Life after the Lottery Ch. 25

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We leave for Hawaii
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Part 32 of the 90 part series

Updated 11/08/2023
Created 05/14/2011
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drmac100
drmac100
1,233 Followers

We leave for Hawaii

Dawn and Amy spent the next week getting ready for the trip to Maui. It seemed the two of them were running into town almost every night to get something else. I told Amy to make sure she took Sam to the swimsuit store and get her whatever she wanted. I gave her a credit card for Sam and anything she might need and got her some cash.

When Friday night came Dawn and I went to bed early because we had to get up about 3:00am to leave for the airport. About 10:00pm Amy stuck her head in the door of our bedroom to check on us.

"Amy, come on in," Dawn said when she saw her.

"I just wanted to see if you two were asleep yet," Amy said as she walked into the bedroom.

"I can't sleep, I'm too excited," she told Amy. "Get in bed with us so we can talk."

Amy slid into the bed next to Dawn. Now I couldn't sleep because the two of them were talking. I thought they had discussed everything already and now Amy was talking about her and Sam getting sunburned.

"Amy, I have a suggestion," I interrupted.

"What?"

"I think it would be a good idea for you and Sam to spend some time at the tanning salon before you leave so you can get a start on a tan."

"James, redheads don't tan, we freckle," Amy replied.

"It wouldn't hurt," I said.

"Maybe, but you better plan on keeping the two of us covered in sunscreen."

"I can see that happening," I said with a laugh.

"I bet you can," Dawn said.

It was about midnight when I asked the two of them if they planned on getting any sleep; we had to get up about 3:00am.

"James, I won't ever go to sleep," Dawn said.

"May I make a suggestion," Amy said with a smile as she looked over at me.

"What Amy?"

"You two have to get up in a few hours anyway so why don't we just have sex for the next couple of hours."

"That sounds like a good idea Amy," Dawn said. "After all, we won't see you for two weeks."

"I should have known," I said.

Amy and Dawn started giggling.

"You two go first, I want to watch," I told them.

"Our pleasure," Amy responded.

I watched Dawn and Amy make love to each other for about an hour. I always enjoyed lying next to them while they kissed and caressed and enjoyed each other. Dawn took her time exploring Amy's body and driving her to multiple orgasms with her tongue. Amy returned the favor by kissing every inch of Dawn's body before she went down on her. After plenty of hot screaming and moaning orgasms they rested a few minutes then started on me.

Dawn straddled my face so she could watch Amy slip my cock in her and fuck me. I took care of Dawn's pussy while she and Amy kissed and played with each other's tits. I drove Dawn to the heights of ecstasy while she ground her pussy down on my mouth. She came over and over again as I took my time sucking on her pussy and clit. During all that Amy was doing a good job of getting all she wanted for the next two weeks.

When Dawn couldn't stand anymore she moved so that she was straddling my stomach so her tits were touching Amy's while she continued to impale herself on my cock. I watched as Dawn wrapped her arms around Amy and began kissing her deeply. Amy got turned on even more. While the two of them were in an embrace kissing Amy began to grind her pussy down on my cock in a rapid motion. I could hear Amy moaning into Dawn's mouth as she began to build to her orgasm.

Dawn had slipped her arms up under Amy's arms and was holding her head so their kiss didn't break while Amy started humping me faster and faster. I could feel Amy's pussy muscles tightening up as she ground into me. Amy was groaning loudly into Dawn's kiss. This was something the two of them had never done before and it was a real turn on for me.

I felt Amy begin to jerk; I knew she was near climaxing.

"Mmmmmmmm!" Came from Amy as she started coming hard.

Dawn held on to her as she jerked over and over as an orgasm rocked her body. More groans and sounds came from Amy as she jerked. I could feel Amy's juices flowing around my cock and down between the cheeks of my ass.

Amy forced her way out of Dawn's grip.

"Oh god!" She said as Dawn pulled her head down on to her shoulder.

Amy was struggling to breathe as she wrapped her arms around Dawn and held on as she kept pushing herself to continue to hump my cock.

"Oh god Dawn, I'm coming again!"

Amy shoved her pussy down as far as she could onto my cock as I felt her hips jerk and twitch.

"Mmmm!" Came from Amy.

Amy stopped her grinding and just sat holding Dawn. I could feel the muscles inside her twitching as she sat.

"Dawn, trade places with me, I am wiped out."

