Jessie and Billy

Story Info
Another online relationship culminates.
4.9k words
4.47
10.6k
2
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

They both thought it was a little crazy. Crazy, but incredibly exciting. They had known each other for just over a year when the decision was made for them to finally meet up in person. Though there had never been any physical meeting before this, each of them knew every inch of the other's body. They were as intimate as two people separated by the lengths of three states could be. And now they were going to be together for the first time...

Jessie was a nervous wreck. She was not sure why she had agreed to meeting up with Billy and was wondering how good of an idea it really was. The hotel bar they planned to meet at was not very crowded this early in the evening. She sat at a table sipping her drink and thinking of how she had gotten to this point. Remembering the chance encounter with a faceless screen name and how it had lead to a hot session of cyber sex brought a grin to her face. She remembered how she thought it was so amazing how his words were able to turn her on so intensely. The cyber sex gave way to an exchange of pictures. They were tame at first and then not so much. She thought his cock looked good in the photo, but she was completely blown away when she saw a video of him cumming. He had claimed he produced a lot of semen and yet she was still not prepared for such a sight. It was only a matter of time before they both hooked up their webcams and began intense sessions of dirty talk and masturbation for each other. The grin on her face became a full on smile. She sipped her drink again while she eagerly waited for him to show up.

Billy stepped out of the hotel shower and reached for a towel. He still could not believe he actually traveled all this way to meet a woman he had been cyber fucking for over a year. He was incredibly excited, as evidenced by his stiffening cock, but also afraid. He knew she liked him for his words and his potency. He knew she thought his cock was a good size. What he did not know was how this meeting would turn out. As a man he wanted to end up in bed with her, pounding into her pussy for as long as possible. As the guy who had been chatting with her all this time he wanted to strengthen the connection they had made. What did she want? Billy thought Jessie was a very beautiful and hot woman. Perhaps the hottest woman he had ever known. Her hair reached her shoulders and framed her gentle face perfectly. Her smile was brighter than the sun. She had legs that went on forever. And then there was her chest. Possibly Billy's favorite of her attributes, there was no denying that her breasts were enormous. He often fantasized about the attention he would pay them if given the chance. He continued to dry off and noticed his dick was now rock solid. He did not want an unsightly bulge in his pants when he met her. A few minutes and several strokes later Billy unloaded gobs of baby batter into a handful of tissues while thinking of what he would love to do to the woman he was about to meet. He cleaned up, got dressed, and headed downstairs to the bar.

The two of them saw each other almost immediately. There was no mistaking the other's face. Jessie stood up as Billy walked toward the table. Two of the brightest smiles in history spread across their faces when they realized they were actually meeting. Without thinking, Billy and Jessie opened their arms to embrace the other. Their hug was warm and friendly. Despite their already intimate relationship Billy tried not to let on how much he was enjoying the feeling of Jessie's breasts pressed up against his chest. Thinking along the same lines as him, Jessie resisted the urge to grind her crotch into his and feel his bulge through her jeans and panties.

They sat and talked for a while. The conversation was light and a little awkward. Billy and Jessie knew what they wanted from the other. The attraction between them was strong and undeniable. The problem was initiating a move toward a more adult themed evening. Despite having seen and fantasized about each other's naked bodies, they now conformed to societal etiquette.

"I can't believe we are finally here together. In person," said Jessie.

"I know," replied Billy. "It's almost surreal."

Silence. The two of them sipped their drinks while simultaneously thinking of something to say and hoping the other would speak first. Billy, not coming up with anything to say, allowed his cautious guard to fall briefly. His gaze lowered and focused on Jessie's massive chest stretching out the logo on the front of her t-shirt. His appreciative glance lasted no more than a second, but it was long enough for her to notice. Her realization of where he was staring was just enough inspiration for her to break the ice.

"Um, Billy?"

"Huh? Oh! I am so sorry."

Jessie giggled out loud as Billy's face turned beet red.

"It's okay, Billy. I know how much you like them. You've told me a million times."

"I know, but it's just so weird now that we are both here together. I just don't want you to think what we do online is all I'm interested in."

"Don't worry about it. If I didn't want it, I wouldn't be doing it."

