Charlie’s Stepmother 19 & 20

By brhmsj

berlioz53@yahoo.com

Copyright 2023 by brhmsj, all rights reserved

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This work is intended for ADULTS ONLY. It may contain depictions of sexual activity involving minors. If you are not of a legal age in your locality to view such material or if such material does not appeal to you, do not read further, and do not save this story.
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Charlie’s Stepmother 19

Another Trip to New York


“I’ve arranged for you to get some days off from school so that I can take you to New York next week,” Fran told Charlie one morning. “I have some business and I know you enjoyed the last trip. There are more people you should meet, too.”

“Wow! Thanks Fran. That will be cool.” Charlie had enjoyed that visit. The sightseeing was fun, Fran’s friends were, if nothing else, interesting. Unconsciously what had been most significant for him had been the control such a trip allowed Fran to have over him, different from at home. It may not always have been fun but it was comforting. Charlie had come to like submitting to her.

The night before their departure Fran helped Charlie organize things. Charlie pulled his vibrator from the drawer and with a smile said “we’ll need this.”

“You’re a good little boy,” Fran replied. For once that phrase didn’t seem quite so bad. “But that’s not all.” Charlie was chagrined to see that his hairbrush, paddle, and chastity cage were added to the vibrator in his suitcase. Nothing to do about it but accept.

The clothing she chose for him ranged from his usual casual to some of the fancy dress clothes she’d bought for him over time. He did feel quite the adult in those clothes so, unlike most teens, he looked forward to wearing them. Charlie had already packed the special cum absorbent pants. Fran was pleased not to have had to ask.

Fran woke Charlie early. She pulled back the covers, let him use the bathroom, then put him over her lap for a spanking. Charlie expected she would. A reminder to behave during the day’s travels. It didn’t hurt all that much but he’d feel the sting on the airplane ride. The vibrator was packed so Charlie would not be cumming on the plane. Or so he thought.

The ride to the airport was uneventful. This time they were flying on a carrier which provided rather secluded first class accommodations. Charlie was very impressed! His seat had him essentially out of view of other passengers.

When the flight was underway and food had been served Fran ordered “take those pants off!” Charlie wanted to protest but knew he shouldn’t. He slipped off his shoes, then pulled off his pants. He was wearing a pair of fancy briefs Fran had given him. “Did I say that you could wear underpants today?”

“No, Fran.” She hadn’t said anything, one way or the other.

“Get them off!” He obeyed, releasing the erection that the excitement of potentially being on display had caused. The prospect of being seen made him nervous but there was a thrill, too, especially as he was hard. “You’re getting another spanking when we get to the hotel.”

“Yes, Fran.” She passed him a towel, the reason clear. Masturbating, half naked, on an airplane was, of course, a new adventure. Having been given the implied permission Charlie gladly wrapped his hand around his hardon. He did his best to take his time but soon was shooting into the towel.

“Good boy,” Fran said when he was done.

“May I. . .?”

“Not until I say so. That question has earned you the paddle later.”

“Yes, Fran.” Weirdly the prospect of a paddling was proving exciting. Or maybe it was just the prospect of some extended time of just him and Fran. Between getting up early and having shot, Charlie was sleepy and dozed off.

He was awakened by a steward asking “what have we here?” His eyes popped open to see a young steward quite obviously enjoying the sight of a half naked youngster. The man gave him a conspiratorial smile. Charlie felt that his secret was safe. Also it was fun being caught with no pants.

The steward was bringing refreshments before the end of the flight. He put their food down and with a wink at Charlie moved on to the next passengers.

“My, my, you’re turning into a little exhibitionist,” Fran said when they were alone again. Charlie blushed but maybe she was right. After the snack Fran told Charlie to get dressed. Arrival and taxi to the hotel were uneventful.

As on their previous trip, Fran had booked adjoining rooms with a communicating door between them. After the luggage was delivered and unpacked she said, “alright, young man, out of those clothes. It’s time for your spanking.” Silently Charlie obeyed. He waited, standing, next to the bed.

In a moment Fran came in. She picked up the paddle which Charlie had placed on the bureau, sat in the chair and beckoned the boy to get over her lap. Charlie silently obeyed.

SMACK SMACK SMACK A short hand spanking. Charlie remained calm. That changed quickly when the paddle began to land on his bottom. WHAP WHAP WHAP WHAP WHAP “Owwww!” This was a true punishment spanking. WHAP WHAP WHAP She didn’t intend to break the boy, she was asserting her authority over him, authority she expected to be obeyed throughout this trip. And at all other times, too.

