Chapter 2: Teenage Explorations

MAY 2000, SOPHOMORE YEAR

"See? He's got that look again!"

I rolled my eyes at Kenny Doyle and took another bite of my Salisbury steak. I wasn't sure why they called it a steak. It pretty much looked like a cross between meatloaf and a hamburger patty. But for now, I concentrated furiously on my food and made sure I didn't drift away to la la land again.

It was so easy to drift. Just last night, I'd cum three times with a beautiful woman. I'd had sex. I wasn't a virgin anymore. And the memories of what activities had taken place were simply so wonderful that I couldn't help but glow and smile beatifically.

The first time Keira had given me a blowjob, I walked around school with a calm serenity. I'd no longer had that manic urge to get off with a beautiful girl. Now that I'd actually had sex, I not only found that serenity, but also a cool confidence.

I was a true man. I was a functioning, productive male of the species. I'd had sex with a beautiful woman, and no one could take that away from me. No longer was I just another teenage virgin spending half of his day trying to figure out how to lose said virginity. No longer was I worried about orgasmic release. I knew it would come again. So absent of that concern, I had plenty of time to focus on other things. My world was simply ... clearer.

I held my head high as I cruised down the school's hallways. I wasn't just a leaf on the wind anymore. I was the wind itself, moving however and wherever I wanted.

Kenny had picked up my new attitude immediately. He said I looked different, but when he pried me about the sex question I just ignored him. There was nothing in the world that could get me to do or say anything that might lead to me no longer having sex with Keira.

So at lunch, as usual, he called in reinforcements. Once again, I had half the table staring at me to see for themselves if I was really different.

I guess I was.

I tired of staring at my food within two seconds. Instead, I simply picked my head up and focused in on each of my observers, one at a time. Individually, I dared them to say something. What could they do?

Abigail and Allison Sanders immediately backed down when I glared at them. Daniel Chen got a smirk on his face and nodded knowingly. Cassidy O'Leary canted her head and started to re-evaluate me. And then there was Megan Kwan, sitting right beside me. She was looking prettier and prettier, and after the fun I'd had with Keira last night, I started to imagine what it would be like doing the same to Megan tonight.

Megan was the first to speak. "You're right, he IS different."

"Yeah," Cassidy put in. "He's ... somehow stronger. And a little scary."

"Scary!" Abigail Sanders agreed, followed in stereo by Allison's agreement, "Scary!"

I sighed. "Will you stop talking as if I'm not here. And I'm not scary. I'm just the same old Ben."

"You seem more confident, Ben," Daniel pointed out.

"I'm telling you, Ben's having sex with someone," Kenny stated emphatically. "He's got that look."

Then almost immediately, everyone at the table turned and lasered their gaze on Megan.

The young girl suddenly saw the dozens of eyeballs locked onto her and she paled visibly. "No! No," she protested.

"No, we're not having sex!" I said loudly, drawing attention back to me.

"If not her, then who?" Cassidy glared accusingly at me.

"Will you guys cool it? Isn't it enough that I'm just feeling good about having a date tonight?" I reached to take Megan's hand on top of the table and squeezed it. "Look, everyone here knows I'm taking Megan out tonight."

I turned to look at her and without thinking, I moved my hand up to sweep her dark bangs out of her eyes and behind her ear. "A very pretty girl wants to spend a night out with me, and I couldn't be happier," I said sincerely.

Megan beamed happily and she squeezed my hand.

Then I whirled and glared at everyone else. "Now I'll thank you to butt out!"

The date was perfect.

Megan's parents greeted me and expressed some concern that their daughter was going out. She was their little girl and the idea of her being out with a boy scared them a bit. Still, Megan actually hadn't dated since the last time she went out with me, and the Kwan's seemed comforted that their daughter was going with a nice boy they already knew (me).

So when Megan came downstairs, we all suitably oohed and ahhed as the young lady had put on makeup, done her hair, and was wearing a cute but age- appropriate dress. Megan's appearance was far beyond her usual T-shirt, jeans, and ponytail daily approach.

Dinner was great. We went to a burger joint where we ran into a bunch of our other classmates. But after chatting a bit we got our own little booth and settled in to enjoy each other's company. Being prior friends, conversation came easily to us and I didn't have to force anything like I did occasionally on previous dates.

