She Lost A Bet With My Mother

She Lost A Bet With My Mother

Fbailey story number 584

She Lost A Bet With My Mother

I was sitting in my bedroom playing a game on my computer when I heard a soft knock on my door. I said, “Come in.” A very attractive woman entered wearing a business suit with a nice skirt.

She said, “I lost a bet with your mother. I need you to cum inside me so that I can let your mother inspect me and get this bet over with.”

I looked at her as she lifted her skirt and sat on the edge of my bed. She said, “Come here young man and let us get this over with as quickly as possible. I have things to do.”

I looked at her as she sat there staring at me. I said, “But I’m a virgin.”

She replied, “I know that. That is why your mother sent me up here to you. Now let us get started.”

I smiled and said, “Then take your clothes off. I ain’t never seen a naked girl before.”

She shivered and said, “Young man your English is atrocious. You should never use the word ain’t and I am no girl, I am a fully grown woman, a lady in fact.”

I replied, “And I’m a horny fourteen-year-old virgin boy that ain’t never seen a naked lady before.”

She thought about it for a moment and said, “Oh! All right, you win.”

I watched her as she took my chair out from under me and moved me to my bed to sit down. She then unbuttoned and removed her suite coat before she hung it neatly on the back of my chair. She was wearing a silky white blouse that I could see through. She had on a very sexy white lacy bra. It was much prettier than my mother wears. She unzipped her skirt and slipped it down her legs. She removed it from around her ankles and folded it neatly to lie across my chair. She slipped off her high heels and placed them side by side in front of my chair.

I asked, “What’s that.” Then I pointed at her waist.

She replied, “It is a waist chincher. I wear it to make my figure look better. Men appreciate a woman with an hourglass figure.”

She then reached back and unhooked a dozen or so tiny hooks like Mom has on her bra. The chincher was placed on her skirt and then she unhooked her bra from behind.

When she pulled it off I practically shouted, “You’ve got small tits.”

She blushed for the very first time and replied, “Young man, I have small breasts like all of the women in my family.”

I said, “But your bra is so big. I don’t understand why.”

She replied, “My breasts are slightly smaller than an A-cup and I have found that a C-cup makes my suits look much better. My padded bras make up the difference.”

She then lowered her panties, stepped out of them, and placed them on her other clothes. She then stood before me naked. “Okay, I am naked, now can we get on with it?”

I asked, “Ain’t girls supposed to have hair on their cunts?”

Again she blushed and replied, “Again with the ain’t. Yes, women have pubic hair. I choose to shave it off.”

I asked, “Why?”

She replied, “Because I have found that men like that little girl look so I give it to them. I have also found that men will give a woman oral sex if he does not have to spit out pubic hairs as he does so.”

I asked, “What’s oral sex?”

She blushed and said, “Is this turning into an anatomy lesson?”

I asked, “What’s an anatomy lesson?”

She answered, “Okay, okay, you win. I will have the sex talk with you. Anything to speed this along.”

She said, “Oral sex is when a man goes down on a woman. Before you ask, he licks this.” Then she pointed to her pussy slit.

I said, “Okay, I want to do that.”

She kind of huffed but got on my bed and lay back in the middle. She positioned me between her legs and then lowered my head to her crotch. She pointed out her pubic mound, her outer and inner lips, and her vagina and clitoris. She told me to lick her clitoris if I wished to give her oral sex.

She held her pussy lips open for me, I reached under her legs to hold on, and then I plunged my head into her crotch. I gave it a couple of licks and decided that I liked it. I then started racking my teeth along that tiny protrusion causing her to go absolutely wild. When she reached for my head I thought that she was going to push me away but instead she held me tightly against her crotch. She moaned and she groaned and then she pushed me away saying, “I cannot take anymore orgasms, three is more than I have ever had before. In fact no man has ever given me one before.” I shoved my face back into her pussy and started racking my teeth on her clit again. She passed out after two more orgasms.

As she lay there I remember hearing the other boys talking about blowjobs so I crawled up to her face and stuck my cock in her mouth. As soon as my cock got inside her wet mouth I exploded. She gagged, coughed, and shouted, “You little bastard you came in my mouth. It was supposed to go in my vagina. Now what am I going to do?”

I replied, “I can cum in your cunt if you want me too.”

She said, “It is my vagina or my pussy if you must use that word but it is not my cunt. Do you understand?” Then she thought about what I had said and asked, “You can ejaculate more than once a day? How many times a day can you do that?”

