Alex's Adventurous Diary Memoirs Ch. 02

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.


Freshman at Upper Brow University

My freshman year at Upper Brow University was exciting because I had my own apartment within walking distance of my classes. Two short blocks to the campus allowed me to carry a full course load and permit me to develop my journal. The four years of undergraduate work and two years of grad school whizzed by and my major consideration is whether I want to work another eighteen months to obtain a doctorate and live my life as a professor.

One of the best decisions I ever made in life was inspired by my father who convinced me to make an entry into a diary every day whenever possible. I have been doing this since I entered grade school, and the brief entries resurrect my memories now that I am twenty-four years old.

After Bill and I separated when I started college, we both agreed we would always be friends and stay in contact, and to this day, we communicate by text or phone bringing one another up-to-date on the important things in our lives. I always knew I could bounce anything off of Bill and receive an honest opinion in return, and I have always responded in kind.

Men suffering from indecision appear to be more unusual than women, but their issues always seemed more complex. I met a short man that was a sophomore the second week I was at Upper Brow, and I felt sorry that he suffered from severe shyness with women. Joe was a nice looking red haired man that wore sunglasses whenever he could, and I learned it was because he didn’t want to make eye contact with people he didn’t know, especially women.

Rather than approaching Joe and attempting to be his friend, I decided to observe his behavior as often as I could, and after a month I thought I had him figured out. We were in the same creative writing class with 100 other students and I started to look for him when I entered the classroom.

The first time I sat beside him I asked if the seat was reserved, and he responded, “only for you.” After that, I sat with him for every class, and generally I had an opportunity to chat some with him. I could tell he liked my attention, but he never initiated a conversation. After three weeks, we had been together for nine classes, and I asked him if he’d come to my place for dinner that night.

Being someone that was very unsure of himself, he was obviously surprised that a very attractive girl would be interested in him. I know that sounds somewhat conceited, but without a doubt, God gave me a very attractive face and body, and I thank Him for it every day. I used to be somewhat shy and never dated until I was finished with high school when I met Bill.

I was hoping I could do for this man what a Bill did for me a few months ago, and I was convinced Jon was not the nothing he thought himself to be. Yes, he was a little dorky, but that could be fixed easily, and when he matured in a couple of years he would be a desirable catch if he could free himself from his poor self-esteem.

When he arrived for dinner which was a simple chicken pot pie momma taught me to bake years ago, I had no plans to get past first base with Joe, but I intended to at least get a goodbye kiss when he departed. Surprisingly, Joe arrived with a beautiful fall colored flower arrangement that boasted of mums, sedum, and heliopsis. The colors were complimented my kitchen table and lasted nearly two weeks.

I took the flowers from him and thanked him profusely before giving him a strong hug and a soft kiss on his cheek. “What a thoughtful gift, Joe, they are absolutely gorgeous.”

That compliment brought a wonderful smile to his normally solemn face, and he seemed to relax in my presence for the very first time, but his face blushed red from embarrassment of a little kiss. I knew he had this idea that he didn’t deserve an attractive woman kiss him albeit gently on the cheek, but his demeanor improved and he became much more talkative and started to break free from his encumbrances and share something about his life, which had more setbacks than he deserved.

I didn’t generally drink and had nothing to offer Joe other than a Diet Coke or lemonade, but he preferred water with plenty of ice. As we ate, we sat beside each other rather than opposite, and during the meal, I actually held his hand briefly on three occasions when he was telling a life story.

Joe was an only child and was raised by a single mother who found herself pregnant when she was a senior in high school. He told of her sacrifices to get him through high school, but academic scholarships and financial aid were paying his college expenses and his mother helped him with a few dollars every week for sundry items. His home was only about twenty miles away but they had only one car so he stayed on campus and went home monthly to do the laundry.

I wanted to bring Joe out of his shell and introduce him to love and affection, but I realized it would take more than a single date to accomplish that feat. He confided that he had never dated a girl before and he was unsure of himself, but he didn’t object to a firm kiss on the lips when he left an hour after dinner.

The next day in class he was much more receptive and talkative and said he treasured their date more than I would ever know. I decided to proceed further, but first I wanted to call Bill and explain the situation and what I hoped to accomplish with Joe, and I was surprised by his suggestion.

