Tom's Adventures Ch. 05a

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Tom & Jessica go on their first real date.
5.7k words
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Part 6 of the 7 part series

Updated 10/17/2022
Created 08/20/2006
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Chapter 5a: The Date

Tom was nervous. His hands were damp with sweat and his eyes were darting from side to side. As he stood there, his feet were fidgeting. It was early September, so the heat wasn't what was making him sweat.

Tom was standing on the side of the basketball court of the university that he attended. He stood about 6 feet tall and was a forward on the team. Because he was an athlete he had a well toned body. His dark blonde hair was cut short, above the ears. Basketball practice had just ended, but that's not the reason he was sweating.

The women's basketball team had just taken to the court for their daily practice. Tom kept looking for one lady, but didn't see her. Suddenly, he saw her appear from the locker room on the opposite side of the court.

Jessica came running out in shorts that hung down to her knees and her practice jersey. Her dark brown hair was pulled back into a pony tail. Her six foot body bounced as she jogged onto the court. Her athletic body was well toned and muscular. Her breasts hardly bounced due to the sports bra she was wearing. Tom started fidgeting more and more.

He hadn't been able to stop thinking about Jessica since the night his sister brought her over for the poker night. So far, to his knowledge, she's the first woman he'd had intercourse with. To his knowledge, Jessica was the one that he had laid when the lights were turned out and the women screwed the first guy they bumped into.

"OK, here goes!" Tom thought to himself as he jogged out onto the court towards Jessica. A lot of the ladies looked at him and whistled or cat called. Tom didn't hear them... he was on a mission. "Um... Jess! Can I talk to you?"

"Hi, Tom! Sure!"

"I was... um... wondering... do you want... would you... geez... like, um... doyouwanttogooutonadatewithmesaturday!" He blurted.

"Excuse me? What did you just say?" Jessica asked with a smile.

Tom took a deep breath and closed his eyes. When he opened his eyes, he looked into hers. He saw the blue of her eyes and said, "Would you go out on a date with me this Saturday? I'd like to spend some more time with you." Tom felt his face blush as he said this.

"I'd love too!" Jessica said. "What would we do?"

"I... um... don't know... I'll think of something," Tom said.

Jessica leaned in and kissed Tom on the cheek. "I look forward to it. Call me and let me know the details." She turned and headed back to practice as the coach blew her whistle. Tom turned and headed into the locker room. Several days later....

Tom climbed into the shower. He put his hand under the water and then put his entire body under the spray. He heard the door to his sister's bedroom open. The bathroom separated their rooms. Both he and Suzie attended the local university and still lived at home with their parents.

"Hey! I'm in here!" Tom shouted.

:"Not like we haven't seen each other naked, bro! Geez! I just have to use the john," she said. Tom looked through the clear shower curtain and saw his sister yawn as she sat down on the toilet. Tom lathered up his hair with shampoo.

His sister finished and as she stood up, Tom saw her reach for the handle on the toilet. "DON'T YOU DARE...." It was too late. The toilet flushed. Tom jumped back in the shower as the water became scalding hot. His footing slipped, and he landed on his back in the bottom of the shower, his head hitting the side of the bathtub. Tom screamed. The pain in his head, combined with the scalding water raining down on him was too much pain.

Suzie jumped into the shower, her nightshirt still on, and helped her brother get up. "Slowly! You really hit your head! How do you feel?"

"I feel fine now," Tom said. He looked up and her night shirt was basically transparent due to the water hitting it.

"I can tell," Suzie said. She looked at his cock and it was becoming more and more erect. Tom stood up and his body pressed into hers. His cock was touching her stomach, as it was now fully erect. Tom looked into his sister's eyes. She looked up at him and smiled. "Well, since I'm already wet, I may as well shower too!" She took off her now soaked nightshirt and tossed it over the shower curtain. She stepped back and tilted her head and brushed her blonde hair.

As she shampooed her hair, she grabbed Tom's cock and pulled him towards her. You better rinse that shampoo out of your hair, bro. If it dries, it becomes a pain." Tom and Suzy moved around; their wet, naked bodies rubbing up against each other.

Suzy giggled. "You better save that for Jess. If you can't get it up tonight on your date, she'll be disappointed." Suzy grabbed her loofa and started soaping up Tom's chest. She got down on here knees and washed his legs. She slowly worked her way up his legs and when she reached his crotch, she paid extra special attention to his erect cock. "We gotta get this extra clean for her."

