Life after the Lottery Ch. 15 Pt. 2

I had stopped licking her and was focusing on getting her wet and loose. I remembered the big butt plug Amy had used to pry her open the first time and knew Dawn was a long way from being stretched that much. I sat up some so Sam could see what was going on. I thought to be safe I would stretch Dawn some more before I tried to enter her. I took my other hand and slipped two fingers into her pussy and worked them around at the same time I was working two fingers in her ass. Dawn's moans began to grow louder, her exhibition seemed to be getting lost in the sensations. I withdrew the two fingers I had in her pussy and gently withdrew the two fingers I had in her ass. I placed a third finger from my other hand with the other two, I slowly pushed them up against Dawn's hole. I was shocked to see that it had remained slightly open after I remove the first two fingers. Gently I pushed the three fingers into Dawn, she moaned deeply. More and more I pushed until I had my fingers all the way inside her.

"That feels good James," Dawn said softly over her shoulder. "Spread me open more."

I was delighted that Dawn was really getting pleasure from this, I wasn't sure how it would go for her the second time. I worked the three fingers in and out some more, stretching her as I did. I pulled them most of the way out and then slipped the fourth finger up, two from each hand, and began inserting it gently.

"Oh yes!"

I slowly pushed all four fingers into her loose asshole, I was really getting turned on doing this while I watched. I knew Dawn had a lot of control but she seemed to be ready and able to let me do what I wanted now. In and out I slipped all four fingers, once they were meeting no more resistance I pulled all of them out as Dawn moaned. I looked down and saw Dawn's asshole staying open, I couldn't resist it, I leaned forward and stuck my tongue deep into her open asshole.

"Oh my god!!" Dawn screamed.

I had to continue exploring her insides while I had the chance. Dawn began to push back against my face, I had all of my tongue in her and was licking her insides.

"I want you in me James!!"

With hesitation I removed my tongue from inside Dawn and moved up so I could place the head of my serious hard-on against the lips of Dawn's pussy. Even though her ass was remaining open I wanted to get my cock lubricated. I eased my cock in slowly and purposefully into Dawn's pussy, sliding in and out a little until I was all the way in her. Dawn moaned louder as I used her pussy to lubricate my cock. Once I felt good and wet I pulled all the way out of her pussy and placed the head of cock at the opening of her ass. Without any pause I pushed forward and watched the head of cock enter easily into Dawn's ass.

"Oh yes, yes!! That feels so good!!"

I pushed ever so slowly until I was about halfway in and I begin to feel resistance both inside her and around the shaft of my cock. I paused a moment.

"More! Put it all in me!"

Gently I eased forward, feeling my cock slowly spreading Dawn's asshole open even more.

"Mmmmm!!!"

Dawn pushed back against me. Another moan and she pushed back some more. I had three quarters of my cock in now. I grabbed her hips and slowly withdrew a little and then pushed forward again, Dawn continued to moan and groan loudly. I pulled out some more and pushed back in, pushing in a little further each time. There was only about an inch of the base of my cock still showing when she shoved back hard, I watched as all my cock went fully into her ass.

"Oh that's it!!"

I started pushing forward hard against Dawn's ass, feeling the head of cock deep inside her. Then I slowly began to slip in and out of her, with each push back in Dawn's moans got louder. I slowly sped up my pace, pulling a little further out each time and then pushing all the way back in.

"Oh god yes, that feels wonderful. Give it all to me James!!"

I followed Dawn's command and began a faster pace, slipping most of my cock out and pushing it back in. Dawn began to push back and meet each of my thrust. This was even better than the first time with Dawn, the turn-on of watching my huge cock slip in and out of my wife was causing my cock to swell more. Dawn moaned and groaned and cried out while I pumped her for about 10 minutes. I wanted to see if Dawn would reach an orgasm with me just pumping her ass. She continued to shoved back against me meeting each thrust.

"Oh god James I'm going to come!!"

I could feel Dawn's energy as we touched. She began to drive herself back against me, I could hear my balls slapping against her pussy. Each time they hit she grew tighter.

"Oh James!!!" I knew from that cry that Dawn was about to explode.

I quickened my pace building up to my own explosion.

I felt Dawn's asshole tighten around my cock.

"Now!!!"

Dawn's back began arching up and down as her orgasm hit, I shoved in as far as I could and held it while she jerked with the beginnings of her orgasm.

"Come in me now!!!"

I let go of the hold I had and felt the first of many loads shoot out and into Dawn, it felt extremely hot inside her. Each time Dawn's back arched up I shot another load into her.

"You're so hot!!! Fill me up!!!"

I felt the cum stop shooting from my cock but it still continued to spasm, my ass muscles kept contracting trying to send more into Dawn. As my own spasm rocked through my body I jerked and thrust into Dawn.

"Oh that feels so good!!" Dawn screamed out as she thrashed her head from side to side.

I was spent, I could feel my cock twitching but I had no more energy or cum to give her. I leaned into Dawn and placed my hands on her back and steadied myself. Dawn was squeezing her ass muscles together clamping down on my cock. I began to rub her back hoping she wouldn't stop squeezing my softening cock. Dawn raised her head up.