WHAP “Owww!” A few more whaps, some kicking from Charlie, and it was over. She rubbed his bottom briefly then let him up.

“We’re having dinner at a restaurant with some friends of mine but nothing before then. I’m going to rest and I advise you to do the same. I expect best behavior tonight and being well rested will help insure that. I’ll lay out your clothes later.”

Charlie understood the instruction to rest to be an order. After the paddling he was happy to lie down for a while. Face down for the moment. He had his phone. He put through a Skype call to Max.

“Hey! How’s NYC?” Max asked when he answered.

“Sore at the moment,” Charlie replied with a chuckle. He told Max about his day – the spankings, the pants off on the plane. “The bit about the underpants was sneaky but I knew she’d be spanking me today. It goes with a trip to New York apparently.”

“You OK?”

“Oh yeah. You know that I kinda like her. . . her interest in me, I guess you’d call it.”

“I guess that’s what it is. Not much here. Timmy has a ‘date’ for lunch with some girl. I think he’s hoping he’ll get a little action. He’s not the Don Juan he thinks he is.” They laughed. Unlike his older brothers Timmy had discovered girls and was eager to explore this new world. “But he is a little sex fiend.” More laughter. “What’s up tonight?”

“Dinner with some friends of Fran’s. Likely a boring group but I’m expected to be decorative. I get a good meal out of it.”

“You gonna see that old dyke, too?”

Charlie laughed. “You mean Marguerite? I’m sure we will, though Fran didn’t say. After Marguerite’s visit to us I suspect if we do visit her I’ll be naked for the whole time, showing off for her old lesbian friends. You’d think they wouldn’t be interested but I think they enjoy seeing that Fran has an obedient puppy.”

“You think you’re a puppy?” That sounded kinky and interesting.

“No, just a turn of phrase.” But an idea had been planted in two heads. A bit more chat and they wrapped up.

Before they did Max said “oh, and it looks like Gerry will get Patrick over to use the pool. Could be interesting. I’ll let you know.” Patrick’s reluctance to visit and be naked was well known. Yes, it could be interesting.

Call done, Charlie dared to roll over onto his back. Not too bad; he’d had worse. He did doze off for a while, awakened by Fran. “Get cleaned up while I put your clothes out.” Charlie disappeared into the bathroom. He was naked already so not much preparation needed. He decided to take a quick shower. The water didn’t sting his bottom but he did feel it. Something reassuring about it.

When he returned there was handsome suit waiting on the bed, accompanied by a shirt and tie. And the silk briefs which made him smile. He quickly dressed. The underpants felt great and the suit fit perfectly. Fran had put out stylish shoes and socks. Charlie was pleased with how he looked when he checked himself in the mirror.

“My, my, aren’t you the handsome thing,” Fran said when Charlie had been let into her room.

“Thanks. This is a great suit. Thanks for getting it.”

“I’m glad to. Anything for my men,” she answered with a smile. Comments like that always brought on a slight blush from Charlie.

With that they were out the door. The restaurant was the one they’d been to a couple of times on the previous trip. Charlie was delighted. He’d enjoyed his time there and the food was very good. When they went through the door, the maître d’ recognized Fran and said “your party is waiting over here” and escorted them to a table. Charlie spotted Albert from the previous visit, this time with a different young man. Albert and his friend rose in greeting.

“So good to see you, dear,” he said to Fran, then they exchanged air kisses. “This is Martin,” Albert said, gesturing to his comrade. Martin shook hands with Fran. When he turned to Charlie, Charlie said “I’m Charlie” as they shook hands.

“I’ve heard about you,” Martin said as they sat. Charlie had no idea what to think that meant, given what some of Fran’s friends were like. He noticed two more unoccupied seats.

“I’m sure you remember Fred,” Albert said to Fran.

“Of course! ‘Uncle’ Fred.” They chuckled at that.

“Yes. He has a new protégé he is eager to show off. I have no idea what to expect.” With no preamble he said, “Martin needs to be dealt with when he get home. I expected better.” Martin blushed deeply at that. Charlie wondered if that meant a spanking.

“I made sure Charlie was ready for the evening,” Fran said with a sly smile. That confirmed for Charlie that Martin was getting a spanking later. He shot the man a sympathetic look. He, too, was blushing now. He was given a glance of solidarity by Martin. What could he have done already which warranted a spanking? Or did Albert just spank because he wanted to, like Fran?

