When I was 14 I had only had the boy-girl experience of 'feeling-up' three girls, all about my own age when I was 13 and 14. In each of these experiences, I had been lucky to have met girls who had been as eager and curious as me. All of the experiences had taken place with girls I had met during my summer vacations at a cottage that my parents had built in a nearby state that was only a 90 minute drive from our city home. Perhaps the city girls of the Midwest 1960's were not yet as liberated as those who grew up in the country.
My first 'feel' was with a 12-year-old 'year-round' neighbor who lived down the road from our cottage and who would walk to the beach with my older sister and me when we went down to the lake to swim. We played 'horse and rider' with the other kids at the lake with each boy carrying a girl on our shoulders while we tried to pull the other horse and rider down into the water. I liked having Patsy up on my shoulders and we 'won' more than we 'lost'. There was always a lot of pushing, splashing and dunking. The wetter the better.
Each time, I guess we each were trying to catch a 'feel' of the budding breasts that were perking up under the old one-piece bathing suits that all the girls wore in those days. Patsy was just starting to develop and had no more than a teacupful in the budding breast department. Needless to say, I often developed a boner [small, but certainly hard!] that was at times a bit embarrassing and at other times extremely amorous.
One day, after a 'win', Patsy and I swam out to the raft that was anchored about 100 yards off of the beach. Mostly the older kids used it to sunbathe and dive off of. This day, a hot but hazy afternoon with thunderstorms off and on, we were alone. We swam under the raft and held on to the 55 gallon drums that were used as floats. Patsy was behind me and as I turned to look for her I felt her hands touch one of my feet and then run up my leg as she started to surface. This time, however, she let her hands stop when they got to my swimming trunks and she lightly touched the boner that was jammed inside the suit.
When she came up for a breath, she let her hand slip inside my swim suit and for the first time I felt a female hand grasp my dick. We didn't say anything and she gentle pushed my suit down as she extracted my hard-on from its hiding place. She was obviously a bit more experienced and later told me that my dick was the seventh one that she had jacked-off. The water in the lake was very warm and her stroking soon had me near the cum-shooting point. As I held on to the float, Patsy kept up her jacking and soon had me shooting cum into the greenish lake water.
'That was neat', she said as she felt my pecker begin to shrivel in her hand. She then moved in front of me and slipped the straps of her swim suit off of her shoulders and pulled the top down around her waist.'Suck on my titties', she asked. I ducked under the water and moved my mouth from nipple to nipple as she placed one of her hands behind my head and held my face tightly against her chest. Then, as I came up for air, I moved my hands so that one was earnestly rubbing and pinching her breasts and hard nipples and the I moved the other hand into the crotch band between her legs.
Patsy held on to me with her arms around my waist and I quickly stuck one finger under her suit and felt her pubic hair around her pussy slit. It didn't take long for the same finger to easily slip into her now widely open legs and dig into her wet cunt hole. My very first pussy! I surely didn't know anything about girls and masturbation, but she had her eyes closed and was pushing against my hand as she bucked up and down on my wagging finger. I don't know if she came, but she soon shook and shivered and told me she was cold [the water must have been 85 degrees!?!] and we slowly swam back to the beach.
This 'first-time' was not the last, and on three other occasions that summer Patsy and I went to the raft she gave me a hand-job while I got to suck on her tiny tits and finger her pussy. While we never went any further, I was very disappointed that Patsy and her parents had moved out of their house that winter and she was not there when we returned to our cottage the next summer. Thanks, Patsy, where ever you are!
That September, I returned to my high school and felt like a real 'stud'. There was a new girl, Karen, in my German class who had recently moved to the area with her mother and brother. Her parents were divorced and in the 1960's that was sort of unusual. Her younger brother, Mike, was on the Frosh-Soph football team with me and we became friends since we lived on the same 'alley' [but different streets] and both walked home along the same route after practice.
So, Mike and I would be at each other's homes after school and I got to see Karen and some of her friends after school, as well. Mike and Karen's mother worked long hours and they were pretty much on their own until 7 or 8 at night. The house that they lived in was a three-story home with an apartment in the basement, and an attic above their apartment on the first floor. Their uncle Bud owned the house and lived in the basement.
