John turned eighteen that day. His father was at work. His mother and sister Lisa were spending the day shopping, saying they wouldn't get back until very late in the afternoon. He decided he wanted to pamper himself, celebrating in the best way possible. That way was by dressing up as a female. John had been a crossdresser since he was sixteen. He believed he had managed to keep that part of himself hidden from the rest of the family.
After taking a luxurious bubble bath, he carefully made up his face. A pair of false lashes followed. He admired his efforts in the mirror, then went to his room to retrieve a pair of breast forms, clip-on earrings, and a wig hidden away in his closet. He stopped by his mother's room, picked out a pair of her lacy panties, and put them on. Finally, in Lisa's room, he sprayed on a dash of perfume.
He took out a strapless bra, pantyhose, and a long slip. After filling out his bra and donning the rest, he went to her closet. Since he had the day to himself, he had decided to go for an elegant look, settling upon a long, formal strapless dress.
He put on the outfit and a pair of his sister's high heels. Gracefully, he walked around the house, enjoying every minute of his girl time. The opportunities like this didn't come along that often. He wanted to enjoy it as much as he could, especially on his birthday. Using his phone, he took some selfies in a full-length mirror. Later on, he planned on transferring them to a password-protected file directory on his computer.
Despite his precautions, he hadn't been careful enough. He had gotten a little lax in hiding his activities. His mother and sister started to notice their things being out of place from the way they remembered leaving them. Guessing that the culprit likely was John, they decided to see what he was doing while they were gone.
Lisa set up a hidden spy camera in her room, as did her mother. When they reviewed the video from the cameras, they were surprised to see John in dresses and makeup. Once the shock wore off, his mother and sister started hatching a plan. Rather than confronting him right away, they decided on something different. Telling him that they would be gone most of the day, they guessed he would use that time to get dressed up once again.
However, unbeknownst to him, they only planned to be gone perhaps ninety minutes or so. They felt it would be enough time for John to get himself situated so they could catch him in the act. When they returned, they noticed the doors and curtains closed. Lisa gave a knowing look at her mother. They walked around to the back door. Quietly opening it, they crept in and entered the living room.
John was paging through his sister's fashion magazine, wishing he could wear the dresses some of the models had on. Lost in his thoughts, he was brought back to sudden awareness when he heard a gasp. He looked up to see his mother and sister standing there. 'Oh shit,' he thought to himself.
"Mom! Look at him," Lisa said. "He's got makeup and a dress on. He looks like a girl! Hey, wait a minute, that's my prom dress! What are you doing in my prom dress?"
"So what is this, John?" his mother said. "Your sister and I thought you might be into our things for some reason, so we set up spy cams. That reason why didn't dawn on us until we caught you on video in our rooms. Even though I see you now with my own eyes, I still can't believe it. What do you have to say for yourself?"
"I can't help it, Mom. I just have to do it There's something about wearing these things that makes me feel more complete."
"Stand up. Let's see you."
John meekly obeyed.
"Lift the dress," she told him.
"Heels, pantyhose… So whose panties are you wearing?" his mother asked.
"Yours," came the reluctant reply.
"And I see you have a bra on, too. Is that mine or hers?"
"Hers."
Lisa remarked, "I guess I am not losing my mind. I thought some of my things had gotten moved around, but I didn't remember doing it. This explains it."
"Well John, I hope you're feeling photogenic," his mother said. She used her phone to take pictures of him. His sister did the same. "Once your dad sees these, he won't know what to think," she continued.
Suddenly Lisa started laughing. "What's so funny?" John asked.
"You mean aside from coming home to find my brother wearing my clothes, looking like a girl? Oh, lots of things." At that point, Lisa went over and whispered in her mother's ear.
Her mom smiled and said, "Oh, that's right. The family tradition. With all this going on, it had slipped my mind for a minute. Well, I'll talk it over with your father. When he gets home, we'll show him everything. But I'm sure he won't mind at all."
