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The Loneliness Tree

The first time I kissed Brad was under the loneliness tree. It was the night before prom. He was my date, and I considered myself lucky. My mom wanted some pictures, so we went out under the big oak tree in back and posed. It was the tree I sat under when I was feeling lonely and put upon, when my teenage angst made it impossible for me to share myself with company. After he’d pinned the corsage on me, I gave him a kiss, which Mom also got a picture of.

Our first date went really well. We didn’t have another until graduation. I went with him to the party after graduation. I’m not sure that he even thought of it as a date. I’d kept hoping he’d ask me out so we could spend some time alone, but he didn’t. We hung out together with friends, but I never really got to be alone with him until after the graduation party.

We had made out a little bit after the prom, but I’d had on my prom dress, and he had on his tux, and neither of us was really very comfortable.

Bradley Case had been my friend since I joined the band, one of the group of fellow band geeks that I spent time with both in and out of school. I played clarinet, and he played saxophone, so we were both in the woodwind section. We both were in the marching band, as well as the concert band which played at assemblies and gave performances in the gym a few times a year. We were also both in the jazz band, a smaller group. We even had the same piano teacher. We'd spent a lot of time together on the band bus, at games, at band practice and band camp, and I really liked him.

He was a bit of a geek, but so was I. I didn't have any deep romantic feelings for him, and didn't imagine that he had any for me, but I did think he was cute and nice, and supposed that he'd be gentle.

I wanted gentleness the first time. Never having fucked before, I didn't know what to expect really, but I didn't want to be grabbed and ravished and tossed aside after like a used sock. If I'd wanted that I'd have picked one of the jocks. There'd be time for all that later, anyway. What I was looking for was a guy I liked, but who I didn't have to commit to.

The best thing about Brad was that he had been accepted to Yale. Brad was probably the single smartest kid to ever attend Russell High School in Hadley Grove. That was another thing in his favor. I didn't want to be deflowerd by some idiot. The first time should be special, and just having some random date pop my cherry didn't seem special. I was sure that was bound to happen sooner or later. Brad would be here for the summer for practice, then he’d be out of the way at Yale, and I could begin college with some experience.

I believe in planning ahead. Life is too important to leave to chance. Look at my dad, for instance. He spent the years of his youth stoned out of his mind, wandering the country playing guitar and leaving his life pretty much up to fortune. I didn't think fate would smile on the same family twice, so I had to build a life for myself from the ground up. My own college plans were settled, more or less. I'd be going to UGA, band scholarship, majoring in music. Music was my life. I guess it runs in the genes. Brad, talented sax player and moderately good pianist that he was, didn't think of music as either life or lifestyle. He'd probably end up playing the sax in the White House, like Bill Clinton, or doodling around the keys like Truman.

After graduation, I’d gone home to change, then Brad picked me up, and we went to a graduation party. It wasn’t the graduation party that the popular kids, the cheerleaders and jocks were having, of course. It was given by one of our friends, Cara Lightbow. Cara’s parents had a really nice place with several acres and a big inground pool. There was beer and pot, and loud music. Brad and I left early and went back to my house where we watched TV and talked until my parents left us alone and went to bed.

We had our first real make out session then, on the sofa in the living room. It was amazingly delicious. He wasn’t the first boy I’d made out with. I’d had actual dates before where I’d made out and fought for my virtue. I’d always liked it too. None of them ever really got me to the point where I was ready to have sex with them, and none of them was willing to devote the necessary time it might take. Plenty of girls put out. Those of us who didn't seldom had steady boyfriends.

Most of the month of June slipped away while I was drumming up my courage. As much as I wanted to fuck, I just couldn’t bring myself to let him go all the way. There was a point where I stopped him. At first it was outside the bra, then inside the bra, then outside my pants. Inside the pants was really nice. I almost gave in the night when he put his hand in my shorts and touched my pussy for the first time through my panties. They were soaking wet and I let him work my shorts down to my knees and put his hands in my panties, but I wouldn’t let him take them down.

