When we married I had only a handful of anal experiences… relishing each one. My wife and I had one during our year and a half courting period. I had gone out with my buddies and came home all worked up and drunk enough to have my decision making abilities hindered to say the least. Needless to say, it wasn't one of my finest hours and didn't make it an experience Fili wanted to repeat.
Regardless, over the years we gradually started towards that direction albeit on a much slower course. One reason for such slow progress towards our goal was Fili's size. Standing 5'7, she was a petite little thing at only 112 pounds… and tighter than any woman I'd ever been with been with. Other contributing factors might have been that Fili was lactose intolerant and prone to some pretty painful gas after ingesting anything dairy or that contained beans. She also didn't eat enough fiber… so all stars had to be aligned in order for me to explore that nether region of bliss.
It didn't take long after our marriage before I was wrapping a hand behind her and circling her anus with a well licked finger whilst she ground down upon me. This, understandably, led to my insertion of said finger… and with a quick popping in and out provided Fili with the most intense of orgasms.
One fingertip became a finger length… that, eventually, turned into two fingers. On rare occasions we would slather on the KY liberally both to my ever so hard cock (it's amazing what anticipation and foreplay can do to a person) as well as working some on/in her oh-so-tight ass. We would work ever so slowly to allow my cock access and most times would have to abort due to extreme discomfort. Ah… but those handful of times where acceptance was granted led to phenomenal sex… satiating that desire in me for at least a few days.
One such memorable experience was on the first evening of our second anniversary vacation to Hawaii. Maybe it was not eating anything on the plane, the heat, the bubbly waiting for us in our room or the beautiful environment, but, that night I was really able to pound away. Lying on her back on the suite's sofa, each leg supported by hanging over my elbow, Fili was lovingly encouraging me to go faster and harder and we ended in a mutual screaming orgasm that I'm sure was heard throughout the resort.
After a few years of marriage just about all of our butt fucking had been done with Fili either lying prone on her flat tummy or on all fours doggy style. On the more successful ventures, she would moan how much she wished she could have two of me in her at the same time. One to grind down on and one to have sliding in and out of her sweet ass.
The idea had some appeal to me. I had been with two women long before meeting Fili and the idea of having another guy join us had never really crossed my mind. I guess that's a typical male double standard, though. But, being an impresario of sorts, my pleasure came from giving pleasure and if Fili might enjoy experiencing double penetration, I wanted to be able to let her try.
We started a little fantasy talk during sex, my finger(s) playing the role of the other man. We tried a bunch of different toys including a dildo with a ring that slipped over my cock. Some worked better than others, fingers providing the best results most frequently. Afterwards, we'd pant and talk a bit more seriously. Eventually, we started chatting with others on line… meeting some couples over drinks… sharing meals… all with the understanding we had some similar interests in exploring sexual fantasies.
During this exploratory period I started probing her ass with my tongue. Usually, it would start out with something like a hand warmed oil massage. Shoulders to back, back to butt, hands spreading butt cheeks, tongue pointed, circling butt… running the course of her crack than diving in as far as I could stick it out… (do they do tongue enlargements?). This was fun foreplay and provided better results but still not quite the frequency I desired.
Finally, after what seemed months of unsuccessful (although rather entertaining) introductions we decided to share a weekend beach house with a couple who were pretty much in the same boat as we were. After a fine meal, a few bottles of good red wine and a soak in the hot tub, things got rolling. Out first experience with swinging – jeeze, we both hate that term! For hours we kissed, rubbed, went down on each other. Pedra, the other woman had the same desire to try double P and Fili encouraged her to seize the opportunity. Fili was amazed at how easily Pedra, straddling her hubby – Roger, was able to take me into her ass. Granted, it wasn't nearly as tight as Fili's… and, well, at 5 inches I'm admittedly not the hugest of men (but I've been told by more than one woman I had the perfect sized cock for anal). We fucked and grinded until Pedra shuddered with a momentous orgasm… trying all the while to explain how good she felt by repeating, "I feel so… so… fucked!" to which we all laughed.
The stars weren't aligned that evening for Fili to try her first shot at double P. Nor were they the second, third or fourth time with Pedra and Roger. Or with a new couple whose first experience went very much the same way. In all of that though Fili started feeling self conscious about not being able to have anal as frequently as I desired. Bothered even more when she discovered that usually, before Pedra got the DP, we weren't just fucking when we swapped… Pedra was straddling my hips, lowering herself on to me and I was fucking her ass as kind of a warm up.
This discovery was just prior to a business trip I had to take the next day. Gone for a week, I thought I was going to explode if I had to stay away another day. Upon my return, I was met with a most glorious homecoming. It seems that Fili had given quite a bit of thought towards what was happening between Pedra and I and it occurred to her that we had never attempted it from that angle.
In bed that night, we were having a lot of fun… so much so that I wasn't even thinking of going back there. Fili was unusually wet as I found out later she was way turned on by the surprise she wanted to try out on me. She rolled me over on to my back and started grinding away… using my cock as her play toy and rubbing her clit over my very trimmed pubic area. She had a wild look in her eye and a devilish grin when she lifted up and with out aid of lubricant reached behind her to grab my swollen cock and slide it ever so slowly into her puckered ass. She opened her mouth with a silent "Ohhh!" taking in more and more. My head literally 'popped' in. Eventually we required a little squirt of lube back there and then we were on our way to the races. Once applied, she was effortlessly gliding up and down with an amazed look on her face… like a kid riding a bike for the first time without training wheels.
She lowered herself all the way to the base of my shaft and once again began rubbing her clit on my pubic mound. Her earthquake of an orgasm gave me the final squeeze which caused me to blow my load… which caused yet more aftershocks for herself. She collapsed on me damp with sweat, breathing heavy. In between breaths, she said she had thought about what I had shared with her and had an intense desire to try it for herself. She said it was so much easier that way and was glad she could get off with me 'back there' and at the same time grind her pussy all over me… she finally got to have two of me – so to speak.
We echoed that combination every night that week amounting to more anal sex than I'd had in the past year. We were even able to do it standing up in the shower on weekend afternoon. Either it's because the stars have finally clicked into place (hey, this is my year… the year of the horse!) or my little pony, Fili, has just learned a great new trick!