tagFirst TimeTiffany

Tiffany

byJayEll©

There she was: Tiffany Cartwright. The brown-haired girl I had fallen for at first site. We had pretty much been in the same class since elementary school, so she knew who I was, but I doubt that she cared.

Every day after school I would sit under a tree and pretend to study while I watched Tiffany and the other cheerleaders practice their drills, and cheers. I had done so for almost the last 4 years, with our senior year coming to an end in a few months. During that time I continually attempted to muster the courage to ask her out, or just to say more than hello or goodbye, but never did. I really wasn't expecting her to come over and talk to ME; but she did.

Practice was over, and I waited a few minutes as I usually did, before packing up my books to head home. Just as I slung my bag over my shoulder I heard somebody call my name, "Bradley, wait!" I took a few steps, figuring it had to be some other Bradley, because there was no way the person whose voice that belonged to was calling after me. She called again, "Hey Brad!" This time she was closer. I turned around and froze at what I saw. Tiffany Cartwright was jogging in my direction, calling MY name! I looked around once more before she reached me, just to make sure there weren't any other, more popular, better-looking Bradleys around.

She walked the last few steps to where I was standing. "Hey," she said and gave me a leg-melting smile. My jaw lay slack for a moment before I got my cool.

"Uh… hey, T-Tiffany," I said as smoothly as possible. "What's up?"

"Not a lot, I was just wondering if I could ask you a favor?" If she had asked me to rob a bank or assassinate the President, I would have without hesitation. But after a quick nod from me, she just said, "I've got this big Math mid-term coming up, and I'm a little embarrassed to say, but I really need some help if I'm going to get a good grade. I've noticed you always studying so hard and I thought you might be able to help me."

She didn't know the studying I did was just a cover to check her out, but as luck would have it, I was a wiz at math. If it had been English, or history, it might have led to embarrassment later. Either way, my answer still would have been, "Y-yes, of course. I'd be helpy to hap you. I mean happy to help you."

She smiled at me and bounced on her toes a little. I couldn't help but notice how her Breasts bounced inside that cute cheerleader top she had on. She wasn't top-heavy or anything, but definitely larger for her size.

"So, when do we start professor?" she asked and looked me straight in the eye. I lost myself for a moment in her hazel eyes, before I noticed her pink lips repeating the question, "Uh, when do we start, sir?"

"Oh, uh, Bradley is fine. And we can start whenever you have some time."

"Ok, well if you're free tonight, I'm just going to run in and shower. Then we can go study at my place." Her place!? Immediately my eighteen year old mind began conjuring up some steamy fantasies. I was brought quickly back to reality when I noticed she was still waiting for my response.

"That'd be great. I don't have plans tonight," or any night for that matter, "shall I wait here and give you a ride, or meet you at you place later."

"I'll need a ride. Be right back!" And with that she turned and ran back into the school. Thoughts of what she was about to do, plus a little imaginative embellishment, began to arouse me almost the moment she disappeared into the school. I high-tailed it to my car, to avoid any embarrassment and/or public humiliation I might receive had anybody noticed my newly pitched tent.

It didn't take her long to shower and come back to the car. She had, of course, changed out of her cheerleading clothes and into something at least, if not more, appealing to the eye. She was now wearing a black pair of fleece pants with the word "angel" printed across her round backside and the matching hoodie-style top that ended at her bare midriff (which was trim and tanned, but still soft-looking.) I averted my eyes just in time to avoid getting caught staring.

The trip to her house was quick and uneventful, as was the majority of the rest of the evening. There were several times I thought she was flirting with me, but I dismissed the thoughts as wishful thinking. At the end of the study session we decided to get together four times a week for the next three weeks until her test was over.

Over those three weeks I became very relaxed around her, and hoped she had warmed up to me enough to be able to spend time together after she had taken the math test. On our last day, she said with a pouty look on her face, "Oh, I can't believe the test is tomorrow and we won't have an excuse to see each other anymore."

At first, I interpreted that was a nice way of saying, "I'm done with you, back to the nerdery with the other geeks until I have need of you again!" But my disappointment was short lived when I noticed her face suddenly light up with an idea.

