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My Third Time

After Jessie confesses her love for Kasey, what happens next?

After Kasey and I made love the second time, I seriously started to question what I wanted to do with my life.  I really hated the fact that I had this male appendage, yet the last two nights with Kasey made for a convincing reason not to get rid of it and remain transgendered.  Yet, the hate for having any male parts was strong, and I didn’t know if I could live life with it even though Kasey showed me how much pleasure could be had.  All I would go back to is time.  I had a lot of time to make my final decision.  No need to rush it, just time to see where Kasey and I would go with the situation.

I made Kasey and I breakfast, and was glad that Friday was a two class day for both Kasey and myself.  This meant that by 10:30 am, we would be done with classes for the weekend.  While eating breakfast, we talked more about what happened last night.  Neither one of us wanted to shy away from our feelings which made for a better Friday morning. 

She looked at my with those beautiful doe like eyes as she asked, ”Where do we go from here?”

I looked at her and replied, “Where do you want to go with this?  If we do make this a committed relationship, the campus will think we are lesbian lovers. Are you okay with that?”

Kasey didn’t even bat an eye, “Absolutely. I am so in love with you. I don’t care what the rest of the world thinks of us.”

“You may change your mind when you come to my home town you know. They tend to be more closed minded and hateful.”

“Jessie hun, I can deal with that. As long as your family is supportive and happy about I, that is all I care about.”

“Okay. But don’t say I didn’t warn you. The kids I grew up with were viscous to anyone who supported me, including my best friend Tracy. They were really mean to her.”

“Again Jessie hun. All I care about is your family.”

I was relieved when I heard that, however I knew I would be a wreck when the time came for her to meet my parents.

Kasey and I went out the dorm together and towards our first class. We happened to have class in the same building which was good, however unfortunately, we were not in the same class together. We were about half way to our building when Charles walked by.  He stopped once he recognized me, turned, and yelled out, “Jessie! So glad to see you.”

I blushed a little when I turned to see him, “Hi Charles!”  He reached in and gave me a hug. This caused me to blush even harder.

“I am so sorry I made you uncomfortable earlier this week. I really like you a lot, and was hoping that you would have stayed longer.”

Kasey looked at me as I looked down like a school girl and smiled a little. I lied a little when I replied, “You didn’t. I just had to go.”

“No. I think I scared you. How about we go out for dinner tonight?”

I stammered a little as I didn’t know what to say. “I don’t think it would be a good…”

Kasey interrupted, “How about picking her up at the dorm around seven tonight?”

With a shocked expression, I said “Kasey!”

Her little impish smile came out. When neither of us replied, Kasey stated, “Good. Seven it is then. See you then Charles. I’ll make sure Jessie is ready for you!”

Charles walked off as I stood there in total shock. Kasey smiled and then said, “It is obvious by the look and actions you did when he approached you that you were interested in him.”

“But Kasey, I am in love with you.”

“I know that. But for some reason, I pick up that you are conflicted. It tells me that you need to explore yourself a little more to make sure you are happy with the path you take.”

“But, Kasey, I am happy. I have you in my life. I want to keep it that way.”

“And I am happy, too. I want you in my life, but I want to make sure you have nothing you’ll regret which would cause animosity toward me.”

We continued walking down to our class, “I love you so much Kasey.”

I took her cheek into my hand, and rotated her head ever so gently. I then gave her a soft and sensual kiss to her lips.  She responded with a second kiss, but then stopped.

“I don’t want people to yell get a room at us, when we already have one.”

With that, she smiled and winked at me. She held my hand as we walked to our class.

During class, my mind was so not there. My professor knew that this was one of my favorite classes, so she kept calling on me to answer questions. I failed miserably that day with her questions. I just couldn’t focus as my brain kept thinking about Kasey and how much I loved her, and Charles who for some reason I lusted after. Needless to say, that class was pure torture on me. On my way out, my professor stopped me and asked if anything was wrong. I just shook my head and said I was just really tired. I knew she didn’t buy it, but right now I didn’t care.

