by D. L. Savage
My heart was pounding as I spat on my fingers then reached down and stroked the wetness onto his cock, getting him lubed up and ready for what was coming next. It was crazy, I mean I’d never done anything like this before with a guy, but now Penny was taking over completely – and she seemed to know just what to do!
Still stroking his cock with one hand, I reached around and tugged the string of my thong to one side, just enough to expose my ass. And then, very gently I lowered myself onto him, guiding the bulbous head of his cock towards my tight little hole, shivering as I felt his warm meaty girth touch against me there.
I pushed harder onto him, trying to relax, as his cock head pressed against my entrance, but for a moment it felt like it was no use, that he was just too big for me, and I started to panic that this was a crazy idea, that I’d bitten off more than I could chew.
But I forced myself to relax, letting myself soften, letting my muscles relax for him, and slowly – very slowly – I felt my ass parting, and his hot meaty thickness sliding deep within me.
“Oh my god, you’re so tight,” he growled, his eyes blazing up at me, his hands around my slim waist and hips softly starting to buck as he slowly and tenderly began to take my virgin ass.
At first, the sensation was so strange – so new to me – that I was still trying to make sense of it. I could actually feel him, feel that big hard dick sliding deep into my hole. And what’s more, as I began to relax into it, I could feel the pleasure growing inside me, seemingly with each fresh thrust of his hips. It was like the curve of his dick was hitting some magic button buried deep in my ass, because before long, it felt so damn delicious that I could feel the unmistakable swarming pleasure of my orgasm approaching.
“Oh Alex,” I moaned softly, as the sensations quickly magnified inside me. “I think I’m ... I think I’m gonna ... come.”
And as I said the words, he seemed to take this as his cue to go even faster and harder, slamming that big dick into my ass now, the sensations increasing tenfold inside my body, quickly tipping me past the point of no return ...
“Come for me, baby,” he urged, his eyes locked onto mine as he drove his dick even harder into my tight little sissy ass. “I wanna see it,” he added.
And before I could stop him, he reached between my legs and tugged the gusset of my thong to one side, exposing my still limp little dick and balls, which began jiggling and flapping with each powerful thrust of his hips.
“Oh, oh, that’s it,” I cried out, and with a final deep delicious shudder, I came harder than I’d ever come before in my whole life, my ass clamping tight around his dick and my cock starting to spray streams of fresh white cum all over his muscular chest.
“Damn, that’s so fucking hot,” he groaned, his eyes fixed on my dick, and the sight of it squirting like that must have tipped him over the edge too, because a moment later I felt his whole body stiffen beneath me, and with a low growl, he grabbed me tight, holding my slim body hard against his, his cock pulsing and pumping, buried right to the hilt in my ass as he blew his own load, as the last of my orgasmic pleasure swept around my still-quaking body.
And after we’d both come, we stayed like that, wrapped together on the couch, his dick still deep in my ass, our lips locked in a passionate yet tender kiss. It felt so good, so right, so perfect, and I was thankful I’d confessed everything to him – to this amazing guy who actually wanted me for who I really was, deep down: the girl inside me who had finally come out, for good.
I knew I still had a long way on my journey to truly becoming Penny. I still had to tell my family, I still had to tell my other friends, and I still had a lot of work to do on my body and face, before the changes became truly permanent. And that was not to mention the future trials and teasing that Mistress Cartwright was sure to put me through if I carried on working for her. But I didn’t care. With Alex by my side, I just knew deep down that everything would be okay.
THE END
4
Blackmailed by Bethany
Tony groaned, his cock twitching and pulsing in his grip, ready to spurt at any moment now.
Was this really happening?
He couldn’t tear his eyes away from the screen of his computer. Because there, right before him, Bethany Turner — the absolute hottest, sexiest girl in the whole freaking college — was dancing for him on webcam!
Tony watched, absolutely transfixed, as she moved her hands up her slender body, her flimsy little vest stretched so tight, he could clearly see the see the points of her erect nipples beneath the thin white fabric.
She turned, so her back was to the camera, then bent forward, her bare butt flashing out from beneath her mini skirt.
Tony’s stomach lurched and his small pathetic cock twitched once more in his grip.
He couldn’t believe what he was seeing.
Bethany's beautiful, lightly tanned body looked so perfect, so fucking sexy. Her ass was deliciously pert. And between her legs, Tony could make out the swollen lips of her pussy, so clearly visible beneath her tight white thong.
With her back still to the camera, Bethany's hands started to slowly slide up her body, caressing her curves. Her left hand was moving upwards, perhaps to toy with her rock hard little nipple, while her right hand had moved down — to that hot wet place between her legs, the place that Tony had fantasized about on so many occasions but never dreamed he would actually see with his own eyes!
Because Tony was a scrawny, nervous geek and Bethany Turner was queen of the whole fucking campus.
It was almost too good to be true.
So how had this happened?
Tony still couldn’t quite get his head around the sequence of events that had led him here to this moment, stroking his hard, twitching cock as he watched beautiful sexy Bethany toy with herself too …
It had started so naturally, so normally, with a simple little request after class.
