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. My babysitter (Samantha) has watched us have sex, and confessed to Angela. That set Angela thinking, and she agreed I could start seducing Sam, but without letting Sam know that it was planned. This has just gotten to the point where I've had sex with a blindfolded Angela with Sam silently being wanked off by me; then me blindfolded, pretending that I didn't know Sam was giving me a blowjob whilst I was supposed to be in 69 with Angela.

Angela has informed me that she's off to the US for a year, just as we're getting close. And she's agreed we should have 12 partners whilst we're apart: one per month; long enough to have good sex with them, but not long enough to fall in love.

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

Peter: Angela's young neighbour

Charlie: Angela's friend

Jules: Angela's friend (never met)]

I lay and chatted with Angela for a while, and got to the point of whether I should visit Sam or not during the night. I was torn in two: I wanted to continue our little liaisons, after all, as far as Sam was concerned, I still didn't know about her and Angela ganging up on me and me coming down Sam's throat. So, if things went as they had done recently, I really ought to visit her in the middle of the night again. But on the other hand, I was bloody knackered.

Angela thought maybe I should leave it for the night, and let Sam stew things over and get used to the idea of the three of us just having had sex.

Sleep won the battle, but then matters were taken out of my hand...

I awoke, still during the black of night, to feel a hand on my cock, wanking me slowly. It must have been happening for a while, as I was almost at full erection. I took a hold of the hand, and gently nudged it, to encourage Angela. Then I realised that the forearm was leading out to the side of the bed, away from Angela.

Goddamn it, Sam had snuck into my room!

After a moment, there was some shuffling under the edge of the duvet, and her hot mouth enveloped my head, her tongue swirling around my helmet, teasing me, bringing me on. I reached down, and pressed gently on the back of her head, nudging my cock deeper into her mouth. At the same time, I ran my other hand, the one nearest her, down her back, working out how she was positioned. She was pretty much at right angles to the bed, so I leaned over to place my hand in the small of her back, and pulled her waist towards me. She got the message, and turned so that her bum was nearest me, her upper body now lying diagonally across me as she blew me.

I reached down with that hand, and felt my way around her bum, fondling her cheeks, reaching between them to rub up and down her cleft, feeling her lips start to open, and smelling her arousal start to fill the air. She moaned quietly around my cock as I slipped a finger between her lips and deep into her, feeling how wet she was already.

After a few minutes of fingering her, during which I added another finger, she began bucking back against me, pushing her cunt further down onto my fingers. I pulled away, and started to spread her juices back towards her asshole. She groaned quietly again, and reached back with one hand to grab my wrist and guide me directly to her ass. I felt her hand then slip down to her cunt as she started to finger herself.

I pressed forward with my finger gently, feeling her asshole open up to me. As my fingertip entered, she groaned again and stopped sucking me, lost in the sensation of being entered like this. I wanted to wake Angela up and get her to watch, but I couldn't think of a way to do it without her asking out loud what was going on, as she woke up. So I just enjoyed it while I could, intending to wake her up after Sam had left and get her excited by the story.

As I felt Sam's asshole loosen up, I collected more juice from her cunt, enjoying a moment of feeling her fingers against mine in her wet hole, and spread them back to her ass. Then, when I'd lubed her up as much as possible, I gently started inserting two fingers into her. She lifted her mouth from my cock and groaned again, still muffled by the duvet.

If she keeps that noise up,

I thought,

Angela's going to wake up anyway.

.

As I pushed my fingers in, I felt her hips pull away from me a bit... and then push back, urging my fingers deeper. With my hand still on the back of my head, I pulled her head back down to me and she willingly complied, but started by running her tongue all the way down the length of my cock to my balls, licking them a bit before sliding back up again and opening wide to suck my head into her mouth.

After another minute or two, Sam's asshole was loose enough for my two fingers to slide relatively easily in and out, and her hips were again pushing back and forth as she wanked herself on my fingers. In my head, I flashed back to one of my favourite porn clips: the girl is kneeling on a dining chair, facing the back of it, her ass thrust out. The guy, nicely lubed up, slips his cock into her ass, and as the girl gets into it, he stops moving and lets her do all the work, the camera looking down from above as she fucks herself on his cock. I imagined doing that with Sam, her large but firm ass spread wide as my cock ploughed her asshole, and I could feel my come getting closer.

