Please Send Nudes

***All characters are over 18 and are fictional. Any resemblance to any real-life persons or situations is purely coincidental.

...

BRENDA

Brenda felt ridiculous. She didn't know why she let her friends talk her into trying something like this. She knows that younger women than her do this quite often for their men, but she was in her early 40's now and felt it was unbecoming of her. But she was dating a younger man now, and her friends convinced her that she needed to do things like this to make sure he forgets that she's older than him and that she still likes to have fun. So, she decided to do this one thing and text him sexy pictures of herself.

She had no problem being sexy for him. Even at 44, she knows how to keep a 33-year-old man satisfied in bed. She basically lets him do whatever he wants in bed with her, including things she would never do with her ex-husband or any other lover she's ever had. But she was concerned about the idea of sharing those kinds of pictures with Mike.

At first, her friends tried to convince her to send Mike nude pics of herself, but she was completely against that idea. She had heard too many stories of how that could go wrong. Sometimes it's the boyfriend who posts them online without the girlfriend's consent, other times it's because the phone gets hacked and then those photos are leaked online. She even heard very upsetting stories of how people would use those pics to blackmail the woman. She didn't think Mike was the type to misuse her pictures, but she was still concerned that it would get out there somehow.

So, her friends convinced her to do the next best thing and just send him underwear shots of herself. She still had concerns about that kind of thing getting out there, but she felt it was safer than nudity. She didn't think someone would try to blackmail her with bra pics when in the past she had posted pics of herself online in a bikini.

Mike was away on a business trip for a couple of weeks, so she thought it was a perfect time to try it out. When he's back in town, he could see her in her underwear as much as he wanted, but being away, he won't be able to see her like that as much. She also thought it was a good way to get him excited about seeing her again when he returned to town.

So, there she was, late at night in her bedroom, dressed only in her underwear, trying her best to take some sexy selfies of herself. She got a little excited about the idea of it at first, but after so many pictures, she was beginning to feel ridiculous about it. After what felt like a hundred shots, she felt she was going too far with this and didn't think she needed to resort to this kind of thing for a man.

She was about to put away her phone and put an end to this nonsense when she got an Instagram notification. She saw that Mike had posted something and was excited to see what it was. He would sometimes post something about himself and what he was doing, but most of the time he posted some of the funniest memes of everyone she knew on social media. This time it was just a regular picture of himself with a group of his coworkers out for dinner, with the caption mentioning how they were out having fun after a hard day at work. Brenda liked the picture and made a simple comment on it.

She was about to put away her phone when she got a better look at the picture. He was at a round dinner table with his coworkers, about ten of them, all dressed casually. But right next to Mike were two women sitting next to him. They were both pretty, very young, and showing way too much cleavage for a dinner party.

Brenda could see it was just a casual dinner with his coworkers and there was nothing to be concerned about. But she couldn't help looking at those bitches, as she referred to them in her head, sitting next to her man dressed like that. She didn't think he was the type that would cheat on her, but that doesn't mean he wouldn't be looking at their tits when he got the chance. She couldn't blame him; he was a man, after all, and men liked to look at tits. But she suddenly got jealous of those two unnamed women and wanted Mike's focus to be on her. Brenda knew she had nice tits herself and decided to send him a reminder of that.

Brenda was a beautiful woman. She was about 5'5" with long, wavy black hair, and always kept herself in good shape. She had good D-cup breasts that were still holding up pretty well for a woman her age. She had to accept that her ass had grown slightly bigger over the years, but not significantly.

She resumed taking more pics of herself and didn't stop until she was satisfied that she had gotten plenty of good ones to send to Mike. She deleted some of the pics that got blurry and cropped a few of her favorite ones. When she felt she was ready to send them, she opened up her messenger app, searched for Mike's name in the recent conversations list, attached the pics to the text, and hit send. She followed the pics with a simple text saying how she was thinking of him.

She then relaxed, put on her pajamas, and watched some TV as she awaited Mike's response. She hoped he would send her some pics of himself with a sexy message. She was feeling really good about herself and was even considering sending nude pics next time.

Some time had passed and there was still no response. She wondered what was taking him so long; seeing something like this should make any man quickly respond. She considered that he might still be out to dinner with his coworkers and was just waiting for some privacy before he could respond to her. She was considering a number of possibilities for why he wasn't answering, and the more she thought about it, the more worried she got. Soon, she was thinking about how much of a very bad idea it was to send him those pictures.

She didn't want to be that kind of girlfriend who gets upset when her boyfriend doesn't respond to her texts too soon, but she was finding herself becoming one of them. She finally decided to send him a message to see what he was doing that was keeping him from responding to her pics. She knew it would make her look bad, but she felt she had the right to know why.

When she opened up the text chain for Mike, she noticed something very odd. The pictures she sent him were not there. She was sure she sent him the pics; if they failed to be delivered, she would've gotten an error message about it.

Suddenly, she had a disturbing thought. She went back to her recent conversations list and opened up another text chain that was at the top of that list, and was horrified by what she saw.

"Oh... My... God," was all she could say.

