A Change of Scenery Pt. 01

Jimmy tried to back away when Bridget cupped her hand near his cock but she wasn't having any of it. He groaned in discomfort as he felt Bridget's soft hand on his member. She stroked him teasingly and ever so slightly dropped his boxers down. Caught in the moment, Jimmy didn't even realize Bridget pull his boxers down and off releasing him. The cool air felt nice on his cock and he looked down to see his hand wrapped around her cock while her hand was wrapped around his.

"Wait... I can't..." he weakly protested.

"You can't what?" Bridget asked intrigued. Jimmy knew there wasn't much he could say, his cock was doing the talking, he was obviously aroused despite what was happening. A sharp moan escaped him when he felt Bridget tug on his cock. She led him to her bed and sat him down. He looked up to see a smiling Bridget before him, "Now what can we do to help our little problem?" she asked him. He looked to her throbbing cock, then to his. "I think we should have some fun!" Bridget closed in on Jimmy and pushed him onto his back. Her leaking cock pressed into his shirt and could feel the hot sticky dampness soak through.

Jimmy wasn't sure what Bridget was doing since he was so preoccupied with her ragging hard on pressing into him. He failed to notice her taking off her shirt and then slide back down so they were face to face. He now noticed Bridget's breasts, in the past he would've loved to have seen them, but given the circumstances he wasn't sure how to feel about it. Bridget kept smiling down at him and he smiled back nervously. "Ah there we go! Finally something a little positive!" Bridget smiled again and worked her way down Jimmy's torso. She planted a soft, surprisingly soothing kiss to the head of Jimmy's cock. He moaned with no control and wondered what was going on, this doesn't seem right... he thought.

Her lips on his cock were too good to be true but he couldn't deny the pleasure and rested his head back in satisfaction. She kept teasing him, never venturing any further than the tip of his cock. Her lips were so good, the soft warm wetness. He shuddered a few times when her tongue flicked across his opening. "Mmmm, that's my boy!" she moaned.

Jimmy was so relaxed by this point he didn't notice Bridget preparing herself. All the while she was servicing Jimmy; she was applying a generous amount of lube to her aching cock. With a pop from her lips, Bridget pulled away and smiled down at her new boy toy. Jimmy opened his eyes after he noticed that the warm wetness was gone. He saw Bridget evilly smiling down at him. He looked down to her crotch and saw her erect seven inch cock glistening with lube.

His eyes were wide and before he knew what was going on; the tip of Bridget's thick cock was firmly against his virgin anus. Jimmy tried to pull away from Bridget but she had her hands locking his ankles, "Oh no you don't!" she laughed, "You're not getting away from me! Especially with that cute little ass of yours!" Jimmy squirmed below Bridget but couldn't, for the life of him, get free. Bridget just kept laughing away at his struggles. Her hunger for his boy pussy was at its peak now and she couldn't control her desire any longer. She pressed her thick meaty cockhead into Jimmy's asshole.

"No!! NO!! NNNNOOOOO!! AAAAAAAAAHHHHHHHHHHH!!" he screamed as Bridget took his virginity. The pain was nearly unbearable as her cock penetrated the weak boy, "Oh god yes!!" she moaned, "such a nice and tight boy pussy you've got!" Jimmy screamed and screamed each inch Bridget pushed into him, "AAAAHHHHHHH!! NNNNOOOOOOO!! NNNNNNOOOOOOOOO!!"

"Shhhh, that's a good little boy!" she cooed as the last few inches buried inside him. Her barren crotch nestled up against his butt cheeks and she sighed, "God you're sssssoooo tight!! I don't think I'll last very long!" Jimmy involuntarily pulsed his rectum around Bridget's cock and she giggled and moaned at the wonderful feeling, "Ooohhh! Keep doing that!" He realized what she meant and tried with all his might to stop what he was doing. He was completely ashamed of himself; here he was lying on his back with this 'girl' imbedded inside his asshole. And none of that was the worst part; the worst part was his cock was achingly hard. The pain in his asshole was subsiding but it still hurt like hell. He was sweating profusely, trying to resist her, but he knew the more he resisted the tighter his asshole would be.

"MMM!! Such a nice boy pussy! And you've got such a big boy down here too!" Bridget grasped Jimmy's eight inch cock and gently stoked it with a few fingers. Quiet gasps escaped Jimmy and he felt horrible about all this. Bridget smiled at him seeing his precum ooze out his tip. Jimmy wasn't having any of it though; he turned his head to the side and tried to pretend this wasn't happening.

"They all start out like this, but soon, and I mean soon, you'll need me inside you. Molly isn't quite there yet, but she will be too!" Bridget pulled out and gasped at the amazing suction Jimmy's rectum was giving her. She almost popped her load right then and there, but she held herself just long enough to stop it.

