Babysitter Boss

Bryant tried to act calm but knew this was not a place he should be. He hoped only Courtney and Jessica where in the house but he couldn't be sure.

"Ok Bryant" Courtney began, "Jessica here is aware of our little deal and she finds it very funny. Since we obviously need to take this up a little further she is going to help me."

Bryant looked Jessica over. The first thing he noticed at the door were her large breasts, obviously much softer and squishy than Courtney's. She was also a bit thicker in her legs but still an attractive young woman.

Bryant didn't like that Courtney was talking about this with her friend, he could not let this get around campus, that made him legitimately nervous.

Jessica looked overly excited which added to Bryant's growing concern.

"So here is the deal Bryant" Courtney continued "your going to wear this."

Courtney then removed a small group of metal rings from her backpack. It took Bryant a moment for his brain to figure it out, it was a cock cage. It looked as if it would barely fit his dick, and obviously would not allow him to get hard.

"Wait..." Bryant began but stopped quickly. If his wife had stripped to her underwear and allowed Courtney to shove her fingers down her throat he was going to have to say yes to whatever she wanted. His wife was simply in too deep. "Ok" Bryant finished.

Jessica actually clapped her hands and jumped up and down just a little. Her tits jiggled wonderfully.

Courtney smiled. "Good boy, but I'm not totally mean, I will let you jerk off one more time before you put it on so go ahead."

"Ummm OK" Bryant said realizing he was half erect already. He began to look for a bathroom before realizing that would not be the way it would work. "I'm guessing you're going to watch?"

Courtney and Jessica smiled, Jessica much broader than Courtney.

Bryant undid his pants went to sit on the couch.

"Oh no" Courtney corrected "on your hands and knees on the floor, you can cum on the floor and then clean it up."

Bryant lowered himself to the floor, his cock now rock hard. Part of him was very excited that Courtney was obviously a filthy minded enough girl to make this really interesting.

He looked up at the two young woman and began to stroke himself. Jessica stared directly at him, alternating her eyes from his face to his cock. Courtney was on her phone.

"If you can cum in under two minutes you can clean up the jizz up with a towel instead of your tongue."

Bryant began stroking faster, "Jessica can I please see your tits." He asked trying to sound as desperate as possible.

Jessica looked at Courtney who shrugged. Jessica lifted her shirt up allowing her mountain like breast to fall free.

Jessica played with her left nipple as she held her shirt up with her left hand. It was all Bryant needed. He had not seen new breasts in person in years, as he began to spray the floor with his semen he knew he was comfortable within the two minute window.

Courtney shook her head, "quick on the trigger there huh?" She tried to mock Bryant.

"Your friend is beautiful, I couldn't help it." Bryant replies trying to get on Jessica's good side. It seemed to work, Jessica blushed a little.

Courtney handed Bryant a towel and he wiped up his cum and the little drip still on his cock.

Bryant truly did not remember the last time a woman other than Angela had touched his penis, but moments after he put the towel down he had four delicate hands on his dick. He stood and watched as the two girls slowly squeezed his manhood into the strange contraption. He felt his balls compress as they strapped the base on. His cock seemed to swell between the rings as the girls molded it into place. He tried to breathe slowly as his manhood was shrunken into its new home.

Once he heard to final lock click into place he looked down at his almost crushed cock. The two girls were having trouble containing their laughter, which shamefully made his dick strain against the rings even more. He was embarrassed to admit that being laughed at turned him on.

"It looks like it's trying to escape!" Jessica giggled.

"Well it better not." Courtney said. She then continued "Every day at lunch hour to come over and have Jessica check that your still wearing it. If you make it the next two days Angela will join us here after work for a little group fun."

Bryant was relieved that Angela would get to join in soon, he really wanted her to.

Bryant dressed and walked back to his office. It felt incredibly lumpy but he really didn't feel like it could be seen through his pants. The people he passed didn't seem to look at him unusually at least.

When Bryant got home that night Angela met him with a grin. She had obviously gotten an update.

As they went up to bed Angela finally asked to see it. Bryant showed it to her and again felt the throbbing grow and showing it to her aroused him.