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Bill said, “Make Joe earn it. Use the carrot and stick technique. Assuming you don’t end up being his long-term lover, he needs to change his behavior if he expects to be successful with women.” I appreciated Bill’s suggestions, but I planned to use my own techniques to see what would bring him out of his shell.

I didn’t offer him dinner the following week or encourage him to make a move though I remained very friendly. The following week Joe asked me if I’d go to the football game with him on Saturday afternoon and I accepted and met him at the stadium a few minutes before the game.

Tickets were free for students, but Joe offered to buy me a Coke and a hot dog, but I declined, partly because I wasn’t very hungry and also because I knew he had little money available for such luxuries. We had a swell time, and I could tell he was proud that I was with him, and I noticed many others checking me out from near and far.

When the game was finished Joe walked me to my apartment and announced he had a great time at the game, and it felt wonderful to have me sitting by his side. I agreed that I enjoyed being with him too, but I had some studying to do before Monday.

It was then he asked if he could have another kiss before he left, and he took me in his arms and gave me a very warm hug and tender yet somewhat passionate kiss. I was impressed at his progress and invited him, to come in for a few minutes. I wanted to see how much farther he would proceed before I walked him to the door.

Joe wanted to talk, and he began to reveal his loneliness and fear of rejection. I felt sorry for him because I knew I didn’t want a long-term affair with him, I just wanted to teach him how to communicate with a girl.

He opened his soul like a book and admitted he didn’t understand girls. He said he always wanted to make love to one, but he wasn’t sure how to begin or what women even wanted from a man. Before he was finished opening his heart I found myself telling him about my childhood and never dating until I was out of high school. I admitted I didn’t attempt to attract men, and I dressed more masculine and wore my hair in a short pixie.

I explained my boobs were tiny but I didn’t care and as a matter of fact, I explained, I didn’t care then either as we talked more intimately. I explained, “I found a man that explained what men like, and he very carefully took my virginity. I knew we were just friends, and I’d like to be your friend and teach you what women like, Joe.”

I sensed he perked up with that idea, but he was somewhat miffed when I explained I had no plans to be a steady date with anyone for a few years at the very least. I refused to offer to teach him, but I opened the door for him to ask me to take his virginity and teach him how to be more attractive to women.

I knew he could kiss reasonably well, he had good tastes with flowers, and he was already more open and willing to talk to me.

“Joe, have you ever made out with a girl? I mean more than a simple kiss like we had together?”

Joe looked sheepish as he shook his head no, but he continued, “But I want to learn how Alex. I know I could be a good student.”

I told Joe I was going to make an exception for him, but I needed some time. Would you be able to come back for dinner at 7 pm, Joe? We will have something to eat and you can spend the night with me. Just remember that this will be a teaching experience, not a love affair. I will expect you to put some of my ideas to work and have success with other women, that like you are lonely and don’t have someone to hold them tight and kiss them goodnight and love their body just the way it is.

It was 7 pm right on the button when Alex rang the doorbell, and again he brought me a precious little stained-glass sun catcher with a bright yellow sunflower for my window.

“Joe, this is wonderful, where did you get this sun catcher?”

“I make these in my spare time, Alex. It’s a hobby I have and it allows me to relax and make something beautiful that most people like.”

We didn’t have much for dinner, but I did make a tuna casserole and a small green salad. I was beginning to think Joe hadn’t eaten for a week, but he may have been trying to tell me he thought I was a good cook. After we did the dishes together I took his hand and led him to the sofa and kissed him hard. “Let’s make out a little, Joe.”

“What’s the first thing you want to do, Joe? Tell the truth now.”

“I want to do everything, but first I’d like to touch your boobs and see if they are as soft and warm as other guys say.”

I told him that he needed to take that objective in steps, and I identified the multiple steps of touching my sweater, gently rubbing my breasts through the sweater, getting under the sweater to touch the bra, and finally slipping his hand inside of the bra if there is room. “Go ahead and follow my steps using your right hand. Remember, you need to do this while kissing me.”

