A Canadian Virgin

I will always remember the feeling of Sean’s cock, sliding so hotly into my waiting, yearning pussy. It was so different than the fingers of the few boys I’d permitted to slip one inside of me, so different. His cock was so much bigger than their fingers, yet felt natural in there whereas their fingers had felt alien. Sean was sitting on the edge of the dock and had me sit on his lap, facing him. Then he just grabbed my ass in both hands, lifted me up, and guided me onto his cock. It was so good, so hot, so what I’d wanted my first time to be. I was 20 and just losing my virginity, but this was at least as good as I’d dreamed it would be and probably far better. But let me tell you the full story…

I’ve never been the most beautiful girl, and in fact I’m kind of geeky. Not good enough at sports to be top level, I was never the less in good shape (skinny) and tried to take care of my body. Maybe this is what caused me to hold on to my virginity for so long. I wasn’t a brain, happy being a “B” student. I live in Quebec, Canada with my parents. I know they love me, but from birth they’ve continually tried to mold me into something I’m not. Mother always encouraged me to ‘dress pretty, because you’re not...’ though in looking at the words written they’re not nearly as encouraging as I’d have liked them to be. But it was her way. She never dressed me like a whore, but always bought me clothes that could be whore’s clothes with just a little bit of tuning.

I’m not a whore, never wanted to be one, and when many of the girls in high school were sleeping with their boyfriends because it seemed the thing to do, I decidedly didn’t do it. I even had one ex-boyfriend run around telling everyone we’d slept together, because I tried to use it to keep him rather than letting him get away. I said nothing to refute it which convinced most people he had slept with me. I didn’t care, my body is mine and I plan to keep it that way.

The one thing mother does believe in, preaches really, is ‘always make yourself up, Jadyn. Men love a woman that uses makeup to enhance what God did or didn’t give her. So you need a little extra…’ Yes, I know, hurtful words but she meant well.

This year for our annual family getaway the three of us, Mom, Dad and I, were flying to St. Maarten in the Caribbean for two weeks. From everything I could find out about the place I knew I was going to love it there. Quebec is gorgeous in the summer time, but being stuck here all year simply makes me die to leave.

At the end of our first week in St. Maarten we all had dirty clothes to wash. We were staying in a timeshare the parents had bought years before, and went down to use the laundry facilities which were by the swimming pool. I love my parents dearly but learned years before that I was better at doing my laundry than either one of them would ever be. I offered to do it for everyone, but Mom and Dad were a little bored and lazy and decided to come along anyway. After we’d started the firsts loads Dad went off and bought us all ice cream. St. Maarten in the summer is hot, humid, and sunny. It is a wondrous difference from Quebec, though in reality the weather isn’t all that different. I’d packed very lightly for the trip, for I knew I would only wear the barest minimum of clothes on this trip. In fact, the only thing I had left to wear on that wash day was a long red printed cotton skirt that wrapped around and had ties, and a sports bra in white. I didn’t even have any clean underwear, and instead of putting on soiled ones I went without. As I walked along the friction and the breeze conspired to make my pussy feel more free than usual.

So there we sat on the step outside the laundry room eating our ice cream. Being the semi-tomboy that I am I was pressing my knees in and out, trying to bring a breeze to the heat in my crotch. It was hot here, and the forced air felt good. Then I looked across the pool area and saw a rather tall man looking at me and smiling. I looked around to see who he was looking at, and realized it really was me. I smiled back. He was at least 35, which was at least 10 years older than I ever would think about dating. Then mother and dad decided to go back to the room, and leave me to finish up the laundry. I said bye to them, and when I looked back across the pool the mystery man was involved in a conversation with two women, older than me and probably much more suited for him. But then he looked back at me and smiled. As he did so I realized that my legs were spread widely apart and he could see my exposed pussy, that’s why he was smiling.

I pulled my legs together and as they moved centimeters closer together at a time his smile faded by that much each time. My knees moved apart, his smile grew broader.

