Uncle Bob Ch. 24 – Anal

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Chapter 24. Like a Virgin

© Bad Hobbit 2023

Author’s Note: Well, I’ve finally created something that feels like an ending. Sure, I could go on, but after 24 chapters and over 250k words, I feel Bob and Stacey deserve to be left to themselves for a while. Please let me know what you think of the whole Uncle Bob saga – improvements I could’ve made, things I could have added, or should’ve removed. And I hope you enjoyed the ‘awesome’ ride.

*****

They say that in space, no one can hear you scream. However, in an over-water bungalow in Bora Bora, the walls aren’t very thick. Stacey’s screams could probably have been heard all the way to Papeete, and definitely in the neighboring villas.

I could figure out why she was screaming. She was on her back, her legs spread wide, and my cock was regularly pounding her ass. In addition, I’d pushed a large rabbit vibrator (‘with thrusting action’) into her sweet, drooling pussy and my abs kept shoving the toy deeper into her each time my cock got balls-deep. The rabbit’s ‘ears’ were mercilessly buzzing her clit, and she had no control because her wrists were tied above her head to the bed-frame. And I was pulling on a chain between a pair of nipple clamps. I think she was probably coming for over a minute before she started begging me to stop. I held on for maybe a minute longer before I unloaded a full Bucket o’ CumTM into her ass, but I really should’ve worn ear defenders.

And being a regular nice guy, I left the vibrator in place after I’d pulled out of her dark hole. As I cleaned up, I started to wish that I’d brought a ball-gag with me. With her ankles tied to the bedposts so that she was almost doing the splits, she was unable to do anything more than writhe and scream.

“AAAAARGH! PLEASE STOP! OH FUCK! FUCKFUCKFUCKFUCK! PLEASE, PLEASE STOP IT! I CAN’T TAKE ANY MORE! AAAAAAIIIIIIIII!!!!!”

I could see her whole body shaking, bouncing and twisting on the bed, so I decided that I should give her a break. I pressed the button to switch off the vibrator, and after maybe another ten seconds, Stacey stopped twitching and slumped back onto the bed, panting like she’d just run a sprint race.

After a few minutes, I called reception and asked for a couple of Mai Tai’s to be sent up, untied her and gently rubbed her wrists and ankles.

“I love you so much, Uncle Bob,” she said, dreamily.

“And I love you infinitely, Stacey, baby, but please can you get into the habit of calling me just Bob?”

“Sure, just Bob,” she said with one of her beautiful smiles. Then she threw her arms around me and kissed me.

We only broke off when the cocktails arrived.

*****

We’d moved on to Bora Bora after our friends had all gone home. After our wedding “after party”, Yves had shaken me awake. I was lying with Stacey, still asleep, cradled in one arm. I looked up to see Monique, still enticingly naked, standing beside her boyfriend.

“Should we ask them to bring breakfast yet?” Yves clearly hadn’t forgotten that, despite having fucked the bride a couple times the previous night, he was still working for us.

“What time is it?”

“After nine. It will take them perhaps thirty minutes to bring it across. Or I could delay a little longer.”

I looked around. Craig, Martin and Dolores were sitting, admiring the view out into the lagoon. Barbie and Hannah were still asleep. I could see Josh emerging from the water. Everyone was still naked, and half of my guests seemed to still be asleep.

“Can you give it a half hour?” I asked. “I need to get folks up and maybe showered first.”

Bien sûr,” Monique replied. “We have sarongs for everyone, so you will not be naked when the staff arrive.”

Whether that was meant to be a helpful suggestion or an instruction, I wasn’t sure. Some of my guests seemed to think Monique was a little ‘bossy’, though I explained that she needed to ensure things happened according to plan and didn’t get too wild. Josh had referred to her as ‘Auntie Monique’, and a couple of the guys had laughed at the humorous title. I wondered it was particularly amusing, given that half the girls still called me Uncle Bob.

Although the staff had seen the titties of all the ladies present on the previous evening, my guess was that we should now try to be a little more demure. The sight of the residue of the previous night’s debauchery – naked bodies, fluids liberally sprayed on bare skin, sex toys scattered around – might not be the best thing to show off to some impressionable local girls and boys.

When breakfast arrived – tropical fruits, cereals, sublime French pastries, coffee and some freshly-cooked bacon and eggs – we were all awake, showered and wearing sarongs. There wasn’t a cock, a pussy, a titty or a sex toy to be seen – the ladies’ sarongs covered them from bust-line to knee. As we sat and ate, I heard some of the gossip.

