The Stepmother Ch. 1

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Stepmother teaches stepson a lesson.
2.7k words
3.9
216.5k
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Part 1 of the 3 part series

Updated 10/31/2022
Created 10/31/2001
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When I was eighteen years old, my father remarried. Along with his new wife, came her two daughters, Susan and Kelly. Both girls were older then I. Dad was rather well off and the three of them moved into our large country house. The first year was rather unsettling for me. My stepmother, Jane seemed to dislike me for any reason she could. She would defend her daughters when they did something wrong and she would be the first to blame me for anything. I tried my best to stay out of her way and to try to keep dad happy. That year I began to masturbate a lot. At times I would sneak a pair of dirty panties from the hamper and shoot my load into the crotch of them. It was in the summer when I heard the news. My father was killed in a car accident while away on business. I was heart broken and during the services I wondered how things would change since he was gone. Little did I know that things with Jane would get worse. She collected a lot of insurance money and was set for life. She did things for her daughters and berated me for asking for simple things. I had few friends since we lived in the country. Most of my summer was spent doing chores around the house and the girls would go out with their friends since they a car at their disposal. After doing my chores, I would take a swim in the pool and then a shower. I would look for dirty panties to beat off on.

It all came to an end on Friday night. It was after we had finished dinner and Susan looked at her mom and said, " I think Billy has been beating off in my panties."

"Is this true?" Asked Jane. I looked at her and could feel my face blushing. "Well is it?" She added. Before I could answer her, I felt the palm of her right hand slamming the side of my face. The force almost knocked me off my chair. Jane looked at the Susan and told her to go her the special bag. Susan's eyes lit up as she and Kelly took off to mom's bedroom to retrieve the bag. Jane looked at Billy and told him "I guess your silence means yes. It's about time someone teaches you a lesson about taking another persons private clothing and doing something so vile as to beat off in them."

"You are to sit in that chair and don't even think of opening your mouth you cock beater." Jane got up to fix a drink and then lit a cigarette. The girls had returned from the bedroom with the bag. "Girls, I want you to assist me in teaching Billy a lesson about what he has done." Mom asked. "Sure mom." Both relied in harmony. "Stand up Billy." Jane ordered. Billy stood up from the kitchen table. "Now take your shirt off and don't make me ask again." Billy complied and removed the shirt. "Now drop your pants!" she barked. Billy hesitated because he just remembered he was wearing a pair of Kelly's pink cotton panties. "Are we having a problem?" asked Jane. "Girls, do it." Kelly and Susan grabbed Billy by the arms to hold him. Jane walked in front of him and undid the top of his pants. Billy pleaded for them to stop with no avail. She took a puff of her smoke and then pulled his pants down. Bill was now standing with his pants around his ankles wearing the pink panties. Kelly giggled, "Mom looks like we have a panty boy here."

"I can see that." Replied mom. "To the basement girls." Ordered mom.

The girls dragged Billy down to the basement. Mom took the bag and went into the bathroom. She changed into an outfit from the bag. When she appeared from the bathroom Billy saw her in and outfit he could not believe. She wore black high heels with black thigh high hose. Jane wore a black leather bra that left her nipples exposed. At her age, Jane had a good firm body. Billy looked her over and noticed Jane's very thick pubic hair covering her pussy. The girls cooed at mom telling her what a hot outfit he had on.

She walked over to Billy and without warning kneed him in the balls. She girls kept a hold of him as he screamed in pain. "The problem we have here Billy is that you have a cock. Men do more to fuck things up because of this. So now is the time to show you that your cock is worthless and your days of beating off are over." Jane lectured. Jane opened the bag and removed a pair of leather cuffs. She put one on each of his wrists and attached them to the eyebolts in the ceiling. She went back to the bag to remove two more cuffs and then put them around his ankles. Jane then removed a spreader bar from the bag and then slid it open at to spread his legs apart. Billy was now spread wearing only the pink panties. The girls sat on the couch and watched. "Mom?" asked Kelly. "Yes dear." She replied. "When did you get this stuff?"

"Years ago when your father was still around. Now you know why he was always to nice to us." She replied.

Jane went to the bag and retrieved a key. She then walked over to the storage cabinet and unlocked it. She swung the door open and looked at its contents. She reached and removed a long leather strap. It was like the ones you used to find in barbershops. Kelly and Susan looked at mom as a wicked grin came across her face. Kelly whispered to Susan "Hate to be on the receiving end of that!" Jane set the strap down behind Billy who had not yet seen it. She reached around Billy and her hand pulled the top of the panties down below his balls. She pulled them up tighter between his ass cheeks. Now his cock and balls were exposed. "Mom?" Asked Kelly. "Yes Kelly."

