Uncle Bob Ch. 14

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Hannah gets some slut-training from Stacey the slut-princess.
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Part 14 of the 24 part series

Updated 04/10/2024
Created 10/03/2009
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Home is where the ass is

The next day, our last in New York, was a wet, sticky, joyous blur. I awoke as Hannah's thighs settled on either side of my head.

"Breakfast, Uncle Bob. Stacey got me nice and juicy. Now you just need to eat."

A moment later, I felt the now-familiar, but certainly not unwelcome, feel of my slut-princess sliding her mouth down my cock.

"Morning, Hannah, morning, Stacey," I managed to say before Hannah's fleshy pussy lips descended onto my mouth.

"Mng unn buuu" I heard, as Stacey rudely tried to speak with her mouth full. After that, my mouth was pretty full too, nibbling Hannah's interesting pussy lips and sucking on that big clitoris. I found that if I pulled the hood back with two fingers, sucked it between my lips and strummed the tip with my tongue, I could get Hannah into a kind of rolling wave of orgasms.

Stacey, meanwhile, wasn't going for the slow tease either. I felt her cute, button nose hit my belly repeatedly as she skull-fucked herself on my cock. I didn't even bother to hold back; Stacey knew what she was doing and I was very happy to give her an early protein breakfast, unloading the replenished stock of jizz that my balls had manufactured overnight down her throat in a very satisfying manner.

And then Hannah, still trembling from her extended climax, climbed unsteadily off my face, and Stacey bounced into the saddle. I traced an unusual buzzing to a vibrating butt-plug, as she pressed her wet, fragrant, delicious and wide-open pink slit into my face. I just had time to extend my tongue and make her squeal before she butted her clit up against my nose. I tongue-fucked her for a couple of minutes, teasing in a way she would find very stimulating and a little frustrating, before getting up close and personal with her clit. I managed to reach up and grab hold of her tight, skinny butt cheeks and hold her down on my hungry tongue while she squealed and wriggled, trying to moderate the powerful sensations that were sending her into her own extended orgasm. I tortured her for at least two minutes - hard to keep track of time when your face is covered in pussy - before she managed to squirm free, gasping and giggling madly.

The three of us showered together, with lots of rubbing, kissing and caressing, before Stacey stepped out to dry her hair. Hannah stayed in the shower with me, then dropped to her knees and sucked me until I was hard enough to fuck her from behind, up against the tiled wall, giving us both our second orgasms of the day. I left Hannah in the cubicle, trying to clean out the trail of jizz that was trickling down her legs.

We sat in a booth at the deli and had a light and rather late breakfast.

"OK, girls, what would you like to see today? I thought maybe a trip to the top of the Empire State, maybe a stroll in Central Park, or we could take in a gallery."

"Uncle Bob," Hannah said, leaning across the table. I could see her lovely rounded tits down her low-cut t-shirt. "What I'd most like to see is - is whether your lovely cock will fit inside my ass. After last night, and then again this morning, I'm sooo horny, Uncle Bob. You said that I shouldn't try anal until I really, really wanted it. Uncle Bob, I, like, sooo want it now. I cleaned up good after you left the shower, and I lubed and put in a plug. Look."

She turned around, knelt on the bench opposite me and hitched her skirt up to her waist. Of course, no panties. I noticed her pussy lips were wet, and there was a small dribble of cum leaking out of her sweet pink fuck-hole, still a little open and stretched from our shower session. And between her honey-brown butt cheeks, the same vibrating butt-plug that Stacey had been wearing while I ate her a little earlier. I quickly glanced around to check that no-one was watching. Shit, this could get complicated.

I knew I'd much rather explore Hannah's tight anal cherry than the Big Apple any day. I looked at Stacey. She was smiling and nodding. "And Uncle Bob, when you've fucked Hannah's ass, could you please fuck mine again. And maybe she could, like, wear a strap-on and fuck my pussy at the same time?"

Oh my God! Remember what I said about a guy being fucked to death? But there was more.

"But first, Uncle Bob, we need to go shopping. See, Hannah doesn't have anything slutty enough, and she needs to be super-slutty if she's gonna take it up the ass. I saw a shop just a block away where we could so get her some slutty outfits. Can we, like, go there now?"

So I again sat outside the changing room in a rather sleazy-looking lingerie and sex-toy place while the two girls giggled behind the curtain of the changing room. I heard a few gasps and 'ohmygods', before the curtain was pulled aside and the girls emerged, clutching a tight bundle of items.

"No peeking, Uncle Bob. We'll get these bagged up and then you can pay for them." Story of my life.

