Tutoring Candy - Cover

Tutoring Candy

Copyright© 2018 by DelawareDan

Chapter 1

Erotica Sex Story: Chapter 1 - Mom's friend Carol had a daughter who wanted to join our swinging group just as soon as she hit eighteen. A couple of weeks shy of her birthday, Carol brought her over to our place so that we could walk the course. Turned out she needed just a little bit of extra tuition before she was ready to face her first sex party. And then, of course, it was only natural for us to give her some more advanced tuition!

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Ma/ft   Fa/Fa   ft/ft   Fa/ft   Mult   Consensual   BiSexual   Incest   Mother   Son   Brother   Sister   Father   Daughter   Swinging   Anal Sex   Oral Sex   Safe Sex   Sex Toys  

The second swinging party I attended, the April one, I’d donned a face mask and once again successfully sneaked into what was supposed to be my own home without being spotted by the party hosts, my parents. After meeting up with my new friend Jessie, and somehow surviving undetected a threesome with her college roomie, my sister Laura, I’d then gotten together with a real nice lady, Carol, and we’d talked for a while as we cuddled after some great loving. We were both greatly amused at the fact that the two girls I’d just been with were right now taking care of Carol’s husband and son! (I found out six weeks later that Carol was Mom’s gynecologist and friend, Dr. Carol Bowen, and Mom eventually told her who I really was, though that’s a longer story for another time.)

One of the things we discussed was if I might help introduce her daughter Candy to the parties, when she turned 18 in three months time. (Carol had no idea that I was there despite my parents attempts to hide the parties from me, or that they were utterly ignorant of my presence.) Of course I said that I’d be honored to help, despite not having the slightest conception of how I might deliver on my promise. I heard nothing more on the subject, not even when I revealed my knowledge to my shocked parents and demanded that I be allowed to play a full part in my parents’ sex party swinging group.

Having been told by her older brother George what a whole lot of fun he was having attending the parties, Candy was real keen to join in just as soon as she was old enough to be accepted. A fortnight before her birthday, Carol brought her over to our house to be shown what went on at the parties. There was a whole lot more for her to discover than she had learned with her high school dates, and I was the lucky guy who got to be her guide.


After our confrontation with our parents about hiding the sex parties from me while encouraging my sister to take part, family relationships were slowly beginning to get back to how they’d been eighteen months earlier, although they’d never be quite the same again, way too much had changed. Anyway, we were on friendly speaking terms, even if I didn’t yet actually trust them 100%.

The morning of Saturday 6/23, Dad was out golfing with some business contacts so hadn’t taken me along, my sister Laura and her girlfriend Jessie were out shopping at the mall, and I was doing some laundry out back when Mom hollered for me.

I found her in the kitchen with Carol and a very pretty redheaded girl, who Carol introduced as her daughter Candy. Carol had her red-gold hair in a rope braid today; she looked real sexy. I just said ‘Hi’ as I wasn’t too sure about the etiquette of how to greet Carol outside of a swingers party; I thought about kissing her on the cheek, but as she made no move, I didn’t approach her. Mom passed me an iced tea and told me to sit down with them. “Mike, you remember Carol told you that Candy was interested in coming to the parties, once she’s 18? It’s her birthday very soon, and we wanted to show her what to expect. You couldn’t help us walk the course with her, could you?”

“Yeah, sure, what do you want me to do?”

“Just do whatever we tell you.”

That wasn’t an entirely helpful reply, but I let it pass. It did turn my bullshit detector back on; I felt that I should have been told about this in advance rather than being bounced into it. After all, I was the person Carol had originally suggested this to, not Mom or Dad.

Mom ignored me and turned to our guest. “Now, Candy, honey, I know that your Mom and Dad will have said this a thousand times already, but I’m going to repeat it one more time. You can’t tell even your very best friends a single thing about what we’re going to tell you now. It’s not illegal, but there are some po-faced straitlaced people out there, who could do us a lot of damage if word leaked out. To keep us all safe, NOBODY outside this group must ever know about the parties. Do you understand that, sweetie, how serious I am?”

“Yes, Mrs Noble, I do. Mom says that she could be banned from working if people found out about this. I’ll keep the secret, I promise.”

“What happens at a party stays at a party?”

“I got it. Like with Vegas?”

