3 comments/ 160836 views/ 11 favorites The Stepmother Ch. 1 By: Clausimotto 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. The Stepmother Ch. 2 After the ordeal, Billy was dragged up the stairs. He was taken to his bedroom where his cuffs were tied to the bed. Billy lay on his back, in a dazed state while Jane and the girls stood over him. Jane mentioned, "Tomorrow I think Billy should go see my nurse friend. She can give him a check up and also she can show Billy how to take care of his slut hole. Then we'll take him shopping for some little girl panties and since he's going to be tied down every night for awhile, perhaps he'll need some diapers." Susan and Kelly looked at each other and smiled. "Poor Billy. He has no idea how much worse it'll get." Jane told the girls it was time to shower up and get a good night rest, since tomorrow was going to be a busy day. The following morning, Jane woke up, put on her robe and headed towards the kitchen. She passed Susan's room and saw her and Kelly sleeping in their panties. She admired how pretty they had become. Jane walked into the room and kissed them both good morning. As their eyes opened, the girls noticed their mom's nice tits. "Mom, you sure have a great body." Said Susan. "Why thank you. You girls are very pretty and have matured into nice your girls. I bet you both drive the boys crazy." Replied Jane. "We do." said Kelly. "And sometime we have the same effect on girls to." She added. Jane looked at both at told them. "Eating a cunt every now and then is good for you. Now get ready cause Billy is going to have a very busy day. I want you girl to go braless, just panties if your cunts are still dirty." "Ok Mom." They replied. Jane walked into Billy's room. He was somewhat awake. She began to untie him. As she did she asked him if he was going to behave enough to shower. Billy said "Yes." "You have a busy day ahead of you and I don't want any trouble from you cock beater. I'm sure you can recall the pain by getting kneed in the balls. After you shower I want you to wear shorts with no underwear and a t-shirt with sneakers. Do you understand? And one other thing, you are never to stand up to pee. Since you like wearing panties and being a sissy boy, you'll sit on the toilet. Also, until I can trust you, you'll be tied to the bed every night and I'll put you in a diaper so you don't wet or shit the bed." She added. "A diaper?" asked Billy. "Do you have a problem with wearing one at night and using it for a toilet?" Jane asked. "No ma'am." He replied. "The better you obey me and my daughters the better things will get for you. Disappoint us and you feel the wrath. Do you understand?" "Yes." He replied. "Now go get cleaned up and ready. You have 15 minutes and then come down to the kitchen for some breakfast. Billy got some clothes out of his dresser and then walked over to the bathroom. He started the shower and then sat on the toilet to pee. Jane went back her room, freshened up a bit, got dressed and went to the kitchen. When she arrived at the kitchen, Susan and Kelly were eating some toast with coffee. Both wore short jean cut-offs and tight cotton shirts. Jane could see their nipples against the material of the shirts. "Morning girls." Said Jane. "Mourning Mom." They replied. Jane fixed a cup of coffee and then picked up the phone. She was calling her nurse friend Pat. "Hello." Answered Pat. "Pat, its Jane, how are you?" "I'm fine replied Pat." "I need your assistance Pat." She asked. "What's up?" replied Pat. "My stepson Billy was caught using my daughters panties to beat his cock off with and he's been caught. I would like to bring him by this morning so you can examine him and teach him how to maintain his slut hole. "So Billy is a sissy boy huh? She replied. "Yes I am afraid so. So you interested Pat? "Pat was only wearing a robe and she could feel her pussy getting wet at the idea. "How about 1 hour? Asked Pat. Jane replied "See you then." Jane hung up the phone and finished her coffee. Billy had just entered the room after she hung up the phone. He looked at the girl's tits and then went to the fridge to get some OJ. Jane told everyone to be ready in 10 minutes. "Where we going asked Billy?" "Since you like being a panty boy, thought me and the girls would take you shopping to buy you your own panties." "You think I'm going out in public with you all to buy panties?" he replied. "Think you have a choice in the matter? Asked Jane. Before Billy could answer, Jane kneed him in the balls. Billy dropped to the floor screaming. "You just don't understand Billy that your pathetic cock and mind are mine. The faster you accept your place as a cock beater sissy boy, they better things will get. The better you try to please me the more rewards you'll get. I'm sure you'd love to lick my girl's cunts. Please me and you'll be