PainLove - Bk. 04 - Ch. 24-28

Chapter 24

It was getting dark when the doorbell rang. There was no money at the table by the door, but Rob opened the door without concern. There, to his surprise, stood Cathy. Quickly Rob swung the door open to admit her. He gave a curtsy as she stepped past him, causing her to stop and give him a quick kiss. "It's good to see you're having fun with this."

Rob was getting Cathy settled in her guest room when the doorbell rang again. By the time he got to the top of the stair, Iris, fully dressed, was opening the door. She took the dinner and paid the delivery man. It was Chinese this time. Cathy and Rob descended the stair and helped bring the containers into the dining room. Michelle joined them, coming from her library.

Dinner was a merry affair as the four of them ate, drinking tea and wine. Iris showed Cathy the photos she'd taken of Rob and described with glee taking him outside.

Cathy gave Rob a wink. "My, Rob, we shall do this on my doorstep one day."

Rob gave her a smile and said, "You don't worry me. If it weren't for the privacy Michelle has, I'd have not gone out the door."

Michelle agreed. "If it weren't for the privacy I'd not allow such a thing. I live with these neighbors."

They stayed at the table, chatting, for quite some time after they finished eating. Rob cleared away the dishes and made another pot of tea. The casual attitude of the ladies made him think there might be nothing more this evening. The ladies rose and left on occasion, Rob thought nothing of it. At some point Michelle didn't reappear.

Cathy said, "so what about something sweet to end the evening?"

"Shall we go to the playroom?' Iris crooked an eyebrow to Rob in invitation.

He put down his teacup and put his napkin on the table. "What is your will, Mistress?"

Iris and Cathy laughed. They were being deliberately informal this week, making his more formal response amusing.

"I've heard you don't like calling Helena's room a dungeon, you prefer to call it a playroom. In the spirit of the fun we're to have tonight, I agree with you," Iris said. She rose from her seat, dropping her napkin. "Shall we go to the playroom together, dears?"

Cathy, Iris and Rob all went together down the stair to Michelle's basement. He gave no thought to Michelle's absence, the ladies had frequently changed who would play with him. Iris led all of them into the playroom through the red door, ignoring the formalities Rob had previously experienced. Rob was surprised how much space was available in the Mistress' changing room and how many wardrobes and drawers were there. She must have a lot of gear, Rob thought. But they swept through without slowing.

Once in the playroom, Rob discovered Michelle was going to participate. She sat on her throne, the platform and chair he had knelt before during his first session. She was dressed as a domina, wearing an open-cup bra, a waist-cincher with garters holding up stockings, all in black. Her eye makeup was dark, her lips dark red. Rob, out of the habit of controlling his erection, began to harden at the sight over her. Cathy smiled as she his dick in hand, using it to lead him to stand before Michelle, with Iris on one side and Cathy on the other.

Michelle rose and stood before him, her feet apart. Rob saw she was also wearing no panties, her lips were prominent. He continued to harden in response to what he saw. Iris glanced down, saw what his dick was doing and reached down hold it in her hand.

Michelle spoke formally. "So, slave, it appears it does turn you on to be dominated."

"Yes, true Mistress, in some situations. It's not true just any day, it isn't true under every circumstance."

Iris gave him a squeeze in response. Rob was unsure whether it was approval or reprimand.

"Tonight you shall take your rightful place as my devoted slave. You shall be collared and swear your devotion to me."

She paused, waiting for Rob to reply, but he had nothing to say. He continued to look Michelle in the eye and waited calmly to find out what this all meant.

Her eyes looked amused, but her face retained its severe expression. "What are you waiting for, slave?"

"I am waiting to see how you intend to play this evening, Michelle."

Now Michelle's face had a genuine smile. "Okay, Rob, let's play."

She reached to the table at her left hand and picked up a collar. She held it up for him to see. It was dark blue leather, nearly two inches wide. There was an ornate "M" embossed into the leather at the front with metal studs in an arc on either side of the letter. He could also see a padlock dangling from the buckle; it could be locked in place. "Rob, Do you accept my collar to wear?"

Without hesitation, he answered. "Yes, Michelle, I will wear your collar, for this weekend."

Cathy questioned his confidence. "You can see it can be locked on, it will only come off when she wishes?"

"I agree to have it locked on, for this weekend." He was calm, his eyes still on Michelle.

Iris asked, "what will you do if it isn't taken off at the end of the weekend?"

"I'd question what it means."

"It would mean I am keeping you." Michelle's face was serious again.

"Michelle, I freely consent to wearing your collar for this weekend. You know I cannot consent to more than this weekend, just as you know you cannot keep me. I doubt I'll be the worst reason you'll find little pleasure in keeping me, but you can expect me to contribute to your woes." Rob was surprised how easy it was to remain calm and respond reasonably to her implied threat.

Michelle smiled again. She removed the padlock from the collar, opened her fingers and let the lock drop to the platform with a clunk. "You shall wear my collar for the weekend." She stepped down to him and placed it over his neck. Iris and Cathy took the ends and put it around his neck.

"A collar is not a symbol of submission." Michelle spoke as the two others secured the collar around his neck. "It is a symbol of an intimate connection between two people. It's a symbol of each of the two people giving a gift to the other. It's a symbol of devotion, each to the other. A mistress can have many submissive clients, but few wear the collar."

Michelle picked up small box from the table. "You might know it's customary for the slave to receive a necklace to wear on those occasions when a collar isn't appropriate. In most cases, the necklace, male or female, is a heavy chain of silver or stainless steel. The weight is intended to remind the wearer the collar should be there." Opening the box, she showed to Rob a fine, gold necklace with two charms, a filigree heart and a key. "We thought in your case something more feminine would be appropriate. Rob, I give you this gift to wear instead of the collar, when the occasion dictates discretion. After you no longer wear my collar, I trust you will still wear the necklace, simply to show you value your memories of our time together."

She stepped down from her platform, put her arms around him, kissed him on each cheek, then kissed him on the lips. She gave him the box.

"Thank you, Michelle. I will happily wear this necklace." He surprised her by returning her kisses. "This is very sweet of you, all three of you, I appreciate your thoughtful gift very much."

Cathy and Iris stepped forward as well, crowded together in something of a group hug. Rob's dick had softened a bit during the discussion, but more than one hand reached to grip it as they stood in a convivial cluster.

Michelle looked around. "Right. We came to the playroom, let's play."

Michelle led them to the her X-cross. She stood beside it and said, "Rob, no flogging, no clamps, no pain tonight. I think we're all going to enjoy this equally." Iris and Cathy helped him out of his dress and petticoats, then Michelle guided him to step up onto footrests on the cross, facing outward instead of inward. She secured his wrists, then his ankles, then wrapped a wide leather belt around his waist and the cross. She disappeared from his view and began working right behind his head. Soon her hand touched his forehead, tilting his head backward. Since she had told him there would be no pain, he was far less apprehensive, far more relaxed as he complied with her guidance. He found she had added a headrest. She adjusted the height so his head landed in a comfortable spot. Rob noticed she added the head support but didn't secure him to it, leaving him free to move his head.

