Life of Paul: Rendezvous: Ashley

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All characters appearing or mentioned in this story are 18 years old or older. This story is a work of fiction and any reference or description to actual persons is unintentionally.


April 1998

I was skating at the school with my friends one spring afternoon when a very interesting thing happened.

No, it wasn’t that I finally landed that fakey to backslide down the quad stairs that I’ve been attempting for the last hour. Although in hindsight that would have been almost…Almost as cool.

It was that fact that a very feminine voice in our all male skating group was calling my name. Turning to the pleasant sound, I found that the voice belonged to Ashley.

Ashley was on the color guard and also a cheerleader part time, so she was slight of frame but still curved in all the right places. Her long platinum hair framed her high cheekbones and wide smile below her sky-blue eyes. She wore a simple summer dress with spaghetti straps that went low enough on the top to show her firm B cup breasts, and high enough on the bottom to show her firm tanned thighs.

We had a few classes together, and chatted once in a while but nothing more than that. She was what most people would associate with a typical California surfer girl (which is fine cause she also surfed), but the fact she was talking to me in a more serious tone made her more atypical in my opinion. Also the opinion of my friends as they also could not believe that this fine example of high school honey could possibly be talking to one of us. Skaters at my school were not held in as high esteem as the typical football and basketball jocks, and we certainly didn’t have cheerleaders. Still, she was here. Hooray.

“Hey, Paul”, she said. “Got a sec to talk?”

Do I have a sec? What the hell would I say, no?

“Yea,” I said, totally suave and not at all voice high pitched like, “sure thing.”

I rolled over to her and sat down on the steps. Skates made things difficult to do cooly, but I managed to sit down without embarrassing myself.

“So whats up,” I asked.

“This is sort of awkward, and you can say no if you want, so please don’t let me go on if you aren’t interested.”

I stared for a second. “I can’t imaging saying no to anything you ask, which is both endearing and possibly a little sad.”

She laughed at that. “Cute. Ok, here goes.

“So I overhead Amber this afternoon while she was in the locker room after P.E. She was talking to a couple of other girls and she mentioned something that got my attention.”

Amber. The woman who made me a man. We hooked up quite a few times (I could boast and say hundreds but you know I’d be lying) since my birthday, and she said that she was going to help me expand my horizons. I didn’t know what she meant at the time exactly. I also didn’t really care because at the time she was naked and riding me. Before my attention drifted too far away from Ashley I pulled myself from my memories.

“What was she talking about, dare I ask?”

Ashley reddened a little before answering. “The other girls were asking about why she didn’t seem to be dating anyone for the last few months. They pressed her and she finally answered that she found a hook-up that satisfied her in every way she wanted, so she didn’t need the hassle of a boyfriend.

“Anyways, the others kept pressing and she finally told them that you were the one satisfying her. And at this point, I got rather more interested.” she said.

“Oh,” I piqued.

“Oh shut up,” she jibbed. “Anyways, she told them that you did all the things typical high school boys don’t and that if they didn’t believe her that they should try you themselves.”

“Huh,” I said. “She she basically said ‘For a good time call Paul’?”

Ashley reddened a bit more. “Basically,” she said. “But that also got me thinking about a couple of things.”

She took a breath before continuing. “I… I haven’t had the best of luck with boyfriends either. And since Amber is quite satisfied with your… attention to detail shall we say, I thought that maybe you can help me with my problem.”

I was telling myself to be cool, but it was hard to hide both my excitement and the growing erection in my overly baggy skate pants.

“So,” I asked, “how is it exactly you think I can help?”

Ashley looked around to make sure we were not overheard.

“I want to ask you if you’d help me have an orgasm,” she said quietly and quickly.

Aaaaand now there won’t be any hiding of my boner. I also looked around to make sure we weren’t overhead.

“So,” I started, “you’d like me to pleasure you until you cum. Are you serious or is this like a candid camera type thing?”

Ashley smiled nervously. “No, no tricks. And if possible I’d like more than one if you’re up for it. See, I’ve had sex but none of them ever made me finish. And they typically finished before I could even start to have fun. It was disappointing to say the least. And, since Amber had such…intriguing things to say about your skills, I figured you would be someone who can help me.”

I pondered istanbul escort this for a moment. Here was a gorgeous eighteen year old woman who’d never had an orgasm, asking me of all people to help her with that. On the whole, the absurdity of it all had to be reflected upon for a moment. But, only a moment. There was a woman who needed help after all.

