From Tomboy To Boy

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A girl becomes a man.
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Mike Flannigan is a wealthy man who, at the age of forty, could certainly afford to retire from his law firm with a lot of money to spend. He had always been the most driven person in his family. He was born in 1951 in Dallas and lived there for most of his life. His parents were a working-class couple, a policeman and a teacher. Mike Flannigan went to college and eventually became a lawyer. By the age of thirty, he was a partner at his own law firm of Flannigan And Associates.

Mike Flannigan is the kind of guy who believes in living well and working hard, not necessarily in that order. He never married, but his sister Nicole certainly did. Nicole Flannigan was a year older than Mike. She got married to her sweetheart Jason Green right out of college. He was an accountant and she was a reporter. They did fairly well for themselves in Dallas. They had twins, Luke and Nancy, born in 1980. Both of them were in college now. Mike Flannigan had never been a family type of guy. He preferred flying solo, to tell you the truth. He never married, nor did he ever come close. He was a lifelong bachelor. He had a relationship with a woman named Michelle O'Shea once. Michelle O'Shea was a barrel racer and teacher down in Amarillo. A really fun and exciting gal. They were together for eight years. Their relationship ended when she asked him to marry her. Mike didn't want to get married.

He never really discussed it with Michelle. From early on, Mike had discovered that he felt a certain attraction to men. While in college, he had a few discreet sexual encounters with young men he met in bars and clubs. He even had a two-year relationship with Blake Alton, a young black man he met in law school. Blake Alton was a good-looking stud who also happened to be married but he still had dealings with men on the side. They split shortly before graduation. Blake and his wife Susan had decided to move to Memphis after she got her Bachelors degree in nursing. Mike hadn't let anyone, man or woman, get close to him since. And although he deeply cared for Michelle, he wasn't about to marry her. Mike's parents divorced while he was in high school and he didn't want to go through that. Ever.

After his retirement from the firm, he decided to move elsewhere. He had recently bought a house in Boston's Back Bay. It cost him six hundred grand. He liked the neighborhood. He had to get away from Texas. He was fed up with his home state. Too many people down there hated his guts. He had made powerful enemies in his day. From the sheriff's department to the district attorney to the head of the Women's Caucus. Yep, the guy had enemies. Nobody gets to be a multi-millionaire without making a few enemies. For these reasons, and a few others, Michael Jerome Flannigan moved to Boston. What he didn't know was the hidden history of the neighborhood in which he lived. The Back Bay was very queer-friendly, something that the Texan lawyer didn't know when he first moved in. Although Mike had a few sexual encounters with men in his day, he didn't consider himself to be gay. Maybe he was a bit more bisexually inclined than the average male but he didn't think of himself as queer. Queers were flamboyant guys in pink. He certainly wasn't like that.

Mike liked traveling in New England. The places he saw fascinated him. The whole region had so much history and culture. It was so different from Texas. He liked it. He was away from home so often that he hired somebody to take care of things while he was gone. He interviewed several people and finally settled on a tall, slim black girl named Ryan. Ryan had short hair, brown skin, delicate features and walked with a somewhat masculine gait. Mike rolled his eyes when he saw the broad. Oh, well. There were so many queers and dykes on the Back Bay. She didn't look older than nineteen. Mike hired her to clean the house and maintain the gardens.

One day, Mike returned early from a trip to Plymouth. He entered his house. That's when he got the surprise of a lifetime. He went into the bathroom to piss, and saw that there was someone already there. Ryan stood in front of the toilet, and was taking a piss. Mike's eyes went wide when he saw Ryan's big black cock. The chick had a dick! Ryan turned around, and gasped when she saw him. She blurted out that she could explain. Mike recoiled. What the hell was that? Mike had never seen anything like Ryan, at least not outside of porno DVDs featuring transsexuals. Damn!

