Uncle Bob Ch. 20

She looked at me with alarm. I smiled and held my hand up. "Chelsea, neither Stacey nor I care that you stripped and turned tricks. We know you needed the money to support you and your mom after your brother OD'ed, so you obviously used the assets you were given to do the best you could. I have a brain that's kinda hard-wired for logic, so I used it to make money from IT. You have a body that makes men drool, so you used it to make money the best you could. That's no shame on you; just on our crappy society that gives people no choice when they're in that position. But even if you'd been a rich girl who'd done it as a lifestyle choice, I still wouldn't judge you for it. Men and women have sexual needs. It's guys who go to strip clubs and hire hookers, so it's them who should be more ashamed of it than the women who provide the service."

She smiled back at me - and then emptied her glass again and poured herself more wine.

"Thanks, Bob. I really appreciate that. I wanted to go to college, but then - then you're right. Kevin - Kevin died and my mom needed me and I had to find the money somehow. When I met Michael, and he liked me and gave me presents and paid for stuff, I thought all my troubles were over." She sighed and took another sip of her wine.

"Look, maybe you just need to sit down with Michael and tell him how you feel. Do you enjoy sex with him? I mean, normally."

"Sure, I guess. I mean, he doesn't always make me come, and sometimes, like I say, he's a little rough, but yes, it's usually good. But - but now he wants me to do things I really don't want to do."

"Like what?"

"Like - like - like he - he wants - he wants to - to. Oh, I can't say it."

"Come on, Chelsea, please don't be shy with me."

Her face took on a very dejected expression, and she said in a quiet voice "He wants to fuck my ass."

I smiled. "Chelsea, it's OK. Sometimes - a lot of the time - that's not too bad. It might even feel good."

"How would you know?" Her speech was slurred and a little angry. "I mean, you're not a woman. Unless - unless you're gay, you won't know how it feels."

"Chelsea, I've done it with enough women to know it can feel good for them. Some even come from it. And I know one woman - no, two women - who love it so much they actually demand it."

"Sure, you - you say that, but like, I tried it once with - with a client, when I - when I was a hooker. It hurt like crazy. Then - then Michael tried to shove it in, like, two days ago, after he'd tied me up and spanked my ass with the paddle. And it hurt again. It hurt real bad." She took another swig of wine.

'Fuck', I thought, 'I don't even drink beer that fast.'

"Chelsea, look. Yes, I know it can hurt, but the secret is in the preparation. My brother sounds a little clueless, but if you clean and lube and stretch the hole the right way, it can feel really good for both of you."

"Oh yeah? Maybe I should get a strap-on and stick it up your ass! See how - how you feel about that." She took yet another big mouthful of wine and then refilled her glass, emptying yet another bottle.

"Look, Chelsea, girls can enjoy it. They really can."

"Sure. Sure, I know that - that Stacey says she really likes it. And she said that you were good at it."

I suddenly felt a chill.

"Chelsea, what did Stacey tell you?"

"Well, see, she said - she said she saw her boyfriend getting off with her mom. It was at my wedding. And that she said she'd insisted that Dolores had to - to take it up the ass, from you, as a kind of punishment."

I breathed a sigh of relief. "She shouldn't have told you that. That was private. Dolores wouldn't want you to know that she did that."

"But Stacey said that she'd enjoyed it. She said that Dolores had really gotten into anal after you'd made her do it. But what I don't understand is - is how Stacey knew you were good at it." She gave me an inquisitive look, even though her face showed she was more than a little loaded.

Now don't get me wrong here. My favorite type of woman is Stacey. OK, Stacey and Hannah and, yes, Barbie. They're all young, fit and naturally beautiful. But when Chelsea raised an exquisitely-shaped eyebrow, and looked hard at me with big, green eyes under perfectly painted lids with long false eyelashes, and her big, pink-lipsticked mouth kinda made a little pout, I felt a pulse in my groin. Maybe it was because, despite being as artificial as spray-cheese, she was still a horny-looking bimbo. Or maybe it was a little pulse of terror at the thought that she knew I'd been fucking my niece up the ass.

"I - I told her I was good at anal. That I'd learned with my previous girlfriend."

"Sure. And when I worked as a stripper, lots of guys told me they were good at all sorts of things. Y'know, oral, fingerwork, fucking. Most of them were shit. I had to pretend I was enjoying it when I'd rather have had my teeth drilled. Now I guess it's none of my business, but I wonder why Stacey believed you were good at anal."

"Maybe - maybe you should ask Stacey that." I was stalling.

