A Night to Remember

[Homer A.C]

A night to remember
Author: Homer A.C
Pairing: M/FFF
Cast: Nick Lackey, Jessica Simpson, Ashlee Simpson, and CaCee Cobb
Usual disclaimers... note that I am not making any money from this and these events never happened nor am I implying that they did. All these events happened here in my head!
Summary: the girls treat ashlee simpson to a unforgettable 21st birthday party.


I am the luckiest bastard on earth. I have a very sweet and sexy 26 year old wife with huge natural tits and a tasty pussy that I have been married to for 3 years. She was a virgin when I met her and I am the only man she has ever been with. Our sex life is great and I should be content right? Well, lately when I am balls deep in my sexy wife’s pussy, the only thing I can think about is how good it would feel to have my tongue buried in her sister’s ass while my wife rides me. But how to make it happen …

It was a Tuesday night in October and my wife’s kid sisters birthday coming up. Ashlee Simpson was turning 21.

“What should we do for Ashlee’s birthday?” Jessica asked.

Without even thinking I blurted out, “Why don’t you take her out for a night on the town? Maybe go catch a male stripper show or something”.

Jessica blushed. “I can’t do that. I wouldn’t feel right”.

“Well you know your sister has been a little down since she broke up with Ryan. This might bring her spirits up”.

“Do you really think so?” she asked.

“Sure, you can take CaCee along as well and at the end of the night the girls can sleep here”.

“That sounds like fun”

“Hey of course, together you can all have some fun, especially with the strippers”.

“Oh I won’t really enjoy it. I have all I want right here at home” Jessica said sincerely.

“Yeah right”, I laughed. “Wait till some hunk is stirring your drink for you while you are shoving money into his g-string”.

For that I got a playful slap but the sex was unbelievably hot that night. As we faded to sleep Jessica murmured, “I think you might be right about Ashlee. I’m going to tell her we go out this Friday night.”

Friday night arrived and Jessica was dressed to the nines in a sexy little black dress. It showed off plenty of legs and especially her large big tits! The skirt length was mid-thigh and gave me an instant boner when I saw her come down the stairs. Just as we started to fool around a little, Ashlee and CaCee arrived and I kissed Jessica goodbye. Ashlee looked sexy in a tight blue tube top and hip hugging low riding jeans, as did CaCee who was dressed in a skimpy white halter top and tight jeans.

“Have fun ladies” I said as I gave Jessica’s ass a little grab. “You aren’t wearing any panties you little hussy!” I hissed as the others giggled.

“It’s a new thong I bought, and you will get to see it later. Now get your hands off the merchandise and let us get going” Jessica replied.

This was working out better than planned and I knew I was going to have fun tonight. The ladies left and I made myself a drink and thought about the different ways tonight might play out. Maybe I would be able to convince my wife and the others to join me for a late night skinny-dip in our pool. After a few more drinks I nodded off while watching TV. It was around 1:30 am when I heard someone fumbling with the front door. I got up and opened the door and found the girls giggly and quite tipsy. They all stumbled in laughing hysterically and CaCee made for the bathroom.

As I made the girls some drinks, I noticed that Ashlee was her exuberant self, laughing at something that the girls had been talking quietly. But Jessica wasn’t laughing. She seemed serious, like something was bothering her.

“What’s up ladies. Did you have fun?”

Ashlee smiled, “You should probably tell him Sis. He’s pretty smart and will figure it out anyways”

“Tell me what?” I looked directly at my wife.

She shot her sister a dirty look as Ashlee then said, “She touched one of the stripper’s cocks and we got kicked out …”

“SHUT UP ASHLEE” Jessica yelled.

“Ah, he’s a big boy Jess, I think he can take it.” CaCee said coming back into the room.

Inside I was jumping for joy, but instead I put on my serious face and said, “Is this true Sweetie?”

Jessica didn’t answer me but the look in her eyes told me it was true. Feigning indignation I grabbed my drink and stated, “Well I’m going out to the pool”.

