My Journey to Become Amanda/Transgender/High School/Shemale

By Amanda Sutton

Published on Sep 18, 2019

Highschool

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My Journey to Become Amanda

By Amanda Sutton

Warning This story contains graphic gay and transgender sex. Including gay and trangender porn movies. It is meant for those 18 and over. If you are younger than that or would be offended by depictions ofgay and transgender sex stop reading now.

This story is the property of the author. If you wish to repost this, youmay as long as you have my permission first and you do not profit from it. This story is fiction.

Any resemblance between anyone alive or dead is coincidental.

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SMAACK. You could hear the smack across my face and even though I knew it would happen I couldn't get away from it. Not that it would have mattered, he would have just picked me up and do it again.

He started yelling, "what the fuck is wrong with you boy? I say boy because you are one and you better get your act together because I don't raise no sissy faggots".

What he was referring to was that I was wearing a bra, panties, dress, I had made myself up and the wig my sister got me was on.

You would swear I looked almost 100% like the girl that I am inside.

"Now take that shit off and dress like a boy. How could you be as stupid as to wear that shit to school. And I don't want you saying you're a girl again.

And get your hair cut or I'll get you a crewcut". He then looked at my sister Claire. "You think it's funny helping him dress like a girl.

Am I going to find out you're a dyke" (she isn't by the way)? I swear to god if you help him, I will spank you like there is no tomorrow."

My mother was going to say something, but he gave her a "shut up" look.

My given name is Andrew Gates, though I think of myself as Amanda. I am a 15-year-old teen girl stuck in a teen boy's body.

My 17-year-old sister is the only one who is somewhat understanding, my older brother is 20 and has smacked me around telling me what a fucking embarrassment it is having a fag brother. Some kids at his High School made fun of him having a fag brother and he beat the shit out of them.

(yeah, he's 20 and a Senior in HS. Not the sharpest knife in the drawer).

I am bullied all the time because I insist as dressing as a girl. I've gotten hit, one time some guys said they were going to gang bang the tranny I told them if they did, they would be sort of gay. They beat me and broke a rib and called me a fag. I insisted on wearing girl clothes to school and one kid Tommy tried to force me to give him a blow job which I got saved from at the last second. He saw me later and gave me a black eye.

Even some of the girls said, "you're not one of us, don't try to use our bathroom you freak".

(I use the handicapped bathroom, which was forced on them by state law. This town would not take the initiative. This is Trump country here).

Why wasn't I born in a city. Even South Bend has a gay mayor. I walk down the hallways at school and get called a fag, homo, cock sucker, everything.

Except I'm not a fag, I am a transgender girl.

I headed upstairs with my sister Claire. "You wore one of my dresses. Look I got you your own bras, panties and other stuff but I thought we agreed no more of my stuff.".

She had caught me for the first time at 9 wearing her clothes. At first, she thought it was cute, then funny, then she realized what was going on in my head.

She bought me some of my own clothes, showed me how to apply makeup and got me a couple of wigs though with my blue eyes I usually wear the blonde one.

"I'm sorry, I wanted to go out and the skirt you bought me is getting a little tight. Your flower print dress which I love was the perfect fit. I felt so good wearing it." "Until dad caught you. Look I'll get you some more stuff." She paused and smiled. "And you can keep the flower print dress."

A few days later I knew my father would be working late and my brother was with his girlfriend and I took a walk in my girl clothes.

I had on my B bra stuffed, a pink dress, matching top and flats. I was walking through a nearby park when I realized I was being followed by a middle-aged man.

He caught up with me.

"I know you're packing something under the dress if you're in this part of the park." I was a bit scared. "I'll give you $10 if you let me blow you." He wanted to pay me so he could suck my cock? Freaky. But I had never had a blow job and he want to pay me so what the fuck." "$20" I impulsively said.

"Deal" he said. He lifted my dress, pulled my panties down. He then kneeled on the ground and fuck. He's sucking my cock.

It felt good except it's a cock I don't want and ...I shot my load right into his mouth."

"Um nice. How much do you want for the return? I'll give you an extra $30" he said.

Now I would have done it for free, the chance to be a girl to a man. I kinda had an idea what to do, so I began licking his pole and then took it in my mouth and sucked it. I grabbed his pole to keep it still and he said, `Stroke it while you suck it'. After a couple of minutes, he made a grunting

sound and I found myself with him coming in my mouth. And I wanted to swallow it, which I did.

