Almost First Time

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Shy virgin guy's sexual awakening.
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Author's Note: All characters are fictional; any resemblance to real persons is coincidental. All characters are 18 years of age or older at the time of any sexual activity.

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Prologue

1973. I was a twenty three year old virgin. I had dated from time to time, beginning with my first date (when I was a seventeen year old senior in high school). I even had been in two relationships. Unfortunately for me, due to my shyness, my upbringing and my choices of companions I had no experience with the opposite sex beyond chaste kisses and hand holding.

My primary interest in life was watching baseball. I chased across the country to follow my team on the road. Houston had become my favorite road trip. I scheduled another trip to Houston to watch my favorite baseball team play in the Eighth Wonder of the World, the Astrodome. I was also looking forward to seeing Bonnie.

Bonnie

Bonnie was the most recent of my serious girlfriends. We had met while I was a Student-Teacher at her high school in December of 1970 as a 21 year old college senior. She was now an 18 year old high school senior, a few days from graduation.

Bonnie had knocked on my classroom door, where I frequently stayed, during my lunch period. Several days before, Randi, one of the students in my Bookkeeping class, had asked if I minded if she remained in the empty classroom during lunch to study, that the cafeteria was too noisy. Since I normally remained in the room at that time for the same reason I gave her permission, and from that day Randi spent every lunch period studying industriously. Bonnie was a friend and neighbor of Randi's, and she asked to speak to her.

Bonnie was a sixteen year old tenth grader. She had shoulder length dark brown hair worn with bangs, sparkling brown eyes hidden behind large circular dark framed eyeglasses, a petite nose, and bow shaped lips, and was about 5'5" inches tall. She was wearing a long winter coat, which hid her figure when I met her. As time passed and I had the opportunity to see more I came to appreciate her 34 B breasts, her narrow waist, her curvy hips and behind, and her shapely legs. At first glance she appeared to be girl next door cute, not beautiful. Upon closer examination I realized that she carried herself differently than the other girls in the school, having an air of self-assurance and maturity that the others were lacking.

Randi and Bonnie carried on their conversation. At some point, I was asked if it would be OK for Bonnie to also stay in the room. Thinking nothing of it I agreed, and from that day to the end of my term of Student-Teaching Bonnie was an almost daily lunch visitor.

The girls soon began including me in their conversations, and I quickly began to feel attracted to this young student, who was more than five years my junior. The more we talked, the more I looked forward to our daily lunchtimes together. When we first met the thought of a romantic relationship with her didn't even enter my mind because of our age difference, but as the days rolled by and we drew closer my interest in spending time with her grew. The closer I came to leaving the high school and her the more I realized that I didn't want to lose her.

1971

Too soon, my student teaching assignment came to an end, and I returned to college for my last semester. Shortly before I left the school I learned from one of my students that the bowling team coach had resigned, and decided to volunteer to coach the team, enabling me to remain involved with the school on a more regular basis. Later, when I learned that Bonnie was friends with several of the bowlers I impulsively decided to ask her if she would become student manager of the team. She readily agreed.

I quickly began to look forward to seeing Bonnie at each week's match, and we chatted together while the matches were going on. Once or twice she and a couple bowlers on the team asked for rides home, which I readily accommodated.

As the season wound to the end I took Bonnie aside, and I told her I would like to date her once I was no longer considered school staff. I asked her if her parents would permit her to date a 21 year old college senior. She quickly agreed to ask them.

After what felt to me like forever, but in actuality was a short time, Bonnie told me that she had spoken with her parents, and they had agreed to permit her to go on a date with me. We quickly arranged a time and place for our first date, and I nervously prepared to meet her parents for the first time.

The time came, and I was a nervous wreck as I approached Bonnie's home. I tentatively rang the bell, and was relieved to see Bonnie open the door. I entered, and she introduced me to her mother and father, who were (thankfully) pleasantly polite with me. We chatted for a few minutes, told her parents what our plans were, and excused ourselves.

