Jessie & Matthew's Awesome First Time

It was quite a few years ago now, but I remember it like it was yesterday. I had just turned 20 years of age. I hadn't had a serious boyfriend until Matthew. He was 21. I was a virgin, he wasn't. We had been going out for quite a few weeks and I had strong feelings for him. He came from a wealthy family and was involved in the family business. He was 6ft tall, dark-haired, blue-eyed, good-looking and fairly slim. He owned a red Porsche, which I have to admit, made him just a little more appealing! But other than that, he was a sweet, caring, funny, hard-working and good-natured young man. Just about everything a girl wants. I had told him I was a virgin, and he was very respectful of that. He promised that when the time came, he would be very gentle, and that he wouldn't pressure me too much. I had always been a bit apprehensive about doing anything sexual. There was a male I had known for a very long time who was obsessed with sex and was always talking about it and trying to seduce every woman he came across. He had even spent time in prison for persistently sexually harrassing my best friend. He was such a dirty person, and I had probably developed a subconscious notion that sex was dirty. I had never masturbated or used any kind of sex toy, so at the time I didn't know what an orgasm felt like. So, after weeks of kissing, French kissing, the odd love bite, one session of dry humping (that had made me sooo wet), and one occasion where Matthew had felt my breasts under my shirt, but over my bra, I knew the time to go all the way was fast approaching. I had stopped Matthew from getting in my pants or seeing me naked up until then. He was very much the gentleman and had said "whenever you're fully ready, baby". And so, it was late on a Friday night in late spring, after we had come home from watching the sprint cars together, that Matthew drove me home in his Porsche, and I invited him into my unit and into my bedroom to see my collection of shells I had previously told him about. My bedroom contained a double bed, but he'd only been in my room once or twice before. A storm had been developing outside for some time. Storms were unusual this time of year, and this one was a very humid tropical sort of storm. As I showed him my shells, we could hear the rumble of thunder outside. Then would you believe it, the power went out! "Oh no! Now I'm not going to be able to see to get home", Matthew said. "I might have to stay here with you". I chuckled nervously and told him we should wait to see if it came back on. I was a bit cold and so got into my bed, fully clothed. He sat on my bed and we talked in the dark for a few more minutes. The power still hadn't come back on. "Please, please, please can I stay?", Matthew pleaded. "Ok", I said. This wasn't quite how I'd planned to lose my virginity, but what the hell. I wasn't too concerned about pregnancy or anything, because I knew I had already ovulated that month and I also knew Matthew didn't have any STDs. Besides, I wanted to have his babies one day anyway. I could hear Matthew take off his clothes and then felt him slip into my bed beside me. He wasted no time. He leaned across and kissed my cheek and put his arm across my front. His left hand moved up and cupped my left breast. We were then kissing and French kissing and his hand was eagerly massaging both my breasts through my clothes. I was getting pretty hot! He was kissing my neck and he started unbuttoning my blouse, working his way down till all the buttons were undone. He massaged my breasts through my bra. "Sit up", he told me. "Get your shirt off". I did as he told me. I laid back down again and he began fondling my boobs again. He reached around the back, searching for a way to unclip my bra. "It opens at the front", I told him. He found the clip and pulled my bra out from under my back and off completely. "I'll just throw that away", Matthew said cheekily. "We don't need that any more". I giggled. He kissed me and his left hand began caressing my bare breasts. I have very large breasts. I had heard Matthew teasing and laughing at a woman on TV before about her large breasts and so I was a little apprehensive about mine. But he began whispering things to me like "oh baby, they feel soooo good", so I could tell he liked them. And it felt so good for me too, having my tits felt! He kissed my neck and nibbled my earlobe and his left hand worked on my boobs. He tweaked my nipples with his thumb and fingers. It felt so good! I was so hot and I could feel the blood rushing to my vagina. I could feel myself getting really, really wet. I caressed Matthew's bare back, and his face soon followed his hand down to my tits. He started kissing my cleavage in a circular pattern. Then he took a nipple into his mouth and began sucking one breast whilst