Dear Diary - Cover

Dear Diary

Copyright© 2026 by callmeQ67

Chapter 2: July

Coming of Age Sex Story: Chapter 2: July - On a girl's fifteenth birthday, one of her gifts is a journal which she uses to record her innermost thoughts. She’s ashamed of her body because she is developing more slowly than her friends and classmates. Little does she know that there’s at least one man who finds her attractive for the very features that make her feel deficient.

Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/ft   ft/ft   Consensual   Mother   Daughter   Black Male   White Female   First   Facial   Masturbation   Oral Sex   Small Breasts  

July 1, 2025

Mom took me to the mall when she got home from work. We got two new bikinis for me, ones that will actually fit my boobs. Then she said she wanted to look at work clothes (boring!) so we agreed to meet in an hour. I went into CVS to look for a new hairbrush, which I did, but guess what? They sell vibrators and other sex toys there! I couldn’t believe it. I picked out a cute pink vibrating penis that’s about four or five inches long.

I was really nervous in the checkout line. I thought they might ask for I.D. or something. But the cashier was a creepy older man who just leered at me and said, “Have fun, sweetie.”

Eww!

July 2, 2025

DeWayne is spending the night again. I can hear them having sex as I write these words. While my mom and DeWayne are fucking, I’m fucking myself with my new vibrator. Omg! I came so hard and so many times!

I hope DeWayne is still here in the morning after mom goes to work.

July 3, 2025

I waited for my mom to leave for work before going downstairs this morning. While I was waiting, I tried on a bunch of different outfits. Is it wrong that I wanted to wear something sexy for my mom’s boyfriend? Yeah, probably.

I decided on spandex volleyball shorts that cling to my butt like a second skin, and a matching sports bra on top.

As expected, DeWayne was in the kitchen. He was wearing jeans and a tight t-shirt. Oh my gosh, looking at his muscles makes me weak in the knees. To make sure he had a good view, I bent over more than was necessary when I got the milk out of the fridge. I can’t say for sure that DeWayne was checking out my butt, but he had a big smile on his face when I sat down across from him.

We talked a little but I don’t remember anything we said. I was very nervous. And I felt weird about trying to make my mom’s boyfriend notice me that way; trying to look sexy.

When DeWayne got up, he kissed the top of my head. I’m not sure what to make of that. It was kind of a fatherly gesture, so a bit anticlimactic after I’d done my best to look provocative. Maybe I’m reading him all wrong and he thinks I look like a little kid.

July 4, 2025

Today is a big holiday here in the USA so my mom and DeWayne both had the day off. Liz invited me and Janice over for a barbecue and pool party at her house.

Mom and DeWayne took me over there and they stayed just long enough for a drink. Thank goodness mom had lemonade even though all the other grownups were drinking beer or wine. That would be so embarrassing if she got drunk and stupid in front of my friends and their parents.

The other moms were all clustered around DeWayne and he turned on the charm. It was almost sickening to watch how they fawned over him. He probably could have had his way with any of them lol.

I introduced him to Liz and Janice and he was polite as always. The three of us were all wearing bikinis but get this: he didn’t ogle my friends even though they’re both super-hot. Instead, he complimented me! He told me I looked fantastic in my new bikini. That made me feel really good.

DeWayne is so sweet!

July 5, 2025

Liz called this morning and she gushed on and on about DeWayne. She was all like, “He’s so handsome! He’s so sexy! He looks like a movie star!” and lots of other stuff I can’t remember. The funny thing is, she’s never talked like that about any of the guys at our school. When I pointed out that he’s over forty years old, she said it didn’t matter.

Interesting. It seems I’m not the only one who thinks an older guy can be attractive.

Later, Janice called and said a lot of the same things lol. I mentioned that DeWayne was eating pineapple for breakfast one day and my mom was being all silly. So Janice explained to me what that was about. Eww gross, mom!

July 6, 2025

The weather was sunny again so I decided to lay out in the backyard to work on my tan. I was changing into my bikini when mom said she was going out to do some shopping. I figured DeWayne would go with her, but I bumped into him in the hall. He was wearing a pair of gym shorts and there was a very prominent bulge in the front.

Oh my god, I thought. Is that what I think it is?