At that Charlie became aware of new arrivals. The three men stood to greet the newcomers. They were a man of indiscriminate age who had an air of authority about him. Charlie was finding that made the man very attractive. A new feeling. With him was a young man who appeared to be college age. Also quite attractive.

“Fran, darling,” Fred said as he bent over to give her a real kiss on the cheek. “It’s been too long.”

“Yes, it has.” She indicated Charlie. “This is my stepson Charles, otherwise Charlie.”

“Ah, yes, the stepson,” Fred said as he shook hands with Charlie. “This is Andrew who I’ve taken under my wing for the time being.” Andrew said nothing but shook hands with Charlie, Albert, and Martin. Another interesting comment – “under my wing for the time being.” Charlie had no doubt that these two young men were under the authority of the older men, much as he was with Fran. Had they chosen to have these “mentors”?

Everyone seated, an officious waiter approached, clearly sizing up the three younger men at the table. Without consulting the wine list, Albert ordered two bottles of wine. “I know Charles is underage, but would you allow him some wine?”

“Yes, he can have a bit tonight.” Charlie couldn’t help but beam with pleasure at hearing that.

“We won’t get him drunk!” Albert replied with a chuckle. Charlie noted no reaction from Martin or Andrew.

“Fran, darling, what are you doing out in the boondocks? We miss you here in the Big City.”

Fran laughed. “You needn’t be concerned. I can manage affairs just as easily at home as I could here. My two men keep me plenty busy, too,” she added with a glance at Charlie.

“Judging by this one, I’m sure they do. Where is the husband? I haven’t had the opportunity to pass judgement.”

“He couldn’t make it this time. You’ll meet him in due time. No need to be overly eager.” More laughter from the older adults.

There was more banter of this type after the orders were taken. Martin and Andrew showed every sign of being quite curious about Charlie though they were doing their best not to be looking over his way. Rather unsuccessfully. Charlie was sizing them up, himself. It seemed, though, that the three younger men were not to talk.

The talk amongst the older adults was general for quite a while. Then Fred said “I had to settle down Andrew before we came out.”

“Only one way to do that,” Albert said.

“Exactly. The added threat of the paddle after dinner was quite helpful.” Andrew put his head down in shame. “None of that, young man!” Fred said sternly when he saw the reaction.

“No, sir,” Andrew said meekly.

“Some have a lot to learn, as we know,” Albert said. “Fran, from what you say it seems you have things well under control.”

She smiled at Charlie. “Yes, I think so. Don’t you, dear?”

“Um. . . yes. . . yes, definitely,” Charlie stammered.

“Excellent when a boy understands that,” Fred said, his voice indicating approval. Now that Charlie and Andrew had used their voices it seemed that the three younger diners had permission to talk. As they were seated together it was easy.

Charlie tried starting things by asking Andrew if he were in college.

“Ah, I have been. I’m, ah, taking some time off to, ah, sort out some things, I guess you’d say.”

“I’m, well, I’m unemployed for the moment,” Martin said.

“Are you staying with Albert?” Charlie asked.

“He, ah, he let’s me use a room.”

“Fred is putting me up for a while,” Andrew said. Both seemed reluctant to reveal their actual situations. Charlie didn’t know how to ask further. “So, Fran is your stepmother.”

“Yes. She and Dad got married a couple of years ago.”

“And she took you on when they were settled?” Martin asked.

“Well I guess you could say that,” Charlie responded. “Dad gave me a choice. Things are working out.” He wasn’t going to say much, either.

“Lucky boy,” said Martin. Andrew nodded in agreement.

Fred suddenly cut into the younger men’s discussion. “Talking about your spankings?” he asked in a voice that purposely carried to adjacent tables. All three younger men could see that other diners had picked up on that. There were three blushes.

“Um. . . we, ah. . .” Andrew said. After a pause he added “we, ah, weren’t quite on that. . .”

“Well you should compare notes,” Fred answered. A couple of heads turned. Charlie, Andrew, and Martin couldn’t know at this point, but spanking was an oft-discussed topic in this restaurant. When Charlie relaxed from his embarrassment he did cast an eye across the room. There were other tables of older adults, including some women, with younger men. No younger women, he noted.

More embarrassment followed. “Do these two have vibrators?” Fran asked. Chuckles from the other two men. “That’s confirms that!” she said in response. Charlie glanced at his companions. Their faces told him all he needed to know. He wondered if they had the pants, too, but had no idea how he’d approach that topic.

