Dear reader, this is my first effort at fiction, but after enjoying so many writers' efforts for years I felt I should try to give something back to the wonderful people who write and publish these marvelous stories. This is a story of a sissy by a sissy for sissies – and hopefully a few cute admirers as well.

Book I – Awakening, in five chapters, deals with a 48 hour period where our heroine realizes and actuates her sissy-self. If it is well received, I plan on writing several sequels relating Dani's, and her kinky little band's, future exploits.

It is rated X, and deservedly so, as there is graphic sex and references to all sorts of other wonderfully kinky things. Please be of appropriate age or be gone! I hope you enjoy it as much as I enjoyed writing it! Either way, please do let me know.

 

Dani's Story

by sissystevie

 

Book I – Awakening

Chapter I – The First Evening

 

I suppose it was always meant to be. I always knew that I was sissy. Plain and simple, just a sissy! It just took the proper push.

Over the years many fellow students made fun of me for being a little too "pretty" with a nearly hairless slim girlish body, longish blond hair and bright blue eyes. My puffy little nipples were conflicting sources of public embarrassment and secret pleasure. My peenie simply refuse to grow when other boys started developing real penises.

A group once pinned me down and masturbated my tiny little peenie to demonstrate what a sissy I was – an act of abasing humiliation and abuse that strangely continued to excite me for unknown reasons.

Early during my senior year I had a crush on another boy at school. He was a total jock but loved having his body rubbed. He would even, on occasion, give me a nice back rub. Lord knows I had to remain either seated or on my stomach as when we touched my little peenie would go berserk, even to the point of leaking!

For years I had been fixated with my mother's beautiful clothes, especially her lingerie. I even had a treasured little collection of soft, silky items that I had managed to "collect," mostly from Mummy, over the years and relished wearing them whenever I had the chance. And I thought Mummy had no idea!

The "push" came during my senior year spring break from boarding school. We traveled to Puerto Rico with my mother and stepfather, both avid golfers. I had just turned eighteen, but still had my young girlie looks. I really wasn't entirely sure why I was brought along as I did not even like golf, let alone play it, but went along thinking that I might have some special free time to myself.

After arriving and unpacking, Mummy announced that we all were going out to a supper club with an old friend of theirs, a wealthy English ex-patriot named Sir John Strong.

Interestingly, she suggested that I wear a pair of light weight tropical silk-linen white slacks that she had earlier insisted I pack. However, when I struggled into the slacks as they appeared to be much tighter than when I last worn them. Could I have grown that much? There also was a seemingly curious flare at my feet. I did manage to get them on and zipped up. As I went to put on my belt I noticed that the loops were missing. There was only a tab closing in front. Even more curious! Were these even the same slacks I had packed?

As I was pondering the strange slacks, Mummy swept into my room to pick me up. She was indeed an impressive woman and long the object of my secret desires – tall, shapely, but trim figure, flowing long blond hair cascading across part of her face and extending down just above her shoulders. We shared the same crystal blue eyes. She was wearing a white majestic crepe de chine blouse with a bow about her neck and matching broad legged slacks.

She immediately noted that that my boy briefs were causing unsightly lines under the slacks. "Danny, how could you dress in such an unbecoming manner? Not only are your trousers a mess, but nothing else matches! Your shirt is far too thick and clumpy for your pants. How can you do this to me when we are dining tonight with an old dear friend of mine whom I have not seen in years? And with so little time until we are due to meet him.

Danny, I am not pleased! Not only will you change to please me, but I shall severely punish you if you displease me any further with childish protests. Remove all your clothing, everything, and wait for me to return. We have so little time and I need to improvise."

Mummy had great sway over me when she was angry. Something deep inside me needed to please her. Although Mummy often commented on my appearance, especially if I was sloppy or looked unkempt, this seemed a considerable step forward. She was particularly determined and not to be crossed.

She returned shortly carrying a bag. I stood before her in my robe, totally embarrassed, but quite concerned about her anger. "Danny, dear, you shouldn't act like such a little boy!" she admonished me. "I only want you to make a good impression on my old and dear friend, Sir John. You are in the tropics and should dress accordingly. Additionally, sweetie, it is high time that you began dressing in a way appropriate to your true self."

With that she held out one of my favorite white satin panties from my "secret" collection. Even worse, I had originally taken them from her drawers and worn them often in my private moments. Now they were now freshly washed and ironed!

My hand came to my mouth, and I think my faced must have changed through five shades of red in mere moments. She smiled and said, in a gentle but very firm voice, "Now, sweetie, you should know that there are no secrets from your Mummy. Just put on the panties like a good boy. We both know it will not be for the first time!"

I started to protest, but she merely held her figure to my mouth and whispered, "Now dear, you know that you are not too old to be spanked, and for your little collection you should and shall be thoroughly thrashed! Now you are going to dress exactly how I wish you to and without any silly little pantyboy protests! Now remove your robe this moment and begin dressing as I wish. You hardly need to displease me any further!"

Turning an even deeper shade of red, if possible, all I could manage was to squeak out in a far higher voice than I desired. "Yes, Mummy dear." I slid the soft panties up my legs, trying to adjust them properly before my little peenie became too stiff to manage. "Smooth them out properly, sweetie. I know you know how," she commanded. Well smoothing out the panties had the predictable effect on my little lollipop! I tried to hide it as best as I could, which any sissy will tell you is next to impossible.

"Danny, dear, your little teapot tells me all I need to know. Pay no mind to it – it is simply part of who and what you appear to be!" she admonished me. "Here put on this blouse. We are running out of time!" she said while handing me a silk shirt-blouse from her bag.

I nearly fainted. It was sheer white silk with puffy long sleeves and turned-up cuffs at my wrists. It felt like a clean crisp breeze coming across my body as I slipped into it. I actually had goose bumps! I fumbled with the cloth covered buttons as they appeared to be differently located from what I was used to. It was quite tight on my waist, but opened up somewhat at my chest. I quickly realized that my now very hard puffy little nipples protruded through the sheer fabric in an almost obscene manner. The collar seemed different – much larger and softer than I was used to. "But didn't Mummy call this a blouse?" I thought to myself. It surly looked and felt like one, and also with the buttons on the left side.

