Gender: Male Age: Secret Location: N/A
A wild but popular young boy falls for the girl that others tease.
Young, first time, reluctance, romance.
There’s kind of always one or two guys in a middle school class that seem to catch a lot of the girls’ attention. I got lucky and happened to be one of those guys for my class. I wasn’t some super stud or anything, things just kind of fell out right for me.
First off, I was a year older than the rest of the guys when we entered middle school in sixth grade. I had kind of lost most of my second grade year to my parents’ divorce. Mom had to move twice that year, and it was a mess. When she finally moved me back to her hometown, she begged the principal, a nice lady who had actually been one of Mom’s high school classmates, to just let me do second grade again. I was mad as hell, but it was a great idea in the end. Instead of being a third-grader who was behind, I was a pretty average second grade student.
Secondly, I had two older sisters and they really were awesome to me. I took the divorce really hard, and they found some comfort of their own in helping me through it. The habit of guiding me and counseling me just kind of stuck. They made sure Mom bought me kind of trendy clothes and kept me in haircuts that the older guys were wearing. They constantly advised me on how to talk to girls. My sisters were kind of on the wild side, so they thought it was cool for me to have lots of girlfriends. Enya, the younger of my two big sisters seemed to get especially excited when I told her about making out with, or later scoring with, girls. That all kind of made sense when she “came out” in her junior year of high school.
The third factor that helped me get lots of girls was that I had a bit of a devilish streak. I was nice to people and everything, but I got into just enough trouble and just enough fights that I got the reputation of being “cool.” It didn’t hurt that being a year older than the other kids in my class I won almost all of the fights I got into. I did lose one, but nobody else in my class had ever managed to win a fight with Erica Klout either.
None of these things were planned on my part, but they all came together to make me appealing to a certain kind of girl. The sweet preppy cuties generally preferred the more handsome of the straight-laced guys, but the girls who liked a little trouble or had a bit of a wild side often gravitated toward me.
In the beginning, I kind of just drifted where the girls pulled me. Whichever of the wild girls was queen bee in their clique got me for as long as she felt like. In fourth and fifth grade, this usually meant we made out a few times after school and then she kicked me to the curb and moved on to the next boy she liked. Another girl would come along and the cycle would repeat. I never fell in love with any of these girls, but I liked them well enough.
When things ended, the only part that was at all upsetting to me was how mean the girls got to one another. They weren’t really in love with me or anything, either, but they sure loved having their little dramas. Sometimes I was expected to take sides. Enya would tell me to not get caught in that trap. “Liam, they’ll just yank you around and in the end both of them will get mad at you.” So, I never said a bad word about any of the girls, and it would end up paying off later when they sometimes decided to take me back.
By the time I hit sixth grade, I was twelve, almost thirteen. I had come to hold a few opinions of my own. Kissing girls was fun. Getting to play with their titties was more fun. Jenny Plotz had let me finger her kitty for about two minutes and then given me a blowjob for about thirty seconds. That was frustratingly short, but those things had been darned fun when I was doing them. So, followed my sister Erin’s advice and began to actively flirt with the girls I liked. Well, basically, I began to flirt with whoever seemed “the girl most likely to….”
This paid off in an unexpected way. I went to a make out party with Hannah Moeller. Hannah was a very pretty little blonde, and I’d always thought she was kind of sweet. She should have been really popular. But she was kind of caught between cliques. She was neither a preppy princess nor a wild girl.
In sixth grade, she decided she was going to push into the wild girl crowd. She began bragging to the other sixth grade girls that she was going to get to go to a make out party because the older girls had decided she was ready for that kind of thing. That wasn’t really the reason, but I didn’t know that yet. Sixth graders were usually not invited to the seventh and eighth grade make out parties, and it did sound cool to be invited. But actually there was more to the story than Hannah let on. Hannah’s cousin was throwing it, and Hannah was so desperately pressing to forge an identity that she had had threatened to squeal if she didn’t get to come. Not knowing the whole story, I just figured that Hannah was ready to do some things the other girls weren’t doing yet. So I flirted with her, and she invited me.
I got to the party and started making out with Hannah but got shut down between somewhere between her titties and her fuzzy parts. Hannah’s cousin, Megan, was the hostess and was already in a pissy mood because the boy she had invited got grounded that afternoon and couldn’t come over. She was dateless at her own make out party. When she heard the little cousin who had blackmailed her into an invitation telling her date, “I’m really sorry, but I’m not ready to do that.” Megan got downright feisty.
“You’re embarrassing me, Hannah! You weaseled your way in here and now you’re acting like a little baby in front of all my friends!” Now, this wasn’t really fair. Hardly any of the older girls there were doing anything below the waist, a few were, but most weren’t going any further than Hannah had.
Hannah snapped back at Megan. Megan called her a “little baby tease,” and the other older girls laughed at Hannah. She got upset and ran from the party without ever saying a word to me. I think I was supposed to follow her out, but I was kind of embarrassed myself. I didn’t really know what to do.
“I’m sorry, my little cousin’s such a bitch, Liam,” Megan said. “You’re a really cute guy. If you weren’t two years younger than me, I’d probably make out with you myself.”
I took a shot. “Actually, I’m only a year younger than you. I turned 13 in October. I got held back in second grade because we moved around a lot.”
“Shit, Megan,” one of her friends said. “He’s only eight months younger than you. You turned fourteen in February.”
“Well…” Megan said.
“He’s fair game!” another girl said, “and he’s a hottie.”
“Keep it in your pants, woman!” the girl’s freshman boyfriend joked. Everyone laughed.
