Where Is This Leading?

My hands were shaking as I slipped them into the elastic of the thong. It always seems to me to be a really symbolic moment when a woman takes her panties off for her lover. More so than when he pushes them down or even when he rips them from her. By her doing it she's offering herself isn't she? She's voluntarily removing the last bastion of her defences, the remaining separation between her and her nudity, and the last vestige of respectability. Once they've gone she's vulnerable, open and wantonly available, well at least that's how I felt when I pushed my panties down and reached towards my foot to take them off.

As I stood up totally naked apart from my strappy, mid-height heeled sandals, so Jon reached for my hand, the one holding my panties. He gently pulled them from me. His eyes boring deep into mine he put them to his face and rubbed his nose in the gusset, taking deep breaths as he did so. I'd heard of men smelling their lover's panties, but I had no experience of it. I would have thought I'd feel at least a little bit odd watching a man do that, but I didn't. As Jon ran them over his face standing naked before me, so I found it not at all off-putting; not a major turn-on, but certainly an action that very much went with the circumstances.

Still holding my panties in his hand he put his arms on my shoulders. He looked deep into my eyes for a moment and then kissed me long and lovingly. Slowly his arms went round me, they pulled me to him, he pressed himself against me and our bodies moulded together. My breasts were squashed against his chest, the fronts of our legs were as one and of course his erection surged up the softness of my stomach. It was all rather lovely.

He squirmed his cock against me and cupped the cheeks of my bum in his hands. He squeezed and kneaded them all the time kissing me so beautifully. He stroked my bum he pinched it, rubbed it and caressed it. He was doing that for ages, but I didn't care, I loved it. I have such a sensitive bottom, all over and between the cheeks. And somehow he seemed to know that, but then perhaps all women do. His fingers probed and prodded, slithered and slipped everywhere. Over my cheeks, between them, on the entrance and further onto and into the slimy wetness of my pussy that was wet to overflowing.

I got my hand between us and my fingers tingled with want as they found and then ran up and down his erection. It was everything an erection should be; hard, warm, smooth and slightly throbbing. It felt lovely.

At last we went to bed, but clearly not yet to make love, well not as I knew it. He positioned me carefully on my front and lay beside me. He kissed me and ran his hands through my hair, ruffling it, piling it up on my head and then, as he shoved his tongue very deep into my mouth pulling it, quite hard.

"Oooo," slipped from my mouth.

"Sorry my love, don't you like it?" He asked not in any way, though, lessening the tension as he added. "I am sure you will get to love it."

In all my active life I had never been confronted with the pain thing. I had never had full anal intercourse, been tied up or restrained. None of my motley gang of male lovers that for some reason I suddenly recalled had reached double figures, had suggested any form of spanking, BDSM or anything that most people might call kinky. And to be truthful I'd never really given that side of sex much thought, but now having my hair pulled in a way that hurt me I was forced to.

It was odd, but then many aspects of sex seem to be odd to me; so much so that I'm beginning to think that odd is natural and natural is, oh shit, I don't know, far too deep a topic for me. But it was strange to me that the pain from my head was merging with the sexual pleasures his other hand was providing by stroking all over the back of my naked body. And the rather aggressive nature of him tugging my hair as I lie somewhat restricted beside him, was in stark and I have to say pleasurable, in an odd way, contrast to the tender kisses he was planting all over my face and lips.

Jon had slid the hand that wasn't tugging my hair down my back and had reached my bum, He'd stroked it and squeezed it and that, together with the kissing and tugging of my long blonde hair, had created the most unusual, yet wonderful combination of feelings.

"Ok Chrissy?"

"No, er yes, yes, it's ok Jon," I replied, not at all sure that it was ok or why I was saying that.

"You have the most glorious arse," he murmured as he stroked it very gently. He repeated all he had been doing when we were standing beside the bed but now the emphasis of his caresses was between, as opposed to on, my cheeks. He eased my legs apart and with them went the cheeks of my bottom. He spent ages gently running his fingertips along that sensual groove, on, over and past the extra sensitive entrance to my anus, onto the base of spine in one direction and into the totally sodden mess that was my pussy in the other.

I was starting to cum. I just couldn't help it. I don't think anyone, even my ex-husband had worked me up so much as this fifty plus year old man was now doing.