"Yeah, maybe I should. But first - first I need to visit the bathroom." She got up, rather unsteadily, and headed in the direction of her room. She was clearly loaded, so I checked she was OK on the stairs. And frankly, looking up at Chelsea in her tiny bikini, the thong panties having slipped between her pussy lips, wasn't the most unpleasant of sights.

Once she was in her room, I called Stacey. To my surprise, she answered immediately.

"Hey, Uncle Bob!" she said with some enthusiasm. "Hannah and me were just talking about you."

"Hey, sweetie, how's it going?"

"Oh, college is OK, but living away from you totally sucks."

"Sweetie, I feel much the same. You can tell me about what's wrong in a moment, but I need to talk to you about Chelsea. What did you tell her about you and me?"

"Only that you were my amazing uncle and we were like, totally close."

"And not that we were so close that my cock was regularly inside your ass?"

"No! Why would I do that?"

"Well, she's staying with me right now and she's suspicious about how you knew I was good at anal. And about who had already been fucking you up the ass when you insisted that I do that to your mom. Any ideas?"

"Er, I guess - I guess she must've thought about it a lot, 'cuz I didn't say that we'd, like, done it. Do you think she'll tell Dad about it?"

"I think that's unlikely. She's pissed with your old man right now. But there's always a chance that she'll throw it at him as a weapon. 'Did you know your little girl takes it up the ass from your brother?' Actually, I think that's unlikely. Michael wants to fuck her ass and she's scared of it. If she said something like that, he'd just come back with 'So why won't you take it up the ass from me?' But it's going to be embarrassing explaining to her what we've been doing."

"Uncle Bob, it sounds like she's already figured it out. I agree. I don't think she'll tell Dad - or Mom - and she's not the kind of gal to call the cops either. I really think she appreciates that we're her friends. I guess you just have to fess up. But if she doesn't want to try anal, get her to call me. Or - or better still, show her some of our videos. That'll show her how good it can be. Then maybe she could try it. With you. You're the most awesome anal teacher."

"'Anal teacher?' Does that mean I'm an asshole?"

She giggled. "Uncle Bob, me and Hannah are so missing you. Look, sex here sucks like a porn star. I've now fucked guys precisely three times since you left - just three, in all those weeks. And not one of those fucks would rate more than five on a scale of one to ten."

"Were these pussy or ass fucks, sweetie?"

"Duh! As if I'd let some no-hoper fuck my ass if they can't even do the business in my pussy. And, before you ask, yes of course I stayed safe. So no gorgeous feeling of a dick deep in my ass, no dribbling cum and almost no orgasms for poor Stacey. I only get off with Hannah and Amy-Beth. Maybe I need to become a full-time lesbian."

"Good idea. Do that until I get there, and I can then convert you to getting properly fucked all over again."

"Sounds like an idea. I certainly won't get any fewer orgasms that way."

"And how's Hannah doing?"

"Oh, she's found a cute boy called Martin who's nice to her, but he's still pretty clueless in the sack, or so she says. Me and Hannah and Amy-Beth just seem to use the strap-on more when we wanna get fucked. Seems like we know more about how to do it than the boys here. Amy-Beth keeps asking us to fuck her ass with it. But Uncle Bob, we need you! Yes, you! When Hannah and me remember all the fantastic sex we had with you - in New York, in Florida, on the road - and compare it with what the pretty-but-dumb boys here can do, we so miss you. Please can you visit, soon? Just think, six wet and willing holes for you to use, any time. Amy-Beth might join in too, so that'll be nine! We'll do anything you want. Anything, Uncle Bob. We're all total sluts for you."

Fuck! I was getting a boner just listening to her.

"OK, Stacey, I'll check out flights and see when I can get to you."

"Yay! Make it soon, please." She must have turned to Hannah, and I could hear her say "Uncle Bob's coming over to fuck us!"

I heard Hannah say "Ohmygod! Yes, yes!"

My pants were now straining.

"Honey? Honey?"

She clearly put her phone back to her ear. "That's awesome, Uncle Bob. I promise we'll both be sooo slutty for you. And - and I'm sure Amy-Beth's gonna want it too. There's gonna be cum, like, everywhere!"

"Baby, please slow down. I'll be there as soon as I can, but right now I have to focus on Chelsea. As you know, she's not in a good place, and you told her she could stay in my house, so here she is and I can't leave her until she's ready."

"Oh, Uncle Bob, you know what to do. Just fuck her up the ass. She'll enjoy it, and she can go back to Dad and let him do it to her, because she'll know how to make it feel good. And Dad might even be grateful to you."

