**The following is a story of sexual discovery between two sixteen year old best friends.**
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“Ungh!” I yelped, as the head of his cock entered my opening, I gripped the bed sheets beneath me with my nails dug in, this was my first time and it hurt so much the pain was almost unbearable, I lay there with my eyes closed so tightly my eyeballs began to ache, biting my lower lip and holding on to the bed sheets with every bit of strength I had, I was scared, I kept thinking “How could something so huge fit in to such a small hole”.
In any other situation with the amount of pain I was feeling I would have made it stop, cried and screamed out for my mother for comfort and safety, but not this time, this I craved, I needed it, my pussy was soaking wet and waiting for it, my entire body was aching with an uncontrollable and natural desire for it, to hell with the pain, “Keep going” I uttered, willing him to carry on and as his shaft slid further inside me I could feel the walls of my insides squeezing around his enormous girth.
He was half way in me when he briefly paused before slamming it in reverse dragging a pool of clear fluids along with it, when his tip hit the rim of my opening I could feel the juices flowing out of me like a water balloon had just burst all over my pussy and with the head of his cock teasing me once again he pushed it back in, “Ungh” I yelped again, “Oh my God!” I groaned as he thrust his shaft back inside of me, even deeper this time.
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**Wait. Wait. Wait. I’m getting ahead of myself here. Let me start at the beginning.**
I’ll start with a bit of background…
Sean and Hailey were sixteen years old when the following events occurred but had met at the tender age of seven after Hailey and her single mother moved in to the house across the street. Her mother became good friends with Sean’s father, who was also single at the time, and they spent a lot of time over at each others houses and that is how Sean and Hailey were introduced and how their friendship started. Their parents also worked at the same factory on the outskirts of town so Sean and Hailey would more often than not sleep over at each others homes, obviously they had a babysitter when they were younger but were deemed old enough to look after themselves when they got older and were left alone while their parents worked the gruelling night shifts.
They would do everything together, eat together, went to the same school, on outings and holidays together, they and their parents would treat each others homes as their own and would come and go as they please, they were inseparable and their friendship flourished as the years flew by.
Sean was about 5’5”, had short dark brown hair, blue eyes and was really skinny, he’s what you may call “Lanky”. He was the shy one who was always hesitant when meeting new people or trying something new, he wouldn’t be your top choice when picking a team to play football with but he’d always be there when you needed him and he was fun to hang around with, he wouldn’t say boo to a goose. Hailey would describe him as super sweet and cute.
Hailey, was around 4’8” and extremely petite for her age. She didn’t let her small height affect her though, she loved all kinds of sport and was an active member of the school badminton team. You wouldn’t think she’d be able to keep up with the other much taller players but she did, she was so athletic and could probably give some NBA stars a run for their money. Height not a factor. She was outgoing, bubbly, friendly and a bit of a nut. Her hair was a light shade of golden honey that she hadn’t cut since she was nine and it had grown down to her elbows and always in a ponytail at the back, her eyes were a deep emerald green. Sean would describe her as a twitchy, fidgety, over-hyper pain in the backside.
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**Day 1 – Tug of war -** From Sean’s Perspective:
Dad was working the night shift again so I stayed over at Hailey’s that night, we’d spent the last few nights at my house so it was a nice change to be over at hers for once. After eating a large pizza with stuffed crust and finishing off a large bottle of Coke we spent the rest of the evening in the front room cuddled up on the sofa binge watching the latest season of Stranger Things, it was our favourite show, I think we got to episode five when, after a long day of school, we were both tired so we turned everything off and tidied our stuff away and went upstairs to bed.
Hailey’s room was at the back of the landing facing the front of the house and it was your typical girl’s room with walls covered in posters of her favourite pop group, some Korean boy band called BTS that made me want to rip off my ears every time she played their stupid songs. Her bed was against the wall at the back of the room, a single with yellow sheets and pillows with floral patterns around the edges, she loved flowers and the colour yellow, I wouldn’t be caught dead with anything like that on my bed.
After a quick wash and brushing our teeth I put on my pyjamas, nothing special, plain black bottoms and no top, it was really hot that night. Hailey, had pyjama shorts and a strappy vest top with a BTS logo all over it. And yes, they we’re yellow.
We always slept in the same bed next to one another, we’d done it since we we’re kids so it was natural for us to share the bed. I was always shoved against the wall, you wouldn’t believe how many times I’d banged my head against the wall over the years turning in my sleep, I’m surprised I don’t have brain damage. It always took Hailey ages to calm down, she was so hyper, tickling me and fidgeting but eventually she relaxed and got comfy. As always we’d spoon each other and cuddle to keep warm as we both drifted off to sleep.
