Painful Pilates

Theo settled onto the ground, trying to catch his breath. He was in training as a Pilates instructor, and had been diligently working at learning all the different exercise variations for his upcoming practical exam. He found most of them relatively easy, but the sheer volume of things he had to practice over the last week or so had started to take its toll. Things that had once been simple were turning into a struggle. I just have to keep pushing on for awhile, he thought, and soon the exam will be done and I can rest for as long as I have to. He looked back into his workbook to see what was next on the list, when he heard someone enter the room.


“Hey Theo! How's the studying coming?” a female voice called out.


Theo looked over to see Sadie, his boss/instructor, strolling into the room. While their relationship at its core was that of a coach and student, Theo had to admit it had been getting flirty recently. Maybe it was inevitable – Theo was a fit man in his mid-20s, and while Sadie was quite a bit older than him (having just turned 50) she was in very good shape for her age. A lifelong Pilates instructor, she stood at 5'10 with supermodel legs, a chest that looked like it was meant for someone twice her size, and a bubbly personality. While her frame was quite slim, her years of instructing had left her with deceptive strength. On top of all of that, she had recently gone through a divorce and was starting to show signs that she was back out on the prowl. Theo felt it harder and harder to resist making a move on his instructor, and her increasingly flirty nature was not helping.


“It's going well I think... just getting a bit fatigued from all the practice. Hopefully I nail the test the first time so I don't have to go through this again!” Theo said as he looked up from his book. If he was being honest, he had mostly looked up to see what Sadie was wearing that day. Somewhat to his disappointment, she was dressed conservatively in a pair of black workout leggings and a sweater, hair tied in a ponytail. His disappointment didn't last for long, however, as she bent over to pick up a piece of equipment from the floor, giving Theo a full view of her toned butt for a few seconds. He felt an erection start to grow and he quickly looked away, hoping it would die off before she noticed.


“That's great! You're pretty confident with all the moves then I take it? Maybe I should quiz you on a few at random to see how your knowledge is.” Sadie said as she walked over. “Let me see.... number 46.”


Theo quickly glanced at his workbook to check, feeling his stomach drop when he saw what exercise it was. It involved him rolling the front of his pelvis over top of a semicircle shaped piece of equipment. He had never wanted to admit it, but he hadn't practiced that one after the first time as it had nearly crushed his balls. Clearly the exercises were designed for a female group, and they had never considered the limitations of having a set of dangling testicles in the way. Not wanting to admit this to his boss/crush however, Theo attempted the move while trying to hide his considerable discomfort.


“Hmm, it's close, but not quite.” Sadie said as she examined Theo's form. “Here, I'll demonstrate it for you. Come around to my side.” Sadie stripped off her sweater, leaving Theo's prior disappointment in her conservative clothing choices a thing of the past. Now in a pair of tight leggings and a white v-neck t-shirt, there was almost too much to see for Theo to focus on her form. He forced himself to not ogle his instructor's body as she rolled her smooth crotch effortlessly over the rounded piece of equipment.


“Now move around to the front.” she said as she continued to roll back and forth. Why does she want me to watch from the front, Theo thought to himself. There isn't really a reason to see this one from the front side -


Theo's train of thought was cut off almost immediately by the sight he was treated to. Due to the rolling motion and deep v-neck shirt she was wearing, he had a very generous view of Sadie's ample chest. It took everything Theo had to not pop out of his pants right there. She has to be doing this on purpose, he thought. After what felt like an eternity of waiting, she finally hopped off the equipment and motioned for Theo to try again.


He gave it his best effort, trying to ignore the crushing pain in his balls as he rocked back and forth. As much as he tried to stomach through it, he couldn't keep the look of pain off of his face. Sadie noticed his discomfort quickly.


“Theo, are you okay? You're making a weird face, are you alr-” Sadie cut herself off as she looked down and realized what had been happening. His balls were being crushed by the exercise! She couldn't contain her laughter.


“Oh my God, Theo, stop! I'm sorry sorry!” she said in between giggles. “We have so few guys take this course I forgot that some of these exercises need to modified for the, uh, family jewels. I guess when you don't have them it's easy to forget.” As Sadie said that she spread her legs out slightly, almost teasing Theo and his pained state.


“It's okay, they're just a bit sore. I'll manage.” Theo said as he forced his eyes away from his instructors smooth crotch. He almost felt envious in the moment. “What should I do next?”


Sadie turned away from Theo and bent over to look at his workbook, pretending to choose an exercise. Realistically, she didn't need to bend over or spend this much time looking at the book – she already knew what she wanted to have him do. But it had been awhile since her divorce, and she hadn't fooled around with a man in quite some time. Despite Theo being much younger than her, she quite enjoyed teasing him and the reactions she could get out of the guy. Briefly flashing her assets and watching him struggle to not get horny was both funny and flattering to her.


“Let's try number 58.” Sadie said. “The one minute plank. I'll demonstrate first.” Sadie dropped into a plank and gave a series of brief instructions as she held it. Theo was struggling not to look down the massive canyon that opened up in the front of her shirt in her current position, but couldn't help at least stealing a few glances. At last the minute was up, and it was Theo's turn to attempt the exercise.


