Jakob & Jessie–The Improbable Couple

NOTE: This is a repost because there was a single reference to being underaged that has now been corrected. It is a multi-chapter story that doesn’t make sense without the first part.

This is a story about two misfits who discover they aren’t misfits after all. They just needed to find the right fit.

Chapter 1

Jakob was pissed! He didn’t want to go on the stupid senior trip in the first place and now, because his dad had to get back to the farm chores, Jakob was more than an hour early for the departure. Moping, he boarded the coach, went about two-thirds of the way down the aisle, and climbed into a seat. He hated most of his classmates and thought that they hated him. He was just a dumb-ass farm boy; they lived in town or in the new residential developments on what used to be farm land. They watched HBO and Showtime; he didn’t even have cable. They had I-pods; he had chores. He had nothing in common with any of them, yet here he was seated on the coach, getting ready for the trip to Disney World. Damn his mother, anyway! Damn this whole fucking idea! He kept his head down, making believe he was looking out the window while the other seniors got seated, joking and laughing all the way down the aisle.

Suddenly, a shadow was cast over him, as someone stood at the empty seat. “Is this taken?”

“Oh, no,” Jakob thought, “this is the last thing I need.” He looked up and almost died. It was Jessie, the most beautiful, sexiest girl in the class—the one with the hottest body, the best breasts, the tightest ass, the hottest legs in the entire county. Jakob looked around; all the other seats seemed to be filled.

“Well, aren’t you going to answer me? I know you weren’t raised to be rude.”

“S…Sorry,” Jakob gasped. “I guess you can sit there. I’m not saving it for anybody.”

Jessie smoothed the rear of her short shorts, noticing all the attention her superbly sculpted ass was getting from her classmates—girls as well as boys. Then she slid into the seat, bumping into Jakob as she did. “Now it’s my turn to apologize. Sorry for being so clumsy. I almost sat right on top of you.”

“It’s OK, no harm done” Then Jakob turned back to the window, afraid of the reaction a glance at Jessie would cause. When she turned away for a moment he snuck a glance—just a few seconds. Her breasts were magnificent—firm and round , coming to a point where her nipple pressed against the tightly stretched fabric of her bra and t-shirt. Her abdomen was firm and flat; her waist was tiny flaring to round hips. Her legs were long and slender. Where they met was a three-inch space. Oh, that space was so incredibly inviting! Jakob figured she must have dates and boyfriends by the hundreds. It was only a few seconds but his body reacted to the sight. He could feel the denim covering his thigh stretch around his growing erection. Just then Jessie turned back toward him, looked down and smiled. Jakob turned six shades of red in embarrassment. He was mortified, not that he had reacted—that she had so readily found him out. He decided then that Jessie was a real tease.

Finally, the teachers arrived and the coach pulled out, beginning its day-long trip to the park. Jakob tried to shrink against the bus wall—anything to get away from Jessie. However when one is 6 feet, 2 inches tall and weighs more than 200 pounds that’s no easy task. She, however, seemed to take Jakob as a challenge to her femininity. She stretched in the seat forcing her breasts against the straining cloth of her shirt. Jakob looked on in awe. He never thought such thin cotton could be so strong. When she brought her arms down to her sides she brushed against Jakob’s bicep. Her touch felt hot to Jakob; a jolt of electricity surged through him at her touch. Jessie just looked—and smiled.

Jakob was getting really uncomfortable. His erection just wouldn’t go away. In fact, it seemed to grow larger, much to his continual embarrassment and Jessie’s continual amusement. Jessie rose half-way out of her seat and looked around. Most of the other kids were either sleeping or engrossed in their MP3 players or video games. She sat back down, turned to face Jakob and said, “You seem to have quite a problem there. I feel responsible. Why don’t you let me take care of that for you?” Her deft fingers fell upon his cock with a vengeance. She rubbed him up and down.

“Why are you doing this? Jakob whispered desperately.

“Let’s just say I don’t enjoy seeing another human being in distress, especially when I am so obviously the cause. I am the cause, aren’t I?”
Jakob could barely speak so he just nodded agreement. Shielding with her body she moved her hands up to his belt and in only a few seconds his cock sprung loose. Now it was her turn to be amazed. Jakob’s cock was not less than nine inches long and very thick. She shuddered to think what a weapon like this could do to her pussy. She could barely reach her long fingers around it. She slowly began to stroke this magnificent beast. Jakob was spellbound by this vixen so determined to jerk him off. Jessie speeded her motions; Jakob could barely breathe in his excitement. A sudden shudder signaled the onset of his orgasm. As Jakob’s cock began to twitch uncontrollably, Jessie leaned forward to take him into her mouth. She had just engulfed the head when it exploded in an orgasm more forceful and more intense than any he had ever experienced. Stream after stream of hot searing cum rammed into the back of her throat. Jessie just managed to swallow it all then licked all around the tip successfully cleaning it of any remaining semen. She gave his monster cock a final kiss and put it back into Jakob’s pants. She leaned forward, kissed Jakob on the cheek and whispered, “Maybe you can return the favor later.” If Jakob was embarrassed before, he was horrified now.

