Blue Monday

Clapping her hands together, Jessica pointed towards the couch with her right hand index finger.

"Go sit down and make yourself comfortable."

"I guess I should take my clothes off too."

Jessica shook her head.

"No, let me strip you instead. It's better that way since this is your first time. I'm gonna give you something you'll never forget."

She giggled at him again as James stepped his way over to the couch. As he sat down on the left side, Jessica followed. She took a seat directly in James' lap, straddling him. This was the first time in his life he had a girl sitting on his lap, but this wasn't just any girl. James moaned and moved his hands to her hips. Jessica could feel his bulging cock poking between her thighs. She made an effort to grind her hips while calling out to him.

"Mmmmm, what are you waiting for, James? You can put your hands all over me."

Jessica spoke in a seductive tone. Still grinding on his lap, she moved her hands up to the shoulder straps of her bra and then undid it. James wasted no time sliding his fingers up her sides, but when she pulled the bra off, his attention went to another place. She dropped the bra to the floor and then stopped grinding. Jessica shook her tits left and right until James pushed his hands down on them. Letting out a soft moan, she giggled at him.

"Yeah, there you go. Give 'em a hard squeeze, mmmmmmmm!"

Biting her lower lip, she moaned. James could feel her hardened nipples poking into his palms. He leaned his head in, eager to open his mouth and suck on the right boob. Jessica guided his face between her tits. Shaking them again, she forced her big beauties to beat up against his cheeks. James squeezed them and then shook his head around while slobbering. Jessica laughed loudly at his attempt to motorboat his tits. For a virgin, he knew what he was doing so far. Moving his lips back to one of her nipples, James eagerly sucked while Jessica patted him on the head. She was pleased with his efforts, but the reveal of her breasts was only the beginning.

"Sit up for me."

She commanded him while getting off his lap. Standing on her feet again, Jessica turned around. She leaned forward and slid her hands into the side straps of her thong. James sat up, gazing into her perfect round booty. The thong fell and then Jessica bent over further, splitting the crack of her ass. She shook it up and down, pulling her right hand back to playfully spank herself. Swaying her hips left and right, Jessica slowly turned around. James raised his eyebrows when he finally witnessed her pussy. Though he had seen it behind sheer clothing earlier in the day, now it was fully exposed. Completely shaved and glistening with fresh dew. Jessica watched his eyes before she slipped her right hand down and carefully stroked her clit with her middle finger.

His eyes glanced up, as if James was almost caught in a trance. Her beauty alone was enough to leave him motionless, devoting all of his attention to her. The only piece of her outfit she kept on was the thigh-high blue socks. The temptation was there for him to go ahead and strip. His cock was desperate and awaiting the touch of her hand. He knew better than to pleasure himself as Jessica's green hues glared back at him. She slid her finger beyond her clit, sinking it between those pretty pink folds. Exhaling deeply, she softly moaned. That was all Jessica did to break the silence before reaching out and grabbing the ends of his shirt. She tugged it and then James helped himself. Pulling the shirt over his head, he slung it to the floor to reveal his skinny chest and pale skin. When he glanced forward after tossing the shirt, Jessica had fallen down to her knees.

Her big green eyes glared up at him as she bit her lower lip. Poking her head out from between his legs, she quietly patted the bulge in the front of his shorts. The grin across her lips told him everything he needed to know. For what was about to be his first blowjob, Jessica had the glare of a true vixen. She grabbed the front of his shorts with both hands and began to tug them down. As the shorts fell down to his ankles. the last piece of clothing on his body was that pair of white underwear. Jessica giggled at the sight. He expected her to say something about his tighty whities, but she kept her lips sealed. When her fingers finally pulled his underwear down, James let out a sigh of relief. His hard cock flopped out, now free from the clothed prison. The briefs dropped down to his ankles, where he shook his feet free, now leaving his underwear and shorts on the floor.

"Mmmmmmm, look at this."

Jessica wrapped her left hand fingers around his cock while speaking quietly. James moaned at the subtle squeeze she gave his erect pole. Gazing at his face, Jessica giggled.

"What a treat. I get to suck it first before any other girl gets their hands on you."

As she began to pump her hand up and down, Jessica spoke again.

"You never forget your first blowjob. That means you're never gonna forget about me, darling. I think that makes me special, huh?"