“What was it like?” Amy-Beth asked Hannah.

“Well, it hurt a little at first. Like, he’s pretty big. But then, I guess, I got into it and it felt good.”

“What?” I asked, butting into the conversation.

“Oh, Hannah let Martin fuck her ass last night. I mean, I watched, and at first, I thought Hannah was gonna scream, but then it looked so hot.”

‘Shit!’ I wondered. ‘If Hannah can take Martin’s plus-sized dick up her ass, she won’t want mine anymore.’

“Yeah, it was good, and I came, eventually. But, like, I couldn’t do that every time. I preferred it when Uncle Bob fucked my ass. It was, like, easier to get started and I came quicker.”

I smiled. Well, at least it seemed that particular opening was still open to me. I went for another coffee, and met Chelsea. There was something about her, now that she wasn’t with Michael, that seemed less plastic, more ‘ordinary’. But then who am I to judge what ‘ordinary’ is?

“Oh, hi, Bob. It was totally wild last night. Thank you so much.”

“Glad you enjoyed it. I noticed you getting adventurous with some seriously big cocks. I hope they haven’t spoiled you for Brad.”

She smiled. “You know, it felt exciting at the time, and I’m glad I tried everything I did, but Brad – well, he’s my guy. He’s kind, and he’s a generous lover, and – and, well, I love him. I guess I didn’t fully realize that until lately, but ever since we met, he’s made me so happy. So no, big cocks can be fun, but my guy’s quite well-enough hung to give me pleasure, and he doesn’t leave me sore afterwards!”

Monique and Yves were circulating, checking all was well. “So how was last night for you?” I asked when they arrived next to me.

Incroyable!” Yves said with a wide-eyed smile. “Never have I done anything like that. Your friends are very, er, aventureux?”

“Yeah, I guess you could call us adventurous, or uninhibited. Some of us are just plain crazy. But you seemed pretty adventurous yourselves. How was Craig’s cock, Monique?”

I swear I saw Monique blush. “Er, énorme. Yves, he is bien doté, but Craig is – so – so – huge!”

“But did you enjoy it? You seemed to be from where I was situated.” Though, I reflected, I was situated most of the way up Barbie’s ass at the time, and as there are few more sublime places for a guy to be, maybe I wasn’t too focused on what Monique was doing.

“Yes, it was exciting. More so, I think, because Craig is so muscular and – and black. I have never had sex with a black man before yesterday. There is a certain frisson about it. Do you understand?”

“Yes, I understand. And was it good, having my wife licking your pussy at the same time?”

Ah, oui! I have only once had some sexual liaison with another woman, around four years ago, when Yves and I agreed to invite a friend into our bed. She was leaving for France, and we both agreed she was very attractive, and she had confided in me how she thought Yves was sexy. It was good, but – but with Stacey, it was better. And with that strange one with the tattoos and the black lipstick, er…”

“You mean Amy-Beth? Sorry, did I miss something?” Amy-Beth had re-colored her hair to black before the wedding. I felt it looked much better than the blue she’d had before, and together with her new confidence and her trademark black lipstick made her look interestingly scary – kinda like Wednesday from the Addams Family, but with nipple piercings, tattoos and an anal-sex fixation. (Though I still think Christina Ricci was and is hot, and if she ever asked me to fuck her ass, I wouldn’t hesitate).

Yves smiled. “After you had finished with Barbie, you went to sleep. But some of us continued. Amy-Beth wanted me to – to fuck her, and she wanted to have some sex with Monique. It was, how you say, sublime. I think she had perhaps four orgasms. And Monique, I think she may have had two.”

“Perhaps more; I lost count,” Monique smiled back at me. “But others continued after us. I am sure several of your guests took advantage of each other’s willing bodies. Your belle-mère, she did not seem to want to sleep. I think she tried to enjoy every man who was still awake!” ‘Yes,’ I wondered, ‘that’s Dolores alright.’

I circulated, and heard numerous other stories. It seemed that everyone had enjoyed – well, almost everyone else. And that was perfect.

We posed for some more photos – the ones we could put on Facebook, show the folks back home – wearing sarongs that covered everything essential and with Stacey, Hannah and me once more garlanded with flowers to look like we’d just had a more-conventional ceremony. With the light in front of us, it wasn’t obvious that we were all naked under the thin wraps of cloth.

