A Frustrating Experience With Masturbation

This story is mostly fiction, though you could say it’s loosely based on real-life events and some of the sexy things my keyholder has told me—most of which she hasn’t actually done. -NN It had been a few months since my wife caught me masturbating. We’d been married for over ten years when she walked into the bedroom, surprising me because I thought she was in the shower. She was shocked. Deep down, she knew guys did that, but she preferred not to think about it. Now, she couldn’t help thinking about it. It made her feel like she wasn’t sexually satisfying or upholding her duties as a wife. I assured her she was fine and that masturbation is just something men do regardless of how often they get good sex. She still didn’t like the idea. She decided that the chastity games we used to play for a day or two needed to become a lifestyle to break me of the habit. She was serious about it. Not only did she buy a custom metal cage to replace our cheap plastic one, but instead of locking it with a padlock and keeping the key, she put a rivet through the lock hole on the device. The only way to take it off is with a power drill. At first, I was let out after a week or 10 days, maybe two weeks at a time. She didn’t want me taking any chances by masturbating again, but she also didn’t want to keep me locked up forever. She wasn’t into heavy punishment and had always felt self-conscious about teasing too much; she thought she wasn’t good at it or wouldn’t be able to come up with things to say. So, I started keeping a journal in a Google Drive file of sexy teasing lines she could use to turn me on, along with my fantasies that she could talk dirty to me using. She assured me that no matter what happened, she wouldn’t do anything either of us wasn’t 100% comfortable with (like bringing home another guy and cuckholding me), but she was certainly okay with dropping hints about doing it and keeping me guessing as to whether or not she actually would. She picked up on the fantasies about punishment quickly. She occasionally gave my butt a hard smack and grinned, sometimes saying “maybe I will have to start using a wooden spoon on your bare ass” if I upset her. But she never did any of it until last weekend. Friday night was teasing night. Usually, she keeps me in my cage while making me finger her to an orgasm as I lick her nipples. Last Friday, she took it a step further. She let me out of the cage during this act and stroked me. It had been 22 days since she locked me up last time—easily the longest stretch we’d gone. She said this was a reward for not masturbating in those past months. She stroked my throbbing cock while I fingered her to an orgasm that bent her in half. I thought it was going to be my lucky night and that we were going to have sex. But she had been reading the Google Drive file, knowing my fantasies about getting close to the edge only to be denied and forced back into the cage. She quivered through the aftershocks of her orgasm but continued brushing her fingernails up and down the length of my cock. I waited for the moment she would tell me to grab a condom and climb on top, but that didn’t happen tonight. “Ok, cage it back up,” she said. I protested! She had never done this before! What changed? “You’ve been doing good not masturbating,” she explained, “but you’re just too clingy when you get horny. You need to work on being horny and not being clingy. No orgasm for you tonight; that’s why we went 22 days last time, and we’re going longer this time.” She rubbed lotion onto my cock and started working the cage back on. When it got close, she grabbed the base ring, forced the cage onto the post of the base ring, picked up a rivet and the rivet gun, and I was once again secured tight, cock still pressing against the metal, straining in unbelief. The next morning, I slept in, which was unusual. Even on Saturdays, I’m rarely awake later than 6:30 AM. It must have taken too long to fall asleep last night for me to sleep until 8:30. When I got up, she was sipping coffee and working on her computer. I poured my own coffee. She looked at me and asked, “Look around, did you forget to do something yesterday?” I looked around. At first, I didn’t notice anything right away, but then I realized I hadn’t done the dishes last night. But here they were, clean. She must have done them when she got up this morning. I started wondering where she was going with this as I said, “Yeah, I forgot to do the dishes.” “Yep,” she responded. “And I’m going to get rewarded for it, and you’re going to be punished for not doing it.”

I smiled; she had never actually punished me before. This started sounding like fun! “When do we get started on that?” I asked. She chuckled. “Later, after we get all the work done outside.” Darn, it sounded promising. Later that afternoon, we had cleaned up the yard, mowed, and gathered brush piles. We had a late lunch, and she asked if I wanted to take a bath with her before she got her reward and I got my punishment. I agreed; if we were going to get “naughty,” it would be good to get cleaned up first. In the soaker tub together, she played with my cage using her foot. We sat and talked, enjoying each other’s company. As she decided the bath was ready to end, she told me that for her reward and my punishment, we were going to masturbate together. I knew she wasn’t going to keep denying me forever, although I was a bit shocked that she would let me masturbate since that’s why she’d been keeping me locked up in the first place. She told me to get dried off, go fetch her office chair and put it at the foot of the bed, and bring her Hitachi wand. I did. I was so excited I was practically dancing! I was going to jerk off, and she was going to masturbate too! We had never done this before! She came out of the bathroom. “Grab the strapon too,” she commanded. “The one with the 9-inch cock on it.” Curious, I thought… why do we need that for masturbating?

