Please Teach Me Jack

4077 words | 12 |4.97

Little Brinnley asks for help with a problem.

I’m a 40-year-old professional, living in North Carolina. My wife, Linda, and I live in an upscale neighborhood on a lake outside of Charlotte. I have always been pretty straight-laced in moral character, no alcohol or drug usage and happily married with no children.

My wife’s best, Autumn was going through a nasty divorce and over the past 4-5 months was spending more and more time at our home. Autumn had two children, Hunter, who was a handsome, blonde six-year-old, and the epitome of a young boy who loved baseball, dogs, and baseball. Brinnley was a soon-to-be very attractive teenager, but just turned eleven the month prior, and occupied her time with swimming competitions and riding horses when she got the chance. She stood maybe at 4’8″, slender, with exaggerated features that would eventually grow into a beautiful form, with large, round gray-green eyes, and long, straight, dark brown hair. At first, I was not happy with a couple of kids taking up my weekends and the occasional weeknight, but I soon started to enjoy their company and energy.

One Friday night they came over and I volunteered to watch the kids while Linda and Autumn went out to dinner and a movie. Autumn had a difficult day with her ex and the kids were tense because of mom’s anxiety.

Hunter had a school field trip all day and was exhausted. For the first time I knew him, he fell asleep on the couch soon after the ladies left. Brinnley asked if she could use the pool and I agreed. It was a beautiful Spring evening and I had a chance to catch up on some reading on the chaise lounge by the pool.

Brinnley was wearing a two-piece pale yellow bathing suit from last summer that was quite faded and skin-tight. “Do you like my swimsuit? I wore it during my meets last summer. Mom only lets me wear it at home, she says it’s a little too faded and small now.

After jumping off the diving board a few times; she walked over to my side, faced the pool, and started bending over, touching her toes with her legs shoulder-width apart. Bent over, she looked back at me from between her legs and said, “Look, Jack, I can touch the edge of the pool.” I looked up from my book at her upside-down face framed perfectly by her thin sinewy thighs and her pert, firm little butt cheeks. The bottom part of her suit was so snug against her little muff, that it formed a perfect miniature camel toe, with the material wedged in her little crease.

I had never before thought of Brinnley in any sexual regard. None. I never thought of any prepubescent girl in that manner. Ever.

She stood, turned around, and walked over, standing within inches of me. I could immediately see why her mom only allowed her to wear it at home, it was completely transparent. A slight cool Spring breeze kicked up, and I couldn’t help but notice her hard, pointy puffy nipples encircled by larger-than-expected shadowy areola straining through the faded yellow top. She saw me looking at her budding nipples, met my eyes, and made them stretch out a little bit more inhaling a deep breath and in a serious manner asked, “Jack, I need to ask you something.”

“Sure, Brin!” I said, trying to snap out of my nascent, unwholesome thoughts. However, when I lowered my eyes, I focused again on the pinched cloth between her tiny pussy’s lips. I consciously checked myself again, “What the hell is the matter with you, Jack, she’s eleven!”

“I want you to be honest, okay? Real honest, because you’re a guy and I can’t ask my mom or Linda. When I stay with my dad, he is constantly making fun of me, calling me bubble butt and jelly bean butt,” She turned around and slightly bent over again, pushing her bum back within a few inches of my face. “Well, is he right? Is there something wrong with my butt?”

She turned her head and watched me staring at the most perfect tiny ass I have ever seen. I don’t remember, but I’m sure my mouth was hanging open and my eyes glazed over in a hypnotic state. “You don’t think it’s too hard from all the swimming, do you? I watch some other girls walk and their butts jiggle, but mine is hard as a rock. See?” She reached back and squeezed each cheek with her hands and her fingers refusing to sink into the skin at all, just like she was gripping two softballs.
“Jack, please answer. Am I that ugly?”

I shook my head to clear my impure thoughts and said, “Brin, your dad is a freakin idiot. Your butt is perfect, your legs are perfect, your body is perfect and you are going to grow into a very, very beautiful young lady. Trust me, you are perfectly built, just the way you are. You are going to have the guys all over you in a couple of years.” I never liked her dad, he was rude and ignorant and I never blamed Autumn for wanting to divorce him.

Turning back around, pushing her nipples out, she glanced down at each bump, making sure I was looking, and questioned again, “What about my boobs? Daddy said I don’t even have boobies. He thinks it’s funny that Mom makes me wear a training bra to school.

