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Shanna Does Manhattan

Shanna's desperate quest to become a complete person

It was an all-too-familiar scene. I met with a handsome guy for a drink and some conversation Yes, you've read that story before. And you know how it ended. Twice, in fact. First with Kyle, and then with Matt.

The flavor of this week was Sean. He had responded to a personal ad in which I clearly stated that I was a T-girl. So he knew when he sat down with me that I was not like other girls. Sean was a confirmed tranny-chaser.

He was about five years older than me. Not too bad looking, but certainly no model or movie star. He was thin, had a mop-top bush of dark brown hair hidden under a red "goober" hat. He had mysterious brown eyes. And he was very intelligent. But he was also somewhat less than perfectly masculine. He wasn't the type of guy who had "straight" written all over his forehead in big bold letters. It was more like "straight" followed by a big bold question mark.

"So if you don't mind me asking," I said. "What is it that attracts you to girls like me?"

"Well that's a pretty loaded question," he said.

"Start unloading," I said.

"Well, I like your courage," he said. "You know, living as a transgendered woman in a world where not everybody understands you. I like that girls like you know what they want and aren't afraid to go after it, no matter what the cost."

"Very good answer," I said with a smile. "I like you."

"And of course," he said, taking hold of my hand and caressing it for a minute. "It doesn't hurt that you have a little extra, if you know what I mean."

I took my hand away abruptly.

"I know exactly what you mean," I said. "And you should know that I would do anything in the world to get rid of that something extra if I could. Anything."

"Why?" Sean asked. "It's what makes you different. I mean, you're a chick who can both fuck and be fucked. Who wouldn't want that?"

"A complete woman," I answered. "And that's what I intend to be. Why? Because I know what I want and I'm not afraid to go after it, no matter what the cost."

And so the story began...


I had made an appointment with Dr. Ginsburg, a prominent sexual reassignment surgeon in the Tri-State area. Together, we went over surgery options and discussed them in detail.

"The most common technique is known as the Penile Inversion Techniue," he said, pointing to a chart. "Here, we create a vaginal canal from the skin from the shaft of the penis. The head of the penis is later converted into a clitoris."

"Those don't look like very good results," I said.

"There is another procedure, known as the Suporn Technique, developed in Thailand by the world-renown Dr. Suporn," he said. "Here, the vaginal canal, the labia, and the vulva are all created from the scrotum, while the head of the penis is converted into a clitoris, as in the Penile Inversion Technique."

"I like those results," I said. "You can't even tell."

"That's because the male scrotum is simply a vulva and labia that fused together in the womb, thanks to the Y chromosome. It's the same structure," he said.

"In any case," he continued. "The chances of being able to achieve an orgasm are about fifty-fifty. For the rest of your life, you will need to dialate using a dildo or vibrator to prevent the vaginal walls from collapsing and fusing together."

"Okay," I said. "So here comes the obvious question. How much does all this cost?"

"Fortunately for you, you won't be needing facial feminization surgery," he answered. "You don't need breast augmentation. You don't need electrolysis. Your voice is fairly feminine, thanks to the hormones you began taking at 16....

"...But the sexual reassignment surgery is a bit pricey."

"Ballpark figure?" I asked.

"About fifty-thousand," he said. "Most insurance plans don't cover it. But some do. You might want to check with your employer. And if they don't cover it, we offer something called Care Loan, which helps patients pay for cosmetic and elective surgical procedures. Would you like to see if you qualify?"

I had nothing to lose.

"Sure," I said.

Dr. Ginsburg left the office for a few minutes. To me, this might as well have been a lifetime. Then, he returned.

"I'm sorry, Shanna," he said. "We weren't able to get an approval, based on your income and credit history. But do check with your employer."

The next day, I had a meeting with Fiona, my boss.

"I'm sorry, Shanna," she said. "Our insurance plan covers hormone replacement therapy and counseling, but not sexual reassignment surgery. That's considered a cosmetic procedure."

Two doors slammed in my face in as many days. My completion as a human being was blocked by my income, my student loans, and the fact that I was not fortunate enough to live in a liberal country with socialized medicine covering transgender medical needs.