They both smiled at each other. The tension was beginning to ease. Still neither one of them knew what to say after that. Silence resumed for the longest minute either of them had ever experienced. Finally, it was Jessie who decided to move things in a more productive direction.

"What are we doing here?"

"What do you mean?"

"We both know what brought us together," she said. "For some reason though you and I just aren't clicking the way we have before."

Billy lowered his head. "I'm sorry. I just never thought this would actually happen. That I would be this close to you and now I am just so afraid of blowing it."

Jessie reached out a hand and lifted Billy's head. He saw her smiling at him. It was the smile he had admired for over a year on his computer screen. He smiled back at her. There was silence again, but it was a comforting silence, as if they both knew what the outcome would be and were waiting for it to unfold. Billy decided to try something. It was a gamble, but he felt it would work. It had to work.

"You want to try something with me?"

Jessie's perfect smile widened. "What did you have in mind?"

Billy leaned across the table and whispered in Jessie's ear, "Let me pay the tab, we'll walk to the elevator, go up to my floor and to my room, and then we will have some of the hottest sex in history."

He sat back down and waited for a response. He did not have to wait long. Within seconds of making his proposal Billy felt a bare foot run up the inside of his leg and rest in his crotch. Jessie stared straight into his eyes while she moved her toes up and down the length of his hardening cock through his pants. Billy took in a sharp breath before signaling the waiter to come over. Once the tab was paid Jessie and Billy rose from the table. He was trying desperately to hide his growing bulge from the other patrons in the bar. By the time they reached the elevator Jessie was hanging off of his arm.

Once inside, Billy pressed the button for his floor and then spun around to pin Jessie against the back wall of the elevator. He caressed her soft face before touching his lips to hers. It was the first time their bodies had ever made direct contact of an intimate nature. Their mouths parted slightly and allowed the other's tongue to enter. Passion was beginning to overcome the awkwardness they had earlier shared.

A bell rung and the doors of the elevator opened. They broke their kiss and gasped for breath. They were drunk on sensuality at the moment. They stumbled out into the hall, Jessie following Billy's lead back to his room. They reached his door and shared another deep kiss while he fiddled with the key card. Once the lock clicked the door flew open and the two of them tumbled in the small room.

Jessie and Billy were holding each other's faces, their lips locked together as they sat down on the edge of the bed. The makeout session continued for several minutes, allowing their kisses to move from each other's lips to their cheeks, chins, and necks. Jessie sat back for a moment.

"I have never wanted anyone so much in my life," she said.

"Me neither."

With that Jessie reach under the hem of Billy's shirt and pulled it up over his head. She put her hand on his chest before telling him to lay back. She swung a leg over him and held herself up on all fours. Hovering over his body she began to plant gentle kisses across his chest and down his stomach. Occasionally she allowed the tip of her tongue to trail briefly over a section of his skin. Billy loved the sensations. He shook every time Jessie worked another inch closer to his cock.

The naughty minx reached Billy's belt and immediately began to unbuckle it. Within seconds his pants were undone and being worked down his legs. Jessie moved back up to where his boxers were coving the incredibly hard tent pole between his legs. She grabbed his shaft through the thin material. A wet spot appeared indicating his pre-cum had begun to flow. She lowered her head and kissed his balls through his boxers. Knowing how close he was to having his fantasy girl make actual contact with his cock was killing Billy.

Billy felt Jessie's gentle hands reach up and grab the waistband of his boxers. She pulled them down so slowly it was almost criminal. The tension on his firm shaft was becoming unbearable. Finally, with one last agonizingly slow tug, the band pulled pass the head of his dick and all seven inches of stood up proud. The cool air conditioned air of the room contrasted with the heat emitting from Billy's rod.

"Oh my," said Jessie. "It's even nicer in person."

"Thank you," was all Billy could think to say.

Really, it was all he had time to say. Jessie wasted no time in wrapping her fingers around the spear she had freed. Her hand began to glide up and down the shaft bringing immense pleasure to the man laying before her. Without thinking she started to kiss and then lick anywhere her hand was not already touching. Starting with Billy's balls, Jessie gave his genitals a long overdue tongue bath. She made sure to note just how big, full, and heavy they felt in her hands.