Mom chuckled. “Yes, absolutely like Vegas. Thank you, Candy. We’ll trust you. And please call me Abby. Things get kinda informal when there’s a party on.”

Mom turned back to me. “Mike, will you please finish your drink, and then get the boxes and wristbands out of the hall closet so we can run through that side of the evening. I’ll get some masks from my sewing room, and meet you all in the hall.”

I did as she requested. Mom came down with the box of masks, then sent Carol and Candy outside with instructions to wait twenty seconds and then come back in, as if they’d just this minute arrived for the party. We sorted through a few wristbands, and then our ‘guests’ walked in.

“Now, baby. We don’t use names from now on, just wristband numbers. Everyone wears a mask, and it’s for everyone’s benefit that nobody’s true identity is revealed.”

“Okay, Mom.”

Carol laughed. “Wrong answer, sweetie! It doesn’t matter today, but you’ll have to watch it when we come to the real parties. Wouldn’t want anyone to think that Old Mother Bowen needed her hot daughter beside her as a lure to net them both some young studs, would we?”

Candy giggled, Mom and I looked at each other in amusement. Dr. Carol Bowen was one of the hottest MILFs in a pretty select group; Mom had some very good-looking contemporaries who kept themselves in great shape. Carol was a wet dream herself; the two golden-red-headed babes walking together clothed were enough to turn a few heads; I suspected that naked they would be an absolute sensation.

Carol handed her daughter a mask and one of the pink wristbands. “The wristbands just help people refer to you, and they’re useful if you see someone you want to try out a little later in the evening. We also play some games where we use them. You can put the mask on now, or in a minute. Now, when you get to the table, you’ll also find some pills. They’re called Cialis, and although they are primarily prescribed for men to keep their erections going, they seem to help women have more, quicker and better orgasms.”

She reached into her purse and pulled out a bottle of Cialis tablets. She opened it and poured out four pills onto the palm of her hand. “Just the one is enough.”

Carol passed one to her daughter, took one herself, and gave the others to Mom and I. I copied Mom as she swallowed hers straight down. Candy was hesitating.

“Honey, do you want a glass of water to take that with?”

“Please, Mom.”

They headed off to the kitchen. I turned to my mother. “Mom, this isn’t a drill, is it?”

She smirked. “No, Son, it’s for real. The others will be back after lunch, and then we’re all going to have a private party. It’s up to you to make sure that Candy is up for it!”

I laughed. “So, no pressure, then? Thanks a whole bunch for giving me so much warning. You said that the party was tonight; I might have been all sweaty from my workout, or out on a run.”

“No, that wasn’t gonna happen, I was keeping an eye on you. Now, remember that your sister is really looking forward to trying out that new fresh pussy! Since you burst onto the scene, she claims that she’s not being lesbian and bisexual enough!”

I groaned. For a pair of self-avowed lesbians, my sister and her girlfriend Jessie did require me, the third occupant of their bed, to spend one heck of a lot of time with my dick buried in one or other of them. “Those two are going to kill me with their appetite for cock, and then she says she’s not getting enough!”

Yeah, that was most definitely a smirk on my mothers face.

These last six weeks since I’d come home from college and moved into my sister’s bed, I was having more sex than I’d ever dreamed of, and more than I’d actually believed my body was capable of. At least my balls were adjusting to the increased demand, and I was mostly able to keep up. Sis and Jessie had drained me below the reserve tank a couple of times, and I suspected sometimes that they were doing it on purpose to stop me getting complacent. At least they had each other to play with when I was ‘recovering’; my problem was that witnessing their lesbian loving merely hastened the return of my erection, and hence shortened my rest period.

The other two returned from the kitchen. Carol started instructing her daughter again. “Now, everybody will have a test certificate to show that they are clear of sexually transmitted infections or STI’s. We have an arrangement that you show it to the people you meet in the hall, to check it’s current. Here is yours from when we did those tests last month; we’ll need to do them again before each party. See this bit at the bottom with the date? That’s the important part, it’s got to be within the last ten days or so, so you know it’s an up to date test. Remember what I said about going with anyone else outside the group?”

“Must ALWAYS use condoms?”

“Yes, that’s an absolute must. Have you been sticking to that?”

“Yes, and I haven’t been with anyone since you did the test, actually not since school came out.”