Wearing a shirt and shorts, I went through the French doors to our deck and although it was dark out I knew the girls could clearly see me. I stripped down to my trunks and walked into the pool. I watched the girls, through the glass in the doors. It looked like they were having an intense argument. While the sisters continued to fight, CaCee came out to talk to me and I convinced her to get in the pool with me. Slightly drunk, she giggled and stripped down to her underwear before dipping into the pool. Laughing hysterically, we sat in the corner of the pool drinking and laughing.

Finally after a few minutes we saw the girls hug each other, and while Jessica went upstairs, Ashlee came out on the deck.

“Don’t be mad at Jessica Nick, I put her up to it. I made her do it.” I remained silent while I sipped my rum and coke. “C’mon Nick. How can we make it up to you?”

Bingo.

Now I was getting somewhere.

“Well first of all, you can get in the pool with us” I told her.

While Ashlee argued she couldn’t because she didn’t have a bathing suit, CaCee reminded her it was her birthday and told her to relax as she too didn’t have any swimmers but instead was swimming in her underwear. Not wanting to disappoint me, Ashlee then stripped out of her outfit and climbed into the water with us. A minute later, Jessica then came out with a fresh tray of drinks and for a minute looked shocked to see us all in the pool together having a good time.

“I’m sorry Nick. How can I make this up to you?”

Score again!

Sounding defeated I said, “I dunno, come sit in the pool with us and tell me everything”

The girls then persuaded her to strip and get in the water and reluctantly she did. Joking around and wanting to help Jessica feel comfortable CaCee then pulled her top off and Ashlee did the same, leaving them both topless in the pool. I was surrounded by tits! Still shy but feeling better Jessica finally did the same. It was like I was a master hypnotist. Not only did I convince both Ashlee and CaCee to strip down to their undies, but I now had them all topless as well.

Still timid about her body, Jessica was now only dressed in her new black thong she had told me about earlier. She looked terrific. Ashlee was in a pair of high cut blue undies while CaCee was now completely naked, throwing her wet panties across the deck. Not getting away scott free, the girls then demanded I take off my trunks to make it fair. I did and I threw them over towards where CaCee’s panties were.


Ashlee whistled and then told Jessica, “Wow Sis you look hot in that thong. No wonder the stripper’s wouldn’t leave you alone.”

Jessica blushed as she snuggled up to me in the water. Seeing I was also naked she couldn’t stop laughing. Covering her huge breasts with her hands the other girls laughed at her telling her she was being stupid. CaCee and Ashlee weren’t shy. Making fun of her, Jessica went red but finally let go of her tits to show everyone her delicious nipples. Just like Ashlee’s they were pink and similar in size and shape. CaCee’s nipples were noticeably darker than the sisters. I was in heaven. Drinking hard and having several shots for the next few minutes we were all really buzzed.

The girls were so relaxed and drunk, CaCee and Ashlee were mucking around licking alcohol of each others necks and bodies. Meanwhile Jessica and I sat opposite them, touching and rubbing each other while we watched! Seeing how drunk Jessica got I then asked her, “So why don’t you tell me what happened tonight?” Jessica was silent.

“Um okay, well this guy ...”

“More like this big dick’d stud!” CaCee yelled, making her and Ashlee laugh.

“… well this *guy* was dancing right in front of me on the stage and I kinda grabbed him”

Ashlee said, “It might be easier if you just demonstrated on him Sis.”

With that Jessica closed her hand over my hard on and gave it a couple of gentle tugs. I gasped out loud.

“See, that’s the exact reaction Fireman Dan had when Jessica grabbed him,” CaCee laughed.

“Are you going to tell him what else happened?” Ashlee laughed, “or should I just demonstrate too.”

“Go show him!” CaCee dared her.


Ashlee looked at her sister who drunkenly smiled and nodded to her to go ahead and do it. Ashlee then moved over to grab my cock and yank it a few times making jump. Feeling how excited I already was, Ashlee’s eyes flew open.

“Oh my God Cee, you gotta feel this!”

Without even waiting for Jessica’s comments CaCee moved to also stroke my hard on under the water. While all three girls played with my dick, Jessica grinned proudly as the girls asked her a thousand questions. Jessica then whispered to me, “Can you ever forgive me?”

“Did you have fun tonight?” I asked. “Yes” she smiled.

