Kay had asked, "Do you want to set things up with Danielle or should I?"
I stared at her for a moment, processing how fast she'd already moved-on from me... fucking the shit out of her friend, Katie, and was planning ahead.
I loved that about Kay— always moving forward, progressing in life.
Now that Andrea was out of the equation, Danielle was obviously next up on the fuck-list. I had thought about it for a moment and decided that I quite liked the idea of Kay "setting things up" with Danielle, acting like her pimp in a way.
When I told Kay about how she should pimp-out Dani to me, she gave me her classic wicked smile and started texting furiously. It was the season of giving, so hopefully Dani would be available soon after all family festivities.
In the next days following Christmas, this scene would repeat itself many times over: Kay's phone would buzz, she'd read a message, then look up at me and say something like, "She's asking me what kind of lingerie you like."
Another notable highlight from her phone messages was, "You prefer shaved pussies, yeah?"
All I could do to close my mouth and nod.
It was hard not to be flattered by the interest Danielle was taking in my preferences. Although, truthfully I knew it was more about her than me.
On that note, let's talk about Danielle for a moment.
The truth is you probably know a “Danielle”, if not in-person then definitely on social media. Picture your stereotypical sorority girl/ insta-influencer: a rich girl who is at university whose main objective is to party and get fucked into the next solar system. Her #lifestyle seemed to be centered on getting and keeping people's attention. She absolutely lived for admiration, especially from guys.
Knowing that her bubble butt was her biggest asset, she usually wore booty shorts, leggings, or really, really, short skirts; she would then revel in the attention from every guy (and girl) who stared at her. Pretty sure she dyked-it up a few times throughout those four magical years at college. Became a bit of a "crack addict", if you know what I mean.
Danielle is about 5'5ft, with shoulder length platinum blonde hair. She has Slavic, Eastern-European features; I think her family were originally from Russia or Ukraine. She seemed nice enough, but I had always thought of her as a bit of a bimbo— A Bratislava Bombshell.
As most of what she talked about seemed to be make-up and fitness. She claimed to be a “lifestyle influencer”, but her Facebook (remember this was a decade ago) had over 10k followers/friends and was mostly filled with photos of her showing off her ass. She was ahead of her time, for sure.
Not that I was complaining, especially since I had finally got a FB account during that time. I had definitely been missing out prior to those years.
Aside from all this, something else had occurred to me. When I thought about it, I realized that Kay, Katie and Andrea had created their strange rule with the intention of protecting and preserving their intense childhood friendships.
On the other hand, Danielle (the original outsider) seemed to be participating mostly just out of sluttiness.. now if that isn't enough to make a guy sit up and pay attention I don’t know what is!
One of the things Danielle and Kay had discussed was whether I'd be using a condom. None of us particularly wanted that and since Danielle was on birth- control (as I believed all the girls were), the consensus was that Danielle and I would both forgo the prophylactics and I’d straight-up inseminate her, naturally. At the end of the day, it is what both parties want. Women want to feel you spray your hot load against their cervix, nice and deep. It’s like crack to them.
Planning my hook-up with another girl in such detail with my actual girlfriend was a surreal experience to say the least. It turned us both on like crazy and Danielle's texts would often lay unanswered, as I fucked Kay silly.
Our kink play had also been getting more intense, with Kay wanting me to be more into verbally degrading to her. She wanted me to describe in detail what I'd like to do to other girls while fucking her.
We almost always watched porn while fucking, and she would prompt me with questions like:
"Wouldn't you rather be fucking her?"
"Tell me why she's hotter than me."
"My pussy isn't enough for you, is it?"
I was initially reluctant to say such things to my wonderful girlfriend, but she seemed to really want it and in the end I was happy to oblige. For selfish reasons, I was also probing her attraction to the women on screen.
I would tell her how she would have to lick my cum off their tits, or prepare/summon another girl's pussy for me to fuck.
