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Jenna's Second Lost Bet

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She couldn't quite believe this was actually happening. This had to be one of her fantasies. It was true that she and Jim had been dating now for a little while, but even so, despite everything, she just hadn't considered that a day like this would actually come.

Jenna and Jim were in her room. She had done it again. She had challenged the boy to a game and had lost. Now she was having to fulfill her side of a bet. Last time this happened, she had had to perform a lap dance. You think she would have learned from that. Now, she was stripping in front of him.

Jim sat on her bed, and Jenna could tell he was just as nervous as she was about this. Not only because she was stripping, but the last time they had had a bet, Jenna's mom had walked in on them. This time, Jenna's mom was out, but that didn't mean she couldn't come back suddenly.

Jenna took in a deep breath to calm herself. She was just taking off her clothes. She'd strip, let Jim see her naked for a minute, then dress again before anyone knew anything had happened. That was her plan, anyway.

Jenna grabbed the bottom of her shirt and began to lift it up. Underneath was a black, strapless bra, and Jim's face began to go deep red at the sight of it. Her bra was the sort that was worn simply to cover, not necessarily for support, as it was barely anything at all.

Jenna's hands moved down, grabbing onto her shorts. She unbuttoned them, then slipped them down, revealing the black panties she wore beneath her shorts. She looked again at Jim, who was turning an even deeper shade of crimson. As he stared at her, she felt a sense of excitement. The boy of her dreams, or at least of her fantasies, was looking at her body.

Jenna reached behind her back and unfastened the bra. She used one hand to hold the bra to her chest for a moment before letting it drop to completely reveal her chest. Jenna's body was starting to get hot now. Despite losing clothes, Jim's eyes on her breasts made her yearn for more.

Jenna's hands again reached down, grabbing her panties on the sides. With a good solid push, she slid her panties down, dropping them to the ground. She wrapped her arms around her stomach as she found herself getting even hotter. She could only guess she was likely as red as Jim was.

Jim's eyes searched up and down Jenna's body. She stood there, allowing him to enjoy the view. After a moment, she turned around, allowing him to get a view of her bare back and butt. She even stuck her butt out and wiggled it a bit for a moment. As she turned back, she could see how red Jim had become, and the thought of him began to consume her.

It took only a moment before she stepped up to him. Jenna reached her hands out and grabbed Jim by the wrists. She moved her hands closer until they had placed Jim's hands on her breasts. Jim stared at her breasts for a moment before looking back up at Jenna.

"You like them?" Jenna asked with a smile.

"Y-yeah." Jim began to feel her chest, gently massaging her breasts with his hands. Jenna let a light moan escape from her mouth as her hands let go, settling at Jim's sides. Jim's hands continued to caress Jenna's breasts and she let out another light moan.

With little thought or consideration, Jenna began to unfasten Jim's pants. Jim stared in surprise, but did not speak as she gently pulled his pants down to reveal his boxers. She could see the bulge that had formed, and it enticed her even more.

"You know... we could do it..." Jenna spoke as she grabbed at Jim's underwear. She pulled it down to reveal him and she gently placed her hand on him. "If you want to, that is." Her hand wrapped around him and began to gently move up and down, stroking him.

Jim startled a bit at the sudden advancement of the slightly older woman, but he was having a hard time resisting. Not only did her hand feel good on him, but one of his own hands had moved down Jenna's body and had begun stroking between her legs. She was starting to get wet, and he was starting to get hard.

With no refusal given, Jenna soon brought herself down, putting her mouth around him. She lowered her head, taking him deep into her mouth. Soon, she began to bob her head up and down and Jim began to moan. She continued to bob her head for a moment more before stopping and looking up at Jim. "I like it so far."

"Good." Jim allowed her to continue to bob her head up and down on him for a good minute. He was getting so hard and he wanted more. Jenna seemed to sense this as she pulled off of him and smiled as she climbed onto his lap. A moment later, her hand took hold of him again and she held him straight as she now brought her body down onto him. She let out a light moan as she slid down, pushing him deep inside of her.

Jenna began to rock her body back and forth, allowing him to feel her moving against him. This motion alone caused him to moan heavily, and she wondered how long the boy would last. As she continued to rock her body against his, moans of her own began to escape from her mouth.

The two continued as she rocked herself back and forth steadily faster. However, it did not take long for Jim to become in control. Without much thought, Jim rolled himself on top of her, lying her against the bed. He planted his feet firmly on the ground and began to thrust his body back and forth inside of her.

This sudden motion made Jenna moan louder. She preferred to be on the bottom, and now she was. Jim stopped only long enough to lift her legs up into the air before pressing back inside once again. His thrusts were slow at first, but they steadily built up in speed. Jenna could feel him moving back and forth against her inner walls and it made her moan even louder.

He was good, surprisingly good. He had lasted longer than he had thought and had even become dominate. This enticed her heavily, her moans growing even louder as his thrusts quickened.

Jenna felt the pressure building in her body. She couldn't hold out much longer herself, yet he was still going full force. She wondered how she could be outdone by him until he spoke up, "I-I'm about to cum!"

Jenna couldn't help it. Those were the words that caused her to lose control. She felt her body suddenly release against Jim, and in retaliation, he released into her. The two gave loud moans as their movements slowed until they became steady and eventually came to a stop.