The main courses were done. “I’ve already taken care of dessert,” Albert announced. He certainly had! A cake in the unmistakable shape of a paddle was put down on the table by the same waiter who had a supercilious smile as he placed the cake.

“Something good for boys,” the waiter said when he had the cake in place.

Fred was laughing. “This always is a perfect ending to a good meal,” he said. So, this wasn’t the first time. Charlie wondered if such cakes were a secret part of the menu.

“Charles, you’re the youngest. I think you should do the honors,” Albert said. Charlie blushed. This was all so new. Fran nodded approval. Charlie did his best to create equal slices all around. No one complained. The cake was delicious, another perfect item from this restaurant. Charlie was uncomfortably aware that the cake was seen by diners at other tables. The waiter had not been subtle about transporting it or putting it down.

“And who gets the real thing later tonight?” Fred again, and again purposely loud enough for other tables to hear. Again deep blushes on the part of all three younger men.

“Well? Speak up!” Albert said, quite sternly. He’d already said that Martin was getting spanked when they got home.

Martin looked ashamed. “I’m getting it later,” he said slowly.

“Oh?” asked Fred with an evil grin. “What is ‘it’?”

Martin looked at Albert, pleading in his eyes. “Tell him!” Albert ordered.

“The paddle,” Martin said in almost a whisper.

“Speak up!”

“The paddle. Sir!”

“Good boy. And what about you, young man?” This directed at Charlie. For a moment he was stunned.

“Be a good little boy and answer,” Fran said quietly but the threat was clear.

“I, uh. . . I got the real thing before dinner. I hadn’t behaved properly.” He couldn’t believe he was saying that. Something about the atmosphere at the table made it happen. He wasn’t sure if later he could even tell Max about this part of the evening.

“I’ll be assessed when we get home,” Andrew said, still red faced.

“You know what will happen already, don’t you?” Fred asked.

“Yes, sir. The paddle, sir.”

“That’s a good puppy.” Charlie had no idea what that remark meant.

With that the older three went back to their own chat. After a tense silence the younger three started conversing again. This time on subjects other than spanking. Charlie wondered if a bedtime spanking was in the works for him. It would be like Fran to make sure he wasn’t left out, as it were. As long as it wasn’t the paddle again.

Dinner was wrapping up. “He’ll have the vibrator tomorrow,” Fran was telling the men. “It’s wonderful at keeping control.”

“You have chastity, of course,” Fred asked.

“Of course.” Now the older three were standing. The others did, too. Fran gave the men air kisses. “This was lovely. I’ll try not to make it so long before the next one.”

“I hope so,” Fred responded. “We do miss you.”

“I know. I miss you, too.”

“Will you be naked when you get back to the hotel?” Andrew whispered in Charlie’s ear.

“Yes, I’m sure I will,” he responded. Martin’s nod affirmed that there would be three naked youngsters.

“‘Boys shouldn’t be modest’ is his mantra,” Martin replied.

“Her’s, too.” With that they were out the door and the group broke up.

Back at the hotel Fran did, indeed, order Charlie out of his clothes. “Did you like the two boys?” she asked as he undressed.

“Yes, I guess so. I don’t feel I really go to know them.”

“No, you wouldn’t from one dinner. Albert and Martin are good mentors, giving young men guidance and helping them get set in life. Andrew was having a hard time at college but it looks like he’ll be ready to go back in the Fall. Martin is having a harder time getting his life organized but spankings and chastity are getting him calmer. He’ll do fine in the long run.”

“I see.”

“Now, into bed with you young man. We have a lot to do tomorrow.”

“Yes, Fran. Are we meeting Marguerite at some point?”

“Tomorrow, in fact. I’ll give you a little trim in the morning. She’ll like that.” Charlie knew which hair would be trimmed. This also confirmed what he suspected – that he’d be naked at Marguerite’s this time. Would he have to “perform,” too? Oh well, just try to take it in stride.

“May I. . . before I go to sleep?”

This time Fran didn’t embarrass him with saying “masturbate.” “Yes, dear. I think you should. I’m sure the dinner talk was stimulating.” She came into his room and gave him a kiss on the cheek, then went back to her room, closing and locking the communicating door behind her.

Charlie was glad to be alone. He messaged Max to see if he were still awake. He was. With a quick video call Charlie told Max some of the evening’s events.