I fetched it anyway and brought it to her. “Put it on,” she said. I did. We’d done this before where I got to pound her after fingering her, but it was never her favorite activity, so this started confusing me even more. “Sit in the chair,” she ordered.

I obeyed. She took some zip ties from her desk and tied my wrists to the chair arms. She was going to make me watch her masturbate! Then she tied my ankles to the legs of the chair, followed by tying my right elbow to the back of the chair. I couldn’t have been more excited! What she did next made me start to understand what my punishment was going to be. “I still feel really self-conscious about you seeing me masturbate,” she said, “so I need to blindfold you.”

I nodded and agreed. She grabbed a black washcloth from the bathroom, put it over my eyes, and used industrial package wrap to secure it to my head. “Can you see anything?” she asked? “I can’t see a thing!” I replied honestly. “Good,” she said. “But I don’t think I’m going to be able to get into this if I can hear you, so I need to keep you quiet while you’re masturbating. Open your mouth and let me put my panties in it as a gag.”

I gladly opened wide. Not only did she put her panties in my mouth, but she placed a ball gag on top of that! She strapped it down tight! “Are you ready?” she asked. I nodded, intent on keeping very silent. She took a pair of diagonal pliers and cut the zip tie on my right wrist. The one around my elbow still kept my arm secured to the back of the chair. “Now, hold your palm face up.”

I did, and she poured a healthy dose of KY jelly into my palm. “This is how my reward and your punishment are going to work. I’m going to lay down and enjoy myself with my wand, while you…”

“I’m going to pump that strapon like it’s the last time you’ll ever get to masturbate. That is your punishment: you will masturbate with this strapon. You’re locked in your cage, unable to see me, and I expect silence from you while you keep pounding away at the strapon with your hand. Enjoy your little session; I know I will enjoy mine.”

So it turned out I wouldn’t actually get to climax myself—just pump the strapon while she enjoyed her own release. I began moving up and down the 9-inch strapon’s shaft slowly. Hearing the Hitachi turn on, she told me not to be shy because she certainly wasn’t. As she let out a soft moan, I pumped with slightly more force… perhaps if I was vigorous enough, I might achieve an orgasm after all. Her voice grew louder as I increased my speed. The lube squished with each motion; I caught her giggle when she looked over at me and saw the tortured expression on my face as I desperately tried to convince myself that this method would work for climaxing too.

She gasped loudly, held her breath for a few seconds, then began panting. “It gets me so hot pinching my own nipples while I masturbate,” she breathed out sharply before letting loose a long groan. All the while, I was furiously pumping that strapon, listening intently to every sound.

My cock strained hard against the cage in an attempt to reach full erection; I could feel it pulling and stretching my balls. She started panting rapidly, then took a deep breath—a familiar sign that she was nearing her peak. Knowing if we didn’t climax together soon she would be finished with me for good (and denying me my orgasm), I pumped the strapon as fast as humanly possible.

She took several quick breaths followed by one long inhale which she held…I knew it was imminent and kept pumping steadily.

“OOOOAAAAAAAARRRRRGGGGGGGGGHHHHHHH,” she cried out as the wave of her orgasm crashed over her, “Oh yeah! Oh yes! AHHHHHHHHHHHHHHH” rolling through successive waves. I pumped with all my remaining strength but couldn’t feel a thing happening down there.

It became clear that not only was I far from climaxing myself; I likely wouldn’t at this rate either. The sound of her turning off the wand reached me, followed by footsteps approaching.

“I’m going to read for a bit,” she said as she brushed the warm wand under my nose, leaving behind her scent on my upper lip. “Keep pumping. Don’t stop until I tell you to. You used to love masturbating; now you’ll do it until you hate it.” She paused thoughtfully. “Hmmmm… perhaps War and Peace? Or The Complete Works of Shakespeare? We shall see how long your arm lasts before it refuses to lift anymore just to stroke that strapon. And don’t forget the dishes this week,” she added with a teasing chide as she settled back onto the bed with her book.

My arm was already growing sore, yet I continued pumping away, wondering exactly how long she intended to make me endure this…”