Note this story contains anal sex. If that's not your thing, look away. Otherwise enjoy.
This little piece of filth is a work of fiction. You must be 18 or over to read this story, which is provided for entertainment purposes only. Any resemblance between the characters to real people of the same name is a coincidence.
Deep Inside Pippa
Yeah, so I’m a good-looking guy and I always get attention at the gym or the beach. Even my friend Audrey says I could have any woman I want. But she knows I’m a pervert. She knows my biggest turn-on is to use my good looks to take advantage of young cuties and ply them with alcohol so I can get inside their hot little butts.
When I first saw Pippa I knew I had to have her. Young-looking and soooo cute, and the sweetest little ass. Man, I just had to get inside that. And I wasn’t afraid to use Audrey to get what I wanted.
I was at a bar on the beach with a couple of buddies. Audrey came in with this blonde cutie in a white dress and they sat on a sofa in the corner. A little later Audrey went to the bar and I called her over.
“Hey babe, how you going?”
“Oh, hi Rick!”
She hugged me and held on a little too long, so I risked a quick feel of her ass. Nice.
“Who’s the pretty girl?”
“That’s Pippa. Would you like to meet her?”
“Sure.”
Despite the lame-ass Limey-sounding name, I was surprised when Pippa came over and she spoke and I realized she wasn’t English. Unlike that Kate Middleton's sister Pippa. Remember the one who upstaged a royal wedding with her bum? What a legend.
Anyways, it wasn’t long before Audrey fucked off to speak to some other friends and as she walked away she leaned towards my ear and whispered, “she’s a dirty little girl”. Fuckin’ A in every sense. Pippa sat beside me at the bar and I bought her a glass of white wine. Hell, I even had one myself, which is pretty fuckin’ gay, but you know, needs must.
She had to show ID, so she was at least eighteen, which was another green light. I saw her attention occasionally wander to my eyes and toned arms. Everything looked good and I bought her another drink.
Then it was time to make a move.
“So, Pippa, I guess you’ve just started college. What’s your subject?”
“I’m an English lit major. You know, Shakespeare and all that.”
“Oh, impressive. That’s what I did too.”
“Wow! Really?”
“Yeah, though I don’t use it much these days, I’m more into business. I’m forming a tech start-up with some buddies. A payment gateway. Kinda like PayPal, but better.”
“Wow. Now that’s impressive.”
No. What was impressive was that my story was complete bullshit and she’d fallen for it. I’d inherited a pile of money from good old gramps, dropped out of an engineering degree after a year, bought a nice apartment here at the beach and was basically living the good life.
It was time to move in for the killer punch.
“Shakespeare, eh? So, Pippa, what would you say about the relationship between gender and power in Antony and Cleopatra?”
I tell ya, even I’m impressed with the shit that comes out of my mouth sometimes.
“Um, I have to say I haven’t studied that yet.” She looked at me all glassy-eyed and touched my arm. “Brains and beauty.” Then she blushed.
I stroked her cheek. “You flatter me, Pippa. Hey, my apartment is just over there.” I indicated its direction with my head. “How’s about we go and have a more private drink. Just the two of us. You like whisky and coke?”
“Sure.”
She leaned forward and kissed me. Kid you not, she made the first move. I took her hand and led her out of the bar. I gave Audrey a sly thumbs-up on the way. Audrey winked back. She knew, and I knew, that Pippa’s ass was mine.
********************
We stood in the kitchen and I handed Pippa the glass.
“Thanks.”
“No problem. Cheers.”
“Cheers.” She took a sip and moved towards the sliding door that led to the balcony. “You have a really nice place here.”
“Yeah, I like it.”
She went outside and leaned against the rail. From behind it looked like she wasn’t a natural blonde, but I like that bleach look with the dark roots. It’s kinda slutty. In addition to the white summer dress, she wore Roman sandal shoes with leather straps, like in Gladiator, but with a small heel. So fuckin’ hot. I moved in behind her and felt her sweet ass cheeks against my groin and I got hard. I leaned forward to smell her beautiful long hair.
“God you’re so sexy.”
“So are you. Mmmm. You’re getting excited.”
“How could I not? That ass.” I took her hand. “Come back inside.”
I took the drink from her hand and placed it with mine on the kitchen benchtop. We kissed.
“Here.” I turned her around so her back was to me. She gripped the counter top. I lifted the hair from the back of her head and pushed it over a shoulder and kissed and bit her neck.
She wriggled. “Oooh, you’re making me shiver.”
I untied the thin string that held up the top of her dress and it fell away to free her small titties. I reached under to cup them. The nipples hardened. Wonderful. There was a small crucifix in between.
“You a good Catholic girl, Pippa?”
“Yes.”
I reached forward and down, past her flat tummy and in to the front of her panties. Down to the slit.
“Oh, good girl, nice and smooth.”
I reached under, through the soft skin folds of the slit, searched for the little cleft. Her hand gripped mine.
“No. I-“
“Holy fuck. Are you a virgin?”
“No.” She took my finger and moved it back around and rubbed it between her ass cheeks. Then she looked into my eyes. She couldn’t say what she wanted. She was too embarrassed. That look was the sexiest fucking thing I’ve ever seen in my life.
I moved forward and whispered into her ear. “Stay just like that. I’ll be back. Don’t fucking move!”
I sprinted to my bedroom and launched myself at the top drawer of the bedside table. I grabbed the lube. Fuck the condoms.
When I got back to the kitchen she was still in the same position, looking back at me. My fucking God. I got my shorts off and on to my knees and threw the lube on the floor. I reached up and lifted the bottom of the dress up over her ass. “Here, hold it up.”
