Session

"I'll be over at 8:00." Matt read the text from Andrea with a touch of dread. He hadn't heard from her in over a week and was beginning to think maybe their previous encounter was a one and done sort of thing. It obviously was not to be that way. Matt was beginning a relationship with another girl who he hadn't even begun to discuss with the kinky things that he needed, even craved. He was feeling a bit nervous about the situation, but now Andrea had her blackmail. The pictures were likely dated, and even if they weren't, what they were of was enough to crush anything he had going with anyone. He wasn't even sure what to reply with. "K" was all he could bring himself to do.

He tried to keep him occupied for the next two hours, reading, playing a game, watching TV. But he was sidetracked completely and inevitably it lead to watching porn or reading erotic stories. He couldn't even imagine what sort of punishments she had in mind for tonight, or where she was getting them from.

At the clock neared 8:00, he figured he might as well get ready. He unlocked the door, then walked back to the computer. It was a little cold out, getting closed to winter, but he new he'd likely be naked anyways and took his shirt off, his nipples were already hard and sensitive and he delighted in pinching them a bit as he watched the last bit of porn. His cock was already hard against the leg of his jeans. He turned off the computer and sat on the coach as the clock turned to 8:00. He had butterflies in his stomach as he watched the clock. If she was in a mood worse then last week, who knows what sort of pain she would inflict on him. That thought made him even harder.

It was then that he heard the door being opened. He stood up quickly as the moment he's been nervously awaiting finally came reality once again. He walked into the kitchen as she opened the door from the foyer. Yet again, she had the same long coat on but this time boots on. She smiled at him as she put a little bag on the table and walked up to him. "Kiss me." She said.

He obliged and leaned in as they met lips, she immediately brought her fingers up to his nipples again and squeezed as her tongue tickled his lips. She pulled her mouth away after they kissed for about 10 seconds. Her fingers still squeezing his nipples. Her grip tightened, "Mmm, I've missed these." She once again began using her fingernails on his nipples and pinched them painfully. His knees got weak as he moaned. She lifted her head and again they started kissing.

After a minute or so she finally let go of his nipples and pulled away from the kiss, "take off your jeans, and sit on the cough." Without a moments hesitation, he stripped off his pants and sat on the couch as he was instructed. She watched him lustfully, "scootch to the end. Yes, just like that. I love how hard you are already. I can't wait to hurt you." She took off her long jacket. This time she was completely naked underneath except for the same fishnet stockings and a tall pair of black boots. She grabbed the bag on the table and sauntered over to the couch. Her nipples were hard, she had perfect c-cup breasts on her small frame. Her sex was shaved bare as it usually was and her tan was a bit darker then normal. This sexy little one hundred pound girl would hurt him tonight, and he was so hard as the night unfolded. She put her bag down on the couch next to him and took his cock into her hand. She rubbed it up and down and brought her lips down. Slowly she licked his cock head as she looked up at him. She then plunged her head down his whole shaft, taking him deep into her throat. He gasped and leaned his head back in ecstasy. Her hand pushed his legs apart as her hand found his balls that hung off the end of the couch. As her mouth and throat worked on his cock, her hand sensually played with balls, lifting them and lightly squeezing them.

Her mouth came off his cock with an audible pop from the sucking she just gave him. "Mmm, I've always enjoyed doing that to you." She crawled up his body again and kissed him deeply for a few moments.

"Okay, now it's time to hurt you. I know, you can't wait." She smiled at him. "Where did you put that syringe I brought last week?"

"Its in the drawer, all cleaned."

"Good." She got up from her knees and walked to the bedroom. He could hear her open the drawer where they had kept all the sex toys. She lingered longer then he thought she needed to if she was just getting the syringe which was right on top. Finally, she walked back into the room. She had a few other things, some rope and a pair of metal teethed nipple clamps.

She plopped the rope down on the couch but still held the nipple clamps in her hand, "I miss using these." She grinned as she leaned over him. She flicked his nipples a few time to get them as hard as possible. She then put the teethed clamp over his nipple one at a time and tightened them until he gasped. She then gave it one last twist ensuring they were biting into his nipples deep enough to cause the perfect amount of pleasure and pain that she knew he enjoyed.

"I'm going to tie you up. I have a feeling if I don't you won't let me finish what I'm intending to do tonight." He smiled as she tied his ankles to the couch and eventually his hands together behind his back. She made sure everything was tied tightly enough so that he truly wouldn't be able to fight her. The idea made him hard but also just a touch fearful about what she had in mind.

She got down on her knees between his spread legs. The next thing she pulled out of her little bag of tricks was a full tube of lubricant. He had an idea about what she intended with that and smiled, it had felt sooo good last time when she filled him up with lubricant. His dick was hard as could be as his thoughts began to wander. She indeed filled the syringe as full as it would go with lubrication. "I know, you liked this last time." She grinned as she brought the tip of the syringe to his hard cock. She slowly pushed it in and began to push down on the plunger. Matt began to moan has he felt the cool liquid pushing into his urethra. Such an exotic feeling, the lubricant being pushed into his cock. It sunk into the depths of his cock. He pushed his hips up, welcoming the waves of pleasure as the mass amounts of jelly was forced into his cock. Andrea pushed the last bit into his cock and pulled the syringe away. "Some day we'll see how much we can get into you." She smirked as she put the syringe down and tugged on the chain between the nipple clamps. Matt gasped as a spasm of pain shot through his nipples, down his body into his loins and resulted in a small spurt of lubricant pushed out of his little hole and down his shaft.

