A Week with the Randalls Pt. 04

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Lilly shares a night with Brittany and Brad.
3.9k words
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Part 4 of the 4 part series

Updated 06/08/2023
Created 01/11/2017
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TUESDAY

Brittany and I had the house all to ourselves, with Mr. Randall in his office and Amber, realizing that she'll have to bump into Britt if she stays home, decided to spend the day shopping. Even though both of them promised Mr. Randall that they will give their best to get to know each other, Britt made clear she had no intentions of getting closer to Amber, and Amber avoided any kind of confrontation that could cost her her marriage to Mr. Randall. She obviously hit the jackpot and was aware of it, and she was sly enough to know her way around the problems that might come her way.

We decided to sunbathe and relax today. We didn't talk about our plans for that night, but it had to come up at one point since it was on my mind throughout the day, and surely it was the same with Britt. As we laid each on our own lounge chair I sneaked a peek at her every now and then, thinking about what tonight would be like. She was slimmer than me but still toned, with long legs and a nice, full ass. Her bikini top was untied and scrunched on her boobs, just so to cover her nipples, so to avoid tan lines. She laid her forearm over her eyes, covering them from the sun. I wondered what it would be like, having sex with my best friend.

Almost as if she knew what I was thinking, she peered with one eye over to me. "Hey," she said. "What are you thinking about?"

I took a moment and said, "Well, you know..."

She laughed, "Don't worry about tonight. It's gonna be fun. I mean you had threesomes before, right?"

Fuck. No, I hadn't. Britt realized that from the lack of an answer. "What? Lilly, really?" she pressed her bikini top against her breasts, so it wouldn't fall down as she sat up. "I had no idea! You are always so open towards everything, so I just thought..."

"Yeah, well you know, it just never came up."

She looked at me with a concerned expression. "But you know you don't have to, you know?"

I started laughing, "Of course I know, Britt. It's not like you pressured me. I think it's gonna be really fun. Besides, you get to pop my threesome cherry," I winked at her.

"Well it will be my pleasure!" She was upbeat immediately and laid back on the lounge chair. "Brad and I did it so many times, I'm not even sure with how many people. Girls mostly, since Brad would get kind of awkward when there's another guy. To be completely honest," she giggled, "Brad isn't the sharpest. He loves when there are two girls, then he feels special. When there's another guy, he gets competitive and pouty."

"And with girls?"

"Then he's great. He likes attention, but he also likes pleasuring. One time there was this really shy girl with us, I don't even know how that came to be, but we realized we'd have to be more attentive, so it was all around her that evening. He didn't mind at all, we ate her out, kissed her all over, and after a few times, Lilly, she turned out to be such a little slut in bed! Or anywhere else where it would go down."

I laughed. I had no idea Britt had such a big sexual past.

"But one other time," she continued, "there was this guy with us, and he was very attractive and very confident. He was so assertive, and he started fucking me from behind while I sucked Brad's cock. But this guy was so good that I couldn't even suck Brad, I came twice almost immediately and I guess Brad felt left aside, he didn't even try to get in the mix."

Britt was talking so nonchalantly, and I felt my blood rushing through my body and my pussy swelling, imagining her all tired from some guy slamming it to her hard from behind, not stopping until she couldn't take anymore.

"So this guy leaves after sex, and Brad is next to me, pouting and not wanting to look at me. So I had to be like, baby, I came so hard thinking about you watching me getting fucked from behind... It took a little convincing, but he bought it, 'cause his dick sprung up immediately," she laughed.

"But the most stupid thing we did..." she shook her head with disbelief, "was having sex with a professor."

"What?! You never told me that!"

"Yeah. We were almost done with high school 18 and crazy with hormones, and she was our science professor. She was so sexy, a real milf type, in her forties. She had long brown hair and big boobs and was quite strict. Brad once told me that out of all of the girls in school, he'd love to fuck her the most, and we started talking about it more and more. We saw it as kind of a way to say goodbye to high school."

"Going out with a bang?" I couldn't help but ask. Britt laughed.

"Exactly. So the opportunity finally came at the office party at my dad's firm - they just closed a huge account and Brad went as my date. And we couldn't believe our eyes when we saw Mrs. Simmons there! It turned out her husband works there. She was in a tight dress and Brad and I knew we had to do it that night. So we came up with a plan. We went up to her to say hi, and I pretended to accidentally spill my soda on her dress, so I could ask my dad to go to his private bathroom to clean it up."

