Jan

it or not if I don't try it at least once. As for the lubrication part, wouldn't something like baby oil or lotion or something be just as good?'

Obviously, she wasn't willing to be talked out of it. And I had to admit, the idea did have more than a little appeal to me.

I finally gave in to it, and told her 'Okay, Kelly, if you really want to try it, we will – but the first time you feel any pain or unpleasantness or anything like that, you tell me – I am NOT going to do anything that would hurt you just so you can try a new experience.

Got it?'

'Yes, Dan, I've got it. I don't want it to hurt, either, so you can be sure I'll say something!'

'Okay, if that's settled, then we're going to need something to make it easier.'

'Uh, I've got some baby oil that I use on my skin after I shower; you said that would work, didn't you?'

'Yeah, that'll be fine.' I answered. Getting up, I said 'Do you want to get it, or should I?'

'I'd better go; it's in my backpack, and you'd never find it.'

With that, she got up as well, and as she went past me, I patted her on the butt and said 'On your way back, you might want to run it through the microwave for a few seconds – unless you like cold oil on your butt!'

She paused briefly, laughed, and said 'No, not particularly!' before giving my still-erect, if somewhat sticky, penis a squeeze before taking off again. Watching as her ass cheeks clenched and unclenched while she walked caused me to twitch several times in anticipation of what was yet to come (pardon the pun).

Shortly, I could hear the door to the microwave open, and perhaps ten seconds later, the ding as it announced it was done. A moment later, I could see Kelly appear in the doorway, and enjoyed the view as she walked toward me: breasts jiggling ever so slightly, dark hair bouncing around her head, the ebb and flow of her leg muscles as she walked, the sway of her hips, the eager anticipation on her face as she got closer.

Handing me the bottle of warm oil, she looked at me, expectantly. I answered by telling her 'It's probably best if you get on your hands and knees, like before. I'll do the oil part, and we can go from there, okay?'

She nodded her assent, and was soon on her hands and knees again, her cute ass pointed at me as she looked over her shoulder; ready, if slightly nervous.

I kneeled down too, and after opening the bottle, squirted a small puddle into the palm of my hand, which I then laid at the top of the crack of her ass, and tipping my hand a bit to allow the warm oil to trickle down between her cheeks. Her eyes got wide as the oil seeped down the crack, and then sliding over her anus. Using another, smaller, amount of oil, I repeated the action, but this time, after letting it roll out of my hand, I spread her cheeks slightly, and worked the oil around a bit, making sure it was well distributed. Getting into it, she rested on her elbows, so that her ass tilted up more, and bringing her pucker more into view.

Holding the bottle, I allowed a little bit to dribble out, directly on her anus, causing her to flinch, then moan. Using my forefinger, I started working it into the folds first, then, with a little more pressure, farther and farther into her rosette, until, finally, I had the first digit of my finger inside. She was moaning constantly now, and rocking herself back toward me, so I didn't hesitate to drip more oil onto my finger as I worked it in and out of her sphincter, getting her well lubricated.

When I judged that we had enough oil to last the duration, I pulled my finger back out of her rectum, twisting it back and forth as I did so, and earning a gasp and disappointed murmur as it popped free.

Squirting a little more of the cooling oil on my hand, I liberally applied it to my erect penis, particularly the head. Satisfied that we were both as ready as we could be, I sealed the bottle and set it aside, pausing to wipe off the excess from my hand.

Easing forward, I used my hand to direct my erection down slightly, until it was pointed at her nether entrance, then placing the head against it. Seeming to realize that the angle was wrong, Kelly got back on her hands, leveling things out and lining them up better. Pressing forward, I was unable to wedge enough of her open to make my entry.

Releasing the pressure, I caressed her hip, and told her 'Kelly, I know you're nervous, and maybe even scared. I'm NOT going to force my way in, because that would hurt you. If you want me to do this, you'll have to relax, and let me in.'