Finally, we collected our things – including the boxes of sex toys – Yves and ‘Auntie Monique’ shepherded us to the canoes, and we guys paddled us the short distance back to the motu and our rooms. We said our thanks and goodbyes to Monique and Yves. The goodbye kisses were a little more passionate than might usually have been given to wedding planners. I guess it’s a little different if almost everyone there had fucked one or both of them. Stacey and I agreed to see them again when we arrived in Papeete on our way home.

Later, Stacey and I went for a late afternoon drift-dive in the lagoon. It was one of the best I’d ever experienced; great coral, masses of small fish, silver-tip reef sharks and spotted eagle rays. Then, as we waited, hanging in the water for our safety-stop, a pod of dolphins went by. Stacey was so excited she was bouncing around on the dive boat. The others had taken a snorkeling trip and were thrilled by what they’d seen.

That evening, we all ate together in the hotel’s restaurant, and then Stacey and I went back to our villa. Stacey insisted on showering first – we usually showered together – and came out in a bathrobe that, as in most hotels, was far too big for her. “Take your time,” she smiled at me. I guessed that she may have had something planned, and when I emerged from the bathroom, maybe twenty minutes later, wearing a towel around my waist, I was greeted by a jaw-dropping sight.

Stacey was dressed in white lingerie. Her cupless bra just – and only just – supported her flawless little breasts. Her tiny, sheer thong panties were crotchless, the thin silk ribbons between her legs framing her smooth, pouting pussy lips. Her long, skinny legs were sheathed in white stockings, topped with silk garters. She had on high white patent leather heels with sexy ankle straps. And a white lace choker, with a sweet bow. She’d done her hair in cute little bunches, tied with white ribbons, and topped it all off with a bridal veil. Her makeup was just a little over-done, her eyes dramatically shaded, her lips bright red. Fuck! I mean – fucking fuck!

She was looking down, demurely, clutching a small posy of white flowers in front of her. I guessed she must have pulled it together from her bridal bouquet.

“It’s our wedding night, er, sir. We’re alone at last. I’m kinda nervous. You see, I’m still a virgin. I want to please you, but I’m shy. I know some men can be – can be quite big, and I know that they – they want to use all the – all the holes a girl has. But, sir, I’m – I’m a virgin, everywhere. I’ve never had – had a boy inside me before. You will – you will be gentle, won’t you. Please?”

Like I said – oh fucking fuck.

Stacey loves role-play. We’ve tried all sorts, from the street hooker she played soon after we’d started our little adventure to saloon girl, to schoolgirl, to cheerleader, to Lara Croft (she doesn’t have the tits for it, but whatever). Usually, she likes to be slutty. She loves raunchy outfits, thrives on being as naughty as feasible. Sometimes she’ll do something with Hannah or Amy Beth, maybe with collars and leashes or leather or whatever. One time, she flaunted some tattoos and piercings that freaked me out until I realized that the tattoos were decals and the piercings were just clips. (She did, however, get a belly-button stud for her nineteenth birthday that I didn’t disapprove of).

But this? The towel struggled to contain my boner. I’d relieved her of her virginity in two of those three holes around a year earlier – her throat had already been plundered by some lucky, undesiring asshole before she left high college. But now we were playing ‘conventional marriage’; the groom deflowers the bride on her wedding night. That girl never ceases to amaze and excite me. I’m the luckiest fucker in the world.

And I was gentle. Often, Stacey is so juiced-up that we’re straight into hardcore. She’ll swallow my length, or straddle my face. Sometime she’ll just mount me, throwing her legs over me or spreading them wide, or maybe even insist that I remove her anal plug and stick my cock in. It’s not often that she gives me time for a lot of foreplay, or to be romantic.

This was different. I carefully pulled the veil up and laid it behind her head, lifted her chin and kissed her. It was soft and very loving. We kissed like that for a few seconds before she dropped the little flower posy and put her arms around me. After a minute or so, I let my mouth and hands wander over her perfect little body. I loved the smoothness of her skin, the way she bent her head back to allow me to lick and kiss her throat, on either side of the narrow choker. I moved behind her, loving the fine hairs on the back of her neck that brushed my lips. I traced the indentation of her spine with my tongue, ran my nails lightly down the backs of her arms, teased her inner elbows with my fingertips as I returned to lick her shoulders.

She turned her head to kiss me again, and I slid my fingers around her to caress her prominent hip bones. The towel fell from my waist, and as I pulled her gently toward me, my erect cock pressed into her back.

“Oh my! You’re awfully big!” she gasped. Fuck, she really knew how to do the role-play to perfection.

