Anal at Last

[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. Then one night, the babysitter (Samantha) that normally looks after my son had stayed the night to give her father, a widow, the house to himself on his first date since his wife died. I'd gone out for a drink, and come back home forgetting that Samantha was staying. Angela turned up unexpectedly, and we'd ended up with me coming all over her face in a good old "money shot" - and I saw movement in the dark hallway that must have been Samantha watching from the shadows. She wasn't there when I looked, Angela and I went to bed, and wanked each other off over fantasies about a threesome. Fortunately, Samantha said nothing about it the morning after, but there was some sexual frisson between us, I thought. Later, I'd read Angela's email (which I'd seen when I helped fix her PC), where she shared intimate details of our first anal sex, with Jules, a friend of hers, along with some hints about some fantasies of hers that she'd like to enact with me...]

The next few days were really spent either with Daniel, or getting everything ready for the conference. Angela and I spoke on the phone a few times, but nothing sexual happened, other than me having a few wanks thinking about her. During the course of the calls, I mentioned how much I wanted her, joking that it was her body I wanted, not her chat or her mind, and I kind of got the impression that she might even have been rubbing herself as we talked.

So off I went to the conference. Busy times ensued, having to spend the evenings socializing and networking, and the days either speaking or listening. Daniel was staying with his aunt for the 5 nights I was away, and I made a point to speak to him by phone once or twice a day, and by webcam first thing in the morning before I started the day's work.

Samantha had phoned me before I left, asking a favour. Her dad was going out with "that woman" again, and she wasn't ready to meet her. So she'd told her Dad that she was staying with a friend for the night, making sure that she wasn't in her own home when the date was around. But her friend couldn't put her up as her parents had some family members visiting, so Samantha was kind of stuck with nowhere to go. Before she even asked, I offered my place, since I knew she had the key (just in case anything should happen whilst she was babysitting). She was ever so grateful, and said she promised to look after it.

So, one night during the conference, I logged onto my mail to fire off one to Angela, a little e-porn about what I was going to do to her one night when I got back. I sent that off, and then, on impulse, logged into Angela's mail again.

Yep - another mail from the mysterious Jules:

"Ang, just a quick update. I managed to get the photos printed off at home - it was too much of a risk at work. They turned out pretty good - Andy's going to come in his pants when he sees some of them.

I still can't believe we did that - and that you weren't the least bit put off by me being there. Still I suppose the page 3 models and porn actresses get used to it, and at least you know me, and I'm not some sad fat bastard who works in that industry so he can wank himself silly over the beauties he's seen through a lens that day.

I've dropped the photos round to his house and spread them round as agreed. He'll be delighted to discover the treasure trail that leads to the pot of gold at the end :-) Mind you, he'd better appreciate it... I went through four DVDs before it verified OK, fucking cheap blank discs. Good old TDK worked though - never let me down yet, and God knows I've used enough of them when sending porn over to you.

Note to self: must give you the keys back before his conference ends!

Hey, I've got a better idea: maybe I'll keep the keys, and sneak in one night whilst he's asleep, creep up to his room and let him have my wicked way with my ass instead of yours. Heck, maybe I'll give you the keys back but make a secret copy of them and do it anyway, without telling you :-)

(Oh, and just to confirm your suspicions: I did watch the movie you took with the mobile. Obviously. How was I going to pass up that opportunity? His cock looks mighty tasty, and seeing you give him head was quite the turn on as well. Only two points: first, next time use a real camera, not your mobile phone; second, try not to wake him up - I would have loved to have seen you swallow his come down, instead of hurriedly stuffing your camera under the bed as he woke up - I missed the best bit, spoilsport!)

(OK, third point: can I join in next time? Do you think he'll like having two hot mouths round his cock and balls at the same time?)

Your partner-in-porn, Jules"

Wait a minute - they were leaving photos at my house.

Shit, what if Samantha sees them!

I started replying to Angela to say not to send the photos, and then remembered that I wasn't supposed to be reading her mail.

Fuck! What now?

I could phone Samantha and tell her the house was off-limits. I'd need to find an excuse, but I can do that later. Then I saw the date on the mail - it was a couple of days old.

