Note: This story is 100% true of my first time with a guy. However I am no longer a goodie two-shoes and have many more stories to share if reviews are positive.
My freshman year in high school was a year in which I changed. I had always been a popular girl, and my father's success as a lawyer led me to private Catholic schools all the way through high school. I wasn't a devout Catholic, but I followed all the school rules and never set a foot out of line. All of that was about to change.
In eighth grade, a year before this story takes place, I really began to develop as a young woman. I was, as I said, rather popular, even before this, but when my breasts really began to grow I became the center of attention for many guys. I befriended them, but being a "good girl" I never did anything more. At the end of the year, I was finally asked out by a guy named Alex. I had never been asked out before, so I said yes, quite excited.
Over the summer we hung out and enjoyed going to friends' parties and the movies, and a whole list of other events. By the beginning of freshmen year we were still going out, and I was as happy as I could be. I tried out for and made the junior varsity soccer team while most of my friends only made freshman. I was voted as one of the four freshman class officers, something that would help me apply for colleges. But it is still a huge transition from junior high to high school. Whenever Alex and I went to parties, usually hosted by a sophomore that we were friends with, I noticed a lot of alcohol and marijuana, something that made me uncomfortable. Many of my friends, however, were fine with it, and eventually started doing things to get the booze they wanted. I pretended not to notice, and I focused on Alex. But he was getting distant, tired of a girl that would barely kiss him while all his friends were getting blown by girls.
It happened one day at school, a Friday. There was a party that night at Mallory's house, and we were going. But every time I tried to talk to Alex that day he always found a way to escape before I could talk to him. I asked my friend Lea, one of the girls that was adapting well, what it meant and she said she thought he was going to break up with me.
"Why would he do that though," I asked, astonished. The thought had never crossed my mind. What more could he want? He had a popular, successful, attractive girlfriend that was infatuated with him. I had even made out with him in front of a group of people at a party!
"I don't know," said Lea. She was about 5' 2", the same height as me, with a smoky voice and large, brown eyes that matched her soft, velvety black hair perfectly. She was one of my friends that had also made the JV soccer team, and she was pretty thin, with very nice sized breasts, about a C-cup. "Do you guys do anything together?"
"Yeah! All the time. We go to the movies and parties, and we hang out together at our housesand all sorts of stuff," I answered.
Lea laughed. I blushed, partly in embarrassment and partly in anger. What was wrong with that? We did a lot of stuff together. "No, no, no," she said when she was done laughing. "Like have you guys done it?"
I blushed again, this time all embarrassment. "No! Of course not. Why would I? Everyone says we're supposed to wait for marriage."
Another fit of laughter. LEa then said, "That's a load of B.S. Faith. Waiting doesn't matter, no one cares anymore. And that might be why he doesn't want to go out with you anymore. You have to keep him interested."
"How do I do that?" I asked. I was genuinely interested--even though I didn't want to lose my virginity, I didn't want Alex to dump me. "Without...sex," I added quietly, fearing that someone in the classroom might hear me.
"Well," she said. She frowned as she thought. "Are you going to the party tonight? The one at Mal's house."
"Yeah," I answered. "Alex is too."
"Can I ask you a question before I give you advice?" she whispered. Without waiting for a reply she continued, "What in the world is wrong with him that you won't fuck him? He's hot and if you weren't going out with him, I'd do him."
My mouth was wide open as she said this. I had never heard her talk like this! "Well, there's nothing wrong with him, I mean I know he's cute but...I'm nervous about sex. What if I get pregnant?"
"Condom," she replied. "Duh!. Use one and you won't get pregnant. I thought you were supposed to be smart."
The conversation continued until the end of class. As the bell rang and we ran out of class, Lea turned to me. "Come over my house after soccer. Text Alex and tell him you'll meet him at the party. We can get ready at my house and I'll tell you what to do"
At 5:30 we finished practice and Lea's mom drove us to her house. The party was at 7, but Mal wanted us there at 6:30, so we were in a rush. Lea somehow convinced me to just shower at the same time as her, that her shower was big enough. It definitely was big enough, and I didn’t want to be late so I finally relented. We undressed and climbed into the shower, helping each other clean some hard to reach places. When we were done we climbed out, and I wrapped myself in a towel.
“I don’t think so Faith!” she laughed. I turned, completely surprised. I had no idea what she was talking about. I asked her what she meant, and she opened a drawer and pulled out a razor. “Take the towel off,” she commanded. I dropped it and followed her finger. She pushed me onto a small stool that was in the bathroom and began to go to work. She shaved of every last hair of what had been a very large bush
“Why did you do that?” I asked. I noticed that between her legs was shaved too.