“I’ll tell you everything when I get home,” he promised.

“Can I watch?” Max asked. Both boys liked a session at bedtime, when they could get one. Something about masturbating on camera for his friend was very exciting, making him quite hard. Charlie didn’t want to take long but when it was over Max said it was great. With that they signed off.

Tomorrow would be another day.




Charlie’s Stepmother 20

New York, the Next Day


Breakfast was room service. Fran wanted Charlie to stay naked for a while longer. He’d be naked quite a bit today, not that she’d confirmed that yet. Or if she would at all until it was time. Room service also meant that Fran didn’t have to change out of her comfortable, and sexy, night wear. A relaxed morning.

She woke Charlie by pulling back his top sheet, exposing his morning wood. He had long since stopped being bothered by her seeing him hard in the morning.

“Breakfast is on the way. By the time you take care of this it should be here.” With that she went back to her room, closing the connecting door to give him privacy. Charlie didn’t take long, took a quick shower to clean off the semen, then knocked on the door. Fran opened it and welcomed him in. Breakfast was spread out and ready.

While they ate there was time to discuss their fellow diners from last night. Charlie wanted to know why Fred was called “uncle.”

“Years ago one of boys called him ‘uncle’ and once Albert heard about it, it stuck. Fred often requires that his boys call him that. You should, the next time we meet.”

Charlie stored that away. He wondered if “Uncle” Fred would tell Fran to have him spanked for not calling the man “uncle.” Or, for that matter, would he want to do the spanking himself. Would Fran let someone other than Bunny spank him? There were other things on Charlie’s mind at the moment.

“Fran, what did Fred mean by calling Andrew a puppy?”

Fran chuckled. “It’s a form of play or a form of domination. Or both. The submissive boy behaves like a puppy. There’s special gear for those who want it. Finish your breakfast and we’ll go to the Village where I can show you some things in the shops.”

On the cab ride Fran explained about certain fetishes. Charlie and Max had read about some things on line but had not researched it much. Charlie had no idea there were so many variations of relationships.

“So, do guys go to Fred because they want to be a puppy? Or whatever?”

“Some do, but sometimes he finds young men who need to be submissive even though they don’t know it. His training can be quite rigorous.” She left it at that. A few minutes later they pulled up to a block with various shops of sex toys. They had visited it on the last New York trip.

Inside Fran showed Charlie the leather section, including some of the puppy play items.

“Guys really put on those masks?”

“Oh yes. And any puppy needs a collar and leash,” she said, indicating an array of collars. Charlie took it all in silently. “Should I put you on a leash?” Fran asked after a moment. She was smiling as she asked it.

“Um. . . do you want to?”

“That’s not what I asked, naughty boy. How should I deal with that?”

After a pause Charlie said quietly, hoping no one could hear, “a spanking?”

“Or some time your cage. I’ll think about it. But you haven’t answered the question.”

“No, I don’t think so. I mean, no, I don’t. I don’t think I’m a puppy type.”

“It’s not always for the puppy to decide if he actually is a puppy.” Said with another smile. She looked like she was considering it. For Charlie or David? Or both? To Charlie’s relief, no puppy things were bought. She did buy another chastity cage. “Gives us a bit of variety,” she said as she made her choice.

On the ride back to the hotel Fran said that they’d be having lunch at Marguerite’s. “I’ll put out the clothes for you.” Charlie both liked and didn’t like that she selected his clothes. It was comfortable to let someone else make those decisions and she did dress him in great clothes. On the other hand, he liked the autonomy of making his own choices. He knew to obey.

At the hotel Fran said “take a quick shower. I’ll be waiting for you.” Charlie didn’t think he needed another shower but he did as told, giving himself a thorough scrubbing. When he emerged from the bathroom he saw the day’s outfit waiting on the bed. He was pleased with what he saw. Also on the bed was his vibrator. He wasn’t surprised. He’d wondered when that would appear.

“Marguerite is expecting you to be wearing your vibrator and we can’t disappoint her, can we?” Fran said as she applied lube to the device. Charlie went over her lap for the insertion. He liked the intimacy of doing it that way. After a few mild swats to his bottom, Fran slid the vibrator into him. It always felt good to have it in. Reassuring, somehow.

As he dressed, Charlie realized that today’s pants were not the special absorbent ones. What did that mean? The vibrator was in him so that meant he’d be made to cum at Marguerite’s. Then it hit him – without the pants! He’d be naked, hard, and shooting in front on Marguerite and her guests. He blushed at the thought, followed by a bit of exhibitionist excitement. Life certainly had changed for him since Fran entered his life, he thought as he finished dressing.

