A Sissy Maker Tale Pt. 07

Sissy Candi re-entered her Mistress's bedroom exactly at the thirty minute mark per the instructions given to her. Once again, what impishly stood before the two women was a totally transformed sissy.....from the blonde haired pink-clad slut that had been previously tested with her corner time, there now stood a vision is black, from her submissive toes to the top of her head. Black pumps with 6" heels were locked in place. Black thigh high sheer stockings were held up with a leather garter with oversized straps. A black crotch less silk panty was in place, allowing for the caged clitty to be prominently shown, leaving nothing to the imagination. Once again, a corset, this one black, was impeccably molded to the sissies waist and torso, still allowing access to the slut's sensitive nipples. A black leather collar was locked in place and was partially covered by the auburn locks that cascaded down the sissy's neck. The cock-slut had totally re-imagined her makeup to match the new ensemble, with smoky eye shadow that gave her eyes a shouldering, sexy look.

Candi was the perfect looking submissive sissy. Every detail of her appearance had been methodically achieved with what could only be explained by months and months of extreme training by Mistress Alexandra.

But the story of how Candi came to be might surprise you.

Adam ( Candi's pre-sissy name) was a highly intelligent newly divorced 28 year old who was involved in the finance sector, scrunching numbers all day long in the risk-management department of the brokerage in which he worked. An MIT graduate in engineering, Adam was introduced into the finance business by a college friend, who flat out told Adam that the money was in finance and that with his brain Adam could go places and earn some decent money. So Adam applied and was immediately accepted at a firm with branches on both coasts, which allowed Adam the luxury of staying in California, a place where he grew up.

A year into his job, Adam met his soon to be wife, Christy. A quintessential Ivy leaguer, Christy had transferred to the West Coast and was working in the same firm as Adam. A chance encounter at lunch led to a dinner date and the rest is history as they say. Adam was smitten from the outset and for the first time in his life had met a woman who truly liked him and was interested in him. Never a lady's man, Adam had been in a few short-lived relationships in the past but nothing serious ever transpired. Adam was fit, athletic and good-looking but the one part of his body that betrayed his confidence was his penis. Because of its small size ( 4" when fully erect ) Adam was so self-conscious that he actually avoided sexual contact rather than pursue it. It was only after six dates with Christy that he finally found himself naked in her bed. And much to his chagrin, she didn't seem to mind the size of his cock. Or at least she didn't ever mention it to Adam. Perhaps Adam thought, Christy was a virgin and really had no idea as to what a normal sized cock should be.

Unfortunately, the sex that occurred prior to their marriage could only be described as that of a clock....the same movements over and over again. Oral sex was virtually non-existent, but neither seemed to mind. It was almost always a case of a missionary position fuck followed by some loving cuddling. Adam never seemed to notice that his soon to be wife never achieved a mind-blowing orgasm throughout their dating period.

And so it came to be, that only after two years of marriage, Christy met a new colleague on a business trip and after enjoying more than a few drinks after work, she found herself in his hotel room. He was the exact opposite of her husband. He was enigmatic and sexy. He was confident and mysterious. And he definitely knew what he wanted. He almost tore her clothes off and she surprisingly did the same to him And as she pulled the boxers down she was met with a fast growing cock the almost twice the size of her husband's. And when her new found lover told her to suck his dick, she did not hesitate at all. She was entranced by the cock in her mouth and slowly began to lick and suck the growing member. He instructed her as to what he liked and she was in heaven pleasing this man with her oral ministrations. Even when he stuffed the cock down her throat she still was loving all that cock sucking was entailing. And when he shot his huge load, she was shocked at the force and the quantity of his cumming. Sperm squirted out the sides of her mouth and at that moment she knew she would never be the same!

And after spending all night getting fucked, having her pussy and ass eaten and doing the same to her companion, she was convinced that the man she married really wasn't much of a man when it came to sex.

The divorce shocked Adam and after it was finalized he finally found out about his ex-wife's lover and how she had been fucking him during their marriage. He was crestfallen and swore to himself he was done with relationships involving the opposite sex.

