I sat in the hotel room admiring my new flail. My brother had bought it for me earlier in the day. I swung it around, careful not to bash it against anything. I took a couple swings at the bed, pleased at how the heavy spiked ball bounced off the mattress. I knew this little toy would bring me all sorts of fun when I got it home!
My brother and I were in Conchella, where they hold the sci-fi, fantasy and gaming convention annually in southern California. This was my first year at the con. I was what was referred to as a "Con virgin". That in addition to the fact that I was still a standard-issue virgin. The con was great! I'd met some cool people, got my brother to buy me the flail, seen a lot of neat stuff, and had a real fun time!
Currently, though, fun wasn't really happening. I put the flail aside and turned on the TV as I stripped to my boxers and got into the bed. Outside the hotel room I could hear people wandering around, laughing, talking, having a good time. Me, I was stuck in the room, unable to leave because it was after midnight and I was a minor. Only thirteen. It sucked.
Eventually my eyelids started to droop as I watched the same boring TV shows that I could see at home. It just wasn't gripping me. I pondered cracking open a can of Mountain Dew and drinking that to get myself some caffeine. But... no, why bother? I turned the television off, masturbated to a quick orgasm and snuggled under the blankets to drift off to sleep.
I woke up with a sudden start. Keeping motionless I heard the soft sounds being made by people trying not to make any noise at all. I cracked open my eye. From the position where I was laying on my side, I could see, in the illumination from the outside lights, my nineteen-year-old brother, Sean, was sitting on the other bed in the room, only a couple feet from me. He was currently making out with a girl. I couldn't see that many details on her, but what I saw was nice.
As the girl gave a little giggle at something Sean was doing, he hissed, "Shhh! Be quiet, Jenna. You'll wake Omri up." As he turned his head to look at me, I quickly closed my eye. "Omri? Omri, you awake?"
"See, he's still out," the girl said quietly. "Are you sure we can do it without waking him up?"
"Of course. I can be pretty quiet when I want to."
"Alright." They went back to kissing.
My penis stiffened up as I played back what they'd just said. "Do it"? Were they going to have sex? My god that would be cool to watch! I very slowly moved my hand down into my boxers and fondled myself a little as I watched the action on the bed.
It was hard to see what was going on, exactly. I could hear them kissing and saw my brother take off his shirt, tossing it onto the floor. Seconds later I heard some giggling from the girl and saw her shirt join my brother's on the floor. Damn, this was cool! I slowly wrapped a pair of fingers around my penis and gave it a couple real strokes now.
Jenna sat up on her knees. I could see her breasts now. I'd never seen any in real life before. It was too bad it wasn't bright enough to see all the detail, but what I could see was nice enough to fuel many a masturbation fantasy!
Jenna leaned down and gave Sean a kiss as he reached up and squeezed one of her breasts. He whispered something faint to her. She nodded and kissed his chest, moving her face downward as she unbuttoned and unzipped my brother's very tight vinyl pants that he'd insisted on wearing. She reached inside and pulled out his penis, which was really hard. I'd never seen another guy's stuff before, at least not outside of the locker-room and never hard.
Then Jenna took my brother's penis, gave it a few strokes and lowered her head down onto it. I couldn't see everything she was doing at this point, but I certainly knew what a blowjob was, and knew that my brother was now getting one. Lucky jerk. My masturbation continued unabated. I was trying to be careful not to cum, though. I wanted to wait and see if they ended up fucking.
Sean sat up a little after a couple minutes and started struggling out of his pants. Once he was naked, he pulled Jenna's face up to his and started kissing her as he undid her jeans, working them slowly down off her hips. I thought it was kind of strange that he'd be kissing a girl after she'd had his penis in her mouth, but apparently it didn't bother him too much.
Now Sean rolled Jenna over onto her back and pulled her panties off. I could see his penis pointing almost straight up. I wondered if this was the moment. Would this be where I got to see them fucking? I certainly hoped so!
But no. Once Jenna was naked, Sean simply put his head down between her legs and started moving his face all around. I knew what this, too, was. I always though the idea of going down on a girl sounded pretty gross, but Sean seemed pretty into it, and judging from the fact that Jenna was currently holding a pillow over her face to keep from making too much noise, see must've been having a REALLY good time.
Finally Sean lifted his face and started kissing his way up Jenna's body. By the time he reached her face, his whole body was laying on top of hers. I pictured his penis rubbing against her vagina. I wondered if he'd stuck it in yet? I didn't think so, but I wasn't certain, of course.
Then he whispered something to her. I didn't catch the whole thing, but I did hear, "...condom?" from Sean.
Jenna shook her head. "No..."
This must be it, I thought. If he was asking her about condoms, then they must be ready to actually start fucking! I couldn't wait to see it! My hand on my penis was now moving a bit faster than it had been before.
