Chapter 1

Ahh, the Summer of ‘69 or as I liked to think of it, the “Summer of Love”, of Woodstock, of Sex, Drugs and Rock and Roll, of hippies, of free love and for one young boy, the best summer of my formative years. Yes, that makes me old now but that summer I was at the grand old age of 14. As far as I was concerned I was well on my way to being a man, having developed a new found excitement at checking out girls, women, anything with two legs and some breasts. Heck, even a bucket of KFC was looking good to me. My only problem was I was almost painfully shy and scared to do anything but talk to a girl.

First, a quick little background: I lived on the outskirts of a small college town in a middle class family with a school teacher for a father and a wayward mother. She had a job selling things at home parties to other bored housewives which she managed to parlay into an easy way to run around on my father. Mom would disappear shortly after dinner to one of her “house parties” and dad would grade papers from school then have a few drinks and head off to bed. Of course, at the time I was too naive to realize mom was cheating and dad was drinking to blind himself of the fact. All I knew was I had an excuse to be able to stay out later than most of my friends because dad was passed out and mom wasn’t home.

I lived in a small neighborhood with a community pool (we didn’t belong as my family couldn’t afford the extra expense) but my best friend’s family were members and through guest passes I got to go quite often. For the past few summers I had begun to take notice of the neighborhood girls and women, noting their poking nipples on the cool summer mornings, the way those skin tight one-piece bathing suits of the day accentuated that creviced small mound that called to me from between the junction of their legs and those tight asses, oh those tight asses ... I guess the reason to this day I am an ass man. But, being painfully shy I knew I was destined to only look from afar, only to touch or kiss in my dreams.

And to ever see one naked? Remember that at that time about the only place we ever got to see a naked woman was when we found some old Playboys in the trash or just had a brief lucky moment. I had only got to glimpse one female naked (my little sister) until the prior summer when my best friend and I talked my sister and 2 of her friends (who were sisters and lived up the street) into playing strip poker. My sister was 11, my best friend was 12 as was one of the sisters, Cindy, I was 12 and the other sister, Sherry, was 14. I always thought Sherry was gorgeous but being an “older woman”, I knew I would never have a chance with her. The rules for our game of poker were; the first one naked had to stand in the center of the room, arms held out to the sides, for two minutes one way and then turn around and stand two minutes the other way. My goal of course was to get Sherry naked as she was the only one in the room with tits, even if they were only barely there. With luck and a little distraction cheating on my part when I dealt, for the first time I saw a pussy that had hair on a living breathing female. Sure I had glimpsed my sister a few times in the bathroom but she was bald as a cue ball down there. Sherry, on the other hand had just begun to get that soft, sparse, feathery patch of pubes that a budding young lady began with. Getting to stare at it for 2 minutes gave me ammo for many a wet dream after that night. I was so fascinated by seeing hair on a pussy that I barely even remember her small perky tits, just beginning to pop out and her glorious dark brown areoles (she had an olive complexion) with tiny nipples that stuck out from the excitement we were all feeling that night.

But I digress ... that fall a small shopping center opened up down the street from my neighborhood. A small local donut shop was one of the tenants and the owner only hired very pretty local teen girls and young women to work behind the counter. My friends and I began to make this our hangout but the owner, who only worked during the days, had made a rule that you had to purchase donuts or drinks to remain inside. They had a long counter with swivel seats and a few booths to sit at. Since I was the “leader” of the gang I hung out with, everyone knew the seat at the far end of the counter was mine when we were in there. It was against the far wall and I took to sitting there for two reasons, the wall to lean against while I sat sideways to the counter and the view. I found my love for coffee that Summer of ‘69, not because I liked the taste, but because I could sit there and drink a cup of coffee for a couple hours, especially since you got one free refill, thus giving me a reason for hanging out on a budget.

The girls hired at the donut shop were all from the immediate area, most I had known for years as they lived in my neighborhood. They ranged from 16 to the oldest, 21, and wore a required outfit of white skirts and white blouses. As stated before, I had chosen my selected seat for the view. In ‘69 the style for skirts were at an all-time short length and when the girls bent over to reach the donuts in the front display case I got to watch my version of Heaven. All those 16-21-year-old asses framed by silky smooth panties, the hint of camel toes showing, an occasional glimpse of a stray dark “pube” or two escaping from confinement, long slim creamy thighs all led to what seemed to me to be a constant erection from my pubescent cock. Now I had no idea at the time if I had a “big one” but through those sly peeks that all young boys did in the gym locker room I knew I had as big as most and bigger than the majority and spent most evenings in the donut shop trying to hide the fact that those young ladies had me straining the fabric of my shorts.