Somehow this was different than one of the boys at college sneaking a peak. He thought I’d intended to show off my personals to him, and something about it turned me on. I was embarrassed for the two women, one of which had to be his wife or girlfriend, but he kept smiling as I flashed him, so I continued. Sensing he was tuning them out, both of the women stood up and I heard them both say, “nice to meet you, Sean isn’t it?” Then they left. That left only this man, Sean I now knew, as the only person around that had a clear cut view up my skirt. Heavens, I’d never done anything like this before and didn’t know why I was now, but the movement of air felt good and knowing that he was watching also felt good. He wasn’t looking at my makeup (way too heavy for the pool, but mom had insisted), he wasn’t looking at my clothes really. He was looking at me for me and that felt great.

We kept up the flashing smiling game for the entire time it took me to finish the washing. In fact, when I had everything hung up or folded, I set them aside, and sat back on the rock for an encore showing. He even applauded lightly when I sat back down, and I could see he was showcasing a growing cock in his shorts. I felt so bad yet so good. He was interested in just me. I was to learn how much soon.

Just then two couples walked by Sean and invited him in to the bar for a drink. I guess he couldn’t quite tell them exactly why he couldn’t go, and they were pretty insistent, so he went with them. He gave me a wave and blew me a kiss, though it did seem like the kiss was blown toward my now very moist pussy.

I fairly ran the clothes back to our two bedroom suite, disposed of them quickly, then told my parents I was off to do some looking around and left quickly, but not before mother could tell me to dress up before I went out. Not a chance. There was a man that liked the way I looked and I was going to see what came next.

Fortunately the bar was right next to the pool, so when I got back there I went into the bar and ordered a Perrier and took it back out side. But not before I’d had the chance to say a quiet hello and brush up against Sean, whoever he was. Not ten minutes later as I sat on the deck looking at the rapidly falling sun, Sean walked over and sat across from me, his own Perrier in hand. He didn’t speak, he just smiled. All of a sudden I didn’t know if I had the courage to flash him this close. I looked round, and there were only a few people in the pool area and they weren’t paying attention to us.

Slowly my knees started to spread. I could feel the heat rising in my pussy. I knew I was moist, then reached under my skirt to lightly trace my finger across my pussy. Sean smiled bigger as I watched his cock grow. He’d look me in the eyes, and the thing that struck me greatly about the whole afternoon’s flashing session was that he didn’t try to mask what he was doing. Most men that catch a lash of panties or bra turn away nervously as if they’ve done something bad. He just smiled.

As I ran my finger lightly through those tender lips he smiled even more. By now my skirt was laid off on both sides of my ass, almost fully exposing myself to him. I pulled my knees in, pushed them out. The feeling was one of amazement just knowing that I was holding his full attention. You have to remember that I was still a virgin and waiting for the right moment. That didn’t mean this was it, that just meant that I was loving this feeling.

Somewhere over my shoulder I heard mother speaking with father. I slouched down in the chair and looked, and they were both in the bar for happy hour. Dad always was keen to save a few cents on his large daily ration of beer. I looked back at Sean, not knowing what to do. But I did know that if they walked out and saw me here they would be very interested to know why the two of us, the only two people on this entire half of the pool, were seated five feet apart from each other looking directly at each other.

“My parents,” I said, pointing to the bar. “Can we go somewhere else?” I asked.

Quickly Sean stood and walked to the end of the pool area to a metal gate. “Quick, down here,” he said, leading me down the steps. The pool was on Oyster Bay, and sat on a very rocky coast. The steps led down to the pump room, thought there was also a cement walkway down there that jutted out into the ocean. We were right on the Northeast corner of St. Maarten and the Atlantic Ocean, continually buffered us with waves and wind. Sean sat down, his back to one cement piling. I sat five feet away, my back to another one. This time I pulled my skirt completely behind me to where I had something comfortable to sit on yet otherwise was showing myself off to him entirely. This was by far the most adventurous thing I’d ever done.

I looked at him, closer this time. HE was definitely at least 33 and maybe more. Mom would freak if she had any idea of what I was doing, though she was the one that was always pushing me out there to meet a man. ‘Someone to take care of you, you’re not pretty enough to be a model or actress, so you’ll have to find a good hearted man for you,’ she’d said on more than one occasion. I didn’t care about the age thing, he was thrilled to be watching me and I was thrilled to be showing off to him. Then it hit me, that I needed to do one more thing. I removed the sports bra. For all practical purposes I was naked, sitting on a cement ledge, with a man I’d not spoken with, and it made my body scream with pleasure. My nipple jutted out to the front, I could feel the heat between my thighs, and my head felt a lot loose.

