Insidious Angel Ch. 01

Jon clicked on the button labeled [ MESSAGE ].

He found that he had to upgrade to a paid membership to send messages to other users. He quickly pulled out his credit card and entered the details. In a few moments he was staring at a blank message box. What should he say? He wanted to be respectful with his message and keep it brief. This young woman clearly knew her worth and he didn't want to be kicked to the curb immediately.

He wrote, "Hello Miss Angel. My name is Jonathan. I am very interested in getting to know you and learning how I can be a benefit to you."

Jon clicked [ SEND ]

He could see that Angel had been online the previous day but not yet today.

He reached down and felt that he was still very erect. In the last few years of his marriage he had often needed Viagra to have intercourse with his wife. Now this tantalizing young lady had thoroughly aroused him with one photo and a few written words.

He got up and went to his room. He removed his pants and underwear and laid on his bed. He popped open the sugar baby app and scrolled to StrictAngel's profile. He gently stroked himself as he looked at her photo.

After a few minutes Jon was very horny. He decided to go into the bathroom to masturbate into the toilet, as he did every few days.

Before he stood, his inbox revealed he had a message. His stomach jumped. He released his swollen cock which fell against his stomach. Precum dibbled from his penis as he opened the message.

He read, "Hello potential Daddy, Thank you for your message. I see that you are local to me. There are two possible ways you may serve me. I receive many messages so I need you to show your sincerity. I know some women on this site take an initial tribute and vanish. I can assure you that I'm much more interested in your long-term servitude than a single payday. You may send me a financial tribute through the gifting portion of my profile. You decide how much. After that you will receive a personal message. One last thing, you are NOT allowed to masturbate to my photo."

Jon looked down at his hard cock dribbling on his stomach. He had never encountered a sexually dominant woman. He said to himself, "Holy shit, this woman is exciting as hell; long term servitude?" He read again, "Not allowed to masturbate to her photo?"

Jon stood and pulled his underwear and pants up over his erection. He was very horny but the idea of holding off for her was unusually exciting. He went back out to his living room and sat in his recliner. He clicked back into StrictAngel's profile. He found the gifting section. He decided to gift her $50. He sent the gift.

He sat and waited, staring at his inbox. It was Friday night about dinner time. After fifteen minutes Jon saw that StrictAngel had logged off of her profile. He realized she likely had better things to do on a Friday night than message potential sugar daddies.

The next day Jon found himself logging in and checking his messages every few hours. After a long and boring day it was time for bed. Jon stripped down to his underwear and got into bed. He lay in the dark and, of course, his thoughts were on the mysterious confident young Angel. Soon he realized his underwear was wet. He was dribbling precum again.

He slipped his hand into his underwear and grew hard in seconds. Jon imagined Angel's picture, then remembered her message forbidding masturbation to her picture. Of course he wasn't actually looking at her picture but he could see it in his mind's eye. He stopped himself. He eventually drifted off to sleep.

In the morning he immediately logged in to his profile. He was dismayed to find no message. Sunday was usually his cleaning day so he tried to keep himself busy. He cleaned his kitchen, and bathroom. He even organized his garage.

By dinner time he was getting discouraged. He was worried that he was simply a fool that had been conned by a smart young girl.

After dinner Jon logged back into his profile. He was excited to see that he had a new message.

He opened the message and read aloud, "Hello Jonathan, thank you for the tribute. If you want to learn more about me, we can schedule a short phone call. I require a phone interview before meeting in person. If that goes well, I will give you instructions to meet me in a public place of my choosing. There, you can bring me an additional tribute and we will have a discussion about our possible future together. My email address is FallenAngel@nowmail.com.

Send me a clear picture of your face. In the email tell me your username, phone number and three times that you would be available to answer my call. Give me three, two-hour windows in the next week. Don't miss my call. My number ends in the digits 9966."

Jon realized his heart was pounding. He was actually excited, and possibly a little nervous. He checked his schedule and typed out a message. He made the subject his username; Jon1969. He typed his message, "Dear Angel, Thank you for responding. I am available to talk on Tuesday or Thursday evening from 7:00 to 9:00 pm, or Sunday afternoon from 3:00 to 5:00. He added his cell phone number. Then he took a selfie, attached it and sent the email.

Jon sent the message. He wondered how long they would talk on the phone. Two hours seemed like a long time.

