Like virtually every young man growing up, I was a raging mass of hormones during my late teenage years. As a result of my upbringing and the heavy-handed morality of church and society, I was likewise conflicted. This was the sixties. Ozzie and Harriet slept in separate beds on their family TV show, and their sons Ricky and Eddie were pillars of wholesomeness, unlike anyone I knew. But at the same time, sexual boundaries were beginning to change.
Magazines had a lot to do with it.
With the introduction and subsequent popularity of Playboy magazine, attitudes began to change slowly. Hugh Hefner had carved an enviable niche for himself. His glossy publication contained thought-provoking articles by well-known writers and familiar faces. Still, the real reason for its popularity lay in the photo spreads of gorgeous, naked, young women. And even though the magazine may have been relegated to the privacy of bedrooms and not the living room coffee table, it opened the door to what eventually became a sexual revolution. Ultimately, Playboy and the other rags that followed provided masturbation material for millions of males.
Including me.
So by the mid-sixties, reputable newsstands began to openly display "girly" magazines, often partially hidden from less welcoming eyes in special sections. Free browsing began to be discouraged.
"You buying or just renting? No browsing!" Words to that effect became a familiar refrain.
The magazines were not welcome in our protestant house until many years later when even my mother seemed to be open to what had become common. So, I secretly hid a stash hidden between my mattress and box springs for nighttime relief. I assumed that, like me, many of my seventeen-year-old friends whacked off regularly to those naked pictures. Playboy was a huge upgrade from National Geographic magazines that occasionally showed large-breasted indigenous natives in topless attire.
Any port in a storm.
Penthouse and other sleazier publications followed Playboy and were closer to actual pornography with their graphic displays of women. Airbrushed pubic areas gave way to exposed labia. The boundaries of acceptability expanded until periodicals showing couples in simulated sex became available in public newsstands to anyone who had the cash to buy them.
A small local store in our town that sold everything from cosmetics to cameras eventually added a large magazine display as well as a carousel with fuck books hidden behind a short wall to keep them out of the eyes of children and stuffier types. These "novels" were not romance books with busty women in suggestive poses on the covers. These were honest-to-god fuck books where someone was getting laid or having some form of sex on nearly every page. I added a dog-eared copy of one of my favorite magazines between the mattress and box springs of my bed.
The naked form was no mystery and fantasy sex permeated my brain. Jerking off to those pics became an obsession. Busty, slim-hipped, beautiful women dominated my thoughts. I couldn't wait to get out of high school and into college where I would get laid regularly. Or so I thought.
My late-night enjoyment only required a free hand. That system worked fine until one day I reached for them and they had mysteriously disappeared. My mother never said a word about it to me, but she was no doubt disgusted. My stash was gone.
The real thing: actual live sex was still a ways off.
My early dating in high school was closer to puppy love than anything sexual. But after a few trial-and-error dates with various girls my age, I did meet a cute Catholic girl from a private school across town. She was a cheerleader and full of boundless energy. She lived with her divorced father who worked long hours and had strict rules about boys in the house if he was not present. Anita broke them repeatedly. Not that it made any difference to me. As horny as I was, our relationship developed at a painstakingly slow pace. Even after several dates, kissing was almost platonic. It was a long trial period before we reached the point of "making out." French kissing was a giant leap forward.
Parking at a scenic vista where we could have a modicum of privacy, I eventually groped my way to second base with her. Anita's breasts were average-sized on her petite frame, but they seemed solid enough, and after repeated wrestling bouts on the front seat of my Volkswagen bug, or if I was lucky, my parents' Olds, I learned how to unclasp her bra with one hand. Before she realized what was happening I had my hand partially on a bare tit for brief periods. I was pretty sure that she wanted me to fondle her for a bit before she stopped further progress. I also learned that she began to have a hard time saying no as long as we were alone, which was rare. And speaking of hard times, my cock was ready to burst during such expeditions. And she knew it. Prick-teasing was a specialty of hers.
She even joked about it.
"I'm thankful I don't have a big thingy like guys do. That seems to cause so much discomfort. You're always adjusting things down there. It must be painful."
I wanted to remind her that if she would just let me plant my "big thingy" inside her, the pain would go away, and I'd do a lot less adjusting. But I just smiled instead.