Giving him a smile she said, "ready?"

Rob nodded to indicate he was ready.

The X began to tilt, moving Rob backward, all the way to flat on his back. Iris stepped up to him, looked down, then stepped away. The other two moved something on the floor below him. He realized it was a platform of some kind when Iris took a step up and was well above him. He saw she reached out to tug on ropes hanging from the overhead on either side of his head. Pulling up her skirts, she showed Rob a reminder the women had agreed to wear no panties this entire time as well. She stepped over him and let her dress fall over his head, enclosing him in a tent, just his face and her lips, already starting to swell from arousal.

He could reach up to kiss her by craning his neck, but he knew he wouldn't be able to reach up there for long. Just when he was about to say something, there was a soft click and his face was swung up to meet Iris. His mouth opened as he reached her and he immediately began to lick her in earnest. This was domination he could enjoy.

As soon as he began licking, a hand wrapped around his hardening dick and began to slowly squeeze. Instantly, Rob felt the arousal of the teasing he had already endured. He almost stopped licking to enjoy the attention, but he knew he wasn't destined to orgasm for at least another day and continued to play his part.

Over the first two minutes there were subtle changes in how hard his mouth was pressed against Iris, then it seemed to stay at amount of force. Iris was responding, moving her hips and definitely getting wetter. He thought he could make her come pretty quickly, but she didn't let him concentrate on any one spot to have what he wanted to give her. She was moving forward and back, directing his licking and sucking mouth where she wished. He could tell by the range of motion she was working her way to have him lick her arse. He tried to tell her to go right ahead, but he quickly realized he wasn't in charge, someone else was deciding what his mouth should do. He just kept licking.

When she finally got his mouth to her arse, he didn't hesitate. He licked eagerly, even trying to penetrate her with his tongue. Iris was clearly enjoying what he was doing. She gasped and bore down on him, only to have him move to maintain the force set by some mechanism. After enjoying his mouth in her arse she moved back to present her cunt, this time letting him give more attention to her swollen clit. The hand on his dick was supplemented by a tongue circling just the head. Rob could tell this was all intended to tease, he wasn't going to move much close to an orgasm under the expert care of - whoever was doing it. He tried to simply ignore it and focus on what he could do.

Suddenly Iris pushed herself down on him and began to come. Rob felt himself moving down slightly as the cross he was strapped to rotated as Iris pushed down. Throughout and after her orgasm, Rob continued to lick whatever he could reach.

The curtain of Iris' dress lifted from around him, Rob had a quick view of Cathy over his dick and Michelle stepping to his head. Soon it was Michelle's dress covering his view and Michelle's cunt requiring his attention. The hand on his dick left, then after a short pause a hand returned, from a different angle.

Michelle was much quicker to move to where Rob could lick her arse. She had done it before with him and he had responded well when Iris required it of him. She took her time, giving Rob just enough access to give soft licks to her nether hole for quite some time before bearing down and giving him the chance to truly ream her with his tongue. She shifted to have him lick her cunt but gave him little access to her clit, then shifted back to her arse, this time bearing down firmly from the beginning. Michelle seemed to have a way to push down harder without the mechanism compensating. As she bore down, his nose was held between her cunt lips, making him feel a little breathless. She never held him in the position too long so he made no effort to protest. When she returned his oral attention to her cunt, she finally gave him the chance to lick her clit and soon she was having her orgasm.

When Michelle stepped off from over Rob's face, Cathy immediately took her place. "I can't believe you just go along with rimming. What a treat." Soon she had Rob's tongue working on her arse. She wasn't at all unpleasant, but the experience to his mouth and nose was muskier than it had been with Michelle or Iris. She shifted to guide his mouth and tongue to her cunt. Soon enough she too was coming.

Rob imagined, after the third woman had an orgasm, the session might end or at least move on. He was kept on the cross. The three ladies gathered around him, Iris now without her dress and wearing a black, leather corset with her breasts exposed. His mouth opened eagerly to receive her nipple when she bent over to feed him first one, then the other. As he sucked on her nipples, Iris told him what was coming next. "I love smothering. It gives such a feeling of control and power, to both of us. Tonight, I'm going to smother you. If you die, at least you'll die with the taste of my quim in your mouth."

The threat he might die was just building the dominance drama; Rob chose not to respond. It was out of the question these three women would suddenly change their stripes and do something which might really hurt him. He did nothing to respond, just continue suckling at Iris' nipple, his gaze vacant. A hand softly surrounded his hard dick and a finger began caressing, enough to keep him hard but little enough it was clear there was no orgasm for him.

Iris swung her leg over his face, facing so she could look down to see his eyes. Rob was eased up to meet her cunt with his mouth and began to lick.

"If you want to live, you'll keep licking no matter what." Iris's voice was stern. "If you stop licking, the smothering will only get worse."

Hollow threats, Rob thought to himself. The thing you say to a man who doesn't like to go down on women, not to a man who loves it.

Iris kept his tongue on her clit and quickly reached her second orgasm. Then she reached down to hold his ears, one in each hand. Tugging upward, she pressed his mouth against her cunt. Her position left his nose free and he could easily breathe. Her tugging at his ears didn't hurt very much, most of her tugging just moved him head up or down on the tilting cross.

"That's it, boy," Iris whispered. "You just keep doing that." She shifted back, so his tongue was better positioned to push into her cunt, which placed her clit just on his nose. He saw this and moved his head side to side a bit, to give her stimulation.

"Good lad. Get me a third cum or die trying." With her hand behind his neck, Iris pulled him up tight to her. He had a much more limited ability to breathe. He realized he could get the best breaths as he swung his nose to one side other the other. His nose stimulating her clit became a bit more vigorous. He pushed his tongue into her sweet, hot cunt as far as he could as he moved his face from side to side. He was getting short of breath, he felt himself panicking. Suddenly, without giving it any thought, he strained to turn his face into her thigh, his mouth wide open as he panted for breath.

"Keep licking!" Iris commanded. She took him by the ears and forced him roughly back into position. He resumed, but with less enthusiasm. Iris established a pattern of smothering him long enough to make him breathless, then letting him breathe, then repeating. Rob didn't notice as Iris smothered him for a longer time then gave him less time to recover with each repetition.

The lack of oxygen caught up with him, he began to feel a euphoria, but was also aware his heart was faster. The stimulation to his dick somehow became the only feeling he was experiencing. Licking of the cunt covering his face was almost automatic. Eventually he began to fade, his movement faltering. Immediately Iris stepped away, then tilted his head back to make sure he could breathe. He didn't quite pass out, but with his face uncovered he could feel his vision was blurry and narrow. Soon he could see the faces of all three women gathered over him. He felt a clunk, then he was tilted further, his head lower. He found himself recovering more quickly. He was tilted in the other direction, not fully upright, where they released him from the cross.