“Trust me. Guys don’t like it when you aren’t shaved,” she said. “Now let’s get dressed and see what we can do for you.”
We hurried into her room, and she quickly dressed herself in a tight pair of blue jeans with a white and blue Abercrombie shirt on. All the while she told me what to expect, what to do, how to hold it, how to suck it. She was uncomfortable, and still completely nude. Lea turned when she was done and reached into her drawers, searching. She pulled out a black piece of cloth, handing it to me. I asked what it was, unsure what kind of clothing was so small.
“It’s a thong,” Lea said exasperatedly. “Just put it on.” I complied, and pulled the thong up until it was in place. It felt weird, uncomfortable bordering on painful. Lea was slightly thinner than I was, so the already tight thong was wedged even tighter on me. She pulled out a matching black lace bra and handed it to me. I put it on, and found another tight fit, as Lea’s reasonable C-cups were much smaller than my DD’s. The bra pushed my breasts up, made them appear larger than normal. “Good,” Lea whispered. “It’s time you start showcasing those beauties.” Next from the drawers was a pink Hollister T-shirt. I pulled it down over my head, and was definitely uncomfortable with the tight fit around my chest. Then came a skirt, which, thankfully, fit fine and was not incredibly tight. Then she pulled out some black pantyhose and I pulled them up my legs. She wore a simple pair of white flip-flops, but handed me a pair of knee-high black leather boots. “My dad got them in Italy when he went there for work,” she explained. They had a zipper in the back, and I pulled them on. I thought I looked trashy, but Lea was pleased and began to straighten my shoulder-length brown hair. I decided to curl her hair, thinking that it looked cuter than when she straightened her own hair. She then put makeup on me. I don’t pretend to remember all of it, but there was bright red lipstick and mascara. When I looked in the mirror I was amazed at the transformation. I looked a lot older, more mature, and WAY hotter!
“Wow,” I breathed. “You’re the best Lea.” I hugged her, and was pleased to have her hug me back. She hurriedly put make upon herself with a small bit of help from me,and we were ready to go. It was a short ride to Mallory’s house, so we were at the house right at 6:30, greeted by Mallory. Lea’s mom got out to talk with Mallory’s, but her older sister, Jennie, informed her that they had run to the store to pick up some sodas and chips for the party. After that, Lea’s mother left, and we followed Mallory and Jennie back inside.
“They’re not really getting soda,” said Jennie. “They left an hour ago for the weekend. I’m gonna head out now, I have a date.” She grabbed her keys and left the three of us alone until the party started. Lea had already told Mallory, a sophomore, at soccer, and the two continued to tell me what to do with Alex. Mallory was really impressed by the makeup and outfit I was wearing, and agreed that it would drive Alex crazy.
She had already had Jennie, who was over 21, buy her alcohol for the party, and she proudly opened the refrigerator to show us it was filled with beer. There really was soda, as well as rum, tequila, vodka, and some Mike’s Hard Lemonades. They were her favorite. She took out three and opened them, handing me and Lea one. I had never had alcohol, and was nervous about drinking for the first time, but Lea encouraged me, saying it would help with my nerves to have a few sips. I gingerly took a sip and was pleasantly surprised. It was really sour, but I still enjoyed the taste.
It wasn’t long before other people started arriving. The first was Jimmy, a friend of Mallory’s who drove himself. He showed her something he had brought. I couldn’t see what it was, but I figured he was probably one of the guys responsible for bringing weed.
“That’s good shit,” Lea whispered. “Don’t worry we won’t make you try any tonight. How’s the lemonade?” She laughed as I looked down at the already empty bottle. I saw that her and Mallory still had their bottles. I blushed, but she just laughed again.
At around 7:20 we went downstairs into her basement, and I brought another lemonade down with me. By 7:30 there were about forty people at the house, which Mallory told me was just about everybody. I still hadn’t found Alex, but Lea told me to just sit tight and wait—I didn’t want to look too anxious. It took another ten minutes for him to find us, sitting on the couch in the basement. His eyebrows shot up in surprise, both at the bottle in my hand and at my clothes. I stood up and planted a French kiss on him, just like Lea had told me to do. Then he sat down, and I sat on his lap.
