Rory

“10 years! And the worst part is that I don't even know why I was with her!”

Jaslyn snorted a laugh. “I do! She was the first girl to even look at you twice back in high school! It was only natural that you'd want to be with her.”

Rory shook his head in self-deprecation. “Yeah, but 10 years?! Why did I stay with her that long?”

“Because she didn't dump you sooner,” Jaslyn stated with a shrug.

“Ouch! You're supposed to be my best friend,” Rory grumbled unappreciatively.

“Exactly! I've known you longer than anyone but your mom, and I know that you were only with Sarah because you didn't think you'd find anyone else willing to be with you. How many times did I tell you to kick her to the curb and look for someone better?” Jaslyn asked smugly.

“I wanted to marry her!” Rory shouted, then downed his entire tall glass of beer before slamming the empty cup on the table.

Jaslyn sighed and shook her head. “I know I sound like a bitch, but I told you a long time ago that she was only playing with you until she found someone better. That was okay when we were in high school – after all, how many boyfriends did I go through? But now that we're adults, we need to be picky. Don't settle for just anyone; hold out for the real thing!”

“Wait, is that why you stopped dating completely after your breakup two years ago? I mean you always had a new boyfriend every year, and then suddenly nothing!” Rory exclaimed, still baffled by her sudden change in demeanor back then.

Jaslyn nodded, a look of enlightenment settling on her face. “Yeah, I guess it was. At the time, I just thought that I was so hurt by Justin leaving me that I wanted to swear off men for a while, but now that I said, it's true. I got tired of trying everyone in the hopes that they were the right one. Now, I'm just going to wait for a sign from above.”

“What kind of sign?” Rory wondered. Talking about her love life took his mind off of his love life for a few moments.

Jaslyn laughed as she shrugged. “I don't know! Maybe a frying pan over the back of my head?”

“What?” Rory scratched his head in confusion. “Like a caveman? Someone knocking you out and dragging you back to his place?”

Jaslyn couldn't help but laugh so hard that she spit out the sip of beer she'd been taking. “No!!! Who would want that?! Besides... it's not only illegal, but seriously creepy and stalkerish!”

Rory laughed for half a second before his morose mood returned and he sighed. “The worst thing is that deep down, I think I have always known you were right. I would wake up next to Sarah each morning thinking: 'Huh?! She's still here...' That's not what I should have been thinking. Right? Shouldn't I have been thinking something about how beautiful she is or how much I loved her?”

Jaslyn was tempted to smack some sense into him, literally, but she settled for growling in frustration. “Listen, I came halfway across the country to commiserate with you, but if you are just going to wallow in self pity, I'm going home! Rather than whine, why not do something?!”

Rory huffed, more than a little offended by her abrupt attitude. She had been his best friend since they were 9 years old, and she had always been mouthy and rude, so he really had no idea why he expected sympathy and tenderness from her. With a sigh of aggravation, he asked: “What? What exactly should I do?”

“Duh!” Jaslyn snorted impatiently. “A rebound fuck! Go pick a woman for a one night stand, and then screw her until you pass out. You'll feel better in the morning.”

Rory scoffed incredulously. “Yeah right! Like I can just have my pick of any woman here! I've only ever been with Sarah, and I've never even flirted with anyone else!”

Jaslyn growled. “Rory... At our age, it's a hell of a lot easier to get laid! People come to places like this to hook up, and so long as you seem interested, all you really need to do is tell whatever woman you are attracted to that you need a rebound. You'd be surprised at how many of us like knowing beforehand that the guy isn't interested in anything serious.”

Rory looked around with new eyes, and saw that there really were quite a few single women who seemed to be on the lookout for a good man. He met the eyes of at least three, and they each smiled at him encouragingly. With a groan, he returned his attention to Jaslyn. “I'm sorry, but I just can't! I have never liked the thought of having sex with a stranger...”

“Pathetic...” Jaslyn muttered. “Fine, whatever! I guess I'll just go back to my hotel room. If I am not here as a crutch for you to lean on, then you'll have to talk to other women!”

Rory sighed in frustration. “If you leave, then I am just going to leave too. I'm not interested in hooking up with a random stranger just yet.”