Nodding his head, James took a deep breath and swallowed.

"Yeah, but you were already special, Jess."

Her eyes locked on his face as she parted her small pink lips. James watched in amazement, first feeling her breathe across the head of his shaft before sliding it in.

"Ohhhhh, man..."

Moaning, James braced himself as he stretched his fingers out. His eyes never left Jessica's face as he watched the cosplay queen begin sucking him. Her hand shoved down to the base, still gripping his rod. She took her time, slowly sucking the first few inches. As she began to bob her head up and down, all he could do was think about how often he dreamed of this moment.

"That feels so good. Please keep sucking, Jessica."

Again, he swallowed his breath. James watched her lips pull back to the head. Jessica released him with a loud popping sound.

"Mmmmmm, you didn't have to say please."

Giggling at him, Jessica kissed the head of his cock. She began to stroke it up and down with her left hand but only momentarily. Her hand rested down at the base in his bush of pubic hairs. Studying those fingers twisted around his shaft, James suddenly caught sight of a tattoo on her middle finger. He had never noticed it before in her photos or earlier in the day. A wi-fi symbol with three bars was etched into her skin. Looking back into her eyes, he watched Jessica lick the underside of his shaft. The tip of her tongue swirled around the head, and then she shoved it back between her lips.

"Oh god! Yes!"

James called out to her in excitement, now feeling his cock back inside her mouth. Jessica devoured him, sucking inch after inch. She used her hand to stroke up in time with her lips sucking, giving him the pleasure of a blowjob and a handjob at the same time. Groaning out, he was so tempted to lower his hand on her head like he had witnessed in porn videos, but James maintained himself. So far, he felt that he had some ways to go before reaching his orgasm. That was something he had not considered so far, but the nervous tensions earlier were still bubbling within him. Jessica pulled her lips back to the head of his shaft and released it again with another popping noise.

"Mmmmmm, yeah!"

Flicking her tongue, she spit on his shaft. Her eyes moved to his face as she grinned up at him.

"You like that?"

"Yes I do. I love what you're doing to me."

Jessica spit on his cock again. She began to wank him again, pumping her hand up and down. Her eyes did not glance away from his face as she jerked her hand faster. James took a deep breath, then watched as she parted her lips and stuck her tongue out. Smack. Smack. Smack. She slapped the head of his dick against her tongue. James expected her to suck it again, but Jessica was not quite done toying with him yet. Lowering her head, Jessica kept her left hand fingers wrapped around his cock. With her right hand, she was able to squeeze his nut sack hard.

"Ohhhh! Fuck!!"

She giggled at his reaction.

"That surprised you, didn't it?"

"Sure did, you can say that again!"

Laughing at him, Jessica squeezed his nuts once more with her right hand.

"For your first blowjob, I think it's important that these aren't ignored."

He knew what she was referring to. Within seconds, James could feel her wet tongue lapping over his hairy ball sack. Groaning out in pleasure, he called to her.

"Jessica! Ohhhhhh, god!"

Her left hand wanked his shaft, pushing up and down while her right hand fingernails grazed across his nuts. She used her right hand to help shove one of his balls into her mouth. Those feelings made him want to immediately stand up, but James maintained himself.

"Keep sucking it, oh man!"

The more he moaned, the faster she pumped her left hand across his rod. James could see the entire length of his shaft stretched out across her forehead. After sucking one nut well enough, Jessica popped it from her lips and shoved the other one in. 'Mmmmmm', she made a muffled moaning noise while slobbering all over his ball sack. Her right jaw briefly inflated before she released the other ball from her mouth. To finish him, she lapped her tongue across his sack for a final time.

"I'm not done yet, sit back and relax!"

Jessica winked before sliding his cock back into her mouth. At long last, she unwrapped her left hand fingers. She began to bob her head up and down, now using both hands to push down into his legs. Without her fingers in the way, Jessica could properly deep-throat. Over and over, she bobbed her head up and down, devouring his dick with ease, while her big green eyes never glanced away from his face. With each passing second of sucking, James noticed her pushing it deeper down her throat.

"Oh my god!"

He cried out to her, scrunching his face up and gritting his teeth. Jessica's actions had only made James more excited. She shoved her lips all the way down, sending the head of his cock to the back of her throat. It was amazing to witness his entire rod disappearing between her lips.

