Kathryn's Question

Story Info
Two young friends become something much more.
6.5k words
4.68
952.9k
117
0

Part 1 of the 5 part series

Updated 10/28/2022
Created 09/13/2006
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

You know when people use the term "I almost swallowed my gum?", well, I actually did when Kathryn asked me that question. Went into a coughing fit, too. Lovely...

We were both just 18 and had been friends since second grade. Kathryn's house backed onto mine and our relationship had started the way many young ones do: us staring at each other over the dividing hedge from the safety of our own yards. Her family had just moved in; I'd lived in my house all my life.

"What's your name?" I'd asked.

"Kathryn. What's yours?"

My parents and older brothers, everyone actually, had always called me Bobby, but here was this pip-squeak kid with huge eyes using her formal name on me as if she was someone special. "Robert," I replied.

And it was done. Over the last two weeks remaining in that summer vacation we became friends, two peas in a pod as my father was fond of saying. Truth was, there was a lot of truth in that. We were both awkward even as kids. Both of us wore glasses, for instance, and even for seven-year-olds that wasn't too cool. For the entirety or our school years, we basically only had each other as friends.

The other kids, picking up with their infallible radar that we were different, zeroed in on us with their cruelty. It's always thought that boys are the worst at this, but the whispered stories that Kathryn told me of the misery inflicted on her by her gender made it clear that I had no idea what cruelty could be.

We had a lot of things in common: we both enjoyed reading widely, we actually LIKED school and did well there. I wanted to be a university professor and Kathryn wanted to be a psychologist. All our classmates aspired to, it seemed, was taking over their fathers' hardware stores, or opening a beauty parlor, something that didn't require a whole lot of book learning. Just two wanted to be doctors -- but only if their pro football careers didn't pan out. Such was life in a small, southern town in the '50s.

So we bonded. It wasn't a gender thing, either. We were just two outcasts against the world, best buds, and each took solace in the other's company. To our parents' amusement, we always referred to each other formally. For some reason I could never imagine calling my friend Kathy, or worse yet, Kath. It just didn't fit.

Fast forward eleven years. I'd turned into a gawky string bean, just over six feet tall. On hitting puberty, I'd had a bout of acne, not really bad, but enough to make my face a bit pocked. This was the mid-60s, after all, and treatment for that sort of thing was expensive.

Kathryn had gotten somewhat tall too, being now nearly 5'7". Her hair had grown very long indeed and she usually wore it in a braid. As for the rest of her, she wore those "granny dresses", several years before they were trendy. This was in response to the inevitable gibes and taunts in the girl's locker room. Kathryn had grown very quickly at age twelve and consequently had been very skinny. Coupled with her rather large feet, glasses and the fact that she was late to develop "other things", she been the target of all the "popular girls" and made to feel more of an outcast than ever.

She developed asthma and this eventually enabled her to drop Phys Ed. Smart Kathryn had set up the whole thing, though, and while she did actually have some trouble with her breathing, after a little research at the public library, she figured out how to fool her parents, doctor and the school into thinking she was much worse off than was the case.

In short, we were both class A "dweebs" as far as the other kids, and truth be told, many parents and teachers were concerned.

We were the brains in a school that really didn't honor such things. In our school, football was king. And when it wasn't football, they made do with basketball and baseball. If you were good at sports, you were golden, so the jocks ruled the roost. If you were female, your existence revolved around whether you were going to be able to crack the Varsity Cheerleading Squad or by going out with one of the jocks. Rumors swirled around those girls willing to do "anything" to snag one of these sought-after males.

Rather than withdrawing like Kathryn, I tried playing sports. Football was out since I was so slight. They would killed me. I wasn't very good at basketball, but baseball, that I could do. I had a good quick eye and natural swing, but it always seemed to amaze everyone when I jacked out another home run. My dad, originally from Boston, said I swung the bat just like Ted Williams, the "Splendid Splinter". It wasn't much, but my involvement in at least one sport (and a couple of games my hitting had saved over the years) kept the worst of the jocks off my back. They still made me feel like an outsider every chance they got, though, since baseball was definitely the bottom of the sports pile.

Kathryn would come to a lot of the games and sit in the stands with a quizzical expression on her face, book in hand to read until the next time I was at bat. She always sat by herself.

