Jon's Education

I'm Jon, a relatively average boy from upstate New York. I've got dirty blonde hair, broad shoulders and a squishy two-inch penis. However, when it's erect it grows quite a bit, reaching a length of just over 10 inches. Despite such endowment, I've always been really shy and unable to talk to most girls.

This story takes place shortly after I turned 18, when I was still in high school, but on a week-long break.

My dad was taking my older brother and I several hours away to visit our cousin as she was having a break from her military school in New England, though she was raised out in the Midwest. We checked in to our hotel, which was a large suite with a few rooms, before we picked up my cousin from the bus station.

I had always thought Jennie was the prettiest girl in my family; she had long braided brown pigtails and a slender figure. Even though her muscles were getting bigger, she still looked quite bony to me. And she was just a couple years older than me.

We had quite a bit of fun catching up and playing board games and cards the first couple days, but my dad and brother wanted to see an NBA game the next evening. I wasn't very much into sports and my cousin, Jennie just prefers soccer, so we decided to stay at the hotel and hang out instead.

After they left, Jennie and I were alone in the hotel suite. Jennie was sitting on the sofa in a nice forest green top and jeans, watching something on the TV, but she quickly turned it off when I entered the room in my jeans and polo shirt. I sat on the sofa with her, that's when I noticed her personalized black choker that said "Jennie" on it in sparkly letters.

Jennie asked me "How's school going, what are you into now?"

"Alright, no problems with teachers or subjects, just, well, nevermind." I said shyly.

"Hey, I'm your cousin you can tell me anything, what's on your mind?" she prodded.

"I lack confidence when it comes to girls!" I blurted out.

"Oh, I see. Hey, guess what? I'm a girl, ask me anything you want." Jennie suggested.

"Well, what do girls want, like how can I get them to like me or something?" I asked.

"Every girl is different, I would say a lot of them like guys who can take charge and know what they're doing." Jennie told me.

"Like what do you mean, are you talking about.. um... making love or something?" I asked sheepishly.

Jennie laughed, "You're so cute, sure, that's part of it. What do you know?" I blushed, thinking about the little I knew about. "Hey, come on, talk to me, I won't judge you for anything you say." Jennie encouraged.

"Well, I've only seen some naked photos online and in magazines, but I imagine a lot, I guess that's not real though. I don't even know how to kiss, this is so embarrassing, but do you think you can teach me?" I asked hesitantly.

Jennie smiled, I couldn't imagine what was going through her head, but I was nervous and afraid; would she be disgusted by the idea.

Maybe she could read my emotions because what she said next calmed all my anxiety about the situation, though I still felt as though I would embarrass myself. "I suppose you are cuter than most of the boys I've kissed, and we're just cousins, right? So, I guess it's ok, how about you show me what you got, go on and give me a kiss, and then I'll coach you, ok?" Jennie told me so sweetly.

"Uh, uh, alright!" I said, maybe a bit too excitedly. I pursed my lips, closed my eyes and leaned forward to kiss my cousin, I'm pretty sure I was sweating or clenching my fists, but then my lips landed, they were pressing against hers, which felt so soft, I melted and leaned back a little.

"Wow was that your first kiss?" she asked and I nodded. "It was good for a peck, but you won't want to stop there if you want the girl to like you or even think that you like her. You should like open and close your mouth a bit, and use your tongue some. Let's try again, you got this!" Jennie shared her tips and words of encouragement.

I nodded in agreement, thinking about her advice a second before leaning in again. This time with moving lips and trying to lick into her mouth, I could taste her saliva and smell the air coming out of her nostrils. After kissing like that for a bit, Jennie pulled away and I almost fell forward, eliciting a giggle from her.

"Wow! You're a fast learner, you've already mastered that, perhaps you'll be a natural. Let me give you a few more pointers, ok? Use your hands, hold a girl, here like this." Jennie said before grabbing me and placing her hand on my lower back and her other on my neck. At this point I was past any reservations about it and my cock began to grow, I stepped back because I was afraid she might feel it and be weirded out.

Jennie continued with a smile on her face, "Also, try sucking on my lips or giving a little bite every once in a while, I think it can be a real turn on for most girls."

