First Love

Authors Note: This is a longer story with a lot of time spent on emotions and character and development. If you enjoyed this story or if you hated it please take the time to vote and to tell me why - Aspiring Romantic.

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We’d been making out for close to fifteen minutes, and things were starting to get pretty hot. Jill leaned forward and pressed her ruby red lips to mine, and I responded by pulling her closer to me. The feel of her feminine body aroused me to new heights. There seemed to be a fire burning in my pants, and I was eager to douse the flames. “Perhaps this will be the night,” I thought to myself. As we continued to kiss, I took a quick look at my surroundings. The pine bench in the dugout seemed to be up to the task…hopefully Jill would be too.

Slowly, I ran my hand up her slim leg. Just touching her in an erotic way was enough to send bolts of electricity through my body. She responded with a soft moan. Again, I pulled her tightly to me, making her aware of the stiffness in my pants. We stopped kissing long enough to take a seat. Next door, the crowd continued to roar at the football field, but I was oblivious to them as I marveled at Jill’s beauty. She was a true knockout, and I felt fortunate to be dating her. Chin-length blonde hair framed a cute face, which was highlighted by big blue eyes and a slightly upturned nose. Her lips were full and pouty, and the deep red lipstick she wore accentuated them. Her body was slim and curvy with nice full breast and an ass made to fill out jeans, although she hardly ever wore them. Tonight, she was wearing a pink button down sweater that hugged her bosom, and an ankle length blue skirt. In looks and attitude, she was the prototypical “goody-goody school girl”, and I was very attracted to her…mentally and physically. The fact that she was somewhat bookish made her less popular with most guys, but her brains had never intimidated me.

Sitting on the dugout bench at the empty baseball field, our passion drew us together again. Jill kissed me forcefully, and I allowed my hands to slide down and stroke her butt. I had touched her ass on several occasions, but it still excited me. After three months of dating, we were still virgins, so every little step counted. We had been at the fondling stage for what seemed like an eternity, but I had yet to remove any of her clothing, which led me to believe that actual sex was still a long way off.

We kissed aggressively, and I started to lean back, allowing Jill to straddle me. We both started to breathe heavy as our crotches rubbed together fiercely. Jill slid her hand down and started to rub my swollen cock through my pants. This had become part of our routine a few weeks earlier. Her motions were haphazard and sloppy, but it was a step in the right direction.

“I’m so turned on,” I whispered. Jill responded with a soft moan. Her short blonde hair hung in her face as she continued to grind her hips against mine. She supported herself with one hand, while the other frantically stroked on my cock. Instinctively, I reached up and started to unbutton her sweater. I got halfway down, exposing a pretty bra with a pink floral pattern that was being stretched to its limits by two very full breasts. Her nipples were extremely hard, and I could see them protruding through the satin material. I was shocked that things had gotten this far, and I didn’t want her to stop and think.

Eagerly, I leaned up and began to kiss her neck, quickly working my way down to the tops of her breasts. Jill continued to moan softly as she rubbed her crotch against mine. I reached up and took a breast in my hand, rubbing on her nipple through the thin fabric with my thumb. Jill responded with a high-pitched squeal of delight. I reached up and grabbed the top of her bra, planning to gaze upon a woman’s breast for the first time, and then suddenly Jill was pushing away.

“No…no,” she said standing up. She took a few steps back, still trying to catch her breathe. Her hair was slightly damp from her own sweat, despite the chilly night air.

“What?” I asked as I stood up. “What’s wrong?” I got up quickly and walked over to her. We started to kiss, and my hands returned to her perfect butt. Initially, she returned my kiss, but after a few seconds she put a hand on my chest, pushing me away again. She reached down and started to button her sweater.

“We can’t do this,” she said. “Not here.”

“Well, we’re smart kids,” I responded. “I’m sure we can think of someplace else to go.”

She looked at me with a stunned look. “No, what I mean,” she stammered, “is that we can’t do this. Not now. I’m not ready.”

I spent the next ten minutes trying to change her mind, knowing in my heart it was hopeless. It was hard to hide my disgust and frustration. Finally, she finished by telling me we should cool down for a while, and that she was going to sit with her friends.