All through school we'd been the top two in our class and this had led to some friendly rivalry. We each spent far more hours than necessary on papers and preparation for tests just so we would be sure to beat the other. There were many times where we were the only ones in our grade to get 100s on tests and each of us maintained averages above 98, year in, year out. We'd also spend hours discussing politics, literature, art, whatever took our fancy. Kathryn and I both felt that the other was the only person we could really talk to.

Of course, we often studied together since we could work more efficiently. That was what we were doing in the basement of Kathryn's house on the day she asked "The Question".

So here I was, literally choking on my gum with Kathryn pounding me on the back. Eventually, a glass of water got the coughing under control. Kathryn was very apologetic for catching me off guard like that and tried to pass her question off as a bad attempt at trying to be funny, but I quickly made my exit.

After passing through the hole we'd worn over the years in the hedge dividing our yards, I ran into the house, up to my room and flopped down on the bed, feeling more of a dweeb than ever. Truth was, I had a major crush on Laurie, captain of the cheerleading squad, a total blonde fox and girlfriend of Todd the captain of the Varsity football team. She sat in front of me in English and History, but we'd never exchanged more than a dozen words. Laurie was always turned away, speaking breathlessly to her friends about her life of parties, shopping and cheerleading. I definitely lusted from afar.

Truth was, when Kathryn asked her question, I'd been daydreaming about Laurie and remembering how I'd jerked off that morning in the shower, thinking of her lustily kissing me. THAT'S what had caused me to unfortunately swallow my gum.

Now I looked like a fool in front of my closest friend. Somehow I suddenly felt un-loyal to her, even though, I'd never remotely even thought of Kathryn in that way. How could I? She was my best bud.

As I lay there feeling sorry for myself, the phone rang. My mom called upstairs, "Bob? Are you home?"

"Yeah," I called out.

"It's Kathryn on the phone. She wants to talk to you."

I wished I'd opted for a long walk. "Tell her I'm coming."

I heaved myself off the bed and went downstairs with all the enthusiasm of a condemned man walking his last mile. My mother handed me the receiver and smiled.

"Hi Kathryn."

"Robert, I am so sorry for what I did. I don't know what came over me."

"It's okay."

"No, it's not! I feel just terrible."

"It's already forgotten." Yeah, right.

"Will you come back after lunch? We still have a lot more studying to do for that Physics test. You're better at it than I am, and I really need your help."

"Well, okay..."

"Thank you, thank you, thank you! You've always been my best friend. See you around 1:00?"

"Sure."

I put down the phone and stood there, amazed by what Kathryn had said. In all the years we'd known each other, she'd never once said that I was better than her at anything academic. It wasn't true, either. She was every bit as good at physics as I was, better probably.

Kathryn was sitting on her back steps when I came through the hedge. Her face brightened as soon as she saw me. I stopped and looked at her differently than I ever had. I tried to really SEE her for the first time.

She still had those same big eyes, amplified by the thickness of her glasses, but her hair (combed out that day) was dark brown and lustrous in the sun, framing her oval face beautifully. In her typical long dress, sitting up quite straight with hands clasped tightly in her lap, she reminded me of one of those Madonnas you see in old religious paintings.

"Still my friend?" she asked tentatively.

I nodded. "Yup. For always."

She stood, smoothing her dress. "Then let's get to work."

The house was quiet as we walked through the kitchen to get to the basement stairs.

"Are your folks out?"

"Yes," Kathryn answered over her shoulder as she started down the stairs. "They've gone to pick up Melanie from college. Won't be back until tomorrow afternoon."

As we settled down to go over our lab notes something was different. For the first time in my life I was thinking of my best friend as a female. She was at the opposite end of the old sofa, knees making a tent under her dress, a pose I'd seen her use a thousand times before. Now I found myself wondering what was under that dress.

From what I could tell, Kathryn was having trouble with her concentration too. Normally, she would be flipping back and forth through her lab notes, collating facts and results and writing them down in an orderly fashion in her "studying notebook", but right then she'd been on the same sparse page for more than 10 minutes, eyes seemingly boring holes in the paper.