"Er, Stacey, what the fuck? 'Hey, Bob, thanks so much for fucking my trophy wife up the ass. It was exactly what she needed and now we're so happy together.' Doesn't sound like Michael to me. My guess is he'll hire some muscle to come around and see just how much shit they can beat out of me."

"Look, Uncle Bob, just - just give her what she wants. I know you're not getting enough since Hannah and me went away. I mean, fuck - how could you? Me and Hannah drained your balls all the time, so my guess is that there's like a gallon of cum in there waiting to be unleashed. Go ahead - squirt it up Chelsea's ass."

"You're honestly telling me to sodomize your stepmom?"

"Yeah, I guess. I made you do it to my mom, so you have to keep up the succession." She giggled.

"OK already. Just don't ask me to do it to your dad. Although that's a thought..."

She screeched with laughter down the phone.

"Please, Uncle Bob, I'm sure you'll know what to do with Chelsea, and she'll love you for it. You did it to me and Hannah and Barbie and Mom and Amy-Beth, and they all thought it was totally hot. Chelsea needs it. If you want, get her to call me and I'll tell her myself. But Uncle Bob, please, please be here soon. Hannah and me and Amy-Beth - we need it too. Now I've gotta go. Just thinking about you ass-fucking me has got me so wet that I need to get Hannah to go down on me. And maybe we'll use the strap-on on each other's asses to remind us of you. Love you. Ciao."

Before I could even echo her 'love you', the line went dead. I loved talking to Stacey, but every time it seemed to create some massive weather system that swept over me - a Category 5 hurricane of love and sex, down a phone line. My head was in a spin - and my pants were making a tent, thinking about all the naughty things I would do to her and her more-curvy friend when we next met.

But talking of curvy, I was concerned that, while I'd been on the phone to Stacey, I hadn't heard Chelsea emerge from the bathroom. Cautiously, I crept upstairs and peered into what had always been Stacey's bedroom. Chelsea was lying on her side on the bed. She seemed to be asleep. And she was naked. I could see her unfeasibly-large but still nicely-shaped titties, sticking out unnaturally despite the pull of gravity. Her long smooth, elegant thighs were in a kind of scissor position and I could see her smooth, elegant pussy.

I stepped back, feeling like some pervy voyeur, as the strain in my pants increased. OK, so Chelsea wasn't Stacey or Hannah or Barbie, but given the opportunity and my current state of desperation, there would be no question - yes, I would love to fuck her. But only if she asked me to.

So I headed back downstairs, grabbed a beer and, following Stacey's suggestion, started looking through some Bob 'n' Stacey porn - also including some Bob 'n' Hannah and Bob 'n' Barbie porn for good measure - trying to find something that, if she was amenable, might persuade Chelsea to allow me to show her how to enjoy having a dick in her ass.

Maybe an hour and a half later I was on my third beer, and had found a half-dozen examples of one or more of my lovely young partners enjoying anal with me, when Chelsea appeared, and sat down at the table opposite me. I should say at this point that she was wearing just a short, silky robe, barely a few inches down her thighs and kinda gaping at the top, so her arrival caused quite a stir, especially inside my pants. She looked a little worse for wear. 'Loaded' was almost an understatement. But, somehow, her makeup was still looking fresh.

"Sorry, I needed a little lie-down. I guess I had a lot to drink."

"No problem," I replied. I'd had earbuds in, and I stopped the video and shut the laptop down when she arrived.

"You - you looked in on me."

"Er, yeah. I thought you were asleep. I was worried. You were lying on your side, so I thought you'd be OK. You'd had a lot to drink and I didn't want you to choke on your own vomit - or anyone else's."

She gave me a strange look - unsurprisingly, really.

"So didn't you like what you saw?"

"Sure, you're very hot. But I guess you know that."

"I can't help it. I have a body that was made for sex. I was born like it."

"Guess your mom had a hard time giving birth. Just squeezing those tits of yours out must've been quite a trial for her."

She looked at me as if I'd lost my mind, which I felt was unfair. In reality I'd probably just mislaid it somewhere.

I smiled at her. "Sorry. I guess what you meant to say wasn't that you were born with that body, but that it developed naturally, hopefully after puberty."

"Bob, has anyone told you you're weird?"

"I've been called a lot of things. 'Weird' is one of the lesser insults. In fact, when I think about the people I know who would usually be considered 'not weird', I'd be happy to take weird."