Jessie placed her lips on the tip of Billy's cock and kissed it sweetly. She ran her tongue along her lips to taste the bit of pre-cum that had smeared on. It was sweet and salty. She wanted more. Her lips returned to the head of his engorged cock and parted to allow it to enter her hot, salivating mouth. When her mouth formed a tight seal Billy began to speak.

"Oh god. That is so good. Your mouth feels amazing on my cock. Please suck it. Suck it more. Oh god."

Jessie was pleased to hear her oral endeavor was appreciated. She eased more and more of his cock into her mouth, sliding her tongue up and down its length as she consumed it inch by inch. Soon enough she had all seven inches in her mouth and deep throated Billy's big cock.

"Fuck that feels good!" cried Billy. "Don't stop baby. Please don't stop."

Encouraged to hold him in her throat as long as she could, she did so. Eventually Jessie needed air, but that did not stop her from sucking hard on Billy's cock as she pulled her mouth off of it. While gasping for air Jessie noticed a line of pre-cum linking her lips back to the tip of his cock. In one cool motion she twirled the thin line of goo around her index finger. Then, looking into Billy's eyes, she held the finger to her lips. Playfully she grinned before slipping the finger in her mouth and licking it clean.

"Mmmmmmmm," went Jessie.

"You like the taste of my pre-cum, baby?"

"Very much."

"I've got a lot more where that came from."

And with that Jessie drove her mouth back down Billy's pole. Her blowjob became more intense. She switched it up between sucking on his cock and running her tongue up and down his thick shaft.

"I want your cum, Billy. Please give it to me."

"Oh god! Here it comes!"

Jessie sealed her mouth over Billy's cock just in time to have the first thick rope of cum blast out onto her waiting tongue. It tasted just as good as his pre-cum if not better. She barely had time to swallow before another gob splashed inside her mouth. That too was followed by another and another and another. She knew he came a lot, but this was unreal. Jessie could swear his shots were getting thicker as his orgasm went on. Billy could do nothing but lay there and enjoy the euphoria produced by exploding in her mouth.

When Jessie had swallowed the last of Billy's cum she stood up and looked down at him. He had a big stupid grin on his face like he had just been named king of the world. She could not help but smile back.

"I guess you're feeling pretty good right now, huh?" she asked though she knew the answer.

"I am feeling very good, but I could be feeling better."

"And how could you be feeling better?"

"I'd be feeling better if you let me return the favor," Billy said with a wink.

Jessie reached for the top of her jeans and began to work them down her hips and thighs. Before too much of her panties were in view she turned around to let Billy watch as her lovely ass was revealed by the falling pants. After the jeans were on the floor and kicked to the side Jessie turned to face him again. Her hands played with the top of her panties until they too were pushed down her legs and onto the floor. Billy's eyes went wide as he saw her pussy for the first time in person. It was shaved and just as inviting as it had been every time he had seen it online. Jessie walked the edge of the bed and then did something unexpected.

Jessie reached up the back of her t-shirt and undid the clasp of her bra. After a few seconds of skillful fiddling she managed to remove it completely while never taking off her shirt. Knowing he was now only separated from the amazing set of breasts he lusted after by a thing layer of cotton made Billy's cock twitch and begin to come back to life. Jessie noticed the movement between his legs and smiled again. She crawled up onto the bed and straddled Billy's torso.

Billy could feel not only the heat coming off of Jessie's pussy, but also tiny bits of moisture falling from her cunt onto his stomach. His cock was at full attention again and beginning to point back and up toward where Jessie's ass was. She looked down at Billy and put her hands on his shoulders to get his attention.

"Billy, I know what you really want. You want to see my tits, don't you?"

Billy gulped and then nodded.

"If I show them to you, will you be nice and eat my pussy?"

He nodded again.

"Good. Now ask me nicely."

"May see your breasts, please?" Billy asked.

"I don't know. I think you can ask nicer than that," she teased.

"Miss Jessie, I would love nothing more than to see your amazing tits. May I please see them in all their glory?"

"Much better," she said.

Jessie moved her hands from Billy's shoulders to the hem of her shirt. In one smooth motion she lift the garment up over her head and flung it across the room. Billy was in a state of awe. He was dumbfounded. Mere inches from his face were the most magnificent breasts he had ever seen. The inspiration of so many fantasies was finally within his reach. Despite all his excitement and enthusiasm he could not move a muscle.

