Book I – Awakening dealt with a 48 hour period where our heroine realizes and actuates her sissy-self – it is a coming of age story. Book II covers the remaining eight days of Dani's vacation and her kinky little band's further exploits. Although each Book is meant to stand on its own as complete, the reader is urged to first read Book I.

This chapter is rated XXX, and deservedly so, as there is graphic sex as this sissy explores her most slutty side. Please be of appropriate age or be gone!

 

Dani's Story

Book II – First Days

Chapter I – The Third Evening

by sissystevie

 

I stood in perfect sissy deportment to one side of the large solid cypress door awaiting my Master, my locked satin covered collar attached to a chain and padlock extending from the wall. In my hands just, below my exposed titties, was a small silver tray with a chilled martini resting in some form of chilling device. I would be the first thing he saw as he opened the door.

"Thing," I thought to myself. "Was I now a thing? What an interesting concept."

I had come so very far in such a very short period of time – only two days! It really took but a few well directed pushes from my mother and her so willing accomplices to covert me from closeted lingerie wearing sissy to the frilly and frankly slutty maid standing in this elegant foyer.

Here I was, completely feminized – my longish blond hair colored and curled into a French twist perfectly atop my head, hairless from my well plucked eyebrows down, newly pierced ears with cute tiny gold hearts dangling down from the studs, slutty very heavy makeup over some form of long lasting coloring on my lips, eyes and cheeks, pierced ears, painted nails, perfumed, and wearing an outfit more designed to reveal and expose rather than conceal my most private of parts.

My revealing little – very little – outfit started with a white bridal satin bustier that not only so tightly laced my waist that breathing, itself, was a concern, but also shaped and formed my little sissy titties into delicious A-sized mounds. Bizarre nipple and whole breast suction together with electro-stimulation devices had been used to further the effect. The bustier was finished with eight suspenders ending in silver metal clasps covered with satin ribbons attached to my seamed white lace stockings.

A large frilly white garter adored my left leg and a thick gold and pearl anklet with a little dangling heart sat on my right leg. I also wore a matching necklace with another gold heart draped between my burgeoning boobies.

A matching, in so many ways, pair of panties performed much the same function – satin and lace surrounding, but neither concealing my little clitty, nor my now non-virginal sissy pussy. My clitty was further displayed in a little "garment" known as a peenie petal – a tiny doll-sized white satin skirt trimmed with petal-like frills and lace that settled its little doll-sized 'waist' at the base of my peenie and pink purse. A satin ribbon drawn tight and tied off with a pretty broad sissy bow secured it in place. The final touch was a silver bell, which rang out with my every movement, hanging down from another white satin ribbon tied off just below my clitty head!

My dress was made from black taffeta with white satin ruffled trim. It had very high puffy short sleeves finished in white satin bows and a bodice that went beneath my small budding titties, completely and provocatively fully exposing them. A small white bib apron made from organza and satin with an impossible huge bow in back was tightly tied about my corset-slim waist. An outfit that prominently displaying precisely what a normal outfit was meant to cover! Long fingerless lace gloves with necklace-matching pearl and gold bracelets with heart charms finished the outfit.

The very short skirt stood out nearly perpendicularly from my waist as it rested on the froth of white petticoats – far too short to cover anything a skirt should cover: clitty, garters, stocking tops were all exposed. My open panties with my clitty flower and bow-topped white satin ribbon holding my a little silver sissy bell were clearly visible.

My lips and nails were scarlet red and my makeup overdone in a tarty French maid's manner. Blue frosted eye shadow matched my crystal clean blue eyes. The black liner and mascara was thicker than I had ever worn.

A white high maid's bonnet with draping satin ribbons, white lace open fingered gloves, white chiffon and satin apron with a huge bow in back and black five inch stiletto satin heels with matching toe bows finished off my uniform. I had never felt quite so exposed, nor quite so openly slutty. It excited me profoundly!

