Anal at Last

Angela left the next morning, a cheesy grin on her face all morning. I leaned into her car window to kiss her goodbye.

"Last night was.... fantastic," she said. "I can't believe how many times I came, or how quickly... Fuck, you're good. I still can't believe Sharon let you go, but thank fuck she did." She winced. "Ouch, I'm sore this morning. You're too big for that amount of sex, at least not without feeling it the next day. The girls will be wondering why I'm walking funny today."

I smiled. "Why don't you tell them? Well, let them guess, and then when I meet them at your leaving do, it'll give them something to wonder about. Plus, one or two of them might be interested in our little deal..."

"Oh, I'm going to let them know alright... but only so that I can tease you all night long, and then let you take it out on me when we're alone. Well, alone as we can be with Peter and Simone around. I'm SO looking forward to that!"

She left then, waving through the rear window.

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Sam phoned later that day, wanting to come around that afternoon, if it was OK.

Jesus, I thought. I could do with a rest.

But of course, I said yes. Who could resist?

When she arrived, we spoke about Angela's leaving do, and I phoned Tina, Angela's colleague at work who was sorting out that end of things. Between us, we arranged a few special things. I ordered her favourite flowers to be delivered en-masse to the venue on that day (a nearby hotel), as well as some to the office. One of Angela's colleague's boyfriends had a side-line as a party DJ, so he was doing the music, including a lot of the cheesy stuff she liked when growing up. Tina also mentioned that they had something special planned for Angela on the night, as a kind of private joke between them all. She wouldn't say any more, despite my teasing, so I said I was waiting with baited breath to find out what it was. She replied that I wasn't the only one, but refused to say more.

As I hung up, Sam walked into the office, having obviously waited till I was finished. I turned round, and was stunned to see her naked already. I'd guessed that something was going to happen, but I didn't expect her to make the first move so boldly. Her nipples were erect, she had a flush to her cheeks and chest, and I could smell her excitement in the air.

"Andy," she said, simpering slightly, with an impish grin on her face. "I wonder if you could help me out. I've got something stuck."

She came up to the desk, walking slightly oddly, and leant over it, sticking her ass out. And to my delight, I saw a small dildo poking out of her asshole, wet with lube. "Could you maybe wiggle it about, and see if it comes out?" she said, looking over her shoulder at me as she parted her legs further, arching her back to get her ass sticking out as far as possible.

"Why Sam, you little devil," I breathed, as I reached up to the dildo. I started to slide it in and out of her ass. It wasn't a big one, maybe 4-5 inches long, and not too thick. She groaned as I fucked her ass, her head dropping down onto her folder arms, her legs spreading wide, her ass tilting towards me.

With my spare hand, I ran a finger up her cunt lips, feeling how wet they were already, making her shiver in response. "Sam, baby, you look so good like that... Is this the first time you've used this?"

"Yes... Oh Andy... I wanted to do it myself, but I wanted you to do it as well... I got so turned on at the thought of you doing it to me, so I waited... I've played with myself so much over the last few days, while... Oh that's good... while thinking about doing this.... But I didn't use it till now... It's so big Andy... But it feels so good..."

With the hand that I was rubbing her lips with, I extended two fingers, pushing them inside her, feeling her cunt tighten as I did so. Then I pulled out those fingers, knelt down behind her, and pulled her hips towards me, making her cunt stick out more. She was still hairless there, obviously keeping on top of her shaving routine, and her puffy lips stuck out nicely. I ran my tongue up her slit as I carried on fucking her with the dildo, and she shuddered as she groaned my name.

I carried on licking her cunt, feeling her juices flow more and more, as I fucked her, eventually getting the dildo to the point where the entire length of it (less the handle) was going into her ass, slowly but evenly. She was dripping wet, her juices running down my chin, her hips pumping to get the dildo into her ass each time. Her breath was coming hard and fast, and I knew she was about to come.

I pulled away, and lifted her up, turning her round, and pushing her into my chair, slouched down. I knelt down again, lifting her legs up over my shoulders, and planting my mouth on her cunt again. From this angle, I had a much better angle of attack, and I really went to town on her, as I reached up and started with the dildo again. She started climbing the peak to orgasm, her breath coming faster and faster, moaning my name, her hands coming down to press the back of my head into her mound. As my tongue started flicking across her clit, she came, her thighs clamping tight around my head as she screamed my name.

