Charlie’s Stepmother 3 & 4

By brhmsj

berlioz53@yahoo.com

Copyright 2023 by brhmsj, all rights reserved

Charlie’s Stepmother 3


A Trip to New York

At dinner one night David announced that he had a business trip to New York City coming up. “I’d love to have you both join me. You can see the sights while I’m in my meetings. What do you think?”

Charlie was thrilled. He’d been to NYC once and always wanted to go again. So, his answer was yes.

“I think that sounds delightful. I could do some shopping, maybe take Charlie to a fine menswear store.” Charlie wasn’t sure how he felt about that!

“Excellent. I hoped you’d agree because I’ve already booked two rooms at the hotel.” They all laughed. “I know it’s short notice but we leave first thing in the morning the day after tomorrow. I’ve called the principal and it’s fine for Charlie to miss a few days of school.”

“Thanks, Dad.”

Then Fran dropped the bomb. “You both know that you have spankings coming. I’ll save them for the hotel. That will help make them more memorable.” David and Charlie went a bit pale at that but she was right, they had earned spankings and knew they would be coming. Nothing more was said about that and the conversation turned to getting ready to leave.

When they got to the hotel Charlie was impressed with the two rooms and excited to know that one was just for him. There was a connecting door between them. Likely Fran would let herself in when she wanted but that was to be expected.

David’s first meeting was mid-afternoon. “Plenty of time for other things,” Fran said as they moved into their rooms. “Charlie, get your things put away and come back here.” Before they had packed at home she had made it clear that he was to bring his hairbrush and thermometer and have them on the side table by the bed at the hotel. Charlie obeyed.

“Yes, Fran.” He knew what would happen when he returned. Charlie unpacked quickly, making sure all his clothes were put away properly and his suitcase stowed in the closet. In a few minutes he was knocking on the connecting door between the two rooms. Fran opened it and, sure enough, Dad was naked. There was no need for instructions, Charlie quickly undressed, putting his clothes neatly aside.

This was not the first time that Charlie saw his father get spanked or David saw Charlie spanked. However, it would be the first time that they’d been spanked together. An exciting prospect for the teen and his slight chubbing confirmed that. It wasn’t lost on either adult that it was happening.

“Up on the bed you two, on your knees, your naughty bottoms high in the air.” The two obeyed. Fran had them move closer so that they were touching.

Once they were set to her satisfaction she went to work. She had brought her small leather paddle, the one with holes in it. No hand spankings today. For a while she alternated bottoms, smart stinging swats landing on each. Charlie wanted to be stoic in front of his father but he was the first to break and cry out as each swat landed. He was rewarded with a series of ten swats, each accompanied by a loud “ow!” from the boy.

It was only fair that David get his ten now. By the third he, too, was crying out. Now she alternated groups of swats. Charlie was beginning to break some more, collapsing a bit as the strokes continued, but he managed to stay in place. When David received his swats he tended to move his bottom side to side in the useless attempt to avoid the blows.

Not much longer was needed. Fran’s goal was to have two very red bottoms, but no tears. She wanted to make sure that David would not be sitting comfortably at his meeting, nor that Charlie would be comfortable sitting on the subway or in a taxi. She would be with Charlie and could threaten another spanking if the boy showed his discomfort. She enjoyed that kind of control over both of them. He had been spanked once for wincing in a chair when others could see. Fortunately for him it was when they got home, but still, he didn’t want that to happen again. All part of Woman Power.

When the spankings were done to her satisfaction she said “Charlie, you should shower then we’ll go out. I know a good place for lunch, then we’ll decide what to do with the afternoon. Don’t you dare look uncomfortable in the restaurant!”

“I won’t, I promise.” One spanking today was plenty. He heard the connecting door lock behind him and guessed that Dad and Fran would be having some fun before everyone left.

Charlie showered and put on clothes he thought appropriate for the sort of restaurant that Fran liked. When she opened the door to his adjoining room she was pleased with how he looked and told him so. Fran was looking very smart in her outfit. This would be a special afternoon.

“I’m going to make this a special trip for you, and not only because I’ll be keeping your bottom red,” she said as they walked to the restaurant. For the moment she explained no further. Charlie did not like the prospect of regular spankings but something was exciting about it, too. When Fran promised something special it always was. That thought helped mitigate the thought that likely he’d be spanked again today.

At the restaurant Charlie did manage to show no signs that it hurt to sit. He appreciated the approving looks that Fran gave him during the meal.

“You’ve been a good boy today,” Fran said as she hailed a taxi. Charlie sat carefully when they got in. The softer seat of the cab was easier to sit on than the hard chair in the restaurant. Nonetheless, Charlie still felt the sting from his paddling. The cab took them to Greenwich Village, a new area for Charlie.

Fran knew the neighborhood well and gave the boy a tour. She had a destination planned but there was no need to hurry and she wanted to show off the neighborhood to her stepson. Charlie took it all in, with a bit of awe and delight. After about forty-five minutes she directed them to a favorite store, one that sold sex toys.

“This is one of the places where I’ll make things special for you,” she told him before they entered. Charlie’s eyes widened when he got inside and saw the array of toys, playthings, and fetish items on display. Naturally he’d seen such things on line but this was real life. He took note of the array of cock cages, comparing them to what he had. Did people really use these other things? Fran let him explore a bit. After a while she led him to the section with butt plugs, dildos, and anal vibrators. “Because you’re such a good little boy, I’m going to buy you a vibrator,” she said. Charlie looked at her questioningly. She smiled at him.