Lisa smiled and looked at her brother, "I think you'll be surprised at what Mom and Dad had planned for your birthday tonight. It will just be a little different from what we all had originally expected."
Confused, John asked, "What's this 'family tradition?' I don't remember ever hearing about one." His sister and mother smiled at each other.
His mother said, "If I told you now, it wouldn't be a surprise. Plus, as I mentioned, I need to run something by your dad first."
"Mom," Lisa asked, "I just thought of one more thing. Do you think that..." and finished the sentence, whispering again in her mother's ear.
"Oh! OK, maybe later on this week," her mother replied. "In the meantime John, go take off that dress. You will be paying the dry cleaning bill for it, young man, or should I say, 'young lady?'"
"Lisa, would you go to your room and pick out a pretty outfit for your new sister to wear? After all, she can't wear this one to the mall. Since that dress seems to fit her fairly well, I'm guessing that she and you are about the same size. Why don't you find her something feminine and girly? At least, more so than she already is! She and I are going shopping to start building her new wardrobe. We'll have to get her some dresses and pretty lingerie, along with all the basics. Oh, one more favor. Please take all your former brother's boy clothes, put them in bags and drop them off at the Goodwill. He is gone. Your sister will not need them anymore. We can loan her some clothes until she can get her set up with her own."
John exclaimed, "Huh? 'New sister?' And the mall? I have to go to the mall in a dress?"
"Well, you'll have to touch up your makeup first," his mother said. "No one will think you are anything but what you now seem. Your old life is gone. This is your birthday, in more ways than one. It's obvious you want to be a girl, so you're going to get your wish. You will be wearing skirts and dresses as long as you live here. Maybe once you come to accept these changes, I might let you wear some pants again, as long as they are feminine. Also, your shoes will always be high heels of one sort or another. You can wear wedges, pumps, stilettos, or anything else, as long as the heel is at least three inches. You will only wear flat-soled shoes if there is a good reason to do so."
She continued, "While we're at the mall, we'll get you fitted for your very own bra. Soon you'll have a drawer full of pretty things to wear. Then you won't have to borrow ours all the time."
Lisa smiled, saying, "You know, I think I'm going to like having a sister. We can share clothes and so much more. I'm not happy that you borrowed my things. But even more than that, you look better in my dress than I do! I can't believe it. My brother looks good in my dress!"
His mother began to say, "John," but stopped. "You know, 'John' is certainly not a name for an attractive young lady like yourself to have. Do you have a girl's name you like?" John was at a loss for words. So much had happened in such a short time. He was still reeling from having his secret exposed to the family.
"Hmm, maybe 'Jennifer.' That's a pretty name. Yes, I think you are a 'Jennifer.' Now Jennifer, go take care of your makeup before we go out. In the meantime, I am going to call your father. I think I should tell him the news now instead of waiting for him to get home. Oh, do you have makeup hidden somewhere, or did you borrow ours?"
"Um, both, Mom."
"Your sister and I will help you go through your collection so we can decide what you should toss. We'll also tell you what to keep so you can stay pretty. From now on, I want you to make sure you are fully made up every day, once you are showered and ready to get dressed in the morning. Then, keep it on all day until you are getting ready for bed at night. Just touch it up when you need to. Women shouldn't sleep in makeup, not even you."
She carried on, "One more thing. Being a woman is more than just being able to wear dresses and makeup. Soon, you will have to live and work entirely as a woman. It won't be easy. A lot of people won't understand, but it's what you will learn to accept because this is your new life. Now go get ready," his mom said.
As Jennifer walked away, she could hear her mother on the phone. "Honey, there's been a change of plans for tonight. You see, we now have two daughters. Yes, that's right. We came home to find John all dolled up, wearing Lisa's prom dress. Surprisingly, she looked pretty good in it. Yes, 'she.' You would never have known there was a boy underneath. Lisa can't get over it. So we decided that John will be better off as a girl. Her name is going to be 'Jennifer.' I am going to take her to the mall to get her some things she'll need so she won't have to always borrow from her sister and me. Lisa will tell you all about it. I'm sure she'll show you the pictures of your lovely daughter when you get home. But I think that maybe you should do the honors tonight instead of me. You will? Great. See you when we get back from the mall."