“I love you,” she said, giving me a light kiss. I didn’t respond, as I walked off into the shadows, feeling a mixture of guilt and pleasure for snubbing her. She stood staring at me for a few minutes, and then walked back to the crowded stadium to find her friends. I knew she would be near tears, and despite my desire to go and comfort her, a part of me felt that she deserved to have her feelings hurt, even though she had done nothing wrong.

I stayed hidden for the rest of the evening, sitting in the shadows trying to understand my emotions, avoiding Jill, but keeping an eye on her at the same time. When the football game ended, I knew she would look for me, but I remained out of sight until I saw her leave with her friends. I was planning to sulk a little longer, when I suddenly realized that I didn’t have a ride home.

I started to walk around the stadium, hoping to find one of my friends, but they had apparently all left. They probably assumed that I was off fooling around with Jill, which was exactly where I wanted to be. I was about to give up when I bumped into Ashley Welch.

“Hey, how are you,” she called out, walking over to give me a hug. I had known Ashley most of my life. She was a year older than me and lived next door. We had been best friends when we were younger, and she was the first girl I had kissed in junior high. In high school, Ashley had become extremely popular, due mostly to her good looks, great personality, and the fact that she was a little slutty—at least according to the rumors. As a result, the two of us had grown apart over the past few years, but she was still very friendly every time I saw her.

As she hugged me, I felt the familiar stirring in my jeans. Apparently, my blood was still flowing from earlier. I pushed her away quickly, hoping she hadn’t noticed. “Ashley, I have a huge favor to ask?”

“What is it?” she asked with a smile.

“Can you give me a ride home? I missed mine.”

“Sure,” she said. “I was about to leave…I’m eager to get out of this outfit.” She was referring to her cheerleading uniform, which she looked spectacular in. It was comprised of a short green pleated skirt, and a white sweater with green lettering. Ashley was a short girl with a very petite, athletic body. She had a pretty smile, long dark hair, and big brown eyes. I had fantasized about her plenty of time in her uniform…the thought of her taking it off made my blood start to boil. It seemed like the built up frustration from Jill was causing me to get horny at the drop of a hat.

Ashley grabbed her pom-poms and said goodbye to her friends, then we walked out to her car. “So, we haven’t talked in while,” she said after we left the parking lot. “Where’s your girlfriend tonight? Aren’t you dating that blonde girl? I can’t remember her name.”

“Jill,” I answered. “We got into a bit of a fight, and she went home with her friends.” I don’t know why I told Ashley the truth, but I had always been honest with her, and lying then didn’t make sense. She asked if I thought we would get over it, and I told her we probably would.

“So, what was it about?” she asked. “Jealousy or sex?”

I was astounded by the question. “What?” I responded.

“At your age, there are only two real things to fight about,” she began. “Either someone is jealous, or someone has a problem with the sex.”

“We’re not having any sex. That’s the problem,” I answered.

“That sucks. How long have you been dating?” she asked. I told her it had been three month. “Holy shit!” Ashley exclaimed. “You must be going nuts. What the hell’s wrong with her?”

“She a virgin,” I answered. “Both of us are. Apparently, I’m the only one who wants to change that.”

“Even for a virgin, that’s a long time,” she said. “I mean, I gave it up to Richie Jones after two months, and I was a year younger than Jill.” I was a little surprised by the way Ashley was talking. I had never heard a girl use the phrase “gave it up.”

“How about a blow job?” Ashley continued.

“No, she doesn’t do that either,” I responded. “Right now, I would be happy just to get a hand job from her, but I haven’t been that lucky either.

Ashley giggled. “That sucks,” she said, “but it’s not what I was asking. What I meant was, ‘How would you like a blow job from me?’”

I stared at her with a blank face, not knowing how to respond. Surely, she must be joking. I was still thinking up my response as we pulled into her driveway.

“Cat got your tongue?” she asked. “Look, my parents aren’t expecting me in for another hour at least. I usually go out with my friends after the game, but tonight I brought you home instead. You got a hard on earlier from me hugging you, so I know your horny. I enjoy doing it, and I’m pretty sure you will like it, so why not?”

I started to protest, but there was no point. Obviously, I hadn’t been able to hide my erection earlier. Finally, I was able to speak again. “Where will we do it at?”