Oh my god, she might already have seen the photos...

I got out my phone. Samantha didn't answer, I got her voicemail.

"Samantha, listen, it's Andy. I hate to do this to you, but I need to ask you to find somewhere else to stay. Er... let me know if it's an issue, and I'll get a hotel room for you. Don't worry about the money, it's all my fault. Umm... basically, Angela's arranged a bit of a surprise for me for when I get back... and .... er... it might ruin the surprise if either you're there when she sorts it out, or if you're there afterwards. I'm really, really sorry - let me know if you need the room, and I'll book you somewhere nice. You can pamper yourself - have a spa break, you know, massage, sauna and all that. Really, don't feel uncomfortable, it's all my fault. Let me know, OK. Err... bye!"

Hopefully that'll do it. I'd need to work out what the "surprise" was for when Samantha asked (I couldn't really say that it was sexy photos and a movie of me getting head), but I'd got a couple of days to work that out. I sat back, relieved, hoping that Samantha got my message. Then I texted her, asking me to call her urgently, just to make sure she'd got the message. I didn't have her dad's number, so I couldn't call her at home.

I spend the rest of the evening frantically checking my mobile for responses, making sure it was turned on, etc. Nothing. Not a peep.

I managed to eventually get to sleep. I must have been fretful, as all sorts of sordid dreams ran through me. Angela and her friend taking photos of Angela wanking her ass with her dildo, while the two of them watched the webcam shots of me wanking. Angela and her friend getting carried away and having sex together, all tongues and nipples and hands in cunts. Angela and Jules kneeling before me, both of them sucking me and licking my balls, till I come all over them and they lick it off each other. Samantha at the spa, getting massaged, and the masseur getting a little bit carried away, brining that sweet little girl to a screaming orgasm. A male masseur (me?) coming in at the noise and fucking her doggy style, taking her virginity. The still-virginal Samantha in my house, staring at disbelief at the lurid photos of Angela wanking, and unable to contain herself, Samantha wanks herself off with a screwdriver from my toolbox. And so on, and so on.

I woke early, around 3:00 according to the alarm clock, to my phone text beep. It was Samantha:

"Sorry it's late. Got your message. It's OK, decided to stay with friend after all. Didn't want to be alone at the moment. But it's a bit cramped sharing a bed with her. Sorry again to call late, sounded urgent. Call me any time if it's a problem. Sam x"

Phew.

I drifted off back to sleep. This time, the dreams were about Samantha and her friend, sharing a bed, getting hot and bothered, unable to find a position to sleep in that didn't involve them touching in some way, then resigning themselves to it, curling up together, cuddling, enjoying the contact. A touch, a kiss, a questing hand, opening thighs, thrusting hips, writhing tongue, quiet moans.

I awoke. Fuck, my cock as hard as steel. I pulled out my phone, and took a shot of it. Sent it to Angela with the note:

"Baby, woke up thinking of you. Got a present for you. Will give it to you when I get back."

A few minutes later, she texted me back:

"Thanks for waking me, bastard. Can't you control that cock of yours, at least till I'm awake. Can't wait till you give me the present, as long as it's given good and hard. Have fun playing with yourself till then, you sad little man."

Unfortunately, I'd woken just before my alarm went off, so I had no time to easy my throbbing erection. Just had to reconcile myself with having saved my bacon regarding the photos.

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

The conference went on for two more days, then I left to go home. En route, I got a text from Angela:

"Hopefully, this'll catch you on the way home. Next time you go away, can I come with you? Was feeling really horny today - would have liked a lunchtime shag. Shame that we won't see each other tonight. Hope you enjoy your surprise!!! Ang."

I didn't respond for a bit, and then remembered I wasn't supposed to know anything about the surprise, so I pulled over and texted back

"What surprise?"

A few minutes later, she came back:

"Oh, just something special I thought you deserved after your hard week's work. Can't say more - it's a surprise!"

So I left it at that and drove home.

