October 17, 2008

A Year in the Life of Madison Semmes – Part 07 – November
Alex Hawk

October rolled into November. I was still getting poked on a regular basis by Lucien and his brother, and very occasionally by Scott. He and Kelly seemed to spend a lot of time fucking now that they’d started. I still hadn’t gone with my plans to sleep with Jacob, but I figured it was only a matter of time.

Kelly and I spent a lot of time talking about sex since she’d started doing it with her brother. I knew she was happy with him, but she also wanted to get some other boy’s penis inside her, and wanted to try it with a virgin. I thought for a bit about setting her up with my brother, but I wanted his cherry, so instead I figured I’d find a boy we could share.

And so, on the day after Thanksgiving, Kelly and I went down to the local mall. It was something we both wanted to do anyhow, you know, for window shopping. I figured we could also probably pick up a little something to share.

Eventually we got into the food court and settled down outside a Starbucks sipping a couple lattes. We’d already been wandering for a couple hours. I’d seen and rejected several boys for various reasons. Now, however, as we sat there together, I spotted the one I thought would be just perfect!

He was sitting on a bench about twenty feet from us. He had emo-style blond hair and blue eyes. He had a skateboard sitting on the bench next to him and was flipping through some skater magazine. He looked bored. He looked perfect.

“That one,” I said quietly, pointing towards the boy.

Kelly turned and looked. “Oh. Wow. Yeah, he’s a hottie.”

“You want him inside you?”

She giggled a little. “God, you’re graphic!”

I shrugged. “You know why we’re here and what we’re looking for. So you want him in you, or not?”


“I don’t know if he’s a virgin,” I pointed out. “But even if he isn’t, you still wanna do him?”


“Ok.” I took a sip of my latte and said, “Hey! Hey, you!” The boy looked up. I gestured at him. “Yeah, you. Come here.”

He picked up his skateboard and walked over. “Yeah?”

“Sit down for a second,” I said, pulling out the chair between Kelly and I.


“I’m Madison. This is Kelly.”

“Oh, hi. I’m Jesse.”

“Nice to meet you,” I said with a smile.

He smiled back. “So… what can I do for you?”

“Well, we were both sitting here talking about how hot you are,” I said, looking right into his eyes.

Jesse blushed, making me relatively certain he was still a virgin. “Thanks.”

“So what brings you out here today?”

He shrugged. “Just doing some window shopping. Trying to find out what I want to get people for Christmas and stuff.”

I nodded. “Sounds kind of like what we’re doing.”

The three of us sat around just chatting and making small-talk for a bit. Jesse, I learned, was fifteen, lived not far away, and single. Oh, there was some other stuff I learned, too, but that was all that I really cared about.

After nearly half-an-hour of chatting, I said, “Well, Jesse. It’s been really cool talking with you.”

“Oh, thanks!” he said. He looked a little disappointed. Obviously he thought Kelly and I were leaving. I figured what I said to him in the next few minutes would make him a lot happier.

“You said you live nearby, right?” I asked, leaning close to him.

“Uh, yeah.”

“Good.” I leaned even closer and whispered into his ear. “How would you like for the three of us to go back to your place and you can fuck me and Kelly for a few hours?”

“Uh! What?” he asked, blinking in surprise.

I placed a hand on Jesse’s thigh and moved it slowly upward to rest on his crotch as I whispered again, “Do you wanna fuck me and Kelly?”

“Are you serious?” he squeaked.

I gave his penis a gentle squeeze through his jeans. “Oh, yes…”

Kelly smiled at Jesse. “She asking you the question?”


She moved closed and put her hand down next to mine on his lap. “Well?”

“Uhm… well, look, I mean… you’re both nice and all, but…”

“But?” I asked, kissing his cheek.

“Well,” he said, blushing, “I’m still… you know… a virgin…”

“So?” Kelly said.

“Yeah, so?” I echoed.

“Well, it’s just that I want my first time to be, you know… special.”

I laughed and kissed his cheek again. “Look, Jesse. You’ve got the chance to fuck two girls for your first time. It doesn’t get much more special than that.”

He laughed a little in response. “Yeah, that’s true, I guess.”

“So?” I squeezed his penis again. “You wanna go fuck us, and have a great story to tell your friends for the rest of your life, or do you wanna pussy out and spend the rest of your life wishing you’d fucked us?”

“Are you both really serious about this?” Jesse asked, looking at both of us.

As his face turned towards me, I put a hand on the back of his head and pressed my mouth against his, working my tongue inside and giving this beautiful virgin the best kiss I could possibly manage.

“What do you think?” I asked after I broke off the kiss.

Jesse swallowed. “Ok.”

“Good!” I stood up abruptly. “Let’s go!”

“Now?” he asked in surprise.

“You know a better time?”

“Well, no.”

