Step-Sissy

Karen Jensen


I was, for the most part, pleased with my dad's remarrying. We had been living in a small 1 bedroom apartment and his marriage allowed us to move to a large house, where for the first time I had my own room. My new stepmom was nice enough and as an added bonus was smoking hot. In the 6 months we had been living there I couldn't count the number of times I jerked off fantasizing about her. The only downside was my bitchy stepsister. At 16, Megan was 2 years younger than me, and everything that I wasn't. She was a straight A student, whereas I had graduated with barely a C average. She was a star on both the girls’ basketball and soccer teams. I had no interest in sports and had never played any.  Megan lost no opportunity to belittle me when we were alone, though, when our parents were around she was a perfect angel.

Everything changed that summer when our parents took a belated honeymoon. Being the elder, I was left in charge and Megan was told that she had to listen to me. I thought it would be a great 4 weeks having the bitch as my slave.  My problems began the day my parents left. After lunch the sink was filled with both the lunch and breakfast dishes. Smiling to myself, I knocked on Megan's door.

"Yeah, what is it?"
"The sink is full. Wash the dishes!"
"Why should I do that?"
“Because I told you to.”
“If you are so anxious for them to be washed, do them yourself.”
"It's not men's work and since you’re the one wearing a skirt, you do it!"
"Really, you're playing the sexist card?"
"Yes, if I have to I will."

She opened her door and walked towards me. Wearing a bright red sundress that ended several inches above her knees and with her long blonde hair hanging straight, she could have had any guy she wanted. She walked right up to me and stared right into my eyes. She had an air of confidence about her that I lacked and I must confess I was feeling somewhat intimidated. Without thinking about it I took a step backward.

"I think you should wash them. In fact, I insist that you wash them."
"That's not gonna happen. Now do as I told you. Our parents left me in charge."

I hoped she didn't hear the nervousness in my voice. A big grin broke out on her face.

"Our parents left me in charge" she echoed in a sarcastically. "We can settle this now. I'll wrestle you. Loser washes the dishes."
"You're on!" I replied, smiling. "No way was a girl going to beat me" I thought.

She took a step back and smiled at me. It was not a friendly smile. I watched as she put her hair into a pony tail and slipped off her shoes. We were the about the same height, but I probably weighed about 10 pounds more than she did. And, of course, I was a guy and she was a girl. Outwrestling her should be no problem, I thought, but as she walked towards me I began to have a little bit of doubt. I noticed the muscles in her arms from the weight training she did and her eyes revealed a determination that suddenly made me question my rash agreement to her challenge. I decided that accepting her challenge may have been a bit rash.

"Listen, I don't want to hurt you. Let's just call it a draw. I'll wash them this time and you can do the dinner dishes what do you say?" I said, taking another step backwards and hoping to avoid the confrontation I had brought on myself.
"No! We are going settle this now! And when I beat you, you will be my slave until our parents return. Are you ready to rumble sissy boy?"

She took a couple of more steps towards me while I took a couple of steps back.

"I don't want to fight you. You're just a girl and I might hurt you."
"Just a girl! You're in for it now sissy boy!"

She laughed as she advanced towards me. I was against the wall and had no place else to go. She made a motion as if to slap my face. I put my hand up to block her and she grabbed it. She easily twisted my arm behind my back, laughing as she did so. She lifted my arm up forcing me to bend over. With her other hand she reached around, unbuttoned my shorts and pulled them down. Then she started spanking me. I struggled to free myself, but I was helpless to stop her. I realized then how much stronger  she was than me and I really was no match for her. I felt my eyes tearing and I tried desperately, but unsuccessfully, not to cry. She kept hitting me and it hurt. I begged her to stop but she kept spanking my ass. My tightey whiteys offered little protection. At that moment I became aware of another problem. I was actually getting an erection. Despite the pain, I was turned on.