Was this really happening to me and why was this happening? I glanced around making sure Hunter hadn’t awoken or no neighbors were looking or listening across the fence. “Don’t listen to your dad! He is just angry about the divorce, and is trying to make you feel bad by being mean.” I looked directly at her raised, puffy nipples with a tiny peak in the center of each. I felt my dick starting to swell and could easily imagine my teeth squeezing those tiny hardened peaks. My breathing was quickening and I could tell my face was red.

While I was mesmerized with the two hardened buds I heard her say, “Did I cause that? Is that what they mean when a guy gets excited?” She was looking at the growing bulge in my nylon swim shorts.
“Oh my god, I’m going to hell,” I thought. I quickly stood up, not knowing what I should do next, but standing up was the last thing I should have done as my dick was now at its full six inches and straining to escape the tops of the shorts.

“My god! That’s huge, Jack. Did I do that? I’ve never seen one that big. Hunter’s is teeny-weeny; I see it all the time. I accidentally saw Daddy a couple times when he was peeing, but he is nowhere near that size. Did I cause that? I heard a couple of girls in class say that men get like that when they get excited about a woman.”

I grabbed a towel from the chaise and hurriedly wrapped it around my waist. Slightly stuttering, “Come on, Brinnley, we better get inside. Trust me, you are very beautiful, your dad is messing with you. Let’s get inside so you can take a bath and I can check on Hunter.

Hunter was out like a light, still sleeping on the couch and Brinnley went into the guest room to bath. I heard the tub filling with water and grabbed a glass of ice water, trying to will down my hard-on.
“Jack! Jack! Could you bring me a towel, please, I forgot to grab one.” I got a towel from the hallway bathroom and walked into the guest room.

Standing in the doorway to the guest bath was Brinnley without a stitch of clothes on. She was holding her hands together in front of her little pussy. Her long hair was pulled back, exposing perfectly formed cone-shaped nipples rising almost a good inch from her chest. Much darker than I expected and the nipple extended out another pointy quarter inch from the coned areola. I was frozen in place. We stared into each other’s eyes and she slowly moved her hands apart exposing a tiny wisp of fine, soft hair curling into the top of her slit. I was sure she twirled that little tuft of fur and pushed them between her lips on purpose. I couldn’t breathe. Time stopped. My dick was now harder than I ever remembered and forming a huge tent in my shorts. I couldn’t move, my tongue slowly circling my lips, searching for a drop of moisture.

“Well? Be honest. Am I that ugly or weird? You’re not saying anything.”

“Brinnley…” I stammered, searching for words and air. “You are absolutely stunning. Your titties are perfect, they’re perfect! Your pussy is gorgeous and don’t your dare shave down there. Your hair is growing in perfectly and the way it lays between your lips makes it picture perfect. You are perfect!”
She stepped forward, raised up on her toes and with tears in her eyes, kissed me on the cheek. “Thanks, Jack. Thanks so much. You have always treated me like an adult and have always been honest with me.”

She took hold of the towel, turned, and walked slowly into the bathroom. Stopping at the door she looked back, saw me looking at the tightest, firmest ass I ever saw. I swallowed hard, tried to breathe and caught her watching me squeeze my dick. She sat the towel on the sink and looked back at me with those watery large doe eyes. Her hands were akimbo, resting on the curve at the top of each cheek. She slowly slid them down ever so slightly causing the twin globes to spread open, just providing a glimpse of a dark pink star. “Are you sure my bum is okay, Jack? It’s not like a jelly bean, is it?

I was speechless. All I could manage was to shake my head in the affirmative.

We heard Hunter call out.

“Thanks for being so nice, you’re the only man I know who doesn’t treat me like a little kid, she said as she slowly closed the bathroom door.

“Jack! Jack! Are you in here? I’m hungry,” I heard Hunter yell out again.

“Coming, Hunter. Getting your sister a towel.”

While getting the kids a snack the phone rang. Linda and Autumn had a fun evening unwinding but ended up having a few drinks too many and thought it best if they just got a room and not drive home from the other side of Charlotte. I hurriedly agreed, assuring them the kids were no problem and they should be safe. I hung up the phone, questioning my sanity. I told the kids about the change in plans. Brinnley and I looked at each other across the dining room table with an air of excitement and unknowing. Here I was, telepathically communicating with an eleven-year-old girl that she had my total attention and interest.