She forgot that there was another way for personal photos to be mishandled. In some instances, the person sending the pics would accidentally send them to the wrong person. When Brenda was searching for Mike's text chain, she was in such a rush to send him those pics that she accidentally picked a text of a person with the first two letters of his name, and that's all that she saw; she didn't even bother to look at the last names. So, instead of sending it to the name Mike, she sent it to the name Mitch, who happens to be her son.

She was freaking out about it all. She did her best to calm down and think about what she had to do next. She realized she needed to go to her son's room before he had the chance to see those pictures and delete them. There was no way for her to get to his phone without him knowing, so she considered the idea of coming clean about what she had accidentally done. She hoped he wouldn't judge her by this; she actually hoped he would think it was a funny story. Either way, she needed to come clean so she could delete those pics before he saw them himself.

She was about to head out to his bedroom when she suddenly got a text from Mitch.

The text read

"Can we talk about this?"

MITCH

Mitchel, or Mitch as he liked to be called, was in his room working on a series of job applications he found online. He had graduated from college six months ago and had a good internship afterwards, but when it seemed like they weren't going to keep him after the internship was over, he decided to start looking around for other work. He was fortunate that he at least found a paid internship; those are very rare. It didn't pay well, but it kept him from going broke from working for them for free.

He went through several applications very easily. Others demanded more information, which was very time-consuming. But the hardest part was tailoring the resumes and cover letters to the jobs he was applying to.

He had to stop briefly when he got some text messages from his mother. He thought it was odd, because he knew she was in her bedroom at the moment. She wouldn't text him if they were in the same house; she would either call out his name or come to his bedroom.

He didn't answer her right away; he needed to finish up a complicated job application that, for some reason, needed to ask him a series of questions. Of course, they were written in a very complicated way that could have multiple answers. He had done enough of these questionnaires to put down what he felt was the right answer, but it was still an annoyance to have to go through them.

When he was done, he decided to finally check his texts. He didn't answer his mother's right away because he saw one from an ex-girlfriend and was hoping for a booty call. Turns out, she just wanted to know if he had any extra weed on him. He let her know he was all out, which sucked, not just because he didn't have any weed for himself, but he hoped to turn that into a potential booty call.

He then answered a few other texts he missed from his friends for some simple bullshitting that guys do with each other. Finally, he had to answer a message from his current supervisor asking if he wanted to come in early tomorrow morning for extra hours. He could've been able to do it, but made an excuse about why he wasn't able to. He felt that if he was going to be let go soon, he shouldn't have to put in that kind of extra work. He would still do his job well, but that's about it.

Finally, he decided to answer his mother's texts. He felt bad for putting it off until last, but he thought if it was that important, then she would just come to his bedroom or yelled for him from the other side of the house, since they were in the same house. He figured she must be sending him some memes that her boyfriend Mike likes to share. He already follows Mike on social media, so he would already see whatever he posted. He just saw one about a dinner party he was at with his coworkers.

Mitch liked Mike; he was the best of all of his mother's previous boyfriends. Ever since she got divorced ten years ago, she has dated some real losers. Some were just straight-up assholes, and he didn't like the way they treated his mother. Others were just boring and dull, but at least they weren't assholes. She had a few good ones in between, but there never seemed to be that many or last that long.

Then she dated Mike, who was a very cool guy. Mitch was originally concerned about his mother dating a much younger man, who was literally halfway between his and his mothers. Mitch was 22 himself, with Mike being 33 and his mother at 44. All three of them joked about that weird number alignment. But Mike always treated his mother well and she liked him a lot; to Mitch, that's all that mattered.

He opened up the text and was instantly shocked by what he had just seen. His mother just sent him several photos of herself in a variety of positions, dressed only in her underwear. Living alone with her for most of his life, he had seen his mother in her underwear on multiple occasions, but never for too long, and never like this. At the bottom of the text was a message saying how she was thinking about him.

He took a long moment to think about what had just happened. He was, of course, a little freaked out about this. But when his mind began to settle down, he started thinking about it more clearly. The only explanation is that she must've tried to send the pics to Mike, not him. He could only surmise that she got the names mixed up, most likely because of the first two letters of their names.

He decided they should talk about this because eventually she was going to see the mistake she had made and have a freakout of her own. He sent her a message asking her if they could talk about this and awaited her response.

THE KITCHEN

Brenda texted him back right away, and they both agreed to meet in the kitchen to talk about what had just happened. Mitch arrived first, but it was several minutes before Brenda showed up. She was very nervous about having this kind of talk with her son. She was sure that at his age, he had one or two previous girlfriends who did the same thing for him, so he might understand. But that doesn't mean she was looking forward to having this discussion about how his own mother tried to do this for somebody. But she also recognized her son as an adult now, and she was certain that they could handle this like adults.

She slowly walked into the kitchen and found Mitch sitting at the table with a couple of beers ready for them. She sat across from him, took the beer that he handed to her, and took one long drink from it.

"So, about those pictures," she began to say. "There's an explanation for them."

"My guess is that you sent them to me by accident. I'm assuming they were for Mike."

Brenda breathed a sigh of relief. By understanding the situation right away, it made her feel more relaxed that she didn't have to explain this to her son.