"Oh god that was fantastic!!"

"See Sam, it is something that can be enjoyed," Amy said.

I turned to look at Sam and I saw that she had her hand between her legs again.

"He is so big though," Sam said.

"It takes practice Sam. You have to start out with something small first, like one of your college guy's pricks," Amy told Sam with a giggle.

"I don't know," Sam said.

I pulled my limp cock from Dawn's ass and watched as the cum spilled out, her asshole was still stretched open. Dawn reached back and took the opportunity to stick two of her fingers into her ass and work them around some, then she pulled them out and stuck them in her mouth and sucked the cum from them.

"You want to feel Sam?" Dawn asked her.

Sam looked Dawn in the eyes.

"Go ahead and stick your fingers in and feel," Dawn said.

Sam slowly reached forward and slid first one finger and then a second into Dawn's ass, I was surprised when she pushed them all the way in and worked them around. Sam removed her cum covered fingers and slowly placed them up to her lips. She slowly slid them into her mouth as she licked the cum from them. She had them all the way in when she closed her lips around them and sucked on them.

"Mmmmm!" Escaped from Sam.

"Amy?" Dawn asked.

"I'll take the more direct approach," Amy said as she pushed me away and drove her tongue deep into Dawn's ass.

"Oh god Amy!"

Amy slurped and licked for several minutes until she had everything she wanted. Amy then sat up on her knees and looked at me.

"Kiss me James."

I leaned forward and kissed Amy deeply, our tongues working around inside each other's mouth for a long time.

As Amy parted she whispered ,"I didn't know if you would do it."

I reached up and grabbed Amy's breast through her top and smiled.

"Amy, can I ask you something," Sam said.

"Yes."

"Have you let James fuck you in the ass?"

"Yes, several times."

"Are you sure it didn't hurt?"

"Sam, it will hurt a little the first time, but once you relax you will find it pleasurable but not every woman likes it."

"I don't know."

"We can experiment if you want," Amy told her.

"I am not sure."

"Sam, you had an orgasm when I stuck my tongue in your ass," I said.

"That's different."

"Would you like me to lick your asshole right now?"

"Yes."

"Why don't you get up on the couch like Dawn is," I told her.

Sam stood up and removed her pajamas and climbed up on the couch. I got down on my knees behind her. Her pussy was already swollen and wet, she may have been unsure about something being stuck in her asshole but she had sure gotten hot watching.

I leaned forward and began licking her pussy to relax her. She moaned each time I licked.

"That feels so good."

I slipped my tongue into her pussy and decided I was going to get her to an orgasm first. I sucked on each of her pussy lips and alternated between that and probing her with my tongue.

"Oh James, I am getting so hot."

Her juices were flowing well now. I leaned in and licked her clit as best I could, she began to moan more and more. I wanted to get her off with my tongue so I didn't use my fingers. Sam continued to moan and squirm for several minutes until I could tell she was approaching her first orgasm.

"Mmmmmm!"

I flicked her clit with my tongue.

"Oh yes!"

Sam pushed her pussy back into my mouth. I placed my mouth over her pussy and sucked hard.

"Oh yes, yes, yes!"

I pushed my tongue and licked her insides.

"Oh my god, I am about to come!" Sam screamed.

That was what I wanted to hear. I pulled my tongue out of her pussy and licked up her crack to her tight little asshole. I flicked my tongue over her asshole.

"Oh my god!"

Sam pushed back and I forced my tongue into her ass as far as I could.

"Oh no!"

Sam pushed back harder and I pushed my tongue in farther and licked.

"Oh my god James I am coming!!"

Sam jerked several times as she pushed back and then she let out a scream and jerked over and over.

"Ahhhhhhh!!"

Sam pulled away and continued to spasm. She was gasping for a breath. No one said anything we just let Sam's orgasm pass.

"I am starting to love that!"

I put my hands on Sam's ass and stroked it, she jumped slightly when I touched her.

"Sam, I think you are ready," I told her.

"What?"

I slid my hand slowly toward her now wet asshole. Slowly I used the tip of my finger to stroke her asshole.

"Ummmm."

Slowly I pushed the tip of my finger up against her tight little opening. I began to slowly wiggle the tip of my index finger into her.

"Ummmmm."

I pushed my finger slowly in up to the first knuckle.

"Oh my."

I wiggled the tip around just inside her opening. Sam was good and wet but resisting.

"Sam, just relax."

I wiggled my finger some more and she seem to loosen. I just pushed in softly and slowly, sliding my finger in up to the second knuckle.

"Oh my."

I wiggled around until I felt her relax some more. I slowly pushed in letting my second knuckle slip by her opening.

"Ouch."

"Relax Sam."

I wanted until the tension left her asshole then I pushed more, letting my knuckle slip farther in.

"Ouch."

I waited. I pushed the remainder of my index finger in, it was all the way in now.

"Oh!"

"Are you okay?"

"Yes."