We both enjoyed our evening, and each other's company, and we agreed to see each other again. At the door she said goodnight, and gave me a quick hug, the extent of our physical contact. Our intense whirlwind romance ensued.

From that night on we considered ourselves a couple. We spent all our free time together, and spoke on the phone whenever we were apart. I fell in love with my young girlfriend, and our relationship came to include frequent kissing and embracing, but nothing more. I considered Bonnie to be a virtuous, well raised young lady, and I did not expect her to be willing to engage in anything beyond hugs and kisses. (In those days nice girls didn't, and well-bred young men respected that. I also knew the law, which in our state said that she was under the age of consent.)

I was a normal 21 year old guy, so inappropriate urges frequently made themselves known during our alone together time. One time we spent an evening alone in her home when her parents were called out of town for a family emergency. While we kissed and hugged on her living room couch for hours I was able to resist the temptation for my hands to explore her feminine charms, respecting the trust her parents were showing by permitting me access to their precious young daughter. Also, I was proving to my overprotective parents that I could control my physical needs and stay out of legal trouble, as I was being hassled constantly by them regarding the improper nature of the relationship and the potential legal risks.

Many days we spent hours alone in a nearby national park, lying together on the green grass, hugging and kissing while we talked. I made certain that my hands never touched her inappropriately while we kissed and hugged, in spite of the desires I was experiencing.

After several months of being together on an almost daily basis, Bonnie's infatuation with the attentions of an older man wore off, and we gradually drifted apart. I was still as pure as snow, and so was she! I was also heartbroken at my loss, but I had always known that she was too young for our relationship to last. The last time I spoke with her she told me that her father's employer was transferring him to Houston, and they would be moving.

When she moved we lost touch. Bonnie went on with her life in Houston, and I went on with mine. I dated from time to time, but nothing clicked with any of the girls I went out with. Two years later I was still a totally inexperienced virgin.

1972

Upon my arrival in Houston the day before the first game of the series I checked into my hotel, across from the stadium. As I had nothing to do that evening I decided to see if I could find a phone number for Bonnie, whose family had moved to Houston in 1971, shortly after we had ended our very intense, but very platonic, six month relationship that we had ended not long before her move.

Browsing the phone book in the hotel room, I quickly found a listing for her parents, and gave her a call.

Bonnie was surprised to hear from me, but greeted me warmly. We talked for some time, catching up on the year since we last had seen each other. After we had talked for a while I asked her if she would like to spend the next day at AstroWorld, the amusement park that was adjacent to the stadium. She agreed. She gave me directions to her home, which was quite a distance from the hotel, and we made plans for me to pick her up early the next morning.

After I picked her up we spent a delightful day at the park, riding different rides and chatting. We particularly enjoyed the novelty of the bumper boats, banging into each other's boat and splashing each other with cool water on a hot summer day.

At some point during the day I invited her to come with me to that night's game, and she agreed, so we went back to my hotel room so I could pick up my team gear.

When Bonnie came into the room with me I was uncomfortable, having an attractive underage young lady in my hotel room. I had the urge to reach out to pull Bonnie into my arms, but since she had behaved as a friend the entire time we were together, not a girlfriend, I decided that it would not be a good idea. I didn't want her to think that I had invited her to my room to take advantage of her, so I quickly changed my shirt, grabbed my baseball cap, and we left for the Astrodome.

The game and the company were enjoyable, so much so that I didn't care if my team had won or lost. Afterward I drove her home, returning to my hotel room alone, wondering on the long ride what might have been.

The next day we spent the morning together, exploring the city until it was time for me to leave for the airport. When I dropped her at home we said our goodbyes.

1973

For the third season in a row I scheduled a Houston road trip. This time I was looking forward to more than baseball. Since my time with Bonnie the last time I visited had been so enjoyable I was looking forward to spending time with her again. After the last visit I had realized that I still had feelings for her, and probably always would. I realized that geography was more than likely an insurmountable roadblock to renewing our previous romantic relationship, but I was happy to spend time with her when we could.