Over the first few weeks, Mike and I talked guy stuff and he must have felt comfortable telling me some of his 'secrets', not the least of which was about a trunk that was up in the attic that belonged to his uncle. Upon sharing this information, we went up the back stairwell and I got to see the treasure trove of nudist magazines, Playboys, and 'French cards'. The French cards were mesmerizing for me and when Mike let me borrow a few, they became intense fodder for many masturbation sessions. Mike and I never did any mutual masturbation in that attic, but we did share stories about our 'private' jack-off experiences with each other.
Then Mike shared another 'secret'. He had found [or made?] a hole in the wall of a closet that was in an unused ['junk room'] bedroom that shared a common wall with his mother's bedroom. He told me he often watched his mother through that peep hole. I got really 'hot' hearing that news and begged him to let me sleep over so that I could also get to see his naked mother. The next weekend didn't come soon enough!
I made arrangements to spend both Friday and Saturday night at Mike and Karen's house. At that time, I had not really thought about Karen as a girlfriend because she always talked about a boyfriend who she had dated in 8th and 9th grade at her previous school. Since he now lived in another state and long distance phone calls were very expensive she had only been communicating with him by letter and only 1 or 2 phone calls each month.
That Friday, Mike and I had a football game and we didn't get back to his house until after 7pm. His mother wasn't home from work yet and Karen was in her room with a girl friend. Mike jumped into the tub to take a bath [showering at the locker room was sort of 'gay' in those days] and we usually washed up after we got home. I was next and as I was filling the tub, Karen knocked on the door to the bathroom [they only had a single bathroom, the same as at my house] and I told her to wait a minute while I grabbed a towel. She didn't wait! And she walked into the unlocked bathroom just as I was covering up my soft dick. Her smiling apology for barging in was embarrassingly accepted and I waited in the hallway while she peed.
I then completed my bath [no showers in those days, either] and believe-it-or-not, I put on my pajamas. It was after 8pm when Mrs. Hanson got home and she had stopped for pizza since she knew she was having a houseful of hungry teens. She was probably 35 or 36 [age, not breast size!] and was not beautiful, but was pretty in a 1960's Midwest USA mom sort of way. She had short wavy brown hair that she wore in what was called a 'flip', was tall at probably 5'8' or 5'9' and very slim. She really didn't have very large breasts, and they were actually smaller than her daughter Karen's. She always wore nice dresses and high heels with nylons and that night was no different.
She had bought two pizzas and a six-pack of cokes and we all [Mike, Karen, her friend Claudia, Mrs. Hanson and me] all sat around the kitchen table and ate pizza, talked about our football game [we had won 12-6 over a nearby rival high school] and then about general school stuff. Mrs. Hanson knew that Karen and I were in the same German class and she told me that she had met the children's father when he had been stationed in Germany with the Army and her father was based at a US Air Force base close to the Army base.
She told us that she was a senior in a DOD high school and had met their father when he attended a dance at the Army base Officer's Club. She indicated that this had been after WWII when the US forces were still acting as 'occupation forces' and the stationing of dependents had been a recent thing that the Army had done so the soldiers would not have to rotate back to the states every year and they would stay in Germany for 3-4 years. She also told me that she spoke some German and would be willing to help Karen & myself if we wanted or needed help.
After dinner, we all helped wash the dishes and clean up and then Karen and Claudia went into Karen's bedroom and Mrs. Hanson left for her room. I think my dick was already getting hard, as I watched her walk out of the kitchen. Mike smiled and we both sort of winked at each other, as we walked down the hall and entered the unused bedroom that was next to his mother's bedroom. We quietly walked through the room and entered the walk-in closet that had clothes hanging from the rack but Mike had moved all the boxes from the floor. He had created a virtual jack-off den, with two pillows on the floor and some old towels nearby to catch his cum.
We had not discussed how we would share the closet since the peep hole was only big enough for one person to look through at one time. The actual hole was about 2-3 inches around and had initially been caused by the door knob from his mother's closet hitting the plaster when it was opened. Now, the plaster had been broken through and the hole between the wood laths provided a perfect view of Mrs. Hanson's bedroom. When I kneeled against the wall, I could see Mrs. Hanson sitting on the end of the bed and all she had on was her half slip and her bra. I could have shot my load right then. We had been a bit slow getting into the closet and she had already taken off her dress and it was draped over the bed.