"It looks so tight." Angela muttered as she reached out and felt the cages weight.

"It's very tight especially when I'm turned on." Bryant said.

"Does it hurt?"

"Not really, it's not comfortable though." Bryant said, trying to slow his breathing and relax.

Angela looked him over before telling him she had bad news.

Bryant just looked at her waiting to find out.

"I have a homework assignment from Courtney. I have to masturbate in front of you. You have to watch the whole thing. I'm sorry hon." Angela did sound sorry.

Bryant knew better than to try and cheat, he settled into the one chair in the bedroom and watched his wife undress.

Her nipples were hard as she was clearly excited. Bryant realized that his torture probably turned her on, which in turn made him more aroused.

Angela lay in the bed and began touching her breasts and then her stomach before rubbing the inside of her thighs. He legs spread further and further as her hands began rubbing the length of her vagina.

Her breath picked up as she focused more and more on her clit. Bryant has not watched her play with herself in a long time, and even then it was more a tease before sex. He realized how much attention she paid to the skin around her pussy, he would need to remember that the next time he was with her.

Angela loved that Bryant couldn't get off, the sight of his cock all boxed up like that was really hot to her. She was even exaggerating her moaning now to make him as uncomfortable as possible. She reminded herself that this whole fantasy was his idea and she should not feel guilty taking it as far as she wanted to.

As she got closer and closer to cumming she began rubbing her clit harder and harder, god she loved being free to get off as he sat there with his cock throbbing. She couldn't wait to tell Courtney how much her husband's helplessness turned her on.

Her orgasm was loud and aggressive. It was better than any orgasm Bryant had given her in years, She bucked her hips up into her hands as she used both of them on herself. She squirmed and gasped as she came in front of her impotent husband.

As Angela lay in her bed recovering she realized it wasn't just that her husband's cock was locked up that got her off, it was because he had come up with this game but she was the one who was going to take it to the next level. He should have been careful what he had wished for because there was no way she was going to hold anything back.

**********

Fourteen hours later Bryant stood in front of Jessica, exhausted and naked from the waist down. He had not slept much the night before. Between the show his wife had put on and knowing it was going to get even more extreme kept him from relaxing.

Now this was happening. He had thought she would just look at it to make sure he had not pried the cage off of himself, but she was more curious than that. She ran her fingers over the ridges and under the base where her skin brushed against his balls. Bryant was truly starting to be concerned that the way his cock swelled against the metal rings might damage it. It felt so tight when he became aroused, which seemed to be happening a lot lately.

"Does it hurt?" Jessica asked, her fingernails still grazing his balls.

"Not really pain, more just uncomfortable." Bryant answered again, trying not to think of how odd it was to be discussing his cock with a twenty year old.

"I love how it looks." Jessica said, no longer even looking at Bryant. She was moving her face closer and closer to him.

Her chin was only an inch or so from him when she looked up. "I can do whatever right?"

Bryant wasn't really sure. Angela had said he had better do whatever Courtney wanted to do, and Courtney had said Jessica was helping her so he guessed it was OK. "Ya, I think."

Jessica smiled and Bryant watched as she extended her tongue to meet the restrained head of his cock. Bryant was enthralled with the image of a woman who was not his wife licking his cock, even if he couldn't fully enjoy it.

Her tongue pushed against the flesh of his organ that had swelled through the rings. She pushed her tongue against it, looked up at Bryant and did it again. She giggled a little bit. Then she grasped the back of his cock and rang her tongue up the length of him, over each ring and then back against his skin.

"OK your good." Jessica said suddenly standing up and back away from him.

Bryant felt light headed. Just like that he was supposed to go back to work. This was going to be a long few days.

**********

The next few days did not include much sleep for Bryant, but Angela seemed to be managing just fine. He knew something different was happening that night but the only detail he knew was that a new babysitter was coming over so they could both be at Jessica's.

Bryant was amazed at how calm Angela seemed as they walked into the girl's house. They shouldn't be there for any reason and if any other college employees saw them coming or going it would be a real problem.

