Jess, Ch 2: The Surprise Next Door

Desperate times call for visiting the virgin neighbor boy.

Jess waved goodbye to her parents as they drove off for traditional weekend dinner and movie date. They had almost skipped it to spend more time with her since she was only home for a few days, but she insisted on them having a good time. As they drove out of sight, Jess smiled; she was about to have a good time too.

Jess unbuttoned her jeans as she walked to her room. They slid off her gently curving hips as she shut the door. She was so horny, but it seemed the universe was conspiring against her having a good orgasm since her break from school had started. Her room was next to her parents, and she couldn’t risk them hearing her. This limited her to rubbing her clit with her face pressed against the pillows to silence her moans. Which just left Jess more frustrated; she needed something inside her. She had planned on taking a toy in the shower, but her parents were remodeling, so the only available shower was in the master bathroom. But now her parents were gone, and Jess would have the house to herself.

She shuddered as she touched her pussy through her panties, which were already damp. They were plain, girly pink briefs. She couldn’t risk her parents seeing her racier underwear, they might suspect her new college lifestyle and insist she switch to a local school. She pulled off her shirt to reveal a boring white bra that covered her full breasts well. She couldn’t wait to get back to school and put on her lacy thongs and sheer demi bras that barely held in her D-cup tits and large pale nipples. Jess opened her suitcase and fished out her laptop and the small bag carefully hidden in the bottom. As she waited for the computer to start, she shut the blinds before she removed her bra. After all, she couldn’t have the neighbors see her.

She worked very hard to get her innocent angel reputation in her hometown. Years of being sweet, with her long wavy strawberry blond hair looking perfect, her naive-looking green eyes, and always wearing tops that hid her ample breasts and unflattering swimsuits had made it so that her parents trusted her at a party school across the country. Jess unlocked her computer and opened her folder of homemade movies. She knew which one she wanted to watch first.

It was a movie of the last time she had sex, the night before break started. She hit play and took off her panties as the video showed her tying her roommate Melanie spread eagle to the bed. Her hand moved down her thin patch of pubic hair to touch her clit as she watched herself kissing her roommate and teasing her with a vibrator. In the video Jess slipped the vibrator into Melanie’s pussy. While she watched, she slipped a finger in between her own pussy lips and moaned, happy there was no one to hear her. “Stop teasing me Jess, please,” Melanie had pleaded. The vibrator had been set too low for her to get off.

Watching the video, Jess pulled her finger out of her pussy and reached for the small bag. It was torture, what she did. Jess thought about that night, leaving Melanie tied up with the vibrator on low and bringing a fuck buddy to have sex on top of her while she was forced to watch.

Tom had pounded her doggy style with her tits bouncing in Melanie’s face, just out of reach of her lips. Melanie whimpered with envy as Jess had three powerful orgasms and Tom sprayed his cum all over Melanie’s tits before she was untied and had a massive orgasm of own. Melanie swore revenge, but for now Jess was going to enjoy the movie.

When Jess opened the bag however, her eyes widened. The bag was empty, her favorite rabbit vibrator and all her other toys were gone! But the bag wasn’t completely empty, Jess found a photo. It was her vibrator, pushed into Melanie’s bald pussy! There was a message written on the picture, “Payback’s a bitch!” Jess could have screamed. She needed her favorite toy in her, she needed a mind-blowing orgasm!

The sound of a car outside took her away from her misery. Jess peeked through the blinds to make sure her parents weren’t back for something forgotten. It wasn’t them, but her neighbors, heading out. She was about to leave the window when a dim light came on next door, in the neighbors’ son Jim’s room. Then Jim shut his blinds. Seemed like he wanted some privacy too.

She thought about Jim, he had just hit a growth spurt since she went to college and he started high school. He was completely average physically, still a little shorter than her, but not ugly at all, yet she knew that he was socially awkward and had no friends. A wicked smile appeared on Jess’s lips. No friends, no one to believe him. Desperate times called for desperate measures, and she was beyond desperate!

Reaching into her suitcase Jess pulled out the only sexy underwear she had packed. The blue bra wasn’t sheer, but it was lacy and cut low enough to expose the top of her areolas. And the matching panties weren’t thongs or crotchless like she preferred, but they let the bottoms of her round ass cheeks hang out. She tossed her shirt and jeans back on and hurried over next door. Sneaking in through the back door Jess made her way to Jim’s room. Her nipples grew hard as she heard moans through the door.