“You deserve a different kind of stimulation than just my finger can give you.” Charlie blushed at her frank, intimate comment in such a public place. No one reacted. Such talk was normal here. “Now, let’s check sizes here.” Fran knew what would be best for the boy but wanted to see what he considered. Charlie still was inexperienced enough that he really couldn’t judge.

“You know best,” he said to Fran after a moment or two of looking.

“Good boy,” she replied. She did know best and they would buy whatever she decided whether or not Charlie expressed a strong preference. “This will do nicely,” she said as took one down. It had a remote which would make it easier for Charlie to turn it on and off when he used it, but more important, to her, she could take the remote and control the boy’s stimulation. That was the important thing. She intended to be in control of the vibrator far more often than he would be.

Before taking the vibrator to the cashier, Fran looked over the butt plugs. She ended up making two selections – a set of five graduated plugs that were good for anal training and a plug designed to stay snuggling in place, letting the wearer keep it in as he went about his day. Charlie was a bit wide eyed again as he saw her make the choices. This was all so new. He figured, though, that since her finger and the thermometer were such fun, these toys would be even more fun. He started to get hard at the thought. Fran saw the slight bulge in his pants. She had taken over buying his pants, making sure they were tailored to show off his package and always make an erection obvious. This still embarrassed Charlie but he did his best to accept it graciously.

On the way to the cashier Fran made sure Charlie saw the display of strap-ons. She already had one and it had given David quite a bit of pleasure. She wasn’t sure if it would be appropriate to use on Charlie. It would be a much more sexual act than inserting a finger or plug. Time would tell. She could tell that Charlie took note of them though he didn’t comment or ask questions.

Toys paid for, Fran took him to Washington Square they hailed a cab and headed to midtown and the Empire State Building. “This is ridiculously expensive now but it’s something you have to do in New York.”

“Wow, thanks!” Charlie said. He thought it was well worth it when they got to the observation level. Fran pointed out the many landmarks visible. This was great! All the while Fran was thinking about the fun she would have with Charlie’s new toys. She would have fun and the boy would be satisfied. A good situation for both of them she thought. The excitement of taking in the view had put the toys out of Charlie’s mind.

By the time they were done on the observation deck it was time to return to the hotel and get ready for dinner. David’s meeting today included dinner so he wasn’t expected until around ten. Fran had made eight o’clock reservations at another favorite restaurant which meant that there was time at the hotel before dinner. Time to rest, perhaps, but time enough to refresh Charlie’s bottom as necessary and perhaps to introduce him to one of his new toys.

Fran genuinely did want to lie down for a while when they returned. She let them into her and David’s room. The connecting door had been left unlocked so Charlie could come in with her and get into his own room. “I’d like to lie down for a while and suggest that you do the same,” she said as they entered. “So, go to your room, dear, and take off all your clothes. I’ll call you later.”

“Yes, Fran. Thanks for a great day!”

“Of course. I like doing things for my good little boy.” She gave him a kiss on the cheek and sent him off. “Don’t close the door, dear.” Charlie did as told and soon was naked and lying on his own bed, catching up on emails and messages. He knew that the instruction to strip meant that something would happen before dinner. He expected a “refresher” spanking, hoping it would not be too hard, and also hoped that she’d used one of the new toys on him. He got hard, which felt good, but did not fondle himself.

About forty-five minutes later he heard “Charlie, dear, come on in.” He obeyed. His erection had subsided so he was his normal soft size, a sight Fran enjoyed equally with seeing him hard. He was so like his father!

Fran was sitting on the edge of the bed, the new toys beside her. “Hop up over my lap, honey,” she said in a very inviting voice. Charlie was excited to do just that and wasted no time getting in position. Even if it included a spanking, this was going to be fun.

“Hm, the color has settled. How is the sting, dear?” She pressed on his bottom. Charlie let out a small response of discomfort. “That’s good,” she said, sounding quite pleased. “Still, we don’t want things to fade away before bedtime.” With that she spent about five minutes with a hand spanking, making sure that Charlie’s sting was back and increased, along with the color. Charlie’s responses were delightful to her, indicating that her efforts were successful. She wasn’t out to break him, just make sure he felt it during dinner later. She was satisfied with the color, too. She’d consider a bedtime refresher. A boy does sleep better after a bedtime spanking.

Spanking done, she said “you took that very well, dear. I’m really proud of you, Charlie. You’ve come a long way.” Charlie blushed at the compliment. It was weird getting complimented for taking spankings, and weird at his age to get any compliments while lying naked over her lap, but he was pleased to hear it coming from her.

“Now, time for your reward for being such a good boy today and to give you some new training.” Whatever was about to happen he knew it involved penetration, something he’d come to love in a short time. Fran had lube nearby and no sooner had she finished speaking but Charlie felt her finger at his back door, as it were. She teased him a bit, enjoying his gasps as she did. It was getting easier and easier to enter him. He became hard quickly. When she did apply the pressure her finger went in quickly and fully, Charlie raising his bottom to meet it. She spent some time working him, getting pleasure from feeling his erection grow against her thighs.

