An Anal Massage

Hi, I'm Vicky. I'm a twenty-two year old single girl with a very healthy sexual appetite. Now I don't consider myself a pervert, but I've always liked a bit of variety in the sex department. I want to be able to say that I've tried most things, and one thing I always wanted to do, though please don't ask me why, was anal sex. That was why I asked my then boyfriend, Alex, to do it with me. But, oh boy, did I regret it!

Neither of us had done it before and so neither of us knew the importance of using enough lubrication. We didn't have any actual lube with us on that particular evening and so Alex used spit. We'd seen it used in porn films and figured that would be enough. Well, it might be enough for a porn actress who is used to having bloody great cocks and dildos shoved up where the sun don't shine, but it wasn't enough for me. I can still remember the searing pain when he tried to push himself up into me. I screamed and pulled away, and from then on I refused to let any man put anything near my behind ever again. That is, until I met Jason, and that's why I'm writing this story.

Jason is a bit older than me. Not a lot, he's twenty eight, but it's enough for me to look on him as a man of the world, someone who's experienced and who knows what he's doing in the bedroom. Enough, I suppose, for me to trust him.

Because we've both got a fairly adventurous streak we did a few things that I'd blush to tell you about, and then after a while, when we ran out of spontaneous ideas, we started discussing what we'd thought about trying but had never done - and that's when the subject of anal sex came up. Brought up by me, before you ask, because I still regretted not being able to do it.

I told him about my unsuccessful attempt with Alex and why it had put me off trying it again. He nodded sagely when I told him that my little hole was out of bounds and as I explained why, and then he went on to tell me that he'd done it with two of his previous girlfriends and that they'd both enjoyed it enough to climax every time. I thought at the time that was probably a bit of an exaggeration, but I believed he'd managed it without actually ripping their passages to shreds - after all, I know a lot of people do enjoy it, so it can't hurt everyone. I still wasn't ready to let him do it with me though, the memory was too painful.

'But Vicky, you wanted him to do it, didn't you?' He asked me, sounding puzzled.

'Well, yes. But I didn't know it would feel like having a red hot poker pushed up me.' I told him.

'It shouldn't have.'

I sort of knew that, but it had. I'd figured that maybe I was too tight in that department.

'It's okay saying it shouldn't, but it did.'

I must have sounded cross, I know I felt it. I was still irked that I couldn't take it like other women and enjoy it.

'If it hadn't.' Jason asked. 'Would you have done it again another time?'

It seemed a silly question to me. Of course I'd do something again if I enjoyed it the first time. That was the reason for trying it in the first place.

'If I enjoyed it I would, obviously.'

'I mean to say, you haven't got any sort of moral objection or anything?'

'No, just an objection to pain. That's all.'

'Would you try it again if you were sure it wouldn't hurt?'

'Yes I would.' I told him without thinking. 'If other people can enjoy it, why can't I?'

'You can.'

I could suddenly see where this conversation was headed. Yes, it was something I'd really wanted to try, it had that aura of kinkiness about it that appealed to my exploratory side, but I wasn't going to expose myself to that kind of pain again just to tick a "done it" box. Even so I realised abruptly that I was actually considering it.

'How?'

'From what you've said.' He explained. 'You tried to do it without making yourselves slippery enough first, so when he tried to enter you, instead of sliding through without your sphincter really noticing, his cock tried to force it's way in and that made you instinctively contract to keep it out, and that's why it hurt. If you did it again and took it slow and easy, and you were really, really, well lubricated, I reckon you'd find you enjoy it.'

'Hmmm. Let me think about that one.' I prevaricated a bit. I was tempted, but not quite enough yet.

I must give Jason his due, because he did let me think about it. The subject was never mentioned again until I brought it up a week or so later.

'If I let you, how would you do it?' I asked him suddenly one evening.

'Slowly,' He answered, instantly knowing what I was talking about. 'Very slowly and step by step, so that you'd have the chance to back out any time you wanted.'

'How can you do it step by step?' I was confused, to me it was step one, the penetration, that hurt.

He grinned. 'Well, I won't just ram my cock up you, even if you were as slippery as a politician. I'll start with the tip of my finger and see how things go.'

