She Made Him Her Pretty Teenage Step-Sister

Written by Karen Jensen – Illustrations by ENEG

Chapter 1 – Transformation

She-Made-Him-Her-Pretty-Teenage-Step-Sister-00aIt had been a tough year for Norman Malone. His mother had died when he was an infant and his father had just remarried the beginning of last year. He had moved to another town to live with his new wife and left Norman with friends to finish the school year. When summer arrived and school let out, Norman also moved, leaving his friends behind. He was there just a few weeks when his father suddenly died of a massive heart attack.

Now he was living with his step mother and step sister Andrea, who at 17 was the same age as Norman. He felt like he was living with two strangers. His stepmother was nice enough to him, and tried to make him feel welcome in her home, but Andrea made no pretense of liking him at all and looked upon him as an intruder in her life. She went out of her way to make his life miserable and it seemed that no matter what Norman did for her, it was not enough.

It was a couple of weeks after the funeral. His step mother had gone away for the weekend to try to get over her grief. Norman was downtown having a soda, also trying to forget his sorrow. He felt a tap on his shoulder and looked up to see Lois, his sister’s friend, a girl Norman developed a crush on the first time he met her.

“Hi, Norman. I’m really sorry about your dad. Is there anything I can do for you?”

“Oh, uh, no thanks Lois. I’m just drowning my sorrow in a soda. Can I buy you one?”

Lois sat down and they talked for awhile.

“Look, Norman, no one is home at my house. My folks went away for the weekend. Would you like to come over and go swimming with me?”

“Yeah, I’d like that.”

It was a short walk to her house. Norman’s spirits picked up immediately and he considered himself to be very lucky to be spending the afternoon with a beautiful girl like Lois. “Just go into the bathroom and get undressed. I’ll get you a swim suit and hand it to you through the door.”

Norman was really excited and in no time at all was standing there naked. Spending time alone with Lois was more than he dared dream.

“I have a suit for you, give me your clothes and I’ll hang them up while your changing.” She took his clothes, and gave him what she had, and went to put away his clothes.

After he did as he was told and she handed him the bathing suit. He was stunned when he realized she had given him a girl’s bathing suit. It was a one piece purple bathing suit with little pink flowers on it.

“Hey, I can’t wear this. Don’t you have a boy’s suit?”

“None that are clean. Who’s gonna see you besides me. I think you’ll look cute. Why don’t you try it on and see. I promise I won’t tell anyone” Norman was at a loss. He really wanted to be with Lois and she seemed pretty anxious for him to put on the bathing suit. He was embarrassed at the prospect of having to wear a girls swim suit, but he knew he couldn’t very well walk around naked.

“Hey Norman, what’s taking so long. Come on out. I promise I won’t laugh.”

Reluctantly he slipped on the girl’s swimsuit and shyly stepped out of the bathroom.

She-Made-Him-Her-Pretty-Teenage-Step-Sister-04“Wow, you do look really cute”, Lois exclaimed. “Let me give you some finishing touches, so you’ll look better in it. I am going to put some water proof eye makeup on you and this bathing cap. This way if anyone does come over, they will think you are a girl.

If the neighbors see you, they won’t think I had a boy come over alone and tell my parents.”

She put her water proof mascara and eyeliner on his eyes, and a touch of eye shadow on his eyelids. She adjusted his bathing cap, and then quickly applied a coat of light red glossy lip stick to his lips, making him look like a real attractive teenage girl with sensual kissable lips. She inserted a pair of foam shaped pads into the top of his swimsuit and adjusted the cups so they looked natural in appearance on him if he were a real girl.

Norman was shocked at her moves and her suggestion but offered no resistance. What she said made some sense to him, and wearing the suit wasn’t so bad after all. In fact, though he wouldn’t admit it, he kind of liked the way the it felt.

The two of them played and swam, and Norman was less aware of how he was dressed. He winced when she started calling him Nancy, but as she explained, if anyone did come over, they would hardly think he was a girl with a name like Norman. They were enjoying themselves so much that they were unaware of the passing of time when they heard the gate open and looked up to see Andrea staring at them.

“Who is your new friend, Lois? I don’t believe I have met a girl like her before. Why it looks like my step brother Norman in drag”, she laughed.

Norman was mortified. If Andrea told his stepmother about him wearing girl’s clothing, she might throw him out of the house. And then where would he go?

“Look, Andrea, I can explain.”

“Save your breath Nancy. When I get these pictures developed, you’ll be the laughing stock of the school. Good job Lois. Did you have any trouble with HER?”

“None at all. It was easy.”

As the realization that the whole thing had been planned by Lois and his step sister hit him, he was crushed and wanted to cry. He had been having such a good time with Lois, and he thought she was really interested in him. All she wanted was to help his step sister humiliate him. He realized he somehow had to deal with Andrea, and convince her not to show the pictures, she was taking of him.

“Please, Andrea, I’ll do anything. Don’t show anyone those pictures”.

“I’m sure you will brother, or should I say sister? From now on you will obey me and do as I say, or these pictures will be spread around school. Do you understand me?”

“Yes, Andrea, I understand” he said submissively.

“Now get out of those clothes. We have something more appropriate for you to wear.”

Norman was soon standing naked in front of the two girls. His face was red from the unbelievable embarrassment he felt. He didn’t know what they were going to do with him or why, and was afraid to ask.

“Norman, you know that Lois and I are having a party tomorrow night. Mother insisted that we invite you. She didn’t, however specify how you were to be dressed. Since we are short one girl, we decided that you would be her. We are going to dress you as a girl and teach you to be a girl. Who knows, tomorrow night you may meet Mr. Right”, she laughed.