"Wow girl, you are good. What's your name"?

"Amanda."

"Cute name. I'm uh, Joe. You know as a girl you are very cute. Be here tomorrow, I may be bringing you more business". As he walked away, I thought great, I'm a transgender prostitute now. And it didn't bother me. I could save up money for hormones. I am a girl and I want a girl's body. I went home, changed before my father got home and hid my clothes away in the drawers Claire gave me in her room.

I was extra careful now when I was wearing girl clothes. I would wear pajamas and just before bed switch to a nightgown. I began sneaking out of the house to the park. The guy was there, and he was with a friend, Frankie. I blew them both. Then another guy showed up. It was one of my neighbors and he recognized me.

It was Tommy's father.

"Andrew, shit when my son told me you were dressing like a girl, I didn't believe him. Shit. I mean what are you doing here? I heard a scream and ran over to this part of the park and..." He babbled on trying to talk himself out of his situation. He knew he couldn't tell my father because then he would be admitting to soliciting an underage transgender girl. However, my cover had been blown and some word got out and next time I went looking for men I was grabbed by the police.

My father showed up. I was still in girl clothes and my mascara was running from crying. My father talked to the police and got me released. He didn't

say a word until we got home. He beat the hell out of me, and my brother joined in because if anyone knew he would be the laughingstock.

Claire helped me clean up. My mother had totally tuned this whole thing out and acted like it never happened, that her son wanted to be her daughter, that I had been caught for prostitution or that I may have a broken rib from where my brother kicked me.

"Jesus, what were you thinking when you went into the park?" Claire was angry. She felt I broke her trust.

"It started out as nothing. These guys would pay me to blow me. And occasionally I blew them just like any 15-year girl. When was the first time you gave a blow job? I'm sure it was probably 15 also."

She turned red but ignored that comment." Getting paid, you're desperate."

"Desperate to get out of here to a place where I'm accepted as Amanda."

Frankie managed to contact me and rented a motel room, so I didn't have to do it in the park. There was a new guy who wanted me to fuck him up the ass.

Again, paying me! He gave me $200 to fuck him in the ass and then blow him. And every one of them called me Amanda.

I was at home one day when Claire came running into my room. "How much money do you have?" she asked. "Doesn't matter, I took money out of my bank account.

You need to leave now." She was scared and I was ready to freak out.

"What's going on" I cried.

"Dad was on the phone with transporters. He is paying people to physically take you to a gay conversion camp. Even mom tried to intervene, but he shot her down".

God what is wrong with my father, what is wrong with me? I grabbed my clothes both boy and girl. Took the money.

She gave me a burner phone, I needed to leave my iPhone so they couldn't track me. "Stay in contact and for God's sake, keep yourself safe."

She gave me a hug. "I love my sister Amanda." I cried as I left.

Dressed in girl clothes I went to the motel. Frankie showed up. He saw I was crying. I told him the story of my father plan for me.

"You need get out of here. You know I have a friend in LA who can probably help you. He helps kids like you." He gave me the name of a guy and a phone number.

"How can I thank you?" I sorta knew the answer before he answered. He took his cock out of his pants, I got between his legs and sucked his cock.

He grabbed my ass, lifted my skirt, pulled down my panties, bent me over and popped my cherry. It hurt but the thrusts of his cock made me feel like a girl being fucked. I actually got hard from it and jerked myself while he had me on my back. He pulled out and just shot his load in my mouth.

Then he let out a little laugh and before I came, he pulled my legs back, so I came in my mouth and on my face.

I fell asleep. I didn't know it, but Frankie got on his computer. He hooked up with a dark website and texted "New one for you. All ready. She will call." As soon as the message was read it disappeared.

Frankie helped me get a bus ticket and I managed to get on without my parents noticing. I took the four-hour trip to Philly, bought a ticket for LA, I also boarded a bus to Jacksonville Florida and got off at the last second to help throw them off the trail. I called the guy a ½ hour before I got into LA.

I told him I had a blue skirt and white top on. He met me there.

"I'm Kenny" he said to me. Frankie called me and told me your story (which he hadn't because he couldn't risk being tracked). I recalled it for him.