“Enough of that. Now for the real fun.” She withdrew her finger. Charlie could tell she was getting something ready for him, but no idea what. There were a few options at hand. Something hard was pressed against his anus. “Just relax, sweetheart,” Fran said, letting him get used to the feel of something other than a finger or thermometer. He was relaxing. She applied gentle pressure to the object which was his vibrator. Charlie kept still, letting her ease it into him. Once it was past his sphincter the entry was easy. He needed some time to adjust to the feel of something new and larger inside him, time Fran allowed. When he gave a sigh indicating his full acceptance of the intrusion, Fran picked up the remote. She selected the lowest setting and touched the button. Almost immediately Charlie let out with “oh my God!” He’d never felt anything like this, never imagined anything like this.

“You like that honey?” Fran asked.

“Yes, Fran,” he gasped in reply.

“Good. We’re going to have a lot of fun with this.” A touch of the remote and the next level began. That was all it took for Charlie to start writhing over her lap, unconsciously stimulating his erection as it slid over her thighs. Fortunately Fran had placed a towel over her lap before taking the boy over it. She had changed into slacks that could be ejaculated on but the towel would save the bother of attending to that.

The moaning, writhing boy over her lap, stimulated by the vibrator, was a great pleasure. Little did he know that this was yet another aspect of her Woman Power control over him. She would relinquish the remote only under special circumstances. This kind of pleasure for the boy was at her command. Seeing how he responded she knew that a vibrator for David would be ordered soon. He should had be given one by now in any case.

Charlie was gasping and moaning, almost thrashing about, enthralled by the sensation. Fran smiled at the confirmation that his anus was one of Charlie’s most erogenous zones. It was often true of men, but too few, even gay men, knew it. It was easy for her to tell when he was close. She left the vibrator setting as it was, letting Charlie bring himself to climax. He gave out a yell and she could feel him exploding into the towel. “Oh! oh! oh!” he was crying out as the orgasm overtook him. Orgasm done, he lay there, spent. Fran helped calm him by rubbing his bottom. Not hard enough to make the sting hurt any more than it did already, just gentle and loving.

When Charlie seemed calm again she removed the vibrator and asked “do you want to get up?”

“Yes, please.” Charlie sounded still a bit weak. He’d recover. Once he was up Fran used the towel to clean off his softening penis then put aside the towel and stood, taking the naked boy in her arms.

“You enjoyed that, didn’t you?”

“Yes, Fran.”

“Good. We’ll have lots of fun with that and your other toys. You’re a good little boy and you’re learning well.” She kissed the top of his head. “You’d best go back to your room and get your strength back before we leave for dinner, which won’t be long. I’ll be in to lay out your clothes.” That was new twist on things. As he retreated to his room he wondered what her selection of his wardrobe would be. “Keep your door open,” she instructed. He did. He saw no need to dress so did not.

About twenty minutes later Fran came into Charlie’s room holding his clothes. Where did those come from, he thought. She showed her pleasure at finding him still naked.

“Knowing that we’d be at fine restaurants in New York I bought you some appropriate clothes.” He noticed that she had changed into a short-skirted power suit with high heel shoes that seemed to indicate that she meant business and was not to be trifled with. A new look but not a surprising one Charlie reflected, given what he’d come to know of Fran. It was an exciting look. It made him feel more submissive to her, too.

She laid out the clothes on the bed. “An adolescent boy always looks good in a silk shirt,” she said as she put it down. “Especially with a physique like yours,” she added with a warm smile. “This is in a style which doesn’t require a tie, even in fine establishments. This jacket goes very nicely with it.” She put down a dark jacket in the very latest cut. Next the pants. “These are special ordered. You’ll wear no underwear with these.” He guessed, it proved accurately, that they were cut specifically to emphasize his package. What he didn’t know was that a hardon also would be quite obvious.

“We can’t have boring socks, either,” as the last item was placed on the bed. They both laughed. The socks weren’t a bright color, but a sort of navy blue with various designs on them. “Wear your black shoes,” she said. “Don’t dawdle! We need to leave in about ten minutes.”

“I won’t!” He was as good as his word. As he dressed he was amazed at how perfectly everything fit. Had she ascertained his measurements just from all the time she’d handled him naked? It was like magic. The pants were the most comfortable he’d ever had.

Fully dressed, he presented himself in Fran’s room. She gave a gasp of pleasure. “Oh, don’t you look handsome! Everything fits so well.”

“Yes, it does. How did you know?”

“Oh, I have my ways,” she said with a sly smile. He wouldn’t pursue it.

The restaurant, besides its excellent cuisine, was one where people went to see and be seen. Also where women like Fran could take the men and boys in their charge and show them off. Charlie quickly was aware that both women and men were checking him out as they made their way to the table. Various waiters detoured by their table as the evening went on, some not making any effort to make their looks at the teen discrete.

“You like it here?” Fran asked after a while, having watched Charlie reacting to being seen.

“Yeah, it’s. . . it’s really amazing.” Fran was pleased to hear it. Charlie may not have caught on that she was showing him off but he was proving a great success, which is what she wanted. Charlie was hardly the only young man being shown off by an older adult, male and female.

Fran had friends in New York and it was likely some would be here tonight as they often dined at this establishment. Sure enough, as they were eating the main course a woman who, to Charlie, seemed rather formidable stopped at the table. Fran rose and they exchanged the fashionable air kisses.

“Is this the stepson?” the lady asked before Fran could make introductions.

“Yes, this is Charles.” How formal! “Charles, this is Dorothea. She is well known here in New York.”

“How do you do, ma’am?” Charlie said as he stood and extended his hand.