The days dragged by very slowly. By Tuesday evening Jonathan's balls had a subtle ache. He hadn't felt it since high school when his hormones were raging. Back in those days he'd sit in one class or another with a hardon in his pants as he ogled one of many gorgeous young women.

At eighteen years old he could masturbate daily and be just as horny the next day. Now in his fifties, he only got horny when he looked at nude women online. That was changing now. He was purposely avoiding X rated pictures to minimize his need to pleasure himself. He was saving his orgasm because Angel told him to. He found that he would often get partial erections and his balls would ache.

He sat next to his phone for two long hours both Tuesday and Thursday nights. She didn't call.

Once again, on Sunday afternoon Jon sat down with his phone and waited. The minutes ticked by like hours. He had not masturbated for over a week. He could not remember the last time he had gone that long, even in marriage. The dull ache in his balls was impossible to ignore. He was beginning to realize he had developed a masturbation habit.

By 4:30 pm he began worrying that she wouldn't call. He was working through different scenarios in his mind of what he should do if she didn't call. How long should he wait to message her again?

Suddenly his phone rang. The phone number was not in his contacts but it ended in 9966. Jon's stomach flipped. He cleared his throat and took a deep breath before he answered, "Hello, this is Jonathan."

Angel's voice was feminine and sexy, "Hello Jonathan, it's Angel. Actually my name is Angela. How are you?"

Jon was nervous at the thought of talking to this beautiful young woman, who was half his age. He said, "Um fine, I'm fine how are you?"

"Well I'm amazing. As I indicated in my message, conducting a phone interview is a personal requirement of mine for anyone who wants to, serve me."

Jon said, "Yes, I understand."

Angela continued, "I obviously received your email. You are quite handsome Jonathan."

Angela was playing up to Jonathan's ego. After all, he was old enough to be her father. Jonathan said, "Uh, thank you."

Angela continued, "Tell me about yourself Jonathan."

Jon said, "Well, I'm 52, divorced with three kids. I've been an engineer for my entire career. Now I manage a department of about twenty-five engineers. Uh, let's see, I don't really have any hobbies."

Angela said, "You're in management huh? So your days must be full of decisions and telling people what to do?"

Jon said, "Yeah, my days can be stressful."

Angela said, "Don't worry Jonathan, when you're with me you won't need to make any decisions at all. How does that sound?"

Jon said, "That actually sounds good."

Angela continued, "How old are your kids?"

Jon said. "My oldest are twins at 25 years old and my younger daughter is 22."

Angela said, "So what's your living situation? Do you own or rent? Do your kids live with you? Do you have a roommate?"

Jon said, "Both my boys are married. Honestly I don't see them much since their mother and I divorced. My daughter is a senior at State. She graduates in the spring. I live alone, but my daughter visits me around the holidays and stays over sometimes in the summer."

Angela said, "So you have a lot of personal time on your hands huh?"

Jon said, "Yeah, I suppose I do. In fact, that's how I ended up finding you."

Angela said, "So you were surfing the web one night and stumbled upon my profile."

Jon chuckled nervously and said, "Yeah, that's right."

Angela continued, "So what is your idea of the perfect sugar arrangement?"

Jon said, "Uh, well, I guess I never thought of it."

Angela giggled and said, "So you just want to leave it to me? Okay, I'll give you my PO Box and you can send me a check every month."

Jon nervously stammered, "Uh well uh."

Angela said, "Jonathan, I'm kidding. Relax, this is supposed to be fun."

Jon was relieved. He said, "Oh yeah, sorry, I'm just a little nervous."

Angela said, "Why are you nervous?"

Jon said, "Well you're just so uh, attractive."

Angela said, "Why thank you Jonathan," she continued, "but think for a minute. You reached out to me for a reason. What are you hoping for?"

Jon said, "Well, I was never able to approach really pretty girls so I guess I'd just like to be with you. You know, go out to dinner, or whatever."

Angela said, "I get that. So I'm sure you realize that a lot of guys want to be with me."

Jonathan said, "Yes."

Angela emphasized, "Jonathan, when I say a lot I mean, a lot. I receive about twenty new messages a week. The good news is, that only a few people get to the point where you are right now."

Jon said, "That's good news."

Angela agreed, "It is good news," she continued, "but I need to make some things clear."

Jonathan said, "Okay."

