Anal At Last Ch. 08

And I know what that issue is, I thought.

She looked away, thinking. "Well.. there is something... it's a bit embarrassing... I'm not sure I want to talk about it."

"Well, it seems to me you NEED someone to talk to, even if you don't WANT to talk about it. But if there's someone else you'd rather talk to, I'll shut up now and we can talk about the weather."

"No, no, it's not that.. you're great to talk to. People my age don't know any better than me, so they're not much help, and people your age .. sorry, I'm not saying you're THAT old!... are often a bit too stuffy or embarrassed themselves to be of any use. You seem more...." She paused.

.".. more what?" I pushed.

"Well, more like someone my own age, but less superficial. Someone who still knows what it's like to feel a real spark for someone, rather than being stuck in a rut that older people get into. I've seen you with Angela... I mean I've seen the two of you together... No, what I mean is -"

I nearly leapt from the chair in delight, but restrained myself to grinning as I saw my chance. "Samantha, I hope you're not saying that you've been spying on Angela and I when you've stayed over? Not after I was telling you to not get caught with your boyfriend?"

"No!" She looked panicked, eyes wide. "No, Andy, you're making this worse. I mean that I've seen the two of you together, in the kitchen, over breakfast, and so on, and I've seen the look in your eyes when you're talking about or with Angela, and you've still got some fire in you. I guess my brother's the same, but there's no way I can speak to him about this kind of thing, and my dad's... well, he's my dad. And my friends are too young."

"OK, well, I'm glad to be able to help. I'd like to think that all the trouble and confusion I went through might be of use to someone else at some point! So... what's the problem?" I ended, gently.

Another slug of wine, more dutch courage. She flushed again, embarrassed.

"Well, it's like this... not sure where to start ... something's happened recently... there's a man, well, a boy, you know what I mean... "

Did she mean me, when she said 'a man', and then corrected herself so I wouldn't guess who she really meant?

"Is this the guy from your church?"

"No, someone different. I've known him a while, but never really thought anything of it. Oh, I like him, he's a nice guy, strong and silent type, not flashy at all...but I've never thought of him in THAT way... but something's changed recently, and I find myself thinking of him a lot."

I'll BET something's changed - you've seen him come all over his woman, that's what!

"I don't really know where to go from here, but it's set me thinking about this whole sex before marriage rule. I mean, it's not like I want to leap into bed with him - I'm definitely saving that for marriage, as something special for my husband. But... well... I find myself thinking about what it might be like to BE with him - you know, kissing, holding, waking up in his arms in the morning, that kind of thing." Another gulp of wine. "Sorry, this is really embarrassing. I think I've had too much wine. I'd better go." She stood up, collecting her things.

I stood up as well, moving in close to her, taking a gentle hold of her shoulders. "Samantha, don't be silly. I'm not at all embarrassed by this - I just wish I'd had someone I could talk to, a woman obviously, when I was your age. Here, sit down." I gently pushed her back down on the sofa, and then I took a seat beside her, sitting sideways on.

I wondered how to lead the conversation towards my sordid little goals.

"So what's caused this change, Samantha?"

"Err..." More flushing. "Well, I kind of saw him recently... he was with a woman, well, a girl... that he's been seeing for a while."

"OK... I'll assume they weren't just shopping, as that probably wouldn't have changed your opinion of him... Did you catch them doing something a bit more intimate?" I didn't want to push too hard.

Samantha gulped. "Yes.... but that's all I'm saying. It's just set me thinking, that's all."

"And keeping you awake at night, I'll bet," I joked, imagining her laying in bed, playing with herself as she mentally replayed what she'd seen, both in person from the darkness of the stairs, and also probably from the DVD and photographs. "So what's the problem - is it that you've been having these thoughts ... jesus, I sound like a catholic priest at the confessional... or that you're having them specifically about him, when he's seeing someone already?"

She thought for a bit, reaching out to put the wine down on the coffee table to let her shift position. That brought her leg a bit closer to me, almost touching. I noticed her hand wasn't as steady as it should have been when the put the glass down. Obviously, the wine was getting to her a bit.

"Both really. I do find him quite attractive... now, although like I said, I never thought about it before... but I'm also a bit jealous of his girlfriend."

Ah, jealousy, music to my ears.

