Halloween! Let's Pick a Pumpkin

"You want to do what?"

"Let's go to that farm out on 8th line to pick some pumpkins! It IS Halloween on Saturday," said Jill.

"Can't we just buy some at the store?" David asked with a perplexed look on his face.

"NO; this will be more fun I promise," Jill said, kissing him on the lips before getting up from their bed and heading to the shower. "This is something I do every year and carving pumpkins you have picked yourself is much better! I need to get the perfect shapes and sizes for what I want to carve."

"You carve pumpkins for Halloween?" David exclaimed, "Please tell me you have not been hiding your inner Martha Stewart for the past 6 months!"

"NO silly... I just love Halloween. Decorating the house, finding the right pumpkins and carving them, dressing up, giving out candy to the kids, dressing up, the parties later on in the evening after the candy is all gone, did I mention dressing up?" Jill smiled back at him before going into the bathroom, the shower drowning out his reply which was a nervous laugh!

David and Jill had met at a party during the May long weekend. It was one of those 80's retro parties where everyone dressed up as their favourite 80's rock star, only music of the 80's was played all night and drinks that were popular then were served. "OH!" David said out loud with a smack to the forehead, he finally got the 'dressing up' comment! How could he have not figured this out by now? At the party, Jill had on the full Madonna regalia... bra on the outside, short skirt with leggings, hair teased to its full height with headband, jewellery everywhere. It had taken 5 minutes just to get all those damn necklaces off and her arm bracelets rattling while she jerked him off had been quite the distraction.

There were other times since then that she had dressed up for him, like the night in July when they played doctor and nurse. He really liked the night she dressed up like an escort and he picked her up at a hotel bar downtown. Now he realized why she has a Wonder Woman costume in a garment bag in the back of her closet and why, on more than one occasion, Jill would show up at his place from work in one of her conservative designer suits with expensive, tantalizing lingerie underneath complete with garters to hold up her silk stockings.

"Your turn," Jill said as she walked back into the bedroom naked except for the towel around her hair.

"Come here and fuck me," David said as he pulled back the covers to reveal his hard cock, ready for action. He had been stroking himself as he thought of the last time she dressed up for him, Jill had been bent over the back of his couch, skirt pulled up over her ass, the green garter straps standing out against her pale skin. She had taken off her panties before arriving at his place, knowing her outfit would have him at attention as soon as he heard her stiletto's clicking on the tile. Jill had wanted him to fuck her immediately; she'd missed everything that was said in meetings all afternoon as she daydreamed of his urgent hardness driving into her.

"No, you can wank off in the shower," she said, smiling, "but hurry up; we don't want to get there too late. All the good ones will be taken."

"It's 7 on a Sunday morning! How will they all be gone soon?" David teased knowing he would get nowhere with his argument.

"Today is the first day and it opens in an hour!" Jill replied, throwing her wet towel at him. "Get up oaf; I will buy you a coffee along the way!"

* * * * * * * * * * * * *

"Is this the farm?" David asked for the third time.

"Yes, yes! This is the right one," Jill nearly squealed. To David, she seemed like a kid in a candy store all jumpy and fidgety, wanting to get to the goodies as if they would suddenly vanish.

Getting out of the vehicle, David was surprised by the size of the place. There were at least 100 acres of pumpkins, the vines still vibrant green in the morning sunshine, the orange pumpkins barely visible through the thick foliage. The few pumpkins he could see dotted the landscape for what seemed like miles. In reality it wasn't quite that large, but to a kid from the city, any patch of grass bigger than a postage stamp seemed huge.

"Come on lazy," Jill said grasping his hand in hers, pulling him along the tractor path to the outer reaches of the field.

"I have been coming here at least 10 years. They have the best pumpkins. The freaky shaped ones are in that far back corner, so that's where we're going. I don't want those typical round ones everyone looks for. We're looking for three: one very oblong, one shaped like an egg and one that is very deformed. You can carry all that right?" she said laughing and giving his bicep a squeeze.

"Well, yeah, sure! Boy, you've really given this a lot of thought already. What are you planning to carve in them?"

"I'm not sure, yet. I like to get them first and see what inspires me." She paused, seeming a little serious for a moment. "Thank you for indulging me this David. I know this probably isn't what you might think of as fun for a Sunday morning. It really is my favourite holiday and you will find out just how favourite it is! I promise to be very good later!" Jill said with a sly smile before giving him a peck on the cheek.

It took them about 15 minutes to get to the back of the field. They stopped and looked at various pumpkins along the way as Jill reminisced about Halloweens past and the various things she had carved into the pumpkins. She did not tell him about the time she was emptying out a particularly large and very full pumpkin. As she pulled the mushy insides out of the pumpkin with her hands and felt the gooeyness between her fingers, she became so aroused she needed to pleasure herself right then and there. Leaning against the counter, two fingers burrowed deep in herself, by the time she finally came, Jill had been coated in the stringy mess. It was during the clean up in the shower later that Jill decided it was time to shave all her pubic hair, to finally go totally smooth and remain that way.

