Seven Lessons Ch. 02

Previously... Bryan is an arrogant biggot. This Halloween season, someone has decided to teach him a series of 7 lessons. Yesterday the lesson was acceptance, but as he chose not to accept the lesson, he ended up with no body hair, wearing a bodystocking and being fitted with a chastity device. Will he learn his remaining lessons?

That night he had many erotic images flood into his dreams, lingerie, fetishwear and sex, lots of sex. Hardcore action of all persuasions had filled his sleeping thoughts with him in both the receiving and giving roles. And then there were the bells, the bells were tolling for him.

Actually, as the fog cleared, the bells became more insistent and he realised that the noise was being caused by the doorbell. He jumped out of bed, put on his robe and slippers and answered the door.

The UPS man smiled at him, "package for you sir," with rather too much emphasis on the sir. He signed for the package, closed the door and caught sight of his reflection in the mirror.

The image staring back at him explained the courier's reaction in an instant. He was still wearing the bodystocking and chastity device, but the house robe he had put on was fairly sheer black nylon with pink laced edging, which effectively made it see-thru and added to this he was wearing matching fluffy mule slippers! As he wondered where they had come from, he was starting to doubt whether yesterday had been a one off.

He started to open the package and to his dismay, on the top of it was another perfectly hand written note.

Good morning Bryan, hope you slept well last night!

Lesson 2 - Humility

In the box you will find a classic french maids outfit.

Your task for today is quite simple. Wear the outfit for the whole day whilst tidying your apartment.

Housekeeping has taken the day off today, so make sure that everything is cleaned to the same standard as you expect the hired help to achieve.

As with last time, you have one hour comply with this task or you will have to face the consequences.

There was no way he was going to tidy his apartment, especially as he had paid an agency to provide him with cheap migrant workers to do so! In fact, he was going to stop this madness right now. He took off all of the clothes he was wearing, bundled them into a bag and got dressed in his work attire. He took the box delivered this morning along with the bundle of clothes and threw them into the boot of his shocking pink smart car. He paused for thought, he was sure he actually owned a much bigger, manly car than that.

Having decided to pay one of his sales contacts a visit to see if he could upgrade them, he set off thinking about how to get his dick out of the damn device it was locked in. When he had become stimulated and his dick had started to grow, the device had prevented it and left his mind full of sexual imagery but his equipment unable to function and this was driving him to complete frustration. Worse still, the more frustrated he got, the more he thought about sex, which was a vicious and near unbreakable circle of torment.

After paying a visit to his sales call, he was going to find doctors surgery nearby so he could get the thing taken off by someone who would not know him or anyone he was acquainted with. Then he was going to drive somewhere private and burn it and the damn clothing!

A quick glance at his watch confirmed that it was now past the deadline to comply and nothing weird had occurred. This was great news, he could concentrate on business and not worry about the stupid "curse" that had alledgedly been put upon him. In fact, he was convinced that he must have been drugged yesterday to have done those thing. He turned off the highway onto the gravel driveway of a country house; he came to the conclusion that he had been a bit hasty with his celebration.

After retrieving his box from the back of the car he found attached another envelope. This one addressed to a "Mistress Rose". He walked up to a large oak door and used the old style pull bell. Moments later a maid of sorts appeared at the door, but his was no ordinary maid.

For a start the uniform was very short and made from shiny satin with several white lacy underskirts. The ruffled skirt did not cover the wearers six suspender straps which were attached to vintage style seamed stockings. To complete the uniform were stiletto heels and black elbow length satin fingerless gloves with white lace wrist decoration. Although the maid's makeup was flawlessly applied and demure, there was no mistaking that the wearer was a man!

The maid held out a hand and introduced herself, "I go by the name of Girlyboy with which you should address me at all times," and added, "we have been expecting your visit today, so if you would like to go into the changing room opposite and put your uniform on, I'll pass the letter onto the Mistress and come back to find you, ok?"