Because of my work schedule I couldn't get to Houston in time for the first game of the series, arriving late at night- too late to call Bonnie. As soon as I woke up the next morning I ate a light breakfast and then made the phone call that I was looking forward to.

When Bonnie heard my voice she greeted me warmly, even telling me that she was expecting to hear from me the day before, since the team was in town. I suggested we get together, and she responded by inviting me to the house. Since she was the Houston expert I figured I would follow her lead since I was free until game time that night.

Bonnie opened the door and greeted me warmly, dressed casually in shorts and a T-shirt. Her mother was just leaving to run errands. We began talking about what we could do, and I quickly learned that I would be unable to spend much time with her this trip; the only free time she would have was until her mom returned from her errands. She suggested that we just hang out, and I agreed to the plan.

Bonnie's younger brother made an appearance, quickly making a nuisance of himself, like most younger brothers do. After a few minutes of annoying us he said "If you drive me to my friend's house you can be alone with my sister and do anything you want to her".

I responded by telling him "Your sister might have something to say about that", but we agreed to drive him. He quickly got ready, and the three of us drove to his friend's house and dropped him off.

When we returned to her house Bonnie asked if I enjoyed George Carlin. We sat cross legged on the floor, listening to the comedian's humor while we talked. Bonnie told me about what she had been doing since we had last been together. From our conversation I learned that she went "fishing" regularly with an ex-boyfriend, and that those "fishing trips" were actually what today we would refer to as booty calls. She joked that she often asked herself why his new girlfriend didn't wonder why he was always so tired after his fishing trips.

That information opened my eyes, as I realized that my pure, innocent Bonnie was no more! I decided that since she was no longer virginal she might be willing to help me with the unwanted burden of my virginity. With that thought my body began to respond. I could feel my underwear get tighter as my penis began to swell and lengthen. I decided to risk rejection, and asked if I could kiss her. Bonnie lifted her arms to embrace me and drew her face closer to mine.

I leaned over and kissed her inviting lips gently once. Hearing no objection, I continued kissing her. My arms embraced her, soon caressing her softly. She kissed me back, and pulled me closer.

Eventually my hand moved toward her chest. It slid slowly across her rib cage, and gently across the surface of her T-shirt covered breast, discovering for the first time the unique soft firmness of a breast. I gently stroked and squeezed it, feeling the intensity of her kisses increasing as I touched it, eventually moving on to its' twin. After a few minutes of my touches I slid my hand beneath the waistline of the shirt, slipping my hand over her bra covered breast. Bonnie responded by pulling back from me, grabbing the bottom edge of her T-shirt and pulling it over her head, revealing her plain white bra.

I returned my hands to her bra covered breasts, feeling the silkiness of the material and the hard points beneath. Soon, wanting more, I slid a strap from her right shoulder, loosening the cup from Bonnie's right breast, and slipping my hand beneath the cloth. As I touched her silky smooth skin I felt the sharp intake of breath in response to my touch. For the first time I was holding a bare breast in my hand, feeling the smoothness of the skin, the weight of it resting in my palm, and the resilience of her soft flesh as I caressed and squeezed it.

I removed my lips from Bonnie's, and kissed my way across her chin, down her neck to her nipple. I kissed it gently, then began licking it with the tip of my tongue, eliciting a gasp, then soft moans as I caressed her breast with my tongue. Simultaneously, my right hand was rubbing and squeezing Bonnie's left breast, first on top of then beneath the material of her bra. Bonnie reached behind her back and released the clasps holding the bra to her torso, and slid the straps from her arms, leaving her naked from the waist up. I leaned back and gazed at the size 34B half grapefruits standing out proudly from her chest, the pink circles surrounding her pointy nipples and exclaimed that they were beautiful, quickly returning to stimulating them with my mouth and hands.

Since Bonnie was naked from the waist up I decided I should also be and pulled my shirt off, then I reached over and embraced her tightly against my chest, kissing her deeply. As I felt the pressure of her breasts flattening against me I leaned her back, reclining her on the carpeted floor and stretched out beside her on my side. I returned my attention to her breasts, while she caressed my bare chest, causing my nipples to become erect and my organ to grow harder inside my pants.

