She's The Man: I Don't Care If You Are Bisexual (mf,anal)
by The Fan ([email protected])

Viola/Sebastian stood in the middle of the dorm room, after hours. The tall
tomboy looked at the figure of a tall, muscular young man who lay in bed. His
name was Duke and he was a handsome lad. The captain of the school's soccer
team, which Viola/Sebastian was also a member of, though she was disguised as
a male student under the name of Sebastian. It was a very long story and not
one she cared to get into.

Viola/Sebastian could not remember the last time she felt so confused. First,
her high school dropped the girls soccer team and she wasn't allowed to try
out for the boys team. Then, she thought of a plan. She would enroll at
another high school using her twin brother's identification to join their
boys team so she could play soccer, the sport she loved. What she hadn't
counted on was falling in love with Duke, the handsome soccer team captain.

It was so hard for her to stay away from him. He was so handsome and
gorgeous. Unfortunately, he was attracted to a bitchy girl named Olivia.
Olivia was a man-hating manipulative bitch who had a thing for Sebastian,
who was really foxy tomboy Viola/Sebastian in disguise! Viola/Sebastian
was falling deeply in love with Duke, who unfortunately thought she was a
man and she couldn't risk him finding out. He might tell on her and she
would lose her spot on the boys soccer team since it would be proven that
she was a girl.

A couple of nights ago, Viola/Sebastian had seriously considered telling Duke
but instead, she chickened out. She couldn't risk telling the boy she loved
how she felt because she was disguised as a man and he would surely reject
her. If he found out she was a girl, he might reject her for deceiving him.
If she came onto him in her disguise as a male, he would deck her. So, what's
a girl to do?

Viola/Sebastian was rummaging through the room while Duke showered with the
other male soccer players when she found something. A little black book.
Curious, the tomboy read through it. Amazingly, its contents were Duke's very
private thoughts. This was Duke's very own private diary. Viola/Sebastian
read from it, and its contents were both revealing and fascinating:

“Dear Diary,
It's me, Duke. Of course, who else could it be? These days, I
feel so confused. I mean, I like Olivia and she doesn't like
me. She's hot and all and I really want her but why does she
have to act like a witch all the time? She treats me like I'm
not even human, man. That's cold. Something weird is also

I'm starting to have the dreams again, about boys. I know. I
tried to put it behind me. I like girls, no doubt about that.
But as much as I try not to, I still like boys. Not just any
boy. I like my roommate, Sebastian. He's so pretty, he could
almost pass for a girl. I like him but he's straight and
he'd probably deck me because I'm bisexual.

Oh, well. My life is going to hell. The girl I like doesn't
care how I feel and the boy I like will deck me if I ever
tell him how I feel. I hate my life.

Viola/Sebastian read and re-read the passages of Duke's diary. She smiled
sadly. The young jock's diary revealed a guy who was full of pain. Duke
walked around like he was king of the world but inside, he was suffering.
Viola/Sebastian seethed with anger when she thought of how manipulative
and bitchy Olivia was. She was shocked by Duke's admission of his
bisexuality. Whoa, if he liked girls and guys, what did it mean? Would
one girl ever be enough for him? Viola/Sebastian looked in the mirror,
and saw her reflection.

Since Viola/Sebastian looked like a man in this disguise, and Duke did say he
was attracted to the man she pretended to be, maybe they could be together.
Oh, she would be deceiving him by pretending to be a boy but hell, she loved
him and wanted to be with him. Maybe he would forgive her. She gently tapped
Duke's shoulder. He did not move. Gently, she stroked his cheek. He was still
asleep. Viola/Sebastian placed a kiss on the lips of the boy she loved. Like
in the fairy tale, he woke up.

Duke's eyes snapped open. He woke up from a rather strange dream. He was with
Olivia, and she was naked and enticing, and they were about to make love when
suddenly, his roommate Sebastian materialized in the dream, stark naked. Torn
between a lovely female and a handsome male, the bisexual athlete screamed in

He woke up, to find Sebastian staring at him, smiling.

"What are you doing?" Duke asked Sebastian. "What do you want from me, man?"

Viola/Sebastian looked at him. "I'm sorry for waking you up like this, Duke.
I have a confession to make. I like you, man. I like guys. I want to be with

The tomboy looked at the jock, and waited for his answer.

Duke surged from bed, grabbed Viola/Sebastian and glared angrily at the
person who had woken him up.

"Look, Sebastian. I am not gay!"

Viola/Sebastian looked at the boy she loved. Sure, while he thought she was
a boy, he could smash her to pieces for coming onto him. But she didn't care.
She wanted him badly, and she would do anything to get him.