I made up my mind. 'You can do it then.'

I'd just given him the go ahead to do something with me that I'd not enjoyed when I'd tried it before. I remember thinking that I must be mad.

'Sure?'

I swallowed hard and nodded. 'I am if you promise to take it easy.'

'I promise.' He paused. 'When we're in the right mood and when we've got some lube.'

We didn't arrange when we would give it a try, looking back I think he was expecting me to say when I was ready, but I didn't and time marched on. In fact it marched on so much that I'd almost - well, I won't say forgotten, but I'd put it to the back of my mind. It was, in fact, nearly two months before anything happened.

'Want a massage?' He asked me one evening at his place. He's given me a massage several times before and they were wonderful. Slow and sensual sessions that ended in two naked and oily people making very beautiful love.

'Yes please.' I answered, instantly looking forward to it.

His single bed is quite narrow and doesn't have an attached headboard. What headboard he has is screwed to the wall and the bed is pushed up against it, and so when the bed is pulled away from the wall a little way it makes an ideal impromptu massage table. As before he placed a towel on the bed and then I stripped off and lay face down on it, my legs a little apart and my arms away from my sides with my palms facing upwards. While I got myself ready he warmed some massage oil and stripped down to his shorts. The first time we both stripped all the way, but having his gorgeous cock waving around in front of me was just too much of a temptation and we nearly succumbed before much was done in the way of massaging.

The next time he kept his shorts on at least for a while. He spent a long time massaging my back, getting me all warm and welcoming before he rolled me over and started work on the important bits, and you know exactly what I mean. Eventually I saw him push his shorts down and I knew that the massaging was done and the screwing was about to start, but by then I'd already had two orgasms and he was getting pretty desperate. The sex that followed has to be the most intense I have ever experienced - fantastic.

That's what happened each time after that, more or less, and so that's what I expected to happen again. In the event it turned out to be just a little different, but as I lay on the bed watching him put the warmed oil and a couple of spare towels on the bedside table I didn't have any warning of what he had in mind.

He's good, I have to say it, he's very good. He sat down beside me and began on my hand and arm, spreading warm oil over my skin in long languid strokes of his hands from fingertip to shoulder. I almost purred at the sensuousness of it, but then he took each of my fingers in turn, wrapping a couple of his own around them and rubbing softly along them back and forth. The way he did it made it impossible to believe he was not imitating a slow wank and I am sure it was done simply to plant erotic thoughts in my mind - not that I hadn't got them already. From there he began to work his way up the oily skin of my arm, beginning by pressing his thumbs into my palm as he massaged my hand and somehow making that feel sexy too. By the time his hands were massaging the top of my arm I was already getting so turned on that I was sorry he still had his shorts on. Though maybe that was from simple expectation of what might follow.

Then he did the same with my other arm, taking his time and making sure that I enjoyed it, and then came and knelt at the head of the bed to do my neck and arms. I couldn't help it; I just stared hungrily at the bulge that was his erect cock trying to push its way out his boxers. It was only a foot or so in front of my face, and I'm sure he knew it. I desperately wanted to reach out, pull his shorts down and take it in my mouth. How I resisted I don't know.

Maybe he realised he was pushing his luck because, instead of running his slippery hand down my back as he had the last time, something that would have made him lean forward and bring his cock within sucking range, he contented himself with going as far as my shoulder blades before he got up and went to the other end and began on my feet.

'Don't move yet.' I pleaded. 'I was enjoying the view.'

He chuckled. 'Don't worry, you'll get better acquainted before we're done, I promise.'

I smiled to myself and relaxed, anticipating what was to come.

My feet and legs received the same wonderful treatment as my hands. Pouring warm oil into his hand and then smoothing it into my skin he started at my instep and worked his way slowly and luxuriously up each leg, giving each one a long slow massage as he inched his way higher and higher. I just lay there, softly murmuring encouragement and gratitude. As he reached my thighs he gently parted my legs a little further so that he could kneel on the bed behind me. I knew what he could see, but I didn't care, he'd seen it all before and from a much clearer angle.

