Cindy arrived at Max's for her first weight-loss massage, though she wasn't there to lose any weight. The measurable goal she and Max agreed to was that she ride her bike thirty-five miles a week, which she would verify by texting Max a selfie of her with her bike, showing the odometer. She needed to reach 665 miles on the odometer, but she only got to 650. She knew she missed her goal for her first appointment, and she knew that meant some kind of punishment, though she had no idea what it would be.

On arriving, she went to the back bedroom as usual, undressed, and got on the massage table. Max arrived a few minutes later. He reviewed their agreement for the massages, explaining that each week she would be rewarded with an enhanced massage, which was her positive incentive to keep on the program. However, if she failed to meet the goal for the week, as she had this week, she would be disciplined first, and it was now time for that.

Max helped her re-position to the end of the table, having her lie on her stomach and bend at her hips so her feet were on the floor. Then he spread her legs and strapped each to the bottom of a corner leg of the table. This spread Cindy open at the crotch and she felt her pussy was very exposed, but she didn't mind since the erotic part of the massage was her favorite, and the reason she kept coming to Max.

Next, he reached into his nearby bins and brought out a wooden paddle with holes in it, showed it to Cindy, and said she'd get twenty swats for missing her goal. Starting with small whacks, he hit each of her cheeks and counted. Whack! Whack! She felt some pain, and it wasn't too bad, but Max kept at it, hitting her harder as he proceeded. Whack! Whack! It hurt noticeably now, and yet Max continued to spank her. Cindy squirmed and tried to wiggle away but could not since her legs were secured to the table. Whack! Whack! Cindy began to cry out in pain as Max counted out loud. Whack! Whack! Seventeen, eighteen... Whack! Whack! Nineteen, twenty.

The spanking was finally done, and Cindy could feel the heat and pain in her now bright pink cheeks. It was uncomfortable, but it was over now, and all that was left was the part she waited all week for, her “enhanced” and very intimate massage. Max put the paddle away and came to her with aloe lotion, which he rubbed on her pink cheeks. The heat and pain subsided almost immediately, and Cindy was thankful. The discipline hurt enough to make her decide to try harder to meet her goal next time, but it also left her surprisingly aroused. She wondered, was it the spanking that aroused her, or just the anticipation of the erotic massage?

Max brought his hands to Cindy's legs and caressed her from her knees, up her inner thighs, to her pussy. Up and down he traced, lightly, teasing, making Cindy squirm from the ticklish feel of his fingers, though her movements were limited by her restrained legs. Max would intentionally graze her pussy lips before moving back down, teasing her even more, and it was frustrating Cindy. She was ready to be played with.

So, when Max finally began to caress her slit, she immediately started wiggling in delight. He ran his fingers up and down her snatch, opening her lips, and dipping into her already-wet vagina before tracing back to her clitoris. He ran a finger around her opening for a moment before pressing a finger into her, then quickly added a second finger and began to finger-fuck her. With his other hand, he reached between her legs and applied a vibrator to the soft folds of her pussy and pushed it up and down her slit. With Max's fingers in her and the vibrator on her, Cindy began to convulse with delight and squirm for all she was worth. As the vibrator worked its magic, Cindy felt the intense sensations at her clit, and combined with Max's fingers in her, she completely lost it! Her cunt was alive like never before, and she jerked and spasmed as she came, her orgasm causing her to squirt her juices onto Max's hand, her thighs, and the floor.

Cindy loved the intimate massage part of the weight loss massage program Max used, and realized that while the spanking hurt, it was also a good prelude to his pussy play, and that maybe the pain even turned her on.

o o o

The next week, Cindy again fell short of her goal and knew she'd be disciplined, but she didn't mind the thought of it. She wondered if she'd subconsciously missed her goal on purpose. When she arrived for her massage, she went to the back room as usual and got ready, a little nervous and a little curious about what lie in store for her.

Max came in and reviewed her results. He said since she missed her bike riding goal again, and by even more than the previous week, she would receive harsher discipline this time. He helped re-position her on her stomach, bent at the end of the table with her feet on the floor, and he again strapped her legs to the corner legs of the table, spreading her open and exposing her pussy below her rear. But this time he also stretched her arms above her head toward the top of the table and secured them with straps. Cindy was almost immobilized and felt extremely vulnerable.