I smiled and said, “A dozen times. I’m a very horny fourteen-year-old.”

She smiled for the very first time and said, “I have never had sex with a teenage boy before, not even when I was a teenager.”

I asked, “When did you loose your virginity?”

She replied, “I was twelve years old and he was forty-two.”

I asked, “Was it your father?”

She said, “No it was the man that repaired our washing machine. My mother did not have the money to pay him and offered to let him fuck her. My mother was a crude woman. He wanted me instead and he got me.” She was thinking and then she added, “He came around to fix things that were not even broken just so that he could have sex with me.” She contemplated what she had said and asked, “Can we get back to business? I need your cum in my pussy. Then your mother will feel me up, find the mess in there, and agree that I fulfilled my end of the bargain.”

I said, “Not so fast. I want to learn more and I want to cum in you more than once.”

She blushed and said, “Okay. This ring around my nipple is called an areola. If you suck on my nipple getting my areola wet, then you can blow on it and it will crinkle up. If you can reach up inside my pussy far enough you can find my G-spot. That will drive a woman insane.”

I asked, “Even more than what I did to your clitoris?”

She blushed and said, “Maybe we should try it.” She found some lubricant in her purse and greased up my hand and her vagina. With some effort I got my hand up inside her and used my knuckles to rub the inside of her pubic mound. She went crazy and there was absolutely nothing that she could do about it either. She couldn't get my hand out or shove it in any further. She thrashed about on my bed trying desperately to dislodge it from inside her but to no avail. I rubbed her through eight orgasms until she could not move another muscle. I had drained her of all her energy. We took a nap with my hand still inside her.

Mom came in an hour later and shook us awake. Mom asked, “Are you two done yet?”

The lady answered, “No! He still has not cum in my pussy.”

Mom said, “Okay. In that case I’ll fix some dinner and you are welcome to spend the night in his bed.”

The woman asked, “Will it take all night?”

Mom replied, “If he is anything like his father was…then yes. Hell, I might find six or seven loads of his cum in you by then. Remember…do not clean up, I need to feel you up first.”

When Mom left I started to rub her G-spot again. I was much gentler that time. Then I asked, “What bet did you loose?”

The woman laughed and said, “For about a year now your mother and I have had a running bet as to whom could sell the most houses in a month. I always win and your mother has to let my clients fuck her. This month I lost and got you.”

I asked, “So how many clients has my mother fucked in the past year?”

The woman replied, “At last count…thirty-seven.”

I asked, “Where and how?”

The woman said, “Well since I am her boss, I have a private office. She gets naked and I show the client in.”

I said, “You made her get naked but you resisted getting naked for me.”

She blushed and said, “But your mother is not me. She is used to being naked and fucking strangers.”

I said, “Only because you made her do it.”

She looked at me and replied, “Listen here young man, your mother is just slightly above being a slut. She loved every cock that entered her cunt.”

I could not believe that this sophisticated woman had lowered herself to my level. She could swear with the best of them.

I rolled my knuckles around inside her pussy and said, “I want to butt fuck you next.”

She blushed and replied, “Okay if you must. At least your cock is relatively small. My washing machine repairman wasn’t. He only did it one time though. My mother wouldn’t let him do it to me again. So he started butt fucking her. After that we got a new repairman.”

I spent the entire night fucking her. I stuck it in her ass, in her pussy, and in her mouth. When morning came around Mom entered my room and reached under the covers. She shoved three of her fingers into her boss’ pussy and came out with a sloppy hand. Mom said, “Okay, your bet is paid. You may leave whenever you want too.”

The woman asked, “What if I don’t want to leave? What if I want to sleep with your son every night? He is quite the young man.”

Mom said, “Yes, he is. Okay, you can move in with us but I still want to fuck your clients as well as my own.”

I asked, “Mom, you fucked your own clients too?”

Mom smiled and said, “Yes, I did and they didn’t have to buy a house to do it either.”

I asked, “So how many men have you fucked in the past year?”

Mom laughed and said, “What makes you think that they were all men?”

I watched as Mom pulled the covers down, got between her boss’ legs, and stared feasting on my mess.

I though about fucking my mother but I decided that I already had my hands full with one woman.