She then handed me the white slacks to don. With a smile on her face she watched as they more easily slide up my legs to close tightly high on my waist and taunt over my bum with a slight divide between my sissy cheeks. That surely wasn't there the last time I worn them! Also, the waist really did seem much higher now that I had on sheer panties. Now I noticed that the pockets were gone! Curious indeed!

Next Mummy stepped behind me, wrapped a coral-pink raw silk sash, a form of cummerbund, about my nipped in waist, and hooked it behind me. I was mortified, but my peenie loved it, growing with each new assault provided by the clothing Mummy was forcing upon me. "Whatever would people think as I went out in public?" I thought, but did not dare say.

Stepping back to inspect her girlish son, Mummy said, more to herself than to me, "Good, but she still needs work."

"She?" I wondered.

Mummy produced a pair of shoes and two small boxes from the bag she had carried in.

The shoes were slip-ons with low two inch heels in matching pink silk to the sash. Worse, each show had a wide bow attached to each toe. The ugly old boy socks that I previously had on were not even considered. Smiling her approval, but saying nothing, Mummy proceeded to open the first box. It contained some gold jewelry. Before I could utter the slightest protest, Mummy ordered me to extend my arms. Within a flash, a gold and pearl braided bracelet appeared on my right wrist and a girlish pearl ring on each hand. Next a gold strand went about my neck, a sweet heart hanging from the center, just where my blouse opened up. I then was ordered to lift my leg and a thin rope gold anklet, again with a dangling heart, was attached. My heart was racing and my face flushed. My entire body now was tingling, nipples like little bullets, peenie totally out of control, and I feared, leaking! I could not imagine what the second box could possible contain.

"Sit in the chair next to the desk, sweetie. Not a word of protest from you either. I need to finish you up so you are presentable to Sir John. Yes, dear," she swooned, "you look adorable, just as you should look. So utterly appropriate for you! Isn't this what you always dreamed of? Especially when you were leaving sticky little messes in all that pretty lingerie you managed to collect?"

"Place your right hand over here, towards me," she commanded. "Oh, these nails need professional attention, but we do need something for this evening." With that, she produced a file and quickly shaped my somewhat long nails into a more feminine shape and applied a fast-dry coat of coral-pale frosted pink nail polish.

"You secretly love this, don't you, my little sissy?" Indeed I did! The feeling was incredible. A first coat of nail enamel has a special tingly feel, and the look of the frosted gloss is just so very special! Inwardly I swooned. Outwardly I was horrified.

She produced tweezers and plucked some offending hairs from my brows. Next was light blue eye shadow and brown liner to both my eyes and brows, followed by some red blusher, which I hardly needed owing to my nearly constant embarrassed blushing. "Now be a good girl and purse your lips." She showed me how to present my lips for lipstick and deftly applied a liner followed by a light frosted pink color. The effect was almost electric feeling the smooth gloss upon my pouty lips. "Better," she said more to herself than me, "I'm almost done with my little sissy. It's nice to see you appreciate the wisdom of obeying your mother!"

"Now for your hair." She began rearranging my hair using a teasing brush, thick comb, some gel and finally a spray. It was combed over in the opposite direction and teased and sprayed up to create a bob effect. Lastly two small gold hoop clip-on earrings were attached to my lobes, and with a couple of dabs of Mummy's very own perfume, I was pronounced ready.

Now go look at yourself in the full length mirror, Danny – or maybe we should make that "Dani" with one 'n' and ending in an 'i'?" she said. "Go look and tell Mummy what you see while I tend to your handbag." "Handbag?" Oh my, I thought!

I looked and was astounded! Standing before me in the mirror was the most effeminate of boys. My face and hair were really that of a young girl. The bob effect combined with the light, but effective, make up was incredible. I was transfixed. My heart was beating a thousand beat a minute. However, when I looked down at the rest of me I was almost moved to tears!

The blouse, and yes, that's exactly what it was, was incredible. It clung to me like a second skin about my waist and little titties and then flowed about my neck, shoulders and arms. "Titties," I thought, somewhat shocked at referring to my chest as such. The blouse's large rounded collar was indeed amazing, as I had suspected. It was simple even though oversized, yet it floated above my natural neckline and softly curved downward in the most delicate manner. The soft sheer silk was unlike anything I had ever experienced, or even dared dreamed of. The tight waist gave way to the high rise of trousers, which I now clearly realized had been extensively altered, if not remade.

The pink raw silk sash contrasted so effectively with the pure white blouse and slacks. The pink matching shoes with their outrageous bows served to further compliment the whole look. I was not really a girl, but I realized once and for all that I certainly was a sissy boy – and a very elegant one at that! The sparkle of my jewelry perfectly finished off the overall effect.

I was in rapture! Mesmerized actually. I began a slow swoon before the mirror, twisting and simply feeling the effects of soft fabrics across my skin. I was lost within myself utterly. Mummy noticed, but for the moment remained silent.

She approached me from behind, placing her hands about my slim waist. "Here, Sissy, ("Sissy," again – although this time it really did seem to fit thoroughly) take you pretty handbag. You will need it to repair your face during the evening." I accepted the handbag willingly as it so perfectly fit. It was a small clutch bag made from the same pink raw silk that matched my sash and shoes. "Sweetie, I think you have found yourself, but only time will tell," Mummy whispered in my ear. "I have known that you were different for many years, it's time to explore this side of you, and so you shall!"

"Now, sweetie, for a few quick snap shots, I need to remember this moment and your first pretty sissy outfit." Mummy produced a small camera and made me pose while looking at myself in the mirror. Mummy knew full well that I would entrance myself through my image in the mirror and forget about pictures being taken – and so I did!

Mummy announced, "We're off! Be sure to mind your best manners or I shall deal with you very severely, as I should for all those times you naughtily played with and even stole my most intimate things!"

The walk though the hotel was incredible. Here I was, paraded about as a total sissy boy – a sissy, plain and simple. I was led by my magnificent mother who in turn was escorted by her consort second husband.