Jaslyn downed the last of her beer, thumped the glass on the table, and then belched loudly. “If that's how you really feel, then come back to my room with me. So long as we are getting drunk, we may as well do so somewhere where we can pass out and not get arrested for disturbing the public.”

“Yeah, and we can play cards like we used to,” Rory suggested. “I can still kick you ass in Canasta.”

“Sure sure,” Jaslyn stated, rolling her eyes.

They walked back to her hotel room, then helped themselves to some of the booze she'd brought with her. She knew that he was likely to get wasted, cry his eyes out, and then wake up feeling like a new man. Looking back, she half wish she had called him to come commiserate with her back when Justin broke up with her, but she had been so hurt that she didn't leave her room or talk to anyone for at least a week! By the time she had even told Rory about her breakup, she was already almost over it, and he probably thought that she had taken it as well as all the previous ones in which she had simply shrugged, and then gone out and gotten laid.

Strangely, even though they had enough alcohol to completely overdose on, they just didn't drink much of it. Both sipped on it as they played cards. Ironically, talking about their childhood memories had them laughing. Jaslyn almost felt like this was no different than the many times they had hung out together growing up.

It's amazing how not even a separation of years can change things between us. This made her happy because she'd been a little afraid that they had grown apart in the five years since she'd moved away... to get away from Sarah!

At midnight, she stretched and yawned. It had been a long day, and she was more than ready to kick him out so that she could get some sleep. She grabbed her bag to rummage through it in search of her nightshirt. Rory looked lost in thought, staring at the cards on the table as if they held the answers to all his problems.

“Damnit!” Jaslyn roared unexpectedly. “I forgot my dildo! How am I supposed to get to sleep now?!”

Rory had chosen that moment to take a sip, but completely spit it out; spraying the entire table. “WHAT???”

Jaslyn rolled her eyes. “Oh come on, there's no need to freak out. Of course I have one! I haven't had a boyfriend in two years! In fact, I have a couple of toys to help me sleep.” She was still rummaging through her bag. “But I didn't bring any with me, grr! I probably assumed that I'd be passed out by now and not need anything...”

“Uh...” Rory murmured, not quite sure what to say. They had talked about everything under the sun in their long friendship, but hearing about her masturbation habits at this precise moment was downright flustering!

Jaslyn tossed her bag away with a decisive, growling sigh. “There's no use for it! You are just going to have to be my dildo tonight!”

“WHAT?!?!” Rory gaped at her in astonishment. “You want to have sex with me???”

“Absolutely not!” Jaslyn shouted, mildly repulsed by the very idea. “I just want you to be my dildo while I masturbate.”

“... … ...” Rory stared at her in open mouthed confusion, sort of tilting his head side to side as he tried to figure out how to respond to that. “Uh... How would that work?” He was now looking at her like she was crazy.

“Simple!” Jaslyn stated. “Didn't Sarah ever masturbate in front of you? It's the same thing really, just a bit more interactive.”

“Uh... no... I don't think she did,” Rory murmured, trying hard to remember if Sarah had ever even touched herself when they had sex.

Jaslyn sighed, resigned to explaining things to him like a school teacher. “Well, it's like this; I will masturbate like I normally do, but instead of having one of my toys inside me, it'll be you. You'll do exactly as I tell you to, and then when I am done, you can go home or whatever. But just to be clear, we are not having sex!”

Rory scratched his head. “How is this not having sex?”

“Duh! If we were having sex, you'd be moving in and out of me with the goal of getting off. The way I do it, you'll probably get bored anyway. Trust me, you won't feel like we had sex when I'm done.”

Rory was open mouthed in confusion again, and decided to fill his mouth with the last of the tequila sunrise in his cup rather than try to figure out how to respond to her. Jaslyn stood up and grabbed his hand.

“Come on, this normally takes about an hour, and if you pass out on me, I'll frickin' kill you!” She warned quite seriously.

“But! Wait! Why do you even need help masturbating?!” Rory wondered, dragging his feet on purpose.

“I've been an insomniac since birth; you know that! This is literally the only thing other than sleeping pills or alcohol that gets me to go to sleep,” Jaslyn informed him. “Do you think I would even consider this if it wasn't necessary?”

“Uh...” Rory wasn't sure what to say. He wanted to be insulted, but at the same time, he had never thought about her in this way either, so it was more than a bit weird for him too.