“Now, that’s my handsome good little boy,” Fran said when Charlie came into her room. It gave him a warm feeling. He’d come to like being called that even with its implication of childishness. Fran was dressed smartly in a skirt suit. Charlie had come to take pride in how his stepmother looked on festive occasions. A biological mother and son couldn’t love each other any more than these two did. Charlie felt no disloyalty to his mother because of this.

They arrived exactly one o’clock at Marguerite’s building. Charlie sensed that Fran needed for them to arrive at exactly that time. Did Marguerite have some sort of hold over her? It was hard to imagine Fran in anything but the dominant role, though Marguerite certainly was formidable.

Inside, the elevator whisked them to the apartment. They were the first to arrive.

“So good to see you, and right on time!” Marguerite said in her deep voice as she greeted them. The ladies exchanged the requisite air kisses, the Marguerite shook hands with Charlie.

“Thanks for having us,” he said.

“Such a polite boy,” to Charlie. Then, to Fran, “is he properly prepared?”

“Oh yes,” Fran replied. This must mean the vibrator. He’d just have to wait to find out what was what today.

The elevator whirred and two of the ladies from the last visit’s tea got off, one rather severely dressed in mannish clothing. Fran knew them. The greetings of old friends were exchanged.

“Good to see you again, Charles,” said the one in men’s attire. “I understand we’ll see more of you today.” She was quite serious in that comment but her companion chuckled.

“And quite worth it,” Marguerite added.

Two more trips by the elevator and the luncheon party of all women was complete. “We’re fortunate to have a waiter today,” Marguerite said with a gesture to Charlie when everyone was there. A glance from Fran told him what he already knew. Trying to remain cool about it, Charlie undressed completely, carefully setting his clothes aside on a chair.

Sounds of approval from all the guests. “Have you considered shaving him?” one woman asked.

“I prefer my men to look manly,” Fran replied.

“Well, he certainly does,” said another woman.

“Please, everyone be seated,” Marguerite said with a gesture toward the dining room. “Charles, I’ll show you what you need to do.” She took him to the kitchen where everything was ready. All he had to do was bring out things at the appropriate time. She put a serviette over his arm in the traditional style. “Must have you wearing something,” she said, chuckling at her own humor. “Serve the wines first. Ask the ladies which they want, and pour carefully. Then you will set the bottles on the side table and let the ladies serve themselves the food. You then step aside to be ready for anyone’s needs. Be sure to keep the water and wine glasses full.”

“Yes, ma’am.” The bottles of wine were on the side table. Marguerite led the way. Charlie waited for her to be seated, then served the wines requested. That done, he returned the bottles and went back to the kitchen for the various platters of food. As he crossed the room he felt a mild vibration in his rectum. It was pleasant, not enough to get him hard. Yet.

Having served the platters, Charlie stepped aside to keep an eye on the proceedings and to wait further instructions. As he waited he felt the speed being turned up on the vibrator. For the moment he remained calm but the pulsing got high enough that he felt his cock growing in response. He remained quiet but his face became flushed with embarrassment and excitement. He saw that one of the ladies noticed. He had feared that this was why he had the vibrator in him. Now the fear was coming true. A nod from the first lady got the attention of some of the others. Soon he was being looked at by everyone on one side of the table.

The speed increased. Charlie began to twitch in response, followed by a quiet “oh oh oh” as the stimulation increased.

“Charles, stand over here where we all can see you,” Marguerite said. Casually said, but a command, nonetheless. Charlie moved to where all could watch. He was going to ejaculate in front of these women and there was nothing he could do about it. Before the sensations fully overtook him he wondered why these older women, all of whom must be lesbians, would want to see a teen boy have an orgasm. An orgasm induced hands-free, caused only by stimulation of his sensitive prostate.

Now he was shaking and twitching. He was getting close. The “oh oh oh” became a long moan, then with a shudder, he shot. For distance, too.

“My, my, my,” said one of the women.

“You must be very proud,” another said to Fran who beamed with pride.

When Charlie settled down, Marguerite said “use that serviette to clean up.” Another command. The women enjoyed the site of the boy on his knees on the floor, mopping up. For the first time in all of this, Charlie felt humiliated. Mess cleaned up, he returned the serviette to the kitchen, found a new one, then resumed his spot.