We chatted for a minute and he was looking me up and down while trying not to be too obvious about it. I can hardly believe what happened next. That lump in his shorts began to move and grow. OMG! And then it got really awkward—he caught me looking at it!

When I looked up, he was grinning at me. I blushed about a hundred shades of red. Then I turned and fled down the stairs.

I grabbed a beach towel and went outside, still feeling super embarrassed. I couldn’t believe he caught me looking at his dick. Because that’s what it had to be, right? Anyway, I spread out my towel and lay down. The sun felt really good on my skin and I gradually relaxed. But I couldn’t help thinking about that lump in DeWayne’s shorts.

I must have dozed off because the next thing I remember was DeWayne’s deep voice saying he brought me a cold drink. My brain felt fuzzy with sleep but I mumbled some thanks. DeWayne sat in the chair next to me and when I glanced his way I saw that he was looking me over and smiling.

I’m sure I looked a mess because the sun was really hot and I was sweating. As if that wasn’t bad enough, I remembered that I’d pulled my shoulder straps down to prevent tan lines. The top of my bikini was hanging down so that my nipples were barely covered. Feeling very self-conscious, I pulled the straps back up on my shoulders.

Here’s where it gets really weird. DeWayne said, “Aww, you didn’t have to do that. I was enjoying the view.”

I was too embarrassed to say anything.

“Look, I don’t mean to make you uncomfortable,” he said. “But the fact that I’m seeing your mom doesn’t stop me from enjoying the sight of a pretty girl. And you’re a very pretty girl.”

That threw me. I think I’ve made it clear that I’m very insecure about my looks. I don’t think I’m pretty at all, especially compared to my two best friends. And now here’s a really attractive man telling me I’m pretty! I have to admit it was flattering.

Just my luck that he’s way too old for me and he’s my mom’s boyfriend.

“It’s very sweet of you to say that,” I answered, after a longish pause. “But I’m just a skinny dork with braces on her teeth.”

“I think you look cute with braces.”

Could that really be true? wondered. “I wish the boys at school thought like you.”

“Are you kidding me?” he said. “I figured a girl like you would be fighting off the boys with a stick.”

“Hardly,” I said. “They totally ignore me, or they treat me like I’m an annoying little kid.”

“Those boys are dumb. They don’t know real beauty when they see it.”

As DeWayne spoke, he looked my body up and down in the most blatant, unapologetic way. Like he was drinking me in with his eyes. I suppose I should have been creeped out, or found it demeaning or something like that. But that was not my reaction at all. No, it was a huge ego boost to be objectified by this sexy older man.

Just then, we heard my mom’s car pull into the driveway. DeWayne stood up, and now I had no doubt—his cock was making a very large bulge in his shorts.

“Catch you later, gorgeous,” he said before going into the house.

Holy shit, I thought. Did that really just happen?

I went inside a little later. I didn’t see mom or DeWayne in the kitchen where I expected them. But when I went upstairs to change, I heard them having sex. And a really disturbing thought popped into my head—could he be thinking about me while fucking my mom?

July 7, 2025

If I were a nice girl, I would have cooled it with DeWayne. I would have done everything possible to discourage him. He was my mom’s boyfriend after all, and he was almost three times my age. But I’m not a good girl. I flirted with him shamelessly the next time I saw him. I wore revealing clothes just to see the lust in his eyes. When he was sitting at the table, I purposely bent over him so he could look down my shirt (I have some actual cleavage if I’m wearing the right bra).

July 9, 2025

I got up way before mom left for work this morning. I fixed my hair, dabbed on a little perfume, and applied some make-up (but not too much). Deciding what to wear took a while. I ended up donning the tennis dress my mom bought me when I was taking lessons two years ago. It’s really cute, but I’ve grown a lot since then so it’s really short on me now. It barely covers my butt.

DeWayne’s mouth almost fell open when I walked into the kitchen. “Good morning, DeWayne,” I said, and turned a little pirouette. This was the first time I’d ever called him by his given name. It felt kind of exhilarating but at the same time I was super nervous.

He just stared at me for what seemed a long time. I was afraid he was going to laugh. But then he gave a low whistle and said, “Oh, you naughty little girl.”

“Whatever can you mean, sir?”

“You know exactly what I mean,” he replied, getting up from the table. He came over to where I stood and gently placed one of his huge hands at the back of my head. Then he bent down and kissed me—on the lips! I didn’t even think about it, I just parted my lips and then his tongue was in my mouth.