"I'm going to get you a room tonight at a hotel. There are other kids in that hotel, and they are runaways also, so you better hide your stuff when you're not there.

I was afraid what was next.

"Frankie tells me you give great blow jobs and you can be fucked in the ass." He unbuckled his pants. "Can you do it as a boy?"

"But I'm a girl" I replied.

"Look, I do gay porn movies. My clientele likes boy fucking other boys bareback. I have a couple of custom orders that I need someone your age for.

If you want to make some decent money, you'll do it my way. Lots of actors and actress porn stars have done gay for pay. Think of it that way.

You are a girl who likes boys. You play a boy who likes boys."

He was paying me decent enough money to do the bottom, so I did it. I met my "co-star" Chuck and we talked for a little bit about how the scene would work out.

Chuck is cute. About my age, he had a washboard stomach, curly brown hair and wow, a big cock.

We started out running into a bedroom set and began kissing. Our shirts came off and we undid each other's pants. We reached into each other's underwear and began rubbing the cocks. We continued to kiss while we jerked each other off and rubbed out cocks together. He began to blow me.

We switched I sucked on his cock. "Shit you are good" he said.

"Don't make him come yet" Kenny yelled. "He has to fuck you. Do it now." He put some lube on my ass and bareback worked his cock in. It didn't hurt as much and but did feel good as I lay on my back getting fucked.

"On all fours" yelled Kenny. I got on all fours and he fucked me some more. The camera man got Chucks ass from behind so he could see him fuck me.

After a some more fucking he yelled "69 and come in each other's mouths". We paused for a second while Chuck wiped his cock off and 69.

In a couple of minutes with me blowing him from under I felt him move, grunt and come. I came a minute later. We were told not to swallow as we kissed.

He dropped the cum from his mouth into mine. I did the same and we both swallowed what was left in our mouths, leaving cum on our faces.

"Cut, that was beautiful boys. "Chuck told me he was staying at the same motel I was out and maybe we should room together. He winked. I said yes.

That night I put on my girl clothes. Chuck was surprised but was okay with it since he was gay, and I was willing to be the sub in the relationship.

We fucked again without cameras. One day he said to me that he was gay and liked guys as guys, not as girls.

I managed to get my own room. Rejected by a gay guy because I am a girl.

I got called the following day for another gay movie. I played the younger brother. My "older brother" brought a friend and the friend said, "Billy says you suck his cock anytime he asks."

"So, you want head?" I said. I pulled down his pants and began blowing him. I stopped and took my clothes off. "I like being naked when I give a blow job".

I ran my tongue on his balls and around his pole before taking hic cock in my mouth. I bobbed my head up and down and jerked it as I sucked his cock.

My "brother "took off his clothes and sat next to his friend.

"Hey little brother don't forget me" and I blew him while jerking his friend off and then switched. "My little brother likes to take off his clothes because he is hoping he gets fucked in the ass also "said the guy playing my brother I got spit-roasted, his friend fucking me while I blew my brother and then they switched, this time with me on my back with the friend shoving his cock into my face. They both came on my face." Cut", yelled Kenny.

I got cleaned up and got in my girl clothes. I was fixing my makeup when "My brothers' friend "said that I make a cute girl, He knew a director who would love to film me like a girl. Kenny hit the roof. "Fuck, now I have to go making all these arrangements. This be better be worth it, I have a ton of orders to fill."

He had me put on a schoolgirl outfit with red and blue striped knee-high socks. He shot that, my skirt up and panties off. Had me pull the skirt up so he could shoot my ass. Spread my ass cheeks. Open top to see bra. Take off everything except bra and my girl socks. Jerked off. Videoed me giving myself a self-facial with my ass and legs high in the air as I pointed my cock to my mouth. Kenny looked impressed.

"Like I said, I have orders for movies. If you want to do it anymore it has to be as a guy. I don't have time to fuck around. I'll send out a post on the website we are using now and see if it's worth it".

The following morning Kenny burst into my room. He pulled his cock out. He looked excited. boy he must really want a BJ I thought as I took off my nightie.

"No leave it on" he said. I was happy with that and sucked his cock until he shot off and I licked it clean.

