Babysitter Boss

"Of course I sucked his cock. I knelt on the floor and tried my best to take his whole hard cock into my mouth but of course it didn't all fit!"

Angela loved how aggressively Bryant ate her when they role played her having had sex with another guy.

"I gagged and gagged on him until he finally shoved my head down so hard! It hurt!"

Bryant groaned as he kept lapping at her clit.

"Of course I would never let you do that!" Angela was having trouble focusing on the story as she felt like she was going to cum.

"He then pulled his cock out of my mouth and fucked me so hard!"

God she was close, she just needed something that would get him really worked up.

"When he came he sprayed it all over my face like a fire hose!"

Suddenly Bryant's tongue was gone.

"You said fire hose last time, say something else." Bryant requested.

This threw Angela off and she made a mental note that she had been saying 'fire hose' to often. She also made a mental note that she made mental notes about odd things.

"Ok ok ummmm... first he pulled his cock out of my wet pussy and slapped me with it. I could feel my wetness on my face."

That got him to start working hard again. Angela was about to cum.

"He made me drink all of his cum, even the part of his load that got on my face I had to lick up."

She couldn't talk anymore. She grabbed Bryant's head and bucked her hips as she came. Warmth filled her body as her pussy contracted.

**********

Angela and Bryant's sex life had always been good, and even after twelve years of marriage and one kid they still liked to fuck each other and try new things. Bryant had been on this cuckold fantasy for almost a year now. It had taken Angla a little while to get up to speed but in the last few months she had really started to get into it even more then Bryant was.

The idea of a strange man enjoying her and then gloating about it to her husband had sparked something in her. She thought about the stories she would tell him, the types of men she would pretended to fuck. She had told all kinds of stories to him, old men, celebrities, anything she could think of. Recently though she had found what she liked best, students from the college they were both employed by. Angela enjoyed using some of the pictures from the school website to make the stories more realistic and Bryant clearly got excited when he would see those students around campus, reminding him of his wife's fantasies. The difference was that Angela had started to wonder if would ever be possible to take things further than fantasy.

Bryant and Angela had met years ago as students at the university that they now worked. Angela worked in the small advising office and Bryant on the business side managing the schools endowment.

Courtney was their new babysitter, she seemed reliable and upbeat. Courtney was one of Angela's advisee so Angela knew she was a Dean List student. They had not realized how few date nights they had over the last few years until they were able to go out regularly.

Two days after the last cuckold roleplay Angela was very relieved when she arrived home late and Courtney had already given their son dinner and bathed him. They ran down what had gone on with him during the day and confirmed their schedule for the next day.

As Courtney left she added one more thing "Hey, his iPad isn't working and he was pretty upset he couldn't do his little game. He had earned his time."

"OK, thanks for letting me know, I will look at it tonight." Angela reassured her.

Angela never really understood why this happened after each update but she always got it working again. She did worry about how much her son loved his game but she wasn't going to make Courtney have that fight with him.

The next day Courtney arrived in the early afternoon. She was very happy to see the iPad was working again. As the screen turned on she noticed that the messages app had a little red 572 on it. She hated those red bubbles.

Courtney let him play his game for the 30 minutes he was allowed each day and told him if he was good he could have ten extra minutes since he didn't get to play yesterday. Once he was settled with a coloring book Courtney opened the iPad back up, she could not go on knowing that red dot was just sitting there, calling for attention.

Courtney intended to open the app, tap through the threads until all the dots were gone and be done with it. Then she saw the first line from a text from Bryant that read "Fuck him however you wa" before it was cut off. Courtney looked over and made sure the coloring was going well. She had a few minutes to poke around.

Courtney spent more than a few minutes going through the old messages. This had happened to her once, after a software update her iPad had synched up with her phone and her messages had gone to both. The iPad contained the couple's private messages for the last few weeks.

She couldn't help but respect the two of them. They had been together for most of her life and they still wanted the other one to fuck the shit out of them.