When I said things like that she would moan like a wild animal. It was enough to make me hopeful that post-Danielle, I wouldn't have to return to monogamy.
Although we never openly discussed it, I was becoming increasingly hopeful that Kay would someday be up for a threesome.
With these happy thoughts to keep me occupied, the rest of the week passed by quickly. Soon it was time for my fuck-date with Danielle. The plan was to meet at a local bar and then head back to her place. Considering that I'd never had a conversation with Danielle that lasted more than 2 minutes, I was eager to skip the bar and get to the all important, fuck-festivities. However, Danielle had insisted on meeting there. Well, some liquid courage never hurt, I'd thought.
It was a mild night; the moon was as full as my balls. I kissed Kay goodbye first on her upper and then lower lips. I told her I'd see her soon and the look she gave me told me she'd have her fingers in her pussy the moment I shut the door behind me.
At the bar I got a beer and waited for Danielle. Of course she was late. She was probably masturbating before our meet-up. The bar she'd picked was pretty fancy; it seemed to me like she was really playing up the whole spoiled immigrant, rich brat angle.
I was halfway through my amber ale when someone put their hands over my eyes and said, "Guess who!"
I rolled my eyes and sighed but played along, " My nine O'clock?"
She giggled and took her hands away.
I leaned back to check her out. Wow.
Danielle had certainly dressed to impress. After hanging up her jacket she revealed what she was wearing: A tight black dress with holes cut-out on the sides to create her signature look of having her ass half-exposed. Her insane cleavage was peeping out the top of her dress, making her breasts look much bigger than they were.
I looked her up and down appreciatively, and noticed the eyes of many guys she'd passed on the way to our table were still following her. I could only imagine the view from the back. Danielle seemed like she'd walked out of the front cover of Vogue magazine, airbrushed and everything. Her hair, nails, make-up, every inch of her looked professionally done. The truth was that she did look hot, but more like a doll than a real woman.
As she took her seat opposite me and leaned toward me, I realized she was waiting for a compliment.
"Wow Dani, you look perfect," I told her honestly. "Just like a doll." I added.
She pouted her bright pink lips, blew a kiss at me and said, "Like a fuck-doll, I hope."
Holy shit, I remember spitting some of my drink out. I felt my dick starting to twitch in anticipation.
Dani was soon drinking a fancy cocktail—a cosmopolitan or some Sex & the City type of shit— and talking about something or the other. My eyes had wandered back down to her pushed-up tits. She laughed, snapping me out of my thoughts "Hey, are you even listening?"
"Don't bother," she giggled. "I know where your mind is. You want to see them?"
"Hell yeah. Let's get the bill."
"No," she smiled at me. "I mean right now".
I was about to ask her what she meant, but my question was soon answered.
Right then and there she began to roll down the top of her dress. We were right in the middle of a crowded bar, but Danielle didn't seem to care. She was looking right at me as she rolled her tight dress down from the shoulders until her boobs were completely out in the open. All around us people were talking and drinking,
Danielle had just taken her breasts out for me to admire.
Unbelievable, that was my life at that moment.
My dick grew harder as I stared at her small perky tits. Due to how slutty she dressed all the time, I felt like I'd seen her topless already, but what I didn't know before was that pierced through each of her pale pink nipples was a silver metal rod. Fuck, I was developing a serious thing for girls with piercings.
I looked around to see that a few other people had noticed Dani's little show-and-tell; they were nudging each other and one guy seemed to have taken the liberty to film some of it on his phone. Dani followed my gaze and saw that she had an audience. She smiled widely and turned back to me. Very deliberately she brought her hands up and pinched her nipples with her fingers, while squeezing her tits together with her shoulders. It was loud in the bar but I could have sworn I heard someone gasp. It was either Dani’s voluptuous display of womanhood or the pickled eggs really good there.
A second later she had her top back on. I was still speechless.
This girl was such an attention-whore, she had my dick rock hard.
"Let's go," I said.
"Noooo let's stay a little longer."
