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My first story begins with Val, the story of how he lost his virginity. Believe it or not, but this is what he said…
There were three Megans: Megan M., Megan H., and Megan W., Each a different personality, clique and look.
Megan M. was a tall, slender, attractive girl; she had a light brown hair that went to just below her shoulders and light brown eyes. She was very athletic, Varsity Soccer and Volleyball. She was a shy girl who had the kindest of voices. She was the kind of girl whose voice you never minded hearing. She didn’t have the largest breasts, but her tight uniform shirt always made you want to see more. She didn’t have the biggest butt, but her skirt could never be too short.
Megan H. was a shorter girl, around five feet tall, she was one of the more popular and outgoing girls. She had dark brown hair and dark mischievous eyes. Megan H. had breast that were barely b-cup but that was fine, because she was sexy as hell anyways. Even the way she talked could turn you on, and just about everyone that hung out with her had fantasized about being with her, even the girls.
Megan W. was shy and brainy. She was the kind who did chess club and robotics. She had long dirty blonde hair that went to just below her shoulders, and light blue-green eyes. Just because she was nerdy did not mean she wasn’t hot, she was thin with b-cup breasts, she was also a little above five feet.
Val was not the most athletic guy; he was around 5′ 10″ and wide shoulders. He wasn’t fat, just naturally wide with a little muscle. He had light brown eyes and dark black hair. Val was also one of the smarter kids, AP classes and higher level math, you know the type. From what he says, he is around 7″ long and 1.5″ wide.
Enough descriptions, let’s move onto the actually story.
Megan M. and I had our first and last classes together. We never ran out of things to laugh or joke about. It was nice to start and end days with that kind of humor. Our first hour was Theology, a private school (remember?), and on that particular Monday we were missing class to watch another movie on how bad sex and masturbation was, and how we should save our selves, the usual. Megan and I sat in the back row, avoiding as much of the crowd as we could, so we wouldn’t get scolded for our comments and laughing. The teacher didn’t mind too much, mainly because he had started to doze off before the intro was over. For the most part it was just the same-old cheesy movie that showed how “dangerous” sex could really be and how sinful it was. Both of us laughed at the quality and budget the movie was made with.
Then it hit the second topic, masturbation. It talked about porn, and I saw a lot of guys start to shift uncomfortably. A scantily clad ex-porn star started going on about how bad she felt about being in the industry. I quickly adjusted to give my boner more room. Megan noticed and quietly laughed, starting to make jokes about my “pre-dick-ament”. I looked her in the eyes and quietly said
“It’s no laughing matter; it hurts a lot when left unattended. From what I understand, if left too long it can be traumatic”
That’s when things too an odd turn.
“Well I really don’t want you to be in any kind of pain!”
That’s when in one swift move, she looked at the sleeping teacher, unzipped my pants, and unleashed my cock. It was almost fully hard, and her soft tender hands were helping to wake it up.
While still looking like she was watching the movie, she made sure no other students or the teacher could see what exactly she was doing.
She gently squeezed at the base and brought her hand to the tip. Within seconds my cock was so hard it actually hurt, she kept gently stroking it, making sure she hit the bottom, then the very tip. It was then that she very innocently looked up at me and asked
“Doesn’t cum shoot out near the end?”
Being in such bliss I was hardly in any position to do any kind of thinking, I found the will power to nod yes.
“We can’t have it shoot out all over my school shirt and arm!” she whispered.
I realized she had a point, double checking to see if anyone herd, I looked her in the eyes and said
“Wait, what if you swallow it? It would take care of the mess.”
Her eyes widened, she seemed excited to try that. Doing one last double take, she plunged her head into my lap and gave me the best (and first) blowjob ever. She went slow, taking about half, then coming up to the tip and plunging down. She kept this up for another minute or so, before I started to feel my balls tighten.
“Megan, I’m about to cum.” I quietly warned her.
She popped her head up and tightly squeezed the base of my cock, man did that hurt.
“I don’t want to end the fun just yet.”
She zipped up my pants and motioned me to follow, being near the back we were able to sneak across the hall to the bathrooms without being herd. We snuck into the second girls stall and started madly and passionately kissing. Her tongue plunged into my mouth and wrestled with mine, then explored every nook and crevice in my mouth. I reluctantly moved to kissing her neck madly.
