Queen of Paradise

"Well, Maria your husband is lucky he is one of that kind of men where woman's clothes look just as good on him as the women they were made for" Mark replied with a smirk on his face. "I'm sure with the top on he would look just like a teenage girl from the neck down" he continued "and you must know how sexy women feel in soft satiny things." "Oh he knows, believe me, Mark judging by the instant hardon he got when he first put them on, we actually had to wait several minutes before we could leave our suite" Maria laughed as she patted Marks' arm.

Mike was really embarrassed now how could his wife have embarrassed and humiliated him like this. Maria could sense it and decided to ease up for the moment on her husband.

"Oh come on now honey we are just teasing you. Come sit down and have your drink with us" she instructed. For his part, Mike was all too eager to sit down and avoid being the center of attention for everyone in the pool area.

After several minutes of small talk, Maria could see that her husband was still extremely uneasy about sitting at the table in his bright metallic pink girl's bottom next to a man that quite literally any woman would want. Maria began "Mike honey we meant only the kindest of compliments, you really do look sexy in those bottoms really! Guy or girl, you look great! I really mean it! Look at all the other guys here at the pool in thongs and bikinis and you really do look hotter than any of them! Right Mark?" Mark nodded in agreement and said" I think I have a way we can settle this. Tonight is the Queen of Paradise contest."

"What's that" Maria questioned excitedly.

"Every year we have a drag contest when men dress as women and the most beautiful one is given the title Queen of Paradise," Mark explained.

"Oh that would be perfect for Mike don't you think Mark?" Maria exclaimed.

Mark replied "I would not suggest it if I did not think he could win."

"No way, there is no way on God's green earth that I am gonna dress up like a woman for a contest NO WAY!" Mike protested.

"Oh come on honey what's the harm." Maria said, "And after all, you did it for our sorority party in college and that was fun."

Mike replied "That was done as a joke,"

Mark interrupted "Oh this is no joke Mike there is a $5000.00 dollar prize for the winner among other benefits."

"That settles it, Mike, we are winning that prize! Don't look at it as an embarrassment look at it as your opportunity to prove that you are clever enough to win $5000.00" Maria declared. Mike was still shaking his head in disapproval.

Mark suggested then he just tries, he had a Broadway makeup artist staying at the hotel for the weekend that he was sure would help. "Let her work on you for a little bit and if you don't like the results then you don't compete," Mark said. "See honey, that's how you can do it, just try and if we don't like the results we don't enter and it is $5000.00" Maria finished. Possibly it had been the unusually strong alcohol drinks that he had been consuming or the pleading in his wife's eyes but reluctantly agreed with the caveat that if he did not think it looked good he would not enter. Maria agreed but added that since it was the three of them involved in the endeavor that the three would judge.

Mike started to protest when Mark interrupted with "Let me call Miss Stephanie now and get this transformation started." Mark was off the phone shortly and stated Miss Stephanie was up for the challenge and staked her professional reputation on the fact that we will not be able to recognize you when she is finished. She is waiting for you upstairs in suite 1023 and no need to change into anything she has everything she needs. "But Maria what about you I don't want to leave you alone." Mike protested.

Mark jumped in with "OH, She is in good hands I will show her around the shops and boardwalk and possibly get a bite to eat after that."

Maria smiled and put her arm around Mark and explained "See honey I am in very good hands. Now hurry along I am dying to see how you look all made up."

Mike didn't like the sound of that but got up from the table and headed towards the pool area exit and the elevators. The last thing he heard before leaving the pool was Mark order a bottle of Champagne for their table.

A few seconds after the knock the door to room 1023 swung open. Standing there in from of Mike was a beautiful brunet woman with perfect breasts, beautiful lips, tight fitting mini dress and a certain something he couldn't quite place. "Well, well, well you must be Mike. Don't just stand there come and let's see what we have to work with."

With that, Mike cautiously walked into the suite and glanced around. Miss Stephanie must have sensed his nervousness and took control of the situation. She instructed Mike to take off the shirt, which he immediately did and Miss Stephanie slowly walked around him as if inspecting a piece of art for purchase.