As a good Catholic girl, she wore an armor of guilt that was difficult to ignore. Her religious indoctrination crept into all kinds of discussions regarding not just sex, but other sins, too. Heaven forbid that either of us have "impure thoughts." Of course, pre-marital sex was a step toward the fires of hell, but her church had an answer: confession. All sins disappeared when absolved by a priest who could purge those moments when temptation proved to be too much. I figured we could fix anything with a trip to the confessional. Nothing like a couple of "Hail Marys" to absolve those dirty thoughts and deeds.
Thankfully, Catholic morality didn't come to mind when we found passion in one another's arms. I eventually discovered I could gradually work my hand from her knee toward the sweet spot where her thighs met. The closer I got to that treasure, the more passionate she became. She turned into an animal, breathing heavily before making me stop short of going "all the way." I was plagued with a chronic case of blue balls as a result. Regardless, I dutifully obeyed and fantasized that the next time we'd go just a little further. I convinced myself that I was the only boy in my class who was still a virgin. But the opportunity to plant my cock in her sweet pussy seemed like an impossible goal.
So, when she revealed to me that her father would be leaving town on a Saturday business trip soon, I could think of nothing other than planting myself between her legs and getting the monkey off of my back. She had already crafted a plan that sounded promising. I'm not sure if it was an answer to my insistent begging and pawing, but the rationale was unimportant. We could be alone in a bedroom.
"Dad will be gone and since there is no school to worry about, why don't you come over early that Saturday morning and wake me? Just make sure his car is gone. He's catching an early flight and won't return until late afternoon."
From that point on, my cock was continually hard in anticipation.
When the appointed time arrived, I hardly slept the night before, and my mother was suspicious when I arose at the crack of dawn, showered, dressed neatly, swathed myself in cologne, and was out the door before eight. I had concocted some story that was, no doubt, unbelievable, but how could her son get into trouble early on a Saturday morning?
I arrived on the dot of eight after surveying the premises for any signs of a parent. I parked in front of another house to avoid neighborly suspicion and quietly walked to the front door. I knocked and waited, my cock tenting my pants.
Nothing happened. "Shit! I hope I didn't fuck up the date!"
I knocked again, this time more insistently, and finally, to my relief I heard the padding of bare feet approaching the door.
When the door swung open, I faced a still-sleepy eighteen-year-old in a frumpy robe. I prayed the deal was still on.
"Hi. Is Anita home?" I joked.
"I was sound asleep, you goofball. Let me brush my teeth so give me a few minutes and then come back and come on in. No need to knock. Dad's gone."
I returned to my car and waited for several minutes. Months passed before I returned to the door, and acting as casually as possible, I turned the handle and walked in.
I felt like an intruder even though I had been invited in. The house was deadly quiet and messy, as usual. I removed my jacket and found my way to Anita's bedroom. She was face down and soundly sleeping, but I knew better. This was part of her act.
I quietly slipped up beside her and kissed her neck and her ears. She groggily rolled over and acted completely surprised to see me. She put on a chirpy smile as if this was completely unexpected and normal.
"Ben, what are you doing here? What a nice surprise! I was dreaming about you, but I can't tell you what we were doing. It was a bit nasty. Come here... crawl under the covers with me. It's nice and warm."
I followed orders and slipped under the covers. She was wearing only a thin nylon nightie and panties. I lay beside her and kissed her tenderly. My cock was painfully tenting my pants and Anita giggled when she saw it. In seconds we were locked in an embrace and our tongues danced in each other's mouths. I gradually worked her nightgown up from her waist, and for the first time, I had an unobstructed view of her beautiful tits. She had two perfect banana-shaped cones capped by large, puffy areolae that covered the entire ends of her breasts. I almost shot my wad when I saw them. They begged to be sucked.
I planted my lips on a ripe tit and kissed her large nipples for the first time. Her moaning only encouraged me and as awkward as it was, I was able to remove my pants with minimal contortions. Soon I was in my boxers and between her legs, our groins grinding against one another. My cock was like an iron bar.
"That feels so nice when you suck on my boobs. Don't stop. It sets my brain on fire."
My hands explored every inch of her and after getting no arguments, I worked my fingers inside her panties and the beautiful forest of her pussy hair. My fingers discovered her labia and clitoris and suddenly my index finger was inside her wet cunt. She gasped and suddenly her tongue became frantic in my mouth.
I worked my finger back and forth slowly as her hips responded in kind. Her pussy was sopping.
At one point, she stopped and looked at me as if pleading to continue. But she never said a word.