Sweat was already building up on Bridget's make-up encrusted face. She was really having a difficult time controlling her cock. Every so often she'd have to stop her pumping just to contain herself. One particular plunge was almost too much, but she held back. Bridget stayed buried inside Jimmy until the feeling subsided but then she stayed there longer just in case.

Each plunge produced a thin glob of precum from Jimmy and Bridget couldn't help herself stroking his big cock. "Such a big boy for such a big slut!" the pain was starting to subside now and he was getting used to Bridget's girth. It was actually starting to feel pleasant, which he hated about himself.

Bridget noticed how Jimmy's demeanor changed gradually from a standoffish mood to more relaxed. She could still tell he was fighting his emotions but she wasn't at all surprised by that. All of this thinking had relaxed Bridget enough to finish the job. Before getting back into it Bridget grasped Jimmy's throbbing cock and began stroking him. Gently at first but soon she was stroking him with a purpose.

Feeling like Jimmy was relaxed enough now; Bridget began pumping her meaty cock in and out of his almost painfully tight ass. She smiled hearing his moans of pain and pleasure, "that's a good boy! Take my meaty cock!!"

Bridget's bed started to shake under her penetrations. Long deep thrusts filled Jimmy's little hole causing him to squeal like a little girl. Bridget began upping her thrusts until she was gliding in and out of his tight little hole as if she'd been doing it all her life.

"Fuck!! This is too good!! UUUUUHHHHHHH!!" Bridget slammed her hips as hard as she could and embedded her meaty cock inside Jimmy. She spewed her salty seed, shooting six volleys before collapsing on top of Jimmy. Under any other circumstance Jimmy would be in heaven now, having a naked girl on top of him, pressing her boobs into his body.

Bridget rose from Jimmy's body, "I usually spray myself onto my new comers first, but your ass was just too good to pass up!" Jimmy laid there, confused and still guiltily horny.

Bridget, as swiftly as she entered Jimmy, pulled out. Her softened cock glistened with lube and cum. "Clean me up," she demanded. In a moment, Bridget pinned Jimmy down with her thighs and her limp cock probed his lips. She pushed her hips forward trying to get him to open his mouth but Jimmy wouldn't budge. "You do know, the longer you wait the more time it'll give me to recover and do this all over again..." she smirked. Jim processed what she was saying and reluctantly opened his mouth. "That's a good boy!" Her cock slipped right past his lips and modestly filled his mouth. "You better work that tongue of yours," Bridget demanded again. Again, reluctantly Jim obeyed and swirled his tongue around Bridget's mushroom head. "Mmmmmmmmm..." she had to close her eyes, feeling the warmth of his mouth.

Jimmy hated having Bridget's cock in his mouth. The salty taste of her cum was no welcome treat, let alone having a cock in his mouth. It did feel oddly arousing to have her warm appendage in his mouth. He tried not to think of it as a cock, but a large soft clit.

Soon that soft clit was becoming hard again. Quickly, he cleaned up the remnants of Bridget's orgasm in hopes of her pulling out and letting him leave.

To his surprise Bridget did pull away, "Mmmm, that was good. I don't want to spoil myself any more so that'll be all for now." The weight of the bed shifted as Bridget jumped off, bent over, presenting herself, and pulling her panties and shorts back up. She slapped her ass, "Maybe one day you'll get to hit that! Now get cleaned up and outta here!" With no hesitation, Jimmy was out in a jiffy.

Bridget returned to her computer, laughing at all the missed texts. She sat back down, typing away and giddy with excitement for the coming days.

*********

That night, Jimmy was incredibly horny; he masturbated three times before he was satisfied. Strangely, he thought about Bridget and her cock.

Chapter 5

The next day Bridget was already waiting for Jimmy, "Hey there!" Jimmy didn't say anything. "Follow me." At first he didn't respond, "You'd better follow me, if you know what's good for you." Jimmy perked up and grudgingly obeyed.

He followed the girl to another secluded area. It was weird this school had so many isolated areas. She led him in the room and shut the door. Today she was wearing a short skirt, which showed her shapely legs. Despite knowing what was beneath her skirt, Jimmy couldn't help staring at her smooth feminine legs. A single chair in the room and Bridget took it. It was already facing where the two entered and Bridget beckoned Jimmy to come closer. He did, not wanting to anger her any further. Once close enough, Bridget held Jimmy's hands in each hand, as if they were together. "Mmmm," she moaned, "isn't this nice?"

Again Jimmy didn't say anything.