I felt Amy slide up and off my cock as she swapped positions with Dawn. Dawn took her place and slid her soaking pussy down onto me.

"I'll take care of this real quick," Dawn said to Amy.

Dawn began humping me like mad; she was thrusting her hips into me as quick as she could.

"James come in my pussy!!" Dawn screamed.

Dawn was hot as hell and was determined to get me off. Her rapid thrusting was really making my balls tense up, building to an explosion of cum. I watched Amy lean forward and grab Dawn's head and pull her to her lips for a deep kiss, holding on tightly as Dawn continued.

My cum was starting to build but I held on until Dawn was ready. She was moaning over and over into Amy's mouth now. I could tell she was about to explode, undoubtedly Amy knew also. I watched her remove her hold on Dawn's head; she reached down and started rubbing Dawn's clit.

"Oh Amy, I'm coming, I'm coming!"

I felt Dawn's pussy clamp down on my cock as she began jerking hard. I shoved up as best I could with the two of them sitting on me and let go. I felt my cock pulsating as it pumped load after load of cum deep into Dawn. Dawn was moaning over and over into Amy's kiss while Amy continued fingering her clit.

Dawn broke free of Amy's hold.

"Oh my god I'm coming!!" Dawn screamed.

Dawn jerked against my cock as I continued to empty my cum into her. Each time she jerked she screamed she was 'coming'. Dawn humped against me until she was spent. Amy wrapped her arms around Dawn and pulled her tight so she could hold her up.

"Mmmmmm," came from Dawn as her head lay on Amy's shoulder.

"Oh my god, that was much better than sleep," Dawn said as she sat up.

"Much better," Amy agreed.

"What time is it?" Dawn asked.

"It is about 2:15am, are you two ready to shower and get ready to leave for the airport?"

"Yes," Dawn said.

We all got up and headed to the shower, we had plenty of time to spend there before we had to leave. As soon as we got in the shower, Amy lay Dawn down on the seat in the shower and sucked my cum out of her pussy. Dawn had another orgasm while she did. We took a long time washing each other before we got out.

Amy left to go get dressed while Dawn and I got ready.

"Dawn, you are going to be very tired when we get there," I told her.

"I don't care. I can sleep on the plane."

"Don't forget, we have to change planes in LA."

"I can sleep from there to Hawaii."

Dawn was drying her hair and putting on her make-up while I shaved.

"Are you two about ready?" Amy asked from the bathroom door.

I turned to look at Amy. Her hair was still wet and she had slipped on a pair of jeans and an oversized t-shirt.

"You ready already?" Dawn asked.

"I'm just the driver," Amy replied.

"Amy, what should I wear on the plane?" Dawn asked.

"It depends."

"Depends on what?" Dawn asked puzzled.

"Depends on what you are going to spend the next 6 or 8 hours doing."

"What are you talking about?" Dawn asked as she stopped putting on her make-up.

"I would just say dress comfortably," Amy added.

"What would you consider comfortable?" Dawn asked.

"Why don't you wear that short pleated black mini-skirt you have and the shear black top with a black bra."

"Amy, I don't think they would let me on the airplane with that top on!"

"Wear a light sweater; it will be a little cool this morning anyway."

"Amy, if she dresses like that something is liable to happen on the plane," I said.

"I know," and Amy turned and walked out of the bedroom.

"James, should I dress like that?"

"You dress however you feel comfortable; if you want to wear that it's okay with me. It will be warm when we get there so it would be comfortable. I just may have to beat the guys off of you."

"Okay, I'll wear that then."

I went to get dressed while Dawn finished her make-up. I was going to wear a pair of lose fitting pants and a polo shirt. Flying was not one of my favorite past times, as tall as I am I always flew first class so I would have room for my legs. Dawn was so small she could sit in the bathroom of an airplane and be comfortable.

Dawn came out of the bathroom wearing a black bra and a pair of tiny black see through panties. She looked hot with the black on. She went to the closet and came back carrying the shear black blouse she had and the pleated black mini-skirt. I watched as she assembled her outfit. The blouse was very shear and I could clearly see the black bra she had on. It was at least a modest bra, not one of her usual lacey items. She had worn this before when we went out to eat and it always turned many heads. She slipped on the mini skirt. I was surprised she decided to wear it; I thought she would have been more comfortable in a pair of shorts but I never knew what Dawn would do when challenged.