The women guided him to sit in a chair waiting for him right before the cross. Michelle stood on one side, Cathy on the other, supporting him. Iris knelt, her face close to his, watching him carefully. Rob, taking slow, deep breaths, began to recover and soon had the strength to sit upright on his own.

Iris spoke to him gently. "Tell how you feel, Rob."

"It was scary, the breath control, Iris, it gives me the shivers to remember it. But it was also fun. Toward the end I felt kind of out-of-body. One day I may be willing to repeat it." He smiled. "The fact I just said those words scares me."

Michelle wanted to make sure he didn't get overly excited. "It's only for the experts to do. I've trained, but I haven't the experience Iris has to do it so well. I wouldn't do it without another present, for safety."

Iris added a detail. "Ordinarily, we would have made you come just as you reached your limit. I've done that to men who said it was the best orgasm of their lives. You, of course, must wait a bit longer to get your reward."

Cathy extended her hand to him. "Come, Rob. The session is over for now, it's time for some proper aftercare." Taking her hand, he let Cathy lead him up to his bedroom, where she soon had him dressed in a satin nightgown and matching robe. As he dressed, Michelle came in to drop the clothing he'd left behind in her dungeon. She reached out to him, fingers traced a line on his skin, following the line of the collar he now wore. The touch to his skin reminded him - he'd quite forgotten it was there.

They all joined in the living room where Iris was serving hot coffee and brandy. Rob was seated on the couch with Cathy and Michelle seated close to him, on each side. The conversation was light, sometimes talking about the session they'd just had, other times the change of season or the new scandal among members of Parliament. Rob sat there, feeling a little sleepy, not contributing much unless he was asked a question. Eventually, it was time for bed and Rob found himself in Michelle's bed, between Michelle and Cathy. They kissed and caressed him, soon letting him fall asleep.

Chapter 25

Rob awoke Friday morning to find Michelle gone, but Cathy still in bed beside him. He tried to slip out quietly, wanting to leave her to sleep, but Cathy, suddenly alert, slid over and got out of bed right behind him.

She took his hand and led him to the shower. "You know what happens now, don't you?"

"I do know and I consent, dear." Rob gave her a kiss.

In the shower, Cathy embraced him for a sensuous kiss. "How far are you willing to go?"

Rob answered by dropping to his knees. He guided Cathy to stand over him and closed his eyes. Soon he felt a hot stream running across his face and down his chest. Cautiously, he stuck out his tongue, found the stream of urine. Keeping his tongue on her stream, he rose up only a few inches until his mouth met her. He kept his face in position, but put his tongue back in his mouth and let the hot urine stream down his chest until she had finished. He licked her clean.

Rising, he moved to rinse his mouth, but Cathy insisted on a wet kiss, her tongue probing his mouth. Only then did they both rinse their mouths.

"I don't think you object to a golden shower, you just object to someone assuming they can do it without talking with you."

"One someone in particular." Rob regretted his harsh tone and compensated by wrapping his arms around her. Taking the soap, he washed her down, all she had to do was turn and lift her arms.

Over breakfast, Cathy announced they were taking Rob shopping. "We want to get you a proper party frock. Wear a bra and stockings under your trousers." She grinned. "Unless you want to wear a dress as we shop."

Cathy came into his room as he was dressing and rummaged in his wardrobe. She came out with the black, Mary-Jane shoes with a two-inch heel he'd been wearing with his maid costumes. She insisted he wear them when they want dress shopping. "You can't possibly wear male shoes when you try on a dress," she challenged. Rob sighed. They were innocuous enough under his trousers. She also had him take off his collar, replacing it with his necklace.

Soon Cathy and Iris were with him in Cathy's car, driving to the center of Northampton. Cathy parked just off the town center and let them to a boutique dress shop on a side street. The clerk greeted them as they came in, Cathy telling her they would browse before asking for help.

At first, Rob was a little self-conscious, but soon was enjoying looking through the dresses on display. The shop specialized in nicer dresses, of the sort worn to cocktail parties or for a night of dancing in a nightclub. Cathy and Iris were each looking over the dresses on display, but they were also keeping an eye on Rob to see what he was doing. Cathy and Iris each pulled out a dress or two and set them on the rack beside the fitting room.

Rob found a dress he though was just beautiful. In deep purple satin, the dress had a handkerchief hem and a panel of black lace on the bodice, the purple fabric visible through the lace. Even with the dress on its hanger, Rob could see he would be showing a great deal of leg. He glanced toward Cathy and Iris, saw them just browsing. He plucked up his courage, looked for the size he expected would fit and took the dress over the to clerk. "I'd like to try this one on."

The clerk glanced over toward Iris and Cathy. Iris saw the situation and responded. "Don't worry about us. We're here shopping for him."

The clerk, still looking uncertain, nodded. "As you wish, sir."

In the fitting room, Rob quickly dropped his male clothes and slipped into the dress. The heel wasn't as high as he would wear with the dress for an occasion, but Cathy was quite right. His Mary Jane shoes were better for trying on a dress than barefoot or men's shoes. The dress had a snug top and the skirt had more flare than Rob had expected, but he thought it would look good.

There was no mirror in the fitting room, Rob had to step out to the mirrors. As soon as he came out, he found Cathy and the clerk waiting expectantly.

The clerk was impressed. "Oh, you're right. He does know what he's doing. Is that stockings you have on, sir?"

Rob gave a small smile and tilted his head. He stepped over to the mirror, smoothing his skirts as he looked at himself.

Iris joined them. "Quite pretty. Rob, you do have a good fashion sense. Refined, not flashy."

The clerk stepped over to him, studying the dress and its fit. "Something's missing, this dress is more fabulous than we see here." She looked at the black lace bodice and snapped her fingers. "Of course! I'll be right back." She went off across the shop to where the dress had been hanging.

When she returned she was carrying a black petticoat with a hem trimmed in a wide band of lace matching the dress. When she held it up for his inspection, he saw the lace trim matched the lace on the dress. "These go together, the petticoat is included in the price for the dress. May I help you into it?"

Without waiting for a reply, she spread the waist of the petticoat and stooped to guide him to step through. She drew the petticoat up Rob's legs, stopping to comment on his stockings and suspender belt. "You aren't compromising on this, are you sir? What's the occasion?"

"I'm not entirely sure, sometimes these ladies don't tell me things until the last moment."

Iris had the answer. "We're hoping you might wear it to the party Saturday night, Rob."

Rob suddenly blushed as he felt the store clerk lift his dress in back, snug up the petticoat's drawstring and tie it. He looked at the mirror and immediately protested. The petticoat was not at all concealed by the dress. "Shouldn't it be worn higher? Are you sure these two go together?"

"Just a moment please." The clerk went to the computer at the counter and spent a minute searching. "This dress was shown in pret-a-porter last Paris Fashion Week, there's a video." She turned the monitor to show them a video clip of a model walking down the runway. On the model, the petticoat hung well below the hem of the skirt, swishing with each stride. "It's the latest clubwear fashion. Steampunk-inspired but still modern, flirty and very feminine." The dress, with its high hem in front, did look more demure, with the black petticoat providing added coverage.