She nodded, and I could see her making a conscious effort to relax which, after a few moments, she did. Pressed against her, but not pressING against her, I waited a bit longer, as she got more control, and eventually calmed enough that I thought it worth making another try.

With her reduced tension, I again pressed myself against her, gently, so that she would know I wasn't going to hurt her. She relaxed even more, then, and I gradually increased my efforts, until, finally, I popped through – and immediately stopped as she cried out. Holding very, very still, I waited to see what she wanted to do: get used to the sensation, or end it. After a bit, she told me 'Yeah, that's it – just hold still for minute. I want to get used to this, first.'

I asked her 'Kelly, are you okay? Am I hurting you? Are you sure you don't want me to stop?'

'No! Don't stop! Just hold still, okay? That's a lot bigger than your finger was, and I just need a minute to get used to it. It doesn't hurt, exactly, it just feels BIG back there, like that. Just give me a minute, okay?'

'Okay, whatever you want – a minute, two, five, whatever you need.'

Satisfied that I wasn't going to move, she hung her head, and started breathing deeply, in an effort to let herself loosen up. It worked, and after a couple of minutes, I could feel her pressing back against me, when she said, 'It's okay, now. I think I'm okay with it, but go slow at first, would you?'

'Anything you want, Kelly.'

With that, I firmly, but carefully, increased the pressure, until I started to slide into her again, slowly. She accepted it, and as I got further into her, and as the sensation remained pretty much constant for her, relaxed even more, until I was finally fully embedded in her ass.

Once there, I again stopped, both to give her time to adjust, and to savor the sensation of having my entire length inside her incredibly tight back entry, and the feel of her crinkled anus clamped so tightly around the base of my member.

Leaning forward a bit, I reached around her, to take her breasts in my hands, squeezing them and playing with the nipples – not just for the sheer pleasure of it, but also to try and distract her, and help her accept my presence in so intimate an area. It seemed to help, because it wasn't but a few minutes before I felt her again starting to move under – and around – me, if only experimentally. Giving her some time to work out how it felt to her, I continued to fondle and caress her breasts and nipples, until she finally spoke to me again.

'Wow!'

'Wow good, I take it?'

'No,*I* took it – but yes, 'wow' good.' she giggled at her own joke.

'You've got a twisted sense of humor, Kelly – but I like it!' I laughed, with her.

That said, we were quiet again for a while as she continued trying different things: arching her back, moving from side to side, tightening and then relaxing her anus, and so on. I waited, patiently, though getting more and more aroused with each of her efforts. After a bit, she spoke to me again, saying 'Uh, Dan?'

'Yes, dear?'

'Uh, I think I'm ready to, uh, start now.'

There wasn't any response that seemed appropriate, other than to grasp her hips again, and start moving inside her; short, slow strokes at first, and as she got used to the, gradually increasing the length and speed of my actions, until I hit a rhythm that seemed to make both of us happy. Feeling as good as it did, I didn't mind in the slightest when she reached back between her legs and started playing with her clitoris, and sliding a finger inside herself to keep it lubricated. Occasionally, she would reach further back to play with my testicles as they swung forward, but mostly she kept her attention on herself. That was fine with me, since the feeling of having her tight, if now stretched, anus sliding up and down my length, and the heat of her bowels wrapped around me was more than enough to please me. In fact, it didn't take but a few minutes before I felt that 'old, familiar feeling' settle in, and knew that this time, I was free to take it to completion.

With the beginning of the end, so to speak, my pace started to increase, as did my 'enthusiasm'; that told Kelly that it wouldn't be long, and she redoubled her efforts on her clitoris, and in her vagina – while still eagerly accepting my faster, harder thrusts into her. A very few minutes later, I could feel the tightening in my balls, and pumping into her hard enough to make her grunt with each entry, it wasn't long before I finally went over the edge, spraying the inside of her bowels with the first of many shots. It was apparently enough of a sensation for her that