“Okay guys, you two can share the guest room bed tonight. So let’s start getting ready.”
I was cleaning the plates when Brinnley came back out of the guest room in a pair of shorts and pullover, asking if I had a T-shirt she could wear because she had forgotten her pajamas. I said sure and told her which drawer in the master bedroom to look. A minute later she came running through the house back to the guest room with a shirt in her hand.

I walked back and told them good night. Brinnley looked at me with wonderment in those magnetic green-gray eyes. I knew the night was not over, especially when she said, “I’m still not real sleepy, the time at the pool has me a little excited.”

“Try and get some sleep, I’m going to wrap myself up in a blanket on the Lazy-Boy couch and watch some TV in the den for a while,” giving her a knowing nod. I leaned over and gave each a kiss, but with Brinnley’s lasting a couple of seconds longer on the nape of her neck next to her ear, making sure she felt the tip of my tongue on her skin.

Turning on the TV in the den, I gathered a blanket and reclined on the Lazy Boy. It wasn’t long before I felt my dick hardening. I glanced over the back of the chair before sliding my nylon shorts off and tossing them on the floor at my side. A minute later, I extended the footrest and started slowly stroking myself, picturing my little goddess standing in the bathroom doorway. I was just increasing my tempo when not surprisingly, I heard a soft whisper behind me, “Jack. Jack. Hunter is asleep already. Can I watch TV with you?”

I slowly released the grip on my dick and looked at Brinnley as she walked around the chair and glanced at my shorts on the floor before focusing her eyes on the protrusion coming up from the blanket covering me. She was wearing my favorite sleeveless T-shirt. I could see the entire side of her rib cage through the opening, her little titties completely bare. We both had some idea that what we were about to do was exciting yet unbelievably frightening. She reached over, lifted the blanket, and looked at my hard cock, before she slid up between my legs. She straighten out her legs, wiggling back into me, making sure the top of her butt and lower back were resting firmly against my cock. She pulled the blanket over us, grabbed my hands, and wrapped them around her, “Hold me, Jack, I’m chilly.”

After a couple of minutes of listening to each other’s heart pounding she whispered, “Jack, I feel funny inside. Like tingly, but I don’t know what to do. I touched myself in the tub. You know, down there, and the tingling feeling got so strong I thought I was going to pee. When I was washing my chest, it almost felt like my boobies were hurting. I don’t know what to do, Jack. What am I supposed to do? What’s wrong with me?”

“Awww, Sweetie. You are starting to grow up. That’s all. You are getting feelings that you need to learn how to take care of yourself. There is absolutely nothing wrong with you. It’s called puberty. You’re just there a couple of years earlier than most girls. She laid her arms on mine and pulled them tightly around her little body.

“You know we shouldn’t be acting this way. You and I can get in a lot of trouble if anyone ever finds out what happened in the bathroom and you sitting here with me like this. Your mom would be furious and I can get into a lot of trouble.”

“I know that, Jack. I’m scared too because I don’t know what to do. I touch myself because it feels good, but then I don’t know what I’m supposed to feel or do. I can’t ask my mom, I can’t look anything up on the computer, she would find out, she watches everything like that. I can’t bring myself to ask my girlfriends, they’ll think I’m stupid because they all claim to be so smart about that stuff. You’re the only person I can trust. I know you won’t hurt me or laugh at me. Please, Jack. Please help teach me. Please?”

“Oh, Sweetie. Do you know what you’re asking of me?” I was already losing. My fingers softly drawing tender little circles on her sides through the t-shirt. I knew exactly their destination.

“I know. I know it’s a lot, but I have no one else to teach me. I go crazy some nights, like tonight. I’m a mess inside, I’m so tingly inside I think I could just scream. I keep thinking I’m peeing because I’m so wet down there. Like right now. Please, Jack?”

I emitted a silent whimper. I cursed myself for my next words, “Brinnley, listen. Okay. I will help you. But I want you to learn how to help yourself. Everyone satisfies their own tingly feelings sometimes when they’re alone. Everyone, you, me, your mom, Linda and there is nothing wrong with that. There are just some things you and I can’t do together. But, yes, I will help you. But our secret kiddo, no one can ever know, not your friends, Hunter, your mom, no one. You understand why, right?”

“I know and I know why, too, Jack. You’re the only person I trust. I know my mom does it because I have stood outside her door sometimes and listen to her. Sometimes she’s so loud the bed makes noises.