“Remember that old fort we had growing up? Let’s go there. I’ve used it to fool around plenty of times”

Once again I was shocked. I had been using the fort as a place to make out with Jill, and even had a box of rubbers stashed there for the future. It was amazing that we hadn’t bumped into Ashley there one night.

Sheepishly, I agreed to go with her. After all, how could I say ‘no’? We got out of the car, and she walked around and gave me a kiss, firmly pressing her taut, petite body against mine. It took me less than a second to become rock hard. “You’re going to love this,” she said with a wicked smile. She briefly squeezed my cock through my pants before turning away. It was only a brief touch, but right away I noticed she had a lot more knowledge of the area than my girlfriend.

She led the way around the side of her house in the dark, while I followed, enjoying every movement of her tight little ass. My dick was so hard that I could barely walk. I couldn’t believe what was happening. This was like a story from the “Penthouse Forum”, or one of the porno movies I had watched with my friends. Here was a pretty brunette cheerleader, in uniform, asking to suck my cock for no apparent reason. Apparently, all the rumors at school were true. Ashley was a slut, and at that moment, I couldn’t be happier to learn the truth.

I followed Ashley into the woods, following the winding trail by heart. I had been down it thousands of times. At the end was a small wooden shack, next to a small stream. Our fathers had built it years ago for the two of us to play in. Inside, there was a homemade table where Ashley used to throw her tea parties, and there was a mattress in the corner where the two of us used to “camp out” as children. All in all, it was a nice little fort, although it had no electricity or running water. We went in, and Ashley turned on the battery-powered lantern in the corner.

“Are you nervous?” she asked. I shook my head. “Don’t be,” she said, stepping towards me. “I know what I’m doing.” Seconds later we were kissing, and I was hotter than I had ever been in my life. Maybe it was just the knowledge that I was actually going to do something serious, but I was more turned on then I’d ever been with Jill. As we kissed, Ashley stroked my cock through my pants. Instinctively, I slid my hand up her bare thighs, lifting her green pleated skirt, fondling her ass. She began to take control, pushing me towards the mattress on the floor. Before I knew it, I was on my back with her on top of me.

She positioned herself between my legs, and quickly opened my pants, and for the first time in my life, a woman’s hand gripped my erect cock. My whole body shivered, and I thought I would cum right away. Somehow, I managed to hold out.

Ashley reached down, grabbed her sweater, and quickly pulled it over her head. I was delighted to gaze upon a white sports bra, with a small amount of flawless cleavage protruding. “I don’t need to mess that up,” she said. I wanted her to take off the bra, but I was to shy to ask.

She leaned forward, and her long dark hair tickled my throbbing shaft. I moaned with delight. She looked up at me and smiled. “Do you know why I brought you here?” she asked. I told her I didn’t. “I don’t really know either,” she continued. As she talked, she rhythmically squeezed the head of my cock with her hand. “Let me tell you a secret,” she began. “I had a crush on you for years growing up. I know that’s a silly reason to do this now, but I guess old feelings die hard. I’d never even thought about dong something like this until we hugged earlier, and when I felt you getting hard, I couldn’t resist. I couldn’t get it out of mine.” She smiled at me again, and this time I saw a bit of innocence in her eyes. She followed the innocent smile with a naughty grin, and placed her tongue on the tip of my penis. Slowly, she licked up and down my shaft. My whole body began to quiver with delight. The feeling was unlike anything I’d ever expected, yet still amazing.

I had never suspected Ashley to have a crush on me when we were younger. In truth, it probably wouldn’t have mattered. She was very tomboyish growing up, and I had never thought of her that way. It wasn’t until high school, when she became feminine and popular that I started to notice her, but by that time we hardly ever talked, and she was just the subject of my fantasies. But now, the fantasies were coming true.