Then I felt a tap on my other shoulder, and looked around. I couldn't really see much, but I could feel Angela leaning up next to me in the dark. She leaned in real close, and whispered, "I know what's going on. Sam woke me up to ask if she could do this, but you're not supposed to know that I know. Just pretend I'm still asleep." Then she pulled back and lay watching me. With a rustle of the duvet, she lifted her hand up and out of the cover, gently pushing her fingers into my mouth. They were covered with her juices, and I licked them off eagerly as she smiled at me. She then slid her hand back under the covers, and sighed huskily as she resumed fingering herself.

One thought went round my head:

Jesus, these two women really ARE going to kill me. How on earth am I going to keep up this pace till Angela goes away?

Then another voice drowned out the first one:

Shut the fuck up and enjoy it, stupid!

I smiled to myself, and started thrusting my cock into Sam's mouth, feeling her respond by the clenching of her ass round my fingers. I moaned out loud, quietly as though trying not to wake Angela, but doing it for both Sam's and Angela's benefit.

I could feel the movement of Sam's arm as she wanked herself, and it was getting more and more obvious. She must have been getting close to her come as well, so I managed to position myself so that I had two fingers in her ass still, while pushing my thumb into her cunt. It was a bit of a struggle in the position I was in, but the groan she gave as I pushed all three digits in told me that it was worth it. Her own finger slipped out of her cunt to give my thumb room to move, and I really went to town, plugging both her holes with fast, sure strokes, stopping occasionally to pull out and spread more juices round her asshole, then pushing all three fingers back in again.

I could feel my juices boiling, and I clamped down on the back of her head with my hand. I didn't push down, but simply stopped her withdrawing, and then my cock leapt as I spurted into her mouth. She grunted, and started swallowing, and within a few moments, I felt her holes clench around my fingers as she came as well, and she emitted a longer groan that vibrated round my sensitive head as my spasms died away. A few seconds later, Angela's arm came up to mine, and gripped tightly, her nails digging in, and I heard her breathing freeze as her orgasm came too. I slipped a hand down to her groin, and gently rubbed up and down her wet lips as she came out the other side of her come, turning my head to kiss her as Sam continued to mouth my cock a bit.

Then Sam pulled back, and I broke the kiss with Angela. Sam withdrew from under the cover, and shuffled up the bed to where my head was. Then she leaned over to kiss me, her lips parting and her tongue pushing inside me, the remains of my come on it. I reached up to pull her head tight into mine, pushing my own tongue back at her, breathing heavily to show my excitement.

When we broke apart, I whispered "Thank you... You're getting better at that", very quietly, pretending to not still want to wake up Angela, even though we all knew that Angela knew what Sam was doing. It dawned on me that it was a good thing that this wasn't a menage-a-quatre, as that would get REALLY confusing.

She then stood up, and crept out of the room, closing the door behind her. After a few moments, to make sure she wasn't coming back, I turned to Angela.

"You trollop," I whispered. "Fancy getting off on me getting a blow-job from another woman while you're in bed with me."

"I couldn't help it Andy. It turns me on so much to see you with Sam earlier. She's a lovely young woman, and like I said, I'm glad that it's you teaching her these things, not someone that's going to take their fun and then leave her when they get bored. I only wish I had someone like you when I was younger.... Oh boy, the fun I could have had if only I'd started early."

I pulled her in close for a hug, kissing her. "You know, I'm glad you didn't... If you'd started earlier, you might not have met me now... and I'm very happy that you did."

She looked up at me, a soft look in her eyes. Then her eyes hardened. "Yeah, right, you're happy that I let you fuck me up the ass every time we're together, and then let you seduce Sam, that's what you mean!"

"Well... yes, that as well. But honestly Angela, I'm really happy right now. I think you and I are getting on well, and I'm glad to have you in my life."