Oh my god, gathering my thoughts I formulated a plan. “Okay, Brin. Here’s what we will do. Let me hold you. I want you to lay back against me, close your eyes, and enjoy the sensations you’re about to feel. And, don’t worry about peeing. You’re not really going to pee, you’re going to have an orgasm. It’s what happens when the tingly feelings go overboard. Like when you hear your mom’s bed creaking. It’s natural and it is the most satisfying feeling a person can do by themselves or with another. Okay? Lay back, close your eyes and enjoy.”

I held her upper thighs and bum and pulling her tight against me.

“Is that your thingy I feel on my bum. Are you still hard because of me? Am I causing that?”

“Yes, Sweetie, you sure did,” I whispered as I pulled her hair away from her neck and placed my hands on her tummy. As soon as my lips touched her behind her right ear, I felt her body shiver and watched the goose bumps grow on the back of her neck. I placed my hands softly on her tummy and ever so lightly began running my fingertips up and down her front, circling but not yet touching those beautiful puffy buds.

I was soft, slow, and methodical. I really wanted her to have a very special moment. As I continued kissing and nibbling behind her ear, she started to lightly gasp, and whimper. Sliding her firm little ass around until my dick was wedged between those two unbelievably firm cheeks. It was then I realized she did not have on any panties. The way her tiny globes gripped my cock it was impossible for panties to be there.

“Okay, sweetie. Sssshh. Try and be quiet. We don’t want to wake Hunter. Okay?” I began to tighten the circling of her nipples with my fingertips, ever so gently caressing the areola at the edge. They were so hard I could easily discern the exact edge of her buds. She started twisting her upper body around to make my fingers contact her nipples. She planted her feet on the outside of my legs, her knees bent and apart. I pulled my fingers away. She grunted in frustration. I reached down and slowly started to slide the T-shirt up from where it had gathered at her waist. She gasped and froze!
“Please. please, Jack. Do more. I want to scream.”

This isn’t about me, Sweetie. This is for you. I slowly traced my fingers up the inside of her thighs. As I neared her little pussy, her inner thighs were coated with syrupy wetness. She gasped again, shifting her bum around, in an attempt to have me touch her slit. I pulled my fingers away. She gasped loudly again, gripping the rolled-up T-shirt and sliding her wet bum back and forth on the leather chair. I briefly held her hips firmly rocking my cock into the crevice of her well-toned muscular ass.

“Okay, Sweetie, it’s your turn. Time for you to do this yourself. I want you to move your hands down there. There’s something I’m going to show you.” I held her hands and placed them on her pussy, but not before slowly teasing her with each of my index fingers squeezed in between the sides of her pussy and slightly open thighs. When I had them in place I pushed my index fingers inward, squeezing the sides of her pussy together, causing her to expel a gush of syrup, much like squeezing the juice out of an over-ripe fruit. Her breathing was ragged and labored, like not being able to get enough oxygen into her lungs.

My rigid cock was straining, about to explode. This time as I traced my fingers to her front I gently gripped each nipple between my thumb and index finger and squeezed, then released. I then firmly squeezed each puffy nipple, pulling on them. She continued gasping and moaning. Her arms began moving back and forth under the blanket. I soon heard the squishing of her little pussy and her fingers began furiously rubbing it. I started kissing and and nibbling behind her ear with more pressure, every now and then allowing my tongue to glide over her ear.

“Oh my. Oh my, Jack. What’s happening? I’m going to pee, Jack.”

“No, you’re not, Sweetie. You’re going to climax, you’re going to cum. Keep going, rub faster, harder. Come on, Baby! Faster, faster!

I slid my hands to her side, reached in through the sleeve holes, and squeezed the nipples, skin on skin. I latched on to her tiny granite hard nipple and squeezed again. Rolling the nipple with my finger tips, releasing then grabbing the entire bud and twisting.”

She was thrashing around like she was being electrocuted, spasming uncontrollably, her knees swinging back and forth wildly. I covered her ear with my mouth and inserted my tongue while I pinched hard on her entire nipple, pulling as hard as her little body could take. Her legs shot out in front of her like spring-loaded wooden planks, her breath continued in gasping uneven intervals. I felt a wetness discharge and coat my thighs trying to hold her in the saddle. She was squirting everywhere with her lower back wedged tightly against my cock. I pinched her nipples again, pulling them sharply away from her chest. She emitted a small scream and soaked my thighs again with more warm honey, her fingers still feverishly pawing and slapping at her pussy. I exploded, cumming harder than I ever came in my life. Now, both our laps were saturated in sweet-smelling girl cum, and the back of the T-shirt she was wearing was coated with 8-10 ropes of my cum.