"Oh God Jon, I'm cumming," I moaned as my entire body started to shudder.

"I know Chrissy that is the idea you know."

Even in the throes of my strong orgasm I couldn't help smiling and saying.

"Oh shut up."

All hell broke loose in my mind. As my body shuddered and shook with the sensations, I couldn't help realising that I was cumming without any form of penetration, without my clit being rubbed or the lips of my pussy being stroked. Yes Jon made me cum merely by stroking my body and my bum.

As I soared up that wonder wall of such incredible feelings, another thing happened. Jon smacked my bottom several times. It was not that hard and not that much, but enough to make my bum sting and me recognise what he was doing. I did not think that much about it. I put it down to being just one of those spontaneous things we might all do when hugely, sexual stimulated; like pinching too firmly, squeezing a breast or a cock too hard, scratching, sucking or biting. Nevertheless, the combination of the pain from him pulling my hair, the stinging from where he had spanked my bottom and the pleasure he was giving me with his fingers made me cum, very heavily indeed.

He then fucked me. Straightforward, me on my back, him on top, my legs wide open and wrapped round him. It was quite quick and quite hard. There was obviously no foreplay. He didn't need to get me wet and I didn't need to get him hard, what we had been doing for the past half hour or so had done both of those necessities. He didn't mess around either.

I'd hardly finished my bum oriented orgasm when he turned me onto my back and I watched as he slid into a condom, a black one I noted with a tad of amusement. My pussy was still tender and my breasts and nipples were still pulsating from what he had done to me moments ago with his hands when he laid on top of me. I willingly opened my legs and wrapped my arms around him as he held his cock against my lips. I was obviously soaked and my lips were inevitably bloated with the blood that rushes to them during an orgasm; I'm told that makes a woman's pussy tighter.

I had no complaints, just a straightforward hard and fast fuck and that, to be honest is what I wanted. Well actually what I most wanted would have been to have waited for a while to let my climax fully subside, have a few drinks, maybe smoke a weed, enjoy loads of foreplay and then a long languid fuck or two. But I wasn't experienced enough to even say to him what I would have preferred, let alone directed events that way. And in any case I think I am much more of a follower as far as that's concerned.

So it was a quick fuck and I was on my way home shortly after.

*

We agreed to have the dinner we had discussed earlier on the coming Friday, the day after tomorrow.

Even though I was busy with studying lighting and sound for college and doing some freelance copywriting on the Thursday, I thought about Jon and what we had done quite lot over those two days.

My thinking about my actor lover was along these lines.

I liked Jon and clearly, I fancied him, I mean I had fucked him hadn't I?

He did something to me no others had done. Just how and why I couldn't say, but he did. I found him intellectually attractive. Maybe a father figure, was that it? A deeply buried desire to have sex with my dad? Shit, I had once had hots for my mum, not dad as well, surely? Not a threesome with my mum and dad? I told you I was odd as far as sex is concerned didn't I?

But there are limits aren't there? Could I really feel comfortable on a date with a man of his age? Could I cope with the stares and the whispers and the questions if anyone at the college found out, as they were bound to do?

Working away in my cubicle in the ad agency in Covent Garden, my mind kept returning to Jon. I thought of his obsession, or so it seemed, with my bum. I thought how amazing it had be made to coaxed to cum with hardly any vaginal or clitoral stimulation and no penetration at all. I would never have believed it, but it had happened. I thought about the way he had pulled my hair and how surprisingly that had added to the excitement. Also, of course, I thought about how as I was climaxing he'd smacked my bottom several times.

I had no experience of this pain and pleasure concept. I could not envisage being hurt and becoming turned on by that. I had no realisation at all as to how a man could hurt me and that would give me sexual pleasure.

*

I could hardly believe it. I had heard of it of course, but so far had never experienced it.

Jon's cock that was just about to fuck me had gone soft. One moment he had a full erection that I had stroked as he'd kissed me and the next as he tried to enter me so he lost it.

"Oh fuck, bollocks," he moaned his head falling onto my chest. "I'm sorry."

"What is it, what's the matter?" I asked genuinely concerned that perhaps he was ill, or worse was having a heart attack.

