Jason And Elaine

RockYourWorld

Literotica Guru
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Mar 9, 2006
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An "Older Woman" Adventure

What was the old line from all those old Penthouse Forum letters – “I never thought that anything like this would ever happen to me!” That had to be what Jason was thinking.

Jason had been to his best friend Austin’s house for family parties so many times, he had lost count. They were a great family, throwing parties of all sizes all of the time. People from all over the neighborhood, as well as Austin’s relatives would all come, making each party a unique mix.

Several things were consistent at all of the parties, and one of those was Austin’s mother’s drinking. It was nothing too excessive, just enough to loosen her up to allow her to have a good time, and maybe tolerate the people she didn’t care much for. Elaine was a great woman. Jason and Austin had been good friends since they were 10 years old, and now that they were halfway through college, Elaine and Jason felt like they had known each other forever.

At this particular party, Austin hadn’t planned on drinking much himself, or even staying up very late. He and his dad were going off on a hunting trip early the next morning, and that morning was coming up fast. Austin had told Jason to enjoy himself, and also told him to take the guest room, saving him a drive home, and went off to bed. The party did thin out a bit, and soon Jason, a few neighbors, a few of Austin’s relatives, and Elaine were left.

Elaine was feeling pretty good. Martinis were her drink of choice, and she had had more than a few. She had just let a few people out the front door and was walking across the living room when she saw Jason.

“Hey, sweety, you still up? Having a good time, I hope?” She stopped right in front of him, looking in his eyes and smiling. Sure she was drunk, but she seemed to be looking at Jason like he was the man he now was, and not the kid she seemed to treat him like sometimes. “I’m glad you’re staying in the guest room…I’d be worried sick if you were driving home after you’ve been drinking.”

“Driving home is the last thing I want to do” said Jason. “Thanks for the guest room. You all have always made me feel welcome here.”

“You ARE welcome here, and you know it!” said Elaine, touching his shoulder. She may have just wanted to emphasize her point, but she kept her arm on his shoulder and began to rub it back and forth, softly, not letting go. Jason stood still, liking the feel of her hand on him, letting her do that as long as she liked. The thought that maybe she liked doing it crossed his mind for the first time, but he quickly dismissed the idea that his best friend’s mom was hitting on him.

The party seemed to break up quickly, as the collective energy seemed to drop suddenly. Soon, it was just the family in the house, with Jason in the guest room. After he had flopped on the bed, he thought about Elaine. He thought about her not as his friend’s mother, but as a sexy older woman, a way that he had never thought about her before. He realized that if he didn’t know Austin, and Elaine was a stranger, he would think she was sexy and hot. Why couldn’t he think of that way, regardless? Those thoughts rattled around in his head until he finally drifted off to sleep.

The next morning, Jason was pleasantly surprised by the fact that he felt pretty good. He had dreaded a hangover, but his head was missing the anticipated drumbeat. He made his way down stairs, knowing that Austin and his dad would be gone on their trip. He had a feeling that is was still pretty early – he didn’t see a clock anywhere - so he figured Elaine might still be asleep. Maybe he could sneak to the kitchen for some instant coffee or juice and not disturb anyone.

But as he walked into the kitchen, there was Elaine. She stood by the sink, her hair clipped up behind her head. She was wearing a t-shirt that she most likely slept in, and immediately, Jason began to wonder if the t-shirt was all she was wearing.

Elaine smiled as Jason entered the kitchen. “Good morning,” she said through a dazzling smile. “I hope you slept well.”

“I sure did,” responded Jason. “Feeling better than I thought I might.”

Elaine turned away from the sink and poured Jason a coffee as he sat at the small table against the wall. “Well, you look good, too, so your day is off to a good start.”

Jason laughed and blushed. “Thanks. You look good, too.” Jason has expected Elaine to dismiss the remark, and maybe deny it with modesty as most women seemed to do at such remarks. Instead, she leaned back on the kitchen counter, crossing her legs. Again, from the way the shirt hung on her body, Jason attempted to peer through his peripheral vision whether she was wearing panties.

