Caught! Pt. 06

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Jon tells Dr. Robins about his first love.
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Part 6 of the 19 part series

Updated 06/11/2023
Created 03/22/2022
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JQueen9
JQueen9
666 Followers

Sam, short for Samantha

Jon's therapist gave him homework. When he claimed every relationship he'd had ended in disaster - with one important exception - she told him to compile a list of every girlfriend he'd ever had. They'd go down the list during counseling sessions.

His one successful love affair was with his high school girlfriend, Samantha, who insisted that everyone call her Sam. She dressed in boyish clothes and kept her hair very short. When Jon got to know her, he realized that the girlish teenager he'd enjoyed hanging around with since he was a kid was actually a very feminine, sensitive young woman he couldn't help but love.

They made wonderful memories together.

XXXXXXXX

Everything changed when Jon got his driver's license. Jon's older brother was a bit of a dope whose behavior troubled his parents; part of the reason Jon worked hard to be a good son and a good student was that he wanted to be someone who made them proud and didn't cause trouble.

They encouraged Jon to participate in his school's extracurricular activities as well as the social events organized for his classmates. The boxing team gave him friends and fitness. He went to bowling parties, events at the skating rink, dances, and gatherings at the homes of his classmates. As Jon got older his mother devoted more and more time to chauffeuring him and his friends, so she was relieved when he got his license. No son had ever done more to prove he was responsible enough to drive, so they gave him keys to a car his father didn't use much anymore. It was nice driving to school. It was nice giving rides to friends.

A frequent rider was a cute girl named Samantha, but who insisted she be called Sam. He'd known her since elementary school, and had enjoyed the bubbly optimism she always conveyed. They felt very comfortable around each other, and as the months went by, they found themselves spending time together in the school library, the cafeteria, and social events. They were both happy, well-adjusted kids who were fascinated by almost everything around them, and they realized that they enjoyed experiencing things together. Sam was the first girl Jon invited on an actual date, and his parents approved. They knew Sam, knew her parents, and thought that Jon's friendship with her was more evidence of his good judgment and maturity. It helped that Sam was the kind of girl who didn't wear make-up or the revealing, sexy clothes favored by some teenage girls. Sam gave off a boyish vibe.

The chemistry between them developed immediately. Jon could drive Sam wherever and whenever he wanted, so they began having long, intimate conversations that grew increasingly romantic.

As Jon felt their mutual attraction grow, he did something that revealed a lot about the kind of boy Jon was. He went looking for reading material offering dating advice for teenage boys. He found a lot of crap that focused entirely on birth control and sexually transmitted disease. Jon knew all that; he wasn't an idiot. But there was one essay written by a woman who gave blunt, practical, honest advice for young men who wanted to know how to treat their girlfriends. The author knew that boys were especially interested in what they would eventually call seduction, and she offered suggestions that were so sensible Jon never forgot them.

The idea was to recognize that teenage girls needed to be treated with extreme respect, and that this was the key to becoming romantic. She talked about the importance of good manners, mature behavior, and listening - really listening - to everything girls had to say. Listening, she said, is the most intimate thing a boy can do with a girl.

When it came to cultivating a physical relationship, the author said that girls wanted physical intimacy, but that many boys didn't understand what that actually meant. The key was taking one step at a time, and allowing girls time to enjoy each one. The obvious place to start was holding hands. Do that for a while, enjoying the feeling, before moving on to kissing. Don't rush on to French kissing, touching, or any of the steps that would come in time. Let things develop naturally. Savor the moment, for God's sake.

She said that it was obvious that boys needed consent every time they wanted to move on to a level of deeper intimacy, but that the girls didn't want them to bombard them with an endless series of questions seeking permission to hold hands, kiss, and all the rest. Girls wanted to express consent in a much more romantic fashion. A boy should place his hand next to the girl's hand and let her react. If she didn't move away, that meant it was okay to hold hands. Moving closer and closer, until their faces were almost touching, was the way to get consent to kiss. It was such sensible advice that Jon wondered why no one had said anything like this in the sex education classes he'd attended, which always acted as though teenagers were some kind of feral beasts when it came to romance.