“Great, so that’s all fine. Now, I happen to know that the rest of us have valid certificates, so we’ll take them as checked. Next, we take our clothes off and put them in one of these boxes – they’ll be perfectly safe out here. When we come over for the first actual party, you’ll keep your panties on at the start to show everybody that you’re a newbie, and they’re not to come on to you too hard. That’s to ensure that you only do what YOU want to do.”

My Mom had started stripping off her clothes, so I followed suit. Carol too was undressing, so Candy, after looking unsettled at my presence, copied her.

I stole the odd glance at Candy’s body as it came into view; she was a young eighteen, not yet fully developed, but showing promise of a superb figure like her Mom. She wasn’t completely shaved; as she stepped out of her thong I couldn’t help but notice there was a red-gold landing strip on her pubis, but I certainly liked what I saw. A couple of times I caught Candy looking at me as well; I grinned at her as our eyes met, and she shyly smiled back. Our clothes off, we put our masks on, and Mom stacked the boxes against the wall as our two guests donned their wristbands.

Jeez, I was correct. Carol and Candy naked together were a serious hazard to public safety. I’d have to be careful; a guy could easily walk into a wall with these two distracting him.

“We’ll show you round first. Upstairs there are six bedrooms, and you can use any of them. If the door is shut, the people inside are requesting privacy, so please respect that.”

We trooped round, pointing out the bathrooms and bedrooms, and the locked sewing room. Then we toured the old family room, the kitchen and the great room before Mom pointed out the stairs to the basement, and we ended up in the den. Mom gestured for us all to be seated. “Now, Candy, this is not high school dating. We are all here to enjoy sex, not to play games or tease. Everyone is equal, and we all have rights and responsibilities. No means no; you do NOT have to have sex if you don’t want to, and if you ever have trouble with someone, make sure you scream loudly for help and we’ll all come running. Not that we have had many problems, because now everyone understands the rules. If you have the hots for a guy or girl, then just ask them if they are interested. They can only say no, and they should do that politely. Don’t be shy of coming on to someone you like the look of; don’t wait to be asked because you might miss out. Now, there is a certain etiquette. It’s considered a little abrupt to go up to someone and ask ‘Do you want to fuck?’, but ‘do you want to go find somewhere quiet?’ means exactly the same. If you aren’t sure, by all means say something like ‘can we make out for a bit and see how it goes?’. Of course sometimes you don’t need to say anything, you can just catch someone by the hand or the dick and see if they follow you.”

Candy looked a little wild-eyed, but nodded.

“Now, how do you like your pussy being eaten?”

“It’s okay, I guess.”

Mom put her hands over her face. “GOD! Why oh why can’t they teach high school boys to eat pussy? Oh honey, it can be incredible. You are going to have a treat when you have it done properly. There are some pussy eaters in our group who could go All-American, they’re that good. You better put that on your bucket list. How about blowing a boy? Do you spit or swallow?”

With a nervous glance at her mother, Candy agreed that she did indeed swallow on occasion.

“Okay, that’s good. Swallowing gets it nicely out of the way, and reduces the mess. Now, number one here is getting to be a real good pussy licker. Would you like him to show you?”

Another nervous look at her mother, who patted her hand. “Why don’t you two go upstairs and get to know each other a bit better. He’s a real nice guy. We’ll be down in the basement if you want us. And remember, sugar, if you want to stop, just tell him. He won’t mind a bit; it’s entirely your decision.”

I stood up and held out my hand; Candy nervously took it, and we headed up the stairs to Laura’s room, and closed the door behind us.

I turned and looked at Candy. “Candy, those are the rules. I promise, if you want me to stop, tell me, and I will stop, immediately. You aren’t going to have to continue one second longer than you want to. Just say the word if you are unhappy, and I’ll take you straight back to your Mom.”

She still looked worried. “What about you getting blue balls?”

I laughed. “That old high school line! Yeah, if a guy gets too worked up, his balls will ache. But that doesn’t ever mean you have to be the one to give him relief – he can jerk himself off and it will have the same effect. And here at the parties, it’s just a matter of finding another girl who does want to do it, so there’s no hard feelings. So please, don’t you worry about me. I’m old and ugly enough to look after myself.”