As with the previous day, despite wanting to leave and run away, he found himself in the changing room unpacking his maid's uniform against his will. The uniform was identical to Girlyboy's in every way apart from the black bob-style wig. Although he had never worn these clothes or anything close to them before he found himself adorning them with ease.

The final items to go on, apart from the shoes were the vintage silky stockings. As he rolled them up his legs they felt incredible and if he wasn't wearing the cage he would surely be sporting a hardon right now. Instead he was moaning in frustration and precum was dribbling out of the head of his cock into his tight black lycra panties. Finally he slipped his feet into the shoes and stood up, feeling his calves stretching, buttocks being thrust out and his weight moving forward and the lacy underskirts caressing his thighs.

The door to the changing room opened and the other maid entered. Clasping her hands together and giving a delighted squeal she said, "You look fabulous darling, mistress will be pleased, after we've put some makeup on you of course."

She proceeded to apply a very pale foundation layer to contrast with the colour of the wig, eyeliner, dusky eyeshadow and cherry red lipgloss. When she had declared herself satisfied with Bryans "new super-sexy look", she checked the time and said, "Mistress will see you in the study now, hurry along as she doesn't like to be kept waiting."

Bryan knocked on the door to the study and waited patiently until a stern voice called "Enter". He walked into the study aware that he could walk in heels easily despite having never attempted it before. The room was dominated by a mahogany desk at which sat a stern looking woman who appeared to be in her mid forties. She was reading the letter he had handed to the (other) maid. Her makeup was tastefully done, dark hair slicked back into a tight laced ponytail and a wearing a very professional looking black business suit.

Bryan stopped at her desk and felt the need to stand up straight, keep quiet and fix his stare into the distance behind Mistress Rose.

Looking up she said, "I have here a letter from a good friend of mine that says that you are somewhat disobedient and that you need to learn the lesson of humility, is this correct Brianna?".

Of course it wasn't correct and his name was Bryan, not Brianna he thought. He was going to put her right on that point! He opened his mouth and said "Yes, Mistress". "Not again," he thought and came to the realisation that his afternoon definitely was not going to go as planned (again).

Mistress stood up and circled Brianna and inspected his appearance and uniform. She lifted his skirts, checked his makeup and that his seams were straight.

She announced, "Well, it appears that despite your inexperience at this you have managed to present yourself rather well, although I suspect that you may have had help from my Girlyboy with the makeup. Now, in the box on the side of my desk are some cleaning materials. I have an errand to run and whilst I'm doing this you can clean my study. If you do a good job, there will be a reward for you. If not, you will be severely punished. Do you understand Brianna?"

Bryan meekly answered "Yes mistress" and stood still until she had left the room.

Brianna toiled for hours, polishing, shining and cleaning every nook and cranny of the study until his knees and back ached. One small mercy was that the focus had moved away from his frustrated thobbing penis and the now very moist underwear. Once he had finished his tasks, he stood bolt upright next to the desk, eyes towards the door and waited for the Mistress to return. Whilst waiting he ran the last couple of hours through his mind and could not remember at any time that he had been forced to perform these tasks.

After having watched the clock on the wall count agonisingly through another 45 minutes the soles of his feet and calves killing him, the door was opened and in she walked. Brianna's eyes nearly popped out of his head when he saw her outfit. Consisting of a black latex, fully enclosed catsuit apart from the crotch and ass which was open, a latex hood with eye, nose, ponytail and mouth holes, a red leather studded collar and red thigh-length side-zipped stiletto heeled pvc boots. On her wrists she wore red leather wrist-cuffs with built in rings, her boots also had rings fixed to them at ankle level and most amazingly, both of her prominent pussy lips had four smaller rings in each spread over their entire length.

When she stopped in the middle of the room he dropped to his knees, crawled over to her and kissed the foot of each boot and stayed in that position. "Very good my little pet, I may have use for you yet! Now stay there whilst I check the room" she ordered.

As she walked around the room, checking various items for cleanliness her heels echoing off of the floor. Her voice interrupted his thoughts, "You've noticed my outfit, not very domme is it?" After a pause of 5 or so seconds, she asked, "Well?".