“Oh, good manners, too,” said Dorothea making the boy blush. She took a long look at the bulge in his stylish pants as they shook hands. Fran invited Dorothea to sit. As Charlie sat down he realized that he was being assessed by this woman. Fran had talked about him, this was clear. How many of her friends had heard about him? What had they heard?

“I’ve been so lucky. A man I really love who came complete with a son who has been easy to love, too. My boys are quite a bit alike,” she said. The way she said it made Charlie think that she was alluding to their genitals. Dorothea did smile in a knowing way.

“Yes, I can see that.” Did she know Dad? Their conversation turned to other matters, none of them of interest to Charlie. He took time to look around the room as he ate, taking in the décor and looking at some of the other diners. This was high class. Some glances were returned as he looked around. A couple of women who appeared to be in their early twenties sitting with an older woman all gave him a long look which held his, much to his embarrassment. A male couple noticed him and it seemed that they were discussing him. An older, well-dressed, man was dining with a much younger man. Charlie noticed that the man was looking over at him quite a bit. As Charlie surveyed the room he realized that he was feeling equally flattered by the attention of both women and men. He’d never felt like an “object” for attention. Apparently Fran was turning him into one. He needed to think about that. Later.

Charlie was taken from his revery by Dorothea saying his name. “It’s been a pleasure meeting you, Charles. I do have to get back to my party, now.”

“Thank you, ma’am,” Charlie said as he stood. “I’m glad to have met you.”

“I’m sure Fran will be telling me good things about your exploits and development,” Dorothea added. Charlie suspected what that meant and blushed deeply which made Dorothea chuckle and give him what he interpreted as a knowing smile. After another round of air kisses with Fran, she returned to her table.

“I’m sorry I don’t see more of her,” Fran said. “We have a lot of things in common which always makes for a pleasurable time together.” What did that mean? They returned to their dinners, saying little for a while. As they were finishing Charlie noticed the older gentleman approaching.

“Fran, where are you hiding yourself these days?” the man said when he reached the table. His smile indicated a warm relationship with her.

“Oh, Albert, you know what’s going on,” she teased. He leaned over and kissed her cheek. “Albert, I want you to meet my stepson, Charles.”

Charlie stood and extended his hand. “Pleased to meet you, sir.”

“My, my, so this is the boy,” Albert said. “I couldn’t help but notice him but didn’t want to make any assumptions. A striking lad, I must say. And such smart clothes. I’m sure you’re responsible for that, my dear.”

“Yes. I surprised him with them. He looks even better in them than I expected.”

Albert seemed to undress Charlie with his eyes before he spoke again. Charlie squirmed a bit. “Lucky you,” Albert continued. “Terrance over there,” he indicated his table, “has not been the most cooperative when it comes to sartorial issues. However, he will come around.” He and Fran smiled knowingly. Charlie suspected what the smiles meant. “Send me an email with information about where you got those pants when you have a moment.” Charlie was very aware that Albert had been looking at his bulge. His cock stirred a bit. The pants were designed to show that, too. Both Albert and Fran did notice, Fran smiling with pride.

“Of course I will,” Fran assured him. “Do you have time to sit?”

“No, not really. I do need to keep an eye on Terrance.” Albert sighed. “The boy has been a lot of work but it will pay off in the end. However, I could not leave this restaurant without saying hello to you and meeting this fine young man.” He leaned over and put another kiss on her cheek. “Au revoir!” He returned to his table. As Charlie sat he noticed Terrance shift a bit uncomfortably in his chair as Albert returned. Fran had understood what Albert was talking about but Charlie had no way of interpreting it, other than wondering if Terrence was getting spanked by the older man. It seemed likely he would be.

“Albert is a good fellow. Been around for years. Lots of money in the stock market, travels constantly, always at the opera and theatre. He’ll have Terrance under control, no doubt of that.” Fran said nothing to explain. Dinner done, Fran ordered desserts for both of them. Charlie had no possible complaint about her choice!

As they made their way out, Fran stopped at various tables to say hello to acquaintances, all of whom gave Charlie approving looks. He was beginning to enjoy this.

Back at the hotel, David had returned from his meetings and dinner.

“Oh, you’re here,” Fran said, happy to see him.

“Yes. Things got dull so I came back. Better to be with you two. How was dinner? Who did you see?”

“Dinner was excellent, as always, except that you weren’t there. Dorothea was there, being the Wicked Witch of the West as only she can.” They both laughed knowingly at that. “Albert had his latest project in tow.” From his father’s look in response to that Charlie suspected that Dad didn’t know much about this. “However, the important thing is that Charlie was a great success.” Charlie, yet again, blushed slightly with embarrassment. It was beginning to sink in that she really had been showing him off to the world.

“I expected no less,” said David, his pride evident. He went over and gave his son a hug.

“Thanks, Dad,” Charlie said as he returned the hug.

“Well, I for one want to get out of these glad rags and relax,” David said when the embrace ended. With that he did begin to undress. “Charlie, I’m sure you’d like to do the same.”

“Sure Dad,” Charlie replied and went into his own room. Had Dad been checking out his bulge, too? While Charlie and David undressed, Fran changed into a nightgown and robe. She was both fully covered and provocative. David’s immediate erection was proof enough that it was working.

“I do have something to do with Charlie before bedtime,” Fran said. David knew what. Fran left the door open so that David could hear. She’d be doing the same with him later.

“Good boy,” Fran said as she entered and saw that Charlie was naked. “Time for your bedtime spanking. It’s always a late night when I go to that restaurant and we all need our sleep for tomorrow.”