I begin to bend my finger and work it inside Sam's ass, she was incredibly hot. I turned my finger a little as I worked it.

"Oh my, that feels so different."

I pulled back on my finger until the middle knuckle began to spread her asshole again.

"Oh god."

I held the knuckle there, stretching her asshole a little then I pushed back in.

"Oh that feels good."

"Sam, can I stretch you more?"

"Go slow."

"I am going to pull my finger out, this may hurt a little."

I slowly pulled my index finger out of her asshole, I felt her tighten up as I did. I slipped my middle finger in her pussy and lubed it up, then I placed the tip at her asshole and pushed slightly.

"Relax Sam."

The first knuckle of my middle finger slipped in. I held it until she relaxed. I pushed further letting the second knuckle slid in.

"Oh my."

Sam seemed to be relaxing. I pushed in more, my finger slipped past the second knuckle, Sam tightened up a little. I held my finger there and worked it around inside her. When I felt her relax I pushed it all the way in.

"Mmmmmm."

I slowly begin to twist and work my finger around inside Sam, feeling her hot folds.

"Mmmmmm."

"Does that feel good Sam?"

"Yes."

I looked over at Dawn and motioned for her to lean over. I whispered in her ear and she shook her head and got up and left.

"Sam, I am going to slip my finger in and out, you just relax."

I slowly withdrew my finger and then pushed it back in.

"Ummmmm."

Sam was wetter now as I continued to slip my finger in and out and work it around.

"That is starting to feel good."

I pushed my finger in hard and felt the warm folds of her insides. I took my other hand and slipped a finger into her pussy.

"Oh yes."

I slipped another finger into her pussy and began to rub her G-spot.

"Oh James that feels good."

Dawn came back, she had a double penetrating vibrator in her hand and a bottle of lube. Dawn poured the lube onto the vibrator.

"Sam. I am going to pull my fingers out but I don't want you to move."

"Oh please don't stop now."

"I'm not, I just have something else for you to try."

I slowly pulled my fingers from her pussy and then my finger from her ass, I knew the vibrator would be okay because the part of it for her ass was only as big as my finger. I set back and Dawn placed the tip of the vibrator against Sam's pussy and slipped it in until the second part touched her asshole.

"Oh, what is that?"

"Just relax," Dawn said.

Slowly Dawn pushed the double headed vibrator into Sam's pussy and ass.

"Oh god, that feels good."

Dawn pushed it all the way in and began to slowly slip it in and out

"Oh my god, that feels great."

Dawn reached up and turned the vibrator on.

"Oh shit! Oh god!"

Dawn slipped the vibrator in and out faster for several minutes. Sam began to moan as she pushed back against the vibrator each time Dawn pushed forward. The vibrator in her ass was about as big as my finger, the one in her pussy was about an inch and a half in diameter. I watched as Dawn worked the vibrator in and out. Sam squirmed and wiggled now.

"How does that feel," I asked Sam.

"It feels good!"

"Does it hurt?" Dawn asked.

"No, not now."

I looked at Dawn and she looked at me. Dawn pushed the vibrator in and out several more times and then pulled it all the way out then she immediately placed the tip of the larger end up to Sam's ass and pushed slowly.

"Oh no, ouch!"

Dawn pushed the vibrator all the way in, Sam was now feeling something deeper in her than before.

"Oh my god!"

Dawn pushed hard and then pulled out some and pushed back in.

"Oh god!" Sam cried as she began to push back.

Dawn worked the vibrator a little faster.

"Oh god, I feel like I am going to come!"

Dawn moved a little faster with longer and more deliberate strokes.

"Oh yes, I'm coming!"

Sam pushed back harder and faster jerking her hips as she did.

"Yes!" She screamed as she threw her head back

Dawn shoved the vibrating dildo hard into Sam's ass and held it.

"I'm coming!!"

Sam's back arched up and down several times, then I saw her squirt a little from her pussy.

"I'm coming!!"

Dawn stroked the vibrator in and out several times. Sam's back arched up as another orgasm ripped through her body.

"Shit!!"

Sam began to collapse.

Dawn slowly withdrew the vibrator from her ass, knowing it might hurt as she pulled it out. Once it was out of her ass Sam collapsed onto the couch moaning.

"Sam are you okay?" Amy asked her sister as she rubbed her ass.

"Oh god yes!"

"Did you like it?" Amy asked.

"Oh god yes," was all Sam could say.

Amy rubbed her sister's ass tenderly. Sam rolled over and sat up on the couch.

"That was great! You were right Dawn."

"I thought you would enjoy it if you tried, are you sure you are okay?"

"I hurt a little but I am okay. I don't think I am ready for James but I liked that."

"Good, you can experiment more another time." Dawn said to her.

"I can't wait."

We all had some laughs for the rest of the night then we all showered and went to bed, Amy and Sam went to bed together and left Dawn and me in our bedroom.

"I think everyone had a good time," Dawn said.

"It was quite a different Christmas wasn't it?"

"Yes it was."

We held each other and went to sleep very happy.