Suzy leaned forward and took the tip of Tom's cock in her mouth. "Uh, sis... that feels so good," Tom moaned. Suzy licked the side of his cock and then took the tip back into it. She then stood up.

"Wha..." Tom looked at her shocked.

"Sorry, bro," Suzy said as she stepped out of the shower. "You gotta save it for Jess. She's been looking forward to this date since you asked her earlier this week."

"Great. I get to go on the first ACTUAL date of my life with blue balls," Tom groaned. He turned and rinsed the soap off his body.

A few hours later...

Tom was nervous, again. He was standing in the lobby of the girls' dorm, waiting for Jessica to come down. He had in his hand a single red rose. He was dressed in cacky pants and a red button down shirt. Jessica came walking into the lobby. She looked stunning.

Jessica was wearing a yellowish sun dress and white sandals. Her light brown hair was hanging down to her shoulders. She had a pair of sunglasses on the top of her head. Over her shoulder was a large bag. She walked up to Tom. Tom took the bag from her. He held her hand as he took the bag and slung it over his shoulder. He leaned over and brought her hand to his lips and left a small kiss on the top of her hand.

As he stood up, he presented the rose to her. "A beautiful symbol for such a gorgeous lady. Unfortunately, the symbol doesn't come close to matching your beauty."

Jess giggled as she took the rose. "How sweet! Thank you. Nobody has ever given me flowers before."

"Really?"

"Well, my dad has on my birthday or stuff like that, but never a non-relative."

"I take it the bag has the change of clothes I instructed you to bring?"

"Yeah, I'm curious as to what you have planned. I'm kind of nervous bringing an overnight bag on a first date, if you can call this our first date."

"Oh, this isn't an overnight bag, at least that's not the intention I had in telling you what to bring." Tom took her bag and led her outside. He walked Jess around the front of his sister's mustang convertible and opened the passenger door for her. As she got into the car, he looked at her long, muscular legs and got a real quick glimpse between them. She wasn't wearing any underwear.

Tom closed the door after she was in the vehicle. As he walked around the back, he tossed her bag into the back seat, next to a bag he had packed for himself. He got in and started the car.

As they pulled out of the university, Jessica put her hand on his thigh and said, "So where are we going?"

"Well, first I thought I'd treat you to a beautiful lunch followed by something most city-raised-girls don't get to experience."

"Ooo! Now you've got my attention!"

As they drove to their destination, they talked about classes and basketball. Jessica sat back in the seat and let the sun bask down on her. She noticed they were now in farmland. Wheat fields and corn fields wherever she looked. There was the occasional cattle pasture or beautiful old farm house that they passed. The radio was set to a country station. Songs like "Angels Among Us" or "Butterfly Kisses" kept playing over and over.

Finally, Tom started slowing the car down. As they turned off the road, Jessica saw a sign that said STATE PARK. Tom stopped the car under the vestibule of the main lodge. "Wait a sec," he said as he jumped out of the car. He ran around the front of the car and opened the door for Jessica. As he took her hand and assisted her out of the car, he tried to sneak a peek at her bare pussy. No luck.

As she stood up, Jessica gave Tom a quick peck on the cheek. "This is exciting. I haven't been on a real date since my senior high school Prom." As they entered the lodge, a teenager gave Jessica a once over and Tom handed him the keys to the car. The teenager winked at Tom and Tom just smiled.

The couple walked through the lodge and into a restaurant at the back end. There was nobody else in the place. A waiter came over and escorted them outside onto the patio. Tom pulled Jessica's seat out for her and assisted her with pulling it up to the table. Then he sat down in the seat next to her.

They were sitting along a rail. As they looked over the rail, they noticed that they were out over a body of water. Ducks were swimming towards them, obviously used to people throwing food to them as they ate on the patio. Either side of the patio was covered with trees. As they looked out towards the water,

The waiter came back with glasses of water and a bottle of wine. "The manager has already ordered for you. Your appetizers and entrees will be out shortly," the waiter said.

"Wow. That's surprising," Jessica said as the waiter walked away.

"Not really. My Aunt is the manager of the lodge. My uncle is the chef here at the restaurant. This is the best food in the state."

The couple sat there and drank wine, ate sushi and calamari as appetizers. For the main course, they were served a sampler plate of asparagus, salmon, trout, spiced chicken, and mozzarella sticks.