Then I got ballsy and motioned for him to remove his shorts, fair being fair. With a shrug he did, and exposed what looked like a good 7 inches of cock for my eyes. As he did, I inched closer to him. He set his shorts back on the concrete as I got close enough to him that my thigh touched his. My hand reached out and touched the first real cock I’d ever held. Okay sure, back in 5th grade I’d touched Donnie Leach’s cock, but that was just touchy feely. And maybe a few times since then. Yes, there’d been times on dates when I’d been dating a boy for so long that I had to do something to show him I had some interest in him, so I’d grabbed his penis through his pants mainly. But that was it. I'd let boys touch me on the breast at times, even more rare would one be allowed to touch my pussy, and most rare were the only several boys that had been allowed to slip a finger inside. Mainly because all they did was run the finger in and out, and at the time I didn’t even recognize that the reason I let them do it wasn’t to get the finger in me, it was because if they held their had just right the heel of the hand would rest on my clitoris and bring on a warm feeling.

As I held Sean’s cock, we both turned to face each other, knee to knee. He reached out, and lightly stroking my thighs began to work higher. Clumsy me, I’d just reached right out for his cock and started to stroke.

All of a sudden it was his thumb that was pressing onto the skin over my clitoris, then slowly it worked inside and was directly on that button. Then another finger started working its way up and down my now eager pussy. Shit. I didn’t know anything about him but I was about to reach a point where it would be impossible to get him to stop. I didn’t know what to do, but stopping didn’t seem right.

Sean was sitting on the edge of the dock and had me sit on his lap, facing him. Then he just grabbed my ass in both hands, lifted me up, and guided me onto his cock. It was so good, so hot, so what I’d wanted my first time to be. He let me drop down a little ways onto his cock, then stopped my motion and lifted me up again. It was a good thing because inside of me everything felt real tight, and his cock pressing into me was hurting.

Again he let me settle down onto his cock, then when there was only resistance and no penetration he stopped. He repeated this at least four times, to where I began to wonder if I would ever really get to lose my virginity. Maybe I was too tight, or needed a smaller cock, like a pin prick sized one or something.

He repeated it once more, and this time I took my feet and pulled on him, pulling myself even tighter onto his cock. And then I felt it start to slid into a space it had never been before. I let out a soft squeal, because it really did hurt. Far worse than the first few times I got menstrual cramps and didn’t know what they were. Far worse than when I’d been kicked by that bitch Cindy Norman in soccer, worse than anything ever yet. But it also felt good. I finally had a man’s cock inside my pussy.

Sean continued to lift me up, then slide me down onto his cock. I had my face buried in his shoulder trying to be quiet, but then he started to moan and I knew it was okay to do. I moaned, he moaned, then we stopped moaning and fucking and for the first time his lips met mine. Our lips slammed into each other, and I distinctly remember that rough feeling of his day old growth of beard on my soft chin. It hurt but I wasn’t going to stop him.

Then I heard it, mother’s voice. “I heard something over this way, maybe it was just the ocean,” she said.

Fortunately Sean was a very tall man. I could just barely peak over his shoulder and see mother and dad walk to the edge of the pool and look down at us. More fortunate was the fact that it had grown pretty dark and their were no lights here, for when their eyes adjusted I heard mother cry out, “there’s someone down there… and they’re… oh my god, Dean, let’s go!”

Next I heard a very nice moan escape Sean’s lips as when the parents had appeared I tightened all of my muscles, all of them. I guess my very tight pussy had become even tighter.

I never once heard either of my parents call out my name, so it was pretty clear they didn’t know it was their daughter on the ledge. I broke out laughing, then started to rise up on Sean’s cock and lower myself back down again. All of the excitement must have combined in my body, for several stroked later I felt a boiling sensation start in my lower back and work its way up my spine, taking in the top of my head, then down to my breasts, and lastly to my pussy when I experienced what had to be me first orgasm. I bit solidly into Sean’s shoulder to keep from screaming out for joy. Together we thrust wildly at each other and I focused on the pleasure not the pain from what had so recently happened. I was a women now!

