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Skater Boy Hookup

"A skater boy hooks up with a cougar."

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It was Summer, and like every summer, I could be found at the local skate park. I was nineteen and I loved to skate with my friends, grinding the rails and getting some air. It was a thrill and felt exhilarated doing tricks that felt dangerous and foolhardy to me at the time.

As usual, I was rubbing my leg and laughing after a fall when a friend of mine nudged me in the ribs.

“Dude, you see that car. She’s been parked there watching us for the past three days. I think she has a thing for young guys.”

I laughed, thinking that was a bit far-fetched. I decided I wanted to see what the deal was anyway. I made my way out of the park to where the car was parked. As I got closer the window wound down and I could see the woman inside.

“Hi there, I’m Wendy.”

Wendy was a woman in her fifties and seemed to be really nice. She had short blond hair and seemed to be quite fit. Not quite a MILF, a cougar more like. She wore a summer dress that left little to the imagination. I could see her cleavage with her breast itching to be released.

“Come inside, sit next to me and let’s have a chat.”

I may have seemed like a deer in headlights as she just laughed at me.

“Oh, come on. I don’t bite unless you want me to.”

She laughed again and it put me at ease. I opened the door and, per her instruction, slung my skateboard onto the back seat. As I got comfortable, I could see that she had inched her dress up slightly and I could see her pussy, as she wasn’t wearing any panties.

“So handsome, tell me about yourself. I saw your fall; hope you are okay.”

I laughed and started telling her about myself.

“I am Jake, I’m nineteen years old. I go to college but like to hang out and skate in my spare time.”

she seemed to hang on to my every word and it was only then did I realized that her hand was gently caressing my crotch, her fingers tracing the outline of my cock.

“Sorry honey, my mind was elsewhere. I really want to see it. It feels so nice and hard. I bet a teenager like you can keep going for years. I’ll show you mine if you show me yours.”

She smiled sweetly at me and hiked her skirt up even further and I now had a clear view of her glistening pussy. As quickly as I could I undid my zip and pulled my eight inches out of my trousers.

“Ooh, that is a lovely-looking cock. and bet it feels great in the hand, here let me touch you.”

She wrapped her hand around my cock, making more noises as her hand slowly slid up my shaft.

“I bet you please many girls with this beautiful thing.”

I blushed.

She switched hands and leaned closer to me. Her face was inches away from mine and she seemed to move close to me.

“I bet all the girls love you. kiss me handsome, I want to feel your tongue down my throat.”

I don’t know what it was, but she seemed to put a spell on me, and I was only too willing to go along with everything she wanted. Our lips met and for a few seconds that’s all we did, press our lips together. Then we both seemed to get the same idea, our lips parted, and I slid my tongue over hers. It was soft, slow, and deliberate. We seemed to make out for an age as her hand slid aimlessly up and down my shaft.

I was just comfortable sitting there in her car sliding my hand up her thigh as she jerked me off. She seemed to move uncomfortably and pulled away from our kiss. Her hand slid faster and harder on my shaft.

“Sorry handsome, but I need this cock in my mouth. I am going to suck you dry.”

I watched as she lowered her head down to my lap. As she slid her lips around my cock, she pulled down her dress slightly revealing her soft C-cup breasts. She moaned as her mouth engulfed my cock.

She knew what she was doing and started to jerk my cock as she sucked and slurped on it. She seemed to moan like it was giving her as much pleasure as she was giving me. It turned me on so much that I could not help but hold the back of her head, pushing it down further on my shaft. She moaned in approval, her tongue sticking out and licking the top of my balls each time she got to the base of my cock.

The way she seemed to jerk and suck me off was pushing me to the edge. She seemed to get off on it too. Her mouth sucked like a vacuum, and it didn’t take long for her to bring me to the edge.

“Fuck, you're going to make me cum,” I moaned.

It only seemed to strengthen her resolve, and she sucked me harder. Her hand worked me hard, making me grunt and moan till I could not hold back anymore. With one last grunt and moan, I relaxed. I let loose a jet of my hot cream into her mouth and she just continued sucking me, swallowing my load like it was her morning coffee.

When she came up for air, she smiled at me. She could see what she had done to me and giggled. She licked her lips and then kissed me once more. Her mouth was salty with my cum but I didn’t mind as her hand still jerked my softening cock.

“That was wonderful, Jake. I bet you can get hard again quickly. Want to come home with me and fuck my brains out? You can fuck me however you want I’m all yours, no need to worry, my husband is away and we have the house to ourselves all night long. Call your mom and tell her you are staying at a friend's tonight.”

I laughed and made the call as she started up the car. I was about to put my cock away, but she stopped me, telling me that she liked looking at it.

As she drove, she lowered her top revealing her soft breasts making me hard once more. She told me to gently stroke, and it was not too long before we reached our destination.

Wendy led me inside her house, which was tastefully furnished. She led me upstairs by hand and I watched as she slowly undressed for me. I pulled off my clothes quickly my rock-hard cock standing to attention.

