Prom Date Ch. 01

Of course, a number of girls made comments about not seeing what Lilly saw in me, but I didn't mind. I've been the butt of way too many jokes, over my lifetime, to not have developed a thick skin.

I drove Lilly home after school and made arrangements to pick her up at seven, and then went home to change. It was Friday night and my older sister was home from college, which happened almost every weekend.

"You have a date?" She asked incredulously. "A real date with a real girl?"

"Lilly Crowel."

"Wait. I know a Lilly. She was a sophomore cheerleader my senior year. That Lilly?"

"Yeah."

"Wait, my geek brother is dating a cheerleader? What's the gag? That's not true, right?"

"No, it's true."

"So how does this happen? I mean...come on, seriously?"

"Well, just for the prom."

"No, you're taking her to prom? Are you demented? It has to be some kind of joke on you, right?"

"I hope the hell not. There's only a twenty percent probability that this is an elaborate joke."

"Twenty percent huh? How do you figure?"

"Well, it was in the seventies, but since she started...um...uh... well, it's gone down"

"She's starting what?"

"Nothing."

"Yeah, right. Come on. Spill. She's starting what?"

"Nothing."

"I'm not letting this drop, and you know how I can be."

Over the years I'd learned, the hard way, that she could get me into a leg hold around my waist, that I seemed unable to break, and then tickle me until I finally gave in. She hadn't put me in that hold for a long time, but then I hadn't forced her to. "Alright, she's teaching me about sex."

"Teaching you how?"

"Well, we made out in that back of my car one day and played with each other until we came. And yesterday we did the same thing in the gym after lunch. She actually sucked me off."

"Wow! Little brother getting sex lessons from a cheerleader, who'd have thought. What I want to know is why? You do know, don't you? She's using you for something."

"Jason, her boyfriend, dumped her, right before prom, to go with some other girl. She wants to get back at him by dating way under her class. I guess that's supposed to say how low he actually was."

"Wow! And you bought into that? How hard up are you?"

"Well, I guess pretty hard up to agree to this. But I can't back out now, it wouldn't be fair to her."

"Fair to her? Really? What part of this is fair to you?"

"Well, I'm getting sex out of it."

"Good God David! Don't you have any self-respect?"

"That's the second time today I've been asked that, and the answer is still the same. We both know the score, so what's wrong with it?"

"Fine little brother, but when she walks away, don't come crying to me about it."

"I don't plan on it."

An hour later I'd picked Lilly up and we were pulling into the theater parking lot. "Before we go in, you need to know something." She said softly.

"Okay."

She had on a very short pleated skirt and a knit sweater shirt that I was beginning to think was a favorite style for her. As I watched, she reached under her skirt and worked her little bikini panties off hanging them on the rearview mirror. Next, she pulled up her top, pulling it up over her tits. She had on a bra that didn't have any shoulder straps, and in moments her bare tits were on display for me. She dropped the bra on the seat and pulled her sweater back down. "Now you know what I'm wearing under this. Consider it an invitation after the lights go down."

"How far can I take it?" I asked, thinking about just how I could get her naked, but knowing I wasn't brave enough to try.

"The more you uncover, the better the climax needs to be. So, don't start what you're not willing to finish."

"Fair enough."

She slid out my side after I got out, her skirt pulling up to expose her pussy as she did. She grinned and whispered, "just to get your hard-on started."

"As if I needed that, after watching you take your bra off!"

"Never hurts to see more of the girl you're gonna be playing with."

"I guess that's true." We walked arm in arm to the theater, stood in line to get popcorn and a soda, and then headed to the theater for our movie. Lilly picked some seats near the back and settled into one of the recliners She flipped the arm up and patted the seat next to her, I gladly took it and she snuggled up against me, pulling my arm around her shoulders and my hand down onto her left breast. For someone that was just using me to get back at her ex, she was surprisingly amorous, or she was one good actress.

We shared the popcorn while the previews of upcoming movies played, Lilly lifting the drink and straw to my lips so I wouldn't have to move my arm. By the time the lights went down for our movie to start, we'd killed more than half the popcorn. With both of us reclined in the big seats, she set the popcorn in the seat next to us and spread her legs, hooking one over mine.

I wasn't sure what I should do at that point. I knew what I wanted to do, but was it what she expected me to do? After several minutes, she reached up moved my arm from around her shoulders and pulled it down, laying my hand on her skirt covered crotch. I grinned to myself and pulled the skirt material up as far as I could. She didn't seem to mind that her pussy was completely exposed. I started to gently stroke my fingers on her soft, delicate, inner lips, working my finger slowly between them. Her pussy was surprisingly wet, and I smeared that moisture all over her lips to allow my fingers to slide easily over and between them.