As the bottle of wine was finished, Tom's aunt and uncle came out and introduced themselves. After a few minutes of talking, Tom's aunt said, "Tom, you better go change. Ricky will be here for your afternoon fun."

Tom stood up and took the back of Jess' chair and pulled it away from the table as she stood up. Tom took her hand and led her back through the restaurant. As they exited the restaurant, the teenager that took the car keys from Tom earlier walked up and handed Tom the bags that were in the back seat. "Jess, this is my cousin, Ricky."

After the introductions were finished, Tom led Jessica to the women's' restroom. "I'll meet you back out here after you get done changing." Tom then went into the men's restroom and changed into a pair of jeans and a red t-shirt. As he walked back out into the lobby, Jessica was already changed. She was wearing a pair of form fitting jeans and a spaghetti strapped top. Her hair was pulled into a pony tail.

Ricky came up to them both and took their bags from them both and led them outside to the front of the lodge. Where cars usually pull up, there were three beautiful horses tied to a hand rail.

"Oh wow! I've never been horseback riding," Jessica said.

"Well... this is just a part of it," Tom said.

Ricky put the bags down and led Jessica over to one of the horses. This is No Cents. She's our most laid back. Ricky showed Jessica how to approach the horse. Jessica stood there petting the horse's nose as Ricky fed it a sugar cube to keep it calm. Ricky then gave Jessica a quick verbal lesson on how to ride.

"Ready to try it?" Ricky asked her. Ricky then helped her mount the horse. As she tried to get her leg over the saddle, Ricky put his hand on her ass and "pushed". Tom noticed this and grinned as he thought Ricky kept his hand there a bit too long.

"Is this jealousy I'm feeling," Tom thought to himself as he mounted his own horse.

Ricky led Jessica's horse over to the grass and handed the reigns to her. She took to it naturally. She walked the horse around the parking lot and surrounding area. Ricky and Tom kept their horses close to her that they could talk and possibly rescue Jessica should she have any problems.

"It's almost six. You guys better get on the trail," Ricky said. "Mom packed a picnic snack and stuff in the saddle bags. I'll see you at home later." Ricky then turned his horse and rode out towards the road that exited the state park.

"Home?" Jessica asked.

"My aunt and uncle have a ranch that borders the state park. They lease the land to a guy who trains horses. C'mon. We don't want to miss the sunset in a few hours."

They rode along the trail. Jessica took to riding a horse naturally. The trail crossed streams, went down into gullies and back up. They occasionally had to duck in order to avoid hitting their heads on low hanging branches. They talked, and laughed as they rode.

Occasionally, Tom found himself behind Jessica. He would stare at her shaped ass bouncing up and down in her saddle. More than once he had to adjust himself in his saddle because of the hard on stretching against his jeans.

After a few hours of riding, the trail widened so they could ride side by side. Tom looked over at Jessica and noticed that the strap had fallen down from her shoulder and her breast was exposed. Tom was staring at the breast and wasn't watching the trail. As the horse entered a small clearing, Tom's head hit a low hanging branch and he found himself sprawled on his back for the second time that day.

Jessica jumped off her horse and ran over to Tom. As she kneeled down, he looked up at her and smiled. "This is the second time today that I've hit my head and seen beautiful women looking down at me. Are you angels?"

Jessica giggled and said, "Well you know how the song goes... 'Angels Among Us'". She took Tom's hand and tried to pull him up. He pulled her down onto the ground. She fell on top of him. Their mouths found each other and they enjoyed a long, passionate kiss.

As the kiss broke, Tom remembered the horses. "We gotta get the horses before they wander off!" Tom jumped up and hustled over to get the reigns on both of the horses. They were in a small clearing. There was a small sand beach along the lake, and the trees were so thick, it was hard to look into the woods. Along one side of the clearing, there was a wood rail. Tom took a couple pieces of long rope and tied the horses to the wood rail. He then took a bucket that was in the trough and filled it up with water from the lake.

Tom then took the saddles off the horses and emptied the saddle bags. In one of them were a few blankets. One of which he spread out on the small beach. Next to the blanket, he laid a bottle of champagne and a few bottles of water.

Jessica went to the water's edge and started washing off a bit of dirt that was on her arm from when Tom had pulled her down to the ground. Tom was looking at her bent over. The top of her ass crack was peeking out of her jeans. The strap was still low on her arm. She looked up and saw Tom staring at her. "What?" she asked.