On the way back to the hotel, Hannah keep making little shrieking noises and twisting and squirming. I looked at Stacey, who had one of her 'naughty' smiles on. At my implied question, she simply said "I have the remote".

In the room, Stacey insisted that she and Hannah used the second bedroom, while I prepared the room we'd all been using on the last two nights. I could hear squeals and giggles coming from behind the closed door, so I went to the bathroom, cleaned up and made sure my balls and cock were free of hair. I cleaned my own ass out pretty thoroughly, too; not that I wanted anything up there, just that I might - if I was lucky - get rimmed. I put on a loose pair of cream silk boxers that Stacey had brought me back as a present from Italy and went back to what I was now calling 'our' bedroom.

Then I quickly checked the hidden cameras I'd set up before the girls had first arrived, and reviewed - on fast-forward - some of the footage I'd already taken of our earlier sessions to make sure it was all good. I adjusted the angle of one of the cameras to ensure we'd have a perfect view of what was about to happen. I had two 4Tb drives set up and attached to the computer, so I cleared the computer's SSD onto one of them, as I guessed I might need all of that space before I could edit anything down.

Then I heard the other door open, so I quickly turned the cameras on and lay back on the bed. Stacey and Hannah appeared through the door, and I almost came in my new boxers. Stacey had on this black body-harness set - basically a set of straps that crisscrossed her body, leaving everything important exposed - with a black leather collar, suspenders, stockings, knee-high boots and a little fluffy tail plugged into her butt. Hannah had a cream satin corset that cupped under her lovely tits and just helped them jut out a little more, with suspenders and white stockings and some strappy heels. Her hands were held behind her back by - as I soon discovered - a pair of cream leather cuffs. And she was wearing a matching cream leather collar. With a leash, being held by Stacey. My silk boxers were straining.

By the end of the bed, Stacey took up a pose, one hand on her hip and the other holding the leash up. Hannah was standing demurely, looking 'submissive', her head bowed. My eyes were drawn to the bare, milky-coffee skin of her pussy. It glistened, and there were some little trails of liquid on her upper thighs. The girl was creaming.

"Uncle Bob," Stacey said in a nonchalant tone, "I've brought you this slut for your pleasure. She says she'll let you do anything to her. Anything. Do you understand?"

Oh my God. "Sure, Stacey, I understand. But Hannah..."

"She doesn't want to be called by her name. She is simply to be referred to as 'slut'."

I moved my gaze to Hannah's face. She looked shyly at me and nodded. Shit, Stacey had done her work well.

"OK, slut, what do you want me to do to you?"

"Nithg"

"Speak up, slut. What do you want me to do to you?"

"Anything, sir. I'm here for your pleasure. All my - all my holes are yours to use."

She suddenly gave a little squirm and a gasp. I saw that, when Stacey lifted her hand from her hip, she was still holding the remote.

"Oh please, please - AH! Ohmygod - please - please fuck my ass. Gotta - gotta - AH!" Hannah's body was twisting and writhing like crazy. I saw Stacey move the dial back and Hannah stood up straight again. There were tears running down her cheeks.

I wanted to hug her. When I'd first met Hannah, sure, I'd wanted to fuck every hole in her delectable light-brown body. As I'd come to know her better, I realized that she was a little fragile underneath - maybe more than a little - and I'd felt I needed to comfort and reassure her. But now...

I climbed off the bed and walked behind the pair of beautiful and raunchily-clad young women who were presenting themselves for my pleasure. Over breakfast, I'd surreptitiously taken another Cialis, and I hadn't so much got wood as developed a chromium steel rebar. I gently placed my hands on Hannah's shoulders and slowly slid them down over her lovely, firm tits. She was trembling.

"So you want me to fuck your ass, slut?" I whispered in her ear.

She swallowed hard. "Y-yes, please, s-sir. AH!" A sideways glance told me Stacey was tormenting her friend with the anal vibrator again.

"Stacey, do you have the key for Hannah's - this slut's - cuffs?"

Stacey held the key towards me. I took it and unlocked the handcuffs.

"S-sir, aren't you - aren't you worried that I'll - I'll run away if my hands are free?" she murmured.

"No, slut. I need you to kneel on the bed and stretch your hands out in front of you. Right down now, so your face is on the sheet."

Hannah obeyed, climbing onto the bed with a little difficulty in her heels. I moved around and re-fastened the cuffs on her wrists, peeled off the boxers, then pushed my hand into her hair and turned her head toward me, presenting my cock, a few inches from her face. She dutifully opened her mouth and let me slide my dick slowly inside. I fucked her mouth in a leisurely fashion for around a minute, before pulling back and moving around behind her.