Brittany was laughing and giggling through the story. "Brad and I escorted her there and as I was cleaning it up, I grazed over her breast a few times, just to see how far I could take it. Well very far, it turned out, as she wasn't stopping me. She locked eyes with me as I didn't even think at that point, I dropped the paper and grabbed her breast, massaging it. Without saying a thing, she put her hands on my shoulders and pushed me down to kneel in front of her. She then pulled her dress up and raised her knee on the sink that we were standing next to.

"She had this skimpy thong on and pulled it aside with her fingers while gently pulling my head closer with her other hand. I went at it like crazy and she moaned a little, before looking at Brad. He was standing by the door, and couldn't believe his eyes. "What are you looking at, Wilkins?" she said. "You always had a big mouth, come here and help Miss Randall." Brad walked over next to me, and she said, "No no, Miss Randall is doing very well in the front, I want you kneeling behind me."

"And the funny thing is, Brad always wanted to do that to me, but I never let him - so to have Mrs. Simmons order it to him, well he might have just as well died and gone to heaven. When he got his tongue in her ass, that's when she really started moaning and grinding against our faces, and as she got hotter, she ordered Brad to fuck her. He jumped to his feet and pulled his pants down with his underwear and after a few slow pushes into her, he went at it fast and hard.

"He grabbed her dress and pulled it up to take it off, since her boobs were what we usually fantasized about, and she had no complaints. I lapped my tongue fast against her clit, sucking it from time to time, and with heavy moaning, she came hard, but Brad wasn't nearly done, so he just continued thrusting and I got up and pretty much ravaged her tits, sucking and biting. They were just so big and... mmmm... I can't even describe them."

A flashback of me sucking Amber's boobs went through my mind.

"Brad then came in her butt and I think that was the best fuck of his life. She then told us that she hopes that it was everything we've hoped for," Britt laughed. "She just couldn't be fazed. We then left her to refresh herself, and after that, she just returned to the party as if nothing ever happened."

Both of us got lost in our thoughts. I was curious how tonight is going to go, but neither of us spoke any more of it and we spent the rest of the afternoon swimming and sunbathing.

The sun started going down, so we went to our rooms to shower and get ready. I picked the nicest lingerie I had, even though I knew I wouldn't be in it for a long time, but it was a nice way to boost my confidence. At 8 PM I went down to the foyer, where Britt was already waiting. We got in the car and the chauffeur drove us to a part of town full of modern skyscrapers and dropped us in front of one of them.

"I'll call when we need to be picked up!" Britt said to the chauffeur on her way out.

She took my hand and we went into the building, where Britt got warmly greeted by the doorman and we got into the elevator. Britt pressed the button that took us to the penthouse.

"What does Brad do?" I asked.

Britt started laughing. "Brad? Absolutely nothing. But his dad is a huge CEO and his mother is a designer, and he is the only son. So he is covered."

The ride was long, and when the elevator doors opened, there was the most unbelievable apartment in front of me. Everything was sleek and modern, and through the huge glass door that led to the balcony, I could see the whole city. Brittany and I entered and I looked around in awe.

"You're here!" Brad greeted us. He went to Brittany and gave her a deep kiss while pressing her to him. He then turned to me.

"Hi, Lilly," he said and approached me. He took my head gently with his hands and kissed me, almost coyly at first, but as I pressed my body against him, the kiss deepened and his hands were low on my back. I almost giggled, thinking how I was scared how we were going to hit it off. We obviously won't be having any problems.

He took my hand and then Brittany's and led us into the bedroom. In the middle of it was a huge bed, by which were three buckets filled with ice and in each one a bottle of champagne. The best one possible, I presumed. Two outer walls were glass, top to bottom. I never had sex while overlooking a few million people, I thought.

With more gentle kissing, we all started undressing each other. Britt and I kissed briefly through the undressing, which seemed surprisingly natural. We smiled at each other as we got on the bed in our underwear. She pulled my bra straps down and kissed my shoulders while cupping my breasts and pulling them out of the bra. I felt Brad behind me, unclasping my bra and kissing my back. I was dizzy with arousal, and when Britt's soft lips wrapped around my nipple, I had to lay down.

