The Pick Up

Story Info
Feminized by an angry girlfriend, he waits on a corner...
1.9k words
4.43
27.6k
20
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

The Pick Up

A Short Story

By Maryanne Peters

It was a late model Corvette -- electric blue. It pulled over close to the fountain and the passenger window whirred down.

"Are you Jake?" The question seemed wrong, but this was the redhead in the short black skirt and heels. She was examining her long hair and looked up to speak to the driver.

"Yes, I am. Who are you?" Her voice was incongruous. Masculine but not completely male.

"My name is Omar. Mary couldn't make it. She sent me around. Hop in."

Jake paused. It was not the fact that this was a stranger. He was stranded and he needed the lift. This would not be easy. The car was low. The skirt was ridiculously short, and "the stylists" as the bitches called themselves had his package taped down tightly. Could he even get into this car?

Butt in first and swing the legs around. That is what they said. Omar had pushed the door open a little. He dropped into the seat. His shoes were bought around, heels that he had trouble walking in, and his little matching clutch bag into his lap. Yet another task done.

"You must have a story to tell," said Omar. Thankfully he was not laughing.

"It was Mary's idea. She said I always looked like a slob with my long, oiled braid and wispy black beard. She said she would pay to have me look better presented to go out tonight. I just had to go around to this salon in the mall. And look what they did to me!"

"You look nice," said Omar. "Real nice."

"Those bitches took my clothes. Then they gave me a glass of wine with a roofie or something. They ripped every hair off my body. They straightened and dyed my hair!"

"That reddish color suits you," said Omar. "It looks good with your green eyes".

Jake looked at his driver in disbelief, but Omar was pulling out and now looking elsewhere. Jake reached up and pulled down the vanity mirror. "My eyes are green. Nobody notices but I guess the eyeliner makes it more obvious." His eyes did look good with a dark surround.

"You have great legs too," said Omar.

Jake was suddenly conscious of how naked they felt without hair on his body, and how pale they looked. But this guy was right. Those legs did look good. He spotted through the open toe that his toenails hand been painted red like his top, the same color as his fingernails. Somehow they made the whole thing come together. Mary was right -- he never paid much attention to his appearance, but this is not what guys are about. Women have more scope.

"Thanks for doing this, Pal. You have a really nice car here. Are you driving me to Mary's place, or my place?" Jake asked.

"We're going straight to the party," said Omar.

"Mary won't want her date looking like this!"

"Mary is going with John," said Omar. "You're my date tonight. And you look absolutely perfect to me."

"You're kidding!" Jake was in shock. "Did Mary arrange this? That bitch."

"She said that you were complaining about how easy it is for girls. You told her that girls just have to look good and give a few favors and they can live a life of luxury without any effort or any pressure on them."

"I did say that," admitted Jake. "It's true don't you think? You're a guy."

"I think it's the way it ought to be," said Omar smiling at his passenger. "Men like me live to give women all that they need. Maybe you will find that out?"

"In return for favors? All men want something in return."

"Not all men get what they want. Some men deserve it, and some don't. Tonight you can give me only what you think I deserve," he said, changing up a gear and accelerating along the straight road.

"Me?" Jake was trying to work out what was happening here.

"She said that you need to find out how easy it is for girls. Giving you a boyfriend is a head start. That's me. I promise to look after you, and try to make you happy. What will you do?"

Jake laughed out loud -- a deliberate male laugh. He stopped himself and turned it into a giggle. "I will massage your ego, of course," he squeaked.

"Perfect," said Omar. "And no eying up other guys."

"There's only one man that I am girl for," Jake breathed. He stroked Omar's arm playfully. He could play this game. He could see out this joke. But Omar's arm felt like teak. This guy was built. Jake felt suddenly quite weak and vulnerable.

"Can I call you Jacinta," Omar asked.

"Sure," said Jacinta.

As they drove on she checked the contents of the bag she had been given. A folding hairbrush, Lipstick, mascara, some tissues, and a tampon -- clearly a joke item -- and a there was no money or any sign of Jake's credit cards.

"I have no money," she said. "But I guess that I have a boyfriend -- right? Like I said -- easy for girls."

Omar smiled. He pulled over beside the large house overlooking the bay and got out to open the door for Jacinta.

"If we see Mary and John maybe you should put you arm around me?" Jacinta suggested. "I just want to push her buttons a bit."

"We both want to push some buttons," said Omar.

They walked inside. Things were well underway. Jacinta felt curiously confident.

"Jacinta," she said to the first stranger who approached. "This is my friend Omar." For some reason it felt good to say that too.

"There they are," said Omar. "Just give them a wave and I will give you a cuddle."

John and Mary were standing together talking. They looked across and Mary waved. Jacinta gave her a fake smile and turned away to look at Omar.

"Now that's done I just don't want to look at them," said Jacinta. "Or even run into them."

"Then we will grab a drink," suggested Omar. Near the kitchen there was a line of tequila shots. Jacinta downed three.

It seemed like she knew very few people there, but with the alcohol on board she was ready to meet a few. Rather than the liquor working against her feminine pretense it seemed to encourage and improve it. She appeared female, she felt female and so she acted female. It all seemed so much easier that she thought.