Jakob had absolutely no experience with girls. Living on the large family farm had isolated him from his classmates. This did not mean, however, that he had no experience with sex. He masturbated regularly, sometimes two or three times a day often dreaming of Jessie, and he had fucked Sarah, the family mule, any number of times. He could not imagine that a girl could be so forward. The trip wasn’t even an hour old and she had not only jerked him off, sucked up his cum, and licked his cock clean, she had all but invited him to do the same to her. Maybe this trip wouldn’t be so bad after all.

Summoning all his courage Jakob turned to Jessie, looked her in the eye, and said, ”OK, why me?”

Jessie turned, “Why not you?”

“You are the most beautiful girl in the class. Hell, you’re the most beautiful girl in the county. Why aren’t you sitting with the popular football stars, or some other jock?

“Jakob, this body isn’t the blessing you might think it is. Most boys are intimidated by me and the girls are either jealous or just hate me because they think I’m so popular with the boys. The truth is…I hardly ever go out on dates. When I do, all the boy can think about is groping me. I’m just as lonely as you are. Different reason, maybe—but just as lonely.”

Jakob could barely believe his ears. Then Jessie continued, “You probably think I’m brazen the way I did what I just did. I was terrified you’d reject me. Yours is the first cock I’ve ever seen, let alone touched or licked.”

Now Jakob was speechless. He had been so jealous of this gorgeous creature, and now he learned she was just as human as he was—just as desperate as he was. He reached out, taking her hand in his. Her skin was so soft in comparison to his calloused work-hardened paw. He looked at Jessie and saw that there was a tear in her eye. He wiped it from her face with his finger. Jakob was what people used to call “raw-boned” in the style of Gary Cooper or Randolph Scott. He had a big frame with large hands and feet. His body was toned by years of hard farm work—digging, lifting, and moving stock. But he was not a hard person. He had a tender sensitive side which he usually showed by his love of nature. He hated hunting because he couldn’t bear killing any magnificent wild beast. He tolerated fishing only by telling himself that fish were such a low species that they actually caught themselves most of the time. He loved his mother and his sisters, the only females to date he had ever really known. He really didn’t know if he was doing the right thing; he was afraid he might offend. He was working on instinct because he really had nothing to fall back on, but apparently he did the right things now. Jessie moved in close and leaned her head on his shoulder.

Chapter 2

As Jessie snuggled closer Jakob raised his arm, making room for her. He was careful where his hand fell, making sure it didn’t touch her breast. Jessie looked up at him, kissed him on the cheek, and snuggled even closer. She reached back and took his hand, placing it on the one spot Jakob had tried so hard to avoid—her left breast. “I like to have them rubbed and massaged,” she whispered into Jakob’s ear. Slowly Jakob took her breast into his hand. His hands were huge, but it was all he could do to fit the entire breast into it. He gently squeezed and massaged her, eliciting a moan from Jessie’s lips. He moved his hand up to her nipple. It was rock hard, but extremely sensitive. As soon as he touched it, Jessie squirmed up and planted a hot kiss right on his lips. Her tongue found its way into his mouth where it intertwined with his. It was Jakob’s first real kiss and it was a kiss to remember! Nervously, he looked around to see if anyone had noticed what was going on—all the other kids were either still asleep or totally self-absorbed. Satisfied, he returned the kiss with enthusiasm. Jessie had her hand in Jakob’s lap where she immediately noticed Jakob’s cock reacting to her. “Hmmm, we are definitely going to have to do something about this, aren’t we?”

“Sorry, I just can’t help it.”

“You don’t have to apologize. Just take a look at my shorts. I’m soaking wet. You’re having the same effect on me.” Then she kissed him again.

A lot of the kids started to move about, waking up or just restless so the two new-found lovers decided they had better cool it. They still held hands, but that was all. Before they knew it the coach was making a pit stop. All the kids exited the bus right behind the teachers to hit the rest rooms and grab a snack. Jakob and Jessie were the last off the bus so they could sneak another kiss. This time Jessie grabbed his hand and put it right onto her wet crotch. “When we get to the hotel…” she looked up and promised. Jakob dropped her hand once they were off the bus, not sure if Jessie would want to be seen in the company of a loner like him, but she grabbed it right back, holding it tightly until they parted at the rest rooms. Before separating she reached up and kissed him right in front of more than thirty classmates. Some of them looked shocked, but Jessie didn’t care. She kissed Jakob again then got onto the inevitable long line to pee. Jakob was done first, of course, so he bought a large coke and some snacks to share from the convenience store. He was already out when Jessie exited the ladies room. She walked right up to him and squeezed his arm. It was the equivalent of an animal marking its territory—THIS IS MINE, KEEP AWAY! Jakob had never felt better.

A couple of the jocks decided they would make some trouble. They’d teach this farm hick a lesson. Who was he to start up with a babe like Jessie? They stopped him on the way back to the bus. Jakob did his best to elude them, but a confrontation was unavoidable. It wasn’t that Jakob was afraid—he was afraid he’d really hurt someone. One of the boys took a swing at Jakob, hitting him squarely in the stomach. Jakob shook it off like it hadn’t even happened; it had no effect on him. He grabbed the boy by the shirt and lifted him off his feet—all 180 pounds of him! Jakob just held him in the air for several minutes when a teacher arrived. “What’s going on here?” he demanded.

