Chapter 5

Meanwhile, on the subject of anal sex, I was on the verge of rather special breakthrough in my continuing, still intensifying sexual and emotional odyssey with Nicki. Ever since I had fisted Jenny's bum, I had been yearning to experience for myself those awesome sensations that I had seen as expressions of wonder on her transported face. Weeks of delicious anal play with Nicki, occasional buggery with John, and even some reaming and stretching on my own with slyly measured vegetables, had brought me to the moment when I wanted to find out at last if I could take my lover's fist in my bottom. Despite my impatience, she had insisted we take our time, so she could teach me the muscular exercises she practices religiously, for bum and pussy both. My pelvic floor had never been stronger! Despite the stretching I was now capable of, I had actually learned to tighten enough to enjoy Jerome's cock properly for the first time in years! Nicki is even stricter than Jenny about regular exercising - that's why her pussy still looks so small and neat, and her asshole can pucker tight as a virgin on my finger, and yet open to let me fist into it smoothly just a few moments later.

I want to tell you a little more about Nicki. She's one of those rare, wonderfully lucky women who find out at an early age what their sexual preferences really are, and how those preferences can be expressed. Nicki definitely prefers women to men, but isn't dogmatic about it. She says she's mostly lesbian, rather than bisexual, because for her a very few carefully chosen men occasionally have their uses, even in bed, and reckons that the best anal sex, apart from fisting, can be with an understanding man. Not, she is likely to add, that there are many of those around! Like Jenny, she discovered vaginal fisting all by herself, but unlike Jenny who was in her early twenties at the time, she was only sixteen! For two years it was her secret vice, and then she met an older woman, her first serious lover, who taught her how to make the most of her gift, and also to love anal fisting, and much more than that besides.

Nicki was introduced to a decadent lesbian scene that involved sex in gay clubs, many dark nights of S&M, drugged out weekends on Ecstasy, orgying with strange women, and found out eventually exactly how far she was willing to go in search of pleasure, and where the line was drawn. After a couple of happy, frenzied years of hedonism, the jealousy and possessiveness of her older partner began to impinge seriously upon the pleasure, which was waning anyway as the shock of the new wore off. At the end of four increasingly traumatic years, the affair broke up messily when Nicki, eventually realising that she wasn't the slutty, helpless submissive she's always been told she was, and one day refused to get her clit pierced and her arse tattooed with her lover's name, as she had been ordered to do. When it was all over and the dust had settled, Nicki then enjoyed the next half dozen quietly promiscuous years that were drawing to a close when I met her. At twenty-eight, Nicki already had twelve years of fisting experience, compared to my six months.

When had I watched her, naked on her knees, with a casual jerk of her hips sinking a lube-shiny hand deep into her own arse, I envied her in my soul, but knew that soon, with her help, I too could become one of that select band of women who found pleasure in bum-fisting, and one, maybe I could even be as... self-sufficient... as her!

One November Saturday, I sent the boys off to the Science Museum with their father, and I went over to Nicki's, my heart pounding because I had made up my mind it was going to be today. My body had been telling me the time was right for a couple of weeks. My lover let me in and kissed me tenderly.

"How do you feel?" She asked.

"I feel good... I feel ready," I confirmed, nodding firmly.

I knew this was quite a big step, and I was glad Nicki had made me wait until now.

We went to the bedroom. Away from the steel grey light of late autumn, with the curtains drawn shut, it was very warm, cosy and softly lit in her inner sanctum. Nicki had strategically placed several mirrors for us to enjoy the view. With little preamble, we slipped out of our clothes, smoked a spliff to help me relax, and had a special cuddle. When we were both feeling giggly stoned, and very comfortable, Nicki brought out the lube, a very large dildo, and a bottle of poppers - which I hadn't needed (except for in a couple of moments of wild greed) for quite some time. Fully equipped, she climbed back onto the bed. I opened my thighs wide, laying back against the heaped pillows, and stroking my already moistly aroused pussy. Nicki smiled at me as she lubricated the dildo with a special silicone based oil she had discovered, that remained slippery for ages. I had become very fond of that foot long, three-inch thick, black latex shaft. It had entered me many times recently, mostly in the arse...

"Kneel on the bed, put your arse in the air for me," Nicki instructed. I rolled over and I lifted my bottom, exposing the rosebud more clearly, and resting my elbows on the bed. I felt Nicki slide a well-oiled finger into my rectum, and moaned softly. A few moments later, the head of the dildo was touching my anus.

"Higher... make it pout, and then relax..." Nicki told me. I positioned myself as she wanted, clenched, pushed and then softened my sphincter muscles as I had now learned. Then I arched, gasping with pleasure as the huge head of the dildo spread me, wider and wider, so that I clutched at the bed, willing my bottom not to fight it. I yelped and grinned greedily to myself as it's long, bulbous glans slid slowly into me. Very slowly, Nicki penetrated my arse, inch after inch of dildo filling me with its firm but slightly flexible rubber girth. I breathed slowly with each thrust, feeling it begin to probe deeper inside, and squirmed, because I now knew ways to take even more. It was so long... I closed my eyes, panting in shallow breaths, and used my imagination to see it moving in my bowels... It felt monstrous, and splendid. I winced as it hit the end of the tunnel. Then Nicki pulled and thrust it, and exultantly I let my arse open to it as she had taught me, soon allowing it to plunge in and out with surprising ease. I love that big sweet, anal gliding so much! I stroked my clit as she buggered me, my pleasure growing huge, wild, and wanton. Feeling that, she pulled the dildo all the way out, and squeezed it right back in again.

"Oh God yessss! I gasped.

Nicki penetrated me like that again and again, until my asshole stayed open at each slurping exit, and the massive glans popped my ring exquisitely. The shaft was as thicker than her wrist, and I was taking it with ease. This dildo was solid rubber, and pretty heavy; soon Nicki was literally dropping it into my arse, the weight of it alone carrying the massive shaft almost to my limits! My finger blurred on my clit, and in seconds, I felt the violent shaking bliss of orgasm engulf me. Nicki always says it's good to come like this, when you're a beginner, because it loosens the muscles more, once the initial tension has been spasmed out of them. I cawed and clutched at my quaking pussy, the strong contractions gripping my arse muscles around most of the length of the shaft.