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Guiding Kaylee

"Dan helps out Kaylee, who doesn't know how to cum."

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I sat on the edge of the kitchen bench, chewing on a raspberry liquorice stick. My eyebrows were furrowed and I wanted to bite my fingernails—an annoying habit that was extremely hard to drop. My mind was running on the same loop that it had been for weeks. Is there something wrong with me? Does anyone else have this problem? Sean surely doesn’t. He seems to get along just fine when we are together. So why can’t I? It’s not like I don’t want it. I do. So badly. All the time. There’s a constant pressure between my legs and all I think about is sex. So why can’t I cum? I can’t even do it by myself! I sometimes hear my brother fucking his girlfriend in the next room and they certainly sound like they aren’t having any troubles! Unless she is faking it? What if it’s not even really possible? If that’s true, then why is everyone always talking about it?

My heart skipped a beat when I realised that I wasn’t alone in the room. Dan looked at me over his shoulder and had a funny look on his face. He’s been best friends with my brother for as long as I can remember and knows me pretty well too. Dan poured an orange juice and then grabbed an extra glass from the cupboard and poured me one too before he came and stood next to me, wordlessly handing me the glass. Dan’s presence wasn’t helping my current predicament. He’s sexy. Way sexier than my boyfriend with short cropped blond hair, sparkling blue eyes and classically handsome features, including dimples that indent his cheeks when he smiles. I probably shouldn’t think that, but with all the sexual frustration ebbing around inside of me… well, I couldn’t help but feel that way. And, as I’ve heard, many girls experience the same feelings around him.

“Are you having boyfriend troubles, squirt?” He flicked his fingertip across my nose.

“Don’t call me that,” I scrunched up my nose. “I’m almost twenty.”

“Hmm, but you’ll always be my squirt,” He grinned and I got the full effects of his dimples. “And I can’t help but notice you avoided the question…”

Heat rushed to my cheeks as I contemplated sharing my predicament with Dan. He’s really smart, studying some fancy science degree at University and he’s had his fair share of girlfriends and one nightstands. But admitting that I can’t orgasm…? That’s pretty embarrassing, especially in front of someone as sexy as Dan. I didn’t want him to think of me as being sexually defective.

“I… um… it’s not Sean,” I sputtered out.

My cheeks were practically on fire and heat was spreading down my neck. Dan’s head cocked the side and curiosity was written all over his face. I pushed my auburn hair over my shoulders and tried to breathe normally. I tossed the liquorice stick aside and started chewing on my thumb nail. Dan’s warm hand gripped mine, which sent warmth curling around in my stomach, and removed my thumb from my house before he placed my hand on the bench next to me.

“You aren’t into him anymore?” Dan asked.

“It’s not that,” I chewed on my bottom lip. “Not at all. I just… I can’t…”

“You’re not ready to have sex? Is that asshole pressuring you?!”

I flinched in the face of his unexpected anger. “No! We’re having sex! I wanted to have sex! It’s just…”

“Just what?” He coaxed softly. “You're red as a tomato,”

“I can’t cum,” I held my breath after I made the quiet admission. I started to feel lightheaded and my heart was beating so quickly and so loudly that I could hear my blood pounding in my ears. The adrenaline was really pounding as the silence stretched between us.

“That’s probably just him,” Dan said, sounding thoughtful. “What about by yourself?”

“Not at all. Not ever.” I covered my face with my hands.

Dan drew my hands away from my face and helped me down from the bench.

“Come on,” he murmured.

***

Excitement and trepidation thrummed through me when Dan closed my bedroom door behind us and locked it. I took a few steps away from him, even though he didn’t take any steps towards me. My mouth was dry and my heart was beating like crazy in my chest. I like Sean. He’s my first boyfriend. He took my virginity. He’s nice. Why, if I really felt that way, was my clit pulsing in time with my heartbeat?

“I won’t touch you,” Dan said, but his voice was husky.