“I mean, yea, sure I’ll help you,” I said. She seemed to visibly relax some as I spoke. “So, were you thinking now, or maybe after some coffee or dinner?”

“No, now works,” she said, and stood up. “I know a spot that will work great. Come on.” She started walking off. I scrambled to get up and followed her.

“Catch up with you all later,” I yelled to my friends. I could only imagine their faces when they saw me walking (or rolling) off with Ashley, but then I was watching her walk so I didn’t much care about their faces just then.


Ashley lead the way through one of the main buildings to the theater department. We accessed the back stage area where a great deal of props were housed, including a conveniently large four poster bed.

“The group is getting ready to do a version of Charlie and the Chocolate Factory,” Ashley explained. “The bed was for their home scene. It’s an actual bed so I think it will work great.”

“Convenient. But won’t it bother you that we’d get it…dirty,” I asked?

“No,” she stated flatly. “The ones doing that scene are all assholes so it’ll be funny to see them lying in our dried mess.”

I couldn’t argue with that fact. Nor was I inclined to do so given what Ashley wanted from me just now. She went over and jumped onto the bed. Leaning back on her hands, she looked relaxed but her face was still nervous.

“So,” she said, “how do you want to begin?”

My skate boots were quick release so I took them off and walked to her. I was trying to remember all the lessons that Amber taught me about pleasing her. She was vocal and authoritative cause she knew what she wanted. Ashley had a goal, but not much of an idea how to get there.

“Well,” I said, “I have some ideas about giving you what you want, but some of it involves me telling you what to do. Do you feel comfortable with that?”

She pondered a moment and sat up straight. “Yes,” she said softly, “I am OK with that.”

“So if I said to stand up and take off your panties, you’d do it?” I asked.

She stared at me for a second, wondering if it was a further question or a command. She smiled slightly, stood up, and made a slow show pulling her dress up over her ass and pulling down her black panties. She stepped out of them and kicked them over towards my skates, never taking her eyes off of me.

“Good,” I said, “now turn around and kneel on top of the bed.”

Still smiling, she complied. She didn’t have to bend over while she got on the bed, but I definitely appreciated having a look at her ass.

She stood kneeling on the bed, looking over her shoulder at me. “Now what?” she asked. In answer I took off my skate boots and kneeled on the bed behind her. My crotch rubbed lightly against her backside, to which she pressed against me slightly. Brushing her hair to one said, I whispered in her ear, “I want you to touch yourself.”

She cocked her head towards me at this command. “Why?” she asked.

“You want me to please you. But I can’t please you unless I know what you like. And I can’t know that until you know that.”

“Now,” I said, moving my hands up and down her naked thighs, “touch yourself. Rub and pinch and push until you feel yourself swimming in your own pleasure.”

I moved my hands up her stomach to her breasts. Finding her nipples I squeezed gently and elicited a sigh from Ashley. Continuing to rub her breasts, she moved her hands towards her pussy. She lifted her dress front until her hands found naked flesh. Her fingers started to explore her wet folds, pinching her clit and rubbing her lips. With one hand she started rubbing small circles at the top and with her other plunged two of her fingers into her pussy.

“Thats it,”, I whispered, moving one of my hands to cup her clenched ass cheek, “touch yourself like you want me to touch you. Feel yourself climbing higher and higher, aching to feel the release you want.”

“Yes,” she whispered back. She started to move her hips back and forth, rubbing her clit faster. “Yes, please touch me like this,” she pleaded.

“Soon enough,” I said. “Now I want you to cum on your fingers. I want you to squeeze your clit and plunge your fingers deep inside you.” She complied and to assist I moved back to her breasts, squeezing her nipples hard through her dress top.

After a few moments her hip movement became faster and faster until she stopped suddenly, still furiously rubbing her clit. “OOOOooooohhhhhh oooOOOOOOOOOHHHH,” she screamed. She collapsed forward, breathing heavily. On all fours with her dress above her ass, she made quite the temping sight. But she asked me for something specific, and I had a plan for how I was to go about that.

She spent a few moments avcılar escort recovering and then flopped down on the bed on her back. She smiled up at me.

“I know I did the work on that, but that was fucking fantastic.” she said between breaths. “It was intimate and hot and I can’t believe I just played with myself in front of you.”