When I got there, I opened the front door. In the middle of the hall was a piece of paper. As I got closer, I saw it was the back of a photograph. I picked it up, and saw an arrow drawn on it, pointing to the kitchen door, with "NEXT" underneath it. I looked that way, and saw another photograph just under the door. Turning over the one in my hand, I saw a picture of Angela wearing a black ensemble - blouse, skirts, stockings, shoes, holding a large card over her head saying "WELCOME BACK. ENJOY". She had a big smile on her face, laughing with the person holding the camera.

I went on to the second one: another arrow and the word "NEXT" - presumably to lead me on to the next one in the series - and this time the picture was of Angela sat on a chair, leaning forward, exposing her cleavage, as she undid a shoe.

The next one was of her looking down at her hands as she undid the last button on her blouse, her chest and stomach slightly exposed, showing her Wonderbra-enhanced cleavage.

Next: her blouse off, her bra and skirt nicely showing off her figure, reaching up to unclip her hair, lifting her boobs up delightfully.

Next: she's undoing her skirt.

Next: her skirt is off, leaving her stockings, knickers, and bra. She's looking mighty fine, sat astide a dining chair in the manner of Christine Keeler in that famous photograph.

Next: her ass is towards the camera, one leg raised on the chair as she is undoing one stocking.

Next: she's sat on that chair normally, both stocking off, legs spread, facing the camera. One hand is inside her bra, the other inside her knickers. Her eyes are closed, head rolled back slightly.

Next: a close-up of her bra-less breasts, one nipple being played with by her hand.

Next: she's naked now, again with her back towards the camera, hands up as if covering her breasts, her naked ass tense as she stands in just her high heels.

Next: she's lying on the bed, one hand playing with a tit, the other with her cunt.

Next: a close-up, two fingers parting her lips and pushing inside her.

Next: she's kneeling on the bed, ass towards the camera, one hand between her legs.

Next: same position, but this time she's got her vibrator just entering her cunt.

By this time, I was feeling a bit hot under the collar myself, so I took my jacket off and threw it on the bed, kicked off my shoes, and went looking for the next photo.

Next: same position, vibrator well into her cunt, hardly any showing outside it.

Next: on her back, legs spread, vibrator in one hand, half-in half-out; the other hand rubbing her clit.

Next: a real close-up - her labia clinging to the vibrator as it was inside her, her juice glistening in the light, the other hand separating her lips at the top to show off her clit.

Next: Back on all fours, one hand still using the vibrator inside her, the other reaching back to run a finger down the crease of her ass.

I started rubbing myself through my jeans at this point, remembering everything we've done anally since we met.

Next: same position, but one finger actually in her ass. She's got her head turned round to the camera, eyes half-closed in ecstasy.

Next: same position, but she's running the vibrator between the cheeks of her ass, other hand reaching back to finger herself.

Next: a closer view, the tip of the vibrator just pressing into her rectum. Lots of sheen from either lube or her own come.

The dirty tart was turning me on. I undid the belt and fly of my jeans, reaching in to pull my cock out of my boxers, surprised to find a wet patch at the end where I was already so turned on.

Next: The vibrator was in her ass by I guess a couple of inches, her sphincter muscles closed tight around it.

Next: She's standing up, no dildos to be seen, holding another place card up, saying "Watch the DVD". I looked around, and there on the bed was a blank DVD case. I whipped out the DVD, and booted up the PC ready to watch it. Whilst I was waiting for the damned thing to boot up, I kicked off my clothes, and sat at the PC, gently wanking as I looked through some of the photos again.

Eventually, the PC opened up the DVD file listing. Two files, both movies, so I double-clicked the first one. It seemed to be what I'd just seen in photos, but filmed. It jumped occasionally as her position changed, or presumably as the photographs were taken, but essentially was a static tripod filming.

I watched her strip in front of the camera, showing off her great body in ways that can't be seen in static photos. Every so often, she would bring her hands to her tits, her smooth flat stomach, her bum, her mound, and rub, or tweak, or otherwise play with herself through her clothes.

I watched her start to play with herself, moaning to the camera, writhing her hips, thrusting her groin into her hand as she wanked herself. Then she grabbed the vibrator from somewhere off-camera, and started running it around her tits, her nipples, down her stomach to her groin, and then pushed it inside her, grunting as she did so.