Once he got into position, Sadie went down onto her knees in front of him and leaned forward as she counted. Once again Theo had a clear view down her shirt, and this time he couldn't help himself. His erection started to grow, and to his horror Sadie moved around to his side right as it happened.


Sadie grinned to herself as she moved to Theo's side. Her teasing had worked, and the young man had a very clear erection showing through his gym shorts as he held the plank. “What is this?” she exclaimed with feigned shock as she reached out and gripped his now rock hard cock. “I can't believe you're getting horny while we work on your test! This deserves punishment!” Sadie couldn't help but laugh as she said it, not able to keep up the thin disguise of what she was doing any longer. She switched her grip to his nuts, giving them a gentle squeeze. She felt the young man's boy tense up immediately.


“You have 40 seconds left on this plank, and you bet my hand is gonna stay where it is for the remainder!” she said with a cackle. She was very much enjoying the cougar role, being able to dominate this muscular young man under her care. She also noticed that he seemed even harder after she started squeezing his balls than before. Was this turning him on? She increased her grip strength to medium, which was still quite substantial given the shape she was in. Theo's body tensed up even more but he still said nothing. He was definitely enjoying something about this, Sadie thought to herself. Suddenly, the one minute timer they had set went off.


Not wanting the moment to end, Sadie exclaimed “30 more seconds! For, uh, extra credit!” As the 30 seconds went on she increased her grip strength progressively, crushing the young man's balls in her hand. He was still rock hard! Eventually though, his balls couldn't take it any longer and he collapsed on the ground. Sadie let go and allowed him to cradle his testicles.


“Hmm, not bad. You almost made it! Can't be easy to hold a plank that long while a strong lady such as myself crushes your bits. I assume anyway, I obviously wouldn't know.” she said as she gently ran her hand over her groin. She leaned in to the young man, pressing her DD chest into his back as he lay in the fetal position. She slid her hand into his pants and began to gently stroke his still rock hard dick. She seductively whispered into his ear, “I could feel you get harder the tighter I squeezed those big nuts of yours. Is someone into pain? Does this little boy like having an older woman dominate him?” Sadie leaned over and looked into Theo's eyes. The look she saw told her everything, he was loving the attention. She kept stroking him for a minute before standing up, leaving him with his nuts filled to the brim and no release.


“We still have one exercise left to test! Again with extra credit involved. If you can pass this one, there will be a special reward as well. Let's go with... number 74, sixty seconds of sit ups. Let's go! Start!” Sadie didn't want to give him too much time to think about his aching dick and balls. As he started doing his sit ups, she stripped off her leggings leaving her in a pair of pink lace panties and her t-shirt. Her toned legs and butt added another layer of distraction for Theo. Once again Sadie saw the young man's shorts bulge with an obvious erection, which made her grin. She stepped forward and put her bare foot on Theo's crotch, gas-pedaling his throbbing testicles as she counted down the time left. Theo could barely take the combination of the exercise, the pain in his balls, and the magnificent upward view of Sadie's body all at the same time. It wasn't helped by her turning around halfway in, continuing to gas-pedal his swollen nuts but now with her ass in plain sight.


“Aaaand, that's sixty seconds! Good work Theo, not easy to do in those circumstances.” Sadie said as she removed her foot from his crotch. He collapsed back, hands laced over top of his eyes. This surprised Sadie, she figured he'd be holding his nuts like last time. Clearly she didn't cause him enough pain. She then realized he was still on his back, knees bent and legs spread. Oh no, I'm really about to do this, she thought. A wide grin took over her face and she drew her leg back and throttled it forward into Theo's exposed balls, feeling them crush into his pelvis as she made contact. Theo looked like he had been shot – he grabbed at his balls and quickly rolled onto his side as Sadie laughed hysterically.


“I'm so sorry Theo! I couldn't resist!” Sadie exclaimed, almost crying from laughter. “You just left the boys exposed like that, after all the abuse I put them through. How could I not give them a good ol' soccer kick. I do feel kind of bad though... I should make this up to you somehow. Would you like to hit me back?” Sadie was grinning as she said it, knowing full well she could never be made to experience what he was going through in that moment. “Oh that's right, I don't have balls. Wouldn't really be fair would it? Maybe mommy needs to make it up another way...”


Sadie rolled him onto his back and pulled his shorts down, exposing his somehow still hard cock. She pulled her panties aside, beginning to ride him with vigor. The young man barely lasted a minute after all the teasing, erupting inside of the older woman. She smiled and slowed down. Still got it, she thought to herself. The young man fell onto his back, exhausted from the massive release. Sadie leaned forward, pressing her breasts into his face. This was so that he couldn't see her knee rise up like a piston and smash into his balls with a moderate amount of force. He attempted to curl up like he had before, but Sadie's body blocked him this time.


“Now, that was quite fun for both of us I think. I would very much like to continue on. But, if you tell anybody about this, mommy will have your nuts in a garbage bag before you can blink. That knee I just gave you was maybe fifty percent. I'm assuming you don't ever want to feel what full force is like?” Sadie said, inches from Theo's face. He nodded quickly and with a terrified look in his eyes. “Good boy. I think arrangement will be good for both of us. Now clean yourself up and ice your balls before the next group comes in.”


Sadie stood up, putting her leggings and sweater back on. She winked at Theo before exiting the room, leaving him to contend with his empty, aching balls.