Alex's Adventurous Diary Memoirs

This work is completely fiction. My definition of fiction includes literature in the form of short stories and novels that describe imaginary events, places, and people. That means it never happened, might be impossible, and may be illegal. The intention is to provide a stimulating story to the reader. My stories are not something I approve or suggest people try. If you are looking for non-fiction episodes in life, my stories will be unappealing to you. If you don’t understand the meaning of fiction, please look the word up in any dictionary.

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Tomboy Alexandra Changes

Perhaps I am a little strange for a vibrant young woman, but I am not into girlish things. I didn’t object when dad directed me towards a woman’s college, but I was happy a men’s college was situated directly across the street from Upper Brow University. They used many of the same facilities like the library, cafeteria, sports facilities and auditoriums, and actually, some of the courses were mixed sex, too, but the dormitories banned opposite sex visitors past the parlor. I wasn’t really into men yet either, though I had more male friends than female as I grew up in our little town of 10,500 people.

I’m not sure when it all happened, but as far back as I can recall, I preferred the games boys played, and I liked my hair short and easy to care for. I admired the long beautiful curls that were so prevalent then, but I didn’t want to be bothered. Mom and dad understood, and although they really didn’t like to see me playing football, they permitted me to play all sports until I was well into puberty, and by then I realized I needed to make some changes in my life.

Everyone called me Alex but my real name was Alexandra, which I really didn’t like. Alexandra sounded too formal and obsolete, but Alex was who I was, particularly with my short pixie like haircuts that followed me through several years of school. Due to my light skin, blond hair, and light blue eyes I needed to be careful in the sun to avoid sunburns, but redness followed me everywhere I went when I blushed at the slightest social discomfort. Thankfully, that characteristic became more infrequent when I entered high school.

Dad, in particular, was supportive in my athleticism even though he had two sons that played sports with me. Donnie was a year older and Ronnie was a year younger, and looking back, I think dad knew my brothers would never permit anyone taking advantage of me. It’s safe to say I was a rough and tumble daughter that was unaware that she compared favorably when she was among girls my own age.

When we started physical education classes in seventh grade, I looked pretty much like my classmates other than the length of my hair, but by ninth grade, I was a little behind most of them in maturity. As a matter of fact, I was the smallest in our freshman class, but I didn’t seem out of place.

My first day of high school brought a new girl to school, and it was I who had grown out my hair over the summer and started wearing clothing that was more suitable for a young lady in high school. I was still on the smallish side, but mom assured me I would catch up to my classmates before my senior year was finished.

I wasn’t happy that I had more work to do every morning as I applied my makeup and worked on my longer hair, but I did enjoy the new ogles I received from the boys. My name, Alex, meant, “Defender of Mankind,” and I wanted to be a defender of people like me that chose a lifestyle different from others.

Before I confuse anyone, I had no repulsion to girls, whatsoever; I just preferred to be with boys and enjoyed the activities they pursued. I found them easy to communicate with, but I had no sexual attraction for either sex. I was not ready for sex until after I turned eighteen and graduated from high school, but once I knew the pleasures I received and the appreciated gifts I provided, my new life as a young adult provided energy to help those less fortunate.

During the summer after I turned eighteen and I graduated, my doctor started me on birth control pills using the argument that it would help keep my monthlies regular and allow me to plan better for the times I would have my periods. I was never sure, but I thought mom probably suggested to the doctor that I should have the prescription fearing that some guy would make her a grandmother before she was ready.

It was a good idea because it was that summer that I first became more interested in men. At eighteen, I continued to be much more interested in typical male activities like canoeing, hiking, and fishing, and I joined groups that mainly consisted of young men. As I became more interested, I joined groups from neighboring towns, for I wanted to maintain my sterling reputation in my hometown. I didn’t want people to think I was something I was not.

Our town was near three other towns about the same size that was separated by about 30 to 45 minutes, so I preferred to join those groups. I was unaware of any men in our town that I attracted and none attracted me, so it was a good thing I moved along to other groups.