“Oh, nothing, Mr. Kanicky,” said Jessie. “Jakob was just showing the guys how strong he is, right?”

“Yeah, right,” the others said a little too quickly as Jakob slowly lowered the unfortunate adversary. He patted his head and smoothed his shirt condescendingly. “Just a dare, Mr. Kanicky, that’s all.”

“Well, let’s get back on the bus. It’s time to go.”

Once back in their seats Jessie said, “You were incredible. I had no idea you were so strong. You always seem so meek in school.”

“That’s because I don’t like school or any of my classmates. Sorry…I didn’t like any of my classmates, and I still don’t like most of them. Besides, I’m not all that strong compared to some of the other farmers. It’s hard work and long hours. You have to be strong—inside as well as outside—because there are so many things that can go wrong—rain, hail, drought, heat, cold, insects, you name it.”

“If it’s so hard, why do it?”

“That’s just it—the challenge.” Jessie saw for the first time the real Jakob, and she was impressed by what she saw—a real person of real strength, a person who worked hard and loved it. She had a new sense of respect for him. She already lusted for him, now she thought she could even love him. She snuggled up to him giving him a terrific hug.

The rest of the trip was mostly uneventful, but in mid-afternoon Jessie asked Jakob for his jacket. Jakob was puzzled. It was hotter than hell in the bus. Jessie just spread the jacket over her lap. Then she seemed to wriggle around quite a bit. When she was done she took Jakob’s hand, moved it under the jacket right onto her bald pussy. Jessie had removed her shorts and underwear right in front of him. Her pussy was dripping wet. Jakob put his finger onto her slit and moving it up and down made her even wetter. He looked at Jessie and saw that her eyes were closed, her breathing shallow. He’d seen similar scenes in internet porn so he knew he was moving in the right direction. She gasped when he pushed his finger into her and she swooned when he started to rub her clit. Moving his finger in a circular motion he felt her button respond. It hardened as Jessie’s breathing became more rapid. Suddenly, her body shook and shuddered as a powerful orgasm claimed her. Jakob continued his motions until he was sure it had passed. Then he removed his fingers and put them into his mouth. Damn, she tasted wonderfully! They rested, arm in arm, until the bus arrived at the Orlando hotel.

Chapter 3

Once off the coach Jakob grabbed his bag and took Jessie’s, too. He walked off easily under the load. Jakob had only brought a few shirts and shorts, a bathing suit, and something to sleep in; Jessie had a full suitcase of stuff. Jakob was sure he didn’t want to know what she had in there, but it sure was a lot. Later in the evening there would be strict rules separating the girls rooms from the boys, but now the kids roamed freely around the hotel. That’s how Jakob wound up in Jessie’s room—alone with only her. The roommates had dropped their bags, redressed in their bikinis, and headed straight to the pool. Jakob dropped her bag and turned to leave. “Where do you think you’re going?” Jessie asked.

‘Uh… I figured you’d want to change and go to the pool.”

“Wrong! I can swim anytime. Right now I want to fuck and that requires two people—me and you! Close the door, lock it, and get over here before I change my mind.”

Jakob did as instructed. He closed and locked the door, making sure to throw the security bolt. Then he turned to Jessie. She moved forward, threw her arms around his neck and initiated a long hot kiss. Jakob’s arms encircled her waist, pulling her even closer to him. “This is fantastic,” thought Jakob; not surprisingly Jessie was having the exact same thought. Jessie broke the kiss and stepped back. She pulled her Tee over her breasts and head revealing a lacy bra which she quickly opened and dropped to the floor. Jakob was spellbound. Her breasts were even more magnificent in the flesh. She just as quickly she dropped her shorts and thong, revealing her cleanly shaven pussy. Even at a distance of four feet Jakob could see tiny droplets dripping from her labia. Jakob pulled at his shirt, dropping it into a pile where it was soon joined by his jeans and boxers. His erection stood at full attention as they once again moved together. Now it was Jessie’s turn to be amazed. Jakob had the body of a Greek god. He never used the exercise room in school. He got his muscles tossing bales of hay like they were softballs.

“Uh, maybe we shouldn’t do this,” he whispered. “I don’t have any condoms.”

“Silly boy, I’m a virgin and I’ll bet you are, too.” Jakob simply nodded. “And,” she continued, “I’ve been on the pill since I was twelve. I guess my mother couldn’t imagine anyone who was as developed as me not wanting to fuck my eyes out. But, here I am eighteen and a virgin—but not much longer, I hope. All my contacts with boys always seemed so wrong; this seems so very right.” She leaned back onto the bed, spread her legs, and raised her knees inviting his entry. Jakob, using his farm sense went to the bathroom where he procured a large towel. Placing it under Jessie, he climbed between her legs. He lowered his head until it was just even with her pussy. He licked her from her butthole to her clit. Jessie responded with a series of gasps and moans. She grabbed his sun-bleached blond hair and pulled his head into her wanting pussy. It wasn’t long before she was experiencing an overpowering orgasm that took over every part of her luscious body. When Jakob reached up to tweak her nipples she jumped a foot into the air, collapsing totally drained onto the bed when she fell.
“Ohmygod,” she uttered between gasping breaths. “I’ve never cum like that before. Don’t tell me you learned that on the farm.”

“No,” he laughed, “I watch porn on the internet just like everyone else.”

