(Note to readers, Please start reading at Jim and Heather #1, this series will make much more sense! Thank You)
This time Jim had a little bit of a surprise for Heather, "If I win, I want to watch you masturbate with this," he said, grinning at her startled expression as he put the large dildo on the table. It was a dark tan color, 6" long and 1" around; nothing too hefty although slightly longer than the vibrator she usually used on herself, "It's got a remote," he showed her as he continued to grin.
Heather just laughed at him, "Fine, but if I win, you've gotta eat me out while you masturbate."
Squirming a little at the thought of having to show her just how much she turned him on, for some reason it seemed kinda embarrassing, he nodded. And they turned to watch the swimming. One nice thing about the Olympics, it gave them so many opportunities to bet.
Jim whooped and cheered as two of his picks came in first and second on the 200 butterfly, their chosen race. Flicking off the TV, he tossed the dildo to Heather with glowing eyes.
Just as she had found it exhilarating to strip for him when he was supposed to be masturbating for her, Heather found that her body thrilled a little to the idea of masturbating in front of him. Deciding to give him a little show, she slowly stripped off her shirt and jiggled her breasts at him as she reached back to undo her bra. Rather than taking it off right away, she pressed her arms against her breasts to create a deep cleavage as she leaned forward and let the bra drop from her body. She could tell that he was already hard. Slowly she slid out of her jeans and then her underwear before sitting down and leaning back on the couch. Spreading her legs so that he could see her pussy, she started to toy with her breasts.
Lightly running her fingers over her nipples, she squeezed her aching breasts, bouncing them slightly for him. Pinching her nipples gently, she tugged and her hips responded as she moaned. Jim could see the juices starting to glisten between her pussy lips, and he wanted to dive in there with his mouth again. With one hand she reached down and brushed her fingers over her pussy before putting them up by her clit and spreading the lips with her fingers as she brought the dildo down in her other hand. Rubbing it up and down her wet slit, she lubricated it with her juices as her hips moved in harmony with the stimulation.
Moaning, she started to press it into her hole with each slide, just a little bit, stretching out the entrance to her pussy. Breathlessly excited, Jim pushed the button on the remote that turned on the vibrator inside the dildo to its lowest setting. Heather shuddered as it unexpectedly came to life right on top of her clit.
"Oh God," she said, as she pressed it firmly on the aching bud before running it back down her pink wetness. This time she pressed it a little more into herself, and rather than pulling it back out she started actually working it in and out of her pussy. Jim felt faint with lust as he watched her pussy stretch open for the toy, it’s first few inches buzzing inside of her body. With every stroke its slick shaft pressed more deeply into her, and he turned up the intensity to the second of its six settings and put it on "pulse". Heather gasped as the vibrator started to send the vibrations in short quick bursts, buzzing a little harder than it had before. She started thrusting harder with it, burying its entire length into herself and then pulling it out halfway before shoving it back in. This was a much more high-tech vibrator than the one she'd bought herself at the adult store.
Her pussy slickly accommodated every thrust, her legs spreading even more so that Jim could really see the dildo penetrating her. His dick was throbbing as he wished that it was his dick that was inside of her. Next best thing though... he turned the intensity up to the third level and put it on "wave". Now the vibrator went from the lowest to the highest in quick little waves that flooded through her, teasing and manipulating her pleasure spots. Shuddering, she held it inside of her as its waves got more intense - Jim had pushed it up to level 4.
Suddenly the dildo was out of her hands and moving inside of her, but she didn't protest when she realized that Jim had taken hold of it. Instead she just reached up and started playing with her aching nipples, adding to the sensations that were taking over her body. Twisting the dildo inside of her, Jim attached the clit stimulator to it and pressed it against the little nub. Heather almost screamed with pleasure as the rubbery attachment buzzed against her, she could feel her orgasm rising deep in her belly. Seeing that she was going to be losing it soon, Jim turned it up to level 6 and put it on twist, so that the end of the dildo started turning inside of her and pressing against her g-spot with every rotation.
It looked like she was practically levitating as her body arched and she cried out, her breasts bouncing on her chest as she humped and convulsed with passionate cries, her hands clutching at the pillows. Jim held the toy inside her, slowly lowering the levels of intensity so that her orgasm was long and drawn out but without ever becoming painful from too much stimulation - just like the girl at the store had told him to. When Heather was finally calm, he was grinning at her as he pulled the vibrator from her slightly sore but very fulfilled pussy.
Opening her eyes she looked at him, "Thank you..."
Noticing that he had a slight problem of his own, she grinned and sat up, leaning over to undo his pants. Jim watched in amazement as she voluntarily pulled his dick out and then pressed her mouth over him, sucking him down deep with her hand fisting the part that wouldn't fit. Almost as soon as she'd bobbed her head a few times, his over excited dick throbbed and he came inside her mouth, his hands pressing her down the furthest she'd ever gone as she swallowed frantically.
"Thank YOU," he breathed as she finished.