My brother took his penis in his hand and sort of pushed down and forward. I saw his body move lower and closer than it could had his penis been anywhere but inside Jenna's vagina. As he let go and put his hands on either side of Jenna's body and began moving his hips, I knew now that, for certain, I was watching people have sex.
Under the blanket my hand now started moving faster and faster, in time with my brother's thrusts into Jenna's body. I could hear both Jenna and Sean making little noises of happy pleasure as they fucked. It was pretty obvious they were both having a fantastic time screwing. I felt jealous as hell.
"Sean? Can we do doggie?" Jenna whispered.
"Sure!" My brother pulled back and sat on his knees. I could see his penis sticking up, now shinny with wetness. Jenna turned around and got on all fours. Sean moved in behind her. He soon had his penis in her vagina once more and was happily fucking away.
Each time my brother pushed into Jenna I heard a faint slap sound from his pelvis hitting her butt. Also her breasts swung back and forth in time to my brother's fucking. I kept my eyes fixed on them while wondering what it must've felt like for my brother to actually have his penis in a girl.
I began masturbating faster and faster, and suddenly felt my orgasm hit. I had to bite my lower lip to keep from making any noise as the best orgasm I'd ever had took hold. I did my best to make sure my sperm all hit the sheets and not my body. Since I was laying sideways this wasn't that hard to do.
Now I watched as my brother had his orgasm. He made a couple little noises and pushed hard against Jenna's backside as he climaxed. I wondered what it felt like to actually do that inside a girl. I bet it was pretty sweet.
After Sean was done cumming he pulled out and flopped down onto the bed next to Jenna. He whispered something and she giggled a little. Then I heard her say softly, "I gotta go to the bathroom," as she stood and went to said room.
I laid there in the darkness, wondering if they'd maybe fuck again. Nope. Once she was out of the bathroom Jenna got dressed and quietly left the room, giving my brother a little kiss as he let her out the door. Then, still naked, he walked over to his bed, got under the blanket, said, with a quiet chuckle, "I hope you liked the show, Omri. I saw you spankin' it, so I know you were awake."
After a couple seconds I muttered, "Sorry."
Sean laughed a little. "It's ok. Glad you liked the show. Now go to sleep."
Moments later I followed his order.
By the time I woke up the next day, my brother was already gone. As soon as I thought about how cool it had been to watch him fucking Jenna last night, my penis turned into steel. A quick masturbation session dealt with that issue. Then I cleaned up, got dressed and headed out into the con.
Today was an exciting day at the convention. There were a couple big-name authors here for it and I got to meet them and get stuff signed. I bought myself a couple anime DVDs down in the dealer's room and spent some time hanging out in Hospitality, talking with people and looking at girls.
Then the curfew rolled around. I sighed as one of the security people told me that I needed to leave the convention area. I went back to my room, turned on the TV and sat on my bed, trying to figure out what I wanted to do.
Just as I'd made up my mind that I might as well jerk- off and go to sleep, I heard a knock on the door. I went over and opened it. And there was Jenna.
"Oh, hi! You must be Omri."
"Uh... yeah, that's me."
"Cool. Sean told me about you. I'm Jenna. Is he here?"
I shook my head. "No, I don't know where he is."
Jenna frowned a little. "Oh. I was supposed to meet him at Hospitality, but he wasn't there. I waited around for a bit and I thought I'd come and see if he was here."
"Well..." I waved my hand around. "You can come in if you want, but he's not here."
"Ok." Jenna walked in and looked around. She grinned. "Well, unless he shrunk, he's not here."
I smiled a little. "Yeah."
"You mind if I wait for him?"
I shook my head. "I don't mind. I don't know when he'll be back though."
"That's ok." She sat down on Sean's bed and I sat on mine. "So how old are you, Omri?"
"Really? You look a little older. I thought like about fifteen."
I blushed a little. "No, I'm thirteen. I just had my birthday a couple months ago."
"Oh, ok. Well, I'm seventeen myself."
"Are you having a good time at the Con?"
"Oh, yeah! It's my first one."
"Oooooh... a virgin, huh?"
"Uh..." My brain froze and then caught up. I smiled shyly. "Oh, yeah. A con virgin. Yeah."
Jenna smiled. "It's been a long time since I've been a con virgin... or the other kind..." She winked at me. I wasn't sure what to do, so I just giggled a little. "I hope we didn't wake you up last night when we came in," she continued.
"Uh... no, not at all," I said, but I could feel the blush spreading from my chest up to my face and ears.
Jenna blushed a little herself and laughed. "We DID wake you up!"
"Well, maybe a little," I confessed.
She laughed some more. She had a really nice laugh. "Well... that's ok. How much did you see?"
