Still trying to deal with the idea of my oldest niece asking me to sodomize her, I dealt with her first request by telling her "It can sound good and bad because it CAN be both. Which one it's like depends on what the person is trying to make it like. When you hear someone say that another person got fucked in the ass, they mean that that one person was badly mistreated or cheated by someone else. Anal sex is still kind of a big taboo for a lot of people, which is why you don't hear about many people actually doing it; that's part of the reason that just the idea of receiving anal sex is considered a bad thing. Have you ever heard someone talk about something happening to someone else, and hear them say something about Vaseline?"
She nodded, and I told her "Anal sex can be very painful if the two people aren't very careful, and take their time about making it happen — a person's butt doesn't make any kind of lubrication like you do in your vagina, so they almost always have to use something else. People say Vaseline because almost everyone knows that it could be used for something like anal sex; the whole thing together means that a person figuratively had anal sex, but that whoever was doing it to them was nice enough to make it easier and less painful than it could have been.
Other times, you might hear say something that would make it even worse, like doing that with a sandpaper condom. You understand?"
She considered it for several seconds before answering "Yeah, I think so. So most people talk about it like it's bad because of that taboo thing, and I can understand that it wouldn't be fun if someone did that when you didn't want them to. But it can be good if the two people wanting to do it are extra nice about it… kind of like when you had sex with Karen the first time, only more."
"Yeah, that's pretty much it.", I agreed.
"Then if I wanted to, would you do that with me? I know you'd be extra-special nice about it, and I know you wouldn't hurt me that way, and I really want to find out if it's as sexy as it sounds. So would you help me with it, Uncle Ted?"
It was the damnedest thing I'd ever been asked, and left me with mixed feelings — as loathe as I was to do anything that would hurt her, the idea of her giving me her anal virginity had its own distinct appeal…
Donna must have known that I needed a little time to consider what she'd asked, since she sat quietly on my lap without saying a word as I tried to decide how to respond to her request.
When I'd finally gotten things straight in my mind, I looked into her eyes as I told her "You sound like you really do want to try it" — "I do!", she emphasized — "and you also sound like you only want to do it if it's going to feel good" — she nodded her head that that was the case -
"so I guess we can try it. But if it starts to hurt you, or anything bad happens, we stop… right then. Right?"
"You bet, Uncle Ted! I really do think it sounds sexy, and I really do want to try it — but not if it's going to hurt. I know you'll be nice about it, so if anything goes wrong, then I know that it's something I shouldn't do, and we'll stop."
With that reassurance from her, I was considerably more at ease about the two of us finding out if her anus could accept my man-sized erect penis. Still looking into her eyes, I asked "You remember what I said about your butt not making any kind of lubrication?" She nodded that she did, and I asked her "Then you know we're going to need something to make this as easy as we can for you. Do you have anything that you think you'd like to use?"
Blushing faintly, she answered "When I started thinking about asking you to do this with me, I, um, I remembered what I heard people say about using Vaseline, and realized what they meant. I don't have anything like that, but I thought that maybe the baby oil I use on my skin would work
— wouldn't it?"
"Yeah, I think that would be fine. Was there anything else that you thought of?", I asked. Even though I liked the idea of getting my cock between her cute little ass cheeks, I wanted to know if she'd thought things through, too.
Her blush darkened before she answered "Um… I, uh… I'm… I'm empty — you know, inside, so there won't be any, um, mess. And… and I figured that if we could do that, then it would probably stretch me… you know, there, kind of like what happened with Karen when she was with you the first time. Except that because my butt isn't where I'd usually have sex, it might, uh, bother me more… you know, afterwards. That's why I wanted to try it on a weekend like this; I figured I'd be okay by the time I had to go to school again on Monday, if that happened. And…
and I know that if we can do that, and you climax, then… then your stuff will be inside me -
except that after we do that, I might not be able to um, close myself all the way, and that your semen might… might leak out of me. If that happens, I think I'll be embarrassed — not about you leaking out of me, but because I couldn't stop it from happening, is all."
She'd pretty well deal with everything that I thought could or would happen, so there really wasn't anything else for me to do but ask her "I'm guessing you wanted us to do that tonight?
Now?"
A trifle embarrassed, she answered "Well, yeah, if we can…" as I watched her nipples erect slightly in anticipation.
"Did you bring the baby oil with you?", I asked.
"No. I wasn't sure that you'd actually say yes, and I didn't want to seem like I was just assuming you'd do anything I want by bringing it down. It's up in my room."
"Well, I did say yes, so I think you'll want to go get it, don't you?"
She nodded her head, but sat there for a couple of seconds before realizing that nothing else was going to happen until we had some kind of lube readily available. Blushing again, she quickly scooted herself off my lap and headed for the stairs; as she hurried away, I couldn't help looking at her tight little butt and thinking about what we would be doing. So that I wouldn't frighten her or make her nervous by having a raging hard-on when she got back, I managed to limit myself to only getting semi-erect; when she got back downstairs with the bottle, I saw her looking at me when she saw what state I was already in.
Before she could sit in my lap again, I got out of the recliner and went to stand in front of her.
Gently taking her by the upper arms, I told her "Donna, sweetheart, this is something really special — not just for you, but for me, too. You're offering to give me a very special part of yourself, and I want you to know that I know how special this is. You know I'm not going to hurry you, or do anything to hurt you; but I want you to know that I'm not going to be angry or upset or anything if you want us to stop… any time, for any reason, or for NO reason. Even if you decide you don't want this to happen, it'll be okay with me, because that last thing I'd ever want you to do is something that would make you unhappy. So don't worry about ME, at all. Just do what you think is right for you, and everything will turn out all right… okay?"
Smiling, she nodded before telling me "I will, Uncle Ted. Thanks for telling me all that, even though you didn't have to — I already knew that stuff."
With that, I tilted my head forward so that I could kiss her; as it progressed, I slowly moved my hands from her upper arms to her back, then gently pulled her close so that I could gently hug her. She hugged me back, and when our lips finally separated, she looked up at me and said "I love you, Uncle Ted, and I know I can trust you. That's why I wanted to try this with you."