"Looks like Billy was last in line when dicks were passed out." She replied giggling. "Let's check this out." Replied mom. Jane walked in front of Billy and noticed his small cock. "I see you got your puny dick from your late father. Let's see how big it really isn't." She laughed. Susan got off the couch and walked over to a small table and picked up a cloth measuring tape. "May I measure it mom? Asked Susan. "Be my guest. I don't think it will hurt anyone." She laughed. Susan proceeded to measure the length. "Damn mom. It's only 3 inches. Not even worthy of being called a cock." The girls laughed and Billy head his hung low in shame. "Were you expecting to fuck a girl with this? Kelly asked him. "Billy could only nod yes."

"Mom. Can I get him hard to see if it gets any bigger/"

"Please do." Jane replied. "I guess I should find something slippery to jerk his little dick with." She sighed. "I've got the answer." She perked out. Susan pulled her panties down half way to her knees. "Good thing I'm having a heavy flow right now." She said smiling to mom. Kelly got off the couch to watch this closer. Susan put here right hand between her legs and started to rub her dirty pussy. She then began to finger it and soon enough, her hand was covered in goo. She took her right hand and began to jerk off Billy. After a few minutes Billy's cock was hard. Susan grabbed the measuring tape again. "Damn. Only grew and inch. Guess you better find something else to fuck Billy, cause this dick isn't big enough." She laughed at him. Kelly looked at her mom and asked, "Can we see how much he spunk's?"

"Sure." She replied. "Kelly pulled her panties down and removed the Kotex pad. She spit on her right hand and began to jack-off his dick. "Be a good boy Billy and make your mess in my panties like you like to. " She told him. She held the crotch of her panties at the end of his dick. Kelly kept teasing him and she could feel his cock swell. "Come on Billy. She me how you cum in my panties you sissy!" She yelled. Billy could not hold back and began to moan as he pumped a rather large load into the crotch of her panties. She held the panties so the cum would not drip out and laid them on a nearby table. "Very good sissy boy." She added. "Now clean off my fingers sissy boy."

"I'm not licking up any cum you lezbo cunt." This infuriated Kelly. Mom grabbed Billy's dick and began to squeeze it hard. Billy began to cry out as the pain shoot through his body. "Open you mouth sissy boy or I'll swear I'll rip this little dick right off of you." Billy opened his mouth and Kelly slid cum covered fingers in his mouth. "Suck'em clean panty boy!" She yelled. As Billy sucked her finger clean, mom released the grip on his dick. When it was done Kelly remarked, "He did a really good job sucking. I wonder how good he might sucking a big fat cock."

Doesn't Billy look cute in your panties?" she asked. "You bet mom. Looks like a real sissy boy." She replied with a giggle. "Girls. I want you both to be comfy while I punish our little panty boy." The girls looked at each other and both got up from the couch. The stood in front of Billy and removed their shirts. Billy for the first time saw their breasts covered by white cotton bras. Kelly was the oldest at 20 and showed a nice pair of 36D tits with large nipples. Susan was a year younger at 19 and showed a nice 36C pair of tits with large nipples as well. The girls the turned around and pulled their shorts off. They bent forward to wiggle their firm asses at Billy. Both wore white cotton panties.

Billy noticed their pubic hair outside the panty lines and also noticed at large bulge in the middle of the panties. The girls looked at each other and grinned. Both turned around and Billy could see the bulge again. The girls giggled again and pulled their panties down far enough for Billy to see the dirty Kotex pads. Mom was getting a kick out of this. "Ok girls, settle down on the couch and watch me punish this nasty cock beater. I did the same for your father when I caught him doing the same thing." She told them. "Is my little panty boy ready for some punishment and humiliation." She asked Billy. By now, Billy could only nod his head.

Jane stood behind Billy and picked up the leather strap. She wrapped one end around her right hand for a good grip. "Billy, how many strokes do you think you deserve?" Billy was never punished before by his late parents and seemed confused. Before he could answer, "I think 20 licks should be sufficient." Quipped Jane. Jane raised her right hand and with a side ways forward motion, she brought the thick strap across his ass. Her aim was slightly off and the belt wrapped over his right thigh and the tip of the strap hit the tip of his dick."

"Billy yelled out in pain." The girls were laughing and noticed how red the tip of his dick was from the blow. "Billy. Be a man and try not to cry like a sissy boy. I'd really hate to have to gag you and if I must do so, you won't like it. Trust me!' Jane told him. Billy tried to hold back the yelling but on the 10th lick, he yelled out rather loudly. "Billy. I warned you and now I'm going to having to shut that loud mouth of yours. Girls, any suggestions?" The girls thought for a moment and then Susan replied. "I know what to use?"

"What is it you have in mind." Asked Jane. "Well I have to change my Kotex and I thought Billy would love to have my dirty one shoved in mouth since he like the smell of pussy so much." Susan replied with a giggle. "Excellent idea Susan!" Laughed Jane. Susan ran upstairs to get a clean pad. She came back and stood in front of Billy and slowly pulled down her white panties. Billy could see her thick bush and then he noticed the large dirty pad. Billy began to protest as Susan pulled the pad from her panties. "Panty boy, time to shut you up. Hope you like the taste of my dirty pussy. From now on, the only time you'll ever see it, is when it's dirty." Billy began to resist Susan from putting the pad in his mouth. Susan swiftly kneed him in the balls and as he screamed out in pain, she stuffed the pad in his mouth. She then walked over to a work bench, cut off a piece of duct tape and then covered the pad and his mouth closed. "Very good." Jane told Susan. "Thanks mom."