“Well, you certainly must have paid a lot of attention. My whole body is tingling, and I’m a wreck.”

‘You still look just as beautiful to me; actually more beautiful,” he said as he leaned forward to kiss her. Their tongues danced with their desire. Jessie reached down between her legs feeling the heat emanating from his rock hard cock. She rubbed the head, now dripping with pre-cum all over her slit. Positioning the head just above her hole she thrust her hips forward forcing his cock head two inches into her. She groaned as the monster started to stretch her vaginal walls. Placing her hands on his butt she pulled him into her. All the while they maintained eye contact, showing each other their want, their need for each other. Jakob pushed a bit further until he met resistance. His cock pressed against her hymen. “I don’t want to hurt you,” he whispered. Jessie’s response was to once again thrust her hips up and forward, rupturing the hymen in an instant. She cried out and tears came to her eyes. Jakob stopped, keeping his cock still in her pussy. He kissed her tears from her cheeks until Jessie pulled his head and lips down to meet hers. Just before they met she whispered to him, “I’m OK, push it in all the way. Please…please fuck me. I want you all the way in me.”

Jakob reared back to gain momentum and pushed forward in several small thrusting motions until his cock had reached the end. His pubic hair was up against her perfect smooth labia. He started a rhythm, slow at first and Jessie matched it. They humped together for several minutes. Although soaking wet, her pussy generated heat and friction for them both. Their tempo increased, Jessie meeting each thrust with one of her own, until Jakob arched his back forcing his cock even deeper into her, if possible. A low guttural growl escaped his lips as his cock throbbed within her. Suddenly, he erupted into her womb. Years of frustration were released as what seemed to be a gallon of cum escaped from his balls, up his erection to drown her womb in hot sticky white semen. Literally millions of sperm rushed into her womb. This eruption was just what was needed to trigger yet another orgasm from Jessie. She writhed uncontrollably beneath her lover. Finally, they collapsed drained and drenched in their sweat.

It was several minutes before either could speak. Just as Jessie opened her mouth they heard noise in the hall and a key in the lock.

“Shit,” said Jakob, “I’d better get dressed.”

“Oh, no!” replied Jessie leaping from the bed. “I want these bitches to see exactly what they’ve been missing. I’ll unlock the door and be right back.” She tiptoed to the door and released the security bolt then ran back to the bed enveloping Jakob in an embrace from head to toe. She wrapped everything she could think of around him—arms, legs, head—absolutely everything. Then she kissed him. They were in that position when her roommates opened the door.

“What the? Jessie, what the hell?” The three girls stopped halfway across the room.

When Jessie rolled off Jakob the girls got a good view of his body and his equipment, still fully erect.

“Oh my god. Jessie, you lucky bitch, you. Look at the size of that thing. He didn’t put all of that into you, did he?”

Jessie just smiled and pointed to the cum flowing out of her pussy.

“Damn, girl, I don’t think I’ve ever seen so much cum in my life.” I wouldn’t mind some of that if you’re willing to share. It was Denise, long acknowledged as the class whore.

Jessie just laughed, “Sorry guys, I got here first and I’m claiming squatters’ rights. You can just find your own cock to fuck.”

The other girls feigned disappointment, but they still couldn’t take their eyes off Jakob’s body. Eventually Jakob rose from the bed, his cock still dripping cum. Denise rushed over and licked it from his tip. Jessie pushed her away. “If anyone’s going to lick up that cum it’s going to be me!” She knelt before Jakob and pushed her lips around his cock. She drank his cum, just as she did earlier and licked the mammoth organ from tip to stem cleaning it as she went. Jakob was more than a little embarrassed. He wasn’t used to standing naked in front of anyone, let alone three hot bikini-clad girls.

“I really think I should be going. It won’t do us any good to get caught like this.” He picked up his clothes and in a minute he was dressed again. Denise went to the door and checked the hall—no sign of the teachers. Jakob ducked out the door and down the nearby stairs rather than wait for the elevator. It proved to be a good decision as three female teachers exited when the door opened.

Chapter 4

Once the door was closed all the girls rushed Jessie for the details; of course they assumed that she was experienced sexually because of the lushness of her body. They just could not believe that she had been a virgin, but they were convinced when she showed them the towel Jakob had so wisely brought from the bath room. They asked when it had started; startled to learn it was just earlier today. Slowly they pulled all the details from Jessie although she was reluctant to tell all. Their eyes went wide when she described how she had jerked him off on the coach then swallowed his cum. They were all ears when she told how Jakob had masturbated her later in the ride. But, mostly, they were incredulous about the size of Jakob’s cock. Jessie described their coupling, intent on making them jealous. And jealous they were. Their boyfriends all had smallish to normal sized cocks in the five to six inch range and none of them could approach Jakob’s girth. When Jessie described the feeling of stretching her pussy walls to accommodate all of his cock the girls swooned with desire. They were totally jealous of Jessie and angry at themselves for never noticing Jakob throughout their years at school.

