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. Then we teased Sam in various ways in the garden…

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)

]

Angela came round that night

"Well? What happened?"

"What do you mean?" I asked, pouring out some wine.

"You know full well what I mean. Did Sam say anything about our massages?"

"Not really, but come upstairs and watch this." I handed her glass to her, and headed upstairs to the office. I sat down at the desk, and patted my lap to indicate that she should sit down on me. She did so, putting her glass on the desk. She was wearing a tight jumper and a short black skirt, no bra by the looks of things, the bottom of the jumper just clear of the skirt, leaving a bit of flesh on show. I nuzzled into her neck, and ran my hands up just inside her jumper, resting them on her waist. .

"Feeling horny Andy? Did you get excited seeing our little friend in her bikini?"

"Not as excited as she did seeing me, I think".

She whipped her head around to look at me. "What happened?"

I nodded my head towards the PC, indicating that she should watch it, as I pulled one hand away from her to operate the mouse and keyboard. I found the recording of the afternoon's entertainment, and started it playing. It started with Sam putting oil on Angela's back, followed by Ang sliding her bikini bottoms down and encouraging Sam to do her bum. I would have loved to seen it for real, hiding behind something as Sam fought the conflict between her desire to be nice, and her lack of desire to touch another woman's ass.

Ang wriggled her ass on me. "Mmmm. It seems that you quite like this, judging by the lump in your pants. I'm glad you've got a dressing gown on. I love the easy access that provides." She pulled her jumper up and off her, confirming that she had no bra on. I ran my hands up her front, lightly stroking her stomach on the way, to cup her tits. I gently tweaked her nipples, as she ground her ass against me.

"Oh, that's nice baby. I've been feeling horny all afternoon. I kept thinking of what it was like to feel Sam's ass, and how she jumped when I groaned. I wonder what would have happened if I'd kept quiet? Do you think she would have slipped a finger up to my lips baby?"

"No, and you're not doing that until I can watch from a hiding place much closer to you than I was then. I want to see the first time you get together - the first time she tastes a woman. Then when you're finished I'll punish you for being a two-timing tart who can't keep her hands to herself."

I let go of her tits, eliciting a slight groan of disappointment from her, and fast forwarded the video to the point where I came in to the garden after putting the trunks on.

"Ooh, baby, you look so good in trunks. I bet she just wet her pants at the sight of you. But why didn't you wear the nice new ones?"

"You told me to be nice. Do you think she would have appreciated it if I strolled in there with my cock peeking over the top?"

"Well, I guess not," she pouted. "Ooh, look baby, you're rubbing yourself up. I'm surprised you didn't just whip yourself out and start having a wank there and then..."

"Next time," I said. "Next time." I slid one hand back up to her tits, playing with them both, and the other one I slid up her thigh, stroking closer and closer to her mound.

Angela watched as I lay down on the sun bed and Sam started oiling me. "Mmm, she's taking a long time baby. Do you think she was enjoying that?"

"I know she was... Wait till you see what comes next."

"What baby? Tell me now."

"No. You'll have to wait."

"Oh, baby, please tell me," she whispered as she opened her thighs, grabbed my hand, and slid it up to her cunt. She was knicker-less, and already wet. She moaned as I slid a finger up her lips, parting them, her hot smell filling the air.

On the video, I almost turned over, then stopped as I realised I had a hard-on.

"Andy, you dirty bastard, did that give you a hard on? Was it as big as the one you've got now? I would have loved to have been there, so I could have gone down on you while she watched. Do you think she would have played with herself while you fucked my throat?"

I lifted her off me, opened my dressing gown up with one hand, whilst helping her pull her skirt up with the other. My cock burst free, aiming up at her. She reached between her legs, grabbed my meat, and lined herself up. Then she just dropped down, forcing my whole length into her in one go.

"Ahhh FUCK that's good. Jesus you’re big baby… Oh yeah, that's what I've been waiting for all fucking day." She slid back up again, watching the video-me turn a bit to show Sam my bulge.

"Oh Andy, you big tease. That was so obvious. Did she look?"