My second class wasn’t much better. I focused on Kasey and the two amazing nights of us making love to each other. I certainly couldn’t have asked for anyone better in my life. But then Charles snuck into my thoughts of Kasey. I was grudgingly beginning to think that Kasey was right. I had to go through this date regardless if I wanted to or not. Fortunately, this class went by without incident for me. I hurried back to my dorm room as I couldn’t wait to see Kasey. When I arrived, Kasey smiled and bounded her way to me. She jumped into my arms and gave me a very passionate kiss. I couldn’t resist her luscious lips as I went in for more kisses. Kasey broke free and placed a finger on my mouth.  She then lowered herself onto her knees and lifted my skirt up. Soon, she was licking the tip of my manhood and then she suddenly took me in her mouth. The sensation was driving me wild. Each time she took me deeper in her mouth, the more I felt like thrusting into her. I was torn about receiving pleasure from the last part of my body that I disliked, so I started to fantasize that I just had an abnormally large clitoris. The image in my head was getting me more and more excited. I was really getting into having my large clitoris getting the attention of my love.

Suddenly, my legs were starting to buckle. Kasey hit a spot where I was just moments from orgasm. She could tell that I was about ready to let loose, so she stopped sucking, and stroked it as fast as she could. I was moaning like crazy.

“Oh god, baby. I’m going to cum!”

She aimed my clitoris toward her mouth. My clitoris jerked once, and a load of my cum shot into her open mouth and down her chin. Kasey continued to stroke me to the rhythm of my orgasm. The next stroke and my clitoris shot another string all over her forehead and down her left cheek. Then another shot went all over her neck and upper chest. The final spurt she took right into her mouth.

She stood up with a smile and gave me a very passionate kiss. Kasey fed me my own cream. The texture was really odd to me, yet there was something about it that it was meant to be tasted. It was slightly salty and yet there was also a weird sensation that came from having my cream in my mouth. It wasn’t the best tasting, nor was it the worst. I eventually swallowed what Kasey fed me, and then slowly licked my cream off of her chest. Kasey scooped up what she could on her face, and proceeded to feed me that cum as well. After I swallowed the last part of my cum, Kasey kissed me again.

“God, you make a beautiful lover.”

I smiled and replied, “You’re the beautiful one. I’m the lucky lover. I’m lucky to have such a beautiful girlfriend that also loves me.”

Kasey kissed me again and said, “You’re so sweet. I love you and would like to have your very large clitoris tease my pussy for hours, but, we need to go get something for your date.” 

She grabbed my hand and out the door we went.

We ended up at the local mall with three anchor stores. I was all smiles when we pulled into our parking spot as I had never gone shopping with a girl friend. Kasey started at Nordstrom which to me after seeing all of the shoes, it was a total dream of a store. I found so many cute shoes that I wanted to buy. My favorite sandals were a four inch heeled black sandal by Jimmy Coco. They looked really cute on me, and I was falling for these shoes. Once Kasey saw the look on my face, she looked at the price tag.  Kasey then turned to me and stated, “Girl, I love you. But damn you have expensive taste. “

Kasey showed me the price, and I just about passed out. The sandals were $995. As I was a mostly broke college student, these shoes were way out of the question. After I took off those heels, Kasey grabbed my arm and said, “Let’s go look at some other stores."

Next stop was DSW Shoes. Kasey and I had way more fun there as there were a lot of shoes to choose from, and they weren’t as big of a hit on the bank account. I kept gravitating toward high heeled sandals, so Kasey decided to shift gears with me on how I should dress up. Eventually, I ended up buying a pair of silver platform sandals with a 4-inch stiletto heels. They were really sexy on me.

Next we went to Saphora to buy some make-up. I was giddy as a child in a candy store looking through all of the selections and colors. Kasey and I picked up several colors of eye shadow, shimmer powder, and lipstick to name a few. What I didn’t realize at the time was that the items Kasey picked up and purchased were actually for my date night.

The most fun that I had was at Victoria’s Secret. Initially, I didn’t want to go in there, however Kasey took my arm and dragged me inside. It was my first time ever being in a Victoria’s Secret. Even though I was essentially living as a female, was a female mentally, and loved a lot of the items they sold, I still felt some embarrassment over going inside the store.

A very pretty college freshman stopped us and asked if we needed help. Kasey said, “My friend Jessie here has a date with a very handsome man tonight. I was hoping that you would be able to provide a suggestion or two for something cute, yet sexy, but not slutty.”

The freshman looked me up and down then said, “You look to be about a size 12, with a band size around a 36, and a B cup. Does that sound close?”

