Life after the Lottery Ch. 45

"Oh Gary! Do you like doing that?" Helen asked.

I didn't hear Gary say anything.

"Yes Gary, that's it!" I heard come from Sam.

Helen was moaning hard. I was tonguing her ass and she was watching her husband. A few minutes later she was screaming she was coming.

"Oh my god!! Yes!!"

Helen jerked hard then I felt juices squirt from her pussy and run down my neck.

"James, stop!!"

Helen got off my head and turned around and straddled my cock.

"Oh yes, you are so big," she said as she worked the first few inches into her pussy.

"Just do it, Helen," Sam said.

I looked at Sam. She was on all fours and Gary was working his fingers in and out of her ass.

"Tongue me, Gary!"

Gary pulled his fingers out then started licking Sam's asshole.

"Oh fuck yes!" Helen said watching her husband. She forced her pussy all the way down on my cock.

"Ahhhhhhhhh, yes!" She exclaimed as she slid down.

I felt some resistance before she got all of it in her, but she paused a second then used her weight to push all the way down.

"Ohhhhh, I have never had a cock in me this big!" I think Helen had forgotten her husband was sitting there. "Gary bought me a vibrator this big, but this is so different, and warm."

Helen sat for a minute and then began to work her hips. Being an older woman, she knew what to do. I reached for her breasts and rubbed them for a minute then began squeezing her nipples as she kept going. She would alternate between grinding her hips into me and leaning over and putting her hands on the bed and working her pussy up and down. She had several nice orgasms over the next half hour.

Sam was enjoying being fingered and licked. She had come at least once from Gary tonguing her ass.

"Oh, that is so nice! I'm so full." Helen had her head swiveled so that she could look at her husband, "Gary, will you do that to me from now on?"

"Yes I will! Just before I slip my cock in your ass!" Gary said.

"Helen, James always does this to us just before he slips his huge cock in our ass."

"He can get this thing in your small ass?" Helen asked.

"Yes."

"Oh my god."

"Gary...I will let you fuck my ass...if you let James do Helen's ass," Sam said.

"Oh my god!" Gary said.

I could see his cock was turning purple again.

"Helen?" Gary said.

"I don't know, Gary. He is stretching my pussy pretty tight!!"

We watched as Gary worked his fingers in Sam's ass. Helen was still working her pussy on my cock. Sam was moaning as Gary worked on her. Helen kept working her pussy until she came again.

"Oh fuck!! Okay!!" Helen screamed.

"Gary, I guess that means you can finish the job," Sam said.

Sam was up on all fours on the bed. I watched as Gary climbed on the bed behind her. He grabbed his cock and started it into Sam's ass.

"Ohhhh yes! Fuck my ass Gary!"

Helen was slowly working her pussy on my cock as she watched her husband. He was taking his time slipping in and out of Sam. Helen was hot, I watched as she ran her hands down to her pussy and started fingering her clit.

"Oh god Gary, harder!"

Sam looked over at me and smiled as she grew hotter and hotter. I winked at her and she smiled. Gary grabbed her hips and began slamming into Sam's ass. I was enjoying watching Sam's tits swing as she got fucked. I returned my attention to Helen, she was humping me faster and was rubbing her clit harder.

"Fuck her Gary!" She shouted.

Gary was working his cock in and out of Sam hard. Sam was enjoying it.

"Fuck me!!" Sam screamed.

"Ahhhhhhhhh!!" Came from Gary as he started pumping cum into Sam's ass.

"Oh fuck!! Came from Sam as she came hard.

"Oh...my...god!!" Helen screamed as her fingers became a blur over her clit. She started jerking and screaming as juices kept gushing from her pussy over and over. "Oh god...never!!" Helen kept coming again and again.

"Oh fuck, Sam. That was wonderful!" Gary said.

I watched Sam push her ass back into Gary. He leaned forward and reached around Sam and grabbed her tits.

"Ahhhhhhhhhh!!" Helen screamed as she tensed up then fell on top of me.

"Oh James, your cock feels so fucking good inside me!"

After Helen was rested she sat up. She pushed herself up on her knees and grabbed my cock and placed the tip at her asshole.

"Let me do his!" She said.

Helen held my cock as she pushed, but she was so hot, she pushed hard. My cock slipped into her ass and she pushed down.

"Oh my god! You are so big!"

Helen removed her hand from my cock and began pushing down. Inch by inch she slid down as she bit her lip.

"Damn!" Gary exclaimed.