Brad then started kissing my stomach and tucked his fingers around my panties and pulled them down my thighs. My pussy was so swollen and wet that I shuddered when the air lingered over my slit. Brad kissed his way down and with his tongue, he gently spread my labia. His tongue swirled around as I pushed against him, I wanted him to enter me so bad, but he was determined to tease me more.

Britt kissed my neck and licked my earlobes, and her hand caressed me, all the way down to my pussy. She started massaging my clit, and Brad pushed his tongue inside of me and started massaging my velvety walls from in circular motions. They were so well played, I could see that they knew exactly what the other one was doing and what that was doing to me. I didn't care how many girls they did this to, at this moment I felt like the only girl in the world.

As my moans got deeper and breathing faster, Britt's hand went faster and Brad somehow managed to get even deeper inside of me. The orgasm started overcoming me.

"Aaaahhh... Aaaahhhh... Ohhh yeaaah..."

My body was convulsing as a held Brittany's hand firmly with one hand and clenched Brad's hair with other. I started screaming as the orgasm shook through me and when I thought I couldn't even take anymore, Britt and Brad kept on going, prolonging this sweet agony that they inflicted on me. Finally, with one long scream, my back arched and pelvis got lifted off the bed and just fell back down. I was catching my breath and trying to make the ceiling stop spinning and Brad brought himself up.

He and Brittany kissed over my chest and smiled at me. They caressed me, helping me to relax after this shock of energy. I was exhausted but the adrenalin pumped through my veins. I wanted to fuck them both just as good as they did me, so I started kissing them. Britt was kind of pushing Brad aside, I could see that watching me cumming made her hot, she wasn't gentle anymore as she was grabbing my ass and biting my lip.

I pushed her on her back and straddled her, pinning her arms over her head. Her gaze was lustful and her mouth agape, waiting for my tongue. I kissed her deeply, rubbing my wet pussy against her stomach. I kissed my way down her body, getting to her nipples and pulling on them with my lips, rolling them with my tongue and grazing my teeth gently over her tits. Her hips were bucking and her hands were in my hair. I went further down and her breath became shorter.

I looked at Brad, fearing that maybe he would feel left out, but he had his eyes pinned on me, his thick cock rock hard in his hand. He obviously didn't seem to mind not getting any attention, and honestly, even if he did, even if there was an earthquake starting at that very moment, I was still going to eat Britt's pussy out until she couldn't take it anymore.

I went at her pussy ravishingly, almost savagely, and Britt let out a small scream immediately. My tongue went straight into her soft hole, I was kissing and sucking on her lips passionately as she bucked and wanted to get me deeper in. I grabbed her hips to fuck her harder with my tongue.

"Oooohhh Lilly... Fuck me... Aaahhhh... Lilly... AAAHHHH!!" She was screaming and moaning.

I guess the sight was too much for Brad to stand because he got behind me and immediately pushed his dick into my pussy. As he started pounding me just like he did Britt in the woods and the realization made me moan, which send shivers through Britt's pussy.

She started cumming, pressing my head deeper between her hips with her hand.

"AAAAHHHHH!! YESSS!! AAAHHHHH!!" Her juices were dripping down my chin, and when she came completely I slowed down my tongue and gave her pussy a few tender kisses.

I got on top of her and straddled her with my legs wide spread and my ass in the air so Brad could keep on giving it to me from the behind, while I brought my chest down to Brittany's so I could kiss her as she was coming down from her orgasm. She was kissing me back gently and my tits were grinding against her's rhythmically with Brad's thrusting.

Brad caressed my butt cheek and then gave it a slap, which made me let out a little scream of excitement. It kind of woke me up from my dream like state of kissing Britt.

"Seems to me you have some energy that needs to be let out." His dick fell out of my pussy as I turned to him completely. "So I am going to make sure that after I'm done with you, you can't go around slapping girls' butts," I said playfully and pushed him on his back.

His dick was nice and thick, but it wasn't especially long, so I had no problem getting it all the way into my mouth and giving it a long, hard suck all the way to the tip. Brad let out a deep, long breath. I took it all in and repeated that a few times and then started sucking faster. I could feel that he rock hard from watching me and Britt and then fucking me, so I let him out of my mouth so he wouldn't cum yet, and paid some attention to his balls. I took them in my mouth one by one.