I quickly removed her shirt and bra and sucked on each of the beautiful mounds, first around the nipples and then right on them. Then I slid her skirt and panties to her ankles and started kissing her pussy. My tongue explored the walls, and then it hit something, her hymen. I quickly stood up and asked her
“Megan, are you sure you want to go through with this?”
She looked me in the eyes, with an almost pleading look in her eyes, I automatically knew the answer. I gave her a quick warning about how it was going to hurt, removed my pants so I didn’t get blood on them, and then lifted her up. With my left hand holding her weight I positioned my cock to her pussy, started a kiss and then I dropped her down. She screamed in my mouth, I let her become comfortable with the size, then started to slowly fuck her. I lasted a good minute or so before I felt that familiar tingling. I warned her again.
“Cum in me.” She ordered.
I didn’t need to be told twice and unloaded spurt after spurt. I set her down on the toilet and wiped off my cock. I grabbed some more T.P. and wiped off excess semen. I gently licked her outer lips, finally getting a chance to get an up-close look at her pussy. It was a brilliant pink with a finely groomed landing strip of light brown hair. I went to work licking the outer lips and flicking her clit with my tongue. After I cleaned her up and we both got dressed, we snuck back into the auditorium. Man was I glad I brought gum.
The movie was almost over and no one seemed to notice we were gone. They were going over the consequences of pre-marital sex, and of course Megan and” I giggled, when something they said made me think. Teenage mothers.
“Shit!” I whispered.
“What?” Megan quietly asked.
“I came inside you, are you on the pill?” I was really worrying, I was not ready to be a dad, and I sure as hell knew I wouldn’t just leave Megan.
“Its fine,” she said, “I am on the pill, and I’ve been on it for almost a year now.”
“Phew” I said. Dodged that bullet, I thought to myself.
The bell rang and I walked her to her locker, the entire way talking about nothing in particular.
I replayed what happed through my head over and over during second hour. I was excited to see where this relationship was going. I was so lost in thought I was having a really hard time paying attention. After second hour I walked to my locker and exchanged books, all with my head in the clouds. And that?s when it happened.
“Shit!” Megan H. said.
“Whoops sorry.” I replied, my head was so high in the clouds; that I accidently bumped into her and knocked a few of her books down. I helped her pick up her books, because we had the same third hour I walked with her to class.
“You ok?” She asked, “You seem kind of out of it.”
Man she had no idea.
“Yeah, I’m fine. I just had a hell of a morning.”
Megan H. and I were good friends. We had third and fourth hour together, and shared a taste in music. We talked about upcoming bands and some small talk about classes.
We headed on to Spanish, fourth hour together. Our fourth hour was an odd one, it was split into three 30 minute sections; we had class the first and last part, and a lunch break in the middle. We continued talking about music, discussing the work of Miike Snow and Green Day, their older stuff. That’s when it happened.
“Val, are you still a virgin?” She asked.
I just had to avoid the topic for another minute or so until the lunch bell rang.
“I…uh…um…” I stuttered. Man I was sweating bullets and nervous as hell.
“It’s ok if you are, I’m just curious.” Then the bell rang.
Phew dodged that bullet. I started to get up and walk to the lunch room when she tugged at my shirt urging me to stay seated. After everyone had left the room, teacher included, she asked me again
“So are you a virgin?”
I started to stutter again, I looked into her mischievous eyes and saw that she really wanted to know. I was stunned; I froze and didn”t know what to do. She helped me with that. She guided me to my feet and into the hall. She pulled all the way to the end of the school that students hardly went to, near the auditorium. She pulled me to the women’s restroom and into the second stall over.
Still frozen I mindlessly followed her; curious to see where this was going. She positioned me in between her and the stall door. She sat on the toilet and unzipped my pants. She maneuvered my cock through the underwear and out into the open. Even though I had just fucked this morning, I was practically hard already.
I could feel her warm breath on my cock. She gripped it and started pumping faster and faster, working to get it as hard as it could be. She then took it into her mouth. All seven inches. In one thrust. To say I was impressed was an understatement. She wrapped the bottom half with her tongue and moved it left and right all while deep throating it. I really didn’t know how long I would last if she kept this up. After a few more minutes of this bliss, she stood up.
“I guess I get your V-Card, huh?” She said.
I didn’t reply at all, I just turned her around, lifted her skirt and started massaging her ass. I moved her panties out of the way so that I could admire all of her. I gently used my pinkie and ring fingers to finger fuck her. I started very slowly and built up speed; once I was about mid-speed I extended my pointer finger to start to massage her asshole.
“Shit!” I could hear her gasp.