"I can do it!" she proclaimed "Absolutely! No one will recognize you." "Come sit down" she directed Mike to a table near the balcony and went to the mini bar and took out a bottle of champagne. The two sat and sipped champagne as Miss Stephanie outlined the transformation process. After several glasses of the bubbly, Miss Stephanie stated it was time to begin. "First we must get rid of all the hair on your body" she stated and led him to the master suite bathroom. "Take off those pretty bikini bottoms" she directed as she reached for a bottle of Nair.

Michael was familiar with removing pubic hair as both he and Maria preferred the smooth look and feel of hair free genitalia however he had never fully removed all body hair.

The shower took about fifteen minutes. As soon as Michael stepped out of the shower he could feel the difference on his totally hairless body. It was strangely exquisite and somehow gave rise to a sexual twinge deep inside. He naturally had very little body hair but now the touch of the towel to his arms and legs excited him. "Was this what a female always felt?" he thought to himself. There was a pink silk cover up put out for him that he eagerly slipped on. The feel of silk against his now smooth body was an immediate turn on even though the wrap only reached his mid-thigh. Miss Stephanie entered the bathroom, stared at the now smooth and hairless body and said: "let's have a look."

She walked over to him and undid the front of the wrap. Michael's embarrassment and excitement mixed with the new physical sensations he was feeling were impossible to conceal and his five-inch cock was now clearly semi erect. Miss Stephanie stepped behind him and reached under his wrap and ran her fingers from the back of his scrotum to his asshole.

"Good, very smooth, you must have done this before." She smirked. She returned to the front of his body. His cock was now fully erect. Miss Stephanie now had a devilish grin on her face.

Mike's face was beet red. "It's very helpful that you have fine feminine body hair, it makes removal so much easier." She explained. With that, she reached out and grabbed his erect penis with one hand and with the other began to feel for any hair around his balls, base of his penis and around the top of his penis. "Great!" she said. "Excellent job!" During the examination, she had been moving his erect penis from one side to the other as a doctor would during and examination. This was getting to be too much for the hairless silk clad man.

There was now pre-cum leaking from his cock. This fact did not go unnoticed by Miss Stephanie. She moved her thumb slowly back and forth over the head of the leaking cock while she cupped his balls in her free hand. Mike began to quiver a little bit helpless to control his leaking cock. Gently dropping to her knees Miss Stephanie aligned her mouth with the dripping cock. First there came a slow lick over the bulging cock head to clean the pre-cum.

"We'll need to take care of this before we can continue" she stated matter-of-factly. She proceeded to gently kiss the head of the still leaking cock and then in one move she engulfed the entirety of his smooth cock. She was clearly an experienced cock sucker. The look of pure ecstasy on Mike's face as she was able to swallow his entire cock and use her tongue to lick his balls at the same time was driving him to the point of no return. Mental guilt gave way to physical uncontrollability and He began to ejaculate what seemed to him to be endless ropes of cum down the gorgeous woman's throat. It seemed like forever before Miss Stephanie slowly rose to her feet. With a devilish smile, she moved her lips to his. It was a long sensuous kiss that began with cum from Miss Stephanie's mouth and tongue being forced into Mike's mouth. This continued for several minutes until there was no more semen to go back and forth. As quickly as it began it was over.

"Ok, with that out of the way we need to get started here baby doll. I'm going to turn you into a woman that even your wife won't recognize!" Miss Stephanie declared.

Miss Stephanie put rollers in Michael's hair and led him to a salon-style hair dryer. While his hair was drying she applied glue on nails to his fingers and painted them a very feminine glossy pink color. The thought went through Michael's mind that this was the second time in as many hours that he had tasted and swallowed his own cum.

With hair dry and nails done Miss Stephanie was now ready to move onto makeup. Michael kept looking at his female nails. How feminine they looked and how different his hands felt. He knew how delightful he felt when his wife would run her nails over his face, his body and especially his cock. He daydreamed about what his hands would feel if they were caressing the body parts of another. What would it be like to be in his wife's place to gently stroke her husband's cock and balls? His cock began to twitch again and he forced his wandering mind back to earth.