"Oh, boo hoo," pouted Bridget, "Now kneel the fuck down!" Her tone changed drastically, frightening Jim. He did as she instructed and knelt down in front of Bridget, "That's a good boy!" she praised, again changing mood. With no warning Bridget grasped the bottom of her skirt and lifted the hem. She revealed her pink panties with no shame. An obvious bulge was there and she instructed Jim to remove her panties. "Do it now!" Jimmy hesitated. He just happened to look up at Bridget and saw the raging glare. That told him enough and he grabbed at her hips. "No, just move them to the side." He understood and grabbed near her bulge. She smiled as her little boy toy unwrapped her penis. It was already semi hard once free from its confines. "Aaahhhh," sighed Bridget, "Much better! Now, SUCK!"

There was a slight hesitation on Jimmy's part, but he was starting to understand his place. He leaned forward and licked the head of Bridget's cock. "Oooohhh!!" she squealed, "very nice, but I want you to SUCK!!" Jim gave in and plunged his mouth over her semi hard cock.

"That's my boy!" she groaned. Her hand went to the back of Jimmy's head and guided his head along her growing shaft.

Soon, she was her full seven inches and slamming Jimmy's head. "Fuck that feels good..." she groaned. The warning bell for classes rang and a sense of urgency ran through Jimmy's mind. I can't be late for class, he thought. He grabbed onto Bridget's cock and opposite his mouth, pumped her member. "Ooohhh baby... you know how to work it..." Bridget threw her head back in bliss as her balls tightened.

Jimmy felt Bridget's cock swell inside his mouth and furiously tried to make her cum.

"Oooohhhhh sssshhhhhiiiiiiittttttt..." Bridget groaned as her cock spewed her pent up energy. Jimmy didn't even need to be told that he had to swallow. He figured the happier she was, the happier he'd be. He sucked on her cock until she was drained completely dry.

In an instant, Jimmy was up and out of the closet, leaving Bridget to bask in her orgasmic glory. Phew, that coulda been worse!

********

Bridget didn't even notice Jimmy leaving, so when she rolled her head forward and saw him gone she was miffed. Oh, that boy! He'll get it for sure! She smirked as she tucked her cock back into her panties and skipped out of the closet.

********

The day was a good day for Jimmy for the most part. He was pleasantly surprised Bridget wasn't following him around the school. He didn't even see her at lunch, ah, what a weight off my shoulders, he thought.

The end of the day came around and he was at his locker as usual. Thursday, just one more day and the weekend! that thought was in his mind until he noticed a presence, or at least someone looking at him. He got up and turned around.

Bridget...

She was standing there, smirking evilly at him. "How's my best friend?" she asked.

"Shit..." he said under his breath.

"I asked you a question!"

Jimmy looked to Bridget, "Fine..." he sighed.

"Grab your things and let's go!" Bridget's mood changes scared Jimmy, in one moment she may be cheery and happy and the next she could be devil incarnate. He had a feeling, though, that the cheery attitude was all a charade.

They walked to Bridget's, Jimmy nervous the entire way. Before he knew it, they were already in Bridget's large room.

Jimmy set his things down on Bridget's bed; unbeknownst to him Bridget slipped her panties off from under her skirt. He looked up to see Bridget head over to her computer and take a seat. By now he knew the routine; he'd do the school work while she chatted or played online games on her computer.

An hour passed before a strange sound from Bridget's computer startled Jimmy. It almost sounded like a girl, almost a moan...

Jimmy looked up to see what was up. He wasn't expecting to see Bridget's legs up on her desk and stroking her cock. Her cock splayed her skirt out at the front as she jerked herself. Despite the angle she was sitting in Jimmy could clearly see her glistening cock. He heard another moan. This time he was sure it was coming from the computer and not Bridget.

As quietly as he could he got up to investigate, could she really be looking at porn, with him in the room? As he neared her computer, the screen became clear. An image of a transsexual girl undoubtedly being sucked off by a man. Jimmy watched the images and peered down to Bridget's cock. She was timing her stokes with the action on screen.

The video was rather short and skipped around. Bridget kept her timing with the video. Towards the end the girl was pounding the guy, as was Bridget pounding her cock. She didn't last long and moaned in her seat, spewing out her semen all over herself and the keyboard.

Jimmy couldn't believe he stood there and watched the whole thing, what was even more embarrassing was the fact that his cock was rock hard in his pants. He was about to turn around and pretend he didn't see anything but he bumped into something causing Bridget to spin around, "Mmmmm, so you saw my little private time did you?" Bridget wasn't mad or embarrassed about the situation, if anything it was turning her back on. Her cock had gone soft but was already thickening back up. Jimmy stood there blankly, caught red handed.