He lowered is eyes and said, "No Mistress, sorry Mistress."

"Well, I'm holding a fetish Halloween ball this Sunday and I'm going to be going as a submissive, does this shock you?" she asked.

Thinking about his answer for a couple of seconds he replied, "A little, Maam".

She informed him that, "In order to be an effective dominant, I need to experience the submissive from time to time. I find it best if I give up control once in a while. In fact I've been dominant for so long that I really need to have my limits tested to extreme levels! I'm so excited, I can hardly wait."

He noticed that her heels were now directly in front of him and that she was facing away. He looked up and saw that the Mistress was leant forward, her butt cheeks sticking out prominently above his head. He heard the door open and the sound of a second set of heels moving across the room. Mistress spoke, "Ah, Girlyboy, would you care to inform our guest as to what he should do when a Mistress presents her bottom to him?".

The reply came quickly, "Yes, Mistress Rose. A sissy should feel honoured to place her face between the queen's wonderous globes with his nose above her gloriously scented hole and revel in the smells and feel of the goddesses behind."

Brianna immediately moved into the position described and tried to lick her asshole, much to the Mistresses disgust!

She wheeled around and instantly slapped him hard on the face, "You do not use your sissy tongue on me unless instructed to do so, is that clear?"

His cheek was stinging and although he wanted to stand up and hit her back, he realised that his ordeal would probably only get worse if he did so. To placate her, he apologized, "Forgive my ignornance please Mistress."

"Since it is you first indiscretion and you have done a magnificent job on the cleaning, I will let you off with a spanking, 5 strokes I think," and after sitting on the edge of a chair and patting her lap, added, "and since I'm feeling generous, you may have your treat after your punishment."

Spanking! There was no way he was going to let a woman spank him he thought. He stood up, walked over to her, led over her lap and pulled up his ruffled maids skirt to reveal his soft bottom. Almost immediately the first blow landed on his right cheek with a resoundingly loud smack. He jumped a little and yelped with the pain that had just been inflicted upon him.

"Girlyboy, unless my pet wishes to endure many more blows, what should she be doing right now?" she questioned.

He had forgotten that the other maid was watching this punishment unfold. "The pet should count each one and thank the Mistress after each Maam," came the reply.

"In that case, we'll start the count from the next one," the Mistress informed him and planted another firm slap on the other ass cheek.

"Ow, I mean ONE, thank you Mistress." Both of his cheeks were burning now and he was worried that the next blow was bound to land somewhere that already hurt. When it came, to his surprise it was on the same cheek as the first one, but slightly higher so there was no overlap. "Ouch, TWO, thank you Maam". Now he had his teeth gritted and beads of perspiration were forming on his face. He was amazed at the strength she possessed and he squirmed as he waited for the next one.

As the blow connected, parallel to the last one, Mistress Rose ordered "Keep still bitch."

"Thank you, THREE, Mistress," came his acknowledgement. Number 4 was a wide palmed blow across the whole area that had been spanked up to now, but despite the searing pain he was able to follow the required instructions.

He guessed the last blow would be something special and tried to prepare his mind for it. When it came, it knocked the wind out of him instantly, landing on the back of this thighs and slightly catching his balls. The pain erupted and he called out, "Ow, shit, fuck" and quickly added, "Five, thank you Mistress".

"For a first time, that was just about good enough," she praised him, "now stay still whilst my Girlyboy applies a healing salve for you." He could feel his face redden to the same colour as his ass probably was, knowing that shortly another man, a sissy at that, would be touching his bare bottom. A bottom that had just been spanked by a woman! Tears started to run down his face, but he did not move from his current position.

He felt the cold cream land on each cheek and a smooth pair of hands start to work it into his tender skin and as it was massaged into his ass it felt kind of good. He relaxed and his cock started to harden, only to be restricted by the chastity device. As the maid's skilled fingers did their magic he let out an involuntary moan and when she brushed them over his most private of holes, he gasped audibly and shivered with pleasure.