I’d been French kissed once before, but that boy didn’t know what he was doing.

DeWayne was gentle but insistent, and soon my tongue came out to play with his. There was something very sensual about it, and it made my little pussy tingle. I put my arms around his neck and he lifted me off the floor. I wrapped my legs around his waist and we made out like crazy, our tongues playing tag with each other. My boobs rubbed against his chest and my nipples ached almost painfully.

He finally put me down and said, “Baby, I’m sorry but I need to go to work. I’m giving a big presentation this morning and I can’t be late.”

“That’s a shame,” I said. My legs were shaking, I was so turned on.

“It sure is,” he agreed. “Do you see what you’ve done to me?”

I must have looked puzzled, because he took my hand and placed it on the enormous bulge in his wool dress trousers. Oh my god! I’d never touched a guy’s thing before, and I could feel the heat of it even through the layers of fabric. I squeezed it a little, but DeWayne grabbed my arm.

“I really need to go now,” he said, looking at his watch. He hesitated for a moment before saying, “I’m sure I don’t need to tell you that we have to keep this on the down low, right? Just between you and me.”

I nodded.

“Not a word to anyone,” he repeated. Then he picked up his laptop case and turned to go, flashing me a quick smile before leaving the kitchen. “Catch you later, gorgeous.”

I heard the front door open and close. Moving to the window, I saw DeWayne get into his Lexus and drive away. Then I jumped up and down and screamed. I’d set out to attract a sexy man and it had worked!

My first thought after that was to call Janice and Liz to share my news, but of course I couldn’t do that. I had just sworn to keep it a secret. Besides, what would they think of me? What kind of girl does what I’d just done?

That thought was troubling, and it caused my mood to deflate a bit. But I was still feeling super turned on so I ran up the stairs to my bedroom. I looked at my reflection in the too-small tennis dress. Dammit, I did look sexy! I raised the hem far enough to see my panties, and just as I expected there was a huge wet spot.

I got out my vibrator and fucked myself silly.

July 10, 2025

DeWayne didn’t stay at our house last night. I didn’t ask why, of course. That would be too weird. I had been looking forward to catching him alone in the morning, so it was really disappointing. On the plus side, Janice and her mom picked me up and took me to Liz’s house to hang out at her pool. It was fun being with my friends even though I’m envious of their looks.

But maybe that’s changing a little. After DeWayne said so many complimentary things about me, I’m feeling a little better about myself. Apparently, it shows because Liz and Janice both asked why I was smiling so much. Liz even asked me if I’d started dating someone! I had to say no, but it was hard not to tell them everything.

I mean, it’s the biggest thing that’s ever happened to me and I can’t tell my best friends.

July 11, 2025

DeWayne didn’t stay at our house again last night. It sucks, but tomorrow’s Saturday so he’ll almost certainly spend the night tonight. Unfortunately, mom won’t be going to work in the morning so I don’t know if I’ll be able to catch DeWayne alone.

It’s evening now, and I never got a chance to spend any time with DeWayne today. He and my mom are out to dinner at a fancy restaurant downtown. I was in the kitchen making something to eat when he came downstairs. He was dressed in a blazer and dark jeans.

“You look really nice,” I said.

“Thanks,” he said. “You look very nice yourself.” Really? I thought. I was wearing sweatpants and an old t-shirt.

He crossed the room and wrapped his arms around me. Within seconds we were making out and it nearly made me swoon with pleasure. My nipples started to ache again, so it was a relief when he broke our kiss and starting feeling my boobs through my t-shirt. His eyebrows went up when he realized I was braless.

Oh god! When he thumbed my nipples it sent an electric current straight between my legs. He had just put his hands up my shirt when we heard mom coming down the stairs.

DeWayne went into the living room and greeted her as if nothing had happened. I was still in the kitchen panting with lust. I swear if mom hadn’t been there, I would have undressed and spread my legs for him right there on our kitchen table. I didn’t trust myself to face my mom right then, so I just shouted, “Have a nice time!”

It’s now about midnight. Mom and DeWayne got home a little while ago and they didn’t waste any time going to her bedroom. This probably seems pretty twisted, but right now I’m watching interracial porn on my computer while listening to DeWayne fuck my mom just down the hall. I’m slowly fucking myself with my vibrator as I watch a pretty blonde girl suck and fuck two big black guys.