"Admit you're a sissy; that you will obey me for the next 4 weeks and I will stop."
"I'm a sissy. Please stop."
"And you will obey me!"
"Yes! Yes!"
"Say it,"
"I will obey you!"
"The whole thing!"
When I hesitated she spanked me a few more times bringing fresh tears to my eyes.
"I am a sissy and I will obey you!"

Then she pushed me to the floor. I lay there crying, feeling like the sissy I had admitted I was. She stood over me and stared. The look in her eyes was one of utter disgust.

"Get up you pansy!"

I forced myself to my feet. I turned away from her and reached for my shorts, hoping to hide my erection from her. Her words stopped me.

"You won't be needing them" she said. "In fact, take off the rest of your clothes!"
"What?"
"You heard me! Take them off now! And face me!"

I turned towards her removed my socks and my shirt. She laughed as she saw the bulge in my under pants.
She motioned with her finger, clearly indicating that I should remove my underpants as well. I started to turn around. She twice slapped me in the face, bringing another round of tears.

"Did I give you permission to turn around? Face me and take them off!"

I tried unsuccessfully, to stop the tears and pulled down my underpants, covering my genitals with my hands.

"Hands at your side!"
"Please, don't make me do that?"
"Would you like a bare ass spanking, sissy boy?"

I shook my head and put my hands to my sides, revealing myself to her. I dropped my eyes to the floor, unable to look her in the eyes. I heard her giggle and looked up. She was clearly staring at my cock, which, though not very big was a hard as it could get.
“You will obey me or suffer the consequences. Do you understand sissy boy?
“Y..y..yes”.
"Go stand in the corner facing the wall and if you don't want to be across my lap, you had better not move!"

I did as she ordered, wondering what she had planned. I lost track of time and was starting to feel an urgency to pee. Then I heard voices, girls' voices. I heard footsteps coming towards me and Megan told me to turn around.

Two of her teammates from the basketball team were with her. Rita and Linda were equally sexy and equally bitchy. I knew I was in even more trouble with these two. I immediately covered my privates with my hands and Megan slapped my face, warning me to keep them at my sides. Fearing another spanking, I obeyed.

"Do you believe how tiny it is?" Asked Linda.
"There is no way something that small could satisfy a girl." Rita commented.

Ignoring them I begged to be allowed to use the bathroom.  My need to pee was becoming acute. They ignored me as I bent over in discomfort.

"You know girls, Brian asked me to wash the lunch dishes. His reasoning being that it wasn't men's work and since I was wearing a skirt, I should wash them. What do you girls think?"

"Well, you are wearing a skirt" said Rita "and given his reasoning, you should have been the one to wash the dishes."

I couldn't believe that Rita was supporting me. I didn't have time to relish the moment as the urgency of my situation increased.

"On the other hand, Brian isn't much of a man" she continued laughing. "We could put him in a skirt and then he could wash the dishes.”
"Surely they wouldn't do that" I thought "would they?"

My need to urinate was becoming acute.

"Please let me go to the bathroom. I will do the dishes."

"We better let the sissy pee" said Megan. "I don't know how we would explain his peeing on the carpet to my mom. Come with us!" she ordered me.

I followed her to the hall bathroom.

"Leave the door open and sit on the potty" she said.

The other girls laughed as they watched me, which, of course, made it harder to get it out. But out it came and with it a sense of relief. I wiped myself as my stepsister directed. She ordered me to go with them to her room. They sat on the bed and I was ordered to stand in front of them.

"I wonder how big he can get" said Rita.
“Not very big from what I saw” said Megan.
"Let's all see" said Linda.
"You heard the girls, play with yourself!" Megan ordered me.
"Please, haven't you had enough fun? Let me get dressed and I will clean the kitchen. Pleeease!"

Megan stood up and slapped my face. When I put up my hand to stop the next slap she grabbed it and pulled me forward, forcing me to stumble and fall to my knees. She jumped on my back forcing me face down on the floor and began to spank my already sore ass.

"When I give you an order I expect you to obey!"

I started howling from the pain almost immediately, begging her to stop and promising to do anything she wanted. When she finally stopped, I lay on the floor crying and rubbing my sore ass. I heard the girls whispering but could not make out what they were saying.