I wore a skirt on our next date. I let him open my blouse and unhook my bra, and slipped it off over my arms without taking my top off. He pushed my skirt up a little at a time, touching my legs and panties, rubbing me through the satin and lace until I let him slip them off. I rubbed myself against his erection through his pants that same night, straddling his swollen cock, making the front of his jeans wet with my juices. I loved the way my ass seemed to fit so perfectly in his hands.

He wasn't really any more experienced at this than me, of course. One of the reasons I'd picked him, aside from the fact that he was really likable and easy to talk to, was that he hadn't had much experience with girls.

A couple of weeks before, we'd been talking, and I'd asked him if he'd ever had sex. I knew that he had, of course, knew all the details from the girl involved. I just needed to bring up the subject of sex because it had become obvious that he never would.

“There was that one time with Jenna Brady,” he'd told me. “Johnny and Walter talked her into having sex with me.”

“So,” I'd asked. “How was it?”

“Not that great, actually. It was like a mercy fuck, you know. She wasn't all that enthusiastic about the idea, and really, neither was I. It was pretty good physically. It felt really good, you know? It was really sort of sad when I thought about it later though.”

“You could have turned her down,” I'd told him.
“I couldn't,” he'd said. “I might not ever get another chance.”

That was after I decided that he was going to be the one. I'd had him in mind as my first since I'd decided to get rid of my virginity. I didn't like any other boy as well as I did him. He wasn't the kind of man that I fantasized about, but there weren't any of those in my high school, and if there had been, the chances are they would have dated somebody other than me. He was a guy who was fun to be with, and we had a lot of things in common, horror movies and ancient history, for instance.

I didn't just come out and tell him that he was going to get my cherry, of course. I had to make him think that it was his idea. I didn't want him to think that I was just using him to rid myself of my hymen. I had kissed him first, but only because I thought he'd never get the idea to do it on his own. We'd been friends too long, I guess. He had to accept the idea of me as a lover first. I think that he was surprised that I had sexual thoughts of him.

He's not a bad looking guy. He is pretty awkward, but I planned to help him overcome that. I'm pretty sure he could be very successful with the girls if he had confidence. That would be important to him in college when it came to meeting girls and getting them into bed with him. I felt I owed him that much since he'd always been there for me when I needed a lab partner. He'd cut up my frog.

There were a lot of girls in high school who would have loved to go out with him if he hadn't been so awkward and shy. It wasn't too late for him to get some practice in with some of them before fall semester either. A lot of the girls I knew were curious about his cock. The rumor was that his was the largest male organ in school.

I was certainly not the only girl in our senior class who was still a virgin. A lot of the girls were saving themselves for religious reasons. I wasn't saving myself, and I didn't have any religious objections to sex. I'd just never done it. The truth was, that I hadn't dated much. None of the guys who'd asked me out ever worked at it enough. I was a girl with loose morals and nobody to take advantage of the fact.

I guess I scared a lot of guys away by being snarky and a smartass. There was one guy who used to flirt with me a lot in class, and I kept expecting him to ask me out, but he never did. One day I turned around and said, “You know something, Joey, you really gripe my guts.” I meant that he was beginning to piss me off by never asking me out, but it came out wrong, and he never talked to me again. I was too embarrassed to explain what had caused my outburst.

I really liked Joey too. He might have become my first lover if I had more tact.
I had been sixteen then. Now I was more mature, eighteen and on the verge of graduating high school. I should have spent my senior year fucking, but I'd wasted it on chemistry and physics.

One afternoon, I took Brad into the backyard through the gate. I had him sit on the swing while I knelt in front of him.I could see the outline of his erection pressing against the denim of his jeans. He wore Levi 501's with the button fly, and I carefully unbuttoned them. He felt big. Laying my hand on him, I could tell that he was wide and long. I measured his cock using my hand, finding it longer than the length from the tip of my middle finger to my wrist, and as wide as four of my fingers side by side.