“Come here, Liam,” Megan said. She led me into a little room under the basement steps. It was where the family kept camping gear. We ended up on top of a pile of sleeping bags. Megan was in a mood, and at times she kind of scared me with how aggressive she was. But about half an hour later, I ended up giving that girl the best ninety second fuck I could muster. She didn’t even complain about how quick it was. It was only her second time, and the other boy hadn’t gone any longer.
That was my glorious first time. Not awful, but not exactly the kind of story worth telling in great detail. But the fact of the matter was that I had done it with an eighth grade girl. Back in sixth grade on Monday, you’d have thought I’d climbed Mount Everest. Hannah was upset, of course. I was getting treated like a hero, and she was a laughingstock. She started calling me names and cussing me out. Fortunately, Enya had heard about it already and given me a response. “Hannah, you ran out and left me alone in a party full of people I barely knew. I didn’t take that as a sign that that you wanted to go steady.” That got a few responses of “Oh, burn!” and the like. Hannah, who really hadn’t done anything except hold the line on her virtue, suddenly looked like a fool. I’d have felt bad about it if I hadn’t been a thirteen-year-old boy who had just nailed a girl two grades ahead of him. That sort of thing makes a boy feel a bit full of himself.
The eighth grade girls didn’t start knocking down my door then, but the more adventurous seventh grade girls did. The girls in my class got a little jealous. Well, certain girls did. But since they weren’t quite willing to do what the girls a year older wanted to do, I diverted all my efforts to the seventh graders. They were actually my age anyway. I even learned how to go for more than ninety seconds. I think that one of the times I did it the summer between my sixth and seventh grade years I might have gone over the five minute mark!
The honor roll preppie girls in my sixth grade were kind of fascinated by the whole thing, but they were fascinated from a distance. I think that they were afraid my penis was going to fly out of my pants and fuck them or something. A few of them would actually look at my crotch as if it was a loaded gun with the safety off. Later in the school year, it had become kind of a game for them to prove their bravery by talking to me or smiling at me. They weren’t about to go out with me, but it made them feel bolder to be around me and not freak out. Three, four or five years later, most of those same girls would discover the joys of sex. They would even approach it with the same enthusiasm and constant optimism with which they seemed to approach school activities and anything else their clique now figured was acceptable for girls their age. Their steady boyfriends were kind of the only beneficiaries of all this, but those guys had some real cuties in their beds and backseats in those years. But at twelve, no way in hell were the good girls going anywhere near something as dangerous and dirty as a used penis.
My seventh grade year was when something entirely new happened to me. I had a straight A student actually fall for me. The girl in question was neither a preppy princess nor a blossoming sex bomb. She was “Calamity Jane” Weatherstone. Jane had just moved in at the beginning of seventh grade. She would have been one of the “popular” girls if she hadn’t been so damned awkward. She was tall and thin with bright red hair and a very serious set of braces. She completed the sweet but not hot look with a pair of frameless glasses which were trendy at the time.
Jane could still have pulled off the role of follower in the popular clique if she didn’t seem to find her way into one ridiculous situation after another. She would lock her key in her locker; she would forget her gym shorts and have to wear a pair of the “Old Bertha” loaners the coach made the girls wear so that they didn’t get out of gym class by forgetting them on purpose. She tried playing volleyball, but at the first match she threw the ball up in the air for a serve and missed it completely. Later, she got so caught in the net that the refs actually had to drop the net to free her.
Jane also had some personal quirks that were not in line with the princesses. She didn’t giggle. She either just slid her glasses down her nose and stared at you, or she laughed out loud. Oftentimes her out loud laugh was a bit too strong. And if she really cracked up, she snorted at the end of the laugh. She played in the band, but she didn’t play flute or clarinet or any other girlie instrument. She played the baritone. She was good at it, and that meant she practiced every night. So, every morning, she would drag that bulky case through the crowded hallway and up the steps to the band room. She was constantly bumped and occasionally flattened someone on accident.
But Jane had a gentle nature and was pretty patient with people who were less intelligent than her. That was good, because the group of people who were less intelligent than her included every single person in our middle school. Some of the teachers, and only some, knew their individual subject matter better than her, but none of them had the sheer brainpower she had. Only Mrs. Donegal, the incredibly smart math teacher and Mr. Donegal, her equally smart science teacher husband, really took a shine to her. They would beam with pride when she one-upped them. “A wonder, Jane! That’s what you are!” Mr. Donegal said one day. “If I wasn’t twenty years older than you and happily married, I’d probably have a little crush.” Jane blushed bright red; no one ever flirted with her. Having a good-looking teacher—that most of the popular girls crushed on—gushing about her was a bit of a thrill. Donegal wasn’t a creep, by the way. He was trying to help the rest of us see how incredible she was. Of course, it backfired. The other girls got catty.
Jane’s inability to keep from making comments that went way beyond what the teachers were able to come up with made some of the teachers feel pretty intimidated, and a few of them were outright mean to her. The worst was Mr. Berger. He was very young and wanted to be the most popular kid in school. He taught English and always let the princesses out on passes. He would give them some little errand to do and let them just run around doing whatever for the whole hour and then excuse them from homework. The popular kids loved him, and I hated the guy. I didn’t usually mind teachers; most of them liked me well enough since I wasn’t an asshole to them. But they were supposed to be the grown-ups. Berger wasn’t any more grown-up than we were. He only taught because he wanted to coach basketball.