Jim’s door was cracked open, and he was sitting at his desk with his back turned to her. He was naked, except for a towel on his lap. He was watching porn, with a hand was under the towel. Jess slipped into the room unnoticed. Jim was too busy watching a woman strip out of a cheap schoolgirl outfit. She looked to be about 20 years too old to be in school, with bolted-on DD tits, but Jess massaged her own breasts as she watched the actress suck a cock. Jess wanted a cock in her mouth, too. As the girl started riding the cock, Jess made her move.

“That’s terrible!” she cried out. Jim spun his chair around, pulling the towel around him to try to cover his body. He was a little more muscular than she expected, so that was good. Jim tried to speak, but Jess cut him off. “Those tits are just too fake! Just look at them flopping around! I think real tits are so much better. Don’t you agree?” And with that she pulled off her shirt.

Jim just stared at her, slack-jawed. She knew he was trapped by the sight of her perfect breasts and her nipples pushing against the thin fabric. She unbuttoned her pants, showing off the front of her panties as she walked towards him.

“What do you think of them?” she asked. Jim was still speechless, but his grip on the towel had loosened. She brushed her hand on this towel, knocking it to the floor. Then it was her turn for her jaw to drop.

Jim’s dick was a little longer than average, but Jess had fucked longer. What made her eyes bulge was its girth. It was the thickest cock she’d ever seen! It was at least as big around as a beer bottle! Jess had never put anything that big around inside her, but her pussy was practically dripping with the thought of it.

“Oh My God! Let’s make a deal. You promise to keep your mouth shut, and I’ll let you put that fat cock in me. This is a one time deal, and it’s just sex! No strings attached. And if you tell anyone, I’ll tell them that you’re a liar and a pervert. Do you agree?” With that she let her pants fall to the floor and started running her fingertip around Jim’s fat cock.

“Uh-huh,” was all he could reply. He looked like he was going to cum at any moment, virgins always came quickly. She wanted to stuff her pussy, but she also wanted to see how much of him she could fit in her mouth. She knelt down and wrapped her lips around Jim’s huge cock, but she could only get the head in comfortably. It seemed to be enough though, because as she ran her tongue under the base of his head, Jim started spasming, and fired a large stream of cum at the back of her throat.

Jess swallowed readily, but was caught off guard by the second stream, as big as the first. As the third stream hit her she gagged, and cum started pouring out of her mouth and onto her tits. But Jim wasn’t done. Jess lost count of how many times his dick twitched and sent more thick hot cum falling out of her mouth.

When he was done, Jess swallowed what was left in her mouth, but from her neck to her panties she was covered in a porn star amount of thick jizz. Jim tried stammering an apology, but Jess smiled as she took off her soiled bra.

“That was amazing! And you’re still rock hard, good.” She pulled out her phone from her jeans and handed it to Jim as she wedged his cock between her large, messy breasts. “Take a picture, I want a souvenir.”

He did as he was told, then asked quietly, “Do I get a souvenir too?”

Jess handed him her bra. “Of course! And if you fuck me like a good sex toy you’ll get the matching panties too.” And with that she pulled off her panties and wrapped them around his sticky cock. She pulled him up by his hard-on and moved him onto his bed. Jess straddled Jim and started rubbing his hand into her pussy.

She moaned and said, “Feel how wet I am. God, you’re so big, we’ll have to take it slow.” She rubbed her wet lips against Jim’s dick, then slowly eased them around the fat head. She gasped loudly, her pussy was on fire! Jess rocked back and forth slowly, her moans becoming louder as she slowly slid down his shaft.

Jim looked like he was in heaven. “Can I touch your boobs?” he asked shyly.

“Uhh, yes,” Jess managed to get out between moans. “What–ever…you…want–uuuhhhhh–just don’t…leave any…marks…” So Jim reached up and started kneading her breasts. Jess was almost halfway down his thick pole when he started rubbing her hard nipples between his fingers. This pushed Jess over the edge, and she screamed out and convulsed with a violent orgasm that made her lightheaded.

When the stars in her vision cleared, she realized that she had slid the rest of the way down his cock. It felt amazing! Jess started sliding up and down. Jim was so captivated by her bouncing breasts that he didn’t seem to notice the drops of cum that fell off her and onto him. She leaned forward to put his face between his chest, and he greedily began licking and sucking on her nipples.

