I was a high school sophomore of sixteen when I met the guy who would take my virginity. I knew he would be older because I wanted an experienced lover to teach me the ropes and no ordinary high school boy would be the one to fill that role. I knew sixteen was problematic, but I looked every bit of eighteen and was confident that I could navigate the issue.
Tall and dark-haired with green eyes, he was physically a perfect match for my ideal candidate. I guessed him to be maybe twenty-two or twenty-three, but it didn't really matter, I just knew I was sure that he wasn't in high school.
I'd first noticed him at church about a year ago and since that time I'd become a regular attendee of the 8:00 am mass where I was always able to position myself few rows behind him each week with my impure thoughts. My home was just a short walk from the chapel and my family thought it was wonderful that I was so dedicated to attending on a regular basis, even though they preferred the later 10:00 am mass.
For the past few weeks, I'd felt that my cover might be blown. I'd caught my guy glancing back over his shoulder more and more frequently, as if he was looking for someone that he might be saving a seat for, but who never came. Occasionally, he'd make brief eye contact with me before quickly looking away again like it was unintentional.
Eventually, there came a day where I arrived at my typical 7:58 time, which always allowed me to position myself according to wherever he was sitting, only to find that he was not in attendance. I was bummed, to say the least, knowing that I would have to go a full two weeks now without seeing my fantasy man.
As the service began, I looked down to grab a hymnal when I heard someone quietly excusing himself down our row from the aisle. To my delight (and subsequent terror) I looked up to see my dream guy settle into the vacant seat to my left. With a quick flash of a smile, he reached down and grabbed a songbook of his own before looking straight ahead and joining the chorus.
I didn't know if it was blind luck, an intentional play on his part, or just good old divine intervention answering my prayers. All I knew was that I didn't care, this was the icebreaker that I had waited for but had been too shy to initiate myself.
The priest's invitation to turn and greet your neighbor near the end of the service was the perfect opportunity for an introduction. I offered my delicate hand with a smile and found his to be warm and welcoming with a firm grip by comparison. We made some casual conversation while exiting the church afterwards, before stopping to talk further in the sunshine outside. He soon asked if I'd like to grab a cup of coffee from a nearby coffee shop and I replied that I'd love too!
Thus began an hour-long conversation regarding everything about each of us. My summary of myself was a carefully orchestrated combination of both truth and fiction while I attempted to present myself as an eighteen-year-old senior rather than the younger underclassman that I truly was.
By the time we finished our talk, I had agreed to meet him for a movie the following Friday night, clarifying up front that I would need to meet him there. As I explained it, my parents were a very tough interview, one that would be best experienced at a later time when we knew each other better. I planned to cover myself with my parents by saying that I was meeting my girlfriends at the show and would be home by my usual 11:00 weekend curfew.
On Friday evening, I made sure that I was waiting outside the theatre at 6:45 sharp for the 7:00 movie, looking the absolute sexiest I could manage without causing undue suspicion when I left the house. I was getting a little worried when my phone showed it was 6:55 with still no sign of my date. Just as I looked up from the screen though, he walked out of the theatre doors from inside and said that he had just run inside to grab the tickets since he hadn't seen me there yet. Relieved that I hadn't been stood up, I smiled broadly and said that was great.
We hurried inside and found our seats just as the movie began. I'd read on the trailer for the film that it was 135 minutes long, meaning that with previews we were probably looking at getting out around 9:30 pm if we stayed the entire time. That left me another 90 minutes until curfew, which was a little tight for my intentions but all that I would have to work with.
It was about halfway through the film, when I felt a hand rest on my leg. Startled, I felt a rush of nervous excitement before turning my head to look at my date. Everything in me said to kiss him before the moment passed us by, so I did. Much to my relief, I found my kiss returned with equal zeal.
The next ten minutes or so of the movie could have been blank film for all I would have known. We were lost in each other and oblivious to anything around us as weeks of pent-up lust from our Sunday game of cat and mouse was released. With both of us now indifferent about seeing the rest of the movie, he whispered in my ear if I'd like to take off. I nodded yes and glanced down at my phone. Perfect, I thought, it's only 8:10! Plenty of additional time now to cushion my 11:00 pm deadline.
Exiting the theatre, he asked somewhat cautiously if I'd like to come back to his apartment for a while and watch something on TV that was of more interest.
"Sure," I replied with a teasing smile, "that would be nice."
He said it was only a short walk away, then reached down and took my hand for our stroll. As we walked, I asked if his roommate would be home. Once again I felt a small rush of adrenaline when he smiled and replied that he lived alone.
After arriving at his second-floor unit, we only made it only a few steps inside before the door closed before behind us and he turned to face me. He was quite a bit taller than me and his neck bowed down to look at me just as much as mine tipped back to look up at him.