"Uh... pretty much... everything."
"Oh, god!" she said with another laugh. "Oh... you must've had quite the show!"
"Yeah, I guess..." I smiled a little. "It was a good show."
"I bet! Especially for a cute virgin boy like you, huh?" she asked, looking at me in an odd way.
"Uh... you think I'm cute?"
"You're welcome. May I come sit over there?"
Jenna came and sat really close to me. She said, "So what all could you see us doing?"
"Uh... well... I saw you... uhm... you know... sucking..." I blushed again. "Then him down on you... and then you guys... you know... doin' it..."
"Have you ever done anything with a girl?"
"No," I said, shaking my head.
"Not even kissing?"
"Hmmm... well... we can fix that." Jenna leaned towards me and before I knew what was happening, she brushed her lips gently against mine. "There! Now you've been kissed!"
I giggled again. "Thanks!"
Jenna smiled and then kissed me again, her lips lingering for a few seconds. It was very nice. She pulled back and said, "You really ARE very cute, you know."
"Thank you. You are, too."
Jenna leaned towards me and started kissing me again, this time placing a hand on my chest and pushing me down until I was laying on the bed, my heart beating a million miles a second. Then she slowly worked her tongue into my mouth and my already hard penis gave a jump inside my pants.
"You're a pretty good kisser," Jenna said after a couple minutes of lip locking.
"Thanks," I muttered.
She started kissing me again and I felt her hands tugging at the bottom of my t-shirt. Moving like I was in a dream, I raised my arms up and she pulled the shirt off me. Once I was topless she looked over my bare chest with a pleased expression on her face.
"Very, very nice," Jenna said, placing a hand on my chest and running it along my nipples and down onto my stomach and back up.
"Thank you," I managed to say yet again.
Jenna laughed a little. "You're a pretty thankful boy."
"I have a lot to be thankful for," I said with a smile.
Jenna started unbuttoning her blouse and took it off, then removed her bra and set it aside, giving me a really good, solid view of her bare breasts. She leaned in and kissed me a couple more times, said breasts brushing against my bare chest. I nearly came right then and there.
"Just to get the record straight and kill any suspense," she said, "I AM going to let you fuck me. If you want to."
"You are...?" I said in a voice barely above a whisper.
"Sure. If you want to." She smiled again. "I've never taken a boy's virginity before."
"Oh, god, yes, I want to!" I said, nearly overwhelmed by the idea.
"Good. Your first con and you'll get laid. Not a bad deal, huh?" she said, standing up next to me and taking off the rest of her clothes.
"Not bad at all," I mumbled, looking at her as she got completely naked and got back onto the bed with me.
"You better get naked, too," Jenna said.
"Uh... ok." I felt a little shy at the idea of getting naked in front of a girl, but I knew that it was required if I was going to fuck one. I quickly undressed and then sat back down on the bed, my hands covering my penis.
Jenna gently pulled my hands aside and looked at my erection. "Very nice," she said, taking it in her hand and stroking it slowly.
This time I couldn't even manage to say thanks. I just grinned a little and closed my eyes.
"So I'm going to give you a blowjob right now," she said with a little smile. "That way you won't cum too soon when you fuck me. Just try to let me know when you're going to shoot, ok?"
"Ok," I said with a little gasp. I didn't think I was even going to last long with a blowjob.
Slowly Jenna lowered her mouth down around my young penis. I felt her tongue running all up and down the shaft as her face bobbed up and down, her lips caressing my erection. It was the most incredible thing I'd ever experienced, and sure enough, I wasn't going to last long.
"Ooooooh... I'm cumming!" I managed to gasp out only seconds before I felt my penis begin kicking as my sperm was blasted into Jenna's mouth. She worked hard, swallowing all of it. My first blowjob had lasted less than a minute.
After I was done cumming, Jenna pulled off me, taking a sip of my Coke to rinse her mouth out as she sat back on the bed next to me.
"So how did you like that, Omri?"
After several tries I managed to say, "Oh, I liked that!"
Jenna laughed. "I bet you did!" She wiped her mouth off and gave me another kiss. I blanched slightly at the idea of kissing her right after my penis had been in her mouth, especially after I'd cum in there, but I figured I could deal with it.
We laid there on the bed kissing for a little longer, me on my back and Jenna basically laying next to and on top of me. My penis had stayed pretty hard and she started stroking it while we kissed. Then she pulled of land laid on her back.
"Ok. Time for you to do something to me."
I sat up. "Ok. What?"
Jenna took my hand and placed it on the patch of hair between her legs. It felt warm and wet and a little confusing. I had no idea where anything was or what I was meant to do. Then Jenna extended one of my fingers and pressed it against something. Next thing I knew it was sliding into a very tight, moist tunnel of pure delight. I actually had my finger in her vagina!
