BooksieSilk

Jim and Heather #5

By: jim7489

Page 1, Jim and Heather again raise the ante. The time has finally come. This series may be the lone reason for Global Warming! Enjoy....

(Note to readers, Please start reading at Jim and Heather #1, this series will make much more sense! Thank You)

"If I win... I want to pop our friendship cherry!"

Jim looked anxiously at Heather, waiting for her reaction. He was being awfully bold, but it was true. Throughout their friendship as neighborhood pals, school, college and their business careers they had always been best of friends. Heather would be considered a late bloomer, and now a most attractive and intelligent woman. Though in college she was engaged, the true colors of her fiancée eventually surfaced and that was that.

Secretly, Heather may have judged her potential suitors to the standard of her best friend, Jim. For better or worse. Heather was the girl that Jim was closest with also, from childhood through this present time. Sure they'd keep in touch, but often they wouldn't see each, for quite a while; as time, and obligations permitted. Jim cared about her, maybe more like a sister, which maybe leads to as why, the present interactions of late took so long culminate. Jim was doing this as a bet, but heck, truth be said, he did not mind losing to Heather so far! Was this the culmination of a 20 year seduction, or just fate?

To his relief, Heather smiled at him. She'd actually been expecting something like this ever since their bets had started to push more boundaries, "Fine!" and she'd come prepared, "If I win I want to take your virginity."

Naïve, Jim was confused, "Isn't that the same as what I get if I win?"

"Ohhhhhhh Nooooooooo,"

Her devilish grin broadened and she took the item she'd brought with her out of its bag and placed it on the table,

"If I win, I want to pop your cherry with this."

Staring at the HUGE strap-on, HOLY SHIT! Jim came to the sudden horrifying realization of what she meant. Desperately he thought, I'd better win this one...

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

To Jim's utter relief, he did win, (this time, ugh) and he tossed the strap-on at her to put away (in his mind, the thought of it petrified him)! The thing had been haunting his vision the entire time it had been sitting on the table, and now he could finally get it out of his sight. He had a feeling he'd be seeing it again, next round maybe (Heather, turns out was game for almost anything), but for the moment he didn't have to think about it.

Heather laughed, she wasn't too upset about losing, in fact she was kinda excited,

"Let's go upstairs," she suggested, "I'd rather lose my friendship cherry on the bed." She said, having trouble hiding her excitement.

They laughed and teased each other as they went up the stairs, trying to hide their nervousness. In the room, Jim went still, now, very unsure of himself. Looking at Heather, he saw her shy smile and smiled back. Stepping forward hesitantly. He stopped; she closed the gap to only a few inches. Their arms at their sides, just gazing into each other’s eyes, what had been fun competition and mischievousness in the past was now absent. Jim gently pulled her close to him and pursed his lips, time just seemed to stand still. As he lowered his mouth for a kiss, they just hovered, lips just barley brushing. Heather then nestled her head into his neck, holding him tightly, secure, and savoring the moment. She slowly looked, and observed his gaze, gentle, even loving as it were. Bringing her lips to his it started off gently unsure, nibbling, gently just touching tongues. The kissing then began to grow, for what seemed like an hour. Neither wanted to stop, this moment. In all their years, this was their actual first kiss, and it felt sooooo....right.

With hands wandering, touching exploring, each other like the weeks previous, a first had never happened, and neither wanted this moment to end. Inexperienced they were not, but this time might have as well been their first. They'd been getting much more comfortable with each other lately with each other's bodies; they both paused, and then slowly started to undress each other like it was their first time.

Jim gently laid Heather out on the bed, and started to explore her body with his mouth as she ran her fingertips over every part of him that she could reach; the gentle way that she scratched her nails over him, gave him pause, giving him goose bumps up and down his body. Kissing her breasts he sucked her nipple into his mouth, rolling it with his tongue and biting down gently with his teeth. She moaned, with neck and eyes rolling back and legs moving up against him as her hips slowly thrust for the ceiling. Pressing her wetness against his dick, her smooth silky legs caressed his sides. Groaning, he bit down harder on her nipple and pulled his head away so that it stretched and her back arched again as she cried out in pain. It hurt, but it heated her passion too, so that when he did it to the other nipple she arched her back even before he started to pull, her body just begging for it. When both nipples were swollen and aching from the rough attentions of his teeth he started kissing her neck, earlobes, and collarbone, making her shiver underneath him.

Pausing for a moment he asked, "Do we need a condom?"

"I'm on the pill, remember silly?" she smiled at him, "I went on it forever ago"

"I know," he scowled mockingly at her, "I just wanted to know if you wanted one anyway."

Pausing to think for a moment, she shook her head, "No, I want to be able to feel you, and I want you to be able to feel me."