“Strip!” Jaslyn commanded as she pulled her shirt off. She wasted no time getting naked, but Rory took as long as possible to get undressed. He wasn't sure he should go along with this, and more than half of him was screaming to just leave now. Growing impatient – patience really wasn't Jaslyn's strong suit! – she yanked the rest of his clothes off, and then flopped onto her bed.

“Okay, here's how it works, when I masturbate, I stick a dildo or a vibe inside me, and then move it very slowly as I rub my clitoris with a finger. I take a long time to orgasm, and I like to have three O's before I finally call it quits and fall asleep. What I need you to do is pretend to be my dildo,” Jaslyn stated matter-of-factly, much like a doctor explaining body parts to a patient. “You will stick yourself inside me, rocking ever so slightly or just basically staying still. Whichever is easier for you. When I'm done, you can roll over and get yourself off for all I care, but since this is not sex, you are not allowed to get carried away and bang me. Got it?!”

Rory was looking at her like she was crazy again. “Uh... Are you serious? Because if this is some sort of sick joke, it's not very funny!”

Jaslyn sighed impatiently and tugged on his hand sharply enough to pull him onto the bed with her. “Do you think I'd get naked in front of you if I was joking?”

Rory knelt between her legs, but carefully looked her in the eye instead of at her womanhood. “Why would I do this if I'm not going to even enjoy it, according to you?”

“Because I came all this way to help you, so I figure that you owe me,” Jaslyn stated with the same tone of voice that she'd use to say that she had to go to work and needed a ride. She grabbed his hand again, bent all of his fingers closed except one, and then inserted that one inside her. “You feel this spot? When you are inside me, if you feel like rocking just a tiny little bit, this is the spot I want to to grind against.”

Rory gaped at his finger in astonishment, honestly not expecting her to be serious! “Uh, but that's barely inside you... Isn't the G-Spot supposed to be farther in?”

“Yes, but I really like having this spot rubbed,” Jaslyn explained with a shrug. “Trust me, I've experimented a lot, and this is the best place to rub. However, it doesn't work fast, only slow. If you tried to rub it fast, it wouldn't feel good at all.”

Jaslyn looked at his penis, and then smiled. “Good! It looks like you are ready. You'll need to stay kneeling, maybe even sit on your feet. Whatever works so long as you don't impede my ability to rub my clit.”

“Wait,” Rory protested. “So that's it. You just want me to stick myself inside you without any... foreplay or... anything to relax and warm up?”

“Yep! You're ready; I'm ready; let's do this!” Jaslyn exclaimed, eager to get on with this. It was strange to hear a dildo ask for foreplay, which made her chuckle under her breath.

Rory took a couple of deep breaths, still wondering why he didn't just get dressed and leave. She must be drunk to even suggest this, which meant that he would be the bad guy, taking advantage of her when she's not mentally fit. He looked over her body curiously until his eyes returned to hers. She was glaring at him almost murderously.

“What?” He wondered, not sure why she was looking at him like that.

She pointed at her vagina, gesturing impatiently for him to enter her. He looked around to see if there was any alcohol within reach, because he was certain that he needed a stiff drink to gather up the courage to do what she was asking. His hesitation made her growl in frustration.

“Rory! Just do it!”

With another deep breath and then a sigh, Rory nodded. “Okay okay!”

He slowly shifted her legs over his hips and pulled her closer so that he could do exactly as she described. She bounced her hips a couple of times to help him position her correctly, a finger already waiting to get started rubbing her clit. His penis probed her ever so slightly.

“This has got to be the craziest thing I have ever done,” he muttered. “Like this?”

“All the way in!” Jaslyn ordered. “And then, if you rock and grind against that spot I showed you, that would be perfect!”

Rory pushed into her as deeply as he could, and then tried to comply with her request.

“Slower...” she murmured, her finger slowly drawing circles on her clitoris. “Just a warning, because I like how it feels, each time you move, I'm going to clamp down on you, and then release, like this!” Her vaginal muscles rippled around him in a way that felt incredible! “If you get bored, you can just hold still, but please don't say anything, I need to fully concentrate on what I am doing to get to the big O, and even then, it takes a long time. I wasn't kidding when I said this will take about an hour.”