At that moment, I barely noticed his hands grasp my upper arms because of my intense focus on his green eyes, which grew slowly closer to my own as he moved to kiss me again. His now familiar lips felt soft and warm when they touched mine. He was a really good kisser and I felt my legs weaken just a little in his embrace. As the pressure of his kiss increased, I turned my head slightly and pressed back harder in reply.
One of his hands now slid upward and grasped the back of my neck while his other slid down and wrapped my waist, pulling me tighter against him. I heard myself panting quietly as I was drawn into his advances, then louder to signal my approval. This was much better than the awkwardness and public nature of the theatre.
I didn't know what to do with my hands, so I wrapped them around his waist, resting them safely above his butt. I really wanted to slide them lower and feel it, but I felt shy about what he might think if I made the first move like that. God, why didn't I just put them there in the first place and avoid this dilemma?
Almost immediately, I realized that he wasn't worried at all himself when the hand he had around my waist slid down assertively and then easily cupped one half of my tiny ass. Following his lead I did the same, finding his to be much firmer than I had imagined beneath my small hand.
I felt my body temperature rising quickly as we continued kissing, my blouse beginning to dampen in response to its unwilling separation of our chests. Breaking our kiss momentarily for air, I tipped my head back instinctively to allow his lips to meander down my exposed neck seeking my partially exposed collarbone. My body tingled from the sensation and I felt a heightened excitement I had not encountered before, a craving feeling of surrender, animal desire and need.
One of my hands now confidently slid up beneath his shirt to explore his bare lower back while the other stayed securely anchored to his buttocks, unwilling to give up the territory it had claimed. It was at this moment when I first noticed the growing bulge between us inside his pants. Oh my god, I thought to myself, he has an erection!
I don't know why it surprised me so much, after all, a man needs an erection to have sex, but I'd never seen or felt one in real life before, either inside or outside of a man's clothing. Even more startling to me was my sudden realization that not only was he sexually aroused, but that I was the reason. What was he thinking? Was he imagining me naked? Was he fantasizing about having sex with me? Could he sense that I was a virgin?
I knew that I already that I was wondering similar things about him. Was he as experienced a lover as I hoped he was? How would we do it? Most of all I wondered what his penis looked like. Was it big? From how cramped his pants felt between us it seemed that it must be. I desperately wanted to move my hand down and touch it, but I was much too timid to do such a thing.
Both of his hands moved to my neckline and began to unbutton the top button of my blouse. Oh my god, I thought. This is it, he's going to undress me! He's going to undress me and then he's going to fuck me! The thought of it both scared and exhilarated me. I wondered what it would feel like at the moment when he entered my virgin pussy and proceeded deeper into my unexplored body.
Summoning all of my courage, I drew my hand around his hip and dragged it over the lump that now angled down across his upper thigh. Stepping back from my contact, he created more space for himself more to operate and breaking off my advance temporarily. Didn't he want me to do that? Oh god. Did I do something wrong? Was I too forward?
Standing awkwardly in front of him and still not knowing what to do with my once again empty hands, I stood tall and watched him slowly unfasten each additional button of my blouse in succession as he moved lower. My firm and ample cleavage was increasingly revealed to him in exact three-inch increments, giving him a teasing glimpse of what lay inside.
When the final button succumbed, he gently opened my shirt and slipped it from my shoulders before letting it drop behind me at the waist. Reaching behind myself, I tugged at the cuffs anxiously to pull it free of my wrists before feeling it fall helplessly to the floor.
Standing before him in my bra was both embarrassing and exciting. Did he think I was pretty? Was he pleased with my body? I'd never been with a man wearing only my bra before. Thankfully, he smiled and that was all it took to put me at ease. I kicked off my shoes, making myself even shorter. He laughed and did the same to bring our height disparity back to the original level, before telling me it was my turn.
I reached out and grasped the bottom of his tee shirt near each hip and lifted my arms as high as I could to try to remove it, which still wasn't nearly high enough. He assisted me by pulling it the rest of the way off for me, leaving himself bare-chested. He was athletically muscular and his arms were very nice. Not over the top, just a nice lean kind of build. His abs were well pronounced and they complimented his small waist perfectly.
I felt the tingle again as I stood and looked at him. Oh, I'd seen plenty of men with their shirts off before, I'd just never been the one to make it happen. My mind was racing, constantly thinking about the first real penis I would see soon and what he would do to me with it once I had.
It was his turn again now, but he told me to do it for him. I'd never revealed any part of my body to a man before that couldn't have been concealed by a bikini. I hoped that I didn't appear nervous even though I was. Reaching around behind myself, I unclasped my bra before slipping off each of the shoulder straps and allowing it to drop at my feet.