"Congratulations, you are now my t-girl star. Traction? Three quarters of my customers liked you better as a girl. Every guy wants to fuck the girl with the dick in the video. The teaser of you is gone now and I made this one where it was not downloadable and shit, they all want to get it and download it and see you in other thing"s.

I smiled. "I'll do them on one condition".

"What is it?"

"Estrogen and other female hormones. I get what I want, and you get a girl who slowly changes into a real girl. You get everything from the start to the vagina".

It will take a few years so by the time we finish I may be too old for you anyway." He thought for a second. "We have a doctor we use for STD checks. Maybe she can help you. But I'm doing this out of the goodness of my heart."

Out of the goodness of his heart was my first t-girl movie. Three guys. Three cock sucking and ass fucked. Three facials. What a guy Kenny is (even if I did enjoy it).

I met with the doctor. She was transgender also and I wouldn't have known it if she hadn't told me. Get me get her surgeon I thought.

"Let me see what you're packing down there" she said. I was naked and she grabbed my penis and reached under. "Hmm, not bad. You've started going through puberty which can be a good thing. We want to have enough scrotum to form a vagina, but the double-edged sword is the puberty blockers do exactly what they are called and then we don't have enough scrotum. I am going to put you on a low dose of estrogen, and we'll see in 6 months what's going on with your penis.

If I feel there enough to work with, we start increasing the HRT."

"What do I do for six months?"

"Get a new hairstyle, mani-pedi, make up and a new bra. Get a few. The one you're wearing doesn't fit right."

For six months I was on the low dose. I did notice some changes. I actually had to go get an A bra. I did several fuck films a month.

Anal was pleasurable, the thrusts were such a turn on. I was finding I was a little bit more emotional.

After six months I saw the doctor again. "Good news, the estrogen lowered down the growth of your penis, but I think we have enough scrotum to work with." I was elated.

"I'm going to slowly increase your puberty blockers but once I do that it's really no going back." `I don't ever want to go back."

"This is going to be expensive; I can do this at cost, but it will take money. If you decide to have bottom surgery, you would need insurance and i t will still cost you".

I found I was slowly feeling changes. Kenny is not thrilled that my dick is smaller but as he said "as long as you get fucked in the ass I don't need you to fuck some guy."

Whenever I showed up at the studio (which changed occasionally to keep the feds from finding them) I always gave Kenny a blow job. I don't mind because I love to swallow and enjoy the taste of cum. I usually do the cameraman because as Kenny says, "I don't need the guy coming in the middle of a scene." Kenny usually has a friend on the set (different guys who are probably paying Kenny).

He had a friend, show up one day. Late 40's, okay looking I guess but as long as they follow my rule (that the dick is washed), I'm good.

"Hi sweetie" he said. My friend Kenny was telling me that you..."

"Give the best blow job in town. I know, Because it's true. I undid his pants. My hair had grown almost to my shoulders, so I pushed my hair away and started sucking

his cock. I ran my tongue up and down his shaft. After a while I took it in my mouth and began to suck.

"Holy fucking shit" he said. Probably hasn't had a good BJ in a while. "Oh that is..." He was pretty quick. I kept sucking and swallowed his cum.

I kept sucking until he was done and cleaned up. "OH damn girl, that was hot. I haven't had a BJ like that in a long time."

"Okay" yelled Kenny, "we got worked to do. Amanda, I got a cheerleader outfit and three guys on their way in".

"A gangbang? I just gave three blow jobs and I have a gangbang? This is costing you big time. And if you think I'm ever going to do a DP in my ass forget it.

It's not that big. As it is my ass will be sore for a week" I said as I took off my skirt, changed panties and then a scream.

"Holy fucking shit, she's a guy?" It was Kenny's friend.

Kenny was laughing. "You are going to regret that my friend."He turned to me and said "Take it easy." But the hormones had fucked with my emotions and I was angry. Imagine a girl with PMS.

I put on my skirt and walked over to the guy topless. "Let's get something straight pal. I am not a guy. Yeah there's a penis but I am a girl.

Do I sound like a guy?" He shook his head. "Look at my hands. Guy hands?" He shook his head. Look at my face. Anything masculine?:He shook his head no.

