More Than Jon Could Chew

*Note to the reader- This is my first time writing something of this nature, so bare with me. I'm going to try and make it 2 parts. No more than 3. This is a fantasy story with ties to reality, but most of it is fantasy. Enjoy

*

"Been thinking about you. Wondering how you're doing." Mistress sent that almost three weeks ago, and it's still on my mind. I've been ignoring her for going on 8 months or so, being in a relationship for going on 3 years. Ever since the incident, I've cut all contact to Mistress, though I still regard her as Mistress. I never had any feelings towards her besides friendship and sexual, which was unfortunate because she thinks she loves me...sigh. Now that I'm single, I'm not sure how long I can hold out against contacting her again.

It has been almost a month since we broke up. After weeks of searching the 'net for a "no strings attached" online mistress, I finally cave in.

"I'm probably going to regret this, but fuck it." Reaching for my phone, I realize I have a major rager. I'm really nothing special from about 6" to 6 and a half on a good day and circumcised. I'm not ashamed, nor am I proud, but it is frustrating being what I like to call a "grower, not a shower." One thing I am proud of, is that I know how to use it.

I'm what you call a Switch. Switching from Dom to Sub is pretty easy. And even though I don't have much experience being a Sub, I know I prefer being a sub. Now is my opportunity for Sub experience. While playing with myself, I hammer out a response to Mistress. Explaining that I've been in a relationship since we last talked and how I didn't want to ruin it and such. Not a minute goes by when I get a response. "So you're single now?"

"Yes I am."

"Is it for sure this time?"

"Yes it is. Will you have me back as your Slave?"

"You realize I'm not happy with you, and you will be punished?"

" I do. I'm prepared to accept my punishment. I haven't been a very good slave to you."

"If you say so. Yes I accept you. Put your collar on. 2nd notch. Have you bought anything since we last talked?"

"Yes Mistress. Only thing I bought was a new chastity device. CB6000." I start digging through my closet looking for my collar. It's just a simple spiked collar you wear on your wrist from Hot Topic. It takes me a bit to put it on the 2nd (tightest setting) notch since it has been so long since I've worn it. Upon returning to my phone, I see she has responded with "Do you have rope? Or ribbon? Something you can tie around the collar?" So I grab the nylon rope I had bought a couple years ago and tie it around the collar with a slipknot.

"While lying down, pull it as tight as you can. Then, without loosening it, sit up a little bit and tie the other end around your neck. Send me a pic." I do so. And it hurts exquisitely. The spikes buried deep around my cock and balls. Now it's one thing to have this collar on while limp. It's another with a boner. And she knows this very well. Next thing I know, she's calling. "Yes Mistress?"

"I want you to get your lube and masturbate. Don't get off until I tell you. I want to hear you whimper."

"I understand Mistress. " So getting up, very gingerly, I grab my lube and lay back down. "This really hurts Mistress" I say to her. "Good. I want it to. And I'm not going to help you with this. But you better think about me."

I start stroking myself, and as I grow, so does the pain. Grunting and moaning and pretty soon I'm completely erect. But I can't stroke. "Mistress. It hurts too much!" There's no response. I slowly start stroking myself, playing with the tip. The more I play, there hornier I get, until I start stroking my entire length of my cock. I hear a whisper, "Good boy. I knew you wouldn't disappoint me. Keep stroking. If you get close, stop for a minute and start again." I respond with a "yes Mistress" and continue stoking. Telling her how bad I want to fuck her and how I'd do almost anything to please her.

"you still have that dildo?" She suddenly asks me 20 minutes later.

"I do Mistress. Though I haven't used it in over a year." I reply lamely

"Well go get it and put it in. Make it quick slave!"

So I get up and start digging through my closet for my 8" by 1.5" vibrating strap-on. Cleaning it off and lubing it up, I get on my hands and knees and slowly push it in. once in all the way, I lay back on my bed and start stroking. "How does it feel?" She's asks me quietly. "Ummm. Well it was difficult to get in and besides my torn butthole, it feels nice." I can hear the smile when she tells me "Good. Get used to it."

Another 20 minutes or so go by when she tells me I can cum one condition. I already know the condition because this was a standing rule with her long ago. I have to either shoot in my hand and eat it, or shoot into my mouth. She usually prefers shoot into my mouth because it's messier. Only this time, I have to sit up and shoot into my mouth. "sit up and shoot it into your mouth. Don't swallow it just yet. Send me a pic of it." So I start stroking faster, already sitting up and ready to catch it. Grunting and moaning I start getting close. "Good slave. Shoot that hot cum into your mouth like the dirty cum slut you are. Savor it" that was all I needed. Shooting like a rocket, I miss the 1st shot, square on my nose, splashing on my forehead and eyelids. Shot after shot I aim true and straight to the throat. After about 6 or 7 shots to the mouth, I lay back down with a huge sigh.

As it dribbles down my cock, and with a full mouth I tell Mistress I'm done. She hangs up and I send her a picture of my full mouth and dirty cock. Now that the excitement is over with, pain starts consuming me tenfold. I ask her if I can undo my cock and balls and cleanup. She responds with a laugh, "no you may not slave. I want you to lay there with that mouth full and think about what you did to your Mistress. Lay there until it doesn't hurt anymore."

"Yes Mistress" I respond. I lay there for a good half hour, squirming in pain and feeling gross. Just as the pain starts to recede, Mistress messages me again. "Just imagine what I have in store for you when I get my hands on you. We're going to have so much fun! Or at least I will. You're going to regret ignoring your Mistress. Yes. I have so much planned for you hahaha." So naturally I start imagining what she has planned for me. Knowing what she likes and wants to try, and she knows the things that I want to try or have been curious about. I can't help but get hard again; pain shoots through my body as I ask Mistress if I could get off again. "No you may not, but I want you to stroke yourself for 30 minutes. And think about what I might have planned for you. Only after can you relax and undo yourself."

I do as she says. Stroking away but not ejaculating. Following the half hour of agonizing torture, I undue my restraints and extract the strap-on and ask "May I swallow and clean up now Mistress?"

"Yes you may. Don't take the collar off though. And put your butt-plug in. Leave them until I say you can take them off. We are done for today. When can I see you?"

"Well Mistress, I'm taking 19 days of leave here in a couple of weeks. And there's a few days hat I don't have planned yet." I tell her with a smiley face.

"How many days would I get with you?"

"I can give you 4, maybe 5 Mistress."

"Good. Chastity belt will be on until then. Bring all toys. And I will be going online to find some things for you to buy and bring with you." I know this is not good. She defiantly has something planned. Only a matter of time till I find out