Seeing the confusion on my face, she told me "I want you to have sex with me – in my ass."
I heard Sarah's gasp of surprise, and Helen must have seen how much of a shock it was to me, too, because she said "I already told you that I get sensitive… there… when I'm having sex. You told us that you wouldn't 'push' things while you were with us; and you haven't. When you first started touching me there, you were thoughtful enough to use some of my… wetness to make sure you didn't cause me any discomfort. And you were slow about doing it so that I could let you know whether or not it was okay with me; I expect you know that it was!" – the last part with a small, nervous laugh before she continued "In fact, you were so gentle and considerate about it that you actually made it even better for me when you did what you did while I was having my climax. That got me thinking about trying anal sex again – and particularly with you. I rather suspect that I'll like it, all things considered, if it's done right; and I think that if there's anyone I can trust to do it right, it's you. So assuming that the idea of anal sex doesn't push one of your limits – would you?"
It took me only a few moments to make my decision: she wanted me to, and I was certainly willing enough, so there wasn't anything for me to say to her except "I'm not going to insult you by asking if you're sure – you wouldn't have said anything if you weren't – so yes, I'll do it. I'm honored that you would trust me enough to ask, and I'll do my best to do it 'right', as you say."
A look of relief flashed across Helens face before she turned her head slightly to tell Sarah "Dear, I know it's maybe a surprise to you to hear that I'd think of something like that, but I really have wanted to try it before. I don't want you to think that I want to keep you out of this, either: I'm certainly going to want your help! As much as I want to do this, I'm still nervous as hell about it; and you know just how to help me relax so that it's as easy as possible for me."
Sarah solemnly nodded her understanding and agreement before asking "So… what can I do?"
"First, you can stop looking so damn serious! Honestly, dear, I really do want to do this – here, and now, and with Jim. God! I can feel myself getting so wet, just thinking about it! Then, if you would, you could get the lube from your suitcase; I expect that we're going to need it, don't you?"
The question at the end was what brought a smile to Sarah's face before she answered "Yeah, I expect you will!" before getting up and leaving to do as her mother had asked.
Helen turned to look back at me, and saw that I was sitting there patiently. After she raised an eyebrow, I answered the implied question by telling her "I'm not going to force this, or push for it to happen. In fact, I'm perfectly willing to stop and call the whole thing off any time – but the call whether or not to do that is entirely up to you, and for whatever reason you choose: whether because you think it'll be too messy, it gets too painful, you change you mind, whatever. Even if you want us to stop after things get going, I'll do as you ask. If you're not one hundred percent sure, at any time, then it stops, as far as I'm concerned."
I could see her visibly relax at hearing that, and told her "I already told you that I don't 'push'. And I most definitely don't willingly hurt people. You said that you trust me, and I'm letting you know that you're right to."
A moment later, Sarah reappeared with a tube of something in one hand, and what looked like a couple of different-sized towels in the other; she showed me the brand, and I recognized it as one of the water-soluble types. That little bit of information started a little movie going in mind, visualizing the two of them playing with the 'toys' they'd mentioned. The movie was cut short when Sarah handed it to her mother, who then told me "I'm going to presume that you've done this before – had anal sex. With a woman, I mean."
I couldn't help grinning before I answered "As a matter of fact, I have. With women."
Helen was blushing slightly as she said "Well, I'd welcome any suggestions or advice you might be willing to share. How should we do this?"
Looking into her eyes, my first response was "However is easiest and most comfortable for you."
I followed that up by saying "You said that Sarah knows just how to relax you so that it's easier for you, didn't you?"
Helen nodded, and I went on "Then my first thought is to get that stuff on me. Then Sarah can get you 'relaxed', and when you're ready, I'll use it on you and we can give it a try."
From the expression on Helen's face, I knew that she understood that the bit about me using the lube on her was to give her plenty of time to change her mind, if she wanted to. But to my surprise, she got a look of resolve and anticipation before answering "That sounds just fine, Jim; that's what we'll do." Then turning to Sarah, she asked "Do you want to do the honors, dear?" while offering the tube back.
Sarah considered it for a moment, and then answered "No, Mother, you go ahead. I'm glad to help in whatever way I can; but I don't want to take anything away from what should be your experience."
Helen smiled, and gently caressed Sarah's face before whispering "Of course, dear. Thank you."
That settled, I moved over to where Helen was; she looked into my face for a few moments before uncapping the lube and squeezing a generous amount into the palm of her hand, saying "This is not the time to be stingy with this stuff, is it?", and laughing when I answered "I think not."
A trifle nervous at first, Helen was soon enjoying the experience of getting my erect penis thoroughly coated; once she was satisfied, she picked up the smaller of the two towels Sarah had brought and wiped the surplus from her hand.
What could have been an awkward moment turned into something far more loving when Sarah leaned forward to kiss her mother. That kiss started with obvious love and affection, but ended with no small amount of passion and desire. Another kiss followed that soon had them caressing each others breasts as their tongues danced in each other's mouths. As a third kiss progressed, Helen gently guided Sarah onto her back. When the kiss ended, Helen went about reversing her position, then slowly kissed and sucked her way down her daughters body while Sarah returned the favor. It wasn't long before they were in a '69' position, just as they'd been before – and doing much the same things. It wasn't long before the scent of aroused female waxed strong again, and even less time passed before I heard Helens cry of pleasure and release.
That was the cue for me to move behind her, and after applying a goodly amount of the gel to my fingers, begin applying it to her anus and working it into her opening. Helen moaned in increasing arousal as I proceeded; but it wasn't until I'd refreshed the supply of lube a couple of times that I was satisfied that we could begin.
After cleaning my hand of the excess gel, I gently put my hands on Helens ass and carefully spread her cheeks before moving to rest my penis against her pucker. I paused then, waiting for her to let me know what she wanted me to do. She made her choice known by pressing herself back against me.
The angle was a bit 'off', and the head of my cock slid away. Helen seemed to realize what the problem was, and arched her back slightly to compensate. For my part, I released my hold on one of her ass cheeks to hold my erection steady after getting it repositioned. Again, I waited for Helen to push back against me slightly before trying to press myself into her.
I knew that she was nervous, and slowly increased the pressure I applied to her rectum so that she'd know I wasn't going to 'force' the issue. I felt her begin to calm down, and then deliberately try to relax herself in response. Below us, I knew that Sarah was watching us – I could feel her warm breath on my balls, and her hair softly tickling the insides of my thighs.