"FUCK!!"

His scream echoed throughout the suite. Panting and breathing heavily, little could he have expected her to deep-throat him so suddenly. Jessica held herself there for a moment, leering her eyes to view the conflicted expression on his face. She winked before pulling her lips back and releasing his shaft from her mouth. Strings of saliva dangled from his now shiny, spit-soaked cock back to her open mouth. They dangled before breaking as Jessica smiled wide.

"Mmmmmmm, you've got a great cock, James. It's big enough to take a trip somewhere."

"I think I can guess where that is."

Laughing at him, Jessica shook her head. She moved her hands over her great big tits, shoving them up and then swaying left and right. She did this maneuver to give them a slight bounce.

"Wanna take a trip to Titty City?"

Jessica grinned, quirking her eyebrows up while bouncing her boobs in her hands. James returned the smile, nodding his head and finally standing up. The excitement was too much for him, as he could no longer sit still. His slobber coated shaft swung left and right before James gripped it with his right hand.

"You wanna fuck my tits, James?"

"That's something I've always wanted to do. You have no idea how bad I wanna do this."

Laughing at him, Jessica was quick to reply.

"Well, today is your lucky day! I might as well tell you now, that I love having a big dick shoved between my boobs. You've won a free way ticket to Titty City."

James decided to play along with her kinky talk.

"So how do I get there? Is it by bus, train, or car?"

She pulled her breasts apart, offering a passage right in the middle.

"How about by cock? Go ahead. Slide that big dick between 'em. You know you want to."

He did not have to be told twice. James guided his shaft directly between her big boobs, then pulled his hand away. Jessica squeezed her tits, trapping his cock between them. Flashing her pearly white teeth, she grinned at him before giggling.

"Mmmmmm, doesn't that feel good? I can't believe my tits are the first for your cock. Look at that. Look how perfectly your cock fits right between 'em."

"Ohhh man, I can't get enough! It feels so damn good!"

Jessica squeezed her tits tighter around his pole after that remark.

"Mmmmmmm, yes it does. Come on and fuck my titties, James."

Unable to maintain eye contact with her, James fixated on the view of his cock shoved between her boobs. The head was poking up. Swallowing his breath, he began to thrust his cock between her tits. Jessica exhaled, then broke eye contact to glance down. She giggled at the feeling of his shaft pumping between her tits.

"God, look at that. Your cock is so gorgeous between my tits, isn't it?"

"Oh yeah!"

Still pumping between her tits when he replied, James moaned. He abruptly slowed down when Jessica's eyes glared back at him. He glanced into those deep green hues, taking another thrust. He could slowly feel every inch of his dock sliding up her tits. As their eyes met, Jessica teased him by moving left and right. She smiled, flashing her full teeth while shaking her boobs. Her hands still cradled them.

"Enjoying your stay in Titty City?"

Her dirty question prompted a slow nod from James. Jessica giggled.

"If so, then you can begin fucking these titties as you please. Fuck 'em hard, James."

With a soft moan, he began to buck his hips again. James watched his cock disappear between her tits with the head poking back up. Jessica glanced down for a moment, then leered her eyes back at his face.

"Mmmmm, now you see it..."

As his cock thrust back between her tits, she spoke again.

"Now you don't!"

The head poked back up with a full thrust. James could feel himself finding a rhythm in this movement. It was amusing to him that he was here fucking her tits before he had a chance to experience his cock being inside her pussy. The real sex was still a prize for later, if he could hold himself back from exploding between her boobs. Still pumping his cock between her tits, he watched Jessica glance down. She parted her lips, flicking her tongue across the head when he thrust up. Her eyes moved back to his face before she spoke to him in a low voice.

"That's it, that's it. Fuck these titties."

"I could do this all day!"

Thrusting harder and faster, James groaned out. This feeling was almost too much for him. To think about all the fantasies he had over her boobs and now he was living the dream. Over and over, he pumped his cock between her tits. Jessica made an attempt to spit on the head as it drove up, but she missed and her saliva landed on her left tit. No longer attempting to make eye contact, Jessica concentrated on watching his cock push up between her tits with each thrust.

"Fuckin' A! Woooo, these tits rock!!"

