Anal At Last Ch. 10

[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) was staying at my place one night, and caught me "doing a money shot" over Angela, and I saw her in the shadows of the stairs. None of us broached the issue, but in a deep conversation one night with Samantha, I found myself backed into a corner and admitting that I did think about her naked. She was excited but a bit unsure of how to handle it. The next day Samantha and Angela went shopping together, and paraded their new clothes to me, also making me show myself off in a pair of very tight trunks. Then Angela and I had sex on the sofa, pretending that Sam was watching...

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]

*

I woke the next morning to feel Angela's hand around my cock. I was already hard, and close to coming. She must have been wanking me for some time whilst I was asleep.

"Morning baby. is this for me? It's so big and hard already. What WERE you dreaming about? I hope it was me...."

I groaned and closed my eyes, enjoying the wank. This woman is going to wear me out, I thought. God bless her!

She slid down a bit, and went down on me, sucking my cock as deep as she could inside, still wanking my shaft. After a minute or two, she slid back up the bed. She let go of my cock, and threw the duvet off us both, exposing our naked bodies to the cooler air of the room.

Then she resumed wanking me, and lay her head next to mine. "Did you like last night baby? Seeing Sam in all her new clothes, exposing bits of her that you've never seen before. Just think baby, you might have been the first man to see so much of her ample cleavage, or her midriff, or her lovely legs. I could tell how turned on you were baby, and I knew that after an hour or so of watching her, and me teasing you, that you'd come more than I've seen you come so far. That so turned me on baby. I really wanted to see you come like you did, your jizz shooting up in the air. Did you like listening to my story, and wanking while you imagined my first time with a woman?"

I could feel my come building up, and told her so.

"It's OK baby, I want you to come for me again. Let me wank you till you come all over yourself.... then I'll lick it off you again... I love the taste of your come.... that's it baby.... I loved watching you wank last night... and then fucking my ass again... that's it, let it come, come on baby... you must be so close to coming again... I've got a secret baby - do you know what made it extra special for me last night?"

She had been wanking me firmly, nice long strokes, but then she changed to short, feathery ones, using my own pre-cum to lubricate her fingers as they slid up and down just my head, swollen and sensitive as I was approaching orgasm. She vibrated them up and down, just a fraction of an inch each way, the light, almost non-existent touch driving me wild. I felt my balls tighten.

"Oh god Angela..." I panted. "Keep on doing that... that's fucking amazing.. oh fuck, here it comes...."

She whispered in my ear as she grabbed my cock firmly and gave it a few good strokes. "What made it special is that we had an audience... Samantha was watching... We planned it that way baby..."

WHAT??? That did it. My come exploded from my cock, blasting up my body and splattering the pillow beside my head, then all down my body till the last few drops dribbled out. She kept on wanking me, forcing my come from me, as I gasped through my orgasm. She kissed my neck and shoulders as she slowed down her hands, letting me enjoy the come.

"What...? How...? Why...?" I spluttered, unable to form a coherent sentence because of my orgasm and what she'd just said.

"Why did we do it? As I said, she let slip that she'd seen you come over my face that night, but she was so embarrassed she couldn't say anything. I spent ... oh, god, hours... talking to her, getting her relaxed, getting her to open up. She's such a virgin Andy. Sweet, innocent, and very, very shy. She's never had ANY sexual encounter with a boy, not even a decent kiss, and the first thing she sees is your... delicious ... cock coming all over my face as I beg you to make me your slut. It was a bit of a shock, and she didn't know how to cope with it. So she thought I could help.

"And I think I did. As I say, we talked for hours - all that shopping was done in about two hours, believe it or not, as we talked for most of the day. We had to do the shopping quick so that you wouldn't suspect what we'd actually been up to."

She bent her head, licking some of my come from my chest, then sliding her lips and tongue over my nipples, teasing them, nibbling them, still wanking my softening cock slowly. I was still too breathless and shocked to speak.

