A Little Story about Jack and Diane Pt. 02

Her efforts were rewarded as Tyler seemed to be sporting a perpetual erection the entire time they were working together. She frequently caught him attempting to discreetly adjust his slacks to hide his bulge.

Tuesday and Wednesday evenings were very much like Monday, except that she skipped the quick masturbation and went right to stripping off her clothes and taking her time fantasizing that the vibrator was Tyler's hard cock sliding up and down her slit and plunging into her wetness.

Wednesday night she had the same dream of being back at the island resort except this time it was Tyler that was on top of her from the beginning. There was no sudden shock to rouse her from her dream, so blissfully it continued uninterrupted.

There was a passionate intensity in how Tyler was fucking her. It wasn't the animalistic, raw sex in the stories she sometimes read on Literotica, nor was it the gentle lovemaking she shared with Jack, this was somewhere in between, and it was glorious!

Her dream seemed to jump around and each time she was in a new position - missionary, doggy, prone and even standing with Tyler's arms hooked under her legs, pinning her against a wall with his cock deeply embedded in her.

The entire time she felt herself on the edge of an orgasm that just kept building in intensity. The dream shifted yet again, and she found herself on her back with her legs pulled up to either side of her head like she was being folded in half. Tyler was above her, his hands on the back of her thighs, pinning her to the bed as he worked his cock into her.

His speed and intensity increased, and she felt like she was being pounded into the bed until, with a final thrust, he slammed into her, shooting his sperm deep inside.

Instantaneously this triggered her own intense orgasm and as her pussy convulsed, trying to milk the cum from the cock that was buried in her, the dream faded, and consciousness slowly returned. As she became aware of her surroundings, her heart was pounding in her ears, and she could feel her pussy spasming.

Was it just the lingering after effects of her dream, or did she actually just have an orgasm? She reached her hand down between her legs and jumped slightly as her finger brushed her sensitive clit. Reaching down further she could feel the wetness of her cum running down the crack of her ass and soaking her panties.

She lay there in stunned disbelief, not once in her life had she ever had an orgasm like this one. She thought only teenage boys had 'wet dreams', yet the proof of hers was saturating her underwear!

Diane quietly slipped out of bed, grabbing a fresh pair of panties from her dresser on her way to the bathroom. As she sat on the toilet to clean herself, the dream replayed in her mind and her fingers involuntarily sought out her still tingling clit.

Afraid of being caught, yet needing the release, she worked her clit furiously with her fingers. In her already aroused state, it took less than a minute until she was once again shaking with another powerful orgasm.

Grabbing a wad of toilet paper, she cleaned herself up, doing her best not to touch her now overly sensitive clit. She pulled on her new underwear and dropped her cum soaked panties in the clothes hamper on her way back to bed, making sure to put them under some of the clothes that were already in there.

The clock on the dresser showed it was just after 2am when she carefully slid back into bed so as not to wake up Jack. Thankful that she still had five more hours to sleep, Diane snuggled under the covers and drifted off, wondering if she might dream of Tyler yet again!

As usual, Jack was up and out of the house when her alarm went off at 7am. How he managed to get out of bed and get ready for the day without waking her was still a complete mystery to her after all these years. Diane made her way to the bathroom and turned on the shower before shedding her sleepwear and stepping under the steaming cascade of water.

She went through her usual routine of shaving her legs and other areas of her body. On their honeymoon Diane found out that Jack loved her pussy being shaved smooth, so she'd kept it squeaky clean for him ever since. When she was done, she stepped out of the shower, dried off, wrapped her hair in the towel and continued with her morning ritual; body lotion all over, brush teeth, apply deodorant and pluck out unwanted facial hair.

With all of those mundane tasks completed it was time for hair and makeup. Diane had straight chestnut colored hair and always viewed it as both a blessing and a curse. It was a blessing in that a quick blow dry and brushing was all that was needed to make it presentable. It was a curse because her hair didn't curl well and the one and only time she tried to get a perm, it was a disaster. So today, like most days, she put her shoulder length hair up in a ponytail and then did her makeup.