"I've lost my fucking erection, that's what's the bloody matter," he groaned rolling off me and lying on his back.

"Never mind, don't worry, it'll come back."

"Yeah, you reckon."

"Yes. Yes of course it will, I'll make it come back Jon," I whispered in his ear as I ran my hand down his body, across the slight swell of his stomach and into his pubic hair. I was so used to finding a man's cock sprouting up from them and pointing northward that I was surprised at first not to feel his like that. I could hardly remember ever before holding a flaccid penis; I mean it would be such an insult wouldn't it to be naked with a guy who hadn't managed to get it up? But that's where we were and that's what we had to cope with. It's not all plus points, I thought ruefully, having a yen for older men!

I pulled the condom off and dropped it on the floor. I worked hard. I stroked, caressed and gently rubbed it. I put my fingers round it and I pumped it up and down. There may have been a marginal hardening, but not much and certainly nowhere near what I wanted or needed to be fucked.

However, now I badly wanted that.

We had been in his flat for an hour or so after a nice dinner at a charming French bistro in Southampton Row. This time we had undressed each other and he'd made me cum with his mouth. He was really good at oral.

We played with each other for another twenty minutes or so I suppose, when he rolled me onto my side facing him. He turned onto his side away from me and fumbled in a drawer on the bedside cabinet. Rolling back again, I saw that he'd got a condom, not a black one this time, and was undoing the foil. He had pushed it on and then turned to face me the slightly greasy rubber pressing into my tummy. We kissed very deeply and I felt him moving to position his cock ready to enter me; the latex covered tip was pressing right against the lips of my pussy. It was, though clearly at the wrong angle so when he pushed he did not go up me, but merely slid along my slit and came to that cul de sac at the back end of it. Nice though that was, it wasn't penetration and it was penetration we both wanted.

He tried again. He pulled my leg up and placed it on his hip and once more pushed forward. Again, it did not go in.

"Oh fuck," he said in frustration.

"Come on let me help you?" I replied reaching down for his cock.

Whether he was already losing his hardness or not I don't know but he pushed my hand away.

"No it's ok. Lie on your back."

I did as I was told and he manoeuvred himself on top of me and laid between my eagerly opened thighs. I felt him reaching down, presumably to hold his dick and guide it in that way; little did I know then just what his real problem was!

This time when he pressed it against my lips it felt different, it was a feel I'd never had there before, it was new to me but somehow I knew what it was. Some instinct or intuition told me that he was losing his erection. And trying to shove a soft cock up a wet cunt just doesn't work does it?

So there was I working on making him hard.

My pussy had failed when he put it there, my hands clearly hadn't done the job so there was only one thing left, wasn't there? Oddly, despite the sheer romance, the enhanced eroticism and the deep intimacy of our lovemaking, so far I had not gone down on him.

I wriggled around moving my body so I could get my mouth to him. On the rather narrow bed either, I had to get off it or, kneel alongside him. I chose the latter. Curled up pretty tightly I bent my face to his tummy, took hold of his soft dick and wiggled my body as close to him as possible on the basis that if he was touching my nudity that might turn him on, it always had in the past!

The way I was positioned mean that my knee was pressing into his hip, my legs were at about a forty-five degree angle to the side of his body and my bum was about level with his armpit, but well in reach of his hands.

I licked his rather hairy tummy first and, holding his limp dick up I ran my tongue along it. Nothing happened.

I cradled his scrotum in the palm of my hand and rolled his balls around loving the feeling of them against my skin. At the same time I held his penis and kissed the uncircumcised tip. Again nothing.

"Oh Chrissy I'm sorry, it happens when you get older."

"Don't worry," I replied slightly turning my bent body so that more of my leg pressed against his side.

I resumed my oral encouragement thinking a couple of times that there were some signs of movement.

I had it in my mouth when I felt his hand on my thigh. It slid upwards. I felt such warmth towards him that despite his problem he still wanted to please and pleasure me. I opened my legs a little and sucked hard on the tip of his cock, something I'd read about in a novel; I mean where else does a girl learn to give blow jobs, there's no training manuals on it are there.

His fingers slipped inside me. They ran round my lips, both the inner and outer ones. They touched my anal entrance and pressed on my clit. It was rather lovely and I wiggled my bottom and gave a low moan in appreciation.