Angela said, "I want to make sure you understand that you will never, ever, have sex with me."

Jon said, "Okay."

Angela said, "No Jonathan, I want you to say it, so I know we understand each other."

Jonathan's penis began to stir in pants. He said, "I understand that I will never, ever have sex with you."

Angela said, "Very good."

Now Jonathan's penis was firm. He had never encountered such a confident young woman. Her stern demeanor was turning him on. This was a new experience for him.

Angela continued, "Be aware Jonathan, if you want me in your life, it will be expensive but so worth it."

Jonathan said, "I'm aware. I mean I'm aware that it will be expensive, to have you in my life."

Angela smiled to herself. She was already changing Jonathan's behavior by making him answer her questions very specifically.

Angela said, "I will allow you to make some choices. After all, I don't know you at all. For example, if we were in pubic together would you prefer I call you daddy, or Jonathan, or something else perhaps?"

Jon said, "Jon or Jonathan is fine."

Angela said, "Okay fair enough. As for me, you'll refer to me as princess, whether we are in private, public, or even on the phone. Do you understand?"

Jon replied, "I understand, princess."

Angela smiled to herself again. She said, "Very good Jonathan."

Angela said, "There's another thing I need to be clear on. I expect complete honestly from you. I promise to be honest with you, can you make the same promise?"

Jon said, "Absolutely, I promise to be completely honest as well."

Angela said, "Perfect, so let's get into the real questions here. First, how much money do make per year?"

Jonathan was quiet for a moment and Angela said, "Jonathan, are you there? Give me some honesty."

Jon didn't want to lose Angela already. He answered honestly, "I make $150,000 per year, before taxes."

Angela said, "Not bad, not bad, moving on. What kind of car do you drive?"

Jon said, "I have a Mercedes S 560."

Angela said, "I don't know the models but that sounds nice," she continued, "Let's see, do you own your own house?"

Jon said, "I own a condominium."

Angela said, "Where's it located, roughly."

Jon said, "I'm on the northeast side, not far from the towers shopping center."

Angela said, "Yep, I know the area, my condo is actually not far from there."

Jon was getting more relaxed as he and Angela talked, then she got playful. Angela said, "Okay, tell me Jonathan, how often do you masturbate?"

Jonathan was caught off guard. He said, "Uh what?" His cock twitched and grew firm again.

Angela said, "You heard me Jonathan."

Jon knew he couldn't deny it. Angela would know he was lying. He said, "Usually two or three times a week."

Angela said, "Uh huh, and when you pleasure yourself, tell me about it. Do you watch porn, do you look at naughty pictures?"

Jon could feel his face getting warm as he thought about what to say.

Angela said, "Jonathan, if you want to make it past the phone screening you need to answer my questions."

Jon said, "I uh, I look for pictures of pretty girls, online."

Angela said, "Nude pictures?"

Jon said, "Yeah."

Angela said, "What else? You must have sexual fantasies."

Jon said, "Well, I'm not really that experienced. I married my high school sweetheart and she's the only woman I ever slept with."

Angela said, "Awe, that's so sweet," Angela paused for a moment.

Jonathan didn't know it but he had passed Angela's phone screening. He made plenty of money and, more importantly, he was compliant and sexually vanilla. Also, he was responding nicely to Angela's guidance of how to behave on the phone.

Angela continued, "Well Jonathan, I want to talk more but I'd like to do it person, is that ok with you?"

Jon was elated. He said, "Yes, yes, that'd be great."

Angela said, "I can meet you next weekend, say Saturday at 10am."

Jon said, "Absolutely, where would you like to meet?"

Angela said, "There's a coffee shop on James Street near 136th Avenue."

Jon said, "Yes, I've been there."

Angela said, "Good, so here's what I want you to do. I want you to buy me a book. Nothing fancy, just a paperback book. You choose, fiction, nonfiction, title, it doesn't matter, just buy me a book."

Jon said, "Okay, I can do that."

Angela continued, "Now here's the important part, I want you to put a cash tribute right in the middle of the book. You decide how much. Then tie a red ribbon around the book, just like you would tie a gift. Keep the book right in front of you on the table, that's how I'll spot you in the coffee shop."

Jon said, "Okay."

Angela continued, "I'll try to be there as close to 10am as I can, and I expect you to already have a table. Also, get me a small, black, hazelnut coffee and a blueberry muffin."