Well, one day, Berger said something that was flat-out wrong, and Jane corrected him. I thought she did it in a pretty nice way. Berger got mad. “Well, I guess you would know better, Jane. You’re the school brainiac. No wonder, Mr. Donegal has such a hard-on for you.” Berger had used a phrase that most of us used all the time in a non-sexual way, but he had intentionally used it to link Donegal and Jane in a way that sounded indecent. He knew how a classroom full of twelve and thirteen-year-olds would react. Jane looked like she might be physically sick or have to run from the room in tears. I pulled the focus away from her and put it right on me.
“Apologize to her,” I said in my best attempt at a bass growl.
“What did you say, Liam?”
“I told you you’d better apologize to her.”
“You can’t talk to me like that, son.”
“I’m sorry,” I said, angered by his smart-ass grin. “Apologize to her right now, you fucking asshole.”
“Get out of my class and go to the office.” He still had that little smile on his face. He knew I hated him. He returned the feeling.
“Okay, I’ll go tell the principal that you made an obscene comment to a twelve-year-old girl. Or better yet, I’ll go tell Donegal. Then we’ll all come watch him kick your ass in the parking lot after school.” I got him with that. Donegal would wipe the floor with this piss-ant.
“Mr. Donegal is a friend and a colleague. He’s not going to do any such thing.” Berger was still shaken by the thought that Donegal just might. Donegal was a professional, but he was fiercely protective of the kids. If he knew that Berger had gone after his shining star, it might really get the science teacher’s Irish up.
“Let’s take our chances,” I said. I was feeling cocky at having him a bit cowed, so I pushed it a little more. “And if he doesn’t kick your ass, I will.”
“You’re in way over your head, little boy.”
“So are you. Apologize for being a dickwad, or we’ll see how it all plays out.”
Berger weighed his options. He finally turned to Jane. “I really am sorry, Jane. I guess I was out of line.”
“You guess?” she snapped. Tears were streaming down her face, but my actions had tapped into her temper, and she had transformed her embarrassment into righteous anger. Her whole body was shaking, and I was a little afraid she’d get up and try to kick his ass. I’d have been right behind her.
“I really was out of line,” he said, now fearing that she would go to the office and he would really get called on the carpet. “Jane, please accept my apology.”
“Fine,” she grumbled.
“As for you,” he said, turning to me. “I think you and I are going to have a little talk after class.” He was acting like he was going to be tough with me while everyone was here, but he would puss out after class when it wouldn’t cost him anything. He knew I had him.
“As for me,” I said. “I don’t wanna be in your class anymore. Write me a pass to the library every day and have Jane tutor me there. That way I might actually learn something.”
“Me, too,” said Jake Hansen, one of those kids who got good grades but nobody noticed. “I wanna do that, too.”
“Me, too,” said a girl. I turned to see it was Hannah Moeller.
“Fine, I’d be glad to have those of you with poor attitudes out of the room anyway. That way the real students can learn something.” He wrote the passes.
“Thanks for backing me up,” I said to Hannah as we walked toward the library. I was surprised that she had any positive feelings for me.
“I didn’t do it for you, puke-stain,” she hissed. “I hate Berger, and I think Jane is one of the coolest kids in school.”
“Me, too,” Jake said. “Although, I don’t really think you’re a puke-stain. I think you’re a cum-addled idiot, but you stood up for a really cool girl.”
So, that was it. Jane had a class of three. She made sure she and Jake still got an A and managed to get B’s for Hannah and me. We were good with that, especially since the grades were legit. She made Berger give her copies of the tests, and we did well on all of them.
As time went on, I began to notice that Jane looked at me like I was some kind of hero. I was a little ashamed of that, because I might not have done it if I hadn’t hated Berger so much. Well, maybe I would have. I really felt bad for her that day, and I wasn’t afraid of getting into a little trouble. It all got easier to take, though, when I realized something that Hannah and Jake had known all along. Jane Weatherstone was freaking awesome! She actually taught me way more about books—and she did make us read them aloud with her—than Berger ever could have.
When the Christmas Carnival came around, I asked Jane to go with me. She looked worried. “I don’t know, Liam. I do really like you, but I’ve never been out with a boy before, and you’ve—you’ve actually had sex a bunch of times.”
“Well, I can sort of see where the two things are connected, but did you ever hear of me MAKING a girl have sex with me?”
“Well, no. Everybody seems to think you’re pretty nice.”
“So, then we wouldn’t do anything you didn’t want to do.”
She smiled, and I knew I had a date. But she did throw a whammy at me. “You’re going to have to meet my dad first. Family rule.”
“Oh, crap,” I muttered.
“He’s nice. He just wants to make sure my sisters and I don’t go out with a sleazeball.”
“Ain’t I the kind of guy your dad would think is a sleazeball?”
“I’ve been prepping him against this eventuality,” she said and then smiled and denied me the chance to play dumb. “I kind of thought you liked me, so I told him that you threatened to kick the teacher’s ass if he didn’t apologize to me for making a lewd comment. Then I had to spend an hour trying to keep him from calling the principal and wrecking everything. But I convinced him that you jacked Berger up so good that he’s learned his lesson and won’t ever mess with me again.”
“Jane, I’m still kinda nervous.”
“Well, then you know how I feel. I’m kind of nervous about going out with the guy who’s been having sex since sixth grade.”
“I’ll do it,” I said. “But you’d better put out!”
The momentary look of shock on her face was worth the scare I got when she faked a knee to the groin. For once, Calamity Jane had the perfect amount of control over her long legs. It was close enough to make me believe for a tenth of a second, but my boys were never in real danger. We both broke out laughing. Her laugh ended with a snort that sent us both into a second fit of laughter. When we got ourselves under control, she looked around warily and then gave me a kiss. I thought she was just going to do a quick, “ain’t you cute?” peck, but she held it for a moment. “My first,” she whispered.
