I’m Still Trying to Figure Out What It All Means — Part 6

Or didn’t I tell you that two is always better than one!

The climax of Lesley’s visit, so to speak, came one night when Mark and I took her up into the Berkeley Hills to spend some time drinking and looking over the lights of the Bay area.

This is a lovely place to go on any night that isn’t too cold. The vista is exceptional and, in my opinion, is best enjoyed at night.

We got a six-pack and a bottle of Jack Daniels and headed up into the hills. Mark had the six-pack in the back seat with him and I had put the bottle of Jack under the front seat as I had already opened it and had a swig.

On the way, we got stopped by the cops. It was only the Park Police, but nonetheless, it was still the police. One of my headlights was out, and I hadn’t gotten around to fixing it.

It was a policewoman who stopped us, and I explained I was taking my friend from back East and my other friend from Scotland up to look out over the Bay. She seemed quite interested in our little party. She looked to be about 28 years old or so and gave off a vibe that she would have liked to have joined us. Mark showed her the six-pack to prove that it wasn’t opened and I, of course, discreetly did not mention the Jack Daniels.

It was about 1 AM and I reckoned that she probably got off duty at 2. I very nearly asked her when she was getting off duty and whether she’d like to join us when she did. Unfortunately, I had no guts and didn’t, but I had a sixth sense that the answer may well have been yes. That was the first thing about that night that I have come to regret.

What was the worst thing that could have happened? She might have said, “That’s very kind but regulations would not permit me to join you’. But that wasn’t the vibe she was putting out.

In any case, she let me off with a warning, but I insisted she write out an order to get the headlight fixed, which she did. She then got back in her car and seemed to give off a certain sense of regret before she drove off. It was a very strange and unusual encounter and I wish I had taken the risk because then I would at least know the outcome today, rather than dwelling on it and of course fantasizing for forty years about what the four of us might have done together.

So, we found a nice place down a dirt road away from the main road, laid out our blanket, cracked open our beers, and started our party. Lesley started flirting with Mark outrageously. There was nothing subtle about it, and he was reciprocating with gusto. The two of them were pretty deeply engaged in their banter to the point that I thought, ‘This is ridiculous, if you want to get it on, just do it’!

So, being the perfect facilitator of all things naughty and outside the normal staid channels of human socio-sexual relations, I undid her trousers and stuck his hand down her pants.

We then spent an hour or so finger blasting her and making out with her and generally gratifying her in a most lascivious manner. Objection met we none.

After some time of this delightful diversion, we went back to my apartment, and I have no idea what happened next. I must have passed out. The next thing I became aware of was that we were all in my bed with Lesley between us and that we were all naked. I have absolutely no memory of getting undressed or what happened after we first got back.

To this day, I have no idea if they had sex while I was passed out, and I never asked either of them what had happened while I was unconscious.

In any case, I woke up and found my naked girlfriend lying next to me with her back to me and facing another naked man next to her so I did what any normal red-blooded man would do under the circumstances and started fucking her from behind.

As I was fucking her, I was thinking, ‘Mark, stroke her clit’ but I didn’t say it. I still don’t know why. It would have been such a simple thing to say and, frankly, appropriate under the circumstances. I don’t know why I didn’t.

For some reason, I deeply regret that omission to this day. I really should have said it. Given the situation that we were in, there was no reason not to take this small additional action that would have further enhanced her pleasure. The line had already been crossed when I put his hand down her trousers, so why hold back at this moment?

After I finished, she rolled on her back and Mark was just looking at her as if he didn’t know what to do. I made a somewhat crass gesture with my hand towards her, which basically said, “Take her.”

So, he did.

Surprisingly, he didn’t last too long, so I assume they didn’t have sex while I was passed out. We then all fell asleep as it was now about 5 in the morning, and it had been a long and clearly intense night.

When we woke up, I considered suggesting to them we should all go to Tahoe for three days or so and that Mark and I should use that time to ‘Fuck Lesley senseless’.

I didn’t.

Again, I have to ask myself why? She had clearly loved getting both of our attention. We had made her the Queen of our little drama, and her sexual appetites and physiological response was more than the equal to whatever we could have provided.

This question bothers me to this day. It would have been such a simple act to have followed through on and it would have enhanced her vacation, her life experience and given her a lifelong memory which would have gone far beyond the one night that we shared and abided with her until this day. There was no downside to it, really. I regret not providing friends of mine, both of them really, with that gift.

Find all chapters here.