When she'd recovered, I slid the dildo out, and taking her by the hand, I lead her into the bedroom, pushing her gently on to the bed, and throwing the dildo beside her. "Turn round Sam, lay on your back and let your head hang over the end." She did as she was told, and I pulled my hard-on out of my jeans. She had guessed what was coming, and opened her mouth as I lined my cock up with her, and then pushed in, feeling her hot mouth suck me in.

"Ah fuck, Sam, that's good," I moaned, as I started to fuck her mouth. I didn't go deep, just a few inches each way, enjoying the feel of her tongue on my cock head, and the sight of her naked body spread out before me. I bent forward, reaching out to run a hand up and down her slit, pushing two fingers in again, curling them up to rub against her g-spot. She moaned around my cock, the vibrations adding to my pleasure.

She reached up to play with her tits, stroking herself, tweaking her nipples, her legs opening wide to give me free access. I kept fucking her mouth for a while, still finger-fucking her, but - to be fair to Sam - she was getting better, but wasn't yet good enough at blowjobs to make me come just from her mouth. So I pulled out, stripped off, and lay on the bed. "Straddle me," I ordered her, and she got up, planted herself on top of me, my cock lying along the length of her cunt.

I pulled her down to lay on top of me, kissing her, grinding my hips, running my cock up and down, and she reciprocated, her tongue entering my mouth, her hot breath panting, her wet cunt lips separating as my hard-on rubbed against them.

"I want to fuck you so much Sam... You drive me crazy... I just want to feel you, to be in you... Just once Sam... Just once... I want to look down on you and see you come with my cock in you... See you unable to believe how good I can make you feel..."

"No Andy, no... We can't... I want to as well... but no."

I grabbed her ass cheeks, pulling her down onto me even tighter. "Can you feel me Sam? Can you feel how much I want you? I still think about you every time I fuck Angela... I wish you were there so I could pull out of her, and plunge my full length into you, hearing you scream my name in ecstasy as you come, my cock spurting into your tight virginal cunt..."

"Oh god Andy... You feel so good..."

"And your ass Sam, I want to be there too... You looked so horny with that dildo in you... You dirty girl... I can't believe you did that... But you need a bigger one soon Sam... You need to get used to something bigger... But let me do it... Let me push that big dildo into your tight little ass... Let me see you stretch around it... Let me hear you groan as you take it inside that gorgeous ass of yours Sam."

"Andy... Yes... I'll let you... You'll do it first..."

She was getting turned on again, and so was I. Her cunt was sopping wet; an extraordinary amount of her juices drenched our groins, the slap of it echoing in the room. I pushed her off me. "On all fours, Sam, now."

She quickly did as she was told, pointing her ass towards me, wriggling it in anticipation. I picked up the dildo, and slid it into her cunt, getting it nice and wet. Then I pulled it out, and placed it against her rosebud again. I gently pushed in, seeing her sphincter expand to let the dildo in, seeing the dildo sink a couple of inches in. Sam groaned into the duvet, pushing her hips back against me.

I reached down with the other hand, pressed my erection down, and shuffled forward on my knees, sliding my cock underneath her, along her wet, swollen lips. She groaned again, reaching one hand down to grab me, wanking me slightly. I started to push back and forth, and she let go of me, letting my cock spring up to press along the length of her slit again, my head rubbing against her clit each time I pushed.

Her hips worked with me, pushing back and forth to increase the pressure we both felt, even as I started fucking her ass again with the dildo, reveling in the sight of her asshole expanding and contracting as the wider part of the dildo pushed into and out of her virgin ass.

We kept going; sliding our groins together, lost in the sensations of fucking-but-not-fucking, and I could feel my come approaching fast. I told Sam I was going to come on her again, and she pulled away, flopping onto her back and spreading her legs wide.

"This way Andy... I want you on top of me when you come..."

I lay on top, my cock naturally lining up with her hot cunt, and we started fucking-but-not-fucking again, her lips almost seeming to grip my meat as I slid up and down them. Her legs wrapped around me, her hands pulling my head down to her tits. I sucked a nipple in, licking it, biting it, feeling it get even harder in my mouth. Her hands slid down my back, gripping my ass-cheeks, pulling me in even tighter, pressing my cock hard against her cunt. We were both panting, lost in the throes of the moments just before orgasm... and then we came, simultaneously, my come spurting between us, her legs and arms gripping me tight as she curled up in her orgasm. I kept on stroking, my come squelching between our stomachs, as she groaned, rendered mute by the feelings she was having.

