Boss's Whore - Cover

Boss's Whore

Copyright© 2021 by DDMarshall

Chapter 2

Erotica Sex Story: Chapter 2 - Gail had no illusions about what her boss expected when he hired her. The salary and benefits exceed her worth as a high school dropout. Gail provided the noontime services her boss demanded and entertained him at her apartment in the evening. Gail was content to be able to provide a better standard of living than she ever expected for herself and her boys. That was until her boss demanded more from her and her boys. Along with her boss's new demands, Gail made demands of her own.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   mt/Fa   Coercion   Reluctant   Incest   Mother   Son   Masturbation   Oral Sex  

Saturday morning Steven said he was going to go down to the pool for a swim. Billy was going to go too but Gail asked him to stay and help her for a few minutes. Gail could tell Billy was feeling bad about Friday night and was trying to avoid her. Gail sat Billy down and he hung his head and said, “I’m sorry Mom but I didn’t want you to lose your job. Maybe I should have hit him.”

Gail hugged Billy, “I know honey, I know. I wanted to tell you not to do it but I was afraid to lose my job and not be able to take care of you and Steven. What’s done is done. I’m to blame for not insisting we go to the bedroom and you did what you thought was right at the time.” Gail tried to lighten the mood. “I bet I looked pretty funny with my ass sticking out like that.” Now that Billy felt he was forgiven he blurted out, “No Mom you have a great ass.” That made Gail laugh and Billy felt better. Gail and Billy thought it best not to mention what happened to Steven.

Gail did the grocery shopping on Saturday and a few other errands. On Sunday she took Billy and Steven to see the latest Star Wars movie. Billy could see that his mother was not as happy as she usually is on the weekends when they are all together. He knew it was because of Friday night.

Monday morning came much too fast. She brought Bob his coffee and finished the filing before noon. He called her into the office at noon and locked the door. Gail jerked him off and lapped up the cum while he ate his lunch. She was not allowed to leave him messy in the office. Three more trips for Bob’s coffee and an afternoon donut and it was time to go home.

Tuesday he told her to lean over his desk and he finger fucked her. Of course, he reminded her of how sexy it was to watch Billy do her. His mentioning Friday night concerned Gail.

Gail never resented Bob for requiring the sexual favors she provided. She was forewarned and agreed to service him for financial gain. The man deserved to get what he paid for. But involving Billy was not part of that agreement.

Gail endured the disdain of the other women that worked in the office and the smirks of the men when she reappeared from Bob’s office after the lunch break and went to the lady’s room to comb her hair and freshen up her makeup. But she was determined that he was going to pay for the humiliation she endured that night with Billy. She just had not figured out how to do that without losing her job.

It was Wednesday night and she was on the couch in her nightgown and her feet tucked under her and feeling glum.

“Hey Mom, how come so sad?” Her son Steven asked.

Gail had not even noticed Steven and Billy come out of their rooms. They sat on the couch with her. Gail put her arms around her two boys and admitted, “Things have not gone as I planned lately.”

Steven did not even try to hide his anger, “That ass hole Mr. Whitman again? How come you let him come over and fuck you all the time? I don’t like him.”

Billy and Steven were well aware of what their mother did to earn a living. Plain language was always used in reference to what she and her boss did at their apartment. Gail certainly was not going to call it making love.

“Yes, it has everything to do with him. But if I told him he couldn’t fuck me he would fire me and we would lose this nice apartment. I don’t know if I could even earn enough to feed us if I lost this job. And look at all the nice things we have now.”

Billy also voiced his resentment of Bob Whitman, “Yeah Ma, I hate him too. He lied when he said you liked it when we put our fingers in your cunt.”

Gail hugged Billy a little tighter, “Shush Billy. He should not have taught you that word. Just say pussy.”

Of course, Billy’s slip of the tongue was the first that Steven had heard of the incident and Gail had to explain what happened on that Friday night.

Gail hugged her boys again as she went on to explain that a finger in her pussy was not a bad thing when done properly. “It can be fun when it is somebody I like is doing it. But I am starting not to like him very much after the other night. I don’t know what I am going to do if he wants Billy to do that again.”

“Do you think he will fire you if I don’t do it?” Billy asked.

“If he gets mad enough he might. He knows he can get other girls to do what I do.”

