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 said she wanted me to flirt with Sam, and let Sam flirt with me, but without letting Sam know that it was planned. Also, Angela and I have been watched by Angela's neighbour, Peter, while we had sex in the garden. The next day, we had a threesome with Peter, giving Angela her first double penetration.

Angela has informed me that she's off to the US for a year, just as we're getting close.

After catching Sam watching a recording of Angela and I have sex, resulting in a charged encounter between us, I snuck into Sam's room and wanked off over her.

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 woke early on Friday morning morning, and went downstairs before Daniel awoke to have a quiet breakfast for once. Sam was already there, reading a book over a cup of coffee. She was wearing a dressing gown over her pyjamas.

Damn

., I thought,

I was looking forward to some fine jiggling tits this morning

. She looked up as I stood there in just my boxers, and looked down the length of my body.

"Oh, hi Sam, I didn't expect you to be up."

"I, er, I didn't sleep much last night, and I woke up early so I thought I'd come down and read."

"Oh? I hope I didn't keep you awake?"

She stared at me. "What.... what do you mean?"

"Well, you know, pottering about the house after you'd gone to bed."

"Oh, I see. No, it wasn't you. It was... well, last night."

"Sam I told you, don't worry, it happens to us all."

"But I watched you and Angela, that's a terrible thing to do. That was private."

"Listen Sam, I don't care. It's my fault, as I said. Don't sweat it."

"But - "

"But nothing Sam, drop it, it's not important. Now, do you want a top up of that coffee?"

She started to say something else, and then stopped. "That'll be nice," she muttered.

"One more thing... I wouldn't normally wander about the house in just my undies with you around... but I figure that as you saw me in the same state when sunbathing, you won't mind. Is this OK with you?" I pointed down to my groin as I said that last part.

She glance at me, involuntarily, and flushed, looking down at her book again. "Err, yeah, that's fine Andy."

I made my coffee, and sat the other side of the breakfast bar from her. She remained engrossed in her book. I took it off her, closed it, and put it down.

"Sam, listen to me. What you saw yesterday was something Angela and I like to do occasionally. We like to record ourselves, so that when one of us is away, the other one has something to ... amuse themselves with. Remember the last time I went to a conference, and you nearly stayed over? Good job you didn't as Angela had left some photographs and a DVD lying around, as a welcome home present, and they were more intimate than what you saw last night. Although I've never yet found that DVD, strangely. It must have fallen behind or under some furniture."

She flushed deeply again. Ah ha, that's the proof. She had been over in that week, and certainly had the other DVD.

"The fact that you found it arousing is... well, it's a complement really. It's no different to watching porn, which I'm sure you've never done, but millions have. It's harmless, as long as the people making it are having fun. And Angela and I were certainly having fun when we made that." I looked away, smiling to myself, remembering how good it felt to fuck Angela in the ass while the vibrator buzzed away in her cunt. "Boy, did we have fun," I said, softly.

I looked back at her. "Anyway Sam, seriously, there's no harm done. In fact, when I thought about it last night, it actually got me quite excited to think that you were getting off on watching us... Oh Sam, stop blushing, it's quite natural. When I was your age, I watched quite a few people have sex at parties and the like, hiding in the shadows while they ground away on each other. Again, if you haven't got an outlet yourself, it's perfectly natural to take matters into your own hand. Hell, remember me saying that I still wank even though I've got Angela?"

She turned away when I said that, obviously embarrassed or ashamed of watching me wank so often. Then I remembered that Angela had told Sam to watch us one night.

"Just one thing Sam. Please don't say anything about this to Angela. OK, so we might not make it through her time in the US, but at the moment, she means a great deal to me, and I'd hate for her to think that you and I were up to anything behind her back. I know I reached out and touched your breast, but... well, let's just say it was a moment of weakness. You standing there, obviously in heat, I'd watched you a bit from the window... I couldn't help myself. Please, don't say anything. It won't happen again, I promise."

Sam looked at me. "Oh, no Andy, I won't say a word. I understand." She was fighting back a smile, so at least she was coming round a bit. "Talking of Angela, are you seeing each other this weekend?"