She hugged me tight. Then craned her neck up to kiss me gently. "Me too," she said, and with that, we settled down to go back to sleep.

----------

I woke first the next morning, and slid gently out of bed to go for a shower before Angela awoke. I toyed with sneaking into Sam's room and going down on her to repay her for the blowjob the night before, but I fancied teasing her a bit before making her come today.

So I just showered, and went to wake up Daniel. As we ate breakfast, Angela, and then Sam came downstairs. The two girls looked at each other and smirked, and Sam ostentatiously licked her lips, but that was all that passed between the three of us.

We had a good breakfast, everyone laughing and joking, and I got Daniel loaded into the car. As I went to get in, Angela came out to me. She gave Daniel a kiss goodbye and told him to be good at school, and then pulled me aside to speak to me without overhearing.

"Andy, baby, you look knackered. Are you sure you can keep this up?"

"Angela, I'll give it my best shot or die trying."

"I think you might be closer to the truth than you think. How on earth are you going to manage when you have to service Sam, Charlie, and Jules, as well as your woman-of-the-month, and me, when I'm here?"

I grinned at the thought of it. "Well, as you're involved, I think it's only fair that you get to share some of the burden and let me watch you and some or all of the others together - "

She smiled, and murmured her consent.

" - and then I can stock up on a few more dildoes, vibrators, and maybe a remote control egg so I can make you come in the most embarrassing situations - "

"Ooh, baby, can we get some before I go away?"

" - and then there's Peter to help with you, and I'm sure Charlie and Jules with have some male friends to bring into the fray if I need a little support. And then of course there's Viagra."

"Mmmm," she moaned, "you and the little blue pill. Permanent hard-on. Delicious. Do you think you could fuck me for eight hours solid without collapsing? I'd love to give it a try one night. I've heard that it makes it better for women as well - is that true?"

"I've no idea, never having had to resort to artificial aids before."

"I hate conceit in a man."

"And yet I've never heard you complain about my performance yet."

"Oh, I have Andy. You've just chosen not to listen."

"Well, do you blame me? All you talk about is begging me to stick my hard cock up your ass. It gets a bit tiring after a while. Less talk, more action, that's my motto."

"Andy, I only ask for that because it gets you off quicker, and that means I can get on with other things quicker as well. I don't enjoy it one bit."

"Yeah, yeah. I'll remind you of that next time we're doing it, and I pull out, and you plead with me to stick it back in."

"Again Andy, I just want it all over quickly."

"And yet still you keep coming back for me. What's the matter? Won't any other guy look at you?"

"Andy, you know that's not true. Peter got a hard-on just from feeling my ass in my dress. Do you really think he, or any other man, could resist if I actually TRIED to seduce him?"

"Angela, we're men. And he's a only just out of boyhood. Any port in a storm, and all that! He'd shag a wall if it had a hole big enough!"

She playfully slapped my arm, and then reached up to pull my head down to her. She kissed me passionately, and whispered that she was pleased at the way I was treating Sam, and she looked forward to seeing me with the women-of-the-month over the next year. "But Andy, when I get back from the states, it's going to be me and me alone for a long, long time. I'm going to screw you so hard and so often that people will think you're seriously unwell. You're tongue will be used so much that you'll have blisters. Your cock will be red raw. And your fingers will be in permanent cramps from being in me. I want you to book two weeks off, once I have the return date sorted out, and ... I hate saying this... but see if you can ask his mum to look after Daniel for a while as well. I love him to bits, he's a delightful kid, but I want you all to myself for a while when I get back. And I want you to book us into a really seedy little hotel near the airport on the first night, and fuck me like I'm your little slutty mistress who you've met on a business trip."

I kissed her again, and told her to get going. "Oh, and Angela - I want you to sort out a webcam for work, and to contact me online as you place it under the desk and let me watch you wank yourself one lunchtime this week. I want you to use the rabbit, letting me see you as you push it deep inside you."

She looked slightly shocked, then she flushed, and nodded her consent. "I love it when you're so bossy Andy," she murmured as she flounced over to her car, waving goodbye to Daniel and I as she got in. Then she waved me to come over to the car. I went over, and she handed me some keys through the open window.