He massaged each thigh in turn, straddling my leg and running his slippery hands firmly but gently along either side, pressing into my muscles. It was a proper massage but somehow very erotic too, especially when his hand reached the top of my inner thigh and momentarily touched my pussy. I wanted more than just a fleeting touch, but I knew I had to be patient.

He did this for what seemed to be ages, sometimes stopping at the top of my thighs, sometimes letting his palms slide over my bottom, massaging my cheeks, occasionally pressing them apart so that his thumbs could reach into my crack. I loved every second, but I was eager for him to roll me over and begin on my front. I suppose really I was simply becoming desperate for him to make love to me, so when he abruptly climbed from the bed and went around to sit alongside me I was impatient almost to the point of irritation. I'd forgotten that he'd not done my back yet, but even so when he drizzled warm oil along my spine I was puzzled as to why he had chosen to do it from the side. How was I to know what was to come?

It was nice when he ran his hands along my spine though, his palms flat against my back and his fingers overlapping my sides a little. At first he ran his hands from the nape of my neck down to the end of my spine and back, but then I realised he was very gradually working his way south, massaging my bottom as well as my spine, but only reaching up as far as my shoulder blades. I was as randy as hell, but I was enjoying it and I knew he'd get around to the main event sooner or later, and so I just groaned softly to let him know I liked it, and relaxed. It was as if my noises were a signal because now he ran his hands less and less far up my spine until soon he had got to the point where his hands were concentrating almost completely on my bottom, and I didn't mind a bit.

Suddenly, unexpectedly, he used one hand to open my cleft and trickled oil into it so that it ran all the way down, over my anus and onto my pussy. After that he propped himself up on one arm and used only his free hand to massage my bottom, his fingers running up and down my cleft. It was strange but very erotic, especially when his fingers slid just into my pussy at the end of their journey. It was only a quick entry and I wondered if he meant to do it, until he did just the same again, then I murmured softly and spread my legs a little to give him access.

His reaction was simply to stand up and move away so that I looked up sharply. 'What's wrong?'

'Not a thing.' He smiled as he picked up the spare towels and rolled them up. 'Lift your bottom a moment.'

I made to get up, lifting myself onto my hands and knees, puzzled as to what he meant.

'No, just lift your middle; make a sort of bridge under you.'

I lay back down and then raised my behind, not sure what he intended. But then he threaded the rolled up towels under me so that my bottom would stay raised, and so I figured he wanted to take me doggy style. I wasn't going to argue with that even though it did mean that my front wouldn't get done.

'That's good.' He told me as he sat back down and dribbled a little more oil into my crack. 'Now just relax.'

I really ought to have figured it out at that point, but I still didn't. I did as I was told and relaxed, my legs apart as before.

He wasn't making any pretence of massaging my bottom now; he was concentrating on my crack with his slippery fingers running up and down the length of it from my tail to my pussy, and he was especially concentrating on my pussy. He managed to part my labia with two fingers and slide the other two up and down between them. That was good, so damn good it quickly had me squirming and then gasping each time his fingertips caught under my clitoris. God, I was so damn turned on, I'd got past wanting to make love, now I just wanted to be fucked and I was pretty sure he was soon going to do just that.

But then, with all my wriggling about, his finger found my entrance and slid inside, going deep inside me.

'God, yes.' I gasped, thrilled by the unexpected penetration.

'You like that, then?'

I could hear the amusement in his voice as he began to push in and out. I nodded, not trusting myself to speak without yelling.

'Then you'll like this even more.'

I felt a second finger seek out my hole and plunge inside.

'Nice?'

I nodded again, gasping with pure delight. His little finger now found its way inside me and he had three fingers in my pussy with only his forefinger folded out of the way, and I was half expecting that one to join the others too. In fact for one heart-stopping moment I wondered if he was going to push his whole hand up me. I'd never been fisted, but with me on my front with my bottom in the air and my pussy lubricated with massage oil, it wouldn't have been difficult.