"Hey, why don't we get together tomorrow night and celebrate the A plus I know I'm going to get on that test! Yeah, my parents are leaving for the weekend, so we could order pizza and stay up late watching movies and stuff," she sounded genuinely excited.

"Well, I'd never turn down a night of pizza and movies with a beautiful girl like you," I said in a fit of daring. To my surprise she blushed slightly before leaping across the table and giving me a swift kiss on the lips.

I had no time to react or to remain in shock, for quickly after that she jumped up and guided me toward the door saying, "Now you better get out and let me get my rest, I'll need it if I'm going to be sure to get that A plus tomorrow!"

I don't know for sure what happened after that, but I assume I drove myself, got ready for bed, and went to sleep, because the next morning I awoke in my bed, with my pajamas on backwards, and a feeling of pure elation (and a wedgie.) Taking extra time with my hygiene, I got ready for school and drove quickly so I wouldn't be late for my first class. Not that I learned anything mind you. The day went painfully slow and I never thought it would be over. One time, during my history class, I actually thought I saw the clock ticking backwards.

Finally, at three o'clock, the bell rang. I went to our usual meeting place under my tree and waited for her to arrive. There was no practice for her today, because the basketball team was on an away game, and our school didn't have the dough to cart the cheerleaders around with the team. I saw her and my heart sank. She was wearing a heart-breaking expression and walked with a down-trodden shuffle. I almost burst in to tears just looking at her.

"I didn't get my A plus," she said and the pieces of my heart broke into smaller ones. All was well when I saw her mesmerizing smile break through and she exclaimed, "But I did get an A, one hundred percent!" She kissed me on the cheek and did a little dance that involved a lot of bouncing (oh yes), and a few pelvic thrusts (oh god yes!) "How's 'bout me and you start that celebration?" she didn't have to ask and didn't wait for my answer before jumping in my car.

We made a few stops on the way to her place for our celebration goods: The video store, for our movie marathon, the grocery store, for tons of cheap candy, and the Pizza place, for way more pizza than the two of us could ever eat in one night. "Hopefully," I thought to myself with plenty of doubt, "I'll be there to eat cold pizza for breakfast."

Once we made it to her place, she told me all the details about the test she took and how she expertly answered each question. We ate our pizza and settled on the couch to watch the three movies we'd rented. At first, we started out on near opposite ends of the couch, but by the end of the third movie, she had her laid her head comfortably on my lap. I had to concentrate very hard on the movie to avoid poking her in the side of the head. When the last movie was over she sprang up and said, "Man, I'm not even tired! Wanna watch another one?"

"I'm game," I'd never leave if she didn't make me. We went through a list of movies she had in her living room, which she shot down one by one for one reason another. I was beginning to fear the night was over, when she had another idea light up her face.

"Hey, do you like cheesy old westerns?" she asked and smiled.

"Um, I don't know," I replied truthfully. "I think I've only seen part of a John Wayne movie once."

"Well, my dad has a box up in his room with a bunch of stuff he recorded off of TV; mostly old westerns and stuff. Wanna see what he's got?" and she was away and back with the box before I could nod my head. We rummaged through the box and looked at the tapes, all of which had hand-written titles on the outside like, Great Black and White movies, or, Famous actresses. She grabbed the one titled, Classic Westerns and said, "Well, we might as well start with the classics." I nodded and she popped in the tape, spun around and jumped next to me on the couch. She wasn't close enough for me to put my arm around her, but I put my arm on the back of the couch, hoping she'd see my invitation and take it.

The movie started like any old western. The sky was blue, the sun was blaring down on some cowboys in the middle of a gunfight. "Oh, this is exciting," Tiffany was getting really into it already. Suddenly, the tape went blank and blurry for a moment before a new picture showed up. This one looked like it had been filmed much more recently and was set in a hotel room. A brawny man stood at the edge of the hotel bed wearing only a towel and speaking on a cell phone. There was a knock on his door and a voice from the other side yelled, "Housekeeping!" The man went and looked through the peephole to reveal a smoking hot, fair-skinned, black haired girl wearing a tiny French maid's uniform.