Sensing she had just overloaded his brain, Jessie took Billy's hands in hers and raised them up. She rested his palms over her nipples. The contact was electric. It sparked consciousness back into Billy. Immediately he began to squeeze Jessie's breasts. He kneaded her tit-flesh between his fingers. The rough foreplay felt good to her too. She knew how much he loved her tits. Knowing how much he was enjoying himself just then made Jessie's pussy even wetter.

Even though they both were enjoying the tit play, Jessie needed something more substantial to quell the fire in her loins. Slowly she inched upward until her cunt was just over Billy's mouth. He could smell her sex and her need. She was hot, wet, and horny. She was ready to be touched and brought to orgasm. Jessie leaned forward so she could grip the headboard. Billy's hands slid down the sides of her body and came to rest on her hips. Together they lowered her steamy pussy to his lips.

Billy kissed her swollen cunt lips softly. Her juices seeped into his mouth. She tasted sweet, as he knew she would. He kissed her pussy again. Each time his lips met hers he was rewarded with more of the sweet nectar she produced. After sampling such small portions of her honey Billy stuck his tongue out and licked Jessie's entire slit up and down one time. Jessie moaned in appreciation. Her clit became engorged and began to peek out from under its hood. Billy moved his hands from her hips to her ass in order to pull Jessie tighter onto his mouth. He dove in deep with his tongue, eagerly lapping at her cunt, trying to taste as much of her as possible. He moved his lips up over her clit and sucked on the little nubbin.

"Oh yes! Yes! Right there, Billy!"

Jessie's cries of passion urged Billy on. The tip of his tongue flicked her clit as he sucked on it harder. More of her juices leaked out onto his chin and down his neck as she began to buck her hips on his face. Billy became emboldened by Jessie's obvious pleasure. He began to think over what he knew about her, what she liked in bed. Suddenly an idea came over him. Billy stuck his tongue back into Jessie's pussy and swirled it around. At the same time he moved one of his hands away from her ass and brought the palm right back down on it.

SLAP!

"AH! Yes! Smack my ass, Billy!"

SLAP! SLAP! SLAP!

Billy's hand came down on Jessie's ass cheek again and again. His red palm prints on her skin like a cattle brand. He could hear her beginning to gasp for breath. He knew it would not be long before she came and he would be rewarded with a mouthful of her sweet sweet pussy honey. He redoubled his efforts. His tongue lashed at her clit and dove into her hot hole. Back and forth he switched it up between sucking on her clit and licking her sugar walls clean inside of her. All the while he kept alternating which hand he used to smack her willing ass.

SLAP! SLAP! SLAP!

"Oh god! Almost there! *gasp* Oh FUCK! *gasp* OH BILLY!"

Hearing Jessie cry his name was the last sound that enter Billy's ears before her calves covered them up as they clamped around his head. Copious amounts of pussy juice poured out of Jessie's well eaten snatch. Billy tried his best to drink it all in. Above him, Jessie's body went stiff and then began to writhe. Her back arched as she slammed her pussy down hard on Billy's talented mouth. Jessie's knuckles went white as her grip tightened on the headboard. Her eyes screwed shut and Billy dug his fingers into her soft butt cheeks in an attempt to bring her cunt even closer still.

Jessie rode out the remainder of her climax on Billy's face. Her breathing was incredibly labored as she came down. Ever so slowly Jessie moved over to Billy's right side and lay nest to him. They wrapped themselves in each other's arms and looked deeply into their eyes. For a moment neither of them spoke. They did not have to. They were satisfied for the moment. The awkwardness was completely removed from their meeting. Billy leaned in and kissed her again. His lips were gentle and tender against hers. She kissed him back and their embraced gained strength.

"That was really nice," Jessie told him in between kisses.

"Mmmmm. Thank you," Billy replied. "You were amazing."

Their lips continued to meet off and on over the next few minutes. During that time Jessie noticed something delightful happening. Billy's cock had stayed hard the entire time he ate her out and was now poking her between her stomach and pelvis. She could feel the small droplets of pre-cum from the tip of his dick sticking to her sweaty skin. She could tell he was fully hard without even looking. Her well eaten pussy started to moisten again as well. There was one more thing they both wanted from each other and Jessie figured it was time they got it.

12