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A Helping Hand

Cliche is not what my highschool crush turned out to be....

When I was nineteen I was your pretty average guy. I was five eleven, medium build, blonde hair, brown eyes. Lived in a small as town in the middle of South Carolina. There wasn't much to do and when I wasn't forcing myself into the affliction known as homework I was either entertaining myself with whatever I'd most recently managed to scrounge some cash together to buy, or I was usually hanging out with Kelly, my sister.



She was a year younger than me and the family resemblance was pretty obvious, aside from the fact she was leaner than I was. Blonde hair down to her ass, blue eyes, and yes she had some curves. When she'd turned eighteen she'd decided she'd had enough of our parents' prudish views on just about anything and announced she was going to dress how she wanted to dress, do what she wanted to do and screw whoever she wanted to. My parents were less than pleased but I was happy for her. Conservative and Kelly didn't go together.


When she wasn't hanging out with my she was hanging out with her best friend, Jamie. Jamie wasn't local, she'd only moved here about two years beforehand, and when she did, two things happened. First she and Kelly were best friends inside a week, second I fell for her. Hard. Kelly knew it too and she just loved using it to mess with me. The worst was when she'd stay over. Both of them had long since done away with the motherly bathrobes, Kelly usually just went around in her lingerie and no matter what she did she couldn't separate Jamie from her boy shorts and tight T's. I never minded though. In my opinion the clothes highlighted what was under them better than any underwear ever could.


I'm going to be honest. Most nights she stayed over I spent late nights with fantasies of her keeping me up until I finally broke down and got off. This night was different however. It was the middle of summer and I'd had a shitty night at work after a customer had tried to get me reported for actually showing them how the hell to use the phone they kept insisting was broken. I basically went home and fell into bed.


I didn't even know Jamie was there, not that it was unusual. During the summertime they were rarely apart and tonight was no exception. I must have slept for a little while but it seemed like I'd just gone out when I woke up again. Honestly I thought I was still dreaming because when I woke up I felt a hand on my crotch and it definitely wasn't mine.


After a few seconds of confusion I started to sit up and opened my mouth to ask what the hell was going on when I got pushed back down, a small hand covering my mouth. I started to get up again but froze when my desk lamp clicked on again and I realized it was Jamie who was trying to hold me down.


I opened my mouth to ask her what was going on when she lifted her finger to her lips and shushed me. I just looked at her completely confused. She'd never done anything like this before. We barely even talked, despite the massive crush I had on her. She kept her eyes on me as she reached towards my sheets and started pulling them away. My eyes widened a bit at that. It was hot out, and with no AC I didn't bother wearing pajamas. Or boxers for that matter.


Jamie was the complete opposite of my sister. She was shy and quiet and while my sister was bombshell sexy to most guys at school, the only word that I think really fit Jamie was cute. She was tiny, couldn't have been much over five feet tall and I found everything about her adorable. From her short black black hair to the green eyes that were currently looking into mine.


She finally managed to get the sheets off me and her face lit up. This wasn't the shy unassuming look I'd gotten used to seeing, this was something I hadn't seen before. Needless to say with the girl I'd been sneaking peeks at for years kneeling between my legs when the sheet came away, I was already hard as a rock. She looked down at it, obviously curious as she slowly reached out and wrapped her hand around my cock. She gripped it firmly and moved her hand up and down a few times before letting her hand drop away. I looked down at her in mild confusion. I wasn't all that surprised that she stopped. I hadn't expected this to go as far as she had. I started to get up again when she shocked me by leaning forward and giving my cock a quick lick. She stared at it for a few seconds before leaning forward and slowly running her tongue along the bottom from base to tip.


I just stared at her completely speechless. Given how she normally was I'd never have expected anything like from her. Without warning she leaned forward and took my cock into her open mouth, wrapping her lips around the head and swirling her tongue around it before slowly slipping the entire thing in.


I'm not huge but as small as she was I could tell she was having trouble taking it all. She bobbed her head up and down on my shaft a few times and I nearly came right then and there. She moved her way back up to the head and gave it a gentle suck before letting it slip out of her mouth with a pop and smiling at me. She grabbed my hands and placed them on her head before opening her mouth wide and going down on me again. She was amazing. I'd had a few blowjobs before but nothing like this. The way she took my entire cock into her mouth with the sucking and the way she moved her tongue was driving me completely crazy, but what I really liked was her attitude. She was so eager to get me off she was jamming my cock into her mouth harder than I was pressing the back of her head onto it.


As turned on as I was there was no way I was going to last and only a few minutes later I was tensing as she began to get even wilder. She looked up at me and slowly lowered her mouth over the length of my cock before lightly sucking on it and circling it with her tongue and I lost it. “Shit!” I muttered as I felt my orgasm coming. Jamie quickly slipped my cock out and began rubbing it furiously as she licked the tip in slow circles and I came all over her adorable face.