"I know you're not gay, Duke. You're bisexual. You like girls and sometimes
you like guys. That's okay. I totally understand."

Duke stared at Sebastian. He was shocked. Oh, my God, he thought. Sebastian
knows about me! I'm doomed! Nobody is ever going to accept me again. People
are going to tease and harass me for the rest of my life!

He stared at the most beautiful boy he had ever seen. "I don't know how you
know this but if you go around spreading rumors, I will mess you up."

Viola/Sebastian protested. She could never betray the boy she loved. "I would
never betray you, Duke. I like guys, and I like you, man."

Duke stared at Sebastian. Could he trust this beautiful boy who haunted his

"Promise you won't tell anyone?" Duke asked. Viola/Sebastian nodded. They
shook hands. "Cool."

The tomboy and the jock stared at each other. "I'm going back to sleep," Duke

He went back to bed. Viola/Sebastian did the same. But she couldn't sleep.
Too much excitement in one night.

"So, when did you know you liked guys?" Duke asked.

Viola/Sebastian smiled. When does a girl know she likes guys? "I've always
liked guys," Viola/Sebastian said confidently.

Duke seemed surprised. "You don't like girls at all?" he said. "I've seen you
kiss them at the restaurant. All of our guy friends saw you kiss babes back

Viola/Sebastian told him the honest truth. "It was all for a façade, man. I
wanted to blend in. those girls are friends of mine. They kissed me so I
looked like a macho man and so the other guys wouldn't suspect that I'm...

Viola/Sebastian looked at Duke. The jock was sympathetic.

"It's cool with me, man. I'm a bisexual athlete, something odd enough
already. I'm not insulting anyone for their sexual preference."

Viola/Sebastian smiled. "You know, you're a really cool guy, Duke. Olivia is
a lucky girl."

Duke sighed. "I don't know, man. I get nervous around girls. I never
understand them. They're always trying to make a guy look bad or saying
negative things about men. That's intimidating sometimes and it hurts my

Viola/Sebastian sighed. Back when she was a regular gal and hung out with her
lady friends, she did make some bad remarks about boys. Now, she regretted

"I will never say a negative remark about men in general ever again,"
Viola/Sebastian said.

Duke laughed. "Why can't I meet a girl like you, man?"

Viola/Sebastian's heart wrenched. For a moment, she looked at Duke and felt
tempted to come clean. Let him know that she wasn't a man. She was a girl.
A girl who loved him. Would he understand?

"Something you want to tell me?" Duke asked.

Viola/Sebastian shrugged. "Nope, man. Good night."

Over the next few days, Viola/Sebastian and Duke grew even closer together.
The two "boys" hung out together at school and after school. They went to
movies together. At night, they talked about their lives and fantasies.
Viola/Sebastian told Duke about the boys that "he" used to "date". Duke only
talked about girls.

"Have you been with a girl before?" Viola/Sebastian asked Duke one night.

Duke hesitated. His handsome face, which usually looked so confident,

"I've never been with anyone, man. Boy or girl. I'm still a virgin."

Viola/Sebastian could not believe them ears. Duke was a virgin! No way a boy
this fine could still be a virgin!

"You're joking, right?" Viola/Sebastian said.

Duke shook his head. "Nope. And I'd appreciate it if you didn't tell anyone
about this. The other guys would laugh at me."

Viola/Sebastian sighed. Wow! Viola wasn't a virgin. She lost it to her
ex-boyfriend, soccer star Justin a couple of months ago. That was before he
refused to allow her to join his team and she thought of this gender-bending
scheme to get back at him and his arrogant friends. Now, Viola regretted
giving up her virginity to him. She should have waited for someone like Duke.
Duke didn't say anything for the rest of the night.

One night, after class and soccer practice, Viola/Sebastian went to the
showers. The tomboy-in-male-disguise returned to the room. What s/he saw was
surprising. Duke was sitting on his bed, looking like a man whose world just

"What happened?" Viola/Sebastian asked, alarmed.

"It's Olivia," Duke said softly. "I asked her out and she called me a dumb
jock in front of everyone. Her girlfriends laughed at me and all the dudes
were joking about her busting my balls. I just took off."

Viola/Sebastian sighed. How dare Olivia treat this cute and wonderful boy
like this? The next time they ran into each other, Viola promised herself to
knock out the bitch for the way she treated Duke, and men in general.

"Forget about her, man, she's just a bitch!" Viola/Sebastian said.