“The first thing we have to do is remove any unsightly hair from your body. We’ll do it with this cream” said Lois.

She proceeded to rub the depilatory all over his body. She spared no part except his head, and even rubbed his genital area, which responded predictably.

She-Made-Him-Her-Pretty-Teenage-Step-Sister-07After a few minutes, he felt a burning sensation and was relieved when at last they let him shower. As the cream was rinsed away, so was all his body hair. He was hairless like a new born baby. His skin was as smooth as that of any girl.

After drying himself he stepped into the bedroom where his new clothes were laid out for him. Andrea handed him one garment at a time. He was almost grateful for the cover the panties provided him, and only after they were on did he notice the lace trim. Lois helped him into the yellow bra which matched the panties perfectly. She padded the cups for him.

Next was a slip to match that came barely to mid thigh. She helped him put on his pantyhose and a short yellow dress with a wide black patent leather belt, and a flared skirt that only just covered the slip. They even had a shinny black pair of spiked high heeled shoes which he slipped on to his stockinged feet. Andrea led him to the vanity where she proceeded to make him up.
Foundation, rouge, eye shadow, liner, mascara and a glossy red lipstick soon covered his face. His longish hair was combed into a more feminine style. When she had finished she turned to Lois and said, “I give you Nancy”.

Norman was stunned when he looked into the mirror. The face staring back at him was that of a very cute teenage girl. Though not a beauty queen, certainly an attractive one. He felt all kinds of emotions. Shock, embarrassment, and excitement at the adventure he was to have. The girls had made it clear that for the next 24 hours he would live, act, dress and be a girl. He wasn’t sure what it would entail, but he was beginning to think it might not be so unpleasant, after all.

Chapter 2 – Penetration

Stepsister 1“Come, Nancy, we are going for a ride”.

As the reality of his predicament hit him, Norman became extremely nervous and was about to refuse. He remembered, however, his sister’s threat to show the pictures and thought better of it. And, she had taken additional pictures of him dressing in the feminine garments that would only add to his humiliation.

“Where are we going?” Nancy asked as they pulled out of the driveway.

“Well, we thought you might like a new dress to wear to the party tomorrow,” Andrea replied, “and since you have been saving your money, you can afford to buy one”

Nancy became angry as he saw that Andrea had the wallet in which he was saving his money.

“I was saving up for a new stereo. I am not gonna use it to buy a dress”.

“Don’t be silly, a girl would much rather have a new dress, and, in any case, I don’t remember asking you.” “I’m not a girl!”

“Lois, stop the car and we’ll ask a perfect stranger if Nancy is a boy or girl?”

“No! Don’t do that. I’ll buy the dress” he said meekly.

Nancy found herself holding back tears as she wondered why his step sister hated him so much and how far she would go to humiliate him. He knew better than to argue at this point.

Lois parked the car and the three girls got out. Walking very self consciously between Andrea and Lois, Nancy kept her eyes to the ground and dared not look at anyone they passed. She was mortified she would be recognized as a boy.

She was taken into a dress shop, whose name she recognized since Andrea had talked about it. It was where she usually bought her dresses. The owner greeted the two girls by name.

“This is my step brother Norman. He likes and insist he has to dress up like a girl at all times, or at least most of the time. Lois and I agreed to take him shopping here for a new dress and other things he can wear to a party tomorrow night. He insists we call him Nancy.”

She-Made-Him-Her-Pretty-Teenage-Step-Sister-10Norman was horrified and if he could have found a hole to crawl into he would have.

“Well, I am used to boys coming in here to try on dresses. You would be amazed at how many like to dress up like girls, though many are not here voluntarily. I will let my best salesgirl handle Nancy. She has had much experience with this sort of thing.”

“Maureen, this is Norman, who prefers Nancy. Will you help her to pick out a dress for a party she will be attending tomorrow night?”

She led Nancy to a rack full of party dresses. After taking some measurements, she picked out a couple of dresses and led Nancy to the dressing room.

It was furnished with a comfortable couch and a rack with hangars for the clothes.

“Alright Nancy, take off your dress so that you can try some of these on.”

She started to explain that wearing the feminine attire was not her idea, but Maureen didn’t seem interested. She removed her dress and stood there in the minislip she was wearing, feeling very vulnerable. She tried on several dresses, finally settling on a purple and white see-through. Maureen left the room and came back with a white slip.

“Put this on, it will look better under the dress.”

Nancy was embarrassed to strip that far, but her protests fell on deaf ears. As she removed her slip, Maureen could see the excitement Nancy was feeling.

Maureen locked the dressing room door and moved towards Nancy, who was wearing only her bra and panties. She removed her dress and slip as she advanced on the feminized boy. She reached into Nancy’s panties and grabbed her throbbing cock.

Nancy moaned and found herself being pushed back on the sofa. She reached for Maureen’s tits and soon had one in between her glossy reds lips and gentle sucked it into her mouth. Maureen kept stroking Nancy’s cock, causing her great pleasure but not enough to allow her to come. Suddenly Maureen stopped and climbed on top of Nancy placing her womanhood right over Nancy’s red lips and mouth.

“Eat me!” she said.

It was a command, not a request. Nancy had never done anything like this and was not sure she wanted to, but before she could protest, she found her head buried in Maureen’s muff. With her hands stroking Maurteen’s tits and her tongue working feverishly on her clit, Nancy did not have time to think of her own needs. Suddenly, Maureen stiffened and squeezed her thighs around Nancy’s head. Her juices were running down Nancy’s face, ruining her makeup. Maureen let out a scream, and fell limp on top of the sissified boy.