There she stood in all black. The shear long sleeved top and the mini-skirt. The skirt was not real short like some of her clothes but it was short enough that she had to be careful when she sat down. She liked wearing this outfit when we went out to eat because she liked the men starring at her thighs while she sat, and so did I.

"How do I look?"

"Extremely too hot to be on an airplane, are you going to wear a garter and stockings?"

"I don't think so, is this okay, should I change?"

"Not if that is what you want to wear, but you will have to wear your light black sweater and button it up or they will never let you on the plane."

About that time Amy came back in the bedroom.

"Perfect," she said. "You about ready to go?"

"I'm ready; I just have to get my sweater out of the closet downstairs." said Dawn

"I will start loading the bags in the truck," I told them.

I went on down and loaded all the bags in the Escalade. Dawn got her black sweater from the closet and put it on. It really wasn't a sweater; it looked more like a crocheted top when she had it buttoned up.

We were finally ready to go. I drove while Dawn sat in the front seat and Amy rode in the back.

We were about 15 minutes into the drive when Amy said, "I really want to thank you two again."

"No need Amy, we just want you and Sam to have a good time," I told her.

"I had a good time tonight. I can't wait until I see you two again."

"I think we will all have a good time while we are there," Dawn said.

"I think we will too," Amy replied.

We drove for about 10 more minutes before we were nearing the airport.

"Hey you two, I want you to do something for me," Amy said.

"What Amy?" Dawn asked.

"James, I want you to "do" Dawn on the airplane and tell me all about it when I get there."

"Amy! You are crazy!" Dawn said.

"I bet you two can pull it off. Do it, then you can be in the mile-high club."

"We could also end up in the jail club," I told Amy.

"Chicken," Amy said.

"We'll see," Dawn said as she looked over at me and smiled.

We got to the airport and unloaded all the bags in front of the terminal. I had a skycap load them all up so he could check them in. There weren't many people at unloading but there were a few. Amy kissed both of us goodbye and got in the driver's seat and left. I couldn't wait until we were all together in Hawaii. I had some things planned that the girls didn't know about.

When we got to security there were a few people backed up, all of the post 9/11 security had things slowed down at the airport and there were only three security people on duty at 3:30 in the morning. We placed our carry on stuff on the x-ray machine and watched as the security people pawed through it on the other side. I went through the metal detector first so I could get to our stuff then Dawn followed. The metal detector went off.

"You have got to be kidding," Dawn said.

"Ma'am, do you have anything metal on you?"

"In this outfit, no!"

"Just let me run the wand over you," the guard said.

He ran the wand up and down Dawn as she held her arms out, when he ran it over her front, it went off.

"Do you have any jewelry on ma'am?"

"No."

He ran over the front of her again and it went off, he signaled for a female guard to come over. She came over and took the wand and ran it around Dawn's breast.

"Do you have an underwire bra on?" The female guard asked.

"Yes!"

Dawn was getting frustrated and cranky from no sleep.

"I have to check, sorry," she said.

"How do you plan on doing that?"

"We can go into the room over there; I need to pat you down."

"You mean feel my tits!"

"Can you come with me?"

The guard escorted Dawn to a private room. A few minutes later she and the guard came out laughing. Dawn was still buttoning up her sweater.

"She can go," she told the rest of the guards.

We picked up our bags and went on down to the gate.

"What was so funny?" I asked.

"Nothing, she just liked my blouse. She said she didn't think I could hide anything under it."

We made it to the gate and onto the plane for the first leg of the trip to LA. The first class section of the plane only had 12 seats up front but there were several other people already in first class. They looked like businessmen going to the west coast early in the morning. We settled in for the 2 plus hour flight to LA, we had about a two hour stop over there before we would board the flight to Maui.

We had no sooner lifted off when Dawn leaned her seat back and went to sleep. When the stewardess came by and asked if we wanted anything Dawn was already asleep; I asked for a cup of coffee. There was only one stewardess in the first class section; she was a nice looking brunette. When she returned with the coffee she looked at Dawn's bare legs and asked me if she should get a blanket for Dawn. I told her she was okay for now.

We were sitting in the second row of first class, there was a man sitting in the front row by himself with the light on reading a newspaper. I sipped my coffee while Dawn stirred in the seat next to the aisle. She woke up for a minute and asked me if I was okay then slipped down into the seat further and went back to sleep. When Dawn slid down into the seat more it pulled her short skirt up. I looked over and could tell that if anyone looked when they walked by they were going to see a lot of thigh. I started to pull her skirt back down but decided not to disturb her.