“Do you really think so, Jason? Do you really think I look good?” Her smile was even brighter than before. Instinctively, he glanced at Elaine’s legs, then realized that she most certainly saw him doing that.

“Absolutely, Miss Elaine,” Jason said uncomfortably, even though he ventured another look at her legs. “I hope you don’t mind me saying this, but most of Austin’s friends always say he has the hottest mom out of all of us.”

Her smile continued. “And do you agree with that, Jason?” she asked.

He put his coffee cup down. “It was my idea, “he said. “The other guys just agreed with me.”

She walked over to him and touched his head affectionately, leaning down to kiss Jason’s forehead. Whether she realized that doing so exposed her cleavage to a point in space inches from his face, he would never be sure.

“I tell you what,” she said, moving back just a bit from him. “While it’s just you and me here, let’s forget the ‘Miss Elaine’ stuff. Call me Elaine.”

“That’s cool with me,” said Jason. “Just last night as I was drifting off, I was thinking about you – not as my friend’s mom, but as an attractive woman. Seeing you at the party made me think of you that way…nice, funny, friendly….sexy.”

Elaine giggled. “Do you talk to all the girls like this, Jason, you naughty flirt?”

He blushed as he stood up, preparing to excuse himself and get dresses. “No, just the pretty ones.” He went to walk past her, but she reached her arm across his body and stopped him. Instantly, their eyes met. As her hand touched his arm, she turned him toward her. Without saying anything else, she kissed him again, only this time it was full on the lips. Her breath seemed to leave her in a long pleasurable sigh as their lips touched and stayed connected.

“Thanks,” Elaine said softly.

“For what?” asked Jason, staying close to her.

“For making me feel like a woman, and not a mom or a wife. Its nice to be told I’m sexy. I don’t hear that a lot.”

“You ARE sexy,” said Jason. “Why else would you come in here without any underwear?”

Finally, she blushed. “How did you know THAT?” she asked, now looking into his eyes.

“I didn’t” said Jason. “I just took a shot.”

Elaine smiled and reached for his hand. “Why don’t you come with me,” Elaine said, leading Jason out of the kitchen and down the hall to her bedroom. “Your shot hit the mark, so let me give you your prize.”

******

OOC: Thank you for indulging me in this rather lengthy introduction. I started writing it and just couldn't stop.

I am looking for a lady to play the part of Elaine. If you think you might enjoy this, please send me a PM and we'll talk. I'm thinking this role play would continue through their lovemaking, exploring the thoughts that the two people at different places in their lives would be thinking as this happened.

Thanks, ladies. I look forward to hearing from you. :)
 
Elaine

Except for us the house was em pty and would be all day. That stupid husband of mine would rather be off on a camping or hunting trip than making love to his sexy wife, so I had to make do any way I could, and here was this young stud telling me how hot he thought I was.

Last night after he vretired in the guest room I laid next to my snoring husband wide awake using my vibrator on myself, wishing I had the guts to just get up and go down the hall and sleep with Jason.

I had done it before when our son had guests here oivernight, but that was a girl and worth every risk as we ate each other's pussies and made love until the morning twilight cam e, and i slid out of bed and into the kitchen.

When hubby got up and came for his coffee he didnt know the difference as I just told him I couldnt sleep and got up early/

Over breakfast, facing the girl we winked at each other and neither of the guys noticed, but I never saw her again.

Now I had what I wanted- a virile yhoung guy who ws a close friend of my son's, and I knew this one could last a while as I led him to the master bedroom, asnd once inside, kissed him again and let my tongue tickle his lips until his mouth opened, and his played with mine as my arms were around his neck and our bodies in close contact all the way to our feet.

He had gotten dressed, but I never let that stand in the way as I reached down and undid his belt and zipper, and pushed his pants down. I sat on the edge of the bed and pulled him to me, and engulfed his hard cock with my warm wet and willing mouth as his hands played in my hair pulling me tight.
 
Holy shit! Was this a dream? Or was Miss Elaine really sucking my cock.