I turned around and asked Mike if he wanted to look and he told me it was OK since he had seen her many times and now it was my turn to look. And, look I did. Mrs. Hanson was now unbuckling the side strap on her beige toeless heels and had lifted her leg up on the bed in a sort of crooked sidewise manner and she then slipped the shoe off her foot and tossed it toward her closet door. She then did the same thing with her other leg, crooking it onto the bed behind her and unbuckling the second shoe. It too slipped off in her hand and she tossed it down with the first one.
Now, as I felt my dick throbbing, I unbuttoned the front flap of my pj's and let my hard-on spring through the flap. Mrs. Hanson stood up and with a move that still sends shivers down my spine every time I see a woman unhook her bra and pop her tits free, she reached behind her back and with one hand, unsnapped her bra. Bing! Tits. Real women's tits. Not small Patsy tits. Actually, not large woman's tits. But, tits, none-the-less! And, nice small dark nipples. Mrs. Hanson then walked toward her dresser by the window and opened the drawer to place her bra into the top drawer. She then leaned toward the mirror and with her right hand I saw her squeeze each of her tits, first one and then the other as she looked into the mirror. First breast exam? I don't know why she did that, but it was surely exciting to watch. Then she turned and pulled the slip off and exposed a pair of white panties and my first view of a garter belt on a real live woman! Heaven.
She then went back to the bed and sat on the edge facing my peep hole as she 'popped' the snaps that held her nylons up and in a still vividly impressive mental image, I watched her roll each nylon off of her slender legs and toss them on the floor next to her shoes. Then, thecoup de main, she stuck her thumbs into the waistband of her panties and slid them down and off of her legs. With that move, my orgasm hit the wall and I felt cum pump through my fist and spurt out in the explosive blasts that were typical of the teen penis! I could see the darkness of her pubic hair from the nightstand lamps and ceiling globe in the room and was focused on observing the biggest bush of brown curly cunt hair that I would have the pleasure to see for years to come. Her pubic hair actually started slightly below her belly button and then extended to a flare that moved from directly over her vagina and spread darkly onto her inner thighs. Mrs. Hanson walked over to the closed bedroom door and took her housecoat off of the hook on the back of the door and slipped if over her naked body. Thus ending the best, to that date, visual stimulus that I had ever experienced for masturbation.
I watched Mrs. Hanson leave the bedroom and heard her enter the bathroom and begin to run the tub for her bath. Mike told me to use one of the towels to wipe off my pecker and to dry the now dripping cum off of the wall. Obviously, he had been watching me from behind as I jacked-off watching his mother undress. When I came out of the closet, Mike was smiling and he asked me,'How was that?' My understated reply was,'Great!' We quickly left the room and entered his bedroom that was across and down the long central hallway.
Later, when we heard Mike's mother walk out of the bathroom, he told me it was his turn and he left me with my own recent thoughts as he slipped down the hall and into the jack-off den to watch his mother put on her nightgown. Five minutes later, Mike was back in his bedroom, as he gave me the 'AOK' sign with his thumb and index finger on one hand as he made a 'jacking' motion with his other!
Mike had bunk beds and his was on the top so I took the bottom bunk. About 30 minutes later, Mrs. Hanson knocked on the door and came into the room to wish us a good night. Little did she know how 'good' it had been? Later that night, I was awakened as the bed began to shake as Mike jacked off in his top bunk. We soon were jacking in tandem with me actually shooting my load into the bed sheet slightly before Mike's rocking slowed and stopped. I slept very soundly after that.
While this peeping action occurred on four [who's counting!] other occasions, none carried with them the enormous visual impact that the first time had upon my sexual and masturbatory life. Before Christmas, Mrs. Hanson and the kids moved into another house not too far away and we lost our peep hole, but never the memories.
Now, on to the hay ride! By Halloween, Karen had 'broken up' with her out of state boyfriend and we had started to 'like' each other. Mrs. Hanson had been true to her word and had tutored both Karen and myself with our sophomore German class and we were both doing great with our conjugated verbs and adverbs as we started to conjugate other body parts, both at her house after school and in my garage in the backseat of my father's car. We had not gone further that kissing and some over-clothes breast-rubbing, but on many occasions, I had shot a load of cum inside my pants as we panted and sucked each other's faces.