"I'm just admiring how cute you look," he said.

Jessica then started to stand up. She lost her balance and fell face first into the edge of the water. Tom ran over to her. She rolled over and looked up at him. He was standing next to her, the water up to his shins. She was completely soaked.

"Are you OK?" Tom asked with a smile.

"Yeah, I just lost my balance. But now I'm all wet."

Tom offered his hand and pulled her up. The tank top was almost transparent now. Tom could see her nipples sticking out. The water was cold on his feet and shins. Tom led her up to the blanket and sat down on the edge. He started taking off his socks and shoes.

Jessica then said, "What am I supposed to do? I don't have another change of clothes."

Tom grinned at her. He stood up and walked over to her. He put his hand on her chin and leaned in and kissed her. She moved closer to him and wrapped her arms around his neck. His arms went to her back. As their tongues met, Tom started to lift her top. They broke the kiss long enough for the top to slide between them.

As Tom threw the top towards the blanket, she pulled him back towards her. He felt her hard nipples press into his chest. His hands explored her back and they continued to kiss. Slowly, he worked his hands down to her waist. He put a hand into the back of her jeans as the other hand grabbed her butt through the wet jeans.

Jessica pushed Tom back a step. She had an evil looking grin. She slowly unbuttoned her jeans and pushed them down. She struggled a bit as they were wet and was tight on her to begin with. As the jeans cleared her pubic bone, Tom noticed that she was still shaved. Water dripped from her bare pussy. As she pushed the jeans down, she again, fell to the beach.

Tom went over and kneeled down next to her. Jessica straightened her legs out and Tom took hold of the bottom of the pants. He pulled and the jeans came off without a problem. Tom tossed the jeans towards the blanket. He offered a hand and pulled Jessica back to her feet.

She wrapped her arms around his waste and pulled him to her. They continued their passionate kissing. Tom broke the kiss and started nibbling on her left ear. Her nose was at the base of his neck. She enhaled the aroma of his scent. For some reason, the mixture of cologne and his sweat drove her nuts. She stuck her tongue out and just barely touched his skin. Tom pulled on her earlobe with his lips. She let out a moan.

Tom then moved down her left cheek just pecking her cheek with his lips. Just as he was about to reach her lips again, he jumped over her mouth and pecked his way up to her right earlobe. He then pulled on her earlobe with his lips.

Tom then led her over to the blanket he had spread out on the beach. They kissed again as they both kneeled down on the blanket. Tom gently pushed her down and she lay on her back. "Roll over," he said.

Jessica giggled and rolled over onto her stomach. She put her head in the crook of her right arm so her left ear faced Tom. Tom pulled off his red t-shirt and climbed between her legs. On his knees, he put a hand on either side of her waist. Tom leaned forward and took her left earlobe in between his lips again. After a few tugs, he nipped at her cheek again.

As she reached her mouth, she leaned back and opened her mouth to kiss him. Tom pulled away and grinned. She let out a pout as she put her head back down. Tom leaned forward again and started pecking her neck, just below her hair. Jessica sighed.

Tom pecked her neck and worked his way to her left shoulder. He pulled her arm out to her side and slowly pecked his way down her arm. He then reversed and moved back up to her mouth. As their mouths met, Jessica let out a moan. Tom pulled away and Jessica said, "Your jeans are cutting into my ass." Tom grinned.

He got back on his knees and undid his belt and jeans. He then pushed them down and as his started kissing her neck; he wiggled out of his jeans. Jessica could feel his erect cock pressing into her ass through his boxers. Tom started pecking his way down her spine. As he neared her but, he finished taking off his jeans and quickly removed his boxers, allowing his erect dick to spring free.

To them started kissing his way back up Jessica's back. As he reached her neck again, he laid down on top of her. His dick was now in the crack of her ass. As he took her left earlobe in between his lips again, he pressed his pelvis down into her. She lifted her ass up to meet him. He slid his left arm underneath her and took hold of her breast.

Their mouths met and Jessica let out a soft moan into his mouth. Her breathing was becoming more and more rapid. Tom then started kissing down her spine again. The lower he got the more he scooted down. When he got to her ass crack, he kissed her left ass cheek. He then proceeded down her left leg. When he reached the back of her knee, she let out a giggle and brought her left up. "That tickles," she said. Tom just grinned and kissed his way down to her ankles.

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