Diane walked out of the bathroom and into their large walk-in closet to get dressed. Her ample 32F breasts were pushed up and together a little more than usual thanks to the padded bra she had put on. Her underwear looked good on her, not what she considered sexy, but certainly not granny panties either.

She had paired a loose fitting white silk blouse with a navy blue pencil skirt suit that accentuated her curves nicely. The suit jacket buttoned about half way up causing the lapels to follow the curve of her breasts, giving them the appearance of being even larger than they were. When she was standing, her blouse only revealed about an inch of cleavage, but when she leaned over...well, Tyler would be getting an eyeful for sure!

The skirt was a modest length, coming down to just a couple inches above her knees, with a slit in the back that came up just a little further than any of her other skirts. Diane completed her outfit with a pair of 2" heels.

Standing back from the floor length mirror, Diane was happy with how she looked, she felt sexier than she had in a VERY long time! With a smile on her face, she headed off to work.

The day progressed faster than Diane expected it to and almost before she knew it, it was time to go down and get the last of the reports finished up. Although she knew what remained to be done, she still went down 30 minutes earlier than usual just to look over everything in case she missed something.

The work tables that had previously been covered with stacks of papers had been mostly cleared, replaced by nine stacks of completed reports and 20 piles of the collated report pages waiting to be punched and bound. Diane counted the completed reports twice and then made sure they had sufficient supplies on hand to finish the rest.

Tyler walked into the work room right on time and as they greeted one another, he complemented Diane on her outfit. While she had certainly hoped the Tyler would like her outfit, she was completely caught off guard when Tyler had voiced his approval and found herself smiling and blushing like a schoolgirl! She quickly turned and walked back to the work tables, hoping that Tyler hadn't noticed her flushed cheeks.

Diane had arranged the work table so that Tyler would be on one side, operating the binding machine, while she was on the opposite side, handing him the stacks of papers to be punched and bound. This put Diane in the perfect position to be able to lean forward and give Tyler a clear view down her blouse.

It didn't take long for Diane to see that she was having the desired effect on Tyler, his growing erection wasn't tenting the front of his pants like it had before, this time it was off to the side and she could clearly see the growing outline in his slacks. Surprisingly though, he made no move to hide it this time.

Diane smiled to herself, reveling in the thought that she was still sexy enough to arouse this attractive young man on the other side of the table. Her mind flashed back to last night's erotic dream and in response she felt her nipples harden and a yearning tingle between her legs. She knew she would have another great round of masturbation when she got home from work!

For 10 minutes Diane continued stealing glances at Tyler's erection until she passed him the last stack of papers and just like that, the reports were done.

Looking up, Diane found Tyler staring right into her eyes. Feeling heat rising to her cheeks, she flashed a quick, embarrassed smile and looked back down, unable to hold his gaze. For the first time, she wondered if maybe she had gone a bit too far and Tyler had caught on to what she was doing.

To cover her embarrassment, Diane suggested that they use the remaining time to clean up and put the unused supplies back on the storage shelves.

Because the binding supplies were used infrequently, they were kept on the top shelves, so Diane walked over to move the stepladder to where she needed it and as she walked she could feel her plump labia pressing together, spreading the wetness around and making her panties damp with her juices.

The step ladder was a bit of a ponderous thing that looked as if it had been manufactured back in the 1940's. It had two steps, the top step being more like a small platform, and a safety rail around the sides and front that would keep someone from falling should they lose their balance. Despite its size, the built-in casters made it surprisingly easy to move; allowing Diane to easily place it where she needed to put the supplies away.

Diane stepped up on to the platform and Tyler brought over the three boxes, one at a time. Being only 5'-4" tall, Diane had to stretch a bit to place the boxes up on the top shelf.

As Diane slid the last box in place, she felt someone step onto the bottom step and place their hands on her waist. She quickly spun around, losing her balance a little as she came face to face with Tyler. Diane let out a small gasp as Tyler, with his hands still on her waist, pulled her into him and pressed his lips firmly against hers, snaking his tongue between her slightly parted lips. After only the slight hesitation, and without any conscious thought as to what she was doing, Diane yielded to the lust that had been building up in her for the last eight days and returned Tyler's kiss.