I felt Joe softly touching my sweater while we were kissing, and gradually, step-by-step he followed my instructions until he had his fingers inside my bra and was feeling my small but hardening breasts. “Now, Joe, you need to remove my bra. First, check to see if the clasp is on the front side or the back and then unclasp it.”

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The boy was a natural, as he had my bra opened faster than a cockroach scampering across the kitchen floor.

I asked him to play gently with them, and when he felt ready to remove my sweater by pulling it over my head. I explained if he found the girl resisted he needed to work more on her titties and pull the sweater up far enough to start sucking on a nipple. You will need to read your friend’s signals. You may not continue past the point she resists your movements. It’s like Monopoly; you must pass go before you can move to the next step.

I helped him remove my sweater and bra and allowed him to suckle at my hardening breasts while I started to respond by gently rubbing his penis, which was already hard and pointed towards his stomach. I undid his belt and slipped his zipper down and said when a girl does this she is giving you the all-clear sign. She plans to allow you to have intercourse with her or she will either suck your cock or give you a hand job. That’s assuming you don’t screw up along the way, Joe.

I instructed Joe to remove my blue jeans and my panties and try to completely remove them from my feet at which point I’ll be totally naked. I could feel Joe slipping my pants off with my silk panties intact, and I began to allow some slight moans to acknowledge I was happy with his progress.

I fumbled for his pants and pulled them down with his boxers at the same time and couldn’t help myself from wrapping my little fingers around his cock to feel his size. I was surprised he was as well endowed as he was because of his slim stature, and that was my first but not last time to be surprised when I got to see the package. Men are all wonders, and I have always left marveling at what lies beneath their skivvies.

“Joe, What would you like to do next?”

He responded, ” I want to do everything before the night is over, but first I want to taste your pussy and feel where your clit is located. I want to make you enjoy tonight as much or more than I enjoy tonight.”

I suggested we move into the bedroom where it would be more comfortable, and I decided to leave the overhead light fixture on so Joe could see everything he touched or felt. Joe was strong, and he lifted me from the sofa and carried me to the bed where he gently deposited me with my head on the pillow.

After removing the bedspread and blanket immediately, he explored my pussy by pulling my labia apart and looked for my little button that created the feelings of jubilation as he tongued it softly while only stopping to say he enjoyed the taste and feel. My pubic hair was trimmed as short as possible without putting a razor blade to work, and when he inserted his index finger into my vagina I felt my insides tremble in orgasm.

“Joe, let me suck your cock for a bit, it’s not fair that I receive all the pleasure.” Joe was too busy satisfying me to worry about himself and once again he began to work on my vagina with his index and middle finger as he brought his lips to mine and kissed me deeply.

I rolled Joe on his back and straddled his body and descended on his proud erection with my vagina that was seeking a probing cock to reach an itch deep inside. I rode him with abandon feverishly bouncing up and down over and over until I collapsed with another orgasm that nearly caused me to lose consciousness.

Joe had not ejaculated yet, and I couldn’t believe his staying prowess. After I rested for a few minutes, Joe turned me right side up and lifted my legs on his shoulders and began an onslaught with piston driving force as he lifted me gently with every upstroke and pounded me savagely into the mattress with the down strokes.

I could feel him going deeper and getting thicker when the end was close, and I felt bathed by several hard shots of semen into my cervix. Joe collapsed on top of me as he gasped to replenish his lungs with air to recharge his strength. I knew I owed Joe, but I also knew I wasn’t able to repay him until morning as I was totally exhausted from the best and longest lasting sex I had ever experienced in my short life.

Two hours later, Joe’s cock was still embedded inside of my vagina making like a plug to prevent leakage all over the bed. Fortunately, we were still tacky instead of drying together so Joe lifted me as I squeezed my legs around his waist and headed to the shower. Tomorrow, Joe was going to get another wish, and I was prepared to drain him again with a blowjob before we called the first lessons completed.

I was sure glad I met Joe and became his friend with benefits during my four years of undergraduate work. We were never in love, but we loved to have sex on occasion, and I introduced Joe to several co-eds that experienced his wonderful love tool. He’s a married journalist now with a small red headed son and a beautiful wife that knows we used to be friends with benefits.

Updated: April 16, 2018 — 3:48 AM

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