"Tomorrow, I'm not sure when. She's out tonight with the girls from work to celebrate her coming promotion."

She cracked another smile, trying desperately to hide it. "Oh, Andy, before I forget. I noticed this morning that someone's spilled something on my bedclothes, there are a few drops of something spattered over the duvet cover."

I looked down, pretending to be embarrassed.

Ah, so the mouse has decided to play with the cats has she? Excellent!!

, I thought. "Oh really," I said. "Sorry about that, I didn't notice when I made the bed up."

"That's strange Andy, as I didn't notice them when I went to bed either. It's as if something dripped on them last night. Maybe you've got a leak in the ceiling?" She was fighting that smile still.

"Oh, er, yes. I'll go take a look now. I'll be back in a minute." I headed upstairs, into her bedroom, smirking to myself.

She must think she's so clever

, I thought.

Little does she know the rules have changed after Angela gave me permission fuck the little virgin

. I quickly lifted up her duvet, breathing in deeply, sniffing. Yes, the horny little minx had wanked last night, I could smell her in the air.

After a few moment, I went downstairs, this time with Daniel, who I woke up en route. "No damage visible," I said as we walked back into the kitchen. "I'll keep any eye on it in case there are any more leaks."

She smiled her agreement, and then bent down to pick up Daniel and start getting his breakfast ready. The next hour was a blur as all three of us got ready, with no more talk about last night. When Daniel was finally ready for school, he ran out to the car and got sat into the drivers seat, pretending to drive, like he always did. I quickly picked up my wallet, phone, and so on, and started to head for the door.

Then Sam called out from upstairs. "Andy! Are you still there?"

"Yes," I shouted back up the stairs.

"Could I have a word for a minute? Up here?"

I went upstairs, following the sound of her voice as she called me into her room. She was stood there in her bra and knickers, the red lacy pair that she'd bought when out shopping with Angela, and that she'd stuffed into a bag when I had entered the room with coffee. I stopped still, taking her in. The red material looked great on her creamy white skin, and her tits were cupped beautifully.

She looked down at herself, as if suddenly realizing what she was wearing. "Oh Andy, I'm sorry. Is this OK? I mean, you saw me in my bikini at the weekend, so this is about the same. You don't mind, do you? It's just like your boxers this morning..." She smiled at me knowingly as she said it.

I shook my head, silently. She walked up to me, till she was standing very close. As I was quite a bit taller than her, I had to look down. Her cleavage beckoned me, and I could see her nipples erect underneath, pushing against the material. "It's just that I forgot to ask something earlier in the week. It's my dad, you see. Well, bloody Babs to be exact. She's getting some work done on her house this weekend, and was going to move out to a friends for the few days. But dad's invited her to stay at our place, and... well - "

" - and, you don't want to be at home?"

She smiled again. "Exactly. I know it's asking a lot, but could I stay here? It's only for a few days, Tuesday, or Wednesday at the latest. I'll stay out of your way, honest. And I won't watch any more DVDs without asking you first." She reached up to straighten my collar a bit, the lift in her arms emphasising her large breasts even more.

Jesus, this girl is good when she puts her mind to it

, I thought.

"Would that be OK?" she asked.

I smiled at her. "Of course Sam. Stay as long as you want. You know it's no bother."

"Great," she said. "Just a couple of ground rules first though Andy, after last night. First, try to keep your hands to yourself. As you said, you don't want Angela to be thinking that there's something going on between us."

"Of course. Although it will be difficult if you keep dressing like you are now" I answered.

She smiled bashfully, and then continued. "Secondly, I'll see if I can find out what's causing those drops on the bed. As it was at night, maybe it's something to do with the hot water system going off for the night, and the flow of water changing, pipes cooling down, that sort of thing. I'll try to sleep lightly, so that I'll wake up if I hear anything odd. Then I'll just lay very still in the dark so that I can hear the slightest noise."

"OK," I said, delighted that she was going to play the game.

"Third, it was awfully hot in here last night, even with the window open. Would you mind awfully if I slept naked at night?"