Jennifer and her mom spent a few hours buying dresses, makeup, and many other items for her new life as a girl. They stopped to have Jennifer's ears pierced so she would no longer have to rely on the clip-on earrings. She was afraid someone might recognize her, but no one saw anything other than an attractive, young female. Jennifer thought she even saw a couple of guys checking her out. She had begun to accept her fate, realizing deep down that it was a dream come true.
When the two got home, Jennifer's father was there, waiting to see his new daughter.
"So you want to be my daughter now? Well, your mom was right, you are very pretty. I like your perfume; it smells nice," he said. Turning to his wife he said, "I didn't even recognize her at first. So, have you told her yet?"
"No, Lisa and I both felt it should be a joint, family thing, so we waited for you."
Her father smiled and said, "Well Jennifer, since it's your eighteenth birthday, it's time you learned about our family tradition."
"Yes, Dad, I hear stuff about the family tradition, but no one will tell me what it is. I don't remember any special family tradition for someone's birthday."
"That because you hadn't turned eighteen yet. We thought the best time to tell you would be on your birthday."
"So what is it, then?" Jennifer asked.
"Well dear," her mother said, "when one of the children in this family turns eighteen, the mother takes her son to bed for his first time. She will begin to teach him how to please a woman. Otherwise, the father will bring his daughter to bed. She will give up her virginity to him, becoming a woman. This is something wonderful. It's been passed down in the family for generations. I happily gave myself up to my father when my time came. My mother did the same with her father before me, her mother before that, and back for so many generations, no one knows anymore. For almost every one of those women, it was a positive experience, according to the family lore. I know I have never regretted it. I would gladly do it all over again. I think your sister also feels that way."
Lisa added, "As Mom said, it's been happening in our family for ages. I found out about it on my eighteenth birthday. Now tonight, it's your turn."
"What?" said Jennifer. "You mean you and Dad, Lisa, in bed? With each other?"
"Yes, when I turned eighteen, Dad was my very first lover. He is still the best. He took my virginity and made a woman of me. Now Mom and I take turns with him. I look forward to every time I can go to bed with him. His cock is wonderful!"
Jennifer had started to put the pieces together. Almost. "So it's going to be Mom and me tonight?"
Lisa laughed. "No, silly. You're forgetting, you're a girl now, so you get to have Dad tonight."
"You mean I'm going to bed with Dad?"
"Yes, it'll be great!" her mom said. "You should wear some of those pretty things we bought, so you can look very sexy for him. His cock will be hard and ready for you in no time. Unfortunately, you don't have a vagina, at least yet, but you are going to learn how nice his cock will feel in your butt. Of course, you are going to not only going to have the privilege of him cumming in your butt but also your mouth. You'll become an expert at sucking his cock. One of these days, I suspect you might find yourself pretty popular with the boys in the neighborhood because of that, so your father will be happy to give you lots of practice. I think you'll find yourself looking forward to it."
Lisa chimed in, "And one of these nights, I'll get my chance with you, too." She reached behind her chair and pulled out a sack. In it was a strap-on, vibrating dildo. "Mom said I could borrow it. I guarantee you are going to be pegged sometime before the end of this week. Then when I'm done, you will beg for more. This will be fun!"
Her mother added, "Your dad has a little submissive side in him, so he lets me use it on him now and then. I thought it was a great idea when your sister asked me if she could use it on you."
Jennifer was taken by surprise by all of this. However, she realized she had no choice but to accept her fate. But it was looking like her fate might not be too bad.
Her father said, "Alright ladies, I am going to go take a shower. Why don't you get Jennifer freshened up so she'll be all set for her big night? Jennifer, I will meet you in the bedroom in maybe twenty minutes or so."