"Jealousy's an odd emotion," I said. "For some people, jealousy destroys them, consuming them from the inside. For others, it becomes freeing, showing them what they truly desire, and giving them the strength or drive to go for it.

"For example, let's say this man .. or boy, whatevever... overheard this conversation tonight. He'd probably be jealous as well. Not jealous of you, but jealous of whoever your next boyfriend will be. This boy will know that he's stirred up all these feelings in you, but not be able to do anything about it, and someone else will get the benefit. I mean, you're a pretty girl... albeit one with a lousy dress sense," I laughingly added, as she looked away again.

"He'd be sat there in his room, alone at night after his girl has gone home, thinking how nice it would be if he could get together with you, thinking about how sexy you'd look if only he could get you into some decent clothes." She laughed, but was a bit embarrassed as well, I could tell. "And you know what teenage boys are like.. all those hormones... who knows what he'd get up to in the privacy of his own room, thinking about you...."

She shrieked with laughter. "Andy, that's terrible!"

"No," I answered, "that's boys. And I should know - I was one once!"

"You mean you..."

"Of course, I don't know a single boy who didn't amuse himself. And although no man will admit it, I reckon all grown men still do," I said, with a raised eyebrow.

"Andy, you're awful. Surely grown men ... well... they don't... you know... when they're seeing someone?"

"Every last one of them. Sometimes even with the help of their woman." She looked at me, eyes and mouth wide open.

"Apart from me," of course, I added, as if caught in my own trap, but also with a twinkle in my eye, leading her specifically to the thought of me having a wank.

Her eyes flicked all around the room as she took in what I said, and I noticed they did take in my crotch. And linger for a moment longer than everywhere else, I think.

"Anyway, that's enough embarrassment for now. But that's the point I'm getting at. A nice healthy sex life is important, even if it's solo, even if it's before marriage, and even if it doesn't lead to actual penetration. Whether you're 18... " - I subtly waved my finger towards at her - " ... or 36" - and then towards me, deliberately leading her to think about her and me.. "But there's one pre-requisite..."

She waited for me to finish. I didn't. "Which is?" she finally asked.

I looked up her up and down, taking in her breasts, stomach, hips, and legs, deliberately taking my time and letting her see what I was doing. "You really, desperately, need to get a new wardrobe." And with that, I burst out laughing, partly at the joke, and partly at my evil little plan coming together. She grabbed a pillow, and started hitting me with it, calling me "a horrible man," and other things. She hit me a few times, so I grabbed her forearms to stop her, leaning into her a bit, bringing our heads closer together. I knew now that the wine had done it's job, getting her relaxed, letting her see me as someone she could misbehave a little bit with, rather than just being the babysitter hirer.

"Oh, I lied, there's one more thing you need to do," I said, still holding her steady, "Even with the right clothes, that's not enough, you need to tone up a bit, lose a bit of that baby fat" I said, grinning, knowing that as a teenage girl, she'd fight back at that one. "You bastard," she screamed, struggling in my grip, trying to hit me again with the pillow. I gripped her a bit tighter, and also leant away from the back of the sofa a bit to get leverage, pushing her away from me further into the back of the sofa. We ended up more directly facing each other, our heads moving a bit closer.

She looked a bit too flustered, so I eased back, guardedly letting go off her arms as if scared - or reluctant to set her free. She hit me once, then stopped, pondering.

Then she asked that loaded question: "So do you think I'm fat?"

"A little bit," I answered, with a glint in my eye, hoping she'd rise to the bait.

"You are a nasty person, Andy," she came back, with a lop-sided smile on her face. She sat back, folding her arms as if in a hump.

"Well, take a good look at yourself," I started, "baggy jumpers, loose jeans .. you've gotta be fat under all that excess clothing. Surely". I kept on smiling to let her know I was joking.

"Well I'm not," she retorted. "Just because I wear clothes that don't reveal everything, doesn't mean I'm fat." She was getting a bit pissed off now. Possibly at me, or possibly because she's had this conversation in the past and is fed up with it.

"No, you're right. But there's a difference between dressing smart, and dressing frumpy. And I hate to say it, but you're on the frumpy side, Mrs Doubtfire." She slapped my thigh at that point, deservedly so, but I could tell she'd gotten the joke.

