Dorsai - Taxi

"I think I can take over from here", I assured her. "Think you'd be okay with me behind you?"

It took only a second for her to brighten up and answer "I think I'd be way better than just 'okay' with it!", and giving me a quick kiss before raising up and then easing herself off of me – and softly moaning in disappointment as she did. When she got herself clear of my body, I saw her seem to go "inside" herself as I got to my knees. By the time I was facing her, she'd come out of whatever place in her mind she'd been, and was looking at me rather speculatively.

I simply stayed where I was, looking at her as I waited to see if whatever it had been was something she wanted me to know about. I wasn't anywhere near prepared to hear her tell me "If… if you want to… I mean, if you don't think it's gross, or anything… I… I'd like to find out what it's like to… to be fucked in the ass."

I could only raise my eyebrow in question, and she told me "It's something I've thought about before, and the idea of having a guy doing that to me really turns me on. I never asked anyone to do that before because I didn't want them to think I'd do it all the time, if I didn't like it for some reason. I'm not so much worried about it hurting, 'cause I wouldn't want to do it with someone that I didn't think would take it easy on me, as I am what he might think about me for wanting to try it. But I don't think that you're the kind of person to judge somebody about something like that, and I know that I can trust you to be nice about it, and even stop if I want you to. If you don't want to for some reason, that's fine – I mean, I know that you fucking me the regular way is going to feel good, and make me have another orgasm, and everything. I just wanted to know if you'd be willing to help me find out what that felt like."

While it wasn't my first choice for how to have sex with a woman, I certainly didn't have any objections to Peggy's offer to let me have her anally. She was (obviously) a grown woman, and after she'd explained herself that way, there wasn't anything for me to say, except "If that's what you want, we can give it a try. But the minute, the second, it hurts you, we call it off, right?"

"You betcha!", she hastened to assure me. After a second, she realized that if we were going to do that, it was to her benefit to get something to make it possible; after telling me "Just a sec…", she scrambled off the bed and headed into the bathroom. She reappeared a few moments later with a small plastic bottle in one hand, and a couple of hand towels in the other; when she was on the bed with me again, she told me "This is some baby oil I use to keep my skin soft. Ummm… how did you want to do this?" – then blushed when she realized what she'd just asked before adding "Getting the oil on, I mean…"

I couldn't help but grin at her as I answered "Probably be easier if you got me lubed up, then I did you.", deliberately making the double-entendre, making her blush even deeper… and her nipples reerect.

It took a moment for her to regain her composure; when she did, she set the towels aside and opened the bottle; after she squirted a healthy dollop of the oil into her palm, she reached down to where my erection was waving in the air in time with my heartbeats. It took only a few seconds for her to get me thoroughly coated with the baby oil, and after she'd wiped the surplus off her hand, she handed me the bottle saying "You're not going to be stingy with this stuff, right?"

I assured her that I wasn't, and she turned away from me before lowering herself so that her shoulders were on the bed. Reached back, she put her hands on her ass and spread herself so I could apply the oil. With her spread that way, I could easily see that her labia had gotten darker with her increased arousal – and perhaps a bit longer and thicker, too, in anticipation. After squirting a little of the oil into my palm, I let it warm up for a few moments before cupping my hand at the top of her ass and gently pouring it so that it ran down the crack of her ass and across the pucker of her anus. Using a forefinger, I gently spread the oil around before adding a little more to what was already there; then I slowly and carefully worked into her nether opening, and a little beyond. As I was doing that, I heard her release a couple of soft moans as the area between her labia got visibly wetter.

Once I was satisfied that I could get into her that way, I close the oil and set it aside before wiping my own hand off. Moving closer to her, I levered my erection down and held the end of it so that it was touching – but not pressing against – the rosette of her rectum before telling her "Just so you know, this is only going to happen as fast as you let it. I am not going to push you, and if you want me to stop at any time, I will."

She turned her head enough to look back at me before answering "I know you're not going to do anything to hurt me, but thanks for saying it, anyway. Go ahead, whenever you're ready."

With one hand on her hip to steady myself, I used the other to hold my cock in position as I started pressing myself against her – gently at first, the slowly increasing the pressure to not only reassure her that I was going to take it easy on her, but also to give her time to let me know if she was having any problems or second thoughts.

Once I felt her begin to open up to me, I carefully maintained the same pressure against her so that I kept my promise to her that it would happen only as fast as she let it. I could feel it as she went through a period of relaxing enough to let me in a little ways, tightening again, then relaxing. There were a few times when we (she) lost a little progress, but over the course of the next few minutes, we got closer and closer to getting the head of my manhood through the tight portal of her back entry. I could feel that I was almost through when she suddenly rocked herself back hard and far enough to make it happen.

Other than releasing a loud gasp, she didn't indicate that she had any problems with having me in such an intimate place as she held herself still again. I asked if she was okay, and she didn't hesitate to let me know that she was before adding "It doesn't actually hurt, or anything – it just feels damn strange to have something in me like that… good, but strange. And you feel positively huge! Just let me get used to it a bit, could you?"

I told her that was fine, and waited patiently while I felt her gradually learning to accept what was happening. She released her hold on her ass in favor of filling her hands with some of the bed covers; perhaps a minute went by without my feeling any change in her when she told me "Okay, I think I'm ready. Just take it slow at first, until I'm sure, okay?"

Putting the hand that had been holding my penis on her other hip, I slowly began to press myself farther and farther into her. I could see that her grip on the bedding had turned her knuckles white, but the low moan she made as I carefully sank my manhood into her bowels told me that I was far from hurting her. I stopped my forward movement only when my pubic hair was the only thing between my pelvis and the crack of her ass.

It seemed to take her a few moments to realize that I was in her as far as I could go; when she did, I heard her tell me "This feels so much better than I thought it would! The rest of you was easy, once you were inside; it felt like your dick was ten feet long, you were going so slow."

Though she still had something of a deathgrip on the covers, I could see that her knuckles weren't white any more. Comfortable that she was okay, I held myself still in her for a few seconds before slowly easing myself back out of her for about half my length. After only a brief pause, I pressed myself back into her, then held still. When I didn't move again for several seconds, she told me "That was fine, you moving your dick like that. Keep going!"