I pushed harder and harder until I penetrated her puckered hole, I could feel both her pussy and asshole tighten as she moaned in bliss. I just gave a girl an orgasm, I thought to myself.
While she was leaning over I positioned my cock to her pussy, and pushed in. After a few thrusts I figured I was lubricated enough and stopped.
“What the hell!” She yelled at me “Why the fuck did you sto…”
She went silent as forced the head of my cock into her tight asshole. As I went deeper and deeper into her bowels Megan H. started moaning louder and louder. I reached to her front and started fingering her clit. After a few minutes of this I felt her sphincter start to tighten. It was well more than I could handle. I came pretty hard. Spurt after spurt flooded into her, I lost count after 10. As my cock started to limp, I pulled out with a satisfying pop.
Copying what I did earlier, I grabbed some T.P. and cleaned off my dick. Grabbing more, I knelt down to Megan’s bum and started to wipe off the excess jizz. I then proceeded to lick it extra clean. Once again glad I had some gum.
After both of us got dressed we headed to our lockers, which were right by each other, and grabbed our lunch.
“So, what did you think of it?” She asked me.
“Fucking amazing, and what did you think?”
“Well I’ve never had anyone in my ass before, but that was fucking amazing.”
“Huh, so I popped you anal cherry? A cherry for a cherry I guess?”
“Yeah I guess so. Just remember, anytime you’re pussy hungry before lunch?”
“I’ll make sure I keep you in mind.” I stole a quick kiss then walked to sit with, friends and Megan with hers.
“The fuck was that Val?” My friend Brian asked as I sat down.
“Don’t worry about it man.” I said as I scarfed down my lunch.
The rest of the lunch went by pretty quick. For the rest of the day I thought about how I go to fuck two of the hottest sophomores in the school, within five hours of each other. I was on top of the world. The rest of the day went pretty uneventful. It wasn’t until I went to seventh, the last, hour that I got to see either of the Megans. Megan M. was sitting in her usual spot right next to me. There was a test so we really didn’t talk that much, but I did get to take in her looks quite a bit.
After the test I walked her to her locker and had some small talk. I told her I’d see her tomorrow, then headed to my locker grabbed my backpack and headed out the door. I saw Megan W. Standing next to her car waiting for me. Megan W. was a year ahead of me, a junior, and had given me a ride home since last year.
“Hurry up Val, I haven’t got all day.” She called over to me.
“Ok, ok I’m hurrying.” I called back.
She drove an old white Honda. She was almost the definition of a hipster, large fake glasses, an old looking jacket and large bracelets. She was pretty damn hot.
As I threw my backpack into the backseat, she plugged her iPod into the car’s radio. Miike Snow’s Animal came on and I instantly flashed back to fucking Megan H. My eyes glazed over, cock hardened, and mind wondered. As the song ended Megan asked
“So, anything interesting happened to you today?”
Yeah I fucked two chicks.
“No, not really, just same-old same-old. Anything interesting happen to you?”
“Na, pretty boring” she replied, “just a few tests.”
My mind went back to the other two Megans, and my cock only grew harder. About halfway through, she veered away from the normal path, now making her way to some parking lot. As she parked, I asked
“What are we doing here?”
“Well, these long ass car rides aren’t exactly free…”
“What do you mean, I give you gas money and I only live half a bloc….”
She stopped me with a kiss, gently, without tongue. I loved it. She pulled back first.
“Noticed that hard on you have. Is it just for me?”
Confused, but wanting more I softly replied
“You know it.”
We went back to the gentle kiss, it was so soft. Her lips were warm, and smooth as silk. I felt her hand move down to my chest. She pulled off my shirt, and then I pulled off her shirt and bra. The kiss became more and more intense; I felt her tongue press against my lips. I warmly embraced it into my mouth, our tongues flicked and rubbed against each other. Her hand moved down my chest and to my belt. I started to feel her chest, gently massaging each one; I could feel her humming into my mouth. The soft vibrations intensified the feeling in my mouth. As she slid my pants of I slipped into the backseat, and pulled her into the backseat. I laid down in the back while she straddled my hips, she took her skirt off and slid her panties down, her hair partially covered her nipples in the most beautiful way. As she gently lowered herself onto my engorged cock, she quietly whispered to me
“Please go slowly”
She dropped on top of me, landing on my engorged cock. I felt her hymen rip under the pressure.