However, fear not, many others were extremely interested in the young emerging sissy. Certain women looked, of course not obviously, in appreciation of the mother for a job well done, other women thought of a sissy who might properly serve them. The men, those discriminating enough to know and confident enough in themselves to indulge, just leered with abject lust at the young beautiful sissy boy being pranced before them. Alas, before them I was swishing forward as the newest indoctrinee into the sweet submission of complete pantied nancyboy sissyhood. They knew it, and I was beginning to realize it. Mummy appeared well pleased. The worst part was that not only were my sissy nipples throbbing, but my peenie was entirely out of control. I could no longer even pretend to hide it.

The hotel doorman even held the car door for me. It was a chauffeured Rolls Royce. "Could this be the mysterious Sir John's car?" I wondered.

Once settled in the car, Mummy asked my step father, "Henry, doesn't Danny look pretty tonight? Just as we had discussed, it's simply so natural for him, isn't it?" He observed, "Well, Constance, he never was going to become much a man, better this way I suppose." Mummy offered, "See how he can't keep his hands off his blouse – he really is such a nancyboy!" I turned an even deeper shade of red as I knew it was so true.

Mummy gave me an appraising look. "Yes, you do look well, Dani dear, but I think you need to practice tending to your face. Open your handbag and take out your lipstick and powder compact." As I complied, she said, "Ah, yes, that's good girl. Now open it so you can see yourself in the mirror. Carefully freshen up your lips using the same technique I showed you earlier." Again, as I did, she exclaimed, "Good girl, remember less can be more. Purse your lips. Ah, that's right." However, to my horror, the shade in my new tube was considerable darker, a frosted pink coral color that matched my handbag, sash and shoes. There was little I could do other than accept this small further step to complete sissification – besides, I found that I quite liked the look! I even puffed and carefully rearranged the few errant strands of my new hairdo. Something not unnoticed by my mother and stepfather.

The entrance to the supper club was similar to the reception in the hotel lobby, only with more obvious attention being paid to me. I really did not know precisely how to react. Mummy whispered, "Danny, keep your elbows tight to your sides, take smaller steps with your knees close together and arch your back. Feel how you know you look and act it!" Mortified, I did exactly as she commanded. I realized fully that I was causing a bit of a spectacle, but was completely powerless to change it. Mummy's dominance directed me, and the inner joy of what I was wearing enslaved me.

As we approached the booth I saw a distinguished looking older gentleman I presumed to be the mysterious Sir John Strong stand up to greet us. He was indeed handsome. Quite tall, thin, but muscular, wavy bold white hair, beautifully dressed. I could feel his masculine strength from twenty feet away.

My stepfather reservedly greeted the man and while Mummy warmly shared a kiss and a big hug. Mummy then took my arm and moved me forward before the man. "Sweetie, this is our friend Sir John Strong. John this is my sissy son Dani. He prefers "Dani" with one 'n' and ending with an 'i,'" she announced. Again mortified, I extended my hand only to have it taken softly as a woman's hand would be taken for a kiss, which is exactly what Sir John proceeded to do! I was both embarrassed and excited by the ritual. I could feel the man's strength and virility though his soft grasp. I had never been so affected by anyone and found myself speechless.

"What a complete vision of sweet sissy loveliness," exclaimed Sir John. With that we were seated, Mummy and Henry on one side of the formal table and Sir John and I on the other. As I sat, Sir John quietly cautioned me to sit up straight with legs together like a proper sissy. I obeyed instinctively.

Cocktails were offered and I was allowed a glass of excellent white wine. Sir John ordered dinner for me as I was not given any form of menu, let alone choice. The three adults bantered back and forth with small gossip from times past and of events since they had last been together.

After a few minutes, while the conversation was going on, I felt Sir John's hand touch my thigh and then softly move up and down the mid part of it. I, of course, sat as a proper sissy – back straight, legs together and hands folded. I could not restrain the desire to put my fingers in my new hair style; the feeling of the bob hanging beside my face was far more intoxicating than the wine. When not in my hair – I was troubled I might ruin the arrangement – my hands traced their way down my blouse, lingering on my now diamond-erect nipples.

As minutes went by, Sir John's stoking of my thigh became more erotic as he moved his soft hand to my inner thigh and higher. It was having an almost impossible effect on me and I slowly let out a soft sigh. "How wonderful, darling, you react perfectly!" Sir John whispered to me. With that his soft caress reached my distressed peenie. I knew my panties were already wet from the incessant stimulation of the past hour or so, now I greatly feared a total release, which the tight thin pants would never hide! Only dinner arriving saved me. As we were being served, Sir John leaned over to me and whispered in my ear, "Yes, Dani, you will do and very, very nicely indeed!" He then gave me a short but soft kiss on my cheek.

Over dinner the adults' conversation turned to me. Mummy observed, "John, dear, you seem to greatly approve of our little Dani. Seeing him this evening makes it all seem so natural. As you know, I would have done this several years ago, but I was obligated to allow him every opportunity to become a real young man. Instead, he just seemed to become more girlish and play with more and more of my lingerie, soiling it frequently. How the poor dear thought I would not notice just baffles me. Perhaps he was just trying to get caught. However, he has just turned eighteen and it is time for him to confront his true self, which from this evening appears to be that of a complete sissy nancyboy."

Stepfather somewhat wistfully offered, "Well, until this evening I had always thought there might be some hope for him becoming a real man, like his father, but just to see how he reacts to the shamelessly sissy things he is wearing and how he is secretly gushing over Sir John seems to seal his fate."

"John," Mummy said, "do you wish to see how things develop?"

"Oh, indeed I do," Sir John replied. "However, as we discussed, it must be within the framework of giving him choices as we go. I certainly fancy completing tonight's agenda. We can review the situation fully in the morning and proceed from there."

"Excellent!" exclaimed Mummy. "I do, however, want Dani to make a fully informed decision. Perhaps, John, you could send those two lovely ladies of yours over in the morning to properly dress her? She should experience all the soft frilly delights of being a girl before deciding if she wishes to remains sissy for the remainder of our stay here."

"Of course I shall send Maria and Anna over, and with some appropriate things for Dani to wear," Sir John said. "Then I suggest Dani, you and I go out for a nice lunch to talk thing over."