‘That was wonderful”, she said. “I am going to reciprocate. I will show you what you can expect from the boys at the party”

Nancy didn’t knew what Maureen was talking about. All she knew was she was hard as a rock and needed some release. Maureen removed a plastic dildo from a drawer which she tied around her waist. She applied a coating of lubricant to it and she was now ready.

“Now my dear, I am going to fuck you now, much like a boy would fuck a girl. If you are going to be a girl, you must learn to fuck like one”.

Nancy found herself trembling, but was too frightened to move, as Maureen advanced toward her with that huge cock sticking out. Nancy could guess what she was going to do with that cock, and though scared, lay there as if frozen to the spot.

Once again, Maureen mounted Nancy, only this time she stuck her false penis into Nancy’s rectum. She screamed as the long dick penetrated her asshole. She was lying on her back with her legs in the air and instinctively, she wrapped them around Maureen’s waist. Slowly, Maureen humped her, gradually increasing the depth of her penetration. Despite the discomfort Nancy felt, she was also experiencing a sense of excitement like none she had ever imagined. She could feel her own dick getting harder and harder. As she was approaching a point of no return, Maureen penetrated deeper and deeper until Nancy took the whole length of her dick. The mixed emotions Nancy was feeling caused her to weep and finally when she thought she could take no more, Maureen stopped. Nancy wanted the release that an orgasm would bring, but Maureen was not about to cooperate.

Nancy reached for her manhood, thinking she would finish herself, but Maureen grabbed her hand first. “We’ll have none of that here.”

Before Nancy could protest, she found herself propelled into a cold shower, with her panties around her knees. She was aware of the great embarrassment she had felt before as her excitement subsided, and had to fight to hold back tears as Maureen helped her dress and repaired her makeup.

Chapter 3 – Her First Date

As the three girls left the dress shop, Nancy carried the bag with her new purchases. They got in the car and drove off. Two more stops resulted in new heels, hose and lingerie to go with her new dress. Her stereo fund had a large dent in it.

“Well Nancy, that’s all the purchases for today”, Andrea laughed, as they got into the car and headed for home, or so Nancy thought. Her head was filled with thoughts of her encounter with Maureen, and she was not paying attention to the direction they took. The car came to a stop.

“Alright girls, we’re here. Let’s get a bite to eat. Nancy has enough money left to treat!” said Andrea.

Nancy looked up with a start. They were parked outside the local hamburger hangout. There would certainly be a bunch of kids from school there.

“I’m not really hungry, can’t we please go home, Andrea?”

“No, Lois and I want to eat, and besides, I think it fitting that you treat us for taking you shopping”

The girls went inside and sat down at a table. Lois and Andrea ordered their food. Nancy sat quietly looking down at the table, praying that no one would realize she was not a girl. She only wanted to get out of there and go home.

“Hi Lois, Andrea, who’s your cute friend?”

“Oh, hi Harold. This is my step sister Nancy. She’s visiting me for a few days”, said Andrea.

Nancy was mortified, certain that at these close quarters her gender would be read.

“Would you like to join us, Harold?”, asked Lois.

“Sure, I was just about to get a burger and fries, myself’ he replied, sliding into the booth next to Nancy.

“Hey, are you girls busy tonight? I’m looking for someone to go to the show with.”

“Well, unfortunately, Lois and I are tied up with preparations for the party tomorrow night. I’m unhappy about leaving Nancy alone tonight. I’m sure she would like to go with you, wouldn’t you Nancy?”

Nancy could not believe what she was hearing. She did not want a date with a boy, but the tone of Andrea’s voice made it clear that she could not refuse. In the short time she had been there, she had heard of Harold’s reputation as a ladies’ man, and she wasn’t sure she would know what to do if he made any advances towards her.

“I’ll eat my dinner and we’ll go to the drive-in. We should just make it in time for the show.”

Before Nancy could protest, Lois and Andrea got up to leave. Both Of them with huge smiles on their faces.

She-Made-Him-Her-Pretty-Teenage-Step-Sister-16“Thanks for taking Nancy tonight, Harold. Please drop her at Lois’ house. Her folks are out of town, and Nancy and I are sleeping there tonight. We’ll see you tomorrow at the party”

Soon they were in Harold’s car on their way to the drive-in. Nancy was quiet, responding to Harold in a soft voice, praying she wouldn’t give herself away.

Harold was much bigger and stronger than she was, and she shuddered to think what would happen if he discovered that he was actually on a date with another male.

Shortly after the movie started, Harold moved close to Nancy. “The steering wheel is in my way”, he said. “I need a bit more leg room.”

Nancy nodded nervously and tried to concentrate on the movie. Maybe he won’t try anything on a first date, she thought, and it might work out ok.

Soon Nancy felt Harold’s arm around her shoulder. His other hand was on her bare thigh. The mini-dress she wore provided little cover. She felt both afraid and excited. She didn’t understand the emotions running through her. She offered no resistance as Harold placed his lips on her shinny glossy red ones of hers. Soon his tongue was on her gums and searching every part of her mouth. In spite of herself, Nancy found herself uncontrollably responding. She could feel his hard dick against her thigh. Harold took her well manicured hand with the long feminine highly polished nails and placed it on his groin.

‘Take it out, Nancy!”

She pulled her hand back. Harold unzipped his fly and took her lovely feminine hand again, placing it on his groin. Frightened of him, she reached slowly for his erection and began to gently stroke it.

The realization of what was happening hit her. She was a boy. She couldn’t make love to another male. She could feel the tears in her eyes. She had to get away from him.

“But how?”, she wondered. “I can’t run away dressed like this.”

“What’s the matter sweetheart?”, asked Harold.

“I..I can’t” stammered Nancy.

“Why not? weren’t you enjoying it?”

