Anal At Last Ch. 09

[The story so far: I've recently divorced my wife, and am raising my son by myself. After a long abstinence, I've met a woman (Angela) and we've been indulging in anal sex, new to both of us. In the course of getting to know each other, I'd helped her out with an email problem, and as a result, gotten access to her email, after seeing one from a friend of hers (Jules for short, probably Julia or Julie - I'd never met her or heard of her). My babysitter (Samantha) was staying at my place one night, and caught me "doing a money shot" over Angela, and I saw her in the shadows of the stairs. None of us had broached the issue, but in a deep conversation one night with Samantha, I found myself backed into a corner and admitting that I did think about her naked...

The cast:
Me: 36 yrs male
My son: Daniel
My girlfriend: Angela, 40 yrs
The babysitter: Samantha, 18 yrs
Samantha's dad: Bill
Samantha's brother: David
Bill's late wife: Michelle
Bill's girlfriend: Barbara
Angela's friend: Jules
My ex-wife: Sharon
Daniel's friend: Stephen
Stephen's parents: Ken and Simone]

*

I sat with baited breath. I'd just divulged that I thought about her naked, with all the implications behind that. How would she respond?

She just sat there. Perhaps not the first thing I thought she'd do. Run out screaming? That was on the list of "Possible responses to me telling an 18 year old girl I thought about her naked". Slap me? That was on the list too. But just sit there? No way.

I waited. Letting her finish whatever thinking she was doing.

The doorbell rang. Jesus wept, of all the times to come, why is the take-away coming NOW?

I sat there, till Samantha got up and answered the door, looking like a zombie as she walked across the room. A few moments later she came back in carrying the take-away.

"Mmm. Smells good," she said.

OK, what's going on?, I wondered. She put the bags on the coffee table, went into the kitchen and returned with plates and cutlery, still saying nothing. Then she dished up some of the food onto our plates, and handed one to me.

"Samantha, say something. What's going on?"

"Eat up before it gets cold Andy.... Oh, yum, this beef is delicious."

She picked up the remote control, and turned on the TV. One of those programs came on where people send in clips of their animals doing stupid things. We sat, in silence to begin with; eventually starting to chuckle at some of the clips, till eventually it was like nothing had happened. But I could tell by a glazed look on her face when the adverts came on, that she was still thinking things over every now and again.

But I knew that it had all happened, and that we had to deal with it. So when we finished, I took our plates away (she didn't like spare ribs, unfortunately, so I didn't get my kick of seeing her suck her fingers clean). I sat back down, on the sofa opposite, and flicked off the TV.

"Samantha. We've just had a very open heart-to-heart, and I'd like to know where we stand. Talk to me."

She sat back in the sofa, hugging her baggy jumper around her.

"Andy, it's weird. I mean, I never thought that you would think of me like that... and I'm not sure what I think."

I waited for her to continue.

"Can I be frank with you?" she said, eventually.

"Of course."

"Well - don't get too freaked out here, heaven knows I'm freaked out enough myself - but part of me likes the idea that you think of me that way. No-one has ever felt that way before - or at least they've never admitted it - and it's nice to know that I can have that effect on a man." She took a sharp breath in. "Oh! I don't mean you specifically, of course. Just a man… Any man.

"But part of me is scared that I don't really know how to respond to that. I'm eighteen years old, and I don't know how to handle someone who thinks of me like that. Don't you think that's pathetic?"

"Not at all Samantha - you're not the only one like that. Hell, there were times when I was with Sharon that women came on to me, and I - In fact, now that I mention it, there's a woman at the swimming pool who regularly still does come onto me in the most brazen way, and I STILL don't know how to handle her. And I'm a damned site older than you are. Don't you think THAT'S pathetic?"

She snorted her approval. "Yeah, I guess so. You got me beat. I guess I'm saying it's a lot to think about. And I guess I should be flattered, though."

"So... are we still friends?"

"Oh Andy, you're such a boy sometimes. How can we be friends when all you can think about is what I've got under these clothes?" As she said this, she smoothed down the front of her jumper, allowing her shape to show through for once. Was that deliberate? Either way, those puppies look delicious, I couldn't help thinking. Then she smirked at me, obviously having seen where I was looking. I shook my head, laughing, and turned the TV back on.