Gary was watching my cock slip into his wife's ass as he squeezed Sam's tits.

"Gary, I feel your cock getting hard again," Sam said. Gary raised up and began sliding his cock in and out of Sam's ass again.

"Ahhhh!!" Came from Helen as she shoved herself all the way down.

"You feel good," I told Helen.

"You do too!"

Helen pulled her legs from under her ass and put them up by me and leaned back on her hands, just the way I liked it. She went to work sliding her ass up and down my cock. She knew how to get what she wanted.

"Oh god, this feels so good!!" She was having a good time sliding up and down my big cock.

Helen took her time, but worked her ass hard on me. I was holding her legs and watching my cock slide in and out of her nice looking ass. Her pussy was still dripping from her previous orgasms. Helen sped up, frantic to have me come in her ass.

"Oh god!! "I'm going to come again!!" Helen was breathless as she worked harder. "Oh fuck!! I'm coming!!" Helen had her biggest orgasm so far. She kept slamming her ass down on my cock.

I heard Sam and Gary moaning somewhere.

"Oh your cock feels so good deep inside my ass!!" Helen screamed.

I heard Sam screaming as I watched Helen work her ass. She was slamming down on me hard. I was about to come.

"Fill my ass full of cum, please!!" Helen screamed.

I grabbed her legs and yanked her down hard on my cock and began pumping her full of cum.

"Oh yes!!" I yelled.

"Oh shit, your cum is so hot!!"

Helen was trembling as she sat on my cock after her final orgasm.

"I'm finished," Helen said softly.

We heard Sam and Gary finishing.

I reached for her hands and she took mine and I pulled her up.

"I'm exhausted," she said. She looked spent.

"Oh that was good!" I told her.

"Yes...it...was..."

"Gary, were you okay with that?" Helen asked.

"You looked like you enjoyed it," he said.

"I did, I have never come so much, damn you James!"

"I wanted to make sure you enjoyed your first time with another man, just in case you two decide not to do this again."

Helen rolled her head to look at Gary as he lay with Sam.

"What do you think, Gary?" She asked. As she asked I flexed my cock inside her, drawing her eyes briefly back to me as she waited for her husband to respond.

"I really enjoyed watching and I know you enjoyed it," he said.

"Can we do this again?!" She asked.

"If you are okay with it, I am. I am not sure you will ever get another fuck like that, but I am happy you had a good time."

Helen, with me still inside her, took a moment to look lovingly at her husband before responding softly, "thank you, Gary."

Helen lifted her ass up and I slid my cock out of her and looked at the clock, it was 10 till six.

"Let's go shower first," I told Helen. I got off the bed and helped her up. She grabbed my still partially erect slick cock. I took her to the shower.

"James, that was fucking wonderful, I have never been fucked like that before. I mean it."

"As long as you two enjoyed it and everything is okay."

"I think it is going to be. I think Gary got off on watching me get fucked."

"Did you get off on watching him fuck another woman?"

"Yes I did. You are right, it is very erotic watching him please another woman. I hope some of our friends and husbands want to share."

"Just take it slow. You may want to experiment some more without Gary watching. He will be okay with that. Remember that this isn't for everyone, so pay attention to who you can trust with this kind of thing."

"Are you sure?"

"Yes. I let my wife experiment a lot alone with other women when she wants. When you are ready, you and your friend let Gary watch you in a 69."

"Do men like that?"

"I think it is beautiful, and I'm pretty sure that I speak for most men on this."

We got in the shower. Helen wanted to play with my cock as the water ran over us. While I was soaping up her tits and the rest of her body she kept stroking my cock. Soon she had me hard again so she looked into my eyes then slid down to her knees and sucked my cock into her mouth. She was going at it like she was starved. Much more aggressively than when her husband was watching. I reached down and placed my hands in her wet hair and pulled her onto my cock, sliding more into her mouth. She kept going.

"Are you okay?" I asked her. She slipped her mouth off my cock and looked up.

"I want all of it!" She slid my cock back in her mouth and started shoving her mouth down on me. I took her head and pulled it in harder. She didn't resist so I pushed harder until I felt the head of my cock sliding down her throat. I released her, but she held her head there for a few seconds before I felt her pulling off.

"That is what I fucking want! Fuck my mouth!!"

When Helen slipped her lips back over my cock, I did what she requested. I jammed my cock down her throat as I held her head, over and over I thrust. I didn't get the opportunity to do this often, so I took my time. Helen was being very aggressive as she sucked. I knew we had spent too long at this, but I eventually jammed my cock down her throat and shot a huge load of cum down it. Helen sucked it all out then stood up.