“Well,” I said, “technically you weren’t facing me, and yes, you did do most of the work. But now, I think it’s about time I did what you were asking me to do.”

With that I moved my hands up her shins to her knees, parting her legs. She didn’t resist in the least, and I finally got a good look at her sex.

It was styled with a landing strip. The strip went from the top of her vagina and down the sides of her lips. The rest removed by a bikini wax I would guess. It was a nice sight to behold and I was aching to put Ambers lessons to use on Ashleys engourged sex.

I started kissing her knee lightly. Moving slowly down her inner thigh, I passed my lips over her sweet smelling sex only lightly before moving up her other thigh. She moaned wantonly at my passing it by but I returned with a firm long lick directly up the center, suckling her clit lightly. This brought an excited inhale and more moans from Ashleys lips.

I continued running circles with my tongue as my fingers started probing her depths. Gently at first, feeling her folds give as I entered them, but harder once I found the spot to make her hips buck. I added another finger to my ministrations and increased my tongue pressure, sucking a bit now and again to keep things interesting.

Ashley’s moans increased in both frequency and volume the longer I kept at it. I moved myself with her hip motions in order to prolong her tortured pleasure. Her hands moved to the back of my head, pressing my face down firmer against her pussy. After I thought she had enough teasing, I started flicking my tongue quickly over her clit, pumping my fingers faster and deeper. After another minute the dam finally broke. Her orgasm took her, clamping down on my fingers still stroking insider her pussy.

“OOOOOHHHhhhhhh fuuuuuuuckkkkk Paaauuullllllll,” she screamed. “Fuck fuck fuuuuuuuck”. She lost speech and simply moaned for a bit, pushing my face away from her pussy. I withdrew my fingers gently, eliciting another moan from Ashley’s lips.

Another lesson from Amber; don’t rush and don’t pull out too quick, it could hurt if you do which will kill all your hard work. Thanks Amber.

I laid down next to Ashley, my head on my hand. Her breathing was calming down and she looked at me now with a dreamy haze in her eyes.

“Holy. Shit.”, she said. “I have never had someone do that to me, ever. That was totally amazing.”

She idly drew her hands over her vagina and breasts. “I can see why Amber is so satisfied.”

She rested a few more moments before speaking again. “So,” she started, “I know I said I’d like a couple orgasms if you are up for it. But I feel like I owe you something now too.” She smile as her hands worked their way to my belt. “So, I think I’d like my next orgasm to be from this.”

Her hand worked my belt buckle easily and unbuttoned my skate pants. Since they were so large they were easy to pull off. She was not, however, ready for what was in my pants.

“Holy crap,” Ashley exclaimed. My long, thick, and very hard cock flipped out when she pulled on my boxers. “Amber did not mention this part to her friends.” She ran her fingers over my cock, eyeing it with want and maybe a little nervousness.

“Maybe she thought to leave it as a surprise?” I said, “Amber can be devious when she wants to be.”

Ashley took my heft in her hand, barely getting a hand all the way around my girth.

“When I said I wanted it from this, I had no idea. I’m not sure this is even going to fit inside me,” she said.

“Well,” I told her, “an easy way to find out is to try it out in your mouth. If it fits in your mouth, it’ll fit anywhere.”

She eyed me suspiciously. “Right,” she said, “that sounds like a thing. But then again, I am curious…”

With that she moved towards my cock, licking the tip and the precum now coming out of it. She circled her tongue around the head for a bit before trying to take it into her mouth. She squeezed my shaft gently but firmly as her mouth slowly engulfed the head of my cock. After a few moments, she was taking in not only the head but a few inches of shaft with it.

Her mouth felt amazing on my dick. Her tongue continued to dance around inside while her lips closed around my shaft. She bobbed her head up and down slightly while stroking, which felt like it got me even harder than I already was. After a few minutes she pulled off of me. She looked up at me, smiling. “I guess this will fit inside me. But there is only one way to be sure…”

She stood up on the bed fully and slowly unzipped her dress. She brought it down to her waist and down her hips, dropping it to the bed and then kicking it to the side. I also removed my clothes then, but that was not as tantalizing a sight Ashleys disrobing was.

She şirinevler escort moved to stand over me, my erect member pointing nearly straight up, wanting very much to feel Ashley’s touch again.