“Yes, I was. I just … just can’t tonight”

“Is it that time of the month?”

Nancy breathed a sight of relief. He had given her the perfect excuse.

“Yes, that’s it. I am having my period”

“That’s alright” said Harold, as he put his arms around her again. Before she could protest, he was kissing her as passionately as before. He took her hand and put it back on his prick.

“Stroke it baby, just stroke it”

Nancy did as he requested. She was trapped and decided to make the best of the situation. She thought that if she could make him cum, that would be the end of it.

“Now suck it Nancy”, Harold said, as he gently pushed her head down towards his crotch. Nancy had never imagined anything so big as Harold’s prick. She felt helpless in his arms. She tentatively licked his long pole with her tongue.

“That’s good Nancy. Now take it into your mouth. I want you to taste my cum.”

With that, he grabbed her head with both hands, and forced his penis to slid between her glossy red lips and into her mouth. Nancy thought she would choke on it, but gradually got used to it. As she sucked on his dick, with a steady up and down motion, she could hear him moan. It was obviously giving him a great deal of pleasure. To her surprise, Nancy found her own penis was hard as a rock and felt like it would burst through the flimsy panties she was wearing. At that moment, she felt him spasm, and globs of his warm liquid filled her mouth.

She-Made-Him-Her-Pretty-Teenage-Step-Sister-19“Swallow it. Swallow all of it”

Nancy tried her best to comply with his request. She took huge gulps of his cum, but despite her efforts, it ran down the sides of her shinny lips and out of her mouth and dripping onto her dress. Leaving its small telltale signs of evidence, of what she had just done to his cock.

Finally, Harold was spent, and he leaned back gasping for breath, still holding Nancy’s head down with his penis in her sexy feminine looking mouth.

“That was wonderful Nancy. I wish I could reciprocate. Maybe when your period is over, you’ll let me do the same for you”

Nancy could only nod as she sat up. She had needs of her own and was not sure how to fulfill them. She realized that she had better hide her own hardon from Harold. She quickly crossed her legs and adjusted her skirt to hide the evidence from him. If he found out she was a male, well, she shuddered to think about it.

“It looks like the movie is over Nancy. I had better take you home. It’s late and I’ll see you tomorrow at the party, won’t I?” She nodded. As they drove home, Nancy thought about her day. She had never dreamed when she got up that morning as Norman, that she would end the day as Nancy, wearing a pretty yellow dress and giving another male head. Harold walked her to the door of Lois’ house. He put his arms around Nancy’s waist and bent over to kiss her. She felt herself getting hard all over again as his tongue entered her mouth. She finally managed to break away from him.

“Good night, Harold”, she whispered, “I’ll see you tomorrow”, and she slipped inside the house.

Chapter 4 – Girls’ Playgirl

“Well, well, well, look who finally came home. Did you enjoy your date with Harold?”, asked Andrea. “I guess you did from the looks of it” she laughed as she stared at the bulge in his dress. “I would say something has turned on our little girl. I wonder what it was. What do you think, Lois?”

Nancy was greatly embarrassed and could feel her face turning a deep shade of red. She was also feeling a great need to satisfy the tension that had built up in her groin. If only it wasn’t so obvious to his stepsister and Lois.

“I think our little friend has tasted something other than her dinner” said Lois. “How do you think her lipstick got smudged and what do you suppose this white stuff is on her face, and also on her dress? This was one of my favorite dresses. You now owe me for a new dress!”

“That’s too bad”, said Andrea, “as I recall she spent all her money today on a new dress for herself, and taking us out to dinner. Maybe she can work it off. She could be your personal maid.”

“Good idea”, said Lois. “She can start right now!”

Nancy was stripped down to her bra and panties, which were still bulging from her unsatisfied needs. She was given a short yellow nightie to put on and led upstairs to the bedroom.

“We can’t have her mess up the sheets”, said Lois. “That thing of hers looks like it will burst any minute.”

“What should we do?” asked Andrea.

Lois got some rope, and soon Nancy’s hands were tied to his thighs.

“You’ll sleep on your back, and don’t try anything during the night”, said Lois.

She was led to the bed where she was ordered to lie on her back in the middle. With her hands tied, it was not a very comfortable position.

“Please untie my hands. I promise I won’t make a mess”, she said.

Chapter 5 – Queen for a Day

“Well sleeping beauty, it’s time to get up. You have allot of work to do to get ready for the party.”

Nancy woke up, feeling that she had hardly slept at all. She was aware of the ache in her arms, as they remained securely tied to the sides of her body. The girls untied her and led her to the bathroom. They added to her humiliation as they watched her relieve herself, sitting like a girl, and then bathed her, leaving no part of her body untouched. The frustration she had felt yesterday was reborn, but the girls had no intention of satisfying Nancy’s needs.

After her bath they dried and powdered her, and even dabbed some perfume on her neck, and then led the feminized boy to the bedroom to dress. Today, she would be in basic black. Black bikini panties with matching bra and slip, black pantyhose, black patent leather shoes with medium heels, and a black dress with a white lace collar that went halfway down her thighs made up the outfit. After applying her makeup and fixing her hair, Andrea produced a white frilly apron and cap. When Nancy looked in the mirror, she realized that she looked like a maid, and that was what she was going to be.

Nancy spent the morning doing housework. She made breakfast for her mistresses, cleaned the kitchen, bathrooms, made the bed, dusted, vacuumed, and washed clothes. Lois or Andrea, or both were there supervising her every move, and forcing her to do it over if she didn’t accomplish the task to expectations.

Several times she was near tears, and only with great effort was Nancy able to hold them back. By lunchtime, she was exhausted, and she wondered what else they would have come up with for her do.