I heard my mom moaning with pleasure while I’ve had two or three orgasms of my own. When the two men on my screen finally cum, they do it all over the girl’s face. That sends me over the edge one last time just as I hear mom screaming in ecstasy.

I wonder what the school psychologist would say about that!

July 12, 2025

It’s Saturday, so my mom and DeWayne didn’t go to work. That means I probably won’t get to be alone with him. I’m very jealous of my mom, which is not something I thought I’d ever say. I’ve always thought my mom was really pretty. But DeWayne makes me feel like I’m pretty too, and desirable.

I’m worried, though. I need to think seriously about what I’m doing. I realize there’s no way I’m going to have a relationship with a guy in his forties while I just finished ninth grade. I can’t help wanting him, though. DeWayne is exactly the kind of guy I fantasize about when I watch those interracial porn videos. Just kissing him is not enough. I want to hold his big, black cock in my hands. I want him to use me in any way he likes and fuck me until I can’t walk straight.

God, I wish there was someone I could talk to about this.

July 13, 2025

Mom and DeWayne spent the whole day together yesterday which was frustrating. He cooked an elaborate dinner for the three of us and it was delicious, but it kept him busy all afternoon. He had no time to spare for me. Mom helped him clean up afterwards and the two of them were so lovey-dovey that it made me feel left out and low-key depressed.

They went up to her room pretty early. I didn’t feel like listening to them have sex again, so I changed into my pajamas and went back downstairs to watch TV. I managed not to obsess about DeWayne for a few hours. I was just about to turn off the TV and go to bed when I heard someone coming down the stairs.

It was DeWayne. He went into the kitchen and I followed him. He had just taken a cold drink from the fridge when he saw me. He grinned and said, “Hey there, sexy.”

Imagine that—here’s a guy with a body that looks like it was carved from stone. He’s standing there in just a pair of gym shorts, and he calls me sexy.

“You’re looking very sexy yourself,” I answered. That was an understatement!

He set the drink on the counter and beckoned to me. Of course I obeyed instantly and he bent down to kiss me. His tongue slipped into my mouth and mine into his. I put my arms around his neck and he picked me up as easily as if I were a doll. Shivering with longing, I wantonly rubbed myself on his body.

As we made out, I became aware of something. DeWayne’s lips had a scent and taste that was unknown to me but seemed familiar. I didn’t think much about it at the time, but it made me so aroused that I felt reckless. I broke our kiss and said, “I want to feel your, uh, thing in my hand.”

He put me down and gave me a wry smile. “My ‘thing’ is resting right now. It’s pretty worn out at the moment, if you know what I mean.”

“That’s okay. I just want to see it and touch it.”

Without waiting for a reply, I dropped to my knees. DeWayne did nothing to stop me as I tugged his shorts down. Oh my god, there it was. Even soft, it hung down like eight or nine inches. And it was uncircumcised, which I only knew about from watching porn.

“It’s beautiful,” I whispered, taking it in both hands. It was everything I’d dreamed about. Even flaccid I could feel the weight and the strength of it. It also felt sticky.

Oh Jesus, I thought. It’s sticky from being inside my mom.

That’s when it hit me—that scent on DeWayne’s mouth was also from my mom. He’d been eating her pussy!

A normal girl would have been sickened by this realization. Liz or Janice would probably have turned away in disgust. Not me. I began to stroke his cock gently, watching in fascination as the purplish head emerged from the foreskin on each stroke. I looked up at DeWayne and he was gazing at me with obvious lust in his eyes.

I knew for sure he was getting aroused when I felt his cock begin to get hard. Hot blood pulsed under the delicate skin as it swelled in my little hands. My god, that was empowering! Here I was, the late bloomer with the skinny legs, and I could make this sexy man’s cock hard even after he’d been fucking all evening.

It was growing harder by the moment, and thicker too. My hand didn’t come close to going all the way around it.

I wanted nothing more than to worship that big, beautiful cock.

“Put it in your mouth, baby girl,” he said. He spoke quietly but with authority.

As soon as he said the words, I realized I’d been hoping he’d say that.

