Too Good To Be True Ch 16

Chapter 16

We met up in the main living area, Cindy had just learned how to actually masturbate after standing by naked watching me fuck Courtney.

Cindy was still blushing like mad, "You won't tell mom, will you?"

"I won't if you don't." I told her.

"Deal." Cindy said, extending a pinky.

I laughed and completed the pinky promise.

The drive back was full of small talk about sex between the two girls, occasionally asking for my input.

Mom was happy to see us and dinner went smoothly.

"Did you get Courtney all settled in?" Mom asked when we had finished eating.

"No, honestly we mostly enjoyed the hot tub, and each other's company." I told her.

"Cindy told me she got a new swimsuit, was it a one piece like I asked her to get?" Mom asked me, concerned.

Cindy glanced up at me in fear.

She had nothing to worry about. "Yeah, she and Courtney were wearing similar swimsuits. A guy could wish for more skin, surrounded by beautiful girls." I grinned.

"Oh Tom, that is inappropriate. I am sure they both looked great." Mother chastised me.

"I'm just teasing, they looked great." I assured her.

"Now Courtney, don't let Tom pressure you into anything." My mother worried, "I tried to teach him to be a gentleman but sometimes I think I missed the mark."

"Oh, I know he's teasing. He respects my boundaries, and all I have to do is ask for him to back off and he does." Courtney smiled at me. It was easy to respect her boundaries when they even included fucking other women. I didn't think there was a single sexual thing Courtney had ever said no to, if not openly encouraging me to do to her. I don't think she'd ever told me to back off either.

"And I hope the love birds behaved in front of you, Cindy?" Mom asked.

"Oh, yeah." Cindy assured her, "They were great hosts."

Mother seemed happy about that, as was dad.

After dinner we chatted for a bit before Courtney asked me to drive her home.

"I expect you back in a reasonable amount of time, young man." My mother informed me, with a raised brow.

Good thing we had done that earlier.

As soon as the car left the driveway, Courtney turned to me. "Too bad Cindy isn't at our university. She'd make a great addition to the harem."

"You'd have me fuck my own sister?" I asked her, surprised.

"Why not? It's not like you'd be having babies with her or anything, but you'd make a great first time for her and keep her out of trouble with other guys." She stated. "Besides, you saw how she looked at your dick."

"Yeah, it IS a good thing she is not at our university then." I agreed. I really wasn't sure how I felt about fucking my sister. She was cute and all, but there were some things that seemed like you shouldn't cross that line.

We pulled into her place, and Courtney leaned over and kissed me. "Your mom said she wanted you back quick, so I will have to be fast." And she undid my pants, pulled out my cock and started sucking it.

"Gods, I love how you suck my cock." I moaned.

Courtney worked me down into her throat and did a trick she had learned about from Brittany. Brittany couldn't deepthroat me, but she had friends that had been deepthroating since they were 14. She'd taught Courtney to hum while my dick was lodged in her throat. It was an amazing feeling, having her vibrating on my cock.

I did not last very long at all, and shot my load straight down her throat into her tummy.

She pulled off my cock when I was finished, and licked her lips before kissing me.

"See you in the morning!" And she walked into the house.

When I got home, I went up to my room. My parent's room was on the other side of the house, with the empty rooms that had once held my sister, Melody, and my brother, Joseph or Joe as we called him. Right next to me was Cindy's room, and as I arrived, I heard her in her room, moaning quietly.

I knocked on her door, and said "You may want to put your face in a pillow, if Mom hears you it won't take her long to figure out what's going on."

I heard her scrambling inside.

She opened the door and snapped. "Get inside now."

I stepped inside.

Cindy sat on her bed, and I turned on the light on her desk. Cindy was blushing profusely.

"You... you heard that?" She muttered.

"Obviously." I informed her.

"You didn't stay long enough to have fucked Courtney again." She observed.

"A guy can only do it so many times a day." I informed her. Talking about sex seemed easier, now that the ice had been broken, so to speak.

"Gods, how many times did you guys fuck today?" She gasped.

"Not that it's your business, but three times." I informed her.

"No wonder I needed to... rub another one out." She muttered.

"Yeah, I used to jack off at least twice a day.." I admitted.

"So.. um... I know this is weird, but you said you could hear me... and you said something about a pillow?" She probed.

"Oh, I was just saying, you could either do it laying face down and put your face in a pillow, or just press your face into a pillow as you do it, and it will make it harder to hear you... um... moan."