We spent the next hour or so in near silence, watching TV. Me wondering how this was going to end - would she want to even speak to me in future? Would she think I fancied her? Would she tell her dad? - and her seeming to take a few opportunities to stretch, thrusting her boobs out, or looking at me from the corner of her eye then looking away quickly as I returned the look. But at other times, she looked worried, deep in thought, as though she really wasn't sure what to do next.

Then she stood up. "Andy, I think I'd better go. I've got a lot to think about, and it'll be easier back at home."

"Of course," I said, standing up quickly to help her get ready. "I'll phone for a -". Then I remembered. "Oh hell."

"What's wrong?"

"Well your dad ... errm... after we met at the supermarket... he phoned me later, and we kind of agreed that I'd be out late tonight, to keep you here... " I hastily corrected myself. "- I mean, to give your dad some quiet time with Babs."

"I know full well what you meant. Dad wants me out of the way so he can have Barbara to himself. After all, that's what you men think about all the time, right?"

I couldn't tell whether she was angry or playing. "Well, that's not what I meant -"

"That's exactly what you meant. If you meant it about you, then it applies to my dad as well."

"Now Angela, be real, your dad's a nice bloke -"

"Yes, a nice bloke. But still a bloke. And I thought you were a nice bloke, and you've admitted that you have lewd thoughts about me. Case closed. He wanted me out of the way, so that..." She paused mid-rant. "Oh, what's the use. So that's the plan is it? I stay here tonight?"

"Well, not the plan, but it's a suggestion. And I never said I had lewd thoughts, just that I imagine you naked."

"You can't get that much lewder. Right then..." She paused, thinking for a moment, "If I'm being kicked out of my own bed, maybe we should go to yours. Come on, let's go to bed." She held her hand out to me to lead me upstairs.

Fuck me! I didn't see that one coming!

"I... er.... sorry?", I spluttered.

"Well, if you're having lewd thoughts about me, maybe we should follow up on them. After all, your advice was to practice before I get married."

"You want to ... with me... now?"

She looked at me for a moment, and then burst out laughing. "Oh, Andy, you should see your face. I wish I had a camera." Then she stepped towards me, leaned in, and gave me a kiss on the cheek. "You're a decent man, Andy. It's good to have a friend like you. But right now, I need to think about what you've said. So I'm going to bed. The spare bed. Alone. And you can go upstairs and ... well, think about what Angela said to you on the phone, for example. And please, whatever you do, try to ignore the fact that I didn't bring any pyjama's with me, and I certainly won't be wearing these Mrs Doubtfire clothes when I'm in my bed tonight."

And with that, she went upstairs. No, she flounced up them. How could someone so naive be so coquettish as well. That was enticing combination.

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I phone Angela a bit later.

"Hey babe," she answered, "how are you and sweet, sweet Samantha getting on?"

"Fine... but I had to admit something to her."

"Oh jesus, Andy, what's happened?"

"Well, I kind of painted myself into a corner, whilst talking about how all boys do is think about women, specifically women naked, all the time. And men do it as well. And how boys and men wank alot. And -"

"And she asked you if you thought about her like that?"

"Yes. How did you know?"

"I'm a woman. That's what I'd ask."

"Oh. I see… Well she didn't ask if I wanked over her. Just if I imagined what she looked like naked."

"And I'm guessing from your tone of voice that you said yes."

"What was I supposed to say? She looked like it was really important how I answered. If I said no, she'd have been upset. If I said yes, well... she might have been upset as well, but at least there was a slight chance she might be flattered and pleased."

"What you mean is, if you'd said yes, you were hoping certain things would happen, right?"

"No, Angela, be serious. Well, OK, maybe a little bit. But I would have stopped it, as that wouldn't have been right."

"But it would have boosted your frail little man's ego to know that she, a sweet innocent 18 year old, wanted you, an old fart. I know, I know, I've been there before. So how did she react?"

"Well, she thought about it a lot. We had dinner. She teased me, and now she's gone to bed."

"And you want me to come over and do the whole Samantha fantasy thing again, is that it?"

"Baby, you know that's not what I want. Well, OK, again, maybe a little bit of me. Actually, quite a big bit of me. And it's getting bigger by the second... Anyway, I wanted your advice on what to do next. You're a woman, you should know better than me." I waited for her divine inspiration.

"I'm a woman, am I? Glad to noticed. I was beginning to think that your obsession with my ass had got you all confused. So she's talking to you, joking, flirting, and you're still asking me what to do?"

