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Having Her way (Whisper Twice and Vigilant Thorne)

Miles felt positively crestfallen as he saw how hard it would be to escape. The demeaning clothes in his hand, he looked towards Audrey. "Um, thanks for those?" God, he tried so hard to sound genuine but just couldn't. Well, baby steps. "Can I have some privacy now do I can change?"

He paused as a thought struck him. He walked over to the desk and looked at the album. "Um, and I might need some more private time because...well...you know..." With any luck, she'd be gone long enough to pry off one of those boards.
 
Audrey nodded, blushing heavily. "Oh... y-you like them?" She said happily, but obviously embarrased. "Oh! But don't do that! I'm here now, you don't need to do that anymore! Let me go get your other gift!" She said, slamming the door shut and locking it. "Change into your clothes so you look cute baby!" She called though the door, as she ran down the stairs. She opened the gift and put on its contents, under her skirt. She took the bottle of lube that came with it and ran back up the stairs.
 
Miles ran to the window and started prying at the boards. He pulled with all his might, like his life depended on it, and it just might. But he couldn't even move it. And worse, it seemed that she had coated the edges with something like Vaseline, making it even harder to open. He fell against a wall and slumped to the floor. He was trapped. Well, and truly trapped.

He heard movement downstairs and realized that she wasn't giving him long. Shit, she probably still had that knife. He'd better do what she said.

He shrugged out of his shoes and pulled off his socks. Next came his khakis and Polo... Or what was left of his polo. Finally, with a sigh, he shrugged off his underwear. He grabbed hold of the lace panties and slid them on. He was sure that some men would have issues wearing it. Sadly, his cock was small enough to not cause much of an issue. The skirt came next and he was shocked to find it fit perfectly. Crazy stalker probably knows my every measurement, he thought.

Lastly came the top. He struggled into it and it felt weird. It was made for someone with breasts and he obviously didn't have any. All done, he sat on the bed, waiting for his doom
 
Audrey unlocked the room, closing her eyes. She turned around and opened them, locking the door. Then she slowly turned around. "Oh my god baby! You look so amazing Miles!" She ran over and hugged him, dropping the lube next to him on the bed she kissed him on the nose, smiling at him brightly. Her bulge was poking into his leg slightly. She smelled of sweet laveders, and her smile was pearly white.
 
Miles flinched as Audrey threw herself at him. But the hug wasn't too bad, and the kiss was not a knife in the gut. All in all, he felt he'd made the right decision. He saw her drop the knife on the bed and he reached over to grab it. What he grabbed, however, wasn't a knife. It was a bottle. A dawning sense of dread hit him as he realized what must have been poking his leg. He tried to scramble out of her grasp, but failed. "Please. Please don't do this. You don't have to hurt me. You can just let me go."
 
"What?" She asked, genuinely confused. "I'm not gonna hurt you! I'm gonna love you sweety..." she looked at him excited. Leaning over him as he scrambled back. "Don't worry hun!" I'll be gentle...

As she leaned forwards, her skirt rode up, exposing the massive bulge in her panties. A few leather straps were visible wrapping around her stomach.
 
Miles whimpered as the strap on was revealed in its full glory. He couldn't believe that this was about to happen? It seemed too surreal, like something out of a dream or nightmare. He just wanted to go home.

A tear rolled down his face as Aubrey crawled on top of him and he became too scared for words. He wanted to fight back, but, until he knew where she hid the knife on her body (and he was sure she had it), he couldn't do so.
 
Audrey smiled. "I know... I'm so happy I could cry too, but I'll stay strong for you baby. You can cry all you want. It's ok. We're finally together." With that, she slid down her panties and skirt, exposing the jet black cock in its full glory. The plastic was hard and rigid, and was exactly 7.5 inche's long. Thick veins were carved into the surface for pleasure. She began smearing a fistful of lube over the shaft.
 
Miles was paralyzed. He couldn't move. All he could do was stare at the strap on dido in absolute horror. It was so large, and the veins themselves were huge. He knew where it was gonna go and he clenched himself tight instinctively, even though he was still on his back in the bed and unable to be taken yet. If only he was stronger, he wished.
 
Miles shut his eyes, tears streaming down his face. He tried to clench his buttocks so hard when he felt the cold, wet plastic touch his virgin ass. But he knew he was weak. He was so weak.

"Please..." he begged, meaning it one way and not even realizing it would be taken another.
 
"It's ok hun. I know I can't feel this, but I know you'll feel great." With that, she shoved herself up to the hilt, pushing his tight hole apart. She tried thrusting, but was quite inexperianced. Each thrust pulled his asshole apart, and it would hurt worse due to his tightening and refusal to relax.
 