Looking directly at me, melting me with her beautiful eyes and stunning me with her feminine beauty, Mummy said in a very measured, definitive voice, "Dani, we all know that you are a sissy, the only thing to be determined is the measure of it. You certainly look the perfect sissy; you even act as a sissy. Tonight, sweet girl, you do not have a choice. Henry and I shall leave you here with Sir John, who will be your escort for remainder of the evening. I expect you to be the perfect sissy and comply with each and every of his wishes. Failure to completely do so will be dealt with in the severest manner, and in ways I frankly do not even wish to discuss. You will do this simply because your Mother requires you to. Do you completely understand me?"

Not to mention the impact of Sir John's hand firmly on my little peenie, I certainly did understand Mummy quite fully and completely. As I had no choice in what I was wearing, I now had no choice in what was to occur next. However, mostly I realized that I actually wanted it to happen! I swallowed hard, glanced at the handsome Sir John, looked down and said, "Yes, Mummy dear, I understand and will be a good sissy for Sir John." My fate was now sealed, at least for the balance of the evening.

"Well said, my dear, and I expect it to be equally well done!" Mummy continued, "Sir John will return you to the hotel later this evening. He and I shall confer in the morning. Assuming that you have fully and completely fulfilled my instructions of this evening, Mari and Anna will arrive and properly make you over and then we shall go to lunch where you will be given a choice. You may return to trying to be a regular boy, although I doubt the outcome of that quixotic effort, or you may continue under Sir John's tutelage as a sissy for the remaining ten days of our stay here.

"However, understand this, sweet child, if you attempt to be a real boy all of your little 'collections' and secret sissy games will come to an abrupt end – never more to be indulged! Only rough, rugged boring boy things for you! This evening's little adventure shall be considered your punishment for sealing and soiling my, and who knows else's, lingerie.

Contrary wise, if you elect to accept your obvious sissy ways for the remainder of our stay here, no penalty will be assessed. In fact, we all will be well pleased that you have apparently found a special form of happiness. Your stepfather and I shall pursue our original plan to play some golf as well as entertaining ourselves in our own special ways that we so love to do. You, no doubt, will be enjoying your own alternative forms of entertainment.

"Although I shall remind you of this tomorrow, if you do spend the balance of time here with Sir John, it will be a commitment for the complete period of time and you shall obey him as you would obey me. Sir John will have complete and total control over you. He will be permitted to punish you as warranted. To treat a sissy otherwise would be unheard of!

"It will still be necessary for you to return to boarding school to complete your senior year and graduate. Something that, I think, could prove very difficult in either case. If you wish to be a boy you will have to get over that boy whom you have such a crush on. Yes, dear, I have read your secret journal pining away for him! If, however, you pursue your innate sissy side, being without all you sissy finery could prove pure torment – even if for only a few months. Well, maybe your boy-friend might provide some very real relief. I would also permit and discrete supply of fine lingerie to help you along. Your secret boyfriend would love you in them I'm sure.

"After you graduate you will again be given another choice. Sir John has a wonderful chateau in the south of France where, if you have acceptable progressed, you could summer.

"Dani, please acknowledge that you understand all of this fully and completely."

Throughout Mummy's ultimatum, Sir John's hand continued to torment with pleasure like I had only dreamed of. That, combined with the sensual clothing and my beautiful stern mother's presence, had my head swimming. I merely bowed by head and said, "Yes, Mummy, dear, I promise to be a perfect sissy for Sir John this evening."

"It is best for you and I dare say you know it, my sweet sissy son!" she cooed, pleased with the course of the conversation and apparent outcome of the evening thus far. "Henry and I shall return to the hotel and place you in Sir John's charge for the remainder of the evening. Now sweetly kiss me goodnight like a good girl. We shall discuss it in the morning. I know you will be a good girl this evening for your new Master."

We air kissed and both Mummy and Henry bade goodnight to Sir John and – with a sly smile – me.

Oh my God! Here I was! Was I living out my sweetest dream or my worst nightmare? I knew where all this was to lead – the complete sissy nasty! Was I ready, willing, even able? I actually giggled to myself thinking "Inquiring sissy minds want to know!"

Sir John seemed to notice my slight inward giggle, "A penny for your thoughts, sissy?" he inquired, hand still on my now ranging, leaking and pathetic tiny twinkie teapot. I crossed a line. Actually, I crossed the Grand Canyon in a single, but very appropriately femme, leap! I leaned over and kissed him directly on his lips! Impulse or instinct? Who really knows, but the effect was electric! I had surrendered, at least for the night.

"Sissy, it is time we left," he said, "refresh your face and after that lovely kiss, and we will go to my house. I see that you have accepted your role, now you shall experience it fully. Remember your proper deportment: knees close, short steps, elbow to you ribs, back arched, and proud. Hold you handbag daintily with a limp wrist."

I, of course, did his bidding.

With that, a path from our table seemed to part. There were no tacky bills or waiting to leave. The Maitre d' appeared and simply stated that Sir John's car was waiting. Sir John stood and offered his arm to me. I stood and straightened my slacks and blouse. I found myself puffing and arranging my hair once again. Something deeply inside me wanted to greatly please this man of men. I knew he wanted, no demanded, a perfect sissy at his side. I needed to be just that sissy right now.

His car was a Mercedes 600 SL roadster, thankfully with the top up – my hair would have been ruined! As the car jockey closed the door after me I noticed a distinct bulge in his pants. "Was that I causing such a reaction? Oh, my!" I thought as I marveled if I really could affect men that way – well, at least certain men who understood what I think I was about to learn!

Now my hand willingly found its way to Sir John's thigh. My thoughts were far ahead of my conscience.

Within a few minutes we arrived at his estate, considerable even by my standards growing up on the pampered Main Line of Philadelphia. The entry had large iron gates that seemingly parted as we approached. Was this estimably man also a wizard? The driveway went up a hill overlooking the harbor, with all its lights. The house, itself, was of the gracious old Spanish influence, large and beautifully appointed. I particularly loved the extensive stone and iron work. It seemed almost medieval and somehow castle- or, dare I say, dungeon-like.