Sam loved being treated this way. She'd always had a high regard for Jon, and when he started this series of gentle invitations to intimacy, it made her heart melt. Without ever rushing, they entered the grown-up world of intensely erotic romance. They had long make-out sessions in the back seat of Jon's car, finding remote places to park where they would not be disturbed. Eventually they began removing most of their clothing, touching each other in their most intimate places. It was wonderful. Just wonderful.

Sam may have looked boyish in her clothes, but when Jon saw her nude body he was transfixed. She was a woman, and looked like one. She may have only been a teenager, but Jon felt he was in the presence of a goddess when they were alone. In time their relationship included every sexual thing a couple could do without having actual sex. They'd start making out, and Jon would remove Sam's top and bra. After a while he'd remove her panties, too. She'd sit in the back seat of Jon's car, almost naked, with her legs spread wide so Jon could touch her where she wanted to be touched. It didn't take them long to figure out how to make Sam come. She loved every second of these sexy times, and she always expressed her happiness by returning the favor. She'd unzip Jon's pants, take his cock in her hand, and stroke him until he came in a tissue. The car would smell like sex by the time they were finished. Jon thought that nothing could be nicer than the relationship they enjoyed. Then Sam shocked him.

"I don't want to do this anymore," she said.

It was the most horrible thing she could have said. What was wrong? Sam seemed to enjoy these sessions as much as Jon, and she'd given him no warning of the fact that she was done with them.

"What's . . . what's wrong?" Jon asked.

"I want to stop fooling around like this. I love you, Jon. I want to make love with you. This has been great and all, but it's gone on too long. I want all of you. I want to make love for real."

Wow. Jon had enjoyed his time with Sam so much that he hadn't even thought about the fact that they'd spent more than enough time in the back seat of a car, and it was time for them to have sex. Some of their friends regularly had sex in their cars, and they constantly complained about it.

"We'll need to find a better place," Jon said.

"I know. I've thought about that. I don't have any good ideas about that. I suppose we could find some place to spread a blanket outside. I'm not crazy about the idea, but anything is better than being stuck in this car one more day."

"Yeah. You're right," Jon said. He pulled Sam close to him and gave her a long, soulful kiss. "I'll think of something," he said.

"Bring condoms," Sam said.

"Of course," Jon said, laughing. "I've been to the same classes you have."

For the next several days, Jon could think of nothing but the idea of having sex - real sex - with the girl he loved. They'd expressed their love for each other in every way but that, and it was thrilling to know what would happen next. But where? There was never a time Jon could expect to be alone with Sam at his house; it was the same where Sam lived. They were too young to rent a motel room. There were several nice parks with places to hike, and Jon used online maps to find places where they could get far enough from the trail to avoid being disturbed. But laying on a blanket spread over rocky ground laced with tree roots wasn't the kind of place Jon wanted to be with Sam for the first time.

Then he got an idea. It was perfect.

Jon picked up Sam Friday. They told their parents they were going to see a movie. "Hello, lover," Sam said slyly as she got into Jon's car. "Where are you taking me tonight?"

"Somewhere nice," Jon said, a big smile on his face.

"Where?" she asked.

"You'll see," Jon said.

It was a short drive to a facility that offered long-term parking for recreational vehicles. Jon's father owned a big, nice RV that the family had used a lot for the first two years. They hadn't used it for a while, however.

"Does your family have an RV?" Sam asked.

"Maybe," Jon said.

They parked the car and walked the short distance to the RV. Jon unlocked the door and let Sam inside. He'd created an actual love nest. Earlier Jon had driven to the RV, opened the windows to let in fresh air, change the sheets, and lit a bunch of candles. One of the candles was scented. Sam walked to the back of the RV and saw a queen-sized bed bathed in candlelight.

"Jon, this is very nice," she said. "I wish we'd thought of this sooner."

"I guess. I like the way we've done things so far," he said. "There's no rush. We've got all the time in the world."