"We must have you practice walking like a model." Iris gestured at the video.

Cathy joined in. "Why not? Rob, take a turn down the main aisle here."

Rob obeyed, putting on his best imitation of a model's gait. He had learned well when Michelle required him to practice. He realized he was walking straight to the glass door and front windows with people walking past outside, but he decided to continue. He stopped just short of the door, struck a pose, hip out, then turned and pushed his other hip to the side, before strutting back toward the fitting room. He hear the door open behind him and the voices of girls, which made his ears color, but he kept on.

"I want that one!" A girl's voice behind him exclaimed. Seconds later, two girls, seventeen or eighteen years old, were standing at Rob's side, admiring the party dress. Their attention went to the looping video of the dress on the Paris catwalk.

"Rob, that's a fine choice. Are you interested in trying on more? We've picked out a few." Cathy held up a more conservative dress, lace overlay in medium blue. As the clerk attended to the two girls, Cathy and Iris had him try on the blue dress, which Rob found too frumpy, and a dress in burgundy silk, cut on the bias and slinky.

The two girls stopped their shopping to admire Rob in the burgundy dress.

"What a pretty little necklace, too! What do those charms on your necklace mean?"

"Well, there's a heart and key, what do you think?"

"Aw, that's sweet."

The other girl noticed something on Rob. "Hey, you're wearing girl's shoes, and stockings!"

The two girls crowded Rob to examine him more closely. One of them giggled. "What would Georgie say if I told him I bought a dress because I liked it when I saw a man wearing it?"

When they started to lift his skirt up for more inspection, he decided it was time to stop them. He gently pushed their hands away. "Girls, have just a bit of respect. If I started pulling your skirts in a dress shop, you'd be screaming bloody murder."

The two girls stepped back, looking apologetic. "It's how we treat our friends trying on dresses."

"I doubt your mothers would approve of me as the friend who tries on dresses with you." They all laughed. Even the shop clerk seemed to be more comfortable with the situation.

After trying on two more dresses, now with four customers in the shop to watch his model's walk to the door and back, Cathy and Iris decided the purple satin had the right effect for the party. After they put the dress in the car, Iris proposed more shopping. "Why don't we drop by Bridget's? I'm imagining how good Rob would look in his new dress with black ballet boots locked on his ankles." Not waiting for an answer, she led Cathy toward the new destination.

"Hey!"

The ladies looked back to see Rob leaning against the fender of the car, arms folded. "I'll be happy to go visit the shop, but you'll find yourself facing some resistance to ballet boots."

They took the few steps back to stand with Rob. Iris pulled at his hand. "Come now, Rob. Just the thing to wear to a fetish club meeting tomorrow night."

"Ladies, I think I've made clear, even written it down, stacking up too many things at once is an issue. The answer to ballet boots is no. The answer to ballet boots at the event tomorrow night is hell no."

"What will you wear, then?

"I have strappy, black sandals with a three-inch heel, I think you'll find them quite suitable with the dress we chose. Unlike a ballet boot, I know I can walk in them without stumbling."

Cathy and Iris turned to each other and began laughing. Cathy explained. "Rob, I predicted correctly you would know what shoes to wear with whatever dress we picked out. All right, no ballet boots for you."

Iris had a correction. "At least, not yet."

They spent an hour browsing the costumes and lingerie in Bridget's shop. Bridget greeted them, but didn't invite them up to the floor with the BDSM gear. Rob was relieved, she was friendly to him, and he cordial to her, but his most prominent memory of Bridget was a surprise session, with Helena's collusion.

The three of them left the shop having not purchased anything and returned to Michelle's. Once there, Iris demanded he wear his new party frock for the afternoon, with the appropriate shoes. Rob was happy to comply, but quickly learned the disadvantage of wearing such a short skirt when he was also not wearing knickers. First Michelle, then Cathy, the Iris stopped him, easily reaching under his dress stroke him until he was hard and right on edge. Iris, in particular, was expert. Within an hour Rob was incredibly aroused.

Michelle led them all up to her bedroom, taking Rob to lean over the foot of her bed. "We don't intend to secure you. But we can, if we must or if you would like it."

Rob was agreeable. "Let's try without and see what happens."

Almost immediately, a lubricated finger was probing his arse. Iris slipped up onto the bed and slid down to present her cunt to his mouth. Rob had to bend down further, spreading his feet further to make it easier to lick her eagerly. The finger in his arse became two, not just pushing slowly in and out, but also pressing wider.

Iris came and Cathy quickly took her place, but she turned over and had Rob lick her arse. The fingers were withdrawn and something cool and blunt took their place. Rob assumed it was a strap-on and ignored the intrusion. He thought he knew how it would feel. A hand gripped his hard dick as the dildo pushed in. Rob was surprised as how much it was spreading him. Whoever was pegging him was pushing in a bit, then waiting for him to relax. The steady pressure went slowly but steadily expanded him.

Just when he thought the feeling of the expansion would be too much to bear, he felt the sensation reduce as the dildo - or whatever it was - slipped into him. He was about to turn and ask what was going on, but a hand behind his head pushed him back to keeping licking Cathy's arse. The hand which had been simply holding his hard dick began moving softly out and back, caressing him enough to raise his excitement still further but not quite enough to help him finish.

Cathy turned over to let Rob lick her cunt; he quickly got her to an orgasm. Rob looked around, expecting Michelle to slip in and take her turn as well, but she was not in view. Rob eased himself upright, reminded of the intruder in his bum as he stood.

"Have you worn a butt plug before?" Iris asked.

"Yes, a time or two. This one must be a monster."

"In this line, the one we've given you is a medium."

Rob tried a few careful steps. He quickly discovered, between his heels and the plug, it was much more comfortable to take short steps, feet close together the entire time.

"Look at him mincing like a girl!" Cathy exclaimed.

Michelle reappeared from the upstairs hall. "I require a maid to help prepare dinner. Rob, please put on your uniform and come to the kitchen. Wear those shoes, I fancy them."

Chapter 26

Dinner was a pork roast with roast potatoes and steamed carrots. Rob helped get everything ready for the oven, then polished the table, then set the table. He noticed Michelle, for the first time in his experience, had him set the table for the meal without a tablecloth. He selected a wine from Michelle's cabinet and opened the bottle.

There was some quiet time as dinner was roasting. Cathy led him into the library, where they sat. "Rob, how is this experience working for you?"

"Oh, this is magical. It doesn't seem very dominant/submissive at all, yet I'm doing many things expected of a submissive. I appreciate there not being much bondage to it." He paused. "I don't mind a little bondage, it's just it requires trust."

"What are you learning?"

"I'm learning I'll do practically anything with the right woman, under the right circumstances. Not only that, I'll like it."

Cathy gave him an encouraging smile. "We're trying to make sure you're ready for the right woman." Rob though he saw a hint of sadness in her eyes.

She continued. "You're okay with all the teasing, but not coming?"