“Best I ever had,” I said, not quite understanding why I had liked it so much.
“Not buying that,” she said as she turned and started to walk away. “But thanks.”
I watched her tall frame as she headed off to class. I admired her long legs and slender bottom. I was just a little amazed at how nicely she was put together. Then she ran into an eighty-pound sixth grade boy and flattened him, sending books everywhere. She apologized and started to help him gather up his things. Maybe that should be expected, but it was probably the nicest thing I’d ever seen a seventh grade girl do for one of the little bitty sixth grade boys. Most of them treated those kids like vermin.
Three nights later, Erin drove me over to Jane’s house. “Shit, little brother, hold onto this one. That car in the driveway is worth about twice what our house would sell for. The house itself is worth most of our block.”
“Thanks, Sis. That doesn’t make me feel nervous about meeting her dad at all.”
“Liam, you’re a little shit pain in the ass, but you’re an awesome little shit pain in the ass. Anybody who don’t see that needs to answer to me.”
“Good idea,” I said. “You’re coming with.”
I dragged Erin up to the house with me. She didn’t want to go, but she was offering me good advice anyway. “Say you’re full name and call him mister. Then explain who I am. I can help out then if there’s a tough spot.”
Jane answered the door and was surprised to see Erin had come to the door. She invited us both in, though. Jane sat us in the living room and went to get her dad from “the study.” I looked around at the fancy furnishings and the old-fashioned clock on the mantel of the fireplace. Then I looked at Erin. Her eyes were popping, too. “The study?” I said. “Ain’t that where Colonel Mustard killed Mr. Body with the candlestick?”
“Bon mott, young man,” a deep voice said from the doorway. “Good one.” A six-and-a-half foot redheaded giant extended a garbage lid toward me. Actually, it was just his hand, but it looked that big to me. “I’m Jack Weatherstone. I’m sorry Amelia couldn’t meet you this evening. She’s covering the evening shift for me in the ER. I have a consult with one of the surgeons scheduled for six AM.”
“Dr. Weatherstone,” I said, standing and shaking his hand. “I’m Liam Kilroy. This is my older sister, Erin. She’s our chauffer for the evening.”
“Mom wanted to drive them,” Erin said as she stood and offered her hand. “But she had to work this evening, too. She’s the shift manager at the store, now.”
“Well, it was very decent of you to come in and introduce yourself. It puts me at ease to know Jane is in good hands.”
“So, Liam, why don’t you and your sister have a seat?” He gestured to the loveseat. Jane sat next to her dad on the couch. “I just wanted a minute to get your whole take on the Berger incident.”
“He was out of line,” I said, “but he apologized in front of everyone. I think he learned not to pick on a girl who has friends.”
“I’d still like to see him pilloried,” the huge man growled.
“Don’t know what that means, sir, but I have a feeling I would like to see it, too. I kinda hate the guy.”
“With good reason, it sounds like. But you and the others who backed you up are pleased with the arrangement?”
“They backed Jane up, sir, not me. And Jane’s an awesome teacher! I learned way more junk from her than I would have from that jerk.”
“I’d imagine you’re right,” he said, still not quite satisfied that he hadn’t gone over to the school and bullwhipped the man. “Thank you for defending my daughter’s honor in my absence.”
“Wow! It sounds cool the way you say it. I just got kind of mad and shot my mouth off.” Jane cleared her throat. “Shot off my mouth, sorry for the prepositional ending.”
Erin lost it. She bounced up and hugged Jane. “That is so adorable! You totally have him in line! You go, girl!”
Dr. Weatherstone gave a deep belly laugh. “And here I was worried that Jane wouldn’t socialize well,” he said, still chuckling. “She puts all of us to shame in the intellect department, but it’s hard for a girl like her to make friends. I can see that she has one in you. And it’s no small comfort to see that she has her beau ‘in line’, as your delightful sister says.” He turned to Jane. “You go, girl!”
“Dad, it sounds goofy when you try to talk like a kid,” she said with a roll of her eyes. “Actually sounds pretty goofy when I try it.”
“That may be,” he said. “But I was actually giving you leave to attend the carnival with this young man. You go, girl!” Jane kissed him on the cheek and extended a hand to me. I took it and we walked toward the front door.
“Oh,” her father called after us. “Liam, what do you think of this Mr. Donegal? He is spending a fair amount of time doing independent work with my daughter. I’ve met him, but I’d like your opinion. You seem to have my daughter’s best interests at heart.”
“Donegal’s not a perv or anything if that’s what you mean. And besides, his wife is actually kind of hot. But he’s just spending time with Jane because he figures he’s kind of helping out someone who’s going to be really special someday. Some grown-ups are just really cool.”
“Like you, Dr. Weatherstone,” Erin said. They both blushed. Erin had formed sort of an instant crush on him, and he’d just been complimented by a pretty seventeen-year-old girl.
“Hear that, Jane? I’m cool,” he said and returned to his study. “Remember your curfew!” he called back down the hallway.
“And there go most of his cool points,” Jane said and walked with me to the car.
Jane and I had a great time at the carnival. She did have a minor incident at the Candy Cane Challenge. She was aiming for the candy canes and somehow managed to throw her ring around the volunteer’s pointy elf hat instead. But later I won her a stuffed little Rudolph at the Reindeer Games booth. I got a kiss for that, and we got scolded by Mrs. Donegal. Only handholding was allowed. But because it was Jane, the reprimand was pretty mild.