Karen and I had both joined social Tri-Hi-Y and Hi-Y girls and boys clubs at the local YMCA. At Halloween, they had planned a boy-girl hay ride through the local forest preserves. Karen and I had signed up and now as we waited at the YMCA for the bus to take us to the stable we both seemed excited with the possibilities. The bus came and took us, along with the other six couples who were going on the ride, to where we were going to meet the hay wagon.
When the covered hay wagon pulled up, we all climbed into the hay bed and each couple was able to 'pick a spot' where we could settle into the sweet-smelling hay. In those days, girls never wore pants, and Karen had worn a long skirt that was called a 'granny' dress. As soon as all were 'aboard', we started out on the two-hour ride through what were sure to be 'unseen' trails. We had a warm quilt that Karen had brought from her home and I immediately felt a rush of blood to my penis as I realized that it was the same quilt that had been covering her mother's bed when I had jacked-off watching her mother undress from my vantage through the peep hole at her house.
As we lay back in the hay, Karen reached under her granny skirt and pulled her panties down her legs and over her white socks and black and white saddle shoes. Oh, what a night we were in for! I could hardly keep my pecker in my pants as I watched her fold her panties and put them into her purse. By now, pre-cum was seeping from my pee-hole and I could feel my jockeys getting damp. I didn't have to wait long to begin to get some relief as I felt Karen's hand move to my belt and begin to unbuckle the belt and unsnap my Levi jeans.
Now, as I helped Karen pull my pants down around my knees, we began to kiss and move our semi-experienced hands to each others genital areas. I was quickly moving my hand to push Karen's skirt into a bunch around her waist and began to enjoy the wet love nest that surrounded her pussy slit. As I eagerly explored her pussy lips and the wet opening of her cunt, I felt her grab my now fully erect dick and begin to jack it in the same up and down stroking manner that it was so accustomed to from my own hands.
My fingers entered my second cunt, but this one was not wet from the warm water of a lake, but instead, it was dripping wet from the pussy juice of my 14 year old girlfriend. Karen seemed more experienced then I was as I felt her move her non-jacking hand and begin to hold and rub my aching balls with her lightly touching fingers. She also used her pumping hand to squeeze and release, squeeze and release with each up and down stroke. It was many years until I again met another girl who had so wonderfully mastered the art of the hand job as well as young Karen demonstrated that night in the hay.
My only lament about the evening is that it would be many years before I fully realized the ineptness of my knowledge about the female anatomy and the actual mechanics of female masturbation. All boys should have lessons at some time to allow them the opportunity to equally satisfy their youthful sex partners with masturbation and orgasm. Later, my own education actually came from a young bi-sexual and budding lesbian who taught me the fine art of pleasuring a woman... but, that indeed is another story.
Karen and I continued our heavy petting and whether she had an orgasm, or not, I must plead ignorant. But, there was no doubt that I soon experienced the first of three enormous orgasms that I was to enjoy that evening! Karen was truly an artist. And, she was prepared. She had brought along four soft packs of Kleenex in her purse, and, in addition to my three healthy orgasms, she used several tissues to wipe off her sopping pussy that was emitting the first of my odiferous memories, namely wet, hot and pungent pussy odor. Is there anything better?
While I am certain that all of the other teen couples along that night had a fine time on that hay ride, it remains for me, the epitome of a peak experience upon which all of my subsequent sexual encounters are measured. With the rocking of the wagon and the clattering of the shoed horse hoofs and rickety wagon wheels along the rutted wagon trails, none of us was ever concerned about the enjoyment of anyone but ourselves. And, suffice-it-to-say, Karen and I had a wonderful time.
This night was the prelude to many months of sexual sharing that was unfortunately ended when Karen and Mike's parents went through a marital reconciliation and they moved away to live together again as a family at a far distant military installation. Perhaps that pleasant long ago sexual encounter added not only to my budding sexual experiential history, but also led to my choice, as an adult to join the military. But, that's another story, too.