“You did such a good job as our maid, we are going to reward you, Nancy. We will allow you to go outside this afternoon. It is such a beautiful day, and we wouldn’t want you to miss it”, announced Andrea.

“We have an order at the grocery store for the party tonight. Why don’t you go pick it up. Oh, and don’t get any ideas about not coming back. You will not have any money or keys to our house, and you won’t get far dressed like that.”

“You mean I have to go wearing all these fancy looking girls clothes?” asked Nancy.

“Of course not, silly”, said Lois “Do you think we would make you go out looking like a French maid?”

As Norman heaved a sigh of relief, he heard Lois say “Take off your apron and cap. We’ll comb your hair and fix your makeup. Then you can go to the store.”

Soon Nancy found herself outside the house, with instructions to pick up the groceries and return home. If she wasn’t back in 30 minutes, the whole town would learn of her escapades the last 24 hours. Nancy knew she had no choice but to obey. She had no way of getting away, and even if she did, had nowhere to go. To make matters worse, she was starting to enjoy her new role as a female, and the clothes were exciting her. She was not left alone long enough to satisfy what was becoming an urgent need, at least not until now, and she could hardly relieve her frustrations in the street. She walked to the store, certain that everyone who saw her would know she was not a real girl. To her great relief, people accepted her for what she seemed to be, and in fact, one of the grocery clerks flirted with her and insisted on carrying her groceries home.

When they got home, Andrea was sitting on the front porch with a smile on her face.

“Who’s your friend Nancy?” she asked.

“I..Andrea, this is Robert. He insisted on carrying my groceries.

“Well, Robert I’m pleased to meet you. I’m Nancy’s step sister. We are having a party tonight. Would you like to come? We always have room for an extra person.”

“Sure, it sounds like fun and its a pleasure to meet you too, Andrea. Well, I had better get back to work. See you girls tonight. Good bye Nancy.”

“Oh, g..good bye Robert, and thank you”, she stammered.

“Well Nancy, it looks like you won another heart. What are you going to do with two boys fighting over you tonight. Ha ha, I can hardly wait to see how you handle it. I may take notes. Who knows, maybe I’ll learn something.”

Chapter 6 – The Party

Nancy found herself anxiously waiting for the guests to arrive. She was very nervous and kept looking in the mirror to see if she could detect any flaws.

She-Made-Him-Her-Pretty-Teenage-Step-Sister-44She hadn’t found any, and in fact was amazed at how pretty she looked in the new dress and shoes. The lace bodice of her slip showed through the dress and made her look very sexy. She felt very feminine, indeed, and prayed she could make it through tonight undetected.

As the first guests arrived, Nancy tried to make herself as inconspicuous as possible. Andrea and Lois made sure that she was introduced to everyone, however, and she had difficulty remaining in the background.

Harold arrived and made a beeline for her. When he reached her, he gave her a big kiss. Nancy could feel a stirring in her loins as Harold led her to the dance floor, and soon she was in his arms, being swept around the floor. She could not understand why she felt so good, but found herself wishing the dance would never end. Then Robert came, and the next dance belonged to him. Nancy’s nervousness gradually abated when she realized that everyone was accepting her as a girl, and she alternated dances with the two young men who were obviously very interested in her. She found herself thinking it would be nice to spend the night with one of them. Only when she caught sight of Andrea smiling at her, was she jolted back to realty. She excused herself and went to the bathroom. She tried to figure out how to extract herself from her predicament.

Having no experience with warding off unwanted advances from males, he wasn’t quite sure what to do. She was certain that Harold would not take no for an answer, particularly after last night.

“That’s it”, she thought. “If I play up to Robert, then Harold will leave me alone, and than I’ll tell Robert that I don’t screw around on a first date.”

When she returned to the party, the lights had been turned down, and it was obvious that the boys and girls had paired up and found places where they could have some privacy. She soon found Robert on one side of her and Harold on the other. They literally dragged her to another room. She could see that they were angry about something, and it occurred to her that Andrea or Lois may have told them the truth about her. She became very frightened.

“It is obvious Nancy, that you have been playing Robert and I against each other. We are friends, and will not allow any girl to come between us. After last night, I know you are no shy wallflower. As I told Robert, you gave the best head I have ever received, and I think it only appropriate that you do the same for my friend.”

She watched Robert drop his pants as Harold kept a firm grip on her arm. He forced her to her knees with her head next to his friend’s prick. Nancy could feel the tears well up in her eyes, and before she could protest, she found a long, thick pole being forced into her mouth. She could hear him moaning as he held her head steady while thrusting his cock in and out of her mouth. She found that she was enjoying it, as she had the night before with Harold. When Robert finally exploded into her mouth, she was ready for him and swallowed every drop of his creamy liquid.

No sooner had she gotten to her feet when Robert took her in his arms and kissed her, then she became aware of a hand caressing her bottom, and felt her skirt being lifted up above her waist. Panic set in when she felt a hand pulling her nylons and panties down in the back. She knew she was in real trouble if they discovered the secret she had in her pants, but was helpless to do anything to prevent it. Miraculously, Harold saw nothing, intent on satisfying his own needs. He was preparing to penetrate her anus, neither one aware of the bulge in the front of her panties. Robert released her and she found herself on the couch with her ass in the air as Harold entered her. Soon they were in the throes of ecstasy. It did not take long for Harold to shoot his load. The pretty boy could feel the warm liquid shooting up his ass. It was an incredible feeling, as Nancy imagined herself a girl, receiving her boyfriend’s sperm in her vagina. She also had an urgent need and wasn’t sure how to take care of it.