Then as she was getting really turned on, she turned over onto all fours, and started playing with her asshole, spreading some lube that she had beside her, fingering her rectum, running the vibe around her hole, then pushing it slowly, oh so slowly, inside. God, that turned me on so much. I had to slow down my wanking to avoid coming just yet - after all, I still had one more movie to go. But I rewound the movie and watcher her push the vibrator into that tight little asshole again.

That movie ended soon afterwards, so I ran the second one. She's still on all fours on the bed, but this time watching her own PC. The person holding the camera zoomed into Angela's PC, and I could see the movie taken by the webcam, of me wanking those few days ago.

Angela's voice came over the air: "Do you recognise that baby? That's you, wanking in my house the other day, watching porn, and it's got me so turned on... Did you realise the webcam was running, recording your every move? I've been watching this over and over recently, so I thought I'd give you something in return for when you get back. I hope you like it...."

Then the view changed - somehow, they'd spliced together two movies side-by-side: the first one was the webcam shots of me wanking, the second was movie of her continuing where the photos and first movie had finished off.

As I put my hand inside my boxers in the webcam shot, she pushed the vibrator deep into her ass. "Oh baby, I think it's so unfair of you to keep your cock hidden when I'm showing you my all, don't you think? ... Oh, there you go, your hard penis peeking out of your shorts... oh, god, that's good, you look so turned on baby... did you like the porn I left for you?"

My webcam self then continued wanking, just using one finger and one thumb to move my foreskin up and down. "Oh, fuck, Andy, that's so horny... do you wank like that when you're thinking of me? Or do you save it for when you're watching porn? Are you wanking like that now, as...

oh...oh god this vibe feels so good inside my hole

.... are you wanking like that now, as you see me fuck my own arse? I'm your own little porn star, Andy, I'll do anything you want..."

[My webcam self finally exposed his entire cock for the audience...]

"Oh, there it is, your pride and joy. It's standing up real big baby. Is it big now? Are you liking...

oh fuck that's good

... liking what you see? Does it turn you on...

aahh

... to see me fuck my own arse?... Oh baby, you look so good, giving yourself big strokes... I wish I was with you now so I could reach out and take over ... I love the feel...

oh fuck

.... of your big hard cock in my hands... or in my mouth...."

She was still fucking her arse with the vibe, but... "Oh baby... where have you gone?" She'd reached the point where I'd gone to get her vibrator and knickers.

"Baby, you're so bad.... I wondered what you were doing here when I watched this the first time...

oh, my ass is so full baby

... but then I realised that you'd found my little movie collection.... I wish you were here baby... you could spank me for being a bad girl who downloads porn... "

She raised her voice, making her sound alot younger.

"Will you do that Daddy? Will you spank your little girl next time you see me? Will you put me on your knee, pull down my knickers, and make my bum red for being a dirty little slut? ... Maybe I should wear my schoolgirl uniform... will that turn you on Daddy? "

Oh fuck, she's got a schoolgirl uniform. Visions of Britney Spears in that video came to mind, and I had to stop wanking before I came... I was enjoying this, and I wanted it to last.

"Daddy, I can't believe you called me a horny little minx. I'm such an innocent little girl; I don't understand half the things you do to me... Is it wrong for me to like a little excitement when you're not around?"

"Oh! Daddy! Should you be touching me there? No-one's ever touched be there before..."

Her voice dropped back to normal.

"I miss you baby, I miss your hard cock filling me up...

oh god that's good

... It feels so good when you force yourself inside me... I had to get some porn for when I'm really missing you... when I need you to spank me and fill me with your big hard-on and make me do things that feel so naughty..."

Now she reached off camera again - and pulled out the rabbit!

"Oh, Andy, you found my favourite movie. Did you like it? I heard you talking, telling the girls to do it more, to do it harder, to lick each other, rim each other, and it really turned me on. Are you watching baby? ...

oh fuck

... watch me, I've got a dildo up my ass and now I'm going to push the rabbit inside my other hole.... both holes filled just like in the fantasy the other day ...

oh Jesus that feels tight

... where you said I'd have my toy boy's two mates ...

I don't think I'm big enough baby

... fucking me at the same time... can you see Andy?"