I slipped off her panties along with my shorts and now my rigid cock was aimed at her untrimmed delta. She spread her legs in a gesture of approval. Her moist cunt was a thing of unbelievable beauty. I had fantasized about this moment for weeks and I was about to live it.
"Did you bring a rubber?"
Fuck! I had completely neglected to buy condoms, partly out of embarrassment and partly due to fear my mother would find out since the pharmacy that sold them was run by family friends.
"No, but I won't cum in you."
As if that were possible. I prayed this would not ruin everything. The look on my face said it all.
"Never mind. I don't think I can get pregnant. Go ahead. Put it in me. It looks so big! I can't stop now."
We were both beyond control at this point. She bent her head to watch as I gripped my cock in one hand and rubbed it in her beautiful auburn maidenhair, searching for the entrance to my dreams. Even though it was pretty obvious where I was supposed to plant my cock, the devil is in the details. I was aiming a bit high to gain actual purchase, and after several false attempts, she reached down and guided me into her cunt.
Once the head was inside her, she looked at me with anxiety written all over her face. My cock looked huge perched on the threshold of a real pussy.
"Do you really want to do this? I don't think I can stop at this point. It feels so good. But maybe we should rethink this." She was having second thoughts.
But there was no backing out at this point. We both wanted this in the worst way. We were about to fuck like two consenting adults despite our age, and it was as exciting as it was forbidden.
"I'll stop if you say so." The head of my cock was still buried, but I hadn't moved my hips any further.
"No, go ahead. I want this as badly as you do. Mmmm, you feel so nice inside me. Just don't cum in me."
And with that, I slowly moved my hips forward and Anita reached around and grabbed my ass to pull me inside her welcoming cunt. My cock slowly entered her tight, teenage pussy and we both watched in amazement as it disappeared until I was buried.
"Oh, shit! That feels so good. Nice and slow. You feel wonderful in me."
I had no idea what to do beyond what was already in motion. My dick was buried in my girlfriend's pussy and our groins were joined in consensual sex. My brain was an explosion of synapses. I knew I couldn't last much longer than a few minutes. Jacking off to a centerfold was nothing like the real thing and that experience did little to prepare me for what I was feeling at that moment. I began sliding my cock in and out of her. We were actually fucking for the first time.
Anita had her neck craned to watch as my swollen cock slid effortlessly in and out of her. She had a look of sheer ecstasy and moaned unintelligible sounds, purring and coaxing me with her moans. Her cunt was soaking wet, and my shaft immediately glistened with her milky nectar. As I increased my tempo, her perky tits bounced back and forth with each thrust. I bent over to wrap my lips and hands around them to steady them. At the same time, I tried in vain to stop my ejaculation. But it was too much too soon.
All at once I felt a surge of my own juices race from my balls toward the fat crown of my cock, now buried deep inside her. Anita must have sensed what was about to happen. My cock throbbed uncontrollably.
"Oh, shit! Don't cum in me," she ordered, but it was too late. Two or three spurts shot into her fertile valley before I could withdraw. The feeling of my cock surrounded by her soft pussy-flesh was indescribable. I pulled out, and when my sticky helmet found daylight, it was followed by a gooey mix of semen and pussy juice. My cock was still shooting and the rest of my load lined her bush and stomach.
Anita had a look of panic as she watched the product of our union slowly drain out of her pussy and onto the bed sheets.
"What did we just do? Fuck. You weren't supposed to cum in me, Ben."
I guiltily kissed her cheeks, her lips, and then her nipples as we both tried to catch our breath. It was only then that I realized my original insertion had met with no obstruction. For whatever reason, her hymen was gone. No matter. The monkey was gone. Now all I had to worry about was if I was going to be a father.
"I'm so sorry. It happened so fast. But it was only a little bit that got inside you." The puddle of cum dripping on her bedsheets said otherwise.
Anita's face changed from panic to resignation. She kissed me as if to say "Okay, but never again." We lay there for several minutes, and then she reached down and stroked me. She had never touched my bare cock before. It instantly hardened.
"Since we're already here, wanna do it again? This time pull out if you are going to cum. Not that it's going to make any difference. But at least try not to shoot it inside me–even though it felt wonderful."
I needed no urging. Instantly I was on my knees and pointing my rigid cock at the lubricated entrance to her pussy. I had no problem with my aim the second time. Before the morning was over, we had fucked two more times in a variety of positions. The last time, Anita rode me like a crazed cowgirl.
I was no longer a virgin. When I finally got back in my car, my smile was ear to ear.