Then she saw Max take a flogger from his bin and knew she was in for it. She knew Max that wouldn't hurt her, but it looked like the flogger could be painful. He used one hand to caress her cheeks before he suddenly slapped her rear with the flogger. The many leather strands stung her, and she cried out and recoiled, but wasn't able to move. Max said he would give her twenty strokes and began counting. Smack! Smack! Two, three... The flogger was hitting both of her cheeks with a sharp stinging pain, but one more than the other, so Max began alternating his target with each swat. It hurt a lot, and she wiggled and squirmed, but to no avail; she could not escape the flogger. She began to cry out for Max to stop as her eyes teared up, but Max continued to count: Smack! Smack! Eleven, twelve...

Cindy was hurting, her ass was sore with hot, red cheeks, but she noticed she was also aroused. She could feel her pussy getting wet and she longed for Max to play with her slit, her vagina, her clit. She seemed fixated on those pleasures while he continued to flog her. When Max reached the last strike, she was relieved, but even more, she was completely aroused and so ready for him to touch her.

Max reached around her leg with his left hand to caress her snatch, and she jerked a bit at his desperately desired touch. But then he moved his hand aside and hit her pussy with an upward swing of the flogger! It didn't hurt because it was a light slap, but Cindy was concerned about what he was doing. Max slapped her pussy again, a little harder, and then again and again. It felt more arousing than painful as he struck her closed pussy lips. But then Max ran his left hand up and down her slit, opening her and exposing her tender folds and clit. Cindy was suddenly afraid. But she also felt her wetness begin to leak from her crotch. Was she turned on by the flogging?

The next strike was light, but right on her most sensitive place. It didn't hurt a lot, but she was afraid of the next strike. She tried to move away but could not. Her body tensed in dreaded anticipation. When it came, the next flog hit her cunt dead center and stung so much that she cried out. Max responded with another blow directly on her clit, and she screamed, her most sensitive spot stung with incredible pain! She tried in vain to close her legs. How long would he do this to her, she wondered. Several more strikes landed on her clit, and she pulled at the restraints and screamed as she tried to escape the torment. But, somehow, she was completely turned on and could feel her pussy juices leaking from her as she was nearing an orgasm!

Then, as suddenly as he had started flogging her, Max stopped and put the flogger down. He caressed her pussy, rubbing her slit and caressing her clit. He swirled around it, and she knew she was close to a climax when he stopped and switched hands, playing with her clit with his left hand. Cindy was so turned on now that she hardly noticed when he put one, and then two, fingers of his right hand into her. He pressed deep and turned the fingers down, then flicked them back and forth across her G-spot. The sensation was like nothing Cindy had ever felt, with her clit and G-spot being played simultaneously while the arousing pain of the flogger had not yet subsided. Every nerve in her body seemed to be in her cunt, and she jerked and spasmed, and came with an intensity she'd never had before, her juices flowing onto Max's hand, her thighs, and legs. With Max continuing to finger her clit, she exploded even further, spasming wildly and squirting her feminine juices with force onto his hand. She continued jerking and squirting for minutes, until she was exhausted and collapsed on the table, nothing left in her.

Max let her relax as he undid the restraints and helped her up to lie on the table to recover. He gave her tissues to clean herself, but she ignored everything; Cindy was in the afterglow of the longest and most amazing orgasm of her life!

o o o

After that day, Max's massages took on a whole new importance to Cindy. She craved the visits and dreamed of them all week in anticipation of both the pleasure and the pain she would receive. Somehow, the painful preludes were arousing and a turn-on, and the sex was so much more rewarding than it ever was before Max began disciplining her.

Over the months that followed, Cindy didn't even try to meet her biking goals, wanting Max to discipline her every week. She experienced regular paddling and flogging, and new twists from time to time, like nipple clamps and breast spankings, and most recently a riding crop assault on her inner thighs, pussy, and clit. She liked the pain as it aroused her anew every week, and allowed her to have long, intense orgasms that were always mind-blowing, ones she would never give up.

<< The End >>