I was awoken in the middle of the night, it must have been quite late because the room was pitch black, a few moments after my tired eyes flickered open and I was looking at the back of Hailey’s head my brain woke up and I suddenly felt a flood of sensation racing through my mind, feelings of pain, panic and pleasure all at once, I was instantly confused. I shook and lifted my head off the pillow, flicking the back of Hailey’s hair off my face, and I lifted the bed sheet, I was in shock at what I saw, “Hailey, what are you doing?!” I shouted, in a panicked tone.
Hailey had her arm behind her back with a tight grip around my erection and was rubbing it back and forth, “Sshh” she whispered with a giggle, I couldn’t believe it, I was so embarrassed, why was she doing this to me all of a sudden, she’s my best friend, this type of thing between us never entered my mind, until now, “..but..what are you do-ing..” I replied, starting to lose my train of thought, “Sshh” she repeated, continuing to tug on my erection.
This was all wrong, but it felt so right, it felt so good, but it felt wrong, I don’t know what to think, “..Please..” I groaned, falling on to my back I quickly pulled the pillow from behind my head and held it tightly over my face doing everything I could to stop myself moaning out loud with pleasure, as my back hit the mattress, her grip, her tight unrelenting grip never loosened for a second as she too turned and lay on her back, giggling her face off and she tugged and tugged on my now rock hard enormous shaft, gradually gaining speed.
I occasionally lifted the pillow from my face, not only because I was suffocating, but because I wanted to see what was happening, quickly overcome with embarrassment and an uncontrollable urge to moan the house down I’d press it back against my face. I’d had erections before, heck I’ve even jerked myself off before, what teenage boy hasn’t, but this, this was the hardest I’d ever been and my solo wanks never felt as good as this does right now, “Fuck!” I screamed, the sound muffled by the pillow over my mouth, I could hear the muffled sounds of Hailey’s laughs as she tormented me.
Hailey kept tugging up and down my shaft and getting more rapid, she was tugging my entire length and I could feel the base of her hand constantly pounding against my balls, ‘Bang. Bang. Bang.’, her palm had begun to dry and I could feel the roughness against my skin, I honestly though she was going to tear the skin off my cock and moments before I was about to scream out in pain her fingers must have caught on to my pre-cum which gave me some much needed lubricant relief.
As my breathing became more rapid and my heart began to beat so fast I thought it would burst out of my chest and a feeling of ecstasy flooded my mind, I knew what was about to happen, my shaft began to swell and my balls began to ache, not just from the constant pounding from her hand, but because I was cumming, I could feel the pressure building up at the base of my shaft, but Hailey’s tight grip was preventing it from moving, I wanted to cum so bad my hips began to twist and pull, my legs began to shake as the biological urge to ejaculate overwhelmed me, I needed to cum so badly but I couldn’t.
Unable to take it anymore I threw the pillow off my face and perched myself up with my shaking arms to look down at my distressed cock, “Hailey!” I grunted, “Let go!” I added, but she didn’t, it made her go faster, I turned my head to look at her with an agonised expression on my face, she was just smiling at me with mischief and fascination in her eyes, I wanted to push her away, ‘for the love of God please let me cum’ I thought, I wanted to be angry at her, I wanted to force her to let go but at the same time I kind of didn’t want it to stop, instead of shouting like I should have done I laughed under my breath and smiled back at her before my weakening arms buckled and I fell back on to the bed.
A few more minutes went by as I battled through her relentless tugging and my entire body was shaking and covered in sweat, I was aching all over and I thought for sure if she didn’t let go soon that my balls were going to explode. Then I felt her loosen her grip, did she do it because she wanted too, did she do it because she knew how much I needed her to do it, had her arms finally tired, I didn’t care, I was relieved.
This is it, I could feel it, it was about to happen, ‘thank you, thank you, thank you’ I thought to myself, when her grip loosened my body began to shake and wiggle, with Hailey’s tugging not slowing down but at least she wasn’t strangling my cock to death anymore, my back was arching and lifting off the mattress as the pressure continued to build like a whistling kettle reaching boiling point and with the loudest longest groan of complete ecstasy my shaft swelled and my load exploded out of me, the built up pressure was so intense I swear my load almost hit the ceiling.
As my cum ejaculated from my shaft several times like a geyser I finally felt the sweet sensation of release, I felt Hailey’s body jump beside me, “What the fuck!” she shouted, “Holy shit!” adding a shocked and surprised laugh at the end, “Urrrrgh” she moaned, as my thick white sticky goo continued to flow in decreasing burst, it trickled its way down my shaft, over her fingers and dripped from the bottom of her hand on to my balls.
I lay on the bed catching my breath and felt relief it was finally over, I couldn’t help noticing that she was still holding my cock, which was now slowly shrinking down, she had a look of absolute shock and bewilderment on her face, she was in a daze perched up on the bed with her eyes and mouth wide open, “What’s wrong?” I asked, she didn’t respond until I nudged her with my elbow, “What. The. Fuck. Was. That.?” She quizzed, I laughed with happiness, despite my embarrassment and shock that she would do that to me and put me through such an ordeal I was still a dude, I’d just cum, life is awesome, ‘Wahoo’.