"I'm not asking," I told her. "That is unless you plan to get completely naked here."
Jesus, I shouldn't have given her the option.
When we got to her apartment it was everything I had expected from a spoiled tart like Dani; the place looked like it was sponsored by Gucci and Prada.
"Wait here," she told me. However, I ignored her, and pressed her against the wall. "Just give me a second."
"Why?" I groaned.
"It'll be worth it, I promise". I sighed and let her go.
While she skipped off toward her bedroom, I looked around her apartment.
Her parents were definitely filthy rich; the apartment was in an expensive part of town and looked professionally decorated. I knew for a fact that Dani hadn’t worked a single day in her life, or had any sort of part-time job to pay for her tuition, rent and other expenses. The best part of her place that daddy paid for was the large balcony that overlooked the city.
I was starting to feel like a bit of an idiot standing alone in this apartment, so I went onto the balcony.
Danielle found me there a few minutes later.
"Enjoying the view?"
I turned around and forgot all about the city behind me.
My dick stood at attention the instant I saw her.
The dress was gone: Danielle was wearing absolutely nothing but a tiny thong.
I groaned and kissed her, my hands going straight to her pierced tits. I pulled experimentally on the tiny metal rods and she gasped. My hands went to my pants and she expertly helped me out of my clothes.
No sooner was my dick out; Dani was on her knees in front of me. I moved her so I was looking out at the city scape as she took my dick in her mouth. The anticipation had been killing me, I groaned as she finally began sucking on my dick.
Her pale blonde hair was glinting in the dim light as she moved up and down. She was giving me an absolute porn star-esq, blowjob. She was doing these ridiculous over-the-top moans even though I wasn't touching any part of her but her head and her spit was bubbling up and leaking all over her face as she shoved my cock in and out of her mouth.
I grabbed her head and pushed my cock into her throat. For a second I heard a real gasp and then she went back to her porn star moans. Much as I was enjoying the blowjob, she was really starting to piss me off.
"Get up." I told her.
When she stood up, I spun her around and bent her over the terrace railing. It was at rib height so her torso and tits were hanging over the railing. We were definitely putting on a show for any of her neighbors who happened to be watching. I was sure that’s what she would’ve wanted, regardless. I shifted focus.
For the first time I was looking at her nearly naked ass up close. Now I've said before that I wasn't an ass-man, but Danielle's ass was a work of art. She'd clearly taken a naturally curvy ass with potential and sculpted it into a goddamn masterpiece.
Her ass cheeks were two bountiful, perfect circles and I swear she'd put on some kind of lotion, coconut oil, or something that was making her ass faintly shine and glisten in the dim light. I put my hands on it and marveled at how soft yet firm it was. I massaged her ass for a few seconds and then pushed her thong down so it was a thin band around her knees. I spread her ass cheeks, bending her over slightly more so she was presenting me with her glistening pussy.
I was done waiting. I took my cock in my hand and positioned it. Her wet pussy accepted the whole thing eagerly as I slid into her. I began fucking her hard, pushing her against the railing. Dani immediately began screaming and moaning, leaning over so her tits moved freely in the air.
I looked out at the city lights and then down at the beautiful girl I was fucking from behind. I grabbed her ass again and spread it so I had better access. I was staring right at her cute pink asshole when she suddenly said in this soft high pitched voice, "Yeah daddy, fuck me".
Pause. Hold up.
I'd never been into the whole daddy thing before, but for some reason in that moment it sent an electric volt through my body. It felt like my dick grew a couple inches in that instant. I looked down at Danielle and thought about how this was some rich guy's spoiled brat that I had bent over before me. This guy was probably a multi-millionaire, oil tycoon and I was drilling deep into his daughter's pussy, using her like a fuck-doll.
I put one hand on Danielle's waist, grabbed her by the tits and pulled her up towards me so her back was pressed against my chest. I turned her face towards mine and began slamming into her. "What did you call me?" I growled at her.