I was crushed. My dream of finally having the body of the person that I had always been in my mind was slaughtered by a very rude financial awakening. This is the reason why most T-girls are pre-op. They don't want the "something extra". They're stuck with it.

But I was determined.

I was reminded of that horrible day when I was stuck in the middle of West Virginia on the way to New York. A perfectly disgusting man used me as a piece of human meat and fucked me in exchange for fixing my car so that I could come to New York to pursue my dreams.

My best friend, Monica, once told me that I have assets and that I should use them to get what I want. As the West Virginia incident proved, I wasn't too proud to get dirty and if I wanted something bad enough, there was no road too low for me to travel.

Self-respect be damned. I wanted to be complete.


They say there are three ways to get what you desperately want: beg, steal, and borrow. It was clear to me that borrowing wasn't going to happen. I didn't savor the thought of being sent to a mens' prison where I might not even be able to take my hormones, so stealing wasn't an option either. That left begging. Panhandling, if you will.

I set up a website in which I described my sob story in exquisite detail. At the bottom, I asked for donations for my surgery fund. I even set up a bank account so that charitable and understanding souls could help me with the one thing I wanted most in the world.

After a few weeks, this turned out to be a bust. There was one very kind man who donated $20. This was as much as I was able to raise.

$20 down, $49,980 to go.

It was then that I realized it was time to work my ass, just as I had done at that West Virginia service station.

I placed an ad, which read:

"Southern gal with something extra seeks $ecure gentleman for a good time, possibly a regular thing. Any age, any race welcome. Donations appreciated. Too won 2 five five 5 7 three for ate."

That evening, after I got off work, I met with a young man named Patrick, who responded to my ad. He was a young medical student, about my age, and very handsome. In another set of circumstances, this might be a regular date. He was my type, after all. And because of that, I had to remind myself that this was not a date. I was working.

I walked into Patrick's apartment wearing a dress that exposed my cleavage and a set of black silk stockings and high heel shoes. I hated heels. But men found them sexy.

I began to unbutton my dress as Patrick took his shirt off. There were no introductions. Everything I knew about him was from the text message he had sent me in reply to my ad.

Patrick had one hell of a body. He had a very nice set of pecs and abs. He stood six foot two.

He took off his pants and I leaned against the back of his sofa. Then, he lifted up my dress to play with my ass.

Like Matt, he had a very thick cock.

"This is my first time with a she-male," he said.

I hated being called that. It bears repeating: I hated being called that. However, in the interest of good customer service, I let it go.

"I'll be sure to make it memorable for you, babe," I said.

He pulled out a bottle of lubricant.

"You have lube," I said, surprised.

"I'm studying to be a doctor," he said. "I know my anatomy. And I don't want there to be any problem inserting my penis into your rectum."

"Most guys don't get that," she said.

I felt his finger caress my butt pussy with a cold liquid. Then, I felt his condom-covered cock enter me. This was the first time I could remember ever being fucked with a condom. Most guys did me raw because there was no fear of pregnancy. But Patrick, being a medical student, had other concerns.

He fucked me hard and furious for a half hour before he finally came. Not concerned about my desire to get off, he pulled out his dick and took the condom off.

Then, he handed me $200.

"Here's my donation to your surgery fund," he said with a smile. "Who knows? Maybe someday I can be your gynecologist."

I smiled back at him as I took the money. Then, I left.

As I walked toward my car, the horrible realization set in that I was now officially a whore. Unlike the awful experience in West Virginia, where services were traded for services, this was prostitution in its most classic form: sex in exchange for cold hard cash. I at least took with me some dignity in the fact that I was a high-class call girl, rather than a crack-hustling street walker.


My next trick was an older man named Tom, who lived in Greenwich Village. In his reply to my ad, he mentioned that he was into unusual fetishes and was looking for a "mommy" figure. Strange that a sixty-something man would be looking for a 21-year-old "mommy." But, whatever...

I walked in the entrance of his apartment building and dialed apartment 1207 on the intercom.

"Mommy?" he answered.

"Yes, Dear," I said. "This is Mommy."

Suddenly, the door opened and I went up the elevator to the 12th floor.

The door to apartment 1207 was wide open and I walked in. I was stunned to see what looked like a baby nursery. There were teddy bears and toys everywhere. Tom didn't have normal furniture. He had baby furniture. In the center of his living room was an oversized crib. And in it was Tom himself.