At the end of the night, we kissed in the parking lot for a little bit while we waited for Erin to pick us up. There were a few couples over in the shadows making out and basically dry-humping against the wall. “That’d normally be you, wouldn’t it?” Jane asked sadly.
“I guess,” I said. “But I’d rather be with you.”
“Liam, I’m glad you’re with me, too,” she said softly. She snuggled up to me and held my upper arm in both hands. She looked at the horny couples. “Maybe someday,” she said with a sigh. “But not for a long time.”
“I can wait,” I said with my best smile, the one I knew did things to a lot of girls. It did things to Jane, too, but that didn’t really make her more likely to do anything more than what she was doing at the moment. It was the first time, however, that I really thought about what I was in for with Jane. I had liked being one of the guys getting dry-humped by a girl outside the carnival. But when I looked back at her I realized that she was the one I wanted most to have pressing up against me. Part of that was just that she was right there and I thought she was cute. But part of it was that I liked her more than I’d ever liked any of my other girlfriends. That was why her innocent little kisses felt better than the hot and wet kisses I’d gotten from the others. For the first time, I made a genuine connection between sex and affection. “Jane, will you be my girlfriend?” I asked.
“I want to be,” she said. “But I’m still not going to…” she lifted her eyes toward the couples on the wall.
“I know,” I said.
“Then, yes, Liam. I want to be your girlfriend.” We kissed again, and this time she opened her mouth a little bit and slipped her tongue slightly into my mouth. We frenched for a little while, but she didn’t press into me or invite my hands anywhere besides the small of her back. “Did I do that right?” she asked when we broke the kiss. Her glasses were knocked kind of crooked.
“You’re a great kisser,” I said and slid her glasses back into place. I meant it. She had a nice touch.
That was only one of the many wonderful things I learned about Jane in the next few months. I learned that she could burp the alphabet. I learned that she could shoot rifles and used to hunt when she lived in Wyoming, before her dad got a job as the Chief of Medicine at our local hospital. I learned that she did have great coordination at one thing. She could play video games like nobody’s business. “Lots of time alone when I was a kid,” she said sadly. But then she smiled. “I’m not alone anymore.”
It was true. She had me, and she had become good friends with Hannah. Out of our little English class quartet only Jake didn’t hang out with Jane outside of school. His interest in her faded as Jane took interest in me. He had wanted to kiss her, too. I caught onto it and told him that I was sorry that I had rack-jacked him. I hadn’t done it on purpose.
“It’s okay,” he said. “When things get me down, I just keep repeating my happy words until I feel better.”
“What are your happy words?” I asked.
“Stanford. California pussy.”
“Who’s Stanford?” I asked. He just stared at me. “Well California pussy sounds nice,” I added.
But all of the wonderful things about Jane only made one other thing very difficult for me to handle. The more I got to know her, the more I liked her. The more I liked her, the more I wanted to fuck her. It sounds crude to say “fuck” when talking about an innocent like Jane, but let’s face it. I was fourteen and used to having sex. I had been choosing my other girlfriends mainly on the likelihood of getting into their pants. I did want to fuck Jane. I wanted to fuck her real hard and real often.
A couple times I tried to go a little further and got gently shut down. I stopped trying for a while, but then the horns would pop back up and I’d try again. Finally, one night I could feel how warm she was. I put my hand over her sweater and felt her almost non-existent tits. She moaned softly, but for the first time she didn’t pull my hand away. We were on her couch and no one else was at home, so I tried sliding my fingers under the waistband of her jeans. She pulled it away and I went back to feeling her up over her sweater. She cooed softly, and pressed her long, warm body against me. I decided to try for the hand in her pants again. She pulled it away and I sighed heavily. She got mad. “Dammit, Liam! I’ve only been thirteen for a couple weeks,” she said. “I am not ready to have sex.”
“Well, sorry, but you don’t have to get mad about me trying to get a little something.”
“Don’t say you’re sorry when you’re not sorry,” she said getting even angrier than before.
“What’s the big deal? I don’t get mad or anything.”
“No, but you do get sad, and that makes me feel bad. Besides, it’s not that easy for me to say no all the time. Sometimes I feel like I’m the only one here who has to use her head at all.”
“Well—wait! Did you just say it’s hard for you to say no?”
“Of course it is!” she said. “You think I don’t WANT to?”
“Then why not just do it? I don’t mean IT, but why not just do some things?”
“Because then it would be even harder to say no,” she said.
“And why is saying no so important?” I asked.
“Because I’m not ready!”
“It’s not hard, and it feels great.”
“It’s hard for me. I have to get something stuck inside me, and it scares the hell out of me. Besides, I could get pregnant or something.”
“I’d use a rubber.”
“Knock it off, Liam,” she said, tears welling up in her eyes. “If you really cared about me, you wouldn’t do this to me.”
“If you really cared about me, you’d want to do it with me!”
“I DO want to do it with you. I’m just—“
“Not ready. I know. Heard that before.”
“Heard, but never listened.”
“I’m not doing this anymore tonight. I want you to leave.”
“You’re breaking up with me?”
“I don’t want to, but if this is how it’s going to be, then yes.”
“Fine. Call me when you grow up a little bit.”
“You call me when YOU grow up a little bit!” she snapped and left the room. It was a damned long, cold walk home.