I reached up with both hands to cup her tits. "Yeah, she looked. How could she resist? It's coming soon baby. That's us talking about how she thinks she's fat, and I disagreed."

The video-Sam stood up with me behind her. "You're not - " said Angela. "Oh my god, did she let you touch her? You perv, rubbing your cock into her ass." Despite her words, she ground herself down onto my cock, and starting rubbing her clit with one hand.

"No, not yet. My cock was well away from her. But she loved my touch. She's got a lovely pair of tits baby." I squeezed Angela's breasts, nice and firmly, making her moan. She leant forward slightly, leaning slightly on the desk with one hand, giving her more room to just arch her back backwards and forwards, her hips taking up the whole movement of pushing her cunt up and down my cock, her shoulders stationary, just her back curving back and forth like a snake, just like the other day in the garden when Peter was watching. I leant back in the chair, watching her writhe up and down me.

"I can't believe you felt her ass baby," said Angela as she fucked me more, her juices running down her thighs and onto mine. "Did she like it?"

"She loved it," I answered, as I ran my hands down her slim, firm back to her hips, helping her to pump up and down. I pushed my elbows outwards, my hands cupping underneath her bum, so that my fingers were all pointing in to where our flesh met, and ran my hands up and down the outside of her lips as we fucked. "She was breathing fast, getting goose-bumps, she moaned as I cupped her tits... Did you see her flinch there? That was my cock touching her ass." With that, I slid my hands up her, moving from her cunt to her ass, spreading her juices around. Angela moaned as she watched me pull Sam in for a hug.

"It was nice Angela, my hard cock pressing against her soft belly. She didn't even notice that I was leaking a bit from all the excitement." Angela moaned my name as one of my fingers started rubbing her asshole, spreading her juices, getting her ready. "She said no-one's ever touched her like I did. Can you imagine? No-one has felt her gorgeous tits. No-one has stroked her bubble butt. No-one has felt inside her cunt. No-one has slid a finger into her ass." As I said that, I pushed a finger into her tight dark hole, and Angela pushed back to give me access, my cock still deep within her. Sweat was starting to collect on her back, and I leaned forward to lick some up, as my other hand reached round to stroke her clit.

Angela moaned, "Oh baby, that's it, that's it."

I continued. "And do you know what? She said she liked me touching her..."

"Oh god, baby, I'm so horny. I can't believe you felt her tits. She's a little trollop for letting you do it. Doesn't she realise I said she could flirt with you, but no touching? I never thought we'd be where we are, me getting fucked by other men and you feeling up your little virgin... and ... oh god that's good... I didn't think it would be so fucking exciting."

I slid another finger into her ass, getting ready for what was coming next. "I know you can't hear it, but that's me telling her that I know she keeps looking at my hard-on, and that she needs to get over it before you suspect something."

"But I told her - "

"You told her to flirt, as you just said. What we did goes further than flirting. But I told her that there's only one solution. Watch..." I pointed back to the TV, where I was just laying down with the book on my face.

"Oh my God Andy, what are you doing?"

"I was giving her the opportunity to stare at my cock all she wanted."

"Fuck, that's so dirty baby. Tell me what happened now!" She was really thrusting up and down now, her breath coming hard and fast.

"I don't know - I had my eyes shut, so this is new to me as well."

I leaned back again, slightly to the side to get a good view of the monitor, and started pulling my fingers out of her ass, back to her cunt to collect more juices, over and over, making sure she was very wet back there.

On the video, we could see that for a while, Sam just sat and stared. Then she slowly leaned back a bit, and started playing with her tits.

"That dirty cow," said Angela. "She's getting off on looking at your hard-on. And it's still covered up. Jesus, she must be frustrated.... Can you imagine what she'll be like when she finally does have sex? You'll be so jealous of the guy that takes her virginity, won't you? … Ah god you feel so good baby… I mean, we can talk about you doing it, but we both know it'll be some young stud from her university. You poor, poor man. All this excitement and only me to take it out on...." She leant more upright, taking her weight solely on her legs, and reached back to pull her ass-cheeks apart. "God I'm lucky."