Duke looked so sad. Viola/Sebastian's heart wrenched in her chest. Tenderly,
she cupped his handsome face in her hands and looked at him.

"It kills me inside to watch you suffer because of this girl, Duke."

Duke sighed. "Not my brightest moment," he said. "I'm whining like a fool."

Viola/Sebastian sighed. "You're not a fool, Duke. Unfortunately, you're out
there chasing someone who doesn't love you, and you don't notice someone who

Duke looked at Viola/Sebastian with wide eyes. Had he heard right?

"Yes, I love you, Duke. I always have." Viola/Sebastian smiled.

Duke looked petrified. Viola/Sebastian waited for an answer. When s/he didn't
get one, s/he smiled sadly.

As Duke looked on, the "boy" who was his roommate shrugged off the pain of
unrequited love and went to "his" bed across the room. Unbeknownst to him,
the girl who loved him experienced heartbreak.

Duke got up. He looked at Sebastian, the most beautiful boy ever. A boy so
beautiful he could almost pass for a beautiful girl. Did he care about
Sebastian? Of course he did. He trusted this femininely beautiful 'boy' with
his dreams and secrets. And he felt attracted to 'him'. So what was holding
him back?

"Sebastian," Duke said. "I love you too, man."

Viola/Sebastian almost jumped for joy. S/he wrapped her arms around Duke and
kissed him. "Oh, my God! I love you so much, Duke. I'm going to make you so

Duke and Viola/Sebastian kissed. "I want you!" Viola/Sebastian confessed.

Duke pressed his hard body against Viola's. "I want you too."

"So, how do we do this?" Duke asked.

His words jolted Viola/Sebastian back to earth. How in hell was a girl
disguised as a boy going to have sex with a young man without having him
discover her true gender? The tomboy thought about it, and a wicked idea
sprang into her mind.

"Any way you like," Viola/Sebastian said with a grin as she kissed her lover.

Duke picked her up in his arms. "I want you so badly, Sebastian. You're the
best friend I've ever had. And I just realized how much you mean to me."

He laughed. "I can't believe I wasted my time chasing Olivia, man. Fuck her
sorry ass, man. Fuck her to hell!"

Viola/Sebastian felt her lover's hard cock press against her navel. "That's
nice, Duke. But I'd rather you fuck me instead."

Carefully, in the dark, Viola/Sebastian undressed. She dropped her shorts to
her knees and pressed her body against Duke's, who lay behind her on the bed.
His hard cock pressed against her butt.

This requires careful handling, Viola/Sebastian thought. Any wrong move and
Duke could discover that the "boy" he loved was really a "girl".

Viola/Sebastian took Duke's cock in hand, and masturbated him until he was
hard, then she pressed it against her anus. She hesitated. Although she had
sex with her ex-boyfriend dozens of times before, she never allowed his dick
anywhere near her butt. She had always thought anal sex was dirty, something
only whores and bitches did. Now, she was doing it. She loved Duke and wanted
to make him happy. This was the only way they could make love without him
discovering her little secret.

Duke held Viola/Sebastian by the hips, and thrust into her. Viola/Sebastian
gasped as Duke's cock went into her ass. In spite of the lube, it hurt like
hell. The tomboy bit her lip as her lover thrust into her, fucking her hard.
She felt his hard cock moving into her ass, and stifled a scream.

Duke was having the time of his life. Finally, after eighteen years of doing
his fist, he was finally having sex. And he was lucky enough to do it with a
beautiful 'boy' who loved him. He caressed Viola/Sebastian's smooth and sexy,
hairless butt. He pinched them. His lover finally screamed. Seconds later,
Duke came, sending his hot cum deep inside.

Viola/Sebastian screamed as Duke's hot seed flooded her bowels. "Oh, my God!"
Duke exclaimed. "That is frigging awesome, man!"

Duke placed his arm under Viola/Sebastian's belly and pulled his lover's
lithe body to him. In the dark, Viola hugged her breasts. What they had just
done hurt like hell, though it did feel kind of good for a moment.

Duke kissed Viola/Sebastian on the lips. Viola's heart soared. He loved her.
It had all been worth it.

"No need to thank me, Duke. I would do anything for you. I love you, dude."

Duke laughed and held his lover tighter. They went to sleep. Or, he went to
sleep. Viola/Sebastian lay next to him. She had pulled it off. Made love to
the man she loved. He did not know that she wasn't a man. Her plan worked.
She didn't want to think about the future, or how Duke might feel if he ever
found out that the boy he loved was really a girl. They had tonight and
tonight was theirs.


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