Months went by and Adam immersed himself in his work. His twice daily masturbation sessions kept his mind off of women and he fell into a comfortable routine. All was going well and he was embracing being alone again...finally.

And then....

She spotted him at a Home Depot, picking through the orchids, looking for just the perfect one. He seemed intent on his quest and did not even notice her standing next to him. She had developed an almost sixth sense-like ability to determine the probability of "turning" an Alpha male into what she desired. Alpha, as she saw it, was a guy who was fully employed, was ambitious, and was not wimpy in any way. Wimpy was a definite turn-off for her and she detested weak men. She also preferred thin, athletic men who took care of themselves and were neatly groomed, even in a Home Depot on a Saturday afternoon

"Excuse me", she interrupted his search, "you seem to know a lot about orchids and all I ever do is kill them off. I was wondering if you could give me some pointers?"

Adam looked up and was immediately captivated by the beautiful lady standing very closely next to him. She was tall with long black hair that fell almost to her waist. She had a gorgeous face that merely complimented her perfect body. Her tight jeans left nothing to the imagination and her sexy black high heels completed her statuesque look.

With a face quickly blushing red Adam fumbled for an answer.

And of course this further convinced the lady by his side that the creature trying to find the will to speak before her was a definite candidate for her desires.

"Sorry," She stated. "My name is Alexandra. What is yours?"

"Adam."

" Well Adam, normally when I ask a question of a young man he gives me an answer. But you seem to be hesitant. Do I scare you Adam?"

" No not at all. I was just so surprised you were talking to me."

Alexandra carefully looked for the tell-tale signs of a submissive, and this guy was ringing all the bells for her.

" So Adam, you will help me please? I would be so grateful for any advice you could give me." Help me pick out a nice healthy orchid. Perhaps my luck will change if you do the picking."

Adam was struck by how Alexandra worded her request. Well it really wasn't a request, it was more like an order. "There is a lot more to just picking the right one. Orchids are very temperamental and they need proper care. How you water them and where you place them in your house is vital to their growth."

"It's settled then Adam. Let's pick one and you will follow me to my house and show me just the perfect spot to place it. Don't worry, I live very close just up the canyon at the top of the hill. Now be a dear and choose. Don't be shy sweetie, choose a lovely one for me."

Sweetie? What the fuck thought Adam. I just met this lady and she called me sweetie. But the thought never crossed his mind of not doing what she asked. So he proceeded to pick out a nice purpled flowered one and tried handing it to Alexandra.

" Oh please, carry it to the register for me. That's a good boy. Thank you so much dear."

Her smile stopped him in his tracks. Adam was smitten and it embarrassed him to no end. In his mind he couldn't come close to deciding what was affecting him this way. And for some odd reason he was acquiescing to her wishes and carrying the orchid to the register, following behind her as he admired her luscious ass and suddenly fantasizing about being with her. And when they reached the register, Adam surprised himself by reaching for his credit card and giving it to the cashier.

"Oh no Adam. You don't need to do that", Alexandra cooed.

" Please let me buy it for you Alexandra. A beautiful orchid for a beautiful lady."

This was going better than Alexandra could have hoped for. The cute boy was buying her a gift without even being asked. Rather than delay the inevitable, she decided at that point to proceed rather quickly in her assessment of Adam's sissy aptitude.

Alexandra turned around at Adam as he walked behind her with the orchid.

" Let's take my car sweetie. That way you can hold that pretty plant while I drive. We'll come back for your car later."

Before he knew it Adam was sitting next to the most gorgeous woman he had ever met as she quickly drove her Tesla up the hill. They arrived at her home about ten minutes later, and Adam, even though he was clutching the orchid, jumped out of the car to make sure he would open the car door for Alexandra.

"You know Adam...such chivalrous behavior will no doubt get you rewarded. So please keep it up. Now take my keys and open the front door for me. Come on now, don't dawdle. You don't want to leave me waiting in the heat do you?"

Adam rushed ahead, opened the door and Alexandra swooshed by him and entered. Following meekly behind her, Adam was impressed by the lovely hilltop home. Looking for a place to put the orchid, Adam was somewhat shocked to see a variety of healthy orchids set about the home, all doing what appeared to be extremely well.