My favorite, Kay (the 21-year-old), a local beauty and the night time manager would often sit on the edge of the cooler that was located just in front of my seat during slow times and talk to me. I had known Kay for probably 5 years or so as she was one of the Lifeguards at the pool and always had a bright smile and kind words for even the young punk I had been. At that point I had no idea whether she knew she gave me the perfect view between her thighs as she sat there, but I knew I loved it. The hardest part of our long conversations was trying to peek at that sexy junction without being too obvious. I would occasionally notice a sly smile on her face after a quick peek, giving me the feeling that she knew I was getting a free show, but not knowing for sure. After all, why would a beauty like Kay allow this young boy to see her panties? That just didn’t make sense to me.

Kay was about 5’-8”, towering over my 5’-4” frame that still had a long way to go to reach my present 6’-0”. She had the athletic build of the Lifeguard she had been at our pool in prior years and had maintained it even after going off to college. Her long straight brunette hair hung half way down her back shining and silky. Her perfect, gleaming smile lit up my soul with every time it flashed my way. A long neck led down to smallish still perky breasts that like most young ladies at the time were not covered by a bra, this being the generation of “Ban the Bra”. Kay, besides having been tom-boyish in younger years had adopted the ways of the Hippies and when not in her Donut outfit was usually seen in cutoff jeans and tie-dyed t-shirts. But with those button down white blouses and no bra I often spent a little extra to get a dip of ice cream from the cooler that sat directly in front of my seat, always hoping to get that glorious view down her blouse as she strained to get that scoop I had ordered. I have fond memories of those slight glimpses at the edge of her extra-large areoles but no matter how hard I tried I never got a shot of those tootsie roll sized nipples that always seemed to be screaming at me from within that tight blouse. To me, Kay was as beautiful as any of those Playboy centerfolds I had often worshipped and what was even better than any of those fantasy women was Kay was real and actually seemed to enjoy talking to me. She was every young boys fantasy, an older woman who gave me some of the attention I desired.

One night while sitting at the counter, my best friend and I mentioned to Kay that we often had “sleep-outs” in the fort we had built in his back yard, using this as an excuse to wander the quiet streets of our neighborhood, getting into a little mischief and just having a good time. We often stopped by the loading dock of the grocery store in the shopping center at 3:00 in the morning to help ourselves to freshly delivered orange juice left on the loading dock, moving lawn chairs from front porches to the middle of the front yard and other small pranks. Kay, listening to our tales of fun smiled even more with every prank we described and after a while she said she’d love to come with us some night. As we had already OK’d with our parents for a “sleep-out” that night I quickly chimed in, “How about tonight?” Kay told us that she would get done that night around 10:00, would go home to her parents’ house to shower and change and would meet us when we could get there. With trepidation and the thought that she might back out we had to tell her we would have to wait for a 1/2 hour after my friend Mike’s parents’ bedroom light went out so we could sneak away. We told her this was usually about 11:30 and hoped that would be OK with her. She said that would be fine and we arranged the age-old signal of tossing a pebble at her window on the 2nd floor of her parents’ house. Mike and I headed back to his house so we could tell his parents good night and head into the back yard fort. I was as nervous as any first dater even though I knew this night was only going to be a few friends out having fun and chatting.

It seemed like days when it was only 2-3 hours before the lights went out in his parents’ room and we waited the 1/2 hour to give them time to go to sleep. Like the schoolkids we were we ran and laughed and talked dirty about Kay all the way to her house. When we arrived her bedroom light was the only light on in the house and after 2 or 3 tosses I managed to hit her window with a small pebble. Her beautiful smiling face appeared in the window and after a quick wave disappeared again. Seconds later her light went off and shortly afterwards her front door slowly opened and just as slowly and quietly Kay slipped out and closed the door behind her. We were off for a fun filled and for me unforgettable night.

We wandered the streets of the neighborhood, talking and pulling stupid pranks like leaving sticks or rocks on the front seat of unlocked cars, hanging trash on their car antennas, and other really childish stunts. We laughed told stupid jokes and even quizzed Kay about what we should say to girls when we got the nerve to talk to someone that we really liked. That was my question as Mike really had not been bit by the girl bug yet.

“Kay, I just get so nervous when I try to talk to a beautiful girl. I get all tongue tied and can’t say anything. The more I try to concentrate on what to say, the worse I get.”