“Shit! Megan, are you a virgin?” I asked as she got used to my size. After a few seconds, she found the strength to reply
I let her control the speed, it was easier this way, because she was on top.
She started off slowly, taking her time, but making sure she went as low as she could and then all the way up, until just the head was in her. Megan gently moaned, she started pumping faster and faster, her moans started to grow until I felt her pussy lips clench around my cock. She stopped as wave after wave of orgasmic bliss washed over her.
When it stopped she leaned down for a kiss. While we tongue fucked, a lifted her and switched positions. So now I was on top and could control the speed. I started slowly but soon I was pumping harder and harder. I lifted up one of her legs for leverage and fucked her as hard as I could.
After fifteen minutes of this hard core position, felt the familiar tingling in my balls
“Fuck! I’m Cumming!”
“Shit, don’t cum in me, cum on me.”
With all of the strength left in me, I pulled out but kept vigorously stroking my cock. It wasn’t long before spurt after spurt of semen landed on Megan’s face, chest and stomach. After another slow dramatic kiss, I grabbed a sock and went to work. I wiped my dick off, then leaned down and started wiping, kissing and sucking warm pussy.
After a bit, I slid on my underwear, pants and shirt. I helped Megan slide on her panties, then her skirt, then bra and shirt. After a few more minutes of kissing, we snuggled nest to each other. Eventually she fell asleep. Even though I was also pretty tired, I woke myself up, started her car and drove her home. I pulled into her drive way and somehow managed to wiggle her out of the backseat. I carried her to her door, opened it (she usually kept in unlocked) and laid her down on her bed. Needles to say I left her on her bed for an after school nap while I walked home.
The Next Day
My parents brought me to school the morning. I was feeling great; I got a good night’s sleep and was actually excited for the day. My cock, on the other hand, was sore as hell from all of the sex it had yesterday. I saw Megan M. on the way to my locker; we had some small talk a passionate kiss and then went to first hour together. After the lecturing was over with, we had a few minutes to our selves. Megan was sitting right next to me in her desk and once again we found ourselves wading through small talk. It seemed like nothing had changed, that is until she grabbed my cock.
“What?” she asked.
“Baby, it’s sore as hell. You must have thoroughly fucked me yesterday”
“Yeah,” She gave it a firm squeeze before letting go, “Or you masturbated like hell when you got home.”
“Either way, it’s tender as hell. Let’s give the poor guy a break.” I replied.
We continued our random conversations, and then the bell rang. I walked her back to her locker as usually then grabbed my second hour books. Second hour went by amazingly slow, mainly because I couldn’t wait to see Megan H.
I caught her on my way to Spanish and we had our usual conversations. When the bell rang I saw her start to get up and leave, I tugged on her shirt and had her wait. As soon as everyone, teacher included, left the room I said
“Hey I never got to repay you from yesterday.”
“Oh” was all she could say.
We walked over to the girls stall we went to yesterday. I sat down on the toilet seat and pulled her skirt and panties down. I started to gently kiss her outer lips, sucking and licking them slowly. Man did I go to work. I started sliding my tongue in and out faster and faster. I then moved to her clit, sucking on it and flicking it on my tongue.
“I’m about to…” Was all she let out before a long stream of her own cum shot out. Man I’ve head of squirters, seen videos of it and stuff, but it was not as hot as the real thing.
“Sorry, I generally try not to do that in front of guys.”
“No, its fine” I said, “Actually, that might just have been the hottest thing I’ve ever seen.”
We kissed a few more times, she tried to get my pants off, but I wouldn?t let her.
“Come on, let’s do it quickly.”
“Megan, it’s too tender. You must’ve fucked me too hard.”
“Yeah, that or you jerked off like crazy when you got home.”
What the hell, I thought. Is that just what everyone thinks?
“Either way…” I gently kissed her and we headed to our lockers and then the lunch room.
The rest of the day went slowly. My last hour, with Megan M, went by pretty quickly. After school Megan W. gave me another ride home. She told me thanks for taking her home, but that what happened was an accident. She went on how she almost gave her virginity to her now ex-boyfriend who she caught fucking some popular girl. She really didn’t want to talk about it. The rest of the way home was pretty awkward and silent.
The rest of the week went by pretty similarly. Megan M and I started dating and becoming serious. I did find out more about what happened to Megan W. Turns out, her boy friend was sleeping with? Megan H. Great. Where did she find them? Girl’s restroom by the auditorium. Even better. I knew I needed to stay away from that girl.
To Be Continued?