Eventually the position we were in became uncomfortable, and Bonnie suggested that we get up from the living room floor and move to the couch. I stood up, reached down, took Bonnie's hand in mine, and helped her to her feet, then we walked together the short distance to the couch. Bonnie stretched out on her back across the couch, head resting on the arm rest. Unsure of exactly what was expected of me, and not wanting to ejaculate too soon, I knelt on the floor beside her, leaned over and resumed kissing her and fondling her bare breasts as she kissed me back.

I could feel my rock hard organ in my trousers twitching, about to explode. Fearful that I would ejaculate prematurely, I desperately tried to hold back my release.

Turning my attention to Bonnie's remaining garments, I unbuttoned the button at the waist and pulled down the zipper. I slid my hand beneath the waistband of the pastel bikini panties that I encountered, and my fingertips encountered her soft vee of pubic hair, the beginning of the valley beneath, and the heat and moisture radiating from it.

That act triggered the disaster! Unable to hold back any longer, I could feel the uncontrollable throbbing of my organ as it pumped stream after stream of hot, thick, sticky seminal fluid from the reservoir deep within my body into my underwear as I tried to disguise what was occurring!

My mind exploded, simultaneously trying to deal with that incredible situation combined with my first time close up encounter with real, live female genitalia. Rather than reveal what had occurred to Bonnie, I decided to hide it from her, and remained kneeling on the floor, focusing on experiencing her treasures fully.

Placing my hands on either side of the waistband of her shorts, I slowly pulled them, along with her panties, down over her hips, revealing her feminine treasures to me for the first time. As I pulled the shorts from her waist Bonnie lifted her hips from the couch to assist me. I quickly slid her shorts off her legs, and paused for a few moments as I gazed upon Bonnie's fully naked body for the first time. Her full breasts rose and fell rapidly from her excitement. I admired how her slim waist swelled into her soft hips, which merged into her long, shapely legs.

At the point where her thighs met her torso there was a small vee of soft brown hair partially shielding the treasures beneath from view. My left arm reached out as if it had a will of its own, unable to resist exploring that spot. My palm came to rest on her left thigh, gently pulling her thighs apart until the flower between her legs opened to reveal the pink folds of flesh beneath. It slid higher and higher until it reached the soft warm spot above the junction of her thighs. My fingers stroked the soft hairs covering the warm, moist opening beneath, spreading the slippery moisture I found. As I slid my middle finger along the valley that I found between the fleshy lips beneath her pubes Bonnie's hips lifted uncontrollably to meet the contact, and another moan escaped from her mouth. I continued to slide my finger back and forth in the valley, which opened to my view, revealing the light pink color, glistening with her secretions, along with the opening leading to the tunnel of pleasure within.

Needing to experience Bonnie's treasures completely, I decided I wanted to taste the enticing place revealed to me, so I licked my way from her breast, across her midriff, past her navel, and down the pink valley, sliding my tongue from the top of it to the ending point deep between her legs, tasting the sweet, tangy liquid covering her, and smelling her sweet essence. My tongue probed the entrance to her tunnel, scooping the abundance of juices it encountered deep within.

As my tongue climbed from Bonnie's tunnel of pleasure toward the sensitive little nub at the top of the valley I slid my middle finger into her opening, feeling the smooth, ridged texture of the walls as it probed deep within her depths. When my finger had penetrated her to the hilt I withdrew it slowly to the opening, paused a moment, then plunged it in fully. As my finger entered, Bonnie's hips rose to meet it, then fell as I withdrew.

I began increasing the pace of my finger's penetration, and Bonnie's torso rose and fell rhythmically in response. While I was stroking I kissed my way back across Bonnie's belly and resumed kissing, licking, sucking and caressing her breasts with my lips, tongue and free hand. I also inserted my index finger into Bonnie's tunnel of love next to my middle finger, plunging them in and out faster and faster, feeling her muscles squeezing tightly against them to intensify the sensations she was feeling.

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