Jakob called their room and made arrangements for dinner with Jessie. They met in the lobby—all five of them—Jakob and the four girls. It seemed that he had gone from loner to sex god in a single day. They walked to a moderately priced sit down restaurant. They sat at a table for six and when Denise made for the seat next to Jakob she almost got a kick in the ass from Jessie. “Remember what I said, ‘This is mine. Keep away.’” Denise sulked to a seat on the opposite side of the table while Jessie moved in as close to Jakob as the chairs would allow. Jakob surprised them all by offering to pay the whole bill.

“Just because I’m a farmer doesn’t mean I’m poor. I’ve been working for almost ten years and I’ve been getting paid well for almost that long. I just don’t throw my money around.” Again, Jessie was dumfounded—what a prize she had found in Jakob. They strolled slowly back to the hotel. Curfew was 11 p.m. so they had a few hours to spend together, if only they could shake the other girls. Eventually, Jessie lost patience with them. “Get lost,” she said emphatically, “We want to spend some time together—alone.” Reluctantly the three roommates left, catching glimpses of the tent growing in Jakob’s pants; wishing they had Jessie’s luck.

“I have a confession to make,” she said just before reaching up for a kiss. Jakob looked back quizzically. “I set up our meeting this morning. I got to the bus almost as early as you did then I waited until the bus was filled before getting on. I wanted to sit next to you and I didn’t think you’d want me.”

Now it was Jakob’s turn to be wide-eyed. “Why would you want to sit with me? I’m just about a total outcast in school.”

“That’s why, plus something my mom told me about men. ‘Still waters run deep,’ she said. I thought about who that might apply to and the only person I could think of was you. This trip was the perfect time for us to get together. I just had to have the nerve to act on my impulses. You have no idea how many times I almost chickened out but I figured I had to be bold to get what I wanted. I had no idea how wonderfully it would all turn out.“ Then, after a pause, “I hope I haven’t said too much and scared you off.”

Jakob never said a word. He simply grabbed Jessie and pulled her to him very, very close. “I don’t care how it happened; I just can’t believe it actually has. Now that I have you I don’t ever want to let you go.”

“Let’s find someplace private,” Jessie whispered and then led him away by the hand. They found some deserted shuffleboard courts with a screen of bushes behind them. There was a small space behind the bushes, maybe three feet by ten. It was there that Jessie led Jakob. They couldn’t get their clothes off fast enough, so intense was their desire. This time Jakob lay on the ground pulling Jessie over him. She descended quickly spreading her labia so they would accommodate his huge man meat. She eased down savoring the sensation of having her pussy filled and stretched almost to its limit. When he was fully in her she waited astride his abdomen, eyes closed and breathing deeply. Jakob reached up to her magnificent breasts. They were at least D-cups and possibly even double-D’s, yet they were so firm and upright. He marveled at the feel of them– their fleshiness, the softness of the skin encompassing their mass, the hardness of the nipples. She gasped loudly when he took her nipple into his mouth, suckling like an infant. The sensations in her pussy began to get to her. She started to rock back and forth, rubbing her sensitive clit into his pubic hair. As she did so she became more and more excited. Her reaction was to speed up her motions. It became a marvelous self-fulfilling cycle that ended only when she came in a shuddering orgasm. She almost fell onto him but he supported her with his strong arms. Surprisingly, Jakob had not yet cum so he continued his motions in and out of her dripping cunt. It wasn’t long before Jessie joined him, beginning her journey toward yet another mind-blowing orgasm. Jakob reached down between their abdomens seeking her tiny bud. He found it just in time to throw her over the top again. This time he accompanied her to Nirvana, spurting columns of white hot cum from the tip of his cock deep into her cunt and womb.

Once sated, they lay there silently until they heard, “Encore! Encore!” and “Bravo!” Jessie turned around to find her three roommates peeking through the shrubbery. They were smiling but embarrassed at the same time. “Sorry, Jessie. Sorry, Jakob, but we just had to see that wonderful tool of yours in action.”

“Yeah,” said another girl, a thin dishwater blond, “and you sure didn’t disappoint us. That looked like so much fun. Jessie, when you lowered yourself onto that huge cock I thought I’d faint. I am so fucking jealous.”

Hell, we’re all jealous, aren’t we?” Denise chimed in. “I’d love to have a cock like that in my pussy. In fact, I’m all wet just thinking about it.”

Jessie looked down at Jakob. “You know, I think there’s only one way to get rid of these three. You’re still hard so….”

“I’m not the cheating kind, Jessie. I’m more than happy with you. But, if it’s what you want…”

Jessie leapt up exposing Jakob’s cock, gleaming with her juices. “OK, who’s first, as if I didn’t already know.”

Denise had her shorts off in an instant as she pushed through the shrubs. She wasted no time lowering herself onto Jakob’s cock. “Oh fuck! That feels so fucking good. Give it to me Jakob. Give it to me hard!” Jakob pushed up until his cock was totally seated in her cunt. She was fairly tight, but not as tight as Jessie—maybe because she was more experienced, he thought. Actually, it was due to the child she had given birth to last summer when she was “visiting her aunt.” Denise rode him hard until she came suddenly and with tremendous intensity. She fell forward onto Jakob’s chest.