Charlie knew a bedtime spanking was likely. She didn’t do this often but when she did they were oddly pleasurable. She sat on the bed and Charlie went over her lap, the material of the robe feeling wonderful against his naked body. The spanking was, somehow, comforting and relaxing. It just felt good to be naked over her lap, the lap of a woman who had become so important in Charlie’s young life. It wasn’t a long spanking.

“Just enough to refresh a bit of the sting for bed,” Fran said when she let him up. “You boys will get your real spankings in the morning. Can’t have the sting fading!” She pulled back the sheets for him and tucked into bed, like a little boy. It felt great.

“Good night and thanks,” Charlie said. Before she closed the connecting door he was sound asleep.

Fran recounted their day for David before he went over her lap for a more serious bedtime spanking. David, too, would sleep with a sting and wake up refreshed.

Charlie’s Stepmother 4

The Trip to New York Continues


Charlie did wake up refreshed. As he did he was aware that his father was getting spanked in the next room. At least it sounded that way. He knew Fran intended to spank them both in the morning and that Dad had to leave fairly early. He also was aware that he had his usual morning wood. Unsure if he was allowed to do anything about it, he got up to use the toilet then climbed back into bed, dozing off.

Fran pulling back his covers woke him again. His morning wood saluted her.

“Well, look at you. Eager to see me?” Fran said as she looked him over.

“Yeah,” said Charlie, unsure what he should say.

“Yes, you must be, your head has come all the way out from your foreskin.” Charlie blushed at this. He still was adjusting to how direct she could be about his body. “Let’s get you set up for the day,” Fran said as she sat on the edge of the bed. Charlie knew what she meant, got up and settled over her lap. “We need to get the color back.” With that she started spanking. SMACK SMACK SMACK This would wake him up! SMACK SMACK SMACK Charlie let out with some yells of “ow!” as the swats landed. Fran didn’t care if he yelled and kicked, she was working strictly on his color and would spank for as long as it took for Charlie’s bottom to have the shade of red that she wanted.

SMACK SMACK SMACK It didn’t take all that long for her to satisfied. She’d be spanking both Charlie and David again today, Charlie likely more than one time, so she had no problem with this being a shorter spanking than expected.

Charlie had remained hard throughout the spanking. She wasn’t going to take him in hand but he couldn’t start his day without his morning release. She reached into a pocket in her robe where she had the vibrator, remote, and lube. She tapped him between his legs to get him to open up. Charlie obediently spread his legs. He was sure it would be worth it. It was.

Fran spread the boy’s cheeks and lubed his hole, slightly inserting her finger. She wasted no time switching to the vibrator which went in more easily today. Having experienced it, Charlie was eager for it again. Fran started with a low setting, working her way up to a higher setting than she’d used yesterday. Charlie was twitching and moaning as the vibrations became more rapid. The twitching had him rubbing against Fran’s thighs, as she intended. Charlie was moaning. Fran could feel him swell as he approached his orgasm. With a loud “ohhhhh!” Charlie let go, spurt after spurt onto Fran’s thighs. She didn’t mind. She’d dressed appropriately, along with having a towel in place.

The vibrator was switched off and Fran let the boy relax and restore himself, her hand resting on his lovely bottom. When Charlie was calm again she gave his bottom a pat and said “take your shower. I’ll put out your clothes and we can go down to breakfast.” Before she let him up she removed the vibrator. Charlie missed it right away.

“Yes, Fran.” As Charlie showered he realized he was leaking a bit even after that major ejaculation. Another exciting aspect of all that was going on in his life. Shower done he went back to his room to find clothes ready for him on the bed. Another pair of slacks which required no underwear, the lining seemed even smoother than yesterday’s pair. A casual shirt, bright socks, and a new pair of sneakers. When had she bought all of this, he wondered. Oh well, he was flattered that she made the effort and liked how he looked when he was dressed. He went into Fran and David’s room.

“Look at you,” she said again. “Almost as appealing dressed as naked.” She smiled at him and he couldn’t help but smile back. They went downstairs to the hotel’s dining room for the breakfast buffet which was much better than most such places provided. After all, this was a very high-class hotel.

Breakfast done, Fran said “we need to go back upstairs before we go out for the day.” Charlie was fine with that. Back in the room Fran surprised him by saying “take off your pants, dear.” Charlie obeyed. “Up on the bed on your knees,” she said once his pants were off. “Don’t worry, it’s not a spanking.” That was a relief!

Fran continued once he was in place. “I own you today, dear, and you’re getting something that will let you remember that.” She took her time lubing him, which felt great. Charlie felt lucky to be getting a second round so soon after the first one. Her finger easily had him hard, though that wasn’t the goal. When her finger was removed it quickly was replaced by the vibrator. Fran had made sure to buy one that would stay in place when Charlie walked around.

“There, that should hold you,” she said when the vibrator was in place to her satisfaction. “The padding in these pants is designed to let you cum in them without leaving a telltale stain, so embarrassing for boys. And you will be cumming during the day. I’ll have your remote with me.” Charlie again didn’t know what to say. She patted his bottom and said “get your pants and shoes back on and we’ll get going. There’s a lot to see today.” Charlie redressed and they went downstairs, hailed a cab, and were on their way. Even not vibrating, the device felt good inside him.