As soon as they entered the house Bryant was escorted to a small coat closet off the living room. Through the slots on the door he could see a little of the living room but only small areas. He saw his wife sitting in a chair on the side of the coffee table. Even though he could only see the side of her face he could tell she was smiling. Jessica and Courtney were waiting by the door as if they were expecting company any minute.

That company did arrive soon. That company was just over six feet tall with smooth black skin, a shaved head, a big smile and after only moments in the house Bryant got a look at his well defined chest and abs.

Bryant wondered if all the songs he was going to strip to were ninety boy band songs, but the women did not seem to mind. In fact based on their hoots they seemed to like it a great deal. Bryant watched through the slots as the girls took turns running their hands up and down his chest as he danced for them. His cock was barely contained within a silver sleeve, but his wife seemed to be making an effort to change that.

He felt a pang of jealousy as his wife rubbed the back and insides of the man's thighs. When he stepped away from Angela she would call him back over quickly, rubbing him more and more aggressively. Bryant's stomach clenched watching this but his cock also throbbed.

The show lasted a little over half an hour before he packed his few props up and headed to his car. As Bryant was leaving the closet thinking the evening was over he saw his wife head out the front door holding the stripper's discarded shirt.

"Hey Bryant, you might want to come upstairs for a minute." Courtney said.

Bryant went up the stairs to the front bedroom where he could look down onto the driveway. He saw Angela leaning into the passenger window of the car. He could also see into the car as the interior light was on and dancer inside that car had a huge grin on his face.

He watched them chat for about a minute before Angela moved away from the window, but instead of heading inside she opened the door and slide into the seat next to him.

Bryant saw a brief hesitation in Angela's body language but only a brief one as this young stripper leaned over and kissed his wife. His hand went through her hair and after a moment the kiss broke, he leaned back and Angela's face leaned down into his lap.

Braynt sat next to his babysitter and watched his wife's head bob up and down on a male stripper's cock. The stripper had adjusted his seat to lean back and had even put his hands behind his head.

Bryant was horrified but it got worse when Courtney began talking. "You know I told her that very first night she came to my house that I would never actually do anything that would hurt you guys." Courtney paused as this sunk in.

"So that means your wife is out there sucking that dick because that's what she wants to be doing. Are you ok with that?" Courtney seemed to feel a little bad for the man she just a few days ago locked into a cock cage.

Bryant could not look away as Angela continued to aggressively service this nameless man. She had not begun using one of her hands along with her mouth, and her tits were also being casually groped.

A minute later Bryant realized his wife was taking a mouthful of warm cum that was not his. She held her head still and pumped her hand up and down, Bryant recognizing the look she got when she was swallowing, and she had that look on her face for what seemed like ages. He must have shot a pint glass full of semen down his wife's throat.

Bryant met Angela back down stairs in the kitchen, she was wiping her mouth with a paper towel, her makeup smeared across her face. She looked at Courtney before speaking.

"When can I do that again?" Angela was beaming.

Bryant was stunned but Courtney seemed to have already made plans. "Tomorrow night actually."

"Oh god yes," Angela said before turning to Bryant. "Honey can you believe our game is really happening?"

Bryant could only grunt.

***********

The next evening Bryant sat back up in that same bedroom with Courtney and Jessica, his cock still caged. They had explained to him that in a couple of minutes they would be helping Angela live out the fantasy they had shared about her fucking a student. Colby, the tallest member of the Men's Volleyball team would be the lucky student.

Courtney had assured them he would be blindfolded, he had been told this was a sorority initiation thing, but that would also mean that Angela would be the one controlling the action.

Twenty minutes later Bryant heard the girls downstairs positioning his almost seven foot tall frame. Then he heard Courtney tell him that the pledge would be in in just a minute and that he should give it to her good. Courtney finished by telling Colby that she liked to have her hair pulled. Bryant thought he was the only person who knew that about Angela.

Bryant heard Angela ask Colby if he was ok, if he was comfortable and if he was sure he wanted to do this. Colby responded that he wasn't exactly sure what this was.