He asked me if I liked his little refuge from complicated real life. I responded with a sigh, simply saying, "Oh, Sir John, it's so romantic! So beautiful!" He responded by saying, "Sweet sissy, perhaps for this evening you might simply address me as 'Master.'"

"Now, my little butterfly, come into your Master's cocoon," and after a pause, he added, "It's such a lovely night I thought we might sit by the pool. I have a special outfit in mind for you that both of us should enjoy. Come this way and I will show you to a changing room in the pool cabana. Your outfit is laid out there, sweet sissy. Leave on your jewelry and apply some additional make up to the extent you think it will please me."

He led me through a long stone floored hallway onto and patio and then down to a beautiful slate colored pool. The cabana sat at the far end of the pool. Finding the changing room I quickly located the clothing meant for me. "Oh my," I thought, "another thing I had secretly dreamed of! Was that also in my now compromised journal? I think it was."

Laid before me was a pure white silk bikini. My heart literally skipped a beat. It was exactly like I had dreamed of – I had to get that lovely thing on me! I quickly stripped, again feeling the rapture of the blouse's soft caress against my skin and the sweet kiss of my silky panties being lowered. Almost in a trance I pulled the bikini bottom up my legs. The actual bikini was even briefer than the one in my dreams. The front barely covered my little sissy teapot. A few of my public hairs, such as they were, seemed to hang over its top and sides – something quite troubling to me. As I cast about my eyes, I found a pair of small scissors on the makeup table. The offending hairs were quickly trimmed and now I was able to fully inspect this delicious froth of feminine fashion. Yes, indeed, it only barely covered my peenie and little sissy "purse," but it also barely covered my sissy cheeks. The top of their cleavage was actually visible. The bottom was finished off with two rather large bows on each side and had a little asymmetrical skirt of white chiffon across the front. For the first time in my life I actually uttered, "To die for!" The front even seemed to accommodate my boiling over "teapot" in a most attractive manner.

I could not wait to try on the top, something relatively new to me. It perfectly matched the bottom in both form and function. There were two slightly shaped, but very small triangles to cover my little sissy titties. They were sufficiently sheer to fully show my aching and very hard nipples. It fastened with cute ribbon bows both in front between the cups and at the end of the strap behind my neck. I felt so vulnerable and exposed – and I quite liked it! After preening before the mirror I had to discovery what other delights awaited me.

First I came upon a box with a brand new pair of high heels that matched the bikini silk-like fabric. They had to have been at least four or five inches high and stiletto in shape. Could I manage them? I have worn Mummies heels on several (well, ok, many) occasions – I thought that, too, was now known – and could most likely handle them. However, the most intriguing part was how they would fit on me. Rather than a back, they had long ballet-like satin ribbons that would wrap about my foot. On the inside of their box I found a diagram showing how to wrap the ribbon first about my ankle and then, be still my heart, up my calf, ending in sweet bows! I was in near sissy shock! My hands literally trembled as I put on the beautiful heels and attempted to lace up the ribbons. After some trial and error I finally had all in place and again was overwhelmed with the effect.

The last item was a delicate chiffon caftan, almost like a peignoir, billowing with tiers of sweet sheer folds and layers, but still transparently revealing the sweet temptations that lay beneath.

Now I feared that I had taken far too much time primping and pampering my sissy self. Would Sir John, Master to me now, be angry? Well, he would be even angrier if I failed to adjust my makeup. Thus, to the table I went and feverishly applied, more heavily than I intended—new eyeliner, shadow, powder, blush and lip gloss. I spotted a bottle of expensive perfume and instinctively applied dabs to my neck, chest and wrists. With that, and a quick spray and light brush to my bobbed hair, I took and final check in the long mirror, drew a very deep breath, put my posture in the best sissy form and minced out to meet my Master and my fate.

He awaited me in a chair by a table at the other end of the pool. An iced bottle of champagne was opened beside him. Two glasses were chilling in the ice. Soft music floated about from unseen sources.

He was wearing a silk robe, closed with a tie in front. I approached him in the most effeminate manner possible. I sensed that my hips were moving as I minced, one foot before the other, in the very high heels while trying to keep my upper body erect and straight. The feeling of the silken bikini was amazing. I was transfixed as I walked towards this perfect Alpha Male to whom I knew I would soon utterly submit.

Greatly relieved, I saw a smile on his face – a knowing, confident, dominant smile. When I reached him, without though or guile, I dipped into a slight curtsey, rose, lowered my head, and in a very soft voice uttered, "I present myself for your pleasure, Master."

"Oh, Dani! Yes, you will do very nicely indeed! You please your Master, and that is a very good thing, for your Master shall bring you pleasures you have yet to dream of. I want you to model your outfit for me, but first a little champagne. Sit next to me, my lovely, and have a drink with your Master."

I sat in a manner I thought a ballerina would – yes, Mummy also made sure I saw the complete seasons of the Philadelphia Ballet as well! We drank in silence for a bit, just savoring the moment. Frankly, I needed a few moments to collect myself. After a bit, Sir John said to me, "You of course realize that you are both different and very, very special, do you not Dani?" I lowered my eyes a demurred to him, simply saying, "I am flattered that you think me so, Master."

Now model your beautiful outfit for me, young lady."

I had always loved watching models, especially runway models when Mummy would take me to fashion shows. "Did she know back then? Was this my destiny? Who really cared at that point?" I thought as I realized that the setting, my wonderful outfit, the champagne, the music, the moment…the MAN, was all far too intoxicating!

After taking yet another deep breath and collection my thoughts, I stood up, caught the rhythm of the music and walked away from Sir John. As I went my body began to sway to the beat of the music. Recalling how runway models performed when I reached the end of the pool, I put my hands on my hips and turned, first with my upper body, followed by my hips and finally my feet.

I noticed a flash from a camera in his hand. I quickly though to myself, "Did everyone want compromising pictures of me this evening?" However, the flashing just made me think more about a fashion show model on a runway, and that excited me greatly.

I proceeded to do a runway prance coming back towards him, hips moving, one foot before the other with arms and body tuned to the music. When I was before him, I slipped, with more body than arm movement, out of my robe, tossed it over my shoulder and repeated the runway prance away from him. When I again reached to the far end, I dropped the robe, put my hands to my hips, turned and proceeded, keeping my hands on my hips, back towards him – my eyes locked to his while every other part of my body sexily swayed to the music. The moment simply had overtaken me – I was possessed!