"Now get up!"

I quickly scrambled to my feet, not wanting to anger her any more. Once again I was erect and my face was burning from the humiliation I felt. She looked directly at my penis and nodded. What she wanted from me was unmistakable. I took my cock in my hand and stroked it. The girls all laughed at me.

"Is that as big as it gets?" asked Rita.
“Apparently” said Linda.
"I want you to cum, but you better catch it all in your hand. If any drops on the floor it will mean another spanking" said Megan.

I nodded my understanding and continued to stroke myself. It took little time before I felt the pressure building. I put my other hand in position to catch my cum which soon spurted out. Despite my best efforts some dripped on the floor. The girls were giggling and I started hyperventilating, fearing another spanking. My ass was already very sore and I knew I could not handle it.

"You dripped some on the floor" said Megan.

I begged her not to spank me and tears started flowing again.

"Oh, I have no intention of spanking you."

I breathed a momentary sigh of relief.

"Rita and Linda will administer your spanking" she paused. "Unless.."

I was almost afraid to ask, but I thought I would do anything to save myself from the pain.

"Unless what?"

Megan smiled at me again. It was not a pleasant smile.

"Unless you lick your cum from your hand."

The girls laughed again as they waited for me to respond. I did not like either option.

"What's it gonna be Sissy?" Asked Rita, giggling.
"Do you want us to make the decision?" Asked Linda.

I lifted my hand towards my face and sniffed it. It had a slight aroma, not particularly appealing, but tolerable. I tentatively licked it.  That set the girls laughing loudly, encouraging me.

"Lick it up, now!" ordered Megan.

Fearful of the consequences I obeyed her and licked it all up from my hand. I did not care for the taste but the idea that I had swallowed my own cum bothered me even more.

"Now the floor!"

I wondered if it could get any worse as I obeyed. I hoped this would end it.
"Come, my sissy brother, you have work to do. The kitchen still needs cleaning."
“Wait!” said Rita. “He needs a skirt to be properly attired for the job.”
“I have just the right thing.”
Megan left the room and returned shortly with a white garment of some sort. It turned out to be a bib apron, that when tied around my waist, left only my bare ass showing. The skirt came down to my knees and had lace round the hem and along both sides of the straps going over my shoulders. It was quite a frilly garment and I wasn’t sure I wouldn’t prefer to be naked. But the choice was not mine to make.

“Now you are properly attired” said Megan. “Come with us!’

The other girls snickered while they each took a hand and led me into the kitchen. Megan laid out what she wanted done with the promise of another spanking should I not do the job to her standards.

I washed and dried the dishes, cleaned the sink, scrubbed the counter and stove tops and finally washed the floor. It took over 2 hours and I was exhausted when I finished. I wanted nothing more than to take off the hated apron, put on my clothes, and lie down. I knew better than to remove anything without permission and instead went looking for the girls. I found them in my room. They had removed the door and were putting all my clothes in cardboard boxes. I was hoping they would tire of their game, but clearly Megan planned to continue it for some period of time.

"Oh good!  You're just in time. Pick up a box and go with the Rita to her car. You can stack them in the trunk."

The implications of her request were obvious. I would be stuck dressing like a girl for as long as Megan  wanted.
“Please don’t make me go outside like this” I begged.
“He could get arrested for indecency” said Linda.
“You’re right” replied Megan. “Let's get him dressed in something more appropriate. But first we need to clean him up. Come with us!"
Megan left the room with the other girls close behind. Reluctantly I followed them to the bathroom. I removed the apron when told to do so and Megan handed me a jar of cream ordering me to rub it over my body leaving only my eyebrows and head untouched.

After a few minutes my skin started to burn. I begged them to let me in the shower. Linda told me to wait. The burning became worse and I felt tears coming to my eyes, once again. Finally I was allowed to shower and using a wash rag to remove the cream, I watched my body hair go with it. It only added to my humiliation. Megan gave me some lilac scented shower gel and ordered me to wash myself with it. When I finished I smelled like flowers but did not have time to dwell on it. They gave me a towel to dry myself and took me back to Megan's room.