“Ok. Let’s go back to your place and fuck,” I said with a wicked grin.

Grinning nervously himself, Jesse stood up and he, Kelly and I left the mall.

We talked some more as we walked towards Jesse’s house. Well, to be more exact, Kelly and I talked a lot. Jesse hardly spoke at all. My guess was all the blood had left his brain and flowed to a different part of his body.

Once we got to Jesse’s house, he showed us around a little and then deposited us into the living room. He dashed into the kitchen and came back with three Cokes. I gestured for him to sit between Kelly and I.

“Thank you,” I said, taking the Coke from him as Kelly took hers.

“You’re welcome.” He cracked his open and took a quick sip, obviously to hide some lingering embarrassment.

“So! Where do you want to fuck us?” I asked brightly.

Perfectly timed, too, it turned out, as I watched him nearly spew Coke. “What?” he managed to choke out after a couple minutes.

“Well,” I said in my best serious voice. “We can do it here on the couch, or in your bed. Or your parents bed. Or the kitchen. Really anywhere. It’s up to you. Just so long as it’s some place where the three of can be naked together.”

“Uh… well, I haven’t really thought about it.” He took another hurried sip. “Uh… you’re really… well, serious about this?”

“You mean you STILL don’t believe me?” I asked in mock indignation. “He doesn’t believe me!” I said to Kelly.

“Terrible,” she said, clucking her tongue.

“What can we do to convince him?” I asked.

Kelly appeared to think for a moment. “How about this?” she suggested, and then pulled her t-shirt up off her head. She wasn’t wearing a bra.

“Ah…” Jesse said, looking at Kelly’s small breasts. As he did, I pulled off my own shirt, exposing my equally braless body, and tapped him on the shoulder. “Ah…” he breathed again as he saw me.

I took both his hands and placed one on each of my breasts. “So… you believe us yet?”

“Yeah…” He swallowed, his eyes wide. “Shit, we’re really gonna fuck!”

“Yep,” I said with a giggle. “So… where at?”

“We should probably go up to my bedroom,” Jesse said after a moment.

“To the bedroom, then,” I said, standing up.

Jesse got up a little awkwardly and led the way, Kelly and I following him, my eyes fixed on his firm ass.

“This is gonna be fun, Madison,” Kelly whispered as we walked.

“Yeah! I’ll let you get him in you first, since you wanted a virgin.”


We got to Jesse’s bedroom. It was a little tidier than I was used to seeing for a teenage boy, though he had all the standard posters up on the wall. What was really nice, though, was that he had a good-sized bed. Queen, was my guess.

“Nice room,” I said, shutting and locking the door behind us. Pointing to his bed I added, “Sit.”

Jesse sat.

I nodded at Kelly and the two of us began to remove the rest of our clothes. Once we were naked we each sat on one side of Jesse and began taking turns kissing him. I figured he must’ve thought he’d died and gone to Heaven!

At one point while I was kissing Jesse, I began removing his shirt. Once it was off, I took a moment to appreciate the beauty in front of me. Oh, he was quite nice! I couldn’t wait to see the rest, so I said, “Stand up.”

“Ok.” Jesse stood.

I reached over and unbuttoned and unzipped his jeans. I let them drop and then hooked my fingers into his boxers, pulling them down and exposing his very hard, very smoothly shaved, virgin penis. It put me in mind of Lucien’s, though it was a little bigger. His whole body, did, actually, except that he was blonde and Lucien wasn’t. God, Jesse was sexy.

“All yours,” I said to Kelly.

She moved close and took Jesse’s penis in her hand. Stroking it slowly she smiled, then opened her mouth and wrapped her lips around it. As she did that, I stood up and began kissing Jesse, letting one of my hands drop down to his tight little ass as I did.

“I can’t believe this is really happening,” Jesse whispered as we kissed.

I grinned. “It is. You won’t be a virgin much longer.”


“You wanna learn how to do something girls will go nuts for?”


“Lay back,” I said to Kelly. She did so and I got down between her legs. Without even thinking about what I was doing, I leaned forward, stuck out my tongue and began licking it all over her clit and vaginal lips. I’d never even thought about doing anything lesbian with someone before, but now it was something I wanted to try and, I was learning, wasn’t too bad at all!

“Oh, wow,” Jesse whispered, watching the action.

I worked a finger up into my friend’s vagina and winked at her as I kept licking her clitoris. With my other hand I reached up to caress one of her breasts and play with her nipples, doing to Kelly what I know I liked having done to me.

After a couple minutes of pleasuring my friend, I looked up at Jesse.

“You ready to try this?” I asked him.

“Oh, yeah.”

We switched places. As he knelt down between Kelly’s legs, I said, “Now just lick everything you see, and slide in your finger. She’ll love that.”

“Ok,” he said, and began working, moving his other hand up to one of Kelly’s breasts, just as I’d been doing.