You saw my face before I blew you, anything tip you off that I had a penis and was born in a boy's body?" He shook his head. He knew I was pissed. "My hair is real, not a wig, I have tits. You're staring at my tits. They not be big, but they are real. I go into Victoria's Secret the salesgirls don't suspect for second that I have a penis. I love wearing bra's, panties, stockings and anything girly. I'm like any other teen girl, I give guys blow jobs, I get fuckeddick

is going when I get a chance and guys will be fucking my pussy. So, don't ever think I am not a girl." I started to cry Unfortunately one side effect of the HRT is

I get weepy and this guy set me off.

"Sorry, I get it, you're a tranny and I didn't catch it." Kenny put his hand on his face and shook his head.

I looked at him. "TRANNY"??? Who the fuck uses that word? Why don't I call you a pedophile and perv. You could share a cell with Jeffrey Epstein if he hadn't killed himself. In fact why don't you do that? Get the fuck off the set or I will pull your pants down and bite your dick and fuck your ass." He looked at Kenny.

"Get out." said Kenny.

I wiped the tears and then fixed my makeup.

"This shit with your "friends" is stopping now." I want a cut of that. And I want more from you."

"Jesus, more money?"

"Health Insurance. Go on the exchange ad get me Obama Care." I was getting savvier every day.

I continued to do movies, one day a girl showed up on set Kenny handed me a script. I was going to have sex with my "sister" and her "boyfriend".

You ever eat pussy before"? she asked.

"No."

"Okay, I got to give you a lesson before the movie."

I had never seen a vagina up close before. The folds, the hole, I stick a dick in my mouth but how do I do this? "Okay, now start using your tongue on the outside and

then gently, no don't lap it like a dog, gently. Now start moving your tongue around, like that. You see that little hood? The clit is there that's what I want you to concentrate on while you put a finger in me, that's right, yeah, you got it, not bad for a beginner...Oh fuck, yeah, no don't fucking stop, UHHH." She was breathing hard. "Wow" she said, you got it down on your first time."

I kind of liked when I ate her pussy. Her wetness tasted good. The movie rolled out. She walked in with her boyfriend with me putting on make up (btw I have become an expert with that) bra, panties, skirt and stockings.

"Well, look at this, my little brother likes wearing my clothes. She grabbed my hair," Are you a little sissy faggot?"

"No, I, I just like.."

"Looks like a little faggot to me" said the boyfriend."

"Bet he would love to suck your cock" she said. She looked at me "Is that what you want, to suck his cock, you want to be a little blow job girl?"

He had dropped his pants and she shoved my face to his cock. "Now start sucking "she screamed. I sucked his cock." Oh, you are a little faggot, we're going to have

fun with you."

She took off her clothes. "Eat me, you faggot, see if you can do a woman. "I ate her pussy. She was getting off, I actually liked pussy, but she stuck to the script.

" Jesus that sucks. You can't do woman. I need to get off. She pulled a big strap-on ". Ever get fucked in the ass before. No? Well I'm going to break your cherry and loosen you up for my boyfriend. I was sucking his cock while she fucked me with the strap-on. "Oh yeah, you're a little fuck puppet.

Tommy, why don't you fuck him". He fucked me in the ass.

"You like that you little homo. You like being a bottom. I'm going to invite some friends over. After a few more minutes he came. My sister took the condom and poured his cum over my head into my face."She then had me come in my hand and lick it up.

I did a movie with two other transgender women. They had me dressed up as a boy, they" transformed""me into a girl even though I looked more like a girl than a boy at this point I put on a red bra, matching panties and a red garter belt with red stockings.

"We made you a girl as you wanted. It is time to pay for it." Said one. "Tell us what you are." "I'm a sissy slut" I said.

"Not yet, more" said the other. What do you want to be?" "I want to be a sissy slut. I want to be a cock whore. I want cum dripping out of my mouth and my ass. I want cum, I need cum. I want to be a cum dump.

I want to be a cock whore"

"Then it is time for you to be one. Ask us, beg us."

"Please, I want to suck your cocks, and have you fuck my ass. Make me a sissy fag cock whore."

The first one was wearing a black merry widow with garters and stockings. The other wore a purple teddy. The first one grabbed my head and shoved her cock in my mouth. I sucked on her cock.

"Yes, you love the cock you whore. The other one got to the other side of me. They were standing as I sucked both their cocks. The one in the teddy had me

bend over and fucked my ass. Felt so good.The other had me suck her cock.