"I think these clothes will fit. Put them on!"
First I put on a black garter belt. They had me sit as Rita and Linda each rolled black nylons on my legs. I had to stand so they could attach the garters to them. My cock and balls were still uncovered and I was almost anxious for them to give me panties to wear, just so they would be covered.  That wish would change when I saw the panties. They were white, silky, rhumba panties. The elastic was tight on my thighs and to my horror, I found myself getting erect as they were pulled to my waist. My reaction did not go unnoticed and the girls were merciless with their teasing.

Megan held out a black bra and ordered me to slip my arms through it. She buckled it in the back and adjusted the straps. The corset had forced the flesh on my chest into two small breasts, but not nearly big enough to fill the cups. Megan grabbed some panties and stuffed the bra to give me the semblance of breasts.

Rita was holding a dress for me to put on. It was short and black with a built in petticoat and a white bib apron attached. She slipped it over my head and quickly spun me around so she could zip it up. She ordered me to sit at the vanity where Linda went to work on my face. When she finished she placed a pink page boy wig on my head. I still hadn't seen myself in a mirror and despite the extreme humiliation I felt at being dressed as I was in front of these three hot girls, I was a little bit curious to see what I looked like.

"What are we going to do about shoes?" Asked Linda.
"Mine won't fit her" said Megan "but maybe mom's will. In any case we will have to shop for shoes for her. I will check out mom's closet."

I did not miss her use of the feminine pronoun she used when referring to me but said nothing. I was not about to risk antagonizing her further. She returned with several pairs of shoes with differing heel heights and ordered me to sit on her bed. I plopped down, sending my skirts flying.

"Stand up!" ordered Megan. "When you sit, smooth your skirt under your butt like this."

She sat down demonstrating what she had just told me. That was my first, but certainly not my last lesson in 'being a girl'.

They tried 4 or 5 pairs of shoes on me all were a bit tight but I could get my feet into them. The girls decided on a pair of black sandals with about 4 inch stiletto heels. They were CFM shoes and I could barely stand in them, let alone walk. The girls instructed me in the art of walking in heels and in a short time I was able to navigate. I was far from graceful and my feet hurt, but I was at least confident I would not fall flat on my face.

They finally allowed me to see myself in a mirror. While I would not win any beauty contests, I was more than passable and even what I would call cute. My emotions were mixed. I was humiliated at how easily my masculinity was stripped away yet felt a certain amount of pride at how good I looked. I also was able to see that any movement would cause my frilly panties to be displayed, one more cause for humiliation. I was not given much time to admire myself.
“Turn around” said Rita. When I did I saw flashes go off as she took pictures of me with her phone.
“I’m just going to send these to my sister so she too can have a good laugh.”

I had no time to reflect on the potential consequences of having the pictures floating out in cyber space when Megan got my attention.
"Ok sissy, let's go!" said Rita.
Resigned to my fate I asked where Rita's car was parked. She had a malicious grin on her face when she replied "around the corner."

"Please don't make me walk around the block. The neighbor's will see me."

Before I could even blink, Megan grabbed my arm, spun me around so I was facing away from her, and gave me three hard swats. Fighting back more tears and knowing my sore ass could not withstand another spanking, I picked up a box and followed Rita out of the house. I was grateful that there was no one on the street, but her car was parked on a busy street where there were certain to be people out and about.


I got a lot of stares being dressed as I was and some unkind comments, but people seemed to think I was a girl, though not the kind you would invite into your home for dinner. It took four trips to load her car during which my stress level rose as high as it had ever been.

It was nearing dinner time by the time Rita's car was loaded and the girls decided to order pizza. I heard Megan ask Rita if David was working tonight, but I thought nothing of it. I was lost in my own thoughts, wondering what they had planned for me next. We went to the kitchen to wait for the pizza.  I was instructed to get some soda, glasses, plates, and napkins and set the table.