"Could you make sure I can't be heard?" She begged.

"Sure, but you'll owe me one." I told her and stepped out as she laid back down on the bed, pressing her pillow to her face.

I could no longer hear her moaning outside her door or in my room. And after a minute I shot her a text, "Can't hear a thing."

She sent me back a thumbs up, and we went to sleep.

The next morning I went to get Courtney when I woke at 8:30. It was a little weird for me, sleeping alone and waking up alone. Courtney confirmed it was weird for her too. Luckily we didn't have much time to brood on it as when we got back, Courtney offered to help my mom cock and they immediately were working away to make the rest of the Thanksgiving dinner.

I was told there wasn't room in the kitchen and flopped on the couch in the living room.

Cindy flopped down next to me. "Mom and Courtney are stuck in the Kitchen and Dad is playing solitaire on his computer."

I knew her well enough to know she had something serious to discuss. She was establishing that we were alone and could talk.

"You haven't talked to me like this since I was in junior high." I told her.

"You asshole, that's because you replaced me." Cindy told me.

"What?" I replied, seriously confused.

"We were best friends, we talked about everything, then suddenly, you wouldn't tell me things and were always looking at other girls. What was I supposed to think?" Cindy replied.

"Cindy, I was just discovering girls. You were still in middle school, what was I supposed to tell you? I was watching porn and trying to look down girls' shirts?" I asked.

"It would have hurt less." She told me.

That was a shock.

"I wasn't trying to hurt you, squirt." I told her. "I was trying to not be a monster. I mean, what would you have done if I told you I was trying to see girls naked?"

She thought about it. "I don't know."

"Bullshit. You would have tried to show me your naked body. We both know it." I told her.

"I might have tried to get my girlfriends to show you instead." She defended.

"And that would have been better?" I asked.

"Probably not... though you might have helped them not be so easy for guys to get in their pants in High School." She asserted.

"By getting in their pants in middle school?" I asked.

"Alright! I guess... I guess it was for the best. But I wish I had understood sooner... I.. I'm sorry about how I treated you after Nikki showed you the bitch she was." Cindy told me.

"Nikki helped me learn a lot about how to please women and how to enjoy sex. But yeah, in the end she was just a slut." I told Cindy.

"Yeah. Have you heard how she's doing?" Cindy asked.

"No, I stopped following her before we even graduated." I replied.

"Well, she has 3 kids by 3 dads, and she lost them all when she got caught drugged out in her car with her fourth man, her kids were in the back seat." Cindy told me.

Part of me still hurt for the young woman she had been.

"She's in jail on charges of Cocaine use, reckless endangerment, DUI, and Child abuse." Cindy informed me. "So I think I can at least say I was right and she wasn't the woman for you."

"Where is this going?" I asked.

"I like Courtney, and well... I wanted to talk about yesterday." Cindy told me. "I liked being there with you, and I don't want her to dump you because you were doing things with your sister."

"I don't think you need to worry about that." I told her, "If it wasn't for Courtney encouraging it, I would have called it at the hot tub."

"That's part of what I like about her." Cindy told me. "I wanted to get my brother back, and because she was willing to include me, it made me realize a lot of what I was mad about you for... might not have been your fault."

"Oh?" I asked.

"Well, you said how easy it was to get around the filters... and well, dad had said he'd get an email if I so much as tried, and I'd be grounded for eternity." Cindy confessed. "So I hadn't even tried looking for things... But I looked up some stuff last night, so I know that any more than what we did would have been... incest, and that isn't okay. But I really appreciate you going as far as you did. Then you helped me figure out how I could masterbate without getting caught... I owe you. More than just one. So if you ever need me for anything... just let me know okay?"

And with that Cindy threw her arms around me and hugged me tight.

I wasn't sure about all that we had done, but I was glad to have my little sister back.

Since my parents always made too much food, a few family friends were invited to join us. The Millers had been family friends forever and had two kids. One was in the army and deployed to Germany right now, so he couldn't come. The other was Cindy's best friend, a girl her age named Mary. Additionally, the Fitzgeralds and the Garcia's joined. They had been some of my parents' friends growing up. Mrs. Fitzgerald was unable to have children and so she was like a second mom to me. The Garcia's children were too spread out across the US, and couldn't make it for Thanksgiving.