"Yes, exactly," she replied. "I'm so sorry for this. I kind of rushed it and accidentally opened your texts instead of Mike's. I'm so sorry about this."

"It's alright, I thought it was kind of funny," Mitch said with a chuckle.

"That's good to hear--" she began to say before she suddenly realized what her son just said to her. "Wait, what do you mean it was funny?"

"I mean..." Mitch didn't know how to respond and it took a while to think of what he meant by that.

"Did you not think they looked good?" she asked. "I know those were pictures of me, but I thought I looked sexy in them."

He really didn't know how to respond because she seemed offended and he was afraid he might make it worse.

"Don't get me wrong, you're a very beautiful woman," he replied. "But those pictures... they were..."

"They weren't sexy?" she asked again.

"I would have to say... no," he finally answered.

Brenda felt disappointed. She was already embarrassed that she accidentally sent those pics to her own son, but now she finds out they didn't look good at all. She would understand if Mitch wouldn't be turned on by them; they were pics of his mother, after all. But she hoped those pics would at least have looked good.

"What was wrong with them?" she asked.

"Do you really want me to answer that?"

"The subject has been brought up; we might as well talk about it."

"I don't think this is something you should talk to me about. Maybe you should talk to your friends about this."

"It was their idea," she revealed. "And they gave me a hundred different pieces of advice on how to do this. I'm not going to get a direct answer from them."

"And I would be better to advise you on this?"

"You already know about this, so we might as well talk about it," she answered. "Also, I'm sure you've had one or two girlfriends who sent you pictures like those. They probably sent you nude pictures, too."

Mitch just nodded to show she was right. He decided not to mention that it was more than one or two previous girlfriends who sent him nude pics. He even had a few women who he was just hooking up with on the side do this for him.

He thought about saying no, but felt he may be better at giving her advice on this because of his own experience. He also liked that Mike was the first boyfriend of hers since her divorce that he actually liked, so, if she was going to do this, she might as well get it right.

"Ok, I'll give you some pointers on this," said Mich. "But you do realize how weird it is that you're asking for advice from your son about how to do something sexy for your boyfriend?"

"Yes, I realize that," said Brenda.

"Ok, let's begin."

Mitch already had his phone with him when he came into the kitchen. He opened up the text chain to go through the pics she accidentally sent him so he could get an idea of what advice he should give her. Since he had already seen those pictures, he didn't think she would mind if he looked through them again.

"Ok, let's begin with your choice of underwear," said Mitch. He decided to get to the most awkward part of this whole conversation right away."

"What's wrong with what I'm wearing?"

"Nothing, if you're a grandmother," he said sarcastically.

He could see that comment made her feel bad, but he had to give her the harsh truth so she would learn.

Mitch continued. "I've seen you in your underwear a number of times over the years. They were brief moments, but I did notice, of course. And I have never seen you wear something like this. I have to ask, what were you thinking when you chose this underwear?"

Brenda's face flushed from embarrassment. Her embarrassment tonight just kept getting worse by the moment, but she felt she needed to hear this if she was going to get better at doing this kind of thing.

"To be honest, all of my good underwear is in the washing machine and I haven't dried them yet. So, I picked anything I had because I thought it didn't matter what I wore; men just liked seeing women in their underwear."

"True, but there's a limit," he replied. "Don't you have any lingerie you could've used?"

"I do, but I wasn't ready to go that far in my first time doing this," she replied. "I thought I'd try with casual underwear first."

"Casual underwear can be good, but they still have to look good. The ones you used for this picture covered up too much. You should use something that shows a little extra skin, something for the guy to look at. Even if a guy has already seen you naked, it's still good to tease him a little when you are dressed up in some way."

"Kind of like how I would wear a dress that would be a little tight or a little revealing. Or when I wear a bikini on the beach."

"Exactly," said Mitch. "Next time, show a little cleavage and maybe a little ass too."

Brenda felt very embarrassed after realizing her mistakes. "I can't believe I didn't realize this before; this should've been so obvious to me."

"Don't beat yourself up over that; this is a new experience for you. Your generation never did something like this when you were younger."

"I knew some who did it with regular digital cameras and sent the pics through email. But even then, that wasn't perfect."

"Now let's talk about your poses," said Mitch.

He went through the photos he had and pointed out all of her mistakes. A few looked like she was trying too hard to be sexy, and a few others had such outlandish poses that he couldn't understand why she thought it was a good idea in the first place. Besides that, her facial expressions were ridiculous, and the lighting in her bedroom didn't do her any favors either.

"It felt right at the time I did them," said Brenda.

"Just because it felt right doesn't mean they were right."

He began telling her his suggestions of what she could do to improve her sexy selfie pictures in the future. He told her about how to improve her lighting and how to make sure the background looked decent. He gave her some advice on what kinds of poses she should try and how to use her long hair in them, because that can sometimes help. He also told her how to better show her cleavage in them and to avoid crotch shots because they're overly done. The past part felt a little uncomfortable for him to talk about with her, but he felt that he had already gone this far in their conversation, so he might as well continue.