Now that the floodgates of Diane's lust had been opened, her kissing became more fervent as she reached up and slid her hands behind Tyler's head, pulling him in, crushing her lips against his.

Emboldened by her acceptance of his advances, Tyler moved his hands down her legs, hooked a couple of fingers under the hem of her skirt and worked it up over her generous hips. His left hand went back around her waist and slipped into her panties, grasping and kneading the soft flesh of her buttocks. His right hand made its way down between her legs, rubbing her pussy through the now soaked material of her panties, Diane gasped as she ground her pussy against the fingers that were pressed into her cleft. She moaned into his mouth as Tyler pulled her panties down just enough to expose her pussy and pressed his fingers against the naked flesh of her sex for the first time, sliding past her clit and slipping two of his fingers deep into her. Tyler continued to alternate between working his fingers in her sopping wet hole and stroking her engorged clit.

Diane was just starting to feel an orgasm building up when Tyler hooked his right arm under her left leg and lifted. In response, Diane reflexively shifted her weight to her right leg and wrapped her arms tightly around his neck without breaking their kiss. He then hooked his left arm under her other leg and lifted her up, just like he had in her dream!

Stepping back off of the bottom step of the step ladder, Tyler turned and carried Diane over to the table, setting her down on the edge. With her legs spread and Tyler sanding between them, they continued to kiss as his fingers frantically worked to unbutton her jacket and blouse and then reached around her back, trying to unhook her bra.

Diane, guessing that he didn't have much experience with a front closure bra, reached up and unhooked her bra, allowing her still firm breast to spring free.

It only took Tyler a moment to realize what had happened and bring his hands to the front to begin massaging her breast and gently pinching her rock hard nipples. After a few moments Diane broke the kiss and placed her hands behind her to support her as she leaned back, exposing her breast for easy access.

Tyler wasted no time moving his mouth down to begin sucking on her nipples. He moved his right hand down to her pussy and used his thumb to continue gently stroking her clit as he voraciously sucked and nibbled on her hard nipples, drawing groans of pleasure from her lips.

Tyler reached down, grasped her underwear and, taking a step back, started to remove them. Diane lifted her legs, bringing them together and up towards her chest, revealing her pussy to Tyler as he slid the panties up her legs and over her high-heeled shoes, dropping them on to the table beside her.

His strong hands slid down her calves, grasped her behind her knees and spread her legs apart, fully exposing her wet, bare pussy. Tyler wasted no time diving into her beautiful cameltoe pussy, eagerly lapping up her juices as he probed her slit with his tongue.

Diane stiffened and drew in a sharp breath when Tyler's tongue found her clit for the first time. He switched between sucking on her clit and lashing it with his tongue. In no time Diane was writhing on the table, lifting her hips and grinding her pussy against Tyler's mouth as her orgasm quickly approached.

Suddenly Diane reached up, grasped the back of Tyler's head and jammed his face into her pussy, squeezing her thick thighs together as her body started to convulse. With his head firmly clamped between her thighs, Tyler continued working her clit with his lips and tongue, prolonging her orgasm.

Unable to take any more, Diane released Tyler's head and collapsed back on to the table. As she lay there, still in a euphoric daze, Tyler moved up, his face covered in her juices, and kissed her. She eagerly parted her lips and sucked his tongue into her mouth, tasting her juices mixed with his saliva.

They kissed for several moments until Tyler began kissing his way down her neck and back to her breast. Diane closed her eyes and smiled, remembering that this was exactly what she had fantasized about the other day when she was masturbating with her vibrator.

Tyler's lips left her breast and a moment later her eyes flew open, seeing Tyler above her just like in her dream, as she felt his cock sinking into her well lubricated love hole. A groan escaped Diane lips as the entire length of his cock entered her in one long, smooth stroke. It was immediately apparent that Tyler's cock, while not any thicker than Jacks, was at least an inch or two longer when she felt his cockhead nudge against her cervix...a place that only her vibrator had ever reached before!

After a couple strokes, he established a quick pace; pulling out almost all the way and then plunging back in as far as he could go, his groin slapping against her soft ass.. The intense pleasure of his cock reaching deeper than she had ever felt before far outweighed the slight discomfort every time he bumped her cervix. In fact, it seemed to only heighten her pleasure even more!

