Painfully shy couple take first tentative sexual steps

So though I’d stopped worrying, I was still mortally embarrassed. But I began to process a little of what Sally had said. Particularly about this not being, “out of the ordinary.” Did she just mean that she knew all boys did this? Or was she suggesting this was something she did herself? An idea that really intrigued me.

“Anyway,” Sally continued. “I really am sorry I’ve disturbed you. I’ll let you carry on,” she suggested. Blushing again as she said this, as she shuffled towards the door.

As she reached the door, she paused, with one hand on the handle. Taking a deep breath, she looked back at me and asked, so quietly that I could barely hear her, “actually Jack, would it be OK if I stayed and watched?”

“What?” I spluttered, “did I hear you right? You want to watch me play with myself?”

She wouldn’t look me in the eye. But, staring at the floor, she confirmed that I’d heard her correctly.

“Yes, that’s right.” Sally agreed. “I know it’s a strange request. But I’d love to watch you masturbating…And then see you make yourself come.” she concluded timidly.

My dick, which had shrunk to a fraction of it’s previous size now began to swell up again. Obviously over the last few weeks our relationship had started to become “sexualised”. In that I’d been groping Sally and telling her how sexy she was. But this, clearly, was taking it up several notches.

I was so taken aback, I really didn’t know how to answer. My first instinct was to deny her request and tell her how daft an idea it was. Looking back, if I’d have done that we may never have gone on to do what we subsequently did.

But I was genuinely aroused at the idea of Sally watching me. And cognisant that it signaled a significant step forward in our relationship. Or certainly significant to me, considering how little interaction I’d ever had with any other woman.

My dick, as is so often the way, overcome my brain.

“Ok…” I answered slowly, “if you’re sure you’d really like to do that. I don’t want to do anything to offend you.”

So, taking a deep breath, I removed the pillow from my lap and lay there, completely naked. With my dick now more than half hard.

“Oh my God, that’s bigger than I imagined,” Sally remarked.

Which was kind of her. But, having been in enough changing room showers, I knew I was no more than average sized. But it certainly did my confidence a lot of good.

Emboldened by her apparent approval, I started gently tugging on my cock. Which, after just a few strokes, reached full erection.

“Wow,” Sally exclaimed, with a giggle, “that didn’t take long. That looks really hard now. Almost painful.”

“No, it’s not too painful. Though it can be when I’m really desperate. But, right now, it feels really good,” I grunted in response.

I gave myself another few gentle gentle stokes, then shocked myself, by how forward I was, with my next suggestion.

“This isn’t fair,” I opined. “I’m lying here completely nude, with my genitals on full display. And you’re fully clothed.”

“Genitals,” Sally laughed, “I’m sure that’s not how you normally refer to them.”

Please wait…

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