They went up to Central Park where they walked around, eventually heading toward the Metropolitan Museum. As they headed toward the Museum Charlie realized that he was feeling a tingle and vibration in his rectum. Fran had turned on the vibrator! She had said he would cum today and Charlie knew she kept her word on such matters. Being so public, though, he tried to remain calm as he was being stimulated. He immediately was hard, the pants surprisingly able to take his erection quite comfortably. Fran turned up the power, making it difficult now for Charlie not to twitch and tremble. He hoped no one noticed. Another notch and he lost any awareness of whether anyone was witnessing this.

He knew he was close. “Fran, please, I need to stop,” he said, gasping. He wasn’t going to say “I’m going to cum” so publicly.

“Of course, dear.”

He did his best to keep his moan as quiet as possible. He’d never cum in his pants. He let go with a number of spurts which were quickly absorbed by the special lining. Ejaculation done, he stood gasping for a moment, Fran watching, turning off the vibrator, pleased with the show. As his erection receded he realized that he wasn’t feeling any dampness in his pants. He looked at his crotch and there was no stain. Amazing.

“Ready?” Fran asked when Charlie seemed calm.

“Yes, Fran.” With that they went to the Museum where they spent most of the day, including lunch. Fran made him cum while they were seated in the Museum restaurant. Charlie resented that a bit, feeling like she was toying with him. Which she was. Again he remembered that she had said she owned him today. There was nothing he could do other than try to enjoy it. He gave her a weak smile when he’d shot. He couldn’t read the look she gave him. She was enjoying her day and her boy. Her boy toy.

She made him cum again in the taxi on the way back to the hotel. Charlie was sure that the driver knew that something was going on.

David would be back for dinner tonight. Fran had reservations at another swank restaurant and was looking forward to showing off both of her boys.

Back at the hotel Fran let them into her room. “Get undressed, dear, and we’ll take the vibrator out.” Charlie undressed completely as Fran settled herself on the edge of the bed. Charlie put himself over her lap. Fran pulled out the vibrator and set it aside on a towel. She’d clean it later. Vibrator out, she turned her attention to his cheeks. “My, my, we need to refresh the color here.” With that a series of firm but not painful swats landed. Fran didn’t want to break either Charlie or David before dinner but she wanted to be sure that they were sitting gingerly during the meal.

SMACK SMACK SMACK The color and sting were rising nicely. For Charlie the spanking seemed like a sign of Fran’s approval of him and how he’d responded today to her manipulations with the vibrator. As time had gone on her spankings often were giving him a feeling of security.

“Now, there’s a nice shade of red,” Fran said as she wrapped up the spanking. He couldn’t see the color of course but the sting felt good. “Go to your room and check your emails or whatever. I’ll have some clothes for you for the restaurant when we’re ready.” Charlie got up, gathered his clothes and went next door. He heard Fran close and lock the door behind him. It felt good being naked so he decided to stay that way until Fran produced his clothes for dinner.

When David returned Charlie could hear enough to know that he was back. Things were quiet for quite a while. As it got closer to departure time, though, Charlie was aware that his father was getting the color back in his bottom, too. This time that knowledge made Charlie smile. Another sign that he was submitting more fully to Fran’s control.

About fifteen minutes after the sounds of spanking stopped Charlie heard the connecting door being unlocked and Fran entered. Charlie could see David lying naked face-down on their bed. “Your father is all set, just needs to get dressed soon. As for you, young man, it’s time to get your clothes and get you dressed.” Fran got things out of the dresser and the closet. A dressier pair of pants, shirt, tie, and jacket. “With these trousers you do need briefs,” Fran said as she took a pair of silk briefs from the dresser, a light beige in color. “There you go. Be ready in about fifteen minutes.”

“Yes, Fran.”

The silk briefs felt luxurious. He hoped that Fran would keep him supplied with them. He wasn’t used to wearing a tie but managed to get it properly knotted. “May I come in?” he called to the next room.

“Of course, dear.” It was Fran who replied. David had on a similar, but not matching outfit. Definitely father and son, though. Charlie could tell that Fran would be showing off both her “boys” tonight.

Heads did turn when they entered the restaurant. Again, she had made sure that they had a handsome, young, very attentive waiter. The young man had no luck when he tried to flirt with David but Charlie was responsive, though naïve. The waiter brushed by him more than once and he felt himself rising which felt wonderful in the silk briefs.

Albert was at this restaurant, too. He sauntered over at one point. “So this is the new husband.” Fran made introductions. “Lucky you,” Albert said. David both appreciated the compliment and was a bit embarrassed. “And you brought the boy again. Such a fine specimen.” Charlie blushed. Albert chatted for a few minutes, then returned to his own table.

“He certainly is a character,” said David when Albert was out of earshot.

“That he is,” replied Fran, “but don’t be fooled. He’s shrewd and has amazing connections.” David looked over at Albert’s table where it appeared the older man was quietly reprimanding his young companion, the same fellow from last night. Fran noticed that David was looking. “I’ll tell you more about him sometime.” She left it at that.

Some women stopped by at various times, all eager to meet David. They fussed over him and Charlie. “I’d like to take him home with me,” one woman said about Charlie.

“You won’t!” Fran said firmly but in a tone that showed her friendship with this woman and implied that they’d had similar conversations.

At one point Charlie excused himself to use the men’s room. He’d never seen anything like it. It even had an attendant!

“Everything come out all right?” the attendant asked with a wink when Charlie was done and as he handed the boy a towel to dry his hands. The pants Charlie had on were quite as revealing as last night’s pair and the attendant obviously was looking at the bulge. Charlie thanked him and left. Along the way some younger men at tables have him a nod or a hello.