She lifted her heard again. "Mmmm, you taste nice....Anyway, it took a long time, but she started to open up to me, and she said how much she enjoyed the experience, even though she felt embarrassed, and dirty. Do you know when she went upstairs she wanked herself off in your spare bed, thinking of you coming over my face?" My cock, which had been going down despite her continuing fondling, throbbed, showed signs of interest again. "Oh my Andy, does that turn you on again? You're so predictable! But I'll let you off - I like a man who can come like you did and be ready again so quickly. We're going to have SO much fun together!

"Anyway, she's very shy Andy, and very confused. She finds you sexually attractive - she always has done, even though I think she was scared to admit it to herself at first, but when she saw you and I together that night, well I think she let herself notice how sexy you are."

I grinned at her.

"Oh, don't let it go to your head. You're slim, well-built, mature, attractive, and got a nice sized cock - " I grinned even more - "but I've had better."

"Oh," I said, disappointed.

"Aaah, poor diddums. Did Angie-Wangie hurt Andy-Pandy's feelings? Never mind, I'll make it up to you later... Anyway, so she has finally admitted to herself that she fancies you, but she honestly thinks there's no way you'd be interested in her, even if you were single, and anyway, you've got me, so as far as she's concerned, that's the end of that. You're officially off-limits, even if she could actually pluck up the courage to approach you.

"But on top of that, she's terrified of the first time she'll be with a boy. And remember, that even includes her first kiss with tongues." At this, she lifted her head, and kissed me, sliding the tip of her tongue into my mouth, still wanking me. I kissed her back for a bit, and then we broke for air.

She continued. "So it set me thinking. First, I knew she looked good once she dressed up. Second, you've come several times before now whilst I talked about her so I know you fancy her, you dirty old man. Third, she wanked at the memory of seeing you come on me so I knew she found it a turn on watching you. Then fourth she needs more experience. And fifth..."

She paused.

"And?" I asked

"... and I trust you Andy. I know it's not been long between us, but God help me I trust you. So it was obvious what had to happen next."

"Angela, you devious old trout, what are you up to? And what were you thinking of letting her see me come like that again?"

"She needs someone to practice with, Andy." She saw my face light up. "Down boy, that's not what I mean. Not sexually, just flirting. Someone to dress up for, and who will appreciate it, and even encourage it, without trying to get his cock into her pants all the time or get pissed off if she doesn't put out. Someone who'll flatter her outrageously when she wear's something that's a bit out of her comfort range. Someone who will tease her like you tease me, so she can learn to handle someone coming onto her when it actually counts, instead of freezing like a rabbit caught in the headlights. Someone she can practice chatting up, and practice being a woman for fucks sake, instead of daddy's little girl."

Again, she paused.

She looked me right in the eye. "So I said she could practice on you."

"You WHAT?"

"You heard, Andy. But no touching! And she is absolutely NEVER to find out that you know about this. She can watch us occasionally, when I say so, from the shadows. She can flirt, show off her body, talk brazenly to you, and you can pay her those outrageous complements and make her feel good about herself and her sexuality, but I repeat, she is never, EVER to know that you know about what she and I have agreed. As far as she is concerned, you're just responding to her naturally, as she opens up to you. She can even talk to you or me about sex if she wants to.

"In fact, I've not even mentioned how turned on you are by the thought of her wanking herself silly after seeing you come - see, another throb, you're so shallow! - so you'd better not even come on too strong or suddenly change your behaviour. Just pretend that you're slowly, gradually coming round to seeing her in a different light, and each time she goes a little bit further than she has so far, you can also go a little bit further, as if you're warming to her, and finding her new behaviours and dress-sense more and more erotic.

"But if she finds out that you know about this little agreement, she'll think you're responding to her because I asked you to, not because she's getting more confident and sexy. It'll ruin her self-esteem. And if you do that, you're not the kind of man that I think you are, and it'll be over between us, quicker than you can say Jack Robinson.

"So, you can look, talk, be seen, but it goes no further. No touching. And if she seems scared or worried, you back the hell off immediately and tell me, and I'll find some way to bring the topic up in conversation with her and ease her fears, without letting her in on the fact that you know about the deal. Then you wait for me to give you the all-clear before taking it any further.