Tom was in his 60s, bald with a thin horseshoe of silver hair, heavily obese, and wearing nothing but a giant cloth diaper.

"Mommy," he said. "I wet my pants. I need changing."

I walked over to his crib and unfastened his diaper pins. The cloth diaper was urine-soaked. I took a baby wipe and a piece of paper towel and wiped his cock and balls clean. Then, he lifted his legs so that I could wipe underneath him.

"Mommy," he said. "Will you play with my pee-pee?"

I took hold of his cock, which was growing an erection, and gave him a hand job. I stroked him until he was rock hard. Then, I took his old, decrepit cock and put it in my mouth. I sucked his cock until he came.

"Swallow it, Mommy," he said.

I swallowed the old man's cum, licking the head of his dick clean.

Then, I put a clean cloth diaper on him, fastened the pins in place, and picked up the $200 that he had laying on the table.

Then, I left.


The next night, I met up with my third trick, a woman named Alice.

Alice lived in a large, beautiful house in Queens. Hopefully, I thought, her donation would match the high-class wealthy lifestyle she lived. She introduced herself as she let me in.

"I'm Alice," she said. "So great to meet you. Can I get you something to drink?"

"Sure," I said. "I could go for a drink."

Alice and I sat down in her living room.

"So here's my situation," she said. "I have a beautiful wife who I love more than anything. But she's a business woman. Sometimes it feels she cares more about her work than she cares about me. Still, a woman's got needs. And that's why I answered your ad."

"Well," I said. "I have to be honest. I've never, you know, been with a woman before. What exactly are you wanting to do?"

"Just touch me," Alice said. "It's been so long since I've felt a woman's touch."

"You do know that I have extra parts?" I said.

"All the better," she said with a smile.

"Excuse me," I said. "I need to use the little girls' room."

I went to her bathroom and took a Viagra. I had scored a couple of pills online, just in case I would need to use that abominable appendage between my legs. This would obviously be one of those occasions.

Then, I returned to Alice in the living room.

"Would you like to get started?" I asked.

"Let's go upstairs," she said.

Alice and I went upstairs to the bedroom she shared with her wife. There, we got undressed. As she revealed her body, I saw an older version of the body I longed for. This made disrobing particularly uncomfortable: Alice was a complete woman from birth, while I revealed to her a girl with a penis. A rock-hard penis, in fact, as the Viagra had taken effect.

She laid down on the bed and spread her legs. This gave me the opportunity to explore the organ that I I was determined to someday have. That was, after all, reason I was here to begin with.

I played with her clit and pussy lips, carefully examining her womanhood. As I played with her pussy, I fantasized about that special day when a very special man would do this to me.

"You want to put your finger in me?" she asked.

I laughed.

"I've got long nails," I said.

"My wife wears long nails and nothing pleases me more than having her fingers inside me," she said.

I put my finger into her pussy and felt her warm, wet interior. With the other hand, I played with her clitoris.

"Dr. Ginsburg is going to give me one of these very soon," I said, feeling comfortable enough to open up to her. "I'd give anything to feel what you're feeling right now."

When I finished fingering her, I leaned down to lick her pussy, continuing to explore her most amazing organ with my tongue.

Then, I put my breasts to her mouth, allowing her to suck on them. She wet my erect nipples, sucking and biting on them. The feeling was out of this world.

Then, I threw back my long red hair and prepared to penetrate her with my cock.

I took her legs over my shoulders, as many men had done with me. Then, I slid my disgusting manhood into her.

Thrusting back and forth in and out of her, my cock felt the warmth and wetness of the inside of her pussy. It was a horrifying experience for me, but I was motivated by the thought of someday being in her position with a beautiful man in the position I was in.

I felt her pussy collapse around my cock as she came. Shortly after, I shot my spermless ejaculate into her.

Of all the sex I had since leaving Tennessee, this experience was by far the most humiliating and traumatizing. I would rather be bending over for Terry in West Virginia, as he lubed my ass with his greasy motor oil-laced fingers and sucking on his filthy smegma-covered cock. He may have denied my humanity. But at least he acknowledged my womanhood.

But I had no time to ponder this deed I had done. At that moment, very familiar voice rang out from downstairs.