I heard her moan, ever so softly, when my middle finger found her hard little clit. I was getting good at this, or at least I thought so. As I stroked her, she reached one hand over to me, and awkwardly tried to undo my pants. With my free hand, I helped, letting her even work my pants down over my butt a little to give my dick more room to stick out the front of my pants. She grasped my dick and began to gently stroke it, in time with my finger. Her hand moved slowly, spreading my precum over my head and shaft. The longer we played with each other, the more turned on I got. My excitement soon overwhelmed my hesitation, and I twisted toward her, making it harder for her to stroke me, but allowing me to push her sweater up over both her sexy tits. I leaned my face down and sucked one of her nipples into my mouth and switched hands between her legs. Now I could suck her nipple and push a finger all the way into her hot wet depths.

She stifled a moan by pressing her face to my shoulder. I circled and stroked over her clit with my thumb, while I moved one finger in and out of her vagina. I felt her free hand, the one not still stroking my dick, move to my head and pull it tighter to her breast. I felt her start to tremble, and then muffle a deep gasp into my shirt. I'd learned enough to know she was climaxing, and that she'd want me to keep doing what I was doing. Her orgasm lasted nearly half a minute, her body trembled and shaking the whole time.

Slowly the stiffness in her body faded, the shudders stopped, and she lifted her face from my shoulder. Her hand moved from my head to my hand, gently pressing it to stop my stoking, she held her hand on mine, keeping me from moving it from her pussy. We sat for some time, my hand resting between her legs and my head on her bare chest. I wasn't sure what she was thinking or what I was supposed to do, so I just stayed that way until she gently moved my head.

I'd lost some of my hardness as we were sitting, so I wasn't nearly hard enough to do anything. But that didn't stop her. She pushed me back, then rolled on her side and lowered her head to my lap. I felt her mouth engulf my softened dick and start to suck and tease it. I let my arm rest on her side as my dick hardened under her attention. My hand seemed to move on its own as her licking and sucking renewed my excitement. I felt her soft breast in my hand, and started to play with her nipple while she sucked on me.

I stifled a moan of pleasure, as her magic mouth pushed me closer to climax. I wanted to warn her I was coming, but decided she had to already know. I closed my eyes and laid my head back, allowing the sensations to flow through me. I could feel the warmth and tingling urgency grow and spread. I stifled another moan and did my best not to be obvious as my body jerked, trying to ram my dick into her mouth. I gasped as the first surge of cum flowed up my shaft, squirting into her hot mouth. Over and over my body jerked, pumping my load into her mouth. I heard her gag slightly once, but otherwise she took my load without complaint.

"Fuck, you come a lot!" She whispered, after lifting her head to rest it on my shoulder. I pulled her tighter to me, feeling her squeeze my softening dick gently in return. As we sat there, still exposed, I began to wonder if it was going to be harder than I thought, to end this after prom was over. It had to end. No way Lilly was going to keep dating me, but that didn't mean that I was going to be happy when it was over.

"So, what now?" I asked, as we walked arm in arm from the theater.

"What would you say, if I said I wanted to go all the way with you tonight? Are you ready for that?"

"Sure. Do we need to go buy some condoms or something?"

Lilly giggled softly. "No. But I appreciate you asking. I'm covered that way, and I'm pretty confident neither of us is carrying a communicable disease, so I don't think we need that."

"So where?"

"Car would be fun, but maybe for your first time we should be more comfortable. My first time wasn't, but yours should be. Mom's working late tonight, how about my place?"

We drove to her house and had just gotten undressed when her mom came home. We scrambled to get dressed before we got caught. Unfortunately, all we could do was sit and talk, and of course, make out a little. I headed home about nine, promising to come by the next day.

—-o—-

"You're sure she isn't gonna be home this time?" I asked, as we stood in the basement den.

"She went dress shopping with a friend, they'll be gone for hours." She said, as she pulled me to her for a kiss. We stood and embraced for several minutes before she pulled her lips from mine. "Now, where were we last night? Oh yeah, you were telling me how beautiful I looked naked. Wanna see again?"

"Hell yeah!" I answered with a grin.

She stepped back from me and pulled her t-shirt up and off. "You should know how to undo a bra. Come do mine." She said softly, turning her back to me. I stepped to her and started fiddling with the fasteners. I'd seen them before, so I knew how they worked, but I'd never tried taking one off someone. I used both hands to stretch and unclip the two hooks. "Uh-uh. Do it back up. You need to know how to do it with one hand."

"Oh, okay." I fastened it back and the fiddled again for almost two or more minutes before I found a way to squeeze the material and force the hooks apart one handed.

"Very good." She whispered. "Now slip your arms around me, and slip the straps down my arms when you do."

I followed her directions and ended up with her bra on the floor and my arms around her, cupping both breasts as I pressed myself against her. "Now, kiss my neck while you play with my nipples." I did as she requested, kissing her neck and cheek and experimenting with kissing her earlobe as my fingers gently stroked and teased her rock-hard nipples. "Mmmm you're getting me soooo wet. You want to find out how wet?"

"Yeah." I whispered, pressing my boner against her backside. She took my hands from her breasts and made them flat against her chest. Using her hands to guide mine, she rubbed my hands all over her chest and abdomen, stroking her creamy soft skin, making my hands occasionally stroke over the front of her jeans.

