Gender: Male Age: 18 Location: N/A
At lunch, I sat by myself at a picnic table in the quad. I was picking over the cold, congealed shit that I had gotten from the cafeteria when Kendall came up and sat down at my table across from me.
"Hey Jamie!" she said cheerfully.
"Hey Kendall," I replied gloomily.
"Looking forward to tomorrow night?" she asked.
"Yeah, sure, whatever," I replied. "It'll be super, I'm sure."
Kendall started looking very concerned. "Jamie... is everything okay?"
"Shit, no, it's not okay," I replied. "Dammit, I can't lie to you any more."
"What?" she asked. "Jamie, I don't understand."
I took a deep breath. "Look, Kendall," I started. "I asked you to go to prom with me for one reason – I wanted to get laid. My friend gave me American Pie for Christmas, and it became a painful reminder that I was about to graduate from high school and I was still a virgin. Now, I know you've been trying to change your life, but I thought that maybe if I went to prom with you I could actually have sex. The only problem is that my conscience decided to start objecting – and, well, I just can't do this any more. I feel like shit for trying to pull this on you. You're one of my best friends, and this is an awful thing to do to you."
Kendall didn't say anything for a couple minutes. When she finally spoke, I thought she was going to call me every nasty name in the book.
"Jamie," she began. When I didn't look up, she touched my arm. "Jamie," she repeated.
I looked up. "Look, I have to agree with you. That was a pretty awful thing to try and do.
"However," she continued, "I cannot express how much respect you just gained from me for actually telling me the truth about it. That takes an unbelievable amount of guts, and just makes me want to go to prom with you that much more."
"You still want to go to prom with me after that?" I asked, shocked.
"Absolutely. Are you still picking me up at 6:00?"
Saturday flew by like a blur. I spent the afternoon driving around the East Bay, first taking the wine back to Jason and then taking the condoms back to Connor. I told them both what had happened, and they wished me luck. I kept the roses, though – I was DAMN well going to still go ahead and give those to Kendall, especially after yesterday.
I had just finished getting my tux on when the limo arrived at 5:30. We went over and picked up Kendall and we were on our way.
As we were getting in the limo, I looked her over. Damn, she looked unbelievable, so I told her so.
"Now, Jamie, you're not saying that just to get laid, are you?" she asked jokingly.
"No," I replied, "you really look amazing."
"Thanks," she replied shyly, blushing a little.
Prom was fun. The band sucked, but it was fun anyway. Afterwards, a caravan of limos headed out to Stinson Beach. The post-prom party was being held at Aerin Attias' parents' summer beach house.
The house was huge, but the party wasn't that great. Too many drunk people. After the third drunk person fell on us as we sat on a couch talking, Kendall and I retreated to an upstairs bedroom.
As we sat down on the bed, I started laughing.
"What is it?" asked Kendall.
"Oh, just this," I replied, "and the irony of it all. I spent the last three weeks trying to figure out how to get you into a bedroom at the post-prom party, and now that I decided to scrap that whole plan, here I am – no effort whatsoever!"
"That is a little ironic," she replied. "What's even more ironic is that you might just get what you were going for anyway."
That got my attention. "What?!" I said. "But after everything I said yesterday-"
"Jamie," said Kendall, "I've wanted to have sex with you pretty much ever since I started going to school with you freshman year. You're a fantastic guy, and you're pretty damn sexy."
"Well, thank you," I replied.
"Okay, don't let it go to your head," she continued with a laugh. "The thing is, one of things that I find sexiest in a guy is when he has respect for women, and after your honesty with me yesterday, I just find you that much sexier."
"But you've been working for the last year and a half to try and change your life," I said. "Do you want to throw all that away?"
"I won't be," she replied. "What I have worked for for the last year and a half was to stop having sex with guys who I didn't really even know and then just throwing them away like so much trash. Granted, I haven't had sex at all since I decided to change my life in that way, but this is different. You're somebody I know. You're somebody who if I have sex with you, it will actually mean something."
"Well..." I stopped. Kendall had been my friend for four years, and she was right. We actually knew each other, and this would definitely mean something.
"Your argument is pretty airtight," I continued. "And if it's something you want to do... well, you have my vote."