“C’mon, Denise, give me a chance.” It was Sally, the thin dishwater blond. She was already totally naked, rubbing her pussy in anticipation and trying to stretch it to accommodate this beast. Slowly and carefully Denise rose with the help of the other girls. No sooner was she out of the way than Sally replaced her. It was a struggle to get his cock into her but with effort and patience the job was eventually done. Using her legs as pistons she rose and fell on his cock. It was a good way to maximize penetration depth. She was so tight the friction was intense despite the wetness of her cunt. Jakob’s girth caused his erection to rub against her G-spot with every stroke. It was only a minute before she shrieked in ecstasy.

As she sagged down she was lifted from Jakob and replaced by Stephie. “Be careful, Jakob. I’m a virgin.” The other girls looked at her in disbelief. Stephie had been going steady for more than a year so it was hard to believe. “Joey isn’t very into sex,” she explained. “Sometimes I think he may actually be gay.” What made this so funny was that Joey was always bragging about his sexual prowess. Jakob held her hands as she lowered onto his erection. She was wet enough so that wasn’t a problem, but when he was in about three inches he met the inevitable barrier.

“It’s going to hurt when your hymen breaks, but it will only be a short time before you start feeling good—hopefully very good.”

“OK, what should I do?

“OK, either stay very still and I’ll thrust up or I can stay still and you can fall down onto me. Either way will work.”

“Maybe you’d better do it. I’m afraid I’ll chicken out.” Stephie then closed her eyes and gritted her teeth in anticipation. Only a second later Jakob raised his hips with a sudden movement and Stephie cried out in pain. Jakob held her tenderly until she signaled he should continue. Now he moved slowly until Stephie met his thrusts with counters of her own. Now they moved together, building up steam and speed. Her pussy leaked her juices all over his abdomen and legs, indicating just how eager she was. Stephie was going wild on Jakob’s cock. She rubbed her clit against him with tremendous force; Jakob could see how it was growing. Her orgasm was building slowly but steadily. When her eyes glassed over he could tell she was close. A touch of his finger on her clit triggered her. She shook all over and both were surprised when she squirted again and again, drenching him in her fluids.

“Wow, I’ve never done that before. Jessie, if you ever get tired of him, just let me know. I’ll be next in line. You’re incredible, Jakob. Thanks for making my first time so great.” She leaned down and kissed Jakob on the cheek.

They all dressed and just got into the hotel before curfew. With about ten minutes to go, Jessie took Jakob aside. “Good, just enough time for a long kiss,” she said. Jakob looked at his watch. “This is going to be some kiss,” he thought. It was—ten minutes of dueling tongues, grinding lips, and saliva dripping all over. When it was done Jakob spoke, “Thanks, Jessie—for making this trip so wonderful. I didn’t want to come, but now I’m thrilled to be here—with you. I only wish we were spending the night together—not for sex, just to be close to you would be more than enough.” He turned and led her to the elevator. He got off at 2; she at 4.

Chapter 5

The trip went too fast. The couple fucked at every opportunity. They found a small isolated area behind “It’s a Small World” where he picked her up and lowered her onto his erection. He bounced her up and down until they both came urgently. Fucking at the park was difficult and dangerous. There was always the chance they’d be discovered. Then Jakob had an idea. He was eighteen and, with money in the bank, qualified for a credit card which he’d brought for emergencies. He headed for the hotel reception desk and asked if they had a room. He explained he was there with the high school group but he wasn’t getting along with his roommates who were argumentative and snored all night, too. There was one room, a suite with a Jacuzzi, but the cost would be $290 a night. Jakob brought out his charge card without a second’s hesitation and laid it on the counter. The reception clerk was surprised when it was accepted immediately. Jakob asked for two keys so a buddy could join him. Later at breakfast he gave Jessie the key card. “What’s this?” she asked.

“The key to our room on the sixth floor, number 612. We have it for the next two nights.”

‘Jakob Johannson, you are incredible. I’m going right back to move my stuff up there. I think it will be easier now than later.” Jessie all but ran down the hall to the elevators. Fifteen minutes later she was back with a huge smile on her face. “Did you see that tub? It’s big enough for two. Hmmm! I am getting some wicked ideas.” Then she kissed him once again.

They had a great time at Disney that day knowing they’d have all night to make love. After dinner they walked up the stairs to the room. Jakob opened the door and carried her over the threshold as lovers have done for centuries. Then he threw her onto the bed. They both laughed, thrilled with the privacy Jakob had attained for them and with the intimacy to come. Jessie jumped off the bed and ran to the tub, filling it with warm water. She returned to Jakob and started to undress him. She held his erection tenderly as he began to undress her. By the time he was finished the bath was almost half full. They climbed in carefully, Jessie sitting just in front of Jakob with her back to him. He reached around her to fondle her breasts, rubbing and teasing her nipples. Jessie purred and turned her head so they could kiss. Her tongue found Jakob’s instantly and they shared a jolt of sexual energy. They were hot for each other—so hot they couldn’t wait. Jessie went up onto her knees and leaned forward making her pussy readily accessible to her lover. Jakob followed suit, kneeling behind her and rubbing his cock against her slit. “Please, Jakob, don’t tease me. Please put it in me. You know what I want.”