Then Bryant heard his wife say that she also wasn't sure what this was, but that she wanted to "fuck him till his cock fell off." Colby seemed ok with this.

For the next hour and fifteen minutes Bryant listened to his wife moan, scream and yell about how big the cock that was in her pussy was. When it got quiet Bryant knew that meant she had his dick in her mouth, and when he moaned he knew he was either cumming in her or on her.

At various points Angela demanded to have her hair pulled, her nipples pinched and her thighs nibbled. She yelled for him to rub her clit as he fucked her, she told him to cum in her mouth and she begged him to get hard one more time.

Courtney smiled the whole time, but Jessica actually laughed at him. Jessica then decided it was time to take the cage off his cock. Courtney said no, but Jessica wanted to see if he would get hard while he listened. Courtney's grin widened even more as she got the key out.

While Angela was grunting as she obviously got fucked, Bryant sat with two college girls with his newly freed cock exposed and fully erect. Courtney and Jessica were now openingly mocking him.

"I can tell she hasn't gotten fucked this good in a long time."

"You are going to for sure be able to tell how much he stretched her pussy out, it's never going to be the same."

"Can you imagine how much cum she has swallowed in the last two days?"

"Do you think Colby's cock is more than three inches bigger than yours?"

"I can't believe you asked for this."

That last one stung the most.

Once Colby was clearly exhausted Angela scampered upstairs before he took the blindfold off and Courtney went down congratulated him on such a strong performance and showed him out.

Angela sat down next to Bryant, her hair was crusted with cum just above her ear and she was still breathing heavily. She didn't say a word which made Bryant, who still had his cock out, very uncomfortable.

Courtney was back in the room before Angela even said a word, but what she did say made him feel much worse then the silence that had preceded it.

"That was fucking amazing." Angela said, her face lighting up.

"Tell us everything!" Jessica exclaimed.

Bryant watched as the two girls leaned forward to hear all the details. Angela told them how big his cock had been, how he had thrust it into her harder then she had even taken it before, and even how his cum had tasted almost good.

Courtney and Jessica looked envious of the sex Angela had just had. Bryant guessed that Colby was going to be getting some more action from the other girls.

While all of this truly hurt Bryant's feelings he could help but enjoy how wonderful it felt to have Angela's hand casually caressing his cock. It was almost as if she wasn't even aware she was doing it, so Bryant didn't dare ask her to go faster as she might stop completely.

As Angela was describing how Colby had rubbed her clit as he had done her from behind Bryant let out a small moan, which seemed to remind the woman he was still here.

Courtney looked down at his engorged cock. "Oh my, someone really likes hearing about a real cock!" She giggled at him. Even Angela gave him a shit eating grin.

"I think maybe he deserves a LITTLE reward." Jessica chimed in.

"What do you have in mind?" Angela asked.

Jessica paused and Bryant began praying that she really meant a reward.

"Well I saw this thing online once, it was a woman taking one finger from each hand and running them up and down a guy's dick. Then as he came they took their hands away so that he got off but it didn't really feel that great."

There was a pause before Courtney chimed in "You watch too much porn."

"That seems good to me." Angela said kneeling before her husband.

Bryant wanted to scream. All of this had happened because of a silly fantasy. Now his wife was fucking and sucking every guy she saw and he couldn't even get a real hand job.

Angela our both her index fingers into her mouth, wetting them slightly. She then looked up into his eyes and began sliding her fingers very slowly up and down the shaft of his dick.

Bryant couldn't help moaning even with this pathetic amount of stimulation.

He was even more disappointed in himself as he found himself thrusting his hips back and forth trying to increase the amount of friction on his dick.

"He looks like a dog trying to hump someone's leg." Courtney snickered.

Bryant closed his eyes, he was completely humiliated but couldn't help himself. As he thrust harder and harder he realized Angela had stopped moving her fingers at all.

"Come on baby, you do, let us see how bad you want to make a little cummy mess on the floor." Angela taunted him in a baby voice.

Even with that hit to any part of his masculinity that remains Bryant knew he was going to cum any second.