Despite a very recent and very active romp with my new sissy love, the divine maid Millicent, my be-frilled clitty leaped to attention as I heard Master's Mercedes roadster come to a halt in the driveway. My breathing deepened and my heart accelerated. Every part of me felt so open, so vulnerable and yet so utterly sexually charged! My nipples were as hard as diamonds and as tingly as my clitty! My bosom was thrust out pointing my titties towards where He, my perfect Alpha Male Master, would appear.

I heard first and then saw the knob turn, and then: panic! I had to remember my maidly decorum. I had to execute a perfect curtsey whilst holding his chilled stem glass and chained to the wall! And, without spilling a drop – let alone losing my balance in these impossibly high heels. The phase "Less is more" came back to me. I steadied myself much as I was required to the night before when I was presented as the debutant sissy as the door opened.

My eyes dropped to his groin in dutiful submission and I began my little sissy bob. The only way I was going to execute this little maneuver was to concentrate on the curtsey and my tray, and only those two things. If I fully looked at Sir John I simply would be consumed by other girlish thoughts.

He entered. I went into my dip, completely unaware of how holding the tray so prominently displayed my tiny budding boobies. As I came up, thankfully with the drink fully in tact, I smiled and said, "Good evening, Master. May I offer you a drink?"

Again erect and as stable as one can be in such an arrangement, I watched with great pleasure – and more than a little relief – as he took his drink and said, "Thank you, Sissy. You look particularly fetching this evening. I look forward to your service."

With that he produced a key from a table a few feet from me and unlocked the chain attached to my collar. "Go, see Cook and bring me some hors d'oeuvres. As you must have been told, I will be in the library."

I said, "Yes, Master," has I gave him another curtsey and proceeded to mince off towards the kitchen where Maria and Cook awaited, savoring the sweet swishy rustle of my frilly taffeta petticoats as I went.

There were two women in the kitchen. Maria was Master's principal housekeeper and my sissy mentor. Although appearing quite stern in her tailored satin blouses and tight below-the-knee skirts, I had grown quite fond of this stately lady and her younger assistant, Anna. Cook was just that, the cook, and also a delight. She was an older black woman full of good humor and, like all the women here, underlying strength.

"Ah, the maid returns intact!" marveled a smiling Maria.

"Yes, she seems to have not spilled the drink," replied Cook. "The hors d'oeuvres are on the table there, Sissy. Pick them up and show Maria how you will serve them."

As I practiced serving Maria corrected my posture so that when I bent over to offer the canapιs my exposed titties and rear would be prominently displayed. "Much better, Sissy, off you go and mind your deportment – curtsey coming and going; eyes to his manly parts."

I entered the library to find Master at his desk.

What a beautiful man he was. Even his name, Sir John Strong, evoked power, which he certainly had. Just this one house located high atop sea bluffs in an old Spanish section of Puerto Rico was massive. The night before more than a dozen people slept here. I knew of at least one other of his houses, a chateau in the south of France.

Mummy and my stepfather had taken me here for my spring break from boarding school. On our first night down here, my mother had first tricked me into wearing far too tight trousers and then confronted me with my long history of secretly wearing – and soiling – her lingerie. That was the beginning of many revelations over the ensuing two days.

Mummy had always known that I was simply a sissy, but had promised my late father to wait until I turned eighteen to act upon it. I turned eighteen only one week ago and here I was! Not only a sissy, but a wantonly slutty one about to serve my new Master!

After confronting me, she shamed me into an even more bizarre sissy boy outfit and whisked me out for dinner where I first met Sir John. I was immediately overcome by his Alpha Male attraction. By the end of the night I had quite willingly succumbed to all my girlie desires and his manly needs. By the end of the night I had wantonly flaunted my sissy-self and could quite honestly be called a cocksucker.

During the second twelve hours I had been made over to look completely girlie, dressed in the sexiest of lingerie, again publicly paraded through a restaurant in an even more extreme sissy silk blouse and shorts outfit, accepted to remain as a sissy for the balance of our stay in Puerto Rico, and had given Master his second blow job in the back seat of his Rolls – right in front of my mother!

The third twelve hours saw me have my sissy debut at a gala party and quite thoroughly deflowered by Master. And during the last twelve hours I had sucked Master's cock for breakfast, was taking some form of girlie pill, was dressed in my first petticoated sissy dress and had made love to another sissy – my heartthrob Millicent!