"Alice, honey," she said, calling up the stairs. "I'm home!"

It was the voice of Fiona Charles, my boss.

I heard footsteps coming up the stairs. Alice and I quickly and frantically put our clothes on. But then, the door opened. Fiona stood there, shocked.

"So how long has this been going on?" she asked.

"Honey, I never meant to hurt you," Alice said. "But I've got needs."

I finished getting dressed and reached for my purse.

"I'm not going to sit around here and listen to your marital troubles," I said. "I've got work to do."

Fiona laughed.

"So this is what you're doing to pay for your surgery?" she said. "How pathetic."

"If you offered better insurance, I wouldn't be here, now would I?" I shot back.

I walked out of the room.

"Guess I'll see you at work tomorrow," I said.

"I can't believe you think you still have a job," Fiona said. "Just out of curiosity, how much is my lovely wife paying you?"

I thought for a moment. We hadn't actually discussed the "donation." But then, I was now jobless. So I had nothing to lose.

"Five hundred," I said.

Fiona laughed as she reached into her purse and pulled out some bills.

"Here's three hundred," she said, handing it to me. "I'll add two hundred to your last paycheck."

"Oh, and don't even think about filing for unemployment," she continued. "I know the unemployment people personally. I promise you they will laugh their ass off when I tell them I fired you because I caught you moonlighting as a whore."

"Now get out of my house!" she yelled.

And then, I left the home of Alice and Fiona, jobless and destitute.


Prostitution was no longer my second gig. It was my only gig. The small amount of money I had raised for my surgery fund now had to be used to cover my more basic needs. I arrived home with my landlord waiting outside my door with an eviction notice.

"You never did give me that three hundred," he said. "And now you're a month behind."

"I just started a new job," I said, reaching into my purse to give him all of the cash that I had earned from working my ass.

"You still have to pay your rent," he said.

I flashed him a seductive smile. Then, I walked over to him and ran my fingers up his chest.

"Maybe you can come in and we can discuss this," I said.

He laughed and shook his head.

"I'm not into girls," he said. "$1100 or you're out."

"Fine," I said, reaching into my purse and handing him all the cash I had.

He counted $900.

"Two hundred short," he said. "Until I get it, this stands."

He handed me the eviction notice and walked away.


The next day, I sold my car. New York had plenty of subways, buses, and cabs for me to get around. By not having a vehicle, I was actually saving money for parking fees, insurance, and gas. At least this was how I tried to justify it. The fact is that losing my car meant losing my independence, as well as a quick getaway in case things got out of hand with my tricks. But it was the only way I could recover from the devastating setbacks of losing my job and almost losing my apartment and still having money set aside toward my surgery.

I was truly desperate at this point. I couldn't go on doing one trick per night. I had to do two or three, maybe even four if I were to have any hope of seeing this through. That meant having to walk the streets just like any other whore. Yes, that one bit of dignity I had left, knowing that I was a call girl instead of a street hustler, was now gone.

I could bellyache about how life had dealt me the short end of the stick. However, that wouldn't get me out of my dilemma. Money was what stood between the half man-half woman existence I was living and the complete woman I was desperate to be. That meant picking up and moving on.

I put on my fishnet stockings, red high-heel shoes, and a bright red dress that revealed my titties and my ass. Before I left for the evening, I decided to check my email, just to make sure there wasn't a potential high-priced response to my ad.

There was one response.

"Southern guy here, 23 years old, just got out of rehab and turning my life around. Looking for hot, red-head T-girl to satisfy me in every way. Not interested in being your bottom boy. I want to be your man. Don't have much cash, but can offer you so much more. Meet me in room 815 of the Regency Hotel."

I thought for a moment about this one. Then, I decided street walking could wait.

Shortly after, I hailed a cab and went to the Regency Hotel near Central Park. There, I took the elevator to the 8th floor and walked down the hall to Room 815. The door was ajar and I walked in.

The room was dark and scary.

"Hello?" I said.

Suddenly, a voice broke the silence in the dark.

"I left you a message, but you never called me back," he said.

"Kyle?" I asked.

Suddenly, the lights came on. Kyle sat on the edge of his bed, shirtless and wearing only a pair of shorts.