"It's like I told you, Omar," she said, chinking another shot to his matching glass. "It is just so easy for girls. You just have to look good, and I do."

"You do," said Omar.

"Fuck, Mary is coming over. Can you give me another one of those? I really don't want to talk to her. It will just make me mad. Oh, Mary... hello mwah, mwah." She air kissed each cheek like Jake had seen her do a thousand times.

"How are you finding your time as a girl," Mary smirked.

"It just proves everything I said," Jacinta trilled. "You find the right man. A man who can let you live a life of luxury without any effort or any pressure." She gripped Omar's arm tightly, and for extra impact she looked up at him adoringly, and he looked down at her the same way. But somehow his look for her did not seem an act. Jacinta felt something strange. Perhaps it was unease, perhaps embarrassment, although it did not feel like either.

"Let's go Baby," said Omar. "Excuse us, Mary." When they were down the stairs he added. "Did I do right. You told me that you did not want to be near her, so I brought you down here."

"You know your way around this place."

"This is my house," he said. "This is my bedroom."

"Whoa," said Jacinta, suddenly feeling a little uncertain on her feet. "You are not expecting anything from me, are you? You told me it was up to me to give you what I think you deserve. So don't get any ideas." She put on a mock frown and playfully punched his arm

"What do I deserve?" Omar grinned at her.

"A kiss maybe?" Her head tilted to one side in a playful manner that seemed to disclose just how much she was enjoying this -- how much she loved being a girl.

"Alright," he said, pulling her into the enormous and opulent room. There was the sound of a party above them, and the view of the bay in front of them. It was a dream home. It was clear that Omar was rich.

Somehow that made the kiss all the more deserved.

His tongue was in her mouth and her moth was yielding to it. Jacinta was yielding to him. Her body was suddenly weak, only kept standing by his strength. Somehow there was just enough strength in her arms to raise them and drape them around his shoulders.

She could feel her hands in his short hair, holding their mouths together. She could feel his hands drop to unzip her skirt and let it fall.

Somewhere among the forest of duct tape in her crotch, a tiny faux clitoris struggled to emerge, and then surrendered.

The tape had cleverly left her rosebud exposed, between strips across both buttocks. She found herself lying on the bed with her legs in the air, and the access to her body exposed to the gaze of a man, and somehow that did not seem wrong. There was that look on his face. Not lust but the same look that he had for her when she clung to his arm in front of Mary. He was hers, and she was his.

"I have lubrication, Baby," said Omar. "I want to make sure that I don't hurt you."

She looked into his eyes with trust. She felt his warm finger and cold jelly from some unknown source, gently worked into her. It was the first time anything had passed through that portal, as it now quivered with anticipation.

"Yes. Please be gentle. Yes." She seemed more than ready to receive - she was welcoming.

She dared not look. It was no surprise to her that Omar was big, but he felt even bigger than anybody could imagine. It seemed as if no human anatomy could accommodate something that large, but somehow the fact that the stretching just kept on happening was its own thrill, and then he was inside her and it just seemed right.

He paused for a moment before he started his rhythmic strokes, gentle but firm, in increasing tempo. Jacinta gasped, and groaned, and then she heard the noises from his mouth - the sound of a man being gripped by pleasure. It is a sound that brings its own joy to a woman, even a woman like Jacinta. It was the first of a series of thrills, culminating in the the big one, when she felt him convulse and his fluid fill her.

She had taken another human being into her body. It is not a feeling that a man can know having sex as a man does. He is simply using his organ. So many has never experience the true body only achieved by allowing entry.

It made her smile. It made her look up at Omar's face and smile. Now she understood what a woman gives for everything she receives. She gives herself.

The End

© Maryanne Peters

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
7 Comments
MaryannePetersMaryannePetersabout 1 year agoAuthor

Much of my short fiction sees a guy forced by circumstance or duress (rather than torture) to present as a woman, and then find themselves comfortable in the role. I do not do magic, because as I often say, the best fantasy is one that might just happen - don't you think. Some of my storylines are very unlikely, but I like to think at least plausible? It helps if you think of these key character as being trans-in-denial.

keep reading and I love all comments.

Maryanne

DickStiffDickStiffabout 1 year ago

Unbelievable, you could at a push call it a fantasy?

EricaDoesNowEricaDoesNowabout 1 year ago

reading one of the comments, I wonder HOW they got to Literotica. It's FICTION, even if there are elements of truth. I simply don't understand some folks. Loved the story, Hon!

BrendaNWBrendaNWabout 1 year ago

Lovely and well done ☺ 😘

AnonymousAnonymousabout 1 year ago

Just not believable and hardly forced. A straight guy is knocked out, dressed like a woman, taken to a party where his girl is with another guy and she's magically a convert? I don't think so.

Show More
Share this Story

Similar Stories

The Babysitter Babysitter guy becomes babysitter girl.in Transgender & Crossdressers
Mommy's New Daughter Pt. 01 Mother and friend think of an unorthodox punishment for son.in Transgender & Crossdressers
The Substitute Housewife A young guy is forced to take the place of his boss's wife.in Transgender & Crossdressers
Popping His Cherry She finally makes him her woman.in Transgender & Crossdressers
What My Wife Doesn't Know Cheating / wearing lingerie / submission, then dominance.in Transgender & Crossdressers
More Stories