I could feel her stealing glances at me whenever I was looking down at my notes, because I was doing the same. Finally, we both looked up at the same time.

"What?" she asked with a blush creeping over her cheeks.

I almost chickened out and said, "Nothing," but didn't. It was a fateful step. "Why did you ask me that question this morning?"

Kathryn's blush deepened. "I told you; it just kind of slipped out."

"Yes, but what were you thinking? It had to have been in your brain in the first place."

My friend stared at me for a good minute before speaking. "You have to swear that you'll never tell anyone!"

"Tell them what?"

"What I'm about to tell you, of course! Swear it!"

I rolled my eyes. "Have I ever passed on anything you've told me in confidence?"

"This is different, way different."

"Okay, I swear I'll never tell anyone," I said, raising my left hand and putting my right over my heart.

It was enough to break the tension and Kathryn didn't look quite as much like a deer caught in the headlights.

"This is so embarrassing..."

"You can't just leave off now. You started. Now you have to finish."

She took a deep breath. "It was last Christmas. You remember that Melanie brought her boyfriend home for the holidays?"

I sure did remember the "over superior" Jason who treated me like some miniscule speck barely worthy of his notice. I'd always liked Mel but I couldn't see what she saw in this self-absorbed twerp.

"Yeah, I remember him."

"One evening my folks were out at a party and I'd gone up to bed early. I woke up around midnight, hearing some strange sounds coming from the living room. It sounded as if someone was being hurt.

"Creeping out of my room, I laid down at the top of the stairs and peered into the living room like Mel and I had done when we were kids and my parents were having a party."

I was hardly breathing and was imagining all sorts of directions Kathryn's story could go.

"Mel was sitting next to Jason with her head on his shoulder. Her blouse was open and her jeans were down and his hand was between her, um, legs. His pants were also open and his...his penis was out. She was rubbing it up and down and both of them were moaning."

"What happened next?"

"I got scared that they'd see me, so I slowly moved back and tiptoed into my room."

I'd had a quick peek at a naturist's magazine once. One of the guys on the ball team had swiped it from his parents. The photos in it had been my only experience viewing a completely naked female. Girly magazines were hard to come by in our small town and never showed more than tits and asses.

"So why did you ask me if I, um, masturbate?"

Now Kathryn really blushed, not just her face but her throat and what I could see of her chest also. She got up quickly and asked if I wanted a cold pop. I told her sure and she scurried upstairs as fast as I'd cut out that morning. It certainly took her a long time to open two bottles of Coke!

After she returned, we sat there and drank, Kathryn averting her eyes and me dying to find out what her answer was going to be -- if she could work up the courage to tell me.

Finally, she looked up and I could see from the firm set of her mouth that she'd decided.

"Remember, you swore you'd never tell!"

"Absolutely. My lips are completely sealed!"

"Because if you ever tell anyone, I'll absolutely die! You know how fast these things get around school."

"Kathryn, you know me better than that. Now what is so terrible that you're just about to faint?"

That was a lot of bravado on my part, because the tension in that basement was so thick you could almost see it.

"Okay...When I got back to my room everything was churning in my brain. I'd sometimes wondered what a penis looked like when it was, you know, excited. I saw my dad once when he hadn't shut the bedroom door completely. It sure didn't look like what Jason had!"

"So what happened?"

"I was also pretty amazed at the way Mel was squirming around with Jason's hand between her legs. So I, um, began exploring a bit. I'd never really touched myself down there. I found a spot and...and..."

"And what?"

Kathryn colored wildly again and looked down. "I made myself orgasm," she said in almost a whisper.

Here's where I blew it again. "Women can do that?" I blurted out, amazed.

Yes, I'd heard some of the locker room talk. There were always guys who claimed they'd "done it", but most of the information I'd overheard dealt with what happened to the guys. I knew how female plumbing worked -- we'd gotten that in school -- but I had no clear idea about the fine points of female anatomy. The only thing I'd ever seen was this bush of hair between the legs of the women in the naturist magazine.

Kathryn's eyes got big. "You didn't know that? I thought you'd know a lot more than me!"

If it had been anyone else, I might have tried to lie about what I knew. But this was my oldest and closest friend. I couldn't lie to her.

"I guess not."