An hour of just basically having my dick inside her??? Rory thought in confusion. He could somewhat understand why she thought he would get bored. Wonder what she'll do if I really do get bored and go limp?

For the next half an hour, Rory rocked so slowly that he really didn't move much at all. Jaslyn had her eyes closed and rubbed her clit as she clenched and unclenched her muscles. Her legs would shake from time to time, and she would moan or pant, but other than that, she was pretty much silent. Suddenly, her inner muscles clamped down on him and got tighter and tighter for several minutes. In fact, her whole body seemed to tense up!

Rory was surprised that he suddenly felt like cumming, but closed his eyes and concentrated on other things until the feeling passed. As he did so, she started grunting and gasping, her body shivering as her muscles rippled uncontrollably along his shaft. He groaned in surprise, nearly losing his load.

She rode out the orgasm, and then purposely took a few calming breaths before resuming the circles her finger made. “That was one,” she whispered to herself.

Rory couldn't help but smile at her, even though she wasn't looking at him. Her hips ground into him, forcing him to basically hold still in order to retain his balance. Her muscles felt tighter than they had been to begin with, and she continued to purposely ripple them up and down his shaft. Her finger made her moan a bit more frequently, and her legs trembled nearly the entire time.

About 10 minutes later, Rory was sure that he must be oozing tiny drops of cum inside her. It was so very strange to him that he wasn't really doing anything at all, and yet he was ready to cum at the drop of a hat! He had to stop staring at her lush body, close his eyes, and focus on not pumping her full!

This time, her orgasm arrived with a strange choking sound – like she was holding back a squeal of pleasure. She started whispering: “Oh God Oh God Oh God!” repeatedly like she was panicking, but her vagina felt like it was trying to milk him for all he was worth.

Rory gasped softly, wondering how on earth he was going to hold out much longer. He started thinking about how unfair this was to him. She was using him as a sex toy – expecting him to have the stamina to last until she was done – and yet, she didn't care in the slightest if he got off. At this rate, he was going to have a painful case of blue balls when she was done!

Once again, she rested for a few seconds to relax just a bit before muttering: “That's two,” and resuming her quest for three orgasms.

This time, it took less than five minutes for her to ascend to heaven. Additionally, this one was nearly twice as strong as her previous orgasm. She dug her nails into his legs and held on for dear life as she squealed and arched her back. Rory held her hips firmly, praying for a miracle to help him, but he just couldn't stop himself a third time. With a soft grunt, he flooded her, his climax so intense that he felt like the whole world was spinning!

They both held still and panted for a few minutes, until Jaslyn laughed softly. “Okay, I'm sleepy now!” She opened her eyes to look at him for one second. “You can get out of me now, and then jerk yourself off if you want. I don't think I would even mind if you passed out next to me... Just don't touch me in the morning if you wake up before me.”

“Uh...” Rory murmured, the sound rolling out of his mouth for at least 10 seconds. “Jaslyn... I uh... I –”

Jaslyn grew impatient with his hesitation, wanting him to get out of her so that she could go to sleep. She grabbed hold of the headboard and used it to wiggle herself off him. “Rory! Just get out!” She gasped incredulously as she felt a river of fluid gush out of her. “You didn't!”

“That's what I'm trying to tell you,” Rory mumbled. “I came inside you. I couldn't help it!”

Jaslyn was tempted to kill him, but her lethargy was too powerful to ignore. Forcing herself not to scream at him, she sighed. “Whatever... just... just go to sleep. I'll take care of it in the morning...”

Rory lay down next to her, his mind spinning in utter confusion. In a way, he really didn't feel like they had had sex, but in another way, he felt like they had just had the most incredible sex of his life! His thoughts whirled around and around his head until he gasped in sudden clarity! I'm not thinking about Sarah!

Now it made sense to him how a rebound fling could help someone get over an ex. This revelation helped him realize that he didn't suddenly have feelings for Jaslyn, however... He did wish she would let him have proper sex with her. What she had insisted upon was not only a tease, but really unfair to him.

With a long exhaled sigh, he let go of his thoughts and drifted off to sleep.

Okay readers, I need to know what you think! Is this believable to anyone but me? I can totally picture what happened in my mind, but I'm not sure that I was able to convey it accurately, lol. Anyone else ever tried this???