"Ok David, remember what I told you about walking around the vines. Be careful not to step on any because I don't want you to be a pumpkin-killer."

"I think I see a weird shaped one over there!" David said, getting into the fun of the search and having more of an understanding why this was important to Jill.

They made their way to the pumpkin and sure enough, it was to Jill's liking. David picked it up and carefully navigated his way back to the main tractor trail to place their find there. He'd managed to avoid killing any pumpkins.

Jill squealed in delight as she found a perfectly oval pumpkin. Holding it up, David could see why she was happy with it but also noticed her stiff nipples poking against the light sweater she was wearing.

David made his way to where she stood and collected the pumpkin from her but not before planting a kiss on her lips. Their tongues intertwined momentarily before Jill broke the kiss to resume her search.

The careful walking down the rows and examination of pumpkins continued for another 15 minutes before Jill proclaimed she had found the last one. David walked over to her, preparing to pick up the pumpkin and place it with the other two on the trail but Jill had another idea. Jill pulled him into an enthusiastic hug and he could feel her gratitude to him for having gone along with her pumpkin quest. There was more to it than that, though. She kissed him hard on the lips, her tongue plunged into his mouth, searching and finding his tongue. He captured the intruder, sucking on it and playing with it until Jill moaned and pressed her body against his. They kissed this way for a few moments, enjoying each other in the morning sunshine. Jill's hand then slid down David's body between them to rub the front of his jeans. His cock was hardening with the kiss but Jill's attentions brought him quickly to full tumescence.

"I want you to fuck my mouth David. Let me suck you off out here in the middle of this field!"

"Um, ok," David smiled as he replied. David never ceased to be turned on and amazed at her adventurousness. No where seemed off limits to Jill, and he loved to indulge her if only to find out what next!

"Lay down on the ground, the vines are still high enough to hide us from being discovered. David, I did my hair in two braids for a reason this morning. I want you to hold them tight and fuck my mouth. Use my mouth until I can feel your cum is spurting down my throat."

David could only nod obediently as he lay back on the ground, unzipping his jeans and pulling them down enough to release his cock to the open air. If he had known this morning that he would be getting a blow job in the middle of a farmer's field David would likely have been nervous about getting caught. With Jill, all of that was gone and he simply enjoyed the chance to try something new that pushed his boundaries.

Jill followed him down amongst the pumpkin vines. They simply vanished to anyone who might have been looking from the barn. Jill eased his clothing off, cradling his cock in her expert hands. She brought her mouth down over the bulbous end, sucking on it as she released her hands and took nearly all of him in to touch the back of her throat. David had never fucked Jill's mouth before. She had given him lots of blowjobs, but this was a different request. He had wondered about the braids in her red hair since normally, on the weekend, it was a single ponytail either high up on her head to poke through a baseball cap or low on the back of her neck. He reached up and grasped them both, holding tight to immobilize her head. He looked down and met her eyes to make sure this is what she wanted. David could see that her eyes were smiling, twinkling with delight that her plan was coming together and she was getting what she wanted. Jill often told David about her love of sucking cock, feeling the hardness throb in her mouth and throat, tasting the salty cum of a man and exulting in her power over him as she controlled the timing of his release. Today he understood that she really meant it.

David started slowly at first; unsure really of how hard or fast she wanted it. He obviously did not want to hurt her but she urged him on, with her eyes, with her mouth and soon he was thrusting into her. He looked down to see her eyes closed, enjoying the experience, her lips previously covered with gloss were now wrapped around his thickness; perspiration formed above her lip as she concentrated on giving him pleasure. David could feel her tongue circling the head of his cock at the end of each thrust; he could feel her mouth opening, relaxing and his penetration getting deeper and deeper. He knew by the time he shot his load, his entire length would be in her, the head of his cock well into her throat.

Jill opened her beautiful blue eyes to look up at him and to smile. It was the last thing he saw before closing his eyes and growling out to her, his entire body exploding in orgasm. He pulled on the ponytails one last time; his cock fully engulfed by Jill's wanting mouth and throat, his semen pulsing out the tip, sliding down her throat as his body went tense with the climax.

Jill kissed his lips lightly, her body resting on top of his. David did not remember releasing her or her climbing up on him. Could he have passed out for a moment?

"That was fantastic, thank you," Jill said to him as they kissed one last time. She got up and started towards the main trail, waving to one of the workers to bring the tractor and wagon around to collect the pumpkins.

David lay there for another minute collecting himself and zipping up. As he made his way towards Jill, struggling under the weight of the third pumpkin he had to smile and wonder, "What more Halloween surprises did Jill have in store for him?"