Shaking off my thoughts of the past two days, I approached Master from the side of his desk, curtsied, thrust my titties and derriere out and said in my sweetest sissy voice, "Canapιs, Master?"

"Ah, thank you, Dani," he said as he took a stuffed cherry tomato from my tray as he sipped his martini. "You do make the most delightful sissy maid. Please remain in that position as I wish to admire your pert little titties. From the size of your nipples I must presume that Millicent must have spent some very special attention to them this afternoon."

After eating a few tomatoes and savoring my deeply blushed cheeks, he brought his hand up to my right nipple and began rolling it between his thumb and forefinger, which elicited a soft involuntary moan from me.

Sensing my thoughts, Sir John said, "You know, my dear, it really is not a matter of how far you have come in the past two days, but rather how much you have become your true self. I suspect that it may actually be a relief for you to abandon all those silly boyish pretenses."

"Please put the hors d'oeuvre platter on the table between the chairs next to the fireplace and take my drink back for a refill. When you get to the kitchen ask Miss Maria to please join me. Bring her drink with you when you bring mine."

I placed the platter on the table and showed Master a very full view of my sissy bottom and dipped deeply to show my titties when I placed his empty drink on my tray. With a curtsey I minced back to the kitchen.

"Miss Maria," I announced, "Master requests your presence and instructed me to bring you a drink along with his. What may I get you, Ma'am?"

Maria picked up a portfolio and motioned to a wine glass before her. "Please refill this. Cook will help you with the drinks," she said as she departed.

"Come over here, hunnybunny, and I'll show you how to prepare the drinks," Cook said. I went to the ice box to retrieve the bottle of the white wine Maria was drinking and filled her goblet while Cook went about mixing Master's martini. "Here girl, take the drinks in before the chill goes off. After delivering them, please return to me."

I returned to the library, minding not to spill, repeated by curtsey and bent to offer the drinks. Master and Miss Maria continued reviewing household matters and merely thanked and dismissed me. Returning to the Kitchen, Cook offered me a stool saying, "Good Lord, child, get off those heels for a bit. My-oh-my, but you really are the pretty one! Maybe even better looking that that sweet little Millicent!"

As I blushed, she continued, "I never have seen a sissy so quickly adapt. You must have been one miserable boy!"

"Anyway, sugar, let me go over dinner again. It is a light supper of sliced chilled filet mignon with horseradish sauce and salad. Sir John will have the bottle of claret that is breathing in the pantry. The first tray has his linen and flatware. You will set him a place at his desk and return with the empty drink glasses. His food and wine will be the next trip. Now let's go over how to serve each."

Cook reviewed each step and then told me to check my uniform and face in the servants bathroom off the pantry. A few minutes later the library servant's call rang and I was off.

I entered the library to find Sir John and Miss Maria sitting in facing armchairs in front of the fireplace still in conversation. Master looked up, motioned me to his desk and said, "Please bring in the balance of my dinner now as well, Dani." After a short bob I went to his desk, set up his dinner items, retrieved the empty glasses and returned to the kitchen. I shortly returned with his food to discover that Maria had gone and he was now seated at his desk.

I approached him, gave the mandatory little bob, and said, "Your dinner, Master."

"Ah," he replied, "I really don't know what's better the food or the sweet sound of a beautiful sissy serving me?" To which I just blushed with my eyes cast downward and returned one of my best smiles. For the first time I noticed soft music floating about the room.

"May I pour your wine, Master?" I inquired.

"Yes you may, Sissy."

I poured the wine, a little at first so that he might taste it, and then the balance and stood back. "Will there be anything else, Master?"

"Yes, of course, there shall be several things 'else,' my dear. However, for now I want you to simply stand in front of my desk so that I may look at you while I eat. Leave your tray here and stand with your hands clasped in front at your waist. Mind your deportment!"

I took my position about six feet in front of his large mahogany partner's desk: head and eyes cast downward to the foot of the desk, shoulders back, titties thrust forward, legs and feet together, and hands clasped as requested.