She slowly removed her hand and lifted it away from my soft cock, allowing it to flop on to my still aching sack, she left her hand in the air for a moment and then opened her fingers, her eyes widened more, she gasped, my sticky cum was all over her hand and now forming strands like cobwebs between her fingers, she slowly turned her head to look at me, then without saying a word she spun her legs off the edge of the bed and got up and walked off to the bathroom.
Hailey returned a few minutes later after washing her hands and handed me a towel as she approached the bed, she calmly sat down on the edge of the mattress with her palms clasped together, as I wiped myself down I heard her speak softly, “I’m sorry.”, I’d heard that tone before, but not for a long time, it’s the tone she used when she was a kid, when she knew she’d done something wrong and was about to be told off, “Come here.” I said, grabbing her around her tiny waist and pulling her on to the bed.
We lay side by side and I repositioned her arm across my chest to cuddle up to her, I wasn’t going to tell her off, sure she’d done something completely embarrassing, highly inappropriate and without my permission, but she’s my best friend in the world, she’s, she’s Hailey, I love her, maybe I loved her more than I thought, “Why did you do that?” I asked her, stroking her hair and the side of her face, “I don’t know, I just got sick of it.” She replied, rubbing my collar bone with her finger tips.
“Sick of what?”
– “Do you know how many times that thing has woken me up this year?!”
“What do you mean?”, I knew what she meant, I get random erections all the time during the day, it’s bound to happen at night time while I’m sleeping as well, especially if I’m having a particularly erotic dream, I’m sixteen years old, I’m young, I’m hormonal, it happens.
– “Your nob has been sticking in my back at night, I can’t sleep with it poking at me.”, she replied with a giggle and a grin.
“But why did you do….. that?” I asked, nodding my head indicating towards my crotch.
– “I was trying to move it out of the way without waking you up because I knew you’d be embarrassed, that’s why I’ve not mentioned it before, I didn’t want things to get awkward between us.”
I couldn’t believe what I was hearing, if she thought telling me about my erections or simply moving it out of the way would be awkward, what the heck did she think jerking me off was going to do, “I think we’ve gone way beyond awkward.” I replied.
We both laughed and Hailey lifted her head to look under the bed sheet, “Does it hurt?” she asked, gazing down under the sheet at my limp and wrinkled manhood, well I was only sixteen so probably more of a boyhood, but it was definitely man sized, I put my hand under the sheet and rubbed it, “It aches a bit” I replied, I then twigged that she’d just given me a hand job, even with the pain it was totally awesome, had she done this before, where did she learn to do that, what if she has a boyfriend I don’t know about, what if she loves him more than me, I’m going to lose her, you slut, you dirty little whore, how could you, “Have. Have you. Have you do that before?” I asked, silently praying that she says no, then I heard her sweet voice in my ear, “No!” she replied firmly, I was so happy at her response I squeezed her tightly.
– “I’ve seen it before but never like that, it was huge. Is it meant to get that big?”
Neither of us had done anything like that before, we were only sixteen and weren’t exactly experts on the subject of sex related stuff, I knew my body and she knew hers, that was the extent of our knowledge, sure we’d learnt a bit at school about different bodies and reproduction but nothing like hand jobs or anything, she was as curious about my body as I was of hers, it was embarrassing but I told her, “Yeah. I can’t control it though, it just pops up whenever.” I replied.
That just made her ask more questions, “Was that stuff that came out sperm?” she asked.
“Yes.” – “But how did you know how to do that?”
– “I didn’t. I just guessed.” She replied, then she laughed and turned red, “I saw you wanking in the bathroom a few months ago.” She added.
“What?!”, now I was embarrassed.
– “Remember when you were in the shower, that day we were running late for school, and I rushed in to brush my teeth? It took you a few seconds to realise I’d come in and I saw you wanking off before you quickly turned around.”
I didn’t even realise she’d seen me, “Nooo. Damn.” I replied, placing the palm of my hand over my eyes in total embarrassment, “I keep forgetting to lock the door.” I added.
We continued talking for about an hour or so after that, learning a lot of new things about each other until we eventually realised the time, and to be honest I was completely drained, in more ways than one, so we went to sleep and went to school the following morning.
Our relationship had changed massively that night, we were no longer just friends, and we’d started a journey on to a whole new type of relationship.
Over the next few weeks we explored our sexuality and each other and ended up doing a lot more than just jerking off, but that’s another story, I’ll tell you about in Part 2.
Good night.
Source: reddit.com/r/eroticliterature/comments/k5uqxp/a_tale_of_sexual_discovery_between_two_sixteen