The excitement of the past 24 hours was catching up with her, and he realized that she could not contain herself much longer. If she came, she would give away her secret, but she was powerless to prevent it any longer. The friction of her panties rubbing against her erection was enough to cause her to erupt, soaking her new undies with her cum.

She-Made-Him-Her-Pretty-Teenage-Step-Sister-31Nancy collapsed on the couch with Harold on top of her. She began to cry. Harold slowly lifted himself off the prostrate boy. Nancy rolled off the couch, pulling her dress down in the front, and praying it had not been stained. She got to her feet, pulled up her panties and ran off to the bathroom.

She breathed a sigh of relief when she saw that her cum had not seeped through to her dress. Her new panties were soaked through and her slip was damp. She removed her panties along with her pantyhose. Her first thought was that she hoped they wouldn’t be permanently stained, but realized her first priority was to make it through the rest of the night without being discovered.

Then checking to be sure no one would see her, she made her way to Lois’ bedroom, leaving her cum soaked panties in the bathroom. Fortunately the bedroom was empty. She borrowed a pair of the girl’s panties, realizing that she would probably be punished for it, and replaced her nylons. Then she checked her hair and repaired her makeup, and made her way back to the boys.

When she returned, Robert was gone.

“He has to get up early tomorrow to go to work. He sent his apologies” said Harold. “This means I have you all to myself. Let’s get out of here for a while and go for a walk.”

Figuring that she might be safer outside, Nancy agreed. Holding hands they walked several blocks, coming to a park. They went into the park and stood by the lake watching the moon rise on a beautiful night. She soon found herself in his arms engaged in some heavy kissing. She could feel his erection growing again along with her own. She held her knees tightly together hoping it would subside, but his kisses were exciting her and she realized that her dress was now sticking out like a tent. Before she could stop him, she felt his hand reach under her skirt, caressing the inside of her thigh. He brought his hand up, brushing it against her prick. Then he grabbed it.

“What’s the meaning of this he said?” as he lifted her skirt all the way up, so he could see the bulge in her panties. “Pull down your panties!”

Afraid of him, she dropped them enough so that he could see her erection pop out. She stood there, shivering with fear, as he looked at her with disbelief.

He approached her and surprising her dropped to his knees in front of her. He took her in his mouth and began to suck it. Nancy was shocked, never having had this done to her before and moaned with the pleasure it gave her. When she finally erupted, Harold eagerly drank the warm cum, swallowing every drop. Then they switched positions, and Nancy, anxious to please her new friend did the same. Afterward they embraced, kissing more passionately than before.

“This will be our little secret. Ok?”

“Yes!” Nancy responded. For the first time since her masquerade began, she was totally at ease.

They walked back to the party with Nancy clinging to him. When they got back to the house, the party had broken up. Harold gave her a quick kiss and left. Nancy stared after him as he got in his car and drove off, dreaming about being with him again.

Chapter 7 – Still a Girl

She-Made-Him-Her-Pretty-Teenage-Step-Sister-34Reality hit her as she walked into the house. Lois and Andrea were waiting for her. They took the hapless boy upstairs and stripped him down to his panties and bra.

“Those are my panties!” said Lois. “What are you doing with them?”

“I..I..I had a little accident” Nancy replied, meekly.

“Did you lose your panties while screwing one of your boyfriends?” asked Andrea sarcastically.

Nancy did not reply, but hung his head in shame realizing the implications of his evening’s activities.

“You have to learn you can’t just take someone else’s possessions!” said Lois.

She grabbed him by the arm and threw him to the ground. Norman was shocked at her strength, and before he could get up, she jumped on his back. She began to spank him, and despite his efforts to throw her, he found he was too weak.

“You’re just a little sissy!” she cried. “Making you wear a dress was just what you wanted, wasn’t it? Maybe we should keep you in skirts all the time. You could even go to school in a dress. You’d like that, wouldn’t you?”

“No, no!” he cried. “I wouldn’t. Please stop, you’re hurting me.”

Nancy was crying as his pantied ass became sore from the spanking. Finally she stopped, and ordered him to stand. Still crying he scrambled to his feet, covering his genital area.

“Put your hands at your sides, you sniveling baby!”

He did as ordered, revealing his erection.

“You know, Lois, I believe he enjoyed it. I think he likes dressing up like a girl and being spanked, don’t you Nancy?”
The pantied boy stood there with his head down, trying to stop the flow of tears. The two girls stood there staring at him until he finally gained control of his emotions. His erection, however, had not subsided and was evidenced by the bulge in his panties. Andrea reached into his panties and pulled out his prick.

“Stroke it Nancy!”

Afraid to disobey for fear he would again be spanked, he began to stroke himself. He didn’t want to cum in front of them, but he was too excited, and in spite of his own wishes, his milky liquid shot, splattering on his step sister who stood right in front of him. Once he began to cum, he relaxed a little and enjoyed himself, and didn’t stop stroking himself until he was dry.

Andrea was angry that he had cum on her dress and slapped him hard in the face, again bringing tears to his eyes.

“You better hope it doesn’t stain my dress” she said, “or you’ll owe me a new one!”

The two girls led Nancy to the bathroom where they discovered his cum soaked panties.

“It looks like are little Nancy had a busy night” said Lois, causing him to blush.

“Now wash out my dress!” said Andrea.

“And my panties!” said Lois.

“And you might as well wash those” said Andrea pointing to the panties Nancy left in the bathroom.

Standing there in only his bra, he hand washed the delicate items and hung them to dry. He was then led back to the bed room where he was dressed in light blue baby doll pajamas. Again his hands were tied to his thighs and he was put into bed. The girls were too tired tonight for any extra curricular activity, and it wasn’t long before the three of them were soundly asleep.