She grinned. I sat down on the foot of the bed and motioned for her to sit beside me. I turned so I was looking at her. “Candy, as I just said, we’re going to go no further than you want to go. But if you’ll trust me to push your boundaries a little at a time, I think I can take you somewhere you’ve never been before. Tell me, how many boys have you been with? I mean all the way.”

She blushed. She looked very cute. “Sixteen.”

“Okay, no need to feel embarrassed. Sounds about the right number for your age to me. How many of those would you actually WANT to go out with again? Be honest with yourself.”

That made her think for a while. She had a real cute habit of biting her lower lip between her teeth as she was considering. Being a fully qualified pervert, I spent the time admiring her body. Lovely face, great hair, very kissable nipples and palm-sized tits, trim belly and that fascinating landing strip. Yeah, I was now REALLY looking forward to this chore that Mom had just set me. “Maybe three?”

“Right. So about four-fifths just thought of themselves, not you. That’s high school pussy hounds for you. Now, it’s gonna be very different at the parties. All the guys you’ll meet here have an interest in you wanting to come back to the next party, so they’ll do their level best for you. They won’t brag that they’ve nailed you, there won’t be any gossip, and no-one will get hurt, and certainly not you. Happy so far?”

She grinned at the thought.

“Well, I’d love to get to know that beautiful little kitty of yours better, but would you like to make out for a few minutes first?”

“Sounds like a plan!”

Good, her voice was more confident now. I didn’t get the feeling that I was rushing her. “I’ll lay on my back, and then you can climb on top, which means you can stop and get off whenever you like.”

She nodded, and I stood up and laid myself in the center of the bed, with a pillow under my head. I grinned at her. “No point in being uncomfortable!”

She smiled and crawled up to kiss me. I noticed that she came from one side and kept her lower body away from the danger point that was my erect cock, but we were making a start.

She was a good kisser, if a little self-conscious at first; we made out for a while, and then I turned us on to our sides so that I could move down to her breasts; she gasped as I kissed her nipples and gently squeezed them between my lips. Yep, correct diagnosis, they were indeed very kissable. Not that I’ve yet come across any female nipples that I didn’t want to suck!

From there, it was easy to get her onto her back, and start working my way down her body. It was young and not yet fully formed, but I could see the great potential in it. She was going to be even more lovely than her Mom.

Her belly was flat and toned; the little dimple in the center was crying out to be explored with the tip of my tongue, and then I traced a line vertically down until I hit her landing strip. She shivered again as I followed its edges, and then put my hands under her butt and tilted her so that her delights were fully displayed. Oh man! What a gorgeous pussy! “Put the pillow under your head, Candy, so we can see each other’s faces. You’ve got an incredibly beautiful little kitty, and I want you to watch me getting to know it better.”

She did so, smiling shyly at me.

“Candy, just so you know, I LOVE eating pussy, I have never considered it dirty or perverted, and I’m going to really enjoy the next few minutes – and I hope that you will too. Don’t feel embarrassed, if something feels especially good, say so, and I’ll do it again. It’s all about YOU, so help me make it great for you, willya?”

“Okay, I will.”

“Great! And there’s no need to keep quiet – if you want to make a noise, feel free!”

She grinned, still a little nervous, and then gasped with surprise as I opened her labia with my thumbs and dipped my tongue into her. Never forgetting that I had a learner under me, I really took my time, remembering everything that my girlfriends had taught me, using my fingers as well as my tongue and lips. She made ‘oooh’ and ‘aaaah’ noises in appropriate places, and then as I built it all up, she started panting and moaning. I kept her on an enjoyable plateau for a few minutes, and then took her up to the top of the mountain, feeling her hips move instinctively as she neared her climax. I looked up to see the pink blush cover her tits, neck and face, and then I nibbled her clit and took her over. She let out a scream of joy as her hips and belly bucked, and I quickly raised myself up so I could watch her face. The tremors finished, I moved up beside her and kissed her.

The smile on her face was all the reward I’d ever need.

“Wow, just WOW! I’ve never cum like that!”

“I hope that you’ll say that several more times today!”

She looked me in the eye. “Are you serious? Better than that?”

“Oh yeah, Candy, with your gorgeous body I’m sure we can do even better!”