She slowly started to relax, her hands performing more of a massaging roll as she melted into my body. I stopped all caressing and just held her with a love I had not felt since I was a teenager. It was the most beautiful natural act I had ever experienced.

“Oh god! Oh god! What happened? Oh my god! I peed all over you and the chair. I’m sorry. Oh my god, Jack,” she called out while struggling to inhale oxygen. Hold me Jack, hold my boobies, they feel like they’re on fire. They are shooting tingles clear down to my thingy. I feel like I’m still peeing. I can still feel it running out of me.”

“Oh Brinnley. That was so beautiful. So, so beautiful. Are you okay?”

“This is the best feeling I ever had in my life, Jack. My god. Thank you, Jack. I love you so much for helping me. I will never forget this. Never.”

We stayed under the blanket with my arms holding her snuggly. After a few more minutes I picked her up and carried her into my bedroom. I took off my old stain-soaked sleeveless shirt, placed a large beach towel on the quilt, and laid her down on her back. I turned on the night light, ran the faucet to get the water warm, and used a soft wash cloth to gently clean every inch of her body. She willingly spread her legs wide and did not resist at all when I pulled her feet back toward her head, raising her ass off the beach towel and wiped the warm cloth up the entire length of her backside crevasse. I padded her dry with a hand towel and got her a new T-shirt, before carrying her back into the guest room. She was already asleep when I laid her down beside her brother.

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  • Reply Jay ID:1ennvarozylg

    4’8 and tiny like that? Yeah I couldn’t hold back, she’d be filled with cum

  • Reply [email protected] ID:1qkwnvpb0j

    Amazing please write more

  • Reply HornyDaddy4u ID:60aeri741

    WOW, Didn’t want it to end!!!!

    • Probass ID:2zicqep2v1

      Want to chat

  • Reply Gonzo ID:7mkmumjj42

    I thought this was a very true to life story that could happen any time and actually has to me many times. I am a sucker for a younger female and just love guiding them to their first real cock orgasm. I love to hear their lil moans, grunts and groans. Even their lil whimpers are so damn sexy. Fuck what anyone says I do not care, sex is completely natural and healthy as long as she pursues. It is your choice girls and YOU are in control of your body and if you want cock then by all means you should have it. I feel so blessed in my life to have had so many firsts for so many girls and I will continue as if it is and always have been a miracle so be selected to take them.

  • Reply Anya ID:bhr2s86ii

    Few months ago i would go to by boyfriend’s house usually when he wasn’t home just so i can let his Dad fuck me hard and suck on my pussy.
    I’m 17 and he is 55 there about, I’ve never squirted till he made me , he would fuck me and flick my clit with his thumb till i let my water all out on him!!
    My boyfriend has never acted like he knows I’m fucking his Dad, 3 months ago his Dad traveled out state for work and now he’s back, I don’t know if i should go back and have some strokes or just build my relationship with my boyfriend.
    But what i know is, i love older men and i want to explore more, if Eric’s dad can make me squirt, I wonder what other Older men can make me do? 💁‍♀️

    Older men from 50 above can email me [email protected]

  • Reply lil luver ID:1emqxfj0zyp2

    Excellent story

  • Reply DuckSoup ID:1elkj37lfq04

    Great story that was well told. Most every story has some element of truth in it and I hope that you can share more. I especially like the teaching aspect of the narrative. I too have some rosin on my heels from down east. Do you think you could tell a little more about Brinnley as she matures? The “old teacher” must have been eustatic to have such a willing student! Well done.

    • nawtygrandad ID:3k40n6rn20k

      Couldn’t agree more with your review of this story. It was sweet, very hot and legible! Author well done! Please bring us more of “Jack & Brinnley”.

  • Reply Fat Bastard ID:1367pw4m9k

    Absolutely wonderful story!
    I really hope that you’ll write a continuation!

  • Reply Robert ID:2px1ogoi3dh

    Excellent. Seemed so real. Wow!

  • Reply [email protected] Australia ID:1cn60hrk7z4d

    Just teacher and fuck her make her happy that’s what she wants