Stacy's Bet - Part 1 - Stacy wins a bet and I end up face down with my ass in the air - F/m - rimming and anal play on a guy - bondage | 2016

This is a story about Stacy, who is difficult to explain.

At this point in our relationship, Stacy identified as a submissive . . . but made you fight her or beat her in some way before she would submit. I don't mean, mock rape, because it was never that. No, Stacy wanted to be beaten in a game or physically overpowered and then give in to the winner. She viewed her body, her sexual skills as a prize that she wanted you to win. But she MADE you fight for it, she never just gave in.

She explained this to me once using the classic “caveman” story.

“I'm like a cave woman,” she said, “You have to hit me over the head with your club and then drag me to your cave by my hair, but once I am there, I recognize you as my mate and will spread my legs for you happily.”

Another time, she used the example of the princess whose hand is the award of a contest that all the princes of the land come to compete for, but that she secretly enters herself. In the fairy tales, the princess bests the men. Stacy, wanted to best all the men but one and then give herself to that one for proving himself better.

On top of this, Stacy didn't like to admit or ask me to do certain perversely sexual things that she was interested in. Some things, like anal, she loved and was verbal about, but things she saw as incredibly submissive, she didn't like to admit to wanting. So, she would often, when she wanted to try something new or wanted me to do something incredibly perverse to her, would maneuver me into it or piss me off to get me to go overboard.

As an example, she wanted to try being forced to be my sexy maid one time. Kept nude, forced to do housework, fucked on a whim. Instead of asking, she used it as a bet in a game we were playing. If I won, I got her as my maid slave for the weekend. If she won, I had to take her to see a musical in the city that she wanted to go to and that would be very expensive. I won and she was happy to full fill her end of the bargain.

This is one of those stories. Beware reader, this story contains some violence, some anal play on a guy and some water sports. It contains a lot of sex as well.

*

Part 1 – Stacy and I make a bet

I was spending the summer with Stacy. She was living in a small city about 40 minutes away from an internship I had won and as we were off again on again FWB we decided to spend the summer living together. We had explored a number of kinks including progressively more BDSM related items when Stacy asked me about why I was never submissive.

The answer is that I had a horrible experience my first time being tied up that involved almost dieing. I was already VERY dom and hadn't really been into trying submission in the first place. It was years before this happened and Stacy asked if I would be up for trying with her.

I considered it and she made me an offer. IF she dommed me. She would make the session all about me and that it wouldn't include any pain. That she would basically tie me down, tease me for a bit, sexually pleasure me for a bit, perhaps verbally dominate me and sit on my face. But that there would be no pain involved.

Now here is the thing. I knew Stacy at this point. I knew that I could trust her with my safety. I knew that she was being serious about what she was offering. BUT I also knew that she was most likely hiding something and that this was going to be a set up for something. The idea actually intrigued me and made me nervous. What was she planning? What was she considering?

I decided to go for it, but to play her game.

“Ok,” I said to her, “It will be out next wager. If you win, you can tie me down and play your little game.”

“Ohhhh,” she said “And if you win?”

“If I win,” I said, “You have to tell me the truth, of what you were planning and what secret thing you want to try but didn't want to admit too.”

She gave me a look that said, “that would ruin the fun,” but she agreed.

I don't really remember what the wager was over. Something later that day, an argument over an actor in a tv show or something. The end result was that I lost though. And it would be that night that I was tied down for the second time in my life.

*

Stacy and I took a shower together and while this often ended in sex, she would only let us rub each other a bit, she wanted to save it for later. She did pay special attention to cleaning my butt and I did the same to her as anal sex was common for us.

She was a lovely curvy woman and as we got out of the shower I gave her butt a playful smack and she hit my hand away.

“Nuh uh,” she said, “I'm in charge for the night, you go watch tv for a bit while I get ready.”

About 20 minutes later she called me into the bedroom. She had set candles all around, there were fresh sheets on the bed and she had a few of her sex toys out including the lube. I nervously looked at the candles and said, “we agreed no pain, you aren't planning to get coy with those candles.”

“RD,” she said in a soft voice, “I wouldn't hurt you, I know how you feel about pain. I promise that I will focus on nothing but your pleasure and mine. OH and call me Mistress.” She ended with a big grin.

I laughed, “Ok Mistress.” It was hard to say it without sounding sarcastic.

She was wearing a sexy sheer black nightie with black panties, I was only in my boxers.

I shrugged. “Ok Mistress, you are in charge.”

She nodded and said, “strip.”

I pulled my boxers off, I wasn't hard yet, still nervous about those candles.

“On the bed, on your stomach,” she said. I complied and laid down on the bed. She walked around and with the rope I had bought to tie her down, secured my my wrists to either side of the headboard and then my legs, pulled apart and tied to the foot board.