“The boys admiring you?” Fran asked with a smile as Charlie sat down.

“Yeah, I guess so. I’m just not used to all this, I guess.”

“It’s alright, dear. It’s the big city. You’ll be fine.” David readily had caught on that he and Charlie were being shown off by his wife. It amused him that she felt that way about him and his son. Harmless fun. She certainly knew some interesting people! More than David had realized. He knew that whatever sexual curiosity these women might have about him would not be satisfied. By his own choice he belonged to Fran. As this visit went on he saw that more and more his son belonged to her, too. Satisfying all around, he felt.

Dinner took up most of the evening. David’s meetings began early in the afternoon so he could sleep in, which he was looking forward to. Back at the hotel, Charlie was sent to his own room with Fran saying “I’ll be in to take of you in a while.” When she came in Charlie was naked on his bed, working on his laptop.

“Put that aside,” she ordered. Charlie did and soon was over her lap. A few hand spanks and then he was startled by the hairbrush. It wasn’t too hard a spanking but the hairbrush had never been part of a bedtime spanking. “Ow! Ow! Ow!” A few more swats with the brush and Charlie’s color was back. He was feeling more of a sting than he’d had last night.

Fran let him up. “I know you have other things to take care of,” she said with a wink, gave him a kiss on the cheek, and went back to her room. The connecting door was shut and locked. Charlie took her comment as permission to masturbate as he wished and soon was taking care of the hardon which had grown at the end of the spanking. He managed to cum quietly but the spanking definitely had excited him and he shuddered when the orgasm hit. It was almost like having the vibrator in.

The next day was not quite so busy. David slept late enough that they had to have room service for breakfast. Charlie enjoyed the new experience. Fran told the “boys” that they could not wear clothes until time to leave the hotel. David seemed unfazed but Charlie was rather embarrassed to have the room service man come in while he and David were naked in the room. The room service staff had seen it all so this was nothing new but the young man did take in father and son, silently making no secret of admiring what he was seeing.

Over breakfast Fran told Charlie that they would be having tea with one of her friends. “A lovely penthouse which I’m sure you’ll enjoy. But I expect perfect behavior.”

“Of course,” Charlie answered.

Breakfast done, David dressed for his meetings, kissed Fran and gave Charlie a hug and was on his way. When was gone Fran said “I’ll get your clothes for you. Marguerite expects men to look ‘just so,’ as she always puts it.” They stood, Fran gave Charlie a quick swat on his bottom and he led her into his room.

The clothes she selected seemed rather formal to Charlie who still was learning about all these things. There were no underpants. Sure enough, the trousers, though more formal than yesterday’s pair, were of the same make with the same padding. And sure enough, she told him to get up on the bed, his bottom high for the vibrator. He didn’t like the idea that she might make him cum at this tea party but was obedient. The plug felt good when it was in him again.

When she was done she said “There. Now, get dressed and we can do some sightseeing before we need to get to Marguerite’s.” This pair of trousers felt almost as good as the silk underwear. When fully dressed he felt a bit stiff in the outfit but after a look in the mirror he did feel good about his appearance. He knocked on the door to the other room and Fran bid him enter.

“My, my, you do dress up well, young man.” Charlie blushed at the compliment. She was dressed in a very chic outfit. Charlie knew that they’d be quite a sight and felt some pride at this.

The early afternoon was spent exploring around Times Square, looking at stores and theatres. After a while Fran said “we’re due at three, so let’s find a cab.” That was easily done and they were taken uptown to an older apartment building which still had an elegance about it. The doorman recognized Fran and welcomed them. He called up to the apartment and in a moment an elevator opened. They stepped in, the door shut, and quickly they were at their floor. In fact, the elevator opened into the apartment. Charlie never imagined that such a thing existed.

The door opened and they were greeted by a woman, definitely older than Fran, who Charlie thought seemed rather masculine. In fact, while she was wearing a skirt, her upper half was dressed in a man’s shirt, tie, and jacket. Nonetheless, she made a handsome appearance.

“Fran, darling, so good to see you.” The ladies air kissed in the French style.

“Marguerite, this is David’s son, Charles.” Oh, he was to be Charles this afternoon.

“How do you do, Charles?”

“How do you do, ma’am.” He could tell that he had Fran’s approval with his manners and this lady seemed taken with him.

“Very handsome young man, dear,” Marguerite said to Fran. “Now, shall we?” She ushered them into a lovely living room, filled with antiques and walls covered in paintings. The style of some of them made Charlie wonder if perhaps they were by significant artists.

They sat and the ladies spent time catching up on things. Marguerite asked Charlie the usual things about his life, school, and interests. Again, Fran’s approval was clear, which made him feel relieved and he relaxed a bit.

As the ladies went back to their chat Fran fished for something in her handbag. Charlie felt a tingle in his bottom. He’d forgotten about the vibrator! Was she going to make him cum in front of this woman, someone he’d never met? He tried to be nonchalant, glancing around the room at the paintings and objets d’art.

He couldn’t tell where Fran had the remote but she did have it and was slowly turning up the power. Despite his attempts to remain calm he was beginning to breath hard and gasp a bit. He was rock hard. He didn’t realize it, but these pants did nothing to hide that fact. He was aware that Marguerite was watching him. He gave her a weak smile and tried not to respond to the toy in his rectum. To no avail. He was being made to put on a show and put on a show he was.