I felt so exposed as I knew everything, including my now throbbing little clitty, was exposed to his inspection. I was the possession of this handsome, strong man of men. My Alpha Male Lord and Master!

After a seemingly long silence, Master reached back and pulled the servants call and said, "Dani, maintain your posture but raise your hands and cup your breasts. I want you to feel your growing girlhood."

I complied with a deepening blush. After a little bit I could not resist just jiggling my titties a little, amazed at how they protruded out in the bustier. I loved them being touched, even by myself.

I heard the door open and knew someone at entered, but kept focusing on my little display for Sir John.

"Well, even you cannot resist your little sissy titties, can you?" Master chuckled and added, "Maria, you may commence. Now, Dani, caress them and show us just how much you love having girlie tits."

I sensed the flash of a camera and guessed that was what Maria was to 'commence.' It did seem that these people loved taking pictures, especially of me in my most sissy outfits.

However, the feel of my own little titties excited me terribly. I was beginning to be afraid that I would repeat my famous squirt from the night before when I was presented to all the guests. "Was that what Master wanted?" I pondered.

As if reading my mind, "Sissy, I want you to model for the camera; I do not want you to squirt like last night, even though I think the flashing cameras were part of the reason why you lost control." He chuckled and added, "I dare say you love the camera as much as it loves you! Maria, I fear that we have both a first rate exhibitionist and fetishist on our hands – although that certainly neither is a bad quality to have in a sissy!"

Maria laughed wickedly and said, "Or perhaps just a slut!" She had me prance about to show off my scandalous dress in every way imaginable as she took both still and motion pictures of me. Finally satisfied she told me to go stand before Master and present my titties to him.

I minced over and stood before Sir John, eyes down at his crotch and raised my hands to again cup my breasts. I notice a very distinct swelling under his trousers. He had seemed to enjoy my naughty vamping in front of Maria's demanding cameras.

"Ah, perfect, so sweet and so very much mine!" he exclaimed. He reached out a fondled my nipples, causing me to again sigh. "And, yes, perhaps very much of a slut!" he added.

Still playing with my proffered titties, he added, "Sissy, I noticed you at first seemed troubled by Maria taking pictures and making videos. Perhaps I should tell you more about the reasons for them.

"There are two reasons for the photographs: one prurient and the other practical. In the first case, having an emerging sissy of your beauty and natural grace is a rare thing, and it should be recorded for later enjoyment. In the second case, it is simply a matter of security. Although our merry little group plays in the naughtiest of ways amongst ourselves, we highly value our privacy as many of us maintain very prominent public lives. You have discovered and seen things, even in regard to your very own mother and stepfather, that are best held very closely. Compromising pictures are an effective way of keeping such information tightly held.

"I am now going to use you in the manner that a sissy maid should be used by her Master and Maria shall record every detail of your submission. Do you understand all of this, Dani?"

"Yes, Master, I do," I replied. The posing in such a provocative outfit and self-fondling, not to mention my preoccupation with the bulge in Master's pants, had caused that ball of lust-flame to return to me with force. "May I submit to you now?"

"You may, my sweet sissy. Do what your instincts tell you to do," he softly, but firmly replied, not at all secretly loving my absolute slut-like acquiescence.

I looked up from his pant tops up into his eyes, smiled as I as our eyes locked in complete understanding of my role, and slowly dropped to my knees. As I stared at the beautiful bulge in his trousers, I reached forward with my hands to caress his hips and inner thighs. My head came forward to gently kiss the bulge as I again turned my eyes up to his asking for silent permission to continue.

He nodded, and after again lightly kissing his fly to show my respect, I unzipped him and gently sought out his man-cock with my scarlet lacquered nails. It literally popped out in all its considerable glory. A small man-seed drop emerged, which caused me to quite unexpectantly squeal in delight as I promptly licked it off.

I wanted to take it into my mouth, but decided to first use my titties for our mutual pleasure. I rose a bit and guided his cock between my compressed titties and moaned as their tiny cleavage rubbed the sides of it. When I saw a second drop of precum come out I guided his cock tip to each of my nipples and rubbed his man juice over them. What a divine feeling it was!