We then hurried to make our movie time. Since Megan was still just fifteen, her parents imposed a 10pm curfew. Once we got settled, Megan let me slide my hand into hers and we stayed like that for the entire movie.

Twice, I leaned over and kissed her. Neither time did she object.

Now in the darkness of the theater, usually around the second kiss I would start sliding my hand up from her waist towards a breast, gently moving in to cop a feel. Only two of my school dates had ever let me get that far. The others, including Megan, had reached up to stop my hand well before it got too close.

But I'd already had sex. I'd already suckled the bare nipples of a grown woman with nice big tits. I didn't need to get the cheap thrill of cupping a teenager's A- cups outside both her bra and her blouse. So when I kissed Megan, I didn't bother trying to cop a feel. I just enjoyed her presence and enjoyed the softness of her lips. It was a reflection of the way I felt about her. She was sweet, she was my friend, and I didn't want to treat her like a sex object.

But Megan wanted to feel a little more like a sex object. The third time I went to kiss her during the movie, she seemed pretty impatient. And when I pulled away to return my attention to the screen, Megan just huffed at me quietly, "Stop being such a nice guy, Ben."

Quickly, I turned my head back to hers with a questioning look. "Huh?"

Megan rolled her eyes and then she grabbed my hand and unceremoniously planted it on her boob. Reflexively, I tried to pull away, but she held my hand in place. And even through the padding of her bra and her blouse, I could feel the slight bump of a hard nipple denting the material.

I took the hint and began to squeeze Megan's boob, and this time when I leaned in to kiss her, she met me in a rush of passion.

We didn't go any further than that, although I did fondle her breasts when we kissed twice more before the movie ended. I didn't need to pressure Megan into any more than exactly what she wanted. After all, I knew Keira would be letting me go all the way later on.

At the end of the night, just outside her front door, I gave Megan a goodbye kiss that took her breath away.

The next day was a lazy Saturday. There was only a month to go before finals, but I was procrastinating my studying. In the morning, I met up with the guys to go to the batting cages. In typical teenage fashion, hitting the balls with bats turned into a contest of manliness. Or is that stupidity? In any case, we took turns covering our eyes and crotches with our hands, stepping in front of the fast-pitch hardballs and getting whacked while our supposed "friends" laughed like hyenas.

I went home bruised and battered, but felt I had successfully defended my male honor. Kenny was going to have a hard time living down the moment when he ducked out of the way of a ball at the last second. Even taking two more balls to the chest afterwards weren't enough to erase his shame.

After lunch, my little sister Brooke talked me into helping her with a 5000 piece puzzle she was working on, and we spent a couple of hours lying on the floor of the family room putting things together. The 14-year-old twerp wasn't quite so annoying when she had something to focus on.

In the afternoon, I heard the doorbell ring and my dad went to go get it. A moment later, I heard him say, "Oh, hi Keira."

At first, the name didn't register. But then when Miss McNeil walked into the family room, I suddenly realized my dad was talking to MY Keira. And on this warm mid-May day, she was positively stunning in a baby ringer T-shirt that hugged her tits, a short skirt, and wedge-heeled sandals, all of which showed off her long legs. She looked 21 again. Her dark hair was pulled back and her sparkling emerald eyes shone straight at me as she said, "Hi, Ben. Hi, Brooke."

Brooke politely replied, "Hello, Miss McNeil."

I just stared dumbly. What was she doing here? And good lord she looked hot! Fortunately, silence is the status quo for a teenage boy, so no one thought it odd that I hadn't responded. If I had, I probably would have slipped up and addressed her as Keira instead of Miss McNeil.

My mom came out just then and greeted our neighbor. "Well, hi, Keira! What's up?"

"Good afternoon, Beth. Well, I'd like to talk to you and Michael about Ben."

"What? Did he do something wrong?" My dad immediately put in with concern in his voice.

"Oh no, no. Ben has been wonderful. And he's been so helpful around the house these past couple of years." Keira turned her green gaze to me. "He's growing up into a fine young man."

"Yes he is," Mom agreed. "So what's going on then?"

"Well," Keira began and glanced down at the floor for a moment. "I was thinking to hire Ben."

