tagTranssexuals & CrossdressersHappy Endings Ch. 02

Happy Endings Ch. 02


"So Desiree how did you like your first night at Happy Endings Massage Parlor?" queried Judy as daybreak shown through the open doors she was now bolting shut.

Speaking with slight hesitation, I told her that I think I could become accustomed to the lifestyle quite easily.

"You liked being in control of the men I had you pleasure tonight, didn't you Desiree?" Judy said obviously picking up on my hesitate reply.

"Oh yes, very much so, I could not have dreamed of a better night. I so much loved how beautiful you made me and the effect I had on the men you let me please with my mouth. Only I kind of wanted to take at least one of them to the next level and present my virgin boy pussy to him and truly become the woman of my dreams." I explained with hidden fear I may be asking for too much.

"That will come in time my sweetie, I promise. Truth be told, I have some special clients that I know would love your special attributes. Could I talk you into living in my apartment, right here at Happy Endings?" she asked coyly.

I was silent, thinking of the possibilities.

"Follow me hun." Judy commanded, as if I had a choice for she took my hand and I obediently followed.

Opening what appeared to merely a mirrored wall, with a push of a button, I gazed into a suite of femdom. There in the middle was a gorgeous high posted bed with lace canopy. Silk pink sheets beckoned a naked body to succumb to perverted pleasures. Mirrors again were in all the necessary places for vanity, including just above the bed, with the lace parting just enough to see what needed to be seen.

She continued the tour, opening a walk in closet filled with all the feminine wares a girl could ask for. Heels of all colors, none being less than 5 inches in heel height, stood proudly as if trophies upon the shelves. Drawers of lingerie emitting the fragrance of freshly clean pretties were stacked against the walls. Hosiery of all fashions in slots as if in a department store hung ready for some lucky girl's choice. Dresses, angora sweaters, leather minis, and blouses were hung for what seemed like eternity. At the very end was a vanity with all the necessaries to transform a plain-jane boy into a voluptuous woman.

My knees trembled with excitement. My breasts heaved in anticipation.

"It's all yours for the asking, Desiree. Everything you see before you is exactly your size. All you have to do is to forever say yes to all my wishes." declared Judy.

"Yes, yes, most certainly yes" I replied with no hesitation.

I did not even consider what she meant by all her wishes. All I knew is that Dan had died and I, Desiree was now in heaven.

"Good then, you'll find a romantic bath just over there. I think you should draw a bubble bath and relax for a while. We are closed from daylight til 12 midnight, so you have plenty of time to rest and take it all in. I will come for you at 6pm so we can go out for a bite to eat. You should rise at 3 pm every day to prepare for work. What you wear will be your choice but I insist you either wear garters and stockings or crotch less pantyhose. You will find douche bags to use daily on your man-pussy. You are expected to be clean as a whistle back there. I trust you know how to properly clean your man hole." Judy said.

"Yes, I do." I sheepishly replied.

"Finally, here is the medicine you must take three times daily. They are female hormones that will begin to shape your boyish features into the womanly attributes you were obviously meant to be given at birth. You will find your cock will become nothing more than a method to pee with your balls shrinking rapidly into your groin. Pretty soon you will hardly be able to see anything but an elongated clitty where once your manhood arched proudly." Judy went on to say as she handed me hundreds of pink pills in a baggie.

"My girl Tuesday will drop by daily and promptly at 3:30 pm to aid you in your transformation. You are expected to be smooth and soft like a baby behind at all times. As you earn tips from our gentlemen suitors, you will be expected to save them. As talented as you appeared last night, it won't take long to earn enough for your breast and tush implants. "Judy explained.

"Good night sweetie, see you later on." and she left with a lip to lip kiss.

I could not believe my good fortune, from rest stop whore to queen in waiting; my life had turned completely around in the blink of an eye.

As I filled the bath with the most feminine beads of beauty, I eased my once again boyish figure into luxury. My cock stiffened and I could not help to think that this may be one of the last few chances to stroke it to my fantasies. My long hot pink nails caressed it and it grew larger as my mind ran through all the men I'd given blow jobs to just hours before. With the silken beads, I stroked it faster and faster. I felt the head swell.

"What the fuck do you think you are doing, sissy cunt? I heard Judy say as she suddenly appeared hovering over me.

"Pleasing myself and dreaming of cock." I innocently replied, shocked at her seemingly anger.