Cindy was chatting in hushed whispers with Mary the whole meal. Courtney seemed worried.

"I don't think that girl likes me." She whispered.

"I don't know, Mary is an interesting girl. She and Cindy both kinda stopped talking to me years ago, and maybe since I made up with Cindy, Cindy is trying to get her to talk to me again?" I speculated in a whisper myself.

Courtney did not seem convinced.

The rest of the meal was great. Courtney loved our fried turkey (a second turkey, sectioned, dipped in seasoned flour, egg wash and then fired) and my mother's pie.

"Oh, it is a good thing your family doesn't always eat like this." She groaned, "I'd get fat."

"Like Tina would let you." I chided. "She'd get you whipped back in shape."

After the Millers, the Fitzgeralds and Garcia's left, Courtney, Cindy and I were lounging in the front room. Mom and dad had cleaned up and were taking their traditional Thanksgiving turkey coma nap.

"So Cindy, What were you and Mary talking about?" I asked, "Courtney said that Mary didn't look like she likes her."

"Oh, she was just pissed because I could finally say beyond a shadow of a doubt that you aren't a virgin anymore. She was hoping you two would lose your virginities together." Cindy laughed.

"WHAT!?" I gasped.

"Yeah, She's been planning it since she was like eleven." Cindy informed us. "I had to tell her like a hundred times that you and Nikki were having sex, but she refused to believe it because I never saw your penis in Nikki's vagina. I may have said I peeked on you at the airbnb. So she had to give up the thought of taking your virginity as she gave you hers. Don't worry, she won't say anything about it."

Courtney gave me an "it could happen look", and I had to wonder what the limit on the number of girls she would have in the harem would be.

"Oh my god. You'd let her fuck him?" Cindy gasped, sitting up despite the feast induced sleepiness.

"I'd have rules, and such, but maybe." Courtney stated noncommittally.

"I don't know if that will make her happier or madder..." Cindy giggled.

Courtney shrugged. "I have a psychologist friend I'd want her to talk to first. I'm not sure her fixation on Tom is healthy."

"I can hear that. I had to point out to her that she doesn't turn 18 until January. Right now she is just jail bait for Tom." Cindy pointed out.

Courtney laughed, "Yeah, that would be a must. No underage sex."

I was surprised how easy it was getting for these conversations to happen.

The rest of the day was relaxed.

Cindy had a few questions that popped up. She learned what fellatio was. That Courtney did it with me, and that I gave her oral as well.

"So that's why they call it a blowjob." Cindy mused. "So what is anal sex?"

Courtney looked at me. "Well, do you know what the anus is?" I asked.

"Um, you know I only paid enough attention in biology to pass. I forget all that stuff right after the test." Cindy confessed.

"It's... it's your butt hole." I told her.

Her eyes got wide. "So... you stick it...." and she left it hanging.

"Yep." I told her.

"Have you two....?" Cindy pressed.

"Of course." Courtney told her. "It is actually really good. It can be as good, if not better than normal sex. Though, it gets sore, and you need to use lube. Your vagina lubes itself as it gets wet. Your butt doesn't."

"Oh..." She noted wide-eyed.

We laughed.

The next day, Cindy took my car first thing in the morning and went on the promised shopping trip with Courtney.

Dad enlisted my help on a few projects, including helping put Christmas lights up and getting all of the decorations out of the attic.

Dad and I were exhausted at the end and dad retreated to play his solitaire on his computer, while mom read one of her books in the front room.

"WE'RE BAAAAACK!" Cindy sang as they came in the front door.

"Welcome back! What all did you get?" Mom asked.

"Mom... It's Christmas time now, you aren't allowed to check my purchases during Christmas?!" Cindy objected. "What better time to do Christmas shopping than Black Friday." And she clung to her armful of bags.

"Okay, okay!" Mom conceded. "I hope you had fun."

"Oh, yes!" Cindy celebrated.

She and Courtney headed back to her bedroom and Courtney beckoned me to follow.

"You two had fun, I take it." I asked.

"Hell yeah. She kicks the pants off of Nikki. You can keep this one." Cindy told me.

"Thanks for that endorsement." Courtney laughed.

"So did you actually get Christmas stuff or just stuff you didn't want to show mom?" I asked, sitting on Cindy's bed.

"Both." Cindy proclaimed, "Your girlfriend generously bought all my Christmas gifts AND spoiled me... plus getting some things I think you're going to enjoy later." And she blushed with that last part.

