First of Many by emerge

Rating: 88%, Read 26422 times, Posted Nov 27, 2009

True Story | First Time, Teen Female, Teen Male, Virginity

I had lost my virginity when I was 16, by surprise on a Saturday. I was the singer and guitarist of a band. Our bassist and occasional vocalist when needed was a longtime friend of mine, her name was Sophie. We had known each other since we were little, and though we had changed a lot once we were in middle and high school, we continued to talk to each other pretty often. I was usually a pretty shy person, I had only had one girlfriend before, and other than Sophie, I didn’t have that many female friends. I had not even wanted to be in a band regardless of how good of a singer I was due to my shyness, but Sophie was easily able to convince me otherwise. Cute girls are pretty convincing. But it had been almost a year, since when we were 15 and started the band in the first place. She was not only cute anymore. She had grown very nicely.

We were originally supposed to have a band practice that Saturday, but I was told Dan and Rochelle, our drummer and other guitarist weren’t going to be able to come. Sophie told me to come over anyway to practice some acoustic stuff together. We had been up in her room for about 20 minutes or so, working on some songs that we would be playing at some coffee shop in two weeks. We generally played our acoustic performances just as us two, so it sort of worked out. She was a talented person, so she managed to play guitar also. After finishing a song, she suddenly decided to put her guitar down back on to its stand next to her bed. Her guitar, though black and shiny, seemed almost completely clear of any blemishes or even fingerprints. Her care for her guitar was similar to the way she took care of herself. She always looked good whether she was in her pajamas or fully made up and in a dress.

“Talk to me for a little bit,” Sophie said, with one of her trademark smiles. Something was probably up. She closed the door to her room and locked it. “It probably would be a good idea to do this,” She said.

“Locking the door?” I asked, putting my guitar back into its case. “What are you doing?”

“I just have to ask you a question. It’s about you and Lauren.”

I had broken up with Lauren, my ex-girlfriend of two years almost a month ago. Sophie and Lauren were pretty good friends.

“Did you two ever have sex?” She asked.

I was not prepared for that question. “Well, we went out for two years,” I said, stammering slightly. We had been going out for that long, and had done other things, but neither of us felt comfortable trying it.

“Since you didn’t say yes, I’m just going to go ahead and assume that you never did.” Sophie said.

“Yeah.” For some reason I felt ashamed, even though I knew it would probably have been a bad idea.

“Well, of course I didn’t think either of you would take the initiative,” Sophie said. “No big deal if you’re worried about me judging you. I was just wondering since Lauren wouldn’t tell me. Did you two think about sleeping together?”

“We actually almost did once. Both of us were too scared to actually do it. I guess we felt like we were too young I guess.”

Sophie nodded her head, her silky black scene-styled hair brushed against her cheeks. It looked cute with her pale white skin. Today she was wearing a very tight black t-shirt, with no design on it. The lack of a design made her perky tits look bigger than usual. Though she was usually one to wear skinny jeans, today she wore light gray sweatpants, also form-fitting. She looked good in almost anything she wore.

“So, would you fuck me?” Sophie asked, moving her face very close to mine.

I didn’t know what to say. Half of me hoped she was only teasing me, like she does to almost everyone, but then the other half was dying to do it.

“What?” I asked. I had heard the question, but I asked anyway.

“You heard me, Ken.” She moved her face, almost pressing her lips against mine. It was not a kiss, but the slightest movement of either of our lips would cause it to be one. “Would you fuck me, right now. That was the question.”

It only took another couple seconds of staring at her body that caused my intent on ramming her into a wall to take over completely. I didn’t care if it was a trick or not anymore. Looking back, I didn’t even think to ask why she wanted to.

“Yeah, definitely.” I said.

“Alright then, but you’re going to do exactly what I tell you to do,” She said, once again with a trademark smile. “Kiss me.”

I barely had to move my face forward for our lips to make contact. I immediately felt euphoric with our mouths pressed together, but it was only going to get better. I put my arms around her waist kissing a little more forcefully. We broke apart for a second. I was scared I had messed up or something.

“Scared to touch my ass, huh?”


“I know you fucking want to grab it. You look at my ass more than anybody else I know.”

That was somewhat true, especially when she wore sweatpants like she was right now, it was almost impossible not to look. It was something that you just felt like you’d have to touch. It wasn’t enormous, but she was skinny enough to make it look great on her.

My hands moved down to her ass slowly. I felt the soft fabric of her pants, and the warmth on the other side. I had always wanted to do this. We continued kissing for a little less than a minute. Sophie started to pull off her bra from inside her shirt.

“Hate these,” She said, tossing it onto the floor. Her nipples were now fully visible through her shirt. “I bet you want to see my tits now, huh?”

I had actually seen her boobs before. I hadn’t in the past couple of months, but she always enjoyed changing in front of people when they were over her house, and she had also sent me a couple of pictures through texts. I knew for a fact that she had gone up at least one cup size since I had last seen them, I had noticed the chest area of her shirts getting bigger recently. I felt like my cock was going to burst through my pants because of how hard it was getting.

I slowly made a motion to touch them. I guess my approach seemed a little awkward.

“It’s not like defusing a bomb, you goof. Did you and Lauren do absolutely nothing in two years?” She asked.

It wasn’t entirely true, but it was different because Lauren was my first girlfriend ever, and I was her first boyfriend of longer than a week. Neither of us were very experienced in what moves to make, and when. Sophie was a different story. Though she had claimed she only had full on sex with one guy before, she was certainly a tease to just about everyone, and she had exchanged oral with plenty of guys and apparently even girls while drunk.

