Hey readers! My name is John, if you're my parents or teachers. If you're my friend, I'm Jack. This story is partly true. All the stuff about masturbation is anyway. But the part where I lost my virginity... that hasn't happened yet.
If you want me to keep writing this story, or write another one, or tell you more about myself, or just want to talk, email me at jacksta@ymail.com.
Perfectly, beautifully unapproachable 3. Pussy
Fuuuuuuuuuuuuuuccccccccckkkk. This is torture.
This week, I told Samantha she could be on top. And holy shit, she was taking advantage of that.
She was riding me so incredibly slowly that I hadn't cummed after a half-hour of sex. She would hold her pussy lips right on the head of my cock and just hold it for a while. Then I would feel them part around my cock as she very very slowly lowered herself down, inching it deeper into her. When she hit bottom and grazed my pubes, she lifted back up again, exactly as slowly. My whole shaft tingled as it was slowly rubbed.
My whole body was crying out `I NEED TO CUM NOW!' every second while she was moving her pussy. But she wouldn't let me. She was moving too slowly to push me over the edge, and she wouldn't let me touch myself. This was absolute torture. The kind of torture I couldn't even complain about to anyone! No one comforts you because your sex with a cheerleader lasted too long!
I tried keeping my mind on other things. I wondered whether her cheerleader training helped her keep this up, but that wasn't off-topic enough. Next I triedthe opposite: I tried imagining tons of wild sex fantasies to push me over the edge (let's skip over what went through my mind in that moment!!). 40 minutes after her pussy first touched my cock, I finally got the orgasm I needed so incredibly badly. And it was loud.
"AAAAUUGGGGGGHHHHHHHHHH!!! FFFUUUUUUUCCCCCKKKKKKKK... UUUCCCCKKKK... uuuccckkk... fuckkkkkkkkk."
I never found out whether the neighbors heard me, but James sure did. He came running up the stairs, and opened the door as she was pulling off me. I just laid there, worn out and sore. James crawled up on the bed and started eating Sam out, right next to my head.
Out of the corner of my eye I watched his tongue move around her pussy. Licking around her clit, sticking it in the slit, sometimes sucking her pussy lips up into his mouth. I assumed that by now he had skill, not that I would know. 10 minutes later, she shivered. James looked up at me and gave me a wet smile.
A car pulled into the driveway. Sam dressed quickly to go meet her mother, to give us a minute to get things together upstairs. I stood up and started to gather my clothes on the bed.
"Fucking torture, huh." James had figured out what she had done.
"Yeah," I agreed. "45 minutes."
"Bitch had me goin' for more than a fuckin' hour." It still made me happy when he had things worse than me!
He slapped me on my bare butt before heading into the bathroom to wash his mouth out, and masturbate. I didn't have time to think about that, so I pulled my clothes on. I spread homework around the table upstairs, and I was just scooping it back up as her mother came up. To her, it actually looked like a genuine study session. But really, it was time for me to go home, and we hadn't even said the word `science' all afternoon. It was just sex! Torture sex.
That night, I jerked off as fast as I could, and I can say that I haven't enjoyed a 3-minute session that much since I was probably 10 or 11.
Now let's rewind a bit. That was my fifth time having sex, not my second. Quick catch up!
My second time was the Thursday after I lost my virginity. We went over to Sam's house and had sex in her bed. I had sex with a girl in her bed in the afternoon after school. At 15. Nice! My first time was surreal. This time felt much more normal. Like I was one of the cool boys who has sex in high school. Who doesn't have to make up stories about losing his virginity at summer camp or something. I think I lasted longer because I kept thinking that her childhood stuffed animals could see my anus every time I lifted up before pushing back into her. On the other hand, James was downstairs and wasn't watching, which made it feel so much more normal. But by the time we were done with our study session, I couldn't find the condom anywhere!
