The 25 Orgasm Week - Part 1 - One through Five - xposted | 2016

This is a story about one of the most sexually tiring weeks of my life all caused by a little game I liked to play with an ex who at the time was 24/7 slave, Cynthia, called the rules box.

For details on that box: http://www.reddit.com/r/ReaderAnonErotica/comments/1ttat2/the_rule_box_and_punishment_box_an_explanation/

But basically, a box with self written “rules” to live by for a set amount of time.

This is a story about a challenge a sub gave herself and the increasingly extreme lengths she had to go to to achieve them.

*

Orgasm 1 It was Monday. I had class late in the day, one before and one after lunch. So I had a nice leisurely wake up fuck with Cynthia and then done some homework while she did her chores.

That day Cynthia would finished her most recent rule. She had had to prepare all of my meals for three days, while performing some sexual thing and either tell me while I ate, or give me a note explaining what she had done.

She came in while I worked and handed me toast with two boiled eggs and said, “I stuck a wooden spoon into my pussy and held it their while the eggs boiled.” I gave her a kiss, a swat on the rear and went back to work while I ate.

For lunch, I had opened my lunch that day, a sandwich, chips, and normal fair to find a note that read.

“To Master, a simple lunch made by your slave while wearing a butt plug.”

There was no “rule” about when we pulled the next rule, but usually it was as soon as we saw each other after a rule was finished.

I got home that afternoon and she was on the couch doing homework. It wasn't Friday and we had, since starting the rule box game, felt life was easier if she only greeted me as a slave on Fridays.

She was of course, nude and wearing her ankle cuff and greeted me with a “Hello Master, how as your lunch.” Unless otherwise stated, we assumed at all times that she was in what we thought of as girlfriend submissive mode. I was her master, she was my sub. We had a number of normal rules in place, but they were lax.

“Good,” I said, “better to know what my slut was up to while she made it.”

“It was a fun rule, I might make you more lunches in the future,” she said and stuck her tongue out at me.

“Are you busy,” I asked, “Or would you want to get the box?” As a rule, she had to get good grades and I was NEVER allowed to give her an order, punishment or task that interfered with school work. In fact she got HEAVILY punished for poor grades.

“Oh no,” she said, putting her work away, “Nothing due soon, I was looking forward to it.”

She stood. Cynthia at this point was on the slightly heavy side of curvey. A pretty face, decent breasts and a pleasantly round ass. She kept her brown hair cut around her neck or higher. She had long sense lost any sort of discomfort in being nude around me. As a rule, she wasn't allowed clothing in the house unless we were having company (and depending on the company, sometimes even then.)

I gave her a kiss as we proceeded to the bedroom and I got the box out. It had RULES written on it in thick black marker.

“What are we at now,” I asked. “Getting low?”

She shook her head. “Two more pulls, plus Steve and Sarah added a few to the box when we played cards the other night.” Steve and Sarah were another 24/7 couple we were friends with.

I nodded. “Should I do the honors or would you like too?”

She grinned. “I'd like to please master.”

I held the box out to her. It was a shoe box, the kind you get with a new pair of shoes and I had cut a hand sized hole in its top.

She closed her eyes and said, “This is the best part!” She reached in and pulled a slip of paper, unfurled it, read it, paused and handed it to me.

-Slave may not have an orgasm until Master has had 20. Master may not intentionally force slave to orgasm, though Master may play and fuck slave normally including the use of toys for her pleasure. Each failure adds two more orgasms for Master AND one punishment pulled from the punishment box. All other normal rules including Slave's masturbation tease are too continue as normal. Master may not deny Slave's request of sex if Slave takes the initiative. If sub can finish in less than seven full days, Slave is allowed unlimited orgasms for three days.-

I looked at Cynthia but said nothing. The rule about the rule box was that we pretended to not know who put the rule in. As a few friends, like Steve and Sarah threw them in occasionally, it made it easier. This was a neat little trick to give us a chance to “secretly” introduce kinks that may have been awkward to admit to wanting to try or do again.

In this case though, the rule wasn't written by me and it was damn specific. Normally our friends rules were simple and rarely refereed to us as Master and Slave. She had written this. I knew she was into orgasm denial. In fact, the masturbation tease thing was a standing rule with us for years. Every day I was at class or work, she was expected to spend 15 minutes masturbating to almost orgasm, and staying there and then stopping entirely, not being allowed to cum until I got home.

Orgasm 2

I said nothing and nodded my head. “There's not time limit, I guess it just lasts until I have 20 orgasms. It's a good thing I've only come once so far today.”

She nodded, bit her lip. She had trouble initiating sex. She said it was more from feeling shy than being submissive, though you would think that after being with me for years, having done incredibly perverted things with me, she'd have lost the shyness.

“I think that's right,” she said, “Master, may I suck your dick.”

I opened my mouth and closed it and then just said, “sure.”

My nude slave dropped to her knees, unzipped my cock and began to lick it. She'd start with her tongue on the top of the head of my cock and then run down the base. Then she moved her tongue back to my head, on the side, and licked downward again. Then to the base of my cock had, and down the shaft. So on.