I smiled, but tried to look like I was fighting to keep the smile down. "Well, Sam, that's up to you. Just don't let me catch you wandering round the house naked, alright?" My cock was showing signs of interest at this point.

"Oh, I promise Andy. My only concern is that I sometimes need an extra glass of water at night, particularly when I'm all hot and bothered. So if you do hear me creeping about, I'll just be going to refill my glass, so don't you worry about it. Just stay tucked up in bed real nice, and I'll soon be back in mine again." She looked down then, right at my groin, I'm sure.

Jesus, this girl could seduce a 110-year old hermit

.

"Oh, I've just thought of something else. What if I do spot the issue with those drops? Should I get up immediately, and come and get you, which means I'll be naked. Or should I get dressed and come and get you, which takes a bit longer and might mean it'll be too late to prevent some serious damage?"

"Er... you'd better come immediately Sam. Better safe than sorry, and all that."

"But Andy, can I trust you? Remember when my blouse was undone yesterday, and you touched me like this - " She ran one hand over the curve of her breast as it bulged out over the bra, then down to her nipple, breathing in deeply as she did so. " - you said you couldn't keep your hands off me? How are you going to manage if I'm totally naked?" She breathed in deeply, pushing her tits out even further, one hand still resting lightly on her tit.

My cock was rock-hard by this point, squashed into my jeans, throbbing intensely. "I'll try Sam, I'll try. That's all I can say."

She gave me a huge winning grin. "Good! And one last thing Andy..."

"Yes?"

"Some time tonight, preferably after I've gone to bed so that it's not intrusive, could you maybe find something to do with

that

?" She stepped back a bit and pointed at my cock. "I know it must be frustrating for you to have someone like me around, standing here in my lingerie, pleasuring myself on your sofa, watching your DVDs. And I'm sorry, I'll do my best not to... er, affect... you too much. But if it does get too much for you, please don't hold back on my account. I'm sure you can find something to do in the middle of the night to help you relieve yourself..."

The dirty little minx is basically begging me to come in and feel her up again. I like this girl!

"After all," she continued, "I can hardly complain after you watched me on the sofa last night, can I? Who knows, maybe if we're both feeling frustrated, we could - "

The car horn tooted.

Dammit, I'd forgotten that Daniel was waiting to go to school!

"We could what?" I asked, hoping she was about to say we could watch each other.

"Oh, nothing Andy. Just silly talk. Go now, Danny's waiting." I waited a moment to see if she would say anything else, but she was turning to go back to her clothes and make up. As I walked to the door, I heard her say "Oh!"

I turned back to her, to see her facing away from me, bent over, her hands on the bed as though she'd fallen and caught herself, her back arched, her lovely round ass sticking out towards me, smooth and curvy. I stared, open mouthed.

It seems hours, but only a few seconds later, Sam turned her head over her shoulder and saw me looking. "Oh Andy. That's so ungentlemanly of you, staring at my backside like that." But she didn't move away or stand up.

I took a step towards her, my hand lifting up slightly as I started to reach for her ass. Then the car horn tooted again. Sam stayed where she was, shifting her weight on one left, moving her shapely ass around, and said "Andy, I think you'd better go, don't you?"

I sighed, and left her room, closing the door behind me, but not before I had one last look through the gap as I closed it. She was still bent over the bed, but this time had one hand between her legs, sliding up her smooth inner thigh, up, up, till she turned her hand palm up and rubbed quickly over her mound. The last thing I heard as I closed the door was a soft moan.

Jesus, these two women are going to be the death of me

, I thought.

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

I dropped Daniel off at school, and came back home. When I walked into the living room, Sam was sat on the sofa, surrounded by books and paper, obviously hard at work. She was wearing some of her old clothes - a baggy sweatshirt and a pair of jeans.

"Ah, I see frumpy Sam is with us today", I said, laughing at her.

She glared at me, and turned back to her books. Keeping her head lowered, and flicking through her book as though she wasn't really interested in our conversation, she said "Andy, last night I was wearing nicer clothes, and you couldn't keep your hands off my body. At the weekend, I wore a bikini, and you also couldn't keep your hands off my body. I think it's best for all of us if I were something a little less risque. Don't you agree?"