"Oh you love the cock you whore, don't you?"

"Yes." Oh yeah. They switched. I had the bigger dick in my ass. They both got on top of me and gave me a facial. The camera did a closeup with my face coated in cum (including in my eye) with me lapping it up.

They mostly put me with guys and other she males to fuck me. I continued to take HRT as I would have to for my life. At 19 I had the bottom surgery though Kenny was against it but he was ready to move on from me and I did a couple of movies with my new pussy but wasn't ready to get fucked there and still took it anally. As I dilated, I waited until the day everything was healed and I could move on with my life as a real woman.

Three years Later

Claire Gates was at her desk at Halstead Realty in New York trying to find an apartment for a difficult customer. A girl walked into the office. Claire

looked up. She was wearing a pink floral dress; the top was cut that she could see she had big boobs. Blonde hair, blue eyes. Loral print dress just above the knees,

great legs. Claire was 100% straight but could see how attractive she was.

"Hi Claire."

Claire looked confused. "Do I know...." A look of realization "Oh my God, Andr, I mean Amanda." The two hugged.

"You..I mean...it's great but...I mean... I mean my little sister has come to visit me." She smiled and hugged me again. Little sister. That sounded so good.

We went into the firms small conference room. "Why didn't you tell me?' She looked annoyed. "You were supposed to let me know how you are? A text every couple of months that said, "I'm okay". I was hoping it was you but at the same time my texts bounced back."

"So how do I look?" I said, changing the conversation.

"If I didn't know it was you, I would not have guessed you...I mean."

"Was born in a boy's body you mean."

"Yeah. You have a great body. Your voice is that of a girl, you have a girls' curves,legs, and a set of tits."

"They're real. I got lucky with that. I put my hands on them." Totally real, no implants."

"Just my luck, I get stuck with A tits and you are a C or D. Did you, uhm."

"Yes, I have a vagina. I was nineteen when I had the surgery. When I was 18 I had all my information changed. My birth certificate, social security card, passport and driver's license.

I am legally Amanda Gates. Do you want to see it?"

"I don't need to" said Claire.

"It's okay, I have to pee, you can take a look. I like showing it off."

Claire got a look. "Looks real to me" she laughed. " Of course the only one I got up close and personal inside was my own with a mirror, but it looks real."

`I'm bi. When my pussy was workable I kind of test drove it. Four girls, only one girl figured it out".

I got lucky with a good surgeon. It was expensive and took all of my money to get it done right." I didn't tell her how I got the money to do this and considering the past she didn't ask.

"So, how's the family?" "James Jr. is in jail. The park you um, used was cleaned out but a couple of years ago it became a gay hookup spot again. He went there with a couple of friends and beat two gay guys going at it. Got 10 years for assault and hate crimes." Big surprise, he was a bully and stayed one.

"Dad had a total breakdown. He said you were probably dead and even if you were as he put it "fag" he didn't want you dead."

"Mom?"

She agreed with him that it was his fault and divorced him. I told her I had gotten texts from you to ease things for her.

I don't know if you would want to see her, but I can set it up."

"Thing is, is she ready to find her son never existed, that I was always her daughter?" Claire nodded her head. It was how I really felt my whole life.

"So, where have you been?" she asked.

"Mostly LA. I had someone run a search for you and your real estate license popped up. I made my way to NY, you always wanted to live here. I've actually been here almost a month. I know you were accepting but it's still another thing to see you. I have a waitress job I have to get to later and I'm living in a woman's hotel on East 30th. I have my own sink, but I have to share a bathroom with the 10 other girls on my floor."

Claire thought for a second. "I have a one bedroom, the couch in the living room is a convertible. I want you to move in. This way you only have to fight one woman for the bathroom" she laughed.

"You used to hog the bathroom all the time. Maybe I'm better off with the 10 women" I laughed.

"Ha ha ha. Now that you're a woman you're going to try to hog it. I'm going to get a dresser for your clothes, maybe I'll let you borrow if those big girls of yours will fit but if you think you're going to hog the bathroom; you got another thing coming.' We both began to laugh.

I was a happy woman. My life as a boy was a blip in my life. I have been and have always been Amanda.

I hope you enjoyed this story, I will answer everyone.

Amandasutton403 @gmail.com

END

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