With my other hand I scooped up my own juice from my leaking clitty and brought my sticky fingers to my mouth so I could lick and suck them up.

Now the urgency to taste and feel his cock in my mouth was overwhelming. I managed to fully free his plump balls and went about having my man-cock feast!

Recalling both my prior sessions with Master and my sex-charged afternoon with sissy Millicent, I began a tongue a lip ritual to arouse every sensitive part of both his cock and balls. I used one hand to cradle his balls and the other to about the base of his shaft. I was intoxicated with the differing textures of his balls, shaft and head. As more precum discharged into my hungry mouth I became wantonly consumed with providing him pleasure, licking and sucking the sensitive underside and head. Even the aroma of his most manly of parts moved me even deeper into a sea of lust.

Just as I felt I was about to receive my reward of his sweet, rich cum, he put a hand to my head and withdrew his man-meat from my hungry mouth.

"Sissy," he commanded, "beg for me to fuck you just like the slut maid that you now are! Let me hear how a nasty sissy begs to be made a real man's bitch!"

At first I was somewhat nonplussed by his sudden withdrawal followed by his crude, sharp and demeaning demand. Then it excited me even further. I was a bare-titted and shameless open crotched slut, and yes, I very much wanted to be his bitch. I wanted him to bend me over a take me hard – just like a rutting sire takes his bitch.

No longer was I a simpering prissy sissy, now I was a bitch in heat sniffing for the hard cock that I desperately needed. Quick thoughts passed through my mind, "What power did this man had over me? Or was it I, myself? Was this indeed I, a wanton sissy slut?" The absolute power of teenage libido-lust overcame any semblance of intelligent thought. I became the lowest common denominator in a mating ritual.

"Yes, Master, I am your bitch in heat and I need that big hard cock of yours in me. I need it rammed in me like a bull would. Fuck me, fuck me hard! Fuck me so hard I scream from both pain and pleasure. Make me your slut-bitch! Take me! Own me!"

I think even Master was amazed at both the intensity and the suddenness of my reply. I leaned over and gave his cock a full tongue lick starting between his balls and moving up the underside of his shaft ending at his piss hole – just as a bitch-dog would. I then rolled over to offer my quite open and petticoat framed ass. I loved the idea of having my open panties, garters and stockings displayed – so shockingly open and willing. So utterly slutty!

As I moved my hips in a manner more obscene than any stripper would, I screamed out, "Please Master, rip me in two with that stud ramrod. Your bitch needs you! Please, please fuck me hard! Just fuck this bitch-slut!"

"Well, my little sissy-bitch, that is precisely what you are going to get!" he roared.

I felt a slick finger enter me as he said, "You are going to need this lubricant, bitch, because you are about to be taken in a way you have not yet dreamed of!" As his second finger entered me, he added, "Look at how you so eagerly fuck just my fingers! Dani, you are such a sissy-slut!"

I moaned and in a breathy voice replied, "Oh, yes, Master, ream this bitch! Fuck my sissy-slut brains out!" The feeling of his fingers in me along with the tug of my garters and the abandon with which my ass was displayed turned me on even more.

"Was this really what I am or have become?" whatever semblance of a conscious brain I had left wondered.

With that I felt his cock head on my open rosette and shuttered in anticipation of my coming impalement. My entire focus was on his unseen pole possessing me in the most forbidden manner.

"Yes, you just cannot wait, can you, slut?" he laughed. "Beg for my man cock, bitch!"

I pushed back to try to get his man meat in me, but he had his hands on my hips and deftly moved back. A crack broke my moaning as he spanked my ass-cheek. I was stunned, but actually quite liked the warm feeling as the first stinging feeling subsided. "Crack, crack, crack!" as he spanked me again and again and commanded, "Now beg, slut! Beg for man cock!"

The spanking actually excited me even further – if that was possible. I was almost crying now for want of him in me and was obsessed, "Pleeease, pleeease, Master, fuck your needy sissy. She needs your beautiful cock shoved up her and your manly cum injected into her sissy ass! Pleeease, I beg you, pleeease!"

