Fair is Fair: Now It's My Turn

This is a sequel to "Fair is fair: Trying the Other Side. I recommend reading it first.

My husband Larry was very well aware that I disliked even the idea of having anal sex. Vagina? Of course. Mouth? Yes, and I'll swallow. Cum on my boobs? Sure, no problem. Face, maybe, as long as you warn me so I can close my eyes in time.

In my butt? Nope. No way. Not going to happen in this lifetime. That's why I'm totally surprised to find myself voluntarily lying on the bed, face down and butt up as Larry lubes my anus.

Larry and I both pride ourselves on being open to trying new things in bed. Our rule is that either of us should feel free to toss out ideas for anything sexual we might do. Sometimes these are things for both of us and sometimes they're a fantasy or just a fun image that appeals to only one of us. Offering ideas just to think about can be fun in itself and it's really fun to come up with fantasies when you have a creative partner.

Of course, we don't try everything that is suggested. Not even close. But you never know where an idea might lead. Also, we're both willing to try out new things for each other. One of us might suggest something that the other doesn't jump up and down for but as long as one of us doesn't dislike the idea, we still might try it. That's how you keep your sex life from getting stale and keep your marriage alive. At least, it's worked that way for us.

Of course, there are still some things that we've discussed that one of us wants, maybe even really wants, but the other says no way to it and that's it. No judgement for bringing up the idea but no pressure either. Some things are meant to never come off our sexual bucket lists.

Anal sex was one of those things that, pretty early in our relationship, I learned was on Larry's bucket list. Unfortunately for him, he immediately, clearly, and emphatically found out that it was on my that's not going to happen list.

I didn't feel like I had to justify saying no but I did give him an explanation anyway. I described to him how I had tried anal once with a boyfriend before Larry and I ever met. Let's just say that I didn't enjoy it. The guy didn't use enough lube, pushed in without getting me relaxed, used a bad angle, and generally ignored what I was trying to tell him. If wasn't just the bad anal sex that caused it but we split up pretty soon after that night and I never wanted to repeat the experience. Even though Larry wanted to try it, he understood how I felt and he didn't push me on it.

Although I believe that he accepted me saying no, one night while we were making love, I wondered why he had moved his fingers closer to my butt than he normally did. After, I asked him if he was trying to give me a subtle hint. He denied that but in the conversation that followed, I tossed out an "I will if you will" tease. Pegging him certainly wasn't on my list of things to try and I was pretty sure that there would be no way that he'd ever let anyone put something in his butt. To my absolute shock, he told me that he would if I would. I guess he wanted to try anal sex a lot more than I knew.

Not knowing anything about pegging, I went online the next day to do some research about strap-ons. I found a double-ended dildo that, instead of just fitting into a harness for the woman to wear, had a vibrator that fit inside her. I still didn't feel any real attraction to the idea of me pegging him. No judgment about people who like that, but l honestly didn't see what would be in it for me. At least including a vibrator would make it more fun and it would be a good excuse to buy a new toy.

I showed the webpage to Larry, expecting that he'd have changed his mind by now. Again shocking me, he agreed, so I bought it.

Well, we did it and I found out how much fun it was to be the penetrator instead of the penetratee. Of course, I loved having the vibrator inside me as I pushed in and out of him. I also got kind of a power trip from being in control and I think that was a big part of my resulting orgasm.

But, lying together afterwards, through my post-orgasmic bliss, I realized that it was now going to be my turn. Despite my hesitance, I had told Larry that I would if he would and he did. Hesitant or not, now it was time for me to live up to my part of the deal.

I really hoped that anal sex with Larry would be, if not good, at least not be as bad as it had been during my first and only other time with a guy in me back there. I was going to make sure we used lots and lots of lube and I knew that Larry cared for me so he would go out of his way to not hurt me. Even so, I was still nervous and greatly regretted first making the offer to him and then doing my side of it with him on the receiving end.

If I decided that I couldn't go through with it even after he let me peg him, I don't think he would be happy but I'm pretty sure that that would be the last time I heard about it. Even without Larry making me feel bad, though I would probably beat myself up for disappointing him and for disappointing myself by not following through on the I-will-if-you-will that I had proposed.

