Not because I think I have to, because you're right about that not being a good reason; I want to do it because I think it would be sexy, and fun, and a way for us to share our bodies with each other.'
Okay, she had her head on straight about the why; did she understand the how and what of it?
'You know what I would do, don't you?' I asked.
'Of course I do. You'd be putting your penis in my butt!'
'You're not a very big girl, and I'm a full grown man. Aren't you afraid it'll hurt?'
'I know if it starts to hurt me, you'll stop. I trust you, Dan – that's why I want you to try it.'
'It might be… messy.'
'I know I'm already empty, inside, okay? And if it gets messy from other stuff, well, I guess that's just part of making love that way. Honestly, Dan – I want to try it. For me, and for us.'
'Even if it doesn't hurt at first, you might be sore, or uncomfortable afterwards.'
'No more sore or uncomfortable than if we were able to make love the other way – probably less, even; unless our biology teacher was wrong, I don't have a maidenhead in my butt!'
Well, there was that, of course. My last try: 'What if you don't like it?'
Mildly exasperated by that time, she answered 'Then I don't like it, and I don't have to do it again. But at least I'll know, won't I?'
I thought about it. She certainly seemed to know what she wanted, and what it would involve. She was obviously ready to accept the consequences, whatever they turned out to be. She wanted to try it because she thought it was sexy, and maybe fun. I have to admit that the idea of anal sex with her was a little bit of a turn-on – but I certainly didn't want to hurt her, either. When it got down to the bottom line (no pun intended), I decided that the suggestion had been hers: she wanted to try it, so we would.
'You're really sure you want to try that? With me?'
'I am! And yes, with you!'
'Then we can', I told her.
It took a couple of seconds for it to sink in for her that I'd just agreed to her request to try anal sex. When it did, though, she eagerly sat up in my lap and looked up at me to ask 'Really? You will?'
I couldn't help smile at her eagerness, and answered 'Yes, really – I will. Or I should say, we'll try. If anything isn't right about it, we stop, and that's, well, the end of it.'
She caught the inadvertent pun and grinned before saying 'Yes, we will stop. I don't want to be hurt any more than you want to hurt me. But I really do want to try it. I, uh, know the, uh, main part, I think – but what do we have to do before that?'
'First, I get something from the bathroom that we can use to make you slippery – we want to make this as easy and comfortable as we can.'
'Yes, we do!' she agreed with a smile.
'Then we'll need to get each other ready – you know, excited.'
'We can do that!' Her enthusiasm was actually kind of reassuring to me.
'When we're both ready, we apply the slippery stuff, and see what happens.' At the suggestion that I'd be trying to fit my erect penis into her anus, she didn't even blink; she really was sure about what she wanted.
She didn't move, or say anything, for several seconds so I told her 'I'll be right back.' She just nodded excitedly, and I went into the bathroom to get the water-soluble lube that we kept around. Every so often, Kelly or one of the others would decide that she just had to have anal sex; it didn't happen all the time, of course – but it was often enough to make keeping the tube of lube around, too.
I was back on the bed with the lube, and a towel, in a minute or so – and found Claire all but vibrating in place at the idea that she was going to get to make love with me anally.
Looking at me, she asked 'Um, how do we get each other ready?'
I grinned and said 'If you think you can stand it for a little while, I'd like to use my mouth on you. You can use your mouth or your hand on me, if you want.'
Grinning back, she said 'I want to use my mouth, too!' Somehow, I wasn't surprised.
Making sure the cap was on tightly, I set the lube on the bed, then moved to lie on top of it; Claire quickly climbed on top of me in the reverse of my position. With her being shorter than me, for her to be able to get her mouth on my penis, her cute ass and other fun bits were a little farther away than usual – but it was a sacrifice I was willing to endure.
Raising my head, I found that she was pretty much within reach for what I was planning on doing to her; she'd already gotten started by taking my semi-erect penis in her hand and licking it.
The first pass of my tongue along her cleft revealed that she was already more than a little aroused – her oils were fairly dripping out of her, in fact. But I wanted her as relaxed as possible, so I knew I had to bring her to an orgasm before I was willing to try the rest. It was a 'chore' that I happily devoted myself to.
It was clear to me that the only experience Claire had with giving oral sex was the little bit of tutoring she'd gotten from Kelly and Jan, with me as the subject. But what she lacked in experience, she more than made up for with enthusiasm and a willingness to learn and experiment. As I went about moving her toward a climax, the biggest problem I had was not letting what she was doing get to me – if I had, she'd have had me emptying myself into her eager mouth and dramatically delaying the opportunity to do what SHE wanted.
With what I'd learned about her before, I enjoyed taking several minutes to progressively excite her before bringing her to a gasping, shuddering orgasm.
After she rolled off of me, I reversed my position, bringing the tube of lubricant along with me. Tucking it between one of my thighs and the bed so it would stay warm, I put my hand on her belly and gently caressed her as she got her breathing and senses back under control. When I was sure she had, I still gave her a couple more minutes before telling her 'If you still want to, we can try now.'
The look on her face was one of pure delight as she moved to her hands and knees. Looking back at me, she asked 'Like this, right?'
I nodded, and got to my knees behind her – making no pretense about not looking at the firm globes of her ass, or the area between her slightly parted legs. She tolerated my gaze for all of five seconds before plaintively demanding 'Please, Dan?'
Opening the cap for the lube, I squeezed a little bit onto my finger and gently applied it between her ass cheeks, where I could see the pucker of her anus. When the initial bit had been distributed, I applied a little more generous dollop to her nether regions – only to be surprised and pleased to see her nipples erecting again as I did. A little more of the lubricant, and I had the outside of her pretty much ready; then it was time to prepare the rest of her by working a healthy portion of the gel into her sphincter – and beyond. As I did, I could hear her breathing quicken, and knew that even having my finger moving in her that way was exciting her. It finally occurred to me that she just might be able to take me – and enjoy it.
With her prepped, the last thing was for me to get myself ready, too. Another squeeze of lubricant applied to my erection, wiping the surplus off on the towel I'd brought, and it was showtime.
Putting my hand on her hips, I moved myself close behind her. The angle and distance was a trifle off, and she willingly let me guide her to where we were in position. I reached between us and positioned the head of my penis against her most intimate opening, then pressed forward just enough to make sure she knew I wasn't trying to enter her yet before telling her 'I'm ready when you are, Claire. You can feel me there; but you can also tell that I'm not trying to get into you yet. That's because I want you to know that I am not going to force myself into you. If you want me to do this, you have to relax yourself and let me in. I'll be able to feel it when you do that, and that is the only time I'll try to get in you. Okay?'
'That's fine, Dan.'
'The other thing I want to tell you – again – is that if any of this starts to hurt, or make you feel uncomfortable, or even if you change your mind and don't want to do it – tell me, and I'll stop. I'd be a lot happier about stopping without doing this than I would be about doing it and hurting you.'
'If I want you to stop, I'll tell you – really, Dan.'
I wasn't entirely sure I liked the sound of that, but didn't have anything to object to about it, either.
As I continued holding the head of my erection against her anus, I could feel Claire trying to relax herself as much as she could. I pressed a little harder, and felt her opening give way a little. Holding myself there, I waited for her to get control enough to let me in a little more. After a bit, I thought it was worth trying, and pushed a little harder. She gave way to me, some, and I paused again, holding myself steady against the tight ring of her