Lost in the moment, he was happy for this to continue but was denied by the Mistresses voice, "Stop now Girly, the little slut is enjoying it too much!" The next order came soon, which was to stand up and follow Mistress to the "treatment room".

She led him down a long wide marble corridor to the end room. The door had a plaque on it that confirmed this was indeed the treatment room. As Mistress Rose stepped inside, she flicked the light on to reveal its' contents.

There was a padded leather massage table with a couple of attachments that were obviously designed to hold legs. Mistress climbed on the table and placed her legs on the attachments which left her led down, legs spread and her buttocks only just resting on the edge of the padded table. Brianna quickly realised that this left space for someone to kneel between the legs of the person on the table to provide perfect access to their neither regions. Next to the table, was a sink and drainer upon which stood a bowl of warm water, a towel and shaving kit.

"Brianna, please kneel between my legs and prepare to shave my pussy," she instructed and explained, "when I'm in my submissive role at the weekend I will require a completely smooth and bald cunt. By the way, that is the correct term, when I'm a sub it will be referred to in the vulgar form".

He gathered the equipment together where it could easily be reached and proceeded to lather up the shaving brush. When there was sufficient lather, he began to apply it around the Mistresses beautiful pussy ready for shaving.

Remembering the firm spanking he had received at Mistress Rose's hands, he worried what might happen if he messed this up or cut her. Taking the razor, he carefully shaved a straight line through the foam and rinsed it off in the bowl of warm water. As he got into the swing of things, he treated the area framed by her open catsuit in the same way as his face when he wet shaved, using long and short strokes, cleaning the razor and frequently applying new shaving foam until she had a completely smooth pussy. He had been concentrating so hard that only now, when he was very relieved not to have cut her did he notice that she had been reacting to the strokes of the razor and that she was now dripping wet under her pussy.

"Is the area around my mound nice and smooth?" she demanded to know.

Brianna replied, "Yes Mistress, I think so."

"Then you had better find out for sure, your tongue is a most sensitive muscle, lick all around the shaved area to be sure that it is smooth," she instructed.

He ran his tongue over the areas to the left, right of and above her outer lips, finding it nice and soft and hair free, then applied his wet tongue to the outside of those lips taking in the taste of her freshly produced nectar and wishing that his cock could be free to get hard.

He was brought out of this train of though by the command, "Stop now girl, your tongue has confirmed my baldness and I have to give you your treat." She reached out and pressed an intercom switch on the wall and demanded, "Bring the face strapon and fix it to my new maid."

A few minutes later, the door opened and the maid whom the Mistress had referred to as GirlyBoy arrived with a tray containing what looked like a very realistic double ended strapon dildo, although one of the penis shaped ends was much shorter than the other one.

Mistress Rose told her maid, "Put it on Brianna and then leave the room."

The maid curtseyed and replied "Yes Mistress Rose". Then Brianna felt the straps being lifted over his head and the smaller penis end offered to his lips. He did not dare hesitate to open his mouth as his buttocks were still warm as a reminder to him of what happened when Mistress was displeased. After the straps had been tightened around his head he appreciated that he was wearing the smaller penis gag in his mouth, whilst the other end was effectively a strapon dildo.

"Your treat is to bring Mistress to orgasm using the face harness you are wearing., she instructed adding, "one feature you are probably not aware of is that the dildo you will be using on me is equipped with a powerful vibrator that is at the perfect height to stimulate my clitoris. This is operated by the dildo in your mouth which detects how hard you are sucking. The harder you suck, the more stimulation I get."

He thought it over for a second and decided that the best way to end this humiliation was to fully comply, so he nosed forward and began to run the tip of the dildo up and down her pussy lips, parting them as he did so. After a while, he knew exactly where her pussy parted and where her clit was, so he placed the tip of the penis dildo against her clit and sucked hard on the one in his mouth.

He felt the vibration in his mouth and heard the approving moan of his Mistress. Then he slid the dildo down her folds, parted her lips and started to push forward slowly with his head penetrating deep in to her pussy. Once he had the dong balls-deep in her pussy he wrapped his lips around his end and worked the shaft so that the clit-stim did it's magic.