Ryan came out of the bathroom and looked at Mike. He stared at her. He wouldn't tolerate a chick with a dick working in his house. No way! That would be too weird! Ryan looked at him imploringly and pleaded with him to let her explain herself. Mike agreed, however reluctantly. Ryan told him of her birth as girl and how she felt she always was in the wrong body. Mike listened. In spite of himself, he was moved. He had heard stories about male-to-female transsexuals, men who felt the were born in the wrong body and decided to become women. He had never heard about, much less met, any women who wanted to become men.

Ryan told him about how she took hormones and underwent several surgeries to become a man. Recently, scientists went ninety percent of the way in matters of surgeries and hormones. Ryan now had male genitalia. She wasn't a shemale. She was a female-to-male transsexual. She was a woman who wanted to become a man. The next step for her would be to get rid of her breasts and pump herself full of testosterone so that her feminine outside could give way to her masculine inside. The way Ryan saw herself, she was a man living inside a woman's body. Trapped. Ryan wanted to become a man. Mike listened, fascinated.

Afterwards, he offered Ryan a drink and heard a bit more about her story. Ryan had always been a tomboy. She played soccer, volleyball and even football with her guy friends. And she was pretty good at all of those sports. In high school, she tried out for the men's hockey team and she made it. She was a pretty good hockey player. With her guy friends, she used to play backyard football. She never wore a dress in her life. Hell, she never had a single female friend. Girls didn't like her because they could sense that she was different. Underneath her feminine exterior, she was a man. Deep down inside, Ryan was just one of the guys.

Mike watched this brave young person who sat near him. He listened to Ryan's tale of gender identity crisis. Ryan the tough tomboy who wanted to become a boy. Ryan, the chick who played on the guy's teams. Ryan, the chick who got suspended from high school after beating up one of her teammates girlfriends. Apparently, the girl had hit one of Ryan's guy friends and the guy had walked away. That didn't sit too well with Ryan. Ryan had no problem beating on females. Ryan was very aggressive on the ice but also fiercely protective of her male friends while off it. She considered her teammates to be like her brothers.

When Ryan was done, she looked at Mike. The older man watched her, fascinated. He decided to be honest with her. He told her about his life in Texas, and his adventures in the worlds of bisexuality, politics and Racial Issues. Ryan listened to Mike as he spoke. There was definitely more to the older man than she originally thought. Here she thought he was an arrogant and pompous rich older man. Well, there was more to him than met the eye. He told her about his life, and the men and women he loved. The life of a bisexual man living in Cowboy country. As he spoke, she realized something. He was amazing.

Later, after they had bared their souls to one another, they sat there. Mike suddenly had a brilliant idea. He asked Ryan to go to the bars with him the next night. Whether Ryan considered herself to be a woman or a man, he considered this beautiful transsexual to be someone interesting and he was curious about going to town with her. They went to a gay bar on the Back Bay. Ryan was dressed in a blue T-shirt and jeans, with a durag on. Her usual, butch girl self. Well, butch-girl-who-wants-to-be-a-boy self. They had a blast. Just hanging out at the bar, drinking and flirting with hot guys. A bisexual stud made a pass at Ryan, and she flirted with him, until his boyfriend arrived and told her to back off. Ryan laughed and went back to Mike.

They headed to a gay club next. There were dozens of guys dancing with other guys there. It was a lot of fun. Mike reveled in the sight of sexy young men dancing with each other. He danced with Ryan, and also danced with a Latin stud named Ricardo. Ricardo's boyfriend Ramon came by and Mike went back to Ryan. Nobody in their right mind wants to deal with a jealous queen. While dancing together, something fabulous happened. Mike and Ryan kissed. It was a surprise for both of them. They smiled and giggled. Gay guys around them laughed. In their eyes, Mike was a straight man kissing a black tomboy. Essentially, they were a straight couple. If only they knew what Ryan was packing between her legs!

The next morning found them in bed together. Mike looked at Ryan's body. She was a slender, curvy black girl with a hot booty. Yet she had a big dick. His hand reached for her cock. Ryan smiled as he stroked her. He went down on her, taking her cock into his mouth. He sucked on her cock and balls. They felt and tasted real. The surgeons had done a remarkable job in transforming the black tomboy into one of the guys. Ryan cried out in pleasure as he sucked her off. Finally, she came. Mike watched, amazed. Ah, the wonders of science. He drank her seed. Licked her clean.