The room was cool, causing me to give a little shiver. Looking down at myself, I took a moment to make sure nothing was unexpectedly wrong. I was embarrassed to see that my small nipples were very hard and erect. I hoped that he liked them.
Stepping back closer to me, he gave me another long kiss before picking me up and carrying me toward his bedroom. My breasts were pressed against his bare chest as he walked, his arms controlling me with confidence on our journey to the place where he would have me. Setting me down on the edge of the bed, he gave me another kiss before standing up straight and placing his hands on his hips. Looking up into his eyes, I knew this was his signal for me to end my curiosity.
My hands trembled slightly as they reached up and fumbled with his belt. After some awkward tugging, I was finally able to unfasten it and turn my attention to the waist button and fly. I pulled down gently on his zipper and opened his pants, only to discover that the underwear I expected to see was not there.
Pulling down firmly on the waistband with both hands, his pants slipped lower toward his hips and buttocks, thus enabling me to catch my first glimpse of what I had been waiting for as the base of his penis came into view. The farther down I pulled his clothing, the more of him that was revealed until his pants were finally low enough to fall from him completely. I stared in astonishment, unaware that my mouth was hanging wide open.
Wow. Double wow. My heart pounded faster as my eyes darted back and forth between his eyes and his erection, which stood proudly upright at an angle of about forty-five degrees.
This was no penis, this was a cock. I guessed it to be about eight-inches in size, circumcised and very thick. He was closely groomed as well to my pleasant surprise. It was impressive, beautiful and honestly everything that I had hoped it would be, maybe more.
Stunned, I didn't know what to do next. Should I hold it? Did he want me to put my mouth on it? I was sure my inexperience was clearly showing now.
Panic started to set in. How in the world would such a thing ever fit inside me anywhere! I sat speechlessly and watched him tug his pants the rest of the way off and step out of them.
I lay back on the bed for him, unzipping my own pants. Reaching down, he tugged the cuff of each leg over my feet one at a time until they slipped off to be discarded with our other unneeded clothing. I could see my breasts rising and falling, my nipples still hard, as he reached down to remove the matching lace panties that I had paired with my bra tonight for this special occasion.
Nothing remained for either of us to remove now. I lay naked before him on his bed, fully exposed to a man for the first time. Standing over me was the first naked man I had ever been with sporting the huge erection that he would soon use to take my virginity. I reached down between my legs to see if I was wet. When I lifted my fingers back up for a look, they glistened. I knew I was ready and so did he.
Kneeling down on the mattress, he extended his arms to support himself over me as I spread my legs and allowed him to move between them. It felt naughty to expose myself for him and watch his cock draw closer. He lowered himself until he was able to kiss me again, his lips just as inviting as when we had first entered the apartment.
My breasts compressed under him against his bare chest and his cock lay sandwiched between us against my stomach. He dropped his head and circled my nipples with his tongue before lightly pinching them between his teeth with a teasing bite. It felt incredible.
My desire erupted. All I could think of now was that I wanted him. I wanted him to take me now, to teach me. I ground myself against him trying to make it more obvious, lifting my hips up and down, my uneducated body somehow knowing how to move itself like evolution had intended. He moved lower yet, kissing his way down my torso. Instinctively, I spread my legs wider. I could feel the heat of his breath between them and the warm wetness of his tongue tracing the outside of my narrow little slit.
Using his fingers, he spread it open for himself before pressing his face against me harder. I lifted my hips again in complete acceptance as he flicked at me with his tongue. Suddenly, he touched a spot with his tongue that made me jump. He sucked and circled it, focusing his attention. Oh my god, it was good. A finger slid inside me and added pressure from within me, driving my animal desire even higher.
He sensed my craving now and rolled onto his back to give me the freedom to explore him. His cock stood tall and vertical, large veins traversing it. I reached out and grasped it in my hand lightly until he wrapped it with his own to show me he wanted me to hold it firmer. It was warm and rigid, yet soft and smooth. I slowly began stroking him up and down, unsure of how fast I should go.
Squeezing harder, I watched the skin move up and down freely in my grasp, the head swelling on each upstroke. So that's how it works, I thought. His reaction to my efforts showed me I must be doing ok. I still couldn't fathom how he could possibly fit inside of me.
He asked me if I had ever sucked a cock before, knowing that I hadn't. I shook my head no and he smiled, telling me not to be embarrassed, that he would teach me.
Gathering my courage, I slipped down the mattress to bring my mouth closer to my hand. Up close, his cock seemed even more enormous. I licked my lips to wet them before parting them slightly to cautiously touch the head. It was surprisingly soft, which encouraged me to try a little more.