"She'll be ready," her mother said. "OK, Jennifer, I want you to put on the bra and panties, along with the garter belt and stockings I bought you today. You are going to look so nice for your dad. This has been an amazing day so far. Now, to finish it off, you'll get to learn how to enjoy your dad's cock. Your father is going to make you a woman."
Jennifer complied, and when she returned, her mother said, "Oh, that looks so good on you. I wish you had real boobs, but those breast forms will certainty fill out your bra for now."
"Mom, I have to tell you something."
"You're not backing out of this. You have to do it," her mom said.
"No, I'm not backing out," Jennifer replied. "It's just that after everything that's happened to me, and now, beginning life as a girl, I think I am looking forward to this. I was surprised when it came to me, but I do want to learn how to suck Dad's cock and feel him in my butt. When we were at the mall, it just felt so liberating to wear a dress, especially on a warm summer day. That was what convinced me. I knew this is what I wanted to do."
Jennifer's mom smiled and said, "See? It's wonderful being a girl. Now you are beginning to understand that, too. Being female is hard work, but it's a job you will love. Plus, it has some great fringe benefits, as you will find out shortly. And let's face it, this is more than just tradition. In this family, it's a daughter's duty. Duty to herself, the family, and the legacy of all the women who came before her. Now you are the next daughter in line. Your situation is unique, but not unheard of. I think you will carry on our legacy just fine. "
Continuing, she said, "My mother once told me of a boy in this family long ago discovered in female clothing. 'He' became 'she,' and on her eighteenth birthday, her father made her a woman, just as you will be soon."
"What happened to her?" John asked.
"She came to love her new life. Eventually, she married a man who loved her unconditionally, and they lived out their days together. Perhaps the same will happen to you someday. Now go wait for your father."
Jennifer made her way into her parents' bedroom, just as her dad had finished drying off from his shower. He walked into the bedroom and saw her somewhat nervously waiting for him. She eyed his rapidly hardening cock, wondering what it would feel like once he was screwing her.
"Well, my dear, I hope you are ready for this." He kissed her and said, "So tell me, what do you think we should do first?"
"Dad, just from this afternoon, I realized that I do want to be a woman, so I want you to show me how nice it will be."
Her dad kissed her again and said, "Well, why don't you start by getting your first experience at sucking a man's cock? Grasp it and then stroke it some, like you were jerking off. Now lick it, especially right there," as she began to lick the head. "Then put it in your mouth and suck it with your lips, sort of like a Popsicle or a lollipop. Now back and forth. Good, good."
Jennifer tried to follow her father's coaching as best she could. She had decided she was going to enjoy every bit of her first chance at giving a blowjob, wanting her father to enjoy it, too.
"Here, I'll help you a little," and her father began to thrust himself in and almost out of her mouth with a hand on the back of her head as she continued to suck.
"Now see if you can get it completely in your mouth. It's a little tricky, but you just have to avoid the gag reflex."
She did gag but was determined to keep trying until she finally managed to take the entire length of her father's cock.
Back and forth her mouth and hand went. She stopped for a second and asked, "What do you think, Dad? Am I doing this OK? This is special for me, and I want it to be special for you."
"You're doing fine. Just keep sucking and pumping. I feel like I'm going to cum soon."
Jennifer continued to delicately lick her father's cock and then suck it as she moved her mouth back and forth quickly over its length, relishing the new experience.
She felt her father's buildup. "I'm going to cum," he said, and she opened her waiting mouth to accept his load. Her finger wiped up some that had ended up on her face. Licking it off. She decided that she kind of liked the taste, feeling pleased that she had gotten her father to cum with her very first blowjob. She swallowed and asked again, "Did I do OK, Dad?"
Her dad remarked, "I think you did fine."
"Before this afternoon, I'd never even thought of giving someone a blowjob," said Jennifer. "But now I want to do this again with you when I can. I will always be happy to take care of you. Just say the word. Mom was right. The fringe benefits of being a woman are great!"