I laid down next to Kelly and watched as Jesse began to work his tongue around her vagina. Idly I played with the breast Jesse wasn’t busy with.

“Since when… are you a lesbian?” Kelly gasped as Jesse’s tongue had an effect.

I shrugged. “Just expressing some curiosity.”

“Ok,” she said, and then I felt a finger that wasn’t mine or Jesse’s working its way into my vagina. I looked at Kelly in slight surprise. “Hey, you aren’t the only one who’s curious.”

This pleasant scene continued for a little while, but eventually I got bored with it. I wanted to see Jesse fuck. So I sat up and ruffled his hair.


“Yeah?” he asked, looking up from between Kelly’s legs.

“Ready to stop being a virgin?”

Jesse’s eyes went wide. “Uh! Yeah! Sure, ok!”

“Stand up.”

Jesse did so. His penis was at just about the right level for sex, I thought. A little high, but I figured he’d find a way to deal. I took it in my hands and began stroking it a little. Lining it up with Kelly’s vagina, I whispered, “When you’re ready, just push. I’ll guide you in.”

“Do I need a condom or anything?” he asked, sounding nervous as hell.

“No, it’s ok. We’re on the Pill,” I lied. I wasn’t actually all that worried about getting pregnant. I figured with the amount of sperm I’d had in me over the last few months, if I wasn’t pregnant by now, I wasn’t ever going to be. Though I had to admit one part of me, a very stupid part, was actually hoping I would get pregnant.

“Ok.” Jesse took a couple deep breaths, had a false start, and then I felt his body tense as he pushed forward. I looked around his gorgeous nude body and watched as he slowly sank every inch of his rigid, hairless, fifteen-year-old virgin penis into Kelly’s waiting twelve-year-old vagina. I was so jealous of her right then.

I moved my hand off the base of Jesse’s penis so the last bit could slide in. “There,” I whispered. “Now that pesky virginity is gone. How do you like it?”

“Oh, god… it’s wonderful…” he whispered.

“Good.” I placed one hand on Jesse’s bare pubes, right above where his penis vanished into my friend’s vagina. The other hand I moved up to his smooth, hairless chest. “Now fuck her,” I directed.

Not needing any further direction, Jesse began to move his hips, sliding in and out of Kelly. At first he moved rather awkwardly, like a virgin boy would, but then began to get the hang of it.

All too quickly the other aspect of devirginizing a boy came to light as Jesse began to moan and gasped out, “I’m gonna cum soon…”

“Go ahead,” I whispered to him.

“Uh… oh… oh, god… uh!” Jesse moaned loud and pushed deep as his teenage penis began to shoot its sperm into preteen Kelly’s vagina. I held his naked, trembling body tight against mine as the orgasm washed over him.

Once Jesse finished cumming, I put a hand on each of his hips and slowly pulled back, letting his penis slide out of Kelly’s vagina. Then I hugged him and kissed him.

“How was that?” I asked with a smile.

“Oh, that was just… oh, I gotta lay down…” He plopped down onto the bed next to Kelly.

I straddled Jesse’s waist, letting my vagina brush briefly against his still-hard penis. Then I leaned down and kissed him a few more times.

“I bet you’re happy you said yes to us, eh?” I asked with a smile.

Jesse giggled. “Yeah.” He looked at Kelly. “Did you like it?”

“Oh, yes,” she said, kissing him. “You were my first virgin.”

“Oh, cool…”

The conversation stopped at that point, as I began kissing him again. While we kissed, I felt Kelly moving around behind us and wasn’t at all surprised when I felt Jesse’s penis being moved into position.

Grinning ear-to-ear, I moved back, feeling Jesse’s penis slide deep into my vagina. Once he was all the way inside, I stopped kissing him and whispered, “Surprise!”

“Yeah…” He looked down. “Oh, wow, that feels so nice…”

I rolled us over, taking care to keep him inside me. Once I was on my back, I placed my hands on Jesse’s butt and said, “Fuck me.”

“Ok.” Jesse began moving his wonderful, nude body on top of me. I laid back and relaxed, watching the beautiful sight of him fucking me and savoring the sensation of being inside me. I was so happy I’d decided not to stay a virgin, I thought to myself. Sex rocked!

Jesse wound up cumming in me after less than five minutes, though that was at least long enough to give me an orgasm. About ten minutes after that, he was screwing Kelly again, and making her get off.

We fucked a total of seven times during a three hour period. My favorite part had to be when I was riding Jesse’s penis while Kelly was straddling his face and she and I were kissing. Glorious beyond all imagining!

As I rode home on the bus after all the sex was over, and after plans were made for us to hook up again, I thought about what my next move was going to be. Christmas was coming up soon. Perhaps I’d give Jacob the best present ever by taking something away from him.


Copyright 2008 by Alex Hawk, all rights reserved.