"Sam, yesterday you were caught red-handed, so to speak. THAT'S why I couldn't keep my hands off you. It had nothing to do with what you're wearing."

"Oh, so now you're trying to convince me to wear something slinky again today, eh? No Andy, that's not going to happen. Frumpy Sam is here to stay. I know it's hot today, and these are not the best clothes to wear for hot weather, but they'll have to do. Once again, I find myself at your place longer than expected, and with not enough clothes to cope with all this variable British weather."

"Oh no Sam, you can't blame me for that one. Admittedly, the last time you were here unexpectedly, it was your Dad's and my fault for conspiring to keep you out of his way. But this time, it's all your fault. You knew you were going to ask me if you could stay longer, so don't blame me if you're too disorganized to bring clothes."

"Enough of your chat, Andy. I'm busy. Leave me alone to get on with my work, and you get on with yours. Don't you have a business to run, aside from your Seduction-R-Us sideline?"

I stared at her for a moment, and then shook my head, laughing quietly and headed up to the office. As I went upstairs, I shouted back, "Oh, and Sam? Remember, no DVDs..."

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

A couple of hours later, I went downstairs to make a coffee. I went through to the kitchen without looking into the living room, and started making my drink. I called through to Sam.

"Sam, fancy a coffee or something?"

She shouted back, "God no, it's too hot for that. But you could fetch me an orange or something. With ice, thanks"

I made the drinks, and went through to the living room. The sofa is in the middle of the room, back towards the door, so I couldn't really see Sam other than a book held in her hands, above the top of the sofa. She must have been lying on her back, the book above her head. As I walked in, she leaped up from her position, knelt facing the back of the sofa, reaching out for to me for the drink.

And she wasn't wearing the sweatshirt any more. Leaning over the back of the sofa, her tits, encased in that red bra, were on full display, hanging down beneath their weight, cleavage deliciously dark between her mounds.

I stopped and stared.

"Oh, Andy, behave yourself. It's too damned hot for wearing a sweatshirt, and that blouse needs a wash. I'm sorry to wander round in my bra again, but it's no worse than my bikini. In fact, I think the bikini shows more."

I walked over to her, and handed her the drink. She took a big gulp, and gave out a gasp when she'd finished, obviously delighted with the cool drink. Then she reached into the glass, and pulled out an ice-cube. Then, just like in a hundred movies where the director offers some cheap titillation, she ran the ice-cube down her throat, over her collarbone, down to her cleavage, closing her eyes at the feel of it. "Oh, god," she moaned, low in her throat, "that feels good...."

My cock started to react, as she opened her eyes and looked at me. "Oh, Andy, I'm so sorry, that must have seemed pretty brazen of me. I meant nothing by it. Please, just ignore me." Then she turned around, and sat normally on the sofa, putting her drink on the floor beside her. She patted the seat next to her. "Come on Andy, take a seat, we could both do with a break."

I sat next to her, and she turned sideways on towards me, her lovely breasts on full display in front of me. She saw me looking, looked down herself, and then asked me, "So do you like this lingerie set, then?"

"It's very nice, Sam. I dread to think what you used to wear in the old frumpy days - probably grey knickers like your grandmother wears."

She laughed, and leaned forward, placing her hand on my thigh. "Actually, Andy, I think you'd be surprised. I had this set - " As she said that, she ran her spare hand over the curve of her breast. " - specially fitted, from a proper woman's outfitters. It turns out that the ones I was wearing before were too small. I must have looked a right sight, nice big breasts bulging out over a bra that was too small. Can you imagine that?"

I certainly can

, I thought. But I grinned at her. "Actually, I can't Sam. Perhaps you could show me one day?"

She shook her head, laughing. "Angela was right, you are pretty pathetic. A man of your age desperate for a glimpse of a young girl's bosom."

"Oh? And what else has Angela been saying?"

"Oh, just girl stuff, you know how it is. Actually, she phoned me last night when you were out. She was saying you've got the most amazing hands, and can work all kinds of wonders." She gave me a huge grin, running her hand slightly up and down my thigh.