"Yes, we do," Sam said, wrapping her arms around him. "This is actually happening, isn't it?"

Jon kissed Sam and began unbuttoning her blouse. All those make-out sessions had trained their bodies to respond quickly to each other. They weren't even out of their clothes before Jon was hard and Sam was wet. The first time they were able to lie down next to each other naked felt glorious. They hugged tightly, trying to intertwin their bodies and revel in the sensation of skin against skin.

They moved slowly, touching each other everywhere. Jon rolled Sam on to her back and kissed her more passionately than ever before. His hands caressed her breasts. He put one of his legs on top of her, and she spread her legs in response. Jon was so hard he ached. He reached down to caress Sam's pussy, finding it to be as wet and warm as he'd ever felt. "Jon, that feels wonderful," she said, moaning softly. She moved her pelvis up and down, inviting Jon to touch her ever more intimately. She felt his hard cock press into her hip. They touched, hugged, held, pressed, and finally they were both squirming and panting in desire.

Jon stopped, rose up from the bed, and got a condom. Sam watched him unroll it, glad she had a boyfriend who cared about protecting her. He laid down beside her again, started massaging her wet pussy, and she pulled his hand away. "I'm ready," Sam said. Jon carefully lowered his body onto Sam's, thinking his weight might be uncomfortable. The opposite was true. Sam loved the feeling of Jon on top of her, and she hugged him tightly to pull his body down into her's.

Jon placed his cock at the entrance to Sam's pussy, not sure what would happen next. He knew that girls often felt some pain the first time they made love, and he didn't know how to keep it from hurting too much. His instincts took over, and he slid smoothly into Sam's body. His cock entered her more than halfway, and he felt tightness and resistance suddenly fade away.

Sam grunted in pain. "Is it OK?" Jon said.

"I'm fine," Sam said. "Don't stop. It's not bad."

Jon moved in and out of Sam as slowly and gently as he could. Sam urged him to go deeper by lifting her pelvis up to meet each thrust. Jon had never felt anything remotely like this intense pleasure, and he felt like he'd need to cum soon. Sam experienced some lingering pain, but it was overpowered by blinding pleasure that pulsed through her pussy every time Jon went deeper.

When Sam came, her body got stiff and she arched her back so powerfully that she lifted herself and Jon up off the bed. Jon had seen Sam cum many times, but those orgasms were always gentle, subdued tremors followed by happy giggles. Sam gasped for air, hugged Jon tightly, and pumped her pelvis into him over and over again.

Jon's orgasm was intense and lasting. He thrust into her, hard, every time his cum pumped out of his cock. The pulsing lasted longer than ever before, making Jon feel he was filling Sam with an impossibly large load. He stayed hard for a long time, pinning Sam to the mattress, hugging her so tightly she could barely breathe.

He finally rolled to the side. Both of them were limp afterward. They both had the same thought: they weren't virgins anymore. Yah!

"That was wonderful," Sam said.

"It didn't hurt?"

"It hurt. Not much. But it felt soooo good."

Jon removed the condom and wrapped it in a tissue so it wouldn't make a mess somewhere. He laid down next to Sam and let his hands touch her everywhere she liked being touched. The whole thing was over less than a minute after it began, but they both felt nothing could have made it better. They talked, and kissed, and talked, and held each other, and felt overwhelmed with love. Everything looked marvelous in the flickering candlelight. "I am so glad we finally did this. So glad," Sam said.

They were silent for a long moment. Words added nothing to the experience. They were both very surprised when Jon became hard again. It wasn't something they'd expected. But Jon was a young man, crazy in love, entwined with Sam's body, and soon he wanted to repeat their experience.

Sam stroked Jon's cock, amazed by the way it felt as it grew harder and bigger. "Do you have another condom?" she said.

"I only have 11 more. I hope we don't run out," he said, causing Sam to giggle again. He loved the way that sounded.

Sam opened the condom wrapper and took Jon's cock into her hand. It felt like iron wrapped in velvet. She unrolled it all the way to its base, then squeezed him the way she had many times before during the make-out sessions in his car.