"Dear, you will get plenty of chances. Just remember, your mom and sister also enjoy it just as much as you, so they get to have their turns, too."
"Dad, are you going to fuck me?"
"Of course! Why don't you grab my cock, stroke it and play with it, even suck it some more until it's ready? Then you will get to finally join the generations of women in this family who have preceded you."
Jennifer followed her father's prompting, and quickly, her father grew hard again.
"Now, since this is your first time, why don't you get on all fours? This will make it a little easier for you to take me."
She did as he suggested, and her father proceeded to pour some lubricant along the crack of her buttocks. His fingers poked in and out of her puckered hole, making sure it was ready for the visitor that would soon be arriving.
After lubricating his member, he positioned the head at her hole and slowly entered her.
"This might hurt a little at first, but it shouldn't be too severe. Just let yourself relax."
She gasped. "Are you doing OK, dear?" her father asked.
"Yeah, dad, I think I can take it. Please don't stop."
"We'll do this nice and slow. Let your body adjust to this. Maybe you should even try backing up on it, so you can do this at your own pace. This is going to be the first of many times we have, so I want you to enjoy it."
Little by little, Jennifer was able to take her father's member in her, until she had engulfed its entire length. Her father patiently let her get accommodated to it, then slowly began to thrust in and out of her. Each thrust brought a moan from his new daughter.
He began to increase his pace, then alternated between slow and steady, then rapid, repeated thrusts.
"Oh, oh, oh," escaped her lips.
"Pretty good, huh?" asked her father.
"Oh my god, this is the best. Don't stop!" his daughter replied.
He continued to thrust. In and out, in and out. She moaned in pleasure. In and out, in and out.
"Oh, oh, oh..."
He felt the climax in him about to explode. "I'm going to cum," he said.
"Oh yes, Dad. In my ass, in my ass!"
She felt her insides coated as he ejaculated, "Oh yes!" she cried.
Seemingly spent, her father got off of her, and they lay there, side-by-side.
"Well dear. What did you think?"
She leaned over and kissed him. "Thanks, Dad. That was incredible!"
"My pleasure, dear. You've now been initiated into this family's tradition. We should probably do this tomorrow night, too. You need the experience. I know I won't object to fucking my brand new daughter again. I want to make sure you are loosened up some. Remember, your sister said she would peg you before the week is over."
"Oh yeah, Dad. Mom said she pegs you sometimes. How did that ever start?"
"I let her do it for multiple reasons. It's a change, and I like variety. Your mom likes it when she is the one in control sometimes. When we first dated, she let me fuck her ass on the condition that she got to return the favor. Then she showed me her strap-on. I was rather surprised, but I let her do it. It's been happening ever since when she gets in the mood. I kind of like it that way, too. So now your sister is going to show you what it's like."
"OK, Dad. I guess I'll look forward to it."
"Jennifer, I know you are just starting this life you have been given. You have experienced some things tonight that I believe you enjoyed."
"Yes I did, Dad. I can't wait till we do it again!"
"Well, as I said, probably tomorrow night. But your new life won't always be this pleasurable. When people find out what you have done, they will distance themselves from you. Your friends may ostracize you. But that just means they were never truly your friends. A real friend will stand by you, regardless of the decisions you make in life. They may not understand them, but they will accept you for who you are. It will be hard for you, but have to keep looking forward to the result you wish, living your life as a woman."
"Dad, I don't want to go back to my old life. This is my life now. I will live with the choice."
"Very wise of you, dear. One more thing. I know you are at the beginning of all this. Someday, you may choose to have a sex change. If I'm still around on this earth, I would love it if I was the first man you take to bed, once you are ready."
"Dad, it would be my honor!"
Her dad looked down. His erection was starting to grow once more.
"You know something, Jennifer? I guess this cock of mine isn't quite done yet. So why don't you let your old dad fuck your ass one more time tonight?"
"Oh yes Dad, please!" came the gleeful reply.
As her father entered her again, she smiled and thought, 'Wow, what a birthday!