In the same baby voice she moaned, "Oh fuck, daddy...I need your cock, daddy."
I shoved my fingers into her filthy, fucking, mouth. She immediately began sucking on them while staring into my eyes. When she had gotten each of them really wet and sloppy, I pushed her away from me, bending her over again.
She kept moaning, "Oh, daddy. Oh yes... daddy," as I spread her ass cheeks.
I pulled my cock out so only the tip was still inside her and I positioned my thumb over her balloon knot of an asshole. Just as she turned her head to look back at me, I rammed my cock back in at the same time as I pressed my thumb into her asshole. She screamed. For the first time that night, it was a 100% genuine scream of pleasure and shock, no acting involved.
I knew what I had to do.
At first I continued fucking her like that with my thumb moving slowly in and out of her tight asshole. She was moaning in a deeper pitch and grinding her ass against my thumb.
"You like that huh? You like my thumb in your ass?"
"Oh God yeah.."
"Who are you talking to?"
"You, daddy. I love your thumb in my ass, daddy..."
Dani clearly had some deep, dark issues that I needed to work out for her.
I pulled my thumb out and spat on my fingers. I rubbed my saliva onto her asshole slowly, pressing on it. Dani was gasping and making sounds that were totally different now.
"Tell me what you want, baby." I said. I had no idea where this was coming from but I had fully embraced my new role.
Dani groaned. She arched her back and pushed her ass up against my thumb.
In her soft high-pitched voice she moaned, "Daddy's little slut needs a cock in her ass."
Fuck. I thought I'd been ready to hear that. I pulled my cock out of her and yanked her up. "Lube?" I asked her.
"In the bedroom".
Danielle ran to her bedroom and I followed her.
"Get on all fours." I said and she promptly obeyed.
Why are the hot ones always this fucked in the head, I thought.
Dani scrambled onto the bed, spread her legs and arched her back presenting both her holes to me. She was moving her ass slightly up and down, like she was twerking. Such a good slut.
My dick had been hard for so long now that it was aching, I shoved it into her pussy and sighed in relief. I fucked her slowly and asked her where the lube was. In the bedside table, bottom drawer Danielle told me in between moans.
I leaned down and got the drawer open. Before me was not only a variety of flavored lubes, but a bunch of sex toys including a vibrator and handcuffs. I grabbed the lube and the vibrator. If Dani noticed she didn't say anything. I poured a generous quantity of lube on my fingers
I pushed into Dani's asshole with my lubed up fingers and she immediately collapsed face first into her pillow.
She reached behind with both hands and held her pussy wide open for me. I took my fingers out and positioned my dick at her. Slowly, I began to push in. As my dick pressed into her, I held her hips and pulled them toward me. Her pussy was so much tighter than Kay's, it felt like it was actively pushing me out. Maybe it was because Dani gets fucked in her ass by most guys, and herself late at night?
I waited till I was balls deep in her bubble butt to finally begin fucking her.
Her ass was the nicest I'd ever felt against me. Every time I slid my dick out of her pussy, it felt like I wouldn't get back inside. Her bountiful ass was jiggling with every thrust. I wanted to grab her bumpers and shake them, but Dani had a tight grip on them. She was spreading her cheeks wide open as she gasped and moaned like no sounds I'd ever heard from her before.
All her performances seemed to have disappeared as she had pulled her cheeks apart for me. Now she was twerking her ass and whimpering "Daddy, daddy" in a soft moan each time my balls slapped against her.
I reached down and pulled gently on one of her nipple piercing. She moaned louder, "Oh God yes, give it to me, daddy".
I felt myself getting close to cumming. I grabbed the vibrator and positioned it under her clit. I pulled my dick almost all the way out and I turned the vibrator on just as I slammed my dick back into her pussy. Dani shrieked and began shaking violently. Her cunt’s death grip on me seemed to tighten even more and I began to cum. I continued fucking her as I shot my white hot load deep into her and held the vibrator at her clit until Dani's screams had stopped.