"Oh, it's fine. With Jenny we never got this far, she was too eager to have more fun. I'm fine, this is actually fun and I think it does make me more willing to take things on."

"Hold that thought." Cathy proceeded to talk about relaxing his mind as well as his body. She concluded by saying, "For you, it's about letting go, stopping thinking. You're quite good at thinking, Rob, which generally signals you're not good at not thinking." They talked about the challenge of how to not think. Cathy emphasized focusing on the experience in the instant, identifying in detail the pleasure as well as the pain and putting his attention into experiencing them, both separately and as a total experience. "Don't think back to what has happened, don't wonder what the future holds, just focus on what you're feeling in the moment."

Then it was time to serve dinner. After the four enjoyed the meal, they sat around the table chatting. Michelle served brandy with the coffee. Rob, still in his maid uniform, was starting to wonder whether they had a session in mind for the night.

Michelle tried to pour him some more brandy. "Drink up, Rob."

He put out his hand and gently slid the glass away from himself. "I think I've had quite enough, thanks." He rose and began to clear away the remaining dishes, leaving only the coffee cups and brandy snifters before each lady.

When he came back, Michelle asked him, "Rob, are you all right?"

"Yes, I'm fine, why?"

"I tried to give you more brandy and suddenly you chilled the whole room."

"I'm feeling cautious. No woman one has ever encouraged me to drink more without a motive."

Iris snorted, Cathy grinned. Michelle smiled. "Guilty!"

Cathy went to the bottom drawer of the sideboard. Rob knew what was kept there and sighed. Iris stripped him of his maid's uniform. Rob was already growing erect by the time the dress was up over his head. Iris saw this as she took off his petticoat, leaving him in just bra, stockings and suspender belt. As soon as he'd stepped out of the petticoat she tossed both it and the dress aside on the floor and began stroking him to full erection as Michele cleared away the last cups and glasses. "You were so eager to clear away tonight, I thought you knew what we had planned."

"I've only seen the table without a tablecloth for one reason."

"On the table then. You know what comes next."

Rob knew what she wanted. He slipped up in the table and lay down the center. He extended his arms and legs to where he knew they would secure him.

With three mistresses, it was no time at all before Rob was secured, hands and feet. Michelle didn't secure his head.

Michelle got up on the table and knelt over his mouth. She was close enough he might lick her if he strained, but he chose not to raise his head. A hand wrapped around his hard dick and began to softly stroke.

"Does this seem familiar?" Michelle looked down at him between her thighs.

"Yes." Then he added, "Mistress."

"Do you consent now?"

Rob simply turned his head to his left and held it there.

"Why not?"

"You must be clear about the consent question, Mistress." The hand on his dick gave him a sharp squeeze, not quite painful.

"Rob, I intend to pee into your mouth and have you swallow. Why are you not cooperating?"

Rob sighed. "Because it will spill and spray it all over and we'll all spend a lot of time cleaning up."

"Why won't you swallow?"

"Oh, bugger!" Rob was surprised she didn't understand. "Because I've never swallowed. This isn't the shower stall, but I will spit it out. Ladies, I'm done for the night, let me up."

Michelle didn't move, the hand on his dick kept stroking and squeezing.

"And now you're setting yourselves back," Rob added. He moved his head only slightly, bared his teeth and gently nipped Michelle's leg.

"Here's a new side of you." Grabbing his ears, she guided him to face upward. "Let's move along to something else." She moved herself down to his mouth. Rob licked and kissed eagerly. This was a test, she'd gotten her answer: he wasn't angry enough to force a stop, he had simply given her a clear warning to back down. She ground herself against him, sometimes covering both his mouth and his nose, but not as severe as the smothering from Iris the previous day. After several minutes, she was bearing down hard as she came. Rob would have liked to keep licking her, he quite liked her flavor, but she got off.

Iris replaced her and the process was repeated.

Then it was Cathy's turn. She paused, just above him. "Are you sure, Rob?"

"I'm sure, dear." He understood the question was about golden nectar from the source. A few minutes later Cathy was having her orgasm.

Michelle and Cathy left the room. Rob expected to be released. Iris took his dick in her hands and began to drive him mad with excitement, true tease and denial right up to one edge after another. Rob groaned. "God, you're good."

It was a long time before she stopped and began to release him from the bondage on the dining table. "Iris, Your reputation is a mistress who prefers to beat men, why are you treating me so differently?"

"The subs I toyed with privately got lots of tease and denial. I had one fellow who visited me regularly, twice a month, for five or six years. One year he had only four orgasms. The problem is teasing is mostly mental, not physical. In a club, giving a show, it's necessary to do things everyone can see. There I exhibit my whipping skills.

"Come, time to go up."

In Michelle's bedroom, Rob found Cathy and Michelle wearing nothing but stockings and suspender belts. A chair was in the middle of the floor, a small table beside it held a hairbrush and a riding crop. Cathy sat in the chair and gestured to him. "Come, Rob, time for you to warm up."

After the attention from Iris, Rob was still fully erect. It took little effort for Cathy to trap his hard dick between her legs. He let his weight down on her lap, toes just brushing the carpet and hands on the floor for balance. Hands unclipped his back suspenders from his stockings and tucked them up under the belt. With three women around him he often had no idea who was doing what. Cathy started by moving her legs slightly, causing him to gasp. "I'd say you have him quite ready, Iris." Her hand caressed a circle on Rob's bum. "Rob, we're going to start."

The hand was lifted, then fell. Spanking was now such a familiar sensation, Rob hardly responded. Cathy was spanking him at an unhurried pace, moving her hand around at random so the location of the next sensation was not predictable. Rob felt a familiar series, first it hurt a little, then the pain from each hit seemed to be getting worse, then the sensation of pain was reduced, less sharp, more spread out.

After a time, Cathy stopped, her fingertips gently passing over his skin. He heard Iris' voice. "Such a lovely shade of pink. Nicely uniform, too, Cathy, you're quite good."

The pause was short-lived. Cathy shifted. "Now, Rob, I'm going to use the hairbrush."

She resumed. This time she hit him harder and faster. The vigor took him back to repeat the cycle of experience, feeling the pain of each hit grow, then finally feeling the pain more generally.

"I'd say he's ready, ladies." It was Michelle's voice.

Cathy still hit him with the hairbrush a few more times before stopping. Then Iris and Michelle helped him up from her lap.

Chapter 27

Michelle told him what was next. "Now, Rob, we'd like to challenge your commitment and your concentration. No bondage this time, you must decide to hold still for this. Here is the challenge." She held up the whip Iris had just put in her hand. "Do you recognize this whip?"

At a glance he knew what it was. "Yes, you've used this whip on me before."

"Yes, but only for a few minutes. Your challenge is to bend over the bed and take a whipping. You will also go down on Iris. The whipping will continue until either Iris comes or you admit defeat by moving out of position. Do you understand?"

The ladies were surprised to see Rob hesitate, he seemed to be making an effort to think. "I understand. Sorry, I'm a bit slow right now and I don't think it's the brandy."