There was a tiny bit of cleavage in her tight black shirt. I pulled it down a little more, revealing more of her breasts. I felt them softly for a little bit and then pulled off her shirt to get a full view. She was gorgeous without a shirt. She was athletic, a track runner, giving her a wonderfully flat stomach. There was even a tiny bit of muscle there, but nothing to make her look manly. Her perky tits popped out. They seemed as large as they could possibly be to remain perky. The fact that there was no drooping or sagging made them unbelievably nice. I put my hands around them, and then lightly pinched her nipples. She giggled.

“Oh my god,” I said. “Why are you letting me do this?” In truth, I might’ve known the answer. She was one to get viciously horny, something that her own hand would not satisfy. She needed somebody else to pleasure her, or even just pleasuring somebody else would do it for her.

“It’s fun,” She said, brushing her hand through her hair, and then moving down to undo my belt and unzipper my pants. I continued to play with her nipples, and occasionally she’d close her eyes and look up for a bit, opening her mouth slightly, letting out a barely audible moan. She finished with my pants and she pulled them down, revealing my erection through my boxers, clearly trying to break out. I took off my shirt on my own. I wasn’t big at all, but I worked out occasionally and had more toned muscle and visible and abdominal muscles.

“I’m liking the body,” She said, giggling again. “The cock could be better.”

I was maybe 4 inches at the time, probably smaller than most of the guys she had seen before.

“But it won’t stop me from doing this,” Sophie said, taking my cock into her cute little mouth. She definitely knew what she was doing.

I groaned. It felt amazing. “I hope you know I’m not going to last very long at all, I don’t do this often and you’re fucking awesome at this.”

“Oh, I don’t mind,” She said, with just the tip of my cock in her mouth. Her speaking seemed to send vibrations through my cock and the rest of my body. “But if that’s the case,” She spoke between lunges “We’d better get to the real shit.”

She took off her sweatpants, quickly revealing black panties which she took off right away. It would be my first of many glimpses at her pussy. Not a hair was in sight, and her pussy lips puffed out. I couldn’t believe what I was about to do. It was that moment I realized that Sophie was probably the hottest girl that I knew, and somehow I was about to have sex with her.

I moved two fingers to her already moist pussy, inserting them. It was so tight and warm; I was only imagining how great my dick would feel in there. I pulled them in and out a little bit, testing around. I would probably have to do this anyway because I felt like I was going to explode while my dick wasn’t in any one of her orifices.

“You don’t have to do that, you know,” Sophie said. “I don’t mind cumming on my own after. I just want you to lose your virginity to me, right fucking now.”

“Are you really sure?” I asked, still lightly fingering her pussy.

“I’ll be teaching you to last longer later. That’s not what matters right now.” She said.

I pulled my fingers out, and she flopped onto her bed, on her back. Her legs hung over the mattress, her shaven pussy fully exposed.

“Fucking stick it in me, now!” She shouted.

I listened to her as I directed my cock to her pussy. It was already quite moist so it went in easily, but it was still tight. Nothing had ever felt like this before. I must have left it in for maybe 10 seconds before I started to thrust back and forth.

“Oh my gooood yes!” She shouted, louder than I had ever heard her shout before. “That’s how you do it! Fuck me harder!”

I wondered if anybody else was in the house at the time. Sophie had locked the door for a reason. But at that exact moment, I didn’t care who heard us, I didn’t care if Sophie’s parents found out and both of us would get in trouble.

I continued to fuck her, eventually finding a good rhythm. She continued to moan loudly in extreme pleasure. It wasn’t long before I started to feel myself starting to tighten up, I was breaking my own rhythm and ready to cum. I didn’t have to say anything; the look I gave her told her what was going to happen.

“Inside me!” She shouted.

I heard her instructions, but I exploded on my way coming out of her pussy. The orgasm felt completely different from masturbation or getting a blowjob from my ex-girlfriend, and the load of cum that came out also was also much, much more. The cum splattered against her pussy lips, and as more continued to come out. I attempted to put my cock back inside like she instructed, but I had little control and the rest of the cum landed on her stomach and tits. With her hand, she scooped up some of the cum and placed it in her mouth.

“Mmmhm, You may not have the biggest cock, but that’s a lot of cum,” She smiled. “I’m actually pretty happy this wasn’t inside me right now.” After tasting a little more, she grabbed a tissue from her nightstand and cleaned up the rest on her body. She then started to rub her own pussy, her fingers moving quickly in a circular motion.

“Are you sure you don’t want me to help?” I asked.

“You don’t need to. It’s your first time and not mine. I’ll be teaching you to last longer, don’t you worry,” She said, nonchalantly, but rubbing her pussy furiously.

She orgasmed soon, with her back arching up slightly. I mainly watched her face grow a smile of extreme pleasure. I thought at that moment I would want nothing more than to give that to her.

“Let’s get out of here,” She said, putting her clothes back on.

I put my clothes on and we left the room. She went into the bathroom to clean herself up, but I continued to walk through her house into the living room. There I spotted Sophie’s sister on the couch, tears streaming down her face. She looked at me for a second but quickly turned away. I didn’t know what to say. Did this have to do with what just happened?

Rating: 88%, Read 26422 times, Posted Nov 27, 2009

True Story | First Time, Teen Female, Teen Male, Virginity


Login to join the discussion