But that wasn't his intention; instead he seemed content to thrust his three oily fingers in and out of my very receptive pussy. At first he pushed into me slowly and gently, but he soon began to speed up and do it more forcefully, his three fingers plunging deep into me, making me gasp from the power of it and moan with the pleasure. I could feel the knuckle of his folded fourth finger banging against my anus and even that was giving me a thrill. It wasn't long before I felt an orgasm building, and building very rapidly. The strength of my imminent orgasm even made me reach up and grab hold of the edge of the bed, clinging on for grim death. What I looked like I hate to think.

Then, just as I was on the brink of coming his last finger sought to penetrate me as well. But it wasn't aiming for my pussy; instead, as he drew back it unfolded and found my oil lubricated anus. As he pushed the other three fingers back into my pussy he wiggled this fourth finger so that it simply slid past my sphincter and into my passage. It went in so easily that I hardly felt a thing, except for the unexpected thrill of having him there.

'Oh Jason.' I gasped, alarmed but excited, suddenly understanding what it was all about.

'Sshhh.' He whispered, his fourth finger now plunging in and out in synch with the others. 'Just enjoy it.'

I was enjoying it. My impending orgasm, delayed by my surprise at what he did to me, began to build again, stronger than ever before. Soon I was lifting myself up, almost onto all fours, and pushing back against his hands, willing him to go deeper into both holes and gasping 'yes, yes, yes' just to make sure he knew I wanted him to continue.

And then I came. I don't know how much his forefinger contributed to it, pushing deep inside my back passage, but it was the strongest climax I have ever experienced. I raised myself onto my knees, keeping my head low and arching my back so that my bottom stood up for him and then pushed back as hard as I could against the fingers that rammed into both holes. I gasped loudly, not little breathless gasps but really loudly, almost shouting my enjoyment as long waves of pleasure continued to break inside me.

When it was finally over I just sagged forward onto my stomach, losing contact with his fingers even though my bottom was still raised over the roll of towels. All I could think, apart from missing the sensation, was that he had had his finger inside me and it hadn't hurt.

'God, that was good.' I panted, turning my head and smiling at him.

'I thought it would be.' He smiled back, looking suitably smug.

I hadn't thought about what we might do next, I was still mentally celebrating what we just had done, and so I watched him take off his shorts with unexpected detachment. It wasn't until I saw him pour oil into the palm of his hand and begin to smooth it along his cock that I abruptly realised what he had in mind.

He must have seen the alarm on my face. 'Don't worry, I won't force it, and you know you want to try it.'

'Oh God.' I groaned. 'What if it hurts?'

'If it does, I promise I'll stop. But it won't. You saw how easily my finger went in with oil on it.'

'Yes.' I protested. 'But that was a finger, not your bloody great dick.'

'Thanks for the compliment.' He chuckled, rubbing more oil into himself. 'But it isn't that big.'

I giggled, I couldn't help it. Perhaps it was nerves. 'It isn't that small either.'

'Now, can you get on all fours?' He was ready even if I wasn't.

I hesitated, but then I complied. I knew I would, it was just a question of raising the courage. 'Promise you'll stop if I say?'

'Promise.'

He went around the bed and I felt it sway as he knelt behind me. I couldn't help but tense up a bit, especially when I felt the oily tip of his cock against my behind. This, I told myself, is it. I'd wanted it, asked for it, and now I was going to get it. I felt his hands open my crack and then his tip found my puckered hole.

'Ready?'

'As I'll ever be.' I answered.

It's strange isn't it, but this was something I'd wanted to try ever since I can remember, but now the moment had come I was as nervous as a kitten and teetering on the edge of saying no. Presumably because of that bungled attempt I'd made with Alex. I knew Jason would be better, but that didn't cure the nerves.

He was better. For a start he didn't try to just force himself home in one go. Instead I felt him press against me, the head of his cock finding the centre of my sphincter and pushing on it gently but firmly. At first nothing happened except that I tensed up, I just couldn't help myself. Then I felt myself opening just a little, and then a little more and then, suddenly, the head of his cock was inside me, making me gasp with surprise.

'You okay?' He asked, mistaking my gasp for pain.

'Yes.' I told him, suddenly registering that he had actually entered me and it hadn't hurt at all. 'I'm fine, just take it easy.'

He did take it easy, slowly easing himself deeper until he had to shuffle forward a little, and then he paused again.