"I wanted to do that before, but I didn't think Gary would like seeing me deep throat you. That was good, thank you."

"Thank you."

We got rinsed off and left the shower and dried off. When we went back to the bedroom. We didn't see Gary or Sam. About that time the door came open and Gary and Sam run through it laughing.

"Where did you two go?" Helen asked.

"To your room to shower!" Sam said.

"Gary, I think you have had enough." Helen said as she sat on the end of the bed.

"Emmm, yes! Thanks Sam." Gary said.

Sam turned to Gary and grabbed his hard cock.

"I had a good time too, thanks Gary."

"We hope you two had a good time, and we hope that you will take something away that you can use to enhance your sex lives," I told them.

"I think we will," Gary said. "You two have been nice to let us see what we like."

"Is there anything else you two do?" Helen asked.

"Yes, we like to watch people fuck," Sam said.

Gary smiled at Sam then looked at his wife.

"On the bed Helen, on your knees!" Helen giggled then crawled up on the bed on all fours.

"It's the least we can do for you," Gary said as he got behind his wife and slipped his cock into her.

Sam turned and sat on the bed next to them as they got a good rhythm going. I sat in the chair and watched as Gary pounded Helen. Fifteen minutes later, the two of them came at the same time. There was a knock at the door, I looked at the clock and it was 6:30.

"Just a minute!! That will be the guy coming to fix Sam's hair," I said.

"Oh, good idea, I need to do mine," Helen said as her and Gary got off the bed and found their robes. "We will be ready at 7:30."

I picked up my robe as they headed to the door. I opened the door and they left and I let Andre in.

"Oh me! Having some fun I see!" Andre said.

"A little."

"Where is that beautiful young lady?"

"In here!" I heard Sam call from the bathroom.

We walked to the bathroom and Sam was sitting naked in the chair brushing her hair.

"I guess we will get started!" Andre told her.

I went back to the bedroom and got dressed. I could hear Sam and Andre laughing as I finished. I straighten up the room and the bed, the sheets were covered in cum and female juices. I called housekeeping and asked if they would come and change the sheets later...the penthouse has its privileges. I would also leave $50 on the bed. I sat in one of the big chairs and waited.

"What do you think?" Sam asked standing in front of me with all her long red hair curled in big curls and her makeup perfect. Andre was watching, waiting for my response.

"Excellent! Thank you Andre."

"My pleasure!"

Andre went to pack his things up as Sam turned for me.

"You need to get dressed, it is getting late."

Sam walked over to the packages she had acquired and got out the dress and shoes. She got the black stockings out she had bought and sat on the bed and slipped them on as Andre and I watched.

"Those are so hot!" Andre said.

"Sam, when you sit, the tops are going to show," I told her. She looked at me and smiled.

Andre got ready to go but stopped to watch as Sam stood and slipped the black silk dress on. He walked to Sam and helped her get the dress on and in all the right places.

"You are just perfect!" He said.

"Thank you."

"Yes, thank you for helping," I told him and gave him $100. He smiled and left the room.

"Sam, you look gorgeous."

"Thank you. What time is it?"

"We have about ten minutes."

"That was a first, I have never been with you when you picked up another couple," Sam said.

"It is rare, but you seemed to like the idea."

"I did! Can we do it again sometime?"

"If the right occasion arises. What about Kathy?" I asked.

"That was fun and erotic. The first time I am with another man or woman, I find it erotic. With the woman, I find it challenging to find all the ways to turn her on while I eat her."

Listening to Sam talk, I felt like there was going to be a lot more to her than Dawn and I suspected. She was saying things that only Dawn and I talked about.

"Sam, since you have never been to a strip club, especially one like this, I need to explain a few dos and don'ts."

I was explaining things to Sam when there was a knock at the door. I went and opened it and it was Helen and Gary. I looked Helen over, she was wearing a blue dress similar to Sam's, but not quite as short. Sam came to the door and they looked her over as we walked out.

"Let's go. It will take about 20 minutes to get to the steak place. You two ladies are going to liven up the place," I told them.

Once we were in the limo sitting across from each other, they wanted to talk about how to approach other women and couples. We talked the entire ride as I gave them a quick lesson . Gary had been looking at Sam's legs. I had been looking at Helen's thighs. I was surprised she had on a blue garter belt that matched her dress. The dress was short enough the tops of her black stockings showed too.