"We dropped those bags off at the airbnb before coming back." Courtney informed me with a laugh. "Cindy was blushing nonstop in the sex shop."

"Oh? You went to a sex shop?" I asked, incredulous that my girlfriend would take my sister there.

"Yes!" Cindy called, blushing. "Look what she got me!"

She presented a rose looking device labeled a 'Clitoris Massage and Vibrator'. "She says it feels really good." Cindy told me.

I wasn't surprised. Several of the girls had started playing around with sex toys. They had generally decided they preferred the flesh between my legs to dildos, but Brittany and Suki liked butt plugs to keep their anuses stretched. Debbie was addicted to her vibrating wand, and Tina sometimes did a run with a vibrating egg inside her, for the thrills.

Courtney had the most extensive collection. But she refused to use most of them unless I was also involved, said it didn't feel right without me there.

"That'll help you get an orgasm out when you need it." I chuckled.

"We also discussed how sexy underwear made her feel better about her body." Courtney continued. "Want to show him what you got?"

"I'm not wearing them in front of him. God, I'm not ready for that." Cindy blanched. "Hell, I don't think I could muster the guts to wear that bikini again... could you really see my butt hole when I bent over?"

"It's a lovely butt hole." Courtney assured her.

"Oh God." Cindy breathed covering her face.

"You were horny and desperate for relief. It happens to everyone." Courtney comforted her, "Besides, it was just us."

"You saw too?" Cindy gasped at me.

"I'd be lying if I said I didn't see it. But as Courtney said, you have a cute pink little butt hole." I admitted.

"Oh God." Cindy moaned.

"Anyways, I wasn't saying to wear them and give a show. Just lay them on the bed so he can see." Courtney instructed.

Still blushing like a rose, Cindy laid out the five sexy sets of underwear that Courtney had bought her.

All of them would qualify as lingerie. They were matching sets of bras and panties. Two of the panties were thongs, with lacy nothings covering the front and thin fabric to ride in her ass. Another was a g-string, that didn't have fabric until about an inch away from where Cindy's slit should start, leaving most of her crotch bare. The next has straight up crotchless, and would leave her female parts completely accessible, while supporting and shaping her butt. The last one was an elastic band to go around her waist connecting to fake leather that would stretch tight like a thong in the back but the triangle that made up the front was zippered.

The bras were equally enticing. Paring with the thongs, one bra was lacy and sheer enough it would hide nothing. The other only had the shaping and supporting pieces but left the majority of the breast exposed. Pairing with the g-string was a string top that made no pretense of covering anything, just a ring to set around your nipple and a few strings to enhance your figure. The crotchless panties paired with a cupless bra. And there fake leather, zipper crotch panties paired with a fake leather top that had zippers which would let the cups drop away.

"Fuck, Cindy, these are hot! Did you pick then out or did Courtney?" I asked, trying to avoid the tentpole that was inevitably forming in my pants.

"Courtney helped, but I picked then out." Cindy asserted.

"Do you wear stuff like this to school?" I asked, concerned.

"Oh, hell no." Cindy laughed, "If anyone caught sight of something like these," Cindy picked up the crotchless panties, "I'd be sent straight to the principal's office and then mom would find out and I'd be grounded until I was an old maid."

She set down the panties.

"I wear them when I'm home alone, or when mom and dad are ignoring me. It helps me feel sexy." She confessed.

"So, which one is your favorite? And no pressure but we have a bet going about which one you pick." Courtney asked.

"What are the terms of this bet?" I asked, nervously.

"Not telling you. It might change what you pick." Courtney informed me. "Just pick."

I looked over the tantalizing bits of string and fabric. "Oh, that's just not fair." I told the girls.

"Come on, Bro. Pick one. I promise I won't be angry, even if you make me lose the bet. And Courtney might enjoy losing the bet." Cindy told me.

Fuck, I thought, it's something sexual.

I looked over the sets one more time.

"What if I pick a set neither of you are betting on?" I asked.

Cindy thought about it. "I guess we'd both lose."

Man, I thought, the problem is I could see myself picking any of these. So, I guess I just had to figure it out, and answer honestly.

My mind happily provided me with images of both women in the room wearing each set of skimpy next-to-nothings. I quickly narrowed it down to two sets. In the end one set won out.

I raised a hand high in the air, extended a finger dramatically and brought it down, pointing at the g-string and string bra.