Jakob leaned forward sliding his cock head into Jessie’s waiting cunt. Jessie pushed against the tub, trying to increase the speed of his entry. She welcomed the now familiar expansion of her tunnel and the heat of his organ. In just a moment his tip brushed against her cervix. Jakob began to move very slowly. They both loved the sensation their fucking created. The feeling was unequaled by anything either of them had ever tried. As their pace increased water started to spill over the rim of the tub. Somehow Jessie was able to reach the drain and open it. Their pace was frantic now. Jakob was fucking like a dog when, suddenly, Jessie’s body went rigid. Jakob had inserted a wet finger into her asshole. He rubbed the thin membrane between her ass and pussy. The feeling was incredible, more intense than anything they had ever experienced. Thus, was Jessie introduced to the pleasures of anal sex. Jakob moved his fingers as quickly as he was fucking Jessie, maybe faster. Now Jessie’s motions ceased. She held that position for a moment, until it felt like her whole body would explode. And then it did! Her body shook like a rag doll in a hurricane. She had absolutely no control over her movements and would have fallen forward into the water had Jakob not rescued her.

He lifted her from the tub, holding her while he toweled her completely dry. He ignored his own needs while he tended to her. He carried her to the king sized bed and tucked her into the blankets before returning to dry himself. He climbed into the bed expecting to rest, but he found Jessie almost fully recovered and wanting more. “I loved it when you put your finger in my ass,” she said as an introduction to more hot sex. “I’ve seen porn with anal sex and the women always seem to enjoy it. I wonder if we could do it?”

“I’m pretty big, as you already know. I’m afraid I’d hurt you. If we tried it we’d have to take a lot time to prepare. We’d have to relax your butt muscles before fucking.”

“How could we do that?”

“Probably with graduated butt plugs– I’d put one in your butt and leave it there for maybe an hour, then go to a bigger size, and so on until your butt was used to something close to my size.”

“Seems like a lot of work.”

“It probably is and that’s why I won’t ask you to do it.”

Jessie sat up, grabbed Jakob by the hair and pulled him forward until he was only inches from her face. “The hell you won’t! Do you have any idea how much pleasure you’ve given me—how much you’re going to give me? You are going to continue pleasuring me, aren’t you?”

“Yes, Ma’am,” Jakob gulped.

“Well, that’s good, in fact it’s great, but I have to do my share, too.”

“Haven’t you? Let me see,” he said counting on his fingers,” first, you jerked me off. That was the best jerk-off I’ve ever had. Next, you swallowed all my cum. That was a first for me, but, hopefully, not the last. Then you fucked me—another first. Then we fucked and fucked and fucked. I’ll never tire of that. I’d love to fuck your ass, but I’m not going to die if I don’t.”

“Well, I think I want you to do it, so there!”

“OK, we can try, but it will have to wait until we get home.”

“Speaking of home, what’s going to happen when we get back?”

“What do you mean? Don’t you want to be my girl? Go steady? Get married?”

Now it was Jessie’s turn to gulp. “Married?”

“I’ve been tossing it around. I kind of like the sound of Jessie Johannson. What do you think?”

“Married?”

“Sure, but only after college and we get jobs. Of course, we can still fuck in the meantime.”

“You know something? The first time I saw your body I thought we could have beautiful children together. Now you’re telling me you want it to happen. I can’t believe it.”

“Why not? I’ve loved you from afar for a long time I just never thought I’d ever have a chance with you. That’s one of the reasons I hated school so much—seeing you every day in class, at lunch, after school—and not being able to do anything about it almost drove me crazy. I’d go home every day and run to my room so I could jerk off dreaming of being with you. I must have jerked off dreaming of you five hundred times…at least.”

“You jerked off dreaming about me? That’s quite a compliment. I wish I could have seen you.” After a slight pause, she continued, “Jakob, sweetie, I’d love to see you jerk off. Will you do it for me?”

“I’d rather fuck you but, OK, on one condition—that you masturbate for me.”

Jessie thought about it. This could be really hot, so why not? “OK. You’re on. Shall we make a bet of it? Last one to cum has to give oral to the other and swallow any cum. Agreed?”

“Sounds like a bet I’d love to lose. You’re on! I just want to get some lotion so I don’t get a rub burn. I might want to use this again…and soon.”
Jakob got some complimentary lotion from the bath room and rubbed it liberally over his cock which by now was fully erect. They sat with their backs on the headboard so they could see each other. Jakob started to slowly stroke his throbbing dick. He scrunched down onto the bed so he was more level. He was concentrating on the sensations he was experiencing. Jessie had spread her legs and ran her hand up and down her slit, wetting her fingers. When she moved to her clit a gasp escaped her mouth. She was excited. This was the first time anyone had seen her get herself off…AND she got to see Jakob do it, too!

It was a furious race. In the end there were only a few seconds between orgasms and the combatants were so absorbed in their own pleasure they completely forgot to observe the other. Jakob looked at Jessie and they both laughed. “I guess we both owe each other some great oral.”

“I think you’re right, but just now I see some yummy cum I want to taste.” She licked the head of his shrinking cock first then what was stuck on his hand. Then she moved to his chest and licked her way south to his abdomen. Finally, she cleaned his thighs. Jakob found the experience to be a tremendous turn-on; Jessie loved doing it just as much, even more when she noticed the effect her tongue had on his swelling cock.

“I think I’d better get used to having a continual erection. Being around you does it to me non-stop. I just can’t help it.”

“I’ll be worried about when you don’t get turned on. Hopefully, you’ll be seventy when that happens.”

