“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.