I placed my hand in the small of her back and held her close as my other hand gently held her neck before pressing my lips to hers again. Following her suggestions, I did everything I knew my mouth could, sucking on her lower lip, flicking my tongue around, trying to explore her mouth and giving her lips a little nibble, everything I was doing, she was doing as well. It all felt so amazing, as we continued kissing for several minutes, until my cousin bit my lip a bit too hard.

"Ow!"

Jennie giggled, and grinned. "So, now you're a good kisser for sure, I hope that helps you with your girl problem." she said.

Perhaps feeling a bit cocky or horny or both, I said something I probably shouldn't have "Yeah, I feel confident with kissing, but I'm not sure about second base yet, could you teach me more?"

"We're kissing cousins now, Jon, so I guess I'd be willing to show you a thing or two about that. It's only natural that you'd be curious about that now I suppose." Jennie said with a shrug before lifting her top over her head to my amazement.

She grinned as she caught me staring at her bare abs and bra, and began her lesson: "First, you need to know how to handle a bra, look at the clasp on my back so you can see how it works." I nodded in confirmation and then she turned to show me her back, I leaned in, and examined it before quickly undoing it. "Great, now snap it back on for me and try when you're looking at my face, bonus points for using only one hand!" Jennie instructed as I fixed the clasp and she turned back to face me.

I reached around with my left hand, while trying to look her in the eyes, and fumbled a bit before undoing it again. "Perfect! Now here's your reward." Jennie said as she let her bra slip down, revealing her small perky breasts with pinkish puffy nipples. I ogled them with my mouth wide, surprised to see such beauty in real life for the first time.

"Go on, you'll have to get hands on for this part." Jennie egged on.

I placed my hands on both boobs, cupping them, lifting them up a bit and squeezing them gently before brushing my thumbs over her nipples. Jennie bit her lips a bit, then said "That's a good start, um, go ahead use your mouth, uh, just like with kissing, personally I like men to be a little rough with me so don't worry."

Jennie leaned back on the sofa. Taking her recommendations to heart, I squeezed her boobs harder, squishing them together and moved in closer, straddling her leg and leaning over her, I had to support myself with one arm. With the other hand I held her left boob and descended my mouth over her nipple, sucking and kissing it.

Jennie's mouth gaped at the feeling, so I figured I was doing something right, and continued flicking my tongue on her nipple, kissing around her areola and sucking here and there. Giving her nipple a little bite, her back arched a bit and I switched to her other side, repeating what I had done, although quite randomly as Jennie gave affirming words and noises.

When Jennie's body started to squirm a bit, she tried to pull me off and said "Oh, ok, um, you're really good at that now, so um let's um stop, ok?"

"Oh, but what about third base, I think it is really important, right?" I said, pouting slightly, like a brat.

"It's just somewhat too far, don't you think? I mean, I'm kind of supposed to be the responsible one here, right? Eh, I guess you're right, though; it could be valuable for your purposes. How about I just let you look since you've never seen one, it will help you be ready, ok?" Jennie talked herself into it, without much effort on my part. I hadn't realized it at the time but her eyes kept darting down when she said this, so she must have been seduced by the size of my dick visible under my tight jeans at that point.

Anyway, I simply nodded with a smile and watched as she pulled down her jeans, her butt was a bit bigger and curvier than I had expected, though not too big. And her legs were toned as fuck. Then I noticed her light blue panties were soaked, the wet spot was as big as my fist.

She stood up and let her panties drop to the floor, exposing her cleanly shaven lips. "Here follow me. Many are much hairier than this but I had my hair laser removed." she said as she took be by the hand and led me to her bed where she laid down near the edge and spread her legs for me to get a good look.

"Wow! I could never imagine it looking so sexy!" I said as I glared at the glistening opening and my cock twitched. I got on my knees to get a closer look, and saw some of her juices dripping down, I reached out of instinct to stop it. Catching it as I touched the skin between her pussy and asshole, she shuddered.

"Oh, you were dripping, sorry." I said.

"Um, it's ok, just um, just go ahead and uh study..." Jennie replied with seemingly anxious breathing.

