Maria's First Time

It’s kind of strange, but the boy who took my virginity and gave me my first orgasm . . . I didn’t even like him very much at the start. His name was Mark, and to me just a high school kid who showed up at our house much too often. I was 20 at the time, still living at home with my mom and step-dad, and attending the local community college.

Mark was a friend of my step-brother, but in my mind, a bad influence on him. He was good looking enough, with dark eyes and hair—really quite well-developed for a kid of 18. I’m pretty tall, about 5-9, and he was a couple of inches shorter than me, but that didn’t seem to bother him at all. He was one of those know-it-all guys that we all remember as teenagers . . . or at least that’s the way he came across.

He came over to our house a few times looking for my brother, and when he wasn’t home, Mark and I would sit and talk. I finally decided he was an okay guy, and I got the feeling he was interested in me, too. Looking back on it, he was probably interested in my breasts (my body had sort of “exploded” at 17 and I was a DD) and the fact that I was an “older woman.” He probably enjoyed the thought of having me as one of his conquests.

But we also enjoyed talking to each other, and when he stopped by the house one evening, I guess all the stars were aligned just right for something to happen. I was feeling upset because my boyfriend had stood me up. We were supposed to go out that evening, and I was already dressed. I had put on a pair of tight jeans with a slinky pullover top covered with sequins. The top clung to my full breasts, which were accentuated by my sexy new bra. I was not wearing any panties because I didn’t want any lines to show through the tight jeans. A pair of knee-high boots caressed my calves and completed an outfit designed to get my guy’s motor running.

Only my guy didn’t show up that night. Mark did.

By the time Mark stopped by, I realized that I didn’t have anywhere to wear my sexy outfit, and I was feeling angry and sad and probably a bit needy. We talked for a while and his joking and kidding took my mind off my boyfriend, thankfully. Then he asked if I wanted to go out for awhile. I decided anything would be better than sitting around feeling sorry for myself, so I borrowed my parents’ car and the two of us went for a drive.

We stopped off to pick up some hard cider and drove over to a nearby park where we stopped in a secluded spot and began to enjoy our drinks. The alcohol warmed me as we sat there and drank and talked and flirted. And, of course, it wasn’t long before Mark moved over close to me and began to tease me with light little touches to my arm, my neck, then finally my cheek. He leaned his face close to mine and whispered to me as he brushed my light brown hair away from my face.

I remember wondering whether this guy, who was two years younger than I, was actually going to kiss me. And I didn’t have to wait long to find out. The answer was definitely yes. His lips were soft and moist and his kisses were urgent, as he pressed his tongue between my lips and explored my mouth. My lips had parted easily and naturally as he entered me, even though I knew in the back of my mind that I was cheating on my boyfriend.

But when his tongue found mine and began to dance with it and I felt his warm breath in my mouth, any thoughts of my boyfriend were temporarily replaced with an awareness of this sense of arousal that was building inside me. I knew then that Mark and I were probably going to go well beyond kissing that evening. I was technically still a virgin, as my boyfriend and I had been waiting for the right time to go “all the way.” But I was fairly experienced with oral sex, giving at least, and I suspected there was a blow job in Mark’s future if he kept doing what he was doing.

But I did not want whatever we were going to do to happen in my parents’ car. So I took Mark by the hand and began to lead him into a nearby alleyway. Naturally, he followed very willingly. In just a few moments, we had retreated into the far corner, where the darkness hid us from passersby on the nearby sidewalk.

Just as we stopped, Mark released his hand from my grasp and placed one hand on each shoulder and began to rub and massage me sensuously. I sighed and felt my body relax as I let my head fall backward a little. He moved his body close behind me and I could feel his warmth as he molded himself to me. His warm breath caressed my neck and I could feel the first stirrings of his erection tentatively pressing against my bottom.

He kissed my neck, then my ear lightly and nibbled on my ear lobe as his hands continued their delicious massage on my shoulders. Occasionally, he would let them drift down my arms, tickling lightly as he went, then it was back up to my shoulders. With each trip, his hands circled just a little closer toward the front until he was barely brushing the sides of my breasts.