That got me another shy smile; I suddenly cottoned on that this lovely girl hadn’t received that many compliments about her looks – lewd comments and being hit on by immature jerks, yes, genuine admiration, not so much. So I gave her another one. “I just can’t believe that the dumb high-school jocks didn’t have the basic sense to realize that you’d grace anyone’s arm! Bet you look amazing in a formal gown, with that incredible hair?”

She smiled at that one. “Yeah, I did get an enlargement of my Junior Prom dress photo; Mom insisted!”

“And you looked great?”

“Without getting swollen-headed, yeah, it is my favorite photo of myself!”

“I’d love to see it sometime; I’m sure you looked a million dollars.”

She giggled. “Dad did say something like that when he saw the bills from the shopping trip!”

I grinned and kissed her on the forehead. “Let’s take a break for a few minutes; I bet your Mom is wondering how we’re getting on, and I’d prefer her not to come barging in on us!”

I had already made the decision that after I’d eaten Candy’s pussy, I’d take her back down to her mother, to give her time to accept what had just happened and to be ready to move on to penetrative sex. It was going to take small steps to unlock the treasure that I was pretty sure was hidden inside this girl; having learned what I had about her previous mostly unsatisfactory sexual experiences, I was wary of going too far too fast. I also needed to speak to Carol about managing her expectations of today; Candy was not as experienced as her Mom had suggested. Nowhere near.

I took her hand and led her into Laura’s bathroom, so that she could use a wash cloth on the juices that now covered her groin. I washed my own face while we were there. No point in her being embarrassed or uncomfortable. Then I guided her down to the basement.

Now, that was good timing. Her Mom was just finishing using the Sybian, while mine was working the controls. We stood, still hand in hand, and watched the last minute or so as Carol shuddered out a pretty decent orgasm. Mom helped her lift off, and an already wide-eyed Candy gasped as she saw the rubber cock running with her mother’s juices.

Carol grinned and panted out a greeting to her daughter. “That was real good! Do you want a try on the Sybian, honey? You’ll love it!”

I could see that Candy was tempted, and suspected that she’d prefer me not to be there while she gave it a go; I said that I’d go fetch her a drink, and went out. Mom followed me.

“How is it going?”

“Okay, Mom, I’m playing it real slow. Some jackass high school big shot has made her kinda skittish, but we’re getting there. I’ve eaten her pussy, and she admits that was the best orgasm she’s ever had. I’m sure she’s up for more.”

“Great! Carol really wants Candy to join us; she feels that George has matured and become much more confident as a result of being with the group, and she’s sure that Candy will blossom too.”

I grinned at her. The second party I’d gatecrashed, I’d walked in on Mom urging George to fuck her – only a few minutes after he and his father had been with Jessie and Laura, and I’d been with Carol.

“Have you got him to last longer yet? I seem to remember he went off just too soon for you last time I saw you together?”

She laughed back. “I’m working on it. It’s my summer project. Going pretty well, actually. I’m going to tutor him again this afternoon. If Carol would agree to help out with his training, it would be a lot easier, but she’s not quite ready to take that step yet.”

“I know. Back in April, she wasn’t happy with the idea of us sharing the bed with Sis, Jessie, Kelvin and George. We kind of broke the ice two weeks ago with eight on your bed, though; at least they’ve now had sex in the same room, if not with each other. What time will he be over?”

“Kelvin and your Dad will be bringing George and a selection of pizza back here about one.”

I looked at the clock. That still gave me better than a couple of hours. “And Sis and Jessie?”

“I told them to be back here for twelve, and to come in through the garage.”

Sounded like the others had been given a schedule, and I hadn’t. Warning bells rang again. I called her on it. “So as usual, I’m the mushroom, the one in the dark who’s fed on bullshit?”

Mom looked a little bit guilty; I wouldn’t have picked up on it unless I’d been looking for it. I’d have a word with Sis when she got back. “Listen, Mom, if you’d had the sense to warn me that Candy was coming over, then I’d have been able to talk to Laura and Jessie about the best way to do this. In a way I’m working in the dark, and that’s not fair to me or Candy. Okay?”

“Yes, I’m sorry, Mike, I should have thought of that.”

“Oh, one other thing you better tell Carol. I’m sure that Candy hasn’t had nearly the sexual experience her Mom thinks. Yes, she’s certainly been nailed plenty, but my guess is that a lot of them were trophy fucks, and not many of the boys wanted her enough to make it real good for her. Not even ‘wham bang thank you ma’am‘, more like ‘on, in, grunt, hey guys, I got laid again‘. Understand what I mean?”

