head. I could taste the jism trapped between the head and the skirt of flesh. The taste I'd never imagined; salty, sticky, and slightly creamy with bits of hardness that tasted like pungent salt. I closed my eyes and tried to imagine myself as a seasoned slut, I begged to be Julie. I was all in now, from innocent virgin to free tranny to the magazine cock sucking sluts I'd stroked my cock to throughout my teens. There I was, a helpless girl all in a blink of an eye and the flick of an uncut nasty cock from a pair of zipped trousers.

His hands grasped the back of my head and forced me further down upon his hardening manhood. Choking and tears to the eyes came as I had no other choice but to open wider and swallow, best I could. His musty cock hairs tickled my nose and he held me there. I could hardly breathe, yet I cast begging eyes to his. I desperately wanted to please him.

"How do you like being a girl now, you fucking sissy cock sucking tranny? Do you like your face buried in my cock hair? Like the smell of man? Do you like the feel of cock clogging the back of your throat? I bet you do, now work it faggot, and make me cum down your throat. If you don't do a good job, I just might have to finish off in your pretty ass, your wannabe cunt." he laughing said.

I succumbed to my predicament and feverishly began sucking his cock up and down its length as his hands had freed me from his grasp. My mouth began to ache, the back of my throat felt raw and I longed for this to be over. While I secretly wished another car would pull in and save me from being fucked in my virgin ass, there was a part of me that wanted to grab my ankles and let my intruder from the darkness split my virgin ass wide open with his ravaging piece of man cock. I wanted to be a woman in all aspects. Cum filled mouth and well worn "pussy" was secretly my desire.

It seemed like I'd been down on him forever, constant up and down motion with my lips and mouth, increased tightness of my lips did nothing to make it end sooner. My mouth became numb from cock. Finally, I tasted sweetness with a bit of salt. I knew from tasting my own cum of what was coming next.

I picked up the tempo, anxiously waiting for this act of perversion to come to a climax. My mind conflicted as to how I felt, was it a dream come true or a nightmare? I just needed his cum to fill my mouth so I knew it was over.

There was no doubt as to what I was in for when I felt his hands push my blonde golden locks to the base of his swollen cock. I felt his manhood pulse rapidly and throb, as if it had its own heartbeat. Soon hot gushing fluid shot out with such force it literally shot a rapid stream of man juice down my throat with the onslaught of more man cream filling my cheeks, as my gagging stopped the flow. I could not help but to swallow my first load of cum, as he filled the air with moans of satisfaction.

I felt his hands upon the back of my head loosen only after he marked my innocent face with the last remaining shots of pearly cum from his pulsating tool of humiliation.

As he released his hold upon my head, I stood up, spit the remaining cum from my mouth and ran to my car as fast as I could. Running with the abandon of any teenage girl, I almost got creamed by an incoming car; my crying eyes and hurry to escape the reality that I was now nothing more than a dirty cocksucking slut had evidently left me blinded with fear.

I turned back and saw the man fleeing into the woods as a very beautiful woman emerged from her car, apologizing profusely for almost hitting me.

I fell into her arms crying, even though, in my mind, a part of me wanted that man back to fulfill my desire to be a real woman with my virginity being taken by a real cock.

Crying uncontrollably, I became lost as to where I was and just sobbed into this woman's shoulder.

My savior attempting to calm me in my hysterical state, stroked my hair profusely, murmuring sweet nothings in my ear, only to find my wig falling into her hands.

Again, I was discovered to be nothing more than a sissy boy in a dress. What a coming out night this had turned out to be.

I cried and begged of her to understand that I just liked dressing as a girl; that I had no desire to please that man.

"Oh, honey. I can see he forced you to suck his cock. You still have cum all over your pretty face." she said gently and then caringly placed my wig back upon my head.

She was very sweet and told me of herself. Her name was Judy and she co-owned a nearby massage parlor. She offered to clean me up and make me presentable again. My hair was a mess from being manhandled. My hose ripped from being on my knees. I felt like a whore and readily accepted her kind offer. It took little persuasion to convince me to follow her to her business.

As we pulled behind a nearby secluded building I'd known and passed by before many times, I saw the red lights blinking, Happy Endings Massage Parlor.

She was soon at my door helping me out and we walked inside.

"I can see you haven't been a girl for long, have you? What is your girl name anyway?" she asked.

"Desiree" I replied along with the question as to how she came to that conclusion.

"Well, your walk for one thing. You walk like a boy. Let me clean you up a bit, see if I can find something in your size and I'll give you some lessons." she said with a smile.

We entered a most pretty room, lavender carpet and mirrored walls; in the corner was a makeup table with all the accouterments. She asked I get out of my tattered hose and then added I might as well get naked, that she would treat me to a makeover of a lifetime.

I did just that and as she removed remnants of cum from my face, she began making small talk with me and asked how I became interested in being a girl.

I told her I'd always loved Mother's lingerie and often pranced around in her spiked heels as a child. I told her of the stern warnings that I must never impregnate a girl before marriage, this during my years of puberty. I confessed Mother's demands led me to the belief that if I wasn't supposed to be a man, then I just might as well be a woman and secretly dressed at home every chance I got.

I told her of how I'd lusted after a well hung black boy in school, after seeing his limp cock in the boy's shower. I spoke of how I'd once slyly mentioned my jealously of his big black cock into a short conversation about girls as we walked alone one day. He realized it was nothing more than a roundabout hint that I would like to be his girlfriend and hit me in the jaw.

"So, then I assume you want to be with men. Did you enjoy sucking that man's cock?" she queried.