First I tasted the bead on my finger, mmm, yummy I thought, so I stooped forward and breathed in, taking in the sweet scent. Then, cautiously I traced the outside of her lips with a finger, before sliding my finger down the middle, feeling a small bump, Jennie quivered, then the hole which my finger circled, before easily sliding in past my knuckle, her body shook a tad.

"So, uh, that little bump is my clit, you should probably give it some attention before going into the hole, you can use your finger or tongue or... feel free to try... I mean if you need to practice. If I'm shaking, that means you're doing well." Jennie continued her 'coaching', though not as convincingly as before.

I prodded the small bump with my index finger, rubbing it as her body trembled some more. I decided to try using my tongue, first I gave a gentle kiss with my lips before extending my tongue out, pushing between her lips and flicking up over her clit, another jolt traveled through her body.

Encouraged by this, I began lapping at it, kissing and sucking it from time to time, continuing for several minutes, occasionally inserting my tongue into the hole before licking back up. It was quite yummy, and I was ready to try more, so I pushed my finger in her hole again and explored a little, pushing it in and out. Then I decided to try two fingers and continued licking, her clit with the tip of my tongue.

Before long, she began quaking and I heard her say "I'm almost there, I'm gonna cum!" and I continued what I was doing as she grabbed my head and held it there and her largest convulsion yet shook her body like a vibrating phone as she screamed in pleasure.

She let go and said to "Stop, uh uh, very good. I hope you're ready for the next lesson. Take off your clothes. I showed you mine, now you show me yours, ok?"

She got up and grabbed something from her bag as I pulled my shirt off and undid my belt. Was this really happening? Was I about to lose my virginity to my cousin I wondered and thought, but I was too horny to care. It just felt as if I needed this, so down my pants went, boxers and all, as Jennie came back towards me and my cock sprung out, standing at attention, dripping with excitement at 11 inches I figured as it seemed longer than ever before. Jennie gasped, swallowed and tried to keep her cool as she bit her lips and licked them too.

She ripped open a condom and wavered before grabbing my dick, wiping the precum off the tip with her thumb. Then she rolled the condom onto my dick, which covered just over half of my length. She then licked her thumb as she stared down at my cock with wide eyes.

"Ok, you're going to slay women with that monster, so um, practicing hitting home will be very important for someone like you, otherwise I wouldn't be even considering this with you. You could probably injure some girls, simply because it's so big and long. Um, so you absolutely need this lesson for safety, of course." Jennie said, obviously trying to convince herself more than me, that she was not doing this out of lust.

"Thank you cuz, you're so good to me for doing this. I really need all of this confidence and skill training." I told her, trying to reaffirm her choices thus far, even though I knew I was just a horny teenager about to fuck his cousin.

"Ok, um, let's do missionary first." she said, leading to thoughts racing through my mind, I mean she said 'first', how many positions would we try?

She lay waiting on the bed for me, I climbed on top of her naked body, looked down, seeing my dick hanging over her crotch, then I looked up at her face. And as we looked into each others' eyes, I said "God, you're beautiful. I love you cuz!"

"I love you too, cuz!" she said with a smile and teary eyes. I leaned in and kissed her on the lips, and before long we were making out, our bodies pressing together, skin on skin. My hands held her and explored her body at the same time. As I lowered myself to try to line up the head of my cock with her pussy, I sucked at her nipples a bit and slowly pushed my head in, she was still so dripping wet, that my cock glided in easily despite her skin needing to stretch to hold my girth. Her eyes widened and her body seemed frozen, I pulled out a bit before trying to press deeper and deeper. She was so tightly wrapped around my cock, finally I was in deep enough to feel her juices on my skin as the condom covered part had been fully inserted. Her eyes teared up more, "Keep going, it hurts but it feels so good!" Jennie whispered.

Pulling out and thrusting back in, I began to really fuck my cousin, we both grunted with every thrust and she screamed too. This was too good, and I yelled "I'm going to cum." Her eyes went wide in surprise but she didn't hesitate and grabbed my butt to hold me in. My dick convulsed as my balls emptied my seed into the condom inside of my cousin's pussy.

I collapsed on top of her and we held each other for a moment before Jennie said "So, you're not a virgin anymore, cuz, huh? Feel any different?"

"Sure, do, I've never felt closer to anyone than I do to you, right now." I sincerely confessed.