"Cock dreamer are you? That's perfectly fine but you don't get to please yourself. Only I and the men I present to you get to do that. Do you understand?" Judy barked.

"Yes ma'am. I do. I'm sorry. "I offered.

My cock shriveled in fear and I sunk into the tub, much like a scared little girl.

"I'm not so sure you completely understand my little sissy. You best get out and douche yourself. I will be right back." I was informed.

I was trembling as what was coming next as I filled my backside with warm water, soon finding my stomach ache fiercely and I quickly sat upon the toilet and let out a stream of water so fast it felt as my bum was raw.

"Here, coat it with this as she handed me a tube of KY jelly." she said, as she again abruptly appeared.

I looked up in fear to get the jelly and that's when I saw what I was in for. There upon her well formed hips and naked cunt was strapped the very cock I'd been admiring earlier that night.

It arched out from the most beautiful woman I'd ever seen naked. Her breasts were pert, her waist thin, her brunette hair flowing gently over squared bare shoulders.

"Hurry the fuck up sissy. You are going to get that ass thoroughly fucked." she barked.

I reached around and did as told, coating my soon to become pussy well with the gel.

"Now grab those petite little ankles by dear and brace yourself against this wall for I'm about to give your ass the pounding of your life." she laughing said.

I did as told and soon felt the invasion of cold hard rubber within me. I felt as if I would die in agony as the head broke the barrier of my once male butt hole to my newfound cunt. Once in though I began to enjoy the helpless feeling overcoming my psyche and was surprised to find my once hard male appendage shrink, as if in fear. I could feel a burning inside it yet it would not expand and offer me relief.

As she vigorously fucked me silly, I felt the warmth of semen erupt and coat my legs. I looked at my puny cock and saw I'd indeed had an orgasm yet it remained so small, not at all like it usually did via my stroking with hand.

The fucking slowed and she teased my opening with the well defined head of her cock.

"I see you had your first hands free orgasm, Desiree. Did you enjoy that?" Judy said with a much kinder tone of voice.

"Oh yes, very much so." I replied.

"Good, as you can see your penis now thinks it's a clitty, especially when your ass is filled with a big hard cock. Now lick my tool clean, like a good little sissy cock sucker." she demanded, as I knelt to do just that.

As my mouth bathed her instrument of instruction she continued my lessons by telling me that I would never again touch my penis for pleasure. That any sexual gratification I would ever again experience would be via the acts of being a woman. From this point on, it would be another man's sword or if I were lucky again, her strap on cock giving me the relief of spurting my sissy cum.

I whimpered acknowledgment as she spanked my face with her John Holmes cock.

"Very good sissy, now finish your bath and don't make me come back here again." she said departing the room with genuine laughter.

I re-warmed the bath water and sunk into bliss thinking about my new life. As I removed my makeup, I cried a bit seeing the boy that once was Dan. Nevermore would he be in my life.

After a long soak, I picked out a very luxurious baby pink nightgown and climbed between the silk sheets. Soon, I drifted off to sleep.

The door suddenly opened and I felt the hands of a man grasping me by the head. I looked up and fear flushed my face as I saw him. The very man who'd forced me to suck his nasty cock at the rest stop.

"Like your life now, little sissy boy?" he asked.

"I certainly do for now I will always have access to that sweet tight bottom of yours and I know how much you loved my hooded cock." he said with that devious laugh.

I felt him man-handle me, ripping my gown from my body, while he flipped me over on my stomach, pulling my ass to the edge of the bed. I grasped for anything to escape only to find the silk sheets giving way, preventing any escape. I felt his cock enter my sore puckered asshole and he drove it home, repeatedly, all the while belittling me with monikers such as cock sucking sissy, faggot boy, little wanna-be-cunt. I cried in submission and felt lost from reality. This seemingly went on for hours.

"Dear, what are you sobbing about?" I heard from a man's voice.

I opened my eyes and saw no one but a beautiful woman, standing by the bed in nothing more than a French maid's outfit. Her bosoms overflowed the white lace cups. The tulle skirt barely covered her well formed bottom. I looked around at the bed and the sheets were all intact. My nightgown was intact, still beautifully draped over my body. Although, as I rose, my bottom felt very much fucked. I wiped the tears from my face.

"I don't know, I could have sworn there was a man in here with me. It must have been a bad dream." I told her.