I stared in amazement as she was almost spot on.  “I’m sometimes a size 10, but the other measurements are close.”

The girl walked over to a Chantilly lace log-sleeve teddy and held it up to me. “That, my girl would look phenomenal on you.”

I looked at it and thought it was really cute, yet not really sure if this was appropriate for me and the date situation. Kasey saw my mixed reaction and interjected, “Jessie will definitely try it on.”

“Certainly. I’ll walk you to the changing rooms.”

The girl walked us into a room.  Kasey being the last one to enter the room shut the door and leaned up against it. I looked at the girl and Kasey, realizing that they were not going to leave.

Kasey seeing my conflict explained, “Jessie hun, it is alright. Go ahead and change.” Kasey looked at the girl and continued, “Clarissa here is your personal shopper. She needs to make sure everything fits well, and if not will make suggestions on what else to try.”

I hesitated for a moment. Several thoughts went through my brain. Most of them had to do with Clarissa freaking out that I had a certain male part, and what would I do if she did freak out.

“Jessie hun, trust me.”

I looked at Kasey again, and then slowly took off my blouse, followed by my heels. I turned around so she couldn’t see the bulge as I took off my skirt.  Just as I was removing my bikini briefs, Kasey made a weird sound of shock. My natural instinct was to turn around and see if she was alright. Only issue was that I forgot about Clarissa being in the room too. As I turned, my dreaded male appendage swung around and slapped my thigh. Clarissa immediately noticed what was between my legs.

“Oh, my!”

I stammered, trying to come up with something.

“I told you Clarissa. She is one beautiful girl with a nice extra gift.”

Clarissa looked down at it and placed her hand on my manhood. I was embarrassed. Yet knowing that Kasey set this up, it changed the dynamics of how I reacted.

As Clarissa stroked my man part, I involuntarily blurted out “Mmmmm.  That feels so good on my clit.”

Clarissa looked at Kasey, “Clit?” She questioned.

Kasey responded back with, “Yes. Her clit is nice and hard.”

Clarissa giggled, “I need some of that clit inside me.”

I closed my eyes as Clarissa continued stroking me. Kasey was really enjoying watching her friend play with my rapidly hardening clit. I looked at my love, only to see that her hand was touching Clarissa’s back. With a sexy little smile, Kasey slowly made her way to Clarissa’s beautiful round butt. I was so intrigued by Kasey’s motions toward her friend, that I didn’t notice what Clarissa was doing. Next thing I knew, Clarissa had bent over at the waist, so her mouth could slowly envelope my last piece of manliness while also allowing Kasey to access her womanhood. It surprised me when the head of my clit became totally surrounded by Clarissa’s smooth wet tongue and mouth. I felt really guilty allowing Clarissa to pleasure me, yet I was not going to stop this situation. I was still in shock about the turn of events, but it would pale in comparison as what was about to happen. 

I saw that Kasey’s hand had disappeared under Clarissa’s skirt. A moan suddenly came out of Clarissa’s throat which caused a vibrating feeling to reach my clit. I could only imagine what Kasey’s hand was doing, but it must be  doing something right as Clarissa was moaning louder and I almost released in orgasm. 

“My, my, my you little slut.” Kasey said, “I really think you are into girls after all.”

I nodded my head.

“I wonder what you would do if I did this.”

Kasey then raised her skirt. I finally realized that she had gone the whole day without panties. From everything that had happened since we stepped into Victoria’s Secret, it was clear as day that Kasey had a carefully laid out plan. Sadly, Kasey tugged on Clarissa’s hair in order to force her mouth from my hard and drooling clit. Clarissa looked up at Kasey with a moment of submission and then slight fear.

Kasey looked down at Clarissa, “Yes my slut. I think you REALLY like girls. You sure enjoyed a big hard clitty in your mouth. Let’s see what your tongue will do to tame a wild pussy.”  With that, Kasey shoved her pussy into Clarissa’s face.

“Go ahead and fuck her Jessie. She needs a good hard clit inside of her.”

I was totally bewildered. This Kasey was not the Kasey that I had fallen for. My Kasey was a gentle soul who makes passionate love to me.  In one aspect I was totally turned off. Yet in another aspect, Kasey made me so hot and bothered.  An inner conflict was brewing inside of me. Should I yield to Kasey’s request and make love to Clarissa? Or do I tempt fate and deny Kasey’s request?