Jon said, "I can do that."

Angela said, "One more question before I go."

Jon said, "Yeah."

Angela said, "How many times have you masturbated since my first message to you?"

Jon was proud to answer honestly, "None."

Angela was doubtful. She said, "Jonathan, remember, I expect honestly."

Jon was sincere. He said, "Well, you said I couldn't, do that, with your picture. I really can't get your picture out of my head so I couldn't... do that."

It amused Angela that Jonathan couldn't even bring himself to say the word masturbate. She pressed further. She said, "Jonathan, my first message was over a week ago."

Jon said, "Right, it was nine days."

Angela giggled and said, "But who's counting?"

Jon laughed nervously.

Angela said, "So, are your balls aching?"

Jon said, "Actually they are, most of the time."

Angela said, "I'll tell you what. I'll give you permission to give yourself one orgasm, and I'll even let you do it while you look at my picture. I want your orgasm to happen exactly at 10pm tonight. One orgasm before we meet. How does that sound?"

Jon didn't give a second thought to the fact that Angela was giving him "permission" to masturbate. The fact was, he had accepted her control over his orgasm from her first message.

Jonathan said, "Actually that sounds great. I'm really uh, I could use one"

Angela chuckled and said, "I know Jonathan, I'll see you Saturday and uh, enjoy yourself tonight."

Jon said, "Uh yeah, thanks," they hung up.

Meanwhile at Angela's condominium, she turned to her female slave Tina and said, "Read back what we have on Jonathan."

Tina and Angela had both been on Jonathan's phone call with headphones. Tina was kneeling on the floor next to her princess. She was not allowed to use the furniture. Tina scrolled to the top of the information she had entered into Angela's "client database".

Tina was a middle aged, divorced mother of two. She had a better than average body considering her age of 45 and, the fact that she had two kids. She was wearing only a thick black leather collar around her neck that was secured with a lock. Her pubic hair had been completely removed by a process called sugaring at a salon where she worked.

There were three stainless steel rings pierced through her body. She had one in each nipple and a third pierced through her clitoral hood which carried a small round metal tag. On the tag was an engraved inscription, "Angela's bitch".

Angela was fully clothed. She was wearing a short black skirt with a long sleeve white shirt that exposed her midriff. She was also wearing a pair of black high top converse tennis shoes without socks. She had been wearing her shoes all day.

Tina said, "Okay here's what we have so far. His first name is Jonathan. He's 52 years old, 165 pounds and five foot ten. Based on the phone interview, he is divorced with three adult children. He's a managing engineer making $150,000 per year. He lives alone. He has very limited sexual experience and only with one woman. He masturbates two or three times a week and, he has no social life."

Angela smiled and said, "Well, I'll make my decision after I meet him but he sounds like a very good slave candidate. He simply doesn't know it yet. I'll have to ease him into it slowly."

Tina smiled and said, "This is going to be fun. Your first natural slave."

Angela smiled and nodded thoughtfully. Then she said, "How would you like someone around here to help you with the cleaning and scrubbing?"

"I don't mind cleaning for you princess Angela," said Tina

Angela reached up and cupped Tina's breast in her hand and gently caressed it. She said quietly, "I know but won't it be nice to have help around here? Someone to hand scrub the tile floors and toilets? Someone to keep the floors clean enough to eat from? Someone to hand wash my lingerie and keep all the dungeon toys clean?"

Tina's eyes were closed as she enjoyed Angela's hand on her breast. She nodded and quietly said, "Yes princess."

"What's next on my schedule?" said Angela as she released Tina's breast.

Tina switched over to Princess Angela's calendar. She said, "Slave Darren will be here at 7pm for his weekly chastity cage check and chance to orgasm. That's all for today."

Angela commented, "That's good. I'm looking forward to getting these shoes off, my feet have been sweating for hours." Like several of her domination clients, she had trained Darren to lust after her feet.

Tina clicked on to the next day and continued, "Ok, tomorrow morning at ten, slave Michael is brining your new doggie cage for your bedroom. That should only take a short time. I told him there will be no play, it's just a drop and go."

Angela said, "What time will you be here?"

Tina said, "I can get here by 9:30AM"

Angela said, "Perfect, I might just stay in bed."

Tina continued, "Then you're free tomorrow until three in the afternoon. William is taking you shopping."