"No, no one here but us sissies, Desiree, I'm sure Judy told you I would be here at 3. My name is Girl Tuesday." said the feminine creature before me in an attempted feminine voice, yet clearly throaty as a man's.

As I rose from the bed, I could not help but to admire her femininity. Her legs went on forever and she pranced so delicately on what appeared to be 6 inch pumps. As she bent over to fetch my pillows strewn upon the floor, I could clearly see what used to be her former manhood. Niblets, which once were balls, were tightly hidden behind a small clittish looking dick.

"Is that how mine will look soon?" I asked of Tuesday.

"What, were you spying my pussy, Desiree?" she said smiling. "Yes, I'm afraid so, in a matter of so little time as two weeks, my once 9 inch prick is nothing more than elongated clit, as yours will be also." Tuesday continued.

"Now follow me sweet Desiree and let me prepare you for the day." she instructed.

I followed like a trained pup on a leash and was taken to another room where she had me lay upon a table and I was soon being coated with hot wax where inch by inch, my entire body was made smooth as a baby's behind. After what seemed like hours, I soon felt a cold instrument invade my newfound pussy and with the onrush of warm water, I knew I was being cleaned thoroughly for future endeavors into my newfound cavity of femdom.

Once the rush of being cleansed was emptied, she took me by the hand, and after taping my cleavage, I was once again laid upon the table where she began pushing my balls inside me along with my shrinking cock. With tape, she deftly secured my manhood to the point where I only had the head of my penis open.

"There, with that tape job, you will certainly have to sit to pee." Tuesday instructed as she led me to the vanity.

I was again in front of the mirrors being pampered with the wares of femininity. Shaping of the brows, this time, was permanent as she plucked them to a most delicate shape. With a whirl of brushes and the fragrances of all things girly filled my nostrils, I became lost in my new reality, that it all seemingly ended before I could notice.

To say the least, I was very pleased with the outcome, even more so than last night as I'd been given eyelash extensions top and lower. My lips were crimson red and full with a sheer glossy coating making them beckons for cock. As I peered into the mirror, my eyes saw a star. One so beautiful, I could surely be material for the classiest of magazines.

"I see you have fallen for the eyes, much as I did." Tuesday said, obviously aware of what transfixed my gaze, batting her own luscious lashes.

"Oh yes, you certainly are talented at makeup. I could be on the covers of Vogue with this face" I declared.

"Vogue perhaps, but since you are here at Happy Ending's it will probably be more like Shemale CockSuckers or Shemales International. " Tuesday said with a giggle.

"How did you come to be here?" I queried.

"Oh, Desiree, we never question how we can to be, only of how we can please now that we have been chosen." Tuesday said firmly as she held out my corset and wrapped me in tight black leather. Cinched tighter than the eve before, my hips became even more prominent, yet I found breathing a bit easier.

"Now, Desiree you may now return to your room and get dressed for work. I will return in an hour or so to do your nails and hair." Tuesday said as she rose leaving me face to face with her former bounty almost at my wet red lips.

"Could I touch it? Will it get hard now? I sheepishly asked.

"What my clitty? Barely, but we must never as Judy does not allow it. We are only to be pleased by men or by her." she said as she turned and left the room, with the reminder I should not forget to take my pills.

Returning to my room, I took my dosage and opened my closet of feminine wares and marveled at my choices.

I was immediately drawn to the angora sweaters and I always dreamed of wearing such softness upon my skin. I picked out a black and white number that had pronounced shoulder pads and a sweetheart key hole that would expose the cleavage Tuesday adeptly gave me. With its turtleneck it would encase me with the softness I'd envied women wearing all my life.

To compliment, I chose a very short black bandage style mini skirt made with an equally soft touch to the finger.

Remembering Judy's request I wear either stockings or crotch less pantyhose, I chose a pair of the later in a sheer black color along with a black lace bra.

Searching the drawers yet unopened, I found a treasure cove of breast forms. All sizes and shapes, some with pronounced nipples, some so delicate they would hardly be noticeable. Then I saw the crème de la crème of forms. At least D cup in size, the areole was very stout with hardened nipple at least a quarter inch tall. Yes, these were mine.

Affixing the hooks of my sheer lace bra, I fitted these boobs to die for in their cups and instantly felt my cock swell inside its taped prison.

Next were the sheer black pantyhose which left the breeze of cold air in the room to freely cool my back end vagina.