The stewardess came back by and refilled the coffee for the man in front of us; then she stopped and asked if I needed a refill. I accepted her offer as she leaned over and refilled my cup.

"Are you sure your wife doesn't need a blanket?" She asked me again.

I looked up into her pretty face and she was looking at Dawn's thighs.

"No, really, she is comfortable."

"Okay," she said.

I looked at her nametag, it said Janice.

"Janice, do you think she needs a blanket?"

"Oh no, I just didn't want her to get cold," Janice replied as she looked at me and smiled.

"I think she is okay Janice." Janice looked at Dawn's thighs again and told me that if I needed anything to just hit the call button.

I was looking out the window and drinking my coffee, we were about 30 minutes into the flight, and we still had several hours to go. I heard Dawn stir; I looked over to see if she was awake. She had shifted again and tried to turn toward me. Doing this she had managed to make her skirt slide up even more. Looking at her skirt I realized that it had slid up to her crotch as she had moved. I could clearly see the thin material trying to cover her pussy. I reached over to pull her skirt down but changed my mind and pulled it up another inch, clearly exposing the triangle of thin material over her pussy. Dawn had let her legs parted just slightly so I had a good view of her pussy when I looked.

I heard the man in the front row begin to stir; he was getting up probably to go to the restroom. Being that he was in the front row, he could completely stand up and look back over the rest of first class. I turned my head as if I were looking out the window. I looked out of the corner of my eye as he came around to the aisle, he paused for a second before he walked by, I could see that he was obviously looking at Dawn's crotch.

Seeing that I wasn't watching him he stood for a few seconds and took in the sights. He looked to be about 40 and was a nice looking guy; I knew Dawn would be happy that she was exposing herself to another man.

He eventually walked on by and looked down as he did. I heard him lock the restroom door a few seconds later. I wanted to laugh but decided not to. I enjoyed strange men looking at my beautiful wife, wanting her, wishing they could have her.

There was another businessman in the front in the other row, in the row next to ours there was a couple about our age. The woman was sitting next to the aisle; she had leaned up against her husband and was also sleeping. She was blonde with long hair and a nice looking body; they were dressed casually and comfortably. She had on a pair of baggy shorts and a white blouse; he was wearing shorts and polo shirt.

I heard the restroom door open so I knew the guy was returning. This time I did not act as if I was looking out the window, I sat sipping my coffee. He walked by slowly trying to pause and look at Dawn's crotch but didn't when he saw me looking at him. He did stop facing back toward us and took off his suit coat, sneaking glances at Dawn's crotch the whole time. I looked up at him and he made eye contact with me, knowing I knew he was looking at my wife's crotch; he wasn't sure what expression to give me. I looked up at him and smiled while I took another sip of coffee. He was trying to stuff his coat in the overhead compartment when Janice walked up.

"Here, let me have that sir, I'll hang it up so it doesn't get wrinkled."

He handed Janice his coat and she waited while he sat down. Janice turned toward me and looked down at Dawn's exposed crotch then looked at me and smiled as she walked by.

Janice returned and asked the guy sitting across from us if he needed anything. He woke his wife up and asked if she wanted anything, she told Janice she would like a cup of coffee. Janice went to get the coffee; the blonde looked over at me.

"Hi," I said.

"Hi," she said back nicely. "Where are you headed?"

"Maui, where are you two headed?"

"Same place," the blonde said while she glanced down at Dawn's exposed thighs.

From where she was sitting she could only see that Dawn was showing a lot of leg.

"Your wife looks like she is in a really deep asleep."

"Yes, we didn't get any sleep last night, now she is going to sleep all the way to Hawaii I think."

"Where are you staying in Maui?" The blonde asked.

"We have rented a house on the beach, where are you staying?"

"Black Rock Point. Sorry I didn't introduce myself, I'm Jill and this is my husband Mike."

Mike leaned forward and said 'hi'.

"I'm James and sleeping beauty is my wife Dawn."

"She must have had a long night," Jill said.

"No, she wanted to fuck all night, now she is sleeping."

I heard the guy in front of us choke on his coffee.

"Same here, that is why I need some coffee," Jill said.

"Are you from town?" I asked.

"No, we came from the east coast; we have already been on the plane several hours."

drmac100
drmac100
1,233 Followers