I loved Kasey too much to risk it by denying her request. I moved around so I was by Clarissa’s most beautiful rear end. My hand reached out to her pink lacey panties, and slowly lowered them down her legs. Clarissa stepped out of her panties and spread he legs. I took my hardened clit into my hand and started to line in up to the lips of Clarissa’s shaved pussy. Just as I was starting to move forward and insert my clitty into Clarissa, the changing door opened up.

“What in the hell is going on?”

I looked at the intruder in bewilderment. It was Clarissa’s manager. Clarissa looked up from Jessie’s pussy to her manager

“Whoa, there! What is this guy doing in the changing room? Clarissa? You’re fired!”

Clarissa looked dejected.

“Now before I call the cops, you two get the hell out of this store, and never come back. If I ever see either one of you in this store again, you’ll be arrested for trespassing. Get out now!”

Embarrassed and ashamed, I quickly got dressed along with Kasey and Clarissa and we left Victoria’s Secret. I was bummed though as I really wanted that sexy lace teddy.

Clarissa parted ways with us at the mall parking lot. Once Kasey and I got home, Kasey drew a nice warm bath for me. Once I got in the tub, Kasey proceeded to help me get ready for my date with Charles. We had all sorts of fun in the bath tub, but alas, it had to end. While I was drying myself off, Kasey came back with a small bag.

“Open it, Jessie!”

I opened the bag, and there was my Chantilly Lace Teddy.

“How?” I asked.

“Well, let’s just say I knew you would love it and ordered it for an overnight delivery.” Kasey replied.

I gave Kasey a big hug. Even though Kasey insisted I wear that teddy under my clothes, I insisted that I wanted to save it for something really special. After that, Kasey spent two hours helping me get ready for my date. 

As the clock approached seven in the evening, I was becoming more and more nervous about the whole date. Memories of my High School homecoming disaster were coming back as freshly opened scars. Kasey sensed it and gave me a sensual kiss on the lips.  “It will be okay. I promise.”

We heard a knock on the door. Kasey rushed to the door and opened it up. I walked into the room to see a stunningly handsome Charles with a big bouquet of tiger lilies, which happened to be my favorite flower. Charles saw me approach. He looked me up and down a couple of times. A big smile came across his face.

“Oh wow, Jessie! You look amazingly beautiful!”

“And you look strikingly handsome!”

Charles handed me the tiger lilies. I smiled, “These are my favorite flowers!  How did you know?”

“Let’s just say a birdie told me,” Charles said as he looked at Kasey.

Kasey immediately said, “Not me!”

“Well, they are beautiful. Thank you so much. Let me quick put them in a vase.”

When I returned, ever the gentleman, Charles took my arm and walked me to his car. He opened the door for me so I could get in.  Then we drove off to a well known expensive restaurant. We were seated at an area that allowed us to see the sunset over the lake.  It was a quiet area and honestly, very romantic. All throughout dinner, Charles was quite the gentleman. I don’t even remember what I ate as I was so enamored with our conversation.

He told me a lot about where he grew up, his family, pets, hobbies, and friends to name a few. Every once in a while he would pause and look at me with his sexy blue eyes and compliment me in some way. As the evening wore on, I was melting like butter. When the sun set, Charles leaned over the table and gave me a kiss. I felt those same familiar sparks that I had felt when Kasey and I first kissed each other.

After dinner, Charles asked if I wanted to go to his place and watch a movie. I was a little apprehensive about it, mostly because of all my not so good experiences with men, but I told him I would love to continue our date. When we got to his place, I sat on this very comfortable couch as Charles got a movie set-up. Once the movie started, Charles sat next to me and placed his arm around my back onto my right shoulder. I leaned into him as it felt like the right thing to do. We didn’t even make it five minutes into the movie when Charles made his move and started kissing me. I was getting so excited about a real man giving me the attention as a woman. Our kissing got even more intense then he slipped his tongue into my mouth. Sparks were flying all over my head, and butterflies in my stomach were growing. I was falling for him. Then thoughts of Kasey crept into my head. I backed off from Charles.

“What’s wrong, Jessie?”

“Um, nothing.” I replied.