"Hi Shanna," he said.

I shut the door and walked into the room. He stood up to face me.

"Monica said you were in New York," he said. "And she also said I'd have a hard time finding you in a city of six million people. She was right about that. I've been looking for you for the last few days and was about to give up and go home. But then, I started looking through the ads and here you are."

"Kyle, it's so embarrassing having you see me like this," I said. "Let's just say I'm not the same girl whose phone number you blocked. You know, the girl you fucked and then tossed out like yesterday's garbage."

Kyle shook his head.

"I wish I could take that back," he said. "If it means anything to you, I emptied my savings account so I could drive all the way from Tennessee and pay for this hotel room just so I could see you again. Can you forgive me?"

I threw my arms around him and gave him a hug. Then, I kissed him tenderly on the lips.

"Yes, Kyle, I forgive you."

"Shanna, what are you doing?" he said. "This isn't good for you. Let's go. We can sort everything out when we get home."

"I'm on a mission, Kyle," I said. "No matter how bad things might be right now, I'm working toward a big payoff."

"You mean surgery?"

"Yes," I said. "Without the reassignment surgery, I will never feel complete as a woman. Because below the waste, I'll always be a dude. It's not something I would expect you to understand."

So there I was, the whore that I had become standing face to face with a man who represented a time when I was a much more innocent person. He was my connection to my past, before I had lost myself in this twisted world of prostitution and desperation.

My life was hell. I had lost my job, my car, my independence. I was inches away from homelessness. I was selling my ass on the streets, not just for the goal of having sexual reassignment surgery but for survival. And here before me was a man who had given up so much to rescue me from all that.

Still, no matter how much I wanted to run off with Kyle, I couldn't break away from my resolve. Sexual reassignment surgery wasn't just something I thought would be a nice change. It was something I was desperate for.

As I pondered, I closed my eyes and felt Kyle's hands gently caress my arms and neck. Then, he pulled out the cross necklace I wore between my breasts.

"You're still wearing this," he said. "While you're working?"

"It keeps me spiritually grounded," I said. "You know, so I don't lose who I am even when doing things that destroy me."

"Get your stuff together," he said. "Let's go home."

I held back tears as I held him close and gave him a kiss.

"Goodbye, Kyle," I said.

With that, I turned and left.


I walked down the street so that I could hail a cab and head back to my apartment. I really wasn't in any mood to work the streets. Just then, I heard church bells coming from the St. Jude Parish. I went inside.

The inside of the church was dark, but strangely inviting and very comforting. I held the cross attached to my neck as I walked into the confessional. A lifelong Catholic, I always believed that we could ask forgiveness for our sins, even if we return to sinning before "banking" enough sins to require going to confession again. Tomorrow, I was to begin my street walking. I wanted to go home to Tennessee. But I also wanted to go home complete.

I figured that if something were to happen to me while working my ass on the streets, this would be a good time to get things right with the man upstairs.

I walked into the confession booth and sat down. I gave the sign of the trinity as I heard the priest sit down beside the booth.

"Forgive me, Father, for I have sinned," I said.

"What brings you to confession?" the priest asked.

"I'm a prostitute, Father," I said. "I give sex for money so that I can raise enough for my reassignment surgery. I've betrayed every part of who I am."

There was silence.

"Someone has come into your life to rescue you," he said.

"How did you know?" I asked.

"I can hear it in your voice," he said. "You'd be foolish not to go."

After confession, I returned to my apartment. I just couldn't bring myself to heed the priest's advice. That night, I got on my knees and prayed that God could grant me the strength to persevere and follow this through. Even though it meant sinning against Him and against myself.

I had thrown all of my self-respect to the four winds. But seeing Kyle again only served to bring back my longing for a much simpler day, before I had become obsessed with going under the surgeon's knife to bring my physical body into compliance with my soul. He had reached out to me, tried to atone for the hurt he had caused me, and extended a hand to help me out of my misery. And yet, I pushed him away.

The next morning, I went back to the Regency Hotel.

"I'm looking for Kyle Conner," I said. "Is he still registered in room 815?"

The clerk looked up the guest registry on the computer. Then she shook her head.

"Mr. Conner checked out early this morning," she said.

"Thank you."