It was only a few minutes until the doorbell rang. Megan ordered me to answer it. It was clearly an opportunity to further humiliate me and she was determined to pursue her advantage. With little choice, I stood up, straightened my skirt and answered the door. It was the pizza delivery boy. He was well over 6 feet tall and must have weighed 250lbs. As I would later learn, he was a starting tackle on the football team and also team captain.
He smiled at me and asked if Megan was there. Before I could answer, the girls came out. They obviously all knew him as they each went up to him for a hug. Megan turned around with an evil grin on her face.
“David, meet my sissy stepbrother Brian. When he is dressed like this, though, he prefers Brianna.”
He looked at me anew and with a lascivious grin took my hand and said “Hello Brianna!”.
“Hi David.”
“Aren’t you happy to meet him?” said Megan.
“It is really nice to meet you David.”
He just laughed.
“Brianna! Get some money and pay David for the pizza.”
I went to my room, grabbed money from my wallet and returned.
“Pay the man!” said Megan and the three girls returned to the kitchen, leaving me alone with this mountain of a man who knew my secret.
I handed him the money and told him to keep the change. I wanted to be rid of him as soon as possible.
“Thanks Brianna. See you later!”
“I hope not” I thought to myself.
He pinched my ass as he turned toward the door and I involuntarily squealed girlishly.
"See you around, sissy." he laughed as he went out.
The aroma of the pizza coming from the kitchen was enticing and I thought I would have some. The girls informed me I was on a diet and had to watch my girlish figure. Therefore, my dinner was to be salad, which I had to make myself. The smell of the pizza was stimulating my appetite, and I knew the salad would not satisfy me, but seeing no other choice I obeyed them.
I sat down with my salad at the table. The girls were talking about someone's date and what they thought she should wear. I really wasn’t paying much attention to them as I tried to figure out a way to convince them to release me. The idea of pretending to be a girl for the next 4 weeks was something I didn’t want to think about.  Despite my hunger, I found myself just moving the food around my plate and not really eating much of it. Suddenly, Megan grabbed my plate, dumped the salad into the garbage, and told me to get my ass to her room.
“What’s going on?”
“We have to get you ready for your date and we only have about an hour, so move your ass!”
“What date?”
They did not answer, but took me back to Megan's room where I was stripped down to my bra and panties. Linda removed my bra and handed me different one. It had far less padding, making my boobs look like those of a young teenage girl. Rita opened her bag and pulled out a sundress. It was yellow with white polka dots and as I would soon learn was quite short. I was ordered to lift my arms and the dress was lowered over my head. Linda pulled up the back zipper, effectively locking me in the dress. She had me put on nude pantyhose and a pair of my stepmom's white sandals with a low heel. Now I was dressed similarly to the girls who all wore sundresses. They changed my wig style and put it into a high pony tail. Then removed my makeup and reapplied it, making me appear much younger. The effect was to make me appear like a young high school girl.
“Perfect” said Megan. “She should be a good date for your brother Rita.”
“I’m not going out of the house dressed like this and certainly not on a date with any boy!”
Megan walked over to her dresser and picked up her hairbrush. I realized I had gone too far and pleaded with her not to spank me again. I didn’t think my sore ass could take it.