"So did you enjoy that?" Bridget made an obvious effort to gaze down to his pants and back up. He realized what she meant and covered himself up, blushing in the process. "Ooohh, don't be shy, I'm not!" Bridget spread her legs further still and lifted her skirt all the way exposing her glistening cum covered semi-hard cock. She was slowly massaging it back to life.

"Come here and be a good boy!"

Jimmy backed away, still confused with himself. How did that short video turn him on? It shouldn't have. Sure the shemale in the video was pretty, but still...

She had a...

A...

... A cock...

... She technically wasn't even a she, hence 'shemale.' Could they really be that convincing?

Wait, who was he kidding! Here was Bridget, one of the hottest girls at school and she's a shemale, well a girl with a dick...

"Why?" was all he could muster.

"Because you know you want to!"

She was right, weirdly, he wanted to - for some unknown reason - suck her cock. Like an asteroid caught in the gravitational pull of a larger planet, Jimmy couldn't resist her pull and got on his knees and sucking Bridget off.

"Oohh, that's such a good boy..." she moaned, "Mmmmm..." just as she had earlier, Bridget threw her head back at Jimmy's wonderful sensations. He didn't even need to be told to use his tongue; he was already doing it.

Inside his mouth Jimmy was swirling his tongue around Bridget's sensitive cockhead. Soon he had a hand on her thickening cock and was jerking her. "Oh baby! You know just what I like..." she groaned. Bridget began playing with her boobs through her tank top, flicking her nipples in the process.

"Oh god!! Stop!!" moaned Bridget. She was getting too close, "Please stop!!" Jimmy didn't, he was having too much fun.

Wait fun?

How can I be enjoying this? He thought, I'm sucking another person's cock for god's sake! His thoughts were soon interrupted by Bridget's rude push. With a loud pop! His lips were no longer attached to her warm meaty appendage. He pouted, even surprising himself.

"Wow! That's never happened before," smirked Bridget, "It usually takes a couple weeks to break you newbies!"

Jimmy sat there, on his knees, just taking it in. "Don't talk much now do you?" she asked rhetorically. As had been the norm, Jimmy didn't answer. "Well, you've been such a good boy that I want to reward you!" Bridget got up from her seat and sat on her bed, patting a little area for Jim.

He obeyed without question and sat by Bridget's side. At first the two shared eye contact but Jim broke away first to gaze upon Bridget's engorged member. "Hmmm, you know you want it, don't you?" Again Bridget wasn't expecting an answer and didn't get one.

She stood up and unzipped her skirt while stepping out of it as it hit the ground, "Mmm, that's better!" Her cock swayed as she walked around proudly. It glistened with her recent orgasm and precum. "Now be a good boy and take off the pants!" Jim paused for a second before remembering her threats. He stood and unzipped his trousers and then let his boxers fall. His eight inch erection sprang free showing his own confused excitement.

As soon as his lower half was free of its confines, Bridget pushed Jimmy back onto the bed. This caught him off guard and inadvertently exposed his naked butt to her. "That's what I like to see!" Bridget pounced like a hungry lioness. She was in between Jimmy's legs in no time flat, making sure he couldn't close his legs. With just the lube from her previous orgasm on her cock she searched for his hole before poking herself inside him.

In one plunge Bridget was buried inside Jimmy. She moaned in pleasure while he groaned in sudden pain. Her thick member stretched his tiny hole uncomfortably as he tried to pull away. "Oh no you don't!" Bridget grasped onto his hips to hold him down. Without any consideration for Jimmy, Bridget slammed her meat into him as hard as she possibly could.

Creak, creak, creak...

The bed needed some oil as she shook the both of them. In just a matter of minutes Bridget was sweating profusely. She knew she wouldn't hold out much longer but didn't care, it felt too good. "God you're ssssssooooooo fucking tight!!" Bridget grunted and grunted above Jimmy while he howled in pain.

"Shit!! I'm close!!" Bridget grunted.

Slamming and slamming Bridget fucked Jimmy like a machine. "Oh shit!! OH SHIT!! FUCK!! SHIT!! SHIT!! SSSSSHHHHHIIIIIIITTTTTT!!" One final plunge. Bridget buried herself and unloaded her most potent load yet.

Five quick reams of semen splattered the insides of Jimmy. Wanting to watch Jimmy's expression with what she was about to do next, Bridget pulled out and jerked herself off as quickly as she could. Her hand was a complete blur as she grunted again, "UUUUUUUUGGGGGGGGGGGGGGGGG!!" Two more quick volleys of hot girl semen launched out of her cock, landing on Jimmy's shirt. With a few more slow strokes, Bridget unleashed the rest of her girly orgasm on Jimmy's torso and shirt.