Turnabout is Fair Play

We're about five years married so far and my wife Jamie is pretty straight laced, other than a few visits to couples clubs which she wrote about here in Literotica. Anyway, the one thing missing from our sex lives as far as I was concerned was anal sex. I never had the pleasure before marriage, and Jamie has always resisted any attempts on my part to experiment.

She has considered it unnatural, dirty, and probably painful. No amount of cajoling had convinced her otherwise until recently. Somehow, the subject came up when she was talking to a couple of her girl friends and one said something to the effect that the guys always want to fuck us in the ass, but they wouldn't like it if someone did the same to them. The other girl said she sort of liked anal sex, but that it took her quite a while to get used to it. Jamie of course said she never had done it, and had no intention of doing so.

Later, probably while driving home from their coffee klatch, she got to thinking about what she thought might be fun, and perhaps cure me of my constant attempts to have her do anal sex with me. A week or so later, the next time I hinted at my desire to try, she said, "OK, here's a deal for you. Whatever you want to do to me, I get to do to you first."

My reaction to that was typical male I guess. "What? No guys do that except gay males and prison rape victims! No Way!" But then, later that night I got to thinking that it was a reasonable proposition and it was just between us, so no embarrassment had to occur, and learning together might be fun. So, I told her OK on the deal. She looked a little surprised, but had an interesting grin that I didn't know whether it meant she was happy, or shocked, but it probably meant that she was sure I would chicken out before it was over.

We decided to try first with fingers in the shower. She soaped up a finger and my ass and slowly worked it into me. It was neither good nor bad as it turned out. Then I did the same to her and her reaction was similar. We tried two fingers each and it was similarly uneventful. We decided that maybe fingers were too short to be effective so next time we had a chance we bought some carrots of different sizes. When we tried that, it made a big difference for me. There was a little pain but there was one area that felt sort of good, I now believe it was rubbing some part of my prostate. The carrot had no particular good feeling for Jamie.

We tried a couple different sizes and shapes over the next few nights and we were both beginning to tolerate it pretty well even though admittedly it was better for me and not so good for Jamie. At least we were getting stretched.

I asked Jamie if she was ready for the real thing and she said, "Yes, if you are ready to have my dildo up your ass."

"Wait a minute," I said, "Your dildo is bigger than my penis. We especially bought it that way for times when you felt deprived by my skinny six incher."

"So," she answered, "go down to the sex store and see if you can buy one as small as yours!"

"What an insult!" I thought.

The next day, I did succeed in getting a smallish strap-on ordered on the Internet that I thought would do the job. I was so anxious I even paid for overnight Fed-Ex. I must admit I spent most of the day with an erection, looking forward to the chance to finally put it in Jamie's ass. Had I known the difficulties and discomfort that were ahead it probably would have withered instantly.

Again, home early, rush thru dinner, rush thru shower, skip the newspaper and the TV, and off to bed. Jamie seemed to like the attention, but I could also sense trepidation. By the time we were in the bed I definitely had what is known as a raging hard-on. It even hurt a little it was so engorged. Jamie took one look at it and said, as if speaking to my penis, "Well big boy, you look anxious, but I think you are getting a little ahead of yourself." With that she began to examine the strap-on, adjust it, fondle it, even occasionally fondling my erection. She said I had done a good job getting one my size, and even maybe a tad smaller, but she agreed to continue with the deal much to my relief.

I assumed "the position" and as she fully lubed the dildo and my ass, I felt ready. As she started to enter, it was difficult. It was tight, and mildly painful. As the head popped in it was better, and as she began to slowly ease if farther in, the discomfort became significant and I asked her to stop. She said it was barely past the head, and that if big boy didn't get into her any further than that he'd be pretty sad. I told her to work it back and forth a little and it did deepen slightly before it became too uncomfortable. So we quit.

My erection had vanished by that time, but when she said, "OK, it's your turn," with a smile and a wink, it came right back. She showed me about how far she had penetrated me, and said, "Don't forget you are on the honor system here," and I understood. Not surprisingly the insertion and getting past the head was about the same as when we were reversed and as I approached the magic limit, she said that she felt discomfort and that I should stop. I withdrew slightly and reinserted to ease the way, and immediately blew my load. It was so tight, and I had waited so long, that I couldn't control it at all.

The fact is that Jamie was happy, because she didn't want any more, but said she was short-changed because she didn't get off. My fingers and tongue immediately handled that task with mutual satisfaction being achieved. "Tomorrow is another day," she said with a wink, and I could feel little ole "big boy" getting ready again.

The next night was pretty much a repeat, but with deeper penetration on both sides. The next night we took a rest, and the following night we finally achieved full penetration on both sides. For Jamie, it was no particular pleasure, but represented an accomplishment, meeting a goal. For me it was like a dream come true. Tighter than the tightest pussy I was ever in. When the full thrust allowed her sphincter muscle to grab the base of my cock, I thought my head would blow off, it felt so good.

Now, after several weeks of off-and-on experimenting, anal penetration has become part of our sex lives. When we do decide wordlessly that it will be done, I satisfy her by plunging her big dildo into her pussy with the same rhythm that I am using in her ass. This feels good to her, gives her an orgasm to match mine, and is a good mutual satisfaction. Still, she makes me periodically live up to my end of the bargain, and she fucks me in the ass with the small dildo. The good part is she uses one hand to stroke my cock in synch with her anal thrusts and when I cum, she usually quits.

So, this is the story, with a happy ending, of how I got my wife to succumb to anal sex. It was a fair amount of work, but worth it, particularly since I get off whether I'm doing her, or whether she's doing me.