It took about forty-five minutes for Miss Stephanie to complete the makeup including eyebrow tweezing, fake lashes, eye liner, and foundation and lip liner. She then switched to styling his hair. Since Michael wore his hair at a girl's length she decided not to use a wig. Miss Stephanie decided on the Antonia look for him. It would require the buildup of weight on both sides of the face created by the graduation of curls and a long fringe covering the forehead. That took another twenty minutes. With face, hair and nails done it was time to move onto the lingerie. Clearly, for the title of "Queen of Paradise," it must be the sissiest of all pink that there was. Pink thigh high stockings, lacy pink garter belt, lacy pink push up bra, pink stiletto heels, pink thong covering the gaff and a choker to cover the Adam's apple completed the basic transformation. Michael had not been allowed to look in a mirror while any of this had been progressing and now it was time for him to seen the preliminary results.

Miss Stephanie took him by his manicured hand and led him to a full-length mirror in the master suite. "On three open your eyes and behold Michelle." Miss Stephanie instructed.

When he opened his eyes he was amazed, shocked and excited all at once. He didn't recognize himself let alone worrying about whether his wife would. He was in love with the woman he saw in the mirror! How pretty she was. How absolutely feminine a reflection looked back on him. He had to look very hard to see anything that resembled Michael.

"Well?" Miss Stephanie questioned. "Do you like yourself as Michelle?" came next from her.

It took several moments for him to respond but when he did he could only shake his head yes and say "it's unbelievable I love it." Miss Stephanie stood behind him and adjusted his bra straps and push up inserts. She fiddled with his garter belt stays for his thigh highs making him more feminine than ever. His cock tried to grow but now he felt the restraint of the gaff and was relieved that his hardon would not spoil the moment. "Walking in heels will be very important in this competition" she explained so we better get started on that. It took a few seconds for the words to break through Michael's complete mesmerization with his newly found feminine self but he did try to walk. Thankfully, Miss Stephanie was there to steady him. "Now Michelle, a girl must put one foot in front of the other and move their leading hip at the same time." Miss Stephanie explained. "We want to show off our asses as well as our beautiful legs." She further explained. After fifteen minutes Michelle was able to navigate the room completely on her own and with the confidence and dignity of any runway model.

"Now before you put on your evening dress there is one other part of the competition we must practice for" Miss Michelle stated and added, "It could get messy while practicing so that's why you should practice it in your lingerie." Miss Stephanie matter of fact stated "this is the deepthroat and blowjob competition. Part one is who can deep throat a dildo the furthest down their throat and part two is who can make a dildo ejaculate the quickest." Michelle had a look on his face that said: "no I'm not doing this." Reading this look Miss Stephanie took Michelle back over to the mirror and stated in an authoritative but gentle voice "You are Michelle, not Michael. While Michael might not suck cock Michelle loves too. She wants to be the best girl she can. She wants to be crowned Queen. She wants to win five thousand dollars. Isn't that right Michelle?" "Think of yourself as an actor playing a part it's just that simple." she emphasizes. Looking in the mirror Michael slowly came to see the difference between Michael and Michelle.

Miss Stephanie went through all the tips and tricks of how to deep throat a cock. It was explained that lubrication is key in both deep throat and blowjobs. Michelle practiced on her deep throat skills first. Getting used to the artificial cock pushing up against his gag reflex point took some getting used to. With a little bit of practice and patience, Michelle was soon deep throating the biggest of the dildos Miss Stephanie had. With deep throating mastered Michelle was eager to move on to blowjobs.

This was an entirely different set of skill she began to realize. Lubrication was important, yes, but Miss Stephanie explained that other skills such as tongue movement, hand stroking along with his newly acquired deep throating skills would all have to be used in unison to make the mechanical penis she would be using spew artificial cum down her throat. The rules state that she must swallow all of the cum when the penis beings to ejaculate. Michelle would be disqualified if she choked, gagged or spilled a drop of cum.