Mark may have been only a high school kid, but he had a reputation with the ladies. And I was finding out that the reputation was well-deserved. He seemed to know just what to do to take me to that next level of arousal without pushing too far, too fast.

His lips soon moved to my cheek, then as I turned my head a little more, they found my mouth again and we picked up where we had left off in the car—with his tongue teasing mine sensuously. My breaths were coming a bit faster and I could feel the moisture between my legs, even as I felt his erect cock sort of settle in between the cheeks of my bottom.

We kissed like that for what seemed like a very long time as my desire and his continued to mount. I was becoming so aroused from his sensuous kisses that I hardly even realized when he slid his hands underneath my arms and reached around to cup both of my breasts. Needless to say, my nipples were hard as rocks by then, and he pinched each one a little bit through my top and bra, even as he continued to massage my full globes in his palms.

“God, Maria,” he whispered, his mouth very close to my ear, “I love your tits.”

I felt a tingle surge through me from my nipples down to my wet sex with those words. I’d been a bit self-conscious about how big my breasts had grown, and Mark was the first boy who told me that he liked them. I could tell by the way he was caressing me that he really loved them.

Before I knew it, he slid his hands down the front of my sequined top, then back underneath until they were caressing me through the cotton fabric of my new bra. But before I could protest, he thrust his tongue deep inside my mouth again and deftly raised my bra up over my breasts until he could hold the soft round globes in his warm hands. He continued to kiss me deeply as he lifted my breasts gently with his palms to lightly touch the sensitive undersides.

Things were beginning to move faster by this point and I wanted them to. I couldn’t remember ever being this aroused before. I let out a long sigh and extended my arms to brace myself against the cool brick wall. Looking back, I realize it was a signal of surrender, moving my hands out of the way like that, and Mark recognized it as such.

He removed one hand from my breast and let it drift downward until only the denim fabric of my jeans remained between Mark’s fingers and my now-dripping pussy. He massaged me through my jeans, pressing the fabric against my sensitive lips and making a wet outline with my arousal. With one hand on my breast and the other between my legs, he moved them in rhythm, caressing me sensuously but firmly over and over again. And all the while, his lips, his tongue hardly left my panting mouth, as he pressed his firm chest even harder against my back.

Mark began rolling my nipple more firmly between his thumb and finger, making me moan with the combination of pain and pleasure. Lost it the delicious sensation of it, I didn’t even realize for a moment that his other hand had deftly unfastened my jeans to give him entrance to my most private place.

I gasped as he slid two fingers between my swollen lips and dragged some of my dripping nectar upward to lubricate that most sensitive area around my clit. He slid one finger on either side of my swollen little pearl, moving them up and then back down as he expertly gave me that indirect stimulation that allows the arousal to just keep building and building.

And build it did, as he continued his delicious caresses, his pinches, his stroking of the most sensitive parts of my body. My legs were like jelly and my mind was in a fog of arousal. I hardly even knew when Mark slid my jeans downward until they dangled around the tops of my boots. The feel of the cool air on my ass, and particularly on my wet pussy, brought me temporarily out of my fog and made me realize what was actually happening.

Here I was, leaning up against a brick wall in some dark alley, my breasts released from my bra and my jeans dangling around my knees. The mental picture of this scene was so lewd and wanton and out of character for the nice girl I thought myself to be, that I remember thinking it couldn’t actually be happening.

But it was happening. And what’s more, I wanted it to happen. I didn’t want Mark to stop touching me. I wanted him to touch me more. To touch me harder and more completely. And to make it last for a very long time.

I felt Mark pull himself away from me a bit and heard the rustling of his wind suit pants as he pulled them down, along with his boxers. Then he was back against me once more, but this time it was skin on skin, as I felt his rigid cock slide urgently between my thighs until the swollen head parked itself just a moment at my waiting entrance.

Even as my mind was telling me I should protest at losing my virginity in an alleyway like this, with some guy I really didn’t even much care for, my body was telling me that I needed him inside me at that moment. And my body won out as I pressed my hips backward just the slightest bit, even as Mark thrust forward and entered me.