"Helen, that dress is awful sexy," I told her. She smiled.

"It's not as short as Sam's, but it shows a lot." She said with a smile as she pulled the hem up to show me the garter belt was all she had on.

"Perfect."

We stopped at the front of the restaurant. As we exited the limo and I told the driver to be back at 10:00. I also told him where we were going after that and asked him if he would be available to pick us up about 4:00am. He explained that the hotel limos were on call 24/7. He gave me a number to call.

They were waiting on me at the door as I walked up so we went in and were seated. I asked Sam to not try and order any alcohol. She pouted, but then smiled. We had a nice long dinner with wine and dessert as we talked.

"James, where is this club?" Gary asked.

"Other side of town. It will take about 20 minutes from here."

"What kind of club is it?"

"A very exclusive Gentlemen's club, I am a member."

"That sounds interesting," he said.

"Does gentlemen's club mean strip club?" Helen asked.

"Yes, is that okay with you?"

"Yes it is." She waggled her finger at her husband, "He will never take me to his."

"Helen, this is a very elegant place, you will enjoy it," I told her.

"Maybe the Toad will take me from now on!" We all laughed.

We finished dinner and went to the limo. The ride across town was long enough that dinner had time to settle while we talked some more. When we pulled up, the valet let us out. Gary had gotten out first, when Helen leaned over to get out I ran my hand up the inside of her leg to her crotch, she paused a moment, then she got out. Sam exited and I looked at her ass as she bent over, then I got out.

"I think we will have a good time tonight." I told everyone.

We walked to the door and I showed the hostess my VIP card. She looked at Sam a second.

"You are 18?" She asked.

"Yes," Sam answered.

"You look older than that. This way Dr. Smith."

We were led to a nice table at the front of the stage that I had asked for. The hostess picked up the 'Reserved' card. The music was on and the show was going on as we sat.

"Nice place," Gary said.

We had only been sitting about a minute when one of the beautiful waitresses walked up in a thong and a very small top. They usually waited until after midnight to take their tops off and sometimes their thongs.

"My name is Sara, what may I get for you, Dr. Smith?"

"What would everyone like? A nice wine or some champagne?" I asked. We settled on a nice wine. Sara walked away and we watched her nice ass.

"There are some pretty women here," Gary said as he looked at the stage where a redhead was performing.

"You will find that the women here are very pretty. The members make sure they are well paid," I told Gary. Ashley had told me once that she made well over $100,000 a year just in tips.

"I will keep that in mind," Gary said with a smile.

We watched the redhead finish up before Sara came back with the wine. She sat four wine glasses on the table and opened the bottle.

"I will be your waitress all night. Is there anything else I can get for your party, Dr. Smith?"

"Sara, I need some cash please."

"Very good, I will be right back."

"Gary, if you need cash, she will be back with a form to write how much you need and it will be charged to your credit card," I told him.

"Great, I didn't have time to get any at the hotel."

"Can I?" Sam asked.

"She brought you a glass, I guess so."

I poured the four of us a glass of red wine. Sam sipped it slowly as she looked around.

"The place is full," Sam said.

"Probably about 150 people. The place will get crazy after midnight," I told Sam.

"How do you swing a table in front of the center stage?" Sam asked with a smile. I just smiled back at her.

"How do you do it?" Helen asked.

"I am a VIP a member, there are not many of us. It comes with perks," I told her.

"I'm a VIP member at my club, but it doesn't come with these perks," Gary said.

"Gary, your membership is probably not $75,000 a year."

"Damn," Gary said. "What does a regular membership cost?"

"Regular members pay $20,000 a year. That is why this place is so nice and the girls are so beautiful. It is a very exclusive club."

"Must be at that price."

A gorgeous black girl came out on the stage and started dancing. I had not seen her before and she had an incredible body with excellent tits. We were enjoying her show when Sara came back. She handed me the form and asked Gary if he needed one. He said yes. I wrote $10,000 in $100 bills on it and signed it and gave Sara my AMEX. She waited while Gary finished.

"Thank you, I will be right back."

"I would have thought the waitresses would be topless," Helen said.

"They will be. VIP members get their own personal waitress. I will take care of it."

It was getting close to 11:00 and I figured I could get Sara out of her top and thong before midnight. I had looked around and none of the other girls were topless yet. We returned to watching the show. The young lady was putting on an excellent show for us. She was down to her thong as we watched her dance.