Because of the height of the table, Tyler was thrusting in a slight upward angle which caused his cockhead to slide against her G-spot as he withdrew his cock and push hard against it when he thrust it back in. Diane, feeling the heat spreading through her body, knew an orgasm was fast approaching as Tyler's cock sped up its assault on her pussy. She went rigid when the orgasm hit and her pussy clamped down on Tyler's cock. This seemed to push him over the edge and with a final thrust, he rammed his cock as deep into Diane's contracting pussy as he possibly could, unleashing 5 or 6 strong blasts of his cum deep inside her. Diane could feel his cock twitching with each spurt inside her as her own orgasm continued.

Her whole body tingled and felt like jelly as she laid on the work table, Tyler's cock still embedded deep in her pussy. She felt Tyler withdrawing his cock and was taken by surprise when he slid it right back in again! Even though he had just blasted her cervix with his cum, he was still hard! Diane's pussy felt like it was on fire as Tyler resumed fucking her now cum filled pussy. Tyler placed his right hand just above her pussy and used his thumb to start stroking her clit. He picked up the pace, his pelvis slapping against her plump ass as their mixed cum made her pussy squish with each stroke.

Diane let out a stifled cry and her legs began to shake as she was hit with her third orgasm of the day! Tyler continued to pound into her for another 30 seconds before slamming his cock into her pussy one last time and releasing another volley of his baby juice right against her cervix. It the back of her mind she was thankful for once that she had gone through menopause and didn't have to worry about Tyler's virile young seed getting her pregnant!

Diane lay there feeling completely spent, her thoughts clouded by an endorphin induced haze as she tried to wrap her mind around what had just happened. Tyler leaned over her once again and gently pressed his lips to hers in a tender kiss. Breaking the kiss, Tyler pulled back a little and stared deep into Diane's eyes for a few moments.

"Thank you, Miss Diane, you are the sexiest, most beautiful woman I have ever known! I have been fantasizing about you since the first day I saw you, and I can't believe this has really happened! You've been teasing me so much since last week that I just couldn't take it any longer. I knew today would be my last chance, so I kissed you, hoping you wanted me to kiss you as much as I did. Actually making love to you was so much better than I ever dreamed it could be!"

Diane smiled, blushing at Tyler's compliments. She reached up a hand and caressed Tyler's cheek.

"Thank you, Tyler, you have made this old woman feel sexier than I have for a very, very long time. I caught you checking me out last week and I saw you trying to hide your erection and that really made me feel sexy, so I decided I was going to tease you the rest of the time we were working together. I'm a little embarrassed to admit that I had fantasized about you too, but I never thought it would go this far!"

Tyler looked a little nervous when Diane said that.

"I'm so sorry, Miss Diane; I really thought you wanted it as much as I did. I never meant to..."

Diane placed her finger on Tyler's lips, "Shhh, it's ok, I'm the one who was teasing you, I'm the one that lead you to believe it was what I wanted you to do."

Tyler visibly relaxed, "Ok, I was a little scared you might have thought I forced myself on you. I would never do that to you Miss Diane!"

"I know you would never force yourself on anyone Tyler, you're much too sweet to do something horrible like that. And as much as I fantasized about being with you too, I should never have let it go this far. It would be really bad for both of us if anyone here at work ever found out about this, so please, please promise me that you will never, ever, tell anyone. Also, please understand that nothing like this can ever happen again."

"I understand, Miss Diane; I promise that I won't ever tell anyone!"

"Thank you, Tyler," Diane said as she pulled him in for a final quick kiss, "Now I think we need to get ourselves cleaned up."

Diane pushed herself up to a sitting position as Tyler stood and withdrew his cock, allowing his cum to run out of her pussy and down the crack of her ass. She had to roll to her side to avoid sliding through the puddle of their combined juices as she hopped off the table.

Diane looked over at Tyler, seeing his still semi-erect cock for the first time...the cock that had just given her two of the best orgasms she'd ever had. A part of her wanted to go over, drop to her knees, and take that beautiful cock into her mouth, sucking it until he shot another load of his young spunk down her throat, but she knew she had taken far too great of a risk already.