"I'm in charge of this. I know you, and I know her, and she'll confide in me, and I'll say what does or does not happen. Is that perfectly, absolutely clear?"

I couldn't believe my luck. "Let me get this straight: you want an innocent little girl to parade round my house semi-naked, flaunting herself, chatting me up, asking me all sorts of sordid little questions, watching us have sex from the shadows. All with your approval. And you think I might say no?" I grinned at her as I thought of all the fun to be had.

"Andy, calm down and be serious. It's not for your benefit, although I'm sure that you'll get your kicks. In fact, if you do well, I'll make sure that you get your kicks, but with me, not her. You won't believe some of the things I'm going to do to you and for you, if you stick to this agreement. I'll be your own personal sex toy, your little slut, ready to do anything and everything you've ever dreamed about, and some things that you haven't. Even if we split up afterwards and you live to be a hundred and ten before you die, you'll still go out with a huge smile on your face thinking about what we've done."

I looked her in the eye, trying to work out what was going on. "Angela, tell me one thing. Why? What are you getting out of letting her watch us have sex? Oh, shit, I can't believe I talked about her watching us while I fucked you last night!" I exclaimed, excited but also perplexed by the situation.

"Don't be daft Andy, I wouldn't let her see that!"

"But -" I started.

"I know what I said in the heat of the moment, but I didn't mean it. No, she only watched you wank. She really was asleep when I looked in on her later." She sighed, turning inwards for a moment. "You might not believe this, but I was like Samantha is now, even when I was a bit older, around 20 or 21. And the one big regret of my life is that I didn't take opportunities earlier to gain experience, both physical and non-physical - flirting, confidence-building, and so on."

Another sigh. Then a little smile. "Of course, I've made up for it since," she added. "Especially with the help of this". She squeezed my prick as she said that, seeming to enjoy the fact that I was now rock-hard again thanks to the chat, and what she wanted me to do, and the fact that she'd still been wanking me all this time.

"So I offered your help to let Samantha rapidly catch up with her peers. That's all that this is about. If you think you can't handle all that titillation without having to take it further, tell me now and I'll cancel it with her... tell her I've had second thoughts. But if you do decide to go for it, she must never find out. I like that young girl, and it's kind of a chance to redo the errors I made when I was younger. It's important to me. Promise me that you'll do this according to my rules Andy."

She was deadly serious. Obviously this was a very important issue for her. And to be honest, I liked the idea of flirting with Samantha and then meeting up with Angela to take out my arousal. It should make for interesting times...

"Honey, you got it. And, as we're being honest with each other, I trust you too. I'm not going to do anything stupid enough to risk losing you."

She smiled a little smile, and then lay back on the bed, sighed, and blew her cheeks out in relief. "Phew. Thank God that's over with." She took a hold of my hand. "Thank you Andy, you have no idea how much this means to me."

Then she grinned. "Of course, if anyone was listening in to this conversation, they would be laughing at us, you do realise that, don't you?"

"Well it is a strange situation!" I answered.

"No, that's not what I mean. Listen to us: 'I trust you Andy', 'And I trust you too Angela'. We both know what we meant, I think, don't we?"

I laughed. "Are you saying that we just couldn't come out and say 'I love you' to each other?"

She cuddled into me and sighed deeply. "Well, isn't that what you meant, Andy?" she said softly, stroking my chest with one hand.

"Angela, honey, I hate to break it to you, but it's just sex between us. I mean, you're way below what I normally shoot for! I'm just giving you some sympathy sex so that you don't die a frigid, wrinkled old prune."

She slapped my chest, calling me an evil bastard. Then she rolled over and straddled me, pushing my arms up over my head, and bringing her head down next to mine. "Andy, honey, we both know the truth. You love me, but you're too scared to say it. Admit it baby, say it, say 'I love you Angela'". She was grinding her groin around on me as she spoke, and I could feel her moisture seeping from her.

"OK," I said, and she looked at me intensely. "I love ... the way you can't keep your hands off me. I mean, look at you, we're just talking about your feelings for me, and your juices are leaking all over me already. Admit it Angela, it's YOU who's in love with ME. After all, you said it first."