She was a bit shocked by the content of their messages. Of course there was the boring things married couples had to discuss but the dirty talk was extensive. At first Courtney thought that Angela was really having wild sex with dozens of men. It took her about 200 messages to realize it was a game, but she had to admit it was a good one.

When Courtney got to the messages about her fellow students she began to form a plan. She started taking notes.

Courtney read their texts for the next few days. She would find herself daydreaming not just about the dirty sex conversations but also about how she now had access to the little jokes and comments that they thought were just between them. She loved having a secret window into their lives. She wanted to be a part of that, she wanted to make them talk about her and she wanted to be part of making a dream a reality.

**********

The next Saturday Courtney was at their home as Angela and Bryant prepped to go out to dinner. Bryant was ready and looking at his phone while Angela was still upstairs.

"Courtney can you come here a moment, I want to go over a few things before we leave." Angela beckoned from her bedroom.

Courtney stepped inside the bedroom as Angela was touching up her makeup. As Angela went over the same things about the bedtime routine and dinner plans that she always did Courtney noticed a skirt hanging in Angela's closet. Obviously Angela had considered it and then set it aside as it was pulled away from the rest of the clothes. It was clearly shorter than what Angela had decided on, not a ton, but two to three inches shorter and would show some of her thigh compared to the knee length piece Angela currently had on.

Courtney hesitated, but decided to go for it. "You should be wearing this, it looks great with that top." Courtney said picking up the shorter skirt.

Angela seemed a little surprised, Courtney had never given an opinion like that before. Angela looked the skirt over, she really had a hard time deciding between the two and of course Bryant had not given an opinion at all.

"They are pretty similar don't you think?" Angela said.

"I really think you should switch." Courtney said, holding her skirt of choice out to Angela.

Angela considered that maybe she was mistaken and the other skirt was a noticeable improvement, Courtney certainly was fashionable so maybe she was right.

Angela took the piece of clothing from Courtney and when the young woman didn't turn to leave slid her current skirt down her legs.

It only took a second or two to switch skirts but Courtney noticed the plain black bikini cut panties Angela was wearing. She made a note to change those.

"Oh that looks great." Courtney gushed.

Angela didn't really see the difference but liked the compliment. Angela went to pull her heels on when Courtney interjected one more time. "No, these boots, they go better with the shorter skirt."

Angela hesitated but once Courtney had said it Angela realized she was going to do it, knee high boots did look sexy and being dressed by this nineteen year old was creating an interesting feeling in Angela's stomach. She had not asked for this advice but she was taking it. It was pretty harmless but usually a babysitter, doesn't tell you what is sexy for you to wear out with your husband, and a grown woman wouldn't normally listen to a teenager on this topic.

Bryant took a long look at his wife's unusual attire as she came down stairs but did not say anything about it in front of Courtney.

Courtney smiled as they left, that had gone pretty well she thought.

**********

The next day Courtney texted Angela. "Hey did Bryant like your outfit?"

Angela looked at the text message a little bit confused. Was Courtney being a little too familiar with that kind of question? Angela did not like the idea of sharing what her husband did or did not like with a nineteen year old, no matter how well they knew each other.

When Angela did not respond Courtney followed up. "I was going to go shopping tomorrow and wanted to know if you wanted to come, maybe we could get some similar stuff if he did. It would be fun!"

Angela hesitated, she actually did feel good the other night, and she did like Courtney, maybe a shopping trip would be fun. She could also probably use some advice on some new clothes. What the hell Angela thought as she agreed. She felt silly for thinking there was more to it then there was.

Angela ended up really enjoying their shopping trip. Courtney brought her into stores she normally wouldn't have looked in, and the skirts she got were shorter, the tops tighter and Courtney even got her to buy a few sexier pairs of panties then she would have gotten herself. They giggled together as they picked them out. Angela felt young again.