So, I handed Larry the tube of lube and then lay face down on the bed. Nervously, I parted my legs to offer him access to my anus. With my butt open to him, I started a mantra in my head, reminding myself that fair was fair and that I had agreed to what he was preparing to do. Despite the fear and trepidation I felt about finally letting him push his cock into my back door, I badly wanted to fulfill my part of our deal. I would force myself to accept what was coming and would live with the consequences of having made the offer.

In reality, I realized that even if I didn't like it which was likely, it probably wouldn't be that bad, right? There wouldn't be any permanent damage and, even if it hurt some, I would survive the experience. If the pain was too much, I knew that Larry would stop. In the worst-case scenario, I would feel sore back there afterwards but I would have made my husband really happy. Plus, I would have learned my lesson about making offers without thinking them through.

One other thing floated through my head. Even though I really doubted it, there was always the small chance that I'd enjoy it as much as Larry had apparently enjoyed me pegging him. That had surprised me so maybe I'd be surprised again. Probably not, but maybe?

Standing over me, Larry squeezed out some lubricant from the tube onto his finger and reached down to my butt. The touch of his finger on my anal opening felt strange and the lube was cool as he rubbed it around the outside. I tried to let go of my tension but that was difficult and, rather than relaxing, I clenched up even more when he inserted the tip of his finger to lube me inside. He pulled his finger out and added more lube before returning it. The finger moved in and out and he moved it around in a circle pattern, both lubing my anus and, I think, trying to get me to relax it. He was only partly successful there but the movement of his finger was, if not enjoyable, at least not painful.

After what seemed like a couple of minutes of his finger playing around back there, Larry stopped. I looked over and saw his very erect cock and watched him squeeze some lube onto the tip. His hand sliding down over his cock sort of looked like he was playing with himself. Maybe he was going to do that instead and I'd be off the hook. Nope, that was just wishful thinking. What he was doing was moving the lube down to cover the whole shaft to cut back the friction of him plunging it into me. Finally, he wiped his fingers off on the bedside towel and he pulled me into the position he had chosen.

When I pegged him, I thought about possible positions to use and decided I'd have him bend over the side of the bed with his feet on the floor. Given our height differences, this seemed like it would give me a good angle and it did. Evidently, he was planning to use the same position so I slid my body over to the side of the bed and swiveled to point my legs at him. My head was now facing away from him with my boobs against the mattress, and my face on a pillow. My butt pointed toward him as if it was surrendering itself to him.

Since Larry is a lot taller than I am though, the angle was different than when he was lying here for me. That seemed to make it harder for him to aim at his target and in order to fix that, Larry grabbed a couple of our pillows then tapped the side my hip. I pushed up and allowed him to slide the pillow under me, raising my pelvis up for him.

I didn't feel Larry doing anything so I looked back and saw him standing behind me, just staring down at my butt. At last, he put a hand on the small of my back and stepped in closer. Then, I felt both of his hands on my butt cheeks gently separating them and fully exposing me.

Despite Larry's attempt to relax me with his fingers, I tightly clenched my anus when I felt that first touch of his cock against it. Fortunately, he didn't just shove it in like I had feared. Instead, he moved the tip back and forth against my opening like he was probing for a way in.

Finally, Larry began to push into me but still not hard. It was almost just a pulsing as he pushed gently against me and then pulled back. Despite my resistance to what was coming, I tried to spread my legs further for him, partly to give him access and partly signaling that I was ready for him and fully accepted what he was going to do to me.

Then, I felt my anal ring separating and the tip of his cock started to move into my opening. It didn't really hurt but it didn't feel good either. I felt a mild friction as the skin of his cock rubbed against the skin of my back entrance. Larry must have felt this too--he stopped pushing against me and I felt the coolness of more lubricant being squeezed out onto my anus and onto his cock.