While I was walking home, Hannah was already on her way to Jane’s. Jane had called her by the time I’d bundled up and walked out the door. They had a long talk about me. Hannah knew me fairly well having gone to school with me since kindergarten. She had mixed opinions about me. Of course, she was still mad I fucked her cousin on a night when I had started out with Hannah. But she blamed herself for storming out without me. But Hannah had come to like me through our mutual friendship with Jane. One day she had even told me that she was now able to look at me without wanting to scratch my eyes out.
Somewhere in the course of their conversation, Hannah kind of spun Jane’s head around a bit. Hannah hadn’t been ready to go beyond letting me up her sweater a year before, but she’d begun to believe that she was ready for more than that now. She told Jane that if she had a steady boyfriend she would let him do lots of things, probably even go all the way. Jane was stunned. Her sister in virginity was more than wavering. She was admitting she was ready to shun her purity “for the right guy.”
Jane didn’t have another close friend whose judgment she valued. Both of the kids she was close with thought that thirteen-year-old girls should have sex with their boyfriend. Now, considering that Hannah and I weren’t as smart as Jane, there was some room for doubt about our opinions. But Jane didn’t seize on that. She seized on what her body wanted to do and probably on her fear of alienating the two of us. But I don’t think that either of those things were what finally pushed her to genuinely consider giving up her virginity. Jane and I had something real going on, and she saw genuine value in that.
The next morning she called me. She said she had gone too far in throwing me out. She had been scared and confused, but she had talked about it with Hannah. Jane said that no matter what, she did not want to break up with me. I told her that I didn’t want to lose her, either. “Can you meet me at the mall today?” she asked.
“Yeah, Erin has to drop Enya off for work at Cinnabon anyway.”
We met in the food court a couple hours later. For a long time, we didn’t even talk about the night before. We just laughed and joked about normal stuff. As I finished the second free cinnamon roll my sister had given us, I looked at Jane. She was sipping on a soda but couldn’t eat her roll because of her braces. Her glasses had slid down her nose a little bit. I could see her blue eyes. They almost seemed to twinkle now that she was happy. I realized that she had perfect skin. She didn’t have more than a couple little bumps under her sweater, but her long legs more than made up for her lack of chest. She looked quizzically at me. “God, you are so beautiful, Jane.”
“You’re the best-looking guy in our class, Liam.”
“I think I love you,” I said. “That’s not about getting into your pants, either.”
“It wouldn’t get you there if I wasn’t ready,” she said. “And I think I love you, too.” I kissed her for a long time. It was the first time she had really kissed me for that long in a really public place like this. “Everything in my life is about my future,” she said when we finally stopped kissing. “But I think maybe I need to think about what I want to do right now. I don’t want to end up in the future wishing I’d had more of a past.”
“That’s funny,” I said. “Last night on the way home was the first time I ever really thought about the future. I have no idea what mine is going to be like, but I was really sad that you might not be a big part of it.”
“I know,” she said. “No one else has ever made me feel so happy. I was stupid to ever think we should break up just because I was upset. You’ve just been such a nice guy that you never really made me upset before. I didn’t handle it very well.”
“I was kind of a jerk. I mean, you were right. I was hearing you but not listening. I talked to Erin about it last night, and she got really mad at me. She said I was an idiot to let it get that far.”
“Let’s forget about that,” she said. “We were both kind of jerks.” We kissed and made up the rest of the way. “You know, my parents are still out of town at that convention.”
“How are we going to get to your house?”
“Same way I got here,” she said. “Come on.” Turns out that the daughter of two doctors can afford a taxi fare.
For the first time, Jane and I didn’t go to the couch when we got in her house. I had been her boyfriend for three months and had never even been upstairs at her house. But she led me right to her bedroom. “Um, Jane?” I said as I realized where we were going.
“I told you that telling me you loved me wouldn’t get you in my pants if I wasn’t ready. I’m ready.”
“I was actually just going to ask where you’re sisters were.”
“Oh. Little one is staying with a friend. Big one is probably doing the same thing I’m doing right now.” She looked at me for a moment. “You didn’t act surprised when I said I was ready.”
“You more or less said it at the mall. I was actually listening.”
She grinned. “Of course you were listening when I said that.”
“I love you,” I told her as she opened the door to a huge bedroom all decorated in light greens.
“That’ll do it,” she said with a sigh.
It was all different for me this time. I had always gone through the making out and gradually getting naked process. Jane sat me on the end of the bed and then undressed in front of me. She went slowly, but not as a tease. She was scared and nervous. When she was finally completely naked, she stood in front of me but covered her private parts. She took a deep breath and pulled her hands away. I stared with my mouth slightly open. “Say something,” she squeaked in fear.
“That’s a good thing to say,” she said in great relief. “Can I see you now?”
I had never been timid about being naked before, but her sheer terror that I would be turned off by her naked body kind of rubbed off on me. I stood and slowly undressed. I was afraid that my erection would somehow scare her off or make her change her mind. She had been afraid of getting something stuck inside of her, and now she was going to see it. I wished I had been able to hide my cock or at least not have it sticking straight out at her until we were already in the middle of things.
“You’re so hot,” she gasped.
I stepped toward her then. The closer I was, the harder it was for her to see my hard-on. She opened her arms to me and I stepped in and kissed her. I slid my hands to her bottom. She moved toward me, and my cock pressed into her hip. She looked down and studied it. She timidly reached her hand down toward it. “Wow!” I said again as she took my shaft in her hand.
“This thing is huge!” she said.
“I think it’s kind of the normal size,” I said. Stupid! If a girl tells you have a huge cock, you let her keep thinking you do.
“Maybe it is a normal penis,” she said. “But I know how big my vagina is. And this looks bigger than that.”
“Don’t be scared, Jane. I’ll be real gentle.”