I looked around and got my bearings. Yes it was really happening. She sucked my cock hard and deep as if she hadn’t seen one in years. Maybe she hadn’t, I don’t know. I thought about how Austin and his dad were away on the trip. Miss Elaine knew this too, and felt comfortable enough that we are alone to pull me in here and give me this unbelievable blow job.

Damn, she felt good. I had heard about guys my age getting with older ladies, but it sure as hell had never happened to me. I felt her hand cupping my balls and I let go of her hair to reach for her t-shirt. I had figured out her secret that she had gone to the kitchen without underwear, so I didn’t think she’d care if I took the shirt from her. It was time to see her tits.

And they were great. She had to stop sucking my cock so I could take the shirt off, and when she did, she leaned back and let me see them. She had a really nice smile, and then moved back to my cock, picking up where she left off.

Now, I’m not going to lie. I wasn’t the most experienced guy in the world, sexually speaking. I had heard that stamina was the result of more and more experience, so I began to think I might be in a little trouble here. I hadn’t had a girlfriend in almost four months. The only “experience “ I had recently was with my own hand, and that wasn’t going to help me here. I may have started to panic a little as I started to become afraid that I was going to cum way to fast. Being here with Miss Elaine was a fantasy come true, and I didn’t want it to end in less than three minutes.

But Miss Elaine had to know she was driving me crazy. She had a perfect body for an older lady, and her tits were bouncing up and down as she bobbed on my cock. She was taking it all in, going all the way down on my cock, and fondling my balls as she did it. My breathing was getting quicker and louder, and so were my moans. I looked down at her as she went crazy on me.

“Shit, Miss Elaine! You’d better stop, or I’m going to explode in your mouth!”
 
Elaine

That was the best idea yet. I wanted his cum in my mouth and everywhere else. The thing about seducing a young guy was his abiility to recover. One reason hubby quit playing with me was he would cum once and couldnt again until the next day, so Jason was the answer.

Slurping even harder I suddenly felt a warm spurt down my throat and swallowed every drop, and smiled up at him.

"Get undressed and lay down here and I'll bring it back to life, and then we will fuck", I said.
 
I was glad Miss Elaine was taking charge. I was just too nervous to do anything other than follow along as I was told. We were both naked now, and her body was so fucking hot, I knew I looked stupid staring at her. Her tits were big and heavy and her legs were long and smooth. When she spread her legs, I took a glance at her pussy. I still couldn’t believe this was happening, and I began to think about what it was going to be like to fuck Miss Elaine.

I had this idea in my head of what it would be like to fuck an older women. Girls my age I had fucked were ok, but to be honest, I was so nervous the whole time, that it took some of the fun out of it. I’m pretty sure the girls felt the same way, even if they didn’t admit it. Being with an older woman, I thought, would be different. A woman like Miss Elaine had been at this a lot longer than me. Over 20 years of experience doing anything had to make you good at it, right? I wasn’t going to be stupid and act like I knew everything when I was doing this with an expert.

At first, I thought cumming in Miss Elaine’s mouth was a bad idea. But when I let loose of my load and she looked up at me as she swallowed it, I didn’t feel so bad. The last time I did that to a girl, she punched me and ran off with her clothes. Miss Elaine seemed to like it.

"Get undressed and lay down here and I'll bring it back to life, and then we will fuck", I said.

At the moment, it didn’t seem possible. When I came in her mouth, the orgasm was great. Would I be able to get it up again? Miss Elaine seemed to think so, and the way she was looking, I didn’t doubt her.
 
Elaine

When he pulled off the tee shirt, I was naked and while he undressed he could see a very hairy pussy with my legs wide open taking his picture. When his pants dropped after the shirt, I took his hand and pulled him to me and again in my mouth, he was hard again just as I knew he would be.

I pulled him down over me as I laid back, never letting his cock escape my hand as i pointed him to its target, and he slid right into me. Tongues playing together, I stopped long enough to asked if he liked what he had seen and enjoyed so far, as his cock kept twitching up in me, and then I said "we are going to do this all day, and almost every day from now on, and I will tell that dumb shit of a husband I have everything and you know what? He will love it"
 
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