He took me in one thrust, causing me to exhale in a loud sigh followed by, "Oh my God! Oh my God! Oooh sooo nice! The flame of lust in me now began to burn with white heat.

I tentatively moved my hips again, which he took as a signal that I was ready for the real fucking to begin. "Now Sissy, you will find out just what a hard man-fuck is all about!"

With his hands on my hips he began to pump his cock back and forth in my sissy love tunnel, finishing each penetration to the very hilt. "Pinch your little nipples sissy. Show me how hot you are!"

This was not like our fuck from the night before. This was a rutting man taking his sissy for his own pleasure – ramming his pleasure pole into her at the lowest common animalist level. Indeed I was now his bitch! And I loved it!

I shuttered as an orgasm wracked my entire body. I just kept groaning out, "Oh, fuck me, fuck me, fuck me…" Master was grunting each time his cock assaulting me – each time in a seemingly more urgent manner. I sensed a wetness coming from my soft clitty, but it was in accord with my entire body, not an event onto itself.

Another orgasm stuck me, and just as I screamed out, Master made one final deep plunge into my love tunnel and released his man juice deep in me. My body shook and my head felt light – almost spinning. What had started as another orgasm now went thermo-nuclear. I knew I was screaming, but to this day I have no idea as to what I said, or was attempting to say. I was delirious. I did know that my clitty had again erupted.

The shaking continued and tears began filling my eyes. I could only barely seem to catch my breath. I felt Master soften and withdraw from me. Strong masculine arms wrapped about my small slender frame and lifted me up. He took me into his arms and hugged me as his kissed away my tears.

It was heaven being in this man's arms. I moved my head back, kissed him on his lips and whispered, "Thank you, Master. Thank you so very much!" Then, mustering up what little strength I had left, I slid down his chest and returned to my knees before his manhood. Without comment I took his softening cock into my mouth and began cleaning it, relishing in its pungent taste and smell.

I could feel his man-seed starting to drain back out of me and mix with the considerable mess my little sissy clitty made. It made me feel very slutty indeed – and I was even inwardly more embarrassed to discover that I quite liked the feeling.

"Yes, Dani, you are my good little slut. You are the perfect sissy and have so many new joys to discover. Now, I am going to have Maria take you to your room and prepare you for bed. Tomorrow is going to be a very busy day – first your sissy lessons and then we start a two-day cruise on my yacht."

I rose and tried to curtsey, but started to fall over from exhaustion. Luckily Maria first caught me and then Master grabbed me up into his arms like a baby and carried me up to my room.

He took me to the bathroom and sat me down on the commode just as Maria and her assistant, Anna, arrived. "There, ladies please take care of her quickly and get her snugly away in bed. We must take extra care of this perfect sissy." He kissed the top of my head and said, "You have been just perfect this evening. Sleep well my little girl."

All I could manage was a soft sigh and a barely whispered, "Thank you, Master."

With their customary efficiency, Maria and Anna managed to strip me, took out my new earrings and removed my makeup with a cleanser. I was douched out first with a mild soapy solution and then with a mineral oil solution. A shower hair cap was put on me, and I was guided into the shower for a very quick washing. "We will have to let her hair go until the morning, Anna. This girl needs to get to bed, and quickly," Maria said.

All I could manage was to stand in the shower while Anna reached in and washed me down with a lilac scented body wash. Coming out Maria patted me dry with a warm fluffy towel as Anna cleansed my recent piercing and reinserted clean studs.

"Here, Sissy, take your girlie pills," Maria said as she handed me two pills and a glass of water. "I think you now appreciate the need for them."

Lastly Anna placed a medicated suppository up my very tender sissy pussy. "There, there," she said, "you have been an active girl, but this should make you better – now to get you into a pretty nightie and into bed."

Maria slipped a short pink satin babydoll over my head and then steadied me as Anna first lifted my feet and then drew matching bikini panties up my legs. Both women helped me back into my pretty pink and ever so girlish bedroom.

Before I knew it, I was between the pink satin sheets and fast asleep.

 

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