“I know you will, but I’m still going to be scared.” She kissed me a little bit. Her warm hand was still just wrapped around my cock. “Should I play with it a little bit?”
“Yeah,” I croaked. “That’d be good.” She gently stroked it while she stood leaning against me. Then, she knelt and looked right at it as she continued gently stroking it.
“Am I doing it right?”
“You can go harder than that.”
“Should I suck on it?”
“Yeah, that would be really cool.” She kissed the tip of it and then teased it with her tongue a little bit. It felt like the first blowjob I’d ever gotten. Every touch of her lips or tongue thrilled me. She was making her tongue long and thin and kind of pointy. It made contact with only a little bit of the underside or head at any given moment. I grew weak in the knees and reached back for the bed. She let me sit and then finally took it inside of her mouth. That was hard for her, because her braces only let her mouth open so far. “You might need to take the back bands off,” I said. I’d been through this with seventh grade girls before.
“I should have thought of that,” she said. She took a couple of bands off her braces and could open up wider. She sucked on it very gently and now flattened out her tongue on the underside. She wiggled it back and forth. I groaned, but she could tell it was pleasure. She did it a few more times and I groaned more. She stopped before I got too close. “I don’t want you to ejacu—cum. I don’t want you to cum in my mouth. Sometime, maybe. But I want you to do that inside me for my first time. With a rubber, though. I’ll eventually talk to my mom about getting on the pill. Kind of scared, though.”
“Just don’t ask your dad,” I said. He was the nicest guy I’d ever met, but he could have knocked me right through the wall.
“Not even if I was married!” she said with a little laugh. She kept stroking me gently. “I guess I should, um, lie down and get ready.”
“I can help you get ready.”
“Oral pleasure?” she asked. “You know how?”
“I’ve done it a few times, but I never wanted to do it more than I want to do it with you.” She seemed okay with that. Maybe she was a little relieved now that I had done all this before. It made her feel safer that she was in the hands of someone who was doing more than just guessing what it should be.
She lay down on the bed and tentatively opened her legs a little. I scooted up from the bottom and spread her a little wider with my shoulders. I kissed the insides of her thighs and she jumped a little. She took a few deep breaths, and I moved my kisses further. “Wait,” she said softly. I was afraid she’d changed her mind. “Say you love me again.”
“Jane, I love you. You’re the only girl I ever loved.”
“I love you, too, Liam. Go ahead.” I gently ran my fingertips through the light covering of soft, straight ginger hair on her pubis. She shuddered and took another deep breath. I moved my fingers to the swollen lips of her pussy and parted them slightly. I slipped the tip of my tongue into the opening I had created. “Oh, god that feels nice,” she said in a dreamy voice. I started to run my tongue up and down the length of her slit in slow movements with a little side-to-side action. She had a very light taste to her. It was a little bit like Juicy Fruit gum. I really liked it.
Jane was losing her fear a little bit during this. It was pleasing without being maddening. There was no pain or discomfort, only mild ecstasy. I slowly began to kiss her sex and spiraled, zeroing in on her clit. I gently latched onto it. Sweet Jane did one of those things that was kind of unique to her. “ZOWIE!” she cried. “Do that more!”
Like most boys, I had only half-believed my girl when she had said she really wanted to have sex, but just wasn’t ready for it. Now, I began to realize that her motor ran as hot as mine. I got more assertive in my efforts at her clit and pussy lips. She responded with moans and grasping motions with her hands against my hair. “Hot! Hot! Hot!” she whispered. She twisted her hips and straightened and bent her legs several times.
One of my exes had told me that she found it way easier to take in my cock if she had already cum first. I wanted this to be as easy as possible for the one girl I had ever loved. I kept going at her with licks and kisses until she got close. Then I took her clit in my mouth while I used my fingers at her opening. “Oh, god yes!” she hissed and then made a few gasping sounds. Her final cry was a series of short “W” sounds followed by a nicely rounded “Waah!” She brought her hips up high and then dropped down on the bed, clutching my head in both her open hands and holding me tenderly to her. “Liam, Liam, Liam,” she said softly.
I climbed her and kissed her passionately. She kissed me back with a tenderness that calmed me slightly. “Be sweet,” she said to me and tilted my head up so that she could see my eyes. She liked whatever it was she saw there. “Be sweet like this and I will make love to you.”
“You’re so beautiful,” I said. She smiled sweetly and let me go. She knew I had to go back to my jeans to get a condom. I brought it back with me and let her watch me put it on. She looked up at me, and I could see fear in her eyes, but there was love and desire there, too. She nodded and held her arms up to me. I didn’t go into the embrace, but I took her hands and kissed each one for a long tender moment before I got between her legs.
I looked at her face, the face I had decided was more beautiful than that of any princess or sexy little wild child I had ever known. Her eyes were closed, and her lower lip trembled slightly. I slid the tip of the condom up and down her sex a few times to lubricate it. She flinched at the first touch, but sighed as she felt the gentle action. As sweetly as I could manage, I pressed my head to her tight opening. She whimpered a little, bit her lower lip, and nodded. I pushed in a few inches.
“Oh! Oh!” she cried in fear more than pain. This really did scare the hell out of her, but she wasn’t trying to make it stop. I worked myself back and forth a little, trying to let her adjust to the notion that I was in there. She was tight. I don’t know if she was the tightest ever, I had been with seventh grade virgins before. I still think that hers was the warmest pussy I ever experienced. Maybe it was just the emotion of it all, but she was without a doubt wonderful inside. I began to think that maybe my efforts to let her adjust weren’t quite as comforting as I’d hoped. The really scary moment was still ahead of her, and I was delaying it.
