All her life, Dana had felt different. Born a boy, she always preferred dressing in girl
clothes and playing girl games. She was mistaken for a girl from the time she was
toddling – her feminine face and manner always convinced people. By the time she
graduated high school, Dana discovered her main sexual interests
were in straight men. She didn’t care for gay men, and acted as a lesbian when she
was with women sexually. She had no interest in taking the male part and thrusting
her cock inside of them.
Then, when Dana was 22, she discovered what could have been a dangerous pasttime.
She dressed up as a woman and picked up straight men. Her elegant long legs, tiny waist,
heart shaped face and rounded butt convinced many a man to take her home with him.
She had given over 100 straight unsuspecting males blowjobs while fending them away
from her crotch. She drank over 100 loads of cum while her own cock was craving
release – she would run home and masturbate afterward.
And when she realized how fully she could look like what she felt, a female, her
whole lifestyle changed. She quit her job and spent a couple months off work.
Dana grew her hair, bought a whole new warddrobe and took to life as a woman.
She had the most fun choosing the frilly and lacy lingerie to compliment her
female appearance. Wearing a satin bra and panties always made her feel sub-
missive and feminine and horny.
Dana’s old apartment had been almost, but not quite, feminine. There was
always the family member or coworker to impress that Dana was a sort of
normal man. Now she wanted to be a normal woman. She got a beautiful
4 poster bed with a canopy, and got a matching apricot colored comforter and
sheet set. Her apartment had more art, more light and color. She felt as if she
really belonged there.
Then she went out to see if her new femininity would attract some fun. She
went to a part of Hollywood known for shemales – no sense in attracting trouble
when things were going so well! And within 20 minutes, Glen had come over
and introduced himself.
Glen was handsome, blond and buff. He was the sort of man who opens doors
for women and lights their cigarettes. He make Dana horny and yearning within
30 minutes of conversation with him. She wanted him to fuck her – fuck her hard!
She had sucked a lot of cocks, but had very very rarely been laid, and always
in secret – very brief and not passionate.
Dana took Glen back to her new apartment. He seemed to really like it. He
looked at home on her new couch, and sipped at his drink while looking around.
He complimented some of her art while easing gently toward her on the couch.
He put his arm around her shoulder – just like a man on a date with a woman.
Dana felt so excited – and felt her cock hardening.
Glen started kissing her – long, slow, wet kisses. He pulled her close and began
stroking her back. Dana sucked on his tongue. His mouth was warm and spicy.
One by one, Dana was stripped of all her clothes while Glen remained dressed.
She did manage to open his shirt buttons and stroke his chest hair and tease
his nipples. And then came the moment she was dreading – Glen pulled off
her panties exposing her cock. She had spent so many encounters hiding her
dick that she felt very scared.
Dana didn’t worry for long. Glen took her hard she-meat in his hand and
began stroking her shaft. Dana couldn’t believe how good it felt to have
another person playing with her shaft. She started to open Glen’s pants, but
he gently pushed her hands away. “I like to treat my women right” he said.
And he did. He sucked her nipples, carressing her ass and squeezing her cock
till she was panting out loud. He ran his finger up the crack of her butt,
teasing gently at her anus but not entering it. He licked her chest, her neck
her firm tummy. He told her she was sexy and how much she turned him on.
Then he told her to stand in front of him.
Dana felt exposed and helpless standing there, just as a real woman would.
And then Glen did something that made her crazy – he took her dick in
his mouth and began sucking!
Glen pulled on her buttocks to keep her closer to his face and sucked and
licked her shemale cock. He teased it with his tongue. He blew on it. He
would reach up and pinch one of her hardened nipples. Sometimes he would
pull her ass cheeks apart hard. Dana had never experienced such unbelievable
sex, and was helpless before such horniness.
Then Glen pulled his head up. “Do you want to cum?” he asked her.
“Yes” Dana answered, surprised at how breathy her voice sounded.
“Then tell me how much you want it” Glen told her.
“I want… I want to cum” Dana told him unsurely.
Glen gave a couple hard sucks on the tip of her cock. “Tell me how much you
want it” he demanded. “Beg me for it.”
“I want to cum” Dana said, feeling her balls contract. “I really need to
“That’s better” Glen told her, stroking his cock. “I want to swallow your load,
baby. I want to make your pretty cock shoot for me. Show me how bad
you want it – show me!”
And he began sucking again, a little faster, his other hand carressing her
balls. Dana’s cock moved in and out of Glen’s wet mouth. She wanted
to cum fucking his face – she was desparate for release.
Just then, Glen spat on his fingers, and went back to sucking. And he
suddenly slid two fingers into her tight ass-pussy. She felt her balls
contract and felt her shedick squirting hot thick jizz. Glen sucked it
down greedily, like it was candy. He sucked hard, and wiggled his fingers
inside her virgin butt, and she had never cum so hard in her life. She
shot the biggest load she could imagine, all the time writhing and gasping.
And then he kissed her again, and she could taste her cum in his mouth!