"I wonder what the heck this is," Tiffany wondered aloud. I already knew, but was too embarrassed to say. I'd just let her find out on her own. The man in the movie let her in and locked the door behind her. She bent over sexily, while dusting his furniture to reveal she wasn't wearing any panties. I looked over at Tiffany to see her reaction. She still hadn't figured it out yet. The thought of her being so innocent made her all the more attractive to me.

The camera changed and showed the man again. He had hung up the phone and was staring intently at the maid, or more specifically, up the maid's skirt. The camera panned down a little and showed a huge bulge in the man's towel. The maid turned around, and obviously pretended not to notice. She glanced over again and bit her lip while one of her hands caressed her breast.

All at once Tiffany realized what it was, "Oh my gosh… it's a porno!" Her eyes went wide and she looked at me. I put on my best surprised face and stared back at her. To my surprise she didn't jump up and turn it off, instead she watched intently for a few moments, her face going pink. By now the man and the maid were both completely nude and groping each other fiercely. I watched for a moment out of the corner of my eye, than looked back at Tiffany.

"We don't have to watch this, if you don't want to," she said looking slightly embarrassed now.

"Its up to you," I said, "you can change it if you want to." In truth, I was getting pretty turned on just watching her watch it.

"I'm fine if you're fine," she said quietly, then slowly turned her head back to the screen. I didn't resume watching the movie though. For now, I was intent on looking at her sitting Indian style next to me on the couch. She wore some tight, black, cotton shorts and a little white t-shirt that puckered up in the front just enough to show some skin. If I looked closely I could see the line of her panties under her shorts, and the outline of a white sports bra under her shirt. She had on her feet, a pair of multi-colored toe socks that were just as cute as she was.

I turned my attention back to the movie. The maid, who the man now referred to as either, "dirty little slut," or "whore" was laid backwards on his face and sucking vigorously on his manhood. The camera swung around to show the man using his tongue on her; flicking it quickly back and forth before burying his face. I heard Tiffany make a little gasp and was surprised when I turned and looked at her. She was very flexible, thanks to the cheerleading drills, which explained how she was able to what she was doing; with one leg dangling off the couch now, she was grinding her other heal in between her legs with hand moving it slightly up and down. She didn't notice I was looking. I don't even think she knew realized she was doing it.

We watched the couple have sex in almost every position. The whole time Tiffany's eyes were wide and focused on the action on the screen. Toward the end of the scene, the maid finished the man off with more oral and moaned as he came in her mouth and on her face. Instead of spitting it out and letting it run down her cheek like I've usually seen, she swallowed everything in her mouth and licked up what wasn't. That was nearly enough to make me go off, but I held it together. As the maid finished licking off her fingers, I say Tiffany stick the end of her finger in her mouth for just a moment, and watched her surprise when there was nothing on it.

That was it for me. I jerked a little on the couch and came a little into my pants. Nothing big, but it was enough for a wet spot to appear on my pants. It was then that Tiffany realized both my wet spot, and her own, which was harder to see because of her black shorts. She turned a slightly darker shade of red, but looked back expectantly at the TV. The scene had changed to a pool with two topless women sun-bathing on their towels. All at once the screen went fuzzy and blank, and then a picture reappeared of a cowboy and Indian riding their horses off into the sunset, followed by a giant, "The End" filling the screen and fading out.

"That was some western," Tiffany said laughing, breaking our awkward silence. We began laughing quite hard and she fell over and placed her head on my lap. This time, I wasn't relaxed as before, and she landed right on something hard.

She stared up at me for a moment, not embarrassed at all. Her lips relaxed out of her smile into an intense look. She grabbed my shirt and slowly pulled me down while lifting her head to meet mine. The kiss was passionate, deep and long. I felt like I was soaring through the air. After kissing for a while in that position, I could feel her start to tremble and become weak, so I lowered her back down to my lap. She stared back up at my and smiled. Then bit her lip and avoiding my gaze asked, "Have you ever, you know… done it before?"

After a moment I answered truthfully, but sheepishly, "No. Have you?"

"No. I always thought I'd wait for somebody I could fall in love with before I took that step," she said quietly. This somewhat deflated my hopes, but I wouldn't let lack of sex ruin this perfect night. That kiss I knew I would remember for the rest of my life. I was somewhat surprised by what she said next, "I think I love you. No, I know I do. Do you love me?"