"Hire?" Dad queried.

"I want to do some redecorating around the house. I want to convert the spare bedroom into a real home office. Repaint a bit. Change out some fixtures. I mean, for the past three years, I've left everything exactly the same way it was when Colin died. I didn't want things to change."

Keira took a deep breath and looked over at me. "But things HAVE changed, and I think it's time I started moving on. I can't just be widow McNeil forever."

Mom went over and hugged her neighbor and friend. "Good for you, Keira."

Dad was a little more practical. "But you want to hire Ben? He's good for fixing up odds and ends here and there, but he's not a professional contractor. And besides, he's still in school."

"Well, first off, I'm not doing anything drastic. No knocking down walls or anything like that. Just some paint, some fixtures, maybe assembling some furniture. Nothing he can't handle. I just don't see the need to pay all that money to some contractors. And besides, I'm in no rush. I was thinking maybe one afternoon a week for now. We'll figure something out when summer comes."

"Hmm..." Dad looked thoughtful. "What do you think, Ben?"

I blinked twice before answering a little too eagerly, "I'd LOVE to."

Brooke shot me an odd look, but I ignored her as I explained, "I mean, it's a big project and it'll all be under my control. I've never gotten to do something like that before. And you know I'd just get bored at home during the summer anyways."

"Maybe Saturdays?" Keira added. "I wouldn't want to take him away on a school night."

Mom shrugged. "Sounds okay to me. What do you think, Michael?" she asked my dad.

"I suppose. As long as Ben is willing to do it."

I nodded hurriedly.

"But no slacking off Ben," Dad warned. "If you take this job you have an obligation and responsibility to do it right."

"I will!" I grinned.

Then Dad paused. "Don't you even want to know how much you're being paid?"

Keira and I grinned at each other. If I had my way, I'd be paid in sex. But I didn't say that, stating only, "We'll work it out. Honestly, I'm not doing this for the money."

My parents beamed at me, believing I was solely motivated by my ambition to tackle a project on my own. If only they knew my ulterior motives as well.

"Well, I'm sure you'll pay him a fair wage, Keira. When do you want him to start?" Mom asked.

"How about right now?" Keira suggested. "We'll go over to my house and talk about what kind of projects I'm thinking about. And I'll have him home in time for dinner."

Twenty minutes later I was naked and flat on my back across Keira's bed. Post- ejaculation, my body felt like melting into the mattress as I was floating in a sea of pleasure.

Keira just scooped up the last glob of my cum from her lip and then popped it into her mouth, moaning, "Mmm ... yummy..."

Naked, she crawled onto the bed. Her swaying breasts captured my attention despite the orgasmic fog in my brain. "Have you ever eaten a pussy, Ben?"

"No."

"Will you?"

"For you, anything," I said in a deep and honest voice.

She chuckled. "You know, I believe that." Keira then rolled over onto her back and spread her legs to the sides, her knees in the air as she planted her feet onto the bed. "Now, Ben. If you're going to do this, you've got to do this right."

I nodded while moving around to put my head between her thighs. I looked down at the closed lips of her pussy, studying it and quickly identifying her hooded clit for future reference. "Teach me, Keira."

"You bet I will."

By the time I headed home, I'd picked up the basics of cunnilingus and I certainly knew more about thrusting and angling my cock in the missionary position.

I was also short about three quarts of semen. And when Keira had gone to empty all that out, we found out we'd been just in time since her period was just starting. She said she was going on the pill immediately and hoped to be done with her period by the next Saturday.

I gave my neighbor a passionate thank you kiss that left her breathless and then hurried home. I still had another thirty minutes before dinner, and as it turned out, I needed the extra time.

Brooke had wanted me to help her finish the puzzle. But when I lay down on the floor beside her, my little sister wrinkled up her nose and said, "You smell funny, Ben. What were you doing over there?"

My mind immediately started whirling. I hadn't thought about the possibility of smelling like sex. Would my parents smell me and figure it out? My jaw waggled up and down a few times before I managed to come up with, "I was moving furniture. I guess I got a little sweaty."

Brooke seemed to buy it, because all she said was, "Well you stink. Go take a shower or something."

I agreed and went to wash away the evidence of my illicit behavior.

Then at dinner, I daydreamed about making love.