“No way, I plan to fuck you until the day I die. What a way to go—going while cumming!” They both laughed at the joke, knowing that in doing so they were actually pledging themselves to each other. It was Jakob who said it first. “I’ve never said this to anyone…I LOVE YOU…and I always will.”

Jessie was so taken by this she broke out in tears, but they were tears of joy. She pulled herself to Jakob and hugged him, clutching herself to his chest. “I think Jessie Johannson has a wonderful ring to it. I’ll be thrilled to be your wife. They kissed then for what seemed to be an hour. It was only by accident that Jakob noticed the clock on the bed table. It was after one a.m. They fell asleep in each other’s arms pledging their love to each other.

Chapter 6

Being young (and in love) they woke early, looked at each other and laughed. Seeing your lover first thing in the morning is usually a shock. Jakob was about to get up when Jessie reminded him of their bet. To be fair she suggested they 69; Jakob readily agreed. Jessie moved up straddling Jakob’s face before literally diving onto his cock mouth first. She attacked his cock with her mouth, but Jakob was not to be outdone. He loved the taste of her and this morning he had the benefit of licking all of her dried cum from the contest. He looked at Jessie who was doing her best to deep throat him, but with little success. He was simply too broad to fit into her mouth. Recognizing this she changed tactics, using her tongue more actively. It wasn’t long before she could see the initial results. She could see the monster visibly throbbing with excitement. Jakob meanwhile had moved his attentions to her clit. He first licked in a variety of directions then sucked the nub between his teeth while actively sucking and licking. There was no way she could resist such an assault. Her body surrendered; the orgasm erupted through her body. She shook and twitched but she never stopped using her tongue on him and soon she saw the fruits of her labors. She rushed to place her mouth over his cock head so she could swallow all his precious fluids. She was disappointed when the flow stopped so she pulled on the cock eliciting a few additional droplets for her tongue. They both lay back exhausted. About seven they managed to rise and share the bathroom without incident. Neither was accustomed to peeing in front of the other but they managed it without embarrassment. Both saw this as an element of trust in each other.

Today was their day at Sea World. Of course, they were arm in arm on the way in. There were no more incidents with the jocks, in fact his assailant had approached him to apologize. Everyone accepted that they were a couple. Jakob noticed a small jewelry store and led Jessie to it. “I want to buy you something—a token of our love.” They shopped for a few minutes until Jessie spied a silver band engraved with two dolphins. It looked like they were kissing. It fit perfectly and they told the clerk she would wear it. Jessie showed it proudly to her ex-roommates. When she told them it was a pre-engagement they were ecstatic. They went together to all the exhibits and shows. In their excitement they failed to notice the “Splash Zone” signs at the Shamu show so of course, they were drenched to the skin. It was just another reason to laugh and enjoy each other. Too soon, the day was over and they returned to their rooms—all except Jessie and Jakob, who retired to their suite.

This was an evening for packing and getting ready for the long ride home. Jessie and Jakob worked fast to complete their tasks. Jakob finished in about three minutes; Jessie took considerably longer, but Jakob helped. They showered together, soaping each other and kissing under the streaming shower. Jakob used the soap on Jessie’s ass cheeks and decided the interior of her ass could use some cleaning, too. He soaped his fingers and slid them effortlessly into her hole one at a time. When she was able to handle the one, he added another. Eventually, he was fucking her ass with three fingers. Jessie held herself close to him for support. She looked up, smiled, and said, “I told you I could handle your cock. A little more practice like this and I’ll be ready for you.” They left the shower, toweled each other, and slipped into the bed. It was a king sized, but they held each other so closely they could have used a twin.

Their kisses were long and deep. They touched each other, rubbing and caressing, in the expression of their love. Jakob pulled Jessie on top of him so they could couple and become one. Jessie was soaking wet and she had adjusted over the past days to Jakob’s girth so the entry was easy. All the same she went slowly—very slowly—so she could enjoy every second of their union. Rather than move and bring each other to climax they slept in this position, waking occasionally to rekindle. Finally, around four a.m. they could take no more—they needed release. A couple of rocking motions by Jessie, matched by Jakob brought on a thunderous orgasm to each of them. It was so exhausting they fell immediately asleep, still joined together. When they woke again at six there was just enough time for a quickie, another shower, and breakfast before boarding the coach. A surprise awaited them there. Their seats were covered with Valentine hearts and cupids, no doubt the work of her three friends.

The ride home went much too quickly and they found themselves back at the school. Reluctantly, they exited, standing next to their luggage unable to say good-bye. When they saw the Johannson family truck approach they quickly kissed and embraced. “Tomorrow…” they said simultaneously, then turned away.

Jakob’s mother was driving and she was more than surprised to see Jakob with a girl. When Jakob entered the truck she asked, “So, how was the trip?”

“Great, Mom. Much better than I anticipated.”

“Was that a girl I just saw you with?”

“Yeah, Jessie Holmes.

“You mean Boobs Jessie?

Yes, but from now on you’ll refer to her as Jakob’s Jessie. We’re in love, we’ll be getting married once we’re finished with college. We’re both going to State so we can be together. After graduation we’ll look for an apartment near campus.”

Jakob’s mother just sat there with her mouth open. It was a good five minutes before she was able to drive home.

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