“Hey Tony,” Bethany had asked him, catching him up in the hallway just a few hours previous. He’d been so surprised she even knew his name, and he’d felt himself blushing as she continued to speak, a common occurance for Tony, whenever he tried to interact with members of the opposite sex. “You mind emailing me your notes for class?” she’d asked, so sweetly and innocently.
And of course, Tony had agreed, feeling his heart thumping hard in his scrawny chest as she wrote down her email address on a torn-out scrap of paper from her jotter and handed it to him, her handwriting all curly and cartoon-like, so different to Tony’s geeky, indecipherable scrawls.
That afternoon, Tony had returned to the perpetually sweaty, smelly, untidy dorm room that he shared with Mike, his roommate (who, thankfully was out at football practice), and quickly typed up all his notes from class, emailing them over to Bethany the very instant he’d finished writing them up.
And when his email had shown one new message, a few moments later, he’d felt the first nervous lurch in his stomach as he’d opened her reply. He’d been expecting nothing more than a brief, impersonal ‘thank you’, but instead she’d written something much more personal:
Thanks sexy xxx
Sexy? Tony had thought, staring in disbelief at her reply. What the fuck? Perhaps she meant to send it to someone else, he told himself. Because his luck with girls was practically non-existent.
But just then, his thoughts had been interrupted by a loud ploink noise, coming from the speaker of his computer, accompanied by the following note:
Bethany Turner has requested to add you to her chat contacts. Accept: YES/NO.
By now, Tony’s head was positively spinning and his heart was drumming and pounding in his chest. What in the world was happening? He just couldn’t believe it! Was Bethany Turner really making a move on little old him?
He’d gingerly clicked ‘Accept’, still thinking that this must be some sort of mistake or something, and almost instantaneously the first of a rapid-fire series of messages from Bethany had appeared on his screen:
Hey sexy
How are you?
I’m bored
You online?
Fancy camming with me?
Well, one thing had quickly led to another, and now here he was, his t-shirt pulled up behind his head, showing off his thin pale body, his jeans and boxers hurriedly discarded too. As he leaned back in his chair and masturbated his small pink cock, he just hoped to God that Mike didn’t finish football practice early for some reason and burst in on him.
He groaned again, feeling his cock twitch once more, a clear bead of pre-cum emanating from its tip and sliding down his shaft. He used this clear fluid as lube, lightly stroking his pulsing shaft up and down, trying with all his might not to blow his load too soon, trying to stay in that sweet, trembling place right on the very edge of orgasm, unable to tear his eyes from the screen of his computer as Bethany turned round slightly, so that she was in profile now.
She’d pulled her vest up, and for the first time Tony caught a clear glimpse of her nipple. It was small and a dark pink, the teat standing out so hard and proudly. She was obviously incredibly turned on, and yes, just as he’d imagined, he saw that sure enough she was fondling her breast with one hand while toying with her pussy with the other.
Finally she turned towards him, facing the webcam, parting her thighs a little more, tugging the flimsy gusset of her thong to one side, her mini skirt bunched up around her waist, and Tony felt his cock swell even further in his hand as he saw that her pussy wasn’t totally shaved like he’d imagined it. And her pubic hair wasn’t blonde like her head, either. Fuck. This was such a beautiful sight: Bethany's body was so slim and delicate, her smallish breasts with their rock hard little nipples looked absolutely amazing, and there between her parted thighs, Tony saw that thick rectangular patch of dark black hair, and beneath it her shaved, swollen pink pussy lips.
Her fingers were working fast between her toned, tanned legs and her mouth began to open, her eyes closing, her other hand cupping her breast hard. She leaned forward, her fingers still moving so fast and rhythmically between her legs, her back arching and the unmistakable first trembles of orgasm flowing through her, as she sucked her bottom lip into her mouth, obviously biting down on it to stop herself from crying out in pleasure. And then, just for a brief moment, it looked like a hissing jet of clear liquid squirting out of her pussy too.
Wow!
This unexpected sight was too much for Tony.
He felt his cock swell and jerk in his grip, and he looked down at it, grunting involuntarily, just as it sent out the biggest spurt of thick white cum he’d ever seen. Again it jerked and spurted, jerked and spurted, pumping out squirt after squirt of hot wet cum, all over his desk and computer keyboard and fingers, way bigger a load than he normally shot.
On the computer screen, Bethany opened her eyes, her mouth curling into a grin, her cheeks flushed pink, her cute athletic body still trembling from her orgasm. She covered her shiny wet pussy once more with her panties, tugged her vest back down over her breasts and smoothed her mini skirt back down over her tanned, toned thighs.
There was a long pause, as Tony felt his cock beginning to soften and shrink once more, his heart still drumming away, his breath shivering in his throat as he wondered what in the world would happen next.
He leant forward, about to type something into the chat box when, rather abruptly and unexpectedly, Bethany cut the connection completely.
Tony leant back in his chair, his mind spinning and whirling with images of Bethany's hot body, that thick, dark patch of pubic hair, the way she’d moved her hand in fast little circles as she’d played with her pussy, the image of her leaning forward, sucking on her lip as she came, her pert breasts with their hard, dark little nipples … He almost felt horny enough to masturbate again, immediately, but just then his thoughts were shattered by the sound of the door handle turning behind him.