With his bold exclamation, James continued to thrust. His cock slammed between her tits at a faster pace, the head nearly poking her chin with each full thrust. Jessica almost lost her grip on both tits. She adjusted, using her wrists to push her tits together and freeing her fingers. She immediately folded her fingers, almost into a fist. With each thrust, her hands bounced from the sheer force of James fucking her tits. Her eyes never gazed back up. With each thrust he made, she was still watching the head of his cock pump up.

"Fuck yes!!"

Beginning to slow down a bit, James was concerned that if he continued at this fast pace, he would undoubtedly blow his load. The desire to become one with her was greater than wasting his cum between her tits. Finally, Jessica's eyes returned to him. She grinned, flashing those perfect white teeth.

"Feel like making a run from Titty City now?"

She moved her hands, still cradling her breasts but now using her palms instead of her wrists. Squeezing her tits harder around his shaft, Jessica moaned.

"Mmmmmmm, you're worried about having a leak, aren't you? Don't wanna blow your way out of Titty City with a mess?"

Her dirty words in a low tone were almost enough to make him cum. Glancing down at the head of his cock, she flicked her tongue across it. A small bit of pre-cum oozed from the head. Jessica licked her lips as a way to subtly tease him as he came to a complete halt. James could not fuck her tits any longer. Not without the fear of losing control and reaching his climax too soon.

"Time to leave Titty City, am I right?"

"Ohhhhhh, I hate to say so, but yeah."

Laughing at his words, Jessica pulled her tits apart to free his cock. It flopped around before she grabbed it with her right hand. She then held her tits up with her left arm, propping them underneath. James stood there and watched her rub the head of his cock up against her left nipple. With her eyes focusing on him, she grinned before speaking.

"With one last stop, you gotta pay the toll fee."

Smack. Smack. Smack. She beat his cock against her hardened nipple. Rubbing his rod over to the right side, Jessica spoke again.

"Three hits for both tolls and now you're free to leave!"

Smack. Smack. Smack. Again, she hit his cock against her nipple as James groaned at the feeling.

"I'll be daydreaming about going back to Titty City all week."

Still gripping his cock, Jessica began to rise from her knees. She shoved her breasts against his chest, allowing James to feel those perky nipples his cock was touching merely seconds ago. He cupped her face, feeling her arms thrown around his neck, before they embraced for another round of passionate kissing. He moaned into her mouth, then felt her pull away. Looking back into his eyes, Jessica grinned again.

"I'm impressed you've managed to hold yourself back this far. I think you've had enough fun with my tits. It's time to do some real fucking."

Pulling away from him, Jessica turned to the couch. James watched her bend over, placing her hands down on the cushion seats as she gazed towards him.

"Get behind me. I like to take it doggy style."

As she grinned, James nodded. He began to step around her while speaking.

"You know, it was really hard to stop myself when I was between your tits. I don't know if I can hold back this time when I'm inside you."

Once he was standing behind her, Jessica glanced over her right shoulder.

"I think I get what you're trying to ask me. You wanna fuck me until we both? I'll let you cum inside me, if that's what you want. Don't worry, James. I'm on the pill."

Tossing him a wink, Jessica turned her head and gazed forward. From where he stood, James had a perfect view of her ass. The temptation was in him to reach out and spank it, but instead he gripped his shaft and guided it between her thighs.

"Someone's pretty excited to have their first fuck!"

She spoke while shoving her buttocks back. James' cock slipped, rubbing against her vulva lips.

"Go on, get inside me. I know you've been waiting to do this for a long time."

At long last, James was about to be fully relieved of his virginity. He was no longer nervous, as he was in the beginning. Now guiding his cock beyond her pink folds, the first feeling he experienced was the incredible warmth of her pussy followed by the tightness. Jessica moaned as he began to thrust in.

"Ohhhhh, yeah. That's it! I haven't been fucked by anyone at a good Florida event in four years."

James ignored her exclamation. Only for the time being, he needed a moment to embrace this wonderful feeling. All that time he considered what this moment would feel like. Finally he knew the joy of having his cock inside a warm pussy. His hands found a place on her hips and he began to thrust. Jessica closed her eyes, exhaling her breath.

"Mmmmmm, yeah. Fuck me."

Two words he did not expect a woman to tell him. Now that he had it spoken in encouragement, James continued to thrust. Jessica spread her fingers across the cushion of the couch, keeping her head down as her breasts began to wobble and shake from underneath.