"Hey slut-princess," I said, turning to a smiling Stacey. "Get another vibrator and hold it onto Hannah's - the slut's - clit." As Stacey moved to obey, I started tugging and releasing the anal plug, until Hannah was making plaintive little squeaks and wiggling her hips around, trying to avoid - or accommodate - the powerful sensations.

Finally, I pulled the plug - quite a large one for an anal novice, I thought - out of Hannah's sweet little asshole (she shrieked), and prepared to become the asshole who plundered Hannah's virgin asshole for the first time.

"Tell me what you want, slut. Ask nicely." I tugged a little on the leash.

"Please - please fuck my ass, sir. Please!" she murmured back.

"It'll be my pleasure, slut," I replied. I'd picked up a tube of lubricant from the nightstand when I'd gone to re-fasten Hannah's cuffs - and also get my cock sucked - so I was able to lube up nicely. Then I pointed my iron-hard dick at the recently-vacated little starfish - the hole in the center only a little enlarged by the plug, like a mouth making a surprised 'O' - and pressed.

Hannah made a surprised "OH!" as I started to stretch that tight circle, and then a lot of other noises; gasps, whimpers, moans, little cries of 'ohmygod', and then a longer 'aaaah' as my cock-head popped through the ring - and I was inside.

Stacey shuffled in alongside me, slipped a hand under her friend's hip and pressed a vibrator against her clit. Hannah made a lot more noise, the volume increasing as she now had further stimulation to keep her occupied. I, meanwhile, did my usual gentle in-out to make sure that the lube followed - or preferably preceded - the passage of my cock in her passage. Edging deeper, deeper, stretching, filling - fucking that virgin asshole as gently as I could, with maximum positive stimulation.

"Tell Uncle Bob - sir - what you're feeling, slut," Stacey said in a voice that was meant to be a little menacing, but still sounded cute to me.

"It's - he's - ohmygod - oh fuckfuckfuck! He's - you - you're - you're fucking my ass, sir! Fuck, you're so big in there! Oh fuuuuuck!" A plaintive little whining noise came out of her mouth. "Shit, you're going - going so deep - s-sir! Oh my GAWWWWD!"

"You begged me to do this, slut. Now you have my cock right up your slutty little asshole. How does it feel to be an anal slut at last, Hannah?"

"Oh fuck - it feels - it feels AWESOME!"

"Should I fuck your ass harder, slut?"

"I - I - oh yes, sir. Please, sir, I can take it. Fuck - fuck my ass harder, sir. Please, fuck it - fuck me - harder! Make me - make me your anal slut, sir!"

OK, so at this stage, one of a number of things could have happened. I could have taken Hannah at her word and pounded that little cutie's ass really hard. I could have carried on as I had been doing and just tantalize her until she begged me. Or I could have shot my load immediately because of the sheer horniness of the situation. It was close, either way.

I took a deep breath, forced down the sensations threatening to make me fill Hannah's ass with cum then and there, and gradually increased the pace and depth. After a minute or two more of this, plus a lot of filthy goading, I was thrusting balls-deep, my hip-bones touching Hannah's peachy ass-cheeks at the end of each stroke, pulling back on her ring with my cock head on the back-stroke. I could feel the vibrations coming up through Hannah's pussy as Stacey did what she needed to do with the vibrator. Then, just as I was wondering how much longer I could stand it, Hannah's moans and cries got louder and I finally felt the sensation I was waiting for.

The pulsing in Hannah's ass was fantastic. Fuck, a virgin ass is a delight when you're deep inside and the girl is discovering just how good it can be to get royally sodomized. At that moment, Hannah really was ass-fucking royalty, and she did her royal duty by proudly coming so strongly that she milked my dick of every drop of juice inside it. She was moaning and gasping, between bouts of "OH FUCK!" and "OHMYFUCKINGGOD!" Her legs were shaking, she was thrashing around so much I had to hold onto her hips to stop my dick being wrenched off. And if proof was required that Hannah had achieved the orgasm I so desperately wanted to give her, the beautiful, tell-tale pulsing in that sweet, tight little ass was all the evidence I needed. I guess I added a few noises of my own to Hannah's impromptu jazz vocals. Shit, my own orgasm was so strong I wondered whether my cum would spurt out of Hannah's mouth.