On Monday, after calculating an intercept point midway between Megan's first and second periods, I hurried to that spot and only had to wait a minute before she came walking along, flanked by both Abigail and Allison Sanders. It was my first time seeing Megan since our date.

The girls were chattering on incessantly but Megan abruptly exited the conversation when she saw me waiting for her. "Ben!" she exclaimed happily and ran over to me.

She skidded to a halt about two feet away and clutched her binder to her chest with both forearms wrapped around it. "What are you doing here? Isn't your second period on the other side of the school?"

"Yeah, but I couldn't wait to see you again," I said charmingly. I wasn't really THAT pained with desire to see her again, but I figured it was what she wanted to hear. After all, I liked being with Megan and I DID want to be with her more.

I was right. Megan's face lit up, and then she blushed and smiled and started twisting slowly, as if she couldn't stand still.

I continued, "And I wanted to ask, will you go out with me again this Friday?"

"Yes! Of course!" She was positively effervescent.

"Great! Uh, we'll talk at lunch or something and figure out what you want to do." I grinned, Megan nodded, and the Sanders twins tittered three feet away.

"See ya later," Megan said dreamily as she turned to rejoin her friends.

Megan stayed in a perky mood all week. We sat side-by-side at lunch every day, and on Friday before our date, she tentatively reached out and held my hand as we walked to fifth period. The touch of her hand sent a pleasant buzz all through my body, and I would have loved to keep that feeling forever.

Seeing our fingers entwined, Cassidy started in on the teasing, but Megan defiantly gripped my hand and wouldn't let go. I was just happy a girl wanted to hold my hand in public.

Our date that night was a simple affair. Tacos were the dinner of choice and miniature golf was the romantic date spot. Megan had a quiet focus and precision about her, and I was rather embarrassed when she beat me. But I made up for it when I sunk the hole in one on the eighteenth to win us a free game for next time.

When the alarms went off and all the lights started flashing, Megan leaped into my arms with glee and hugged me while squealing excitedly. And even though I didn't NEED to cop a feel, it was just too tempting to grab some of Megan's ass while she was wrapped around my taller body.

Megan clearly felt my touch. But she didn't glare at me nor slap my hand away. In fact, she simply giggled and then rubbed her own buttcheeks at my hand. When I finally set her down, Megan got a very nice kiss for letting me touch her ass.

Saturday, unfortunately, turned out to be a grueling work day. Keira and I had done nothing but screw the previous Saturday and this time I actually had to do some work so we'd have something to show for it if anyone got suspicious.

Moving furniture around really did get me hot and sweaty. It was another warm day and inside the house it was becoming stifling. I commented on it and Keira teasingly told me to just work naked.

Grinning, I at least took my shirt off and went back to work. But one look at my bare chest and Keira promptly tackled me onto the couch, shucked my shorts, and then inhaled my cock. Then, after one quick cumload into her mouth just to get our rocks off, Keira decided to teach me doggy-style while she knelt on the couch cushions and braced herself against the backrest.

I had to admit, watching my dick spearing in and out of Keira's pussy from behind while I reached around and fondled her breasts was possibly the greatest experience of my life up until that point.

But then it was back to work. By the end of the day, the spare bedroom had been cleared out and a fresh coat of paint adorned the walls. And then just before I went home, Keira threw me onto her bed and taught me more about making love.

JUNE 2000, SOPHOMORE YEAR

It was a Friday when Adrienne Dennis deigned to speak with me once again. I was just leaving the main quad after giving Megan a sweet kiss goodbye, and I was walking on air as I headed off for my next period.

Life was good. School was almost over. I had a budding romantic relationship with Megan, who would be my date later in the evening. And tomorrow, I planned on fucking Keira so many times that she would risk drowning in my cum. And to top things all off, when I'd measured myself this morning I was an even 5'10". As long as my growth spurt kept up, I'd easily be six feet by the start of my Junior year. So naturally, there was an extra spring in my step as I sauntered down the hallway.

"Heyyy, Ben," came the sultry, sweet voice from my left. I turned just in time to see Adrienne fall into step with me, her spray-on jeans hugging her every curve while her big tits wobbled enticingly in her too-tight top.