Ryan smiled at him, and decided to return the favor. Mike watched as the sexy female-to-male transsexual began sucking his cock. Her head bobbed up and down as she sucked his cock and licked his balls. She sucked him until he was rock hard, then climbed on top of him. Ryan lowered herself onto his member. Mike thrust into her. He looked at her. A beautiful young black woman who decided to become a man. She was pumped full of testosterone and no longer had a vagina. Scientists had replaced her vagina with a man's plumbing. He thrust his cock into her asshole. Ryan cried out. He held her by the hips and fucked her. Slammed his cock inside her. It felt so damn good. He came, and pulled out.

Later, they lay in bed, sleeping. A bisexual man lying in bed with his lover, a young woman who was on her way to become a man. Yes, biologically. A chick with a dick. Unlike most chicks with dicks, Ryan wasn't a guy who took hormones to become a woman. Ryan was a girl who wanted to become a man. Mike woke up and looked at Ryan. She was something else. He liked her just the way she was. He couldn't stand women and he couldn't stand men but he liked her. She was somewhere in the middle. Just like he was in the middle, as in bisexual, when it came to the opposite poles of sexuality, which were of course homosexuality and heterosexuality. Maybe he had found the right person to be with.

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AnonymousAnonymousabout 10 years ago
lack of research

Well written. But you obviously know nothing of transmen. You're better off writing about other things. Youre completly misinformed and should of done more research. Transmen are men, not butch woman she he wanna be men. Youre confusing sexuality with gender. When transmen elect to go through any of the things you name, there gender is male. You don't just call them she, that would completly butcher the process of going through there transition, to just still be called the same sex that is imprisoning them. This is bad, and an embarrassment for trans men.

AnonymousAnonymousabout 10 years ago
from one transman to someone whos attempting to write a about one

Im not going to be rude about it. But I need to inform you to correct something. When talking of a female to male in context as you were. They don't go on hormones, and get the surgeries to finally distinguish there sex from others. They ARE that sex, so that means no matter what stage of there transition they are in, you use male pronouns. Usually I don't care, but you make it sound like this person was making a split decision in there head like it's a trend or a choice. It's not a choice, just like it wasn't your choice to be born as you were. It's not a matter of wanting to be a man, they are. She doesn't want to be a man, HE wants to correct natures mistake. Aside from the slight uninformative blunders, it is a great story. However if you choose to write about us, write us how we are. Young men, with a different journey. Getting there pronouns wrong is the most insulting thing you can do

jenellesljenelleslalmost 13 years ago
Felt Incomplete

There are more FTM than people realize. For a lot of reasons, bottom surgery isn't done often. It's very expensive and not as refined as surgery for MTF.

I found this a bit rough. Some of the paragraphs were a bit disjointed and the sentences didn't flow well.

The ending was a bit abrupt. I see more here. He likes her the way she/he is. She wants to be all boy. There could be some conflict there that needs some resolution.

Overall, good as far as you went.

AnonymousAnonymousabout 13 years ago
Need more stories with chicks growing dicks!

Whoever said your story is not well researched didn't do their research either. Seriously Google search: "mega_clit_on_webcam" or "jacking_off_a_huge_clit"

Slits can almost completely become dicks given the right conditions & can even ejaculate female fluids!

Chicks growing dicks are HOT!

All women should grow dicks!

AnonymousAnonymousabout 14 years ago
Great.

"From Tomboy to Boy" - I often fantasize about this scenario: a bisexual woman decides to become a man complete with penis. Testosterone, muscle building, the whole thing. What do you think of female bodybuilders with their enlarged clitorises? That may be the closest thing.

Please explore this theme further - perhaps with a story in which a man and his wife come to the conclusion that she should follow her dreams and become a stud ... saving their marriage!

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