I sensed that he was thinking this was a repeat performance of when we first met.

Charles continued, “There has to be something that is stopping you.”

I hemmed and hawed until I let it all out. “I need to be honest with you. I am in love with someone, yet I am so conflicted. I am in love with a very beautiful person, yet I am falling for you as well.”

He looked at me with those big blue eyes, and I was starting to melt.

I continued on, “I have never been intimate with a man before, and I am not the woman you expect.”  I couldn’t bring myself to tell him why because of fear of getting beat up or worse. Yet for some reason, I thought telling him by grabbing his hand and placing it on my hardened bulge between my legs would be better.

Once he felt that I had something extra, I was certain he would beat me up. But those blue eyes told me a different story. Charles leaned over and gave me one of the most passionate kisses I had ever experienced.

I looked at him with a stunned look. “Are you sure?”

Charles replied, “Absolutely. You are the most beautiful woman I have ever met. I fell for you the moment after we ran into each other at the college courtyard.”

I was so relieved, yet I still had doubts if I should do this because of my love for Kasey. Charles continued kissing me. We were getting so hot for each other, that I started to unbutton his shirt. He followed by removing my shirt and bra.

Charles said, “Oh Jessie, babe, you are so beautiful.” As he moved is mouth down to my breasts. He suckled on each one until my nipples were fully erect. My breathing was getting heavier as he so softly continued his love making on my breasts. My hand made its way down to his crotch. I couldn’t believe the bulge I felt underneath his pants. Charles shifted positions which allowed easier access for me.

I unzipped his pants and fished his cock out of its confines. It was such a beautiful thing to see. I smiled a little at my thought of his cock being beautiful considering I hated my own. I stroked it until a small drop of pre-cum graced the tip of his cock. I moved my head down until my lips were just a quarter inch away from the head of his manhood. I extended my tongue, and ever so carefully licked the tip clean of his pre-cum. I pulled back a little so I could take the time to really appreciate the taste of him. I was surprised that it has a slight sweet and salty taste and not bitter like I had heard it can taste. I was so pleased at what I had just done to him.   I decided right then that I needed to have Charles any way he wanted to take me. 

As I was a virgin being with a man, I knew it would hurt the first time. Yet I finally trusted a male to not hurt me physically and mentally.  Tonight I planned on leaving all of my bad memories from my High School days and moving into a world of being a strong and independent woman.

I looked up at Charles with a smile on my face as I lowered my mouth onto his beautiful cock. As the helmet of his cock passed my lips, I realized that I had an advantage over other women.  I knew what caused pleasure for a man as I was equipped as one.  Even though it was my first time ever having a cock inside my mouth, it was pure instinct that drove me to suck him like only a male would understand.

As I licked and sucked his cock, I would constantly look into his eyes. It was a connection that I was making with him. One that he knew I was totally into him, and totally into pleasuring him. I didn’t care about my own pleasure at this point. I just wanted to be that woman that cared deeply for her man’s needs right now.

It was so awesome to know that I was getting him near the edge of cumming before his cock swelled and got even harder. I would take him out of my mouth each time, and squeeze the base of his cock to calm him down.

“Oh god, baby. You are so good as this. Are you sure you never have had any experience with a man?”

I looked up at him and smiled. “Only myself, and I hated every moment of it.  I didn’t want to stroke the hard piece of manhood between my legs, but it was the only way for me to release my urges. I didn’t have any toys to please me either, as the town I grew up in didn’t have any stores that catered to sex. So let’s just say, I am self taught.”

I continued worshipping his manhood with my mouth. I must have edged him about eight to ten times before he was begging for release.  I knew I had him where I wanted him. It felt so empowering knowing I could grant him release or deny him. Never in my life was I in a place that I could do that to a person. It felt so refreshing to me.

“Jessie, please give me release! I want to feel the orgasm rush through me and into you!”

I stopped giving his cock attention and stood up. Charles looked so dejected. But that wasn’t my plan. I turned my back to him and slowly and seductively removed my girl jeans and panties. I wiggled my nice shapely ass at him. I turned my head, smiled, and winked. Then I ran off down the hallway. I ran into his bedroom, and jumped onto his bed. My breasts jiggled as I landed on my back, and I saw that Charles was close behind. He opened up his night stand and grabbed a small bottle.

