Sexiplicity Ch. 09

"Oh wow... look at that," I said.

"Yep, I've decided, after earlier, to find out what it's like and this is what Mom suggested. Want to help 'train' me?" she said, giggling.

"Absolutely! When do we start," I said, chuckling.

Mom walked over about then and stood in front of the two of us as we looked at the package of anal training toys.

"We can start tonight, after I drop off Becca's things," Mom said.

"Okay, sounds fun," Tiffany added.

As I looked at the toys and the different sizes, I noticed that even the biggest plug was nowhere near as wide as me. I didn't know if I should bring that up or just let it go for now. Mom saw me looking at the plugs and I must have had a look on my face, maybe of worry or questioning at least.

"This is just to get her started, Peter... we have other toys to bridge the gap," Mom said.

"Yeah, Mom says she has plenty of toys to help after I graduate from these," Tiffany added.

"Okay, cool... we'll have to get the whole collection together and have some fun," I said placing a pillow over my lap.

Mom and Tiffany laughed... "Can always count on you, Peter," Mom said.

"For sure, just mention some kind of sexual reference and up springs big Peter," Tiffany said, making them laugh more.

My cock was the brunt of the joke, the all-powerful penis that could and it never ceased to could.

**

That evening, after sunset, Mom took the boxes over to Becca's house and left me and Tiffany at home. She had cut open her anal training kit and was washing the toys in the kitchen while Mom was gone. I got up from the couch and walked to talk to her.

"So, I'm curious. Why are you doing this? Why the change of heart? You've told me before and just today that you don't want anything in your butt," I said.

"I know. And to be honest I'm nervous, but after I saw what Mom did today... how amazing it looked and the way she came. I guess I don't want to be missing out on something if I don't' have to. Besides, if I don't like it and I can't even handle these plugs, then I can always stop," she said.

"Okay, good... I don't want you doing it for me or thinking I'm forcing you to do this," I said.

"I'm not, although I could tell you liked fucking Mom's ass, and I think you came big time."

"I'm not going to lie, it is amazing but I know how big I am and don't want to hurt you."

"Don't worry about me, little brother, I won't let you do anything I don't want to do," she said, drying off her three new toys.

She kissed me on the cheek and walked passed me with her toys. Mom returned a few minutes later.

"How'd it go?" I asked.

"Fine, I just left them on the porch. I don't think anyone saw me," Mom said.

"Was anyone home?" I asked.

"Yes, there were lights on and a car in the driveway... I don't know if Becca was there or not."

"Okay, I guess that's all we can do," I said.

"Guess so... sorry, honey," Mom said, messing up my hair like she does. "Where's your sister?"

"She washed her plugs and took them to her room. Are you sure this is a good idea?"

"Tiffany's not going to do anything she doesn't want to do. You know that," Mom said.

"True, just don't want to pressure her," I said.

"We're not... it was her idea to go to the adult store. She picked out the training kit... I just supported her."

"Okay, then I'll just do what she wants," I said.

"You're such a nice boy, Peter... always concerned about others," Mom said, kissing my forehead. "Let's go see what she's doing."

We walked together down the hall to Tiffany's room. The door was closed. Mom knocked.

"Come in," Tiffany said.

Mom opened the door. "Oh good, you're home," Tiffany said. She was sitting on her bed, reading the instruction to her training kit. "Want to go get your toys and bring them in here or should I bring mine to your room?" she asked.

"I have a few more than you and a bigger bed, come to my room," Mom said.

"Okay, cool," Tiffany said, picking up her three plugs and lube. She smiled at me as she passed us both on the way to Mom's room.

We followed. Inside Mom's room, Tiffany jumped on the bed and set he toys down next to her. "Okay, whatcha got?" she asked.

Mom went to her nightstand and opened it. She pulled out the vibrator I already knew about, the large buttplug that had to be new since my beating and several other things I had never seen before. Seems Mom went on a sex toy shopping spree while I was out of commission. She laid each item on the bed among Tiffany's plugs.

I shifted my cock, which was already well on its way to erect.

"Okay, lets see what we got," Tiffany said. "Large vibrator, large plug, smaller plug but still bigger than mine, a double sided dildo, lube, and what's this?" she said, holding up a small purple toy with a funny cone shaped thing on it.

"That's called a Womanizer... it's a clitoris stimulator and man does it work," Mom said.

"Okay, cool... that will help me relax, right?" Tiff asked.

"Oh for sure, if you don't cum first," Mom said.

"Really, this little thing is that powerful?" Tiffany asked.

"Oh yeah, it fits right over your clit and produces miracles," Mom said, giggling.

"Can't wait to try it."

My cock was throbbing and instead of just letting it ooze all over my pajamas, I just started taking them off. The two women, after discussing the toys, turned and found me naked with my cock pulsing in the open air.

"Well, well, someone's raring to go," Tiffany said.

"Yeah, well I was going to start making a mess in my pants so..."

"No, it's good, I think I'll join you," Tiffany said and started removing her clothing as well.

When she was naked, she scooted to the edge of Mom's bed and laid down on her back, my cock lurched and I wiped the drip of pre-cum around the head before it dripped to the floor.