Suddenly thwack. His hand hit by bottom, quite hard, so much so that I jerked my head and he slipped out. Thwack, smack he hit me twice in quick succession. I grunted and put his cock back in my mouth.

More thwacks and more smacks, each probably a little harder. He was spreading them all over both of my cheeks. I pumped him in and out of my mouth. He was hardening, very slightly and I am sure it was not my imagination.

I looked behind and saw that my bum was in a position where it was difficult for him to reach. I wiggled myself a little further away and watched Jon half roll onto his side. That meant that not only could one of his hands more easily reach and smack my bum, but that the other could reach my dangling breasts and with some fumbling my clit as well.

Clearly realising that I was not averse to what he'd been doing, he smacked me several more times. He was now doing it harder and it was stinging, but it wasn't too painful. Amazingly though, as each time he smacked me, and now he had found a sort of rhythm, his cock seemed to jerk in my mouth. Each smack saw him harden and grow a little.

He was now spanking me with a steady series of smacks that covered every inch of each cheek and was now occasionally drifting down onto my thighs. He was grunting and groaning and moaning and muttering how wonderful I was and what a magnificent arse I had.

Then I had what is in many ways, I now know, the most exciting thing a woman can experience; a man's cock growing to its full erection in her mouth.

And as Jon's cock reached its fullness so now he was thoroughly spanking me. He was though, alternating smacking my bum with stroking my pussy and tits, combining giving me stinging pains with glorious sensations, yes he was using pain and sexual stimulation in equal ingredients to produce the most amazing cocktail of emotions in my mind and feelings throughout my body. He pulled my legs further apart so that my pussy was fully exposed from the rear. He then began slapping my lips. Not hard, but firmly and consistently. It was amazing and I began to tingle everywhere and especially on and in my pussy.

I knew that meant just one thing. I was starting to cum. He must have felt that. When I cum I shudder, I almost convulse at times. My body stiffens and I find it hard to get my breath, especially when my mouth is stuffed full as it was now.

I was moaning, groaning, grunting and whining, as much as one can with a cock in your mouth. I was shuddering hard. I was gripping his cock and slobbering up and down it as if it was the most delicious tasting object in the world. I was licking, kissing, chewing and sucking it. I was ramming it deep into my mouth and then sucking the bulbous head as if it was a lollipop. At times, I shook and shuddered, so his cock would pop out of my mouth and then I'd cuddle it against my cheek, chin or lips. At that moment, I was in love with his cock.

As in love with that as I was, so he was with my bum. Whimpering and whispering how marvelous it was he had stopped his regular slapping of that and my pussy. Instead he was stroking my bottom, caressing it, rubbing my juices over it, licking it and mixing his spittle with my cum. The stinging was still there but that had become something I just cannot describe. Something mystical almost, a combination of the marks, the redness, the heat and the sounds as he'd smacked me and the combination of him hurting and soothing me almost simultaneously. God if only my descriptive abilities were good enough to get across just what that felt like.

Then he just exploded. He did warn me that he was about to cum, but that was too late. Too late for me to get his cock in me, so he could fuck me, too late to get it out my mouth and too late for him to stop. But then I didn't want him to stop.

I am always a little charry of having any form of sex with a new partner when it's unprotected. I am especially concerned when it's with a guy in the theatre for so many are bi, so even greater extra care is needed. However, as is often the case we were both far too carried away to stop, far too aroused to do anything different and far too into each other and what we were doing to give a second thought to the safeness of it.

His cum was spurting into my mouth. I couldn't keep his cock in there, I felt as though I might gag or choke. So then he was shooting over my face and as I leaned back onto my tits. I couldn't believe how much he was producing for it just seemed to go on and on and on So much for older guys not being able to get it up.

*

"Let me do your hair," Jon said.

It was a Sunday afternoon two weeks later. I was in his flat. He had asked me to come round as he had a special treat for me. I had no idea what that could be. Our sex since that time he had cum on my face had been fairly straightforward, although he clearly had an anal obsession for his focus was so much on my bum. He'd lightly smacked my bum a couple of times since that first amazing time when he had lost his hard on, but nowhere near as strongly as he had then.