Jenny lay on her bed so she could watch out the window while she dilated. It was so darn boring she thought but it had to be done. She had been doing it for almost a year now and noticed the progress. She could use the biggest stent. According to the markings she was almost seven inches deep which was deeper that normal. It was June and it had been almost a year since she had begun her vaginoplasty. The surgery itself had gone well and she had stayed four days in the hospital. Then her father paid for a recovery center where she was spoiled rotten by the nurses and other staff members for another four weeks before she was strong enough to manage by herself. She had moved back into the apartment she shared with her friend Frida who would help her when she needed it.
Jenny gently pulled out the stent and lay it next to her. Then she caressed her pussy with her eyes shut. It felt so smooth and soft under her touch. Before the surgery, she only touched her dick when she needed to go to the bathroom. She never jerked off and if she was with a man, she wouldn’t let him touch it. She hated the damn thing and had done so as far back as she could remember. Now she was free of it. She leaned over to her bedside table and picked up a round mirror. She placed it so she could see her new pussy and smiled at how pretty it was. Before surgery, she had shown the doctor a picture of the most beautiful pussy she could find on the internet. The doctor had done an excellent job she thought.
She got up, took a shower, and then dressed. The California weather was warm and sunny so she picked a white summer dress under a white thong and matching white bra. Her father had paid for her boob job when she was eighteen and her C cups sat perfectly on her chest. She had wanted D cups but the doctor had advised her against it saying that C was perfect for her 5’9” body. After a last look in the mirror, she stepped into a pair of sandals and went out to the hallway where her suitcase waited.
“I’m ready, Frida.”
“Coming.”
A few minutes Frida came out of her room dressed in shorts and a shirt tied above her navel, sexy, slutty, and her best friend.
“Ready, to see daddy?” she asked while making sure her car key was in her pocket.
“Yeah, it’s been almost a year. He works so much that he hasn’t had time to visit. It will be nice to spend a month with him in New York.”
Jenny was twenty-one and would start her last year at UCLA that fall. She studied for her BBA with a major in management. She would most likely intern for her dad before striking out on her own. Being a transgendered girl didn’t make life easier but with her father’s name attached to hers, it sure wasn’t impossible to land a good job in the future.
The flight was fine and when she landed in New York she almost ran to the exit. She looked around and there he was.
“Dad!”
A tall handsome man in his fifties rushed forward and lifted her like a doll, high in the air. “Baby girl, just look at you. I have missed you so much.”
“C’mon put me down, you are making a scene.”
“What, a father can’t hug his daughter?” he put her down.
“Off course, you can, let’s get out of here I’m starving.”
He drove them back in his Ferrari and Jenny never got tired of the sound of the engine and the force from it.
“Do you want to go and see Mom?” he asked.
“Yes, I would.”
Twenty minutes later he parked outside the cemetery and they walked in hand in hand. At the grave, they stood in silence and a tear drop ran down Jenny’s cheek.
“I’m so sad I never got to know her.”
“Me too, baby. Your mother was an amazing woman, you would have had so much fun together.”
Caren had died giving birth to Jenny. She had had time to hug her baby one time before she closed her eyes forever and Malcom’s life changed. He was now a single father managing a rather large investment company. He hired nannies and cooks so baby Alex could grow up with all he needed. Every night Malcolm would come home from work and while having his vodka-on-the-rocks bottle feed Alex and then put him to bed. He was also the person who handled everything in the morning before leaving.
Alex was about four when one of the nannies approached Malcom with some concern. The boy didn’t like to play with the other boys and when she bathed him he became hysterical if she got to close to his penis. Malcom took Alex to several doctors and mental health professionals. After almost half a year there was a decision made. Ale most likely had gender dysphoria and he would be monitored weekly. The years went on and Alex became more feminine in the way he spoke and acted. He always wore girl clothes even when he was outside with his father. Malcolm at first didn’t know what to do and signed up for a support group for parents with trans kids.
When Alex, who by now had begun using Jenny as his name was to start his first year in school Malcolm chose a private school. He had long conversations with the headmaster and the teachers about how to handle Jenny. They agreed not to make a big deal out of it and if any other student was concerned, then they would address it. The only issue was the bathrooms and changing rooms for sports. Jenny wanted to use the girl’ and they all agreed they would try it.
By now Jenny was taller than the other kids her age. She had long flowing black hair just like her mother had. She had green eyes and would pass as a girl at first sight. But if you looked at her for a longer time you could see differences and the kids picked up on it the first day of the year. Some concerned parents called but in the end, everything worked out and Jenny spent the next eleven years at that school, making good friends and amazing grades. As a graduation present, Malcolm bought her the C cups and she was the happiest girl in the world.
“Let’s go home, Dad.”
He took her hand and they walked back to the car he drove them the short distance to the building where he lived in the penthouse.
While Jenny unpacked, he made them dinner and then they ate and Jenny told him about the hardship she had gone through post-op.