He helped Iris onto the bed. He adjusted her position a bit, then slipped a pillow under her hips. He bent over to check the positioning and found everything a decent fit. He was grateful Michelle's bed was so high off the floor, but even so he slipped out of his high heels. He gently slid his hands under Iris' legs, tipped his face down to the junction of Iris' legs.

He proceeded to unhurriedly give gentle kisses to just her thighs and cunt lips. He had no idea how to proceed, except he expected trying to rush her to come would only put her off, make her come even slower. He just did what seemed right. He spent the first minutes just kissing.

Before he had even put out his tongue for the first time, he felt the hot explosion of the whip hitting his bottom. He concentrated on just kissing gently. As the whipping slowly continued, he let his tongue just trace along the outermost edge of her lips, drawing a sign of satisfaction from Iris. He continued giving her slow, sensual licks, the whip occasionally giving him a sudden, short burst of fiery sensation. Michelle was not in a hurry, she spaced the hits well apart in time. She varied the timing, Rob soon abandoned the idea of trying to anticipate when he would feel the next one.

The first occasion of the whip delivering far more pain than it had been, for an instant Rob started to rise up in protest, but he mastered himself. Iris didn't realize what had happened; by sheer luck his tongue had been near the back, his reaction had simply brought his tongue quickly forward to her clit, which to this point he hadn't stimulated. Iris's hands were suddenly on his head, guiding him to continue licking her on her clit, but he soon moved away again to kiss, nibble and lick elsewhere.

As the challenge continued, Rob could tell by the copious fluid leaking from her Iris was more excited. The flavor was wonderful and Rob would frequently dredge his tongue from back to front to collect the fluid. The whipping was bearable, most of the hits were part of a dull background, with the occasional sharp pain.

After a long period when the whip didn't hit him, he felt a hand on his shoulder, he heard Michelle's voice, as though from a distance. "Rob, I must suspend the challenge, I don't want to break your skin."

He paused, looking up to Iris. "Shall I stop, then?"

"God no, you bastard! Finish me!"

Rob pulled her to the edge of the bed and knelt to resume licking. He didn't pick up the pace, he spent no more time on her clit, he just continued what he'd been doing. Somehow, he didn't know why, this was the right thing to do. Hands gently rubbed a salve on his reddened bottom, later his garters were fastened back in place. He lost track of time, he didn't care, he was licking a sweet pussy, nothing else mattered. Iris' hand pushed at his head, but he ignored whatever signals she was trying to give him.

Finally the time seemed right. One hand crept to her cunt, she was so wet there was no issue with slipping his thumb right in. He moved his mouth to her clit and began licking more vigorously. When he closed his lips and added a gentle suction to the action of his tongue, her hands pulled his face into herself, her legs tensed and Iris moaned as she began a long orgasm. Rob, of course, kept licking her clit the entire time. When she was finished, he eased his thumb out of her and resumed licking her lips. He was thinking of all the times he had given a woman a second orgasm and intended to try with Iris.

When his tongue first reached her clit again, she tensed and pushed him forcefully away. "Aah! No, too sensitive."

Iris lay, inert and exhausted. Rob continued to kiss and lick her lips for some time after, taking care to touch her clit only only gently.

After some time, her hands gestured to him. "Come here, dear boy."

Rob helped her back up onto the bed. He happened to glance over and saw Michelle sitting on the chair, leaning forward with her chin on her fist, just watching. Cathy stood behind her, also watching with great attention, one hand holding the back of the chair, the fingers of her other hand softly brushing through her pubic hair.

Rob moved beside Iris, put his arms around her and held her, she seemed to need it. Her voice was an exhausted whisper. "That was the best orgasm I've had in years. And you, cruel man, how did you learn to edge women like that? It's like you're a dominant."

"I'm sorry, Iris, I didn't intend to be cruel. I just did what felt right. I think you knew I like going down on women. I just enjoyed licking you."

"It was wonderful." She shuddered, so he held her tighter.

Cathy added, "Rob, I was watching with envy, I can't decide if I want you to do it for me too or if I want to make sure you never do."

"I don't know what I did. I just did what I enjoy doing, without much thought."

Michelle said, "what I want to know is how you took the whipping. I'd have called you a pain slut, but it was more like you ignored the whip entirely."

"I suppose it's what I did. I was busy doing something else."

"Rob! I whipped you until my arm was tired!"

Rob shrugged.

Iris offered an idea. "You might have been in your version of subspace."

Rob was unconvinced. "It didn't feel that way."

Cathy had a different question entirely. "Rob, you could have tried to rush Iris to an orgasm to limit the whipping. Instead, it seemed to me you made a point of going slower than usual."

"Rushing seemed like I'd give her less pleasure. As I said, I just did what seemed right."

Michelle slipped onto the bed behind Iris, Cathy behind Rob. The four of them lay together, then Iris stirred. "Okay, I must get some sleep." She gave Rob a kiss. "You're good at aftercare, no wonder women fall in love with you."

As they untangled to let Iris go to her own bed, Rob stopped and winced. "Ouch! I spent the whole day with the plug in, didn't even notice it most of the time, why does it hurt now?"

Michelle had to apologize. "Rob, it should have come out before now. I'll bet the lube has all disappeared."

Cathy had to laugh. "The original plan was for each of us to take you with a strap-on after a short whipping. You have a talent for changing our plans."

Michelle had a bottle of lube in her hand. "Face down, Rob, I'll get you more comfortable before we take it out."

Michelle probed and prodded, adding lube a bit at a time. Finally she had Rob get up on his knees and she removed the plug. Soon they were all in nightgowns, three of them together in Michelle's bed.

Chapter 28

Saturday morning, Rob awoke before Michelle and Cathy. He couldn't get out of bed without disturbing one of them. Staying in bed, he reviewed what had happened during this second stay at Michelle's. He though about what Iris had done for him, what Michelle had done, what Cathy had done. He appreciated these fine women. These were women he trusted. These were women who showed him their love.

Michelle stirred first, turning immediately to embrace Rob. Cathy woke from the motion and joined the cuddling. Soon the two women were out of bed and going down for coffee. Rob decided to act on one of his thoughts. He went to Iris, who was just getting out of bed.

"I was wondering why Michelle and Cathy each peed on me, but you have not."

She gave him a cool look. "I wouldn't do it without consent. It isn't like me to seek consent, wouldn't you say?"

It took Rob a moment to decode her statement. "Iris, please, I'd like you to pee in my mouth this morning in the shower."

He was surprised she hesitated before answering. "Okay."

Rob helped Iris undress as the shower warmed, then undressed himself. Under the warm stream, Rob put his arms around Iris and gave her a soft kiss. Then he kissed his way down until he was kneeling before her, kissing her mound. He looked up to her. "I'm ready when you are."