For the next twenty minutes or so he basically was ignored. He would fill a wine or water glass as necessary, otherwise had to wait for the ladies to finish the main course. Fran had turned down the vibrator after his orgasm but did not turn it off completely. The mild vibration for the moment was soothing.

“I think we’re done,” said Marguerite eventually. Charlie cleared the plates then put out the plates and utensils for the dessert. “Give us a few minutes before the dessert. In the meantime, do start the coffee.” Charlie returned to the kitchen where a coffee pot was waiting to be turned on. He got it going then returned to wait.

As he stood he felt the vibrations rising. Would he have to cum again before dessert? It had been only about a half hour at most. Teens do recover quickly and be ready for another ejaculation, he knew that, but he did feel he was being toyed with. Yet he was not resenting Fran for doing it.

Sure enough, before long he was hard. The vibrations against his prostate were stimulating him yet again that afternoon. He knew it wouldn’t be long before he shot, did his best not to twitch and shake but his excitement became too much. He moaned as he had before, shuddered, and released a smaller but still respectable load for the ladies.

“They do recover quickly,” one lady commented. Murmurs of agreement.

“Oh dear,” said Marguerite, “it appears you have another clean up job.”

“Yes, ma’am.” Charlie went to the kitchen for another serviette, returned and presented his backside to the women as he cleaned the floor.

When he was done Marguerite said “you may bring the dessert now.” Dessert was on individual plates. Three trips had everyone served. While they began eating he prepared the coffee and brought it out. “The ladies will pour their own, dear,” Marguerite told him. “Stand on this side, please.” She indicated the other side of the table. Now he’d be where the women on the other side could see him in all his nakedness. That was only fair, he supposed.

When the women finished the dessert Marguerite gave Charlie permission to clear, which he did efficiently. That done, she said “Charles, go ahead and sit down in the den while we finish our coffee.”

“Thank you, ma’am.” Since his second ejaculation the vibrator had been on the lowest speed which felt good. He relaxed in a comfortable chair, enjoying the chance to sit. The mild vibration was soothing. He didn’t fall asleep but did get lost in his own thoughts. The women certainly were taking their time with the coffee.

He was startled back to reality by an increase in the vibrator’s speed. It took longer, even without fighting it, but he did become hard again. When the ladies returned to the den for more socializing he was standing up straight, as it were. “A remarkable young man,” someone said as the observed him.

As the ladies were settling the speed was increasing. Nothing was said about getting up so he stayed put in the chair. There was no doubt that Fran was bringing him to his third orgasm in a very short time. It took a bit longer but eventually he let go, moaning and shaking, covering his abdomen with a much smaller load.

“You’d better shower, dear,” said Marguerite when Charlie’s breathing was back to normal. She indicated where he should go. Her en suite bathroom was as stunning as the rest of the apartment. The towel he used when he dried himself was the fluffiest, softest he’d ever used. As he dried off he could hear sounds that the party was breaking up.

“Charlie, come say goodbye to the ladies,” Fran called. He came to the doorway and said goodbye. The women all seemed most appreciative of his being there today. When it was just Charlie, Fran, and Marguerite, Fran handed him his clothes.

“This has been a most pleasant time, as always,” she told Marguerite. “But I think I need to get this boy back to the hotel.”

“Yes, I’d say you should.” Marguerite then wrapped Charlie it what felt to him as the female equivalent of a bear hug. He returned it as best he could. She seemed satisfied. He dressed, the elevator was called, and they were off.

In the cab Fran said “you must be exhausted, dear.” Charlie just nodded. “You can nap when we get back. I am meeting some people for dinner. You’d be terribly bored at this one so I’ll have room service send up a dinner for you around seven.”

“Oh, thank you.”

At the hotel they went through Fran’s room. She opened the communicating door. “Go ahead and lie down or whatever you need to do,” she said. “No clothes until morning,” she added in firm tones. Charlie didn’t object. Even on display, he was enjoying having such a clothes-free day. Sure enough, as soon as he lay down he fell asleep. A couple of hours later he awoke to find that Fran was gone. There was a note saying “enjoy your evening. See you in the morning.” She must be expecting a very late evening.

Charlie dialed Max’s Skype video. He answered right away. He wanted to know everything that had gone on. Charlie gave him a brief recap then again said “I’ll fill you in on everything when I’m back. What’s going on there?”