I spread my legs, and moved my ankles toward my head, exposing my only hole. I was so ready to lose the last part of my virginity and become a total woman. I wanted this so bad. Charles applied some liquid onto his cock, and then dribbled some around my “pussy”. He took a lot of time making sure I was properly lubed up and ready for his manhood. Once he was certain I was ready, he moved the head of his cock to my hole. He slowly started to push it in.

I was so excited at the prospect of losing my virginity that I never tensed up like I heard from other transgenders who had a downright painful first time. I felt a lot of resistance as the head of his cock pressed up against the anal ring, but my excitement seemed to make it pleasurable. Charles pushed in a little harder and I felt the ring and my virginity give way. His cock slid into me much easier. I felt a very sharp burning pain that took my breath away when my ring finally released its gift to Charles. Charles knew to stay still a moment as I regained my breath. Then he started to slowly move in and out of my pussy.

The searing pain was starting to subside and be replaced with pleasure. As Charles continued making love to me, I was getting more and more excited and hot for him. I loved seeing his blue eyes looking and admiring me. I loved watching his six-pack contract and relax as he continued going in and out of me. But most of all, I just loved the feeling of his cock inside of me. It felt so natural for him to be inside of me.

After I started moaning in pleasure, Charles knew it was okay to pick up the tempo. He increased the speed and depth of his thrusts into me. Suddenly, he hit a spot inside of me that sent shockwaves of pleasure going through my body.

“Ohhh god, Charles!  Ohhh fuck, that feels so good!”  Each thrust of his was becoming more intense for me.

“Fuck me, Charles! Fuck me harder and deeper!”  I couldn’t believe that I was talking dirty.

Charles replied, “You like this, babe?”

“Oh, I don’t like it. I love it!” 

My last piece of manhood was responding in ways that I didn’t realize could happen. It was getting harder. Charles continued thrusting his beautiful cock into me. Each thrust felt like a piece of heaven was falling onto me. My body was starting to quiver from the stimulation inside of me. I knew it was only a matter of time before we became one. Charles finally got most of his six inch cock inside of me, and I was having a hard time keeping it together.

“Fuck me, Charles! Fuck me good!”

He smiled, picked up the pace, and thrusted into me harder. His fucking me became so intense and hard, that I could feel and hear his ball sack hitting the cheeks of my ass. It felt so good to me. I was empowered, yet venerable. And I was losing all senses as my climax was building inside. Charles shifted his weight ever so slightly, but it did something really big inside of me. My manhood suddenly twitched, swelled, and got harder. I was about to lose it.

“Oh fuck, Charles! Your cock feels so good inside of me!!!  Keep doing… Ooo, god!!!  That’s…  Ooo, YES!!  FUCK!!!”

My breathing was getting heavier as was Charles. He was entering and exiting me very quickly, so I knew both of us were on the edge. I finally lost it when his thrusting became frantic.

“Ooo, YES! Oooh my, god!!! Your cock! Fuck me with it! Oh, baby!!! Cum with me!”

I was hitting the beginning of the end. I couldn’t take it anymore, and I yelled out, "OOO, BABY!!! CUM WITH ME!  MAKE ME YOUR WOMAN!!! MAKE ME CREAMY!!! I WANT TO FEEL YOU SHOOT INSIDE ME!!!”

I was shocked at how dirty I was talking.

Suddenly, Charles thrusted really deep inside of me and held it there.

“FUCK, JESSIE!!!  I AM CUMMINGGG!!!”

I felt his ball sack against my cheeks pull up closer to his body and release. This was enough to send my own climax through my body. I was shaking a quivering and screaming out in joy. My own nasty piece of manhood jerked and shot ropes of cum all over my stomach as Charles shot his cum deep inside of me.

We finally settled down, Charles keeping himself inside me. We smiled, and I giggled at the feeling that I was now a woman. It was the most wonderful feeling in the world.

As we basked in the afterglow of our love making, I saw movement out of the corner of my eye. I moved my head over to see what moved. As I did, I saw the love of my life, sitting at the edge of the bed with a huge smile on her face.

“Kasey… I ummm.”

She leaned over and kissed me on the lips. “It’s okay, Jessie. I wanted you to experience this.”

“But, I don’t understand? How did you get in here, and why? I love you.”

All Kasey said, “Because I love you…”

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