Showing posts with label Cybersex. Show all posts
Showing posts with label Cybersex. Show all posts

Friday, August 29, 2025

Cyber Connection - Chapter 2: Talking to Jen

 When you wake up the next morning, you check your messages to see if NiceGuy63111 sent anything. No. But he normally doesn’t message in the morning. He works a 7–4 job somewhere, so he’s normally out of the house by the time you wake up.

You look at your watch, and get ready for work. You remember that you’ve got the morning shift.

On your way to work, you text your friend Jen. “Jen, If you’ve got time today, can we meet during your lunch break or coffee break?” You are lucky that she works as an office assistant only a couple of blocks away from the restaurant.

As you pull into the parking lot, your phone dings. “Sure. Shall we grab something at the coffee shop around 10:30?” you read.

“Ok. I should be able to take a break then. TTYL”

The manager is already here, checking to make sure the night team didn’t leave any messes behind when they closed up. You smell the grill and the fryer as they both heat up. You get your cash drawer, quickly you count and confirm what you have, then slide it into the register.

All morning you have felt pretty good after last night. Your smile at each customer has been met by a similar one. It’s almost like your good mood is infectious.

Even the lady who comes back, complaining that her hotcakes weren’t right, does it politely “Miss, I hate to bother you, but my order isn’t right.” She says, handing you her receipt. You glance at it and her tray.

She is correct, so, you hand the receipt back to her. “Ma’am if you wait a moment, I’ll get the right order for you.” You say as you tell the line and they quickly hand the right order, which you in turn hand to her. She smiles and says in a sincere tone. “Thank you. That’s why I like coming here. You’re always so helpful.”

You realize as she sits down that this was the same woman, the other day, complained about her coffee and said that she was never coming back.

As the breakfast crowd thins out, you wipe down the counters and tables.

When it gets closer to 10:30 you tell the manager that you want to take your lunch break early, before the next big rush shows up. He agrees and takes over the register. You grab your windbreaker and cellphone. “Jen, I’m on my way.”

“Okay. I’ll see you there.” She responds.

The weather is nice, and you really don’t need the windbreaker, but you also don’t want your uniform shirt visible while you sit in a competitor’s coffee shop.


You enter the shop, get a drink and a sweet roll, then you sit and wait for Jen. The spices in your drink go well with the frosted sweet roll.

Jen comes in and waves to you. “Let me place my order first, then we’ll talk.” she says. She gets a tall sweet foamy drink and a huge cinnamon roll, then sits across from you.

“So, what’s up?” she asks as she takes a sip.

You look at her, “Do you and Roger enjoy sexting?” you ask.

She leans forward, “Sure. From time to time. Especially when he travels for work. Why?”

You tap your phone and pull up Bobby’s messages from last night. “Has he ever done anything like this?” You ask as you slide the phone to her.

She takes a bite of her roll and reads the screen. She slows down her chewing as she reads the messages more intently. She swallows, then takes a sip of her drink. “You did this last night?” she asks.

You nod. “Has Roger ever done..”

“I wish.” She says leaning back in her chair for a moment. “Maybe next time he travels, I need to really step up my sexting game.” she says. You look around realizing that she said that louder than you expected. She hands your phone back. “Wow! He just described massaging you. No sex, no dick picks, no requests of nudes from you?” she says with a tone of disbelief.

You shake your head and grin. “That’s what I wanted to talk to you about. Should I try take it further? He said he used to be really good at this.”

Jen leans forward again. “What do you mean? Is he some sort of ‘male cyber slut’?”

You shake your head. “No. He told me his marriage broke up from him sexting and online porn.”

Jen takes another bite of her roll. She chews on it while thinking. After she swallows, she asks “Where would you like this to go?”

You take a sip as you think about it. “I don’t know. When we signed off last night, I had to finish myself with my toy.” you say in a low tone.

“So” Jen says in an equally low tone, “you want to know if I think you should ‘go all the way’ with him?” You nod as you finish your drink.

Jen finishes her roll. “Realistically. I would continue to go slow. See if he wants to do ‘online oral’ or something. Save doing more for later.”