I pushed with one slow but strong thrust. Her cherry fought back hard for one instant, but I was able to go through without having to back up and take a hard swing. “OW! Oh, Liam, it stings!”
“I’m so sorry,” I said as I was able to lie on top of her and kiss her now. “I wish it didn’t hurt, but it shouldn’t hurt for long.”
“I know. I know. Still stings.”
“I love you, Jane.”
“That helps,” she said and cried a little bit. “You’re being sweet. I trusted you to be sweet. I love you, Liam.”
I started to move slowly. She drew a few sharp breaths, but didn’t say “ow” or cry out again. She was still shedding a few tears. I made a few long slow thrusts, going as deep as I could go in this position. She winced a little as I worked into parts I hadn’t touched before. “Is it okay?” I asked after a few more strokes.
She grabbed my face with both hands. She kissed me deeply. She smiled even as she gave an emotional sob. “It’s getting good,” she said. I began to move in a more steady rhythm. “Oh, wow!” she whispered. “I like it now.” She looked at me with a little eagerness in her eyes. I began to pick up the pace. “Hot!” she said with a quiet urgency. I had wanted to fuck Jane for a long time. I found myself making love to her instead. It was something I hadn’t really done before. There was less of a pounding action to this and more of a reaching into her with all of my strength. Something in the way I was striving was allowing me to get better penetration than I had with the girls I had taken before.
“You are so wonderful,” I said softly. “It never felt anywhere near this good.”
“UMMM! UMMM! Am I doing it right?”
“Wrap your legs around me and it will be perfect.” She rotated her hips as I continued loving her. Her heels pressed into my backside.
“Better,” she moaned. “Even better.”
I couldn’t believe what I was feeling. She had been the best already, or maybe I had been at my best because I was trying so hard for her. But now she was urging me in with her long legs and her slender hips. Her kisses on my neck and ear were incredibly pleasing. Her hands ran up and down my back in passionate efforts to tell me what her heart felt inside. My body vibrated slightly from her passionate moans.
Some kids had been turned off by how loud Jane could be when she laughed or spoke when excited. That volume returned now, but anyone who experienced it wouldn’t find it a turn-off now. “God, it’s good! It’s good!” she cried. “I love you!”
“Love you, too!”
“Take me! Take me!” she said in a dreamy voice. Her romantic nature was in full gear, now. “My sweet love!” she said in a voice that was dramatic but not in any way false or forced. I continued using every bit of strength I had to make my efforts firm without getting wild or raunchy. After another minute, she cried out in wonder and joy. “You’re sending me over!”
I had never, ever given a girl an orgasm on her first try at sex. To tell you the truth, I had rarely had a girl climax during actual sex. I always tried to find a way to make sure she got one after—if she was willing to let me. Erin and Enya had told me it was a guy’s duty. But now, innocent Jane was going to cum before I did. She made her “W” sounds and her wonderful round “Waah!” She was getting close to being spent, and I was kind of grateful for that. I couldn’t go much longer. I had been working so hard to do everything right for the girl I loved so very much.
It almost felt like my balls contracted right up to my body right before I erupted into her. I groaned, and she squealed. She took my face in both her hands and smothered it with little kisses. I pressed my face to her cheek and returned them. I could feel that she was crying tears of joy. We stayed in one another’s arms for a very long time. My first love; her first time. It was simply as good as it gets.
Remember back in high school when there was the one couple that you knew couldn’t ever end up together but still seemed perfect for each other at the time? That was the role that Jane and I played for the next five years of our lives. Jane had said that she didn’t want to reach her future and not have a past. I became the key figure in a brilliant woman’s past. Even by the end of our junior year, we had agreed that when she left for college, it would be the end of our wonderful relationship.
But we knew that we would get every bit of love out of the time we had left. We did everything we could think of together. We made love again and again, but we also got naughty. In the end, I did fuck Jane Weatherstone, and she fucked me right back. Through it all, there was still the love, romance and friendship that had brought us together. Those emotions were what allowed me to be unselfish and let her go when the time came.
We made love the night before she left for Harvard. When Hannah and I put her best friend and my first love on a plane the next morning, Jane hugged me one last time. “I have the best and happiest past any girl could ever ask for,” she whispered in my ear.
“Go get your future,” I said, fighting back tears.
She didn’t bother fighting back hers. “You get yours, too.”
“I have no idea what that is, but I’ll try.”
“Oh, you’ll figure it out,” she said. “You don’t think you’re smart, but you are. You’ll know your future when it comes your way.” With that, Calamity Jane—now braces-free, contact-wearing and simply a glamorous beauty—became my past.
Her final words to me that day were right. I did recognize my future when it came my way. I married a beautiful blonde girl two years later. She wasn’t a virgin the first time I made love to her, but she had been the first time I’d made out with her seven years before. Hannah and I still see Jane and her husband every few years. We live in the past for a little while; then we bask in the wonderful present we’re enjoying. Finally, we share our dreams for the future.
“Well at least I know I’m gonna get fucked good tonight,” Hannah said once after one of our little reunions. I looked at her with a curious smile. “You two,” she said. “It’s still there.”
“Yeah,” I admitted. “But it’s right here, too.” I took her hand and gave her the smile that did things to girls.
“Yeah,” she said breathlessly. “It really is here, too.”
I had considered myself lucky when I had lots of middle school girls that liked me. I found out that true luck was something else. A man was truly lucky if he found real love once in a lifetime. I was doubly blessed. I had found it twice.
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