As the vibrator did its work he began to twitch a bit in addition to the obvious heavy breathing. He was sitting so the vibrator was in constant contact with his sensitive prostate. He was reaching a point of no return. With a gasp he let go, the semen quickly absorbed into the special lining. Later he noticed that, again, there was no telltale stain. Ejaculation done, he fell back into the chair. As he recovered he realized that the ladies were chatting again as if nothing had happened. Marguerite showed no sign of having witnessed anything unusual.

A few minutes later a maid appeared with a traditional English tea. The food and tea were delicious. Charlie was hungrier than he realized but was careful not to appear glutinous or forget his table manners.

“Enjoying the food, dear?” Marguerite asked at one point.

“Oh yes, ma’am. This is excellent.”

“Good. The tea is a special favorite of mine, too. I hope you’re enjoying it.”

“Yes, ma’am. Delicious.”

Marguerite turned back to Fran. “From the pictures you’ve shown me it is clear that he looks very much like his father.” Charlie blushed slightly. He never enjoyed being talked about this way.

“Very much so,” Fran replied. “There is quite a bit that is similar about them, not all of which shows.” What did that mean? Marguerite had given a knowing smile at that comment. Was Fran revealing personal things to this friend? Somehow it wouldn’t surprise him now that he knew his stepmother as well as he did.

Tea done, the maid returned and cleared things. Charlie heard the elevator door, then footsteps and stood as he knew he should. Four ladies of Marguerite’s age came in. All were dressed quite elegantly, one in what appeared to be a man’s suit. They all knew Fran and were delighted to see her. After their greetings Fran introduced Charlie. Or, rather, Charles. He could tell he was being closely assessed.

Greetings and introductions done Marguerite said “Charles, I’m sure you don’t want to sit around listening to old ladies gossip.” She smiled at him. “You are free to lie down in there if you want. You are welcome to the laptop, too, if that interests you.” She had indicated a door to a bedroom.

“Thank you, ma’am.” In fact he was feeling that he wanted to lie down. Marguerite ushered him into the room. As she left he took off his shoes and got onto the bed. It felt luxurious. Fran certainly had an interesting life that Charlie was only just learning about.

He wasn’t sure if he dozed off or not but he was restored to consciousness by the tingling in his bottom. Not again! At least they couldn’t see him. However, the door was open. It would be too obvious if he jumped up and closed it. Very slowly the power was being turned up on the vibrator. He did his best to remain quiet but gradually the sensations became too much. He was letting out with “ugh! Ugh! Ugh!” as the vibrator did its work. He’d gotten hard the moment he’d felt the pulsing. Now he was writhing a bit, the head of his hard cock being stimulated by the rubbing against his pants. That and the vibrations, especially when making contact with his prostate as he wriggled, had him at peak excitement. With an unintentionally loud groan he shot for the second time since they’d arrived.

No sounds from the other room indicated that he’d been heard. In his excitement he would have been unaware of any comments, though. The conversation level seemed the same. Had no one heard? Why would Fran do this unless she wanted them to know it was happening? He now was acutely aware that he very much was on show while they were in New York and public orgasms were part of it, like to or not.

In the living room the ladies, in fact, were commenting on what they’d heard.

“Is he always so stimulated?” one of them asked.

“Oh yes. He’s quite responsive.”

“And spankings?” another inquired.

“Spankings are regular and his bottom takes them very well. Fortunately I don’t often have to spank for discipline but regular spankings are good for a boy. As you can imagine, his bottom is quite lovely when red.” Now Charlie heard some laughter.

“And the boy’s father?” asked the one in the suit.

Fran chuckled. “Now, now, that’s our business.” Laughter again. “Suffice it to say, he’s well taken care of.”

“Well trained?” Marguerite interjected.

“I didn’t say that,” Fran answered with a sly smile. More laughter. Conversation went in other directions.

Charlie again must have dozed off because next thing he was aware of was Fran gently waking him. “Time to get back to the hotel and meet up with your father.” Charlie was happy to leave. Goodbye was said all around. He and Fran rode down with the four ladies who rather fussed over him in the elevator. A cab had them quickly back to the hotel. David was already there.

After the usual greetings, Fran took Charlie to his room. “Get undressed and I’ll get that vibrator out. Dinner is more casual tonight but I’ll set out some new clothes for you. I think you need a quick shower after your day.” Charlie was glad to have a refreshing shower after having the vibrator removed. When he returned from the bath clothes were waiting for him including silk underwear again. He was pleased.

Dinner indeed was a casual affair and not filled with Fran’s friends and acquaintances. Both Charlie and David were happy with this. They also were happy with an early evening as tomorrow they were flying home.

The vibrator was not produced for Charlie to wear on the plane. He was quite aware that he was relieved that it wasn’t. He was spanked before they left, “so you’ll feel the sting on the flight.” He accepted his fate, though aware that his father did not require the same sting. It seemed one never knew with Fran just what was in the plans. She had told him that she’d be breaking in his butt plugs when they got home. He’d gotten hard when she told him and, as he was naked at the time, she noticed. They both smiled.

It was good to be home. Life returned to its usual routine. Charlie didn’t always enjoy the spankings but he did like the attention it meant he was getting from his stepmother. All in all he thought he probably was pretty lucky. He doubted any of his friends or schoolmates had a life like his!

Soon he’d find out that he wasn’t the only one.