Chapter 8: When you Know She's no High Climber

When you know she’s no High Climber So there we were on the couch, less than an hour after first meeting. I had assured Pauline that I knew exactly how to treat her like a virginal Catholic teenager who was very horny, but also very scared and guilty. That was an outright lie. In fact, I had no idea how to treat any virginal teenager, no matter how horny she claimed to be, and even less clue about relating to a woman in her sixties who wanted to have the “teenage experience” she had missed out on. Did she want to get into some sort of roleplay?

Under these circumstances, I had no idea how to get from holding hands on the couch to what for me anyway, was supposed to be the main event. Leslie had certainly blown my cover about lusting for young teenagers and my longstanding guilt about that, but I was unsure whether Pauline’s comment about “tight slippery little cunts” was a turn on for her, or just intended to get me going. It had certainly done that. I was hard, and my breathing was irregular.

But I had no idea what to do next. Fortunately, Pauline was willing to take the next step.

“I’m going to stay a virgin until I’m eighteen!” I went with Pauline’s lead. We were clearly going to have a conversation about sex.

“How long do I have to wait?”

“I turned fourteen last week.” Shit – She had my number bigtime. My cock twitched and I could hear myself panting, but she went on.

“How old are you?” I decided to wing it since we were clearly into a role play.

“Just turned fifteen, and four years is a long wait. I don’t know whether to tease you a bit, or tell you some stuff, or to ask you some questions.”

“No teasing.” Her voice was flat. “What’s the stuff you want to tell me?”

I kept trying (and failing) to access my naïve fifteen year old self. Eventually I slipped into a “lecturing” mode, still hoping not to break the mood.

“On one level, virginity is simple. Once Tab A has been put in Slot B, neither partner is a virgin.” Pauline giggled, but said nothing, so I went on. “Virginity is like a bubble – one prick and it’s all gone.” She giggled some more. “But its actually more complicated than that. What about gays and lesbians? What about the other places you can put a penis?” Pauline giggled again, so I went further.

“I’ve never had anything to do with girls, but I’ve put my penis between another boy’s legs. Am I still a virgin?”

“Dunno – but what about the Virgin Mary? Does God count?” On the surface, Pauline was engaged and enjoying the game, but her body stiffened slightly as she asked that question.

I pushed a bit more. “Don’t let the nuns hear you talk like that!”

Pauline giggled again, but her laugh had an uncertain edge, and her body stiffened further. I waited.

She took a couple of deep breaths, and then her face crumpled and she let the last breath out with something between a sigh and a sob. “This isn’t going to work!” She let go of my hand and pulled away a little, increasing the gap between us and turning slightly to face me.

“What isn’t going to work?”

“I hoped I could be a young teenager with you and explore sex. I never did as a teenager. I went to a bloody convent boarding with a bunch of uptight nuns. I came home in the holidays to rattle around in this pile.” She paused for a few seconds and gestured to our distinctly upmarket surroundings.

“No boys in the holidays?”

“Are you kidding? Pauline almost snarled, and for a few seconds she was positively ugly. “No tits, no curves, still haven’t got any. Last in the class to get my period.” Her face crumpled again, and she gave another half sob. “I didn’t even kiss a guy until I was twenty, and I was too scared to have sex for years after that.”

“I didn’t have a proper kiss until I was 18, and I was a virgin as far as girls went until I was twenty two.”

“You’re having me on”

“No. I’m telling the truth. Single sex school, Scouts, Army Cadets, then University with no Idea how to talk to any female with boobs and pubes. The only sex in my teenage years was a few jerkoff sessions with other scouts and lots and lots of sex with myself.”

“I masturbated whenever I could, but there’s not a lot of privacy at a convent boarding school.” Pauline inched back towards me, until we were again sitting close.

“You must have had plenty of privacy in the holidays?” Pauline nodded and took my hand. I waited to see what she would do, feeling as clueless as I would have if I had really been fifteen, sitting on a sofa with a fourteen year old girl. Pauline brightened.

“Let’s try being teenagers again”

I slipped back into role. “What about the nuns?”

“They’re all back at St Mary’s, and Mum won’t be home here for another hour.”

“OK – so we are both virgins – and not just horny virgins, we’re both pretty ignorant and we haven’t even had the early teen experience of learning how to talk to the other sex. What do you want to do?”

“I’m actually too scared to do anything” Pauline started to look sad again.

I winged it. “We won’t do anything we don’t both want to do. Perhaps we won’t do anything at all – but we could talk about what we might like to do if we weren’t both too scared and your Mum wasn’t coming home soon.”

“Alright – but we just hold hands and talk.”

“Deal!” I could follow Pauline’s lead. “You said you masturbate. What do you actually do?” Pauline reddened slightly.

“It varies. I usually start by squeezing my legs together. Sometimes I just go straight to touching myself.”

“Where?” Of course I knew – bloody well, but I remembered how exciting talking about details could be.

“The nuns call it “Down there” or our “Private Area”.” She hurried on. “We all know the proper words from sex ed, but the girls at St Mary call it our “coochie”

“Not the other “C” word?” Pauline reddened a wee bit more, but there was an edge of excitement in her voice, and her breathing quickened a little

“I’ve heard it, but its whispered.”

“I didn’t even hear anyone say it until I was eleven, but my life has been almost as sheltered as yours”

Pauline tightened her grip on my hand and leaned a little closer, so I went on. “It’s exciting but also dirty.” Bad move. Pauline pulled away a bit.

“Quit the dirty.” She almost snarled again, and once again looked ugly. “I get enough of that from the nuns. Shaming about pee and bleeding and smell.”

“No! I mean like dirty naughty and exciting. And as for the smell, I only smelled a girl once, but I liked it.”

“I thought you said you had never been with a girl?”

“I haven’t. Another kid was playing doctors with one of the girls at school and let me smell his fingers. What a turn on! Do you like your smell?”

Pauline nodded, so I pressed on. “What about taste? Have you tasted yourself?” It was a risk, but it paid off. Pauline lit up like a Christmas tree. Little Red Riding Hood was right out front.