Just the head alone filled my mouth completely. I could taste my mother’s pussy on it and, god help me, that turned me on even more. It was fully erect now, and felt like hard muscle in my hands. There was a fat vein running along its broad back, and other veins going here and there.

I continued to stroke it while trying to stuff as much as I could in my mouth. The head was pushing against the back of my throat and it caused me to drool. “Oh fuck,” he groaned, as a streamer of saliva ran down my chin.

DeWayne placed one of his big hands at the back of my head and thrust gently with his hips. I began to choke on his dick, and it made my eyes water.

Just then my mom called from the top of the stairs. “DeWayne, honey? Did you get lost?”

“Oh, shit,” he said quietly. He helped me to my feet and picked up the can of seltzer he’d taken from the fridge. “I’m on my way,” he called. Then he kissed me one more time and left the kitchen. I heard him taking the stairs two at a time.

I was in a daze. My legs were trembling such that they could hardly support me, so I sat on a kitchen chair. Did I really just suck DeWayne’s cock? I knew we were venturing into dangerous territory, but I didn’t care. No one had ever made me feel so grown-up and sexy as this forty-something black man.

Eventually I was able to stand. I went upstairs intending to get out my vibrator and put it to use right away. But when I reached the top of the stairs, I heard sex sounds coming from mom’s bedroom. And the door was ajar.

I stood there listening for a minute or two. “Oh god, DeWayne,” my mom whimpered. “Give it to me ... fuck me, baby ... yes, fuck me ... yes ... yes...”

I crept over to the door and cautiously peered around it.

My mother was face down on the bed, her ass high in the air. Luckily, her head was turned the other way. DeWayne crouched behind her like a giant mythological beast, his hands on her waist. The muscles in his legs stood out from the strain and his dark skin shone with perspiration. My mom looked tiny and pale beneath him.

She was mewling like a kitten as DeWayne’s thick black member slid in and out of her. “Just like that,” she mumbled into the sheet. “Keep fucking me just like that ... yes ... yes ... I’m cumming again...”

I stood there as if frozen, watching my mom get railed.

Then, almost as if he knew I was there, DeWayne turned and looked at me. He smiled, and I realized that I was rubbing my sopping pussy as I watched.

“I’m gonna cum, baby,” DeWayne growled. “Yeah ... yeah...” He pulled his cock out of my mom and took it in his hand. With a roar, he shot three or four great jets of semen on her smooth white ass.

I’d seen enough. Too much, in fact.

I tip-toed down the hall to my room and closed the door. Then I fucked myself to a mind-blowing orgasm with my vibrator, wishing it was DeWayne’s magnificent big, black cock.

July 14, 2025

I was too exhausted to put my pajama bottoms back on last night after I’d pleasured myself. I fell asleep wearing only my little camisole top.

My dreams were wild. In one dream, mom told me that she was glad my dad had left because he’s a loser. “And he has a little dick,” she said. In another dream, I was at school and I was naked from the waist down. I tried to hide by sitting at my desk but everyone knew. It was humiliating. The dream was so disturbing it woke me up. It was a while before I fell asleep again.

I did eventually though, and more dreams followed. The last dream was the craziest of all. My friend Janice was licking my pussy, and it was the most wonderful feeling in the world. “I didn’t know you liked me that way, Janice!” I said, and she kept right on eating me. “Oh yes,” I muttered in my sleep. “Please don’t stop ... that feels so fucking good...”

It was only when a hand clapped over my mouth that I understood this was not a dream. I could only just make out his silhouette in the dark, but of course it was DeWayne, not Janice. His lips and tongue were all over my little kitty. He was exploring every fold and the pleasure was otherworldly. I had no idea anything could feel that good.

Instinctively, I started to roll my hips. I held the back of his head with one hand while the other clawed at the sheets. My moans were smothered by his hand.

When he sucked my clit into his mouth and flicked it with the tip of his tongue, I lost control. I came so hard I had to hold DeWayne’s head with both hands because my ass was bouncing off the bed. The release was like an earthquake. It exploded from my very core and radiated all the way to the tips of my toes. My legs shook like crazy.

He knew exactly what to do then, extending my pleasure while bringing me down slowly. I held onto his head until my legs stopped trembling and all the while he lapped softly at my kitty, drinking up my nectar. When I’d caught my breath, he pulled up my top and kissed my breasts, one after the other.