Tony’s eyes darted to the clock in the upper right hand corner of his computer screen - Fuck! It was Mike, back from practice early.
“Wait a minute!” Tony almost screamed, quickly pulling his shirt back down over his torso, then jumping to his feet and pulling his pants on, no time for his white cotton boxer shorts.
He’d just about pulled them up around his waist when Mike finally burst into the room.
“Ha! It totally smells of cum in here!” Mike proclaimed, his tanned, handsome face breaking out in a grin. “You been jacking off again, T-bag?”
“No,” Tony mumbled, knowing how useless and transparent his pathetic little lie was. It was obvious what he’d been doing: his crumpled boxers, the streaks of cum on his desk and computer keyboard, his flushed sweaty face, his sticky wet fingers.
Mike was always teasing him about jacking off, mainly because Mike swore he didn’t ever need to, what with all the regular pussy he got. Because unlike Tony, Mike got plenty of action around campus. Of course he did, he was on the football team, he was handsome, he was well built, he was funny, he was everything that Tony was not …
But then again, Tony reminded himself, as far as he knew at least, Mike had never slept with Bethany Turner, sexiest girl in the whole college …
And Tony was about to open his mouth and brag about what had just happened, when something caught his eye on the screen of his computer:
One new email.
He quickly sat back down at his desk, his heart thudding, hoping it was from Bethany.
“Hey, can you wake me in an hour?” Mike asked, lazily. “I’ve gotta date with Stephanie …”
But Tony wasn’t listening to his roommate anymore. He was too busy looking, in horror, at the email he’d received, from Bethany Turner, at 4:55pm today:
Guess what you dirty little pervert? I filmed the whole fucking thing. And if you don’t want all your friends and family to see you stroking your cock and cumming all over your computer then you’d better meet me at midnight on Friday, outside the laundry rooms.
Attached to the email was a video file.
Tony turned in his chair and looked over at Mike, who was crashed out on his bed now, his headphones on and his eyes closed, listening to music on his iPod.
He double clicked on the file and the video window opened up and sure enough, there he was on screen again: fumbling his pathetic little dick out of his pants and jacking it frantically, his face all twisted up and flushed with horniness, his thin body looking so scrawny and pale and disgusting. He looked like such a pervert. Such a sicko.
And the worst thing of all, he realized, as he watched the video, that Bethany had obviously only recorded his part of the screen — there was no indication that she had been masturbating too.
Fuck.
He felt like he was going to be sick.
What a stupid fucking fool he’d been!
He thought queasily about his friends and family; what they’d do if they ever ended up watching that video clip. No way. He’d do anything, absolutely anything in the whole fucking School, just so his parents didn’t see it. They were old and strict, they were paying his fees, they’d cut his money for sure and never speak to him again if they thought their son was the kind of sicko to do something like this. And his other relatives too would be absolutely disgusted. He imagined family gatherings: the icy stares, the cold prickling embarrassment as he thought again about them watching him masturbate.
No way.
There was no choice.
He would just have to meet Bethany tonight and find out just what she wanted from him ...
* * *
Tony spend the rest of the week at college in a state of queasy anxious dread, wondering just what Bethany would want from him when he finally met up with her on Friday night. He feigned sickness too, staying in his bed, unable to face any of his classes in case he saw here there. What if she’d already showed that video to her friends — those giggling bitch cheerleaders and sorority girls that she always hung around with?
Bethany was a member of Alpha Delta sorority: the absolutely crazie
st, hardest-to-get-into sorority on campus. Rumors about their hazing practices were totally legendary too. Orgies. Blowjob parties. Girls making each other squirt. You name it, they’d supposedly done it. It was the kind of stuff that, until a few days ago, Tony would have feverishly masturbated over himself, imagining Bethany squirting her pretty pussy into another girl’s open mouth perhaps. But now, he just felt sick. Sick and angry at himself, and that stupid fucking mistake he’d made, wishing there was some way he could just turn back time ...
“You gonna stay there in that bed all week?” Mike had asked one morning, looking over at Tony with distain from his perpetually-messy side of the room, pulling a clean shirt over his tanned, athletic torso, his clearly-defined six pack abs another visual reminder of just how much of a weakling Tony was and always would be in comparison to Mike …
“Uh huh,” Tony had nodded, feeling a fresh pang of sickness in his churning stomach as his mind turned, for the millionth time, back to The Webcam Incident.
He just hoped that Bethany hadn’t shown that video to anyone already. Because if she had, his life on campus would be over …
* * *
Eventually Friday night came around. Tony feverishly counted down the hours until midnight, thankful that Mike was out once again, this time at a nightclub somewhere in the city, thankful that he wouldn’t have to make up some kind of bullshit excuse at midnight when he snuck out to meet Bethany.
Finally the hour drew close, and Tony roused himself from his bed, feeling a deep ache in his back from just how long he’d spent lying around wallowing beneath the sheets and feeling sorry for himself. He pulled on a dirty pair of jeans and a stained old, ripe-smelling t-shirt, then laced up his sneakers.