Despite my surprise, it took me less than a second to get my bearings. "Hey, Adrienne. What's up?"

"Nothing much. You're heading out to the 500-wing, right?"

"Yeah, Spanish in 503." I arched an eyebrow. Why would Adrienne Dennis know, or want to know, where my classes were?

"I'm in 507. U.S. History," she said. "I'll walk with you."

Confused, I couldn't help but say, "Uh, you've never walked with me before, Adrienne."

"Well, I make it a point to only walk with the best looking guys on campus. Now you qualify." She dropped her eyes obviously up and down my body. "Why? Don't you want me walking with you?" There was an extra purr in Adrienne's voice that set my heart racing.

Hmm, be within a few feet of one of the most gorgeous girls in the school, a girl who made Senior-class chicks jealous? Let the entire school know that Adrienne Dennis was walking to class with me? Sure, I could handle that. "Hey, hey, just didn't know I'd been promoted," I said casually.

"Well you have been. The girls have been talking about how good you're looking these last few weeks. You grew up overnight, Ben. Height, posture, confidence. It's like you're a whole new man."

I thought about Megan. Last semester, she hadn't wanted to date me anymore. Now, I honestly believed she would agree if I asked her to go steady. And I thought of Keira. I especially thought of what I wanted to do to her tomorrow. I grinned and said, "Yeah, I feel like a new man."

"And..." Adrienne's voice dropped to a conspiratorial whisper. "I have an ulterior motive, Ben."

That got my attention and I turned my head. I knew it was too good to be true. "Oh?"

"Could you ... give me a ride home today? Since you're just a few houses down and all." Adrienne smiled radiantly.

I canted my head in confusion. "Doesn't Robbie normally drive you home?"

She shrugged. "We broke up. We both want to see other people and figured we'd end it over the summer. But Donna Kincaid couldn't wait two more weeks." Adrienne spat the name of the Junior-class school slut like it was a filthy word.

"Uh, sure. Just meet me after school."

"Thanks," Adrienne smiled warmly at me. I was once again struck by how gorgeous she looked, and I fought not to let my eyes bounce down to her cleavage.

"But what are you going to do without Robbie driving you?" I asked.

The buxom blonde shrugged. "There's only two weeks of school left. I'll figure something out."

I bit down on my impulse to drive her to and from school every day. Despite her assurances to my "promotion", I still couldn't conceive that Adrienne Dennis, goddess from Heaven, would want to schlep around in my beater Toyota any more than she had to.

"Well, see you later," I said as we approached her classroom.

Adrienne slowed down and turned to face me with a pleasant smile on her face. "See you later, Ben."

"Mmm..." I hummed as I pulled away from Megan's lips. "See you in a few hours. I'll be there at six."

"I can't wait. Don't be late!" Megan giggled. For a second, it looked like she wanted to lean in for another kiss.

"Hey Ben!" A cheery voice interrupted. Both Megan and I turned to see Adrienne Dennis standing two feet away with her backpack slung over her shoulder.

"Oh, hey Adrienne. I'll be just a minute," I said before turning my attention back to Megan, who shot me a what-the-hell-is-she-doing-here glare at me. I stammered a few seconds while glancing back and forth between the two girls. "Uh, Adrienne lives a few doors down from me. She asked if I could give her a ride," I explained to Megan.

"Oh," Megan said, momentarily mollified. But she didn't stop from looking at Adrienne with undisguised repulsion.

"So I'll pick you up at six, okay?" I said reassuringly.

"Okay." Then Megan leaned into me for another kiss. She made it extra juicy, no doubt for our audience. And then my cute date turned away to meet her parents' minivan.

"Sorry about that," I scratched my head as I turned to head for the student parking lot.

Adrienne fell right into step with me. "No worries. I'm used to girls getting jealous of the way I look," she said matter-of-factly. "Your girlfriend?"

I pinched my eyebrows together. "Uh, not exactly. Tonight will be our third date. Well, fifth technically, but it's our third date."

"Well, good luck then, Ben," Adrienne grinned. "Girls'll usually put out on the third date."

I arched an eyebrow as I glanced over at the blonde, but she just smiled enigmatically.

No, Megan didn't put out that night. I didn't even get my hand into her crotch.