Ashley began to knead my balls gently with her hand. She ran her tongue up and down my ridge, and I couldn’t stop groaning with pleasure. “You’ve got a beautiful cock,” she whispered. I was surprised and delighted by her language. Jill would never have talked like that. She preferred to say “it” or “penis”. “It’s really big,” she continued. I smiled with delight. Like any teenage male, I had looked around the shower after gym, and I knew I was “gifted” compared to most guys. Ashley started to gently rake her teeth up and down my throbbing organ. “Are you ready,” she asked. I couldn’t talk. I just nodded. Slowly, she wrapped her lips around the head of my cock. Again, I felt my body began to quiver. I slid my fingers through her dark silky hair, pulling it back from her face. She shot me a smile with my cock still in her mouth. Then she started to move, taking me in deeper. Her tongue flicked around my cock, teasing it, as she took me into her mouth. My hips started to move uncontrollably, forcing my way down her throat, humping her face. I closed my eyes as she began to suck forcefully, still flicking her tongue around. My breathing got faster as I started humping without abandon. I twirled my fingers tighter in her dark hair, and she responded by sucking harder. Seconds later, I felt myself losing control. For the first time in my life, I orgasmed in the presence of another person. Involuntarily, I continued to fuck her face while my cock exploded in her mouth. Ashley continued to smile as drops of semen ran over her lips, dripping onto the tops of her small breasts and sports bra. Seconds later, it was all over, but my mind was still spinning. It had taken less than 3 minutes from the time she took my cock into her lips, but it had seemed like an eternity.

Ashley laid down next to me on the mattress. I began to thank her repeatedly, and she only smiled. After a while, she put her sweater back on, and we left the cabin, heading home. I started to wonder how this would change our relationship, and what I would do about Jill. Before we went out separate ways, Ashley stopped me.

“There’s a big party tomorrow night,” she said. “I don’t have a date. Would you like to come?”

Jill had plans with her parents that night, so I agreed to go. “This should be interesting” I thought to myself. Ashley hugged me tightly and the two of us kissed.

“I had fun,” she said.

“Me too.” I could already feel my dick getting hard again. I knew I would jack off the second I got inside. I had known about masturbation for a long time, but it seemed I had never done it that often before Jill came along. Foolishly, at the time I thought it was just a phase. Surely, once I was able to “get some action”, I would put masturbation behind me forever.

The moment Ashley kissed me goodnight I realized nothing could be further from the truth. I stood in the chilly night air, watching her every step as she returned to her house. Only half an hour had passed since she had given me my first blowjob. Nevertheless, her touch had caused me to come fully erect once more.

Everything about her made me horny. I loved the way her cheerleading uniform clung to her tight, petite body. The way her ass moved beneath the green pleated skirt was intoxicating. Her dark, silky hair, and porcelain like skin were like something from classic artwork. Her simple, natural beauty was almost unbelievable.

As she entered the back door of her house, I turned and walked home. I went quickly to my bedroom and undressed in seconds. I stood in the dark, with my erect cock standing out in front of me. I looked out the window, and noticed the light on in Ashley’s room.

The events of the evening started to play back in my head. I sat down on the bed and began to stroke my cock as I thought about making out with Jill, and then Ashley. The two girls were very different. Jill was tall and blonde with a curvy figure. Ashley was short, with dark hair, and a tight body. Jill dressed conservatively, while Ashley preferred sexy outfits. Jill was a bookish good girl and Ashley was an outgoing, sensual cheerleader. Again, my life was starting to remind me of the “Penthouse Forum.”

I started to stroke my cock harder, as I drew a more erotic comparison. I had seen both of them in their bra, and Jill’s breasts were round and full. Ashley’s were much smaller, and seemed to be perky. Jill’s kisses were passionate, but Ashley had displayed lust and hunger with her lips. Jill and Ashley had both gotten me turned on through the course of the evening, but Ashley was the only one who did something about it.

In the end, that was the point that stuck, as I began to picture Ashley on her knees in front of me again. I imagined her still in uniform, kneeling on my bedroom floor, with my stiff cock in her tiny hand. I began to stroke my cock fiercely as fantasy Ashley told me how good I looked, and how she was impressed by my dick. Then, she looked at me with those big brown eyes and whispered the magic words. “Fuck me.” My cock spasmed in my hand as I shot my load across the room. A few minutes later, I was under the covers and drifting off to sleep, looking forward to my date with Ashley.

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My bedroom door swung open with a crash, and instantly I was awake. I glanced at the clock and realized it was morning. Standing in the doorway, I saw Ashley and Jill together. The stepped into the room, and Jill slammed the door behind her. I felt my heart jumping in my chest, and I suddenly felt nauseous. Nothing good could come of this situation. Ashley must have told Jill about the blowjob!