Malcolm had difficulty understanding how a perfectly fine dick could be turned into a pussy in a few hours. It was beyond his comprehension. Jenny, who was so proud of her pussy stood up. Walked around the table and pulled up her dress.
“Hey, wait, stop, what are you doing?” he said.
“C’mon, you have seen me naked before. I just want to show you.”
She pulled down her thong around her knees and then pushed her hips forward.
There it was. A perfect pussy that looked a lot better than some of the ones Malcom had seen. He had begun dating about five years after Carol’s death and being a handsome and rich man, he never had problems finding a date or getting laid.
“Wow, that’s amazing.”
“Go ahead, touch it.”
“Nah, I don’t want to.”
“Ok, fine, but look.” Jenny pulled her pussy apart a little. “You see, looks just like a cis pussy, doesn’t it?”
Malcolm was quite uncomfortable and looked away. “Sure, but please put on your clothes again.
Later that night he couldn’t stop thinking that he now had a complete daughter. Ever since that first diagnosis many years earlier Malcom had difficulty understanding how someone could be transgender. He had read all the literature and been to meetings and talks but still, it was hard to come to terms with. He never spoke to Jenny about this, not wanting to disturb her. Seeing her standing before him with a grin on her face displaying her newly made pussy made him finally understand. The road she had traveled since a child was now pretty much at its end. She had completed herself and would now be a woman in all its meanings, or at least as much woman she could ever become. Having children was of course out of the question but as far as he knew, Jenny was not one of those girls who dreamt about having a family. Her studies and later her career was all she thought of. He felt his dick grow hard when he thought back to her pussy and that scared him. He turned on his stomach and sighed before closing his eyes.
Jenny slowly rubbed her clit under the sheet. It was a strange and magical feeling she thought. She used lubricant so she could slide a finger or two inside her and feel the warmth and tightness of her pussy. This was the first time she had masturbated after the surgery. It took a while but eventually, those waves of pleasure ripped through her and she gasped while her fingers rubbed her clit faster and she arched her back before she slumped down on the bed gasping for air. Holy fuck, she thought. If it was this good with fingers, how would it be with a real cock?
She hadn’t thought much about sex until a couple of weeks earlier when she realized that her new pussy was healed and she could have sex as a woman for the first time. God, she was often horny and watched men like a cat watches a mouse. She would fantasize about the different positions and how it would be when one finally penetrated her. She was so ready for cock it was ridiculous and New York in the summer had many men to choose from. There was only one little problem. She was transgender and she didn’t know if she should tell the man she would be with before or just be quiet about it.
The following day she signed up on a couple of dating apps. She took several sexy pictures and added them to her profile. Nothing nude but in a few cute and sexy bras and thongs. She didn’t say she was trans to avoid the men who were just curious and wanted to see a chick with a dick, which she didn’t have.
By noon she had so many messages that she didn’t bother reading half of them. Most were just straight-out booty calls to fuck as soon as possible. Some were from older men offering her money and a small amount were genuine men who wanted to have a coffee or dinner.
“Jenny.”
“Yeah, Dad?”
“I’m having some friends over tonight for a game of poker. Do you want to join us or are you going out?”
“I have no plans. Do they know I’m trans?”
“No, they don’t. All they know is that my daughter is visiting for a month.”
“Cool.”
Jenny dressed in a short skirt and a white blouse showing a little cleavage without being slutty. She put on her makeup and put her hair in a ponytail. Nothing too fancy, but just sexy and professional enough. She hoped to make some good impressions on these men. You never knew who you might meet and making contacts in the business world was important.
The three men arrived separately. The first was Harry, an older gentleman who had been in banking his entire life and was looking forward to retirement later in the year. Then came John. He was the same age as Malcolm and they often played tennis together. He was tall and fit. When he met Jenny his eyes grew wide.
“Wholly shit, Malcolm. Are you sure you are the father to this unearthly being? She is out of this world. What a beautiful daughter you have.”
Jenny blushed and shook his hand. “He is my father, but I guess I got my mother’s genes.”
Last to arrive was a young man, who Malcolm knew through his work. His name was Robert and he worked for a different investment company Malcolm often did deals with. He kept on eying Jenny while talking to her father. He is fucking me in his mind, thought Jenny standing by the poker table holding a glass of white wine. She had already shaken his hand and when she did, there was something there. Robert was a handsome man. Blondish hair, and a square jaw, like one of those GQ models.
Robert could hardly take his eyes off Malcom’s daughter. He was thirty-five but had a thing for girls in their early twenties. Usually, they had had some dick by now and learned to love it. Their fit bodies and smooth skin would drive him crazy and he loved fucking at least two a week if possible. He wasn’t so sure fucking Jenny was a good idea, considering he was good friends with Malcolm and they had business dealings together. So, he decided to leave it to Jenny. He could always say she came on to him.
The game started and Jenny lost in the beginning but after they had had refreshments she came back and took several large pots. At one time she excused herself to go to the bathroom. When she came out Robert stood waiting for her.
“Hi there.”
“Hi.”