The night started off just a little frosty. I figured it had something to do with Adrienne but the last thing I wanted to do was bring up her name only to find out I'd guessed wrong.

I mean, getting defensive about Adrienne Dennis only to find out Megan was upset because of something in her home life wouldn't exactly reassure Megan that there was absolutely nothing going on between me and the buxom blonde, no matter how true it actually was.

But still, Megan warmed up after dinner and she became positively affectionate when I took her for a romantic stroll around one of the many man-made lakes in Orange County.

Later, in the parking lot, we ended up in the backseat making out. That was the first night Megan unsnapped her own bra, then took my hand and pulled it underneath her blouse, placing my palm over her naked breast. I fondled her boob, learning that she was much more tender than Keira was, so I had to be careful not to pinch too hard.

Megan also wouldn't let me see her breasts, only feel them underneath her clothes. And at the end of the night, she gave me a very passionate kiss and thanked me for not pushing her to do anything she wasn't ready for.

The very next day, while I was ripping up carpet and studying the how-to-guide for laying down laminate-wood flooring, I told Keira about Megan Kwan.

I'd been feeling slightly conflicted over my feelings between them, but since Keira was the one giving me regular sex and blowjobs, I wanted to make it clear to her that I'd give up Megan if Keira really wanted me to. It's not that I didn't like Megan. I liked her a lot. But Keira was the one putting out, so if I had to choose, I'd choose the one giving me regular sex.

When I explained this to Keira, she just shook her head and chuckled. "Don't be silly, Ben. Megan sounds like a nice girl and you deserve to have a real girlfriend in your life."

"But ... what about you?"

"Me? I'm not your girlfriend, Ben. I'm your adult neighbor whose just using your body for my pleasure and who could still go to jail for what we've been doing. I'm no girlfriend."

"But you don't mind if Megan and I end up ... doing stuff?"

"Do all you want." Keira shrugged. "Why? How far has she let you get?"

My storytelling came in fits and starts. At first, I felt weird about talking about Megan when all my instincts reminded me NOT to talk about a girl to anyone else. But somehow, I knew that Keira would be OK for me to confide in. It wasn't like she was going to spread rumors around the school, and with her experience, she might even be able to give me advice. So in the end I relaxed and told her just about everything.

"Well, if memory serves me right, the next step, she'll let you put your hand on her from outside her panties. You'd better hope she doesn't wear jeans, or it's never gonna work right." Keira started pacing as she thought about it. "Now what you need to do is figure out how to get her feeling really good from outside her panties. And if you do it right, she'll let your fingers inside her panties and then you can try getting her off."

She tapped her finger against her lip while she paced, and then without further ado, Keira marched over, grabbed my arm, and then pulled me over to the couch. She sat me down beside her and then quickly shimmied out of her skirt, leaving her wearing just her panties below the waist.

"Okay, Ben. Today's lesson: how to rub a girl. You ready?"

"Uh, I guess so."

"Well, let me put it this way. I'm not going to let YOU cum until after you get me off with just your fingers, got it?"

"What?" I protested. I'd been looking forward to some serious fucking today.

"I told you, Ben. Rule #1: You can't cum until you make sure the girl is satisfied. Remember?"

"I remember," I sighed.

"Okay." Keira took my hand and guided it down to her crotch. I felt the coarseness of her trimmed pubic thatch, and further down the slippery softness of my lover's vaginal lips. Keira smiled at me and said, "Let's begin."

"Oh my! Oh ... oh ... oh ... Ben! Ben! Oh, I'm cumming! I'm cumming!"

Megan threw her head back and arched her neck as the orgasm swept through her. And when she pressed herself against the backrest, she pinned my left arm with such force that I nearly lost my grip on her left boob. But her own bra trapped my hand against her naked breast and I continued fondling it while I leaned in and began planting little kisses along the sensitive skin of her neck.

That just caused Megan to squeal even louder and shake even harder while the wet tips of my right-hand fingers kept rubbing her clit. And for the first time in my life, I brought a teenage girl to orgasm.

Like Keira had predicted, once I'd started making Megan feel really good by rubbing outside her panties, I'd gotten her so worked up that she asked me to move my hand inside. Bringing Megan to an explosive orgasm seemed easy after Keira had made me practice and practice and practice on her the previous week.