I slowly knelt down. The panties had a fine web of tiny silken straps across her tight little ass-cheeks, just begging for my tongue to explore between them. I noticed that, being Stacey, she’d inserted a faux-diamond anal plug in the shape of a heart. My tongue wanted to go there, or taste the juices that I could see were already moistening her sweet outer pussy lips, but that would be too soon. My hands traced lines down the fronts of her thighs as my mouth focused on the backs of her legs and that sweet, slightly-goosebumped skin above her stocking-tops. As my hands brushed over the silk of her stockings, I licked the tiny creases where her firm buttocks met her thighs.

Then I scooted around, still stroking the backs of those long skinny legs with my palms as my tongue traced the outline of her panties, up to those sexy hipbones, across her flat stomach, up to her recently-pierced navel. I was determined to avoid her pussy until I could see the juices begin to drip down her legs.

My mouth worked upwards in long, serpentine strokes, as my fingers and nails tantalized the skin above her hips, the insides of her elbows, and swept around to gently stroke and squeeze that tight little ass.

Finally, my mouth skipped over the silky fabric of her cupless bra and licked all around her breasts, before focusing on each nipple in turn. She gasped. “Oh yes!”

By now, my boner was throbbing. Hannah, Amy-Beth, Dolores, Chelsea and especially Barbie can all get me horny as fuck. But Stacey – Stacey can do things to my mind and body that no-one else can achieve. I was so used to Slut-Stacey, Borderline-Hooker-Stacey, Spontaneous-Cocksucker-Stacey, Anal-Princess-Stacey that I’d almost forgotten that there was once Shy-Virgin-Stacey. And for all the raunch that she’d learned over the year of our weird, supercharged, erotic roller-coaster, this was perhaps the sexiest Stacey of all.

A year earlier, my gorgeous niece shyly seduced her devoted uncle, who felt that some radiant angel had just entered his life – even if that angel had then insisted he fuck her ass. Now, it was almost like the seduction was the other way around. Here was Virgin Bride Stacey, shy, nervous, a little afraid, preparing to give her sweet, innocent body to her new husband, as an act of love and duty. And it was totally convincing. If I hadn’t regularly invaded every available orifice on that young girl’s body, often energetically and orgasmically for both of us, if she hadn’t delighted in screaming obscenities and behaving, at times, like an accomplished whore, I could fully believe that here was a dutiful young bride, about to sacrifice her unused and pristine little holes to her new husband for the first time as a gift of love.

But I set apart all my previous memories and focused on our delicious charade. I kissed her again, and guided her hands down to my cock. She gently wrapped her hands around it and gasped.

“Oh, it’s so big – sir. It’s – it’s kinda scary. Do you think – do you think it’ll fit?”

“It’ll fit beautifully, my love. It’ll slide right in, and you’ll love it. But first, we need to get you ready.”

I reached around her and unfastened the non-bra, carefully lifting it away as she raised her arms, before she returned to stroke my cock in a gentle, almost innocent way. We kissed, and I palmed her cute little breasts, rubbing on her nipples in the way I knew she loved. Then slowly I slid my hands down her sides to hook the waistband of her transparent panties. Just as I started to pull them down, she gently took hold of one wrist and guided my hand between her legs. As my finger instinctively parted her pussy lips and dipped into that warm, wet valley between, she moaned.

“Oh, sir, I’m so, so wet for you. I want you. I really do. But – but I’m frightened.”

And she genuinely sounded it. For a second, I thought whether, when we got back to LA, I should take her to a studio and have her audition. Her acting skills were clearly very well-tuned. Of course, she’d probably insist we need to do porn, rather than Hollywood.

“Don’t be afraid, little girl,” I replied. “I won’t hurt you. It’ll all be magical, I promise.” I let my finger slide lazily back into her cleft, and then slowly up inside her.

She gasped again. “Oh, sir! Oh, that’s – that feels – it’s… Oooooh!”

I slowly finger-fucked my faux-virgin bride, just a shallow penetration that teased the entrance to her much-used but now, apparently, inviolate little cunt. She looked into my face with her gigantic baby blues, a shy smile on her face.

“Should we – I mean, do you want to…?”

I smiled back, slowly slipped my hand out of that drenched little slit, and then swept up my new bride in my arms and carefully laid her down on the bed. The veil was still behind her head. She arched her back as I pulled the almost-not-there panties down, leaving the stockings, garters and shoes in place. I slid a pillow under her pert little ass, spread her legs wide and with as much restraint as I could, moved slowly in for the feast.

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