With that, I sadly walked out of the hotel lobby and back outside to hail a cab. I pulled out my phone and called Kyle, hoping he hadn't gone very far.

I reached his voice mail, but chose not to leave a message. My rescuer had come and gone. I rejected him. And now I had no choice but to press on.


The following night, I walked the streets of New York City, trying to turn tricks. I walked up to a car full of young college-aged men as they stopped at a red light.

"You guys up for a girl with a little extra?" I asked with a smile.

They looked at each other and laughed.

"Sorry, dude, not into that," the driver said.

The light turned green and off they went.

Shortly after, I approached a middle-aged man who was walking alone.

"You up for a little night cap?" I said.

"All I've got is fifty," he said.

"I can give you one hell of a blow job for that," I said. "And if you're a good boy, I might even swallow."

Together, we walked into an alley behind the building. We stood next to a dumpster as he unzipped his pants.

I got down on my knees, on the filthy trash-littered ground, and took hold of his cock. I put it in my mouth and sucked him off. I used my tongue to tease and tickle his member, moving my face in and out of his groin.

He pulled my hair, which excited me enough to perform my deed with more aggression. I felt the nipples under my bra become erect, along with my cock, hidden underneath my skimpy red dress.

The pain from the hair pulling made me orgasm. A stream of clear goo from my cock soiled my panties.

Then, he came. A huge load of white spooge filled my mouth. It wasn't tasty, but a promise was a promise. I removed his cock from my mouth and allowed him to watch me swallow his juice.

With that, he zipped his pants back up, tossed a fifty dollar bill on the ground, and walked away into the night.

I walked in the other direction, back to the street, so that I could hustle the next willing trick.

A car filled with black gangsters stopped at a red light. I approached them and was immediately assaulted by the smell of crystal meth and marijuana.

"How's it going, boys?" I said with a smile.

"Oh baby, it's going," one of them said to me.

"How about a white girl with a little extra to spice up your evening?"

They looked at each other and smiled.

"Hop in, baby" the driver said.

With that, I got into the car. It was a four-seat sedan that had six guys sitting in it. I sat on the lap of two of them as we rode down the street to Destination Unknown. I was terrified. My face was up against theirs. They clearly smelled of hard drugs, probably crack or crystal meth.

Then, we pulled into an alley not far from the Regency Hotel, where I had been the night before. Then, we got out.

I took my clothes off and bent over against a pile of milk crates piled against a dumpster.

The first gangster fucked my ass dry. When he came, his cum provided lubrication for the next guy. It was dark and I had no way to see these men who were ravaging my ass. All six fucked me until they came. And by the time it was over, I had a huge load from six men streaming out my butt pussy.

After it was over, I put my dress back on. It was now time to collect the money.

"Five hundred," I said.

"Serious?" one of the gangsters said.

"Okay," I said. "How about a group discount? Two hundred?"

"Bitch, you're joking," he said with a sinister laugh. "How about we party instead?"

This was the moment I finally hit rock bottom. I was a whore. I was trash. And now I wasn't even going to get paid. It was then I realized that I was simply never going to be complete. I was never going to have my surgery. The male body I was trapped in was as good as it was going to get. I had lost my job, my independence, my humanity, and probably my home.

I had nothing to lose.

"Sure," I said with a big smile. "Let's party!"

At that moment, I noticed a pair of headlights turn down the alley. Suddenly, they shut off. I had no idea who it was in that vehicle and I was terrified. My heart raced. The gangsters, however, didn't seem to notice or care.

One of them handed me a crystal meth pipe. I took it in my mouth and used the torch lighter to heat up the meth, getting high for the first time in my life. And then....

Everything went black.

My next memory was awakening in a hospital bed. I looked up and saw bright lights and medical equipment. The next thing I saw was Kyle's smiling face as he held my hand.
Warning: This is an extremely dark story. It is the tale of my desperate quest to become a complete human being. No one who happily lives in the gender in which they were born can truly understand what a person will do when they are desperate for the one thing most people take for granted: a body that matches their mind. This is my story. Here you will find out just how far and how low I was willing to go in order to finally achieve my humanity.

This story represents the dark second act of a three-act play. Be assured that story does ultimately have a happy ending. But as they say, it is always darkest right before dawn.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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