Some of it went into her open mouth but most of it hit her full on and covered her left side from her chin to her eye. She smiled and slowly and ran her finger through my cum, slowly slipping it into her mouth and sucking it clean. I had no idea what to say. I mean the girl I'd fantasized about for the past couple years had just come into my bedroom and sucked me off without a word and done a damn good job of it too.


“'That was amazing', or 'you're incredible' is generally what you're supposed to say right now,” she told me as she got another finger full of cum and began to slowly lick it clean once more.


"Umm, You were amazing. I mean damn I've never had anything like that...but why did you do it?” I asked her as started to finally catch my breath.


“Because I feel the same way you do about me,” she answered with a smile and then a laugh at the look on my face. “Did you really think Kelly didn't tell me anything? Or that it was just her idea to tease you the past couple years?” she asked me.


“Uh. Yeah,” I said feeling like the biggest idiot on the planet. I'd always thought she'd just seen me as her best friends older brother or I'd have made my own move a long time ago. “When did that come up?” I asked her wondering exactly how much Kelly had told her.


“When she was fucking me,” Jamie told me sweetly.


Wow. I hadn't seen that coming. Why was I surprised? Kelly was always a wild child and apparently Jamie was far from the shy innocent image I had of her.


“When she found out I liked you too she suggested this and gave me a few...examples,” she told me with a smile as she stood and placed her hands on my bed, spreading her legs before sticking her ass up and bending over. “Are you going to return the favor?” she asked obviously excited.


Like hell I was going to turn that down. I stood up and moved behind her, looking down at her nice short clad ass before reaching down and giving it a squeeze. She pushed her ass back against my hand and gave me another sultry smile. I reached down and wrapped my arms around her chest before pulling her back against me and holding her their tight. She let out a moan and pressed her ass against my cock as she felt it and I was immediately rock hard again.


I slipped a hand under her shirt and grabbed one of her little tits, giving it a firm squeeze before giving her nipple a pinch and being surprised yet again as I felt cool metal under my fingertips. I began pulling her shirt up over her head and she eagerly lifted her arms to help. As soon as the shirt was over her head she turned and looked at me, showing off the small silver hoops in each of her nipples proudly. I laughed at the sight. Damn, I'd had her pegged so wrong. She blushed a little and reached up to tug on the hoops, her tiny nipples rapidly coming to attention as she did. “Kelly's eighteenth birthday present for me.”


I swear my cock throbbed at the sight. I moved her hands away and pulled on the little hoops myself and Jamie let out a low moan. “Are you two a couple?” I asked curiously as I kept toying with her nipples.


“No. Kelly just helped me...learn some thing about myself,” she told me, her eyelids fluttering a bit.


“Like?” I pressed as I slowly lifted up on the rings and forced her to stand on the tips of her toes.


“Like, sex is fucking amazing, and like everything she has me try gets me off and like I looove being a sub,” she said, the words coming out in a jumble as she began to breathe.


I grinned down at her and let the rings fall before reaching down and slipping my hands around her ass and lifting her up. She took the cue and wrapped her arms around my neck, leaning in and kissing me eagerly. Kelly had done a hell of a job teaching her well...everything really. As we kept kissing I squeezed her ass and pressed my crotch into hers, eliciting another moan. I lifted her up further and brought my mouth to her cute little tits, grabbing one with my teeth and gently pulled. She wrapped her arms around the back of my head and held me there as she rolled her ass against my hands.


“You like those?” she asked breathlessly as she continued to writhe against me.


“Oh yeah, I love piercings,” I told her before pulling the other ring and getting a quiet gasp.


“Maybe I'll get some more then....” she said dreamily. That was a nice image. Without warning I dropped her on the bed and went to pull off her shorts and she once again tried to help me. This time I grabbed her hands and held them above her head, kissing her deeply before leaning down and pulling her rings again with my teeth.


“You like this?” I asked her as I let my free hand drift down her stomach towards her thighs.


“Oh god yes. Please fuck me?” she asked as she opened her eyes. Damn she looked hot. Her hands pinned above her head, that sexy sweat only women can do, and the look on her face. A hungry look. She was loving this. Good. So was I.


“Oh hell yes, but first I'm going to return the favor remember?” I asked her as I slowly slipped her shorts off with my free hand. It took a few seconds, the shorts were tight as hell and I had to lower one side and then the other until they slipped down over her wonderful thighs. As soon as they were clear of her thighs my hand darted between them, my fingers locked in case she tried to close her legs again.


She didn't. Instead I was treated with another moan as the tips of my fingers brushed her slit. I slowly worked a finger into her cunt, surprised at how wet she was. After a moment I realized the shorts she'd been wearing were soaked in the front. She really was enjoying this. I slowly began to slide my finger in and out of her and pressed my mouth over hers.