Britt finally managed to catch her breath, so she got next to us and started sucking Brad's dick while I massaged his balls with my tongue. As she held it in his hand, I started circling my tongue just around his tip. He obviously liked that as his cock twitched. Brad was moaning and watching me and Britt sucking his dick and kissing while interlocking our tongues around the tip of his cock.

"What do you think, Britt? Has he earned to cum?"

"Hmmm, I think he has. I mean, only if he promises that he will get hard again fast so he fuck us again later?" Britt said, pretending to be concerned.

Brad was laughing, "Oh baby, the way you two eat each other's pussies... I will be ready to fuck you senseless in five minutes after I cum!"

"Well that sounds good, I think you've earned for me to make you cum," I said with a smile and took his dick all in once again and started sucking hard. Almost immediately, Brad was cumming and I kept on sucking, stopping just to let Britt take him in her mouth. He was moaning, trying to say something but the grunts made it unrecognizable.

"You two... Almost made my heart stop..." He was breathless, lying on his back, his eyes shut.

"Well I had to return the favor," I said with a smile.

Britt gave me a short kiss on the lips. "Can we manage on our own until Brad catches his breath?" she asked.

I pulled myself closer to her. I sat between her legs, locking my legs around her. We kissed gently, embracing each other and caressing. I couldn't believe that I was so relaxed in bed with my best friend. Our pussies were against each other and we were grinding our wet labia slowly while kissing. Britt threw her head back while I sucked on her rosy nipples.

We cuddled like that for a while, and our grinding became harder, lust overcoming us once again. I bit down on her shoulder and loved the feeling of her wetness against mine. Her clitoris became enlarged and it rubbed against mine, which made me buck my hips harder towards her, and she did the same. I was feeling that I was soon ready to come, it felt unbelievably good, feeling her smooth pussy spread open, wet against mine while our tongues massaged each other. Britt was squeezing my breast with her hand, bucking against me. We embraced each other, trying to find a balance while at the same time pressing and grinding our pussies, our clits stroking each other, we started cumming while moaning in each other mouths. We came with small cries of enjoyment and let our heads fall on each other's shoulders. I could feel her heartbeat on my chest.

Our show got Brad's dick hard again, and Britt got on top of him. His dick slipped right in and she started riding him. I laid next to him and made out with him, he was a great kisser. Between kisses we watched Britt on top of him, her tits bouncing up and down. Her skin was glowy from the sweat which gave Brad an idea.

"Lilly, get one of those bottles by the bed," he said. I grabbed one of them, but couldn't see glasses anywhere, so I thought we'd drink straight from the bottle. But when I gave it to Brad, I realized he had a different idea. He shook the bottle so the champagne bubbled up inside and turned it towards Britt and took the cork out fast, so the champagne blasted Brittany's tits!

We started laughing with surprise and the cold liquid made Britt's nipples stand hard and rigid. I took that opportunity enthusiastically to suck them and licked all of her wet breasts.

Then I got an idea of my own, and rubbed my finger against Britt's wet slit, covering it with her juices and without her expecting, I slid my finger into her butt. She laughed even harder, obviously enjoying my slick finger massaging her hole. Penetration of both her pussy and butt made her start cumming, and she closed her eyes and grabbed her wet tits, massaging them. She was moaning harder and harder, bouncing on Brad's cock more vigorously. She leaned towards Brad, opening her fleshy round butt even more to my finger.

"Aaaahhhhh!!" She came with a deep moan.

"Don't stop! Oh! Keep on fucking me!" Brad grunted as the convulsion of her Britt's pussy made him erupt.

They both came and Britt let herself fall on Brad's chest.

I laid next to them. As I let myself relax, I felt tiredness washing over me for the first time tonight.

We took some time to cool down, only laughing from time to time, commenting how wonderful tonight was. Britt and I then decided that it's time to take off before we fall asleep. Brad suggested that we stay over, but Britt and I were looking forward to sleeping in our own beds, so we got dressed and called the car to pick us up.

We waited in front of Brad's building, night air felt refreshing on our skin. We were quiet as we went into the car, and didn't even talk to the chauffeur since the barrier was up between us and the front seat.

We leaned against each other and I felt myself dozing off when I felt Britt's breath on my face and her hand soft on my thigh.

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