She stopped when I was halfway to a full erection and pulled my pants and boxers off and asked me to sit at my desk chair. We did oral sex in it often and both found our cock sucking positions.

Cynthia was rarely ever able to get me off with just her mouth. She had given up a long time ago, though she had learned to deep throat by then. She did just that to me as I grew harder and harder, slowly sliding her mouth all the way up and then down my cock, swallowing me deep into her throat, sticking her tongue out to lick my balls.

When I was ready, she began to stroke my cock with one hand, matching rhythm with her mouth. I just at back and enjoyed it. After a bit though, I had an idea.

“Masturbate,” I said. “I want to enjoy my orgasm knowing that you can't have one.”

She snorted, but her other hand went between her legs. She kept stroking me and I could see her eyes closed in pleasure as she did so, see her body twitching slightly as she pushed herself closer and then I warned her and began to cum.

Cynthia never liked swallowing semen. She had learned to live with it though and sucked every once of me down.

She pulled her mouth off, smacked her lips and said, “Well Master, one down, 19 to go. I'm going to start dinner and we will have a chat when you refractory period is done.”

I grinned and pulled my pants back on. I thought that this would be a fun.

Orgasm 3

Dinner was chicken tacos. It was tasty. As normal we sat at the table facing each other. Her nude but her ankle cuff and me dressed. There is something so powerful in power exchange about one person being fulling dressed and the other nude.

We talked about our days and what we were working on. When we finished, before she cleared the plates, she got onto the floor, crawled over to me and said again, “Master, may I suck your cock.”

“Of course,” I said and she started to tug my pants off again. I was still a young man at the time and her mouth on my cock, sliding up and down, got me hard again quickly. I thought I was in for another blow job, but instead, she climbed up onto my lap, facing me and with her hand position my cock as she slid down onto me. Her feet could just reach the floor.

I was still wearing my shirt and my pants where around my ankles, but I didn't notice as she started to fuck me. Sliding her body up and down, using her feet and holding onto my shoulders for leverage.

It felt amazing her wet pussy on my cock. Her being the aggressor, her just needing me to get off without any concern for herself.

We fucked and fucked like that, my hands on her ass lifting her, her moaning softly in my ear and saying things like, “Cum in me, fill me with your cum, Master I need you to fill me up.”

It wasn't long before I came inside her. When I finished, she kissed me on the lips, said “Thank you Master,” and carefully climbed off of me, going to clean up in the bathroom.

I shook my head with a bemused smile on my face and went after her to clean up as well. After that we both sat, working on our own projects.

Orgasm 4

It was roughly 8 pm by this point and we were sitting down to watch a show we both liked. I was in my boxers and a shirt and she was, of course, nude. We cuddled and as a rule, she rubbed my cock. It was actually a rule. During prime time tv time, she was required to rub my dick. She didn't have to jack me off, or really do much, just lazily play with my dick as we watched tv.

Tonight though. Tonight she was actively stroking me. She even spit into her hand to use as lube. By the second commercial break I was rock hard, aching slightly, and she said, “Master, during the next commercial, can you fuck me and cum before the show gets back on?”

“I uhhh,” I said. “Sure, I can try, I normally and trying to do the opposite.”

The commercial came on and she dropped into a doggy position on the floor. “Please Master,” she said, “fuck me hard and fast, cum quickly.”

I dropped behind her, slid my cock to her entrance, noted she was wet, and slid in. I started to fuck her pretty hard, as hard and as fast as I could. I focused on the feeling the pleasure of her pussy and then she said, “Master, please finger my asshole.”

She knew me so well. I slid a finger into her asshole and was cumming in moments. I got up, tired, and flopped back onto the couch. She carefully stood and instead of going to clean up, pulled a towel out of no where, I hadn't seen her grab it, put it on the couch and lay across it. She lay perfectly so that her head was on my lap and took my shrinking, sex covered cock, into her mouth.

We watched the tv like that. Her gently sucking me hard again and, while it took well into the next show, I finally became hard again.

Orgasm 5

She stopped sucking on me and produced the lube from no where. Again I hadn't seen her stash it. She lay on the floor, on her back, lifted her legs to her chest and began to lube her asshole. She knew I loved to watch her get herself ready for me for anal.

“Master,” she said, “Do I need to ask?”

“No,” I said and got onto my knees, aimed my cock and slid in. I was tired at this point. If you have never had marathon sex, you don't understand. My cock hurt a bit and the muscles used to fuck where tired. I had no idea how tiring it would get over the next few days.

I started to fuck her ass and she played with her breasts, pinching her nipples and licking her lips at me. Trying to act like a dirty whore to get me off.

“Play with yourself,” I said. And she did. I love looking down, seeing my cock in a woman and her fingers playing with her pussy.

It took a little bit, but I came in her ass and she thanked me. We got up, I stumbled. We went to the bathroom and showered quickly and went to bed where I passed out.