As I neared him, my eyes riveted to his, my hands began caressing my body – starting at my hips and followed in a continuous motion by my derriere, waist, and little budding sissy titties. Finally, in reverse I tussled my bob hairdo, ran my hands over my cheeks – pursing my lips, down again across my erect nipples – pinching them for a tad longer than I intended, about my waist, and ending back about my tush while thrusting my very distressed sissy teapot forward. Amazingly, it all happened just as I reached him.

To this day, I am uncertain who was actually more sexually charged, or for that matter amazed. I knew I was a sissy. Heck, I always knew I was a sissy. All three blind mice could have figured out that I was a sissy! Sir John knew full well that I was a hopeless sissy. But my little "runway" performance shocked both of us. "Hello world," I said to myself, "here's Dani!"

Now, I pondered, just what shall I do for an encore? Well, really there was only one thing to do! When I reached him, I simply went to my knees before him – it just seemed the proper and befitting thing to do! I lowered my eyes and whispered, "I am here for your pleasure, Master." And I meant every single syllable of it!

"Then you shall demonstrate just that my sweet sissy," he said. He dropped a pillow for me to kneel on and said, "Sissy, come, kneel on this, open my robe and kiss my cock. Do this only of your own accord, but in full understanding that it is an act of complete submission and devotion to me, your Master."

Was there really any choice? I had to, despite his caveat, as Mummy had ordered me to. However, that really did not appear to be the prime consideration as I yearned to submit to this powerful man. Moreover, I had secretly dreamed of just this very act for several years and here it was – open and before me! Without hesitation, but with trembling hands and racing pulse, I opened his robe to find myself face to face with the manliest of cocks. Yes, a cock! Not a sissy peenie teapot, not even a preppie jock's wannabe cock, a Master's very real, very present, and very demanding COCK! Of course, I melted. It was beautiful! I was awestruck! Thank God he knew what was going through my mind, or else I might have been punished for hesitating.

After a moment or two, He gently asked, "what do you think, sissy?" Oh my God, talk about the proverbial rhetorical question! I managed to blather out, "I…I…I want to…well, it's incredibly, beautiful…soooo powerful, yes, I want, no need, to worship it, Master. May I?" Talk about surrender!

"Yes, my dear sissy you may, but I want you to explore all of it. I understand that you have yet to suck a real cock, although that is hard to believe for such a girlie boy as you. Sissies like you were born to suck cock, Dani, and I think you know it!"

I almost wept in totally confused humiliation. Was it because I so surely was about to suck a cock for the first time, or because as a sissy I had never sucked one before? Things can be so confusing for us girls…

"Do what comes naturally to you, Dani, but now I command you to service me! It is your honor and privilege to service my cock!" he said. No doubt about my direction now – downward with vigor!

As commanded, I commenced the preverbal "sissy nasty." I fully expected some initial revulsion. It never happened, nor did anything even remotely nasty happen. I simply bent forward, put my hands to his hips and kissed Sir John's ample man-meat. It was so very natural and meant to be. His cock was throbbing, alive and a presence entirely onto itself.

I then explored his cock and found it to be warm and wonderful. As my lips again touched the head I noticed it was damp from pre-cum. Simply by kissing it, I had my first real taste of man cum, and I quite fancied it! As my lips explored his velvet "helmet," I emitted a quite involuntary moan. I was somehow surprised that I could see my pink lipstick on his cock

"Yes, my sweet sissy, you do understand your place now," he whispered. "Now slowly use your tongue to caress it, especially the rim of the head and the underside of its shaft. Ah, there's a good girl! Now once about the head and then slowly down the underside to my balls – I want you to experience then as well."

I followed his command, rewetting my tongue with my lips occasional as I went. My hands touched his muscular thighs and I felt yet another chill go down my spine. He was so strong and powerful, and I was his sissy lover submitting myself utterly to his desire. I started to lick at his massive balls, yet again awestruck by their size. I had of course fantasized about a cock, but never really about balls. It was so new and so terribly exciting!

"Dani, gently cup my balls in your hand, raise them a bit and then softly kiss and suck them," he directed. I again let on a small moan, both from amazement and pleasure. The balls were quite massive and obviously very full. I again shuddered knowing full well where their contents would soon be delivered. "Feel the privilege of having my manhood in your mouth Dani," he whispered. I emitted yet another soft moan.

Master continued his instructions, "Yes, now lick the tender underside of my sack, Ah, you are indeed a natural my pretty, pretty sissy! Trace the sides of my sack next to my thigh, Yes, good girl! Now return to the base of my balls and begin tracing your way slowly back up the tip of my cock with your sweet tongue. No hurry, nice and slow like the good little sissy cock-boy you are!

"Ah, so good my pet – now around the head and be sure to lick the slit at the top. Excellent, now it's time to take the shaft into your mouth. First lick the sides of the shaft to prepare it for your sweet mouth and throat."

I, of course, did his bidding with alacrity.

"Now sweet sissy, make an "O" with you lips and take the head and shaft into your mouth and come down on the shaft. Good girl, but slowly. Become used to it. Yes that's it, sweet sissy, but change your angle so that more of my meat can get into your throat. Go slowly and experiment. Yes, now come up keeping your lips tight about my meat. Ah, now work yourself up and down and keep working your slutty little tongue."

I still remember every second of it. This was not just licking and playing with him, it was wholly and truly sucking his cock! It twitched, throbbed and was so alive in me. At one point as I came up on his cock my mouth slipped off the head with a little pop sound. "Ah Sissy," he said, "Now you know the sound that a true blow job makes. Yes, it announces to all that a serious cock sucking is happening!"

With the little pop I also realized fully just what I was doing and accepted it completely. Yes, I was born to suck cock! I again sighed a moan of lust and returned to that beautiful symbol of manhood with renewed vigor – one hand at the base of his cock and the other gently cupping his massive balls.