"Well.. it's so hard... most of my friends are either from the church, so they dress like me, or they're not, so they dress like, well, a bit tarty, to be honest. And I've not got a mother or sister to get advice from. And I find it hard to find a good balance."

I had an idea.

"Wait there a second," I said as I picked up my phone. I called Angela, and fortunately, she answered.

"Angela, it's me. I need your help on something."

"Hey babe, what's up?"

"I'm just sat here chatting to Samantha -"

"Oh yes," Angela said, archily

" - and she's saying how she's not got an older sister or mum to help her shop for clothes, and she agrees with me that she needs the help." Samantha raised her hand to her mouth, not believing that I was telling Angela everything. "So I thought, seeing as how you dress very nicely indeed" - I lowered my voice, to a more seductive tone, as I said that - "you could maybe take her shopping one day, help her choose some outfits that are not too tarty, but definitely, definitely, not as frumpy as the get up she's wearing now. How's that sound?"

"What you mean is: you want me and the virgin to go shopping, maybe have a glass or two of wine over lunch, get together in the changing rooms, I'd start helping her into her dress, and I'd maybe touch her up as she tries on a bra. She'd get aroused-"

At that, I stood up and moved away from Samantha, so she couldn't hear, fetching my wine glass from the other end of the coffee table to cover my movement, and then stayed standing up.

"- and she'd moan as I slid my hand inside her bra, feeling her nipple harden under my fingers. We'd then kiss, our thighs pushing into the other one's groins, our tongues playing together, her hands coming down to my lovely little bum-"

"Yes, that sounds like a great idea," I said, looking at Samantha and nodding my head as if to say that Angela had suggested something. I was also fully aware of the interest being played by my prick right now.

" - and then I'd run my hand down to that sweet little honeypot, feeling how wet she was already, pushing a finger inside her, making her groan as her pussy feels the first thing ever to enter it. She'd moan your name, imagining it was you taking her - "

"Yeah, she's right here" I interrupted, painfully aware of movement down below. Angela picked up on it... unfortunately.

" - Oh, I'm sorry Andy, are you getting a hard on with all this talk of us to women together, just like in that porn you watched? Is she in front of you? I bet she's sat on the sofa, the one where you sat the other night whilst I gave you a blowjob. Wouldn't it be great if she just came over, knelt down in front of you, looking up at you with those big doe eyes, pulled down your fly, manhandled your beast of a hard-on out your jeans, her eyes wide with horror at how big it is. Then she'd open her mouth wide, and swallow your hot, hard cock?"

I sat down on the sofa, the one opposite Samantha. "OK, baby, I'll hand you over to Samantha to make a date," and then I promptly took the phone away from my ear and put it into Samantha's outstretched hands, before Angela could say anything else. A quick chat ensued, with a few "yeah, that'll be great!" type of comments from Samantha, and then she asked if Angela wanted to speak to me again. She gave the phone back to me. Obviously Angela had said yes.

"OK, it's all sorted, tomorrow actually, to get some shopping done on a quiet sunday. I'll come round afterwards, if you're around, and tell you all about it. And then I'll put on some frumpy old clothes like she wears, and you can fuck me senseless, calling me by her name as you come in me.... Does that sound like fun?"

"That'll be great, honey, see you then" I said, and then I hung up the phone. There was no way I'm standing up right then, so I hurried the conversation forward. "So... all set then?"

"Yes, we're heading out tomorrow, have a glass or two of wine over lunch -"Oh dear god help me, I thought, " - and then shopping afterwards." She paused. "Do you think she was OK about it? I mean, she sounded OK and everything, but you know her better than me. I'd hate for her to think she was badgered into it just because you asked."

"Oh yes, I think she was VERY excited by the idea." Obviously, I didn't say how excited I was.

But I needed to break the ice and give my hardon time to go down.

"So how are you going to manage the clothes size issue? I mean, if you're buying clothes tomorrow, but drop back down to a more normal weight over the next few months, what's the point -" I didn't get any further, she leaped up with the pillow in hand, coming right at me. But she caught her foot on the coffee table leg, stumbled, and fell towards me, her hands coming out to catch her. And you guessed it - one hand landed on my thigh. Half-touching my only-slightly-shrunken hard on.

It throbbed.