That sort of worried me. I have small fingers, but four of them side by side was a pretty wide thing to get up in my pussy. I could feel it move beneath my hand, giving a little jump. "Probably," I thought, "It won't look that big when I get it out of his pants."

It was a lot harder getting it out of his pants than I thought it would be. I could get my hand down in his jeans, and get my fingers wrapped around him, but I couldn't actually figure out how to get it out of his pants. Should I go over his underwear, or try to maneuver it through the hole on the front. The front of his underwear was like a maze. Guys underwear is made in a ridiculous manner. There were two separate openings, and neither one of them was lined up with the other.

It actually looked longer out of his pants, but not quite as wide as I’d thought. It was still pretty big.

It wasn’t my first cock. Not the first one I’d had in my hand, or even the first one I’d had in my mouth. I wasn’t very experienced, but I’d given a few handies and blow jobs.. His was different though. Bigger, wider, longer, prettier. It was awe inspiring.

I kissed the tip of his dick and put my lips on it. It was something I hadn’t had much practice at. I felt clumsy doing it, afraid I’d bite him. He felt big in my mouth. I was uncertain that I’d be able to finish without gagging or having my jaw cramp up. I was wondering how to stop when he started pumping thick fluid into my mouth. I started swallowing. It seemed the logical thing to do at the time. I’m not sure how I would have dealt with a mouthful of come otherwise. I had no idea of how to get his dick out of my mouth without spilling it on his lap. Swallowing it was the only solution I could think of.

He was pushing me in the swing when I told him I wanted him to have my virginity. The swing had been in the oak tree forever. I couldn't remember it not being there, anyway. The ropes and board had been changed, but it always looked the same.

It felt only right that I should ask him there.

He didn’t answer me right away. When he did he said, “Are you sure?”

“Of course I’m not sure,” I told him. “How could I be sure?”

“Now?” he asked.

“No. Now’s not good. Not here under the tree, on the ground. I want it to be on a bed, my bed.”

“Your parents are inside,” he said.

“Yes. They’re going to Daytona this weekend though.”

“You’re not going with them?”

“Of course not. What would I do with my parents in Daytona?”

“Swim, sunbathe, look at motorcycles?”

“I need this opportunity to prove to them how mature I am,” I said. “By not partying and messing up the house with my friends.”

“By having sex?”

“Yes. I can’t stay a virgin forever.”

“And you picked me?”

“Of course I picked you. You’re my boyfriend.”

“I didn’t know that you thought of me as your boyfriend,” he said.

“For someone with a genius IQ you can be pretty thick,” I said.

“I suppose.”

“And it has to be safe sex,” I said. “I’ve started taking the pill, but you’ll still have to wear a condom, because I’m not taking any chances of screwing up your plans for Yale.”

“I can handle that,” he said. “So does this mean I get to see you naked?”

“I suppose.”

“Good. Where can we go?”

“Not now.”

“Oh? Why not?”

“Because that’s part of the specialness of losing my virginity. I’ve never been naked with a boy.”

“Being in the back seat with your skirt up and your panties off doesn’t count?”

“Nope,” I said. “That’s partially dressed.”

“I’m not sure I can wait until this weekend,” he said.

“I’m sure you can,” I said.

It was a very long three days, though. Making out in the backseat of his car, or on the sofa in the basement on those nights, I really wanted to just go ahead and do it. He certainly would have been willing. Part of the excitement was waiting, and I didn’t want to spoil that. He had to work in his dad’s store during the day, so I spent the days with girlfriends or out back under the oak tree. I even kept myself from masturbating on those long hot afternoons while I waited for him to come to me.