Master continued, "Yes you are getting it. Now sissy drag your tongue on the underside of my shaft as you move up and down. Increase your sucking as you reach the top. Ah, excellent! It comes to you so naturally indeed! Think of my cock as your reward for being so beautiful and sexy for me!"

I glanced up at his face, now covered with pleasure. It was my first view of a man from his cock up. I quite liked it. He returned a knowing smile.

I discovered that a man's parts are a symphony of pleasures and sensations. Not only the silky shaft and velvet head, but also the delectable balls – so full of promise of yummy things to come, erotic sides on each thigh bordering on his "package" and then, a fleeting thought about his tender rosebud – did that need licking as well? The very feel of his manliness throbbing in my mouth was overwhelming. His manliness utterly possessed me – making his cock part of me. Nothing else seemed to matter.

Now I noticed changes in him. His face began to become more intense, his balls seemed to change, growing slightly in size, and his breathing became more rapid. Yes, "that moment" was fast approaching.

He, I think sensed a moment of panic in me and placed his hand to the side of my head and gently whispered, "Easy sissy, relax and only suck the top of me. Use your hand to gently stoke the base of my cock and the other hand to softly knead my balls as they start to deliver my man juice to you. Ah, gently, slowly sweet sissy. Prepare to accept my gift."

With that both his hands he tenderly, but firmly, positioned my head so my mouth was just covering his helmet. I knew now there was no choice. I was to receive the great and full measure of his manliness – his seed.

I sucked, used my tongue and kept one hand stroking his base and the other on his balls. How I did it all at once, or even if I really did, remains a mystery. I was now a captive sissy performing her scared duty for her man. I knew I was entering a new part of my life. This was not just a little nancyboy prancing about in her mother's finery, nor was it even the perfect pantyboy being displayed in a nightclub. No, I was about to fully enter the world of functioning cocksucking sissies, from which I somehow realized I would never return!

He body tensed once again. His cock and balls seemed to grow just a bit. "Now, relax and accept your fate, sissy. You know it is meant to be!" he said. I, typically, moaned yet again. I was trembling from anticipation – was it fear or simple acceptance?

He held me at the tip as the first warm burst erupted into my mouth. It was more than I expected and I instinctively swallowed part of it. The slick feel of it more impressed me than the taste. While pondering just that, he moved me deeper on his shaft and the second cum rope entered me, some going directly down my throat. I almost choked for a moment by recovered, swallowing part of it.

Now I sensed not only the taste and feel, but also the smell of a man's cum. Every nerve seemed to tingle in my body. I even notice my little teapot was having its own little revelation. Then a third, smaller shot hit me. This time I moved it about my mouth, accepting it and inwardly realizing that I had indeed crossed a Rubicon. Drops began to seep past my lips as I tried to process completely what was transpiring.

Again by instinct and without his guidance I swallowed again and went deeper onto his burning cock, I gently squeezed his balls as if to milk them further. I was a sissy possessed by this magnificent cock! Something drove me to want more of his sweet cum.

"Oh, sweet, sweet, sissy", he said as he grunted and released a fourth stream into my mouth. "Relax and savor it. Learn about its taste and feel."

I moved up just past its head and slowly mouthed his cum. It was thick, a little salty, but quite nice. The feel of it remained all over my mouth and a little bit down my throat. He was softening and I felt a form of regret, but also satisfaction. For some unexplained reason I again took his member into my mouth and gently drew my lips slowly up its length, gathering the remnants of his man juice. Looking at my Lord and Master directly into his eyes, I licked my lips and caught a small run of cum from my jaw on my finger and licked that clean as well. I then bent forward and gently kissed the tip of his cock, looked up in his eyes and said, "Thank you, Master!"

I simply could not get enough of the passive-aggressive joys of the act. Being on one's knees was so very submissive, taking his piss instrument into my mouth so totally submissive, and then finally eating his sweet cum was utterly submissive. However, making him buck and yearn for more sweet oral pleasure seemed strangely aggressive!

Well, so there. I sucked my Master and loved it, but that was only part of the experience. Oh, yes, I had sucked his cock with alacrity. I adored it, however another unexpected a divine treat, really my final epiphany of this wonderful night, was to come.

Master took me into his strong arms. I melted even further into him with the taste, scent and feel of his man juice still in my mouth. Amazingly, he kissed me deeply, unconcerned about my semen infested mouth. I molded to his embrace, caring only about being his love object.

From my hungry mouth, he moved to my neck and then, moving aside my bra top, to kiss my titties. There, I met my sissy Waterloo! Once kissed I was done! Not only did he kiss my hard nipples, but then tenderly sucked and nibbled on each delicate sissy treat! My puffy hard nipples were more alive as I had never thought possible. Of course the pleasure centered on my delicate little bud, but it also reached deeper within me. I reached out for a held his beautiful cock. I loved the touch and feel of it.

He led me to a chaise lounge and continued his sissy feast. I utterly succumbed to his tender ministrations. Never had I been so completely sexually overcome. Every part of my body surged with energy I never knew I had. I shuddered. Today I know it as a typical sissy orgasm, but that night it was tectonic!

The best was yet to come. Sir John, my divine Lord and Master, was about to introduce me to anal pleasures. He moved aside my bottom, opening both my little teapot and my little sissy rosebud. His lubricate finger entered me. At first it was shocking, then a little painful, then delightful! His mouth never left my puffed, hard nipple. The combination simply overwhelmed my senses. A feeling deep within me grew in intensity like a runaway freight train.

My little twinkling twinkie overflowed, squirting sissy cream at least two feet. My entire body shook with the most amazing, and first true, orgasm I had even had. Hello again sissy world! Dani now certainly had arrived!

Sir John scooped up my warm sissy cream his fingers and fed it to my hungry mouth.

"Well, sissy, now you understand the joys of being just who and what you are," he softly whispered. Then he again took me into his strong arms, softly kissed me and let me slowly recover to something approaching a normal breathing and heart rate. Tears of sheer joy came to my eyes and a found myself almost weeping with spent pleasure.

"Yes, sweet sissy, I understand. You now have discovered the true pleasure of simply being yourself. Weep with the joy of acceptance darling child. Your Master will hold you tight."