“I’ve wanted to kiss your titties for so long,” he said. Then he kissed my mouth, letting me taste myself on his lips and tongue.

“Baby girl, you have the sweetest little pussy I’ve ever licked. But there’s something I want you to do for me.”

“Okay, sure.” I would have done anything he asked just then.

“I want you to shave for me before next time.”

I was thrilled. He’s already saying there’s going to be a next time! I don’t know why he wants me to shave, but I’m not about to refuse. I’ll do anything he wants me to do.

“Just remember,” he went on. “Not a word to anyone, not even your best friends. Understand?”

“Yes, sir,” I replied.

“I’d better go,” he said. He kissed me one more time and quietly slipped out of the room.

I wonder if he washed his face before going back to my mom’s bed.

July 15, 2025

It took a long time for me to go back to sleep after my encounter with DeWayne in the middle of the night. As a consequence, both he and my mom were gone when I woke up this morning. I was upset that he didn’t come to my room after mom left, but I suppose he had another presentation or something. I wish he didn’t have to work.

I had been thinking about him a lot since the first time he kissed me, but now that DeWayne has eaten my pussy I think about him constantly. I mean, like, every waking minute. It actually frightens me how much I want him.

My rational mind understands that it’s kind of sick that he’s fooling around with me while fucking my mom. When those thoughts begin to creep in, my libido takes over and I tell that part of my mind to shut up. I can’t wait to get my hands—and my mouth—on his huge black cock again.

Naturally, I did as instructed and shaved my pussy. It wasn’t difficult because there wasn’t much hair down there. I don’t much care for the result, though. I want to look more grown up, not less. So it’s disheartening to look in the mirror and see my smooth, hairless sex. It’s a good thing I have boobs. Without them I’d look like I was ten years old again.

July 16, 2025

DeWayne didn’t spend the night again, which was disappointing. I guess he has a pretty high-pressure job. I know I’m being unreasonable when I expect to see him every day. But the way I long for him is way beyond reason.

July 17, 2025

I’m so excited—Liz and Janice are going to sleep over at my house tonight! Their moms are bringing them around six. We’re going to order pizzas and watch movies, and we’ll probably stay up talking half the night.

DeWayne is coming over tonight, too. I hope my friends don’t hear him and my mom having sex. That would be so embarrassing.

July 18, 2025

When I started writing in this journal, I had only been kissed a few times. It never occurred to me that I would try so many new things this summer—sexual things, that is. I had no idea my mom would start dating a black guy, and I certainly never thought I’d get involved with him. I was never attracted to any of my mom’s previous boyfriends.

But things have got out of control so fast it feels like a roller coaster ride. Well, what happened last night and in the wee hours of this morning has made the ride so much wilder.

Liz and Janice came over around dinner time like we planned, and we ordered pizzas. My bedroom is pretty small so I had suggested that they bring their sleeping bags with them. That way we could all sleep on the floor in the family room.

We had a great time catching up with each other and we laughed ourselves silly. When it got late, we went up to my room and changed into our PJs. Then we went back downstairs to watch TV some more. Mom and DeWayne went up to her room around eleven. She told us to keep the volume low on the TV and to keep our voices down.

The three of us stayed up talking long after that. Naturally, Janice and Liz wanted to talk about DeWayne. Both of them positively gushed about how sexy he is. They asked what it’s like having him around the house and how I feel about him sleeping with my mom. I was itching to tell them everything but I knew it wasn’t a good idea. Besides, I’d promised to keep it a secret.

Liz was the first one to fall asleep. Janice and I talked a little longer and then she drifted off too.

Me? I started watching porn on my phone.

I found a really hot video with two cute girls pleasuring each other. They were licking each other’s pussies and they sure looked like they were enjoying it. I began to rub my needy little kitty through my pajamas.

The more I watch girl/girl porn, the more I think it seems like something I might want to try. I mean, a girl should know what makes another girl feel good, right? And now that DeWayne has eaten my pussy, I know just how pleasurable it can be.

I was very cautious about touching myself at first. It would be so embarrassing if Liz or Janice caught me! But my caution faded away as I became more and more aroused. I slid my hand inside my panties to rub my clit directly. Every couple of minutes I’d lick my fingers to keep everything wet and slippery. Pretty soon I was on the edge of a nice orgasm.

 
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