She didn't move immediately, a bit stunned I think, and I could feel the heat of her hand on my cock.

Then she shot back away from me, shock on her face.

"Oh god, Andy, I'm so sorry, I didn't mean to-"

"Samantha, it's OK, it's OK. I... er... well.... Angela said something to me on the phone that is a special code word between us. It kind of got me thinking about her, and... well... it's obvious what happened next."

She pulled back further, sitting her ass on the edge of the sofa. I stood up, and started collecting her things together, painfully aware of trying to keep my hard-on out of her sight, and all the time hunched over like Quasimodo from the tightness down below. "Look, it was an accident, a very embarrassing one... here, I'll collect your stuff, you put your coat and shoes on, and I'll phone for a taxi for you."

She swigged the rest of her wine, still sat there with a glazed look on her face, while I finished collecting her items and started phoning for a taxi. Then she looked me in the eye. Oh, shit, what's coming now? She kind of straightened her back, lifted her chin - a look of resolve across her face. As the taxi company answered, she took the phone off me and hung up.

"Andy, don't be silly. I can kind of see what you've been getting at all evening. It's exactly the same thing... You and Angela have obviously got something special going on. One word from her and... er... you react. In a very natural way, I agree. That's OK.... It proves that your ... um... your sex life... has made you mean so much to each other... brought you closer together than I've ever felt with anyone. I mean, just one word and ...." She shrugged her shoulders, eyes darting about while she sought the right word. "Boing!" She smothered a laugh. I looked at her in amazement. Two or three glasses of wine, and she can talk about an erection like that?

"Boing?" I asked, a smile also coming to my face.

"Boing!" she answered definitively, and that set us both off laughing our asses off. Each time we calmed down, we looked at the other one, and started laughing again, giggling like little schoolgirls.

Eventually we calmed down a bit. "Listen, Samantha, I really am sorry, but it's like I said. Men are raging hormones, even old farts like myself, and it only takes the slightest thing to set us off."

"You're not an old fart Andy....Really? The slightest little thing?" she asked, looking down at the hand that had landed on me. Was that a slight note of interest in her voice?

"Yes, really. The slightest little thing. You wouldn't believe how little, even if I told you... which I'm not, no matter how much you ask. Some things are best kept secret from the other sex, never to be divulged. You should know, women keep loads of things from men."

"Hmmm. Like what?" she asked playfully.

"Well, first of all, why you always go to the toilet in pairs when you're out socializing. And you NEVER, EVER discuss what you talk about with each other when men are not around. NEVER, EVER." I needed to get this back to her in some way. "But some things are just more individual things, unique to each woman... such as what you look like under those old sacks you're wearing." I grinned at her, then leered lecherously at her body.

She glared at me, sending toy daggers across the coffee table.

Then she went all quiet. She paused. "Are you saying you want to see me with no clothes on?"

Oh, shit, where's this going to end up?, I thought.

"God no, Samantha, that would be too horrible to even think about" - I smirked as I said it, again running my eyes up and down her body, but letting my eyes say "Yes, Samantha, that's exactly what I'm thinking." I continued with " - but your boyfriend, and that man, sorry, that boy that you've recently begun thinking about, I bet they're both dying to see what you look like."

I looked at her, waiting for the banter to continue. She sat for a moment, obviously thinking about this a bit. She shifted slightly. Was she getting turned on by this, rubbing her thighs together?

"Andy, that's a horrible thing to say, as if they'd think about me that way."

"As I said, you're an attractive young woman under those... HORRIBLE... clothes. And these two people are young men. Full of raging hormones, desperate to find out about women and all their feminine delights. That's what we do. All the time. Even when we dream. We can't help it."

"But you're saying that you don't think about ME that way?"

Oh sweet jesus, just kill me now. She was biting her lower lip a bit, head downcast but looking at me through her upper eyelashes, in the way that Princess Diana did so famously in that candid interview on TV.Fuck me, she's asking that question meaningfully, afraid I might say no, afraid I might say yes... I didn't think I'd ever seen anything more seductive in my life.

I sat back, shaking my head, lowering my voice as I remembered I was dealing with an 18 year old virgin, not a wanton, experienced, older, more confident woman like Angela. "Oh, Samantha, honey, never ask a guy that question. You might not like the answer."