At first anal sex was a definite no with my wife. She made it quite clear from the start and I never bothered raising the issue. One night during some play she was laying on her front as I was fingering her pussy and I leant forward, parted her legs and licked her anus; it just seemed like the right thing to do at the time. As I did this I thought she would either be turned off or make a comment about ‘not going there’ but instead she responded by pulling herself up on to her knees and bending right over, I licked her anus more and used plenty of saliva as I started to push my tongue further in to her.
After doing this for around 5 mins I took some of the lube I had been using on her pussy and gently rubbed it on to and around her anus, I used plenty of it and slowly and very very gently passed my fingers around her anus sliding them around in the lube and she asked me to carry on in a very turned on and sexy voice. After a while I took a beep breath and really gently started to put ONE finger in her anus, I was waiting for the ‘dont do that’ but all she did was move herself nearer me and pushing my finger farther inside, I was surprised to say the least but carried on with this, then with more lube and again very slowly I pushed two fingers in.
She started to move herself forward and back on my fingers so I moved them in and out as if I were fucking her, at this point she became super aroused and was moving faster banging her cheeks on my hand, I used my other hand to rub and finger her pussy and she just went wild, pulling at the bed sheets and shouting ‘yes yes’ and I can’t tell you how amazed I was, this continued until she had an orgasm and laid back on the bed, she was bright red with panting, about 2 mins later she was asleep.
The next time we had sex I did the same as before except this time I took the courage to penetrate her and one thing that made her scream ‘fuck me fuck me’ was having my dick in her ass and my fingers in her pussy, I came so hard in her anus that I was out cold in no time. On the third occasion we had the usual foreplay, some pussy and anal fingering then she broke her own second rule. She gives a great blowjob no problem but I never ever came while she did it. This time she sucked me until I could not hold on any longer and I told her I was going to cum but she just kept sucking until she had the whole lot in her mouth. I have no idea why things suddenly changed like this but let me tell you I ain’t complaining.
I’d had anal sex before (with a girlfriend who found vaginal intercourse uncomfortable and actually preferred anal), but it was another girlfriend’s anal initiation that really stands out in my memory. I would often finger her asshole as I ate her out or when we fucked. She always seemed to dig it, but I was still surprised how readily she agreed when I suggested we give anal a try. She grabbed some moisturizing lotion to use as lube (which I guess isn’t recommended, but we didn’t know any better, and no harm seems to have come of it). I began to go down on her — thinking an orgasm might relax her and make the next part easier — but she was excited to get to it. She slurped at my dick, finding me rock hard already — I was excited to get to it, too — then turned away, presenting her ass.
I lubed her hole with lotion, dipped a finger in, then two, nothing new for us. Then I smoothed some lotion onto my cock and placed the head at her asshole. Leaning into her gently, I slid in with ease. She gasped as my cock stretched her, not a gasp of pain but of pleasure. I withdrew slightly, then slowly slid all the way into her. “Oh my god,” she breathed, pushing herself back onto me. We had started with her on hands and knees, me kneeling behind, but gradually wound up with us both kneeling upright and pumping together. I reached around and squeezed her breasts with one hand.
Her nipples were harder than I’d ever felt them. With my other hand I reached down to play with her pussy. I couldn’t believe how stimulated she was. Her clit was engorged beyond anything I’d seen before, sticking out like a tiny penis. I dipped my fingers into her sopping slit and stroked her rock-hard clit between a slippery thumb and finger, jacking it off like a little cock as I pumped in and out of her ass. She had always been the most orgasmic sex partner of my experience, but I’d never felt her cum before quite as powerfully as she did then, and we came together, me shooting off deep inside as her sphincter muscle spasmed around my cock.
Collapsing to the bed, breathless, we remained spooned together as I slowly melted inside her. She said she felt incredibly full with my cock up her ass and enjoyed her first time so much she suggested anal again when next we got together. Sadly the repeat performance wasn’t anywhere near as magical for either of us. We never tried anal again after that and broke up before long (for other reasons), but I still remember my ex’s anal initiation as the #1 highlight of my sex life.