When the electric shock coming from my cock finally abated and my hair stopped standing on end, I slowly and very gently pulled my softening cock out of Hannah's ass. I could feel a few aftershocks, and heard some sweet little gasps as that lovely girl got a bit of extra stimulation she wasn't expecting.

Then the three of us were lying on the bed in a little huddle, Hannah, still trembling, sandwiched again between Stacey and me. I picked up the key and released her wrists from the cuffs, and she turned to me and gave me a delightful kiss and cuddle. Her face had this dreamy, far-away look. She was smiling, and her mascara had run down her cheeks. She was stunningly beautiful. If I wasn't already head-over-heels in love with my slut-angel, I could easily fall for this beautiful, brave, sweet girl.

"Oh my God, Uncle Bob, that was so, like, awesome," she sighed. Teens never do seem to improve their vocabulary, but I wasn't about to complain.

"Hannah, baby - you were awesome. You were so brave to go with it, to reach out to your sluttier side. Did you really enjoy it?"

"Oh, Uncle Bob, it was amazing. Stacey told me it felt so good when she got really slutty and took it up the ass and stuff, and I was like - well, maybe that's, like, good for you, but I don't know. But she got me to so enjoy being sluttier and sluttier, and I knew I, like, so had to try it. And she'd, like, said that you were so good, so gentle, and you always made her come that way, and I realized that if I didn't try it with you, like - like before we went home, then maybe I'd never get the chance to do it with someone who'd really make it good for me. And you totally did." She kissed me. Like I've said before, she's a very good kisser, even if her vocabulary is as Valley as Stacey's.

Then she broke the kiss, smiled at me and turned to the other slut in the room. "Thanks you so much, baby. You so made all this happen for me." They kissed. I watched. Then they were touching - hands on breasts, sliding over silky-smooth skin. "I was so 'why would I want to be a slut?' And then - then you showed me why. Just how hot and sexy and naughty it is, how I feel totally horny when I'm being slutty." They kissed again. "I love you, Stacey." They kissed again.

"I love you too, Hannah. You're so the best bestie anyone could have."

And they kissed again. And fondled. I like watching girls kiss and make out. I don't know why. But after a few minutes of this delightful spectator sport, I needed a visit to the bathroom, so I left the girls to it. After emptying my bladder and having a thorough clean up, I came back into the bedroom to see them still kissing and fingering each other's pussies, so I went back to the kitchen and mixed another jug of Margaritas. I returned to the bedroom with the jug, an ice bucket and three glasses, to see Stacey bent over Hannah's pussy, licking her clit while fucking her with a big vibrator.

I put down the tray, climbed onto the bed and in one smooth movement, inserted my cock-head into Stacey's wide-open pussy - and pushed. She made a low moaning noise and pushed back toward me, helping me slide deeper. Having gone in balls-deep in one slow but insistent movement, at the end of the back-stroke, looking down at the skinny little cutie below me, her pale skin crisscrossed with those sexy-looking straps, I tugged on the little fluffy tail between her butt-cheeks. Then I pushed my cock in deep again. Then I tugged and wiggled the anal plug around until she moaned some more.

Hannah was moaning hard, and I guessed she was about to come. I watched as her gorgeous face got more gorgeous as her orgasm hit. Her luscious mouth fell open, her eyelids fluttered and the mascara streaks only added to her beauty as a look of total rapture swept over her face. I was again amazed at what an unbelievably lucky fucker I was to have enjoyed so many beautiful girls, often in the most depraved ways, thanks to the beautiful cutie in whose tight, wet, silky little cunt I was currently deeply embedded.

And then I had another depraved idea, prompted by something Stacey had said earlier. Hannah's eyes flickered open, and she breathed 'awesome!' and gave another little post-orgasmic shiver.

"Hannah, baby, do you have a strap-on?"

"Sure. Only..."

I was still thrusting lazily inside Stacey. "Could you get it, please? Now?"

Hannah got up, a little unsteadily, and I was able to admire that pink, fleshy pussy in all its post-orgasmic wetness, before she stepped off the bed and headed next door. I could see a trail of jizz dribbling out of her cute asshole and running down her thighs. 'Shit, I'm such a depraved fucker', I thought.

"What - what're you planning Uncle Bob?" Stacey murmured softly from below me.

"Something you'll like. Now if I pull this cute little tail out, do you think there's room inside for some hard cock?"

"Uncle Bob, there's always - always room in my ass for your cock. You totally rule my ass, you so know that."

"That's right baby." I pulled on the fluffy tail again and she gave a little squeal. A few more tugs and jiggles and she was gasping and moaning beautifully. Then out came the plug - another squeal - and I pulled out of her pussy.

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