Steven asked the question Gail had been asking herself all week, “So are you going to let Billy do it again if butt-head wants you too?”

Gail shrugged as she thought of the consequences if she didn’t, “I might have to if I want to keep my job.”

Billy hung his head and lowered his voice, “I kind of liked doing it when I thought you liked it. But then I saw you crying.”

That put a smile on Gail’s face. “I bet you did, you little scamp.” Gail gave him another hug and a kiss on the cheek and teased him, “It’s not every little boy that gets to play with his mother’s pussy.”

Steven asked again, “So, Ma are you going to let Billy do it again if Mr. Whitman tells you to?”

“I guess I will have to. We really need the money.” Then she thought of Billy and how he might feel. “Billy, would you do it again if Mr. Whitman tells you too?”

Billy certainly did not want to be responsible for his mother losing her job, “Yeah, if it will help you keep your job. But I would rather do it when he is not around. That would be more fun. He scared me a little.”

Then Steven asked a question that Gail would never have expected. “Can I do it, Mom? I have never even seen a real pussy.”

Gail was caught off guard. Here she was thinking she might let her youngest finger fuck her for the second time in front of her boss and her firstborn had never seen a real pussy. A half dozen men have played down there and now it included her youngest. Why not satisfy her oldest son’s curiosity. Gail untucked her legs and pulled up her nightgown and slipped her panties off. She got off the couch and knelt on the floor. She pulled her nightgown up over her hips leaving her whole back end bare as she leaned on the couch. She thought this would be the most comfortable for Billy because it was close to the same position she was in when he did it the first time. “Billy, show your brother what you did then let him do it.”

Gail felt guilty showing herself to her boys like this but she knew Bob was very likely to ask Billy to be involved again. They might as well be prepared and she couldn’t very well refuse Steven if she was going to allow Billy to do it. Billy and Steven got behind her. Gail spread her legs just a bit and laid her head on her arms. She actually felt a tingle of excitement as she waited for Billy to put his finger in her.

Gail could not help but smile as Billy gave his big brother the tour. “See this is Mom’s ass hole. And this is her cu ... pussy. I put my finger right in here.”

Gail closed her eyes and tried to imagine it wasn’t her kids back there. But she could not do it. She knew it was Billy when he slipped his finger in her. His finger moved in and out inexpertly. There was no rhythm, just push in and stop and then pull back and stop. Gail had enjoyed being finger fucked in the past and she thought if they were going to do this they might as well learn how to do it right. She couldn’t help them with their homework but this was something she felt confident she could teach them.

“Stop, Billy.” Billy stopped and took his fingers out of his mother’s pussy.

“Did I do something wrong, Mom?” Billy sounding worried.

“No, you did fine. It will be better if we just do it a little differently. If we are really going to do this you might as well learn the best way to do it.” Gail stood up and pulled her nightgown up to her belly button and laid on the couch with her back against the padded arm of the couch so she was sitting up a bit. “Okay, Billy, get between my legs. Now give me your hand.” Gail held Billy’s wrist and took his middle finger into her mouth to slick it up with her spit, “It’s always better if your finger is wet. Now use your middle finger with your palm up. Go ahead put it in.” Gail sucked in a breath as she watched her youngest boy put his finger in her pussy. “That’s it curl your other fingers back.”

Gail tried to tell herself this was to make it easier for Billy when her Boss demanded another show. And if they put on a good show, she would get to keep her job. Steven would be dating soon and could use some experience. But as Billy started to move his finger in her wet pussy she felt herself getting aroused as she watched her son perform this very sexual act between her legs. After only fucking Minute-Man-Bob for two years she was more than ready for an intimate and erotic venture. How could she have known her own son’s finger could give her more satisfaction than Bob’s cock? Gail smiled at Billy as he looked up at her. “Oh, Billy you are making me very happy.”

Gail coached Billy on how fast to do it and when to put that second finger in her. Gail looked at Steven and he was watching what his brother was doing with rapt attention. She also saw where his hand was as he gripped the outline of his cock through his pants.

“Okay, Billy give your brother a chance. You did great. If Mr. Whitman wants you to do it again I want you to do it just like you just did.”

“So you liked it when I did it?”