Angela had enjoyed Courtney taking the lead, having someone engaged and actively directing her had been nice in a few different ways. She liked having someone else's eye to help her pick out some items she would not have considered. If Angela was honest however that was overshadowed by the slight thrill she had gotten by modeling for Courtney. The thrill had grown the few times Courtney had run her hands over Angela, smoothing her clothing, and Angela had become outright excited the one time Courtney had stayed in the dressing room when she had been in just her panties.

As Angela and Courtney headed to the car Courtney reached into Angela's bag and took her keys. "I'm gonna drive home, I never get drive anywhere." Courtney declared.

Angela had enough fun that she shrugged it off. As they started to pull out from the parking lot Courtney handed Angela a lollipop. "This is for the ride home." Courtney said.

"Oh no thanks, I don't really want anything." Angela said, thinking about some of the chores she would need to do.

"I think you should put it in your mouth Angela."

Angela turned and looked at her young friend.

"It's ok Angela, just put it between your lips for me."

Angela wanted to be angry but something about the condescending way Courtney was talking to her gave her a little tingle between her legs.

"Oh honey, I know you want to do it, just listen to me and suck the lollipop." Courtney demanded.

Angela looked at her and began to get nervous. This sounded just like one of the stories she had told Bryan. Angela took the lollipop and unwrapped it. She placed it between her lips and ran her tongue over it.

Courtney smiled as Angela followed her directions. "Can you guess what is going on Angela?"

Angela looked away, she was embarrassed but wasn't sure exactly why. It seemed obvious to her that Courtney somehow knew something about what had been going on with her and Bryant. Thinking back on her last few interactions with Courtney it seemed she may have known for a little while.

"The iPad hon, all your text messages have been coming to it. You and Bryant are cute, really perverted, but cute." Courtney confirmed Angela's suspicions.

Angela felt her face turn scarlet as she looked down, the grape treat still in her mouth. She found herself humiliated but not angry.

She sat silently until Courtney pulled the car into the parking lot of a closed restaurant.

Shockingly a bar aimed at college students named "Hemingway's Secret" that served only top shelf drinks and oysters hadn't worked out. Courtney pulled around the back of the building away from the road. Angela could see the top of one beat up house that for sure housed more students then the fire code allowed. Other then that this spot felt rather private.

Courtney put her hand on the side of Angela's face and made her look in her direction. She took the stick that protruded from between Angela's lips and pulled it from her mouth.

**********

Angela lay in her bed naked and catching her breath. She had come home and attacked Bryant. She hadn't wanted sex so badly in years.

Now she knew it was time to tell him what had happened. Angela had to start the story a few different ways, and Bryant didn't take it as well as she had hoped.

"Angela" Bryant only called her Angela when he was mad. "You kinda cheated on me."

Angela thought about how she lowered her head to suck that lollipop after Courtney had propped it between her legs. It was like she was in high school again sucking off her boyfriend on a back road.

"She said she would show people the texts about the students. We would lose our jobs!" Angela replied.

"You really think she would do that?" Bryant asked suspiciously.

Angela thought about it. Courtney hadn't actually said she would blackmail them. She had just said she had them and that she knew the guys Angela had talked about and they would really like reading those messages. It had felt like a threat to Angela.

Angela thought back to one of the last moments in the car. She hadn't told Bryant this part. After a few minutes of licking and sucking the sweet candy from between Courtney's legs Courtney had lifted Angela's head and looked her in the eye. Courtney had said "I'm going to slap you in the face, kind of hard and call you a slut. I don't think your a slut but I think you want to be treated like one."

Courtney had then paused, just long enough for Angela to get a little bit scared. Then Courtney had slapped her left cheek hard enough to turn her skin a little pink and then hissed "Get your head back between my legs you fucking slut."

When she had put her face back near Courtney's lap Angela could smell Courtney's excitement.

Angela finally replied to Bryant, "I think she's a little different then the girl we thought she was."

**********

The next Monday Courtney stopped into Bryant's office. He did not have much space as he usually did not have visitors. His hands stopped over his keyboard as she came in. She stood in front of his desk, smiling and slowly picking up a pen, then a coffee mug before finally the wedding photo. Bryant stared at her as she took in the picture before setting it back into place and perching herself on the edge of his desk.