After only seconds of that Jim started bucking his hips against her, and she felt his cock twitching as he pumped jizz inside her. She looked down and saw that it had been another huge load, with cum oozing out of her stuffed hole. And the boy was still hard as a rock!

“You think you can handle being on top, big boy?” He certainly could. He pounded her drenched pussy while she lay on her back. She moaned and wailed as his young balls slapped against her ass. Jim pawed at her breasts and nipples clumsily, trying to thrust with his hips and massage with his fingers at the same time. But Jess didn’t care. This is what she wanted. What she needed. She had two small orgasms before he pulled out and shot a small load on her stomach. Jim seemed to be running out of seed. But his messy cock still looked ready to go. She started to lick her juices and his cum off the head, and she felt some of his jizz leaking from her pussy.

“Oh my God, is that monster prick ever limp?” Jim told her that he probably could only go one more time. “Well as your reward for that last orgasm, I’ll let you pick the position.”

That’s how Jess ended up on her hands and knees, with Jim positioning himself behind her. Cum was still leaking out of her pussy onto the bed. Jim stopped it by easing his cock into her dripping snatch. Jess dug her nails into the pillow as Jim thrust the rest of the way in. Her whole body was rocking in rhythm with his pumping, cum dripping off her body.

Jim slowed down, and just as Jess was about to beg him to fuck her, she felt a finger circling her asshole. “Can I-” Jim started to ask, but Jess cut him off.

“Put your finger in there now, big boy.” He did as he was told, and the sensation was amazing. Jess hugged the pillow to her chest, not caring that it was now covered in sticky semen. Jim kept pumping into her pussy, and with the finger in her ass it finally became too much. Jess started convulsing with her biggest orgasm yet. She screamed with the ecstasy of it all. She collapsed on the bed, shuddering. As her pussy sent convulsions through her, she was dimly aware of Jim’s hot seed dribbling onto her back as he climaxed.

“No more,” she gasped, “I can’t take any more…” She looked over at Jim, and saw that his cock was finally starting to soften up. “That was amazing, big boy!” Jim started looking a little love-struck, and he asked if she could see him again before she left.

“No, this was only a one time thing, remember? Anyways, I’ll need a day or two to recover from this. But since you were such a good boy, I’ll give you one last reward. Who’s the biggest slut, the biggest gossip, and the girl you want to fuck most at school?”

“Sally Myers, Jane Henderson, and… Mary Sanders.” Jim blushed a little at the last name. Jess recognized the names. Sally was definitely a slut in the making, and Mary was rumored to be sweet but naughty, just like her.

Jess cupped her neighbor’s chin in her hand. He didn’t seem to notice that it was sticky with their juices. But then again, they were both covered with cum and pussy juice. “And if they ask you who anonymously sent them a picture of your massive beast, what will you tell them?”

Jim’s eyes widened, “Um, I don’t – that – it wasn’t you. It was a girl I met online. From a different school.”

“Good boy,” Jess put on her jeans, ignoring the cum leaking out of her and down her leg.

“But why?”

Jess put her shirt on, not caring or even seeming to notice that it clung to her body wherever Jim’s cum had landed. Her nipples were covered in cum and spit, and could be seen poking through the fabric. “Because you did well tonight. And,” she picked up her messy panties and draped them over Jim’s almost soft dick. “You simply can’t let that go to waste. You’ll never have to jerk off again.”

Jess started towards the door, but Jim said, “Wait.” She stopped, and he blushed even more than when she had first caught him. “Can I – would it – I’m sorry, I shouldn’t.”

“What is it, big boy?”

“This was amazing. But…I’ve never kissed a girl before.”

Jess laughed, not at Jim, but at his situation. “Oh my god, you’re so sweet.” She walked up to him, leaned down, and kissed him. A slow, sensual kiss, their lips parting ever so slightly so her tongue could enter his mouth and touch his.

They parted, and without another word, Jess went home to shower.

*****

Melanie was in her dorm room, laying on Jess’ bed. She had just used Jess’ vibrator to bring herself to another orgasm, when her phone beeped. Picking it up, she saw it was a picture. Her eyes widened when she saw Jess’ perfect breasts, covered in cum, with the fattest cock she had ever seen sandwiched between them. The message with it said, “I had to find another sex toy, this one definitely did the trick!”

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