Miles screamed as the black cock entered his ass. It hurt so much and it was so big. He tried to relax, to do anything that might make it less again, but he couldn't. He could feel his ass almost being pulled out with each removal, only to feel even worse when it flew back in.

He thought for sure he would die from this, that something would tear and he'd bleed out on this bed, dressed in a skirt, never to be found. And, indeed, at that moment, he wished it was so.
 
As Audrey got better at it, Miles finally was able to stop clenching. He still hated it, this feeling of painful, painful fullness. But at least it wasn't excruciating anymore. At least he didn't think he was going to die there.

He hated how weak he was, how this girl could pick him up or shove something this big into his ass. He hated his friends for not hearing him scream for help. He hated himself for even going along with putting on the clothes. But most of all, he hated how his cock had grown to full size while he ass was continuously filled by a big veined cock.
 
Miles cried softly. "I hate it. Please stop..." But she only increased in tempo. His ass had almost gotten used to the pounding. It didn't seem to close up as much every time she pulled back. It made it easier, but Miles still felt horribly violated.

At Audrey's next comment, Miles ventured to open his eyes. She was over him, thrusting, but now she had a her phone out. Miles quickly covered his face in shame, praying that she would soon get tired. But even, then, his body betrayed him. At she plunged in him again, his cock twitched slightly and he let out a soft moan.
 
Audrey frowned. "You cant hate it! I'm sure you'll love it soon... you'll see!" She insisted. She fiddled with her phone, and began recording the strapon pushing in and out of his ass. With each pull, his asshole stretched out slightly, only to be rammed in again as she thrusted. "Now well always be able to relive this moment..." she sighed happily, recording all of miles's body as she fucked him. His skirt was flipped up around his thighs, and the straps of the dress were dishoveled, pulled down to expose one nipple.
 
Miles didn't like the feeling building up inside of them. The massive strap on kept pounding his ass and his prostate was repeatedly being stimulated by it. He tried to push Audrey away form him, to no avail. Then, he reached up to move the phone, but his hands suddenly flew to grab the sheets as his prostate got more and more stimulation. It was all too much. His ass felt so full and empty at the same time, and his balls began to tighten.

"No. No, please no!" he yelled, this time more to himself than too Audrey. And then, Miles came. His body shuddered and his tiny cock spotted white cream out over his legs and over the leather on Audrey. Miles could register that his body was supposed to be feeling pleasure from this, but his despair kept him from feeling any of it. "Shiiiiiiiit..."
 
Audrey gleefully recorded the entire scene. She smiled and recorded Miles's face as he came. "See? I knew you'd love it!" She said, smiling proudly. She pulled out of him with a 'pop', leaving his asshole gaping wide open. She crawled on the bed, cuddling next to him, smearing cum on her camisole, and his stomach, not seeming to notice it.
 
A cry of pain erupted from Miles' lips as the dildo finally left him. In a way, losing its girth was almost as painful as gaining it. He wanted to rub it to make it feel better, but didn't dare do so. He didn't want to know if he was bleeding.

Miles shuddered as the rapidly cooling cum coated his legs and stomach. His ass felt so empty. He could almost feel a cool breeze going into it. Oh God, he quickly realized. That was a cool breeze going into his ass. Why wasn't it closing?

He tried to shy away from her cuddling, but couldn't. He just wanted to be alone right now, away from the crazy bitch who had just sodomized him. And, he decided he knew how to do it. It was actually something he'd heard was taught to girls to prevent rape.

He closed his eyes and clenched his muscles. It was harder to do on command than he thought. Yet, eventually , a stream of pee burst forth from his penis up in the air. It fell on them both.
 
Audrey's eyes lit up in surprise. She began lapping at his stomach, drinking up the golden liquid like a cat. His piss soaked her hair, and his dress, staining it a bright yellow color, but she didn't seem to care. She scooped up a few drops of his piss, and held them to his lips, urging him to drink. "Thank you so much Baby!" She squeel ed delightfully. "This is such a kind gift!" She was oblivious to his pain, and continued sucking the puddles of piss off of him.
 
There was something that clicked for Miles at that moment. He had kept thinking that this was something out of a nightmare or something that only happened in movies. Anything to fail to accept the reality of the situation. But, as his plan completely backfired, his situation suddenly became very real for him. And that realization sent him into shock.

He didn't even have enough mental strength in his shocked state to seal his lips. His own pee entered his mouth and he didn't even notice how awful it was. His eyes got a glassy stare, like those of the condemned being led to the gallows. And he couldn't even bring himself to shed a tear.
 
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