rewarded, disappoint me and I'll punish and humiliate you more. Am I clear?" "Yes ma'am." Billy mumbled. "Ok girls, pick panty boy off the floor and let's go shopping. The girls picked up Billy and took him to the SUV in the garage. Susan sat in the back with Billy and Kelly sat up front with mom. "Ok girls. Time to go shopping for some new panties for out sissy boy Billy." Jane said as she started the car. She backed out of the driveway and soon the group was on their way. The Stepmother Ch. 3 Jane and the gang were making their way down the road. She looked in the rearview mirror to see Billy still rubbing his sore balls. "Billy?" she asked him. "Yes ma'am." He replied. "Does your little sissy stick still hurt?' Billy nodded. "Good. At least I still know how to knee someone in the balls that makes them still hurt long after doing it." She replied with a grin. Susan looked at her mom's smile and asked where they were going. Jane told her about this specialty store run by a friend of hers. Jane turned on the radio and continued on the way. After about a twenty-minute drive she pulled the SVU into a small shopping center that contained small stores. She pulled in front of a stored called Jodi's. "Ok girls we're here." She said as she shut the car off. In a few minutes Everyone was out of the car and Jane grabbed Billy by the arm and led him into the store while Susan and Kelly followed. A lady greeted them at the door "Welcome to Jodi's. How may I help you? Jane looked the lady who appeared to be in her late forties, petite with a good-looking body. "We're here to get Billy here some appropriate panties and look at other items that may be suitable for a sissy boy." "I see. Well, you have come to the right place. Are you looking for anything in particular? Jane thought for a moment and told her that she was looking for panties that look like little girls panties and that she wanted them to be tight on him and also other pairs for when he wear a pad. Billy cringed when he heard the word pad. Kelly and Susan snickered as well. "I'm sure I can provide you with what you're looking for. "My name is Jodi." As she extended her right hand towards Jane. Jane extended her right hand and grasped Jodi's had to shake. "I'm Jane and these two girls are my daughters. Billy is my stepson." "Pleasure to meet you all. Let's go back towards the back of the store so we can measure Billy for his new panties." They all walked back toward the back wall of the store at stopped at a small platform. Jane looked at Billy and told him to get on the platform. Billy got stood on it and Jane told him to drop his shorts. Billy's eyes widened with fear at the thought of having his pants down in front of a stranger. "Billy, are you try to piss me off again? Jane asked in a stern voice. "No ma'am." "Then drop your fucking pants now or I swear I'll kick your balls so hard you'd wish you never had them. I'm I clear!" She yelled. Billy nodded yes as be unzipped his short and undid the button. They fell to the ground. Jodi looked at Billy and told him to pull his shirt up. Billy pulled his shirt up as Jodi pulled out a measuring tape. "What a small sissy stick he has." She mentioned as she measured his waist. She looked at the tape and it was 26 inches. "How big is your sissy stick?" Jodi asked him. "Not big enough!" Cracked Susan. Jodi measured it. "Only 3 inches. Not really big enough to be called a cock at all." Now I need to measure your sissy stick hard." "What? Exclaimed Billy. Jane reached over to Billy and grabbed his balls. "Unless you want to loose this. I strongly suggest you do what this nice lady had asked of you. Otherwise our next stop will be to my friend the Vet to have it removed." Jane let go. "Perhaps I can help him? Jodi mentioned to Jane. "Sure, but don't spoil the sissy. Jodi undid her blouse and showed Billy her firm tits. "Now Billy, be a good sissy and show me how you beat your meat. If you do it really good for me I'll give you a nice treat." Billy spit on his hand and began to beat his sissy stick. "That's a good boy. I want you to stop before you come, so I'll have the right measurement. Susan looked at Jodi's and asked her where the toilet is. Jodi pointed to the door on the right side of the back wall. Susan headed towards the toilet to change her dirty pad. "I'm gunna cum." Moaned Billy. Jodi measured his sissy stick and it only came to four inches. She held out her right hand below his stick. "Cum in my hand for making your stick hard for me." Billy beat his stick again and moments later, he spot a load into her hand. "Good boy." She told him. Jane could sense the next move and Jodi put the cum filled hand under his mouth. "Here's your reward sissy boy." She laughed. "Billy, show the nice lady how much you like to eat cum." Billy took her hand to hold it steady and then licked up him load.