“Ok, Thanks.” You tell her and check your watch. “I should get back to work.” She nods and looks at her phone. “Yeah, I need to bring back drinks for the rest of the office.” As you both stand up, you hug each other. “So, can you join me and Roger on Saturday?” she asks.

“They post the schedule, later in the week. I’ll know then and text you.” You respond. “Thanks again, talk to you later.” You smile as you leave, and she places a large order to go.

You feel good, and the rest of your shift goes well. No major complaints and nothing out of the ordinary. When you get home, you tingle with anticipation.

“Are you home yet?” you text NiceGuy63111, as drive home. He hadn’t responded by the time you enter your apartment. You change out of your uniform, and into sweats and a T-shirt without a bra this time, then log into your computer. You open the chat app, as you also check emails. He hadn’t responded yet, but you try to keep hopeful thoughts as you make dinner. Heating up one of those easy microwave noodle meals. Not the healthiest of options but neither is the food where you work. You add steamed vegetables to balance it out. You mix it all into a bowl and then sit in front of your computer.

“Hi. I just finished eating dinner. How was your day?” You see the message appear on your screen.

“It went well. I’m eating dinner now too. I made noodles and steamed veggies. What did you have?” you type and take a fork full of food.

“I picked up a burger and fries on the way home. I had a busy day at work, so I didn’t feel like cooking.” He responds.

“What made it so busy?” you ask. He answers, talking about deadlines, customer complaints, and being shorthanded since one of his guys quit. As he vents his frustrations, you type a supportive “That sucks” or “Wow” so he doesn’t feel like he’s ranting alone.

You finish eating and place your empty bowl on the desk. “I wish I was there to help you feel better.” You type.

“I wish you were here too.” He responds. “We could sit on my couch and watch a movie.”

“I would like that.” you respond. “Can we try that as a fantasy? Like you did with the massage last night?”

“Really? Why?”

“Because I want to see if I can help you relax like you did me.” you type.

He takes a moment to respond but then you read “Ok… You come over to my place…..We are sitting on my couch.”

“I’m sitting next to you, leaning my head against your shoulder.” You continue.

“I put my arm around you and snuggle. I have a large bowl of popcorn on my lap. Oh, what type of movie are we watching?” He types.

“Does it matter?” you respond

“The movie helps set the mood.” He continues “Are we watching a Rom-Com, an action movie, a thriller, or a family movie? You don’t need to pick a title, just tell me what you imagine watching with me.”

You think about it then type “I’d like a rom-com, like ‘Pretty Woman’.”

“Ok, so the lights are low in my apartment aside from the TV screen. I have a large metal bowl of popcorn in my lap, which we share.”

You smile at his description, imagining how good it would feel. “I continue leaning my head against your shoulder. I feed you a couple pieces of popcorn, then eat a few myself.”

“Mmmm. I like that. Yes, I gently take the popcorn from your fingers, so you only feel my lips.”

“He is so good at this.” you think. Then you type. “I rest my hand on your crotch and feel the warmth of the popcorn bowl on your jeans.”

He types back, “I move your hand, so you can grab more popcorn.”

“I put it back and rub you through your jeans.”

“Stop. That’s not what I want.” He types.

“Bobby, What if it’s what I want?” you ask. “I want to make you feel better. Don’t you want me unzipping your jeans and stroking or sucking you, to make you happy?”

There is a long pause before he responds.

“I told you yesterday that Sexting was part of what ruined my marriage. I like you. I don’t want rush or push things.”

You type, “But last night felt so good. I want to do the same for you.”

“But it’s not what I want. Not right now.” He types, “I like the fantasy of you next to me. A female friend just sitting and enjoying a movie with some popcorn. It’s not a date or anything. Just two friends enjoying each other’s company.”

“But what if I want more!” you reply. “What if my fantasy is to come over to your place, snuggle next to you, and then have sex? Can’t I get that too?”

There is a long pause before he responds again. “Why don’t we stop here for the night? If you want to sext, in the style that I do, it takes time and a little creativity.”