She stopped in the middle of the street with an over exaggerated pout on her face, looked me right in the eyes and said, “I guess you don’t consider me beautiful.”

As I gazed into those gorgeous blue/green eyes I began to stammer, my tongue tripping over my lips, freezing up at the thought that she called me out on talking to a beautiful girl when I talked to her all the time. As her soul piercing beautiful eyes reached all the way to my heart, making it skip a few beats I was finally able to get out a garbled, “Kay, I think you are the most beautiful woman I know. But that is the problem, you are a woman, that’s different.”

“I’m not trying to impress you,” I lied

“Why am I different? I am a girl, right? You just told me I’m beautiful for which I give you my humble thanks and call into question your eye-sight. You have never seemed to have any trouble talking to me. Heck, I enjoy our conversations. You are one of the most intelligent, well-spoken young men I have ever had the pleasure to talk to.”

Hearing her say this made my chest push out and my shoulders square up from the “young man” comment. A slight bulge pushed out in my cutoff jeans shorts, from knowing now that this beautiful woman enjoyed our conversations.

“Gary, just be yourself, show interest in the girl you are talking to like you do with me, smile with that warm smile of yours and above all apply a few of those compliments, like how beautiful you think I am. You’ll do fine!”

My tongue was on complete freeze frame now and I couldn’t think of anything else to say so I said, “Let’s go have some more fun.”

Mike who was trailing ahead when Kay and I had stopped briefly for our little interlude said he was about done for the night and was getting sleepy. He was always the party pooper when he and I went out for late night excursions, always ready to call it a night because he was tired. At this point we would usually head back to our fort, curl up on the cushions we had collected from discarded couches and chairs that lined the floor of our fort and try to get some sleep before dawn.

Kay, not knowing our routine, asked, “What now?”

“Well it looks like Mike is on his last legs and I guess we ought to head back to our fort. I can’t tell you how much I enjoyed having you along tonight, Kay.”

“Ummm... , not knowing what you guys had planned for tonight I told my parents I was going over to a friend’s house tonight so they wouldn’t worry about me if they checked in my room and I was gone. They’d think it was strange now if I wandered in at 2:30 in the morning. Do you guys mind if I sleep in the fort too?”

My mind began to spin like a top, thoughts flying in every direction my infantile thinking dreaming up the idea that maybe I might get to see her naked. “Sure you can stay but we need to make sure you are gone before Mike’s Mom wakes up and calls us in for breakfast. That would be kind of hard to explain.”

Fantasies were popping up in my brain like mushrooms after a spring rain. Oh my god, this was just unbelievable. Please say yes!

“Then let’s head back to your fort,” Kay said.

I felt my bulge again reacting to my wild thoughts. Thank goodness it was too dark for Kay to see or I would have embarrassed myself to no end. I slowed a step or two to allow Kay to get just slightly ahead of me so she wouldn’t notice it until it went back down home. Bad idea. Her hot ass in those tight cutoffs just made things worse.

A short while later as we tried to figure out how to share 2 blankets between the 3 of us on this cool summer night we found ourselves giggling quietly so as not to make enough noise to wake Mike’s parents. Kay had laid down next to the far wall, I quickly grabbed the spot next to her and Mike laid down behind me. Within a couple minutes I noticed the telltale signs of Mike’s deep breathing and Kay and I continued to whisper as we were still not quite sleepy. My total thoughts were; here I am going to sleep next to a 21-year-old woman that I have had many fantasies and even a few wet dreams about and my 14-year-old cock was hard as a rock. What now?

“Kay, are you asleep yet,” I whispered.

“No, I’m still awake.”

“I’m really not tired yet, how about you?”

“I’m a little tired but we can talk if you want. You know I like when you sit at my counter and talk with me. You can always count on me to be a shoulder to lean on if you ever have any problems you need to hash out.”

Kay had turned back towards me and with our faces just inches apart our whispered conversation covered all kinds of topics; Kay’s plans for her senior year at college, she quizzed me on how I was holding up with my parents crumbling marriage, what we were up to for the rest of the summer, telling jokes, talking goofy, giggling and whispering the whole time. Finally, with a little help from me, our whispered conversation circled back around to my being afraid of girls and how would I ever get the nerve to ask someone to be my girlfriend. Kay’s gorgeous face just inches away, her wonderful personality, the fact that she enjoyed talking to me, the smell of her perfume wafting in my face, her soft warm breath tickling my nose, had me thinking of nothing but females.