It took a couple of minutes for her to get her breathing back under control, and perhaps half again as long before she had enough strength back to raise up and kiss me before telling me "I don't know who you've been having sex with, but she is one damn lucky woman. As nice as it felt to have your cock in me, the way you were touching me was the icing on the cake – I knew I was going to have a nice orgasm, but you made it SO much better with what you were doing."
I happily kissed her back, a couple of times, before answering "It isn't just one; I just tried to learn something from each of them so that I could make the next one feel that much better, is all."
With a snort, she told me "Judging by how you've been making me feel, I'd have to guess that you've probably been with six different women a day for the last ten years to have learned that much!"
I couldn't help but smile at her exclamation before gently pulling her back down so that the two of us could exchange several tender and affectionate kisses. With more of her strength back by then, Peggy started to lift herself up again – and felt my hard cock move inside her. The stunned expression on her face was almost comical, and I managed to keep my expression neutral when she almost demanded "Didn't you cum? Mine was enough that I couldn't tell; I just figured you did. Is something wrong?"
She let me pull her close and kiss her again, then I answered "No, I didn't cum, and no, there's nothing wrong; it's just still a little too soon from last time. If you want us to keep going, then it'll probably happen next time."
It took a second before she was able to respond with "If I want us to keep going? Hell, yes, I do! I wanted to get laid, and you're doing a damn fine job of it, mister! You're making up for months of doing without, all by yourself. IF I want us to keep going…", the last in a tone that let me know she thought I was being particularly dense.
To try and mollify her a bit, I gently pulled her into another kiss – one that went on longer than I'd initially meant for it to, due primarily to her tongue teasing mine into a rousing game of "Tag". Only when it was over (damned if I know who won, and don't care) did she pull back again to say "I'm all for us going on, but not like we just did – I'm too damned tired to finish it."
"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.