Fair is Fair: Trying the Other Side

They say that good communication is the key to a good marriage and I think that's true. It's also the key to a satisfying sex life or it has been for me. And, a satisfying sex life is key to a good marriage, so it all comes back to talking to each other.

My husband Larry and I don't think of ourselves as kinky or at least not that kinky. But, we got bored with missionary position pretty quickly--me faster than him--and we wanted to find out what else there was for us to do. We've adopted a rule that either of us is free to ask the other for anything.

Literally for anything. One night, we played a game of who could ask for the most outlandish activity. I won that one but I won't tell you what it was. Even when we're joking about extreme stuff, we want each other to feel free to throw out an idea for something that we might really want to do. The other one doesn't have to agree of course but there's no judgement about it.

Why do we do this? Well, if Larry's afraid to ask me for something how would I know that he wants it? Maybe it isn't something I'm thinking about or even something I've ever heard of but shouldn't we at least discuss it? A couple of times, I've told him about something that I had been thinking about and I found out that he had the same fantasy. If I had been afraid to ask, we would have missed out on something that it turned out we both wanted to try.

So, good communication equals good sex equals happy marriage.

Regardless of what we're doing, each of us also really works hard to make the other person happy in bed. Larry likes to be edged so I tease him for as long as we both can stand. He knows that not only am I multi-orgasmic, but the second and sometimes the third one is even better than the first. I love his cock but it's not going to last this long so he uses his tongue and his fingers to make sure that I get what I want.

There are some things that I know he likes but that I don't. I might do them occasionally or I might not. I completely shave my pubic hair once a year as a birthday present to him and he won't even hint at wanting it more often than that. For my birthday, he lays on his back and pulls me up to sit on his face, licking me until I'm satiated. He says that my fluids running into his nose is annoying so it's not his favorite position but that he doesn't completely hate it. These things work for us.

I don't want you to think that we do stuff like this all the time. We don't. Sometimes we do quickies and sometimes we fall back to missionary. But we do them enough to keep our sex lives from getting boring. Good sex equals happy marriage.

Besides being open to requests, both of us are pretty open to trying new things. At least once. I've done stuff with him (or maybe for him) that didn't really appeal to me but if they don't offend me either, why not? I don't pretend to understand what makes it special for him, but I know that Larry likes to rub on my boobs until he cums. I can always take a shower after so why not? I like to be rimmed and as long as I've taken a shower first, Larry will go all in, licking my asshole while he fingers me. He says that he doesn't particularly like doing it but he doesn't dislike it either. He does it because he knows I like it.

Open to ideas is very different from open use and both of us accept that. Since we communicate and since we're open to trying new things, we also both totally accept hearing the word no. There are things that we've spoken about that one or both of decides is a hard no, at least for now. They might end up on a "maybe someday" bucket list or they might end up on a "please don't ever mention that one again" list.

One thing that I'm fully aware is absolutely on Larry's bucket list that has been a hard no for me is anal sex. He has apparently fantasized about anal since he first learned about it. I tried it once before I met Larry and that experience was more than enough. I think that it bugs him that I've done it and he hasn't and it's his fantasy. Too bad.

He has told me that he wants to experience it and I've told him it's not going to happen. In keeping with our rules on open communication, having asked and been told no, he doesn't bring it up again. But, when he gives me a back rub and massages my butt cheeks, a finger occasionally reaches toward my backdoor and I know he's thinking of it.

"Are you trying to stick your finger up my butt?"

"No, of course not. You said no." Deep sigh. "And no is no."

Hmm. "Yeah. It's not like I'm saying no randomly. You don't know how much it hurt back there. You're not exactly small, you know?" Maybe a bit of praising his cock will make the rejection easier.

"I guess I know that. Well, I don't know. I've never done it either."

"Maybe you should so you'd know what I'm saying."

"Yeah. Maybe." Long pause. If I do and I can take it, will you try it?"

"Yeah, sure." Oh, shit. What did I just get myself into here? Probably no risk. He's not going to let a guy fuck him in the ass, is he?

"Fine. Go get yourself a strap-on and I'll do it."

"Fine." A strap-on? Did he really suggest that?

Pegging a guy wasn't on my bucket list. Actually, I've never really considered it and it's never come up in our discussions of possible things to try. In fact, I didn't know exactly how it worked. After this conversation, I felt like I had committed enough that I needed to do some research. If I report back what I've learned, I suspect Larry will say thanks, no thanks and we'll go back to finding other, more pleasant things to do.

Online, most of the harnesses I find for a woman pegging a man don't look like they'd be real fun for him which may be why they were in the femdom section. But I also don't see what they do for the woman other than giving her a feeling of power. I don't cum without some attention to my clitoris and just sticking a dildo into him isn't going to do that.

But, I do run across what a double ended dildo that looks more enticing. On the boy end, it had a dildo like the other strap-ons I'd looked at. However, instead of just fitting into a harness, the girl end was a vibrator that fit inside her. As she moves in and out of him, she gets vibed so that she'd be able to cum (I assume probably before him).

In the interest of good communication and before I spent any money, I figured that I should find out if Larry would really follow through if I bought it. Plus, I needed to make sure that I was willing to follow through with my I-will-if-you-will.

"How bad do you want to try anal sex?" Nice conversation starter as we sat down to dinner, right?