That seemed to put Kathryn much more at ease. She took another swallow of her Coke and sized me up. "So, I've told you that I've masturbated. Have you?"

I'd been doing it ever since I'd turned 14. I'd always found touching myself pleasurable when I showered. One day I'd done it a bit too long and was rewarded by ropes of semen all over the shower stall. I didn't know what it was, but I was hooked. Overhearing two guys talk while taking the school bus home filled in the details that I was missing. Ever since then, I made myself cum whenever I took a shower and occasionally while lying in bed. Hand cream was the best for that.

So I girded my loins and nodded. "Yes, I have."

Kathryn's next question shot out with no hesitation. "How many times?"

"I've, ah, lost count."

"Cool... Do you do it every day?"

"Do you?"

Kathryn's eyes got big. "Um...yes. Ever since that first time."

"I do it whenever I shower."

I'm sure that most of you are rolling your eyes at this exchange, but we were two VERY naive kids and for us to talk like this was really thrilling, in the true sense of the word. That day, when she asked me that question in her basement, Kathryn and I crossed a very wide gulf and took our first real steps to adulthood.

Once the ice had been broken, our normal natures took over and we talked further but more on an intellectual bent. It probably sounded rather scientific.

Kathryn, with her newfound discovery of self-pleasuring, had done what I would have expected: she set out to learn everything she could. That hadn't been easy. Our town was definitely repressive on matters of human sexuality. The head librarian, Mrs. MacAllister, kept any books dealing with the subject right behind her desk. If you wanted one, you had to ask her directly. You can imagine how intimidating that would be to a high school kid. Hell, even adults would find it intimidating.

But Kathryn had this sneaky side (she'd weaseled her way out of taking Phys Ed, after all), and she set out to get a look at those books. Volunteering at the library had taken care of that. No one liked to work Friday nights, and Saturday morning was about as popular. It was a simple matter to slip one of the books out last thing at night, and return it to the shelf first thing next morning.

"I learned a lot. They have a really neat book by a doctor named Kinsey. He's studied sex all his life. Some of the things in that book would turn your hair grey!"

"Like what?"

"Like women who want to have sex all the time. It's like they're addicted to it. They're called nymphomaniacs. There are all kinds of perverted things that people do, too."

"I'd like to see that book."

"I'm not scheduled to work Friday until next week, but I guess I could do it." Kathryn suddenly got serious. "I'm glad that you're willing to talk to me about this. I've been dying to talk to someone, but there's nobody else but you. It's not like I could talk to my mom about this, and Mel, well let's just say she's too caught up with herself and Jason right now."

"Do you think they've ever done 'it'?"

"You mean intercourse? I wouldn't be surprised. I certainly heard them doing something in her bedroom a few times when mom and dad were out. Afterwards, she's looked all flushed and Jason looked a bit guilty. I'll bet they've been doing it."

It was getting close to dinner time and I had to be going. We both got up and looked at each other awkwardly.

"Would you come back tonight and talk a bit more? Kathryn asked.

"Yeah. All right. If you want to."

My heart was fluttering because I was finding this really exciting. I'd never talked to anyone about sex, especially someone who actually knew something, especially a girl.

At the back door, Kathryn softly said, "I'll be waiting for you," then leaned forward and kissed my cheek.

I remember thinking all through dinner that my best friend had actually kissed me. My dad asked if I was okay and I told him that I was just going over some study questions in my head. If I wanted that scholarship than I had to do well! Both my parents smiled at me, little suspecting that what I was actually thinking about was Kathryn masturbating.

-=-=-=-=-=-=-=-

We were much more at ease that evening. Funny how much things can change in just a few hours.

We again sat in the basement at opposite ends of the sofa. Kathryn had made brownies. She told me all sorts of things that had been in the Kinsey book and several others she'd read. She knew a lot more about sex than anyone I'd run into.

"I have a really, really big favor to ask you," Kathryn said after we'd been talking about two hours. I noticed that her face was really flushed again and her breathing seemed fast. "It's a really big favor."

"What?"

"Would you...would you show me your, um, penis?"

She was being more careful this time and had waited until I'd swallowed the last bite of a brownie and taken a swig of milk, because if she hadn't, I probably would have choked to death.

12