My whole body froze when Dan walked past me, his chest brushing against mine, before he sat down in my window seat and appeared to make himself comfortable. I didn’t know what he planned. Did we come up here to talk more, in private? My mind had kind of wandered to a different place—a naughty, nasty place. And, yet, I’d still followed him upstairs to his bedroom. Dan motioned for me to sit down on my bed. My feet felt like lead as I complied, walking slowly across the room and sitting down on my bed with my legs crossed.

“What now?” My voice was breathless.

“What do you do when you get off?” Dan asked.

“What do you… what do you mean?”

“How do you go about it?” He persisted.

“I… strip off… sometimes… and then just get down to it.”

His eyebrows furrowed. “Sexy stories? Porn? Your imagination? What gets you going?”

“I’m normally doing it because I’m horny. Sometimes for no reason. Sometimes I imagine… things.”

It was equal parts embarrassing and a turn on to talk about this with Dan. My nipples were sensitive and hard, there was this strange warmth in my stomach, and there was a tingling between my thighs. My cheeks were really hot and I didn’t know if it was from embarrassment or arousal. I get horny and I try and get off, but I’m not sure if I’ve ever been this turned on before—and just from talking! Maybe it’s because Dan is so attractive.

“What about while you’re doing it? What keeps the engines running?”

“Engine’s running…? What?”

“You need to keep turned on while you do it—or you won’t get off… Are you thinking about trying to cum or how good it feels while you do it?” Dan questioned.

“I think about wanting to cum.”

“Are you attracted to me?”

“Yes,” I answered without thinking.

Silence had descended again and my heart started pounding again. I couldn’t believe I’d just said that! My mouth was so dry and my body so hot. My hands were even shaking! I’d never felt like this before. Not ever. Not even with Sean in the middle of sex… The heat in my stomach intensified when Dan casually took his shirt off. He’s never been one for tight t-shirts or public nudity, so I was extremely surprised at the sight of his six pack, muscular shoulders and the sexy tattoos across his chest that I couldn’t identify from where I was sitting.

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As my eyes travelled down further, I got even more hungry when I saw that he had one of those incredibly sexy ‘V’s’ leading down to his jean clad legs.

The embarrassment faded away in the face of the most intense arousal I’d ever felt. I pressed my thighs together, feeling the way my damp underwear clung to the apex of my thighs and I felt sweat gather at the back of my neck. Fuck. I wanted him so badly, Sean be damned.

“Now, take yours off too. Slowly. Let your hands slip over your skin.”

My fingers were shaking as I slowly lifted my shirt over my head, letting my fingertips brush over my hips and across my flat stomach, over my sensitive breasts and then across my collar bone and neck before I tossed the shirt aside. I was glad that I’d worn one of my nicer bra’s today, a lacy lilac number. I didn’t think it could ever feel so nice having my own hands on my skin. I leaned back on my bed, getting comfortable against the pillows as Dan’s blue eyes drank up the sight of the skin that I revealed.

“Perfect,” Dan rumbled deeply. “Trace your fingertips around your stunning, perfect handful sized breasts but don’t touch your nipples.”

I sighed as I did what I was asked, never breaking eye contact with Dan. Shivers raced down my spine as I traced along textured lace and felt my nipples tighten impossibly more. Even with the space between Dan and I, I could see his eyes darken and grow hooded. I traced my fingers across my collarbone and neck and back down again to my breasts. Dan groaned appreciatively as he watched from across the room. I didn’t miss the sizable bulge in his jeans. My thighs pressed together and I felt a pressure building between my legs. I wished that it was his hands instead of mine. The thought alone made me gasp.

“That’s it, Kaylee… touch those nipples now. I can see how turned on your getting, the sweet flush in your cheeks and across your chest. I can see how laboured your breathing is and how hard those perfect little nipples are.”

My fingers brushed across my extended nipples and I couldn’t help but moan. I reached back and undid the clasp on my bra with a flick of the wrist, letting it fall away. Both the sensation of cupping my breasts and of my nipples pressing into my palms turned me on greatly. I tipped my head back with a sigh. Without being prompted, I rubbed my nipples and pulled at them gently.

