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Losing My Virginity

The true story of how I lost my virginity.
My name is Lexy and I had just moved from a more rural area to the center of a very unpleasant Florida town. On top of not being fond of the town I lived in, I didn't know anyone in the area. A few months earlier while I was still at my old house I went to a gathering in the area of town where there are three or four bars on one block, it was called "Friday Night Live". While I was there I met a 6'2" goth boy named Chris. From what I could tell he was toned and had straight black hair that was side swept over his bright blue eyes. Nothing came of it, but I enjoyed his company and we laughed most of the night away. When we departed we exchanged social networking names and email addresses to keep in contact.

After I moved to this new town, I remembered our encounter and decided to contact him. That night he came to pick me up in his Blazer. I had to sneak out after my mother went to sleep because I knew she wouldn't approve of me going off with some boy I didn't know at barely sixteen years old late at night. This encounter went just like the last one only this time when I went to get out of the Blazer he kissed me. I responded with pressing my lips back into his, parting them slightly to invite his tongue to glide across mine. I think he was trying to be sweet, because it only lasted a few seconds then he pulled away and kissed my cheek and told me he hopes to see me again.

We hung out for a few weeks and by then I spent a lot of time at his parents house being it was summertime and there was no school. I probably saw him five days out of the week. His mother seemed nice enough, and his sister was a few years younger then me but really enjoyed me being around to give advice and such.

School started so I had to start seeing him after school and return home at evening time. Most of the time we would just hang out in his car or his bedroom at his house and watch movies, occasionally walking the waterfront. One day we were driving around like we always did and he told me to call my mother and tell her that I would be home later then I expected because Chris' mother wanted me to stay for dinner and that they serve it between 6:30 and 7:00 p.m.

After calling my mother and getting the "A-okay" to be out later, Chris pulled into a local convenient store called "Jiffy" and said he would be right back with drinks. I watched him walk back out with a grey grocery bag in his hand. There was what looked like a Monster Energy drink (what he drank all the time), a Vitamin water (what I drank all of the time) and an unknown black box. From the angle the bag was turned there was no way to be certain but I had the feeling that it was a box of condoms.

He reentered the car and set the bag down in between our seats.

"I got you a vitamin water, the chamomile one. I remember you getting a pink one last time but I couldn't remember the name."

"That's fine, you got it right. Thank you!"

I reached down between the seats and into the grocery bag. As I pulled out my drink I snuck a peek at the box. I was right! It was condoms. Not only were they condoms they were Trojan Magnum XL! That scared me and my heart started pounding through my chest. All sorts of thoughts rushed my mind "What if I do it wrong? What if it hurts too much? He has to be big to need those! What if I make a fool out of myself? Does he plan on going back to his house? His mom and sister are home!"

Although all of these thoughts were racing through my mind I decided to pretend I didn't see the condoms. Who knew, maybe they were for another day and he picked them up because they were on sale. Maybe I was just over worrying myself. He helped me break my train of thought when he turned up the music. We were listening to "The Used".

He pulled out of the driveway of Jiffy and started heading towards his house. On the street he was supposed to turn right he instead turned left. Being worried that he accidentally went the wrong way home I told him that we were supposed to go right.

"I know where my house is. I thought instead we might just go hang out at the park and drink our drinks and spend some time before you have to go back home."

"We're not having dinner at your house?"

"I'll buy you McDonald on the way back to your house. You can get your usual yogurt and large fry."

"Okay, but wont your mother be mad if we don't show up?"

"My mother isn't cooking dinner. I just thought it would be a good excuse to tell your mother so that we could hang out more."

"You sneaky little bugger you," laughing in disbelieve of how naive I was.

Within seconds we were pulling up to the park. Not many people went to this park, as there were many better quality parks within two miles and most people went to those. There were probably a hundred pine trees of a kind I had never seen before. It was also equipped with two tennis courts and a small play ground.

The sun started falling lower in the sky and it made him suddenly more attractive. The lighting made his eyes glisten as he nervously darted them around the interior of the Blazer. To break his own nervousness he started to poke fun at me and tried to tickle me.

As it always did this ended up with us kissing. As he raised his hand and ran it through my hair he put pressure on the back of my head to pull me in closer. The kiss became more passionate going from sweet little touches that barely tickled each others tongues to a forceful rhythmic kiss, lip biting and all. As this continued on he put his hand on my side to coax me over on top of his lap between him and the steering wheel.

As we kept making out he started to rub his hands up the back of my shirt and down my sides. I could feel something between my legs start to tingle and throb. Out of impulse because of how horny I was getting I arched my back pushing my ass slightly backwards making me able to push my vagina into his lap to give myself some stimulation before I went nuts.

I didn't think he would notice that I had done that, but he did. He started rocking his hips upwards causing his already erect penis to rub right up my slit. Although we were both clothed this was an amazing sensation. I responded to his action by matching his beat and grinding up against him. He broke away from our kissing to change the song and complain lightly about the position we were in.

"I'm getting uncomfortable being crammed with two people in between the seat and the steering wheel, do you mind if we move to the back?"

Looking back I noticed that the back seats of the Blazer had been folded down. I wondered if this was just coincidence or how long he was planning on this to happen.

"Sure we can." I crawled between the seats and went into the back and sat Indian style facing the front of the car to watch him. He crawled through as well and kept moving into me, putting his hand on my shoulder, kissing me, pushing me backwards so we were laying. I was on my back and he was on his side so I rolled over so that we could talk face to face.