Video-Sam reached a hand inside her bikini top to play with her nipples in the flesh, and ran the other hand down to her groin, rubbing and stroking through her bikini bottoms. "She must be so horny baby. I know I would be in her situation." Sam's hands suddenly pulled away from her body. I guess she had second thoughts. Damn. I was looking forward to seeing more. But then both hands slid back to her mound, this time inside the bikini.

"Oh baby," said Angela. "This is getting me so hot. Could you hear her baby? Could you hear your little virgin wanking herself as she looked at your cock? Oh fuck, I want your cock in my ass."

She raised herself up, took hold of my cock between her legs again, and lowered herself back down, this time lined up with her asshole. Slowly, she pushed down, and I could feel her rectum opening up, spreading, unable to resist the pressure of my hot hard cock pushing in. Then I was through, the rubber-band of her muscles snapping round me as she grunted with the feeling. I reached round with both hands, one rubbing her clit, the other pushing inside her, trying to reach her g-spot.

"It was torture baby. There I was, cock as hard as steel, my come leaking already, and I could hear her gasp as she was wanking. I could even smell her excitement in the air. And all I could think about was getting you up here and fucking while we watched her wank. … Jesus, your ass it so tight baby… You’re such a slut – taking my cock in your ass while you watch that young girl wank herself because of my cock " Angela was still pushing up and down on my cock, forcing me further into her ass. "I asked her if she wanted to see it in the flesh..."

I felt her ass spasm around me as she turned her head to look at me. "And..?" she grunted through clenched teeth as she pushed down further.

"She declined... so I told her I had to go and have a wank... well, not in so many words, but she knew what I meant...."

"Oh Andy, you're a dirty fucker... when I said you could flirt with her... oh god you're big... I didn't think you'd be showing her your cock and talking about wanking so quickly.... "

She gave one last push, and that was it, I was all in her ass. "Oh fuck that's good," I groaned. She started rising up and down, and I could see her ass cling to my cock as she lifted, and then get pushed inside as she slid down again, her juices shining on my cock. The video became almost static, just Sam sat there, thinking. Occasionally she would look up towards the house, move as if about to head indoors, and then stop, sitting down again.

"I did more than that baby..." I said.

"Oh god, tell me what happened baby, tell me, make me come while you’re talking about another woman..." Her breath was coming hard and fast now, and I could feel her ass and cunt spasm as her orgasm approached. Onscreen, Sam suddenly stood up and strode off-camera, towards the house.

"I went upstairs... got naked... and lay on my bed. I started wanking, thinking about her body, her weighty tits, her firm round ass... Then I heard a noise outside..."

"Oh fuck baby, she watched you wank again? Jesus, that's so fucking dirty. Oh fuck me baby, fuck my ass... I'm going to come... I'm going to come... I - Oh FUCK ME!"

She came then, thinking about me wanking while Sam watched, her ass clenching round my cock, and her cunt flooding my hand with her juices. Sweat suddenly broke out on her back as it arched, pushing my cock as far into her as it could go. I enjoyed the ride, letting her calm down, feeling her asshole slowly loosen. Then I put my hands underneath her ass, pushing her off me.

Her legs shaking, she groaned as she felt my cock slide free of her ass, and I turned her round to face me, starting to pull her down to ride me.

"I want to come in your cunt," I said.

"God Andy, you're a fucking machine... won't you give a girl a break?"

I smiled, and told her to get on top of me and to wank me with her cunt till I came in her. She obediently opened her legs wide to straddle me in the chair, her hand reaching down to guide me into her steaming cunt. She gave one long push, sinking deeper till her ass sat on my thighs.

"Oh god, that's good. But I'm going to be sore tomorrow..." she moaned as she writhed back and forth, not moving up and down, just using the angle to put pressure on different parts of us.

"OK," I said, perkily. "We'll stop now then," and I started to lift her off me.

She grabbed the back of the chair, pulling her back onto me. "No baby, I didn't mean it. I want you in me. I want you to come in me. Do it baby, fuck me. Come in my slutty little cunt. Make me come as well; you know I have a quick come the second time."