Jon felt his heart pound as Sam laid back on the bed and opened her legs for him. There was no need for more foreplay. Jon slipped into Sam again, feeling the tight grip of her wet, warm pussy. Sam's arms wrapped around him again, pulling him to her, urging him to go faster and deeper.

The pleasure was every bit as overwhelming as the first time, but Jon didn't feel the same powerful need to cum so quickly. He tried to relax and enjoy the sensations as Sam squirmed happily beneath him. She came after a few minutes. It wasn't as powerful as the last time, but it was very pleasant. "Stop. Wait a second," she said, telling Jon that she felt so sensitive after her orgasm that he needed to let her recover. Pretty soon she let him know she was ready again, and they resumed their lovemaking.

It went on, and on, and on. Sam came several times, and Jon learned how to stop moving long enough for her to enjoy continuing. Jon's pleasure grew gradually, and soon he was moving so fast and so deep that Sam was almost overcome with it all. When he finally came, his cock throbbed for so long that Sam almost came again.

He laid limply on top of Sam, not moving until he heard her giggle. "Wow," she said. "I think I'm going to want to do this more often." Jon laughed, rolled off her body, and disposed of the condom before it slipped off on its own.

Jon had a surprise. He'd put cans of Sam's favorite soft drink on ice. They were both pretty thirsty, for obvious reasons. It felt nice to sit naked beside each other, talking about how good they felt, and enjoying the moment.

Some time had elapsed before Jon noticed something about the way Sam was sitting. She'd pulled the covers up over her breasts and under her arms, displaying a modesty that seemed unnecessary at that moment. She was so beautiful. Sam's hair was a mess, but Jon didn't mention it because he liked it. Her messy hair was sexy in a way he'd never experienced before.

Jon took a handful of the blankets and began slowly pulling them down. Sam tried to hold them up for a moment, but she let go when she realized what Jon was doing. He revealed her breasts, then her belly, then her beautiful pussy, then her legs, and finally had her naked from her head to her knees. She was so beautiful in the candlelight that Jon could barely speak. He didn't need to. His expression communicated everything to Sam. At that moment, she felt like the most desirable woman alive.

"You're a goddess," Jon said. He could have said almost anything and it would have pleased Sam, but she thought his words were exactly what she wanted to hear.

Jon ran his hand slowly up Sam's leg, across her belly, and down her other leg. He caressed her inner thighs. Her breasts. Her neck and face. Her arms. He was so engrossed in the moment that Sam's expression surprised him.

"I don't believe it," Sam said.

Jon was hard. Again. Teenage boys, right? Sam reached down and began stroking him, making him even harder. Jon reached up and massaged Sam's pussy. They were so spent that their desire wasn't as urgent, but Jon finally got another condom, put it on, and spread Sam's legs again. They made love slowly. They were getting tired. Sam didn't cum this time, but she loved this sensuous, unhurried way of making love - so different from their first two times.

It wasn't easy, but Jon managed to cum one more time. There was nothing in the condom afterward, of course, but it was marvelous that making love offered so many pleasures he'd not expected. He'd expected it to be great, but not this great.

They put on their clothes and picked up the RV, getting rid of evidence that they'd been there. On the drive home Jon wanted to talk about everything. How much he loved Sam. How amazing it all was. How much he'd enjoyed all the specific little things they'd done in bed. But Jon knew that a lot of women felt men talked too much - acting as though men needed to educate women on every conceivable topic. This felt like a time to be quiet, so Jon took Sam's hand and drove her home in silence. Sometimes he'd look at her and smile; she'd smile back.

"I was a virginal girl when I woke up this morning," Sam said finally. "Now I'm an experienced woman."

Jon walked her to the door of her parents house to say goodbye. "Will it always be this wonderful?" he asked.

Sam kissed his cheek. "We'll find out," she said.

JQueen9
JQueen9
666 Followers
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Ellienora35Ellienora35about 2 years ago

I want to know what changed after he and Sam seemed to have such a good start

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Caught! Pt. 05 Previous Part
Caught Series Info

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