“Yes Billy, This time I really liked it. You did it just right.” Gail spread her legs a little wider. “Okay Steven, now you try.”

“Oh wow, Mom. Can I just touch it to see what it feels like?”

“Okay.” Gail’s son was asking to feel her up and to her surprise, she didn’t mind. Watching Billy put his finger in her pussy had sexually excited her. Now Steven touching her was giving her the same feeling. Gail watched Steven as he felt her pussy and ran his finger through her pubic hair. Steven put his middle finger in his mouth to get it wet. Gail’s hips bucked when Steven put his finger in her pussy. She could feel her chest getting hot. “Yes Steven, do it just like Billy did.”

“Do you really like it, Mom?”

“Yes, Yes I do.” She assured Steven then called to her youngest, “Get over here Billy, hurry.” She opened her arms and hugged Billy to her breasts. “Kiss me, Billy, kiss me.” Billy kept kissing her cheeks. “Yes Steven, keep doing it. Yes, don’t stop, oh God, I think I am going to cum.” Gail kissed Billy on the lips when she felt her orgasm take over her body. Her hips bucked and Steven’s finger slid in up to the last knuckle as she moaned into Billy’s mouth. She kissed Billy and had the orgasm she so desperately wanted.

It took Gail a few moments to settle down and tell Steven to stop and take his fingers out of her. Steven was still kneeling between his mother’s open legs as Gail rubbed her hand over her wet pussy. “Oh, my sweet boys. You made me so happy.” Gail sat up and picked her panties off the floor and put them on then straightened her nightgown.

Gail looked at her boys as they looked back at her with that look in their eyes that said, “But mom, how about us.” Steven was still kneeling on the couch as Billy stood nearby. Both of the boys were touching themselves.

Gail knew they were aroused as soon as Billy started fingering her. But she had not thought far enough ahead to think about what she was going to do about it. But now that she could think about something other than her own needs she knew exactly what she wanted to do.

“Well, boys, it looks like we have something to take care of.” Gail reached out with her finger and playfully poked Steven where she saw the bulge in his pants. Gail expected she would take the boys to her bedroom but Steven whipped open his jeans and pushed his pants down and grabbed his cock and stroked it, “Oh God Mom, I need to do this so bad.”

Billy was watching his brother and his mother. He knew he wanted to do it too but wasn’t sure if he should show his cock to his mother.

Gail watched Steven jerk himself off. She was going to let him do it and even help him if he wanted her to. But then she thought of the mess it would make on the fabric of the couch. Gail stood up. “No Steven, not on the couch.” Gail grabbed both of her boys by the hand and took them to her bedroom. “Get your sneakers off.” Gail pulled back the covers on the bed. Take your pants off and get on the bed. You to Billy.”

Gail got on the bed and knelt between her two boys. She took Stevens six-and a half-inch cock in her left hand and Billy’s five-inch cock in her right. “When a girl has a good cum from a boy touching her as you did, this is one of the things they might do to thank you.” Gail thought of other things she could do but tonight was not the time for that.

As Gail started to masturbate her boys she could not help but think about her days in high school and how she did this and more for boys the same age as Billy and Steven.

After playing on the couch with their mother both boys were more than ready. It didn’t take much more than a couple of minutes for Steven to exploded and Bill was not far behind. Gail giggle as they made a complete mess of their bellies and her hands.

Gail went to the bathroom and wet a facecloth with warm water and came back into the bedroom and cleaned her boys up. “Okay boys, one more hour on the game console, and then it’s bedtime. You wore your mother out.”


The last couple of days at the office had been pretty easy. There wasn’t much filing and Bob only wanted a blow job at lunch. Gail would drop dead from shock if he ever offered to return the favor.

Friday night Bob said he was coming over. He followed Gail home and parked in guest parking. Gail waited for him and they walked up to Gail’s apartment together and went in. The kids were watching TV. Gail said hi to the kids and went straight to her bedroom with Bob. The kids knew not to come in there when Bob came over.

Gail took all her clothes off skipping the striptease she usually put on for Bob. She pulled down the covers on the bed and got in. Bob took off his suit coat, shoes, pants, and boxers. He left his shirt, tie, and socks on like he always did. Once he was done fucking her he wanted to be able to leave as soon as possible. He had no other reason to hang around if they were not having sex.

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