She held the dress up as I looked at her sweet ass encased in white silky panties. I ripped them off in one quick swipe.
“Oh!”
I pushed my hand between her legs. “Spread them a little.” She did as she was told. I brought my hands up to those sweet cheeks. How delicious. I pawed at the white buttocks, marvelled in their softness and kissed each one.
Then, the moment I’d anticipated. The parting of the cheeks. The sweet prize revealed. I moaned as I spread them and exposed her tight anus. The dark brown skin around it, the pink oyster meat in the centre. I moved forward and inhaled that wonderful musky scent, then my tongue came out to lap and lick and probe at this sweetest orifice.
“Aaaaaaahhh!”
“Yes honey, how good is that?”
Pippa didn’t reply, but I knew this was just as hot for her as for me. Her legs shook.
“Come on, get down here. Get on the floor.”
Again, she did as she was told, gorgeous girl, and I got her to lie on her tummy and lifted the dress up and spread her legs just enough to make it the sexiest fucking
pose in the world.
I stroked a smooth buttock. “Good girl.” The lube was beside me and I opened it and put a dollop on a finger. I spread the cheeks again and placed the finger at the opening.
“Oooh!”
I stroked in small concentric circles around her rosebud with an index finger, until it was pressed in at the centre, then slowly, slowly, pushed forward. Pippa gave a small hum as I pressed in and suddenly the finger slipped inside. I held it there, then pushed further into the void. I have quite long fingers and it went a good way in, but I didn’t feel any shit.
I brought the finger out again and coated it with more lube. Then I used two fingers. This was the way to do it – slowly. Of course, if it was a one off I could have just ploughed in there, but I felt this naughtiness was something that turned Pippa on as much as me. My dirtiest fantasy come true.
She moaned and pushed back to get the fingers in deeper. This was a good enough sign for me to go forward and take what I’d wanted from the second I saw her. I coated my now stiff cock with a generous amount of lube and got on top of her. I presented my throbbing knob to the dilated anus and pushed.
“Oh God!”
“Yes, good girl. You feel it going in?”
“Yes!”
“That’s it, take a deep breath.”
Pippa inhaled and I went forward again and felt my knob get sucked into her insides. Her sweet body took my long hard cock and it was delicious. I looked down at her slim back and I imagined how far up inside her colon I was.
“Good girl Pippa. Save your pussy for your future husband.”
“Aaaah!”
I felt her shiver under me. Had the little hunny just had an orgasm, deep up her shitter?
I couldn’t come yet – this was too good. I pumped slowly. Pippa looked back. Oh, those gorgeous blue eyes, those adorable freckles across her nose.
“Pull my hair!”
“Yessss!!!” I grabbed a handful of that luscious long hair and wrapped it around my fist. I pulled back, stretched her neck right back, but she kept her eyes on me, determined.
“That’s it, hard!”
This spurred me on even more and I started to pump her shitter. No more mister nice and gentle, this was the pounding her sweet ass needed. Slap, slap, slap.
She responded with involuntary grunts. “Uh! Uh! Uh!”
I had two hands meshed into her hair then and pulled her hair back, looked into her eyes. “Dirty bitch you fucking love this don’t you?”
I could feel her try to nod.
“Yeah, dirty anal slut.” Slap, slap, slap. “Dressed up sweet and pretty yet all you want is a cock in your shitter. Will you ever take a cock in your pussy? Probably not, you’ll love this too much.” Slap, slap, slap. “I haven’t come for a week. Oh fuck, I’ll blast up your shitter, dirty anal cunt!”
This nastiness took us both over and I started fucking like a maniac and all that tension just suddenly came upon me and I screamed.
“Aaaaaahhhhhhh!”
The cum pissed out of me and up into her pooper. I couldn’t see inside but I could imagine how my cock spasmed and squirted thick ropes of hot cum deep into Pippa’s bowels and scalded her insides. I couldn’t help myself and I leaned forward and bit the skin at the top of her shoulder.
“Ooohhhh!”
This caused her to shudder too, and her second orgasm joined mine and we both came in a shivering heap on the floor.
I rolled off her with a delicious wet sound as my cock extracted itself from her shitter. I stared at the ceiling.
After a couple of minutes Pippa got up and went to the bathroom. I took the opportunity to put my shorts back on and grab my drink.
When she came out there was that awkward what-the-fuck-do-we-do-next thing, but thankfully Pippa took the initiative and said that she had to leave. We exchanged numbers, I think more than just out of politeness, as it was a dirty experience I wanted to repeat some time. I think she did too.
I kissed her and she left. I went out to the balcony and watched her walk back towards the bar. There were a couple of guys walking in the opposite direction and I saw them check out her sweet butt when they passed her. Ha, if only they knew she had no underwear on, and probably had an ass full of my cum. Unless she’d shit it out that time she was in the bathroom.
I walked back into the apartment with these dirty thoughts in my head and picked up her ripped underwear and sniffed. Then I unbuttoned my shorts and got my stiffening cock out again. Yes, I’d definitely want a repeat performance in Pippa’s ass. Mm, what if? What if I got a butt cam in the sex shop and put it up inside her ass the next time? I’d be able to see all the cum up inside her. What if I advertised it on that pervy Kristen’s Board website? Come and get it guys – the live stream of Pippa’s home colonoscopy. Yeah, what a great idea. I laughed as I imagined it. There would be so many members of Kristen’s Board into that – the bunch of fuckin’ perverts.
*****