I watched as she lay back on the bed and slid her hand over her glistening pussy. I watched as she spread it open for me smiling as I started to jerk my cock in front of her.

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“Don’t stand there jerking. stick that juicy cock inside me. I want you to fuck the shit out of me. Pound me with your youthful vigour.”

I laughed and climbed on the bed on top of her. Her hand grabbed hold of my cock and guided it into her wet hole. She moaned as I pushed as far and as deep as I could. She was surprisingly tight, and it took my breath away slightly. I lay still for a second like I was getting my bearings before I started to move.

I slowly started to move my hips, sliding in and out of her. She seemed to whimper and pulled me closer so I could get even deeper. I began to pound her harder, fucking her hard as best I could.

Her arms wrapped around my neck and pulled me close. I was laying flat on top of her, her breasts squashed against my chest. She kissed me passionately and groaned into my mouth as she started to kiss me. We made out fiercely as I moved my his at breakneck speed.

“Fuck me, fuck me, fuck me. Yes, yes, yes.”

She wrapped her legs around me, pulling me in even deeper. My head was buzzing with what was going on. She was a freak and loved getting pounded. She seemed to take pleasure more from the fact that I was less than half her age, more than me fucking her.

“Jake, fuck me from behind. Do me doggy. Hold on to my hips and slap my ass.”

I smiled and gently pulled away feeling my dick slide out of her. I watched as she jumped up and got into position on all fours. I held her hips as she reached down between her legs and guided my cock back inside her soaking wet pussy.

Her moans seemed to urge me on, and I started to gently spank her as I slammed as hard as I could. She seemed to like it too as her moans got louder. I grunted slowly knowing that I would not be able to last so long if we continued the way we were.

Wendy seemed to sense it and told me to lay back on the bed. She lay down next to me and cupped my balls. She lent forward and kissed me slowly as her hand gently massaged my balls. The feeling was amazing, and it was nothing I had experienced before. We laid there making out for a good five minutes and my urge to cum subsided, but I was still rock hard. Wendy swung her legs over my body and gently impaled herself on my cock. As she slid down on my shaft, she groaned gratefully.

She bounced on my lap, moaning all the time. I tried to sit up, but she just pushed me back laughing. She was in charge, and she didn’t have to prove it. She seemed to set a new pace, slower and more pronounced. She moved up and down, making my cock enter her hole deeper than it was before.

I groaned slowly, complaining about how close I was. She climbed off me and told me to sit on the edge of the bed. She then sat back on my lap, holding me close as she started to rock up and down on my lap once more.

We were both sitting up, her breasts grazing my chest as she bounced on my lap. She kissed me deeply, her tongue fighting a war with mine. Her hands messed with my hair, making the whole experience all the more erotic to me.

We moaned in each other’s mouths as I felt her pushing me to the edge. She seemed to sense it too and pulled away from me. She ordered me to lie back on the bed and she lay down next to me. Her hand cupped my balls, gently caressing them as she leaned forward to kiss me again.

“I don’t want you cumming so fast, honey. I want you to fuck me for a bit more and then you can cum deep inside my pussy.”

We lay there for what seemed like an age, just heavy petting, kissing and her caressing my balls. After a while she pulled away and lay on my lap, guiding my cock back inside her hole. Her hands rested on my chest as she bounced vigorously on my lap.

Her moans filled the room once more and her fingernails started to dig into my chest. I grunted loudly in unison with her and soon I was sure I was going to bust my nut. I sat up and slid my hand under her ass and picked her up as I did my best to stand up and get off the bed.

I carried her towards the wall and held her up against it while pushing my body against hers. Using the wall to keep her held up I started to pound her as hard as I could against the wall. She seemed to get the idea and wrapped her legs around me tightly and held on to my back as best as she could. I kissed her passionately as I fucked her hard. We made out and I could feel her legs holding me tighter and I was on the brink.

“Yes Jake, cum deep inside me, breed me, fuck me as hard as you can. I want to feel all that hot spunk in my pussy.”

Something about the way she was talking to me and kissing me, and heavy petting me seemed to push me over the edge. I grunted loudly and just stood still pinning her hard against the wall. With one last push, I started to cum deep inside her. She moaned as I let down her legs as I stood up against the wall still shooting my load into her hole.

We stood there for a minute or two, coming down from our extreme pleasure. We kissed slowly before she gently pushed me away. My cock easily slipped out of her pussy, and I watched her climb back on the bed and lay back with a satisfied moan. She patted the bed next to her and I climbed on laying close to her. She rolled over so her body was pressed up against me. her head rested on my shoulder, and she kissed it gently.

“You know the way out. I hope you know how to make your own way home. I'm going to sleep.”

It didn’t take long for her to drift off. I must have laid there for about thirty minutes before I decided it was time to go. I slowly got up and got dressed. I smiled as she moved slightly opening her legs and I could see my cum oozing out of her pussy.

I made as little noise as possible as I went down the stairs and out of the house. My head spun as the thought of what had occurred dawned on me. I laughed a bit as I stepped on my skateboard and started to skate home.

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Written by Sholbin83
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