Chapter 4: We take a huge risk
I mentioned my friend's family was well off, and because my large family didn't make a lot of money, I think THEY had a "soft spot" in their heart for me. So they sometimes took me along on family trips and vacations and the like.
In my 18th year, they decided to take a golf vacation to Kentucky and I was invited along. It had been quite a while since my handjob fantasy was fulfilled by Ms. Nancy, and once again, I was wondering where I stood with her. I eagerly snapped up the invitation, and soon we were driving together to Kentucky for a golf vacation.
I am sure you can imagine the several hour trip was excruciatingly frustrating for me. I sat in the back, behind her husband, and my best friend sat behind his mom. This beautiful woman, who had watched me cum, not once, but twice, and had made me cum while watching her jiggling tits was now mere inches from me and staring from the back seat, I could see the beauty of her face and watch the curve of her breasts in the "comfy" t-shirt she wore on the trip. Unfortunately, she was wearing a bra, so the road bumps were of little benefit during the trip. Still, just being this close to my long-time masturbation fantasy and reality had my hormones churning.
The drive was lengthy and exhausting, but at last we arrived in Kentucky and were introduced to the family in whose home we would be staying. They seemed like great people, and I knew I would be comfortable, even though I was the lone friend invited along on the trip. Our hosts had a home on the golf course. Their residency in the neighborhood included golf privileges for them and their guests, which meant we were going to get to play a lot of golf.
We were all big into golf, especially Larry and me. I probably played as well as I ever had, every once in a while beating Larry, who was an excellent golfer. Something that seldom happened.
Larry and I awoke at the crack of dawn each day to play. The older folks would go out later, because they did a great deal of drinking while on vacation and probably woke up hung over every morning. Whatever the reason, Larry and I were usually done by the time the older folks got ready and went out to play.
This doesn't mean I didn't get my opportunity to see the object of my many teenage fantasies. I got to see her late each morning as she and the other women (some of whom were not so bad either) got ready to go out on the course.
Ms. Nancy played golf in what they call a skort, which is a combination skirt and shorts, and a form fitting, but modest, polo shirt. She had great legs, a sexy mature woman's rear end, and of course, those fabulous C-cup breasts protruding from her polo. She wore her hair fairly short, nice sexy lose curls about her face, and her makeup and lipstick were always perfect. She had beautiful green eyes and long eyelashes that could literally make your knees buckle as she stared into yours.
I couldn't seem to take my eyes off her whenever we were together. I walked around with a constant 18 year old's hard-on, thanks to her, and I am guessing that, if no one else noticed, the smirk she gave me every time we spent just a bit of time together was proof that she noticed my reaction to her. She was discreetly flirtatious, batting her eyes and smiling at me with those pretty white teeth whenever she could get away with it. Women seem to be good at this. Of course, I did the same to her, though it was probably a clumsier effort.
Still, there was virtually no opportunity to be completely alone with her. I think it was her conscious decision, as there were too many people around and I am sure she didn't want to be caught alone with an 18 year old "boy" hundreds of miles from home. The shame would likely have been palpable. Thinking back, I'm not even sure how I would have gotten home. Even in my young mind, I was able to reason through these things and understand why, despite her many smiles, discreet glances, and biting a nail occasionally, nothing overtly sexual occurred during the first few days.
I, of course, was perpetually scheming to find a way to get the two of us alone. It occupied my mind increasingly as the week wore on and as I became more sexually frustrated. I was perpetually hard, but I resisted relieving myself on the off chance that we might find a few minutes to be alone. My sexual frustration affected my concentration, which affected my ability to scheme to find a way to be with her. As the week wore on, it also affected my golf game.
It had been a long week and Larry wanted to play 36 holes on Friday. We were scheduled to leave Saturday mid-morning, and we both wanted to play a lot that day. I was awful, barely breaking 90 both rounds, I was frustrated, I was thinking about a certain beautiful woman, I was thinking I wanted to cum, and I had been unable to fulfill my sexual desires. In my head, "damnit!" was the only thing I could think. If Ms. Nancy had a strategy and wanted me anxious and frustrated, well, it was working.
That evening, after a delicious home cooked dinner prepared by their friends, Larry and I retired to the downstairs gameroom and played some pool (dude was a competitor, wanted to win at everything). In my sexually frustrated state, I was no competition and he won at pool, then dominated me in a game of nerf basketball. He wanted to play some more, but I said "No, let's watch TV and then I'm going to bed." My crotch was throbbing. I was hard as a rock, and I had had no satisfaction, despite being mere feet from my fantasy woman the entire week.
We were watching some mundane network program (back when we only got three channels) and I began to drift off to sleep after a long day and a hearty meal. I stood up, yawned, stretched, and said "I'm going to bed." I was pissed about the way the week had gone. I had been mere feet away from this goddess, this vision, this masturbation fantasy and handjob maven for several days, a woman I desired and that I knew desired me, and yet had been unable to act on it at all. My best friend didn't seem to notice my attitude, but he was, I think, a bit naïve and wasn't really paying attention. He was interested in girls, young ones with perky breasts and tight cute teenage butts.
He could have them, I was only interested in the big breasts of his mom, her sexually mature rear, and those wonderful thighs.
I headed to the bedroom and lay down in my twin bed. Looking over at the clock, I saws that it was after 11 p.m. I heard the sounds of The Tonight Show from the other room. Larry was still watching. I began to doze off.
Probably about 20 minutes later, I heard the TV switch off and my best friend walked into the room and lay down in his bed. There were two twin beds in the basement bedroom that we were using. Having been awakened from my brief nap, I wasn't ready to fall back asleep, so I listened to
Larry's breathing become that slow, regular rhythm of a deep sleep. He was out cold. The guy did everything to the max, so I wasn't surprised he was exhausted.
In my frustrated state, sleep wasn't coming easily for me, and I began churning over in my mind where things stood with Miss Nancy. Was she done with me, was she through taking the risks? Had she "kicked me to the curb," so to speak? I initially thought that my desires weren't really love, but more of an extreme sexual attraction. But I desired no one but her. I hadn't really looked at other women, I hadn't thought about other women, I hadn't been with other women. And there had been opportunities. She was all I wanted. Perhaps I was in love with her. My 18 year old brain struggled to understand the feelings I had.
My bed had heavy covers, a sheet, a bedspread, and a quilt on top. And yet, through all that, in the faint light of the bedroom, I looked down and saw this gigantic tent created by my hard on. "Wow," I thought, "this woman has really had an effect on you."