Her tongue eagerly slipped inside my mouth and began to quiver as I began slipping my finger deeper inside her. Damn she was tight. I kept slipping my finger into her cunt, slowly going faster as I started rubbing my thumb along her clit. I broke the kiss and she started breathing heavily as she began rolling her hips against my hand. I slowed and slipped carefully added another finger. She gasped and began pushing against them even harder. Making sure her hands stayed pinned I leaned down and placed my tongue on her clit before slowly sucking it into my mouth. Her back arched and she grabbed my pillow, burying her face in it. I felt her tighten around my fingers and kept working them slowly in and out as she came. After a few moments she threw the pillow aside and looked up at me with an expression of absolute bliss.


I smiled and leaned down to give her another kiss which she happily returned. “Still want a fuck?” I asked her as I reached down and pulled on her nipple rings again. I could get addicted to those little things.


“Fuck, if you don't do it I'm going to go get Kelly to,” she told me with a smile, her chest still heaving slightly as she recovered from her orgasm.


How could I let that go? With a smile I flipped her over on her stomach and she raised her ass in the air without hesitation. I reached down and squeezed it again and again she pressed it back against my hand. With a grin I pulled back my hand and gave her a light swat and got a surprised squeal as I gave it another squeeze. I got behind her and looked down at her and wondered how I'd gotten so damn lucky. I placed both hands on her sides and gave her ass another squeeze with both hands as I grabbed it and pulled her against me.


She lay limp against the bed, her hands too busy playing with her nipple rings to hold her up. I lined my cock up with her pussy and rubbed her clit with the head a few times before slowly sliding it inside her, savoring every inch of her cunt. As it slid in she let out a low unending moan as she pulled on her rings harder than I would've dared.


She tried to push back against me but I held her still, savoring the tightness before slowly rocking her forward and pulling my cock back. “Fuck yes!” she said, her voice almost as dripping with excitement as her cunt. I started thrusting into her, slowly at first but each stroke became a little faster until I was hammering away at her tiny cunt, my hands on her hips pulling her against me I slammed my cock into her. She closed her eyes and from the way she was breathing I could tell she was close.


Without thinking about it I reached down and slapped her ass again, and not a play slap either. She let out a gasp and then buried her face in my pillow. I felt her pussy tighten around me and a rush of heat and wetness as she came. I didn't slow down. I could feel my own orgasm quickly approaching. Her pussy kept gripping my cock almost like it didn't want to let it out even for a second. I lasted a few more wild thrusts before slamming my cock into her spasming cunt and cumming harder than i'd ever cum before. As I filled her cunt with my cum she let out a shuddering breath and rolled her ass against me taking me even higher.


A second later we both fell back on my bed breathing hard and just laid there enjoying the high. After a few moments Jamie rolled over and laid on top of me before leaning down and giving me a lazy satisfied kiss. “That was amazing,” she practically purred in my ear. “I can't wait to do it again,” she told me as her hand wrapped around my softening cock.


Honestly I would've loved to go again right then and there, and most of the time it wouldn't have been problem. I'm only average size wise but I can go a hell of a lot in fairly short period. Tonight I was still feeling the ass kicking from work and my cock only got semi hard as Jamie kept stroking it.


“I think he's had enough for now,” an amused voice rang out in the silence. A familiar voice.


“What the hell Kelly, you could knock you know?” I asked her as I threw the sheet on my bed over me and Jamie.


“Oh sorry, who was it who set tonight up again? Oh yeah, me. Chill bro, here.” And with that she yanked her bra up over her head and slipped the g-string she'd been wearing far enough down that gravity could take over and pull it to the floor.


“There, now we're all even. Mk?” She asked me quirking an eyebrow. I just stared at her. She'd been pretty free with the clothes lately but this was a step up even for her. Apparently my expression was pretty good because she let out a short laugh before looking to Jamie and giving her a come hither gesture with her finger. “Come on Love, I think he's had all he can handle for now. I'll take care of you for tonight and you can continue this in the morning.”


I was about to tell her to back off when Jamie slid out from underneath the sheets and made to get off the bed before looking back down at me. “Do you mind?” she asked, her eyes a mixture of question and pleading.


Honestly I wanted her to stay in my bed with me, but I was just as glad to have something else to occupy her at the moment. I was drained. Besides, how could I say no to that face? “Go ahead. I think I'll take you up on Kelly's offer in the morning,” I told her giving her another playful slap on her ass as she stood up.


She gave me a smoldering gaze and sensually shook her hips a few times before sauntering to the door and stepping out of my room. “Don't worry Jace, I won't break her. Much. See ya,” she told me before shutting the door as she started down the hall. It took me a moment to register she'd left her panties and bra on my floor. I was tempted to grab them and do what with them I didn't know, but as tired as I was it seemed like a far better idea at the time to sink back into the pillows and let myself drift off to a very satisfied sleep.....


{First story. Be gentle.}

{May be continued if I get any feedback}



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