One group, I was very involved with was a group of hikers in Oak Trail, one of the small communities in our area. I had taken several day trips with them, but this was the first overnight hike I participated. There were ten young men, all young adults in their early twenties, and me! I was reticent to take the trip, but I felt I knew them all quite well, and I was confident there would be no unwanted advances. We hiked for about five hours before we set up camp, and I agreed to stay behind and protect our tents and possessions while the others explored the area.

As I collected firewood for the evening meal and scouted the nearby area, I heard Bill Turner return limping because an ankle injury he received from stepping on a slippery rock as he crossed a shallow stream. His pants were still damp, but his ankle was swollen significantly though it was obviously unbroken. Being always prepared for the worse, I had a roll of three-inch wide elastic bandage material and wrapped his ankle.

It was that day that I got to know Bill as we sat by a small fire and acquainted the other with our life stories. Bill was tall and muscular and was a football player at State College where he played defensive end. I had grown some over the last couple of years and now I reached 5’3″, but standing beside him who stood 6’3″ I felt dwarfed as we sat and talked for three hours before the first of the explorers returned.

It was that fortuitous day when I received a call from Bill a few days later to take me to dinner, and I was beginning to believe I liked being with him. Tall, thin, and good looking was important to me, but he was also a genuinely nice guy that could carry on an adult conversation. That night I received my first gentle kiss as he walked me to my front door, and it sparked a feeling I had never experienced before, and I was astonished when he asked me to join him on another overnight hike to make up for the one we really missed the previous week.

Being as naïve as I was, I was dumbfounded as he asked the question, almost as much as if he asked me if I wanted to have sex with him next weekend. I would have answered, “no” had he asked that question, but hiking and spending the night seemed more acceptable, and I knew I needed to get on with my life and get some experience with men before I started college.

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Mom had said as much about a year ago, but I never saw the opportunity or had the desire until Bill asked me, and I quickly replied I’d love to hike with him. I didn’t say I was interested in anything more than taking an overnight hiking trip, but I knew the subtle question he asked, and I knew that I agreed to sleep with him in his pup tent. At least that’s what I hoped he was asking.

Having grown up with two brothers, I was somewhat familiar with man’s anatomy. I’m sure you know the issues with one bathroom for three people, and although we were modest, there were occasions when we were nude when we didn’t intend to be seen. Ronnie was the biggest offender, probably because he was the youngest, and he wanted to learn what his sister looked like. That said, however, he was never lewd. Still, at one time or another, we had all seen the others naked.

Mom was as good of a mother as I can imagine. She was understanding and nearly always had something comforting to say about any situation that occurred in our household. I needed to tell mom I was going on an overnight hiking trip with a friend, and I was confident she would tell daddy. He was also a gentle and loving person, but daddy held a special place in his heart for me, and I was timorous to tell him my plans to sleep with someone he didn’t know or approve.

When we finished our conversation, mom asked if I had condoms, and I responded that I didn’t, so she went to her room and returned with a box of twelve. She said she didn’t expect me to use them all on the hiking trip, but that I needed to always carry a supply if I planned to be sexually active. I hugged her knowing she always was prepared to help me avoid a tumultuous issue like this.

Mom said, “You may want to want to trim you genital hair if it’s very long, Alex. Many men like a shaved pussy, but even hair that is cut to about half an inch is nicer if it’s not wiry.” I was embarrassed, but I admitted my hair was already short there, and I explained it’s very soft like peach fuzz, so I expected Bill would like the look. Thankfully, mom didn’t ask to check.

Bill called the night before we planned to leave and explained he had a little different plan now that the weather looked like it may rain part of the time we were gone. His family owned a cottage about fifteen miles west of Twin Forks off highway 399. He said there was a lake where we could swim, and to bring my sleeping bag just in case the rain passed and I wanted to sleep outside. We planned to take towels and anything we wanted to eat, but the power and running water was on in the cottage, so we wouldn’t need to cook outside if it was wet.