Luckily Miss Stephanie had a machine very similar to the one that would be used in the evening's competition in her suite. Michelle was amazed when she saw what Miss Stephanie brought out. It actually looked like a portable glory hole. There was a board with a hole cut in it and what looked like a limp cock protruding through. Miss Stephanie explained that to bring this device to orgasm would take two steps.

First, she explained, was for him to get the cock hard. This was best accomplished by spitting, sucking and licking the phallus and balls while at the same time stroking. The machine would gauge all of these actions at once and if done properly the cock would gradually come to full erection. It was at this point step two came into play. Sucking was now most important and that needed to have deep throating mixed in. When the electronics sensed that correct sucking, stroking and lubrication had been present at the same time for a certain length of time the machine would trigger an orgasm without warning.

Miss Stephanie explained to him that when this happens you must have the cock all the way down your throat otherwise you will choke, gag or spill the cum. Miss Stephanie filled the machines cum chamber with a homemade recipe of egg whites, flour, and milk and salt that looked, felt and sort of tasted like real cum. Miss Stephanie demonstrated its use for Michelle. She watched as Miss Stephanie demonstrated the techniques for stage one and stage two exactly as she had just explained. It took Miss Stephanie about two and a half before Michelle saw her quickly stuff the entirety of the mechanical penis down her throat. Michelle could tell the machine was ejaculating and Miss Stephanie was swallowing cum as fast as she could. When the machine stopped pumping cum down her throat she slowly eased the cock out of her mouth. She looked up at Michelle and with a big smile said "Now that's how you give a world class blowjob!" Michelle had been watching Miss Stephanie. He was amazed and deep down a little envious of how easily his tutor had worked the cock to the point of orgasm. The panty clad man was eager to test his skills and wanted very much to match or beat the time of the blowjob she had just witnessed.

Miss Stephanie reset the cock sensors and cum release mechanism as well as the stopwatch function. "Well Michelle are you ready to become a blowjob queen" Miss Stephanie said with a sinister smile. Michelle was mentally convincing himself that this was just a role he was playing. He really was not a sissy cock sucking faggot bitch boy. It was just a roll and once crowned Queen of Paradise and five thousand dollars in his pocket that would be the end of it.

As he approached the limp artificial cock dangling through the hole all of Miss Stephanie's instructions and tips were racing through his head. He dropped to his knees, licked his lips and reached for the flaccid cock. It was now time to go into a full acting mode. If he were to win this he was going to be the best cock sucking slut he could be.

He wrapped his pink nails and hand around the base of the penis and gently started to kiss the bulbous head of the machine cock. It was so real so lifelike. It really was hard not think of this as a real life cock. Kisses turned to licks and his hand began to slowly stroke up and down the base of the lifeless cock. Michelle then moved to lick the cock just as one would lick a popsicle. To her amazement, the cock showed the slightest amount of stiffening. He was doing it he thought. This was great and only served to encourage more of the same licking kissing and stroking of the hardening cock in front of her.

More spit he thought, a harder grip and faster stroke maybe. He began to slap the cock against his mouth and cheek. This greatly increased the speed at which the cock was hardening. With a couple of quick deep throat moves the machine indicated that the cock was now at full erection and ready for stage two. Michelle was really into it now. He had brought the cock to full erection and if all continued as planned he would soon bring the machine cock to orgasm.

Now was deep throat and stroking time to finish the job off. Several things went through Michelle's mind. Keep the cock lubricated. This he could do on each deep throat dive. Time the stroking to his backing out of the deep throat. Keep a keen sense of when the orgasm might begin and remember to then deep throat completely and let the cum shoot down his throat and not accumulate in his mouth.

He was now enjoying the challenge. He was into sucking this cock off to completion. He keeps repeating the same move suck deep be prepared for cum explosion and lubricate on the way down and stroke on the way up. He was in a frenzy now, the movement was automatic, the time was soon approaching he, though. On a down stroke of a deep throat move, he felt the slightest tightening of the base of the life like penis. This was it he thought. Now is the time. He took a deep breath and held his mouth and lips to the base of the cock and the head was down his throat past his gag point.