Where it happened: Beach/Golf Course
Langauge: English
Sex: Male
Rating: 5
Category: Straight
I had worked hard that summer. Not at a job, but on Lauren. She was beautiful, and I had known her since her family moved to my neighborhood when I was 7, or 8 years old. She was in her mid-twenties that year, and spending the season at the private beach in front of the golf course, a block from each of our parents homes.(The country club’s only activity to this day is golf. The beach is not developed for organized use.)
I was a teen who played music and had lots of friends, but still no girlfriend. When I discovered her in her bikini one afternoon, it was not unusual for me to pull up to her blanket and sit down for a chat. When we met I had been too young to really notice how hot she was, but as the years passed it came to my attention. Keep in mind, about 80% of the time there was nobody in sight/could see us.
As a middle aged guy now, I realize that had she been into me it all would have happened right then and there, but this is my life, and it’s never that simple. It took me a few weeks to even work the idea of changing the nature of our now many year relationship. Being several years older, she strongly resisted on that basis. But I was persistent.
I had Summer School (again) and I had no other option than ride my ten-speed the somewhat hilly terrain back and forth five miles each, so it forced me into physical activity. A habit I never really accepted without force. But it let me shed what little fat I had as a teen. I wasn’t ripped, but I wasn’t soft.
School made me be up in the morning, and let out by noon, so I would quickly ride to meet her. I was determined, so after the possibilities were in discussion, I pulled out all the resources at my disposal. I don’t remember where I got it (pre-web), but I read her a list of famous couples with older women, I regularly brought a guitar to sing my basic stuff ( I was already playing professionally at a local level, and did so on a bigger level in the NY area until I was about 30.),as well as a song or two written “just for her” (I was a decent performer, but a bad songwriter), and she seemed to be warming up.
About a month into my endeavor something must have clicked with her. But she still would not admit what she was feeling. Under the guise that since we could never be together, it wouldn’t be so bad if we just kissed.
That was not my first kiss, but it’s the first time I kissed someone I thought I loved.
At that point I had spent most of June and July building to at least the first intimate contact with Lauren. And decades later I won’t pretend to know long that kiss lasted in real time, but when the kiss broke we looked up to see her parents on the dirt path, walking back up the previous ten or fifteen feet since we came into their sight.
I was never really told the consequences of that sighting, but it was always recognized that her parents consider me to be someone who used drugs and alcohol, and in addition, doesn’t share their views on everything from politics, to religion. And since they were correct on all counts, whatever wrath came down on her set my efforts back a bit.
By mid-August she was back to kissing me again and every day I began my advancement to varying success. She’d let me caress her modest, but not small breasts at first through her top, and before long I had made my way under it. We played around with each other while making out. She would be concerned about hurting me when she reached into my shorts and gripped me, it felt great and I encouraged her. Although she didn’t let it get to the point that either of us got off.
On September first we were laying in the mid-afternoon sun playing our usual games when I spotted an opportunity. I was in position to move her bikini bottom to the side and dive right in. So that’s what I did. It was the second girl that let me do that (the first didn’t let me kiss her, no less do anything for me), and I now realize that I didn’t really have any clue as to what I was doing but she said later that she really loved it when I would do that to her.
So we’re on the beach and I’m between her legs. She’s enjoying the attention and whispers to me that we should move up to the fringe of woods up on the cliff behind us, just off the golf course fairway.
We climb the fifteen or twenty feet up the dirt cliff and settle into a small but hidden spot. There were no more preliminaries, this was the time for it to happen. Every guy reading this probably knows the flood of feelings that come to you when you’re still figuring out how to process them. I was feeling better than I’d ever felt before. I had the prettiest girl you could ever hope for encouraging me to thrust myself inside her. Things couldn’t have been going any better when I spotted motion out of the corner of my eye. I am balls deep in the girl of my dreams when I notice a man in his late 70’s or 80’s with two women of similar vintage looking for balls they hit off the fairway. Lauren grabbed the towel from under her for cover, while I I was left on my knees trying to cover my hard-on. The old man noticed what he had stumbled on and quickly guided the women out of the woods before they too saw. But it was way too late to stop. I went right back to work and soon I had to pull out (No birth control) and because I was still shy I held my shooting cock off to the side to avoid splattering her with the results of a powerful orgasm.
We’d continue on for a couple of months, with sex at the beach, on the golf course at night, and in her parents house when they were out.
All these years later I still see her every few years. She’s married and only wants the relationship we had as friends growing up, and prefers to ignore our shared intimacies.
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