I felt his hand sweep my hair back out of the way so he could watch me. With my hand and mouth working together, I found myself able to take in a little more in each time until I struggled at a point about halfway down. I didn't think I could possibly take any more until I heard him encourage me and tell me I was doing great.
I took his encouragement to heart and pressed on more confidently, wanting to prove that I could successfully deep throat him for my first blowjob. I nearly gagged several times trying to take more of him in and he told me to relax my throat. I had barely tried to before the firm pressure of his palm on the back of my head broke the impasse and his cock turned down the back of my throat.
Surprised by his move and unable to pull back, I surrendered as he held me there, subsisting on minimal air while I experienced his fullness inside me. What seemed like an eternity, was most likely only a few moments before I was pulled back off of him by my hair, his cock coated with a long strand of my saliva.
Nature took over now. I knew exactly what to do. Pumping his cock with my hand, my mouth worked in unison with it to pleasure him. In and out of my mouth I took him, sucking and stroking while I looked up into his needy eyes. His cock grew harder and more impressive wanting more. I knew what more was and he would now have it.
Rolling onto my back, I lifted and parted my knees allowing him to move freely into position between them. He told me how beautiful I was and asked that I press my breasts together for him, which I did. I watched as he stroked his cock to return it to maximum hardness, which only took a few moments. When he was ready, he used his hands to push my legs higher and wider, opening my virgin tightness for himself. I expected that his coming penetration would hurt a little and I tensed slightly with apprehension before taking a deep breath and giving myself to him.
Reaching down, I took his cock firmly in my hand and guided him to the precipice of his target. This was it, the moment when I would be deflowered as his experienced cock claimed my virginity. Looking up at him I started to ask him to be gentle with me, only to feel the pressure of his cock parting my tiny slit and eclipsing my words. I winced a little, more from surprise than from pain and told myself to relax.
He asked me if I was ok and I nodded yes, before he gently pushed in a little more. He was very patient as he proceeded, encouraging me and going at my pace. His cock felt enormous inside me and I didn't know how I would possibly take it all. When I thought he could go no father, he pulled back a little before thrusting back a little harder and I felt a searing pain followed by an instantly deeper penetration.
He told me to look down and I did so to see him fully embedded in my no longer virgin pussy. I panted rapidly, knowing the worst was over now and nervously ready for what came next. He told me how tight I was and how good I felt wrapped around his cock. I felt incredible with him inside me.
His pace slowly increased, his ass moving up and down with my hands glued to them until the thrusting became quite hard. The balance of pleasure and pain now tipped more to the pain side, but I didn't want him to stop. I could tell he was an experienced lover, speeding up and slowing down as needed to maintain his stamina. He told me again how beautiful I was and how perfect my body was.
I closed my eyes and focused on the feeling of my first cock sliding in and out of me so effortlessly now, his testicles slapping against me below it. Inside, a strange feeling started to build that was foreign to me.
I heard myself moaning loudly now, begging him not to stop. Then, in mid-sentence my body quivered uncontrollably, erupting in what was undeniably my first orgasm. Oh my god, an orgasm! This was what it was like? I could hear him telling me what a good girl I was as I whimpered with pleasure, fucking me straight through it all until I lay spent below him, begging him to make it happen again.
I whispered softly that I didn't want him to cum inside me, which he agreed to before asking me how I would like him to. I hadn't thought about that. I had no idea how much there would be. Not wanting to show my inexperience, I blurted out the first thing to come to mind. I said that I wanted him to cum on my tits.
Withdrawing from my newly christened pussy, he moved up and stroked himself over me vigorously while I watched him. I'd never seen a man masturbate or ejaculate before and I waited with eager anticipation for it to happen. His cock was swollen and his testicles were very tight. He urgently told me to press my tits together for him which I did. He asked if I was ready.
"Yes," I said before biting my lower lip and pinching my nipples.
With a final few strokes, he slowed his motion and watched with me while a steady stream of clear ejaculate dripped from him, followed by burst after burst of creamy, bright white cum that splattered my naked torso like little pearls. As more gathered and pooled between my breasts he took the head and circled my nipples while his final contractions coated them.
I couldn't believe how much there was. I wondered what it would feel like shooting inside me and what it must taste like. I reached out and took his still throbbing cock in my hand to stroke him a few more times. His cum was slippery between my fingers and the sight of it on my naked body turned me on.
I was already ready to build upon my first sexual encounter, one that I had waited much to too long to experience. Lying there with his cock growing softer in my hand and admiring the sight of my cum covered breasts, I thought of the other sexual firsts I would still experience and how this guy would teach me about each and every one of them. Curfew was nearly upon me though, so my second lesson would have to come later and I couldn't wait.
