Too Good To Be True Ch. 16

"Fuck!" Cindy breathed.

"Yes!" Courtney celebrated.

"I take it Courtney just won?" I surmised.

"Yeah." Cindy grumbled.

"I told you." Courtney laughed.

"Will you tell me what the terms were now?" I asked.

"No," Courtney laughed. "You'll find out soon enough."

And with that, Cindy put her underwear away, hidden deep in her dresser.

We emerged from her room, she had insisted on keeping the gifts hidden, though Courtney had kept the gifts for me and would give them to me for Christmas.

Courtney informed my mother I'd she wanted to send any Christmas gifts to her, then she would hold on to them and give them to me at Christmas, assuring her that she wouldn't let me open them early. My mother was excited by this and got the address to send our stuff too.

Courtney then asked me if I wanted to go shopping with her, after all, it was Black Friday, and there were really good deals.

"Sure," I said, grabbing my coat. "And you get another mall trip out of it."

We hopped in my car, and headed to the mall.

"Will you please tell me what is up with that bet with my sister?" I begged.

"Okay," Courtney relented as we drove, "Well, we were in the sex shop, and Cindy said she bet she knew what you liked better than me, since she'd known you longer. I told her I would take that bet. So we both got a pair of each of those sets of underwear, and the bet was that we'd do Yoga together tomorrow morning, and the loser had to wear the chosen underwear and nothing else. So, if you had picked one of the pairs we hadn't picked, we both would have had to wear it."

"Wait, you're going to make her do YOGA in front of me just wearing that?" I gasped. "She'll be basically naked, and she'll have to show everything!"

"I was more for just doing a fashion show for you, come out wearing it twirl, then she could go put on clothes, but she wanted to 'humiliate' me.... She insisted on Yoga, and was confident enough that she insisted it be an hour long yoga session. She said she wanted to watch you get hornier and hornier until you just fucked me mid yoga session." Courtney laughed. "I think to help her not die of embarrassment flashing her ass and pussy at you, I'll wear the underwear too, and when you get too wound up, you can fuck me. That girl needs to learn that when it comes to showing off my body or doing sex acts with you, there is nothing that could humiliate me."

"Courtney, we need to call it off." I told her, "We can't be making my sister do sex things around me. It's incest and it's not okay, especially when she is being coerced to do it."

"I'm not coercing her." Courtney laughed, "Why don't you text her when we get there? We can grab lunch and you can text Cindy."

"I'll do that." I told her.

We arrived and got some cheap Americanized Chinese food.

I texted Cindy, "So, Courtney told me about the bet. You don't have to do it."

A moment later, Cindy texted back. "Really? You think I am a welcher? No, I would have made Courtney do it and I am not going to pull out just because I lost."

"But Cindy, you'll basically be naked!" I told her.

"You've seen me naked. I'll be fine. Just keep your dick in your pants." She told me.

Courtney was sitting next to me, reading the messages. "Told you she wouldn't back out."

"Oh god." I muttered.

"Oh, don't pretend you aren't going to enjoy it. And you have my full permission to fuck me when you get too horny. I'll even lube up my asshole for you in case you want some of your 'hot piece of ass' while you are staring at two hot asses. " Courtney teased. "Now, let's get your holiday shopping done, and maybe we can go back to the sex shop, after all, I owe you a free for all fuck with me restrained however you want."

We easily found things for my parents and older siblings and a few quiet baby things for my nephew and niece.

"We should get Cindy two presents from you." Courtney told me, "One she can open in front of your family... and one she has to open privately in her room."

"Why do you insist that I get something sexual for my sister for Christmas?" I asked.

"Because she is opening up to the world of sexual experiences." Courtney informed me. "Right now, she is in the lucky position that she has a loving brother who she can ask questions to and trusts. You can either nourish that relationship, or she'll have to find answers elsewhere. Which would you rather? I like Cindy too much to let her ask her questions to random men about sex."

"Fine!" I told her.

"She needs a new laptop...." Courtney suggested.

"A decent laptop is a thousand dollars! You've already spent eight hundred dollars on my Christmas gifts!" I exclaimed.

"Daddy gave me double my normal Christmas budget because with a boyfriend I have more people to buy for. I spent two thousand dollars with Courtney. She was shocked that I didn't bat an eye, but I have fifty thousand dollars and Daddy wants me to spend it all on Christmas." Courtney informed me.