Chapter 8 – A Maid Again

They were jarred awake early the next morning by the phone. Lois got up to answer it and when she returned she got the others up.

“It was my folks. They’ll be home by noon. We’ve got to get this place cleaned up!”

They quickly untied Nancy and ordered him to put on the black dress he had worn the previous morning. He would again be the maid. This time, however, the girls pitched in to help and by 11:00, the house was spotless.

“One more thing to do.” said Andrea.

“What’s that?” asked Lois.

“The bathtub in your parent’s bathroom.” “But it’s already clean.”

“It won’t be after we bathe” smiled Andrea.

She-Made-Him-Her-Pretty-Teenage-Step-Sister-37The two girls and Nancy stripped and got into the huge tub. They relaxed in the bubbles for half an hour before getting out.

Nancy, naked, was ordered to clean the tub. He was dressed in a yellow short sleeved sweater, tight denim miniskirt, yellow bobby sox and tennis sneakers. As he had for the previous day and a half, he looked just like a teenage girl.

“What are you doing?” asked Lois. “You don’t want him to meet my parents dressed like that, do you?”

“Trust me!” said Andrea, as she finished putting on his makeup.

Any fight Nancy had left was taken out of him by the spanking Lois had given him the night before, and he had submitted meekly to their demands this morning. The prospect of meeting her parents while dressed as a girl, shocked him out of his trance, and he began to protest, hoping Lois would side with him.

Andrea, however, was in full control of the situation, and slapped him a few times until he calmed down.

“You will do as I say, little sister, or I will take you over my knee!”

That calmed him down immediately as he realized she was quite capable of doing just that, and would probably enjoy it. The three of them had just gone downstairs when they heard the key in the lock. Nancy was petrified, Lois a bit nervous, but Andrea seemed full of confidence. Her plan was working to perfection.

Lois greeted her parents as they walked in, giving them both a hug and kiss.

Andrea also hugged them and then introduced them to Nancy.

‘This is my new step sister, Nancy!”

“But I thought you had a step brother. Your mother said nothing about a girl?” Lois mother said.

“You must have misunderstood. Nancy is definitely a girl, aren’t you?” she said as she turned to the skirted boy. He nodded but said nothing.

“We have to go home now. Lois, I’ll see you tomorrow. Come on Nancy, let’s go!”

She grabbed him by the arm and threw him to the ground. Norman was shocked at her strength, and before he could get up, she jumped on his back. She began to spank him, and despite his efforts to throw her, he found he was too weak.

“You’re just a little sissy!” she cried. “Making you wear a dress was just what you wanted, wasn’t it? Maybe we should keep you in skirts all the time. You could even go to school in a dress. You’d like that, wouldn’t you?”

“No, no!” he cried. “I wouldn’t. Please stop, you’re hurting me.”

Nancy was crying as his pantied ass became sore from the spanking. Finally she stopped, and ordered him to stand. Still crying he scrambled to his feet, covering his genital area.

“Put your hands at your sides, you sniveling baby!”

He did as ordered, revealing his erection.

“You know, Lois, I believe he enjoyed it. I think he likes dressing up like a girl and being spanked, don’t you Nancy?”
The pantied boy stood there with his head down, trying to stop the flow of tears. The two girls stood there staring at him until he finally gained control of his emotions. His erection, however, had not subsided and was evidenced by the bulge in his panties. Andrea reached into his panties and pulled out his prick.

“Stroke it Nancy!”

Afraid to disobey for fear he would again be spanked, he began to stroke himself. He didn’t want to cum in front of them, but he was too excited, and in spite of his own wishes, his milky liquid shot, splattering on his step sister who stood right in front of him. Once he began to cum, he relaxed a little and enjoyed himself, and didn’t stop stroking himself until he was dry.

Andrea was angry that he had cum on her dress and slapped him hard in the face, again bringing tears to his eyes.

“You better hope it doesn’t stain my dress” she said, “or you’ll owe me a new one!”

The two girls led Nancy to the bathroom where they discovered his cum soaked panties.

“It looks like are little Nancy had a busy night” said Lois, causing him to blush.

“Now wash out my dress!” said Andrea.

“And my panties!” said Lois.

“And you might as well wash those” said Andrea pointing to the panties Nancy left in the bathroom.

Standing there in only his bra, he hand washed the delicate items and hung them to dry. He was then led back to the bed room where he was dressed in light blue baby doll pajamas. Again his hands were tied to his thighs and he was put into bed. The girls were too tired tonight for any extra curricular activity, and it wasn’t long before the three of them were soundly asleep.

Chapter 9 – Auntie’s New Niece

On the walk home they met several people Andrea knew. She introduced to Nancy to all of them as her step sister. They also ran into some of the kids who were at the party the previous night. Nancy wondered how she could ever appear in town as Norman. Everyone would know he had been dressing like a girl. The more he thought about it, the more depressed he became. By the time they got home, he felt like crying.

“Don’t even think about changing your clothes, Nancy!”

He was sufficiently afraid of his step sister by now that he meekly obeyed her, and the two of them were sitting in the living room when Andrea’s mother arrived home. She noticed Nancy sitting there, but did not recognize her. After greeting her daughter she asked about Norman and wanted to meet Andrea’s new friend.

‘This is Norman, mother, though when he dresses like this he wants to be called Nancy.”

Mrs. Malone stood there stunned. She stared at the pretty girl sitting on the sofa, looking sad and afraid. Finally, she realized that the feminine looking creature with the shapely legs showing beneath her miniskirt was, indeed, her stepson.

“What’s the meaning of this, Norman?”

Norman wanted to die right there. Before he could answer, Andrea spoke up, and he was forced to listen to her distorted story about his feminization.