The End
She Lost A Bet With My Mother

Similar stories

Summer School Part 8

Part 8 - Cindy and Daryl Progress Cindy was almost shaking she was so excited to tell Daryl about her talk with her mother. Shit, she was now on the pill! Her doctor’s appointment consisted of a quick peek and feel of her boobs and vagina and she was on the pill! Now she would be safe from pregnancy and Daryl could shoot his stuff anywhere he wanted. He would be soooo happy. Daryl meanwhile was just as excited. Though he had lingering embarrassment from his mom seeing him cum, especially on his own face, he was thrilled to have condoms...


Likes 0

Theres a wolf in the fold...

*the Non-Fiction* It was the first day of class. I wasn't nervous; it's a technical nerd school so I felt right in. My name is T.K., and I was in NO way prepared for classes this semester...sure I studied and aced the class but I failed the most important test.... In my second class I saw this tall looking dude, kind of bumped into him didn't really care about his existence at all....then after passing him I did my occasional look back to check out what I just walked away If I wasn't in love with him I know I...


Likes 0

Barb comes out

Barb’s Adventure Chapter 1 Barb had been raised in a church going household. As she entered her teen years, she heard the stories from some of the kids she went to school with about sex. Cock, oral sex, std’s, and of course babies. She didn’t think about it much. She was from a religious family and of course, she would never have sex before marriage. Through her teen years, she noticed the increase in her senses when it came to looking at and being around boys and men. Her sexuality was awakening. She noticed their smell, looked at their arms and...


Likes 0

Little Daniel

Intro: this story is based on real events however locations have been changed for the protection of others. My name is Tommy and im around 5’3” 145 pounds and in my opinion not gay but totally Bi. Im 16 now and this Story is about actual events that happened when I was 14. Any way to the story. When I was 12 my mom had died and my dad started dating again and appearently he had bad taste in girls cause they were either A: ugly as hell, B: Hot as Hell but thieves, or C:Either and had kids. Well when...


Likes 0

Rich boys love 17

I have decided to write the rest of my story put please note my story isnt all about sex having saying that this part does have sex in it and btw the person who wrote that comment saying they inpersonate me and harvey when he jacks off your gross! when me and harvey faced the front of the class we listened for about 20 minutes then harvey tapped on his desk to get my attention. i looked over at him and he was rubbing him self though his jeans i reached over with my head and wispered need some help with...


Likes 0

The Marriage Bed

She was married off young. She was fifteen when she married a thirty-five year old man, his name was Rohan. She was afraid of him, and he was turned on by her. She was short, had well placed curves. Her breasts were fairly large for her frame and were often displayed prominently at the top of her bodice. Her name was Anna. Anna was not afraid of her future husband at first, but that all changed on their wedding night. She was standing in her dress as he stared at her. Inspecting every inch of her body. She shivered, no gentleman...


Likes 0

End Of School

It was the end of school, end of a life time, end of an era. The interim time when the little school girl was changing into the woman she wanted to be Randy and I had been playing around for months and I was deeply in love, but at the same time worried that I had fallen too hard for him. Randy was more than a few years older than me, I had just turned seventeen .He had everything the other little boys didn’t have cars , bikes , money , credit cards and a gorgeous seven and half inch cut...


Likes 0

Becoming Prom Queen; Chapter 3

Chapter 3 The next morning I woke up to the sound of that jarring rock song blaring from my phone. I was still a little groggy since I hadn't fallen asleep till late due to my awesome masturbation session. Slowly raising my head I grabbed the phone and turned off the alarm. Yawning, I swung my legs off the bed and walked over to my dresser. Well, I thought, time to see what kind of outfit I can come up with that won't give Beth a heart attack. Rummaging through things for a while, I finally picked one out. It was...


Likes 0

My Family 7 re-write

My Family 7 Re-write. We left my Aunt Jenny’s about ten the following morning. She let me drive so she could suck my cock on the way. She told me she was going to miss me and hoped I would come visit her Christmas break and to bring Ester. I would like to eat her fine pussy again. I assured her I would try, at least for three or four days. When we passed one of the big semi-trucks while she was giving me a blow job the guy almost went off the road trying to watch. When I came she...


Likes 0

Summer Fun Part One

I would turn 12 on our last day before summer vacation. I was looking forward to spending a lot of time at our ranch and enjoying the rolling hills, and the lazy summer days with my new friend Janet. Janet and I had met the last week of school. We hit if off right away. She was a beautiful blonde, 5’ 4” tall with a body that just wouldn’t quit. I had found looking at other girls really was beginning to turn me on and I thought she would be that someone special that I could really “get into.” We had...


Likes 0

Popular searches


Report this video here.