Shamefully I replied with a few tears, "Yes, in a way, I did enjoy the feel of my glossed lips caressing it and I suppose I enjoyed being on my knees in such a submissive fashion. I felt very much like a woman although I wasn't prepared to be treated like a slut. I'd envisioned my first encounter with a cock to be much more romantic."

"Ah, there Desiree, not to worry, if you enjoyed it then you are well on your way to becoming a woman that most men desire the most." she cheerfully informed me.

She went on to tell me of the men that frequent her business and that most in fact do tend to like the submissive types, as she began to make up my face. Others she added, like us to be the man, if you get my drift. I have an entire toy section devoted to those types.

I pondered the possibilities as she continued painting my face with strokes of femininity.

"There girl, you look a lot more feminine with a full blown facial makeover, wouldn't you agree?" she asked as I peered into the mirror.

I could not believe the girl in the reflection. My lashes long and sultry curled and black as the ace of spades. Brow arched and darkened, eyelids highlighted in fuchsia and lavender, with eyes framed in bold black eyeliner. Cheeks painted a subtle pink with the hollows darkened giving me that high cheek bone models always sport. My lips were full and outlined with a dark fuchsia lip stick with wet pink gloss making the fullness of them shimmer in the light. My cock was rock hard and pointing skyward without so much of a touch, merely from the reflections of the girl in the mirror.

"Now, now Desiree, you can't be showing off your girly clit. That will indeed spoil all my hard work." Judy said, as she slapped my dick repeatedly.

With fear, it soon retreated as a turtle to his shell and she quickly produced a black silk contraption that fit around cock and balls and pulled them backwards between my fleshy buttocks.

"That's better. Now turn around and let's give you some curves." as she held up the sexiest corset I'd ever seen.

As she pulled the strings tighter and tighter on the gorgeous pink leather corset, my hips swelled and my waist shrunk. So much I felt faint.

She giggled and said, "Not only does that give you an hour glass figure, it should make your voice a bit more feminine, huh?"

I whispered with a hint of femininity, "I guess so because I can hardly breathe."

Next she taped my chest and cleavage was born to my once flat chest. A pretty pink sheer bra held two very realistic D cup silicone breast forms. The hardened nipples protruded proudly beneath the sheerness of the bra.

I could feel my encased male clitty hardened as I peered again into the mirrors presenting the self I'd longed for all my life. I envisioned it being my very own Kotex.

As she handed me a pair of Eva Picone pantyhose, she left the room after spying my shoe size. I opened the package and slid my shaven gams into the most delightfully feeling hose I'd ever worn. Sheer to the waist, with the exception of my delicates being covered with a hint of French lace, they presented my legs and hips in such a girly sexy way.

As I was twirling and admiring my gorgeous legs dropping from pronounced hips, Judy made my heart throb when she came back with a pair of 5 and half inch spiked heels. Mostly black with fuchsia trim, the toes so pointy and daggers for heels, I feel in love with them even more when I noticed the soles were in hot pink leather. I felt immediately like I should be posing for a Fredericks of Hollywood advertisement.

"Those will definitely aid you in your strut Desiree and they fit like a glove, don't they?" she remarked.

I was speechless and even more so when she opened a closet and pulled from it a gorgeous black silk wrap dress with hot pink piping down the edges of the diagonal wrap. Complete with padded shoulders and flowing sleeves, with the same piping in all the right places. It spoke volumes of sultriness.

She opened it and I fell into luxury as once enveloped in its softness and belted in with a classy wide black belt, it left my thighs to be easily seen as I walked. My hips were now pronounced with the cinching of the leather belt. Just above the knees, I felt like a princess as I twirled to the mirror and watched it float sexily, exposing more than any nice girl would dare.

My breasts jiggled and were prominently displayed with nipples pronouncing to the world I was a woman that was to be desired, the cleavage shown convincingly for effect that no man would ever guess the cheeks of my ass held my little sissy dick.

Alas came the crowning glory as Judy entered the room once again with the most long luscious and flowing blonde wig I'd ever seen. Once placed on my head there was no doubt who I was meant to be, Desiree -- The Hot to Trot Transvestite. Its fullness cuddled my now painted face and its long flowing back made me feel incredibly feminine. I could not quit staring at myself, admiring the way it gently flowed upon the fullness of my breasts.

"Men just love blondes with long hair and let us not forget, long nails, I must warn you." added Judy as she sat me down and began adorning my nails with falsies at least two inches long.

"If only that reluctant black boy could see you now, huh Desiree?" she teased further.

As she painted them a daring hot pink fuchsia color, I asked. "How can I ever repay your kindness, Judy? I'll do anything. You've made me so deliriously happy."

"Oh, you will repay me, I have no doubt but first we need to give you a few lessons." and with that she led me to the hallway.

"Let's see your strut and remember with each step you want to pretend that you are seducing a man. Hold your shoulders back and put those tits to work." she instructed as she let go of my hand once she'd led me to the tiled hallway.

The clicks of my heels again clouded my thoughts as I walked down the corridor as if I were on a fashion runway. While I was quite adept at walking in heels from the years of walking in Mother's based upon Judy's critic, I was still walking like a boy, something was not right.

"Watch me, Desiree, watch how each foot is placed in front of the other with each step. See my hips swing, my bottom bounce?" she said, as again my dick hardened at her beauty. Judy was smoking hot with a strut that was out of this world.

"You should feel your hips swing, tush rise and fall with each step and your boobs bounce a bit, your hair with float and bounce off your shoulders. Walk with confidence. Walk like you are every man's dream girl." she followed up.

With a few more practice trips down the now runway of my dreams, I quickly got the idea and was rewarded with a seductive kiss from Judy.

"Oh girlfriend, we are going to have so much fun." she announced.

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