By then, I was as excited as I had ever been, for I feared he planned to cancel after he saw the weather forecast for rain. I had planned for this all week, and I didn’t want to suffer the disappointment. I’m sure the excitement in my voice was apparent when he confirmed he was picking me up at 8 am.

My backpack was stowed, and I brought some beach towels and snack foods, but Bill said he had all the bases covered as I entered his SUV and we headed down the highway for our first overnight. Before we arrived at Camp Water’s Edge, the clouds darkened and the rain began putting a dampener on our hiking plans. I was hoping we could entertain ourselves at least until the rains cleared out so we could hike or swim, but I wasn’t very confident.

I was anxious to unpack the truck after I explored the small cottage with a single bedroom downstairs with a tiny kitchen and a beautiful sitting room with large windows overlooking Lake Timbuktu, which appeared dark and deep under the heavy cloud cover. Upstairs were two other smaller bedrooms with a toilet and washbasin while the main bath was a bit larger with a mobile home size shower in addition to the toilet and washbasin.

We didn’t bring much and most of it went into the bedroom or the refrigerator just as the sky began to clear and the sun peeked through the tall hardwoods. After the last article was properly stored, Bill reached out his arms and welcomed me to Lake Timbuktu with a warm kiss on the lips and admitted he had been waiting impatiently for this weekend, too.

I was hoping Bill would take immediate charge and whisk me off my feet and carry me to the bedroom, but he was too much of a gentleman to be impatient with someone he didn’t know very well yet. I clung to him like a vine to the tree trunk as my heart started to beat faster and my breathing more difficult.

He asked me if I was happy I came with him and asked if I wanted to go check the lake water to see how cold it was. I admitted I’d rather just have him hold me close for a few minutes and get to know him better now that we were finally alone. I told him I had never been with a man before, and I was excited beyond belief, and that I was a little apprehensive at the same time.

Bill looked and me and lifted me from the floor like a doll and asked, “Alex, you aren’t afraid I would hurt you are you?”

That was the farthest thing from my mind, and I explained I would never have joined him for the night if I thought he’d abuse me.

Bill led me to the large wrap around porch and removed the plastic cover, which kept it dry and asked me to join him to watch nature for a few minutes. “I really don’t want to scare you, Alex, I just want to have a wonderful weekend that we will always remember, even when we’re old and gray.”

Bill lifted me easily and carried me to the stuffed couch and held me in his lap as he bent low to kiss my sensitive lips. “We will go no farther or faster than you want, Alex, but I do hope to make love to you this weekend. Just remember you can be in control, and I’ll follow your lead. So as we say in basketball, the ball’s in your court.”

This didn’t ease my mind because I wanted to go farther right then, but I didn’t really know how to send that signal without being incredibly obvious. Sure, I knew I could stand up and lead him to the bedroom or start playing with his manhood, but I wasn’t that forward. I needed him to be the leader.

I could feel him beneath me as I sat on his lap, and he needed to move me on two occasions to be more comfortable for him. Finally, as he was kissing me I stroked his face with my petite hand and whispered he was incredibly handsome. He was rubbing my back, and occasionally I felt him run his hand lower to my butt, and when he did I softly moaned my approval.

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I lowered my right hand from his face and placed it over his breast and placed my left hand on his right hip. By now Bill’s penis was very noticeably grinding against my inner leg as I repositioned myself higher on him, which freed him and allowed better access to my groin and upper legs. I could feel his fresh breath on my neck when he whispered, “Are you comfortable?”

I knew this was my opportunity to move at will and placed my hand in his and asked to go someplace more comfortable. A second later I added, “Someplace like the bed, Bill. That would be nice.”

He likes to carry me, perhaps because I was only about 115 pounds compared to his 180 pounds, so he stood, still holding me in his arms and carried me into the bedroom as he continued to kiss my passionate lips. As he placed me gently on the bed he began to unbutton my blouse and unclasp my front closure bra.

He stopped and asked, “Are you alright with this Alex or should I slow down?”

I replied, “Yes, Bill, I’m fine, you can remove anything you wish.”