People were all over the house, but most of my good friends came down and hung out around where we were already sitting, including Austin, Allison, Bob, Tim and Emily. Then came Mike. He was rolling a blunt, and then lit it before taking one huge, drawn out puff. Then he passed it to Emily. Puff and pass, everyone taking a drag until it got to Alex. He attempted to pass it to Mallory without taking a drag, but I quickly grabbed it. I still don’t know what made me do it, but sitting on his lap I smoked my first joint. I inhaled deeply, imitating what everyone else had done, and my throat got bone dry as I did so. I coughed loudly, passing it on to Mallory as everyone around me laughed. Everyone except Alex. The next time it came around he looked at me before taking his puff. Unlike me, he did not cough, but blew out the smoke. It was obviously not his first time smoking, but I had never seen him do it. I took another drag, making sure that this time I let the smoke out. My throat still felt dry, so I finished my drink, disappointed that it was gone again. I stood up to go get more, but Alex stood and offered to get it himself. He left, and Lea turned to me.
“Damn girl,” she laughed. “I told you that you didn’t have to do that.”
“It’s alright,” I said. I was laughing, but I didn’t know why. “It feels so good!”
“Haha,” Lea laughed at the glazed look on my face. I wasn’t used to the weed, so I was easily twice as stoned as anyone else after only two drags. Lea leaned in closer. “When you finish your next lemonade,” she whispered, “bring him upstairs. Remember what I told you? Just like suck him for a while if you don’t want to go all the way.” I nodded at her.
Alex came back holding an open lemonade for me and a beer for himself. The joint was passed around a few more times before Mike had to roll another one. My drink was getting low again, and I was feeling really giddy. I turned around to Alex. “Wanna go upstairs with me?” I asked as quietly as I could manage.
“I’m fine here,” he said, taking a swig of his beer.
“No. Like upstairs upstairs,” I said. I pointed straight up at the ceiling, and he caught on to what I meant.
“Oh yeah! Sure.” He took my hand and followed me to the stairs. I led him all the way up, past groups of people talking, drinking, and smoking. We went up and I led him into Mallory’s room. It was a huge room, painted pink with various posters hanging from the walls, and in the center was a huge, queen sized bed. I shut the door behind us and we sat on the bed. I leaned in and started to kiss him. It was the most passionate kiss we had ever shared, and my hands wrapped around his neck to support me. I felt his hands, one wrapping around my neck the other at the small of my back. We separated just long enough to breathe before another long kiss. His warm tongue filled my mouth, and mine his. I moaned softly in pleasure at the feeling.
“Why did you want to come up here?” he asked when we separated again.
I froze. I couldn’t do this, I was too nervous! But I looked at his beautiful face, framed by his wavy dark hair, and I knew I didn’t want him to dump me. Forgetting everything Lea and Mallory told me, I answered him by saying, “Why do you think I want to be up here?” His grin showed his sparkling white teeth, perfectly straight, and his blue eyes lightened.
“You mean…you mean you want to have sex?” he asked, astonished.
“I want to take this to the next step,” I answered, mentally kicking myself. It would be hard to get out of here with nothing but a blowjob now. He nodded, unaware of how nervous I was. I reached for the belt buckle, pulling his belt through the loops of his jeans. He was thin, about 160, and stood above me at 5’ 9”. He was muscular though, and when I pulled his jeans off I placed my kinds on his powerful thighs. Then I pulled off his boxers to reveal his cock. It was shaved, about 6 inches long, and already starting to swell up as I gently held it. He let out a deep breath, and I used my tongue to lick all around the head. His breathing got faster as I did so and I could tell he was enjoying this. His cock swelled instantly so that it was easily 7 inches long, and I carefully put it inside my mouth. Lea had used a banana to show me what to do with it, and my head moved up and down, but I took only half his cock into my mouth. Up and down my head moved, and I found myself quietly enjoying the taste. As I took his dick out of my mouth there was a popping noise, and I began to lick the rest of his dick. His head was thrown back now.
“Keep going, baby,” he said, breathless. I gently sucked on his balls, aware of how much it would hurt if I made a mistake. I was relieved that the moaning continued, and I went back to sucking him. His hands slowly pushed my head lower and lower on the shaft, and I gagged. Mal had told me guys liked that, so I did it again and again until I was out of breath. I came back and swallowed the head of his cock, rubbing my tongue around it while it was in my mouth. I began to suck again, and then I tried to deep-throat him again. I gagged, but kept going until every delicious inch was fully in my mouth. Once, twice, three times I did this. The fourth time I felt his muscles tighten, and the first warm spurt filled my mouth. I was completely unprepared and I coughed as I hurriedly took the dick out of my mouth. But the spurts continued, and my face was covered in warm, sticky, white cum. “I’m so sorry, baby,” he gushed. “I couldn’t hold it though and I didn’t want you to stop.”