caressing the other. Oh my God! My heart was pounding. I was moaning softly in pleasure, as Matthew buried himself in my big, bare boobs. His mouth worked its magic, and his hands slid down to my hips. My hands ran through his hair and I caressed his sexy shoulders. I was still wearing pants and Matthew tried at first to slide them down in the dark, but to no avail. He reached to the front for the buckle and unbuckled my pants. He slid down the zipper. "Lift your bottom up", he told me. I did, and he wriggled my pants down to my legs. I pushed them down further and kicked them off. My panties were still on. Matthew reached down the bedclothes and grabbed my pants. "I'll just throw those away", he said. "We don't need those either". Again, I giggled. Matthew pulled me against him and we lay side by side together in silence, my boobs pressed against his chest. We both breathed heavily, caressing each others backs. Then he slipped his naughty hand down the back of my panties and began feeling my behind. He was groping it, as I cuddled him, a little nervously. I'm a voluptuous girl. Not fat, but curvaceous, somewhat big-boned, a Rubenesque, hourglass sort of figure. I have big knockers, wide hips and a rather big bottom. I could tell he really liked my arse. And I liked him touching it. We lay together silently, with his hand squeezing and stroking my bottom. He moved his own crotch against me, and I could feel him move against my pubic bone, as we dry humped each other through our underwear, holding each other lovingly. By now the front of my panties was absolutely soaked. I felt Matthew touch the area between my vagina and my anus, but he didn't touch my cunt just yet. I was about to reach for his backside too, but he retreated his hand and pushed me back down, laying me on my back, kissing my lips and then moving his mouth back down to my breasts again. I moaned in pleasure as my sexy boyfriend sucked on my tits. On my rock-hard nipples. His left hand slid down my body, down to my hips. He slid his hand inside the side of my lacy light blue cotton panties, and tugged them gently. I was breathing very heavily. He slid his hand inside and ran his fingers through my pubic hair. I think he was feeling how hairy I was, and indeed I had quite a bush growing there. Then he retreated his hand and began rubbing my vagina through my sodden panties. I was moaning in pleasure, my whole body tingling. It felt wonderful. I gently held Matthew's head and caressed his back and shoulders until Matthew commanded me rather forcefully, yet in a whisper "get your panties off". I felt my boyfriend take his weight off my chest and I did as he commanded. I slid my hands down to my hips and raised my bottom before sliding my underwear down my thighs. There was a slight sticking from the wetness as I took them off. I wriggled my legs and kicked them off completely. I was now completely naked and I heard the rustle next to me and I knew Matthew had removed his undies and was naked now too. Nervously, I lay on my back in anticipation and Matthew immediately reached across my front again and cupped my left breast. He kissed my cheek and his hand traced its way down my body, from my large left breast, down to my tummy. He briefly felt my navel, and then he slipped his hand down to my vagina. I instinctively opened my legs to give him access. I felt his fingers touch me in my most intimate of places, on my pubic hair, and on my slit. I'd never been so wet in all my life and to tell you the truth, I was a little embarrassed. But I was also really, really excited. Matthew sort of cupped my whole pubic area with his whole hand, the tips of his fingers touching the area between my vagina and anus. Then his fingers moved back to my wet slit. He spread my lips with his fingers. Then he found my clitoris and began to rub it gently, in a small, somewhat circular motion. I moaned softly in pleasure at the sensations. "Is that good, baby?" Matthew whispered in my ear. "Yeah", I whispered back in a gasp, breathing very heavily. My boyfriend was doing things to me that I had never really done to myself, and although it was new to me and nerve-racking, the sensations were pretty incredible. Matthew moved his head back to my tits and sucked on them some more, which only added to my pleasure. I was moaning softly, loving every minute of this exciting, erotic new experience. Matthew rubbed and sort of tweaked my clitoris, which just felt so good. I wondered if I had experienced this thing called orgasm. And then I felt Matthew's fingers move from my clitoris and I felt him inserting a finger into my cunt hole. It was a little tight, but I was so wet and it fit quite easily. My hymen had been eroded by years of tampon use and so I wasn't expecting blood. Matthew slid his finger up and down in my twat and then his thumb began