“Good, because I’m having fun now” I slid my fingers inside her thong and stroked her trimmed pussy.

While Jessica moaned, Ashlee turned to CaCee and the two kissed hard on the lips. As I kissed and fingered Jessica, I could feel another hand join my hand around her pussy and looked over to see it was CaCee. Jessica and CaCee then began to French kiss each other while Ashlee moved behind CaCee and began to play with her tits.

“This is the best birthday party ever,” Ashlee said kissing CaCee’s neck.

CaCee moaned “Oh Jessica you are so lucky. I wish I could suck that magnificent dick”.

Watching them moan and play with each other I nearly blew my load right then and there. Ashlee and CaCee cupped my balls while Jessica pulled me. My other hand found it’s way inside Ashlee’s panties. Unlike her sister her pussy had no hair. Apparently Ashlee believed in being completely shaved clean and spotless. It turned me on even more!

Seeing my reaction the girls laughed and CaCee said. “Who do you think shaved it?!”

We all made out some more and somehow we all climbed out of the pool and went upstairs into the bedroom. With all of us getting completely naked I finally got to see my sister-in-laws cute little beaver. The bald look was enhanced by the fact she was really excited and wet! We took turns lying her on the bed and licked her pussy, fingering her tight little bungholes. It seemed my steel hard shaft always had a pair of lips on them. Since I had been drinking quite a bit I was able to withstand the girls sweet ministrations with out blowing my wad. I maneuvered myself so I was into a 69 position with my wife on top.

Jessica moaned she wanted the others to see just how we liked to fuck! She was sucking my cock like there was no tomorrow and I was pummeling her clit with my tongue. Ashlee moved to play and suck my balls while CaCee licked at Jessica bunghole with her tongue, reaching down to kiss me now and then. Feeling the sisters both lick and suck me at the same time almost made me want to cum! We all moaned loudly as Ashlee and CaCee then swapped positions, and I’m not even sure if Jessica knew her sister was now licking, and pushing two fingers into her pussy trying to make her cum!!

As Jessica screamed out loudly I felt CaCee’s tongue on my ass and that did it for me, and I grunted as I unloaded a huge load right in my wife’s mouth. Jessica was like a woman possessed. She kept sucking me while her own sister, Ashlee finger fucked and licked her dry! Seeing Ashlee make her own sister cum, I was quickly hard again. I pushed Jessica off and pulled CaCee onto my fat cock! She begging me to fuck her like she’d never been fucked before! As Jessica fell to the side trying to calm down, Ashlee pushed her hairless little pussy into my mouth, and started to make out with CaCee!

Bouncing on top of me, I don’t think it was much more than three or four minutes before Ashlee started coming on my face. Fuck I have never seen that much juice come out of a girl before. Jessica’s little potty mouth moaned and yelled for me to fuck CaCee and make Ashlee cum in my mouth! Watching me do this Jessica flicked her love bud and went over the edge. She came so intensely that it turned on the girls and they too came! Seeing CaCee cum so hard Ashlee jumped off my face and told CaCee, “Damn Cee, get off it’s my turn!” and she climbed on me reverse cowgirl style and began to grind my cock.

I spit on my finger and worked it up her tight little browneye while I rose up to meet her downward thrusts on my salami. Ashlee was really tight and couldn’t hold back as I reached around and roughly grabbed her ample tits with my free hands and drove my schlong as deep and hard as I could into her. In seconds it seemed like I had filled her to the top with what felt like the largest cumshot I had ever produced.

I felt so smug. I had arranged this whole little affair to satisfy my own perverse fantasy and I had completely succeeded. That was until as I was drifting off to sleep, Ashlee whispered in my ear, “We know what you were up to”. I sat straight up. Jessica was already asleep. “What the fuck are you talking about Ashlee?”

“You think you’re so smart, suggesting we go to a strip club” CaCee laughed. Jessica and I talked about it and we weren’t sure how far we were going to let it go. I am happy as you have one hell of a cock. I just have one question for you. CaCee turned away from me and proceeded to go to sleep while Ashlee laughed “Just wait till its your birthday Nick!”

End.