As we abated, Sean once again lifted me up and set me on the edge of the dock area. It was dark now, and the lights from the pool cast something of a glow. But I could easily see him look down at the rocks, then twist and drop to the rocks. That put his face right in front of my pussy, and he wasted no time in driving his tongue straight for my now desirous clitoris. My God did his tongue feel good. I’d run my hands through there before, but never had anything like this been felt by me. He licked the clit for a while, tasting each millimeter of my labia, slowly sucking and licking me. Then when I started to build up again to an orgasm he would suck on a thigh, and start to kiss all the way down to my knee. So unlike all those boys I’d been with who only seemed to think that fast a furious was the way to go.

This went on for what to have been thirty or more minutes. By now the half moon was out, couples could be heard walking by above our heads, but he just kept on, and I got bolder about moaning out loud. Then, when I thought I couldn’t take much more, Sean buried two fingers inside me and concentrated his tongue on my clit. He also started this suckling motion with his lips, and his finger touched what had to be my ‘g’ spot, for it was only seconds before I moaned loudly and crumpled over onto his head, another orgasm racking my body. He slowed down the licking and sucking but never stopped, even after I asked him to. He just shook his head and kept it up, and as that orgasm abated he sped up and brought me to yet another one. Over and over he did, until I’d had my sixth orgasm and knew I couldn’t take any more. I laid back on the dock and squeezed my thighs around his head. He just pulled me in closer. Then one of his hands lifted, and while I had the chance I swung my legs up onto the dock and away from his mouth; I just couldn’t take it any longer.

He jumped onto the dock and sat beside me, pulling me up into his arms. I reached over for him and as I did my hand touched his still hard cock. It was brick hard.

“Didn’t you cum?” I asked.

“Not yet. That was all for you, not me,” he said.

I gathered up all of my strength, pushed him onto his back, then took his cock into my mouth. I could taste myself where before I’d only smelled my own musk. I tasted kind of sweet, and forbidden. I licked his entire crotch region, wanting to lap up all of what I’d left there. Then I took the head of his cock and put it into my mouth. I remembered something I’d read somewhere and started to hum lightly. This got a huge moan from Sean and I was glad. Because there I lay with a mouth full of cock and I realized it was also my first and I hadn’t a clue of what to do with it.

So I just thought ice cream and started to lick. His moaning told me I was at least doing something good. He moaned loudest when I licked the underside of his cock, and seemed to love it when I took as much as I could into my mouth. I was very glad he wasn’t bigger. When I took it all into my mouth I gagged, and almost bit him, but held back. This really turned him on. I could feel his cock heavily sitting on my tongue, and each time I took the tip of my tongue and ran it up the underside of his cock his hands grabbed my hair even tighter. What control of this man I now had.

I pulled the cock out of my mouth and looked at it glistening in the semi-darkness. I guess it was 7 inches, that was perfect. More and I wouldn’t have been able to handle it. I ran my hands over his legs, but it felt like I was doing it just to do it rather than knowing what to do. So I decided to gently cup his balls in my hands and lightly play with them. This he liked.

Then I tasted something different. I once again pulled it out to see if he had come but he hadn’t. There was a some fluid seeping from the end of his cock, and I licked it up quickly. His moan was so loud that I knew he wanted me just to suck on the end of his cock. And I was happy; the fluid was almost tasty. A little salty, but not bad. I’d heard so many girls say how gross it tasted that I was hesitant, but his tasted good.

Then as I licked his hips started to roll. His moans were louder, even though both of us could hear people out on the deck above ours heads. Now I didn’t care. I knew my semi-prudish parents wouldn’t return so what did it matter? I took the entire length into my mouth once again, and after just a few more strokes thought my cheeks would blow out as he came into my mouth. This too tasted good. I liked it. Maybe that would be my secret now; I like the taste of cum!

I increased the rhythm of my sucking which caused him to cry out. He half-heartedly tried to pull me off his cock but I just kept pumping it into and out of my mouth. I loved the control. Each time I did anything with my mouth or tongue I could see it register on his face. What control I had.

I pulled off his cock when I was sure I’d swallowed every drop of cum he had. I crawled up into his arms, and as I laid down on his chest we heard light applause from above.