The very next thing he removed were my breasts from under the opened bra and bent down to take them into his mouth one at a time. It was the very first time my little titties were ever touched by anyone but myself, and the feeling was electric as they became solid as a green apple. He pulled me up to remove my blouse and bra completely before he unsnapped my blue jeans and began to tug them down with my fancy undershorts.

As I lay naked in his presence he stood back and I saw him marvel at my body and claimed I was the most beautiful woman he had ever seen. Bill asked, “Do you want to undress me or should I go ahead, Alex?”

I already dreamed of removing his clothes and kissing my way down his body, so I quickly got up and began with Bill’s shirt and started to kiss his breasts and stomach before I removed his blue jeans and shorts and saw my fist erection waving at me as he stepped from his shorts and I clasped his beautiful rock solid penis. I was about to kiss his helmet and cup his testicles in my hand when he lifted my lips to meet his.

Bill said, “Alex, I need to be gentle with you, but at the same time, I’m so excited I’m afraid I could disappoint you and come too soon.”

I asked, “Bill, did you bring a condom?”

Bill responded he did, and he opened the wrapper and asked me to roll it down over his firm erection. I quickly started the process and saw how it fit snuggly all the way to the last roll, but there was still an inch of shaft remaining past the end of the condom.

He didn’t ask me if I was ready, he just lifted my legs over his shoulders and started to insert the swollen head of his penis into my anticipating maidenhead. I could tell he was being gentle but persistent as inch by inch he gained ground until he was about halfway inside. It was then that he asked if I was all right, and I told him to proceed, as everything seemed fine.

The next inch, however, broke the barrier I knew would occur, but the pain was insignificant. I said, “Bill, now you can go the rest of the way. You’ve taken my cherry.”

Even them Bill was gentle, and he never did get his entire penis inside that time, but he began a rapid fire plunging and withdrawing piston-like movement that ignited some feelings I didn’t recognize. And then I flooded my vagina and his penis with fluid I didn’t know I had inside, and I wondered if I urinated as I moved in opposition to his driving force as he pummeled my receptive pussy.

I felt the first eruption in two ways. First, I felt his cock expand in diameter before he ejected fluids into the depths of my vagina. I knew it was semen, but I didn’t expect it to continue five times. I felt it against my cervix and set off another orgasmic spasm in my vagina as I gasped for breath.

Bill collapsed and allowed my feet do drop away from his shoulders as his penis puckered up and slipped outside opening the floodgates of fluids that ran down my butt and onto the towel he placed beneath me fifteen minutes ago. Once again I heard Bill ask, “Are you alright, Alex?”

I responded, “Bill, I’m just wonderful, but I need something to clean myself before I drip on the sheets. I’ve never felt better, Bill. I hope we can do this again.”

That weekend we made love five times, and by the time I went home my boobs and my vagina were sore. It was a special time for me as I had an opportunity to enjoy and give oral sex, but it was the warm companionship and just plain intercourse that I will never forget.

Bill was my first love, and we got together several times that summer before we headed off to different colleges. Now I felt secure about sex, and I planned to have some relationships before my freshman year ended. I knew my intentions were to be careful as I selected my partners and always use condoms. I planned to wait for sex without condoms until my wedding night! Perhaps I should add that I continue to enjoy men’s activities more than woman’s, and I have never ever even considered a relationship with a woman. I love sex with a man, and I love to be with them as often as possible.

When I have a chance, I’ll continue adding to my diary and see if there are more relationships I want to remember in the future. Now that I have finished grad school, I will have more time to reminisce and reacquaint myself with my favorite lovers. Thankfully, my selection process of looking beneath the obvious characteristics has helped my process, and the men I help along the way continue to be important in my life, just as Bill was important as he helped me through my first sexual affair.

I wanted to tell the world of my triumphant affair that weekend, but only my diary knows, and even then I couldn’t dare to write some of the more explicit details. It’s certainly has nothing to do with shame, it’s about joy and keeping it inside and remembering the wonder of companionship and enjoyment Bill provided me that weekend and many other times.
Thanks, Bill!

Updated: April 16, 2018 — 3:48 AM

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