Her hand guided his head under her, he opened his mouth wide in anticipation. A hot stream ran over his chin, he adjusted his position so the salty stream went directly into his mouth. He let it fill his mouth and overflow. Soon it was over. Iris took his hand and helped him rise, but she too stopped him from rinsing his mouth. "I want you to spend some time with the flavor." After a moment she kissed him, her tongue penetrating his mouth so she could taste as well. Then she let him rinse his mouth.

As they were drying off, she asked, "why was your answer different last night?"

"I had one reason when I asked you, but in the shower I realized I had a more important reason. Iris, one thing about our first meeting for which I haven't specifically apologized: the last thing I did was piss on you. I asked you to pee on me as the prelude to my apology to you: Iris, I am sorry I peed on you that dreadful evening, it was rude of me, a final act of disrespect. You deserved better."

"Oh, you're sweet. I accept your apology. What you did for me last night earned you all the forgiveness you could possibly ask of me. Now, you said there was another reason?"

"Yes. With you just now I intended to swallow. I learned I'm not not willing to swallow, may never be. Had Michelle used my mouth last night on the table, I'd have spat it all out, quite rudely. I felt it as I said 'no;' now I've tried and I'm certain. I remember now I'd made quite a dire promise to her when I was under her training a week ago."

"Precisely why I wait for the man to ask me, instead of asking him to consent. He must be willing, not just obedient."

Back in their nightgowns, Rob and Iris descended to the kitchen. Rob made a pot of tea and served Iris tea and toast where she had joined the other ladies at the dining table.

Michelle and Cathy learned why they had come down so late. Michelle made a pout. "I'm a bit jealous."

Cathy agreed. "Me too. There is a certain justice in Rob's choice. But this time will lead to others."

After the four of them had breakfast, Rob turned to Michelle and asked what she had planned for the day.

"We should talk about when you will come. It would be better if you don't come until after we've returned from tonight's party, but we've been quite hard on you. Can you continue?"

He surprised the ladies by saying he was comfortable. They were accustomed to submissives who'd be begging for release after three days of torment.

"Right, then, here is the plan for the day. We've a session planned in the dungeon, should it be in the late morning or the mid-afternoon?"

Rob was surprised she was giving him a choice. "Whatever fits your interests."

The mistresses decided to split the planned session in two. Rob was ordered to strip and enter the black door at ten o'clock.

Rob went to the dungeon a bit before the appointed time. He settled himself to kneel on the floor and tried to clear his mind as he had discussed with Cathy Friday. The method seemed to work, he found himself both unsure of, and unconcerned about, how much time had passed when the door opened and Iris signaled for him to enter the dungeon with a small gesture of her finger.

The three mistresses were dressed for domination. Iris wore a black corset covering her breasts, but pushed them up so they bulged theatrically. Michelle wore a black leather harness, the straps forming the outline of a bra, her breasts supported but fully exposed. A short, black leather skirt was attached to the harness. Cathy wore a dark green, brocade corset, a bit more conservative than the other women.

Cathy pointed to the whipping bench. He went to it and bent over. He saw the knee rests were removed, but he put his arms on the arm rests and waited to be secured.

"This morning is another exercise is self restraint," Michelle said. "We won't tie you. It's up to you to stay in position as long as we have our way with you."

"Yes, Mistress."

A finger began to penetrate his arse, applying lubricant, he supposed it was Cathy.

Iris walked across his view, her strap-on dildo in place. All too soon he felt the cold tip pressing against him. It wasn't too large, he had no difficulty holding still and letting her - whoever it was - penetrate him.

The next surprise almost had him getting off the horse, the woman with the dildo the only thing keeping him in place. A mouth suddenly enclosed the head of his dick and began to slide slowly down his shaft.

"That's right." Michelle's voice came from behind him. "Each of us is going to have our way with you two different ways. Hold still."

Rob was unable to figure out who was doing which to him. He decided he needn't care; it was the three of them. Each time the dildo in his arse changed, the mouth on his hard dick went away for a time. He couldn't tell if it was one woman or each of them taking turns. He was penetrated several times, he didn't count. He was fellated each time he was penetrated, the mouth on his dick exciting, but teasing, not a serious effort.

And then it was over. After a dido was taken out, he felt a hand sharply slap his bottom. Michelle told him, "good job, I'm proud of you for holding still for us."

He didn't move, of course, he knew better than to trust a Mistress at a time like this.

Michelle sounded amused. "We're done, Rob, you can get up. And thank you for waiting for permission, that's good etiquette in my dungeon."

"One more thing," Iris said mildly, holding up a butt plug. Rob thought it looked big.

Michelle agreed. "Ah, right you are. Rob, back down over the bench for a moment please."

Rob complied. He thought they spent more time than necessary lubing his bum again, then the plug was slipped in. It may have looked big, but it slid in and settled in place without too much discomfort. It might have been the same one as the previous day

"Now, Rob, you're to spend the rest of today wearing what's been set out on you bed."

It was up two flights of stairs to get to his room, carrying his nightgown. He realized the plug went in easily because of the pegging he'd received just before. Now, with his arse sore from the dildos moving in and out for so long, the plug caused more pain than he'd expected. By the time he reached his room, he was thinking he'd refuse to go along and take it out. He decide to see what would happen over the first hour.

The bed had a new package of stockings, a suspender belt and a pink, silk shawl printed with flowers.

He spent the morning moving slowly about the kitchen, cleaning. It was something to do, he needed to keep busy. The plug made sitting with his computer unattractive. Apparently the theme of the day was kissing; the ladies would stop him at random intervals, wrap him in an embrace and spend a few minutes in passionate kissing.

The shawl kept his torso warm enough, but his legs were cold.

As he was bent over Michelle's dining table, polishing, he saw the flash of a camera. Iris came over and showed him the photo she'd taken with her phone, his legs with stockings and suspenders. He was bent over the table, his balls visible between his legs and the plug up his bum perfectly visible. "Just a work of art, Rob. Simply a lovely picture, thank you." She kissed him, just a sweet kiss between friends.

Rob prepared soup and sandwiches for lunch, then served. The ladies required Rob to sit fully on his chair along with them. Over lunch Michelle began to talk about the event to be attended in the evening.

"Rob, one of my original purposes was to help you become more familiar with the presence of other people, of other men and women, when doing a scene. There are lots of people like yourself in the scene. Men who like to dress up, to fulfill tasks as a serving-girl or just walk in nice dresses or whatever they feel relaxed in. It's not all S&M stuff. There is a whole world full of people who act differently, simply seeking a place to enjoy themselves amongst others who understand.

"So, we've an opportunity for some familiarization at the event this evening."

Iris picked up the discussion. "You last attended such a gathering at my invitation, though involuntarily." She gave Rob a wry smile. "It was a bad experience for both of us."

Rob still had occasional nightmares about what had happened at the club, the beating and the humiliation. His own retaliation upon Iris hadn't freed him from those bad memories. Time and getting to know Iris much better had helped. But he had no intention of letting these three ladies know about it.