"Susan, I have a question for you? She asked. "What is it mom?" Are you taking precautions during sex?"

"Sure mom. The only time I let boys put their cocks in me is when my pussy is dirty. Never can get preggers this way and sure makes me cum a lot." Replied Susan. "Very good Susan. What about you Kelly?"

"I only let boys put their cocks up my ass." The only thing I put in my pussy are toys. Nothing like a big wad of cum your shit hole." Replied Kelly. "Very good!" Replied Jane. Jane began to resume Billy's punishment. By the time she was done with the 20 licks. Billy's ass was bright red with wide strap marks and tears rolling down his eyes.

Susan looked at Billy and noticed his dick was hard. "Mom?" said Susan. "Yes, what is it."

"I think Billy likes his ass whipping. You made his dick hard."

"Is that so? She replied as she walked around him and looked. "Does being strapped excite my little panty boy?" Jane asked. Billy was still gagged and Jane removed the tap and pulled the pad from his mouth. Billy's mouth was dry and he could barely speak "Do you want something to drink?" asked Jane. Billy nodded yes. She unhooked his cuffs from the ceiling and then laid him flat on the floor. She attached another spreader bar to his wrists. Jane stood over his face. Billy looked up at her thick black pubic hair covering her pussy. "Open up panty boy." Billy was confused again and Jane squatted down and reached behind her to grab his balls. She squeezed them hard and Billy screamed again. "Open your fucking mouth now!" She demanded. Billy opened his mouth and Jane began to let go a steady stream of hot piss right into his mouth. Billy gagged and Jane told him to swallow all of it. "That's awesome mom!" Yelled the girls. "Thank you. Just wait till I train him to suck cum from my pussy and ass."

"Can't wait to see that one." Exclaimed the girls. "Maybe we can invite our faggot cousin over so panty boy can suck a real cock." Added Kelly. "Good idea. I'm sure Johnny would like a nice tight slut hole to fuck too." Replied Jane. "Now lick my pussy clean and make sure you suck that piss off my hair." She demanded of Billy. "Billy complied and when he was done Jane got up looked at him and said. "I think the best thing we can do for Billy is make him a cuckold and marry him off to some wealthy girl who needs to a pussy boy to use. I'm sure we can get a tidy sum from him."

"Excellent idea." Replied the girls.

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7 Comments
AnonymousAnonymous10 days ago

The mom & her daughters should have been wearing nylon stockings & garter belts & high heels to make the story more interesting!!!

AnonymousAnonymousabout 2 months ago

Loved it when the mom spanked Billy & then pissed in his mouth - very sexy!!! The girls should have also pissed in his mouth!

BJBear69BJBear693 months ago

Loved the story!!!! Its ashame that the daughters were not wearing stickings & garter belts for Billy to see them!

AnonymousAnonymousalmost 8 years ago
good one

one day a lady I knew down the street phone me to come over she need some help with some thing I told her I be right over i just got to put some clothes on she told me just a shirt and pants I said what no under wear she said yes ask her what you going to make me wear girl under wear she told me maybe yes or no I told her fine it may be fun to be in women under wear well I got there in a hour I ask her what she need she said come in and I will show you well she show me a wedding grown I need to fix the harm put I need you to wear it but first you were right here your panties put them on and then I will help with the bra I put on the panties they were thong and show my ass then she put on a bra and I felt some thing warm she told me they were fake breasts now stand still till I hook it on you and fit your breasts right I did as told then I heard a lock close she pull the dress over my head and hook it up she show me a mirror I did look like a girl and I had tits too well it take all after noon before she was done she ask if I want to put on one more dress I said yes well it was a short black dress skirt and a white blouse well that day I stray that way when it was time to go I ask if I can keep the bra on and panties and bring them back in the morning she said yes and here wear this nightie at bed time you can feel how we girl sleep in them well that night I sleep like a baby girl in my nightie when I got up and went over to her place she was not up yet I knew were the keg was I let my self in I found a note on the table be a dear and put on the clothes I lay out and bring me a cup of tea I saw the outfit it was a wrap around blouse when I put it on you could see my bra and breasts a little and the skirt was short too when you bend over my panties was showing well I got her tea and toke too her she look at me you look lovey my girl if I never know better you were a man I would ripe your panties off and shove my dido cock in that pussy ass hole I said what stopping you well after that day I became her girly bitch and I move in with her now I wear the panties and that wedding dress well I got marry in it as her wife and now she and me are happy

AnonymousAnonymousover 10 years ago
Go talk to Dad.

They re toast. Or the cops. No way to explain why his ass is bruised. They're off to jail.

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