"Fuck... I guess we could get Cindy a laptop... She was saying she was getting into gaming..." I conceded. Twenty minutes later we were walking out of an electronics store with an Alienware laptop for Cindy.

"God, Melody and Joe would be so jealous if they were there when she opens this." I told Courtney. "Not just because it costs six times as much as their gifts."

Not far from the electronics store, Courtney pulled me into a poorly lit sex shop. Walls of mannequins wearing lacy little bits of nothing lined the walls and shelves of sex toys were everywhere.

"Now, if you want me to step aside so you can buy me something... I'm okay with that." She teased.

"I'm taking you up on that." I told her.

"But I'm paying for your secret gift for Cindy." Courtney informed me.

"Fine." We wandered the isles, Courtney commenting on various outfits, or toys. I made mental notes of a few sexy things I wanted to fuck Courtney in. Then we reached the BDSM section. I had learned that while restraints, handcuffs and such turned Courtney on, they also scared her. She leaned up next to me, but nibbled her lower lip.

It only took me a few minutes to figure out what I wanted in that section and Courtney relaxed as we left.

"So, was there anything that Cindy was asking about?" I asked Courtney, "I don't know what I can get her to help her, sexually."

"Well, she was really nervous about anal sex. She seems to be incapable of believing it would feel good." She admitted, "Not sure what to do to help her with that."

"I have an idea." I said, and I looked around before I found what I was looking for.

"Ooo, that could work." Courtney mused.

It was a set of anal training butt plugs. The smallest ones barely would stretch her butt, but the larger ones would prepare her for a cock, even one as big as mine. Then I got her a vibrating butt plug about as big as the biggest one from the training kit and a good tube of lube to help her with it.

"Happy now." I asked Courtney, when she finished paying.

"Absolutely." Courtney assured me, and the female clerk gave me a knowing look and glanced at Courtney's ass.

"Now, shew. I need to shop for your Christmas." I told her.

"I'll be in the food court." She told me, kissed me and scampered off with the bags of our purchases.

"That ass will be nice and tight still, even with those trainers." The clerk commented.

"Oh, I know." I told her.

I got Courtney several things. Vibrating panties, a dildo specifically so I could do double penetration on her, several sets of bondage gear, vibrating nipple clamps and a sex massage gel that warms itself when in contact with air. I liked her in lingerie, but she just bought herself several pairs of them.

The clerk was impressed with the quantity of my purchases. "Don't break her too hard, she might run." She commented, ringing up a harness that attached to her neck and would keep her wrists and ankles by her butt.

"Oh, she's kinkier than you think." I told the clerk and she nodded her head, conceding that I probably knew my girl better than her.

Courtney was easy to find in the food court with all the bags of our loot piled around her. She saw the multiple bags, and got excited.

"Nah, have to wait for most of this until Christmas." I told her.

"Oh... don't make me wait..." She begged.

"Absolutely making you wait, though there may be a few things in her that you'll get to enjoy before then." I told her, kissing her. "After all, we do have a bet to settle."

"Oh, you got something to strap me down and fuck me?" Courtney asked, aroused.

"Of course." I told her, "You want to keep shopping or want to go to your place and I'll show you."

"Fuck, to the car we go!" She proclaimed.

The purchases barely fit in the car. We got to the airbnb, and we took a good portion inside.

"Ready to fuck me, master?" Courtney asked through lowered lashes.

I took her hand, grabbing one of the bags I had specifically put items in, and led her to the bedroom. I could feel Courtney's excitement as I brought her to the room.

The first thing I brought out was a silken blindfold. Coutney moaned as I covered her eyes and tied it in place.

"I can't even see what you are about to do to me?" Courtney complained.

"Of course not, it's more exciting this way." I told her, and began stripping her. I could never resist sucking on her perky nipples when they came into view.

Once Courtney was naked I led her onto the bed. She shivered as she heard me opening multiple packages. Then I put padded restraints on her wrists and ankles. Finally, I placed a padded collar on her neck. The strap her limbs would be secured to flopped on her back, spanking her lightly.

"Oh, fuck. This is hot." Courtney moaned. I clipped her wrist and ankles to the strap. It was tight enough that in order to work the angle, her legs naturally splayed, opening access to both of her holes as I leaned her back and laid her on the bed.