I can't believe she had to ask. I told her the words I'd been wanting to tell her my entire life, "Tiffany Cartwright, I've loved you since the first time I saw you. I always have, and always will. I never thought in my wildest dreams you'd say the same to me."

She sat got up and moved her way onto my lap. Facing me, she wrapped her legs around me and we kissed again as deeply and passionately as the first. We kiss for what seemed like forever, before she broke away from my lips and began kissing my neck. I knew she could feel how hard I was, but I wasn't trying to hide it anymore. I returned her attention by kissing down her neck and added my own touch by reaching up and massaging her breast. She jumped when I touched her, then relaxed and flung back her head in enjoyment. I used both hands to rub her as best I could through her shirt and sports bra. She stopped me after a minute or two and removed her shirt and bra. Her breasts were more gorgeous than I'd ever imagined, and believe me I'd spent some time imagining them. The nipples were hard and I experimented a little, grabbing them with my thumb and forefinger and turning them just a little. She gave a little squeal, but she must have liked it because she started grinding up against me a little.

I pulled her closer to me and took her breasts each in turn, into my mouth. I flicked my tongue on her nipples, before sucking lightly on each one. My hands remained massaging and caressing her breasts and body as I did so. Her grinding became increasingly hard, and on one extra passionate thrust, I cried out in pain. I was still inside my jeans after all and had a zipper to deal with.

She jumped, realizing the reason of my outcry immediately, and hopped off my lap. While standing in front of me, she did her little joy dance, this time with a little less bouncing, a lot more gyrations, and some added body caressing. In mid dance, she stopped and grabbed one breast in her hand and pushed it up towards her face. She stuck out her tongue and licked the nipple like she saw the maid in the movie do.

"Oh… my… god that's hot!" I couldn't help but tell her. She seemed to have been waiting for some praise, for after I said that she took two steps toward me and began undoing my pants. As she pulled down my pants, my hardness sprang out and, I think, surprised her. She jumped back up and pulled me up off the couch and started kissing me again. It was my turn now. I kissed down her neck and chest and down her stomach until I was kneeling in front of her. A sweet and distinct smell came from beneath her wet shorts. Being eager to explore, I swiftly pulled down her shorts and panties to reveal her little mound. There was some hair, but it was neatly trimmed and cared for, which I guess was because of all the public showers she had to take with the squad. I spun her around and set her on the couch, using the opportunity to remove the shorts from around her ankles. With my right hand, I grabbed one leg and spread it apart from the other. She moved the other one by herself, giving me open access to what I wanted. My lips kiss down her thigh towards the center, but I stopped short of the goal.

"I don't want the other leg to feel left out," I said, somewhat teasingly. After covering both legs with soft, tender kisses, I moved to her beautiful cooch. I kissed it deeply, before I began repeating what I had seen in the movie; flicking my tongue on her, before burying my face and deeply licking, kissing, and sucking on her. Tiffany started moaning softly and pushing her hips into my face.

"Don't stop, that feels sooo good," Tiffany begged. I redoubled my efforts, feeling confident in my ability now. My right hand that I had only been using to steady myself, I now brought into the action. I used two fingers to rub and tickle in addition to my mouth. Tiffany gave three short gasps; then a loud moan as her hips began bucking erratically. I did my best to keep going without getting a fat lip before she cried, "Ok stop! That's too much." She was giggling uncontrollably now. I stood up, my hard rod knocking up against her leg.

She lay there only for a moment before she jumped up to trade places with me. "I hope you enjoy this as much as I did," she said slyly. I knew I would. Her hand grabbed a hold like it was a joystick and she tested it out a little; moving it gently side to side and up and down. She slid her hand down to the base to hold it steady while her other hand caressed the length of the shaft with her finger tips. The tip was very moist already and a drop of liquid ran down the shaft. She looked in awe for a moment before taking the tip into her mouth. For a few moments, she just held it there, slightly sucking. Then, her tongue began exploring the head, swirling around it and tracing its outline.

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byJayEll© 3 comments/ 40252 views/ 8 favorites

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