She started to walk around the bed, letting her fingernails scrape lightly on my bare skin, it felt nice, and then she climbed up onto the bed, straddled my butt and I felt something warm drip onto my back. I tensed, thinking it was wax, but it didn't hurt.

I realized it was some sort of lube that she had warmed and then, as I felt her panties on my ass, she began to massage my back and shoulders. She rubbed a warm oil into my shoulders, and my back, the whole time grinding her pussy against my ass, my legs, my arms. She would straddle my arm and rub her panties up and down its length while she kneaded a shoulder. She pushed her clit into my thigh as she did my back.

Then she did my legs, reaching between and up a few times to rub my cock. It didn't work well. I know there are videos of guys whose cocks seem to bed behind them, mine doesn't. When my cock is hard it sticks straight out and up.

She was able to reach my balls and ass though. She knew how to handle my balls (carefully!) and we had months before began to experiment with rim jobs. She teased my butt a bit, letting her finger slide across it in a way that felt like a tongue. I was incredibly relaxed, almost falling asleep actually, when she decided to take things up a notch.

She untied my ankles and wrists and had me get into a position on my elbows and knees. She tied me back like that to the bed and then put a towel under my midsection. I guessed that she was going to rim me. We had done that a few times. What I wasn't counting on was that she had been reading up on prostate play.

I want to be clear. Up to this point in my life I had NEVER had anything pushed into my ass. I had NO interest in it at all. I had told her so a number of times and the closest I came to it was a few times that she or another woman had pushed their tongue in a bit.

I started to feel a bit exposed, but as she had promised nothing but my pleasure and no pain, it didn't occur to me that she might assault my ass. I actually made a joke about it.

“I hope you don't have a strap on Mistress,” I said.

She laughed. “No,” she said, “just my body.”

Then she moved in behind me and started to lick my asshole. As she did, she reached in and under me, her hands still covered in the oils from the massage, and began to stroke my cock.

She had great stamina and I just relished the sensation and felt her hand stroking my cock to an orgasm when her mouth pulled away from my ass. “Remember,” she said, “you can't cum without permission.”

I laughed at that but said, “sure mistress.” and felt her lean back in to slide her tongue across and around my asshole.

I find rimming to be a pleasant sensation. In no way to I find it to be more pleasant though than a deep kiss. It's pleasant, but alone the pleasure would barely even be enough to get me hard. I do however, find rimming to be very hot mentally. I love humiliation and it's hard to not view someone licking your asshole, even if you are tied down, as being humiliating for them.

So the feeling of her tongue on me, of it sliding a bit deeper into my ass and her hand stroking and stroking my cock, lubed up and warm, sent me close to the edge of orgasm very quickly.

“Mistress,” I said, trying to sound humble and subservient. “May I please have an orgasm.”

She stopped rubbing my cock immediately and her tongue left my ass. “No,” she said and I admit that I groaned in frustration. I felt her tongue go back to my asshole and her fingers began to lightly caress my balls. After what felt like hours, her hand went back to my cock and started to stroke again.

Again I grew close to orgasm and she stopped as soon as I asked to cum. We waited and she started a third time.

This time though, she taunted me. “How badly do you want to cum?”

“Very badly . . . mistress,” I replied. She giggled and started to lick my asshole again.

Her hand quickly whipped me into a frenzy and I asked to cum, expecting her to deny me. She did . . . but she didn't stop stroking me. Instead, her mouth left my asshole and I suddenly felt her finger, heavily lubed, pushing its way into my backdoor.

The shock was enough to keep me from orgasm.

“WHAT THE FUCK,” I roared.

“Does it hurt,” she asked, pulling the finger out.

It didn't. It felt strange, but didn't hurt at all.

“No,” I admitted and felt the finger push its way back in.

“Well too bad, then,” she said, “I promised no pain.”

“You know I am going to make you pay for this,” I said to her and felt her start to fuck the finger in and out of my ass as her hand kept stroking my cock.

“I'm counting on it,” she said, “you may cum as soon as you are ready.”

The finger in my ass was strange. She was fucking me with it and I felt no pleasure from it, but still, the hand on my cock was coaxing me closer and closer to orgasm and finally I came pretty hard.

I don't know if I'm just not a prostate guy, but I've never found anal penetration to add anything to my orgasms. When I was done Stacy pulled her finger out of me and said, “Holy shit, I see why you love anal so much, that was fun and your asshole like spasmed when you came.”

I grunted, still recovering and manged a vague threat about what was going to happen to her when she untied me.

She laughed and said, “Sorry bucko, you are going to have to wait, I'm not done with you yet.”

She left me tied and went to the bathroom to clean up. I did this to her all the time, so it was fair. When she came back, she pulled the towel away and tossed it and then untied me and had be get onto my back, tieing me spread eagle again.

End part 1 - My work: http://www.reddit.com/r/ReaderAnonErotica/comments/1ssuhm/story_index_start_here_to_search/