I looked okay naked. At least I thought I did. I never had the occasion to exhibit myself naked for others, but I assumed that most of the guys would have thought I looked okay as well. My breasts weren't all that big, but they were shapely and bouncy, with nice pink nipples that got stiff at the least provocation and at the least chill in the air. I was very proud of my nipples at eighteen, in fact.

I was feeling a little stupid trying to get his jeans off. I’d thought the hard part would be to get the buttons open, but even with his fly open wide, his jeans didn’t want to come down over his hips.

He helped by standing up and pushing them down to his knees. I realized that I should have taken his shoes off first, and was about to do that so I could get his jeans off over them, when he pushed them off with his feet, sparing me the trouble. I pulled the jeans off, getting his socks with them, leaving him only in his tee shirt and briefs.

His cock sprang out of his briefs when I pulled them down. It bounced. I put my hand on it and kissed the tip. There was a little bit of sperm there, so I licked that off. It had a nice curve to it, with a vein on the bottom as big as one of my fingers. I held it and bounced it off my lips as I pulled down his briefs with the other.
Everything was fine until I got them off one foot. He kicked them off the other foot, slipping as he did so and falling backwards onto the floor.

“Are you hurt?” I asked.

“I’m okay,” he said. “This isn’t nearly as romantic as I’d imagined it would be though.”

“You’re not going to lose your erection are you?” I asked.

“I don’t think so,” he said, getting up.

“Maybe I should have undressed first,” I said.

“I did always imagine a little more foreplay,” he said. “Taking your clothes off a piece at a time, kissing every inch of your skin as I went.”

“There are only three pieces,” I said. I pulled my tee shirt off and dropped it onto the floor, then pulled my shorts down and off. I managed to kick them away without falling.

“Let me take off your panties,” he said.

“Is that some kind of fetish?” I asked.

“No. It’s important for my fantasy though.”

“Okay,” I said.

He pulled his tee shirt off and tossed it across the room

“To teach thee, I am naked first,” he quoted.

I put my arms around him and kissed him on the lips. He tasted minty fresh. Thank God, I’d just brushed. I hoped that I tasted as good as he did.

I could feel his dick pressed against my stomach. “What did you do with the condoms?” I asked him.

“I thought you brought them in,” he said.

“Wait,” I said, trying to think.

“I must have left them on the table in the kitchen,” I said. “Would you get them?”

“I’ll have to get dressed,” he said.

“There’s nobody here,” I pointed out.

“Yeah, but still, I’m not going into your kitchen naked.”

“I’ll get them,” I said.

When I got back to the bedroom, he was lying on his back, his cock pointed toward the ceiling. He bounced it when he saw me. I tossed him the bag with the condoms and got into bed beside him.

He took the box of condoms out of the bag, opened the box and held up a strip. “Extra sensitive,” he read.

“Well, it’s my first time, so I’m extra sensitive,” I said. “Next time I’ll get the ribbed ones.”
I lay with my head on his stomach, holding his cock in my hand. “It’s pretty big,” I told him.

“It’s average,” he said. “I don’t need reassurance. I’m pretty comfortable with myself.”

I kissed it again. “It’s big,” I said.

“Seen a lot of them, have you?”

“A few.”

I kissed him again, running my tongue over the head of his cock.

“They’re fun to play with,” I said.

“I know,” he said. “I play with mine all the time.” He opened a condom and handed it to me. I rolled it down over his cock, doing a pretty good job despite still being a little nervous.

I rolled on top of him and kissed him on the mouth. His lips parted and his tongue slipped into my mouth. His left hand slipped down to my ass, popping the elastic of my panties, and moving down to touch me between the legs.

“You’re wet,” he said.

“Yes,” I said.

“That’s a good sign.”

My nipples were incredibly hard, so hard that they hurt. I pressed my breasts against his chest and kissed him again.

I felt his fingers slip under my panties and touch my pussy. He moved a finger tip along my lips and spread them gently. I had shaved earlier in the day, and hoped that there wouldn't be any stubble or places I'd missed.