Out of her little bag she pulled something that Matt wasn't sure how to respond to. It was a long thick rubbery looking worm. It was nearly two feet long and at least a quarter inch wide, if not nearly a half of an inch. It was a bunch of funky colors too, from orange to pink to yellow. "I found this at Walmart in their fishing section, I knew immediately I wanted to push it all the way into your little hole." She had such a wicked grin on her face as she brought it up dangling over his penis. It was tremendously long and thick looking. "I wonder if there are actually worms this big. Maybe I'll find one some day and we'll use that." She sounded serious.

Another gush of lubricant spilled out from Matt's cock as Andrea positioned the tip of the rubbery worm at his pee-hole. She manipulated his hole and worm deftly and pushed the head of the worm into his cock. He gasped at the size. It was the thickness of the biggest sound they'd ever used. "Mmm, perfect." She said as she began to push the huge worm into his hole. It was stiff enough to be pushed in inch by inch. She seemed to delight in Matt's moans as she pushed it in. And it had a long way to go too. Slowly, Andrea fed the worm into Matt's cock. The girth of it left Matt gasping and moaning. It was certainly soft and luckily did not hurt at all, despite it ridges and life-like textures. He was amazed as he looked down and saw that nearly half had been pushed into his cock. It was then that he could feel it deep in his urethra, passing the part where only the longest sounds reach. The feeling was utterly orgasmic as the Andrea pushed the worm deeper and deeper. He shuttered as he felt the worm find what must have been his bladder. He had never experienced anything like this. She was obviously delighting in the feelings she was creating in his body. But she wasn't done at all, it still had another six inches or so before it would be all the way in. She had no intentions of stopping at this point, even though it was becoming harder and harder to get the worm to go deeper.

She stopped for a moment and took a few moments to take in the yellowy part of the worm that remained sticking out from his cock. It looked like some alien tentacle was sprouting from his cock. She tugged on the nipple clamps a few times. It was obvious that Matt was in a world of his own. The torture of his nipples only increased the pleasure the worm was creating deep inside his cock. She wrapped her hand around his rock hard penis and slowly worked his cock up and down. She could feel the worm and how thick it was in his cock. Now she used both hands to work the worm into his cock. She wanted it all the way in. It took another few minutes as Matt gasped and moaned with his head rolled back but finally the whole length of the worm was buried deep in his urethra. All two feet. It was then that Matt noticed that there was a length of string tied to end of the worm.

"Perfect." She said as she got to her feet.

She turned her petite body around and lowered her wet pussy onto his cock, easing his manhood into the sweet folds. The sensations were incredible. The worm inside created feelings of intense pleasure for both, the worm made his cock even harder along her clitoris and the girth of the worm worked the inside of his cock as her pussy enveloped him. He humped upwards to meet her, thrusting deep into her cunt. She pinched her nipples as she impaled herself. They both moaned deeply awash in pleasure. She road him until she began to tire, though she never found an orgasm through intercourse, it certainly felt good. But it was time for the next stage.

Matt was panting in pleasure as his hard cock pulled free of her pussy. He was fairly close to orgasm, but apparently that would have to wait. "It's time to get back to business. So you mentioned paying me again." She looked down at his hard cock that bulged full of worm. He nodded. "Good." She walked over to his discarded jeans and pulled his wallet out. He only had $40 in it, she removed both twenties and dropped them into her coat pocket. "Well, since you're shorting me this time around, I'm going to have to make this worse for you. Sorry." She grinned.

She kneeled down in between his legs again. Her hand came up and started to lightly smack his dangling sack. He moaned and pushed his body down a bit further and spread his legs as far as he could. She took the invitation to take a little more frustration out on his balls, he accepted the pain with moans. With her other hand she found the end of the worm and worked it further into his cock. It went in further much easier. She pushed it in until the end of the worm was past where his shaft met his body. She stopped smacking his balls and went into her bag again and pulled out a tube of toothpaste. She held the bottle up for him to look at. "This is why I tied you up." She licked the end of his cock, where the string hung out of the tip of his hole.

His eyes widened as she opened the toothpaste and put the end of the tube into his pee hole. She pushed it in as far as it would go. He submitted himself to what would come next and could already feel the cool feeling of the toothpaste within his cock. He mouthed the word 'please no.' Miss Andrea shook her head and started to squeeze out the toothpaste directly into his urethra. He gasped as the cool minty cream started to immediately burn inside his cock. She relentlessly emptied the tube of toothpaste into his cock. The sensation wasn't entirely horrible as the cream pushed into his urethra. It went from cool, to hot to intensely pleasurable. He moaned and panted as she pushed toothpaste deep into his cock. She was surprised he wasn't screaming bloody murder. "Does it hurt?"

"Yes, but it's bearable." He said.

She sorta laughed. "Well I guess that's good, want it in your ass too?"

He shook his head quickly knowing exactly how much that hurt. She shrugged her shoulders and pushed more toothpaste into his cock until he was full up to where the worm was stuck way in his cock. Once his cock was full she put the practically empty tube of toothpaste on the couch and watched as toothpaste oozed from his cock.

"Well, I guess it's time to get my worm back." She tugged on the string. With the slightest pressure the worm started to travel back up his cock. Toothpaste poured from his cock, the burning sensation increased dramatically as the worm forced it's way back out. Matt began to howl as his cock burned. Now Andrea was beginning to enjoy herself watching Matt pant and shake from the pain that tore it's way through his cock. Finally the worm came out of his cock and after a few minutes of tugging and moaning from Matt, she slowly pulled the rest of it out. It popped out of his cock, toothpaste covered the outside of his penis, and created intense feelings there too. However, despite the pain, Matt remained hard the entire time, his balls boiling with cum.

"You should flush out your cock." She said as she started to untie him. When she was done he ran to the bathroom.

When he finally got done and walked back out, she was already gone. There was a note on the table. "Don't cum, I'll know if you do. Miss Andrea."