Pissed Off Boss Ch. 03

Story Info
Rick is invited to boss's house for more filming.
2.1k words
4.52
72.1k
15

Part 3 of the 3 part series

Updated 09/22/2022
Created 04/17/2005
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

***Strapon play and Female domination abound in this chapter (and all others).If this is not your cup of tea then try something else. This is the third part, so you may want to read the first three. Please leave feedback and vote.***

*

Saturday turned out to be quite breezy and cool. It was the kind of day that Rick thought perfect for the beach. There wasn't a cloud in the sky and the cool temps made the strong sun perfect. Instead of heading to the beach, Rick headed to his bosses house. Ms. Pittman had invited him over to her house to work on the latest ad campaign.

Rick shook his head. It was not an invitation that he could refuse, nor did he want to. Within the past few days his boss and her secretary had forcefully fucked him. He would have never thought it possible, but he was quickly becoming accustomed to the domination. The sex was wilder than he had ever imagined, and being dominated by two women only added to the pleasure.

He arrived at the house and could smell food grilling around the back. The house was not overly large, but was deffinetly nice. The sound of splashing water alerted him to the fact that she also had a pool. He rang the door and Ms. Pittman answered. Rick was stunned when he saw her. She always dressed in business attire around the office and he had never imagined her in any other way. She was dressed in jean shorts with a white tank top that showed off a very plump chest. Her hair was down to her shoulders and her make-up was more pronounced.

"I'm glad you could make. I'm also glad that you dressed as I suggested." She said. Rick had dressed in a pair of kaki slacks and a polo shirt. He had also brought his golf clubs, even though he had no idea why she wanted him to.

"Sue and I are already set up to go. I want to get started right away. I am going into the kitchen. Wait sixty seconds before following me in. You will act like you're my husband who is returning from a day of golf. I trust that you can play it by ear." Ms. Pittman instructed him. She stepped aside and ushered Rick into the house.

Rick watched as she closed the door and silently left the room, leaving him alone in her foyer. He hadn't expected for things to move so rapidly and felt as if he had little control in the matter. He glanced around the room as he counted silently in his head. From what he could see, she kept a clean and comfortable house. He counted a full sixty seconds before heading toward the direction she had left. He could hear water running and see the tile floor of room at the end of the hall.

"Hey honey, I'm home." He called out as he stepped into the kitchen.

Rick took quick notice of the cameras that were placed around the room, as well as Sue sitting just outside their range. She was holding a camcorder of her own. Ms. Pittman was standing at the sink, apparently washing dishes. She turned around and on her hands she wore a pair of yellow rubber gloves. She also wore a scowl on her face.

"I'm home? That's all I get?" She sneered. "I've been cleaning all day long while you've been out playing with your friends. When do I get a chance to play?"

Rick rolled with the punches and made thinks up as he went along. "I do work all week long. Why is it such a big deal for me to play a few rounds of golf?" He fired back. She hadn't instructed him on the tone he should take, so he just said what came into his mind.

"So what is that supposed to mean? Just because I take care of the house it's not considered work? I work just as hard as you do." She said and tossed a dishrag to the floor.

"I never said that you didn't..." Rick began.

"I don't care. I'm not doing it anymore. The dishes need to be cleaned and I'm not doing it. You do it." She said.

"Now listen..." Rick tried again.

"I'm not kidding. If you're not cleaning those dishes in a minute you might as well pack up those clubs and everything else you own and get out!" She yelled.

Rick figured it was time to give in to what she wanted. He sat his golf bag down on the floor and walked over to the sink. "Fine, I'll do the dishes. It's not that big of a deal." He said, keeping a tone of defiance in his voice.

Rick could see Ms. Pittman out of the corner of his eye as she sat down on a stool. He washed the dishes while she talked.

"I guess I'm lucky. Most of my girlfriends have husbands who can't even satisfy them in bed, but you do know exactly what to do. And I guess I have to be thankful that golf helps you stay in such good shape. Even your adventurous spirit is a plus. After all, so many men are too stuck in their ways." She told him.

Rick was fast coming down to the last dish. "I didn't mean to keep you from relaxing. I'll try to help out a little more so that you can have your own time to play." He said. Rick was playing the role of a husband who was trying to pacify his wife.

"That's good, since the dishes are the last of the chores. I'm also glad that you recognize my need for playtime. I know you'll enjoy helping me have fun." Ms. Pittman told him.

Rick's hands were in the hot water as she stood up and moved behind him. He acted surprised as she reached around him to unbuckle his belt. His pants and shorts quickly dropped to the ground.

"What are you doing?" He asked, turning his head to try and look at her.

"Finish those dishes. You played eighteen holes today and I'm just going to play one." She said with a resounding slap of his ass.

Ms. Pittman moved around to his side so that he could see what she was doing. She unsnapped her shorts and unzipped them. He watched as she slid her hands inside and withdrew a very realistic shaped dildo. Rick was actually surprised. She had hid it very well, and there had been no bulge to show what she was wearing. The cock looked to be a bit bigger than the ones that she had already used, and guessed that it was from the realistic-porn star line.

"I picked this up while shopping today. Let's see if I can hit a hole-in-one." She said while stroking the latex member.