I decided to have some fun with her before I fucked her. I started nibbling on her neck, and groping her tits. She shuddered and shifted, obviously getting extremely aroused. After a minute, I shifted between her splayed restrained legs and while still groping her tits, I started licking her pussy.

"Fuck, you get me so horny. I want your dick! I want it in me!" She begged.

"Oh, you'll get it... in a minute. When I am done with this." I told her, lapping again at her pussy. I stopped groping her long enough for my clothes to hit the floor. I grabbed the massaging gel and began to rub it into Courtney's exposed body.

"Fuck! That feels so good! Damn it, please fuck me." Courtney begged.

"Oh, but dear, I get to fuck you holes however I want, and I want to make you need it desperately first." I told her. "You just aren't horny enough yet."

"Fuck! You're so mean!" She moaned as I rubbed the gel into her breasts.

I retrieved the dildo and lubed it up, setting it aside.

I rubbed my fingers up and down her slit, and started playing with her clit. Immediately, she came. I kept going, getting her to cum, again and again.

'Please, baby, I need your dick!" She begged, finally desperate.

"How about this?" I asked, and slowly inserted the dildo into her sopping cunt.

"Oh, is that... that's a dildo... I want you in me!" She begged, as I rubbed lube on my dick.

"Like this?" I asked, and with the dildo still buried in her pussy, I pressed my dick into her ass. Her ass and sphincter were not prepared to stop me, and I popped into her ass, the lube making my entrance easy.

"Oh! FUCK!" She gasped. It had been a few weeks since I'd needed to prep her ass for fucking. It was tighter this way now, and Courtney assured me it didn't hurt. "FUCK!!!" She gasped, squirting around the dildo.

I started pounding her ass and ramming her pussy with the dildo, alternating which one was going in.

"FUCK!!!!" She could only gasp, squirting again. "FUCK ME!!!"

I continued ramming my dick in her tight asshole as I pistoned the dildo into her pussy. I clicked a button engaging a vibrating function on the dildo.

"FUCKING GOD!!!" She gasped, her arms and legs pulling against their restraints as she orgasmed again, her pussy spouting her clear ejaculate spreading all over both of our bodies as she came repeatedly.

The sensations of her cumming finally drove me over the edge and I dumbed in her ass. While still thrashing from her orgasm, Courtney's body suddenly seized up and her mouth opened in a soundless scream and her ass clamped down on my spurting penis.

"No more." Courtney gasped, "Oh god, my body is so sensitive... I can't take any more."

I flopped next to her for a second, pulling both my penis and the dildo out of her. Then I began releasing her from her restraints.Once she could, she removed her blindfold and kissed me.

"Every time I think you have peaked, you fuck me even better." She laughed, holding me close. "Double teaming me with a dildo... why didn't I think of that?"

"Because you aren't a pervy man who wants to be in both holes at once." I told her.

"Oh god, if you had two penises... I still prefer your penis to the dildo. Damn, though, that was mind blowing." She gasped.

We cuddled for a minute then cleaned up and returned to my parent's house just in time for dinner. After dinner, I took Courtney back to her airbnb for the night. She was exhausted from not only the mind blowing fuck, but the shopping trips as well.

I got home and my dad was in his room playing on his computer, and Cindy was in the front room. Courtney had paid to get the gifts for my family gift wrapped, and I placed them under the tree, with the exception of the secret gift for Cindy.

"Where's mom?" I asked Cindy, sitting down with the bag with the secret gift for her.

She played with her skirt and replied. "She's visiting with the Garcias. They needed help decorating for Christmas."

I could tell she wanted to say something.

"Tom, Courtney told you about or bet?" She asked.

"Yeah... You still don't have to do it." I told her.

"You don't like looking at my body?" She asked, lifting her skirt, presenting her pussy fully exposed in the crotchless panties. "Tom, don't look away. I want you to look." She said, blushing.

"Why, sis?" I asked, "I mean, you are sexy, but you are my sister!"

"Why does that matter?" She asked, lowering her skirt. "I just want... validation! Is my body attractive? I don't want any of the fuck-boys at my school looking at me, and I don't want to put pictures of my body on the internet! But I need to know that my body is... desirable. For the first time, I feel like I might have a chance attracting a boy I want! I... By myself, I feel like I don't have anything a boy would want... You are only here for a few days... and you won't be here for Christmas... I need to get as much validation as I can while a boy I want my body to be attractive too is here! Then I'll be back to being alone with the mean voices in my head telling me I don't have a butt, and my boobs are too small." Cindy breathed.