"I won't die if we don't but you know that I'd like to. Why? Are you actually offering?"

"Did you mean it about you trying it first?"

Larry stared for a moment and then he nodded. "I guess. Fair is fair, right?"

I clicked the link on my phone and showed him what I had found. He read the description then slowly re-read it. Then he nodded again.

"Yeah, if this is what it takes for me to get to try anal, then I'll do it. I trust you enough to know that you'll live up to your promise if I do.

I smiled at him, clicked the "Buy Now" button, and ordered it. We had dinner and then quickly went to bed. During our love making, I could tell that he was really aroused and his fingers played around my butt and inched toward my butt hole. Me too--really aroused that is. I guess that thinking about our new toy made both of us hot and we had a fun evening.

It came several days later, packaged in a discrete box. I unwrapped it and--of course--tested the fit of the girl end. I found the button to change the vibration patterns and I made sure it was fully charged. I had also ordered lube so we were all set for an exciting evening.

As we did the dishes after dinner, I casually asked "Oh, guess what came today." He knew damn well what I meant.

I took a quick shower and put on a babydoll negligee. I inserted the vibrator end into my vagina and adjusted it for comfort. It stuck out below the negligee and Larry's eyes went wide as I walked into the bedroom.

I had considered the positions that would be available and decided that I would have him bend over the side of the bed. I directed him there and was surprised how he quickly complied without saying a word. I took the lube and squeezed some onto my finger, then lubed up the boy-end of the toy. I squeezed out more and applied it to his anus, putting my finger in where it had never been before. After making sure that he was fully lubed, I wiped my hands on the towel I had put next to the bed and stood behind him.

Bending over, Larry's rear entry was on the perfect level for me as I stood behind him. He was hard but I planned to avoid touching him in the front while I played in the back. I reached down, turned on the vibrator, and took in its pleasant sensations before moving closer to him.

Despite my fingers and the lube having opened him some, his anus looked tightly sealed and looked small compared to the end of the dildo. I thought back to my experience on the receiving end of anal sex and how I felt like he was going to split me open when he pushed into me. I remembered how sore I got from the friction as he pulled in and out so I decided to add some more lubricant to Larry and to the toy.

Neither of us spoke as I held the tip of the dildo against his hole and start to slide into him.

I pushed in as slowly as I could. Even with the extra lube, there was some resistance so I pushed in gently, hoping that I wasn't hurting him. Suddenly the dildo seemed to pop through the sphincter and it slid all the way in causing Larry to grunt. The vibrations inside me as I did this felt nice and I felt my nipples coming erect and my midsection getting heavier as my arousal grew.

Instead of concentrating on the vibration pattern and its effect on me, I remembered that I was the one penetrating him, so I needed to take a more active role. I moved my hips back quickly and then slowly shoved back into him. After a few strokes, I got into a rhythm, moving the toy in and out. I was still conscious of the vibrations inside me and I touched the button again to change to a slower, steadier pattern. I wanted this to last as long as possible.

But I also tried to be conscious of Larry and to make sure that I wasn't hurting him. If he had asked me to stop, I would have, of course, but I wondered if he would have expected anal sex anyway. Moot point since he didn't ask. In fact, he might have been enjoying it. Or maybe not. Larry wasn't one for making a lot noise during sex so, other than occasional murmurs, I didn't know what he was feeling and thinking. At least he wasn't complaining.

As I moved in and out of him, I thought of what we looked like with him bent over the end of the bed as I stood behind him. The image changed to one of me bent over the bed as he fucked me in the ass. Larry had agreed to the first only because he wanted the second and I was committed to giving him the experience that he wanted. But not yet. My plan was that I would keep doing it until I had cum at least once from the vibration. But, I was in no hurry and as long as he wasn't complaining, I would keep going.

I was aroused from more than just the pulsation inside me. There was also the feeling of power and control that came from being on the giving end instead of the receiving end of the penetration. We had implied that this was a one-time thing so that Larry could have his bucket-list anal sex experience. But suddenly, I realized that I absolutely wanted to do this again if I could find a way to get Larry to agree. What other soft no might I have to give into in order to get him to agree? That was to be determined, but I was getting into what I was doing so much that I might be ready to do whatever it took. Plus, we had spent the money to buy the toy so it would be a shame to not get some more use out of it.

Through the tension in my pelvis, I felt pulsing besides that coming from the vibrator. With my pre-orgasmic sounds, I knew that I was heading to a climax and moved my hands to my nipples to help myself get there. Through my noises, I realized that unlike his normal quiet, Larry was moaning too. Each time I moved my hips to push into him, I was (I learned later) pushing on his prostate.

We came nearly at the same time, me pushing into his butt and him pushing into the mattress. I switched off the vibration but kept the dildo inside of him. I laid against him, wrapping my hands around his chest with my head lying on his back as I enjoyed my post-orgasmic high.

When our breathing returned to normal, I pulled out and took the toy into the bathroom to clean it off. I took off my babydoll and climbed onto the bed to cuddle with him. He finally looked at me and just said "wow."

"Yeah, wow" I agreed.

We lay together until I felt him growing hard again. I reached over and handed him the lube and then lay face down on the bed, allowing him access to my anus. I was still nervous and hoped that it would at least not be as bad as my first time. But, fair was fair and there was always the chance that I'd enjoyed it as much as he apparently did.