I rolled off her when I could, and she turned to lay half on me, her heaving tits pressed against me, one leg wrapped over mine. She ran a hand over her belly, collecting some of my come, sucking it off her fingers, and then grinning as she bent down to kiss me, her tongue lined with the taste of my come, knowing how much that turned me on. She reached down to stroke me, giving me a nice firm wank, squeezing the last few drops of come out of me. She broke the kiss, curling down to suck my head into her mouth, cleaning my head.

Then the trollop rolled off the bed, heading for the shower, her large but firm ass drawing my eyes. "I'd better shower Andy. I can't go to classes smelling of your come, can I?"

I lay there, nicely relaxed, listening to the sounds of her showering, and then drying off. She re-appeared, towel wrapped round her. "Andy, I've been doing some thinking. I think we both know that, one day soon, I'm going to want you to take my virginity - " I looked up, shocked. "No Andy, not the usual virginity, but my... well, my anal one. And I want it to be a special occasion. So I've been thinking of when to aim for. There's Angela's leaving do, but that would be a bit tactless, don't you think? So I was thinking maybe the first night after she's gone. I could come here to keep you company, finding you all lost and alone and needing consolation, and then... well, you can guess the rest."

I smiled at her, waiting for her to continue.

"Or, there's the day I finish my exams. Or my birthday; it's only, what, 6 weeks away I think. And it'll be a nice birthday present, I think.... Do you have a preference?"

I thought about it for a bit. "Well, to be honest, I'm going to be kind of busy for the next few weeks with work, and - well - I'd like to be in the right frame of mind if I'm going to finally take that lovely ass of yours, and I'm not sure I'll be in the best mood so soon after Angela leaves." Also, I was thinking of Simone, as I intended to give her the best sex she'd ever had in the month we would have together. "So how's about your birthday? We can tease each other in the meantime..."

She grinned at me. "I can't wait. I'm having a bit of a party, as I missed my eighteenth due to being ill - do you remember?" I nodded. She'd come down with the 'flu. Real bad. Bed-ridden for about three weeks. As usual, she'd been working to hard for her exams, and worn herself out. "OK, so you're invited. I'll let you know the exact details later, as I've not confirmed them yet. But it'll be the usual affair - family, a few friends, some people from uni, that kind of thing."

She came up to me, leaning over me, running a hand down to my cock, wanking me again. "It'll be great to be seen with you, teasing you, letting you feel me up when no-one can see, letting me sit on your lap and feel your hard-on growing beneath me, just like it's doing now."

She licked her lips, looking at my cock as it grew. "I'll be talking about you to my friends, and telling them that I've heard you in bed with Angela, and you sound real good. Maybe I'll even tell them that you accidentally caught me in the shower one day, and stopped to stare. Maybe I'll tell them that we were having breakfast one day, and I caught you admiring my tits, and I saw your hard-on under your dressing gown, then later I walked past your open bedroom door and caught you wanking and whispering my name...."

She bent her head, giving one slow lick up the length of my now rock-hard cock. "Some of them are dead jealous - we all do babysitting, or have done at some point, and you're apparently the best looking father we've ever had between us... although I've obviously had you in entirely different ways than they think."

She swallowed by head into her mouth, her tongue flicking out to lick round my swollen crown. Then she pulled off. "In fact one of them - Jennifer - she was with me in town once when I saw you in the distance and pointed you out. You didn't see me wave of course, but Jennifer later saw you close-up, while I was in a shop, and she's quite smitten with you. She's VERY excited about being able to meet you at last. She's such a tart really - she's had a lot of boyfriends, none for very long, and she lost her virginity a long time ago, I think. She's got a bit of a thing for older men..."

She ran her fingernails over my balls, making my cock throb. "Oh Andy, I hope she doesn't come on to you. How will you cope? Because you know that that if you respond, I'll be annoyed and you won't get to put your lovely cock anywhere near me."