There wasn’t much to report on Max’s end. Both Gerry and Timmy had incurred Bunny’s displeasure with the result that Gerry had sore balls and Timmy had a very sore, red bottom. The boys chuckled at that.

“I guess you’re next,” Charlie teased.

“Did you get spanked today, too?”

“No and I doubt I will tonight. It sounds like she’ll be out late.” After some more chatter, they signed off. Charlie spent some time checking up on emails and other online things.

At exactly seven o’clock there was a knock at the door. Charlie grabbed the robe supplied by the hotel, put it on, and called out “who is it?”

“Room Service,” was the return. He looked through the peephole. Sure enough he could see the cart with food. He opened the door to see the cart with a very handsome waiter behind it. As the waiter pushed the cart into the room he said in annoyed tones “I was told you’d be naked!”

“Oh?” was all Charlie could say.

As he laid out the dishes, the waiter said “Well? Get that robe off!” His forcefulness had the effect of making Charlie start to get hard. It also made him obey. Slightly red-faced he doffed the robe, revealing his semi-erection. “Very good,” was all the waiter said as he finished his task.

When he was done, the waiter turned to Charlie who had been quietly watching. “Now, Mister, I should report you to the lady for being covered when I arrived with dinner. However, I’m a nice guy so I’m giving you a choice. I can report you to the lady and leave you to face the consequences or I can give you the discipline you deserve right now.” Casting his eyes to Charlie’s growing cock, he said “and from the look of things, you are eager for some discipline.” With that he took Charlie by the arm, led him to the bed, then pulled him over his lap.

SMACK SMACK SMACK SMACK SMACK The hits came hard and fast. He had a strong arm! The briefest of pauses and ten more hard smacks came down. Charlie was yelping by now.

“Had you been given permission to cover yourself when the food arrived?” the waiter barked.

“No, sir, nothing was said.” That wasn’t quite true. Fran had said no clothes until morning. He should have known that really meant in any situation. He was regretting it.

“I wonder,” replied the waiter as he resumed with ten more blows.

“Owwwww! Please, sir! I’m sorry!!”

“Hmph.” The waiter rubbed Charlie’s bottom for a while, then ten more came down. Now Charlie was near tears. Two more and the spanking stopped. Charlie lay over the man’s lap gasping in pain. The man produced a tube of crème from his uniform and began to rub it into Charlie’s bottom, making no effort to be gentle. Charlie yelped some more. He calmed down when a finger went between his cheeks and contacted his hole. No entry was made but the contact was welcome.

A few more minutes of butt rub and Charlie was allowed to stand. “Let that be a lesson to you,” the waiter said. “Nothing more will be said about this. Enjoy your dinner.” With that, the man left, closing the door gently behind him.

The food was delicious though Charlie ate it standing up. Before he started dinner he texted Max “spanking. More to follow.” Max replied “wow!” After a while Charlie did sit. Dinner done, he watched some tv. He was still exhausted from the day’s exertions and surprised himself by turning off the tv and getting into bed at ten o’clock. The sheets felt good against his naked skin and still-sore bottom. He heard nothing until Room Service took the dinner dishes and brought in breakfast for two in the morning. Fran must be back and planning to eat with Charlie in his room.

Charlie got up and showered again in hopes of washing off some of the fatigue. When he returned to the room Fran was there, having set out the food and dishes. Remembering her instruction from last night, and the spanking, he made no move to put on a robe or other clothing.

“Good morning!” she said cheerily. “How are you feeling today?”

“I’m waking up,” Charlie replied with a smile.

“Nothing special for today. I have to do some business, so you’re on your own today. Check the guidebook to see what may be of interest. I’m not sure about dinner, other than we’ll eat it,” she added with a smile.

“Sounds good. There is stuff I’d like to see.”

Breakfast continued with just idle chat. When they were done Fran asked with an enigmatic smile “do you need a spanking before you go out?”

“Oh, please, no!” Her look made Charlie pretty sure that she did know what had happened last night. Had she set him up? That waiter definitely wanted to give a spanking and likely would have even if Charlie had been naked. He seemed the type.

“That’s fine. Tomorrow is our last full day. We’ll visit Albert. There are some things you should see.”

“OK.” With that she went to her room, closed the door, and got ready for her day. They left the hotel together, Fran to get in a cab, Charlie to walk to his first destination.

Other than sightseeing and a casual dinner, the day was uneventful. Tomorrow would be quite the opposite. Having been so fully drained, Charlie would not masturbate until the next morning. Unusual to miss a day.





(End of File)