"I think we're close enough for this, aren't we Andy?" she said, smiling.

"For your place?" I asked.

She nodded, looking up at me to see my reaction. I just smiled winningly, put them in my pocket, and walked to my car, waving her off. She rolled her eyes at me, and drove off.

I followed her up the road, tooting the car horn as I turned off towards the school. After dropping Daniel off, I wondered whether to return home or not, and decided to go for a coffee and croissant instead, at the place just down the road from the school. There were always a few yummy mummies in there after dropping the kids off in their 4x4s, so the eye-candy was pretty good to while away some spare time.

The coffee shop was busy, so I only just managed to squeeze into a table for two, and sat down with the morning's paper for a read.

"Mind if I join you?" came a woman's voice later. I looked up, and it was Simone, smiling down at me. I waved her to the spare seat, and took in her appearance as she settled in. She was wearing an all-white suit, tight around the ass and thighs but flaring out a bit round the ankle. She had a black blouse underneath, nicely undone a few buttons to show a hint of her perfect cleavage as she leaned over to put her handbag on the floor. Her boots were black also, with a nice heel, and I looked forward to seeing her walk away later. I love the way women's asses look so much better when they're wearing boots with a heel - all toned and high.

"Nice suit. But it's a bit brave, isn't it?"

"Being white, do you mean? Yes, I did think twice, especially after the mess that Stephen made of his toast this morning. Jam everywhere. But I'm heading out for brunch a bit later, and wanted to look good for him."

I eyed her. "Him? Hot date?"

"God no, I'm meeting Ken. Just want to show him I'm doing fine, and all that."

"Ah, the old 'I'm better off without you trick'. I've been there."

"Well, not so much of a trick. I AM better off without him."

"Oh Simone, sorry, I didn't mean it like that. You do look better off: the new hairdo is fab, you've - if you don't mind me saying - toned that little ass of yours to within an inch of it's life; that suit rocks; you've got a glow to your face that I've not seen for a long, long time." In an effeminate voice, I added "You're looking FINE, girlfriend!"

She laughed, and blushed a bit as well. "Thanks Andy. But you shouldn't be looking, not with you seeing Angela and all, you dirty man."

"Well, it's only looking, Simone. And besides, I think Angela would be upset if I didn't flatter you a little bit now and again. She's not the jealous type, and she likes that I go out of my way to make other people feel good." Obviously, I was thinking of Sam when I said this. "Anyway Simone, there's not a man in here who didn't watch you wriggle that little tush over here a minute ago. It would be wrong of me not to join in with them. Men have to show solidarity in these feminine-lead times."

"Do you think so?" she said, hastily looking around.

"Oh, god yes."

"Well, if that's the case, I'll bet they're all jealous of you right now."

"Correct. And the women are jealous of you, I'll bet."

She thought that through for a moment and then laughed. "That's a bit big-headed of you, isn't it?"

"No, just the truth." I grinned.

We chatted for a bit longer, with the conversation moving onto Angela, and how we were getting on. I told her about Angela going away to the US.

"Really? For a year?"

"Yeah, I know. It's a long time."

"So are you two...." She paused, not knowing how to phrase it.

I completed her question. "Are we splitting up?"

She nodded, grimacing to show how sorry she was to have asked that.

"No, we're going to give it a shot. We've discussed a few things that we can do to help keep things going well while we're apart. You know the sort of thing: frequent texts or quick emails just to show that we're thinking of each other throughout the day; good long chats by phone or webcam; a few visits back and forth. It's not that long really, and Daniel's looking forward to a few visits to the US, so I'm sure that it'll be fine."

That set me thinking, and I started to say something at the same time as Simone did. I let her speak first. "What I was going to say was: If you fancy some time with just Angela, Daniel could always stay with Stephen and I while you're there. You know the kids will love it, and it'll be great for me to have someone else in the house for a while."

I gave her my cheekiest grin. "How's about I send Daniel and Stephen to stay with Angela in the US, and I keep you company for a couple of weeks?"