I reached down and started wanking. "Well, Sam, if this Jennifer does come onto me, maybe I should lead her on, getting you all jealous. Heck, if you won't put out, maybe she will. It sounds like she'll love a good stiff cock in her. Do you think she'll take it up the ass? Do you think she'll come over to me and beg me to use a dildo in her ass like you did earlier? Maybe I'll take her outside Angela's party, push her up against the wall, and take her standing up, from behind, knowing that you'll follow us out." I was wanking hard, determined to bring myself off quickly. "Knowing that you'll watch from the shadows, just like you watch Angela and I. Knowing that you'll be wanking yourself silly, jealous that Jennifer is taking my cock in her cunt in a way that you never will, and that I'm enjoying myself with another girl. After she's come, I'll pull out, line myself up, and slowly push my cock into her ass. You'll hear her scream in agony, then you'll hear those screams turn into moans, as she gets used to me, as she begs me to fuck her ass. You'll creep closer, desperate to see my cock spearing her insides, just like you watched me fuck Angela last week. Then you'll reach me, taking my hand, leading it down to your own ass, begging me to finger you while I fuck her..."

My come was approaching again, so I stood up, pushed Sam onto the bed on her front, and lay on top of her, my cock nestled between her ass cheeks, and started thrusting back and forth. "Then when I'm almost there, I'll pull out of her, bend you over, and slide my cock into you. I'll decide which hole - maybe your ass, or maybe your virgin cunt. Who knows? Maybe I'll alternate to make sure I have both your virginities. You won't be able to resist, begging me to fuck you, begging me to make you come. But I'll be almost there from fucking Jennifer up the ass - it won't take me long to come. You'll feel it - feel my come spurt into you as I grunt your name... and then I'll pull out, zip myself up, and walk way, leaving you high and dry for teasing me all night.... Now stay there Sam... I'm going to come... Your ass is fucking perfect for this... Big and firm... I can't wait to be in it instead of between your cheeks... It'll feel so good baby... Here it comes... Oh yeah... Here... Oh fuck!" I grunted, as my come leapt from my cock, spurting over her ass. She moaned as she felt it land on her, her hips working against me, her firm cheeks cushioning me.

I rolled off her. "You'd better have another shower," I said, laughing at her.

"Too late," she said. "I'll have to go to school smelling like this. Who knows, maybe I'll find a younger model to replace you with?"

I laughed at her. "You wish. But you know they'll be pump-pump-squirt guys, unable to hold it in long enough to make you come like I do. And you'll come running back to me quick as a flash."

She laughed, and headed out to pick up her clothes from wherever she'd left them.

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She texted me later that day. "You'll never guess. Jennifer smelled me. Don't know how. She knows I was with a guy. Lots of questions. Haven't let on that it's you. But might do before the party. If you want me to???"

I scrolled through the photos I'd taken with my phone, and found an old one of my erect cock, that I'd taken when I was at a conference, and which I'd sent to Angela at the time. I sent it onto Sam, with a note: "Don't tell her my name - show her this. Do you think she'll like it???"

Sam came back a bit later. "Couldn't show her. Don't want her to think I'm seeing a peewee herman."

I laughed, and left the conversation at that.

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Mondays, having to get back to work, weren't my favourite day, even though I quite liked my work. What made this Monday even worse was that I was doing my accounts, which is my most hated job. Well, at least until I see the final income figure. So, later that afternoon, when the doorbell rang, I was glad of the distraction.

When I opened the door, there stood Simone, wearing a raincoat. "What's with the coat?" I asked as I ushered her in. It was quite warm outside, and there'd been no rain for a while and none forecast as far as I knew.

"Is anyone else in?" she asked, looking over my shoulder into the house. I shook my head. In response, she undid the belt and shucked off her coat, leaving her standing there with nothing but a pair of stilettos and a pair of stiff nipples. My cock started responding.

"Come here," I said. She stepped into me, her firm breasts pressing against me chest as I cupped her ass in both hands. She groaned as we kissed, reaching up to pull my jumper off me, leaving me bare-chested.

"I've been thinking about you all day Andy. I want you to myself again. Being with Angela is lovely, and I want to do it some more, but right now I need a man who wants me, someone who ... oh god it feels so good to have you against me... someone who will treat me like a real woman, who knows what I want and when I need it... I'm so wet Andy, I've been imagining us together all day..."