"I never said I loved you!" she shrieked.

"No, but you were the first to say 'I trust you', and as you said earlier, we both know that 'trust' is a euphamism for 'love', don't we?"

"Andy, you're so pathetic. How could I possibly love someone of your stature and manliness, after all, you're so out of my league, right? I could never love someone like you, I could only feel awe and lack of self-worth." She laughed, causing our groins to bounce delightfully together.

I wrestled my arms free, slid them down her back to her bum, and pulled her down, pressing my now erect cock into her wet cunt. "That's right honey. It's a bit like the stories of Zeus. I'm just sowing my wild oats amongst the mortals, and you're just my latest conquest. I am after all, a god amongst men."

"That's right Andy... oh that feels good... so as you are such a god amongst men, you'll have no problems doing what I told you to do last night... go down on me and don't come up for air till I tell you." With that, she rolled onto her back, pulling me on top of her, and then she spread her legs, and started pushing on my shoulders.

I resisted the pressure, and raised my body up so that I was in press-up position, rolling my hips to rub by cock up and down her wet lips. "Oh mortal woman, wouldn't you rather I plough you with my mighty staff instead? It's brought pleasure to many, many women before now, and I'm sure you'd like to experience such dizzy heights, wouldn't you?"

"Oh mighty Zeus," she said, still laughing, "give me your rod of pleasure, thrust it into my gates of heaven, show me your strength and virility.... and then you're going down on me, no excuses."

She pulled my head down close to her mouth and breathed into my ear. "Andy honey, I want you to come in me - there's been too much wanking for my liking, and all that come has been going to waste... Come in me, and then go down and lick it all up till I come again. I've always wanted someone to do that to me... will you do it? Will you go down on me after you've come in me? I'll owe you big time..."

"Really?" I asked, with a salacious grin on my face. "What will you do for me in return?"

"Well, I was kind of thinking that actually, you should go down on me in return for you fucking my ass again last night, but if you insist.... You know Britney's video for 'Ooops I did it again'?"

"Doesn't every man?"

"I've got the outfit..." she whispered, as she wriggled her lower body to get my cock lined up with her cunt properly.

Of course, I knew that already from her emails, but I couldn't say that. I also knew she wanted spanking. "Really? Then here's what's going to happen: You're coming over one night after school, in your school costume, when we've got the place to ourselves, and you can do your homework. I'll stand real close behind you and watch you do it. And if I find one mistake, just one, I'll have to punish you. You're not too old to have your ass spanked, you know." And with that, I pushed inside, slowly but surely, one long smooth movement till I was balls-deep inside her.

She groaned into my shoulder as I filled her and stretched her inside. "Oh god Andy, do it. Fuck me and fill me with your come. I want to feel you come inside me... I promise to be good and do my best with the homework, but if I do make a mistake, I hope you don't punish me too badly. My ass is so sensitive baby, and it'll get real sore... oh you feel good... you'll need to rub some lotion in after you've finished spanking me, to help me feel better... that's it baby, all the way out again and then push! Oh sweet jesus you feel good... will you do that baby, will you rub lotion in to soothe my poor butt? You'll have to be careful though, in case all that lube accidentally lets something big into my tight little back hole..."

I kissed her passionately at the thought of that, and then lifted up into a half-press-up position again, my upper body lifted clear of her, only our hips and legs touching. She raised her head to look down our bodies as I started fucking her properly. "Andy, honey, that looks so good... I love seeing your cock in me... you've got a great body honey... show me your cock". I pulled almost all the way out, leaving just the very tip separating her lips. "Oh fuck Andy, that makes me so horny. I love your cock. Do it baby, fuck me, make me come...

"Do you know how turned on I was last night? That's why I wanted you naked when you wanked... I wanted to have your hot body stretched out on that sofa, so I could see your stomach and chest and arm muscles tighten as you wanked... you look so good when you're stroking yourself... and I knew Sam would enjoy seeing you naked with that big cock of yours bursting at the seams...