Before my dad remarried and I entered college, life had been a series of ups and downs. Mom was diagnosed with cancer when I was a freshman in high school, and she finally succumbed to the disease during the summer of my senior year after a long, drawn-out battle with both chemo and radiation treatments. She hung in there until the bitter end, but her last days were an emotional roller coaster for dad and me as we both secretly knew the end was in sight but refused to admit it to one another or ourselves.
During my high school years, her condition affected me in a variety of ways. I tended to engage in risky behaviors and got in a fair amount of trouble at school. Of course, this didn't help our home life. The last thing my parents needed was to worry about me, but it was my way of rebelling to circumstances beyond my control and mom's spiraling health issues.
My friends typically avoided the subject of my home life, and I went through a few typical high school romances that tended to be short lived, mainly because of my bad attitude. I dated a few very sweet girls who tried valiantly to change my bad boy ways, and a couple who got a thrill out of my negative behaviors and trouble making.
Most of the time, I was in a relationship for self-gratification. The one thing my girlfriends had in common was a particular look. Personalities came secondary. Anyone with a brain could see that I liked big tits, and my dates fit that body profile almost always. My brain was in my groin as I was repeatedly reminded by my friends.
At the age of 18 I lost my virginity to an older neighbor girl who was a freshman at a nearby community college. I can't say it was a particularly wonderful experience as it took place on the uncomfortable bench seat of my ancient Chevy Bel Air after we had been dating for about a month. One night when her parents were out for dinner I reached second base with her in her living room by successfully getting her bra off and fondling those perky teenage tits, but she stopped me before I could get into her panties for fear her parents would walk in the door during our wrestling. She did offer hope for future entanglements, however, if we could find a place of privacy.
That prompted an area search, and many miles and a tank of gas later I discovered a hidden parking place with a view of city lights. Even though the heater in my car didn't work, I successfully convinced her this would be a romantic culmination of our relationship as I grappled with first her jacket, and then her blouse. After a few minutes of serious making out, I had worked the clasps of her bra loose and after pulling open her blouse, my lips found a large pink nipple. With Sharon's encouragement, I made a meal on her ripe tits. Soon, I was able to slip a hand under her skirt and inside her panties, eventually getting a finger into her vagina. This caused even greater gasps of pleasure. Then, when my pants and boxers came down to my knees and she saw my rock-hard boner, she gasped again, but this time in awe.
I just happen to be blessed with a rather large cock, and when it is angry, it swells in girth as well as length, prodigiously so. This is something I proudly achieved on a regular basis while locked in my bedroom late at night with an ancient and well used Penthouse publication in front of me and a box of tissues on the nightstand.
So when Sharon caught a glimpse of my virginal penis, she practically fainted. "Jesus, Sammie. You are huge. I don't think that thing will fit in me!"
Despite her reservations, Sharon wrapped her hand around my swollen member and stroked it--almost too professionally for a 19-year-old whom I always thought was sweet and innocent. I was doing my best to strategically place myself between her legs on the narrow car seat, avoiding the Hurst floorboard shifter, and get in a position to finally experience actual fornication. And with her help and a bit of giggling, I soon found Valhalla as she finally was able to insert just the head of my cock between the hairy lips of her pussy.
"Oh my god. I've never seen a cock this big."
This both pleased and disturbed me. Sharon clearly was impressed by my penis, but then it sounded like she had been here many times before, obviously with guys other than me. I guessed she wasn't a virgin.
But at that moment, I just wanted to fuck her, and her pussy felt nothing like my own fist. After some mutual groaning and pleas from Sharon to not cum in her since I didn't come prepared with a rubber, I began working more than just the head inside her, fucking her slowly at first and then rapidly. Sharon stared in disbelief as my huge member stretched her pussy. She moaned in pleasure and managed to just get out, "God, Sammie, your cock is splitting me in two!" when suddenly, approximately 60 seconds later I groaned loudly and exploded with a huge burst of cum inside her.
"Oh, shit! What did you do? I told you not to cum in me, Sammie. Jesus, and so soon! I was just getting warmed up!"
I hurriedly pulled out--too late as my cock continued to squirt hot jizz over her stomach and onto her jutting tits now exposed by the loosened bra. "Sorry," I mustered. "I didn't mean to cum so fast. But I don't think I got much inside you." As if that mattered. Besides, it was a lie. A river of white, sticky cum began draining out of her vagina trailing the sudden withdrawal of my member.
We quickly cleaned up as best we could, and Sharon asked me to take her home so she could try some home remedies in an effort to avoid an unwanted pregnancy. That effectively ended the romance for a while as we both feared the worst. Eventually, though, we realized we had dodged a bullet and none of my soldiers had found a home during the invasion of her pussy.
So, my first experience, while pleasurable for me at least, was so short lived that it only encouraged me to practice more. Unfortunately, my practice sessions were invariably done solo. I was humiliated by my performance with Sharon, and I don't think she was too impressed with my stamina despite the pleasing size of my tool. So, by mutual agreement, more or less, our relationship seemed to dissolve after that. I did fantasize about those fabulous breasts and the sight of my cock being guided by her hand into her waiting pussy. In my fantasies, though, I lasted much longer until she was begging me to stop. Instead of coming in her tight pussy, I filled a handful of Kleenex tissues.
Mom was not doing well during this time, and we had lots of well-wishers and friends who offered help in a variety of ways. One spring day on my way home from school, I ran into a neighbor lady down the block who had befriended mom, and she inquired how things were going. I was walking by her house, and she was watering some flowers along the sidewalk in a tight pair of shorts and a tank top that caught my attention. I thought it was someone much younger until she turned around and gave me a big smile.
"Oh, hi! You startled me! How's everything, Sammie? I haven't talked to your mom in a while. How's she doing?" Like most folks, Mrs. Collins' inquiries tended to be generic so as not to seem intrusive. The handwriting was on the wall as to the probable outcome, but everyone just wanted us to know they cared about what we were going through.
"Oh, you know. Some good days and some bad. Thanks for asking."
"How about with you? Do you have a job lined up for the summer?"
"Naw. Nothing yet. But I really haven't been looking much since school is still going on."