As Larry pressed his cock against my hole, I now tried to press back. I struggled to relax but my tension back there grew more intense as he pushed in. I felt myself stretching as his cock pressed against the first sphincter. It was similar to that amazing feeling of being stretched when he starts to enter my vagina. Yet, it also felt very different and certainly was not that wonderfully divine feeling I'd get in front.

I had no way to know how much of Larry's cock had entered me but my impression was that only the tip of his cock was in. That changed as he continued to press against me and to still gently push himself into me. At first, my body fought his intrusion but the combination of his pressure and the lubricant allowed him to slide further into me.

Suddenly, he was past the sphincter and entered me up to the base of his cock. I think I felt his pelvis and his balls against my cheeks but I don't know if that was really it. My rear opening felt like it was stretched about as far as it could be without me being torn apart. Instead of starting the in-and-out movement that I anticipated from vaginal sex, after Larry pushed himself in, I felt him pause and hold that position.

Larry next pulled himself part way out before he pushed himself back in. Then at last, the in-and-out motion began. Unlike the feeling of fullness I get from penis in vagina sex, my feeling back there was of being overfilled. I was still stretched to my limit but I didn't feel any tearing like I had feared. Some of my fear left me and I was able to partially relax.

The fullness and the stretching back there ranged somewhere between uncomfortable and painful but the pain stayed below an acceptable level. This wasn't the first time during sex that I felt a combination of pain and pleasure. It wasn't the first time that I was able use the pleasure to ease the pain and to use pain to increase my feeling of pleasure.

The lack of natural lubrication back there though definitely made it feel different from vaginal sex. Larry had used enough artificial lube that I didn't feel the vicious level of pain that I had experienced my first time despite the larger girth of his cock. That said, while his movement in and out of me didn't really hurt, it didn't feel good either. The motions of his cock sent only mild quivers to the nerves in my clit and I was forced to conclude that any thought of me coming would just be a fantasy.

I closed my eyes and pushed my face into the pillow. Instead of concentrating on my growing physical discomfort, I tried to focus on my emotions--how I was bringing pleasure to Larry, how I was giving him something on his bucket list, and how I was living up to my part of the deal.

When Larry first entered me, his hands held onto my shoulders giving him balance as he thrust in and pulled out. Now, he slid them around and under my body, cupping my breasts. His soft massaging of my boobs as he held them, along with his gently fingering of my nipples, felt nice and contrasted strangely with his rough movement below my waist. In fact, the breast play managed to pull my mind away from my discomfort below and gave me a level of arousal that I hadn't expected. To my great surprise, I became aware of a growing heaviness in my pelvis and I wondered if a climax might not be out of the question.

This led me to think about how, as I pegged Larry, I wasn't in contact with his cock in any way as I would normally be during sex. In response to his arousal, Larry had rubbed against the mattress until he came. I decided that fair is fair here too, so as he hammered himself into my ass and played with my boobs, I slid a hand down and my index finger went to its familiar spot on my clit. I tried to rub myself in synch with his movement in and out of me. Soon, I was breathing heavily, moaning loudly, and instead of hoping that Larry would quickly finish, I now yearned for him to last long enough for me to cum.

When Larry finally came, he pushed in deeply and grunted and simultaneously squeezed my nipples. That, along with fingering my clit, was enough and I climaxed too.

Larry lay across me and held me there for what seemed like forever, enjoying our orgasms, before he pulled out and went to the bathroom to clean himself off. I finally got up and went to the other bathroom. I checked my butt and was relieved to find that I wasn't bleeding back there.

Was I glad I did this? Well, I was glad that I did it for him and that I had returned some of the pleasure that he brings to our bed. I was relieved that I had been able to do my part of our I-will-if-you-will agreement. I was very grateful that, this time, the experience wasn't as bad as my previous time.

But did I like it? No, not really. I didn't hate like I thought I would and it wasn't really painful. I didn't hate it but I still didn't like it either.

So, would I do it again? Maybe? Larry and I do things to please each other as long as it's not something that we dislike. So maybe. We'll have to see. I really would like to peg him again some time so maybe I'd be willing to give him anal sex again if he'd be willing to reciprocate. After all, fair is fair, isn't it?