It all started at lunch when I offered to show Jay a shortcut around the normal traffic jam caused from everyone leaving our school. I knew Jay had a massive crush on me, but he was not my type. He was by no means unattractive.
He had the stereotypical football player build with those broad shoulders, fairly muscular and very much in shape. His blue eyes matched the blue of the desert sky. As shallow as it sounds, I just preferred my men to be taller, like over six foot tall and Jay was only about 5’ 10”. Aside from that, Jay also had a reputation of being a bit of a heartbreaker and a tease. I never understood it, I had known him since the seventh grade and he was a quiet, intelligent guy that seemed to lack the self-confidence of anyone capable of being much of a heartbreaker. He just seemed clueless or way to causal for someone that had woman falling at his feet. Honestly, I thought he was gay and still in the closet because of his avoidance of women.
After our classes that day, we met in the parking lot and he started to follow me down the road, it was more of an emergency fire road than an actual road. I knew my ’85 Dodge Ram could handle it, but I didn’t take into consideration that he drove a two door Buick. As he followed me, I never thought he would make it. But whenever I looked in my rearview, there he was right behind me as relaxed and confident as I had ever seen him.
I could feel my body betray me before my mind did, something in that confident, controlled gaze moistened my virginal womanhood in a way my good Christian past had never let me experience. As we turned onto the main road, I tried to ignore it, even attempted to get mad at him for tailgating me, but as soon as I asked “Why is he riding my ass?” my mind questioned back “Why isn’t he riding my ass?”
I blushed and felt ashamed of myself for such a naughty thought, however as I saw the turn off for the local make out spot, I turned off and headed for it, signaling for him to follow. I don’t know if he was of like mind at that time, but he made the turn with me.
It was a couple miles up the dirt road to the overlook, and the anticipation was starting to kill me, I felt flushed and clammy while nervous that I had become wet enough for it to be noticeable thought my jeans. I told myself if he plays it right, I’ll let him kiss me, we’ll make out a little bit and then we will part ways. I should have known better, my parents had warned me about moments like this. But I wanted to know what his arms felt like around me and feel his lips against my skin.
Suddenly, as if by autopilot, I’m parked in the overlook and he is standing next to my window. “Sure pretty here” his silky smooth voice drifted in from my driver’s side window. I turn in my seat to look at him, just as he glanced over to me. In a rush of passion, my lips lead me toward him, then suddenly I could feel his lips against mine. I felt him draw back from the kiss briefly, clearly as shocked as I was by my actions.
After a fleeting moment, he stepped back from the kiss and opened my driver’s side door, I turned in my seat and allowed him to move in close to me. I loosely wrapped my legs around his hips. A shock of excitement coursed through my body as his hands slid up the sides of my legs. His strong hands gripped my hips as his lips pressed wantonly against mine.
I parted my lips just enough to allow the tip of my tongue to pass, only to meet the tip of his tongue. As our tongues started to dance together, I felt my reservations slip away, I was his. I wrapped my arms around his neck and pulled him closer to me, and I could feel his right hand slowly slipping up my side. The stiff cotton of my button-up shirt pressing against my soft skin. His hand drifted over my left breast and an excited gasped escaped me. I could feel his hand and fingers kneed my breast softly, the feeling of the lace of my bra teasing my nipple stiff with excitement. I could feel that I had soaked through my panties and dampened my jeans, the denim sticking to the inside of my thighs.
It seemed like he knew my body better than I, as his lips moved away from mine, only to send an overwhelming burst of excitement through my body as he placed light kisses and soft bites up and down my neck. His fingers nimbly unbuttoned my shirt, and I leaned back to allow his kisses to move down along my collarbone before he slipped my shirt off. The straps of my bra were next, slowly slipped from my shoulders. I brushed deeper as I felt his hand slip inside of my bra and when he teased my nipples with his fingers, I knew I was going to let him have his way with me. Without a word, he unclasped my bra, freeing my c-cup breasts from its confines.