"Your wife has a strong jaw." Courtney stated.

If a man had said that Bryant he would have punched him, but he didn't know how to respond to a teenage girl who knew he fantasized about having strange men fuck his wife.

"Does she usually use that jaw with you or just your babysitters?" Courtney said, breaking the short silence.

Again Bryant was quiet. Courtney looked at him. Bryant realized he was getting hard, partly because he was scared of her and partly because Courtney was very attractive and talking about sex turned him on.

After another silent pause Courtney finished before putting an envelope on his desk and leaving the room. "Be the little cuck you want to be Bryant. That way this stays our little secret."

Bryant was left in his office with a hard cock and a slight knot in his stomach.

**********

Angela read the message for a fifth time. If she was going to follow the instructions she needed to leave in an hour. The rest of the pages were the dirty text messages they had exchanged about the students Angela was supposed to be advising. Seeing that made Bryant much more nervous, especially since he felt they could be exposed by accident if Courtney wasn't careful.

Angela was visible nervous as she left for Courtney's. They knew she wouldn't be coming home again that night, the two of them would not see each other until sometime at work tomorrow.

She closed the door and Bryant stared at it for a moment. His wife had really just left to do something sexual with someone else.

The last thing Bryant heard from her was a text message saying she was going inside. His cock throbbed.

**********

Courtney was at Bryant's office before he had heard from Angela.

"Want to see a little glimpse of how your wife spent her night?"

Bryant was truly curious.

"I'm going to show you three pictures, and that's all. Don't ask any questions, do you understand?" Courtney said.

Bryant agreed and Courtney turned her phone towards Bryant, but when he reached for it she pulled it back.

"I show and you look."

Bryant nodded his head and looked at the picture.

His wife sat on the floor in what Bryant assumes what Courtney's apartment. She was blindfolded and wearing only the matching set of pink panties and bra. She was pulling her knees up in front of her as if she was cold or nervous.

Courtney flipped to the next picture. His wife was now kneeling, still blind folded. Bryant assumes it was Courtney's feet that rested on her thighs and that it was Courtney's hand that had four of its fingers shoved into his wife's mouth. Her mouth was clearly stretched to accommodate this intrusion. She did not look unhappy, even though Bryant couldn't be sure with the blindfold on. It took Bryant a moment to figure it out, but based on the angle this picture was taken at the person whose fingers were in his wife's mouth could not have been holding the camera. How many people had been there?

The third picture showed his wife still on her knees but this time her upper body rested on an ottoman. Her panties had been pulled down below the curve of her gorgeous ass. A ruler rested on top of her butt.

Courtney pulled the phone back and smiled at Bryant. "Stand up and put your hands behind your back."

Bryant hesitated, he knew there would be no way to hide his engorged cock if he did that.

Courtney waved her hand at him "Come on do it or I'll email the pictures that have your wife's face in them to all my friends."

He stood up and Courtney grinned at the pronounced lump in the front of his pants. "You really like this don't you?" She asked.

Bryant looked at the ceiling and then nodded yes.

"You want me to do more with her don't you? You want this to happen don't you?" She said, slightly taunting him.

"Yes" Bryant responded quietly. Having it said out loud did make him feel more embarrassed then he thought he would.

"I thought you might, but this isn't supposed to be fun for you." Courtney said "We are going to have to change that. Be at my friend Jessica's house at noon. She's in the red house across from the street from the science building just off campus."

With that she left. Bryant sat down, but never considered not meeting her for lunch.

A few minutes before noon he headed out towards the road. He knew what house Courtney meant and he did not have to walk all that quickly.

At 11:58 he knocked on the door. A girl he did not know but assumed was Jessica opened the door. She looked at him and laughed a bit as she let Bryant in. "Holy shit this is really happening." She said as Courtney met them in a messy but not necessarily dirty living room.