I filled that thing up like as I was at an ExxonMobil station.
Finally I pulled out and surveyed the scene before me. Dani had collapsed face down into the pillows, her ass was still in the air and had my cum leaking out of her pussy.
I massaged her ass cheeks gently and rubbed her back before getting into bed next to her. Dani's face looked absolutely ruined, just like her childhood; her make-up was all over the pillows and her mascara had smeared all around her eyes. I kissed her gently and asked if she was okay.
She looked at me through watering eyes and said, "Thank you for fucking me from behind, daddy".
I wanted to give the girl a damn medal.
In the cab home I felt simultaneously on-top-of-the-world and strangely melancholic. I had now fucked two of my girlfriend's best friends— absolutely incredible on both.
Although it had been amazing, it was now over, and I hadn't scored the trifecta. Impulsively, I took my phone out and pulled up Andrea's Facebook. I had been scrolling through her photos absentmindedly for a few minutes when I realized that I had accidentally liked one of her older pictures at some point.
I immediately removed my 'like' but a second later I got a notification from Andrea. She had followed me. Shit, she knew I was stalking her in the middle of the night. Fuck, me I thought.
To my surprise, she immediately followed up with a message: "You're up late ;) how's it going?"
Andrea had never texted me before. The embarrassment was making me feel hot under my collar. While I was thinking of what to do, the cab stopped and I realized I was back home. I left her on 'read' and went upstairs.
There I found Kay awake and waiting for me. I'd barely gotten out a, "Hey" before she was down on her knees, fumbling with my jeans, trying to get my dick out. I stopped her and tried to pull her up but she was in wild animal mode.
She looked confused for a moment and then her face cleared, she immediately began rambling "Please sire, let me suck your dick. I want to taste Dani's pussy my King."
I laughed and helped her stand up. I kissed her and said, "You probably don't want to taste my fingers though, they were in her spoiled asshole for a brief time".
Kay's face was a mask of shock. "You..finger-fucked her ass?"
"Fuck yeah I did! Oh and by the way, your friend has some serious daddy issues. I am no psychiatrist, but I think he never paid attention to her. Too busy paying for that fucking apartment I bet."
Kay's mouth snapped shut. “Did you though, fuck her in the ass with your cock?” She suddenly seemed absolutely furious. She wrenched free of my grasp and ran to the bedroom, slamming the door shut behind her.
I was at a loss. I had had no idea that anal had been off-limits even though I didn’t fuck her friend in her asshole. Man, women are so touchy with their friendships.
Come to think of it we'd never discussed any rules or boundaries, which is why I had assumed there weren't any. Now I'd upset the world's greatest girlfriend, I felt horrible.
I took a shower and spent the rest of the night on the couch watching old re-runs of Baywatch.
When I woke up the next day, Kay was tucked under my arm sleeping next to me on the couch. When I stirred she woke up and kissed me deeply. I had a feeling I wasn't in trouble anymore.
"I'm sorry, I just got..I guess, jealous.." I hugged her and told her it was completely understandable and I hadn't meant to upset her, that I didn’t actually fuck her friend in her asshole.
"It's just that..you never seemed interested in my ass." Kay added.
"Are you kidding?" I reached behind her to squeeze the ass in question.
Kay was burrowing into my arms, hiding her face now. "No, you wouldn't. Dani's ass is so much better. You wouldn't want mine. "
"No, stop that. Of course I-"
Kay wouldn't even let me get the whole thing out. She interrupted, "I bet the only way you could fuck my ass is if you were looking at hers."
I paused and reassessed the mood she was apparently in. I tentatively reached into her panties and when my fingers touched her pussy, they were soaked. Wow.
I gently rubbed her clit and waited for her to say something else.
After a few long moments of silence I took the leap, "I think you're right." I told her slowly, "So, why don't we invite her to join us?"
Kay moaned and raised her face to kiss me.
To Be continued...