"Want to eat me, little brother?" Tiffany asked.

"Yes I do," I said, falling to my knees and moving my head between her legs. I lost track of Mom as I started munching on my sister's shaved pussy. She tasted tangy and wet as my tongue traveled from the bottom of her sex to her clit, spreading her open. She cooed as I covered her nub with my mouth and sucked on it, rubbing it with my tongue before lowering it to shove into her hot, wet hole. She grabbed my head, fingers in my hair and pulled me deeper, mashing my face into her lips and my tongue as deep as it would go.

I stayed working on her pussy for quite a while before I venture lower with my tongue, to see what she would do if I licked her puckered asshole. When I finally did, she moaned, liking the sensation and I proceeded to work my tongue around and finally inside a bit. She relaxed and let me. Moaning again as I entered deeper into her ass. I heard a strange buzzing noise and opened my eyes to see the clit stimulator over her clit. I guess she picked it up when I was tonguing her ass.

"Oh wow, yeah, oh... damn... this thing is good," She said moving it around on her clit.

I kept darting my tongue into her ass as she played with the toy on her clit. It was about this time that Mom appeared and handed me the first plug in the training kit. I took it from her, removed my tongue and easily slid the first toy into Tiffany's ass. She started to cum before the end cap hit her butt. That toy must be something.

"Oh... fuck... Ahhh, I'm... cumming!" she screamed, legs shaking as her pussy started to convulse from the clitoral orgasm.

All of a sudden, the plug shot from her ass her convulsions were so powerful. I didn't have a chance to stop it but did manage to catch it. Mom took it from me and handed me the next bigger one as Tiffany was still climaxing. She had to take the toy off her clit, I guess it was too intense to continue. I eased the second plug into her wet ass, pretty easy as well, but could feel her spasms from the climax as I did. I held it in this time, until she was done.

"Told you that thing was good," Mom said.

"That's a... understatement... holy shit," Tiffany said.

"You're up to the second plug already, sis," I said, looking up over her trembling body.

"Oh... really... cool," she said between pants.

I had forgotten to wipe my cock and when I remembered, noticed it had already dripped to Mom's carpet. I fixed what I could, rubbing the effluent all over my head and shaft, there was so much. I grabbed the end of the toy in her ass, and pulled on it since she was settling down. It popped out easily and I pushed it back in.

"How's that feel," I asked.

"Fine... good no problems... I kind of like it," Tiffany responded.

Mom then handed me the last toy in the training kit.

"Ready for this?" I asked, showing Tiffany.

"Sure, I think I'm training rather fast," she said.

I pulled out the medium trainer and Mom squirted some lube on the biggest one in Tiffany's collection. Easing the tip into her ass was easy, she just let it in with no problem or hit of flinching. I started pressing it into her, widening her tight hole nice and slow.

"You good?" I asked.

"Yep, keep it coming," she said.

It settled in a second later... seemed my sister was natural.

"It's in," I said.

"Really? That's it? Wow, maybe I didn't need the training kit after all, that was easy," she said.

I pulled on the plug and started fucking her with it so she could feel her ass widen and close, widen and close.

"Mmm, yeah, I like that... it's nice..." she said.

"Try the toy when he does it and see what happens," Mom said.

Tiffany picked up the clit stimulator again as I fucked her ass with the last training plug. She set the simulator on her clit and started to moan. I sped up, pulling it out and forcing it in as my cock throbbed below, fucking my sister with a rubber buttplug as she moaned and seemed on the verge of another climax.

"I can't it's too much... she said," pulling the toy off. "Holy shit... that little thing is amazing."

"You ready for more then?" Mom asked.

"I think so... what's the next widest toy?" Tiffany asked.

Mom started comparing her toys and it was between her double sided dildo and the vibrator, they were pretty much the same size. She ended up handing me the long double sided thing, which was probably two feet long, she showed me how it could bend in half... I'm sure Mom liked to stick it in her ass and bend it around into her pussy while I was in the hospital.

I held it in one hand, Mom squirted more lube on an end and I started pulling the final training plug from my sister's ass. I quickly replaced it with the tip of the long toy. It was wider than the plug and I got some resistance right off. I held it there with some force but didn't press it in yet.

"Okay, honey, now this is where you might need to start pushing out when he pushes in," Mom said, seeing the toy not going in.

"Umm... okay... wow... that seems a lot bigger," she said.

"It's not tapered like a plug so it's going to seem big," Mom explained.

I didn't move, just kept the pressure on her ass, letting her try and open to accept it. It's hard to explain everything going on, the visual splendor I was seeing and the way I felt. My body was trembling, my cock throbbing as I trained my sister's ass and viewed her stunning body trying to take an object about three quarters the size of me, into her ass. Tiffany's hand came up to her clit, the stimulator was too much so she opted for her fingers. I felt her start to push out on the end of the toy as she started to play with her clit.

"That's it... just relax and push," Mom said.