As I slipped the angora sweater over my head, I fell in love with the touch of femininity as it encased my neck with its softness while beckoning to the world for my breasts to be touched. I had to wiggle my seemingly larger hips and ass into the soft black bandage mini skirt and marveled at how my tush felt as it freely bounced as I walked to the endless row of heels.

I chose a pair of 5 and half inch fuck me pumps in black leather with the heel partially in white patent leather. They complimented the white diagonal points on the sweater perfectly.

As I strutted back to the makeup table and squirted a bit of Lauren perfume in all the right places, Tuesday entered the room and let out a cat whistle.

"Oh girl, you certainly have good taste. The men will drool over you in that outfit." she said.

As I replied with thanks demurely, she sat me down and unbeknownst to me, shot my earlobe with a needle and announced I was indeed going to be a long term employee for Judy usually reserved the jewelry for those girls who had proven themselves. Once she'd done the other ear, she told me to stick out my tongue where again she put an unsuspecting hole in my body.

As she fitted my tongue with something cold and hard, she did likewise with the holes in my ears and then told me to hold out my hands.

As she did my nails, this time with permanent feminine appendages of two inch dragon lady acrylic nails, I held out my tongue and saw the gold image of a well formed cock and balls. As my tongue folded over it trying to get used to the intrusion, I turned my head and saw in large gold letters the advertisements my lobes now held of what I'd become. On the left, the heavy adornment spelled COCK, the right said SUCKER.

Once my nails were long and curved, painted bright red, Tuesday held out a gold necklace and clasped it around my angora encased neck. Peering in the mirror I saw it read, "Girl Sunday".

It was then I noticed Tuesday had one just alike as a choker on her neck, except hers read "Girl Tuesday".

"So what does all this mean Tuesday?" I queried.

"Ours is not to ask, Desiree. Only to obey." she replied.

"Now for the piece de la resistance to any man that shall lay eyes on you." declared Tuesday as she fitted upon my lace capped head a gorgeous strawberry blonde wig that fell softly over my shoulders at least midway down my back in length with its front folding so sexily inwards tickling my exposed cleavage. Brushed to its fullest, I felt like a blonde bombshell.

As Tuesday was leaving, Judy entered the room and greeted me with a long deep French kiss and told me how beautiful I looked.

"Desiree, you are quite the vision in that outfit. I love the way it hugs your curves. You definitely deserve this." Judy said, as she handed me a small box.

Inside, I found a two very wide gold cuff bracelets, each with a heart shaped ring dangling sexily from them and inside each were two diamond rings. My heart fluttered as she put them on.

"With these Desiree, I declare you worthy of being class "A" property of Happy Endings. Welcome to the girls of the week club." Judy announced just before delving her long tongue down my mouth.

I was lost in lust for Judy as my mind drifted into complete bliss as she caressed me so caringly.

"Now, let's go hit Swinging Richards for a bite to eat and some brief entertainment. I want to show you off to the world." Judy exclaimed as we departed Happy Endings in her car.

As we entered Swinging Richards, I quickly saw how the name included swinging. For as soon as we were seated at a table, a very well built man completely naked man came to ask us what we would be drinking and to inform us Charles would be our server. I could not release my eyes from his extraordinarily long cock.

"I think Desiree would like to drink from that." Judy said with a chuckle, and actually flicking his man hood with her long nail so that it pointed straight at me.

"Well, Madam. That could be arranged for such a beauty as her." the gentleman replied.

I could feel my cock stir again in its prison of tape. My tits were alive with my heart beat as I spoke sexily with my best feminine voice, "Perhaps, after a few martinis, I'd have the nerve. I know I certainly have the desire."

"Yes kind sir, please bring us two martinis, you're very best vodka. We shall contemplate whether or not my new girl Sunday can handle such a fine cock." Judy told him.

"I love my new necklace Judy, but can you tell me what it means?" I asked once I heard her call me by girl Sunday.

"Oh sweet innocent Desiree, if you haven't noticed by now, I have a "girl" for each day of the week. You see I am quite fond of sissy boys and I find them to be much better sluts for the men I cater to than real women. It's a win-win situation for all parties as you girls are quite grateful for the niceties I bestow on you all and there is not a woman alive that craves cocks as much as a pretty little transvestite. You are my seventh girl to join my stables, thus girl Sunday is your moniker." Judy explained with direct honesty.

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