Ashley slowly squatted down, taking my cock in hand and lining it up with her entrance. She stroked the outside of her with my head, lubing it up with her ample amounts of sweet wetness. Slowly, tortuously slowly, she squatted down on my cock inch by inch. She came down and went back up and each time came down just a bit further. She could have gone down farther but she was toying with me; the smile on her face as she looked at my reaction confirming it.

After what felt like forever, she sank fully down onto my cock; her knees spread out giving me a glorious view of this fine example of woman. Her pussy was fully wrapped around my cock, spread farther than she’d experienced so far but she seemed to be enjoying every inch I could give her.

“Holy fuck,” she moaned. “I can hardly breathe, it feels like it takes up so much space inside me.” She slowly raised herself up and then sank back down.

“ohhhhhh my fuckkking gooodddd,” she breathed. “I am going to ride this monster until I cum. If you feel like you’re getting close let me know so I can slow down.”

“What if I don’t want you to slow down?” I asked.

She put her hands on my chest. “I don’t want to slow down for you; I want to slow down so I can feel every pulse of your cock when it explodes inside of me.”

I must admit, I nearly came right there from her talk. But I managed to hold on for a time while she rode me for her pleasure. One thing about cheerleading and surfing; it gave her great leg stamina. She rode me at a moderate pace, using her hands on my chest as leverage. I knew she was getting close when her pace increased and one hand went to her clit, rubbing furiously. After a few more minutes she sank completely down on me and ground my crotch for all she was worth.

“oh oh oh oh ohhhhh fuuuuuuck Paaaaaauuuuuuuul” she moaned as her third orgasm took her. I felt her pussy tighten gloriously around my cock as her riding slowed, getting me to the very edge. I reached under her ass, lifting slightly so I had room to work. I then fucked up into her just as hard as she did, at a slightly faster pace but still not hurried. Her moans, slightly louder now were encouraging me onward. Her hands moved to my face, forcing me to look into her eyes as I pounded into her.

“Do it. Cum for me,” said Ashley. “Blast your hot load into me”

That did it. A few more strokes and I came hard into Ashley’s pussy. Once I started cumming she sat down with all her weight, grinding on me, which increased my pleasure greatly.

A few moments later, Ashley sank down to her knees, straddling me and collapsed on top of me. Her breasts felt as firm and soft as they looked when she was riding me. She gently kissed my neck and cheek.

“Thank you,” she said softly. “I needed to know how good sex can be. And that was wonderful.”

“My pleasure,” I managed. I was nearly blacking our from the pleasure of it, and I think perhaps we did for a few minutes.

With out wits about us once more, we stayed cuddled next to each other for a bit longer.

“So,” Ashley started, “have you fucked many girls to be able to make them feel like that?”

“That wasn’t fucking,” I said. “That was love making, or passionate sex, but not quite fucking.”

“Oh,” she said, “and what exactly is the difference between sex and fucking?”

Not sure what it is about a woman asking such a question so plainly, but it had the happy effect of returning my hard on in short order. This effect was not lost on Ashley, whose eyes widened a bit at the sight.

“Its more of a demonstration,” I told her. “Get on your knees and turn around and I’ll show you.”

She smiled devilishly at this command and got on her hands and knees. Arching her back slightly, her ass and still wet pussy made quite the inviting sight.

Lining my cock up behind her, I rubbed the tip around her entrance. I grabbed her upper arms and pulled her upright so I could whisper to her.

“Im going to fuck you now,” I said in her ear, “and when I’m close I’m going to pull out, and then you’re going to stroke my cock until I cum so you can see how fucking excited you make me.”

With that I thrust my restored hard on into her pussy in one thrust. Her wetness was more than enough to make the experience pleasurable for her, but it still took her breath away.

Keeping her upright, I moved my hands to her breasts, squeezing them roughly as I pounded my cock into her with all the animalistic need I had. A satisfying slap came with each thrust of my hips onto her ass, and a satisfied moan came from Ashleys lips as I continued my assault. I was getting close but wanted to make sure she got something as well.

“Do whatever you can to cum,” I grunted in her ear. “I want to feel your pussy squeeze me for all its worth.” Her hands moved down to her pussy then, rubbing her clit furiously up and down. Her other hand went to her labia and stroked them with her fingers, also rubbing the underside of my shaft, which set me off faster. I moaned at this touch which Ashley smiled at. Her rubbing intensified until she lurched forward and convulsed slightly when her orgasm hit. It wasn’t as loud as I’d hoped but her pussy clamped down on my cock, squeezing my orgasm out.

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