Closing his eyes, he tried not to groan at the way her words turned him on. Damn but she was beautiful, and she felt so smooth and wonderful underneath him. He descended on her for another kiss, his knees urging her thighs to spread and his dick bumping up against her wet slit. As they continued to passionately kiss he brought one hand down to fist his dick, sliding it around the slick surface of her pussy. Her body jerked as it rubbed against her clit, he pressed lower to find her hole. Once he was sure he'd found the right location, he gently but confidently pressed inwards.

Heather groaned into his mouth and he paused for a moment. Only the very tip of his head was really inside her and he was practically sweating with the pleasure and the need... but her comfort first.

"Are you ok?" he asked, slightly worried.

"Yes," she panted, "Just keep going, it’s just been a while, and you’re not small by any means sweetie...just go slow." She said, with a wry smile.

Only slightly reassured he nodded and lowered his mouth to kiss her. Pressing forwards into her slick walls, he thought he was going to die with the pleasant tightness of her. Fortunately she was quickly adjusting to the way he felt inside of her. It was a pleasurable stretching, everything about it was strange and yet exciting. No dildo or vibrator had every felt like this, he pulsed and twitched inside of her, strangely soft and yet incredibly firm at the same time, he fit was so perfect. She clenched her pussy around him to get a better feel of the sensations and he gasped with shock at the exquisite pleasure that shot straight to his balls.

With one quick thrust final thrust he buried himself the rest of the way in her, her back arching up to meet him as he took the final plunge. Gasping, her pussy completely enveloping him, he just held there for a moment, unsure of his ability to move without cumming. Heather was grateful for the momentary pause as her pussy adjusted; he was much wider and much longer than anything she'd ever had. The way he was laying on her made his crotch press up against her clit, and as he continued to lie there she could feel the little nubbin itch with need.

Jim had paused a bit, there was lack of movement, so she started to move underneath him, her hips gently thrusting and her pussy clenching. It was strange and yet familiar at the same time; Jim groaned as her body rippled underneath him, and he put his arms around her back and started reciprocating the thrusting with her movements, gently at first and then slowly harder and harder.

Heather spread her thighs wider as they started to really fuck, wrapping her legs around his waist and her arms around his shoulders, her nails digging into his flesh slightly as his dick parted her pussy lips. She fucked back, rubbing her clit against his groin every time he thrust home. For his part, Jim thrilled to the fact that she was so involved and the way her pussy felt as it convulsed around him every time he got a direct hit on her clit.

Pressing himself against her smooth body, he buried himself in her again and again and again, for what seemed almost an eternity! Moving his hips up and down, rubbing against her pussy lips and clit. Heather cried out and humped back, her pussy quivering in delight. They found new and different ways to please each other; Jim occasionally stopping as the jizz in his balls threatened to boil over. Always Heather would start the movements again and he'd follow, helpless to the pleasure that she was giving him.

For her part, Heather was a little frustrated with the way he was slowing down and holding back now, her pussy was ready to go and she could feel her orgasm fast approaching. She didn't want it slow now, she didn't want him to stop and gather his breath, she wanted him to fuck her hard and mercilessly! An inner instinct told her that hard and fast was what would get her off right now, so the next time that he tried to stop, she didn't. In fact her movements increased and her pussy gripped his dick like a vise.

With a wild cry, Jim realized that he wasn't going to be able to hold out this time and so he started again, pounding at her while she begged him to fuck her harder, and harder, harder than any women had ever let him! They thrust against each other hard, grinding and plunging, until she suddenly went rigid against him and let out a cry of pure pleasure. He buried his dick into her and lost his breath at the intensity of her pussy convulsions. Jim just kept thrusting even harder and harder, his dick, wrapped in her still convulsing vise like pussy. Squeezing him tightly with her legs around him... pulling him even closer against her clit, he ground his crotch against it with amazing vigor. Her pussy rippled, as huge, strong spurts of cum shot into her body. In his now rigid arms and arching back, and loud acknowledgement of the most intense orgasm he had ever had, she shook and heaved, her nails scratching at his back as her orgasm went higher and higher, burning her up inside; his arms now held her tight against him just as her pussy gripped his dick, and his groin was pressed firmly against her clit. She now felt as a helpless rag doll as he thrusted and thrashed groaning ever so loudly, for another ten minutes, maybe longer.

They were both breathless when their orgasmic pleasure finally released them, and Heather had tears in her eyes from the intensity of hers. Jim brushed them away with his gentle fingers as he looked into her eyes and gently kissed her lips; his hips were still pressed against hers and she could feel the strange sensation of his dick, though still but gently pulsing inside her.

They slowly started to kiss again, slowly and gentle, gradually falling asleep in each other’s loving arms.

To Be continued Tomorrow!