I watched with wide eyes as her ass opened around the end of the toy and it slipped inside, past her taunt ring. I didn't let too much go in, maybe an inch, inch and a half. She was breathing heavily now, rapidly playing with her clit and I knew this was a make it, or break it point. If I went to fast, if I hurt her now, she would never go further. I froze, letting her adjust and Mom nodded at me as if to say I was doing perfect.

Fuck me, it was so hot, so stimulating visually I didn't want to even blink. I thought about what evil Peter would be saying, what he was missing and I almost felt bad because he would have fucking loved what I was doing to Tiffany right then.

"Oh man... that's tight... wow... it's so much bigger," Tiffany said.

"Yeah, we might have needed one more in between," Mom said. "But you're doing great, honey."

It took a while, maybe two or three minutes before I could tell her ass was adjusting, easing up around the toy. I had held it still, just waiting for her, trying not to ruin anything.

"It's getting better, I think you can try and go deeper, Peter," she said.

I slowly, I mean slowly moved the long toy into my sister, watching the rubber slide as her ass grabbed at the toy. An inch took a minute, but it didn't get any wider so now it was all about length. She handled the inch... she handled the second and third before I paused again.

"Mmmm, yeah, it's not bad... its just filling me now, the strain has eased. I can take more," she said.

Three became six and I started to feel some resistance inside of her so I stopped again. Instead of going deeper, I started pulling out, nice and slow.

"Oh, wow... yeah, you're right, Mom... that is a totally different feeling," Tiffany said as the five inches left her body.

I made sure to keep the last inch in, before slowly pressing back up the same distance, to the end of the wet line on the toy. She was busy playing with her clit and I was in no hurry. The six inches were back in her and I was removing them again, loving the effect it had on my own body. I wanted to stand up and shove my cock in her drenched pussy, she was so wet. Her own juices were joining the lube already on her ass.

"Little faster, Peter," Tiffany said.

I sped up the inward thrust and pulled it out faster still. In again, out again as she circled her clit.

"Oh, oh... wow... it... oh shit, it really blends with the clit play well... oh... I like it... oh yes yes..."

The six inches had become seven, then eight as I fucked her faster with the toy. She was basically taking the length of my cock in her body, but not the width. She was doing amazing. Better than I thought she would that's for sure. She started to cum a second time. Her pussy gushed under her hand and I felt her ass clamping on the toy as I moved it in and out. Holy shit, I was aroused, couldn't remember having more fun than I was right then. Tiffany was coming hard as I fucked her with a two foot long toy.

I thought everything was perfect but Mom thought better. Leaning over, she grabbed the other end of the long toy, bent it in two and fed the other end inside Tiffany's convulsing pussy. This sent her into a frenzy as the added pressure and pleasure overwhelmed her. She started to spasm, thrashing on the bed as I held both ends into her body that was already cumming.

"Oh... fuck! Fuck fuck... fuck!" she screamed and came so hard I thought the entire neighborhood would hear her.

I just held the toy in, letting her ride the waves as Mom and I watched her thrash and cum. It was a long powerful orgasm.

"I think she likes anal," Mom said quietly.

"Yeah, we may have a new fan," I said, smiling.

When Tiffany finally finished, she was exhausted. She just laid there, limp with an occasional spasm from the aftereffects of her massive orgasm. I pretty much knew she was done for the night and I wasn't going to get to dip my cock in either hole. Since she wasn't responding, I just slowly removed the toy from both of her holes and left her lying there.

"I think she's done," I whispered to Mom.

"Yes, I believe you are right. You're such a good brother... I know how much that affected you and I'm sure you wanted to enter her yourself. Let me make it up to you," Mom said, raising me up until I was standing in front of her.

She grabbed my hard, wet, cock and instantly sucked it in her mouth as deep as she could. My head fell back in pleasure as the sensation of her hot mouth sliding down my shaft, seized my frame. Mom started working her magic, stroking, sucking, licking and treating my cock to a world-class blowjob. I was already aroused from training Tiffany for so long, so it wasn't surprising when I was on the verge of cumming relatively fast.

It had been a pretty long and eventful first day home and I needed my rest to keep recovering. I think Mom knew that and was working to just get me off fast. A few minutes later the pleasure became too much and, after holding it in as long as I could, I exploded into my mother's mouth. She handled my third load of the day just fine, holding her mouth over my head and stroking me through to completion. Fuck it felt good, my legs shook as the jets of cum flew from my cock into her mouth. She swallowed everything. After three climaxes, I was pretty much empty and it felt like it.

I moved back to my attic room, now that Becca was gone. I took the stairs slowly and carefully, but was glad to actually be back in my bed. I think Tiffany was just going to sleep in Mom's bed, because even after I came and we cleaned up all the toys, Tiffany was still out of it and had fallen asleep. Mom said she'd be fine and told me to go to my room.

What a crazy day! Finally home from the hospital after five weeks, get to have sex with Mom again, lose my girlfriend in the process, fuck Mom's ass twice, anal train my sister, blow a load in Mom's mouth and now going to sleep in my own room with nothing but my own voice in my head. I guess it could have been worse.

My bed felt so much better than the couch and I stared up at my ceiling contemplating the day before drifting off to sleep.