Before you can type a response, he continues, “I’m not saying that I don’t think you can do it, but I am saying that it’s more than ‘get naked’, ‘get hard’, ‘lick it’, ‘suck it’, and ‘fuck until we cum’. Reread what I wrote last night. Read how I described what my fingers did and what you felt.”

“I can do that” you quickly type. “I can focus on describing what you feel, how hard I make you, and how good you taste.” As you read your own words, you think “Where is this coming from? Is it because he turned me away or because it feels like a challenge?”

“Let’s call it a night. If tomorrow you want a sexting fantasy, I’ll be better prepared for it.” you read.

“What do you mean prepared for it? Like having to take Viagra or something?” you ask genuinely curious.

A laughing emoji pops up, with “No nothing like that. It’s more that I need to think of you as a woman who wants to have sex with me. Not a friend coming over.” There is another pause, “As I told you, I’ve made changes to my life. I try not to look at every woman as a sex object, I try to listen and pay attention to them as people, and I try to keep friends as friends. IRL I don’t have any ‘friends with benefits’, so I don’t do that online either.”

“Ok, Bobby. Let’s log off. Talk to you tomorrow.” you say.

“Goodnight.” he types and posts a sleeping emoji.

You aren’t sure if it’s shock, anger, or frustration about what happened, but you feel too keyed up to go to bed. You text Jen. “Hey, You won’t believe what happened tonight…”

(This was Part 2 of my multipart story. If you enjoyed it, Like and leave a comment. If you enjoy my writings, subscribe and follow me. Part 3 will post next week. See you then.)

Friday, August 22, 2025

Cyber Connection - Chapter 1: When Chatting Becomes Something Else

 

You just want to get home and get online. Your job isn’t bad, it just gets frustrating some days. You work at a chain fast food restaurant. When you started, you were on the grill and fryer, but over time you moved up, so now you work the front counter. Today was stressful. The customers were rude and impatient, but not so much that the Manager had to deal with them. Just irritating enough to stress you out.

Walking into your little apartment, you wish you had a pet. A cat or dog. But if you did, then you’d have to care for them and you never seem to have time.

You get out of your uniform and pull on a T-shirt and sweats. As you do, you feel the tension in your neck and shoulders. Grabbing a drink from the fridge, you stretch for a moment then sit down and log into your computer.

After you go through emails, you feel bored and a little tired. Maybe you’ll go to bed early, but first you open up a couple of your chat apps. 

There are a few messages, most of which are from old classmates, including your “BFF”, Jen, talking about plans for the upcoming weekend. Maybe if you aren’t working, you’ll spend time with her and her boyfriend Roger.

A message pops up. You smile. It’s from ‘NiceGuy63111’.

“Hi Bobby, how was your day?” you type on the screen.

He and you have been chatting for months. At first you thought he might be a scammer, but he never asked for anything, nor sent anything that you didn’t want to see.

The only pics you and he have shared are quick, smiling selfies. No nudes or anything that you didn’t want. His comments are sometimes light and flirty, but nothing suggestive or dirty.

You pieced together that he’s a divorced guy in St. Louis, a little older than you. He let slip a few times that he hadn’t been a good husband, but he was still making changes in his life. One of those changes is learning how to listen to women. Whenever you chat with him, he seems genuinely interested in how you are. He makes you feel comfortable and safe.

“How was your day?” he texts.

You quickly type “Fine”. As you still feel the tension in your shoulders.

“Really? Not a stressful day?” You can almost hear the doubt in his words.

“Ok, let me tell you about it.” You reply. Telling him about the irritating customers, frustrations of having to clean up messy tables, and reading texts from your friends who have plans that you might not be able to take part in. As you type, your neck and shoulders still have that tight, tense feeling.

“Damn it. I wish you were here to give me a massage or something.” You quickly type. 

You are about to delete it, but before you can, he responds “Really? I can’t be there, but would it help if I described how I would massage you?”

You chew on your lower lip for a moment. You’ve never tried anything like that. You know that people ‘sext’ all the time. When you were in school, you and your boyfriend at the time, tried it. It was okay. It just seemed rushed and stupid, especially if you were going to hook up later. But this is different. Bobby isn’t your boyfriend, and you aren’t meeting up later, but you think “What the hell. Sure.” 