" Okay you caught me sweetie. I just used the orchid as an excuse to get you up here to spend some alone time with you. Are you all right with that Adam?"

Adam replied, " Absolutely. I am really pleased to be here alone with you. Thank you for inviting me."

Alexandra made her way into the kitchen and emerged with a bottle of wine and two glasses. " Let's go sit out by the pool and get acquainted. You go have a seat, take the wine and glasses, and I am going to get into my bikini."

"Open the wine sweetie. I'll be out in a minute!" Alexandra shouted from the bedroom.

Adam opened the wine and was just about ready to pour when Alexandra came out into the backyard. She was now clad in a bright pink floral bikini that barely covered her amazing body. The bottoms were a Brazilian cut with just a tiny pink string lodged between her well developed ass cheeks. She had on a pair of pink high heels that matched the color of the bikini perfectly. Adam almost dropped the wine as she emerged. Holy fuck he thought. This woman looks like a Goddess!

Alexandra sat so close to Adam on the outdoor loveseat that her thighs were touching his as she began her questioning of him. She wanted to know all about him and eventually Adam was describing his failed marriage and how he had been cheated on. Alexandra was making a mental note of many parts of Adam's story and his history with women. As the first bottle of wine was finished, Adam had become quite comfortable with Alexandra and was opening up to her. She was a very good listener and for the first time since he could remember Adam felt safe and secure with someone with whom he was confessing many things. Alexandra kept pressing on, asking many questions and looking for anything that would further convince her that Adam might be a worthy submissive and eventually a sissy slut for her. This was not her first rodeo so Alexandra was well versed in the art of manipulation and discovering what really excited someone like Adam.

About halfway through the second bottle of wine, which Alexandra had instructed Adam to retrieve from the kitchen and open for them, Alexandra felt it was time to test the waters, no pun intended.

She snuggled up even closer to Adam, and seductively whispered to him.

"Between you and the sun I am feeling very hot and much in need of a swim. Of course I will expect you to join me sweetie."

" I would love to," Adam replied, " but I do not have a swimsuit."

"Oh don't worry about that. I am sure I have something that will fit you. I mean look at your slim waist, you might be very close to my size. Now just sit here and finish that glass of wine while I go find you something to swim in."

Adam did as he was told and soon Alexandra returned holding a pink thong in her hand.

" Her you go sweetie, this will fit you. Now hurry up and go change in the bathroom for me. I can't wait to get in the pool with you."

"But that's a woman's bottom Alexandra."

"So what Adam. It's just you and me here. Now get moving and change immediately. You know how much I hate to be kept waiting."

She handed Adam the thong and off he went. For a moment he hesitated as he got naked and slipped the thong on over his semi-erect cock. She will see the outline and know how small I am her thought. Just when trepidation was setting in, she called out to him to hurry the fuck up. So he scurried out to the pool where Alexandra was sitting with her lovely legs dangling in the water.

" Oh my God!" she exclaimed. " You look absolutely wonderful. And that fits you so well and the color against your skin is heavenly. Now come over and sit next to me so I can feel you. Come on over now sit next to me."

Adam hardened immediately at her statement. No one had ever complimented him in such a way. He carefully walked over to where Alexandra was sitting and sat next to her on the edge of the pool, not only admiring the incredible lady sitting next to him but also the amazing view. Alexandra was telling Adam how, when she bought this house, she definitely envisioned a zero-gravity pool that would appear to fall off the cliff. As she described her vision her hand nonchalantly found the front of Adam's thong and she began to rub his straining erection. Needless to say Adam was not really listening to her talk about her backyard vision. He was quietly panting and the combination of the wine and the take charge actions of Alexandra had him near a climax. Of course Alexandra sensed this and slid into the pool, placing herself directly in front of Adam with her head now staring directly at his hardened little penis and the wet spot that had formed from his leaking pre-cum.

" Well sweetie," she whispered, " it looks like I have aroused you to the point where your little cocklette is straining against my pink thong. Just so you know, unlike your ex-wife, I just adore a man who is less than well-endowed. And in your case it is apparent that your cock was never meant to please a woman. Let's have a look at is, shall we? Now slide that thong down your legs sweetie so I can see your tiny penis."