"Yes. And I'm still waiting for an answer, I hasten to add."

"She seems OK to me. Let her sleep on it. Call me in the morning if the shopping's off."

"Is that it?"

"What did you expect?"

"Well, I was kind of hoping you'd say something which would lead me into seducing you to coming over here for the night."

"So that you could call me Samantha as you came in me? No chance, baby. You're pleasing yourself tonight. Give me a call tomorrow. 'Night!"

And with that, she was gone.

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I sat up for a bit longer, ruminating over everything that happened, and then went to bed. But before actually going to sleep, I logged and quickly checked my email, and obviously check Angela's as well.

There was another mail from Jules. This time, I scrolled to the bottom and read back up the way, from the oldest mail to the newest, in order.

First, there was an initial mail from Jules:

Angela, my dearest.

What's the latest on the Andy front? Is the hunk of spunk still going strong?

I had a chance to watch that video of yours at last. I know I was there filming it, but it's always great to see the output of your own artistry without seeing it through the lens. I think it turned out quite well, don't you?

I bet he wanked himself stupid watching it.

My, how I'd have loved to have been a fly on that wall. I can see it now, Andy wanking that fine cock of his, playing with his balls, unable to take his eyes of you with that vibe in your asshole. I bet he came when you started pushing the rabbit into you as well - no hot blooded hetero man could resist that, I'll bet.

Here's some news: I met a new beau last night: Nick. Or Nick the Prick as I've called him. Not in a bad way (as in, he's not a total prat like that last gym catch), but in a good way (he's scrummy, and almost as well endowed as Andy). Nice fit body. Buns of steel and all that.

Sweet jesus, but it's been a good time since I had a nice stiff cock in me. Nick was great - taking it slowly at first and then getting a bit more physical with each passing minute... and there were a lot of them, let me tell you. He probably lasted longer than any one I've ever been with (and honey, you know that's saying something!). I think I'm walking a bit funny today as a consquence!

Maybe the four of us could get together, waddyafink? I can just see it now, you and me kneeling on the sofa, our arses bared to the world, with Andy and Nick standing tall and proud behind us, unable to believe they're about to fuck the best asses available in the world. Then we'd get the boys lubed up, and let them get us lubed up, and then they push into our rears at the same time, filling us to the brim.

That would be sweet ... you and I getting our arses reamed together... side by side. Will the boys be able to last as long when they're seeing two delectable little pairs of cheeks side-by-side?

Of course, you know my penchant for a little ass-to-mouth, so I'd be forced to go down on both of them after they'd come in our tushes. I hope you don't mind... it might be the only chance I get to touch the fantasy-made-real that is Andy....

Hugs,
J. x

Jesus, she wants a foresome? I wondered how Angela would take that, and read on eagerly.

Jules, you trollop, keep your greedy eyes and grubby little hands of my fellow.

It's going well with Andy, really well. I trust him totally. So stop taking the piss out him.

You know on the video I mentioned wearing a schoolgirl outfit, well I've gone and bought one. Jesus, I look positively nasty in it. I think he'll come in his pants when he sees me - short skirt, blouse tied off at the waist, knee-length socks, and I'll be wearing pigtails. Just like Britney.... boy, that girl's got a lot to answer for. I'm going to surprise him with it soon. I'm loving the pigtails - I'm hoping he'll use them to hold me back while he gives me a right old going over.

Do you think he'll follow up on the "Daddy" section of the video? Now, you know me, I've got nothing like that going on with my dad, where-ever he is now, but it's one of my secret fantasies: to be spanked by some archetypal father-figure, stern, demanding, impossibly turned on at the writhing female flesh beneath him, knowing that it should be avoided at all costs, but unable to resist the call of the loins and the smell of hot female juices wafting up from below his hand..

Andy did get a hard on when we spanked recently (listen to me, it's ALL recently, given how long we've known each other)... I just think he won't go along with the Daddy bit - as he IS actually a dad, it'll seem a bit weird to him. I wish he would though - it'll be the fulfillment of a lifelong fantasy.

If he does, I'm going to do something special for him in return: he mentioned at some point that he's never been deep-throated. I'd love to do it, but never met a man big enough, or important enough to me, for me to bother learning. Do you have any tips?

Angela.