Her expression showed bemusement. "So you looked in on me, but you didn't hang around."

"You were naked. I thought you were sleeping. I just wanted to check you were OK."

"Most guys would've stayed to take in the view. Some might have done more."

"Like you say, I'm weird. But not gay. You're a very attractive woman, Chelsea, and I'm sure you know that. But you're here because you've got troubles and I don't want to add to them."

She smiled. "Stacey said really nice things about you. I thought, 'Yeah, but he's Michael's brother. He's gonna be difficult.' She told me you'd look after me if I stayed here, and you have. I really appreciate that."

I smiled back. "Hey, Chelsea, I'm really not that difficult. Just weird."

Her smile broadened. "But, see, I still don't understand how Stacey knew you were good at anal. So just how weird are you, Bob."

Fuck, I'd hoped she would have forgotten that line of thinking, or been too loaded to consider it any further. I sighed. Right, time to fess up. "OK, do you promise not to tell anyone?"

"Sure. Anything that you say will stay with me. Or possibly between me and Stacey." The smile turned into more of a smirk. I ignored it.

"OK then. One night, a few months ago, Stacey asked me to take her virginity. Boys were hitting on her; boys she didn't trust to treat her well, and who she didn't think were worthy of her. I've always told her she's a princess - my princess - after all, and I guess she'd come to believe it. We'd always loved each other, ever since she was tiny, and she trusts me more than anyone else - even her mom. At first, I said no, but she was insistent. She virtually begged me to do it."

"Sure she did."

"Look, Chelsea, I'm telling you the truth. Call Stacey and ask her. But believe me, she was the one who instigated all of this. And, it seems, for a very similar reason that you're staying with me now. Because she didn't want to have sex with someone she didn't respect, and who she knew would treat her badly."

"OK, OK, I trust you. But you knew that it was totally illegal?"

"Sure I did. But I thought 'no-one needs to know. It can be our little secret. And it'll just be the once.' I was wrong."

"So Stacey wanted more?"

"I'm proud to say that she came on her first time. Not many girls do that. But then - then she definitely wanted more, and one of the first things she was desperate to try was anal."

"Really?"

"She'd seen some anal porn and thought it looked scary but hot." I didn't mention it was my anal porn she'd been watching. "I'd done it with a previous girlfriend - who, incidentally, also instigated it and loved it - so I could honestly tell Stacey that I knew what I was doing. We did the deed and I made her come again. Since then, we've had an ongoing deeply sexual - and deeply loving - relationship. We'd dearly love to get married, but it's kinda technically illegal. But since our relationship turned abruptly sexual, and recognizing that we can't marry and remain monogamous, Stacey has convinced at least three other women that I'm capable of giving them pleasure from anal sex, and I'm proud to say I've proven her right every time. So now you know, what are you going to do with the knowledge. I trust you won't say anything to Michael, Dolores - or the cops?"

"Why would I? I'm seriously pissed with Michael, I don't know Dolores and I don't think she likes me anyway, and every dealing I ever had with the cops in the past turned out badly for me. I hear what you say about anal, but it's really not on my bucket list. I've had two bad experiences, and that's quite enough."

"I understand, but what preparation did you do before those two bad experiences?"

"Well, not much, I guess. Michael slapped some lube on his dick. The first guy tried to shove it with just spit and pussy juices."

"Well it's no wonder you had a shitty time. Preparation takes at least a half hour, and preferably a lot longer. You need to clean, lube, stretch and get excited. Stacey goes around with a butt-plug in when she thinks she'll want anal - which seems to be most of the time. She and her friend Hannah have matching vibrating butt-plugs. They pop them in after cleaning and lubing, and sometimes get off on the vibrations alone. They certainly get juiced-up when they're using them. I think Stacey's left some of her toys in your room. You may like to try them."

"Are you serious?" she said, giving me a concerned look.

"Absolutely. I've been thinking about your options. You could leave Michael, but that might be a financial challenge for you unless you get a great lawyer to help rip up the pre-nup. If you can't think of a neat way of earning a lot of money, you may have to return to your old vocation. I'm sure you'd be very good at it and you could probably earn big bucks, but I get a feeling you don't want to go there. Or you could crawl back to Michael and continue to suffer the pain and degradation he's been inflicting on you. You could see if he'd be willing to join you in counselling but, knowing Michael, that seems unlikely. Or you could prepare and be ready for his next onslaught. You might surprise him. If he found you were happy for him to fuck your ass, and if you even enjoyed it, it could move your relationship to a different level. Your choice."