My third time was a week later. Sam passed a note to me in class saying that we should do something naughty. I met her after school, and we discussed where we'd have sex. She said the library was for nerds, which made no sense to me, but we ended up settling on the boy's lockerroom after school. So we gave the last gym class plenty of time to clear out (I know that if I were the last boy out of the lockerroom, I'd take the time to jerk off before leaving!), then snuck in. We put a couple towels down on two benches, stripped naked, and started having sex. Right when my thrusting started to speed up, we heard masculine laughter and chatter... so we ran naked into a toilet stall in the back. The lacrosse team came in and we just watched through the crack as they showered together. Sam masturbated a little as they joked about each other's dicks and washed themselves facing each other. I wonder if those guys appreciated just how homoerotic they got! But finally, they all left and we ventured back out and I put my dick back in Sam. I cummed, and we sought out James to eat her out. In the mess of finding all our clothes, I left the condom next to someone's locker, and I didn't dare go back to find it the next day.
My fourth time was yet another week later. We had learned our lesson for now and went home for sex. But... Sam's mom was home that day, so she told her she was gonna be at a cheerleader friend's house for the afternoon, and then we secretly went over to James's house so we could be unsupervised. And of course, we had sex on his bed. Screwing his girlfriend on his bed, where he had masturbated for years, was another slap in the face to him. I even offered to let Sam be on top so I could rub my ass on his bed the whole time, but she said that we could do that next time (little did I know!!). I fucked her harder than usual, while James played around spinning in his chair. To rub it in, as my orgasm approached, I pulled out, snapped off the condom, and moved up as if I were going to cum on her face. But then I pretended to miss and shot 3 streams straight onto his pillow. Sam glared at me disapprovingly, then motioned for James to come finish her off. I laid on my stomach watching them, rubbing my bare dick on his sheets. But even that didn't get him to yell at me. I was trying hard to get revenge on him for his past assholeishness! And of course, I forgot the condom in his bed.
Following that session, she told me we needed to talk. It turned out I didn't need to be nervous because she actually just wanted to start doing two tutoring sessions a week — Tuesdays and Thursdays. Twice the sex! That meant that I would now be having sex with James's girlfriend more often than he does. He was getting to fuck her only once a week and she made him say he was happy about it.
So now we're caught up! I've had sex five times, and even though I'd like to forget the last time, it was the first time I remembered to keep the condom. I was ready to repair my relationship with my JOB! Well... the next day I found out he was out sick for the week. I texted him that he should get well soon and that I had something to show him. This meant that I was gonna have sex one more time before seeing him next!
Less than 48 hours after I last pulled out of Sam, we were getting ready to put it back in. We were back in James's room. I noticed a couple streaks across his pillow, where I had blown my load exactly one week ago. Sam said she was feeling dirty, and I tried to be funny by suggesting I fuck her in the shower. But being the slut-bitch she always was, she agreed. I had no idea what to expect, but I couldn't back out now!
Two minutes later, I was wearing nothing but a condom and turning on James's shower. She came in behind me and I turned to face her, nude and hard. I kept trying to think of a way to tell her that I wanted to try to fuck her from behind. But I couldn't figure out how to suggest that without mentioning that that's how I've seen people do it on internet porn videos, and James and I were both pretty sure she wouldn't accept us looking at porn. So as we climbed into the shower, we prepared to do it basically in a standing-up missionary position. I guess it wasn't too bad, because I barely had to bend my knees to line my dick up with her pussy.
I pushed in and started fucking her, but after a few thrusts, the water washed her natural lube out and it got harder to push into her. So I rubbed some extra lube on my dick before pushing in again, but that only lasted for a couple more. After a second application also got washed off, I started to think we'd have to turn off the water, and we'd just be having sex standing up in the shower box. And that sounded terrible.
Not ready to give up, I dried off enough to use a computer, and went back out into James's room. He was lying on the bed patiently. I sat down at his desk to research a bit on shower sex. I made a point to spin around in his chair so he could see clearly that my ass and balls were touching the seat where he sits to work.
After getting through some terrible magazine articles on it, I stumbled on a blog that mentioned using water insoluble lube in the shower and it wouldn't wash off easily. The condom-dissolving kind of lube. So I returned to the bathroom and asked Sam whether she could go without a condom. She thought for a second and said that she was on the pill. I asked about STDs, and she said she had only had sex with me and James since her last test, and always with a condom. I, of course, had never had sex with another girl. But I wanted to sound cool, so I told her that I just got tested. As if I regularly put my dick in different girls so often that I needed to be sure! And we were agreed on the new plan.