“Look at those mouth-watering apricot coloured nipples… I’d just love a taste. Slide your other hand down your stomach slowly, real slow…” The strain in Dan’s voice was seriously turning me on.

When I looked over at him, one of his hands was slowly rubbing the bulge in his jeans. I dragged my fingers from between my breasts, down over my stomach and tucked my fingers of one hand into the band of my shorts. It was becoming impossible not to touch myself. All of this felt like one, massive tease. I looked over at Dan for confirmation as I fingered the top button on my shorts. He nodded his head and his throat worked as he swallowed. I slipped my shorts and underwear down my legs and slipped them over my feet.

“Yours too?” I asked hoarsely.

Dan didn’t waste any time sliding his own jeans down, but I wasn’t about to call him on being hypocrite when I was so turned on. I slid my finger over my puffy lips which had gathered moisture on them and watched with baited breath as Dan revealed his erection. Holy shit. His cock was long, thick and hard—the circumcised head was red, dripping with precum and bobbed gently against his stomach as he threw his jeans aside. I pushed a finger through my wetness and groaned in delight just as Dan’s eyes feasted hungrily on my wet pussy and his hand started moving over his cock. I stroked my finger, up and down, gathering wetness. I lifted a glistening finger for him to inspect before I sucked on the digit.

He groaned deeply and I saw his cock twitch. His was so much bigger than Sean’s. Dan’s was so gorgeous that I wanted to suck it and fuck it—so much more than I ever did was Sean. I pumped a finger inside of myself and my hips arched off the bed. I moved further down the bed and spread my legs so that Dan had a better view and I rubbed my clit with one hand and pulled on a nipple with the other. That pressure in my stomach was back in full force and sending deep shivers outwards from my stomach to my nipples and down to my toes. It felt so fucking good. And from this angle, it almost looked like Dan was jerking it right into my pussy.

I moaned and tossed my head back as I toyed with my pussy.

“Just focus on your clit, Kay, just your clit. Keep the pressure light, but consistent. You can do this while your fucking and you’ll have a better chance at cumming.” Dan’s voice was so hoarse and sexy.

My pussy made a wet sound as I rubbed my clit up and down, trying to keep the pressure light. I chewed on my lip and kept my eyes trained on Dan’s cock and the mesmerising motion of his hand. This whole situation was so erotic.

“How will I know when I’m—‘’

“Shhh, just enjoy it. You’ll know.” Dan rumbled. “Try squeezing your pussy muscles as you play with that sweet, pink clit.”

A moan escaped me and my hips lifted off the bed in pleasure. There were dark spots dancing around and my heart was pumping frantically. Little shock waves sprung from my pussy outwards as I stroked my clit. The pressure in my stomach was building. I was falling towards something. Dan groaned and then groaned again as he watched me and his hand moved faster and it was making me crazy. My hips jerked upwards and I moaned noisily. I couldn’t imagine it feeling much better than this.

“Are you going to cum? Or you going to cum?” I asked frantically.

“Yes,” he groaned.

“Do it on me!” I begged. “Please, Dan, please!”

He scrambled up and took two big steps towards me and it happened. Those waves from before turned into an explosion. My hand gripped my breast incredibly tightly; holding on for dear life. It felt deliriously good. I cried out and my head thrashed from side to side as the incredible waves ran over me.

“Yes! Yes! Oh God, yes!”

It kept going and going and then Dan groaned deliciously and a hot splashed landed on my stomach. With my hand still working furiously between my legs I got on my knees and caught the second hot spurt on my cheek. Dan released a guttural moan and kept jerking his cock. Another creamy load landed on my breast and dripped down to my nipple. Those waves started again and I yelled out as pleasure radiated through my body again. Dan kept stroking and the last drops of his load coated his big hand. I collapsed back on the bed, satisfied for the first time ever.

Dan stared at me with parted lips with his hand still around his semi-hard dick. I pushed up on my elbows and scooped up the cum from my stomach with my fingertip before sucking it into my mouth.

“Mmm,” I groaned.

“You sexy fucking creature!”

“I guess I can cum, after all.” I smiled lazily.

 

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Written by LovelyLady96
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