“I have no intention of spanking you, my sissy brother.”
My sigh of relief was cut short, however.
“Rita will spank you.”
She handed the hairbrush to Rita and I was ordered to lay across her lap with the warning that if I didn’t comply it would be alot worse for me. I was already crying in anticipation of what was to come. The hairbrush was far worse than the hand spanking, but thankfully it did not last too long. I was ordered to get myself under control so they could repair my makeup. Then I was taken into the living room to await my date.
It seemed that Rita’s brother was gay and in the closet. The girls saw this as an opportunity for him to be seen with a pretty girl to dispel any rumors about him. I was warned that I had better act like a girl or there would be hell to pay. I realized that for my own sake it would be better to have people think I was a girl and vowed to do my best.
“Oh, and one other thing, Brianna” said Megan. “Mark knows you love to suck cock, so be sure and show him a good time.”
My face burned as the girls laughed at me, but I only groaned at the humiliations being heaped on me. I wondered when it would end.
I didn’t have long to wait until the doorbell rang. I was ordered to answer it.
“Hi, I’m Mark. You must be Brianna, right?”
I was tongue tied for the moment. He could not have been much older than 15, though he was a couple of inches taller than me and clearly outweighed me by 30-40 pounds. How could I do this, I wondered? I was an 18 year old boy, dressed as a girl, about to be taken on a date by this 15 year old boy. I wanted to cry. I regained my composure, sort of and replied:
“Yes, I am Brianna. Please come in.”
The girls all greeted him with hugs and told him to enjoy the evening. He held the door open for me and took my hand as we walked down the street. Since he was too young to drive we would be taking the bus downtown to a movie. I was grateful we would be in a dark theater. Had I known what was ahead I would have been a lot more fearful of the evening.
Mark paid my fare and his and we walked toward the back of the bus, sitting on one of the seats that faced across the aisle. He put his arm around my shoulder and pulled me close to him. The guy across the aisle kept staring at me, making me even more nervous than I already was. Finally, Mark whispered in my ear.
“Put your knees together or everyone will know you are not what you seemed to be.”
I quickly pulled my legs together and felt my face flush. I couldn’t look at the guy who had been staring at me, and was grateful when he got off at the next stop.
Mark paid for the move without asking me what I would like to see and led me into a theater showing “Poltergeist”. I was never a big fan of horror movies and studiously avoided them. During one particularly scary scene I joined with others in the theater screaming and instinctively turned my head, and leaned into Mark, hiding my eyes in his chest. I felt like such a sissy, but could not bear to watch the movie. He just hugged me tighter.
We stopped for ice cream after the movie and then he took me home on the bus. I remembered this time to keep my legs together. He walked me to the door and before I could stop him he kissed me, probing my mouth with his tongue. I tried to push him away but he was clearly alot stronger then I was and I had to submit to him. I said good night to him and turned to open the door. He grabbed the key from my hand and opened it himself. Then he shoved me into the house, closing the door behind him.
I turned to tell him to leave, but he slapped my face, causing me to stumble backwards. I managed not to fall, but he slapped me again and this time I fell backwards, landing on my ass. I could feel the tears welling up in my eyes and I tried hard not to cry.
“Rita tells me you like it rough.” He said to me. “I hope this is rough enough for you.”
He grabbed my arm and pulled me to my feet. Then he lifted me in his arms and carried me to the sofa where he sat down, flipping me face down over his lap.
“Wait! Please! Don’t spank me. I don’t like it rough.”
“She told me you would say that. That it was part of the turn on for you.”
Then he swatted my ass, much harder than any of the girls had, even with the hairbrush. I was bawling like a baby, begging him to stop, promising him anything if he would. I don’t know how long the spanking went on for, but he finally did stop and dumped me on the floor.
“Ok bitch, suck my cock!”
He dropped his pants and let out the monster. I couldn’t believe how large he was. I didn’t have time to think about hit when he grabbed my hair and pulled me towards him.
“Open your mouth bitch!”
Too scared to resist I did as he ordered and he rammed his cock into my mouth. Holding my head between his hands he fucked my face. He was totally in control and I knew I would be a receptacle for his cum. It did not take him very long to ejaculate into my mouth. With no other choice I swallowed a couple of times before he pulled out, spraying my face, my hair, and my dress with his cum. I sat on the floor crying, watching him pull up his pants and get himself together. Then he surprised me. He gently lifted me to my feet and kissed me.
He lay me down on the couch and gently lifted my dress and pulled down my panties. He then took my cock in his mouth and gave me my first blow job. When I had cum, he kissed me again, feeding me my own ejaculate.
He smiled as he turned to leave.
“See you next Saturday night, sweetie!” and he left me laying there on the sofa.

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