Chapter 10: Back, Jack, and Do It Again

I had a restless night. I usually sleep well after a bit of self pleasuring, but this night was different. I remained uncomfortably ignorant about exactly what was happening between me and Pauline, and I tossed and turned, wondering and worrying. Leslie set me up to have sex with her friend, and after six weeks hanging out for another torrid fuck with Leslie I had thought “Why not?”

Why not indeed? But somehow I had become embroiled in some deep and perhaps scary stuff with a woman who I knew nothing about. We had had two encounters and I didn’t even know her second name. A one night stand or a quick hook-up was one thing. I’d had a few zipless fucks when I was younger, but this was ridiculous! I couldn’t even salve my conscience with the excuse that I was testosterone driven. Sure, I was horny, but at 70, I wasn’t led around by my dick the way I had been in my teens and twenties.

What did I want with Pauline? On one level that was easy. I wanted to turn her on, to kiss and caress her and make her pant and squirm and wriggle. I wanted to pinch and twist and tongue and nibble her nipples until they stood right out from her flat chest and she moaned for me to move lower.

I wanted to explore and massage her groins, to lick and suck her hairless labia, to push my tongue and fingers inside her, and luxuriate in her taste as the whole world smelled of her cunt. I wanted to tease and stimulate her little clit through multiple orgasms until she called enough. Then I wanted to have her. I wanted to bury my length in her deliciously fragrant little slit and take my pleasure, luxuriating in the slippery heat and tightness of her centre. I wanted to feel her moving and straining around and beneath me until my brain exploded and I pumped my cum inside her.

Wow - quite a program!

But on another level, that wasn’t where it was at. Not at all. In fact it was clear that Pauline had some way to travel before she could be fully into sex with anybody but herself. And I was by no means certain that I was the right guy to go on that journey with her – let alone guide her. Sure, I had been able to go along with the teenage role play fairly well as it turned out, and yes, I did turn on to her skinny little body, but in spite of the change in my level of guilt about lusting after teenagers, I really had no idea how to relate to a horny but scared and virginal teenager. And since it was pretty clear that that was what Pauline needed to explore, I had to work it out – and pretty damned quick!

I called Pauline. I knew she didn’t work, even though I didn’t know if she ever had, and if so, at what. I checked out that it was alright to talk about my uncertainties and anxieties with Ryan. At first she thought I was joking, but when I eventually convinced her that I was serious, she said she was reassured that I had anxieties because it made her own hangups seem less peculiar, and she said I should check if Ryan was available after she had worn my dick to a nub. I thought she was probably joking, but either way I had permission to talk.

So I called Ryan. He wanted to go diving, and suggested we could go catch a fish, check out the rock lobsters, and talk about where I was and what I was up to with Pauline. It was a nice day, and he is a good mate, so I hitched up my boat, loaded dive gear, fishing gear, ice, and some food, and as soon as Ryan arrived, we headed out for a few hours at sea.

We slowed down to troll lures through the white water around a headland, and just as we hoped, we soon had a couple of 60cm Kahawai bled and dead on ice. Maori, NZ’s indigenous people named the fish “strong water” because of the powerful fight they always put up, but we fish for the table rather than for sport and our heavy gear had quickly subdued them. The only rock lobsters we could find were well out of reach in the back of very deep, very narrow holes, so our catch bags stayed empty. We consoled each other with the thought that very fresh Kahawai sashimi was a perfectly adequate substitute.

It wasn’t until Ryan had washed down the boat and I had processed the fish and had the fillets back on ice that we actually talked about me and Pauline. Ryan is a patient man, and he listened to me dribble on about my uncertainties for at least half an hour, with the odd quizzical look and a few penetrating questions. Eventually, he must have grown impatient.

“So the problem, at least in your overactive head, is that Pauline needs to explore the teenage experiences she never had, and you are all bent out of shape because you never had those experiences yourself and you don’t know how to act?”

“You got it”

“There isn’t a problem except in your head, you silly old bugger!” I still didn’t get it, and Ryan eventually went on. “Neither of you know how to be horny virginal scared teenagers exploring sex because neither of you have had that experience before!”

“But...”

“But nothing! You can just wing it and so can she, and neither of you know how it really is because as far as both of you are concerned it never really was, and so neither of you can be wrong.”

I didn’t fully understand what he meant, but his advice seemed to reduce my anxiety, so we said our goodbyes, and Ryan went home with most of the fish. I was due at Pauline’s in a couple of hours, and in spite of Ryan’s advice I was still uncertain about how to proceed with her. Then I had an idea. I rang Pauline, and tried to get in role as a teenager.

“Would you like to go out with me tonight?”

“I thought we were going straight back to the couch?” For a second or two I was tempted.

“I think we need to get to know one another better before we go further. Will you go out with me?”

“Okay”

“I’ll pick you up at seven. Wear the same outfit as last time we met.” I did and she did.

Pauline couldn’t decide whether she was intrigued or a bit grumpy about me taking control of our interaction, and when I insisted we travel in my elderly SUV rather than her new Beamer, it became definitely slightly grumpy. I handed her into my vehicle the way I had been taught, and handed her out in the parking lot of the nearest mall with a multiplex. I held her hand as we walked towards the movies, and her mood seemed to improve.

“I never went to the movies with a boy”

“I never went with a girl.”

After a brief discussion, we agreed on “Jacinda”, a recently released biopic of NZ’s recently retired Prime Minister. I wasn’t sure that it was entirely appropriate for a teenage “date”, but verisimilitude has its limits. We stood in line and I bought the tickets, but agreed to let Pauline pay for the icecream. Hokey Pokey of course – this is New Zealand after all. Then I drew Pauline close to me and bent a little to kiss her neck gently and whisper.

“Go to the Ladies and take off your panties. Bring them to me.”

She blushed scarlet and for a second or two I thought she was going to refuse, but after eyeballing me to make sure I was serious, she shrugged and moved off through the crowd. I followed her slowly, and was waiting outside the Ladies when she emerged.

I held out my hand down low between us, trying not to make a performance of the transfer, and Pauline blushed, but produced a wisp of silk, giggled, and gave it to me. I stuffed it in my jacket pocket and led the way into the theatre.

I was pleased to find a half empty row near the back, so I could put Pauline next to the wall. I sat beside her with three empty seats between me and the next patron, a younger woman on her own. We held our mounting excitement in check and sat relatively decorously until the movie started. Then Pauline raised the seat arm between us and we wriggled a little closer together and began to smooch. I had taken my jacket off before we sat down, and had it draped over my lap, but in spite of being in my shirt sleeves I soon began to feel hot in every sense of the word.

Pauline’s lips were soft, warm, and very wet. We teased each other with our tongues, and I began to gently fondle her face and neck. She returned my caresses, but like a good Catholic girl, she let me set the pace and it was at least fifteen minutes before I started to touch her breasts outside her blouse. She made no move to stop me, and as we kept kissing, she took an initiative by slipping her own hand inside my shirt to caress and toy with my chest hair.

“Unbutton your blouse” I whispered. Pauline trembled and unfastened her top three buttons. As she had already rather bitterly confessed, she had no breasts to speak of. I made a mental note to let her know I loved nipples but didn’t much care about other mammary tissue. But talk was later. For the moment our mouths were occupied with each other, and she made no protest when I took both her nipples in my fingers and began to twist and pull them gently.