I felt bad for her. I knew that this was a common problem, young girls who saw supermodels and porn stars and didn't feel like they messured up. That led to far too many of them putting nudes up on the internet, and those came back to haunt them later.

"Cindy... I want to help you, but if we keep going this way, we're going to end up having sex. I can't do that." I told her, "I can't betray Courtney the way Nikki betrayed me." It was a little more complex than that.

"But here's an idea, once I am gone, when you need validation, we can find an app that you can securely send me pictures of your body, so I can tell you how attractive you are." I told her.

"I'd... I'd like that." She accepted.

"Also, um... so I got you a second gift... there is a gift for you under the tree, but I got you another gift... we should open it... in your room." I told her.

Cindy's eyes opened and she got excited. We went to her bedroom and I told her to cover her eyes.

I laid out the training plugs, the vibrating plug, and the lube.

"You can open them now." I told her.

Cindy opened her eyes. Her gaze danced over her gift.

"I don't understand, what are these?" She asked.

"They are called butt plugs." I told her.

"I see that, but what is a butt plug?" Cindy asked cautiously.

"Courtney said you were interested, but concerned about one day doing anal sex." I told her. "I also know you wanted to hold onto your hymen, until you can actually have sex. So these will help you get used to having something in your butt. They will help stretch your butt hole, and get you ready for anal sex, and when you can comfortably fit this one in your butt," I motioned to the vibrating one, "It is a good sex toy you can have vibrating to stimulate your butt, while you rub yourself to orgasm."

Her eyes widened as she realized what the toys were.

"Oh! Thank you!" She celebrated throwing her arms around my neck. Then she pulled back, "Um... could you help me try it for the first time?"

I braced myself, "Yes, I can help with that."

Cindy squealed and flopped down and opened the box for the training butt plugs. The set was a four piece set. The small one was tiny, with a couple of bumps to help it stay in, and they had a curved hilt to nestle into her butt crack and keep them from getting lost inside her.

"Okay, so how does this work?" Cindy asked.

"So you are going to want to lube up the plug, then lay back, expose your butt hole, and gently work it inside. Then you leave it inside for as long as you can, to get used to having something inside you." I told her.

"Okay." Cindy acknowledged, and I helped her lube up the plug.

"Could you put it in me the first time, it scares me." Cindy asked.

I breathed deeply. "Okay, here we go."

Cindy laid back and pulled up her skirt, exposing herself to me again.

"So earlier you struggled with the idea of wearing these in front of me." I told her lightly touching the crotchless panties, "What changed?"

"Courtney and I talked a lot while we were shopping, and I had a lot to think about. I had to figure out what I was feeling and what I wanted." Cindy admitted.

"I guess that makes sense." I told her, and I positioned the plug at her pucker. "I'm going to gently insert it. Relax."

Cindy took a breath and spread her butt cheeks for me.

I pressed and the lubed silicon entered her pucker about an inch.

"Oh, that... that's unique... not bad, but unique." I pressed the first bump into her ass. "Oh, give me a second... okay. You can go."

I pressed the second, slightly larger bump into her ass, then the final, largest bump into her and settled the hilt into her butt crack.

"And it's in." I told her.

"Mmmmm." Cindy groaned, and began playing with her pussy. "It feels so... interesting..." She kept rubbing until she had a climax. "Oh, that is better with the plug in." She gasped...

She looked over at me. "Did... did you get an erection watching that?"

"I did." I confessed.

"Could I watch you masterbate now?" Cindy asked.

"I suppose." I relented. I knew I shouldn't, but I was really horny after plugging her ass with that toy and watching her play with herself.

I brought my dick out of my pants and began to rub my length. I was staring at my sister's slit and the plug in her ass. She blushed seeing where my gaze was, but she spread her legs so I could see better. It only took me a minute to reach my peak.

"Shit, where do I cum? Do you have tissues?" I asked, as my rubbing had its desired effect.

"Oh, I'm out... ah... ah... here, cum in this." Cindy said as she looked around, then grabbed a cup she had on her desk. She handed me the cup, and I held it before my cock and spurted repeatedly into the cup.

There was a couple of tablespoons worth of cum in the bottom of the cup when I was done.