“It’s okay,” I purred seductively. “I liked the taste of it.” And with that I used my right hand to collect as much of the cum as possible before I swallowed it. The sweet, salty taste was heaven, and it turned me on. I stood and wiggled my way out of the skirt and pulled the tight shirt of to show the sexy black lingerie. It had the desired effect, and his cock started to swell again. I unbuttoned his shirt before pulling it off. “Do you want me?” I asked coyly, slowly turning so he could see my firm ass cheeks in the thong.
“Oh yeah baby you know I do,” he said. He reached up and pulled the bra down to expose my tits. “Get on your knees,” he commanded, and I complied. He took his hard cock and put it in between my breasts and I squeezed them together. His hips started thrusting in between the perky breasts, up and down. This went on for several minutes, and then I could tell he was going to cum again. I was ready for it, hoping for it, and I happily welcomed the squirts of cum that covered my neck and ran down my breasts, which he was still fucking. Then I stood up, and we kissed, my tits pushed up against his muscled chest.
When we separated, I bent over and pulled down my panties to expose my freshly shaved pussy. He was sitting on the bed, and his hand reached forward and rubbed the bald slit. I moaned because it felt so good, and he kept rubbing my clit. Then he bent down and pulled a small wrapped object from his wallet, which was still in his jeans. He opened it to reveal a condom, which he used to cover his shaft. Then he pulled my naked body onto his. I straddled his hips, lining my wet pussy with his dick. My hands were on his chest, and his hips thrust up. I felt something in me pop, and my crotch erupted in pain. I whimpered, feeling a trickle of blood run down my leg.
“Do you want me to stop?” Alex asked.
“No. Keep going.” I knew I couldn’t start this and then stop. Lea and Mallory hadn’t told me about the pain though, and I was angry with them at first. But then I realized they must have done it so I wouldn’t be afraid, and I silently thanked them, knowing I wouldn’t be doing this if they had told me.
Alex’s hips kept thrusting in and out of me and the pain started to go away. It was replaced by a feeling that was nothing less than ecstasy, and I ground my hips into his in the same rhythm as his hips moved. Moans were escaping my lips as I bounced up and down on his cock.
“Harder,” I said.”Fuck me harder!!” I was yelling now, telling him to go faster, harder, deeper into me, and he happily complied. My moans were slowly becoming screams of delight and my nervousness was completely gone.
It took nearly ten minutes of pure, blissful, ecstatic sex for Alex to cum again, and right before he did, I reached my own orgasm. My muscles tightened, and looking between my legs I could see a river of my own juices flowing down his cock. As the orgasm faded, I rolled off his cock and onto the bed next to him. We shared a long, passionate kiss, our tongues as intertwined as our bodies were. I broke off the kiss and gave him an impish smile as I moved down to his now flaccid dick. I peeled the condom off, tossing it on the floor, and I sucked all of the cum and my own juice off of his cock and balls.
“Do you want to go again,” I asked him.
“Give me a minute. My balls are sore. Anyways that was my only condom.”
“Well,,,” I was nervous to state what I wanted to do.”What if we..you know.. have anal?”
“What?” he asked me incredulously. “Are you serious?”
“Well I thought we could, I mean that way we don’t need a condom and we can still have sex.” My voice was defensive, even though I didn’t want it to be.
“Do you really want to?” he asked. “I mean we can have sex another time to if you want.”
“We’re already here though. Let’s just do it and if it’s not good we don’t have to do it again,” I answered.
He relented, and I got on my knees, leaning forward unto my elbows. I looked back at him and flashed a reassuring smile. I felt his hands cup my ass. Next I felt his dick as he rubbed it around my asshole. “Do it!” I commanded, and he shoved the long shaft into me. it felt good as he went balls deep into my ass. I was moaning again, and he grunted as he went hard and fast into me. “FUCK!!” I screamed in ecstatic bliss, “ME!!” I started playing with my glistening wet pussy. He fucked until, simultaneously, we had another set of orgasms, and he blew another load in my ass. He collapsed on top of me, and I cupped his balls. “These did a great job tonight baby,” I whispered. “Let me clean them off.” But even my careful cleaning of his cock, with my mouth of course, could do nothing to raise his dick again. He was asleep in minutes, and I dressed and went downstairs to rejoin the party, where I showed everyone I wasn’t going to be the goody two shoes anymore. I drank tequila until my top came off and everyone saw my tits, and was introduced to my new best friend, a bong.
Note: Again this is 100% true and I definitely want to write more stories if this one is well received. Leave comments and I’ll write another one :).