She started to ride up and down my cock, whilst I continued telling her about Sam and I. "I put on a good show baby, you would have been proud of me. I made sure she had a good view, thrusting my hips off the bed." I curled my arms up behind her, grabbing hold of her shoulders, using them to pull her down onto me when she sank down. She started responding immediately, the pressure in her most intimate place preventing her from calming after her first come, and quickly turning into more and more arousal as I ploughed her insides.

"I played with my balls next, my shaved balls... I imagined her coming up to me and licking them, unable to resist..."

"Oh fuck Andy, that's good... Did she? Did she run her tongue up and down ... your hard cock?"

"No, not this time... Instead, I ran my hand round my cock head, making sure she could see how much juice I had leaked because of her." Angela groaned beneath me, her hips bucking to meet my thrusts. Her orgasm was building again. What was it about this woman? Every time we had sex, her second come was so quick! "You're a dirty tart Angela... I can feel you getting off on this... thinking about that little girl watching me wank..."

"Oh yes, Andy, fuck me, I can't help it, you get me so turned on... Ah, that's good, you feel so good inside me baby... You've never been as deep as you are now... Did Sam turn you on that much? .... Oh, that's it... Did Sam make your cock bigger and harder than I can make it? That's bad baby. I'll make it up to you... Tell me what I can do so you're bigger for me, not for her."

"You can start by kissing me..." She reached down with both hands, pulling my head up. Her lips pressed against mine, melted apart, and her tongue thrust out, her breath coming hot and fast as we kissed.

After a few seconds, we broke apart. "Then I want you to let Sam know that I loved feeling her up today. That it turned me on in so many ways, and that I want to find an excuse to do it again."

"Oh yes baby, I'll do it."

"Tell her that I was so turned on, that I fucked you, here in this office, whilst telling you about it."

"No baby, don't make me say that."

"

Tell her

. And tell her to pretend to have a cramp or... or a pulled muscle or something... and get her to ask me to massage it. Make sure she's wearing a skirt, something short so I can see up her thighs...God, you're so wet you little tart, getting turned on by me seducing Sam...

"And tell her how good I am with my hands... How horny you feel with my fingers inside you… How much better it would be than wanking herself in the shadows..."

"Oh Andy, I'm going to come again baby, fuck me harder!"

I put everything into it, and then, as we both got to our peaks, I panted into her ear, "When I came... I took my hands away... let her see my whole cock as my come exploded from it... and I called out her name so she could hear."

That did it. We both came, clenched around each other as all our muscles tightened, my hands pulling her tight down onto my cock, my seed spurting into her womb as her wetness flooded around our groins. Angela froze, her hands pressing my head into her tits, her groin pressed down into mine, her breath held as the feelings rushed through her, and the world stopped as I rode through my own come.

When we could breathe again, she stayed on top of me, the walls of her cunt twitching with the aftershock. We kissed each other, the lips, the throat, tongues flicking to taste each other.

"God Andy, that was so good..."

I murmured my agreement as I nuzzled into her neck, nipping it gently between my teeth.

"There's something I want to say baby. I've been thinking about what I said, about you and Sam flirting with each other."

Oh god, she's going to put a stop to it

, I thought, dismayed.

"It's already gone further than I expected, quicker than I expected. I never thought that within a few days, you'd be feeling her tits and ass, and showing her your hard-on."

I slumped into the chair, expecting what came next.

"I've changed my mind," she whispered.

There. The fun's over

, I thought. "OK, whatever you say," I said, the disappointment clear in the tone of my voice.

She pulled back a bit to look at my face, a puzzled frown on hers.

Then she pulled my head right into her tits, cradling me in close. "Aww baby. I'm sorry. Are you disappointed that I don't want you flirting with that young woman any more? Can you blame me for wanting you to myself? You're too good to share with just anyone baby."

I licked her cleavage, consoling myself that at least I'll get to have sex with the horny woman who currently had my cock deep in her.

"I'll bet you were really looking forward to many a night teasing her, and being teased by her, and then giving me a good hard fucking to make up for it, weren't you?"