Kendall smiled... and then she kissed me.
Now, I've kissed my fair share of girls before, but this was different. Kendall's kiss was electric, almost as if she had a nine-volt battery in the tip of her tongue and it had just shocked me. She broke away from me, and then started to unbutton my shirt.
As she undid each button, she kept kissing down my chest, until she got to my waistline. Then, as she undid my belt buckle...
"Oh, shit!" I said.
She looked up at me. "What?"
"Condoms," I replied. "Dammit, I figured I wasn't going to need them, so I don't have any. Dammit!"
"Jamie," Kendall laughed, "don't worry. I've been on the pill since the beginning of high school. I have to take it – I'm on Acutane. It's not a problem."
"Oh," I said sheepishly, feeling like a total idiot. "Well, don't I look like a jackass."
"Don't worry!" she said with a laugh. "Just relax, and enjoy the moment."
So I relaxed – and thirty seconds later, I REALLY started enjoying the moment.
I had never received a blowjob before, and now I was receiving one from someone who could do amazing things with her tongue. Barely a minute later...
"Oh shit... Kendall... Kendall!"
She didn't skip a beat, as I cummed. She swallowed every drop of it. She reached over, and took a drink of her beer.
"I guess you need a couple of minutes to recover," she said slyly. "Why don't I help the process."
She stood up and stepped back. Reaching behind her, she unzipped the back of her dress. Slowly, she let it slip off of her shoulders, and then off her body, letting it pool around her feet.
Kendall was standing in front of me, wearing black heels, a lacy black bra, and a matching thong. That in and of itself was more than enough to bring my cock back to attention.
"Well, glad to see you're back in action!" she said with a laugh. "However, you have to undress me the rest of the way."
You didn't have to ask me twice. Standing up, I let my tux pants fall around my feet. I stepped out of them and crossed to her. First thing I did was reach behind her.
Now, I had bitched since I was six about taking piano lessons. My parents always told me that I'd be grateful, that I'd be more musical, that I'd have manual dexterity. I thought they were all full of bullshit – until now.
Thanks to the manual dexterity I'd developed, I was able to undo Kendall's bra in under two seconds. I let it slip off of her.
Kendall has nice big tits. Her chest is a 34DD, and it looks absolutely perfect on her frame. I gently kissed each of her breasts, and then kissed my way down the "happy trail" until I reached the thong. Slowly, I slid her panties down her legs, exposing a small "runway" of light brown hair.
Standing back up, I picked Kendall up, and then laid her on the bed. I straddled her, and then...
Oh fuck. I had no idea to do at this point. THIS is what I should've asked the guys about.
I started turning bright red. "Ummm... Kendall... this is really embarrassing, but I have no idea what to do..."
With a giggle, Kendall replied, "Don't worry. I'll take care of it."
Very gently, she grabbed my cock. Slowly, she guided it to her pussy and maneuvered the head inside. "Now, just move forward."
So I did. I gently moved forward, and then when I couldn't go any further, I pulled partway back out. "Good," said Kendall. "Just keep doing that."
So I did. I thrust in, and out, in and out. She had developed her vaginal muscles over the last few years, and though they had gone mostly unused for the last year and a half, she still had some control and was able to do enough to really blow my mind.
The tightness of her pussy plus the gentle squeezing felt incredible. She was unbelievably wet, and seemed to be enjoying it just as much as me.
"Jamie," she whispered, "Jamie, I'm about to cum..."
As she said that, she started trembling, and there was an uncontrolled squeeze in her pussy. Well, that pushed me over the edge, and as she started cumming, I felt my muscles all freeze. Buried deep within her pussy, my cock started shooting cum into her.
As I finished cumming, she trembled a few more times. Slowly pulling out of her, I rolled over onto my back. "Kendall..."
"Thank you," I said, rolling over to face her. I kissed her, softly and gently. "That was even more amazing than I ever thought, even better than it would've been if it'd been the way I planned. I can't think of a person who I would've wanted more to lose my virginity to."
"Jamie," she replied, "I can't think of a person who I would've more wanted to make love to me. You're an amazing guy, and I'll never forget this."
We made love once more that night before we fell asleep. We continued dating – and having some pretty amazing sex – for the next month of school and the entire summer.
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