He laughed "So how are you?"

"I'm doing good, a little confused, but good."

"Let me know if you start feeling anything besides good, okay?"

"Sure, Why would I feel anything worse then good. We're having a lovely time."

"Just making sure, Lexy."

We went back to kissing only this time he put his hand on the small of my back and pulled me into him. Our whole bodies were touching and he pushed his top leg in between mine forcing my top leg to also bend. Both of our bottom legs were straight with the top ones bent causing a great position for him to keep grinding into me but this time just with his thigh, not his penis as it was no longer erect.

He put pressure on me making me roll over to my back and he laid half on top of me half on his side, and trailed his hand around the hem of my pants. You could tell he was contemplating if I would allow this to happen or not and he just took the plunge and dove his hand into my pants and panties.

He matched our kissing to the motion of his hand, pressing down firmly on my mound and vulva rubbing it. Soon enough he took his middle finger and pushed between the lips close to my hole but not quite touching it. From there his finger got moist allowing him to glide his finger up the slit of my vagina and over my clitoris. Once he ran over it he started making little circles. At first lightly and slowly. I let out a small sigh of pleasure. As he started picking up the pace and the pressure, my breathing got more sharp and ragged until he stuck his finger inside bending his finger to press on my g-spot making me moan aloud. He continued the process and did the same thing with my clit, building intensity.

After five minutes I couldn't quiet myself. I was dripping wet and my juices started to soak through my panties into my pants. He decided to tug my pants off and I grabbed the back of his shirt to pull it off. He then took his own pants off. When his pants came off his dick sprung into attention after being tucked away in the waistband of his pants, I assume to not scare me. He had a full six pack, almost eight pack, and very toned arms. This turned me on even more, as if that was possible.

I tugged at his dick through his boxers and I suppose we just decided "screw it" and took both of our undergarments off. At this point I was so nervous I was just following along with anything he did while showing some hesitation. I was all too scared to initiate anything myself. Before he laid back where he was earlier while fingering me, half on top of me half on his side, I took a peek at his raging boner. It was about four of my fingers wide and 8 1/2 inches long. He resumed the same position and I turned to my side and I could feel his hard dick press against the crease where my leg meets my body.

He went back to fingering me.

"Fuck baby, You're so tight," he said, as he pushed a second finger in.

I moaned in almost a yelp.

He started to kiss my chest and neck as he fingered me slowly positioning himself in between my legs. He reached back to grab the box of condoms. They were in shiny gold wrappers. He looked at me looking for permission, and I nodded my head in approval. He ripped the condom open with his teeth and slid it onto his dick. He kept fingering me and just started rubbing his dick between my pussy lips. He removed his hand to push down on his dick so I could feel the head running back and forth over my clit with force. I started moaning harder.

He then positioned his penis at the entrance of my hole and started putting pressure. It didn't hurt as bad as I thought it was going to, I just felt really full. I felt as though if anymore was inside of me I would explode. He pulled out to the entrance and back in, going slightly farther this time. He kept doing this inching his way deeper and deeper into my warm soaking wet insides. I could feel the tightness around his dick resist him from pushing forward but he did anyways. He then got to a point where he couldn't get in any farther. He leaned down to touch his mouth almost to my ear and whispered.

"This may hurt. Hold your breath and tough it out. After a few seconds it wont hurt anymore or be nearly as uncomfortable."

I kissed him and pushed my pelvis up towards him showing him that he could push through it. He did in a fairly quick motion and he was right, it did hurt. He held his whole body still keeping his penis inside of me. Once I stopped clenching my eyes shut he started slowly but surely pumping into my pussy.

It now started to feel good. He was so big every centimeter of my vagina was being stimulated all at once. I couldn't help but to moan and claw into his back pulling him into me harder. He took my cue and started increasing his speed and pushing harder into my cervix. I could feel his rock hard cock pulsating with pleasure from my tight virgin pussy. His glands were so enlarged I could feel them as they passed over my g-spot followed by his pelvic bone hitting my clitoris.

I started to feel a building in me and then muscles inside of me started pushing outwards. Chris had to fight back and push against the muscles. This made me even tighter then before and he started fucking my wildly as if it was to save his life. My head started to clink against the back hatch of the blazer. I used my hands to push my self back towards the front seats of the car, and into him. This gave stability and he fucked me so hard with unbelievable speed paying attention to angle his cock to press on all of the places that drove me crazy.

By this time I was almost crying it felt so good. I moaned out his name repeatedly as I felt something building within me again. This time I wasn't distracted by my head hitting anything and it kept getting more and more intense making my pussy grip his raging dick harder. My eyes rolled back into my head as I started to cum. I squirted all over his dick and balls, and down the floor of the blazer. He pulled his dick out of me and asked me to sit up and open my mouth . I was in such a state of ecstasy I would do whatever he said. Before I could even get all the way up, cum was squirting across my face, into my throat, in my mouth and on my tits. I couldn't believe someone could cum that much!

Once the wave of extreme pleasure passed over us we started getting paranoid because we were on a public road lined with houses at a park! We got dressed in a hurry and climbed back up and into the front seats. He got me my McDonalds and after we chit-chatted and joked around for a while, then he drove me home. I kissed him goodnight and couldn't stop thinking about what happened earlier that day for the rest of the night.

Authors Note: This is my first story, and it is about how I lost my virginity in real life. Hope you guys enjoyed it. Please be easy on me as I've never written anything before!
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