“I can explain, mother” said Andrea, “please sit down. It started Friday afternoon. Lois invited him to go swimming but Norman used it as an excuse to get undressed and try on her clothes. I came over and there he was, wearing one of Lois’ dresses. Not only that, but her underwear and makeup.”

‘That’s not the way it was!” cried Norman.

She-Made-Him-Her-Pretty-Teenage-Step-Sister-40“Quiet! Are you calling Andrea a liar? Continue dear!”

“He apologized for putting on her dress and begged us to get him some girl’s clothing of his own. Maybe we were wrong, mother, but we felt sorry for him and took him shopping. We bought him a complete outfit. He has been dressed like a girl since then, even going to the party as a girl. I think he made out with Harold, last night. I loaned him the outfit he’s wearing, after he begged me.

Please don’t be hard on him. He’s just confused.”

“So, all of the kids at the party, the same ones he’ll go to school with, thinks he is a girl” her mother said.

“Also Lois’ folks and several other people we met today on the way home. Almost everyone thought you said you had a step son, but he convinced them you had a step daughter. I don’t know how you’ll explain it.”

Mrs. Malone sat there quietly for awhile, looking at her sissy step son. He sat there demurely with his legs crossed, a touch of lace from his pretty white slip showing and looking very self conscious.

“He really does look like a girl” she thought to herself. “He needs some instruction in female mannerisms and behavior, but he is very feminine.”

“Alright” she said. “Nancy, you will remain in the house for the next several days while I decide what to do. During that time you will wear only girl’s clothing which you will borrow from Andrea. Andrea, you will lend Nancy any clothes she wants. Is this clear to both of you?”

“Yes mother” they both responded together.

Chapter 10 – Decision Day

Several days later, Mrs. Malone called the girls together to tell them of her decision.

“Nancy, I have decided that you will remain a girl. The two of you will take all of your male clothing and put it in boxes. It will be given to charity. We will shop for a new wardrobe of girls’ clothing for you over the next week. I have scheduled you for a breast implant next week. Whether or not we ultimately change your sex will be decided at a later date.”

Hearing that, Norman began to cry. This had gone a lot farther than he ever thought it would. He begged his step mother to reconsider, but she said that her decision was final, and that he had brought it all on himself, when he decided to wear all those frilly and pretty girls clothes.

“Furthermore” she continued, you have been enrolled at Ms. Kate’s School for Young Ladies as has your sister. The two of you will be roommates, since we can’t very well have Nancy rooming with another girl.”

Now it was Andrea’s turn to object, but she too found her mother was adamant.

Mrs. Malone did not think Andrea’s story rang true and had suspected that Andrea was behind the whole affair. She felt that the damage done, however, could not be easily undone and that keeping her step son in skirts was the best solution.

Sending Andrea to school with Nancy was her way of punishing her, since she knew her daughter would object.

As promised, Nancy’s wardrobe was replaced with skirts, blouses, dresses, lingerie, and all of the accessories appropriate for a seventeen year old girl.

He was told he would finish high school as a girl, and if he chose to move away at that time, he could again resume his male identity.

Nancy never did wear pants again, though he still has his male equipment. Lois was sworn to secrecy as were the two women in the dress shop. It took awhile for him to accept his fate, but once he did he learned to enjoy his femininity.

Andrea, once over her anger, treated him like the sister he had become, sharing her clothes with her, giving her advice about boys, and became very protective of her sister. Nancy and Harold dated when she was home on school breaks.

After college they were married. Though she cannot have children, he revels in being Harold’s wife and taking care of him, as a good wife should.

The End

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stephanie kimberlie prince

The House of Sissify is absolutely the best sissy site on the web. This sissy has learned so much since joining. The advice and support are wonderful. s.he has learned how to love, honor, obey, and worship Superiors and… Read more “stephanie kimberlie prince”

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1 month ago

My whole life i have dreamed about having a couple of girls make me up and try on different dresses ?

6 months ago

i love the story–i wish my sister and her friends had feminized me like that and i could suck my boyfriends

joanna cotton
1 year ago

What a wonderful story…….

1 year ago

What gorgeous illustrations of her transformation. It would be wonderful to be transformed by such a beautiful mistress. Love Priscillar XXXXX

sissy courtney
1 year ago

Delightful reading!

2 years ago

We all Love this long Story of how to become a beautiful sister. So glad you also enjoyed it Pammie and geri Love Prisse

2 years ago

This remains a well illustrated story. Lots more comments will al
ways be appreciated. Much love Prisse xxx

2 years ago

Such a rapid transformation to Nancy was rather too fast. It would have been better for Nancy to have had a further week of training to be a lady before the party. She was lucky to have had the guidance of such a lovely sister as Andria turned her into a new sister. I wonder how they learned to make love to each other when they shared a room at University . It must have been very sexy for both of them. Best wishes to Nancy and Harold much love Prisse xxxxx.

sissy pammie
Reply to  Priscillar
2 years ago

She was so lucky to have a boy that liked sissies.

Reply to  sissy pammie
2 years ago

I agree and I hope they remain together for many months and maybe have a baby girl to enjoy. Love Prisse xxxx

sissy pammie
Reply to  Priscillar
2 years ago

Months? Years, decades, you find someone that special and unique never ever let them go!

2 years ago

That was such a delightful story. This sissy loved it, wishing she was Nancy. When Nancy was denied sex by those truly tormenting and dominating women and weeped, sissy felt her urgency and frustration and cried with her. But despite the torment and humiliation it was beautifully done; just like a sissy should be. Thank You so much for sharing the story. This sissy is still trembling.

2 years ago

What a delightful sister!!!! I do hope they have a baby boy to play with in due time. Much love Prissexxxxx