I closed my eyes to block out the rest of the world. Goosebumps raised on my skin as his lips carefully kissed down my neck. My heart skipped a beat as I felt his lips press a soft kiss along the top of both breasts. Suddenly an electric shock of mind-numbing pleasure crashed over me, causing my womanhood to quiver, as he started to gently suck on my nipples. The feeling of pleasure continued to build as he tongue started to rapidly flick and tease my nipples one at a time. It was only a matter of moments before I felt the muscles of my legs tighten around him, then the walls of my womanhood shudder as I experienced my first ever orgasm.
As my senses returned to me, my face red from embarrassment, I looked down to found him kissing down my stomach. He stopped right above the button to my jeans, oh gods why did he stop. He then looked up at me, his blue eyes meeting mine, I felt my body quiver again as his intentions became clear. I could only manage a weak nod of approval before he freed my body from the rest of my clothes.
I was completely nude, my shoulder length blonde hair would do nothing more than hide the shame of my face if something happened along. My green eyes fixed on him as he started to kiss my inner thighs. Suddenly, I felt his tongue enter me, and it felt like I had been craving that feeling forever. He quickly brought me to my second and then third orgasms without much effort of his part.
I let him carry me to the bed of my pickup wear he gently laid me down. I wanted to feel him inside of me again, I wanted him to be my first and I knew it was going to happen. “Please, please Jay, fuck me” I moaned.
“I’m a virgin” he whispered in my ear.
“Me too” I whispered back.
I could feel him works his pants and boxers down. Then I felt the thick head of his cock press against my wet folds. I kissed him passionately, hooking my legs around him. “Oh Linny” he gasped as his cock slowly sank into me. Even with how wet I was, I could feel the tight walls of my pussy stretching and resisting as he continued to sink into me.
The feeling of his cock slipping in and out of me was the most amazing feeling I had ever felt, and just as quickly as it had started, it was over. Both of us clinging to each other as a shared powerful orgasm rocked our bodies, his hot seed spraying deep inside of me as my juices flowed freely down his shaft.
We had both heard the tales of me passing out after they got off, so we were both equally surprised when he was still semi-hard inside of me after our climax. He slowly started to thrust into me again, the full stiffness of his cock returning quickly. After a few moments of thrusting, he had me roll onto my stomach. When he reentered my body, I experienced a nearly instant orgasm as he took me from behind, his hands reaching around to grab my breasts.
He brought me to two more orgasms as he plowed me from behind, finally filling my body with another hard blast of his seed. When his cock slide from my body for the second time, it felt as if he had taken the last of bit of my strength with him. I limply laid in the bed on my truck, legs hanging off the tailgate. I felt like I was going to drift away into nothingness.
As I laid there, he started to gently massage my back, and kiss my shoulders. The sticky mixture of our juices keeping us together. I could feel the strength return to his cock as he continued to caress my skin with his hands.
When he went to enter my pussy for a third time, there was an instinctual rejection from my body, knowing I could not handle another round of him violating my sensitive pussy. “Please, no, I can’t” I whispered. He stopped and I could feel his hand lightly grab my ass, “How about a different hole, then?” he whispered back.
I felt a surge of terror as I realized what he meant, but it was quickly washed away by a wanton naughtiness that I did not know was inside of me. I nodded and mentioned the coconut oil in my purse, hoping it would help ease his way into my even tighter ass.
Moments later, he was slipping his lubed cock slowly into my ass. It did not hurt like I expected, and after he was about a third of his way in, a pleasured moan escaped me. When he finally started to slowly slide in and out of my ass, I couldn’t help be lose myself in complete ecstasy. I knew he was getting close as he started to grunt and groan with a primal tone only heard in the deepest depths of pleasure. As he released inside of my tight ass, it triggered something inside of me. A cascade of blinding pleasure slammed into my body like waves, so powerful my body expelled the extra juices from my dripping wet pussy in a lewd gush.
He then collapsed into the bed of my truck next to me, breathless. We laid there for what seemed like days, not saying anything. We simply bathed in the afterglow of our carnal pleasures.
Source: reddit.com/r/sexystories/comments/5pf78g/the_first_time_str8_mf