to pleasure my love button again. He continued sucking my tits and kissing my neck and together the sensations were just fantastic! And then he withdrew his finger and removed his head from my boobs, taking his body pressure off my chest. "Hey, come on", he urged rather cheekily. "My pants are off too". I chuckled nervously. I understood exactly what he meant. I had been keen for him to take the lead, after all, he was the experienced one. But I had been a little wrapped up in my own experience, and I hadn't touched his dick yet. Matthew lay side-on and I turned my body to face him. I smiled to myself as I touched my palm against his chest and moved my hand down his tummy and all the way down, till I felt his pubic hair and then I felt this other thing. I took hold of it in my right hand. It was sort of big and meaty and warm. It was quite hard and it seemed to get even harder as I held it. It was quite obviously his penis. I'd never felt a penis in my hand before, although I'd seen a few. And I'd seen a few erections too, in pornography. But it was bigger than I thought it would be, and I wondered how I would get it inside my little hole. (I found out later it's about 7" long, 5½" girth. A nice-sized dick). With my heart pounding, I moved my fingers over it, feeling the texture. It was smooth, and warm, very warm. A really lovely sort of warmth. The end felt different, even smoother and sticky against my palm. It was obviously the circumsized head, covered in pre-cum. Not knowing exactly what to do, I just held his whole dick in my hand for a few seconds. Then I squeezed it. Matthew moaned. So I squeezed it again, and he moaned again. Very curiously now, I moved my hand below his cock, seeking out the rest of his equipment. I knew to be very gentle with a man's testicles. I gently felt his ball sack. It was sort of lumpy and a little hairy. And I was sure I felt these two harder lumps on either side. I smiled to myself and I moved my hand back up to take hold of Matthew's cock again. I held it and squeezed it again. Matthew couldn't wait any longer. He pushed me back onto my back and swung both his legs and his torso over me so he was on top of me. I had let go of his dick and I spread my legs to accomodate him. I could feel his torso against my boobs. "I'm going to fuck you now Pessie, ok?", Matthew said softly. (Pessie is my nickname). "Ok", I whispered back. No way known was there any turning back now! I felt Matthew's right hand slip between my legs. He spread the lips of my twat and I felt the warm head of his penis at my entrance. "I'll penetrate you now, ok?", Matthew said. "Yeah", I replied and braced myself, trying to relax the muscles of my vagina, because I'd been told these should be relaxed when penetration first occurs. I felt Matthew push his dick into me and I gasped at the pressure. He pushed again and I cried out in some pain. "It's alright, baby, it's alright", Matthew whispered reassuringly. "I'll just push it up a bit more". He pushed again and again I cried out. Matthew stayed still for a few seconds, letting me get used to the feeling of his penis in my cunt. My arms were wrapped around him, holding him. I felt him push again and I grimaced and grunted. It was painful and felt uncomfortable, but it was also very exciting. Matthew now had his cock most of the way in and he began to gently thrust. Although it was a bit painful, it also felt good. His dick felt big, hard and very warm and I felt it stretching me like I'd certainly never been stretched before! I began to move my body with him, as he pushed it in deeper and fucked me a little harder. It was a strange combination, this mix of pleasure and pain together. My boobs began to bounce against Matthew's chest as his thrusts rocked my whole body. I was grunting with each downward stroke of his prick. After a short while the pain in my vagina had subsided somewhat, and it began to feel really good. In fact it began to feel really damn good! I spread my legs wider and began to moan in pleasure. Matthew was moaning too, although a little softer than I was. I held him tenderly against me, my hands caressing his back lovingly. I could smell his sweat. He began whispering sweet things in my ear and talking dirty as well, saying things like "I love you so much, Pessie" and "oh baby, your cunt feels so good" and "your cunt's so tight". It was very exciting and enormously satisfying to know that I was giving my man such pleasure. Matthew changed his posture as we rooted. He stroked my hair a bit and kissed my lips. I moaned into his mouth. We were joined as one. I could feel the warmth of his whole body against me, even the beat of his heart. I could feel his thighs against mine, and his chest against my bouncy big boobs. And I could feel his dick, his wonderful warm, hard dick thrusting repeatedly into my