"There," she whispered. "Now move it in and out a little."
"Alright." I began to move my finger uncertainly. The more I moved it, the more Jenna seemed to like it, so I began fingering her faster and faster.
"Oh... yeah... oh, Omri... you're a quick learner..."
"Now," Jenna said after a minute or two. "See this spot here?" she asked, pointing to a little bump.
I wasn't sure this was something that I wanted to do, but I figured if I planned to fuck her, I might as well learn how to do everything else, too. Very tentatively, I leaned my face down and licked the little bump. It didn't really taste of anything, so I kept doing it while sliding my finger around inside Jenna's heavenly vagina.
Jenna started wiggling around a little and whimpering. "Oh... you're a really quick learner! You're almost as good as Sean..."
I grinned but didn't raise my face up. I was actually having fun down here!
Then Jenna, a little breathlessly, said, "Ok, Omri... you can stop now..."
I pulled my face up and my finger out and sat back on my knees. "Did I do it all ok?"
"Oh, god, yes!" She smiled at me. "You sure you haven't done that before."
"I'm pretty sure."
She was still breathing hard. I could see her breasts rising and falling in time with the breath. Looking me straight in the eye she said, "So. Are you ready to fuck me now?"
My penis twitched and I barely managed to squeak out, "Yes!"
"You wanna be on top or do you want me on top?"
"Uh... I don't know. Which is better?"
"Most boys like being on top."
I nodded. "Ok."
Jenna chuckled. "Well... get between my legs."
"Alright." Trembling a little, I moved between them, my teenage penis desperate to do its job.
"Now lower yourself down. Lay on top of me."
"Ok." I felt her wonderful body against mine as I lowered myself down. My penis was between her legs and I felt the shaft resting against her slit. My heart was racing. I was about to get laid!
Jenna held me against her and started kissing me. I kissed back, wondering when the magic moment was going to happen. Then I felt her hand reach between her legs. She took my penis, moved it around a little and then whispered, "Slide it in."
Trembling and shaking, I pushed forward, my thirteen- year-old virgin penis sliding for the first time into Jenna's seventeen-year-old vagina. When I couldn't push anymore, and felt my balls resting against her warm body, my pubes mingling with hers, I knew that I was a virgin no longer.
"There," she whispered, putting her hands on my butt. "Now just keep yourself in me for a little bit. Don't move or anything. Just try to relax."
It took a couple tries before I was able to say, "Ok.." My mind was whirling with everything I was doing. My penis was in a girl's vagina! I was fucking a girl! I was getting laid! I was having sex! I wasn't a virgin anymore! Oh, god it was amazing! It was... it... oh, god!
"Are you cumming?" Jenna whispered.
I gritted my teeth and forced myself to hold back. It wasn't any good. Before I could stop myself, I felt my penis start twitching and kicking inside Jenna's vagina as the biggest, best orgasm I'd ever experienced took hold of my young body, my sperm fountaining out of me and going into her. My mind just shut down from pleasure overload.
I collapsed on top of Jenna, my body shaking as the last of my sperm went into her vagina. As my brain reactivated, I was started whispering, "I'm sorry... I'm sorry... I tried not to... I'm sorry..."
Jenna laughed and hugged me tight, wrapping her legs around my waist. I felt my penis slide even deeper into her. She said, "It's ok, Omri! It was only your first time. Did you enjoy it?"
"Now you're not a little boy anymore," she said, giving me a kiss.
I grinned. "Yeah."
"I'm happy you had a good time."
"Me, too." I kissed her.
Jenna wiggled a little. "Hmmm... I think you're still hard."
"Well... when you're ready, you can start fucking me for real."
"I can?" I perked up. "Ok!"
I started kissing Jenna again as my penis returned to full hardness. Then I began slowly moving myself inside her. It was wonderful! Better than anything! I knew also that this time I wouldn't cum right away, which made it even better!
After a few minutes, blissful, heavenly minutes, Jenna said, "I wanna be on top."
I stopped fucking and took a deep breath. "Ok... how do we do that?"
"Here, hold on to me." Jenna held me tight and we rolled over. One I was on my back she sat up and took a moment to steady herself. My eyes were fixed to her wonderful breasts as she said, "There," and started moving up and down on my penis.
I put my hands on Jenna's thighs as she rode me. I tried pushing up into her, too, trying to coordinate as best as I could. It worked well enough that I felt my orgasm beginning to approach and then, gritting my teeth and pushing deep into her, I let go, my penis blasting the inside of Jenna's vagina with a good, thick coating of teenage sperm.
Jenna and I managed to fuck several more times that night, including a good screwing in the shower. After we were done having sex, we cuddled up together on my bed and went to sleep. It was the best night of my entire life, and I was the happiest boy in the world.