I walked back out and asked James if he had any water insoluble lube. He pointed out that you can't use a condom with it, and I told him that I knew that.
He looked hurt. "She never let me do that..."
But he dutifully got up and opened the bottom drawer next to his bed. He carefully blocked the view of the drawer so I couldn't see what else was in there. I didn't have much time to speculate because he quickly handed me a bottle.
"What do you have that for?" I asked.
"I bought it for my first time, before I knew you couldn't fuckin' use it."
"For when you lost your virginity to Sam?"
He started talking much more quietly. "Fuck no dude. I told Sam she was my first. She's more like the fourth. But don't you fuckin' tell her that or I'll break your motherfuckin' arm to shit."
I nodded, and didn't volunteer the fact that Sam actually was my first.
I started rubbing some of the new lube on my crotch as I turned to go back in the bathroom. I rubbed some more on her pussy and we turned the water back on. The new stuff worked! And it was slick! Maybe even too slick. It was so slippery that her pussy barely felt like a pussy. I closed my eyes and realized that I could have been fucking basically any hole, and I couldn't tell the difference. I reopened my eyes, and the sight of my dick pushing open her love canal and penetrating deep reassured me that I was where I wanted my dick to be. I reached up with my unlubed hand and fondled her right boob.
After about 20 minutes of thrusting in her textureless hole, I finally started to cum. Everything up to that point was kind of lackluster, but it felt amazing feeling my cum squirt out of my cock up into her, and not into a condom. I leaned into her, and moaned with each squirt.
I withdrew from her, and walked out to James. "You're up!"
He jumped up and ran in after his girlfriend. After 10 minutes I heard her gasp a couple times. He came out first with a drop below his lip. She came out after, dressed, and went out of the room to go set up the study session.
Once she was out of earshot, I pointed at his chin and said, "You've got a drop of my..."
He looked in a mirror and then wiped it away. "Asshole," he muttered. "If you ever tell anyone I ate your entire load, I'll rip your other arm fuckin' clean off," he said, turning back to me.
"The whole load?" I didn't know my cum would have all just slid out.
"Shit, I think so. `Least it tastes better than pussy though."
I ignored that comment, and instead went for the joke. "But if you rip my other arm off, how will I ever jerk off?"
He stared at me for a few seconds, then laughed. "Handjobs, I dunno, dude! Unless banging my girlfriend twice a week is enough for you?"
"Not even close, dude!" And I wasn't even kidding.
"Ah, fuck."
After a moment, I pointed at my dick. "So how does this stuff come off?"
"The lube? You just sorta wipe it off. Good fuckin' luck dude." He threw his towel at me.
As I started to work on wiping my crotch, I decided against pointing out I had pushed the same lube more than 7" into his girlfriend's pussy. After a lot of work getting the lube off on James's bed, I finally felt clean enough to get dressed so I could go out and tutor. During our lesson, I distinctly heard the sound of someone jerking off with lube, but I don't think Sam noticed. I heard James groan, and then he came out to join us. He patted me on the face, leaving a drop of his cum on my face. Fuck! I'd never get back at him if he just thought this was all in good fun!
On Saturday when I was just hanging out with friends, I got my first sext message. Sort of. One that I was very glad I was able to hide from my friends.
It was a pic of a hard cock in a condom from James's number. It read, "lube was stil up her farther then i could reach. fuck!!" At this point, I hadn't seen his dick. He was never more than shirtless around me. But I was assuming all along that I was way bigger than him, and the pic suggested that I was right.
I replied quickly, "did it break the condom?" That was something I should have warned him about earlier.
After a few minutes came back, "yeh dud. but ur lube made it feel AMAZING so fuckn thx! plus the stuped bitch got cum in her neway" I assume he meant `dude'.
I texted him back a smiley, and put my phone away.
That's the third chapter! There's a ton more fun stuff to come if I keep getting feedback.
Thank you for all (or maybe most) of the feedback I got for the first one!! It was nice to hear about how many guys jerked off to my story, and how many times! And it was great to know that at least one girl was aroused by my story! jacksta@ymail.com.