“Nice,” he said, his voice husky and deep.

“Very nice,” I said.

He rolled me onto my side and put his hand into the front of my panties. He found my clitoris right away. I was wetter than I’d ever been in my life. It felt so good to be touched, to know that I was going to fuck.

“That feels so good,” I said.

I rolled over onto my back so that he could take my panties off, lifting my hips as he hooked his fingers into them, enjoying the feeling of having them taken off. I was ready for him, wanted him. He looked down at me, looking at my pussy. I hoped that it was shaved close enough. He held my legs at the knees and kissed down my thighs. When he reached my pussy he kissed it to, then licked me all the way up and down.

“You’ll have to teach me to eat pussy,” he said. “I’ve never done it.”

“There’ll be time for that later,” I said.

He slipped a finger into me, slowly and gently.

“Fuck me,” I said. “Fuck me now.”

He moved into position, putting the tip of his cock against my pussy and pressing. He moved it back and forth along my lips, then pushed it against me again. I was pretty sure that he was in the right place, it was where his finger had been a moment before. Maybe he was just too big.

I felt him begin to open me, felt the velvety tip of his cock opening me up, and slide into me. I gasped. There was a sensation of being stretched, and then of fullness as he slid himself completely into me. I wanted to touch my clit, wanted him to touch it. I moved one hand off his hip and touched myself. As I did, he pulled back out, then pushed into me again.

“Are you okay?” he asked.

“I’m fine,” I said.

“I don’t want to hurt you.”

“It doesn’t hurt,” I said. “It feels good.”

“I thought it was supposed to hurt the first time.”

“It hurt a little," I said. “Mostly because you’re so big though. I think"

He had paused with his cock deep inside me. I could feel his balls against my ass. I wiggled a little to get his attention.

“Do you want me to go on?:”

“Go on?”


“I want to be fucked,” I said. “That’s what we’re here for, remember?”

He began to stroke in and out of me. Soon we established a rhythm, a sort of clippity clop two step of sex. I could feel his balls bouncing off my ass as he thrust himself in and out of me, feel my wetness running down my crack. I managed to slip my hand back in between us and rubbed my clit as he stroked away.

When I started to come I couldn’t hold myself back. Any dreams I may have had of mutual orgasm went right out the window when I felt the first wave of orgasm building. I bucked against him, clawed his butt and pulled him against me as I screamed in ecstasy.

I could tell when he started to come. It seemed to take him a long time to stop pumping and grinding against me, and he seemed really short of breath when he rolled off, holding the rubber on his dick with his hand.

He slipped it off and tied a knot in it. There was a lot of come in it, and a lot still clinging to his dick, dripping onto the bed. I reached for a tissue and wiped him off, leaving little pieces of tissue behind on his dick.

“God,” he said.

“Goddess,” I corrected.

“Did you like that?” he asked.

“Yes. Very much. I don’t know why I waited so long.”

“You were waiting for the right guy and the right moment,” he said.

“I think I was waiting for some guy to come along who’d keep trying,” I said. “Without being an asshole about it, that is. There were a couple of guys I’d have let fuck me, but they proved that they weren’t deserving.”

“Am I deserving?”

“Obviously,” I said. “Mom said I could order out, are you hungrty?”

“A little,” he said. “There are a lot of condoms left.”

“Is that a hint?”

“No. Just an observation.”

“We shouldn't be wasteful,” I said.

“No,” he said. "We shouldn't."

It was a good summer, even better than I’d hoped for. As fall and college drew closer, I began to feel a sadness that I hadn’t expected. I began to dread the day we’d have to say goodbye. I wasn’t sure that it was love, but I had certainly formed an affection for him during those hot months.

During the day, while he worked for his dad and I idled away the time of my last summer vacation, I sat in the swing under the loneliness tree and wondered how to talk him out of going to Yale. In the end, I didn’t try. We had our summer, and that had to be enough, even if it wasn't.


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