Jennie smiled, returning her sentiments: "Well, we'll always share a special bond now, a bit more than kissing cousins at this point I suppose. So, for your evaluation for this course, I give you an incomplete! You got off a little too quickly, I can't blame you for your first time and all, but a girl's not going to be satisfied or even want to go on another date if that's all you got. Sorry for being honest, but you gotta make me cum again, aaand again, aaaaaannnd again if you want to pass my class."

"Oh, really? No problem, I often jerk off several times back to back, so I know I'm ready for more if you can handle it." I said cockily.

"Fine, my turn for control, let's see how long you last with me on top." Jennie challenged me, with all pretenses seemingly behind us, we let down our barriers knowing we were just having fun fucking at this point.

I pulled out of my cousin and she pulled off the condom and got a new one on me. Then she climbed on top of me and impaled herself on my still rock hard cock. She was right, I didn't think I could last long with her on top I thought to myself as she bounced up and down, resting her hands on my chest, and shaking her hair. It's pretty obvious why they called it cowgirl. I came again in just a few minutes, longer than expected, but despite the fun she had riding, she hadn't cum again yet. So, now I had to make sure to get her off at least one more time before I came.

Or so I had thought too soon. She came in screaming ecstasy not long after I had.

It was a competition at this point it seemed, as once she realized I had cum again, she stopped and said, "Hah, I guess this one's a tie, come on, you gotta do better than that though. I only got three more condoms, so you lose again and you won't have a chance at graduating because you gotta make a woman cum more than you do."

"Alright, let's try doggie." I said confidently as we changed condoms again.

Jennie assumed the position, getting on all fours on the floor, but she didn't bend her legs and instead appeared to be doing downward doggie. I was too inexperienced to know any difference, so I just grabbed her hips and penetrated my cousin for the third time, thrusting harder and faster than I had during our first position. Jennie finally came after nearly a quarter of an hour of my thrusting and panting, then I reached down while she was cumming and played with her clit, her arms gave out on her and her head was pressing into the carpet while her chest seemed to support her body as her orgasm rolled into another and another before I finally came again.

"Ok, ok, stop, you win this round." Jennie struggled to get out, eliciting a smile from me.

"Here, sit down, I want to ride you in a chair this time." Jennie said after we finished putting on the new condom.

Jennie rode me like hell, bouncing up and down, pleasuring herself on my shaft. Luckily, having cum a few times already, gave me boosted endurance, otherwise, I probably wouldn't have lasted longer than her. Either way after she came, possibly more than once, I came again, filling up the next to last condom.

"Let's 69 for the last one, ok?" I suggested.

"Alright, then we can save the last condom for another time." Jennie said, smirking while giving me a wink.

I got on the bed and she climbed over me, positioning her pussy over my face. I licked my lips in anticipation. She lowered herself as she grabbed my dick in one hand and began sucking my tip. Then she engulfed more of my cock than I thought possible. I extended my tongue and flicked at her clit, and she gagged on my cock. I guess all her orgasm had made her extra sensitive. She could barely keep sucking me as I ate her out.

Eventually, she gave up on sucking my cock and propped herself up to really grind on my face, her pussy slid over my tongue and nose as both dipped into her hole before she slid past them again and again. Jennie constantly screamed as she rode my face. It was very enjoyable for me to be able to help her cum so many more times like that, despite the fact that she forgot all about my dick.

Her convulsing body lay atop mine after she finally had had enough, I gave another lick, and she flopped her arm to swat me. I guess it was really too much for her now.

Panting, she rolled off to lie next to me. "Oh, ok, you pass that section." she said between breaths.

After regaining her composure, my cousin said "I think you've passed all the basics for most girls, but some may like to be used by you and enjoy a little pain. For your final oral exam, you must break my choker without touching it, do whatever you need to, ok? I will obey any command of yours if you call me 'bitch', unless you tell me to break it myself of course. Feel free to get into it, abuse me a little."

I smirked as I thought of the idea of being given full control. It was obvious that it would be my dick examining her oral cavity for this, so I gave my first order: "Kneel!"

Jennie stood there and leaned in, whispering in my ear: "You forgot the magic word."