"You want to tease a girl. Let her know you're enjoying her body and not just trying to strip her. Then you can undo her pants. Dresses are easy, but pants take more work, because we like them tight to show off our curves." She helped my fingers undo the front of her jeans, and then push the waist down at her hips. She wiggled her butt side to side as she helped me push the tight jeans down over her hips, making sure my thumbs hooked her panties and pushed them down as well. "Now, turn me around." She whispered. "Kneel down and you can kiss my stomach and whatever else you want while you work my jeans down my legs."

I did what she said. I knelt down in front of her, and kissed her stomach. As I worked her Jeans down, my face pulled further down, so I was kissing her completely hairless mound. "You like? I shaved it all fresh, this morning just for you."

"Yeah, I do."

"Some guys like some hair down there, others like it bare."

"Have you done a lot of guys?" I asked. as she lifted one foot so I could get her jeans off.

"Me? No. A couple, but girls talk, ya' know?"

"Uh huh." I answered, as I tossed her jeans aside, leaving her naked. "Can I try something?"

"Sure. Whatever you want." I gently pushed her back to sit on the sofa and then lifted her legs like I'd seen in porn videos. I took my time looking at and touching her pussy before I leaned my face between her legs and gently kissed her lips. "Oh yes, now lick it. Use your tongue, like you do your fingers."

I hesitantly licked up her delicate lips, tasting her with the tip of my tongue. Her wetness was kind of tangy, but surprisingly not unpleasant. I worked my tongue on and between her lips, exploring from the entrance of her vagina, up to her hard little clit. She held her legs up and back, allowing me to explore her pussy, spreading her lips to expose her clit. I concentrated on licking her hard nub, teasing and flicking it. I knew I was getting her close to climax, her body trembling, as she gasped for breath.

"Oh, fuck David! You're making me come!" She cried loudly, as the little trembles became whole body shudders. Her juices, leaking from her, were almost sweet and were actually quite enjoyable. Also enjoyable was how turned on this had gotten me. I stood up and quickly pulled off my t-shirt and then shoved my pants down. My rock-hard cock pointed at her, as I stood in front of her. She reached a hand out towards me, and as I moved closer, she grasped my rigid shaft and gently pulled me toward her. She rubbed my head up and down her sopping wet pussy lips, then nestled my head into the opening to her depths. "Now, just push in slowly. Most girls don't like it jammed in, especially not if it's as big as yours is."

"Am I big?" I asked, as I leaned over her, reaching for the back of the sofa.

"I'm not an expert, but you're way bigger than the only other two I've played with. Oh my God yes! Waaaaay bigger! Oh, fuck David! Don't stop! Push it all the way in! Oh my God yes. Now fuck me. Just push it in and out. Oh, fuck yes! God David! You're going to make me come again!" She squealed.

I was pumping my dick in and out, my excitement growing much too fast. I knew I was going to come. I wanted to warn her, in case she wanted me to pull out or something, but my body didn't give me a chance. "Uhhh, fuck!" I grunted, as my body jerked, jamming my cock fully into her. I felt my cum surge forth, deep in her pussy. Squirt after squirt forced itself into her.

"Fuck! I'm coming!" She cried out, as the first surges of my cum flowed into her.

I felt her pussy clenching and relaxing around me, practically milking me as her body shook and trembled. She reached up and pulled me down on her, while she wrapped her legs around me. We were bent awkwardly, so she released me and rolled us over, the two of us falling off the sofa in the process. Laying on top of me, with my, still mostly hard, dick inside her, she started kissing me. It was much like the kiss we shared in the back of the car, but more gentle, more tender.

I felt my cock hardening inside her again and she began to lift and lower her butt, holding her face to mine to continue the kiss. I moaned into her mouth, and my hands moved to cup her tits as she slid her pussy up and down my shaft. She slid her hot wet tunnel on and off my cock, stroking me ever closer to another orgasm. It was building within me and I could tell she was getting close as well. I was almost ready to let go in her when I heard it.

"What the fuck is going on?!" Mrs. Crowel practically shouted, from the doorway.

Lilly and I both looked over to see her mom and another woman standing in the door, staring at us.

"Mom! What are you doing home?" Lilly gasped, rolling off of me, trying to cover her tits and crotch, while I tried to cover my still rock-hard, dick.

"I'd ask you the same thing, but I can see what you're doing. You, young man! Get up!" I reluctantly did, as she demanded, still trying to cover myself. "I think you better pull your pants up and leave! I have some talking to do with my daughter."

"I'll call you later!" Lilly said, as I grabbed my shirt and headed for the stairs, still trying to close my pants, over my, not yet soft, dick. The other woman was standing in the doorway, looking down at my dick, with a very strange look on her face. She hadn't moved and I had to stop in front of her, still trying to tuck my hardon into my pants. I could feel myself blushing as she stared at my dick for what felt like an hour, before she moved to the side to let me by.