Iris continued. "This meeting is different. No outsiders, by invitation only; you're there as Michelle's protege. All must wear fetish clothing. You have been wearing her collar to prepare you for wearing it tonight. Michelle's collar is larger than most, very distinct in its ornamentation. Everyone who sees it will immediately recognize whose it is. It will give you protection, it will tell any other masters and mistresses, hands off. You may speak with people, after asking Michelle's permission. Be polite and show them respect, but be yourself." She felt the need to emphasize one point. "Be polite."

"I shall be polite, as I would act normally people among I don't know. Is that good enough for you?"

"Rob, the members attending are people to whom you would be respectful if you met them on the high street. So, please, behave and just observe and learn. These are not bad people, in fact, I expect you may like most of them."

"I'll behave myself. I assure, you, my primary interest is to stay out of trouble."

"Just so." Michelle was satisfied. "Well, we've the latter half of our plans for the day, then we'll prepare for our visit this evening whilst Cathy and Iris make dinner."

Iris had one more point to add. "Rob, I understand surprises are a particular challenge for you. You'll be in a room full of people, you should expect to be surprised. Prepare yourself to handle surprises with grace. I understand you almost did so at the engagement party. This might well be the last skill for you to master before you can face anything."

Leaving the lunch dishes on the table, the three mistresses led Rob upstairs. He saw the familiar straight chair and table set out in Michelle's bedroom. Michelle sat down and required him to stand before her, his hands behind his neck as she stroked him. Hands slipped the shawl off this shoulder. It took little time for him to grow hard.

Iris snapped another picture, just Michelle's hand holding his erection. Iris showed Rob the picture, it was clear he was naked, but he could see the sleeve of Michelle's blouse. "CFNM, Rob: clothed female, nude male. There are a lot of men who like images like this. I like them too. It's supposed to be humiliating. The man is supposed to look intimidated, ashamed. But you, Rob, you just play along with us and have as much fun as we do." She sighed. "It's difficult to dominate you, but I must say it's easy to have fun playing with you." She gave him a kiss, her tongue forcing an entry and dueling with his.

When Iris began kissing Rob, Michelle bent down and took him into her mouth. Rob felt weak in the knees as soon as she did. He had been kept on edge on for so many days. He quickly regained his composure and just let these things happen.

Iris ended her kiss. The mouth was removed from Rob's hard dick at exactly the same time.

"Come, Rob." Michelle gestured for him to get over her lap. She had pulled her skirt up, showing her stocking-covered legs and the slip beneath her skirt. He obeyed and she took care to assure his erection was trapped in the folds of her silky slip, between her legs. Soon she was spanking him with her bare hand in a steady rhythm, her hand moving all over his bum in a random pattern. He certainly wasn't seeking stimulation, but the motions due to the steady rain of spanks on his bum and her her legs shifting a little sent thrills through his hard dick.

After some time, Michelle let Rob stand, but held him by his dick so he wouldn't step away. "There's more for you."

Cathy took her place, pulling of the hem of her dress to expose another slip. Rob submitted himself to Cathy's attentions with the same arrangement of his captured in the folds of her slip. The spanking from Cathy was with a hairbrush. She was striking each place twice before moving. Rob noticed the second hurt a lot more than the first. With the second strike from the hairbrush, Rob jerked involuntarily, which forced him to constantly thrust his dick into her slip. Rob was surprised how arousing it was, he thought by this point he would become accustomed to such things.

Cathy paused and a hand caressed his bottom. "Lovely color, dear, thank you." There was a pause, then Rob heard Iris' camera again. Cathy had him stand, but like Michelle, she held his dick in her hand to keep him in place.

Iris sat on the chair for her turn. Unlike the two mistresses before her, she had shed her dress and was wearing just stockings, bra and panties. She guided Rob's dick to its familiar position between her legs and clamped him firmly. "I recall hearing you wonder if I was hitting you enough. I'll reply with my paddle."

Rob had seen the paddle, of ordinary size, made from varnished oak. It was small enough for Iris to swing easily, but large enough to really deliver intimidating hits. Iris really put her arm into the first few, moving around at random, breaking up her timing. After five or six, she eased up a bit and fell into more of a rhythm. Iris gave him occasional double-hits to the same spot, to painful the effect. But Rob waited it out, knowing the pain would settle and he was right. It wasn't long at all before Rob found he could just take what she was giving him, not feeling it too much.

But he found he was feeling something else. The sensation in his dick built up slowly, he was sure he couldn't hold back. He tried the mental discipline he'd practiced, but this time his dick was not going to be influenced by his mind. Rob gasped, "Iris, Mistress, I need you to stop!"

She paused, putting her hand on his bum and keeping her legs clamped together to keep him in position. "What is it? Hurting a bit much?"

"No, if we keep up I'm going to cum."

The three mistresses laughed at his words. Iris slowly opened her legs and released Rob, grumbling. "Beat him harder than he says he wants and all he can say is he's going to cum."

Rob turned to her. Following an impulse, he got down on his knees and bent to kiss her feet. "Thank you, mistress, thank you!" He wasn't groveling, just having a bit of fun.

"Well, that's nice, isn't it? Rob, I'd say all three of us deserve the same kind of thanks, wouldn't you?" Rob complied, crawling to Michelle, then to Cathy, to kiss their feet and express his thanks.

"Now, Rob, straight to relaxation." Cathy took his hand, led him to his own bed. Iris then required him to bend over his bed as she inspected his bum. "Still beautifully colored and no damage at all," she reported as she took another picture.

Michelle brought him water to drink. As he consumed the glass, she said, "Soon we must dress for this evening's event, Rob. Will you wear the pretty dress you just bought?"

"I think not. This morning, polishing the table, I thought it through and decided I'd attract more attention than I want, in such a stylish dress. You mentioned men as serving-girls. I imagine it would be better if I wear a maid's uniform. Don't get me wrong, it is a lovely dress, I'd like to wear it out dancing with you some evening." He became serious. "Michelle, I don't want to be recognized, didn't you say you had a mask for me to wear?"

She nodded, this was a good sign he wasn't overly confident. "Yes, of course. I have several masks, let's go choose one." She took him back to her bedroom and rummaged in the top of her wardrobe. She took out a box and scattered several masks on her bed: a kind of Zorro mask, but also ladylike ones, with sparkling stones and feathers. "Mmm, I have the right one here for you. It will match your uniform." She showed him a black mask covering his eyes and the bridge of his nose. On top of the mask black feathers had been applied. Rob tried it on, the elastic was comfortable and it fit his face like a glove. It was made for him. Since only his mouth was uncovered, it was unlikely anyone would recognize him.

"Thank you Michelle. This is exactly what I need to attend such an event. I do hope your collar will provide enough protection against unwanted interference."

"I'll have a word with the wardens to keep an eye on you. And of course I'll be there for you." She paused, looking him over. "You'll want a touch of lipstick at least. You know, it's high time you learn to do your own makeup."

They spoke a bit about what he could expect. Rob would just observe and learn, mind his own business and act politely. She even convinced him to dress in her house, as she would. They would drive to the event with their costumes covered by their coats.