“Oh lord! Okay, Mike, I get it. Shall I send the girls up to you as soon as they are ready?”

I thought about that suggestion. It made sense; although Candy seemed shy, I knew that Sis and Jessie would be able to put her at her ease far more than her mother would. “Yeah, let’s go for that. Naked and unashamed. Better do the masks, though.”

“Okay, it’s your call.”

Mom put a frosted jug of iced tea on a tray with four glasses, and gave it to me to carry. We went cautiously down the basement steps, and heard the tell-tale low whine of the Sybian. We peeked round the corner; Candy was sitting in the hot seat, and her Mom was giving her a gentle level of stimulation. Mom put her hand on my shoulder to stop me going any further, and whispered in my ear. “Let her finish before we go in. It will all be a bit unsettling for her, let’s not spoil it by rushing.”

I nodded and carefully put the tray down on a step. We heard Carol speak. “Okay, baby, I’m just going to increase it a little, and then we’ll let you down. Have you enjoyed it?”

“Oh yes, Mom, it’s amazing!”

We heard the pitch of the machine increase slightly, a few more gasps of delight from the girl, and then the noise diminished and stopped.

“Can we do that again sometime, Mom?”

“Sure we can, baby. Let me help you off.”

There was a small sucking noise as Candy dismounted from the rubber penis, and Mom gave her a couple more minutes to recover before making some noise on the stairs and gesturing for me to pick up the tray. When I got round to the Sybian, mother and daughter were standing together. Candy was a little pink and breathing rapidly, and she drank down the first glass of iced tea as if she really needed it. I poured her another. That went the same way. I offered her a third, but she smiled and shook her head in thanks and refusal.

“Mike, why don’t you take Candy back upstairs again?”

I looked at the girl. “Is that what you would like to do, Candy?”

She blushed, and nodded her assent.

“Okay, we’ll see you two later.”

I took Candy’s hand and led her back to Laura’s bed. She looked at me hopefully. “Mike, could you lick my pussy a little more, and then do you think we might go all the way?”

I smiled at her. It had cost the girl something to make that request. It was only a small step, but it was certainly in the right direction. I had a strong feeling that her wishes had very rarely been taken into account in her previous sexual encounters. “Sure thing, Candy! Let’s make it as good for you as we can.”

I took my time. After her session on the Sybian, she was already partly on the way to her next orgasm, but I took her to it slowly and gently. Jessie and Laura had explained that once the girls got started on climaxing, they got faster and easier, and I hoped that was also true for Candy. I once again introduced two crooked fingers, so she was having her g-spot caressed as I nuzzled her clit to completion and a cry of satisfaction.

There was a huge smile on her face as I made my way back up her body and let her taste her juices on my tongue. Then, after picking up as much of her natural lubricant as my cock could catch, I slipped the head into her pussy and very slowly pushed in and out, lengthening the strokes so that more and more of my cock disappeared into the hot wetness. Jeez, she was tight, even after all the tongue and finger action. It was just as well that my girlfriends had dealt with my morning glory earlier, or I’d probably have popped too early with all the excitement of this awesome new pussy.

I had a sudden flash of insight as to why my Dad had been so keen to nail Laura and Jessie, and now Candy. The older ladies at the parties were mostly enthusiastic and skilled lovers, but there was something extra-special about sliding into a young and inexperienced girl with the intention of making love to her like she’d never felt with the mere boys she’d had before. Yeah, I know it was arrogant of me at the tender age of nineteen, but I got a kick out of being about to demonstrate to her what a real man could do. It wouldn’t have been too big a stretch of the imagination to convince myself that I was deflowering a virgin.

Back in reality, I’d gotten myself balls-deep without hurting her. To give her body time to adjust to the intrusion, I lay there and kissed her mouth until she felt comfortable enough to begin moving her hips to restart the action. I used my experience to make it as good for her as it could possibly be, and it wasn’t long before she started turning pink and making the right noises. Once again, I let her orgasm build until it was unstoppable. I looked into her eyes, seeing the uncertainty and the anticipation, and rubbed one of her nipples between my thumb and forefinger. “Cum for me, sweetie, cum like you’ve never cum before!”

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