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.