Ms. Pittman reached and grabbed a bottle of dishwashing liquid from the back of the sink and then stepped from his line of sight. He felt her move behind him and then her hand on his waist.

"Bend over." She commanded and pushed between his shoulder blades. He was quickly bent of the sink, and soon found her spreading his legs apart. Rick heard the bottle being squeezed, and then felt a stream of the thick liquid running down the crack of his ass.

"That's it." Ms. Pittman said, and Rick felt her rubbing the head of the cock up and down his crack. She coated the fake cock and laid it between his as cheeks like a hot dog in a bun. She slowly slid the length of the shaft back and forth, letting him feel how long it truly was.

Rick caught his breath as she pulled away and redirected the cock on a downward angle. She rubbed the tip at the base of his balls and then slowly slid the shaft along his sack, causing his balls to ride the shaft like a train on a rail.

"You have to have a strong shaft if you expect to drive it deep." Ms. Pittman said with a chuckle. She pulled back and Rick knew that she was ready to get down to business. He felt the tip of the cock as it pressed into his ass. She hadn't lubed him inside as before and he was worried about taking such a big toy. The head retreated as quickly as it had advanced, only to be pushed in again.

Ms. Pittman kept repeating the motion, and pushed deeper with each thrust. It took over a minute before he felt the head pop past the tight ring of his ass, but she still wasn't ready to feed him the entire shaft. He felt the head pull free and his ass convulsed from the stretching. He jumped as he felt the cold angular tip of the dish-liquid bottle push into his hole, and shivered his insides were flooded with cool liquid.

Rick braced himself, as the bottle was pulled loose. The cock returned and the head slid in with less resistance. His slick tube yielded easily to the cock, but the thick shaft still caused him to groan. He felt fuller than ever before and could feel the shaft rearranging the inside of his ass. Rick could feel the head deeper than any other. He took a breath and tried to relax and Ms. Pittman took the opportunity to make one final push. His breath caught in his throat as the head slid into some unseen pocket and her balls touched his.

"Fore!" Ms. Pittman yelled. She didn't give Rick a chance to catch up with her. She wiggled her hips to make sure she was embedded as deep as possible and then began fucking him. She kept the strokes short and deep, making him feel her deep in his ass. Rick tried to keep character while she worked him over, but was finding it hard to do so.

"Thank you dear. I think you found the right club." He groaned.

"That's right. I'm way over par baby." She grunted. Ms. Pittman began picking up the pace as well as the length of her strokes. She was soon pounding the entire shaft into him, with the head, popping out on each stroke. He could feel from pounding that she was coming, but she never lost a beat. The only sign he was given was when she began to slow down.

"Oh that was so good. I think my caddie needs a tip for taking such good care of my club." She told him.

Rick felt her changing her angle and shook as she began sliding into him again. The angle now caused the head and shaft to bump and glide over his prostate with each stroke. His cock had been rock hard since she pulled his pants down, but was now throbbing without even being touched. He felt feverish as she kept up her long strokes, and his entire body was shaking. He moved his hand to touch his cock, but she grabbed it before he could.

"You won't need to do that. I'm going to fuck it out of you." Ms. Pittman said. She kept hold of his hand and grabbed his other with her free hand. Rick gasped as she pulled both of his arms behind his back. She used his arms like reigns and pulled him back toward her as she fucked into his ass.

Rick groaned as she renewed her assault on his ass. He could hear the wet sounds as she plunged into him. He could feel it beginning in the pit of his stomach and he closed his eyes. The pressure built until his cock was flowing. His come poured out like a river and his body shook so that it was if he were vibrating.

Ms. Pittman finished him off by pressing in deep and slowly grinding against his ass. She finally let his hands go, and Rick collapsed over the sink. He saw Sue move into view for a second and the felt the cock sliding from his ass. He hasped as his hole was emptied, but his boss held him in place. She pulled his cheeks apart and Rick could feel Sue near him as she filmed his gaping ass. A few fingers circled the inside of his stretched muscle before he was released with a pat on the ass.

Rick turned around and leaned his back against the sink. He looked in amazement at the cock that had just ravaged his ass. It was glistening wetly as it jutted from Ms. Pittman's shorts. She had upped the ante each time and he was wondering what she had planned next.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
AnonymousAnonymousabout 11 years ago
Jail

That's where the boss belongs - after he gets rich in the lawsuit.

AnonymousAnonymousabout 14 years ago
More Mean?

The word gets out that he gives good head, and other women begin to use him during lunch hour. His lunch is their pussy.

AnonymousAnonymousover 18 years ago
The Best

This is the best story ever. It is very realistic. When Rick turns around to look at the strap-on it makes it true to life.

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Beginning Anew Marcus is forced to stay with his smug neighbour Natalie.in Transgender & Crossdressers
Becoming Taylor's Bitch Oliver crashes a party and meets the girl of his dreams.in Transgender & Crossdressers
Futa House A boy unwittingly discovers a gold mine of girlcock.in Transgender & Crossdressers
Shemale Bar Straight guy goes into a shemale bar and is forever changed.in Transgender & Crossdressers
Brutal Shemale Lovers Pt. 01 Jake gets more than he bargained for from Tanya and Sarah.in Transgender & Crossdressers
More Stories