After a bit, Sir John disengaged me. He looked into my eyes, briefly kissed me on my lips, and said, "Time to get you back to your hotel little one." I reluctantly let go and looked about, not really sure what to do next.

He chuckled and said, "Well, sissy, first we need to clean you up a little bit and then get you dressed. I have some new things for you that I think you will adore. Go use the cabana's bathroom. I will send Miss Maria in to help you fix your face and hair. I also want her to take some body measurements of you. She is a trusted employee and you shall obey her completely. I believe that you will find all the necessary items there. Leave your bikini in the hamper and use the wash cloth on your body, by that time Maria should be there. Once you are prettied up come back and I will dress you."

I reluctantly removed the bathing suit, washed myself. I spotted a short silk kimono wrap, and donned it over my body, naked expect for my jewelry. Maria arrived, took many measurements of my body, including my little twinkie, writing each down on a chart. She closely examined my little sissy titties and nipples. Taking up a small jar and massaging some cream onto my breasts she said, "Here, Sissy, this will help those tender titties."

She did a remarkably quick, but highly effective, repair my face and hair. And before I could appreciate it, she told me to go to the cabana's sitting room. I looked back at the amazing woman, smiled and said, "Thank you, Miss."

Sir John greeted me with a warm smile and said, "Even in just a silk wrap you look stunning. I see you're getting better with your hair and makeup as well, or is that Maria's expert touch? Now come here as I have some lovely things for you to put on."

Next to him on a day bed were the sweetest bra, panty and garter belt set I had even seen. They were again white, but made of fine lace. Master had me step into the panties and then pulled them up my legs and smoothed them out over my hips and derriere. The panties fit like the bikini bottom I had worn earlier and their lace created the most wonderful feeling. The bra was even better! Its underwired cups gathered my flesh about my tender titties. The lace tickled my now very tender nipples divinely. Then he handed me the garter belt and said, "I want to see you put on your stockings. It's the very essence of femininity."

I hooked the belt about me. It was tight about my waist and created a nicely defined waistline. I tucked the suspenders through my panties and picked up the sheer white sheer stockings, admiring their intricate lace tops. First taking off my anklet, I rolled the stockings and began the process of carefully unrolling them up my legs, fully aware that Sir John was watching my every movement. "You have done this before, haven't you, Sissy?" he rhetorically asked. I merely giggled in a girlish way as I coyly looked up at him while re-clipping my anklet above my foot.

"Now, sissy, one more little thing for you to experience and contemplate, he said. "Come over here and bend over this chair. I am going to introduce you to the subtle joys of being plugged – just a small amount this evening to acclimate you to it."

I minced over to offer my sweet sissy ass to my man. "Bend over that chair and pull your panties down," he bade.

With my somewhat tender sissy hole offered I again felt a soft finger covered in soothing ointment tenderly enter me. It was followed by a small long thin object that appeared somewhat soft, almost like jelly. "It's a silicone training plug with some soothing medication on it, sissy. It will not only soothe you but also remind you of your delights this evening," he said.

It did soothe, but also it began to stir those intense sexual feelings I had experienced only a few minutes prior. As I straighten up from the bend-over position I felt the plug realigned itself and enter me even more deeply – another very sensuous feeling. Although a little uncomfortable, I quite liked the filled feeling.

He pointed to my slacks, blouse and accessories neatly hanging on a valet. I wondered to myself how they got there, and it seemed that they also had been pressed. I half thought to myself that a sissy could really get use to this treatment! I minced over and again experienced the rapture of donning such sweet delicate thin material, especially over my full lingerie outfit. The sissy shoes were even yummier with stockings on. The gentle tug of the stockings on the garter's suspenders was just heavenly. This time it just seemed so much more natural to not only don, but to wear such things. Somehow they seemed to glide onto my body.

"Here, sissy, take this bag. It has a pretty little baby doll nightgown for you to wear this evening and also some basic cosmetics to make yourself pretty in the morning. Please leave your stockings, panties and bra on, but be sure to take off your facial makeup before you go to bed with the cold cream you will find in the bag, and then apply the moisturizer. A sissy must take special care of her skin to be her prettiest!" he gently commanded. "Oh, and Dani, do not remove your plug until morning!"

With that, he offered his arm and we were off. I was exhilarated riding beside him in his sporty car. A new joy and confidence literally bathed me. I already was thinking about a long kiss goodnight. The plug firmly set in my derriere was a new experience. I, like every secret sissy, had toyed with things "up there," but never had I experienced something so much "up there!"

Walking to the car was one thing, sitting in the moving car quite another! Not only from the soft plug so deep inside me, but also from the exquisite feeling of the lingerie. The tug of my garters and bra were driving me to complete distraction. My little peenie didn't get hard, but my body was starting to feel that special tingle Sir John has delivered to me earlier. "Oh my," I sighed to myself.

It was late when we arrived at the hotel entrance. Sir John merely mentioned to the doorman to hold his car. He then rounded the car and opened my door. I brought my legs about through the door first, he extended his hand, I allowed him to grasp my limp hand and wrist, and he almost ejected me out of the car. I took advantage of the momentum to wind up in his arms. What a wonderful feeling! Thank God he was so strong and held me tightly as my knees almost failed me. I let out the most sissy of squeaks. Yes, this man was going to get a world class goodnight kiss!

He escorted me to my room, often putting his hand both to my back on top of my bra strap and to my derriere and thighs, feeling my garter suspenders along the way. He asked me for my key and opened the door for me. I turned, looked up into his eyes and simply said, "thank you, Master." He smiled and, yes, I got my knee-buckling kiss! "Oh," I though, "Some dreams really do come true!"

After that I found myself alone in my room. Exhilarated, but now exhausted. I reluctantly took off my outer clothing, removed my makeup, but could not resist reapplying a touch of my lipstick. Whatever disappoint I felt with undressing, it was more than made up for by donning the sweet sissy babydoll. It was a sheer confection ending just at mid panty and fully showing my sweet delicate lace bra, panties, garter belt and stockings.

After looking at the sissy confection in the full length mirror for a little bit, my exhaustion took over. I went to bed and quickly fell into a deep sleep, but still unconsciously rubbing my silken gartered and stocking-covered legs together while holding by bra-embraced chest.

 

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