tight little twat. My whole body was tingling and I remember throwing my head back at the pleasure. I could feel his hands stroking my thighs and I could feel his right hand slide under my arse and grope it for a bit while he fucked me. I moved my own hand down to Matthew's behind and I squeezed it and felt it. I loved feeling his arse. It was fascinating to observe where all the power of his thrusting was coming from. Each thrust was so pleasurable it demanded another. All along the excitement and the sheer pleasure of my experience felt like it was building up to something. And then after about ten minutes of screwing, I began to feel a more intense tingling deep in my genitals, followed by what felt sort of like a need to pee. It was unfamiliar to me, but I kept moving my hips with Matthew. And then suddenly, wave after wave of pleasure hit me and felt my vagina convulsing. It was kind of scary, but exciting, and enormously pleasurable, far beyond any physical pleasure I had ever felt before! I was whimpering loudly, almost screaming with with the sensations, as my cunt spasmed uncontrollably. The contractions had an immediate effect on Matthew as well. I felt his cock sort of jerk, and then I was sure I could feel his gush of semen, and I certainly heard him groan against my ear, three, maybe four times with the exertion. I knew he had cum, and it was enormously exciting and satisfying. With hearts racing at a million miles an hour we lay together, warm under the blankets, moaning softly and breathing heavily as our orgasms subsided. I smiled to myself as I caressed him in my arms. "I love you, Jessie", he whispered. "I love you too", I whispered back, smiling to myself again. Then we lay there in silence with him still inside me for just a little while, before he whispered "Oh baby, that was amazing". I whispered back "Yeah, it was". We continued whispering sweet nothings and declaring our undying love for each other before Matthew slipped his prick from my twat and rolled off of me. I felt my vagina close back to normal, although the lingering pleasure sensation was still there. I felt Matthew put something in my hand. It was his underwear. "There you are. Wipe your cunt on that", he told me. "Ok", I replied, and did as he suggested. When I had finished. Matthew took back his undies and said cheekily "Mmmm, smells good, baby". I cackled at his naughty sense of humour. And so we lay there together, naked in each others arms. I felt so close to him right now. I felt him reach for my left breast again and just hold it in his warm hand. I smiled to myself, like a very satisfied woman. "So you enjoyed it, hey?", Matthew asked me in a cheeky sort of voice. I giggled again and whispered "Yeah baby, I sure did". "Good. Because I most certainly did as well", Matthew said with conviction. I smiled again to myself. "Wow. That was the first time I've ever had an orgasm", I confessed. "Really?", he asked, surprised. "Yeah", I replied honestly. "Really?!" he asked again. "Yeah. It felt fantastic". "Wow", he said. "What, you've never masturbated or anything before?". He couldn't quite seem to grasp that it was indeed the first time I had consciously experienced a sexual climax. "Not all the way to orgasm", I again replied honestly. "Hey, that's really cool!" Obviously it pleased him to know that his penis had even more significance to me. We continued holding and cuddling each other and talking about what our plans for tomorrow were. I heard Matthew yawn and then he said "Baby, I'm actually dog tired. I'm gonna go to sleep. Goodnight". "Ok", I said. "Goodnight". He let go of me and turned over and it wasn't long before I heard him breathing like he was a in a deep sleep. I reflected on my first time intercourse. I was still really excited by it all and I could easily have done it with him again right then. There was still a slight muscular pain in my vagina from the unfamiliar workout it had received. But sharing myself so intimately with the man I loved was a truly wonderful experience. The added thrill of orgasm made it even more special. Wow. My first ever root. And my first ever orgasm. At the time, that was truly the best night of my life. I fell asleep half an hour later, a very satisfied young woman. Over the next few weeks, whenever Matthew wasn't out of town working, we fucked like rabbits. I learned a great many things from him in that time. Matthew and I broke up about eight months later. I was with another guy for a few months and after that ended, Matthew and I got back together again. We've been together ever since, quite a few years now. Our sex life is still pretty awesome. Sometimes we re-enact our first time intercourse as part of our sexual role-play games. It really turns us both on. I have his ring on my finger now and I'll be having his second child in a few months.