“Ok.” You type and watch the screen.

“Imagine I’m there.” He starts. 

“Standing behind you…

“You are sitting…

“and you feel my hands gently caress your neck.” 

He types in small texts with pauses.

“Lean your head forward as I slowly rub and caress your neck….. 

“Now feel my fingers on your shoulders…… 

“I softly but firmly press… 

“moving my fingers in small circles…

“relaxing your neck….

“and helping remove the tension from your shoulders.”

As you read his words, you try to imagine what he is describing. You slowly roll your head and crack your neck. Then you exhale and relax your shoulders.

“That’s it….

“Feel how good my fingers are on you….

“Feel how your muscles are relaxing.”

You pull off your T-shirt and bra, and double check to make sure your cam isn’t on. Then you slowly rub your neck. Moving your fingers as he described. 

“This feels so good.” You text and then lean back in your chair. “Can you massage my breasts?” you type. Then quickly delete it. Almost ashamed of what you typed.

He types “I can massage your front, if you want. It’s your call.”

You chew your lower lip for a moment, then type, “Yes… Please Continue.”

“Ok. Then instead of sitting, imagine lying down with your shirt off…. 

“A pillow or towel is under your head… 

“and you relax as I slowly drip baby oil down the center of your chest. I rub some on my hands…

“then I start with your shoulders and upper chest.”

You get up and head to the bathroom. Finding a small bottle of lotion, you sit back down. Slowly you drip a line between your breasts. It’s cold on your skin. Setting the bottle down, you slowly rub the lotion on your skin.

“From your upper chest you feel as I move down and around your breasts….

“my slick fingers massaging and caressing your warm smooth skin…..

“around and in between.”

As he describes it, you slowly work the lotion around your tits. Your nipples are getting hard. You’ve never done anything like this with Bobby.

“As I rub your breasts, I slowly rub around your nipples….

“I imagine they are hard and sensitive.” As you read his text, you pull and roll your nipples.

“They are” you quickly type and follow with, “You can suck on them if you want.” which you then delete. If he was here, you would say that, but he is halfway across the country, and you don’t have that kind of relationship.

“I move down to your flat tummy…

“softly massaging and caressing your abdominal muscles…. 

“Careful to massage and not tickle.”

“You are so good at this.” You type. “Do you do this kind of thing often?”

“Do you feel better? More relaxed?” he responds.

“Yes. I feel better.” You say, pulling your T-shirt back on. “You didn’t answer my question. Do you do this often? With other people?”

There is a pause before he types his response. “I used to sext all the time. That is part of what broke up my marriage, my online cheating.”

“Oh” you type and then just look at the screen. After a moment you continue. “So why haven’t we sexted?”

“You didn’t seem interested. I enjoy our friendship. I’m trying to be a better person and make positive changes in my life. Sending ‘dick pics’ and sexting with women I meet online is how I used to do things. That’s not who I am now.”

“Oh.” You respond again. “So it isn’t a ‘looks’ thing?”

“Hell no. I’ve told you many times that you are cute and beautiful. I love the selfies you send. If that’s what you want, I’d love to pleasure you. But that’s not the type of relationship we have.”

You read his comments again. ‘If that’s what you want, I’d love to pleasure you.’

“Bobby, can we stop for the night. I really enjoyed the massage fantasy. It helped. I feel so much better.”

“I’m glad. That was the point of the fantasy.” He quickly replies.

“What would you think if I wanted sexting?” you type.

The dots on your screen blink as he is typing something.

He must have been typing and deleting because when it post it’s only says.
“I can do that, if that is what you really want. But lets wait. It’s getting late here and I have to get up early. Goodnight.”

“Of course. Goodnight Bobby” you type and log off.

You tingle with excitement and anticipation. You go to your bedroom and masturbate, fantasizing about him.

(This is the first chapter in what I hope will be a three or more chapter story. If you enjoyed it, Like and leave me a comment. If you enjoy my writings, follow and subscribe.)

Punishment for Not Paying Attention in History Class

  **This is a work of pure fantasy. It is only in the imagination of the writer.** You are taking my college history class. As I’m lecturing...