Adam knew he was being teased and demeaned, but it didn't seem to matter. Without a hesitation, he took off the thong and his tiny cock sprang forward. Much to Alexandra's delight, Adam was not hairy at all. Actually, if one looked closely his pubic hair resembled that of a baby, it being so soft and thin and blonde.

Alexandra laughed out loud, actually cackling loudly as she inspected the tiny cock before her. " Oh Adam, it is so fucking cute. But God only knows there is no way I would even consider that appendage a real man's cock. I mean, it's more like a clitty and from now on I will refer to it as just that."

Adam had had enough. He was pissed and humiliated and readied himself to get the fuck out of there. But just as he was pushing himself up from the pool's edge, Alexandra's mouth sucked in his tiny cock. He had remembered his last blow job was in college, from a girl with virtually no experience who had literally thrown up when Adam came in her mouth. But now, he was mesmerized by what was happening to his penis. Smiling up at him as she fellated him, Alexandra took both her hands and grabbed each one of Adam's nipples. She pinched and twisted them as she continued to suck him. Adam had occasionally touched his nipples when masturbating but the sensation was nothing like this. He was melting before this intoxicating woman and was helpless to do anything but revel in the sexual feelings that were overwhelming him. Alexandra was an expert at edging little bitches and she knew exactly when to slow down so as not to allow her new sissy candidate to cum. Her supple mouth moved up and down his cock and she would eventually take each one of Adam's little balls in her mouth and roll them around while lightly sucking them. As her saliva drenched Adam's cock and balls he was beyond any control. Her lapping and licking was so sensual that his mental state was transformed in such as way that nothing else existed for him but the pleasure he was receiving.

Alexandra had him exactly where she needed him to be. As she released his cock from her mouth, she took one hand off of his nipples and slowly massaged the head of the tiny cock, sensually rubbing it in a circular motion. Adam was so close to cumming that it began to hurt and he began pleading and begging Alexandra to please let him orgasm. And this was it, the moment she needed!

" Well Adam, I will let you cum on one condition. You see sweetie, I want to make you mine and only mine. I must insure there will be no cheating on me from you like what happened with your ex-wife. So if I let you cum, you must promise me that I can lock up your tiny penis in a chastity device until it is ready to be used again. Can you promise me that Adam?"

Alexandra knew the answer already, but she also knew that once allowed to cum, the little bitch would have second thoughts about being locked up. Previous encounters had taught her this and she was now prepared. From under a beach towel that had been sitting next to her, she produced a set of handcuffs. She dangled them in front of Adam and asked him, " So sweetie, I need to cuff your hands behind your back so I can control you when I allow you to ejaculate. I am doing this for two reasons. The first reason is to show you how excruciatingly exciting it will be for you to relinquish control to me. To be at my mercy to see that I give you that orgasm you have always dreamed about. And the second reason, my dear slut, is that once you shoot your seed into my hand, it will be fed to you and I expect you to consume every last bit of it. Do you understand Adam?"

Adam at that point would have agreed to almost anything, so the nodding of his head in affirmation did not surprise Alexandra one bit.

" Oh you are being so good sweetie. Now sit up a bit and put your hands behind your back for me. That's it. And voila, you are now under my control. Are you ready to have me rock your world sweetie?"

Once again, as if in a trance, Adam nodded in agreement. Alexandra smiled and slowly removed her top, exposing her perfect c-cups. She inched even closer to Adam and lifted herself next to him on the edge of the pool.

"Do you want to suck these sweetie? Your Mistress needs your lips on my tits now. So be a good gurl and suckle my breasts. Be ever so gentle and you will be rewarded."

Adam accepted the breast that was next to him and strained to get as much of the nipple and tit into his wanton mouth. He was so green at this Alexandra thought. No one had ever taught him how to orally please a woman. She would be working with a "tabula rasa" with Adam, a blank slate onto which she would apply all of her teachings. She stroked his cheek and mussed with his hair, all the while whispering encouragement.