Only one thought crossed my mind: "Ah man, that's gonna be one hot session. 'Do I want to be the Daddy?' ... who the fuck wouldn't when it's Angela being the girl? And knowing he's going to get deep-throated afterwards?" I could feel my prick paying attention already....

Then finally, Jules' reply:

Ang baby, of course I'll teach you my tricks. But it's gotta be a practical exam, not a theoretical one. Bring that well-used old vibrator of yours over one night (how's about Thursday?) and I'll teach you everything I know. By the time I've finished with you, you'll be able to deep-throat a sword. And I don't mean a pork one!

And if the worst comes to the worst, we'll do this: you turn up in your little girls outfit and get yourself fucked good and proper. Then tie him up, blindfold him, I'll come out of hiding, and I'll give him his deepthroat. He'll never be able to tell the difference. Of course, if he wants it again in future, you'll need to keep on wheeling me out, but I think I'll survive. Hell, maybe I should tie you up as well and let Andy's nine-incher stretch my back passage as well as yours. Sounds, interesting, yes?

Love and kisses,
J.

What? Jules was going to teach Angela how to deep throat? Jesus, I hoped it works. I'd never been deep-throated till that point. And she was joking about standing in for Angela if Angela couldn't do it... wasn’t she?

To say that my dreams were all about Samantha would be a lie. Many of them involved Samantha and Angela. Others involved Samantha, Angela, and the as-yet-unseen Jules, all three of them deep-throating me in turn. Then me tied to the bed, Jules planting her ass on my cock, Angela and Samantha kissing her, sucking her tits, fingering her cunt, licking her cunt and then kissing me.

----------------------------------

I woke up with a raging erection, but could hear Samantha and Daniel downstairs playing, so I took the rare opportunity to lay back and have a quick wank, thinking about Angela coming over later, and her and I having quick and dirty sex together.

Then I showered, dressed and went into the kitchen. I could hear Angela's voice as I went downstairs, the two girls planning their day out. I turned the corner into the kitchen, and there was Angela - dressed in ass-hugging culottes, a blouse with a low-cut neckline, and her hair pulled up in a clip behind her head - and Samantha - dressed only in a pretty tight t-shirt, that came half-way down her thighs, and some pyjama bottoms. And quite blatantly, no bra.

I stopped to take in the scene.

"Andy, sorry," said Samantha, "this is all I had to wear. No jokes about my dress sense!" That made it all the more painfully aware to me that she had not much on, if anything underneath it. And jesus christ her tits looked amazing. Just jiggling around as she shifted position. In fact, I could see her nipples, slightly stiff against the material. Below that, she had what seemed to be a flat stomach (at least, the t-shirt was loose around her waist), a large but shapely ass (the t-shirt hugged it in all the right places).

I stared, my mind gone blank.

"Something wrong Andy?" asked Angela, smirking at me.

"Er... no. I'm just not used to seeing you walk around like that," I said to Samantha.

"It was Angela's idea. I had that old dressing gown of yours on, that hangs behind the door in the spare room. But I was getting hot running around with Danny, so when Angela arrived, she suggested I take it off. And this is all I've got, apart from my clothes which are airing upstairs." As she said this, she grasped the front of her t-shirt to show me what she meant.

My mind seized at this point, unable to deal with the transformation from Big Baggy Jumper Girl to No Bra and Tight T-Shirt girl. I went into auto-pilot, saying good morning to Daniel, playing with him for a few minutes, and then making my breakfast while the girls chatted. Angela kept making eye contact, nodding her head as if to tell me to check out Samantha (like I needed any persuasion!) when the girl wasn't looking. Samantha, for her part, just kept flouncing around. I'd say she was doing it on purpose, but I thought she was just somewhat innocent of the effect it was having me.

As I finished my breakfast, Samantha leapt up from her seat, setting her juicy breasts wobbling under the t-shirt, and said she's going for a shower. Angela moved over to the seat next to me, checked that Daniel was still engrossed, and slid her hand up my thigh.

"Just as I thought," she whispered. "Another hard-on caused by that girl. One of these days that's going to upset me." She slid her hand up and down my bulge as she talked. "She hasn't mentioned anything specific about last night, other than to say that you'd had a big talk about boyfriends, and her dress sense, and you'd made some good points that she was going to take on board. What have you been telling that girl, you dirty old bastard?"